data_sw03 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; racemic 4'-ethyl 5'-methyl(3R,4'S,5'S)-1-acetyl-5-fluoro-2'-(4-methyoxyphenyl)- 2-oxo-4'5'-dihydrospiro[indoline-3,3'-pyrrole]-4'5'-dicarboxylate ; _chemical_name_common 'trans-3a' _chemical_melting_point ? _chemical_formula_moiety 'C25 H23 F N2 O7' _chemical_formula_sum 'C25 H23 F N2 O7' _chemical_formula_weight 482.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.188(9) _cell_length_b 10.623(3) _cell_length_c 28.223(8) _cell_angle_alpha 90 _cell_angle_beta 100.167(3) _cell_angle_gamma 90 _cell_volume 9204(4) _cell_formula_units_Z 16 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9963 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_F_000 4032 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 1.193 _exptl_crystal_size_mid 1.139 _exptl_crystal_size_min 0.963 _exptl_absorpt_coefficient_mu 0.108 _shelx_estimated_absorpt_T_min 0.882 _shelx_estimated_absorpt_T_max 0.903 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.657 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 42994 _diffrn_reflns_av_unetI/netI 0.0252 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.797 _diffrn_reflns_theta_max 27.569 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 10567 _reflns_number_gt 8509 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'SMART (Bruker, v5.054)' _computing_cell_refinement 'SAINT (Bruker, v6.45A)' _computing_data_reduction 'SAINT (Bruker, v6.45A)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'XP (Sheldrick, 1997)' _computing_publication_material 'SHELXL-2013 (Sheldrick, 2013)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+4.7822P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 10567 _refine_ls_number_parameters 639 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.25112(3) 0.17368(8) 0.06526(4) 0.0413(2) Uani 1 1 d . . . . . O1 O 0.26169(3) 0.77929(10) 0.05576(4) 0.0352(2) Uani 1 1 d . . . . . O2 O 0.12746(3) 0.73811(9) 0.01597(4) 0.0313(2) Uani 1 1 d . . . . . O3 O 0.13021(3) 0.41986(10) 0.15188(3) 0.0328(2) Uani 1 1 d . . . . . O4 O 0.16659(3) 0.58731(9) 0.12990(3) 0.0265(2) Uani 1 1 d . . . . . O5 O 0.12511(4) 0.52892(12) -0.20604(4) 0.0446(3) Uani 1 1 d . . . . . O6 O 0.02067(3) 0.49418(11) 0.07292(5) 0.0444(3) Uani 1 1 d . . . . . O7 O 0.01837(3) 0.28613(10) 0.05879(4) 0.0320(2) Uani 1 1 d . . . . . N1 N 0.19908(3) 0.66690(10) 0.03859(4) 0.0225(2) Uani 1 1 d . . . . . N2 N 0.08170(3) 0.38684(10) 0.00047(4) 0.0234(2) Uani 1 1 d . . . . . C1 C 0.21851(4) 0.54497(12) 0.04638(4) 0.0217(2) Uani 1 1 d . . . . . C2 C 0.26223(4) 0.51182(14) 0.05588(5) 0.0288(3) Uani 1 1 d . . . . . H2 H 0.2844 0.5738 0.0580 0.035 Uiso 1 1 calc R U . . . C3 C 0.27243(4) 0.38437(14) 0.06212(5) 0.0319(3) Uani 1 1 d . . . . . H3 H 0.3020 0.3583 0.0686 0.038 Uiso 1 1 calc R U . . . C4 C 0.23985(4) 0.29667(13) 0.05887(5) 0.0280(3) Uani 1 1 d . . . . . C5 C 0.19590(4) 0.32749(12) 0.04946(4) 0.0236(3) Uani 1 1 d . . . . . H5 H 0.1739 0.2650 0.0474 0.028 Uiso 1 1 calc R U . . . C6 C 0.18592(4) 0.45380(12) 0.04321(4) 0.0205(2) Uani 1 1 d . . . . . C7 C 0.14193(4) 0.51626(12) 0.03222(4) 0.0203(2) Uani 1 1 d . . . . . C8 C 0.15347(4) 0.65490(12) 0.02694(4) 0.0225(3) Uani 1 1 d . . . . . C9 C 0.22220(4) 0.78140(13) 0.04768(5) 0.0276(3) Uani 1 1 d . . . . . C10 C 0.19607(6) 0.89860(14) 0.04909(7) 0.0422(4) Uani 1 1 d . . . . . H10A H 0.2157 0.9699 0.0583 0.063 Uiso 1 1 calc R U . . . H10B H 0.1768 0.8888 0.0727 0.063 Uiso 1 1 calc R U . . . H10C H 0.1786 0.9141 0.0172 0.063 Uiso 1 1 calc R U . . . C11 C 0.11159(4) 0.45716(12) -0.01103(4) 0.0209(2) Uani 1 1 d . . . . . C12 C 0.08393(4) 0.38909(12) 0.05323(4) 0.0227(3) Uani 1 1 d . . . . . H12 H 0.0980 0.3102 0.0678 0.027 Uiso 1 1 calc R U . . . C13 C 0.11234(4) 0.50279(12) 0.07110(4) 0.0217(2) Uani 1 1 d . . . . . H13 H 0.0929 0.5783 0.0686 0.026 Uiso 1 1 calc R U . . . C14 C 0.13687(4) 0.49604(12) 0.12227(4) 0.0231(3) Uani 1 1 d . . . . . C15 C 0.19597(4) 0.58898(14) 0.17649(4) 0.0281(3) Uani 1 1 d . . . . . H15A H 0.2092 0.5050 0.1838 0.034 Uiso 1 1 calc R U . . . H15B H 0.1798 0.6120 0.2024 0.034 Uiso 1 1 calc R U . . . C16 C 0.23056(5) 0.68505(16) 0.17287(5) 0.0387(4) Uani 1 1 d . . . . . H16A H 0.2511 0.6886 0.2034 0.058 Uiso 1 1 calc R U . . . H16B H 0.2170 0.7678 0.1659 0.058 Uiso 1 1 calc R U . . . H16C H 0.2461 0.6614 0.1469 0.058 Uiso 1 1 calc R U . . . C17 C 0.11726(4) 0.47476(12) -0.06150(4) 0.0220(3) Uani 1 1 d . . . . . C18 C 0.08213(4) 0.44855(14) -0.09881(5) 0.0281(3) Uani 1 1 d . . . . . H18 H 0.0556 0.4176 -0.0913 0.034 Uiso 1 1 calc R U . . . C19 C 0.08599(5) 0.46750(15) -0.14625(5) 0.0338(3) Uani 1 1 d . . . . . H19 H 0.0619 0.4510 -0.1711 0.041 Uiso 1 1 calc R U . . . C20 C 0.12513(5) 0.51080(14) -0.15799(5) 0.0288(3) Uani 1 1 d . . . . . C21 C 0.16053(4) 0.53444(13) -0.12170(5) 0.0281(3) Uani 1 1 d . . . . . H21 H 0.1875 0.5617 -0.1294 0.034 Uiso 1 1 calc R U . . . C22 C 0.15600(4) 0.51760(13) -0.07383(5) 0.0260(3) Uani 1 1 d . . . . . H22 H 0.1800 0.5358 -0.0490 0.031 Uiso 1 1 calc R U . . . C23 C 0.16478(5) 0.56160(15) -0.22112(5) 0.0379(3) Uani 1 1 d . . . . . H23A H 0.1596 0.5718 -0.2562 0.057 Uiso 1 1 calc R U . . . H23B H 0.1863 0.4948 -0.2118 0.057 Uiso 1 1 calc R U . . . H23C H 0.1758 0.6408 -0.2058 0.057 Uiso 1 1 calc R U . . . C24 C 0.03771(4) 0.39850(13) 0.06339(5) 0.0263(3) Uani 1 1 d . . . . . C25 C -0.02751(5) 0.28453(17) 0.06195(6) 0.0414(4) Uani 1 1 d . . . . . H25A H -0.0378 0.1973 0.0612 0.062 Uiso 1 1 calc R U . . . H25B H -0.0440 0.3308 0.0346 0.062 Uiso 1 1 calc R U . . . H25C H -0.0317 0.3244 0.0921 0.062 Uiso 1 1 calc R U . . . F2 F 0.00618(3) 1.34727(9) 0.18572(5) 0.0638(3) Uani 1 1 d . . . . . O8 O -0.01075(4) 0.74694(12) 0.19128(6) 0.0648(4) Uani 1 1 d . . . . . O9 O 0.12457(3) 0.77006(9) 0.21288(4) 0.0332(2) Uani 1 1 d . . . . . O10 O 0.12769(3) 1.11279(9) 0.09209(3) 0.0313(2) Uani 1 1 d . . . . . O11 O 0.08919(3) 0.94471(10) 0.10912(3) 0.0304(2) Uani 1 1 d . . . . . O12 O 0.11459(4) 0.98763(10) 0.44586(3) 0.0363(2) Uani 1 1 d . . . . . O13 O 0.23501(4) 1.04576(12) 0.17382(5) 0.0505(3) Uani 1 1 d . . . . . O14 O 0.23189(3) 1.25192(10) 0.18918(4) 0.0389(3) Uani 1 1 d . . . . . N3 N 0.05363(4) 0.84984(10) 0.20209(4) 0.0256(2) Uani 1 1 d . . . . . N4 N 0.17033(3) 1.12544(11) 0.24548(4) 0.0263(2) Uani 1 1 d . . . . . C26 C 0.03557(4) 0.97387(13) 0.19669(4) 0.0247(3) Uani 1 1 d . . . . . C27 C -0.00792(4) 1.01056(15) 0.18912(5) 0.0328(3) Uani 1 1 d . . . . . H27 H -0.0307 0.9501 0.1865 0.039 Uiso 1 1 calc R U . . . C28 C -0.01698(5) 1.13821(16) 0.18548(6) 0.0392(4) Uani 1 1 d . . . . . H28 H -0.0463 1.1666 0.1803 0.047 Uiso 1 1 calc R U . . . C29 C 0.01640(5) 1.22342(15) 0.18934(6) 0.0388(4) Uani 1 1 d . . . . . C30 C 0.05994(4) 1.18950(13) 0.19692(5) 0.0312(3) Uani 1 1 d . . . . . H30 H 0.0825 1.2506 0.1997 0.037 Uiso 1 1 calc R U . . . C31 C 0.06884(4) 1.06186(12) 0.20018(4) 0.0231(3) Uani 1 1 d . . . . . C32 C 0.11216(4) 0.99576(12) 0.20852(4) 0.0221(3) Uani 1 1 d . . . . . C33 C 0.09928(4) 0.85676(12) 0.20863(4) 0.0241(3) Uani 1 1 d . . . . . C34 C 0.02846(5) 0.73808(15) 0.19876(6) 0.0407(4) Uani 1 1 d . . . . . C35 C 0.05182(7) 0.61611(17) 0.20471(10) 0.0738(7) Uani 1 1 d . . . . . H35A H 0.0308 0.5476 0.2048 0.111 Uiso 1 1 calc R U . . . H35B H 0.0724 0.6160 0.2353 0.111 Uiso 1 1 calc R U . . . H35C H 0.0677 0.6040 0.1781 0.111 Uiso 1 1 calc R U . . . C36 C 0.14130(4) 1.04805(12) 0.25421(4) 0.0232(3) Uani 1 1 d . . . . . C37 C 0.16891(4) 1.13467(13) 0.19275(5) 0.0252(3) Uani 1 1 d . . . . . H37 H 0.1537 1.2139 0.1802 0.030 Uiso 1 1 calc R U . . . C38 C 0.14244(4) 1.02030(13) 0.17131(4) 0.0239(3) Uani 1 1 d . . . . . H38 H 0.1629 0.9473 0.1726 0.029 Uiso 1 1 calc R U . . . C39 C 0.11931(4) 1.03414(13) 0.11979(5) 0.0241(3) Uani 1 1 d . . . . . C40 C 0.06203(5) 0.94858(15) 0.06109(5) 0.0334(3) Uani 1 1 d . . . . . H40A H 0.0792 0.9235 0.0363 0.040 Uiso 1 1 calc R U . . . H40B H 0.0505 1.0346 0.0537 0.040 Uiso 1 1 calc R U . . . C41 C 0.02536(6) 0.8575(2) 0.06213(6) 0.0519(5) Uani 1 1 d . . . . . H41A H 0.0062 0.8566 0.0306 0.078 Uiso 1 1 calc R U . . . H41B H 0.0087 0.8836 0.0868 0.078 Uiso 1 1 calc R U . . . H41C H 0.0373 0.7730 0.0696 0.078 Uiso 1 1 calc R U . . . C42 C 0.13321(4) 1.02617(13) 0.30381(4) 0.0237(3) Uani 1 1 d . . . . . C43 C 0.13953(5) 1.12617(13) 0.33703(5) 0.0295(3) Uani 1 1 d . . . . . H43 H 0.1488 1.2057 0.3272 0.035 Uiso 1 1 calc R U . . . C44 C 0.13250(5) 1.11106(13) 0.38358(5) 0.0311(3) Uani 1 1 d . . . . . H44 H 0.1364 1.1802 0.4053 0.037 Uiso 1 1 calc R U . . . C45 C 0.11965(4) 0.99418(13) 0.39888(5) 0.0265(3) Uani 1 1 d . . . . . C46 C 0.11333(4) 0.89341(13) 0.36671(5) 0.0257(3) Uani 1 1 d . . . . . H46 H 0.1046 0.8136 0.3768 0.031 Uiso 1 1 calc R U . . . C47 C 0.11993(4) 0.91074(13) 0.31956(5) 0.0248(3) Uani 1 1 d . . . . . H47 H 0.1153 0.8421 0.2977 0.030 Uiso 1 1 calc R U . . . C48 C 0.10380(5) 0.86742(14) 0.46334(5) 0.0340(3) Uani 1 1 d . . . . . H48A H 0.1026 0.8737 0.4977 0.051 Uiso 1 1 calc R U . . . H48B H 0.1260 0.8058 0.4585 0.051 Uiso 1 1 calc R U . . . H48C H 0.0754 0.8404 0.4457 0.051 Uiso 1 1 calc R U . . . C49 C 0.21544(4) 1.13641(14) 0.18348(5) 0.0287(3) Uani 1 1 d . . . . . C50 C 0.27747(5) 1.26686(18) 0.18622(6) 0.0447(4) Uani 1 1 d . . . . . H50A H 0.2834 