data_S:cmpd_(R)-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-N-(4-Methylbenzoyl)-a-methylbenzylamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O' _chemical_formula_weight 239.31 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2681(8) _cell_length_b 5.2570(3) _cell_length_c 15.7174(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.097(8) _cell_angle_gamma 90.00 _cell_volume 674.57(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'transparent block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3038 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2564 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0450P)^2^+0.0578P] 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(2) _refine_ls_number_reflns 2564 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 N N 0.4860(3) 0.3384(4) 0.27383(13) 0.0545(5) Uani 1 1 d . . . O O 0.4775(2) -0.0749(3) 0.23876(11) 0.0708(5) Uani 1 1 d . . . C1 C 0.2047(3) 0.3341(6) -0.03628(14) 0.0603(7) Uani 1 1 d . . . C2 C 0.1857(3) 0.4867(5) 0.03236(14) 0.0612(7) Uani 1 1 d . . . H2 H 0.1182 0.6334 0.0229 0.073 Uiso 1 1 calc R . . C3 C 0.2627(3) 0.4316(5) 0.11495(14) 0.0563(6) Uani 1 1 d . . . H3 H 0.2489 0.5419 0.1611 0.068 Uiso 1 1 calc R . . C4 C 0.3599(2) 0.2166(5) 0.13083(14) 0.0475(5) Uani 1 1 d . . . C5 C 0.3774(3) 0.0603(5) 0.06216(15) 0.0588(6) Uani 1 1 d . . . H5 H 0.4420 -0.0895 0.0717 0.071 Uiso 1 1 calc R . . C6 C 0.3015(3) 0.1202(6) -0.02041(15) 0.0661(7) Uani 1 1 d . . . H6 H 0.3164 0.0120 -0.0670 0.079 Uiso 1 1 calc R . . C7 C 0.4453(3) 0.1453(5) 0.21836(15) 0.0515(6) Uani 1 1 d . . . C8 C 0.5764(3) 0.2965(5) 0.36000(13) 0.0542(6) Uani 1 1 d . . . H8 H 0.5347 0.1357 0.3828 0.065 Uiso 1 1 calc R . . C9 C 0.5393(3) 0.5135(6) 0.41801(15) 0.0682(7) Uani 1 1 d . . . H9A H 0.5745 0.6748 0.3955 0.102 Uiso 1 1 calc R . . H9B H 0.5983 0.4860 0.4764 0.102 Uiso 1 1 calc R . . H9C H 0.4213 0.5196 0.4194 0.102 Uiso 1 1 calc R . . C10 C 0.7581(3) 0.2646(5) 0.35985(13) 0.0552(6) Uani 1 1 d . . . C11 C 0.8420(3) 0.4220(9) 0.31413(17) 0.0932(11) Uani 1 1 d . . . H11 H 0.7860 0.5561 0.2813 0.112 Uiso 1 1 calc R . . C12 C 1.0097(4) 0.3892(11) 0.3148(2) 0.1167(16) Uani 1 1 d . . . H12 H 1.0667 0.5004 0.2822 0.140 Uiso 1 1 calc R . . C13 C 1.0913(4) 0.2011(9) 0.3614(2) 0.1013(13) Uani 1 1 d . . . H13 H 1.2048 0.1765 0.3605 0.122 Uiso 1 1 calc R . . C14 C 1.0111(4) 0.0491(9) 0.4090(3) 0.1255(16) Uani 1 1 d . . . H14 H 1.0690 -0.0807 0.4432 0.151 Uiso 1 1 calc R . . C15 C 0.8438(3) 0.0795(7) 0.4086(2) 0.0934(11) Uani 1 1 d . . . H15 H 0.7886 -0.0298 0.4427 0.112 Uiso 1 1 calc R . . C16 C 0.1248(5) 0.4015(9) -0.12664(17) 0.0917(11) Uani 1 1 d . . . H16A H 0.0182 0.3167 -0.1395 0.110 Uiso 0.50 1 calc PR A 1 H16C H 0.1949 0.3454 -0.1678 0.110 Uiso 0.50 1 calc PR A 1 H16B H 0.1094 0.5861 -0.1312 0.110 Uiso 0.50 1 calc PR A 1 H16E H 0.016(8) 0.513(15) -0.124(4) 0.110 Uiso 0.50 1 d P B 2 H16D H 0.088(8) 0.210(16) -0.164(4) 0.110 Uiso 0.50 1 d P C 2 H16F H 0.198(8) 0.505(15) -0.161(4) 0.110 Uiso 0.50 1 d P D 2 HN H 0.479(3) 0.483(6) 0.2586(15) 0.057(8) Uiso 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 N 0.0637(12) 0.0376(11) 0.0576(11) 0.0003(11) -0.0042(8) -0.0035(10) O 0.0932(13) 0.0384(10) 0.0746(11) -0.0004(9) -0.0052(9) 0.0013(10) C1 0.0535(12) 0.0687(18) 0.0576(13) -0.0042(14) 0.0053(10) -0.0143(14) C2 0.0513(12) 0.0624(18) 0.0663(14) 0.0007(14) -0.0017(10) 0.0027(12) C3 0.0535(12) 0.0553(14) 0.0582(12) -0.0109(13) 0.0034(10) 0.0043(13) C4 0.0426(11) 0.0419(12) 0.0580(12) -0.0055(11) 0.0078(9) -0.0047(10) C5 0.0599(13) 0.0466(15) 0.0705(15) -0.0106(13) 0.0122(11) 0.0021(12) C6 0.0761(16) 0.0656(17) 0.0586(14) -0.0179(14) 0.0170(12) -0.0084(16) C7 0.0502(12) 0.0414(13) 0.0618(13) -0.0021(12) 0.0055(10) -0.0038(12) C8 0.0641(13) 0.0440(13) 0.0522(11) 0.0029(11) 0.0019(9) -0.0064(12) C9 0.0814(17) 0.0599(16) 0.0628(14) -0.0079(14) 0.0101(12) -0.0046(15) C10 0.0620(13) 0.0527(15) 0.0470(11) -0.0031(11) -0.0034(10) -0.0070(13) C11 0.0744(17) 0.127(3) 0.0812(16) 0.039(2) 0.0209(13) 0.011(2) C12 0.079(2) 0.183(5) 0.092(2) 0.034(3) 0.0271(16) 0.001(3) C13 0.0625(17) 0.120(4) 0.116(3) -0.016(3) -0.0026(17) 0.008(2) C14 0.074(2) 0.098(3) 0.185(4) 0.030(3) -0.040(2) -0.002(2) C15 0.0672(17) 0.076(2) 0.126(2) 0.034(2) -0.0178(16) -0.0125(16) C16 0.100(2) 0.112(3) 0.0600(15) 0.0056(19) 0.0004(14) -0.010(2) _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 N C7 1.346(3) . ? N C8 1.457(3) . ? O C7 1.219(3) . ? C1 C2 1.373(3) . ? C1 C6 1.379(4) . ? C1 C16 1.511(4) . ? C2 C3 1.383(3) . ? C3 C4 1.386(3) . ? C4 C5 1.382(3) . ? C4 C7 1.492(3) . ? C5 C6 1.386(3) . ? C8 C10 1.512(3) . ? C8 C9 1.522(4) . ? C10 C11 1.357(4) . ? C10 C15 1.365(4) . ? C11 C12 1.395(4) . ? C12 C13 1.346(6) . ? C13 C14 1.339(5) . ? C14 C15 1.392(5) . ? 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 C7 N C8 121.8(2) . . ? C2 C1 C6 118.0(2) . . ? C2 C1 C16 120.9(3) . . ? C6 C1 C16 121.1(3) . . ? C1 C2 C3 121.5(2) . . ? C2 C3 C4 120.5(2) . . ? C5 C4 C3 118.3(2) . . ? C5 C4 C7 118.5(2) . . ? C3 C4 C7 123.2(2) . . ? C4 C5 C6 120.6(2) . . ? C1 C6 C5 121.2(2) . . ? O C7 N 121.6(2) . . ? O C7 C4 122.2(2) . . ? N C7 C4 116.2(2) . . ? N C8 C10 112.29(18) . . ? N C8 C9 108.7(2) . . ? C10 C8 C9 112.23(19) . . ? C11 C10 C15 117.9(3) . . ? C11 C10 C8 121.6(2) . . ? C15 C10 C8 120.4(2) . . ? C10 C11 C12 120.7(4) . . ? C13 C12 C11 120.4(4) . . ? C14 C13 C12 119.5(3) . . ? C13 C14 C15 120.6(4) . . ? C10 C15 C14 120.8(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.116 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.027 #==END data_S:cmpd_rac-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (rac)-N-(4-Methylbenzoyl)-a-methylbenzylamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O' _chemical_formula_weight 239.31 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 12.3320(10) _cell_length_b 9.7310(10) _cell_length_c 22.9260(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2751.