data_mo_jb141015_1_1_0m _audit_creation_date 2015-10-15 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _shelxl_version_number 2014/6 _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_acknowledgements ; X-Ray services provided by SMoCC - The Small Molecule Crystallography Center of ETH Zurich. ; _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C20 H28 N2 O3' _chemical_formula_sum 'C20 H28 N2 O3' _chemical_formula_weight 344.44 _chemical_absolute_configuration unk _chemical_melting_point ? 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' _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. ; _space_group_crystal_system 'monoclinic' _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7442(9) _cell_length_b 6.1717(5) _cell_length_c 14.9524(13) _cell_angle_alpha 90 _cell_angle_beta 90.609(2) _cell_angle_gamma 90 _cell_volume 899.16(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 966 _cell_measurement_temperature 100.0(2) _cell_measurement_theta_max 24.69 _cell_measurement_theta_min 2.51 _shelx_estimated_absorpt_T_max 0.997 _shelx_estimated_absorpt_T_min 0.986 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6866 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0408 before and 0.0356 after correction. The Ratio of minimum to maximum transmission is 0.9209. The \l/2 correction factor is 0.00150. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0639 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5498 _diffrn_reflns_point_group_measured_fraction_full 0.763 _diffrn_reflns_point_group_measured_fraction_max 0.742 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.487 _diffrn_reflns_theta_min 2.090 _diffrn_ambient_temperature 100.0(2) _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 8.33 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'kappa-stage diffractometer' _diffrn_measurement_device_type 'Bruker Apex2 Duo (Mo)' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'focusing graphite' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed tube' _diffrn_special_details ? _diffrn_standards_number 0 _reflns_Friedel_coverage 0.362 _reflns_Friedel_fraction_full 0.478 _reflns_Friedel_fraction_max 0.435 _reflns_number_gt 2412 _reflns_number_total 3053 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _refine_diff_density_max 0.339 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 591 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.6(10) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3053 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0448 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.0486P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.0969 _refine_special_details 'N-H proton detected on difference Fourier map, but then refined using DFIX restraint. Crystallized from racemic mix. Absolute configuration is not claimed due to unreliable Flack and Hooft parameters.' _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2. Restrained distances N1-H1 0.91 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C8(H8), C11(H11) 3.b Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B) 3.c Aromatic/amide H refined with riding coordinates: C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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 -0.0799(2) 0.8764(4) 0.88560(14) 0.0236(5) Uani 1 1 d . . . . . O2 O 0.2037(2) 0.8208(3) 0.39102(14) 0.0210(5) Uani 1 1 d . . . . . O3 O 0.3664(2) 0.5987(4) 0.44878(14) 0.0191(5) Uani 1 1 d . . . . . N1 N 0.0469(2) 0.6762(4) 0.67010(16) 0.0150(6) Uani 1 1 d D . . . . H1 H -0.020(3) 0.576(4) 0.6626(19) 0.018 Uiso 1 1 d DR . . . . N2 