1.3554 0.1801 0.067 Uiso 1 1 calc R U . . . H50B H 0.2844 1.2148 0.1599 0.067 Uiso 1 1 calc R U . . . H50C H 0.2954 1.2405 0.2167 0.067 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0308(4) 0.0270(4) 0.0636(6) 0.0039(4) 0.0020(4) 0.0073(4) O1 0.0294(5) 0.0355(6) 0.0402(6) -0.0027(4) 0.0046(4) -0.0135(4) O2 0.0274(5) 0.0242(5) 0.0408(6) 0.0031(4) 0.0015(4) 0.0024(4) O3 0.0372(5) 0.0350(6) 0.0263(5) 0.0044(4) 0.0058(4) -0.0048(4) O4 0.0262(5) 0.0319(5) 0.0204(4) -0.0004(4) 0.0012(3) -0.0041(4) O5 0.0417(6) 0.0709(8) 0.0204(5) 0.0032(5) 0.0035(4) -0.0034(6) O6 0.0276(5) 0.0372(6) 0.0726(8) -0.0074(5) 0.0208(5) 0.0006(5) O7 0.0222(5) 0.0344(5) 0.0406(5) -0.0001(4) 0.0089(4) -0.0064(4) N1 0.0218(5) 0.0226(5) 0.0231(5) -0.0001(4) 0.0037(4) -0.0039(4) N2 0.0192(5) 0.0250(6) 0.0258(5) -0.0009(4) 0.0037(4) -0.0013(4) C1 0.0212(6) 0.0243(6) 0.0198(5) -0.0005(5) 0.0037(4) -0.0032(5) C2 0.0199(6) 0.0323(7) 0.0335(7) 0.0003(6) 0.0034(5) -0.0057(5) C3 0.0179(6) 0.0377(8) 0.0390(8) 0.0011(6) 0.0023(5) 0.0034(6) C4 0.0262(7) 0.0246(7) 0.0325(7) 0.0013(5) 0.0029(5) 0.0035(5) C5 0.0217(6) 0.0240(6) 0.0246(6) -0.0003(5) 0.0026(5) -0.0026(5) C6 0.0168(5) 0.0261(6) 0.0185(5) -0.0012(5) 0.0031(4) -0.0014(5) C7 0.0186(6) 0.0215(6) 0.0204(6) 0.0008(4) 0.0027(4) -0.0017(5) C8 0.0228(6) 0.0238(6) 0.0209(6) -0.0010(5) 0.0038(5) -0.0020(5) C9 0.0314(7) 0.0280(7) 0.0239(6) -0.0010(5) 0.0062(5) -0.0095(6) C10 0.0430(9) 0.0255(8) 0.0584(10) -0.0072(7) 0.0097(7) -0.0091(7) C11 0.0169(5) 0.0208(6) 0.0241(6) -0.0009(5) 0.0019(4) 0.0008(5) C12 0.0185(6) 0.0239(6) 0.0260(6) 0.0007(5) 0.0047(5) -0.0002(5) C13 0.0184(6) 0.0234(6) 0.0242(6) 0.0007(5) 0.0059(5) 0.0002(5) C14 0.0208(6) 0.0264(6) 0.0232(6) -0.0014(5) 0.0074(5) 0.0019(5) C15 0.0284(7) 0.0340(7) 0.0201(6) -0.0013(5) -0.0010(5) 0.0013(6) C16 0.0326(8) 0.0497(10) 0.0302(7) -0.0011(6) -0.0041(6) -0.0089(7) C17 0.0220(6) 0.0212(6) 0.0222(6) -0.0004(5) 0.0024(5) 0.0004(5) C18 0.0209(6) 0.0341(7) 0.0285(6) -0.0013(5) 0.0018(5) -0.0046(6) C19 0.0270(7) 0.0465(9) 0.0250(7) -0.0028(6) -0.0038(5) -0.0038(6) C20 0.0322(7) 0.0327(7) 0.0212(6) -0.0002(5) 0.0036(5) 0.0009(6) C21 0.0261(6) 0.0333(7) 0.0256(6) -0.0004(5) 0.0061(5) -0.0047(6) C22 0.0226(6) 0.0320(7) 0.0223(6) -0.0004(5) 0.0008(5) -0.0036(5) C23 0.0522(9) 0.0387(8) 0.0258(7) 0.0013(6) 0.0152(6) 0.0083(7) C24 0.0207(6) 0.0310(7) 0.0276(6) 0.0020(5) 0.0051(5) -0.0025(5) C25 0.0236(7) 0.0496(10) 0.0530(9) -0.0045(8) 0.0122(6) -0.0103(7) F2 0.0399(6) 0.0320(5) 0.1142(10) 0.0026(6) -0.0006(6) 0.0120(4) O8 0.0348(7) 0.0430(7) 0.1115(12) 0.0038(7) -0.0012(7) -0.0198(6) O9 0.0337(5) 0.0268(5) 0.0396(5) 0.0010(4) 0.0082(4) 0.0044(4) O10 0.0350(5) 0.0318(5) 0.0279(5) 0.0040(4) 0.0076(4) -0.0033(4) O11 0.0293(5) 0.0358(5) 0.0249(5) 0.0001(4) 0.0017(4) -0.0084(4) O12 0.0534(7) 0.0321(5) 0.0243(5) 0.0007(4) 0.0098(4) -0.0005(5) O13 0.0275(6) 0.0462(7) 0.0816(9) -0.0036(6) 0.0197(6) -0.0012(5) O14 0.0248(5) 0.0403(6) 0.0518(6) 0.0052(5) 0.0074(4) -0.0105(5) N3 0.0247(5) 0.0240(6) 0.0278(5) -0.0011(4) 0.0036(4) -0.0062(5) N4 0.0205(5) 0.0305(6) 0.0275(6) 0.0006(4) 0.0033(4) -0.0037(5) C26 0.0228(6) 0.0275(7) 0.0237(6) -0.0005(5) 0.0035(5) -0.0050(5) C27 0.0207(6) 0.0396(8) 0.0374(7) -0.0008(6) 0.0030(5) -0.0049(6) C28 0.0199(7) 0.0450(9) 0.0513(9) 0.0013(7) 0.0022(6) 0.0053(6) C29 0.0312(8) 0.0293(8) 0.0538(9) 0.0015(7) 0.0013(7) 0.0067(6) C30 0.0250(7) 0.0260(7) 0.0418(8) 0.0019(6) 0.0033(6) -0.0034(6) C31 0.0178(6) 0.0276(7) 0.0234(6) 0.0009(5) 0.0025(5) -0.0021(5) C32 0.0187(6) 0.0241(6) 0.0235(6) 0.0014(5) 0.0038(5) -0.0018(5) C33 0.0250(6) 0.0260(7) 0.0213(6) -0.0004(5) 0.0047(5) -0.0029(5) C34 0.0373(8) 0.0313(8) 0.0509(9) -0.0002(7) 0.0007(7) -0.0135(7) C35 0.0549(12) 0.0261(9) 0.134(2) -0.0014(11) -0.0008(13) -0.0131(9) C36 0.0184(6) 0.0233(6) 0.0272(6) 0.0008(5) 0.0024(5) 0.0005(5) C37 0.0195(6) 0.0288(7) 0.0271(6) 0.0026(5) 0.0038(5) -0.0020(5) C38 0.0188(6) 0.0269(7) 0.0264(6) 0.0018(5) 0.0055(5) -0.0013(5) C39 0.0207(6) 0.0263(7) 0.0267(6) -0.0016(5) 0.0077(5) 0.0008(5) C40 0.0314(7) 0.0432(8) 0.0241(6) -0.0051(6) 0.0005(5) -0.0015(6) C41 0.0393(9) 0.0750(13) 0.0387(9) -0.0123(8) -0.0003(7) -0.0190(9) C42 0.0167(6) 0.0289(7) 0.0247(6) 0.0011(5) 0.0016(5) -0.0003(5) C43 0.0309(7) 0.0267(7) 0.0306(7) 0.0024(5) 0.0043(5) -0.0044(6) C44 0.0365(7) 0.0273(7) 0.0285(7) -0.0031(5) 0.0027(6) -0.0013(6) C45 0.0241(6) 0.0318(7) 0.0230(6) 0.0022(5) 0.0023(5) 0.0026(6) C46 0.0234(6) 0.0263(7) 0.0265(6) 0.0039(5) 0.0018(5) -0.0017(5) C47 0.0209(6) 0.0276(7) 0.0250(6) -0.0008(5) 0.0015(5) -0.0011(5) C48 0.0418(8) 0.0359(8) 0.0256(7) 0.0049(6) 0.0098(6) 0.0015(7) C49 0.0218(6) 0.0361(8) 0.0279(6) 0.0058(6) 0.0032(5) -0.0034(6) C50 0.0250(7) 0.0564(11) 0.0523(9) 0.0116(8) 0.0056(6) -0.0152(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C4 1.3567(16) . ? O1 C9 1.2125(17) . ? O2 C8 1.2027(16) . ? O3 C14 1.2073(16) . ? O4 C14 1.3324(16) . ? O4 C15 1.4641(15) . ? O5 C20 1.3696(16) . ? O5 C23 1.4205(19) . ? O6 C24 1.1992(17) . ? O7 C24 1.3334(17) . ? O7 C25 1.4495(17) . ? N1 C8 1.4082(16) . ? N1 C9 1.4142(17) . ? N1 C1 1.4305(17) . ? N2 C11 1.2803(16) . ? N2 C12 1.4783(16) . ? C1 C2 1.3878(18) . ? C1 C6 1.3954(17) . ? C2 C3 1.395(2) . ? C2 H2 0.9500 . ? C3 C4 1.370(2) . ? C3 H3 0.9500 . ? C4 C5 1.3886(18) . ? C5 C6 1.3817(18) . ? C5 H5 0.9500 . ? C6 C7 1.5062(17) . ? C7 C8 1.5296(18) . ? C7 C11 1.5401(16) . ? C7 C13 1.5599(17) . ? C9 C10 1.492(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C17 1.4780(17) . ? C12 C24 1.5222(18) . ? C12 C13 1.5298(18) . ? C12 H12 1.0000 . ? C13 C14 1.5120(17) . ? C13 H13 1.0000 . ? C15 C16 1.502(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.3915(18) . ? C17 C18 1.4069(17) . ? C18 C19 1.3801(19) . ? C18 H18 0.9500 . ? C19 C20 1.398(2) . ? C19 H19 0.9500 . ? C20 C21 1.3900(19) . ? C21 C22 1.3945(18) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? F2 C29 1.3533(18) . ? O8 C34 1.207(2) . ? O9 C33 1.2049(16) . ? O10 C39 1.2041(16) . ? O11 C39 1.3328(16) . ? O11 C40 1.4668(16) . ? O12 C45 1.3645(16) . ? O12 C48 1.4305(18) . ? O13 C49 1.1971(19) . ? O14 C49 1.3289(18) . ? O14 C50 1.4474(18) . ? N3 C33 1.4049(17) . ? N3 C34 1.4172(18) . ? N3 C26 1.4305(18) . ? N4 C36 1.2788(17) . ? N4 C37 1.4842(17) . ? C26 C31 1.3871(18) . ? C26 C27 1.3908(19) . ? C27 C28 1.385(2) . ? C27 H27 0.9500 . ? C28 C29 1.369(2) . ? C28 H28 0.9500 . ? C29 C30 1.384(2) . ? C30 C31 1.384(2) . ? C30 H30 0.9500 . ? C31 C32 1.5038(17) . ? C32 C33 1.5304(18) . ? C32 C36 1.5440(17) . ? C32 C38 1.5535(17) . ? C34 C35 1.481(3) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C42 1.4839(18) . ? C37 C49 1.5195(18) . ? C37 C38 1.5322(18) . ? C37 H37 1.0000 . ? C38 C39 1.5119(17) . ? C38 H38 1.0000 . ? C40 C41 1.502(2) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C47 1.3921(19) . ? C42 C43 1.4076(19) . ? C43 C44 1.379(2) . ? C43 H43 0.9500 . ? C44 C45 1.396(2) . ? C44 H44 0.9500 . ? C45 C46 1.3950(19) . ? C46 C47 1.3940(18) . ? C46 H46 0.9500 . ? C47 H47 0.9500 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O4 C15 117.47(10) . . ? C20 O5 C23 118.87(11) . . ? C24 O7 C25 116.04(12) . . ? C8 N1 C9 125.59(11) . . ? C8 N1 C1 109.69(10) . . ? C9 N1 C1 124.22(11) . . ? C11 N2 C12 109.81(10) . . ? C2 C1 C6 121.06(12) . . ? C2 C1 N1 129.39(12) . . ? C6 C1 N1 109.55(11) . . ? C1 C2 C3 117.72(12) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 120.12(12) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? F1 C4 C3 118.32(12) . . ? F1 C4 C5 118.44(12) . . ? C3 C4 C5 123.24(13) . . ? C6 C5 C4 116.49(12) . . ? C6 C5 H5 121.8 . . ? C4 C5 H5 121.8 . . ? C5 C6 C1 121.38(11) . . ? C5 C6 C7 129.10(11) . . ? C1 C6 C7 109.52(11) . . ? C6 C7 C8 102.87(10) . . ? C6 C7 C11 113.17(10) . . ? C8 C7 C11 115.94(10) . . ? C6 C7 C13 116.43(10) . . ? C8 C7 C13 109.61(10) . . ? C11 C7 C13 99.39(9) . . ? O2 C8 N1 126.95(12) . . ? O2 C8 C7 124.97(11) . . ? N1 C8 C7 108.05(10) . . ? O1 C9 N1 119.13(13) . . ? O1 C9 C10 123.48(13) . . ? N1 C9 C10 117.32(12) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C17 122.31(11) . . ? N2 C11 C7 114.20(11) . . ? C17 C11 C7 123.44(11) . . ? N2 C12 C24 108.25(10) . . ? N2 C12 C13 105.45(10) . . ? C24 C12 C13 113.49(11) . . ? N2 C12 H12 109.8 . . ? C24 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C14 C13 C12 116.32(11) . . ? C14 C13 C7 114.45(10) . . ? C12 C13 C7 102.74(10) . . ? C14 C13 H13 107.6 . . ? C12 C13 H13 107.6 . . ? C7 C13 H13 107.6 . . ? O3 C14 O4 125.15(12) . . ? O3 C14 C13 124.96(12) . . ? O4 C14 C13 109.89(10) . . ? O4 C15 C16 106.88(11) . . ? O4 C15 H15A 110.3 . . ? C16 C15 H15A 110.3 . . ? O4 C15 H15B 110.3 . . ? C16 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 118.25(12) . . ? C22 C17 C11 122.63(11) . . ? C18 C17 C11 119.11(11) . . ? C19 C18 C17 120.50(12) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.49(12) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? O5 C20 C21 124.45(13) . . ? O5 C20 C19 115.67(12) . . ? C21 C20 C19 119.87(12) . . ? C20 C21 C22 119.18(12) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C17 C22 C21 121.68(12) . . ? C17 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 O7 124.75(12) . . ? O6 C24 C12 124.74(12) . . ? O7 C24 C12 110.49(11) . . ? O7 C25 H25A 109.5 . . ? O7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C39 