data_johueinm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 F N3 O4, C7 H6 O3, Cl' _chemical_formula_sum 'C28 H31 Cl F N3 O7' _chemical_formula_weight 576.01 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.779(2) _cell_length_b 17.321(4) _cell_length_c 10.313(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.685(4) _cell_angle_gamma 90.00 _cell_volume 1350.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3446 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 21.39 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13169 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4756 _reflns_number_gt 4132 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.0094P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(9) _refine_ls_number_reflns 4756 _refine_ls_number_parameters 377 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.103 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.49147(13) 0.99664(9) 0.29762(9) 0.0794(3) Uani 1 1 d . . . F1 F 0.5601(3) 0.49957(13) 0.36744(17) 0.0658(5) Uani 1 1 d . . . N1 N 0.1538(3) 0.50734(15) -0.1508(2) 0.0364(6) Uani 1 1 d . . . N2 N 0.4762(3) 0.64492(14) 0.2442(2) 0.0400(6) Uani 1 1 d . . . N3 N 0.3136(4) 0.72538(13) 0.4424(3) 0.0419(7) Uani 1 1 d D . . H3A H 0.2063(17) 0.741(2) 0.413(4) 0.063 Uiso 1 1 d D . . H3B H 0.318(5) 0.67578(17) 0.441(4) 0.063 Uiso 1 1 d D . . O1 O 0.0874(4) 0.23563(14) -0.1504(3) 0.0661(8) Uani 1 1 d D . . H10 H 0.147(6) 0.249(3) -0.075(2) 0.099 Uiso 1 1 d D . . O2 O -0.0107(3) 0.30018(14) -0.3394(3) 0.0581(7) Uani 1 1 d . . . O3 O 0.2449(4) 0.30310(13) 0.0534(3) 0.0593(7) Uani 1 1 d . . . O4 O 0.3187(3) 0.64547(11) -0.0225(2) 0.0408(5) Uani 1 1 d . . . C1 C 0.1019(4) 0.44063(19) -0.2088(3) 0.0413(8) Uani 1 1 d . . . H1 H 0.0417 0.4416 -0.2982 0.050 Uiso 1 1 calc R . . C2 C 0.1303(4) 0.3699(2) -0.1471(4) 0.0426(8) Uani 1 1 d . . . C3 C 0.2224(4) 0.3663(2) -0.0107(3) 0.0423(8) Uani 1 1 d . . . C4 C 0.2903(4) 0.43801(19) 0.0500(3) 0.0391(7) Uani 1 1 d . . . C5 C 0.3964(5) 0.4376(2) 0.1795(3) 0.0452(8) Uani 1 1 d . . . H5 H 0.4229 0.3909 0.2242 0.054 Uiso 1 1 calc R . . C6 C 0.4609(4) 0.5036(2) 0.2407(3) 0.0432(7) Uani 1 1 d . . . C7 C 0.4256(4) 0.57604(19) 0.1796(3) 0.0366(7) Uani 1 1 d . . . C8 C 0.3335(4) 0.57615(18) 0.0451(3) 0.0337(7) Uani 1 1 d . . . C9 C 0.2580(4) 0.50875(19) -0.0194(3) 0.0346(7) Uani 1 1 d . . . C10 C 0.0628(5) 0.2993(2) -0.2206(4) 0.0503(9) Uani 1 1 d . . . C11 C 0.1108(4) 0.57724(18) -0.2338(3) 0.0424(8) Uani 1 1 d . . . H11 H 0.2090 0.5991 -0.2663 0.051 Uiso 1 1 calc R . . C12 C -0.0188(5) 