N 0.2169(2) 0.5437(4) 0.82477(16) 0.0150(6) Uani 1 1 d . . . . . C1 C 0.4607(3) 0.1449(5) 0.87014(19) 0.0173(7) Uani 1 1 d . . . . . H1A H 0.3977 0.0326 0.8555 0.021 Uiso 1 1 calc R . . . . C2 C 0.6012(3) 0.1041(5) 0.8685(2) 0.0205(7) Uani 1 1 d . . . . . H2 H 0.6337 -0.0356 0.8526 0.025 Uiso 1 1 calc R . . . . C3 C 0.6936(3) 0.2665(5) 0.8901(2) 0.0199(7) Uani 1 1 d . . . . . H3 H 0.7894 0.2377 0.8901 0.024 Uiso 1 1 calc R . . . . C4 C 0.6458(3) 0.4725(5) 0.91184(19) 0.0189(7) Uani 1 1 d . . . . . H4 H 0.7088 0.5851 0.9259 0.023 Uiso 1 1 calc R . . . . C5 C 0.5063(3) 0.5121(5) 0.91288(19) 0.0177(7) Uani 1 1 d . . . . . H5 H 0.4741 0.6530 0.9274 0.021 Uiso 1 1 calc R . . . . C6 C 0.4120(3) 0.3493(5) 0.89305(19) 0.0151(6) Uani 1 1 d . . . . . C7 C 0.2598(3) 0.3968(5) 0.8976(2) 0.0173(7) Uani 1 1 d . . . . . H7A H 0.2077 0.2595 0.8929 0.021 Uiso 1 1 calc R . . . . H7B H 0.2387 0.4640 0.9560 0.021 Uiso 1 1 calc R . . . . C8 C 0.0755(3) 0.6161(5) 0.83491(19) 0.0144(6) Uani 1 1 d . . . . . H8 H 0.0126 0.4882 0.8319 0.017 Uiso 1 1 calc R . . . . C9 C 0.0395(3) 0.7538(6) 0.9148(2) 0.0196(7) Uani 1 1 d . . . . . H9A H 0.0175 0.6621 0.9670 0.024 Uiso 1 1 calc R . . . . H9B H 0.1162 0.8518 0.9310 0.024 Uiso 1 1 calc R . . . . C10 C -0.0942(3) 0.8617(6) 0.7890(2) 0.0211(7) Uani 1 1 d . . . . . H10A H -0.1109 1.0064 0.7623 0.025 Uiso 1 1 calc R . . . . H10B H -0.1709 0.7642 0.7720 0.025 Uiso 1 1 calc R . . . . C11 C 0.0415(3) 0.7704(5) 0.75889(19) 0.0157(6) Uani 1 1 d . . . . . H11 H 0.1101 0.8908 0.7613 0.019 Uiso 1 1 calc R . . . . C12 C 0.2236(3) 0.4291(5) 0.73830(19) 0.0154(6) Uani 1 1 d . . . . . H12A H 0.1632 0.3003 0.7408 0.018 Uiso 1 1 calc R . . . . H12B H 0.3186 0.3773 0.7296 0.018 Uiso 1 1 calc R . . . . C13 C 0.1810(3) 0.5671(5) 0.65698(19) 0.0126(6) Uani 1 1 d . . . . . C14 C 0.1663(3) 0.4163(5) 0.57678(19) 0.0150(6) Uani 1 1 d . . . . . H14A H 0.0926 0.3101 0.5888 0.018 Uiso 1 1 calc R . . . . H14B H 0.2529 0.3349 0.5694 0.018 Uiso 1 1 calc R . . . . C15 C 0.1328(3) 0.5355(5) 0.4898(2) 0.0159(6) Uani 1 1 d . . . . . H15A H 0.1281 0.4304 0.4399 0.019 Uiso 1 1 calc R . . . . H15B H 0.0421 0.6065 0.4946 0.019 Uiso 1 1 calc R . . . . C16 C 0.2409(3) 0.7038(5) 0.4707(2) 0.0162(7) Uani 1 1 d . . . . . C17 C 0.2611(3) 0.8595(5) 0.54894(19) 0.0155(6) Uani 1 1 d . . . . . H17A H 0.1773 0.9479 0.5562 0.019 Uiso 1 1 calc R . . . . H17B H 0.3381 0.9588 0.5359 0.019 Uiso 1 1 calc R . . . . C18 C 0.2917(3) 0.7379(5) 0.63616(19) 0.0152(6) Uani 1 1 d . . . . . H18A H 0.2971 0.8432 0.6860 0.018 Uiso 1 1 calc R . . . . H18B H 0.3820 0.6654 0.6317 0.018 Uiso 1 1 calc R . . . . C19 C 0.4362(4) 0.7384(7) 0.3893(3) 0.0391(10) Uani 1 1 d . . . . . H19A H 0.4765 0.6546 0.3396 0.047 Uiso 1 1 calc R . . . . H19B H 0.5108 0.8166 0.4211 0.047 Uiso 1 1 calc R . . . . C20 C 0.3299(3) 0.8966(6) 0.3539(2) 0.0267(8) Uani 1 1 d . . . . . H20A H 0.3505 1.0459 0.3741 0.032 Uiso 1 1 calc R . . . . H20B H 0.3260 0.8941 0.2877 0.032 Uiso 1 1 calc R . . . . 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 0.0221(12) 0.0307(13) 0.0179(12) -0.0017(11) 0.0028(9) 0.0148(11) O2 0.0185(11) 0.0270(13) 0.0173(12) 0.0083(10) -0.0008(8) 0.0020(9) O3 0.0161(11) 0.0193(11) 0.0219(12) 0.0019(10) 0.0055(9) 0.0030(9) N1 0.0114(12) 0.0143(13) 0.0191(14) -0.0010(11) -0.0010(10) 0.0010(10) N2 0.0123(12) 0.0174(14) 0.0152(13) 0.0007(11) -0.0001(10) 0.0042(11) C1 0.0194(15) 0.0164(16) 0.0160(16) 0.0022(13) 0.0005(13) 0.0020(13) C2 0.0234(17) 0.0188(16) 0.0194(17) 0.0016(15) 0.0060(13) 0.0094(15) C3 0.0166(16) 0.0260(17) 0.0171(16) 0.0010(15) 0.0016(12) 0.0054(15) C4 0.0198(16) 0.0232(16) 