O11 C40 117.25(11) . . ? C45 O12 C48 117.08(11) . . ? C49 O14 C50 117.16(13) . . ? C33 N3 C34 126.10(12) . . ? C33 N3 C26 109.67(10) . . ? C34 N3 C26 124.16(12) . . ? C36 N4 C37 109.81(10) . . ? C31 C26 C27 121.26(13) . . ? C31 C26 N3 109.73(11) . . ? C27 C26 N3 129.01(12) . . ? C28 C27 C26 117.79(13) . . ? C28 C27 H27 121.1 . . ? C26 C27 H27 121.1 . . ? C29 C28 C27 119.93(13) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? F2 C29 C28 118.10(14) . . ? F2 C29 C30 118.43(14) . . ? C28 C29 C30 123.46(14) . . ? C31 C30 C29 116.42(13) . . ? C31 C30 H30 121.8 . . ? C29 C30 H30 121.8 . . ? C30 C31 C26 121.12(12) . . ? C30 C31 C32 129.20(12) . . ? C26 C31 C32 109.67(12) . . ? C31 C32 C33 102.82(10) . . ? C31 C32 C36 110.06(10) . . ? C33 C32 C36 117.49(10) . . ? C31 C32 C38 116.90(10) . . ? C33 C32 C38 110.75(10) . . ? C36 C32 C38 99.54(10) . . ? O9 C33 N3 127.13(12) . . ? O9 C33 C32 124.77(12) . . ? N3 C33 C32 108.09(11) . . ? O8 C34 N3 118.58(15) . . ? O8 C34 C35 123.41(15) . . ? N3 C34 C35 118.01(14) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N4 C36 C42 121.78(11) . . ? N4 C36 C32 113.75(11) . . ? C42 C36 C32 123.95(11) . . ? N4 C37 C49 108.24(10) . . ? N4 C37 C38 105.21(10) . . ? C49 C37 C38 113.95(11) . . ? N4 C37 H37 109.8 . . ? C49 C37 H37 109.8 . . ? C38 C37 H37 109.8 . . ? C39 C38 C37 115.79(11) . . ? C39 C38 C32 115.01(10) . . ? C37 C38 C32 102.44(10) . . ? C39 C38 H38 107.7 . . ? C37 C38 H38 107.7 . . ? C32 C38 H38 107.7 . . ? O10 C39 O11 124.97(12) . . ? O10 C39 C38 124.79(12) . . ? O11 C39 C38 110.21(11) . . ? O11 C40 C41 106.35(12) . . ? O11 C40 H40A 110.5 . . ? C41 C40 H40A 110.5 . . ? O11 C40 H40B 110.5 . . ? C41 C40 H40B 110.5 . . ? H40A C40 H40B 108.7 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C47 C42 C43 117.82(12) . . ? C47 C42 C36 123.29(12) . . ? C43 C42 C36 118.88(12) . . ? C44 C43 C42 121.30(13) . . ? C44 C43 H43 119.3 . . ? C42 C43 H43 119.3 . . ? C43 C44 C45 120.05(13) . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? O12 C45 C46 124.48(12) . . ? O12 C45 C44 115.76(12) . . ? C46 C45 C44 119.76(12) . . ? C47 C46 C45 119.49(12) . . ? C47 C46 H46 120.3 . . ? C45 C46 H46 120.3 . . ? C42 C47 C46 121.57(12) . . ? C42 C47 H47 119.2 . . ? C46 C47 H47 119.2 . . ? O12 C48 H48A 109.5 . . ? O12 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? O12 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? O13 C49 O14 124.67(13) . . ? O13 C49 C37 124.78(13) . . ? O14 C49 C37 110.52(12) . . ? O14 C50 H50A 109.5 . . ? O14 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? O14 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 175.99(13) . . . . ? C9 N1 C1 C2 -11.7(2) . . . . ? C8 N1 C1 C6 -4.07(13) . . . . ? C9 N1 C1 C6 168.19(11) . . . . ? C6 C1 C2 C3 0.02(19) . . . . ? N1 C1 C2 C3 179.95(13) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C2 C3 C4 F1 -179.88(13) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? F1 C4 C5 C6 179.98(11) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C4 C5 C6 C1 -0.16(18) . . . . ? C4 C5 C6 C7 179.33(12) . . . . ? C2 C1 C6 C5 0.09(18) . . . . ? N1 C1 C6 C5 -179.85(11) . . . . ? C2 C1 C6 C7 -179.49(11) . . . . ? N1 C1 C6 C7 0.57(13) . . . . ? C5 C6 C7 C8 -176.78(12) . . . . ? C1 C6 C7 C8 2.76(12) . . . . ? C5 C6 C7 C11 -50.91(17) . . . . ? C1 C6 C7 C11 128.63(11) . . . . ? C5 C6 C7 C13 63.35(17) . . . . ? C1 C6 C7 C13 -117.11(12) . . . . ? C9 N1 C8 O2 11.8(2) . . . . ? C1 N1 C8 O2 -176.10(12) . . . . ? C9 N1 C8 C7 -166.35(11) . . . . ? C1 N1 C8 C7 5.79(13) . . . . ? C6 C7 C8 O2 176.69(12) . . . . ? C11 C7 C8 O2 52.64(17) . . . . ? C13 C7 C8 O2 -58.82(16) . . . . ? C6 C7 C8 N1 -5.15(12) . . . . ? C11 C7 C8 N1 -129.20(11) . . . . ? C13 C7 C8 N1 119.33(11) . . . . ? C8 N1 C9 O1 -177.51(12) . . . . ? C1 N1 C9 O1 11.46(19) . . . . ? C8 N1 C9 C10 5.40(19) . . . . ? C1 N1 C9 C10 -165.63(12) . . . . ? C12 N2 C11 C17 -179.41(11) . . . . ? C12 N2 C11 C7 3.10(15) . . . . ? C6 C7 C11 N2 104.29(13) . . . . ? C8 C7 C11 N2 -137.17(12) . . . . ? C13 C7 C11 N2 -19.87(13) . . . . ? C6 C7 C11 C17 -73.17(15) . . . . ? C8 C7 C11 C17 45.37(16) . . . . ? C13 C7 C11 C17 162.67(11) . . . . ? C11 N2 C12 C24 137.58(11) . . . . ? C11 N2 C12 C13 15.81(13) . . . . ? N2 C12 C13 C14 -152.89(10) . . . . ? C24 C12 C13 C14 88.79(13) . . . . ? N2 C12 C13 C7 -27.07(12) . . . . ? C24 C12 C13 C7 -145.39(10) . . . . ? C6 C7 C13 C14 32.08(15) . . . . ? C8 C7 C13 C14 -84.10(13) . . . . ? C11 C7 C13 C14 153.92(11) . . . . ? C6 C7 C13 C12 -94.95(12) . . . . ? C8 C7 C13 C12 148.87(10) . . . . ? C11 C7 C13 C12 26.89(11) . . . . ? C15 O4 C14 O3 5.48(19) . . . . ? C15 O4 C14 C13 -175.10(10) . . . . ? C12 C13 C14 O3 -13.08(19) . . . . ? C7 C13 C14 O3 -132.77(13) . . . . ? C12 C13 C14 O4 167.49(10) . . . . ? C7 C13 C14 O4 47.81(14) . . . . ? C14 O4 C15 C16 170.48(12) . . . . ? N2 C11 C17 C22 -160.08(13) . . . . ? C7 C11 C17 C22 17.18(19) . . . . ? N2 C11 C17 C18 20.55(19) . . . . ? C7 C11 C17 C18 -162.20(12) . . . . ? C22 C17 C18 C19 -1.3(2) . . . . ? C11 C17 C18 C19 178.12(13) . . . . ? C17 C18 C19 C20 1.2(2) . . . . ? C23 O5 C20 C21 6.8(2) . . . . ? C23 O5 C20 C19 -174.26(14) . . . . ? C18 C19 C20 O5 -178.65(14) . . . . ? C18 C19 C20 C21 0.3(2) . . . . ? O5 C20 C21 C22 177.18(14) . . . . ? C19 C20 C21 C22 -1.7(2) . . . . ? C18 C17 C22 C21 -0.1(2) . . . . ? C11 C17 C22 C21 -179.50(12) . . . . ? C20 C21 C22 C17 1.6(2) . . . . ? C25 O7 C24 O6 5.1(2) . . . . ? C25 O7 C24 C12 -172.99(11) . . . . ? N2 C12 C24 O6 -98.64(16) . . . . ? C13 C12 C24 O6 18.06(19) . . . . ? N2 C12 C24 O7 79.49(13) . . . . ? C13 C12 C24 O7 -163.81(10) . . . . ? C33 N3 C26 C31 -0.71(14) . . . . ? C34 N3 C26 C31 -177.78(13) . . . . ? C33 N3 C26 C27 179.42(13) . . . . ? C34 N3 C26 C27 2.3(2) . . . . ? C31 C26 C27 C28 -0.4(2) . . . . ? N3 C26 C27 C28 179.44(14) . . . . ? C26 C27 C28 C29 0.0(2) . . . . ? C27 C28 C29 F2 -179.81(15) . . . . ? C27 C28 C29 C30 -0.1(3) . . . . ? F2 C29 C30 C31 -179.74(14) . . . . ? C28 C29 C30 C31 0.5(2) . . . . ? C29 C30 C31 C26 -0.9(2) . . . . ? C29 C30 C31 C32 -179.54(13) . . . . ? C27 C26 C31 C30 0.9(2) . . . . ? N3 C26 C31 C30 -178.97(12) . . . . ? C27 C26 C31 C32 179.76(12) . . . . ? N3 C26 C31 C32 -0.12(14) . . . . ? C30 C31 C32 C33 179.54(13) . . . . ? C26 C31 C32 C33 0.81(13) . . . . ? C30 C31 C32 C36 53.59(18) . . . . ? C26 C31 C32 C36 -125.14(11) . . . . ? C30 C31 C32 C38 -58.93(18) . . . . ? C26 C31 C32 C38 122.33(12) . . . . ? C34 N3 C33 O9 -0.7(2) . . . . ? C26 N3 C33 O9 -177.69(13) . . . . ? C34 N3 C33 C32 178.22(12) . . . . ? C26 N3 C33 C32 1.22(13) . . . . ? C31 C32 C33 O9 177.72(12) . . . . ? C36 C32 C33 O9 -61.29(17) . . . . ? C38 C32 C33 O9 52.10(16) . . . . ? C31 C32 C33 N3 -1.22(13) . . . . ? C36 C32 C33 N3 119.77(11) . . . . ? C38 C32 C33 N3 -126.84(11) . . . . ? C33 N3 C34 O8 -177.20(15) . . . . ? C26 N3 C34 O8 -0.6(2) . . . . ? C33 N3 C34 C35 2.8(2) . . . . ? C26 N3 C34 C35 179.42(17) . . . . ? C37 N4 C36 C42 -175.93(11) . . . . ? C37 N4 C36 C32 -3.90(15) . . . . ? C31 C32 C36 N4 -101.99(13) . . . . ? C33 C32 C36 N4 140.86(12) . . . . ? C38 C32 C36 N4 21.37(14) . . . . ? C31 C32 C36 C42 69.85(15) . . . . ? C33 C32 C36 C42 -47.30(17) . . . . ? C38 C32 C36 C42 -166.80(12) . . . . ? C36 N4 C37 C49 -138.10(12) . . . . ? C36 N4 C37 C38 -15.93(14) . . . . ? N4 C37 C38 C39 154.06(11) . . . . ? C49 C37 C38 C39 -87.54(14) . . . . ? N4 C37 C38 C32 28.09(12) . . . . ? C49 C37 C38 C32 146.49(11) . . . . ? C31 C32 C38 C39 -36.44(16) . . . . ? C33 C32 C38 C39 80.84(13) . . . . ? C36 C32 C38 C39 -154.81(11) . . . . ? C31 C32 C38 C37 90.03(13) . . . . ? C33 C32 C38 C37 -152.68(10) . . . . ? C36 C32 C38 C37 -28.34(12) . . . . ? C40 O11 C39 O10 -4.88(19) . . . . ? C40 O11 C39 C38 176.83(11) . . . . ? C37 C38 C39 O10 17.42(19) . . . . ? C32 C38 C39 O10 136.71(13) . . . . ? C37 C38 C39 O11 -164.29(11) . . . . ? C32 C38 C39 O11 -44.99(15) . . . . ? C39 O11 C40 C41 -168.06(13) . . . . ? N4 C36 C42 C47 -147.53(13) . . . . ? C32 C36 C42 C47 41.27(18) . . . . ? N4 C36 C42 C43 31.90(18) . . . . ? C32 C36 C42 C43 -139.30(13) . . . . ? C47 C42 C43 C44 -0.5(2) . . . . ? C36 C42 C43 C44 -179.99(12) . . . . ? C42 C43 C44 C45 1.2(2) . . . . ? C48 O12 C45 C46 2.66(19) . . . . ? C48 O12 C45 C44 -176.64(13) . . . . ? C43 C44 C45 O12 178.37(13) . . . . ? C43 C44 C45 C46 -1.0(2) . . . . ? O12 C45 C46 C47 -179.29(12) . . . . ? C44 C45 C46 C47 -0.01(19) . . . . ? C43 C42 C47 C46 -0.48(19) . . . . ? C36 C42 C47 C46 178.96(12) . . . . ? C45 C46 C47 C42 0.74(19) . . . . ? C50 O14 C49 O13 -3.8(2) . . . . ? C50 O14 C49 C37 174.11(12) . . . . ? N4 C37 C49 O13 95.19(16) . . . . ? C38 C37 C49 O13 -21.47(19) . . . . ? N4 C37 C49 O14 -82.72(13) . . . . ? C38 C37 C49 O14 160.62(11) . . . . ? _refine_diff_density_max 0.326 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.042 _shelxl_version_number 2013-4 #===END data_mn2191 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; racemic 4'-ethyl 5'-methyl(3R,4'S,5'R)-1-acetyl-5-fluoro-2'-(4-methyoxyphenyl)-2-oxo- 4',5'-dihydrospiro[indoline-3,3'-pyrrole]-4',5'-dicarboxylate ; _chemical_name_common 'cis-3a toluene solvate' _chemical_melting_point ? _chemical_formula_moiety 'C25 H23 F N2 O7, 0.25(C7 H8), 0.25(C7 H8) 0.5(C7 H8)' _chemical_formula_sum 'C32 H31 F N2 O7' _chemical_formula_weight 574.