0.6336(2) -0.2080(4) 0.0611(10) Uani 1 1 d . . . H12A H 0.0026 0.6878 -0.2220 0.073 Uiso 1 1 calc R . . H12B H -0.0744 0.6231 -0.1350 0.073 Uiso 1 1 calc R . . C13 C -0.0656(5) 0.5828(2) -0.3274(4) 0.0623(10) Uani 1 1 d . . . H13A H -0.1492 0.5414 -0.3269 0.075 Uiso 1 1 calc R . . H13B H -0.0723 0.6061 -0.4140 0.075 Uiso 1 1 calc R . . C14 C 0.4800(5) 0.6691(2) -0.0546(3) 0.0578(10) Uani 1 1 d . . . H14A H 0.5758 0.6643 0.0230 0.087 Uiso 1 1 calc R . . H14B H 0.4699 0.7219 -0.0838 0.087 Uiso 1 1 calc R . . H14C H 0.5024 0.6369 -0.1246 0.087 Uiso 1 1 calc R . . C15 C 0.3645(5) 0.71425(19) 0.2176(3) 0.0460(8) Uani 1 1 d . . . H15A H 0.2399 0.7008 0.1950 0.055 Uiso 1 1 calc R . . H15B H 0.3910 0.7445 0.1456 0.055 Uiso 1 1 calc R . . C16 C 0.4132(4) 0.75713(18) 0.3474(3) 0.0401(8) Uani 1 1 d . . . H16 H 0.3914 0.8126 0.3336 0.048 Uiso 1 1 calc R . . C17 C 0.3813(5) 0.7519(2) 0.5818(3) 0.0533(9) Uani 1 1 d . . . H17A H 0.3111 0.7294 0.6383 0.064 Uiso 1 1 calc R . . H17B H 0.3715 0.8076 0.5859 0.064 Uiso 1 1 calc R . . C18 C 0.5723(5) 0.7281(2) 0.6310(3) 0.0514(9) Uani 1 1 d . . . H18A H 0.6167 0.7466 0.7215 0.062 Uiso 1 1 calc R . . H18B H 0.5805 0.6723 0.6321 0.062 Uiso 1 1 calc R . . C19 C 0.6841(5) 0.76037(19) 0.5432(3) 0.0470(8) Uani 1 1 d . . . H19A H 0.8030 0.7398 0.5716 0.056 Uiso 1 1 calc R . . H19B H 0.6912 0.8160 0.5536 0.056 Uiso 1 1 calc R . . C20 C 0.6094(5) 0.7408(2) 0.3959(3) 0.0442(8) Uani 1 1 d . . . H20 H 0.6727 0.7717 0.3426 0.053 Uiso 1 1 calc R . . C21 C 0.6245(4) 0.6560(2) 0.3601(3) 0.0488(9) Uani 1 1 d . . . H21A H 0.7365 0.6458 0.3376 0.059 Uiso 1 1 calc R . . H21B H 0.6136 0.6227 0.4332 0.059 Uiso 1 1 calc R . . O5 O -0.1983(4) 0.95831(15) 0.5255(3) 0.0622(7) Uani 1 1 d D . . H50 H -0.279(4) 0.971(3) 0.460(3) 0.093 Uiso 1 1 d D . . O6 O -0.1643(3) 1.07871(15) 0.6017(3) 0.0623(7) Uani 1 1 d . . . O7 O 0.3386(4) 0.88735(17) 1.0670(3) 0.0812(9) Uani 1 1 d D . . H70 H 0.388(7) 0.916(3) 1.130(4) 0.122 Uiso 1 1 d D . . C22 C 0.0022(4) 0.97849(18) 0.7303(3) 0.0461(8) Uani 1 1 d . . . C23 C 0.0802(5) 1.02661(19) 0.8351(4) 0.0472(8) Uani 1 1 d . . . H23 H 0.0568 1.0793 0.8291 0.057 Uiso 1 1 calc R . . C24 C 0.1921(4) 0.9971(2) 0.9480(4) 0.0526(8) Uani 1 1 d . . . H24 H 0.2420 1.0300 1.0180 0.063 Uiso 1 1 calc R . . C25 C 0.2310(5) 0.9198(2) 0.9587(4) 0.0585(10) Uani 1 1 d . . . C26 C 0.1557(5) 0.8721(2) 0.8535(5) 0.0713(12) Uani 1 1 d . . . H26 H 0.1812 0.8195 0.8593 0.086 Uiso 1 1 calc R . . C27 C 0.0441(5) 0.90055(19) 0.7406(5) 0.0628(11) Uani 1 1 d . . . H27 H -0.0039 0.8674 0.6703 0.075 Uiso 1 1 calc R . . C28 C -0.1252(4) 1.0109(2) 0.6149(3) 0.0473(8) Uani 1 1 d . . . 