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1350 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.71 _reflns_number_total 1350 _reflns_number_gt 1115 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0346P)^2^+0.8495P] 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 1(3) _refine_ls_number_reflns 1350 _refine_ls_number_parameters 337 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 O1A O 0.5042(3) 0.7083(5) 0.2893(2) 0.0878(16) Uani 1 1 d . . . N1A N 0.5763(4) 0.5041(8) 0.3161(2) 0.0574(15) Uani 1 1 d . . . C1A C 0.3390(6) 0.3885(7) 0.1431(3) 0.0687(19) Uani 1 1 d . . . C2A C 0.4331(5) 0.3324(6) 0.1634(3) 0.0689(17) Uani 1 1 d . . . H2A H 0.4592 0.2499 0.1463 0.083 Uiso 1 1 calc R . . C3A C 0.4911(5) 0.3918(7) 0.2078(3) 0.0587(17) Uani 1 1 d . . . H3A H 0.5557 0.3493 0.2212 0.070 Uiso 1 1 calc R . . C4A C 0.4564(5) 0.5131(7) 0.2331(3) 0.0540(16) Uani 1 1 d . . . C5A C 0.3634(6) 0.5731(7) 0.2110(3) 0.078(2) Uani 1 1 d . . . H5A H 0.3390 0.6582 0.2264 0.093 Uiso 1 1 calc R . . C6A C 0.3053(6) 0.5105(8) 0.1665(3) 0.080(2) Uani 1 1 d . . . H6A H 0.2413 0.5530 0.1522 0.095 Uiso 1 1 calc R . . C7A C 0.5144(5) 0.5849(8) 0.2817(3) 0.0604(19) Uani 1 1 d . . . C8A C 0.6444(5) 0.5584(6) 0.3629(3) 0.0638(17) Uani 1 1 d . . . H8A H 0.6443 0.6609 0.3594 0.077 Uiso 1 1 calc R . . C9A C 0.7601(5) 0.5099(7) 0.3539(3) 0.092(2) Uani 1 1 d . . . H9A1 H 0.7631 0.4097 0.3579 0.138 Uiso 1 1 calc R . . H9A2 H 0.8072 0.5524 0.3832 0.138 Uiso 1 1 calc R . . H9A3 H 0.7846 0.5362 0.3148 0.138 Uiso 1 1 calc R . . C10A C 0.5972(6) 0.5223(7) 0.4221(3) 0.0663(19) Uani 1 1 d . . . C11A C 0.6376(7) 0.4213(9) 0.4567(4) 0.102(3) Uani 1 1 d . . . H11A H 0.6982 0.3705 0.4430 0.122 Uiso 1 1 calc R . . C12A C 0.5955(11) 0.3881(12) 0.5108(5) 0.142(4) Uani 1 1 d . . . H12A H 0.6277 0.3184 0.5341 0.171 Uiso 1 1 calc R . . C13A C 0.5075(11) 0.4573(18) 0.5294(5) 0.144(5) Uani 1 1 d . . . H13A H 0.4760 0.4341 0.5659 0.173 Uiso 1 1 calc R . . C14A C 0.4632(9) 0.5587(15) 0.4973(6) 0.146(4) Uani 1 1 d . . . H14A H 0.4012 0.6064 0.5113 0.176 Uiso 1 1 calc R . . C15A C 0.5095(6) 0.5946(9) 0.4422(4) 0.105(3) Uani 1 1 d . . . H15A H 0.4799 0.6677 0.4199 0.126 Uiso 1 1 calc R . . C16A C 0.2737(6) 0.3201(7) 0.0946(3) 0.108(3) Uani 1 1 d . . . H16A H 0.1999 0.3018 0.1084 0.162 Uiso 1 1 calc R . . H16B H 0.3085 0.2335 0.0835 0.162 Uiso 1 1 calc R . . H16C H 0.2707 0.3813 0.0607 0.162 Uiso 1 1 calc R . . O1B O 0.5949(3) 0.2073(5) 0.3170(2) 0.0691(14) Uani 1 1 d . . . N1B N 0.5884(5) -0.0168(7) 0.2928(2) 0.0623(16) Uani 1 1 d . . . C1B C 0.2745(6) 0.0505(8) 0.4346(3) 0.0670(18) Uani 1 1 d . . . C2B C 0.3046(6) -0.0546(7) 0.3988(3) 0.0738(19) Uani 1 1 d . . . H2B H 0.2626 -0.1364 0.3983 0.089 Uiso 1 1 calc R . . C3B C 0.3946(6) -0.0455(6) 0.3631(3) 0.0668(18) Uani 1 1 d . . . H3B H 0.4139 -0.1210 0.3390 0.080 Uiso 1 1 calc R . . C4B C 0.4569(5) 0.0727(7) 0.3623(3) 0.0567(15) Uani 1 1 d . . . C5B C 0.4278(6) 0.1782(6) 0.3990(3) 0.0711(18) Uani 1 1 d . . . H5B H 0.4703 0.2596 0.4003 0.085 Uiso 1 1 calc R . . C6B C 0.3372(6) 0.1667(7) 0.4342(3) 0.078(2) Uani 1 1 d . . . H6B H 0.3179 0.2414 0.4587 0.093 Uiso 1 1 calc R . . C7B C 0.5531(5) 0.0934(9) 0.3223(3) 0.0534(18) Uani 1 1 d . . . C8B C 0.6774(5) -0.0079(7) 0.2510(3) 0.0724(19) Uani 1 1 d . . . H8B H 0.7239 0.0724 0.2616 0.087 Uiso 1 1 calc R . . C9B C 0.7464(5) -0.1397(6) 0.2551(4) 0.088(2) Uani 1 1 d . . . H9B1 H 0.7707 -0.1526 0.2954 0.132 Uiso 1 1 calc R . . H9B2 H 0.8097 -0.1312 0.2294 0.132 Uiso 1 1 calc R . . H9B3 H 0.7028 -0.2189 0.2430 0.132 Uiso 1 1 calc R . . C10B C 0.6365(6) 0.0122(7) 0.1892(3) 0.0644(18) Uani 1 1 d . . . C11B C 0.5483(6) -0.0587(7) 0.1681(3) 0.083(2) Uani 1 1 d . . . H11B H 0.5083 -0.1175 0.1933 0.100 Uiso 1 1 calc R . . C12B C 0.5174(7) -0.0447(9) 0.1101(4) 0.099(3) Uani 1 1 d . . . H12B H 0.4564 -0.0933 0.0954 0.118 Uiso 1 1 calc R . . C13B C 0.5760(8) 0.0400(10) 0.0744(4) 0.102(3) Uani 1 1 d . . . H13B H 0.5557 0.0489 0.0346 0.123 Uiso 1 1 calc R . . C14B C 0.6627(7) 0.1116(9) 0.0947(4) 0.103(3) Uani 1 1 d . . . H14B H 0.7027 0.1701 0.0695 0.124 Uiso 1 1 calc R . . C15B C 0.6916(6) 0.0983(7) 0.1521(4) 0.084(2) Uani 1 1 d . . . H15B H 0.7512 0.1498 0.1666 0.101 Uiso 1 1 calc R . . C16B C 0.1731(5) 0.0420(7) 0.4720(3) 0.094(2) Uani 1 1 d . . . H16D H 0.1902 0.0717 0.5118 0.142 Uiso 1 1 calc R . . H16E H 0.1468 -0.0530 0.4727 0.142 Uiso 1 1 calc R . . H16F H 0.1170 0.1019 0.4556 0.142 Uiso 1 1 calc R . . HN1A H 0.567(4) 0.408(6) 0.314(2) 0.05(2) Uiso 1 1 d . . . HN2A H 0.556(5) -0.094(7) 0.295(3) 0.09(3) Uiso 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 O1A 0.122(3) 0.023(4) 0.119(4) -0.019(3) -0.016(3) 0.008(3) N1A 0.085(4) 0.023(5) 0.065(4) -0.008(3) -0.003(3) -0.004(3) C1A 0.079(5) 0.065(6) 0.062(4) -0.002(4) -0.009(4) -0.009(4) C2A 0.073(5) 0.064(5) 0.070(4) -0.015(4) 0.000(4) 0.002(4) C3A 0.070(4) 0.048(6) 0.058(4) -0.005(3) -0.001(3) 0.003(3) C4A 0.064(5) 0.032(5) 0.066(4) -0.002(3) 0.001(3) -0.002(3) C5A 0.096(6) 0.061(5) 0.076(5) -0.009(4) -0.010(4) 0.016(4) C6A 0.088(5) 0.081(6) 0.070(5) 0.002(5) -0.018(4) 0.017(4) C7A 0.077(5) 0.039(6) 0.066(5) 0.002(4) 0.006(4) -0.004(4) C8A 0.065(5) 0.055(5) 0.072(4) -0.013(4) 0.003(4) -0.010(3) C9A 0.082(6) 0.106(6) 0.088(5) -0.020(5) 0.009(4) -0.003(4) C10A 0.064(5) 0.063(6) 0.072(5) -0.028(4) -0.004(4) -0.012(4) C11A 0.131(7) 0.093(7) 0.082(7) 0.001(5) -0.017(6) 0.007(5) C12A 0.171(11) 0.165(12) 0.092(8) 0.035(7) -0.023(8) -0.042(9) C13A 0.109(10) 0.231(17) 0.093(8) -0.018(10) -0.001(8) -0.069(9) C14A 0.084(7) 0.234(13) 0.121(10) -0.043(10) 0.004(8) -0.004(8) C15A 0.077(6) 0.139(8) 0.099(7) -0.025(6) 0.004(5) 0.014(5) C16A 0.119(6) 0.112(6) 0.093(6) -0.012(5) -0.038(5) -0.012(5) O1B 0.093(3) 0.018(4) 0.096(3) -0.009(3) -0.006(3) -0.002(2) N1B 0.076(4) 0.032(5) 0.079(4) -0.015(4) -0.003(3) -0.001(4) C1B 0.078(5) 0.057(6) 0.066(5) -0.004(4) -0.012(4) -0.004(4) C2B 0.090(5) 0.043(5) 0.089(5) 0.000(4) -0.012(5) -0.007(4) C3B 0.082(5) 0.044(6) 0.074(5) -0.004(4) -0.001(5) 0.002(4) C4B 0.068(4) 0.045(5) 0.057(4) 0.003(4) -0.011(4) 0.001(4) C5B 0.092(5) 0.049(5) 0.072(5) -0.021(4) -0.001(4) -0.001(4) C6B 0.100(6) 0.061(6) 0.073(5) -0.025(4) 0.002(4) 0.009(4) C7B 0.079(5) 0.022(8) 0.059(4) -0.007(4) -0.027(4) 0.012(4) C8B 0.070(5) 0.051(5) 0.096(6) -0.017(4) -0.007(5) -0.002(3) C9B 0.083(4) 0.067(5) 0.115(6) -0.023(4) -0.022(4) 0.026(4) C10B 0.071(5) 0.050(5) 0.072(5) -0.012(4) 0.001(4) 0.006(4) C11B 0.101(6) 0.075(6) 0.074(5) -0.006(4) -0.016(5) -0.007(4) C12B 0.095(6) 0.107(8) 0.094(7) -0.028(6) -0.012(6) 0.000(5) C13B 0.107(8) 0.125(9) 0.075(6) -0.009(6) -0.007(6) 0.031(6) C14B 0.090(7) 0.125(8) 0.095(7) 0.019(5) 0.014(5) 0.004(5) C15B 0.075(5) 