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7859(2) _cell_length_b 12.7763(4) _cell_length_c 13.0960(3) _cell_angle_alpha 81.6796(9) _cell_angle_beta 76.9516(8) _cell_angle_gamma 86.6732(8) _cell_volume 1416.52(6) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9192 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 72.4 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_F_000 604 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.369 _exptl_crystal_size_mid 0.322 _exptl_crystal_size_min 0.196 _exptl_absorpt_coefficient_mu 0.829 _shelx_estimated_absorpt_T_min 0.750 _shelx_estimated_absorpt_T_max 0.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.754 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source microsource _diffrn_measurement_device_type 'Bruker Apex DUO' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 24676 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.496 _diffrn_reflns_theta_max 72.465 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measured_fraction_theta_full 0.963 _diffrn_reflns_Laue_measured_fraction_max 0.953 _diffrn_reflns_Laue_measured_fraction_full 0.963 _diffrn_reflns_point_group_measured_fraction_max 0.953 _diffrn_reflns_point_group_measured_fraction_full 0.963 _reflns_number_total 5357 _reflns_number_gt 5191 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. There are two toluene sites. In one, the toluene solvate occupies a center of inversion. In the other, two fragments occupy a center of inversion. The latter two fragments were refined using rigid group refinements for C7H8 moeities at each having 0.25 occupancy. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.9487P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5357 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.14419(11) 0.30392(8) 0.71490(8) 0.0318(2) Uani 1 1 d . . . . . O1 O -0.00617(12) 0.06462(9) 0.34941(9) 0.0276(3) Uani 1 1 d . . . . . O2 O -0.46067(11) 0.14982(9) 0.49014(8) 0.0228(2) Uani 1 1 d . . . . . O3 O -0.25459(15) 0.51378(9) 0.51273(10) 0.0351(3) Uani 1 1 d . . . . . O4 O -0.20451(12) 0.38026(9) 0.41463(8) 0.0233(2) Uani 1 1 d . . . . . O5 O -0.48333(13) -0.20144(9) 0.92521(9) 0.0289(3) Uani 1 1 d . . . . . O6 O -0.33404(14) 0.45683(9) 0.76308(9) 0.0299(3) Uani 1 1 d . . . . . O7 O -0.50452(15) 0.56584(9) 0.69154(10) 0.0334(3) Uani 1 1 d . . . . . N1 N -0.18955(13) 0.13792(10) 0.47142(9) 0.0185(3) Uani 1 1 d . . . . . N2 N -0.52785(14) 0.29022(10) 0.74478(9) 0.0207(3) Uani 1 1 d . . . . . C1 C -0.08301(16) 0.17761(11) 0.52381(11) 0.0180(3) Uani 1 1 d . . . . . C2 C 0.07884(16) 0.16415(12) 0.50711(12) 0.0225(3) Uani 1 1 d . . . . . H2 H 0.1357 0.1256 0.4532 0.027 Uiso 1 1 calc R U . . . C3 C 0.15435(17) 0.20924(13) 0.57230(13) 0.0259(3) Uani 1 1 d . . . . . H3 H 0.2647 0.2026 0.5628 0.031 Uiso 1 1 calc R U . . . C4 C 0.06840(17) 0.26336(12) 0.65033(13) 0.0238(3) Uani 1 1 d . . . . . C5 C -0.09210(17) 0.27962(12) 0.66713(11) 0.0205(3) Uani 1 1 d . . . . . H5 H -0.1483 0.3187 0.7208 0.025 Uiso 1 1 calc R U . . . C6 C -0.16587(15) 0.23564(11) 0.60127(11) 0.0175(3) Uani 1 1 d . . . . . C7 C -0.33644(15) 0.24213(11) 0.59811(10) 0.0170(3) Uani 1 1 d . . . . . C8 C -0.34327(16) 0.17086(11) 0.51527(10) 0.0177(3) Uani 1 1 d . . . . . C9 C -0.14416(17) 0.08162(12) 0.38379(11) 0.0214(3) Uani 1 1 d . . . . . C10 C -0.26961(19) 0.04564(14) 0.33744(13) 0.0299(4) Uani 1 1 d . . . . . H10A H -0.2225 0.0038 0.2807 0.045 Uiso 1 1 calc R U . . . H10B H -0.3257 0.1074 0.3087 0.045 Uiso 1 1 calc R U . . . H10C H -0.3429 0.0021 0.3926 0.045 Uiso 1 1 calc R U . . . C11 C -0.44667(15) 0.21281(12) 0.70663(11) 0.0179(3) Uani 1 1 d . . . . . C12 C -0.50480(16) 0.38700(12) 0.66896(11) 0.0210(3) Uani 1 1 d . . . . . H12 H -0.6092 0.4136 0.6563 0.025 Uiso 1 1 calc R U . . . C13 C -0.40493(16) 0.35382(12) 0.56401(11) 0.0189(3) Uani 1 1 d . . . . . H13 H -0.4793 0.3435 0.5189 0.023 Uiso 1 1 calc R U . . . C14 C -0.28037(17) 0.42730(12) 0.49654(11) 0.0217(3) Uani 1 1 d . . . . . C15 C -0.0671(2) 0.43246(14) 0.34585(13) 0.0319(4) Uani 1 1 d . . . . . H15A H 0.0100 0.4441 0.3874 0.038 Uiso 1 1 calc R U . . . H15B H -0.0974 0.5017 0.3102 0.038 Uiso 1 1 calc R U . . . C16 C 0.0007(2) 0.35927(16) 0.26570(14) 0.0393(4) Uani 1 1 d . . . . . H16A H 0.0925 0.3913 0.2165 0.059 Uiso 1 1 calc R U . . . H16B H -0.0779 0.3473 0.2263 0.059 Uiso 1 1 calc R U . . . H16C H 0.0315 0.2916 0.3021 0.059 Uiso 1 1 calc R U . . . C17 C -0.45661(15) 0.10435(12) 0.76306(11) 0.0182(3) Uani 1 1 d . . . . . C18 C -0.58205(16) 0.07822(13) 0.84858(11) 0.0218(3) Uani 1 1 d . . . . . H18 H -0.6591 0.1310 0.8690 0.026 Uiso 1 1 calc R U . . . C19 C -0.59641(17) -0.02278(13) 0.90405(11) 0.0227(3) Uani 1 1 d . . . . . H19 H -0.6829 -0.0391 0.9615 0.027 Uiso 1 1 calc R U . . . C20 C -0.48341(17) -0.10029(12) 0.87509(11) 0.0216(3) Uani 1 1 d . . . . . C21 C -0.35809(17) -0.07593(13) 0.78943(12) 0.0236(3) Uani 1 1 d . . . . . H21 H -0.2814 -0.1289 0.7690 0.028 Uiso 1 1 calc R U . . . C22 C -0.34526(16) 0.02493(12) 0.73430(11) 0.0204(3) Uani 1 1 d . . . . . H22 H -0.2596 0.0406 0.6760 0.024 Uiso 1 1 calc R U . . . C23 C -0.6138(2) -0.23222(14) 1.00969(13) 0.0315(4) Uani 1 1 d . . . . . H23A H -0.5965 -0.3050 1.0414 0.047 Uiso 1 1 calc R U . . . H23B H -0.7091 -0.2281 0.9820 0.047 Uiso 1 1 calc R U . . . H23C H -0.6253 -0.1847 1.0635 0.047 Uiso 1 1 calc R U . . . C24 C -0.43505(18) 0.47218(13) 0.71350(12) 0.0239(3) Uani 1 1 d . . . . . C25 C -0.4353(3) 0.65584(16) 0.71822(19) 0.0493(5) Uani 1 1 d . . . . . H25A H -0.4882 0.7212 0.6939 0.074 Uiso 1 1 calc R U . . . H25B H -0.3241 0.6579 0.6837 0.074 Uiso 1 1 calc R U . . . H25C H -0.4470 0.6491 0.7951 0.074 Uiso 1 1 calc R U . . . C26 C -0.0323(2) -0.0889(2) -0.03835(18) 0.0570(7) Uani 1 1 d . . . . . H26A H -0.0552 -0.1511 -0.0659 0.068 Uiso 0.5 1 d . U P . . C27 C -0.0027(2) -0.0982(2) 0.06215(16) 0.0558(7) Uani 1 1 d . . . . . H27 H -0.0046 -0.1654 0.1043 0.067 Uiso 1 1 calc R U . . . C28 C 0.0291(2) -0.0104(2) 0.09970(15) 0.0570(7) Uani 1 1 d . . . . . H28 H 0.0495 -0.0164 0.1686 0.068 Uiso 1 1 calc R U . . . C29 C -0.0655(4) -0.1743(3) -0.0755(3) 0.0382(8) Uani 0.5 1 d . . P . . H29A H -0.0001 -0.2344 -0.0537 0.057 Uiso 0.5 1 calc R U P . . H29B H -0.0450 -0.1609 -0.1529 0.057 Uiso 0.5 1 calc R U P . . H29C H -0.1759 -0.1907 -0.0473 0.057 Uiso 0.5 1 calc R U P . . C30 C 0.1307(4) 0.4900(4) -0.0100(3) 0.0213(17) Uiso 0.25 1 d G . P A -1 C31 C 0.0368(5) 0.5589(4) 0.0524(4) 0.0164(18) Uiso 0.25 1 d G . P A -1 H31 H 0.0835 0.6018 0.0898 0.020 Uiso 0.25 1 calc R U P A -1 C32 C -0.1230(5) 0.5659(4) 0.0608(4) 0.0287(17) Uiso 0.25 1 d G . P A -1 H32 H -0.1851 0.6119 0.1055 0.034 Uiso 0.25 1 calc R U P A -1 C33 C -0.1940(4) 0.5064(4) 0.0047(4) 0.0210(12) Uiso 0.25 1 d G . P A -1 H33 H -0.3035 0.5124 0.0094 0.025 Uiso 0.25 1 calc R U P A -1 C34 C -0.1015(6) 0.4376(4) -0.0586(4) 0.0220(13) Uiso 0.25 1 d G . P A -1 H34 H -0.1481 0.3956 -0.0969 0.026 Uiso 0.25 1 calc R U P A -1 C35 C 0.0588(5) 0.4305(4) -0.0657(3) 0.0199(13) Uiso 0.25 1 d G . P A -1 H35 H 0.1208 0.3839 -0.1096 0.024 Uiso 0.25 1 calc R U P A -1 C36 C 0.3036(4) 0.4809(5) -0.0176(5) 0.0296(17) Uiso 0.25 1 d G . P A -1 H36A H 0.3329 0.5284 0.0268 0.044 Uiso 0.25 1 calc R U P A -1 H36B H 0.3585 0.5005 -0.0913 0.044 Uiso 0.25 1 calc R U P A -1 H36C H 0.3325 0.4078 0.0068 0.044 Uiso 0.25 1 calc R U P A -1 C37 C 0.1040(6) 0.4991(6) -0.0054(6) 0.048(3) Uiso 0.25 1 d G . P B -2 C38 C 0.0317(8) 0.5748(6) 0.0576(6) 0.045(3) Uiso 0.25 1 d G . P B -2 H38 H 0.0930 0.6134 0.0897 0.053 Uiso 0.25 1 calc R U P B -2 C39 C -0.1277(9) 0.5948(6) 0.0741(6) 0.046(2) Uiso 0.25 1 d G . P B -2 H39 H -0.1749 0.6452 0.1191 0.056 Uiso 0.25 1 calc R U P B -2 C40 C -0.2196(6) 0.5418(6) 0.0257(6) 0.053(2) Uiso 0.25 1 d G . P B -2 H40 H -0.3288 0.5567 0.0359 0.064 Uiso 0.25 1 calc R U P B -2 C41 C -0.1488(8) 0.4663(6) -0.0381(6) 0.053(2) Uiso 0.25 1 d G . P B -2 H41 H -0.2099 0.4286 -0.0711 0.064 Uiso 0.25 1 calc R U P B -2 C42 C 0.0112(8) 0.4462(6) -0.0533(6) 0.053(3) Uiso 0.25 1 d G . P B -2 H42 H 0.0584 0.3951 -0.0975 0.064 Uiso 0.25 1 calc R U P B -2 C43 C 0.2764(7) 0.4760(10) -0.0218(10) 0.095(6) Uiso 0.25 1 d G . P B -2 H43A H 0.3221 0.5206 0.0179 0.143 Uiso 0.25 1 calc R U P B -2 H43B H 0.3251 0.4911 -0.0972 0.143 Uiso 0.25 1 calc R U P B -2 H43C H 0.2948 0.4013 0.0034 0.143 Uiso 0.25 1 calc R U P B -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0251(5) 0.0322(6) 0.0448(6) -0.0059(4) -0.0205(4) -0.0021(4) O1 0.0220(5) 0.0322(7) 0.0256(5) -0.0075(5) 0.0025(4) 0.0032(4) O2 0.0154(5) 0.0316(6) 0.0227(5) -0.0071(4) -0.0046(4) -0.0001(4) O3 0.0458(7) 0.0226(7) 0.0328(6) -0.0033(5) 0.0010(5) -0.0049(5) O4 0.0215(5) 0.0241(6) 0.0207(5) 0.0016(4) -0.0001(4) 0.0001(4) O5 0.0327(6) 0.0243(6) 0.0250(6) 0.0042(4) -0.0005(5) -0.0047(4) O6 0.0337(6) 0.0294(7) 0.0312(6) -0.0074(5) -0.0165(5) 0.0071(5) O7 0.0437(7) 0.0256(7) 0.0365(6) -0.0106(5) -0.0202(5) 0.0139(5) N1 0.0145(6) 0.0221(7) 0.0170(6) -0.0007(5) -0.0013(4) 0.0007(4) N2 0.0163(6) 0.0263(7) 0.0183(6) -0.0020(5) -0.0032(4) 0.0029(5) C1 0.0149(7) 0.0184(8) 0.0185(6) 0.0020(5) -0.0018(5) -0.0003(5) C2 0.0152(7) 0.0234(8) 0.0254(7) 0.0011(6) -0.0005(5) 0.0021(5) C3 0.0139(7) 0.0257(9) 0.0363(8) 0.0033(6) -0.0066(6) -0.0005(5) C4 0.0205(7) 0.0219(8) 0.0309(8) 0.0018(6) -0.0123(6) -0.0031(6) C5 