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 Cl1 0.0613(6) 0.1171(9) 0.0558(6) 0.0113(7) 0.0063(4) 0.0093(7) F1 0.0883(14) 0.0573(12) 0.0392(10) 0.0099(11) -0.0102(9) 0.0045(13) N1 0.0378(14) 0.0348(15) 0.0345(13) -0.0008(12) 0.0044(11) -0.0016(12) N2 0.0446(15) 0.0370(15) 0.0339(14) 0.0011(12) 0.0002(12) 0.0043(12) N3 0.0447(16) 0.0323(14) 0.0463(17) 0.0000(13) 0.0062(13) 0.0008(13) O1 0.0703(19) 0.0386(15) 0.081(2) -0.0053(15) 0.0020(15) -0.0060(13) O2 0.0545(15) 0.0565(16) 0.0594(16) -0.0142(13) 0.0055(13) -0.0143(12) O3 0.0726(18) 0.0312(13) 0.0699(17) 0.0107(12) 0.0089(14) 0.0060(12) O4 0.0480(13) 0.0340(12) 0.0387(12) 0.0079(10) 0.0069(10) -0.0046(10) C1 0.0361(18) 0.047(2) 0.0410(18) -0.0037(17) 0.0086(15) -0.0028(16) C2 0.0346(17) 0.0406(19) 0.053(2) -0.0053(16) 0.0111(14) -0.0010(14) C3 0.0371(18) 0.0402(19) 0.050(2) 0.0049(17) 0.0111(15) 0.0047(15) C4 0.0403(18) 0.0365(18) 0.0392(18) 0.0024(15) 0.0070(15) 0.0069(14) C5 0.054(2) 0.0342(19) 0.0467(19) 0.0098(16) 0.0100(16) 0.0124(16) C6 0.0483(18) 0.047(2) 0.0305(15) 0.0037(17) 0.0023(13) 0.0061(17) C7 0.0324(16) 0.0418(19) 0.0357(17) 0.0029(15) 0.0080(13) 0.0018(14) C8 0.0317(16) 0.0376(17) 0.0329(16) 0.0056(15) 0.0097(13) 0.0038(14) C9 0.0290(14) 0.0385(18) 0.0369(16) 0.0013(14) 0.0086(12) 0.0018(14) C10 0.0357(19) 0.047(2) 0.068(3) -0.009(2) 0.0111(19) -0.0050(16) C11 0.0480(19) 0.0404(18) 0.0352(17) 0.0054(15) 0.0023(15) -0.0027(16) C12 0.061(2) 0.054(2) 0.062(2) 0.007(2) 0.001(2) 0.011(2) C13 0.057(2) 0.052(2) 0.064(2) 0.010(2) -0.0123(19) 0.0012(19) C14 0.066(2) 0.060(2) 0.048(2) 0.0131(17) 0.0141(18) -0.0143(19) C15 0.049(2) 0.047(2) 0.0389(18) -0.0021(15) 0.0035(15) 0.0057(16) C16 0.052(2) 0.0309(16) 0.0340(17) 0.0059(14) 0.0041(15) 0.0001(15) C17 0.075(3) 0.045(2) 0.040(2) -0.0045(16) 0.0144(19) 0.0006(19) C18 0.063(2) 0.048(2) 0.0368(19) -0.0046(16) -0.0027(16) 0.0048(17) C19 0.047(2) 0.0365(18) 0.049(2) -0.0075(16) -0.0065(16) -0.0062(15) C20 0.047(2) 0.046(2) 0.0387(19) 0.0024(15) 0.0063(15) -0.0095(16) C21 0.0411(18) 0.054(2) 0.046(2) -0.0108(17) 0.0009(15) 0.0099(16) O5 0.0711(19) 0.0420(14) 0.0633(17) -0.0029(13) -0.0043(13) 0.0052(13) O6 0.0779(19) 0.0382(15) 0.0670(17) 0.0020(13) 0.0094(14) 0.0136(13) O7 0.080(2) 0.062(2) 0.085(2) 0.0213(17) -0.0128(17) 0.0030(16) C22 0.0416(18) 0.041(2) 0.057(2) -0.0011(16) 0.0149(16) -0.0017(15) C23 0.053(2) 0.0355(18) 0.056(2) -0.0006(16) 0.0171(18) -0.0020(15) C24 0.057(2) 0.043(2) 0.057(2) -0.0029(19) 0.0122(17) -0.0055(19) C25 0.043(2) 