0.091(7) 0.085(6) -0.003(5) -0.002(4) 0.001(4) C16B 0.086(6) 0.107(6) 0.090(5) -0.002(4) 0.008(5) -0.011(4) _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 O1A C7A 1.220(7) . ? N1A C7A 1.351(7) . ? N1A C8A 1.461(7) . ? C1A C2A 1.364(8) . ? C1A C6A 1.368(8) . ? C1A C16A 1.527(9) . ? C2A C3A 1.370(8) . ? C3A C4A 1.383(7) . ? C4A C5A 1.384(8) . ? C4A C7A 1.497(8) . ? C5A C6A 1.386(9) . ? C8A C9A 1.516(8) . ? C8A C10A 1.517(9) . ? C10A C11A 1.359(9) . ? C10A C15A 1.370(9) . ? C11A C12A 1.381(12) . ? C12A C13A 1.347(15) . ? C13A C14A 1.347(14) . ? C14A C15A 1.428(14) . ? O1B C7B 1.229(6) . ? N1B C7B 1.340(8) . ? N1B C8B 1.460(8) . ? C1B C2B 1.364(8) . ? C1B C6B 1.370(8) . ? C1B C16B 1.517(9) . ? C2B C3B 1.381(8) . ? C3B C4B 1.384(7) . ? C4B C5B 1.375(7) . ? C4B C7B 1.513(9) . ? C5B C6B 1.382(8) . ? C8B C10B 1.516(9) . ? C8B C9B 1.542(8) . ? C10B C15B 1.373(9) . ? C10B C11B 1.377(8) . ? C11B C12B 1.390(11) . ? C12B C13B 1.368(10) . ? C13B C14B 1.358(10) . ? C14B C15B 1.369(10) . ? 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 C7A N1A C8A 122.9(6) . . ? C2A C1A C6A 118.2(6) . . ? C2A C1A C16A 121.5(7) . . ? C6A C1A C16A 120.3(7) . . ? C1A C2A C3A 121.9(6) . . ? C2A C3A C4A 120.7(6) . . ? C3A C4A C5A 117.5(6) . . ? C3A C4A C7A 124.3(6) . . ? C5A C4A C7A 118.2(6) . . ? C4A C5A C6A 120.8(6) . . ? C1A C6A C5A 120.9(6) . . ? O1A C7A N1A 123.2(7) . . ? O1A C7A C4A 121.1(7) . . ? N1A C7A C4A 115.7(7) . . ? N1A C8A C9A 109.1(5) . . ? N1A C8A C10A 110.6(4) . . ? C9A C8A C10A 114.2(6) . . ? C11A C10A C15A 117.6(7) . . ? C11A C10A C8A 123.4(7) . . ? C15A C10A C8A 119.1(8) . . ? C10A C11A C12A 123.8(9) . . ? C13A C12A C11A 118.0(12) . . ? C14A C13A C12A 121.4(13) . . ? C13A C14A C15A 120.0(11) . . ? C10A C15A C14A 119.2(9) . . ? C7B N1B C8B 121.9(7) . . ? C2B C1B C6B 117.4(7) . . ? C2B C1B C16B 121.6(7) . . ? C6B C1B C16B 120.9(7) . . ? C1B C2B C3B 121.9(6) . . ? C2B C3B C4B 120.5(6) . . ? C5B C4B C3B 117.9(6) . . ? C5B C4B C7B 118.5(6) . . ? C3B C4B C7B 123.6(7) . . ? C4B C5B C6B 120.5(6) . . ? C1B C6B C5B 121.9(6) . . ? O1B C7B N1B 122.4(8) . . ? O1B C7B C4B 120.6(7) . . ? N1B C7B C4B 117.0(7) . . ? N1B C8B C10B 111.9(5) . . ? N1B C8B C9B 109.0(6) . . ? C10B C8B C9B 110.4(6) . . ? C15B C10B C11B 118.6(7) . . ? C15B C10B C8B 119.6(7) . . ? C11B C10B C8B 121.7(7) . . ? C10B C11B C12B 120.2(8) . . ? C13B C12B C11B 119.1(8) . . ? C14B C13B C12B 121.3(9) . . ? C13B C14B C15B 119.1(8) . . ? C14B C15B C10B 121.6(7) . . ? _diffrn_measured_fraction_theta_max 0.411 _diffrn_reflns_theta_full 26.71 _diffrn_measured_fraction_theta_full 0.411 _refine_diff_density_max 0.122 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.033 #==END data_S:cmpd_(S)-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-N-(4-Nitrobenzoyl)-a-methylbenzylamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N2 O3' _chemical_formula_weight 270.28 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.5535(10) _cell_length_b 9.8900(7) _cell_length_c 33.038(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2794.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'transparent block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4679 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4417 _reflns_number_gt 2505 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0754P)^2^+0.0562P] 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 1(2) _refine_ls_number_reflns 4417 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 O1A O 0.7586(4) 0.6191(2) 0.87513(8) 0.0676(8) Uani 1 1 d . . . O2A O 0.1344(5) 0.3406(5) 0.99175(15) 0.1471(19) Uani 1 1 d . . . O3A O 0.0374(5) 0.4983(6) 0.95793(14) 0.1427(19) Uani 1 1 d . . . N1A N 0.8085(5) 0.3990(3) 0.87591(11) 0.0600(9) Uani 1 1 d . . . N2A N 0.1438(5) 0.4265(5) 0.96640(12) 0.0869(12) Uani 1 1 d . . . C1A C 0.2931(5) 0.4447(4) 0.94614(11) 0.0650(11) Uani 1 1 d . . . C2A C 0.4058(6) 0.3481(4) 0.94961(13) 0.0755(13) Uani 1 1 d . . . H2A H 0.3887 0.2717 0.9654 0.091 Uiso 1 1 calc R . . C3A C 0.5446(5) 0.3647(4) 0.92948(11) 0.0666(11) Uani 1 1 d . . . H3A H 0.6213 0.2983 0.9311 0.080 Uiso 1 1 calc R . . C4A C 0.5707(5) 0.4794(3) 0.90687(9) 0.0508(9) Uani 1 1 d . . . C5A C 0.4560(5) 0.5765(4) 0.90479(11) 0.0651(11) Uani 1 1 d . . . H5A H 0.4738 0.6547 0.8899 0.078 Uiso 1 1 calc R . . C6A C 0.3164(5) 0.5601(4) 0.92424(12) 0.0701(11) Uani 1 1 d . . . H6A H 0.2390 0.6259 0.9226 0.084 Uiso 1 1 calc R . . C7A C 0.7196(5) 0.5043(3) 0.88488(10) 0.0526(9) Uani 1 1 d . . . C8A C 0.9546(5) 0.4146(4) 0.85384(13) 0.0645(10) Uani 1 1 d . . . H8A H 1.0126 0.4897 0.8660 0.077 Uiso 1 1 calc R . . C9A C 1.0505(6) 0.2873(5) 0.85908(14) 0.0821(13) Uani 1 1 d . . . H9A1 H 0.9948 0.2119 0.8479 0.123 Uiso 1 1 calc R . . H9A2 H 1.0689 0.2718 0.8874 0.123 Uiso 1 1 calc R . . H9A3 H 1.1487 0.2975 0.8453 0.123 Uiso 1 1 calc R . . C10A C 0.9244(5) 0.4490(4) 0.80991(13) 0.0646(11) Uani 1 1 d . . . C11A C 0.8215(6) 0.3755(5) 0.78768(14) 0.0787(12) Uani 1 1 d . . . H11A H 0.7659 0.3061 0.8001 0.094 Uiso 1 1 calc R . . C12A C 0.7972(7) 0.4017(6) 0.74664(16) 0.0966(15) Uani 1 1 d . . . H12A H 0.7266 0.3496 0.7320 0.116 Uiso 1 1 calc R . . C13A C 0.8754(7) 0.5016(7) 0.72846(18) 0.1015(17) Uani 1 1 d . . . H13A H 0.8610 0.5197 0.7011 0.122 Uiso 1 1 calc R . . C14A C 0.9776(8) 0.5770(6) 0.7512(2) 0.1090(19) Uani 1 1 d . . . H14A H 1.0310 0.6481 0.7391 0.131 Uiso 1 1 calc R . . C15A C 1.0027(6) 0.5504(5) 0.79107(16) 0.0874(14) Uani 1 1 d . . . H15A H 1.0743 0.6021 0.8055 0.105 Uiso 1 1 calc R . . O1B O 0.2608(4) 0.6154(2) 0.60831(8) 0.0707(8) Uani 1 1 d . . . O2B O 0.4036(5) 0.3695(4) 0.80703(10) 0.0987(11) Uani 1 1 d . . . O3B O 0.4669(7) 0.5778(4) 0.80361(11) 0.1373(18) Uani 1 1 d . . . N1B N 0.2303(4) 0.3932(3) 0.60066(9) 0.0523(8) Uani 1 1 d . . . N2B N 0.4232(5) 0.4719(5) 0.78853(12) 0.0843(11) Uani 1 1 d . . . C1B C 0.3928(5) 0.4722(4) 0.74478(12) 0.0621(10) Uani 1 1 d . . . C2B C 0.3069(5) 0.3693(4) 0.72899(12) 0.0640(10) Uani 1 1 d . . . H2B H 0.2726 0.2983 0.7451 0.077 Uiso 1 1 calc R . . C3B C 0.2722(5) 0.3738(3) 0.68792(11) 0.0581(10) Uani 1 1 d . . . H3B H 0.2148 0.3042 0.6762 0.070 Uiso 1 1 calc R . . C4B C 0.3216(4) 0.4794(3) 0.66461(11) 0.0512(9) Uani 1 1 d . . . C5B C 0.4131(5) 0.5791(4) 0.68133(13) 0.0642(10) Uani 1 1 d . . . H5B H 0.4511 0.6485 0.6651 0.077 Uiso 1 1 calc R . . C6B C 0.4487(5) 