0.0184(7) 0.0208(8) 0.0224(7) -0.0006(5) -0.0064(5) -0.0001(5) C6 0.0135(6) 0.0188(8) 0.0181(6) 0.0025(5) -0.0024(5) 0.0000(5) C7 0.0128(6) 0.0201(8) 0.0171(6) -0.0003(5) -0.0029(5) 0.0006(5) C8 0.0156(7) 0.0203(8) 0.0150(6) 0.0008(5) -0.0010(5) 0.0005(5) C9 0.0224(7) 0.0209(8) 0.0178(7) -0.0004(5) -0.0001(5) 0.0026(5) C10 0.0261(8) 0.0391(10) 0.0263(8) -0.0148(7) -0.0043(6) 0.0051(7) C11 0.0116(6) 0.0259(8) 0.0157(6) -0.0020(5) -0.0028(5) 0.0001(5) C12 0.0176(7) 0.0251(8) 0.0191(7) -0.0026(6) -0.0038(5) 0.0062(5) C13 0.0167(6) 0.0222(8) 0.0178(6) -0.0019(5) -0.0053(5) 0.0035(5) C14 0.0208(7) 0.0221(8) 0.0209(7) 0.0018(6) -0.0061(5) 0.0046(5) C15 0.0279(8) 0.0285(9) 0.0301(8) 0.0087(7) 0.0054(6) -0.0031(6) C16 0.0367(10) 0.0396(11) 0.0303(9) 0.0050(7) 0.0089(7) 0.0032(8) C17 0.0142(6) 0.0246(8) 0.0155(6) -0.0012(5) -0.0033(5) -0.0024(5) C18 0.0160(7) 0.0285(8) 0.0193(7) -0.0035(6) -0.0007(5) -0.0004(5) C19 0.0185(7) 0.0304(9) 0.0173(7) -0.0004(6) -0.0001(5) -0.0065(6) C20 0.0232(7) 0.0236(8) 0.0180(7) 0.0007(5) -0.0053(5) -0.0062(6) C21 0.0221(7) 0.0236(8) 0.0228(7) -0.0020(6) -0.0010(6) 0.0009(6) C22 0.0168(7) 0.0242(8) 0.0174(6) -0.0008(5) 0.0008(5) -0.0017(5) C23 0.0347(9) 0.0329(10) 0.0241(8) 0.0057(6) -0.0032(7) -0.0129(7) C24 0.0256(7) 0.0254(9) 0.0206(7) -0.0044(6) -0.0061(6) 0.0075(6) C25 0.0723(15) 0.0266(11) 0.0612(13) -0.0162(9) -0.0375(12) 0.0138(9) C26 0.0184(9) 0.106(2) 0.0422(11) -0.0126(12) 0.0034(8) 0.0015(10) C27 0.0219(9) 0.106(2) 0.0312(10) 0.0027(11) 0.0038(7) -0.0002(10) C28 0.0218(9) 0.118(2) 0.0221(9) 0.0044(11) 0.0035(7) 0.0053(11) C29 0.0371(19) 0.033(2) 0.046(2) -0.0055(16) -0.0116(16) -0.0028(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C4 1.3594(17) . ? O1 C9 1.2128(18) . ? O2 C8 1.2065(18) . ? O3 C14 1.198(2) . ? O4 C14 1.3316(18) . ? O4 C15 1.4636(18) . ? O5 C20 1.3622(19) . ? O5 C23 1.4306(19) . ? O6 C24 1.2045(19) . ? O7 C24 1.3350(19) . ? O7 C25 1.452(2) . ? N1 C8 1.4088(17) . ? N1 C9 1.4115(19) . ? N1 C1 1.4317(18) . ? N2 C11 1.2792(19) . ? N2 C12 1.4625(19) . ? C1 C6 1.389(2) . ? C1 C2 1.3934(19) . ? C2 C3 1.394(2) . ? C2 H2 0.9500 . ? C3 C4 1.374(2) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 C7 1.5057(18) . ? C7 C8 1.5270(19) . ? C7 C11 1.5377(18) . ? C7 C13 1.560(2) . ? C9 C10 1.495(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C17 1.471(2) . ? C12 C24 1.524(2) . ? C12 C13 1.5555(19) . ? C12 H12 1.0000 . ? C13 C14 1.517(2) . ? C13 H13 1.0000 . ? C15 C16 1.506(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.3991(19) . ? C17 C22 1.399(2) . ? C18 C19 1.384(2) . ? C18 H18 0.9500 . ? C19 C20 1.391(2) . ? C19 H19 0.9500 . ? C20 C21 1.396(2) . ? C21 C22 1.380(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C29 1.330(5) . ? C26 C27 1.386(3) . ? C26 C28 1.398(4) 2 ? C26 H26A 0.9677 . ? C27 C28 1.355(4) . ? C27 H27 0.9500 . ? C28 C26 1.398(4) 2 ? C28 H28 0.9500 . ? C29 H26A 0.3624 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C35 1.3902 . ? C30 C31 1.3936 . ? C30 C36 1.4990 . ? C31 C32 1.3822 . ? C31 H31 0.9500 . ? C32 C33 1.3898 . ? C32 H32 0.9500 . ? C33 C34 1.3943 . ? C33 H33 0.9500 . ? C34 C35 1.3886 . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C42 1.3902 . ? C37 C38 1.3936 . ? C37 C43 1.4990 . ? C38 C39 1.3822 . ? C38 H38 0.9500 . ? C39 C40 1.3898 . ? C39 H39 0.9500 . ? C40 C41 1.3943 . ? C40 H40 0.9500 . ? C41 C42 1.3887 . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O4 C15 117.52(13) . . ? C20 O5 C23 117.69(13) . . ? C24 O7 C25 115.39(13) . . ? C8 N1 C9 125.76(12) . . ? C8 N1 C1 109.63(11) . . ? C9 N1 C1 124.43(12) . . ? C11 N2 C12 111.08(12) . . ? C6 C1 C2 121.22(13) . . ? C6 C1 N1 109.35(12) . . ? C2 C1 N1 129.43(13) . . ? C1 C2 C3 117.61(14) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C4 C3 C2 119.71(13) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? F1 C4 C3 118.60(13) . . ? F1 C4 C5 117.66(14) . . ? C3 C4 C5 123.74(14) . . ? C6 C5 C4 116.14(14) . . ? C6 C5 H5 121.9 . . ? C4 C5 H5 121.9 . . ? C5 C6 C1 121.54(13) . . ? C5 C6 C7 128.50(13) . . ? C1 C6 C7 109.96(12) . . ? C6 C7 C8 102.51(11) . . ? C6 C7 C11 113.87(11) . . ? C8 C7 C11 115.22(12) . . ? C6 C7 C13 116.67(12) . . ? C8 C7 C13 108.69(11) . . ? C11 C7 C13 100.36(11) . . ? O2 C8 N1 126.50(13) . . ? O2 C8 C7 125.20(12) . . ? N1 C8 C7 108.26(11) . . ? O1 C9 N1 118.97(14) . . ? O1 C9 C10 122.95(14) . . ? N1 C9 C10 118.08(12) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C17 122.47(13) . . ? N2 C11 C7 114.90(13) . . ? C17 C11 C7 122.62(12) . . ? N2 C12 C24 110.61(12) . . ? N2 C12 C13 106.12(11) . . ? C24 C12 C13 115.27(12) . . ? N2 C12 H12 108.2 . . ? C24 C12 H12 108.2 . . ? C13 C12 H12 108.2 . . ? C14 C13 C12 119.17(12) . . ? C14 C13 C7 112.34(11) . . ? C12 C13 C7 104.07(11) . . ? C14 C13 H13 106.9 . . ? C12 C13 H13 106.9 . . ? C7 C13 H13 106.9 . . ? O3 C14 O4 125.15(14) . . ? O3 C14 C13 126.25(14) . . ? O4 C14 C13 108.59(13) . . ? O4 C15 C16 106.11(14) . . ? O4 C15 H15A 110.5 . . ? C16 C15 H15A 110.5 . . ? O4 C15 H15B 110.5 . . ? C16 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 118.05(14) . . ? C18 C17 C11 119.41(13) . . ? C22 C17 C11 122.53(12) . . ? C19 C18 C17 121.49(14) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 119.59(13) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? O5 C20 C19 124.79(13) . . ? O5 C20 C21 115.48(14) . . ? C19 C20 C21 119.73(14) . . ? C22 C21 C20 120.22(14) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.91(13) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 O7 124.94(15) . . ? O6 C24 C12 124.92(14) . . ? O7 C24 C12 110.13(12) . . ? O7 C25 H25A 109.5 . . ? O7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C29 C26 C27 119.8(3) . . ? C29 C26 C28 120.3(3) . 2 ? C27 C26 C28 119.9(3) . 2 ? C27 C26 H26A 120.0 . . ? C28 C26 H26A 120.2 2 . ? C28 C27 C26 119.3(3) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C26 120.8(2) . 2 ? C27 C28 H28 119.6 . . ? C26 C28 H28 119.6 2 . ? C26 C29 H29A 109.5 . . ? H26A C29 H29A 108.6 . . ? C26 C29 H29B 109.5 . . ? H26A C29 H29B 108.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H26A C29 H29C 111.3 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C35 C30 C31 117.8 . . ? C35 C30 C36 121.0 . . ? C31 C30 C36 121.2 . . ? C32 C31 C30 121.1 . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C33 120.7 . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C32 C33 C34 118.8 . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C35 C34 C33 119.9 . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C30 121.6 . . ? C34 C35 H35 119.2 . . ? C30 C35 H35 119.2 . . ? C30 C36 H36A 109.5 . . ? C30 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C30 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C42 C37 C38 117.8 . . ? C42 C37 C43 121.0 . . ? C38 C37 C43 121.2 . . ? C39 C38 C37 121.1 . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C38 C39 C40 120.7 . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C39 C40 C41 118.8 . . ? C39 C40 H40 120.6 . . ? C41 C40 H40 120.6 . . ? C42 C41 C40 119.9 . . ? C42 C41 H41 120.0 . . ? C40 C41 H41 120.0 . . ? C41 C42 C37 121.6 . . ? C41 C42 H42 119.2 . . ? C37 C42 H42 119.2 . . ? C37 C43 H43A 109.5 . . ? C37 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C37 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C6 0.16(16) . . . . ? C9 N1 C1 C6 175.56(13) . . . . ? C8 N1 C1 C2 179.47(14) . . . . ? C9 N1 C1 C2 -5.1(2) . . . . ? C6 C1 C2 C3 1.2(2) . . . . ? N1 C1 C2 C3 -178.01(14) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? C2 C3 C4 F1 178.07(13) . . . . ? C2 C3 C4 C5 -2.2(2) . . . . ? F1 C4 C5 C6 -178.86(13) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C4 C5 C6 C1 0.7(2) . . . . ? C4 C5 C6 C7 -178.15(14) . . . . ? C2 C1 C6 C5 -2.0(2) . . . . ? N1 C1 C6 C5 177.34(13) . . . . ? C2 C1 C6 C7 177.02(13) . . . . ? N1 C1 C6 C7 -3.60(16) . . . . ? C5 C6 C7 C8 -175.76(14) . . . . ? C1 C6 C7 C8 5.26(15) . . . . ? C5 C6 C7 C11 -50.6(2) . . . . ? C1 C6 C7 C11 130.40(13) . . . . ? C5 C6 C7 C13 65.62(19) . . . . ? C1 C6 C7 C13 -113.35(13) . . . . ? C9 N1 C8 O2 5.8(2) . . . . ? C1 N1 C8 O2 -178.93(14) . . . . ? C9 N1 C8 C7 -172.06(13) . . . . ? C1 N1 C8 C7 3.26(15) . . . . ? C6 C7 C8 O2 177.07(13) . . . . ? C11 C7 C8 O2 52.83(19) . . . . ? C13 C7 C8 O2 -58.84(18) . . . . ? C6 C7 C8 N1 -5.08(14) . . . . ? C11 C7 C8 N1 -129.32(12) . . . . ? C13 C7 C8 N1 119.01(12) . . . . ? C8 N1 C9 O1 174.84(14) . . . . ? C1 N1 C9 O1 0.2(2) . . . . ? C8 N1 C9 C10 -5.1(2) . . . . ? C1 N1 C9 C10 -179.76(13) . . . . ? C12 N2 C11 C17 -175.38(12) . . . . ? C12 N2 C11 C7 5.42(16) . . . . ? C6 C7 C11 N2 110.15(14) . . . . ? C8 C7 C11 N2 -131.79(13) . . . . ? C13 C7 C11 N2 -15.29(15) . . . . ? C6 C7 C11 C17 -69.05(17) . . . . ? C8 C7 C11 C17 49.01(17) . . . . ? C13 C7 C11 C17 165.51(12) . . . . ? C11 N2 C12 C24 -118.45(13) . . . . ? C11 N2 C12 C13 7.24(15) . . . . ? N2 C12 C13 C14 -142.18(12) . . . . ? C24 C12 C13 C14 -19.39(18) . . . . ? N2 C12 C13 C7 -16.11(14) . . . . ? C24 C12 C13 C7 106.68(13) . . . . ? C6 C7 C13 C14 24.42(16) . . . . ? C8 C7 C13 C14 -90.78(13) . . . . ? C11 C7 C13 C14 147.94(11) . . . . ? C6 C7 C13 C12 -105.83(13) . . . . ? C8 C7 C13 C12 138.96(11) . . . . ? C11 C7 C13 C12 17.68(13) . . . . ? C15 O4 C14 O3 7.7(2) . . . . ? C15 O4 C14 C13 -173.09(12) . . . . ? C12 C13 C14 O3 -4.3(2) . . . . ? C7 C13 C14 O3 -126.33(16) . . . . ? C12 C13 C14 O4 176.47(11) . . . . ? C7 C13 C14 O4 54.44(15) . . . . ? C14 O4 C15 C16 176.25(13) . . . . ? N2 C11 C17 C18 15.2(2) . . . . ? C7 C11 C17 C18 -165.66(13) . . . . ? N2 C11 C17 C22 -165.18(14) . . . . ? C7 C11 C17 C22 14.0(2) . . . . ? C22 C17 C18 C19 0.3(2) . . . . ? C11 C17 C18 C19 179.97(13) . . . . ? C17 C18 C19 C20 0.5(2) . . . . ? C23 O5 C20 C19 4.1(2) . . . . ? C23 O5 C20 C21 -176.49(13) . . . . ? C18 C19 C20 O5 178.43(13) . . . . ? C18 C19 C20 C21 -1.0(2) . . . . ? O5 C20 C21 C22 -178.78(13) . . . . ? C19 C20 C21 C22 0.7(2) . . . . ? C20 C21 C22 C17 0.1(2) . . . . ? C18 C17 C22 C21 -0.7(2) . . . . ? C11 C17 C22 C21 179.73(13) . . . . ? C25 O7 C24 O6 8.7(2) . . . . ? C25 O7 C24 C12 -172.64(15) . . . . ? N2 C12 C24 O6 40.6(2) . . . . ? C13 C12 C24 O6 -79.73(19) . . . . ? N2 C12 C24 O7 -138.03(13) . . . . ? C13 C12 C24 O7 101.61(14) . . . . ? C29 C26 C27 C28 -179.2(3) . . . . ? C28 C26 C27 C28 0.0(3) 2 . . . ? C26 C27 C28 C26 0.0(3) . . . 