0.056(3) 0.069(3) 0.013(2) -0.0001(18) -0.0089(18) C26 0.058(2) 0.037(2) 0.105(3) 0.003(2) -0.007(2) 0.0076(18) C27 0.057(2) 0.033(2) 0.088(3) -0.0132(19) -0.004(2) 0.0007(17) C28 0.0484(19) 0.039(2) 0.057(2) -0.0053(17) 0.0180(17) 0.0010(17) _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 C6 1.353(3) . ? N1 C1 1.320(4) . ? N1 C9 1.405(4) . ? N1 C11 1.475(4) . ? N2 C7 1.378(4) . ? N2 C21 1.464(4) . ? N2 C15 1.470(4) . ? N3 C17 1.482(4) . ? N3 C16 1.490(4) . ? N3 H3A 0.8600(11) . ? N3 H3B 0.8600(11) . ? O1 C10 1.309(4) . ? O1 H10 0.8401(11) . ? O2 C10 1.223(4) . ? O3 C3 1.270(4) . ? O4 C8 1.380(3) . ? O4 C14 1.430(4) . ? C1 C2 1.374(5) . ? C1 H1 0.9300 . ? C2 C3 1.421(5) . ? C2 C10 1.469(5) . ? C3 C4 1.434(5) . ? C4 C5 1.394(5) . ? C4 C9 1.411(4) . ? C5 C6 1.344(5) . ? C5 H5 0.9300 . ? C6 C7 1.402(4) . ? C7 C8 1.403(4) . ? C8 C9 1.402(4) . ? C11 C12 1.472(5) . ? C11 C13 1.482(5) . ? C11 H11 0.9800 . ? C12 C13 1.486(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.499(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C20 1.516(5) . ? C16 H16 0.9800 . ? C17 C18 1.509(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.503(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.531(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.525(5) . ? C20 H20 0.9800 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? O5 C28 1.325(4) . ? O5 H50 0.8400(11) . ? O6 C28 1.213(4) . ? O7 C25 1.349(5) . ? O7 H70 0.8400(11) . ? C22 C23 1.386(5) . ? C22 C27 1.387(4) . ? C22 C28 1.468(5) . ? C23 C24 1.377(5) . ? C23 H23 0.9300 . ? C24 C25 1.372(5) . ? C24 H24 0.9300 . ? C25 C26 1.380(6) . ? C26 C27 1.369(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? 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 N1 C9 119.8(3) . . ? C1 N1 C11 116.9(2) . . ? C9 N1 C11 123.0(2) . . ? C7 N2 C21 126.0(3) . . ? C7 N2 C15 121.9(2) . . ? C21 N2 C15 111.2(2) . . ? C17 N3 C16 113.7(3) . . ? C17 N3 H3A 110(3) . . ? C16 N3 H3A 105(3) . . ? C17 N3 H3B 109(3) . . ? C16 N3 H3B 109(2) . . ? H3A N3 H3B 110(4) . . ? C10 O1 H10 105(4) . . ? C8 O4 C14 113.1(2) . . ? N1 C1 C2 124.9(3) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? C1 C2 C3 119.0(3) . . ? C1 C2 C10 120.3(3) . . ? C3 C2 C10 120.7(3) . . ? O3 C3 C2 121.8(3) . . ? O3 C3 C4 121.9(3) . . ? C2 C3 C4 116.2(3) . . ? C5 C4 C9 119.0(3) . . ? C5 C4 C3 119.2(3) . . ? C9 C4 C3 121.8(3) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 F1 118.3(3) . . ? C5 C6 C7 122.5(3) . . ? F1 C6 C7 119.1(3) . . ? N2 C7 C6 123.7(3) . . ? N2 C7 C8 119.8(3) . . ? C6 C7 C8 116.5(3) . . ? O4 C8 C9 