0.5767(4) 0.72173(13) 0.0709(12) Uani 1 1 d . . . H6B H 0.5095 0.6444 0.7333 0.085 Uiso 1 1 calc R . . C7B C 0.2695(4) 0.5005(3) 0.62188(11) 0.0509(9) Uani 1 1 d . . . C8B C 0.1510(4) 0.4060(4) 0.56184(10) 0.0547(10) Uani 1 1 d . . . H8B H 0.1919 0.4868 0.5483 0.066 Uiso 1 1 calc R . . C9B C 0.1923(6) 0.2837(4) 0.53573(12) 0.0792(13) Uani 1 1 d . . . H9B1 H 0.1523 0.2031 0.5482 0.119 Uiso 1 1 calc R . . H9B2 H 0.3039 0.2770 0.5333 0.119 Uiso 1 1 calc R . . H9B3 H 0.1468 0.2942 0.5094 0.119 Uiso 1 1 calc R . . C10B C -0.0224(5) 0.4238(4) 0.56681(12) 0.0596(10) Uani 1 1 d . . . C11B C -0.0997(6) 0.4008(5) 0.60217(14) 0.0803(13) Uani 1 1 d . . . H11B H -0.0436 0.3722 0.6247 0.096 Uiso 1 1 calc R . . C12B C -0.2577(7) 0.4187(7) 0.6054(2) 0.111(2) Uani 1 1 d . . . H12B H -0.3085 0.4011 0.6297 0.133 Uiso 1 1 calc R . . C13B C -0.3405(7) 0.4629(6) 0.5722(2) 0.114(2) Uani 1 1 d . . . H13B H -0.4478 0.4766 0.5741 0.136 Uiso 1 1 calc R . . C14B C -0.2657(7) 0.4862(7) 0.5370(2) 0.116(2) Uani 1 1 d . . . H14B H -0.3215 0.5151 0.5144 0.139 Uiso 1 1 calc R . . C15B C -0.1083(6) 0.4675(5) 0.53455(16) 0.0868(15) Uani 1 1 d . . . H15B H -0.0578 0.4850 0.5102 0.104 Uiso 1 1 calc R . . HN1A H 0.779(5) 0.328(4) 0.8796(12) 0.063(13) Uiso 1 1 d . . . HN1B H 0.247(4) 0.316(3) 0.6120(9) 0.037(8) Uiso 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 O1A 0.094(2) 0.0342(12) 0.0741(16) -0.0009(12) 0.0167(16) -0.0023(15) O2A 0.118(3) 0.152(4) 0.171(4) 0.071(3) 0.070(3) 0.017(3) O3A 0.090(3) 0.174(4) 0.165(4) 0.047(4) 0.048(3) 0.048(3) N1A 0.067(2) 0.0352(16) 0.077(2) 0.0004(16) 0.0191(18) 0.0015(18) N2A 0.085(3) 0.096(3) 0.079(3) 0.007(2) 0.026(2) 0.008(3) C1A 0.069(3) 0.070(3) 0.057(2) -0.004(2) 0.010(2) 0.002(3) C2A 0.089(3) 0.062(2) 0.076(3) 0.016(2) 0.025(3) 0.009(3) C3A 0.084(3) 0.047(2) 0.069(2) 0.0091(19) 0.019(2) 0.018(2) C4A 0.072(2) 0.0354(16) 0.0453(18) -0.0023(15) 0.0035(19) 0.0060(19) C5A 0.075(3) 0.050(2) 0.070(2) 0.008(2) 0.011(2) 0.012(2) C6A 0.070(3) 0.066(2) 0.075(3) 0.007(2) 0.007(2) 0.021(3) C7A 0.074(3) 0.0334(16) 0.0501(19) -0.0040(15) 0.005(2) 0.000(2) C8A 0.060(2) 0.049(2) 0.085(3) -0.001(2) 0.009(2) -0.003(2) C9A 0.069(3) 0.084(3) 0.093(3) 0.003(3) 0.011(3) 0.021(3) C10A 0.059(2) 0.050(2) 0.085(3) 0.006(2) 0.024(2) 0.008(2) C11A 0.080(3) 0.072(3) 0.084(3) 0.005(2) 0.010(3) -0.010(3) C12A 0.090(3) 0.109(4) 0.091(4) 0.006(3) 0.001(3) 0.002(4) C13A 0.094(4) 0.118(4) 0.092(4) 0.013(4) 0.014(3) 0.022(4) C14A 0.113(4) 0.091(4) 0.123(4) 0.043(4) 0.045(4) 0.010(4) C15A 0.083(3) 0.077(3) 0.102(3) 0.013(3) 0.019(3) -0.013(3) O1B 0.097(2) 0.0353(12) 0.0804(17) 0.0030(12) -0.0051(17) -0.0030(15) O2B 0.119(3) 0.105(2) 0.072(2) 0.0157(19) -0.010(2) 0.017(3) O3B 0.210(5) 0.117(3) 0.085(2) -0.021(2) -0.037(3) -0.031(4) N1B 0.063(2) 0.0337(14) 0.0598(19) 0.0023(14) -0.0071(17) -0.0013(16) N2B 0.092(3) 0.087(3) 0.073(3) -0.012(2) -0.013(2) 0.006(3) C1B 0.065(3) 0.060(2) 0.062(2) -0.004(2) -0.011(2) 0.013(2) C2B 0.068(3) 0.056(2) 0.068(2) 0.002(2) -0.002(2) 0.003(2) C3B 0.068(2) 0.0411(18) 0.065(2) 0.0008(17) -0.006(2) -0.002(2) C4B 0.050(2) 0.0357(17) 0.068(2) -0.0045(17) -0.0004(19) 0.0061(18) C5B 0.065(2) 0.048(2) 0.080(3) -0.003(2) -0.005(2) -0.005(2) C6B 0.069(3) 0.056(2) 0.087(3) -0.015(2) -0.015(2) -0.009(2) C7B 0.052(2) 0.0339(15) 0.067(2) -0.0049(17) 0.0016(19) 0.0007(18) C8B 0.068(3) 0.0440(19) 0.052(2) -0.0016(17) -0.0012(19) -0.001(2) C9B 0.085(3) 0.084(3) 0.069(2) -0.016(2) 0.000(3) 0.012(3) C10B 0.067(2) 0.047(2) 0.065(2) -0.0098(19) -0.005(2) 0.001(2) C11B 0.067(3) 0.096(3) 0.078(3) -0.006(3) -0.001(2) -0.008(3) C12B 0.075(4) 0.128(5) 0.130(5) -0.034(4) 0.017(4) -0.013(4) C13B 0.065(3) 0.107(5) 0.169(6) -0.054(5) -0.009(4) 0.005(3) C14B 0.097(4) 0.113(4) 0.137(5) -0.031(5) -0.054(4) 0.028(4) C15B 0.086(3) 0.092(4) 0.083(3) -0.003(3) -0.018(3) 0.012(3) _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 O1A C7A 1.226(4) . ? O2A N2A 1.196(5) . ? O3A N2A 1.188(5) . ? N1A C7A 1.323(5) . ? N1A C8A 1.455(5) . ? N2A C1A 1.453(6) . ? C1A C2A 1.362(6) . ? C1A C6A 1.365(6) . ? C2A C3A 1.371(6) . ? C3A C4A 1.376(5) . ? C4A C5A 1.374(5) . ? C4A C7A 1.487(5) . ? C5A C6A 1.366(6) . ? C8A C9A 1.512(6) . ? C8A C10A 1.513(6) . ? C10A C15A 1.357(6) . ? C10A C11A 1.357(6) . ? C11A C12A 1.396(6) . ? C12A C13A 1.336(7) . ? C13A C14A 1.373(8) . ? C14A C15A 1.359(7) . ? O1B C7B 1.224(4) . ? O2B N2B 1.194(5) . ? O3B N2B 1.219(5) . ? N1B C7B 1.315(4) . ? N1B C8B 1.456(4) . ? N2B C1B 1.469(5) . ? C1B C2B 1.359(5) . ? C1B C6B 1.369(5) . ? C2B C3B 1.389(5) . ? C3B C4B 1.364(5) . ? C4B C5B 1.375(5) . ? C4B C7B 1.495(5) . ? C5B C6B 1.370(5) . ? C8B C10B 1.503(5) . ? C8B C9B 1.526(5) . ? C10B C11B 1.362(6) . ? C10B C15B 1.365(6) . ? C11B C12B 1.366(7) . ? C12B C13B 1.376(8) . ? C13B C14B 1.349(8) . ? C14B C15B 1.362(7) . ? 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 C7A N1A C8A 121.5(3) . . ? O3A N2A O2A 122.6(5) . . ? O3A N2A C1A 119.4(4) . . ? O2A N2A C1A 118.0(5) . . ? C2A C1A C6A 121.8(4) . . ? C2A C1A N2A 119.7(4) . . ? C6A C1A N2A 118.4(4) . . ? C1A C2A C3A 119.2(4) . . ? C2A C3A C4A 120.2(4) . . ? C5A C4A C3A 119.1(4) . . ? C5A C4A C7A 118.1(3) . . ? C3A C4A C7A 122.7(3) . . ? C6A C5A C4A 121.2(4) . . ? C1A C6A C5A 118.4(4) . . ? O1A C7A N1A 120.9(4) . . ? O1A C7A C4A 120.9(3) . . ? N1A C7A C4A 118.1(3) . . ? N1A C8A C9A 108.7(3) . . ? N1A C8A C10A 111.0(3) . . ? C9A C8A C10A 112.9(3) . . ? C15A C10A C11A 117.9(4) . . ? C15A C10A C8A 121.5(4) . . ? C11A C10A C8A 120.6(4) . . ? C10A C11A C12A 121.5(5) . . ? C13A C12A C11A 119.9(6) . . ? C12A C13A C14A 118.3(5) . . ? C15A C14A C13A 121.7(5) . . ? C10A C15A C14A 120.6(5) . . ? C7B N1B C8B 121.2(3) . . ? O2B N2B O3B 124.2(4) . . ? O2B N2B C1B 118.7(4) . . ? O3B N2B C1B 117.0(4) . . ? C2B C1B C6B 122.7(4) . . ? C2B C1B N2B 118.1(4) . . ? C6B C1B N2B 119.1(4) . . ? C1B C2B C3B 117.8(4) . . ? C4B C3B C2B 120.7(4) . . ? C3B C4B C5B 119.9(4) . . ? C3B C4B C7B 123.2(3) . . ? C5B C4B C7B 116.7(3) . . ? C6B C5B C4B 120.4(4) . . ? C1B C6B C5B 118.5(4) . . ? O1B C7B N1B 122.6(3) . . ? O1B C7B C4B 119.6(3) . . ? N1B C7B C4B 117.8(3) . . ? N1B C8B C10B 111.9(3) . . ? N1B C8B C9B 108.7(3) . . ? C10B C8B C9B 112.5(3) . . ? C11B C10B C15B 117.5(4) . . ? C11B C10B C8B 123.6(4) . . ? C15B C10B C8B 118.9(4) . . ? C10B C11B C12B 121.7(6) . . ? C11B C12B C13B 