2 ? C35 C30 C31 C32 1.6 . . . . ? C36 C30 C31 C32 -178.9 . . . . ? C30 C31 C32 C33 -1.9 . . . . ? C31 C32 C33 C34 1.4 . . . . ? C32 C33 C34 C35 -0.8 . . . . ? C33 C34 C35 C30 0.6 . . . . ? C31 C30 C35 C34 -1.0 . . . . ? C36 C30 C35 C34 179.5 . . . . ? C42 C37 C38 C39 1.6 . . . . ? C43 C37 C38 C39 -178.9 . . . . ? C37 C38 C39 C40 -1.9 . . . . ? C38 C39 C40 C41 1.4 . . . . ? C39 C40 C41 C42 -0.8 . . . . ? C40 C41 C42 C37 0.6 . . . . ? C38 C37 C42 C41 -1.0 . . . . ? C43 C37 C42 C41 179.5 . . . . ? _refine_diff_density_max 0.421 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.050 _shelxl_version_number 2013-4 #===END data_mn2188 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; racemic dimethyl(1S,3aR,9bS)-3-(4-methyoyphenyl)-4-oxo-1,9b-dihydro- chromeno[3,4-c]pyrrole-1,3a(4H)-dicarboxylate ; _chemical_name_common 'coumarin 10' _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 N O7' _chemical_formula_sum 'C22 H19 N O7' _chemical_formula_weight 409.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.736(3) _cell_length_b 12.166(2) _cell_length_c 17.785(4) _cell_angle_alpha 90 _cell_angle_beta 91.250(3) _cell_angle_gamma 90 _cell_volume 3836.7(13) _cell_formula_units_Z 8 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 6991 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 26.9 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_F_000 1712 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 0.107 _shelx_estimated_absorpt_T_min 0.959 _shelx_estimated_absorpt_T_max 0.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method \s _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 39895 _diffrn_reflns_av_unetI/netI 0.0534 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.838 _diffrn_reflns_theta_max 27.563 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_point_group_measured_fraction_full 0.997 _reflns_number_total 8768 _reflns_number_gt 5977 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'SMART (Bruker, v5.054)' _computing_cell_refinement 'SAINT (Bruker, v6.45A)' _computing_data_reduction 'SAINT (Bruker, v6.45A)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'XP (Sheldrick, 1997)' _computing_publication_material 'SHELXL-2013 (Sheldrick, 2013)' _refine_special_details ; Each of the two molecules in the asymmetric unit has minor disorder. In molecule1, the OMe group of the acetoxy group has 0.474(3)/0.526(3) disorder and in molecule2, the OMe group has 0.449(6)/0.551(6) disorder. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+1.2177P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 8768 _refine_ls_number_parameters 587 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.30438(8) 0.48223(12) 0.57583(8) 0.0212(3) Uani 1 1 d . . . . . O2 O 0.38220(8) 0.52876(12) 0.48802(8) 0.0238(3) Uani 1 1 d . . . . . O3 O 0.45640(8) 0.20092(12) 0.49664(9) 0.0246(4) Uani 1 1 d . . . . . O4 O 0.46479(8) 0.34287(11) 0.57732(8) 0.0193(3) Uani 1 1 d . . . . . O5 O 0.52756(8) 0.48435(13) 0.17792(8) 0.0271(4) Uani 1 1 d . . . . . O6 O 0.22187(9) 0.07130(13) 0.42847(10) 0.0344(4) Uani 1 1 d . . . . . O7A O 0.14060(16) 0.1471(2) 0.49610(19) 0.0232(9) Uani 0.474(3) 1 d . . P A 1 O7B O 0.11592(15) 0.1834(2) 0.42924(19) 0.0314(10) Uani 0.526(3) 1 d . . P A 2 N1 N 0.28003(10) 0.28875(15) 0.38993(10) 0.0214(4) Uani 1 1 d . . . . . C1 C 0.35043(11) 0.45526(16) 0.51848(11) 0.0163(4) Uani 1 1 d . . . . . C2 C 0.26792(11) 0.40341(18) 0.61960(11) 0.0208(5) Uani 1 1 d . . . . . C3 C 0.23733(12) 0.4425(2) 0.68554(12) 0.0299(6) Uani 1 1 d . . . . . H3 H 0.2414 0.5180 0.6987 0.036 Uiso 1 1 calc R U . . . C4 C 0.20080(12) 0.3695(3) 0.73158(13) 0.0357(6) Uani 1 1 d . . . . . H4 H 0.1797 0.3945 0.7772 0.043 Uiso 1 1 calc R U . . . C5 C 0.19478(12) 0.2599(2) 0.71151(12) 0.0331(6) Uani 1 1 d . . . . . H5 H 0.1696 0.2100 0.7435 0.040 Uiso 1 1 calc R U . . . C6 C 0.22526(11) 0.2221(2) 0.64482(12) 0.0247(5) Uani 1 1 d . . . . . H6 H 0.2209 0.1467 0.6316 0.030 Uiso 1 1 calc R U . . . C7 C 0.26234(11) 0.29479(17) 0.59728(11) 0.0182(4) Uani 1 1 d . . . . . C8 C 0.29297(11) 0.26026(16) 0.52321(11) 0.0165(4) Uani 1 1 d . . . . . H8 H 0.3125 0.1834 0.5281 0.020 Uiso 1 1 calc R U . . . C9 C 0.35759(11) 0.33466(16) 0.49528(11) 0.0143(4) Uani 1 1 d . . . . . C10 C 0.23593(11) 0.26450(17) 0.45611(11) 0.0179(4) Uani 1 1 d . . . . . H10 H 0.1984 0.3245 0.4642 0.021 Uiso 1 1 calc R U . . . C11 C 0.34517(11) 0.32549(16) 0.40887(11) 0.0157(4) Uani 1 1 d . . . . . C12 C 0.39938(11) 0.36053(16) 0.35187(11) 0.0159(4) Uani 1 1 d . . . . . C13 C 0.37712(11) 0.35096(17) 0.27607(11) 0.0192(4) Uani 1 1 d . . . . . H13 H 0.3307 0.3161 0.2633 0.023 Uiso 1 1 calc R U . . . C14 C 0.42130(12) 0.39116(18) 0.22005(11) 0.0211(5) Uani 1 1 d . . . . . H14 H 0.4051 0.3841 0.1690 0.025 Uiso 1 1 calc R U . . . C15 C 0.48979(12) 0.44229(17) 0.23752(12) 0.0197(4) Uani 1 1 d . . . . . C16 C 0.51473(11) 0.44756(17) 0.31210(12) 0.0193(4) Uani 1 1 d . . . . . H16 H 0.5626 0.4787 0.3244 0.023 Uiso 1 1 calc R U . . . C17 C 0.46938(11) 0.40713(16) 0.36859(11) 0.0186(4) Uani 1 1 d . . . . . H17 H 0.4865 0.4114 0.4195 0.022 Uiso 1 1 calc R U . . . C18 C 0.58730(15) 0.5600(2) 0.19365(14) 0.0353(6) Uani 1 1 d . . . . . H18A H 0.6033 0.5942 0.1467 0.053 Uiso 1 1 calc R U . . . H18B H 0.6300 0.5209 0.2171 0.053 Uiso 1 1 calc R U . . . H18C H 0.5697 0.6170 0.2280 0.053 Uiso 1 1 calc R U . . . C19 C 0.43304(11) 0.28530(16) 0.52182(11) 0.0151(4) Uani 1 1 d . . . . . C20 C 0.53536(11) 0.29757(18) 0.60829(13) 0.0245(5) Uani 1 1 d . . . . . H20A H 0.5562 0.3476 0.6466 0.037 Uiso 1 1 calc R U . . . H20B H 0.5716 0.2890 0.5679 0.037 Uiso 1 1 calc R U . . . H20C H 0.5256 0.2258 0.6311 0.037 Uiso 1 1 calc R U . . . C21 C 0.19546(14) 0.1558(2) 0.44659(14) 0.0327(6) Uani 1 1 d . . . . . C22A C 0.1055(3) 0.0406(4) 0.5054(3) 0.0295(13) Uani 0.474(3) 1 d . . P A 1 H22A H 0.0622 0.0476 0.5384 0.044 Uiso 0.474(3) 1 calc R U P A 1 H22B H 0.1422 -0.0107 0.5278 0.044 Uiso 0.474(3) 1 calc R U P A 1 H22C H 0.0884 0.0127 0.4562 0.044 Uiso 0.474(3) 1 calc R U P A 1 C22B C 0.0692(3) 0.0894(4) 0.4111(3) 0.0429(15) Uani 0.526(3) 1 d . . P A 2 H22D H 0.0174 0.1138 0.4005 0.064 Uiso 0.526(3) 1 calc R U P A 2 H22E H 0.0697 0.0384 0.4538 0.064 Uiso 0.526(3) 1 calc R U P A 2 H22F H 0.0889 0.0522 0.3668 0.064 Uiso 0.526(3) 1 calc R U P A 2 O8 O 0.20328(8) 0.54245(11) 0.42371(8) 0.0206(3) Uani 1 1 d . . . . . O9 O 0.12905(8) 0.49001(12) 0.51325(8) 0.0230(3) Uani 1 1 d . . . . . O10 O 0.04139(8) 0.81569(12) 0.47041(9) 0.0252(4) Uani 1 1 d . . . . . O11 O 0.03383(8) 0.64663(12) 0.41918(8) 0.0214(3) Uani 1 1 d . . . . . O12A O -0.0820(3) 0.5263(4) 0.7786(3) 0.0248(11) Uani 0.449(6) 1 d . . P B 1 O12B O -0.0531(2) 0.5467(3) 0.8019(2) 0.0217(10) Uani 0.551(6) 1 d . . P B 2 O13 O 0.27781(8) 0.94664(12) 0.58953(9) 0.0258(4) Uani 1 1 d . . . . . O14 O 0.36052(8) 0.86252(12) 0.51446(9) 0.0250(4) Uani 1 1 d . . . . . N2 N 0.20614(10) 0.73903(14) 0.60968(10) 0.0215(4) Uani 1 1 d . . . . . C23 C 0.15542(11) 0.56586(17) 0.48027(11) 0.0160(4) Uani 1 1 d . . . . . C24 C 0.23697(11) 0.62512(18) 0.37995(11) 0.0194(4) Uani 1 1 d . . . . . C25 C 0.27006(12) 0.5893(2) 0.31479(12) 0.0269(5) Uani 1 1 d . . . . . H25 H 0.2687 0.5139 0.3011 0.032 Uiso 1 1 calc R U . . . C26 C 0.30524(13) 0.6657(2) 0.27001(13) 0.0303(6) Uani 1 1 d . . . . . H26 H 0.3283 0.6429 0.2249 0.036 Uiso 1 1 calc R U . . . C27 C 0.30700(12) 0.7755(2) 0.29066(13) 0.0279(5) Uani 1 1 d . . . . . H27 H 0.3314 0.8276 0.2597 0.033 Uiso 1 1 calc R U . . . C28 C 0.27334(11) 0.80955(19) 0.35629(12) 0.0234(5) Uani 1 1 d . . . . . H28 H 0.2743 0.8851 0.3697 0.028 Uiso 1 1 calc R U . . . C29 C 0.23810(10) 0.73373(17) 0.40285(11) 0.0177(4) Uani 1 1 d . . . . . C30 C 0.20336(11) 0.76412(16) 0.47570(11) 0.0162(4) Uani 1 1 d . . . . . H30 H 0.1823 0.8401 0.4709 0.019 Uiso 1 1 calc R U . . . C31 C 0.13931(11) 0.68610(16) 0.49874(11) 0.0157(4) Uani 1 1 d . . . . . C32 C 0.25587(11) 0.75992(17) 0.54714(11) 0.0184(4) Uani 1 1 d . . . . . H32 H 0.2925 0.6980 0.5426 0.022 Uiso 1 1 calc R U . . . C33 C 0.14333(11) 0.69946(16) 0.58569(11) 0.0169(4) Uani 1 1 d . . . . . C34 C 0.08519(12) 0.66218(16) 0.63801(11) 0.0189(4) Uani 1 1 d . . . . . C35 C 0.10255(13) 0.6611(2) 0.71482(12) 0.0312(6) Uani 1 1 d . . . . . H35 