120.6(3) . . ? O4 C8 C7 117.6(3) . . ? C9 C8 C7 121.8(3) . . ? C8 C9 N1 123.6(3) . . ? C8 C9 C4 118.6(3) . . ? N1 C9 C4 117.8(3) . . ? O2 C10 O1 122.4(3) . . ? O2 C10 C2 122.2(3) . . ? O1 C10 C2 115.4(3) . . ? C12 C11 N1 120.7(3) . . ? C12 C11 C13 60.4(2) . . ? N1 C11 C13 118.7(3) . . ? C12 C11 H11 115.3 . . ? N1 C11 H11 115.3 . . ? C13 C11 H11 115.3 . . ? C11 C12 C13 60.1(2) . . ? C11 C12 H12A 117.8 . . ? C13 C12 H12A 117.8 . . ? C11 C12 H12B 117.8 . . ? C13 C12 H12B 117.8 . . ? H12A C12 H12B 114.9 . . ? C11 C13 C12 59.5(2) . . ? C11 C13 H13A 117.8 . . ? C12 C13 H13A 117.8 . . ? C11 C13 H13B 117.8 . . ? C12 C13 H13B 117.8 . . ? H13A C13 H13B 115.0 . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 103.0(2) . . ? N2 C15 H15A 111.2 . . ? C16 C15 H15A 111.2 . . ? N2 C15 H15B 111.2 . . ? C16 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? N3 C16 C15 110.1(3) . . ? N3 C16 C20 110.7(3) . . ? C15 C16 C20 103.0(3) . . ? N3 C16 H16 111.0 . . ? C15 C16 H16 111.0 . . ? C20 C16 H16 111.0 . . ? N3 C17 C18 109.7(3) . . ? N3 C17 H17A 109.7 . . ? C18 C17 H17A 109.7 . . ? N3 C17 H17B 109.7 . . ? C18 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C19 C18 C17 111.1(3) . . ? C19 C18 H18A 109.4 . . ? C17 C18 H18A 109.4 . . ? C19 C18 H18B 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C18 C19 C20 112.2(3) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C16 C20 C21 103.2(3) . . ? C16 C20 C19 113.7(3) . . ? C21 C20 C19 114.9(3) . . ? C16 C20 H20 108.2 . . ? C21 C20 H20 108.2 . . ? C19 C20 H20 108.2 . . ? N2 C21 C20 103.5(3) . . ? N2 C21 H21A 111.1 . . ? C20 C21 H21A 111.1 . . ? N2 C21 H21B 111.1 . . ? C20 C21 H21B 111.1 . . ? H21A C21 H21B 109.0 . . ? C28 O5 H50 120(3) . . ? C25 O7 H70 118(4) . . ? C23 C22 C27 118.3(3) . . ? C23 C22 C28 119.3(3) . . ? C27 C22 C28 122.4(3) . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 120.9(4) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? O7 C25 C24 123.7(4) . . ? O7 C25 C26 117.8(3) . . ? C24 C25 C26 118.5(4) . . ? C27 C26 C25 121.3(4) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C22 120.4(4) . . ? C26 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? O6 C28 O5 122.2(3) . . ? O6 C28 C22 124.4(3) . . ? O5 C28 C22 113.4(3) . . ? 