0.0136(16) -0.0007(14) 0.0017(13) -0.0011(14) C5 0.0209(16) 0.0196(16) 0.0126(16) -0.0004(14) -0.0010(12) 0.0045(14) C6 0.0182(15) 0.0188(16) 0.0083(14) 0.0035(13) 0.0005(11) 0.0060(13) C7 0.0178(15) 0.0174(16) 0.0166(16) 0.0016(14) 0.0000(12) 0.0010(13) C8 0.0121(14) 0.0136(14) 0.0174(16) -0.0002(13) 0.0008(11) 0.0007(13) C9 0.0167(15) 0.0224(16) 0.0198(17) 0.0008(15) 0.0014(12) 0.0035(14) C10 0.0207(16) 0.0257(18) 0.0169(16) 0.0000(15) -0.0001(12) 0.0079(14) C11 0.0142(15) 0.0138(15) 0.0190(17) 0.0012(13) 0.0001(12) 0.0022(13) C12 0.0160(15) 0.0131(15) 0.0169(16) -0.0003(13) 0.0005(12) 0.0021(13) C13 0.0126(14) 0.0113(15) 0.0139(15) 0.0005(12) -0.0008(11) 0.0016(12) C14 0.0169(15) 0.0101(14) 0.0180(15) -0.0014(13) -0.0021(12) -0.0008(12) C15 0.0144(15) 0.0165(15) 0.0168(15) -0.0032(13) -0.0024(12) 0.0020(13) C16 0.0148(15) 0.0187(17) 0.0152(16) 0.0002(13) -0.0008(12) 0.0023(13) C17 0.0148(15) 0.0120(14) 0.0196(16) 0.0023(14) 0.0014(12) -0.0004(13) C18 0.0135(14) 0.0159(15) 0.0161(16) -0.0032(13) -0.0001(12) 0.0015(13) C19 0.0268(19) 0.052(3) 0.038(2) 0.022(2) 0.0083(16) 0.0088(19) C20 0.0226(17) 0.034(2) 0.0237(18) 0.0099(17) 0.0035(13) -0.0016(16) _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 C9 1.451(3) . ? O1 C10 1.453(4) . ? O2 C16 1.436(4) . ? O2 C20 1.432(4) . ? O3 C16 1.426(3) . ? O3 C19 1.418(4) . ? N1 H1 0.90(2) . ? N1 C11 1.451(4) . ? N1 C13 1.485(3) . ? N2 C7 1.475(4) . ? N2 C8 1.459(3) . ? N2 C12 1.476(4) . ? C1 H1A 0.9500 . ? C1 C2 1.393(4) . ? C1 C6 1.392(4) . ? C2 H2 0.9500 . ? C2 C3 1.383(5) . ? C3 H3 0.9500 . ? C3 C4 1.394(4) . ? C4 H4 0.9500 . ? C4 C5 1.382(4) . ? C5 H5 0.9500 . ? C5 C6 1.391(4) . ? C6 C7 1.514(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8 1.0000 . ? C8 C9 1.510(4) . ? C8 C11 1.517(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.511(4) . ? C11 H11 1.0000 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.538(4) . ? C13 C14 1.524(4) . ? C13 C18 1.542(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.526(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C16 1.509(4) . ? C16 C17 1.525(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.531(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.515(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? 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 C9 O1 C10 109.5(2) . . ? C20 O2 C16 106.0(2) . . ? C19 O3 C16 106.6(2) . . ? C11 N1 H1 110.8(19) . . ? C11 N1 C13 110.1(2) . . ? C13 N1 H1 107.9(19) . . ? C7 N2 C12 109.7(2) . . ? C8 N2 C7 111.9(2) . . ? C8 N2 C12 106.8(2) . . ? C2 C1 H1A 119.8 . . ? C6 C1 H1A 119.8 . . ? C6 C1 C2 120.4(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 120.1 . . ? C2 C3 C4 119.8(3) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 120.1 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.1 . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.2(3) . . ? C6 C5 H5 119.4 . . ? C1 C6 C7 121.5(3) . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C7 119.7(3) . . ? N2 C7 C6 110.8(2) . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? N2 C8 H8 109.4 . . ? N2 C8 C9 118.8(2) . . ? N2 C8 C11 108.2(2) . . ? C9 C8 H8 109.4 . . ? C9 C8 C11 100.9(2) . . ? C11 C8 H8 109.4 . . ? O1 C9 C8 104.4(2) . . ? O1 C9 H9A 110.9 . . ? O1 C9 H9B 110.9 . . ? C8 C9 H9A 110.9 . . ? C8 C9 H9B 110.9 . . ? H9A C9 H9B 108.9 . . ? O1 C10 H10A 110.9 . . ? O1 C10 H10B 110.9 . . ? O1 C10 C11 104.1(2) . . ? H10A C10 H10B 108.9 . . ? C11 C10 H10A 110.9 . . ? C11 C10 H10B 110.9 . . ? N1 C11 C8 115.1(3) . . ? N1 C11 C10 117.5(2) . . ? N1 C11 H11 107.4 . . ? C8 C11 H11 107.4 . . ? C10 C11 C8 101.3(2) . . ? C10 C11 H11 107.4 . . ? N2 C12 H12A 108.7 . . ? N2 C12 H12B 108.7 . . ? N2 C12 C13 114.4(2) . . ? H12A C12 H12B 107.6 . . ? C13 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? N1 C13 C12 112.1(2) . . ? N1 C13 C14 107.8(2) . . ? N1 C13 C18 109.6(2) . . ? C12 C13 C18 110.8(2) . . ? C14 C13 C12 107.8(2) . . ? C14 C13 C18 108.6(2) . . ? C13 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C13 C14 C15 113.2(2) . . ? H14A C14 H14B 107.8 . . ? C15 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C16 C15 C14 110.5(2) . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? O2 C16 C15 109.5(2) . . ? O2 C16 C17 110.4(2) . . ? O3 C16 O2 104.3(2) . . ? O3 C16 C15 109.4(2) . . ? O3 C16 C17 111.0(2) . . ? C15 C16 C17 111.9(2) . . ? C16 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C16 C17 C18 111.6(3) . . ? H17A C17 H17B 108.0 . . ? C18 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C13 C18 H18A 109.2 . . ? C13 C18 H18B 109.2 . . ? C17 C18 C13 112.1(2) . . ? C17 C18 H18A 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? O3 C19 H19A 110.5 . . ? O3 C19 H19B 110.5 . . ? O3 C19 C20 106.3(3) . . ? H19A C19 H19B 108.7 . . ? C20 C19 H19A 110.5 . . ? C20 C19 H19B 110.5 . . ? O2 C20 C19 104.0(3) . . ? O2 C20 H20A 111.0 . . ? O2 C20 H20B 111.0 . . ? C19 C20 H20A 111.0 . . ? C19 C20 H20B 111.0 . . ? H20A C20 H20B 109.0 . . ? 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 O1 C10 C11 N1 162.0(2) . . . . ? O1 C10 C11 C8 35.7(3) . . . . ? O2 C16 C17 C18 176.3(2) . . . . ? O3 C16 C17 C18 -68.5(3) . . . . ? O3 C19 C20 O2 -4.9(4) . . . . ? N1 C13 C14 C15 62.3(3) . . . . ? N1 C13 C18 C17 -62.8(3) . . . . ? N2 C8 C9 O1 154.3(2) . . . . ? N2 C8 C11 N1 62.7(3) . . . . ? N2 C8 C11 C10 -169.4(2) . . . . ? N2 C12 C13 N1 -50.6(3) . . . . ? N2 C12 C13 C14 -169.1(2) . . . . ? N2 C12 C13 C18 72.2(3) . . . . ? C1 C2 C3 C4 -1.2(4) . . . . ? C1 C6 C7 N2 -110.9(3) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? C2 C1 C6 C7 -178.4(3) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C4 C5 C6 C7 178.1(3) . . . . ? C5 C6 C7 N2 69.7(3) . . . . ? C6 C1 C2 C3 0.3(4) . . . . ? C7 N2 C8 C9 64.4(3) . . . . ? C7 N2 C8 C11 178.5(2) . . . . ? C7 N2 C12 C13 -180.0(2) . . . . ? C8 N2 C7 C6 -172.0(2) . . . . ? C8 N2 C12 C13 58.7(3) . . . . ? C9 O1 C10 C11 -13.5(3) . . . . ? C9 C8 C11 N1 -171.8(2) . . . . ? C9 C8 C11 C10 -43.9(3) . . . . ? C10 O1 C9 C8 -14.5(3) . . . . ? C11 N1 C13 C12 44.7(3) . . . . ? C11 N1 C13 C14 163.2(2) . . . . ? C11 N1 C13 C18 -78.8(3) . . . . ? C11 C8 C9 O1 36.2(3) . . . . ? C12 N2 C7 C6 69.8(3) . . . . ? C12 N2 C8 C9 -175.6(3) . . . . ? C12 N2 C8 C11 -61.5(3) . . . . ? C12 C13 C14 C15 -176.4(2) . . . . ? C12 C13 C18 C17 173.0(2) . . . . ? C13 N1 C11 C8 -52.6(3) . . . . ? C13 N1 C11 C10 -171.9(3) . . . . ? C13 C14 C15 C16 57.0(3) . . . . ? C14 C13 C18 C17 54.7(3) . . . . ? C14 C15 C16 O2 -177.2(2) . . . . ? C14 C15 C16 O3 69.0(3) . . . . ? C14 C15 C16 C17 -54.4(3) . . . . ? C15 C16 C17 C18 54.1(3) . . . . ? C16 O2 C20 C19 25.0(3) . . . . ? C16 O3 C19 C20 -17.3(4) . . . . ? C16 C17 C18 C13 -54.6(3) . . . . ? C18 C13 C14 C15 -56.3(3) . . . . ? C19 O3 C16 O2 33.0(3) . . . . ? C19 O3 C16 C15 150.1(3) . . . . ? C19 O3 C16 C17 -86.0(3) . . . . ? C20 O2 C16 O3 -36.3(3) . . . . ? C20 O2 C16 C15 -153.3(3) . . . . ? C20 O2 C16 C17 83.0(3) . . . . ? _shelx_res_file ; TITL mo_jb141015_1_1_0m_a.res in P2(1) REM Old TITL mo_jb141015_1_1_0m in P21 #4 REM SHELXT solution in P2(1) REM R1 0.108, Rweak 0.029, Alpha 0.001, Orientation as input REM Flack x = -0.930 ( 1.222 ) from Parsons' quotients REM Formula found by SHELXT: C20 N2 O3 CELL 0.71073 9.7442 6.1717 14.9524 90 90.609 