H 0.1497 0.6895 0.7323 0.037 Uiso 1 1 calc R U . . . C36 C 0.05280(14) 0.6198(3) 0.76586(13) 0.0422(7) Uani 1 1 d . . . . . H36 H 0.0663 0.6186 0.8178 0.051 Uiso 1 1 calc R U . . . C37 C -0.01700(14) 0.57978(19) 0.74200(13) 0.0317(6) Uani 1 1 d . . . . . C38 C -0.03646(14) 0.58494(19) 0.66626(13) 0.0320(6) Uani 1 1 d . . . . . H38 H -0.0850 0.5614 0.6494 0.038 Uiso 1 1 calc R U . . . C39 C 0.01476(13) 0.62434(19) 0.61512(12) 0.0280(5) Uani 1 1 d . . . . . H39 H 0.0013 0.6254 0.5631 0.034 Uiso 1 1 calc R U . . . C40A C -0.0626(3) 0.4903(4) 0.8532(3) 0.0305(16) Uani 0.449(6) 1 d . . P B 1 H40D H -0.1058 0.4523 0.8747 0.046 Uiso 0.449(6) 1 calc R U P B 1 H40E H -0.0493 0.5540 0.8845 0.046 Uiso 0.449(6) 1 calc R U P B 1 H40F H -0.0196 0.4399 0.8515 0.046 Uiso 0.449(6) 1 calc R U P B 1 C40B C -0.1169(3) 0.4828(4) 0.7809(3) 0.0271(12) Uani 0.551(6) 1 d . . P B 2 H40A H -0.1407 0.4543 0.8261 0.041 Uiso 0.551(6) 1 calc R U P B 2 H40B H -0.1011 0.4212 0.7494 0.041 Uiso 0.551(6) 1 calc R U P B 2 H40C H -0.1530 0.5285 0.7526 0.041 Uiso 0.551(6) 1 calc R U P B 2 C41 C 0.06506(11) 0.72433(16) 0.46197(11) 0.0161(4) Uani 1 1 d . . . . . C42 C -0.03809(12) 0.6747(2) 0.38269(13) 0.0286(5) Uani 1 1 d . . . . . H42A H -0.0594 0.6092 0.3581 0.043 Uiso 1 1 calc R U . . . H42B H -0.0302 0.7321 0.3450 0.043 Uiso 1 1 calc R U . . . H42C H -0.0731 0.7015 0.4205 0.043 Uiso 1 1 calc R U . . . C43 C 0.29826(11) 0.86737(17) 0.55539(11) 0.0189(4) Uani 1 1 d . . . . . C44 C 0.40235(12) 0.96401(18) 0.50779(14) 0.0261(5) Uani 1 1 d . . . . . H44A H 0.4420 0.9547 0.4708 0.039 Uiso 1 1 calc R U . . . H44B H 0.4252 0.9832 0.5567 0.039 Uiso 1 1 calc R U . . . H44C H 0.3681 1.0229 0.4913 0.039 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0235(8) 0.0185(8) 0.0217(8) -0.0063(6) 0.0017(6) 0.0044(6) O2 0.0304(8) 0.0162(8) 0.0247(8) 0.0012(6) 0.0005(7) -0.0010(7) O3 0.0246(8) 0.0169(8) 0.0322(9) -0.0047(6) 0.0004(7) 0.0044(6) O4 0.0166(7) 0.0196(8) 0.0215(8) -0.0027(6) -0.0041(6) 0.0044(6) O5 0.0315(9) 0.0299(9) 0.0203(8) -0.0009(7) 0.0084(7) -0.0118(7) O6 0.0387(10) 0.0201(9) 0.0440(10) -0.0014(8) -0.0094(8) -0.0041(8) O7A 0.0155(16) 0.0156(16) 0.039(2) -0.0038(14) 0.0068(14) -0.0051(12) O7B 0.0151(15) 0.0282(18) 0.051(2) -0.0183(15) 0.0040(14) -0.0080(13) N1 0.0196(9) 0.0261(10) 0.0186(9) -0.0040(7) 0.0039(7) -0.0085(8) C1 0.0188(10) 0.0153(10) 0.0146(10) -0.0009(8) -0.0050(8) 0.0024(8) C2 0.0137(10) 0.0323(13) 0.0163(11) 0.0001(9) -0.0012(8) 0.0042(9) C3 0.0191(11) 0.0489(15) 0.0216(12) -0.0115(11) -0.0045(9) 0.0102(11) C4 0.0180(11) 0.075(2) 0.0135(11) -0.0031(12) 0.0010(9) 0.0110(12) C5 0.0149(10) 0.0669(19) 0.0175(12) 0.0159(12) 0.0005(9) 0.0037(11) C6 0.0139(10) 0.0375(14) 0.0227(11) 0.0124(10) 0.0007(8) 0.0031(9) C7 0.0125(9) 0.0265(11) 0.0154(10) 0.0036(8) -0.0022(8) 0.0046(8) C8 0.0175(10) 0.0123(10) 0.0198(10) 0.0021(8) 0.0036(8) 0.0019(8) C9 0.0151(9) 0.0137(10) 0.0142(10) 0.0000(8) 0.0017(8) 0.0008(8) C10 0.0196(10) 0.0185(10) 0.0157(10) -0.0046(8) 0.0036(8) -0.0042(8) C11 0.0187(10) 0.0133(10) 0.0152(10) -0.0030(8) 0.0017(8) -0.0001(8) C12 0.0173(10) 0.0147(10) 0.0157(10) -0.0015(8) 0.0021(8) 0.0003(8) C13 0.0167(10) 0.0221(11) 0.0187(11) -0.0039(8) -0.0013(8) -0.0013(8) C14 0.0236(11) 0.0265(12) 0.0131(10) -0.0032(8) 0.0001(8) 0.0009(9) C15 0.0225(11) 0.0178(11) 0.0192(11) -0.0019(8) 0.0070(8) -0.0001(9) C16 0.0164(10) 0.0185(11) 0.0232(11) -0.0041(8) 0.0020(8) -0.0027(8) C17 0.0199(10) 0.0190(11) 0.0169(10) -0.0015(8) -0.0008(8) -0.0003(8) C18 0.0455(15) 0.0308(13) 0.0303(13) -0.0036(10) 0.0147(11) -0.0223(12) C19 0.0165(10) 0.0139(10) 0.0152(10) 0.0021(8) 0.0035(8) -0.0013(8) C20 0.0170(10) 0.0222(12) 0.0341(13) 0.0042(9) -0.0041(9) 0.0027(9) C21 0.0331(13) 0.0306(14) 0.0354(14) -0.0166(11) 0.0207(11) -0.0157(11) C22A 0.017(2) 0.016(2) 0.056(3) -0.002(2) 0.013(2) -0.0024(19) C22B 0.023(2) 0.045(3) 0.061(4) -0.034(3) 0.013(2) -0.017(2) O8 0.0198(7) 0.0176(8) 0.0245(8) -0.0027(6) 0.0010(6) 0.0010(6) O9 0.0243(8) 0.0168(8) 0.0280(8) 0.0003(6) 0.0024(6) -0.0023(6) O10 0.0190(8) 0.0214(8) 0.0351(9) 0.0040(7) -0.0015(7) 0.0032(6) O11 0.0158(7) 0.0252(8) 0.0229(8) -0.0014(6) -0.0066(6) 0.0012(6) O12A 0.017(3) 0.031(3) 0.026(3) 0.005(2) 0.003(2) -0.013(2) O12B 0.0158(19) 0.0259(19) 0.024(2) 0.0021(14) 0.0046(14) -0.0034(15) O13 0.0301(8) 0.0201(8) 0.0275(9) -0.0067(7) 0.0064(7) -0.0024(7) O14 0.0155(7) 0.0192(8) 0.0405(9) -0.0084(7) 0.0022(7) -0.0017(6) N2 0.0249(9) 0.0191(9) 0.0204(9) 0.0002(7) -0.0028(7) -0.0009(8) C23 0.0135(9) 0.0182(10) 0.0161(10) -0.0014(8) -0.0054(8) -0.0004(8) C24 0.0137(9) 0.0237(11) 0.0204(11) 0.0039(9) -0.0038(8) 0.0017(8) C25 0.0230(11) 0.0342(14) 0.0234(12) -0.0026(10) -0.0020(9) 0.0099(10) C26 0.0258(12) 0.0467(16) 0.0183(12) 0.0038(10) 0.0007(9) 0.0112(11) C27 0.0183(11) 0.0400(15) 0.0254(12) 0.0132(10) 0.0022(9) 0.0028(10) C28 0.0160(10) 0.0286(12) 0.0257(12) 0.0082(9) -0.0013(9) 0.0019(9) C29 0.0110(9) 0.0237(11) 0.0183(10) 0.0015(8) -0.0033(8) 0.0004(8) C30 0.0139(9) 0.0150(10) 0.0196(10) 0.0001(8) -0.0027(8) -0.0018(8) C31 0.0148(9) 0.0156(10) 0.0165(10) -0.0005(8) -0.0011(8) -0.0002(8) C32 0.0174(10) 0.0168(10) 0.0209(11) -0.0032(8) -0.0035(8) 0.0012(8) C33 0.0201(10) 0.0127(10) 0.0176(10) -0.0013(8) -0.0035(8) 0.0009(8) C34 0.0266(11) 0.0143(10) 0.0160(10) -0.0002(8) 0.0002(8) 0.0039(9) C35 0.0239(12) 0.0501(16) 0.0195(12) -0.0042(11) -0.0004(9) 0.0195(11) C36 0.0334(14) 0.076(2) 0.0175(12) 0.0069(12) 0.0057(10) 0.0311(14) C37 0.0450(15) 0.0235(12) 0.0272(13) 0.0064(10) 0.0194(11) 0.0180(11) C38 0.0399(14) 0.0271(13) 0.0297(13) -0.0097(10) 0.0134(11) -0.0150(11) C39 0.0361(13) 0.0300(13) 0.0179(11) -0.0029(9) 0.0018(10) -0.0157(11) C40A 0.033(3) 0.029(3) 0.029(3) 0.009(2) 0.004(2) -0.008(2) C40B 0.024(3) 0.026(3) 0.032(3) -0.0030(19) 0.008(2) -0.009(2) C41 0.0141(9) 0.0187(11) 0.0157(10) 0.0032(8) 0.0022(8) -0.0009(8) C42 0.0184(11) 0.0349(14) 0.0320(13) 0.0123(10) -0.0123(9) -0.0065(10) C43 0.0170(10) 0.0196(11) 0.0198(11) -0.0015(8) -0.0049(8) 0.0007(8) C44 0.0189(11) 0.0198(12) 0.0397(14) -0.0073(10) 0.0032(10) -0.0050(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.361(2) . ? O1 C2 1.402(3) . ? O2 C1 1.193(2) . ? O3 C19 1.198(2) . ? O4 C19 1.326(2) . ? O4 C20 1.464(2) . ? O5 C15 1.366(2) . ? O5 C18 1.427(3) . ? O6 C21 1.177(3) . ? O7A C21 1.331(4) . ? O7A C22A 1.449(5) . ? O7B C22B 1.444(5) . ? O7B C21 1.476(4) . ? N1 C11 1.277(3) . ? N1 C10 1.458(2) . ? C1 C9 1.530(3) . ? C2 C7 1.383(3) . ? C2 C3 1.387(3) . ? C3 C4 1.379(4) . ? C3 H3 0.9500 . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C7 1.398(3) . ? C6 H6 0.9500 . ? C7 C8 1.496(3) . ? C8 C10 1.548(3) . ? C8 C9 1.551(3) . ? C8 H8 1.0000 . ? C9 C19 1.532(3) . ? C9 C11 1.552(3) . ? C10 C21 1.513(3) . ? C10 H10 1.0000 . ? C11 C12 1.475(3) . ? C12 C17 1.391(3) . ? C12 C13 1.401(3) . ? C13 C14 1.371(3) . ? C13 H13 0.9500 . ? C14 C15 1.394(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C16 C17 1.391(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? O8 C23 1.360(2) . ? O8 C24 1.412(2) . ? O9 C23 1.194(2) . ? O10 C41 1.199(2) . ? O11 C41 1.327(2) . ? O11 C42 1.459(2) . ? O12A C40A 1.431(7) . ? O12A C37 1.486(5) . ? O12B C37 1.317(4) . ? O12B C40B 1.418(7) . ? O13 C43 1.200(2) . ? O14 C43 1.337(2) . ? O14 C44 1.447(3) . ? N2 C33 1.278(3) . ? N2 C32 1.457(3) . ? C23 C31 1.528(3) . ? C24 C25 1.381(3) . ? C24 C29 1.383(3) . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 C27 1.385(4) . ? C26 H26 0.9500 . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 C29 1.396(3) . ? C28 H28 0.9500 . ? C29 C30 1.493(3) . ? C30 C31 1.543(3) . ? C30 C32 1.560(3) . ? C30 H30 1.0000 . ? C31 C41 1.530(3) . ? C31 C33 1.555(3) . ? C32 C43 1.513(3) . ? C32 H32 1.0000 . ? C33 C34 1.475(3) . ? C34 C39 1.384(3) . ? C34 C35 1.394(3) . ? C35 C36 1.375(3) . ? C35 H35 0.9500 . ? C36 C37 1.388(4) . ? C36 H36 0.9500 . ? C37 C38 1.385(3) . ? C38 C39 1.385(3) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40A H40D 0.9800 . ? C40A H40E 0.9800 . ? C40A H40F 0.9800 . ? C40B H40A 0.9800 . ? C40B H40B 0.9800 . ? C40B H40C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 122.88(16) . . ? C19 O4 C20 115.28(16) . . ? C15 O5 C18 117.68(17) . . ? C21 O7A C22A 117.9(3) . . ? C22B O7B C21 114.0(3) . . ? C11 N1 C10 110.86(17) . . ? O2 C1 O1 117.17(18) . . ? O2 C1 C9 123.59(18) . . ? O1 C1 C9 119.22(17) . . ? C7 C2 C3 123.0(2) . . ? C7 C2 O1 121.68(18) . . ? C3 C2 O1 115.4(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 117.6(2) . . ? C2 C7 C8 119.74(18) . . ? C6 C7 C8 122.6(2) . . ? C7 C8 C10 115.19(16) . . ? C7 C8 C9 113.78(16) . . ? C10 C8 C9 102.05(15) . . ? C7 C8 H8 108.5 . . ? C10 C8 H8 108.5 . . ? C9 C8 H8 108.5 . . ? C1 C9 C19 111.71(16) . . ? C1 C9 C8 114.02(16) . . ? C19 C9 C8 108.62(15) . . ? C1 C9 C11 108.98(15) . . ? C19 C9 C11 112.40(15) . . ? C8 C9 C11 100.68(15) . . ? N1 C10 C21 110.38(16) . . ? N1 C10 C8 106.02(15) . . ? C21 C10 C8 110.96(18) . . ? N1 C10 H10 109.8 . . ? C21 C10 H10 109.8 . . ? C8 C10 H10 109.8 . . ? N1 C11 C12 121.28(18) . . ? N1 C11 C9 113.23(17) . . ? C12 C11 C9 125.39(17) . . ? C17 C12 C13 118.09(18) . . ? C17 C12 C11 124.26(18) . . ? C13 C12 C11 117.58(18) . . ? C14 C13 C12 121.06(19) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 120.43(19) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? O5 