119.2(6) . . ? C14B C13B C12B 119.9(6) . . ? C13B C14B C15B 119.8(6) . . ? C14B C15B C10B 122.0(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.209 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.074 #==END data_s:cmpd_rac-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N2 O3' _chemical_formula_weight 270.28 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.88500(10) _cell_length_b 5.45500(10) _cell_length_c 40.4438(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.3670(10) _cell_angle_gamma 90.00 _cell_volume 2610.58(7) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9639 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10329 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5920 _reflns_number_gt 3976 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0507P)^2^+0.4658P] 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_number_reflns 5920 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.15646(10) 0.3913(2) 0.82170(3) 0.0361(3) Uani 1 1 d . . . O2A O 0.04588(11) 0.0455(2) 0.65715(3) 0.0422(3) Uani 1 1 d . . . O3A O 0.06932(10) -0.3323(2) 0.67201(3) 0.0407(3) Uani 1 1 d . . . N1A N 0.16442(12) -0.0084(3) 0.83707(3) 0.0287(3) Uani 1 1 d . . . N2A N 0.06247(10) -0.1130(2) 0.67755(3) 0.0220(3) Uani 1 1 d . . . C1A C 0.07933(12) -0.0370(3) 0.71330(4) 0.0237(3) Uani 1 1 d . . . C2A C 0.04762(13) -0.1969(3) 0.73718(4) 0.0254(4) Uani 1 1 d . . . H2A H 0.0122 -0.3485 0.7311 0.030 Uiso 1 1 calc R . . C3A C 0.06859(13) -0.1312(3) 0.77030(4) 0.0259(4) Uani 1 1 d . . . H3A H 0.0472 -0.2383 0.7871 0.031 Uiso 1 1 calc R . . C4A C 0.12103(12) 0.0915(3) 0.77899(4) 0.0236(3) Uani 1 1 d . . . C5A C 0.14888(13) 0.2503(3) 0.75414(4) 0.0258(4) Uani 1 1 d . . . H5A H 0.1829 0.4038 0.7600 0.031 Uiso 1 1 calc R . . C6A C 0.12785(12) 0.1883(3) 0.72093(4) 0.0252(4) Uani 1 1 d . . . H6A H 0.1463 0.2974 0.7039 0.030 Uiso 1 1 calc R . . C7A C 0.14816(13) 0.1720(3) 0.81449(4) 0.0260(4) Uani 1 1 d . . . C8A C 0.19463(14) 0.0423(3) 0.87236(4) 0.0281(4) Uani 1 1 d . . . H8A H 0.2302 0.2084 0.8743 0.034 Uiso 1 1 calc R . . C9A C 0.28202(14) -0.1445(3) 0.88624(4) 0.0362(4) Uani 1 1 d . . . H9A1 H 0.2515 -0.3103 0.8827 0.054 Uiso 1 1 calc R . . H9A2 H 0.2999 -0.1159 0.9101 0.054 Uiso 1 1 calc R . . H9A3 H 0.3509 -0.1273 0.8749 0.054 Uiso 1 1 calc R . . C10A C 0.09182(13) 0.0441(3) 0.89212(4) 0.0262(4) Uani 1 1 d . . . C11A C 0.01242(14) -0.1440(3) 0.88924(4) 0.0354(4) Uani 1 1 d . . . H11A H 0.0193 -0.2714 0.8735 0.042 Uiso 1 1 calc R . . C12A C -0.07673(15) -0.1472(4) 0.90906(5) 0.0406(5) Uani 1 1 d . . . H12A H -0.1305 -0.2764 0.9068 0.049 Uiso 1 1 calc R . . C13A C -0.08782(15) 0.0364(3) 0.93202(4) 0.0375(4) Uani 1 1 d . . . H13A H -0.1488 0.0337 0.9456 0.045 Uiso 1 1 calc R . . C14A C -0.00999(15) 0.2233(3) 0.93508(4) 0.0367(4) Uani 1 1 d . . . H14A H -0.0170 0.3499 0.9509 0.044 Uiso 1 1 calc R . . C15A C 0.07898(14) 0.2273(3) 0.91509(4) 0.0321(4) Uani 1 1 d . . . H15A H 0.1319 0.3581 0.9172 0.039 Uiso 1 1 calc R . . O1B O -0.38137(10) -0.1508(2) 0.90506(3) 0.0330(3) Uani 1 1 d . . . O2B O -0.17117(10) 0.0938(2) 0.75442(3) 0.0394(3) Uani 1 1 d . . . O3B O -0.10142(10) 0.4302(2) 0.77573(3) 0.0446(3) Uani 1 1 d . . . N1B N -0.41851(12) 0.2544(3) 0.90963(3) 0.0302(3) Uani 1 1 d . . . N2B N -0.15743(11) 0.2449(3) 0.77690(3) 0.0301(3) Uani 1 1 d . . . C1B C -0.21337(13) 0.1971(3) 0.80746(4) 0.0266(4) Uani 1 1 d . . . C2B C -0.20040(15) 0.3660(3) 0.83287(4) 0.0381(4) Uani 1 1 d . . . H2B H -0.1548 0.5076 0.8311 0.046 Uiso 1 1 calc R . . C3B C -0.25545(15) 0.3244(3) 0.86100(4) 0.0376(4) Uani 1 1 d . . . H3B H -0.2488 0.4400 0.8786 0.045 Uiso 1 1 calc R . . C4B C -0.32018(13) 0.1154(3) 0.86368(4) 0.0261(4) Uani 1 1 d . . . C5B C -0.32996(14) -0.0521(3) 0.83788(4) 0.0320(4) Uani 1 1 d . . . H5B H -0.3734 -0.1967 0.8398 0.038 Uiso 1 1 calc R . . C6B C -0.27724(14) -0.0117(3) 0.80929(4) 0.0326(4) Uani 1 1 d . . . H6B H -0.2850 -0.1252 0.7914 0.039 Uiso 1 1 calc R . . C7B C -0.37652(13) 0.0606(3) 0.89455(4) 0.0264(4) Uani 1 1 d . . . C8B C -0.46221(13) 0.2385(3) 0.94219(4) 0.0269(4) Uani 1 1 d . . . H8B H -0.5002 0.0759 0.9438 0.032 Uiso 1 1 calc R . . C9B C -0.55025(14) 0.4377(3) 0.94502(4) 0.0343(4) Uani 1 1 d . . . H9B1 H -0.5157 0.5986 0.9423 0.051 Uiso 1 1 calc R . . H9B2 H -0.5791 0.4286 0.9669 0.051 Uiso 1 1 calc R . . H9B3 H -0.6127 0.4142 0.9277 0.051 Uiso 1 1 calc R . . C10B C -0.36554(13) 0.2516(3) 0.96958(4) 0.0257(4) Uani 1 1 d . . . C11B C -0.29008(14) 0.4474(3) 0.97140(4) 0.0311(4) Uani 1 1 d . . . H11B H -0.2998 0.5768 0.9557 0.037 Uiso 1 1 calc R . . C12B C -0.20086(15) 0.4548(3) 0.99605(4) 0.0360(4) Uani 1 1 d . . . H12B H -0.1496 0.5888 0.9971 0.043 Uiso 1 1 calc R . . C13B C -0.18619(15) 0.2667(3) 1.01919(4) 0.0379(4) Uani 1 1 d . . . H13B H -0.1252 0.2720 1.0361 0.046 Uiso 1 1 calc R . . C14B C -0.26035(15) 0.0728(3) 1.01745(4) 0.0358(4) Uani 1 1 d . . . H14B H -0.2504 -0.0566 1.0332 0.043 Uiso 1 1 calc R . . C15B C -0.34971(14) 0.0653(3) 0.99278(4) 0.0293(4) Uani 1 1 d . . . H15B H -0.4006 -0.0693 0.9918 0.035 Uiso 1 1 calc R . . HN1A H 0.1613(15) -0.161(3) 0.8305(4) 0.036(5) Uiso 1 1 d . . . HN1B H -0.4131(15) 0.392(3) 0.9016(4) 0.036(6) Uiso 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 O1A 0.0509(8) 0.0260(7) 0.0300(7) -0.0025(5) -0.0033(6) 0.0006(5) O2A 0.0555(8) 0.0400(8) 0.0306(7) 0.0035(6) 0.0009(6) 0.0017(6) O3A 0.0521(8) 0.0344(8) 0.0353(7) -0.0037(6) 0.0016(6) 0.0024(6) N1A 0.0404(8) 0.0241(8) 0.0216(7) 0.0004(6) 0.0025(6) 0.0005(6) N2A 0.0234(7) 0.0182(7) 0.0244(7) 0.0028(6) 0.0033(5) 0.0008(5) C1A 0.0242(8) 0.0255(8) 0.0214(8) 0.0001(7) 0.0014(6) 0.0041(7) C2A 0.0261(8) 0.0223(8) 0.0275(9) 0.0010(7) 0.0015(6) -0.0013(7) C3A 0.0273(8) 0.0247(9) 0.0262(9) 0.0038(7) 0.0039(7) -0.0001(7) C4A 0.0227(8) 0.0233(8) 0.0248(8) 0.0002(7) 0.0019(6) 0.0040(6) C5A 0.0267(8) 0.0223(8) 0.0280(9) 0.0013(7) 0.0010(7) 0.0001(7) C6A 0.0272(8) 0.0246(9) 0.0241(9) 0.0048(7) 0.0035(6) 0.0017(7) C7A 0.0254(8) 0.0270(9) 0.0256(9) 0.0002(7) 0.0021(6) 0.0009(7) C8A 0.0341(9) 0.0295(9) 0.0205(8) -0.0017(7) 0.0011(7) 0.0003(7) C9A 0.0369(10) 0.0450(11) 0.0271(9) 0.0027(8) 0.0046(7) 0.0076(8) C10A 0.0299(8) 0.0264(9) 0.0215(8) 0.0019(7) -0.0023(7) 0.0031(7) C11A 0.0374(10) 0.0334(10) 0.0350(10) -0.0086(8) 0.0009(8) -0.0013(8) C12A 0.0342(10) 0.0421(11) 0.0456(11) -0.0033(9) 