90 ZERR 2 0.0009 0.0005 0.0013 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 40 56 4 6 DFIX 0.91 N1 H1 L.S. 5 PLAN 5 SIZE 0.04 0.07 0.16 TEMP -173.17 BOND $H MORE -1 CONF fmap 2 acta 52 REM REM REM WGHT 0.040900 0.048600 FVAR 0.96230 O1 4 -0.079936 0.876421 0.885597 11.00000 0.02210 0.03073 = 0.01788 -0.00169 0.00275 0.01477 O2 4 0.203737 0.820849 0.391018 11.00000 0.01851 0.02704 = 0.01730 0.00828 -0.00078 0.00204 O3 4 0.366438 0.598713 0.448775 11.00000 0.01612 0.01933 = 0.02195 0.00188 0.00547 0.00300 N1 3 0.046887 0.676152 0.670102 11.00000 0.01140 0.01434 = 0.01910 -0.00100 -0.00102 0.00096 H1 2 -0.019899 0.575938 0.662554 11.00000 -1.20000 N2 3 0.216936 0.543747 0.824765 11.00000 0.01225 0.01745 = 0.01523 0.00066 -0.00011 0.00417 C1 1 0.460729 0.144925 0.870143 11.00000 0.01941 0.01638 = 0.01603 0.00223 0.00054 0.00202 AFIX 43 H1A 2 0.397738 0.032572 0.855522 11.00000 -1.20000 AFIX 0 C2 1 0.601248 0.104096 0.868530 11.00000 0.02336 0.01880 = 0.01944 0.00160 0.00599 0.00945 AFIX 43 H2 2 0.633719 -0.035640 0.852558 11.00000 -1.20000 AFIX 0 C3 1 0.693648 0.266482 0.890123 11.00000 0.01656 0.02597 = 0.01708 0.00103 0.00159 0.00539 AFIX 43 H3 2 0.789422 0.237697 0.890148 11.00000 -1.20000 AFIX 0 C4 1 0.645795 0.472457 0.911843 11.00000 0.01980 0.02316 = 0.01364 -0.00065 0.00166 -0.00113 AFIX 43 H4 2 0.708847 0.585148 0.925879 11.00000 -1.20000 AFIX 0 C5 1 0.506265 0.512087 0.912877 11.00000 0.02086 0.01960 = 0.01262 -0.00035 -0.00095 0.00453 AFIX 43 H5 2 0.474143 0.652970 0.927387 11.00000 -1.20000 AFIX 0 C6 1 0.412005 0.349330 0.893046 11.00000 0.01819 0.01876 = 0.00835 0.00352 0.00048 0.00601 C7 1 0.259822 0.396752 0.897606 11.00000 0.01782 0.01740 = 0.01664 0.00155 0.00002 0.00101 AFIX 23 H7A 2 0.207702 0.259451 0.892936 11.00000 -1.20000 H7B 2 0.238735 0.464010 0.955978 11.00000 -1.20000 AFIX 0 C8 1 0.075455 0.616120 0.834914 11.00000 0.01208 0.01364 = 0.01739 -0.00021 0.00081 0.00065 AFIX 13 H8 2 0.012577 0.488216 0.831872 11.00000 -1.20000 AFIX 0 C9 1 0.039454 0.753812 0.914769 11.00000 0.01673 0.02238 = 0.01980 0.00076 0.00144 0.00345 AFIX 23 H9A 2 0.017541 0.662124 0.967035 11.00000 -1.20000 H9B 2 0.116210 0.851783 0.931008 11.00000 -1.20000 AFIX 0 C10 1 -0.094241 0.861742 0.788958 11.00000 0.02067 0.02573 = 0.01695 -0.00001 -0.00009 0.00793 AFIX 23 H10A 2 -0.110907 1.006363 0.762337 11.00000 -1.20000 H10B 2 -0.170869 0.764247 0.771967 11.00000 -1.20000 AFIX 0 C11 1 0.041512 0.770393 0.758893 11.00000 0.01424 0.01385 = 0.01900 0.00122 0.00006 0.00220 AFIX 13 H11 2 0.110141 0.890781 0.761257 11.00000 -1.20000 AFIX 0 C12 1 0.223578 0.429109 0.738300 11.00000 0.01603 0.01315 = 0.01690 -0.00034 0.00054 0.00212 AFIX 23 H12A 2 0.163235 0.300253 0.740835 11.00000 -1.20000 H12B 2 0.318648 0.377253 0.729596 11.00000 -1.20000 AFIX 0 C13 1 0.181019 0.567142 0.656980 11.00000 0.01263 0.01131 = 0.01392 0.00054 -0.00084 0.00161 C14 1 0.166266 0.416326 0.576783 11.00000 0.01695 0.01006 = 0.01799 -0.00142 -0.00214 -0.00077 AFIX 23 H14A 2 0.092597 0.310086 0.588773 11.00000 -1.20000 H14B 2 0.252933 0.334870 0.569393 11.00000 -1.20000 AFIX 0 C15 1 0.132778 0.535503 0.489838 11.00000 0.01443 0.01650 = 0.01675 -0.00316 -0.00238 0.00199 AFIX 23 H15A 2 0.128080 0.430383 0.439888 11.00000 -1.20000 H15B 2 0.042055 0.606516 0.494642 11.00000 -1.20000 AFIX 0 C16 1 0.240881 0.703848 0.470666 11.00000 0.01482 0.01870 = 0.01516 0.00024 -0.00076 0.00228 C17 1 0.261150 0.859459 0.548944 11.00000 0.01482 0.01200 = 0.01964 0.00227 0.00137 -0.00038 AFIX 23 H17A 2 0.177252 0.947947 0.556162 11.00000 -1.20000 H17B 2 0.338150 0.958792 0.535874 11.00000 -1.20000 AFIX 