C15 C16 124.87(19) . . ? O5 C15 C14 115.73(18) . . ? C16 C15 C14 119.40(19) . . ? C15 C16 C17 119.73(19) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 121.16(19) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? O5 C18 H18A 109.5 . . ? O5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 O4 125.90(19) . . ? O3 C19 C9 121.87(18) . . ? O4 C19 C9 112.11(16) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O6 C21 O7A 114.4(2) . . ? O6 C21 O7B 121.7(2) . . ? O6 C21 C10 127.1(2) . . ? O7A C21 C10 110.3(2) . . ? O7B C21 C10 105.9(2) . . ? O7A C22A H22A 109.5 . . ? O7A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? O7A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? O7B C22B H22D 109.5 . . ? O7B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? O7B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C23 O8 C24 122.45(16) . . ? C41 O11 C42 116.00(17) . . ? C40A O12A C37 111.6(4) . . ? C37 O12B C40B 110.7(3) . . ? C43 O14 C44 115.98(16) . . ? C33 N2 C32 110.40(17) . . ? O9 C23 O8 117.30(18) . . ? O9 C23 C31 123.87(18) . . ? O8 C23 C31 118.83(17) . . ? C25 C24 C29 123.0(2) . . ? C25 C24 O8 115.49(19) . . ? C29 C24 O8 121.46(18) . . ? C24 C25 C26 118.5(2) . . ? C24 C25 H25 120.8 . . ? C26 C25 H25 120.8 . . ? C25 C26 C27 120.2(2) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C28 120.3(2) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C29 120.5(2) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C24 C29 C28 117.42(19) . . ? C24 C29 C30 119.25(18) . . ? C28 C29 C30 123.32(19) . . ? C29 C30 C31 113.46(16) . . ? C29 C30 C32 116.63(16) . . ? C31 C30 C32 101.17(15) . . ? C29 C30 H30 108.4 . . ? C31 C30 H30 108.4 . . ? C32 C30 H30 108.4 . . ? C23 C31 C41 111.26(16) . . ? C23 C31 C30 112.94(16) . . ? C41 C31 C30 109.36(16) . . ? C23 C31 C33 108.01(16) . . ? C41 C31 C33 114.43(16) . . ? C30 C31 C33 100.47(15) . . ? N2 C32 C43 112.60(17) . . ? N2 C32 C30 105.48(16) . . ? C43 C32 C30 109.71(16) . . ? N2 C32 H32 109.7 . . ? C43 C32 H32 109.7 . . ? C30 C32 H32 109.7 . . ? N2 C33 C34 121.41(18) . . ? N2 C33 C31 113.08(17) . . ? C34 C33 C31 125.28(17) . . ? C39 C34 C35 117.6(2) . . ? C39 C34 C33 123.73(18) . . ? C35 C34 C33 118.6(2) . . ? C36 C35 C34 121.3(2) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C35 C36 C37 120.5(2) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? O12B C37 C38 133.3(3) . . ? O12B C37 C36 107.8(3) . . ? C38 C37 C36 118.9(2) . . ? C38 C37 O12A 105.5(3) . . ? C36 C37 O12A 135.6(3) . . ? C37 C38 C39 120.1(2) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C34 C39 C38 121.5(2) . . ? C34 C39 H39 119.2 . . ? C38 C39 H39 119.2 . . ? O12A C40A H40D 109.5 . . ? O12A C40A H40E 109.5 . . ? H40D C40A H40E 109.5 . . ? O12A C40A H40F 109.5 . . ? H40D C40A H40F 109.5 . . ? H40E C40A H40F 109.5 . . ? O12B C40B H40A 109.5 . . ? O12B C40B H40B 109.5 . . ? H40A C40B H40B 109.5 . . ? O12B C40B H40C 109.5 . . ? H40A C40B H40C 109.5 . . ? H40B C40B H40C 109.5 . . ? O10 C41 O11 126.12(19) . . ? O10 C41 C31 121.93(18) . . ? O11 C41 C31 111.91(17) . . ? O11 C42 H42A 109.5 . . ? O11 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O11 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O13 C43 O14 124.98(19) . . ? O13 C43 C32 126.03(19) . . ? O14 C43 C32 108.87(17) . . ? O14 C44 H44A 109.5 . . ? O14 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O14 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O1 C1 O2 -175.46(17) . . . . ? C2 O1 C1 C9 5.9(3) . . . . ? C1 O1 C2 C7 -14.9(3) . . . . ? C1 O1 C2 C3 165.98(18) . . . . ? C7 C2 C3 C4 1.1(3) . . . . ? O1 C2 C3 C4 -179.78(18) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C3 C2 C7 C6 -1.3(3) . . . . ? O1 C2 C7 C6 179.70(17) . . . . ? C3 C2 C7 C8 176.48(19) . . . . ? O1 C2 C7 C8 -2.5(3) . . . . ? C5 C6 C7 C2 0.7(3) . . . . ? C5 C6 C7 C8 -176.98(18) . . . . ? C2 C7 C8 C10 -91.4(2) . . . . ? C6 C7 C8 C10 86.2(2) . . . . ? C2 C7 C8 C9 25.9(3) . . . . ? C6 C7 C8 C9 -156.45(18) . . . . ? O2 C1 C9 C19 75.9(2) . . . . ? O1 C1 C9 C19 -105.57(19) . . . . ? O2 C1 C9 C8 -160.52(19) . . . . ? O1 C1 C9 C8 18.1(2) . . . . ? O2 C1 C9 C11 -48.9(2) . . . . ? O1 C1 C9 C11 129.63(18) . . . . ? C7 C8 C9 C1 -32.5(2) . . . . ? C10 C8 C9 C1 92.20(18) . . . . ? C7 C8 C9 C19 92.74(19) . . . . ? C10 C8 C9 C19 -142.53(15) . . . . ? C7 C8 C9 C11 -149.04(16) . . . . ? C10 C8 C9 C11 -24.31(18) . . . . ? C11 N1 C10 C21 -136.5(2) . . . . ? C11 N1 C10 C8 -16.3(2) . . . . ? C7 C8 C10 N1 149.36(17) . . . . ? C9 C8 C10 N1 25.58(19) . . . . ? C7 C8 C10 C21 -90.8(2) . . . . ? C9 C8 C10 C21 145.44(17) . . . . ? C10 N1 C11 C12 -177.40(17) . . . . ? C10 N1 C11 C9 -0.7(2) . . . . ? C1 C9 C11 N1 -103.2(2) . . . . ? C19 C9 C11 N1 132.41(18) . . . . ? C8 C9 C11 N1 17.0(2) . . . . ? C1 C9 C11 C12 73.3(2) . . . . ? C19 C9 C11 C12 -51.0(2) . . . . ? C8 C9 C11 C12 -166.47(18) . . . . ? N1 C11 C12 C17 176.1(2) . . . . ? C9 C11 C12 C17 -0.2(3) . . . . ? N1 C11 C12 C13 -0.7(3) . . . . ? C9 C11 C12 C13 -176.95(18) . . . . ? C17 C12 C13 C14 -3.1(3) . . . . ? C11 C12 C13 C14 173.85(19) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C18 O5 C15 C16 -15.0(3) . . . . ? C18 O5 C15 C14 164.8(2) . . . . ? C13 C14 C15 O5 -176.78(19) . . . . ? C13 C14 C15 C16 3.1(3) . . . . ? O5 C15 C16 C17 176.43(19) . . . . ? C14 C15 C16 C17 -3.4(3) . . . . ? C15 C16 C17 C12 0.5(3) . . . . ? C13 C12 C17 C16 2.8(3) . . . . ? C11 C12 C17 C16 -173.99(19) . . . . ? C20 O4 C19 O3 1.1(3) . . . . ? C20 O4 C19 C9 177.04(15) . . . . ? C1 C9 C19 O3 -164.13(18) . . . . ? C8 C9 C19 O3 69.3(2) . . . . ? C11 C9 C19 O3 -41.3(3) . . . . ? C1 C9 C19 O4 19.8(2) . . . . ? C8 C9 C19 O4 -106.86(18) . . . . ? C11 C9 C19 O4 142.63(16) . . . . ? C22A O7A C21 O6 -17.2(5) . . . . ? C22A O7A C21 O7B 95.9(4) . . . . ? C22A O7A C21 C10 -168.1(3) . . . . ? C22B O7B C21 O6 18.6(5) . . . . ? C22B O7B C21 O7A -81.4(4) . . . . ? C22B O7B C21 C10 174.5(3) . . . . ? N1 C10 C21 O6 50.2(3) . . . . ? C8 C10 C21 O6 -67.0(3) . . . . ? N1 C10 C21 O7A -163.4(2) . . . . ? C8 C10 C21 O7A 79.4(3) . . . . ? N1 C10 C21 O7B -103.9(2) . . . . ? C8 C10 C21 O7B 138.8(2) . . . . ? C24 O8 C23 O9 178.96(17) . . . . ? C24 O8 C23 C31 -1.9(3) . . . . ? C23 O8 C24 C25 -166.01(17) . . . . ? C23 O8 C24 C29 15.8(3) . . . . ? C29 C24 C25 C26 -0.7(3) . . . . ? O8 C24 C25 C26 -178.87(18) . . . . ? C24 C25 C26 C27 0.1(3) . . . . ? C25 C26 C27 C28 -0.2(3) . . . . ? C26 C27 C28 C29 0.8(3) . . . . ? C25 C24 C29 C28 1.3(3) . . . . ? O8 C24 C29 C28 179.36(17) . . . . ? C25 C24 C29 C30 -177.67(18) . . . . ? O8 C24 C29 C30 0.4(3) . . . . ? C27 C28 C29 C24 -1.3(3) . . . . ? C27 C28 C29 C30 177.59(18) . . . . ? C24 C29 C30 C31 -27.4(2) . . . . ? C28 C29 C30 C31 153.68(18) . . . . ? C24 C29 C30 C32 89.6(2) . . . . ? C28 C29 C30 C32 -89.3(2) . . . . ? O9 C23 C31 C41 -82.6(2) . . . . ? O8 C23 C31 C41 98.3(2) . . . . ? O9 C23 C31 C30 153.99(19) . . . . ? O8 C23 C31 C30 -25.1(2) . . . . ? O9 C23 C31 C33 43.8(2) . . . . ? O8 C23 C31 C33 -135.31(17) . . . . ? C29 C30 C31 C23 38.4(2) . . . . ? C32 C30 C31 C23 -87.27(18) . . . . ? C29 C30 C31 C41 -86.0(2) . . . . ? C32 C30 C31 C41 148.25(16) . . . . ? C29 C30 C31 C33 153.25(16) . . . . ? C32 C30 C31 C33 27.54(18) . . . . ? C33 N2 C32 C43 138.80(18) . . . . ? C33 N2 C32 C30 19.2(2) . . . . ? C29 C30 C32 N2 -153.02(17) . . . . ? C31 C30 C32 N2 -29.44(19) . . . . ? C29 C30 C32 C43 85.5(2) . . . . ? C31 C30 C32 C43 -150.96(16) . . . . ? C32 N2 C33 C34 174.77(17) . . . . ? C32 N2 C33 C31 -0.1(2) . . . . ? C23 C31 C33 N2 99.6(2) . . . . ? C41 C31 C33 N2 -135.93(18) . . . . ? C30 C31 C33 N2 -18.9(2) . . . . ? C23 C31 C33 C34 -75.0(2) . . . . ? C41 C31 C33 C34 49.5(3) . . . . ? C30 C31 C33 C34 166.50(18) . . . . ? N2 C33 C34 C39 176.4(2) . . . . ? C31 C33 C34 C39 -9.5(3) . . . . ? N2 C33 C34 C35 -6.0(3) . . . . ? C31 C33 C34 C35 168.19(19) . . . . ? C39 C34 C35 C36 2.6(3) . . . . ? C33 C34 C35 C36 -175.2(2) . . . . ? C34 C35 C36 C37 -1.2(4) . . . . ? C40B O12B C37 C38 16.0(5) . . . . ? C40B O12B C37 C36 -166.8(3) . . . . ? C40B O12B C37 O12A 7.6(5) . . . . ? C35 C36 C37 O12B -179.4(3) . . . . ? C35 C36 C37 C38 -1.7(4) . . . . ? C35 C36 C37 O12A 176.9(3) . . . . ? C40A O12A C37 O12B -21.1(5) . . . . ? C40A O12A C37 C38 165.2(4) . . . . ? C40A O12A C37 C36 -13.5(6) . . . . ? O12B C37 C38 C39 -179.8(3) . . . . ? C36 C37 C38 C39 3.2(4) . . . . ? O12A C37 C38 C39 -175.7(3) . . . . ? C35 C34 C39 C38 -1.1(3) . . . . ? C33 C34 C39 C38 176.6(2) . . . . ? C37 C38 C39 C34 -1.9(4) . . . . ? C42 O11 C41 O10 -3.5(3) . . . . ? C42 O11 C41 C31 178.92(16) . . . . ? C23 C31 C41 O10 178.81(18) . . . . ? C30 C31 C41 O10 -55.7(2) . . . . ? C33 C31 C41 O10 56.0(3) . . . . ? C23 C31 C41 O11 -3.5(2) . . . . ? C30 C31 C41 O11 121.93(17) . . . . ? C33 C31 C41 O11 -126.28(18) . . . . ? C44 O14 C43 O13 -4.4(3) . . . . ? C44 O14 C43 C32 171.87(17) . . . . ? N2 C32 C43 O13 -26.7(3) . . . . ? C30 C32 C43 O13 90.4(2) . . . . ? N2 C32 C43 O14 157.08(16) . . . . ? C30 C32 C43 O14 -85.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 O9 1.00 2.53 3.498(3) 164 . C20 H20B O2 0.98 2.57 3.106(3) 114 3_666 C20 H20B O14 0.98 2.66 3.485(3) 142 3_666 C22A H22A O10 0.98 2.48 3.175(5) 128 3_566 _refine_diff_density_max 0.393 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.058 _shelxl_version_number 2013-4 #===END