0.0035(8) -0.0079(8) C13A 0.0301(9) 0.0471(11) 0.0358(10) 0.0000(9) 0.0055(8) 0.0039(9) C14A 0.0412(10) 0.0370(10) 0.0326(10) -0.0063(8) 0.0063(8) 0.0034(9) C15A 0.0363(9) 0.0296(9) 0.0303(9) -0.0020(8) 0.0022(7) -0.0009(8) O1B 0.0431(7) 0.0280(7) 0.0292(6) 0.0023(5) 0.0090(5) -0.0017(5) O2B 0.0444(7) 0.0454(8) 0.0301(7) 0.0017(6) 0.0117(6) 0.0041(6) O3B 0.0403(7) 0.0509(8) 0.0442(8) 0.0079(7) 0.0126(6) -0.0116(7) N1B 0.0426(8) 0.0281(8) 0.0208(7) 0.0037(7) 0.0076(6) 0.0040(7) N2B 0.0268(7) 0.0357(8) 0.0281(8) 0.0052(7) 0.0050(6) 0.0036(7) C1B 0.0253(8) 0.0309(9) 0.0243(9) 0.0036(7) 0.0050(6) 0.0011(7) C2B 0.0449(11) 0.0335(10) 0.0371(10) -0.0019(8) 0.0103(8) -0.0136(8) C3B 0.0506(11) 0.0339(10) 0.0293(10) -0.0081(8) 0.0096(8) -0.0123(9) C4B 0.0288(8) 0.0274(9) 0.0219(8) 0.0018(7) 0.0020(6) 0.0010(7) C5B 0.0392(10) 0.0300(9) 0.0279(9) -0.0020(8) 0.0091(7) -0.0078(8) C6B 0.0417(10) 0.0311(10) 0.0260(9) -0.0054(7) 0.0078(8) -0.0050(8) C7B 0.0282(8) 0.0284(9) 0.0222(8) -0.0012(7) 0.0007(6) -0.0025(7) C8B 0.0341(9) 0.0272(9) 0.0201(8) 0.0021(7) 0.0058(7) 0.0008(7) C9B 0.0358(9) 0.0362(10) 0.0315(10) 0.0035(8) 0.0071(7) 0.0046(8) C10B 0.0311(8) 0.0258(9) 0.0214(8) -0.0011(7) 0.0083(7) 0.0057(7) C11B 0.0376(9) 0.0278(9) 0.0289(9) 0.0000(7) 0.0091(7) 0.0037(8) C12B 0.0362(10) 0.0348(10) 0.0377(11) -0.0100(9) 0.0061(8) -0.0006(8) C13B 0.0381(10) 0.0439(11) 0.0304(10) -0.0088(9) -0.0043(8) 0.0092(9) C14B 0.0464(11) 0.0352(10) 0.0254(9) 0.0009(8) 0.0012(8) 0.0095(9) C15B 0.0364(9) 0.0278(9) 0.0245(9) 0.0001(7) 0.0065(7) 0.0019(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 O1A C7A 1.2331(19) . ? O2A N2A 1.1988(16) . ? O3A N2A 1.2210(17) . ? N1A C7A 1.344(2) . ? N1A C8A 1.465(2) . ? N1A HN1A 0.873(19) . ? N2A C1A 1.4994(19) . ? C1A C2A 1.380(2) . ? C1A C6A 1.380(2) . ? C2A C3A 1.386(2) . ? C2A H2A 0.9500 . ? C3A C4A 1.396(2) . ? C3A H3A 0.9500 . ? C4A C5A 1.390(2) . ? C4A C7A 1.507(2) . ? C5A C6A 1.385(2) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C8A C10A 1.521(2) . ? C8A C9A 1.524(2) . ? C8A H8A 1.0000 . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A C15A 1.382(2) . ? C10A C11A 1.391(2) . ? C11A C12A 1.387(3) . ? C11A H11A 0.9500 . ? C12A C13A 1.380(3) . ? C12A H12A 0.9500 . ? C13A C14A 1.374(3) . ? C13A H13A 0.9500 . ? C14A C15A 1.390(2) . ? C14A H14A 0.9500 . ? C15A H15A 0.9500 . ? O1B C7B 1.2325(19) . ? O2B N2B 1.2266(18) . ? O3B N2B 1.2135(18) . ? N1B C7B 1.340(2) . ? N1B C8B 1.463(2) . ? N1B HN1B 0.823(19) . ? N2B C1B 1.480(2) . ? C1B C6B 1.375(2) . ? C1B C2B 1.378(2) . ? C2B C3B 1.383(2) . ? C2B H2B 0.9500 . ? C3B C4B 1.385(2) . ? C3B H3B 0.9500 . ? C4B C5B 1.384(2) . ? C4B C7B 1.501(2) . ? C5B C6B 1.383(2) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? C8B C9B 1.520(2) . ? C8B C10B 1.521(2) . ? C8B H8B 1.0000 . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B C15B 1.384(2) . ? C10B C11B 1.392(2) . ? C11B C12B 1.386(2) . ? C11B H11B 0.9500 . ? C12B C13B 1.389(3) . ? C12B H12B 0.9500 . ? C13B C14B 1.374(3) . ? C13B H13B 0.9500 . ? C14B C15B 1.388(2) . ? C14B H14B 0.9500 . ? C15B H15B 0.9500 . ? 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 C7A N1A C8A 122.04(15) . . ? C7A N1A HN1A 119.5(12) . . ? C8A N1A HN1A 118.4(12) . . ? O2A N2A O3A 126.12(14) . . ? O2A N2A C1A 117.57(13) . . ? O3A N2A C1A 116.29(12) . . ? C2A C1A C6A 122.83(15) . . ? C2A C1A N2A 118.65(14) . . ? C6A C1A N2A 118.51(13) . . ? C1A C2A C3A 118.47(15) . . ? C1A C2A H2A 120.8 . . ? C3A C2A H2A 120.8 . . ? C2A C3A C4A 120.28(15) . . ? C2A C3A H3A 119.9 . . ? C4A C3A H3A 119.9 . . ? C5A C4A C3A 119.42(15) . . ? C5A C4A C7A 117.59(14) . . ? C3A C4A C7A 122.99(14) . . ? C6A C5A C4A 121.03(15) . . ? C6A C5A H5A 119.5 . . ? C4A C5A H5A 119.5 . . ? C1A C6A C5A 117.91(14) . . ? C1A C6A H6A 121.0 . . ? C5A C6A H6A 121.0 . . ? O1A C7A N1A 123.11(15) . . ? O1A C7A C4A 120.87(14) . . ? N1A C7A C4A 116.00(14) . . ? N1A C8A C10A 112.17(13) . . ? N1A C8A C9A 109.22(13) . . ? C10A C8A C9A 111.35(13) . . ? N1A C8A H8A 108.0 . . ? C10A C8A H8A 108.0 . . ? C9A C8A H8A 108.0 . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C15A C10A C11A 118.21(16) . . ? C15A C10A C8A 120.14(15) . . ? C11A C10A C8A 121.53(15) . . ? C12A C11A C10A 120.62(17) . . ? C12A C11A H11A 119.7 . . ? C10A C11A H11A 119.7 . . ? C13A C12A C11A 120.38(18) . . ? C13A C12A H12A 119.8 . . ? C11A C12A H12A 119.8 . . ? C14A C13A C12A 119.55(17) . . ? C14A C13A H13A 120.2 . . ? C12A C13A H13A 120.2 . . ? C13A C14A C15A 120.08(17) . . ? C13A C14A H14A 120.0 . . ? C15A C14A H14A 120.0 . . ? C10A C15A C14A 121.16(17) . . ? C10A C15A H15A 119.4 . . ? C14A C15A H15A 119.4 . . ? C7B N1B C8B 122.78(15) . . ? C7B N1B HN1B 119.6(13) . . ? C8B N1B HN1B 117.2(13) . . ? O3B N2B O2B 124.49(14) . . ? O3B N2B C1B 118.04(14) . . ? O2B N2B C1B 117.47(14) . . ? C6B C1B C2B 122.53(15) . . ? C6B C1B N2B 118.98(15) . . ? C2B C1B N2B 118.49(15) . . ? C1B C2B C3B 118.35(16) . . ? C1B C2B H2B 120.8 . . ? C3B C2B H2B 120.8 . . ? C2B C3B C4B 120.56(16) . . ? C2B C3B H3B 119.7 . . ? C4B C3B H3B 119.7 . . ? C5B C4B C3B 119.51(15) . . ? C5B C4B C7B 118.90(15) . . ? C3B C4B C7B 121.55(15) . . ? C6B C5B C4B 120.82(16) . . ? C6B C5B H5B 119.6 . . ? C4B C5B H5B 119.6 . . ? C1B C6B C5B 118.21(15) . . ? C1B C6B H6B 120.9 . . ? C5B C6B H6B 120.9 . . ? O1B C7B N1B 123.38(15) . . ? O1B C7B C4B 120.80(14) . . ? N1B C7B C4B 115.82(14) . . ? N1B C8B C9B 109.27(13) . . ? N1B C8B C10B 110.20(13) . . ? C9B C8B C10B 112.96(13) . . ? N1B C8B H8B 108.1 . . ? C9B C8B H8B 108.1 . . ? C10B C8B H8B 108.1 . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C15B C10B C11B 118.78(15) . . ? C15B C10B C8B 120.32(15) . . ? C11B C10B C8B 120.89(14) . . ? C12B C11B C10B 120.38(16) . . ? C12B C11B H11B 119.8 . . ? C10B C11B H11B 119.8 . . ? C11B C12B C13B 120.17(17) . . ? C11B C12B H12B 119.9 . . ? C13B C12B H12B 119.9 . . ? C14B C13B C12B 119.65(17) . . ? C14B C13B H13B 120.2 . . ? C12B C13B H13B 120.2 . . ? C13B C14B C15B 120.20(17) . . ? C13B C14B H14B 119.9 . . ? C15B C14B H14B 119.9 . . ? C10B C15B C14B 120.82(16) . . ? C10B C15B H15B 119.6 . . ? C14B C15B H15B 119.6 . . ? 