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 C9 N1 C1 C2 5.3(4) . . . . ? C11 N1 C1 C2 -180.0(3) . . . . ? N1 C1 C2 C3 -0.2(5) . . . . ? N1 C1 C2 C10 178.5(3) . . . . ? C1 C2 C3 O3 176.5(3) . . . . ? C10 C2 C3 O3 -2.2(5) . . . . ? C1 C2 C3 C4 -4.3(4) . . . . ? C10 C2 C3 C4 177.0(3) . . . . ? O3 C3 C4 C5 5.4(5) . . . . ? C2 C3 C4 C5 -173.9(3) . . . . ? O3 C3 C4 C9 -176.9(3) . . . . ? C2 C3 C4 C9 3.8(4) . . . . ? C9 C4 C5 C6 3.1(5) . . . . ? C3 C4 C5 C6 -179.1(3) . . . . ? C4 C5 C6 F1 178.7(3) . . . . ? C4 C5 C6 C7 0.3(5) . . . . ? C21 N2 C7 C6 25.3(5) . . . . ? C15 N2 C7 C6 -143.3(3) . . . . ? C21 N2 C7 C8 -154.6(3) . . . . ? C15 N2 C7 C8 36.7(4) . . . . ? C5 C6 C7 N2 173.8(3) . . . . ? F1 C6 C7 N2 -4.6(5) . . . . ? C5 C6 C7 C8 -6.3(4) . . . . ? F1 C6 C7 C8 175.4(3) . . . . ? C14 O4 C8 C9 -106.1(3) . . . . ? C14 O4 C8 C7 74.1(3) . . . . ? N2 C7 C8 O4 8.8(4) . . . . ? C6 C7 C8 O4 -171.1(3) . . . . ? N2 C7 C8 C9 -171.0(3) . . . . ? C6 C7 C8 C9 9.1(4) . . . . ? O4 C8 C9 N1 -4.7(4) . . . . ? C7 C8 C9 N1 175.1(3) . . . . ? O4 C8 C9 C4 174.2(3) . . . . ? C7 C8 C9 C4 -5.9(4) . . . . ? C1 N1 C9 C8 173.4(3) . . . . ? C11 N1 C9 C8 -1.0(4) . . . . ? C1 N1 C9 C4 -5.6(4) . . . . ? C11 N1 C9 C4 -179.9(3) . . . . ? C5 C4 C9 C8 -0.3(4) . . . . ? C3 C4 C9 C8 -178.0(3) . . . . ? C5 C4 C9 N1 178.7(3) . . . . ? C3 C4 C9 N1 1.0(4) . . . . ? C1 C2 C10 O2 4.3(5) . . . . ? C3 C2 C10 O2 -177.0(3) . . . . ? C1 C2 C10 O1 -175.9(3) . . . . ? C3 C2 C10 O1 2.7(5) . . . . ? C1 N1 C11 C12 111.6(3) . . . . ? C9 N1 C11 C12 -73.9(4) . . . . ? C1 N1 C11 C13 40.9(4) . . . . ? C9 N1 C11 C13 -144.6(3) . . . . ? N1 C11 C12 C13 -107.7(4) . . . . ? N1 C11 C13 C12 111.0(4) . . . . ? C7 N2 C15 C16 151.2(3) . . . . ? C21 N2 C15 C16 -18.9(3) . . . . ? C17 N3 C16 C15 167.2(3) . . . . ? C17 N3 C16 C20 54.0(3) . . . . ? N2 C15 C16 N3 -82.2(3) . . . . ? N2 C15 C16 C20 35.9(3) . . . . ? C16 N3 C17 C18 -59.4(4) . . . . ? N3 C17 C18 C19 57.9(4) . . . . ? C17 C18 C19 C20 -52.9(4) . . . . ? N3 C16 C20 C21 77.6(3) . . . . ? C15 C16 C20 C21 -40.0(3) . . . . ? N3 C16 C20 C19 -47.5(3) . . . . ? C15 C16 C20 C19 -165.1(3) . . . . ? C18 C19 C20 C16 48.3(4) . . . . ? C18 C19 C20 C21 -70.4(4) . . . . ? C7 N2 C21 C20 -175.5(3) . . . . ? C15 N2 C21 C20 -5.8(3) . . . . ? C16 C20 C21 N2 28.0(3) . . . . ? C19 C20 C21 N2 152.4(3) . . . . ? C27 C22 C23 C24 -2.0(5) . . . . ? C28 C22 C23 C24 176.1(3) . . . . ? C22 C23 C24 C25 1.0(5) . . . . ? C23 C24 C25 O7 -179.5(4) . . . . ? C23 C24 C25 C26 0.1(5) . . . . ? O7 C25 C26 C27 179.5(4) . . . . ? C24 C25 C26 C27 -0.2(6) . . . . ? C25 C26 C27 C22 -0.9(7) . . . . ? C23 C22 C27 C26 1.9(6) . . . . ? C28 C22 C27 C26 -176.1(4) . . . . ? C23 C22 C28 O6 2.6(5) . . . . ? C27 C22 C28 O6 -179.4(4) . . . . ? C23 C22 C28 O5 -176.1(3) . . . . ? C27 C22 C28 O5 1.9(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.194 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.045