0 C18 1 0.291690 0.737944 0.636159 11.00000 0.01347 0.01585 = 0.01615 -0.00321 -0.00012 0.00147 AFIX 23 H18A 2 0.297139 0.843212 0.686029 11.00000 -1.20000 H18B 2 0.381979 0.665430 0.631668 11.00000 -1.20000 AFIX 0 C19 1 0.436212 0.738396 0.389289 11.00000 0.02678 0.05216 = 0.03843 0.02241 0.00830 0.00878 AFIX 23 H19A 2 0.476483 0.654579 0.339586 11.00000 -1.20000 H19B 2 0.510846 0.816551 0.421076 11.00000 -1.20000 AFIX 0 C20 1 0.329879 0.896572 0.353929 11.00000 0.02257 0.03408 = 0.02365 0.00987 0.00352 -0.00157 AFIX 23 H20A 2 0.350488 1.045937 0.374135 11.00000 -1.20000 H20B 2 0.325961 0.894069 0.287749 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_jb141015_1_1_0m_a.res in P2(1) REM R1 = 0.0448 for 2412 Fo > 4sig(Fo) and 0.0662 for all 3053 data REM 229 parameters refined using 2 restraints END WGHT 0.0409 0.0486 REM Highest difference peak 0.339, deepest hole -0.256, 1-sigma level 0.049 Q1 1 0.4001 0.6158 0.3590 11.00000 0.05 0.34 Q2 1 0.3991 0.5342 0.3252 11.00000 0.05 0.22 Q3 1 0.2809 0.8131 0.9812 11.00000 0.05 0.20 Q4 1 0.4166 0.5695 0.6208 11.00000 0.05 0.19 Q5 1 0.1778 0.4975 0.6166 11.00000 0.05 0.19 ; _shelx_res_checksum 37586 _shelx_hkl_file ; -1 0 0 258.17 5.40 1 0 0 256.67 5.40 -2 0 0 570.94 11.50 2 0 0 543.15 11.50 -3 0 0 20.00 4.10 3 0 0 31.60 4.80 -4 0 0 46.50 6.10 4 0 0 49.50 6.20 -5 0 0 26.00 6.30 5 0 0 25.10 6.00 -6 0 0 137.59 10.70 6 0 0 124.59 10.20 -7 0 0 433.56 17.20 7 0 0 435.46 17.70 -8 0 0 57.79 9.90 8 0 0 50.69 9.20 -9 0 0 25.10 8.90 9 0 0 33.10 9.20 -10 0 0 1.20 7.90 10 0 0 12.20 8.20 -11 0 0 15.50 9.90 11 0 0 25.60 9.50 12 0 0 6.90 9.70 12 -1 0 19.00 10.30 -12 1 0 27.40 11.40 11 -1 0 25.00 9.70 -11 1 0 19.10 10.20 10 -1 0 21.70 9.30 -10 1 0 55.29 11.50 9 -1 0 30.50 8.70 -9 1 0 52.09 10.70 8 -1 0 77.69 10.10 -8 1 0 64.99 10.10 7 -1 0 388.56 16.20 -7 1 0 343.17 17.10 6 -1 0 618.94 19.00 -6 1 0 621.44 19.70 5 -1 0 226.68 11.30 -5 1 0 218.58 11.80 4 -1 0 545.65 14.80 -4 1 0 532.85 15.60 3 -1 0 469.65 12.10 -3 1 0 472.05 13.00 2 -1 0 2042.20 29.10 -2 1 0 2014.90 29.70 1 -1 0 5629.54 68.39 -1 1 0 5637.14 69.09 -1 1 0 5594.94 69.09 -2 -1 0 2036.00 27.40 2 1 0 2059.09 31.20 2 1 0 2003.70 28.30 -3 -1 0 471.65 11.00 3 1 0 465.75 11.80 -4 -1 0 557.14 13.90 4 1 0 557.74 15.10 -5 -1 0 240.38 10.50 5 1 0 240.88 11.80 -6 -1 0 580.84 17.10 6 1 0 589.54 18.40 -7 -1 0 359.16 14.80 7 1 0 353.86 16.40 -8 -1 0 103.69 10.60 8 1 0 49.70 9.40 -9 -1 0 27.20 8.30 9 1 0 41.10 9.60 10 1 0 36.80 10.40 11 1 0 23.00 9.90 12 1 0 19.10 10.10 -12 2 0 160.48 18.90 11 -2 0 11.10 8.40 -11 2 0 0.60 9.40 10 -2 0 9.40 8.10 -10 2 0 13.10 9.60 9 -2 0 20.80 8.30 -9 2 0 35.10 9.90 8 -2 0 189.28 14.30 -8 2 0 211.38 16.10 7 -2 0 100.19 10.10 -7 2 0 121.99 12.60 6 -2 0 197.88 11.60 -6 2 0 206.08 13.30 5 -2 0 178.88 9.70 -5 2 0 154.28 10.80 4 -2 0 400.46 12.50 -4 2 0 428.96 14.30 3 -2 0 356.46 10.30 -3 2 0 359.56 11.70 2 -2 0 1152.78 19.20 -2 2 0 1176.08 19.90 -1 2 0 458.75 8.50 -1 2 0 471.25 8.40 2 2 0 1210.58 17.30 2 2 0 1215.38 17.40 3 2 0 380.26 9.90 3 2 0 372.56 10.10 4 2 0 401.06 12.50 -5 -2 0 158.58 7.50 5 2 0 170.48 9.90 -6 -2 0 233.18 9.90 6 2 0 229.38 12.40 -7 -2 0 130.89 9.60 7 2 0 112.79 10.90 8 2 0 197.78 14.90 9 2 0 26.80 8.80 10 2 0 7.50 8.70 11 2 0 8.80 9.70 12 2 0 169.08 19.10 -11 3 0 25.00 11.00 -10 3 0 40.70 11.90 -9 3 0 6.90 8.90 8 -3 0 48.80 9.30 -8 3 0 42.10 10.20 7 -3 0 133.59 11.10 -7 3 0 136.89 13.40 6 -3 0 95.19 8.80 -6 3 0 96.59 10.80 5 -3 0 791.02 18.30 -5 3 0 780.02 22.10 4 -3 0 411.36 11.20 -4 3 0 414.06 14.70 -3 3 0 783.12 18.00 -2 3 0 211.08 8.40 -2 3 0 215.88 8.20 -1 3 0 52.09 4.00 3 3 0 837.92 15.30 3 3 0 828.12 15.10 4 3 