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 O2A N2A C1A C2A 150.62(14) . . . . ? O3A N2A C1A C2A -30.80(19) . . . . ? O2A N2A C1A C6A -30.56(19) . . . . ? O3A N2A C1A C6A 148.02(14) . . . . ? C6A C1A C2A C3A -2.0(2) . . . . ? N2A C1A C2A C3A 176.77(13) . . . . ? C1A C2A C3A C4A -0.3(2) . . . . ? C2A C3A C4A C5A 2.0(2) . . . . ? C2A C3A C4A C7A -178.87(14) . . . . ? C3A C4A C5A C6A -1.6(2) . . . . ? C7A C4A C5A C6A 179.24(14) . . . . ? C2A C1A C6A C5A 2.4(2) . . . . ? N2A C1A C6A C5A -176.37(13) . . . . ? C4A C5A C6A C1A -0.6(2) . . . . ? C8A N1A C7A O1A -0.6(2) . . . . ? C8A N1A C7A C4A 178.17(13) . . . . ? C5A C4A C7A O1A 24.8(2) . . . . ? C3A C4A C7A O1A -154.34(15) . . . . ? C5A C4A C7A N1A -153.94(14) . . . . ? C3A C4A C7A N1A 26.9(2) . . . . ? C7A N1A C8A C10A 95.89(18) . . . . ? C7A N1A C8A C9A -140.17(16) . . . . ? N1A C8A C10A C15A -135.27(16) . . . . ? C9A C8A C10A C15A 101.98(18) . . . . ? N1A C8A C10A C11A 48.7(2) . . . . ? C9A C8A C10A C11A -74.00(19) . . . . ? C15A C10A C11A C12A -0.3(2) . . . . ? C8A C10A C11A C12A 175.76(16) . . . . ? C10A C11A C12A C13A -0.1(3) . . . . ? C11A C12A C13A C14A 0.2(3) . . . . ? C12A C13A C14A C15A 0.2(3) . . . . ? C11A C10A C15A C14A 0.7(2) . . . . ? C8A C10A C15A C14A -175.43(15) . . . . ? C13A C14A C15A C10A -0.6(3) . . . . ? O3B N2B C1B C6B 179.99(14) . . . . ? O2B N2B C1B C6B 0.1(2) . . . . ? O3B N2B C1B C2B 0.8(2) . . . . ? O2B N2B C1B C2B -179.12(15) . . . . ? C6B C1B C2B C3B -1.0(3) . . . . ? N2B C1B C2B C3B 178.15(15) . . . . ? C1B C2B C3B C4B 1.2(3) . . . . ? C2B C3B C4B C5B -0.2(3) . . . . ? C2B C3B C4B C7B 177.26(16) . . . . ? C3B C4B C5B C6B -0.9(3) . . . . ? C7B C4B C5B C6B -178.50(15) . . . . ? C2B C1B C6B C5B -0.1(3) . . . . ? N2B C1B C6B C5B -179.27(15) . . . . ? C4B C5B C6B C1B 1.1(3) . . . . ? C8B N1B C7B O1B 7.6(3) . . . . ? C8B N1B C7B C4B -171.51(14) . . . . ? C5B C4B C7B O1B 35.9(2) . . . . ? C3B C4B C7B O1B -141.58(17) . . . . ? C5B C4B C7B N1B -144.95(16) . . . . ? C3B C4B C7B N1B 37.5(2) . . . . ? C7B N1B C8B C9B -153.10(15) . . . . ? C7B N1B C8B C10B 82.23(19) . . . . ? N1B C8B C10B C15B -123.12(16) . . . . ? C9B C8B C10B C15B 114.35(17) . . . . ? N1B C8B C10B C11B 55.49(19) . . . . ? C9B C8B C10B C11B -67.04(19) . . . . ? C15B C10B C11B C12B 0.0(2) . . . . ? C8B C10B C11B C12B -178.61(15) . . . . ? C10B C11B C12B C13B -0.1(2) . . . . ? C11B C12B C13B C14B 0.2(3) . . . . ? C12B C13B C14B C15B -0.2(3) . . . . ? C11B C10B C15B C14B 0.0(2) . . . . ? C8B C10B C15B C14B 178.61(15) . . . . ? C13B C14B C15B C10B 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.222 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.045 #==END data_S:cmpd_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-N-(4-Methylbenzoyl)-a-methylbenzylamine/(S)-N-(4-Nitrobenzoyl)-a- methylbenzylamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H31 N3 O4' _chemical_formula_weight 509.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4413(9) _cell_length_b 5.9721(7) _cell_length_c 23.394(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.670(9) _cell_angle_gamma 90.00 _cell_volume 1316.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'transparent block ' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3967 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3426 _reflns_number_gt 2424 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0272P)^2^+1.3794P] 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 -2(3) _refine_ls_number_reflns 3426 _refine_ls_number_parameters 351 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _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 O1A O 0.1797(3) 0.9069(7) 0.74295(13) 0.0319(11) Uani 1 1 d . . . O2A O -0.0073(4) 0.0379(7) 0.53911(14) 0.0579(10) Uani 1 1 d . . . O3A O 0.1937(4) 0.1784(8) 0.51864(14) 0.0606(11) Uani 1 1 d . . . N1A N -0.0525(4) 0.8385(9) 0.75423(16) 0.0256(12) Uani 1 1 d . . . N2A N 0.0884(5) 0.1770(11) 0.54623(17) 0.0423(13) Uani 1 1 d . . . C1A C 0.0788(5) 0.3421(13) 0.59245(19) 0.0334(16) Uani 1 1 d . . . C2A C -0.0162(5) 0.3021(13) 0.63364(19) 0.0347(15) Uani 1 1 d . . . H2A H -0.0752 0.1731 0.6319 0.042 Uiso 1 1 calc R . . C3A C -0.0227(5) 0.4557(11) 0.6775(2) 0.0303(14) Uani 1 1 d . . . H3A H -0.0874 0.4324 0.7064 0.036 Uiso 1 1 calc R . . C4A C 0.0641(5) 0.6438(11) 0.67997(19) 0.0267(15) Uani 1 1 d . . . C5A C 0.1578(5) 0.6796(13) 0.63685(18) 0.0342(15) Uani 1 1 d . . . H5A H 0.2169 0.8085 0.6380 0.041 Uiso 1 1 calc R . . C6A C 0.1644(5) 0.5271(13) 0.5924(2) 0.0371(16) Uani 1 1 d . . . H6A H 0.2269 0.5504 0.5627 0.044 Uiso 1 1 calc R . . C7A C 0.0681(5) 0.8076(11) 0.72814(19) 0.0273(13) Uani 1 1 d . . . C8A C -0.0550(5) 0.9695(11) 0.80730(18) 0.0271(14) Uani 1 1 d . . . H8A H 0.0112 1.0992 0.8047 0.032 Uiso 1 1 calc R . . C9A C -0.2045(5) 1.0599(11) 0.8132(2) 0.0299(14) Uani 1 1 d . . . H9AA H -0.2329 1.1519 0.7797 0.045 Uiso 1 1 calc R . . H9AB H -0.2059 1.1513 0.8479 0.045 Uiso 1 1 calc R . . H9AC H -0.2708 0.9346 0.8157 0.045 Uiso 1 1 calc R . . C10A C -0.0055(5) 0.8276(12) 0.8587(2) 0.0265(14) Uani 1 1 d . . . C11A C -0.0625(5) 0.6164(11) 0.8665(2) 0.0306(17) Uani 1 1 d . . . H11A H -0.1307 0.5584 0.8387 0.037 Uiso 1 1 calc R . . C12A C -0.0215(5) 0.4896(12) 0.9139(2) 0.0345(17) Uani 1 1 d . . . H12A H -0.0627 0.3464 0.9189 0.041 Uiso 1 1 calc R . . C13A C 0.0795(6) 0.5703(12) 0.9543(2) 0.0361(17) Uani 1 1 d . . . H13A H 0.1083 0.4832 0.9870 0.043 Uiso 1 1 calc R . . C14A C 0.1371(6) 0.7769(13) 0.9464(2) 0.0365(17) Uani 1 1 d . . . H14A H 0.2073 0.8324 0.9737 0.044 Uiso 1 1 calc R . . C15A C 0.0947(5) 0.9079(12) 0.89909(19) 0.0312(16) Uani 1 1 d . . . H15A H 0.1347 1.0523 0.8946 0.037 Uiso 1 1 calc R . . O1B O 0.3174(3) 0.0831(7) 0.25493(13) 0.0312(11) Uani 1 1 d . . . N1B N 0.5479(4) 0.1534(10) 0.24366(15) 0.0273(12) Uani 1 1 d . . . C1B C 0.4251(6) 0.6567(14) 0.4081(2) 0.0379(17) Uani 1 1 d . . . C2B C 0.5097(5) 0.6930(13) 0.3623(2) 0.0378(16) Uani 1 1 d . . . H2B H 0.5657 0.8251 0.3616 0.045 Uiso 1 1 calc R . . C3B C 0.5138(5) 0.5407(12) 0.3179(2) 0.0352(15) Uani 1 1 d . . . H3B H 0.5728 0.5686 0.2873 0.042 Uiso 1 1 calc R . . C4B C 0.4321(5) 0.3472(11) 0.31787(19) 0.0270(15) Uani 1 1 d . . . C5B C 0.3450(5) 0.3124(13) 0.36278(18) 0.0338(15) Uani 1 1 d . . . H5B H 0.2867 0.1827 0.3629 0.041 Uiso 1 1 calc R . . C6B C 0.3425(6) 0.4640(14) 0.4070(2) 0.0417(18) Uani 1 1 d . . . H6B H 0.2830 0.4363 0.4375 0.050 Uiso 1 1 calc R . . C7B C 0.4283(5) 0.1833(11) 0.26998(18) 0.0252(13) Uani 1 1 d . . . C8B C 0.5532(5) 0.0253(12) 0.19069(18) 0.0276(14) Uani 