0 404.66 11.80 4 3 0 399.76 11.90 5 3 0 783.52 19.50 6 3 0 92.39 9.10 7 3 0 130.99 11.80 8 3 0 55.79 9.70 9 3 0 -1.40 7.20 10 3 0 26.60 9.50 11 3 0 26.00 10.60 -10 4 0 111.39 16.10 -9 4 0 12.00 9.00 -8 4 0 -4.00 7.30 -7 4 0 15.10 8.30 -6 4 0 249.78 15.70 -5 4 0 37.70 7.90 -4 4 0 224.88 12.40 -3 4 0 56.89 6.70 -2 4 0 8.70 3.60 -2 4 0 6.40 3.40 -1 4 0 6.60 2.60 3 4 0 56.99 4.50 3 4 0 57.29 4.40 4 4 0 213.88 9.40 4 4 0 210.08 8.70 5 4 0 32.30 6.20 6 4 0 232.48 12.50 7 4 0 49.80 8.70 8 4 0 2.10 6.60 9 4 0 2.70 7.60 10 4 0 128.59 14.80 -9 5 0 18.50 10.50 -8 5 0 18.30 9.50 -7 5 0 25.90 9.10 -6 5 0 107.99 12.30 -5 5 0 9.60 6.90 -4 5 0 3.30 5.60 -3 5 0 175.68 10.90 -2 5 0 9.60 4.40 -1 5 0 248.98 8.30 -1 5 0 234.38 8.50 0 5 0 -1.90 2.10 0 5 0 -1.00 2.20 2 5 0 -0.10 1.90 2 5 0 1.70 2.00 3 5 0 176.78 7.70 3 5 0 173.78 7.00 4 5 0 7.40 4.20 5 5 0 3.00 4.80 6 5 0 102.29 9.80 7 5 0 19.80 7.50 8 5 0 6.60 7.10 9 5 0 26.30 9.10 -8 6 0 57.29 12.40 -7 6 0 38.70 10.40 -6 6 0 34.20 9.40 -5 6 0 40.00 8.60 -4 6 0 22.10 7.20 -3 6 0 75.69 8.70 -2 6 0 120.69 9.10 -1 6 0 34.40 5.20 0 6 0 141.89 7.00 1 6 0 34.30 3.90 2 6 0 133.59 6.20 3 6 0 79.59 6.00 4 6 0 25.80 5.30 5 6 0 34.00 6.50 6 6 0 36.50 7.50 7 6 0 31.50 7.80 8 6 0 39.40 9.90 -6 7 0 2.90 7.70 -5 7 0 -2.80 6.70 -4 7 0 147.89 12.90 -3 7 0 181.38 12.60 -2 7 0 134.29 10.50 -1 7 0 98.29 8.50 0 7 0 3.30 4.00 1 7 0 94.49 7.00 2 7 0 123.09 7.20 3 7 0 174.98 8.80 4 7 0 148.09 9.60 5 7 0 3.40 5.10 6 7 0 4.80 6.30 0 8 0 46.80 6.50 0 8 -1 93.19 7.50 6 7 -1 6.30 5.90 5 7 -1 5.40 5.10 4 7 -1 8.20 4.40 3 7 -1 37.30 4.70 2 7 -1 202.88 7.10 1 7 -1 83.99 5.80 0 7 -1 40.20 5.00 -1 7 -1 129.49 8.70 -2 7 -1 47.90 7.20 -3 7 -1 54.69 8.30 -4 7 -1 4.50 6.50 -5 7 -1 14.20 7.80 -6 7 -1 13.40 8.30 8 6 -1 27.30 8.60 7 6 -1 17.70 7.20 6 6 -1 113.09 10.10 5 6 -1 49.90 6.90 4 6 -1 104.89 7.50 3 6 -1 145.49 6.30 0 6 -1 51.49 4.00 -1 6 -1 232.48 9.20 -2 6 -1 54.49 6.80 -3 6 -1 110.39 9.70 -4 6 -1 72.79 9.40 -5 6 -1 7.70 7.00 -6 6 -1 30.40 8.70 -7 6 -1 26.60 9.80 -8 6 -1 16.70 9.40 9 5 -1 23.20 8.90 8 5 -1 11.30 7.40 7 5 -1 17.90 7.00 6 5 -1 165.68 11.50 5 5 -1 263.37 11.90 4 5 -1 215.18 9.10 3 5 -1 1.50 2.40 3 5 -1 3.20 2.40 -1 5 -1 138.79 6.20 -1 5 -1 151.68 6.40 -2 5 -1 20.90 4.70 -3 5 -1 24.50 5.70 -4 5 -1 77.69 9.10 -5 5 -1 132.49 12.10 -6 5 -1 17.50 8.10 -7 5 -1 54.99 10.80 -8 5 -1 10.00 9.00 -9 5 -1 12.60 10.10 10 4 -1 23.40 9.40 9 4 -1 -4.40 7.10 8 4 -1 13.90 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8.40 4 2 -16 15.10 9.60 3 2 -16 2.90 8.70 2 2 -16 0.40 8.50 1 2 -16 40.40 11.20 0 2 -16 12.90 9.30 -1 2 -16 76.79 13.00 -2 2 -16 37.10 11.00 -3 2 -16 33.00 11.60 -4 2 -16 92.09 14.30 -5 2 -16 -10.40 8.80 -6 2 -16 60.89 12.80 7 1 -16 9.30 9.90 5 1 -16 53.09 12.20 4 1 -16 6.40 9.20 3 1 -16 6.20 9.10 2 1 -16 -2.40 8.00 1 1 -16 27.20 10.50 0 1 -16 25.10 10.10 -1 1 -16 5.10 8.90 -2 1 -16 70.79 12.40 -3 1 -16 28.20 10.80 -4 1 -16 -4.10 8.90 -5 1 -16 2.80 9.80 -6 1 -16 -3.70 9.40 6 0 -16 4.70 10.00 5 0 -16 -0.30 9.00 4 0 -16 126.79 15.80 3 0 -16 -4.90 8.50 2 0 -16 -2.90 8.10 1 0 -16 0.60 8.90 -1 0 16 29.80 9.40 0 0 -16 15.60 10.10 0 0 16 14.50 8.70 -1 0 -16 38.90 11.00 1 0 16 31.30 10.00 -2 0 -16 37.20 11.50 2 0 16 52.59 10.50 -3 0 -16 -6.80 8.30 3 0 16 -0.40 7.90 -4 0 -16 45.90 12.30 4 0 16 60.69 11.70 -5 0 -16 4.40 9.90 5 0 16 16.50 11.60 -6 0 -16 59.59 13.40 -7 0 -16 40.60 13.30 7 -1 -16 13.20 10.60 6 -1 -16 35.80 12.20 5 -1 -16 67.09 13.30 -5 1 16 96.09 15.00 4 -1 -16 11.80 10.10 -4 1 16 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11.60 1 3 16 151.78 17.40 2 3 16 12.20 10.10 3 3 16 19.90 10.80 4 3 16 2.90 9.70 5 3 16 98.89 15.70 -3 4 16 28.30 12.00 -2 4 16 18.40 11.00 -1 4 16 41.40 12.70 0 4 16 -5.50 9.30 1 4 16 50.79 13.10 2 4 16 3.60 10.40 3 4 16 35.00 11.60 3 3 -17 16.90 9.80 2 3 -17 23.60 10.40 1 3 -17 28.80 11.00 0 3 -17 182.78 18.10 -1 3 -17 21.20 10.70 -2 3 -17 22.90 11.00 -3 3 -17 30.20 11.50 5 2 -17 40.60 12.00 4 2 -17 47.70 12.30 3 2 -17 -5.30 8.20 2 2 -17 15.40 10.10 1 2 -17 151.18 16.90 0 2 -17 4.60 9.30 -1 2 -17 -8.40 8.50 -2 2 -17 309.37 21.70 -3 2 -17 75.69 13.80 -4 2 -17 17.20 11.10 -5 2 -17 38.90 12.60 6 1 -17 32.70 11.80 5 1 -17 -1.50 9.10 4 1 -17 31.30 11.50 3 1 -17 -17.80 7.80 2 1 -17 28.30 11.30 1 1 -17 -2.40 9.20 0 1 -17 35.80 11.70 -1 1 -17 63.49 13.10 -2 1 -17 7.70 10.00 -3 1 -17 143.79 17.50 -4 1 -17 -7.80 8.90 -5 1 -17 9.50 10.70 6 0 -17 -11.00 9.30 5 0 -17 -6.80 8.90 4 0 -17 3.90 9.80 3 0 -17 13.30 10.30 2 0 -17 12.90 10.10 1 0 -17 12.20 9.70 0 0 -17 -6.30 8.70 -1 0 -17 -5.80 8.60 -2 0 -17 34.60 11.90 -3 0 -17 -5.70 9.00 -4 0 -17 3.10 9.60 -5 0 -17 -3.80 10.20 -6 0 -17 2.50 10.50 6 -1 -17 12.70 11.40 5 -1 -17 10.30 10.40 4 -1 -17 43.10 12.40 3 -1 -17 -0.10 9.90 -3 1 17 12.20 9.60 2 -1 -17 27.80 11.40 -2 1 17 28.50 10.80 1 -1 -17 0.80 9.60 -1 1 17 22.20 10.10 0 -1 -17 32.80 11.40 0 1 17 41.20 11.50 -1 -1 -17 43.10 12.00 1 1 17 49.00 12.30 -2 -1 -17 9.70 10.30 2 1 17 14.90 9.90 -3 -1 -17 163.28 17.90 3 1 17 149.59 16.70 -4 -1 -17 11.70 10.60 4 1 17 9.00 9.60 -5 -1 -17 3.80 10.10 5 1 17 20.50 11.10 5 -2 -17 62.79 14.10 -5 2 17 36.60 12.10 4 -2 -17 24.20 11.50 -4 2 17 23.80 10.80 3 -2 -17 14.30 10.40 -3 2 17 9.00 10.20 2 -2 -17 29.40 11.30 -2 2 17 30.10 11.40 1 -2 -17 157.38 17.70 -1 2 17 144.69 16.60 0 -2 -17 -4.90 9.20 0 2 17 18.10 10.30 -1 -2 -17 -0.90 9.40 1 2 17 5.60 9.80 -2 -2 -17 327.57 22.20 2 2 17 371.76 24.50 -3 -2 -17 77.29 13.50 3 2 17 100.79 15.40 4 2 17 19.80 11.00 5 2 17 53.79 13.20 -3 3 17 16.70 10.40 -2 3 17 24.60 11.40 -1 3 17 13.00 10.80 0 3 17 181.58 19.20 1 3 17 18.40 11.10 2 3 17 28.20 12.20 3 3 17 39.60 12.80 0 3 -18 58.09 13.50 3 2 -18 26.50 11.90 2 2 -18 -6.00 9.80 1 2 -18 8.80 10.50 0 2 -18 -24.70 7.60 -1 2 -18 136.89 17.00 -2 2 -18 19.50 11.30 -3 2 -18 8.10 11.00 4 1 -18 3.60 9.60 3 1 -18 30.00 11.20 2 1 -18 23.80 11.40 1 1 -18 94.09 15.40 0 1 -18 16.90 11.00 -1 1 -18 -9.50 8.70 -2 1 -18 43.40 12.30 -3 1 -18 71.79 14.70 -4 1 -18 97.69 15.90 4 0 -18 10.20 10.70 3 0 -18 9.10 10.20 2 0 -18 38.60 12.70 1 0 -18 21.90 11.00 0 0 -18 11.80 10.40 -1 0 -18 23.60 11.20 -2 0 -18 44.30 12.90 -3 0 -18 10.40 10.40 -4 0 -18 32.60 12.80 4 -1 -18 10.70 11.00 3 -1 -18 20.00 11.20 2 -1 -18 -0.20 9.40 1 -1 -18 110.09 16.20 -1 1 18 110.49 15.30 0 -1 -18 23.40 11.00 0 1 18 20.40 10.40 -1 -1 -18 9.10 10.50 1 1 18 7.60 9.50 -2 -1 -18 18.40 11.20 2 1 18 42.00 11.30 -3 -1 -18 90.69 15.10 3 1 18 91.29 14.20 -4 -1 -18 81.49 15.40 4 1 18 103.89 15.90 3 -2 -18 49.99 13.40 -3 2 18 67.09 14.20 2 -2 -18 1.90 9.90 -2 2 18 4.90 9.60 1 -2 -18 10.80 10.00 -1 2 18 24.60 11.10 0 -2 -18 10.90 10.30 0 2 18 9.40 10.50 -1 -2 -18 157.98 18.30 1 2 18 143.59 17.70 -2 -2 -18 9.20 10.40 2 2 18 0.20 9.60 3 2 18 -4.70 9.30 0 3 18 83.89 15.00 2 1 -19 8.00 11.10 1 1 -19 54.59 14.00 0 1 -19 14.40 11.50 -1 1 -19 46.40 13.70 2 0 -19 0.10 10.50 1 0 -19 17.70 11.20 0 0 -19 -9.60 8.90 -1 0 -19 10.00 11.40 -2 0 -19 62.29 14.50 2 -1 -19 10.50 10.60 1 -1 -19 91.99 16.10 0 -1 -19 -3.70 10.20 -1 -1 -19 69.99 15.00 _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 4412 _olex2_date_sample_data_collection 2015-10-14 _olex2_date_sample_submission 2015-10-14 _olex2_submission_original_sample_id jb141015_1_1 _olex2_submission_special_instructions 'No special instructions were received'