1 1 d . . . H8B H 0.4875 -0.1054 0.1926 0.033 Uiso 1 1 calc R . . C9B C 0.7033(5) -0.0634(12) 0.1852(2) 0.0344(16) Uani 1 1 d . . . H9BA H 0.7319 -0.1540 0.2190 0.052 Uiso 1 1 calc R . . H9BB H 0.7690 0.0628 0.1826 0.052 Uiso 1 1 calc R . . H9BC H 0.7056 -0.1557 0.1507 0.052 Uiso 1 1 calc R . . C10B C 0.5048(5) 0.1674(12) 0.13931(19) 0.0252(13) Uani 1 1 d . . . C11B C 0.5618(5) 0.3785(10) 0.1321(2) 0.0294(15) Uani 1 1 d . . . H11B H 0.6304 0.4355 0.1599 0.035 Uiso 1 1 calc R . . C12B C 0.5200(5) 0.5064(11) 0.0850(2) 0.0333(16) Uani 1 1 d . . . H12B H 0.5609 0.6501 0.0803 0.040 Uiso 1 1 calc R . . C13B C 0.4194(5) 0.4277(13) 0.0447(2) 0.0364(17) Uani 1 1 d . . . H13B H 0.3916 0.5164 0.0122 0.044 Uiso 1 1 calc R . . C14B C 0.3587(6) 0.2191(13) 0.0517(2) 0.0397(19) Uani 1 1 d . . . H14B H 0.2880 0.1649 0.0244 0.048 Uiso 1 1 calc R . . C15B C 0.4020(5) 0.0908(11) 0.0987(2) 0.0321(16) Uani 1 1 d . . . H15B H 0.3609 -0.0527 0.1034 0.038 Uiso 1 1 calc R . . C16B C 0.4219(6) 0.8229(15) 0.4567(2) 0.056(2) Uani 1 1 d . . . H16A H 0.3573 0.7692 0.4848 0.084 Uiso 1 1 calc R . . H16B H 0.3889 0.9682 0.4416 0.084 Uiso 1 1 calc R . . H16C H 0.5176 0.8392 0.4751 0.084 Uiso 1 1 calc R . . HN1A H -0.128(7) 0.753(15) 0.744(3) 0.10(3) Uiso 1 1 d . . . HN1B H 0.624(4) 0.228(8) 0.2549(14) 0.008(10) Uiso 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 O1A 0.0217(19) 0.035(3) 0.0393(18) 0.000(2) 0.0017(14) -0.004(2) O2A 0.073(2) 0.050(3) 0.052(2) -0.016(2) 0.0110(17) -0.008(2) O3A 0.062(2) 0.070(3) 0.0528(19) -0.013(2) 0.0245(17) 0.014(2) N1A 0.018(2) 0.027(3) 0.031(2) -0.006(2) 0.0019(16) 0.000(3) N2A 0.049(3) 0.041(4) 0.038(2) -0.001(3) 0.006(2) 0.009(3) C1A 0.035(3) 0.038(5) 0.027(2) -0.002(3) -0.002(2) 0.011(4) C2A 0.036(3) 0.032(4) 0.036(3) -0.006(3) 0.001(2) -0.003(3) C3A 0.026(3) 0.030(4) 0.035(3) 0.007(3) 0.008(2) -0.003(3) C4A 0.023(3) 0.028(4) 0.030(2) 0.001(3) 0.004(2) 0.011(3) C5A 0.032(3) 0.036(4) 0.035(3) 0.002(3) 0.006(2) 0.000(4) C6A 0.035(3) 0.047(5) 0.031(3) 0.002(3) 0.012(2) 0.005(4) C7A 0.022(3) 0.028(4) 0.032(2) 0.010(3) 0.001(2) -0.006(3) C8A 0.024(3) 0.021(4) 0.036(2) 0.000(3) 0.000(2) 0.000(3) C9A 0.027(3) 0.020(4) 0.043(3) -0.004(3) 0.002(2) 0.006(3) C10A 0.017(3) 0.030(4) 0.033(3) 0.000(3) 0.0050(19) 0.001(3) C11A 0.022(3) 0.037(5) 0.032(3) 0.000(3) -0.004(2) -0.002(3) C12A 0.029(3) 0.033(5) 0.041(3) 0.002(3) 0.002(2) -0.009(3) C13A 0.035(3) 0.036(5) 0.038(3) 0.001(3) 0.002(2) 0.010(4) C14A 0.038(3) 0.038(5) 0.032(3) -0.006(3) -0.008(2) -0.002(4) C15A 0.025(3) 0.030(4) 0.039(3) -0.004(3) -0.001(2) 0.001(3) O1B 0.0214(18) 0.034(3) 0.0379(18) -0.001(2) -0.0005(14) -0.004(2) N1B 0.018(2) 0.035(3) 0.029(2) 0.002(2) 0.0004(16) -0.004(3) C1B 0.039(3) 0.038(5) 0.037(3) -0.004(3) 0.002(2) 0.008(4) C2B 0.040(3) 0.030(4) 0.044(3) 0.004(3) 0.000(2) -0.001(4) C3B 0.034(3) 0.039(4) 0.032(2) -0.006(3) 0.004(2) 0.006(3) C4B 0.020(3) 0.034(4) 0.027(2) 0.007(3) -0.0027(19) -0.002(3) C5B 0.027(3) 0.043(5) 0.031(2) 0.005(3) 0.001(2) -0.005(4) C6B 0.040(3) 0.057(5) 0.028(3) 0.003(4) 0.005(2) 0.002(4) C7B 0.024(3) 0.025(4) 0.026(2) 0.001(3) -0.0032(19) 0.009(3) C8B 0.023(3) 0.026(4) 0.034(2) -0.008(3) 0.006(2) -0.005(3) C9B 0.024(3) 0.038(4) 0.042(3) -0.001(3) 0.002(2) -0.002(3) C10B 0.026(3) 0.021(4) 0.029(2) -0.006(3) 0.004(2) 0.005(3) C11B 0.030(3) 0.021(4) 0.037(3) -0.004(3) 0.000(2) -0.003(3) C12B 0.036(3) 0.020(5) 0.043(3) 0.004(3) 0.001(2) -0.001(3) C13B 0.037(3) 0.039(5) 0.032(3) 0.004(3) -0.005(2) -0.001(4) C14B 0.033(3) 0.046(5) 0.039(3) -0.005(4) -0.009(2) -0.006(4) C15B 0.030(3) 0.022(4) 0.044(3) -0.008(3) 0.003(2) -0.006(3) C16B 0.079(5) 0.052(5) 0.037(3) -0.012(4) 0.001(3) 0.013(5) _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 O1A C7A 1.239(6) . ? O2A N2A 1.230(6) . ? O3A N2A 1.220(5) . ? N1A C7A 1.339(6) . ? N1A C8A 1.469(6) . ? N2A C1A 1.471(8) . ? C1A C6A 1.369(9) . ? C1A C2A 1.378(7) . ? C2A C3A 1.381(8) . ? C3A C4A 1.389(8) . ? C4A C5A 1.400(6) . ? C4A C7A 1.491(8) . ? C5A C6A 1.386(8) . ? C8A C10A 1.520(7) . ? C8A C9A 1.525(6) . ? C10A C15A 1.380(7) . ? C10A C11A 1.388(9) . ? C11A C12A 1.378(7) . ? C12A C13A 1.387(7) . ? C13A C14A 1.366(9) . ? C14A C15A 1.393(8) . ? O1B C7B 1.237(6) . ? N1B C7B 1.333(6) . ? N1B C8B 1.460(6) . ? C1B C6B 1.390(10) . ? C1B C2B 1.394(7) . ? C1B C16B 1.510(9) . ? C2B C3B 1.383(8) . ? C3B C4B 1.390(9) . ? C4B C5B 1.391(6) . ? C4B C7B 1.486(8) . ? C5B C6B 1.377(9) . ? C8B C10B 1.518(8) . ? C8B C9B 1.526(7) . ? C10B C11B 1.385(9) . ? C10B C15B 1.391(7) . ? C11B C12B 1.378(7) . ? C12B C13B 1.378(7) . ? C13B C14B 1.385(9) . ? C14B C15B 1.381(8) . ? 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 C7A N1A C8A 121.3(5) . . ? O3A N2A O2A 123.3(5) . . ? O3A N2A C1A 118.4(5) . . ? O2A N2A C1A 118.3(4) . . ? C6A C1A C2A 123.4(6) . . ? C6A C1A N2A 118.5(5) . . ? C2A C1A N2A 118.1(6) . . ? C1A C2A C3A 117.8(6) . . ? C2A C3A C4A 121.0(5) . . ? C3A C4A C5A 119.4(5) . . ? C3A C4A C7A 123.3(4) . . ? C5A C4A C7A 117.2(6) . . ? C6A C5A C4A 120.1(6) . . ? C1A C6A C5A 118.4(5) . . ? O1A C7A N1A 122.6(5) . . ? O1A C7A C4A 120.4(4) . . ? N1A C7A C4A 117.0(5) . . ? N1A C8A C10A 110.5(5) . . ? N1A C8A C9A 109.3(4) . . ? C10A C8A C9A 111.5(4) . . ? C15A C10A C11A 118.7(6) . . ? C15A C10A C8A 120.7(6) . . ? C11A C10A C8A 120.5(5) . . ? C12A C11A C10A 120.9(5) . . ? C11A C12A C13A 120.3(6) . . ? C14A C13A C12A 118.9(6) . . ? C13A C14A C15A 121.2(6) . . ? C10A C15A C14A 119.9(6) . . ? C7B N1B C8B 122.6(4) . . ? C6B C1B C2B 117.6(6) . . ? C6B C1B C16B 121.4(5) . . ? C2B C1B C16B 121.0(7) . . ? C3B C2B C1B 121.4(7) . . ? C2B C3B C4B 120.3(5) . . ? C3B C4B C5B 118.6(6) . . ? C3B C4B C7B 122.3(5) . . ? C5B C4B C7B 119.0(6) . . ? C6B C5B C4B 120.6(6) . . ? C5B C6B C1B 121.5(5) . . ? O1B C7B N1B 122.0(5) . . ? O1B C7B C4B 120.8(4) . . ? N1B C7B C4B 117.1(5) . . ? N1B C8B C10B 110.7(6) . . ? N1B C8B C9B 109.6(4) . . ? C10B C8B C9B 111.2(4) . . ? C11B C10B C15B 118.4(6) . . ? C11B C10B C8B 120.3(5) . . ? C15B C10B C8B 121.2(6) . . ? C12B C11B C10B 120.5(5) . . ? C11B C12B C13B 120.5(6) . . ? C12B C13B C14B 119.9(6) . . ? C15B C14B C13B 119.3(5) . . ? C14B C15B C10B 121.3(6) . . ? _diffrn_measured_fraction_theta_max 0.868 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.868 _refine_diff_density_max 0.235 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.057