# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_saka360_pbcn _database_code_depnum_ccdc_archive 'CCDC 927187' #TrackingRef '18152_web_deposit_cif_file_0_MasamiSakamoto_1362111942.trans-3,4-diphenylsuccinimides3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N O2' _chemical_formula_weight 251.27 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.1134(11) _cell_length_b 13.6354(11) _cell_length_c 7.2439(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1295.26(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 1314 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 24.53 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details 'SADABS Sheldrick 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 5675 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1154 _reflns_number_gt 977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.3103P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1154 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.02525(10) 0.13819(10) 0.09705(17) 0.0230(3) Uani 1 1 d . . . C2 C 0.01091(10) 0.24599(9) 0.14492(17) 0.0209(3) Uani 1 1 d . . . H2 H -0.0521 0.2694 0.0807 0.025 Uiso 1 1 calc R . . C3 C 0.09807(10) 0.31091(9) 0.08511(17) 0.0224(3) Uani 1 1 d . . . C4 C 0.19619(10) 0.29663(10) 0.15358(19) 0.0281(4) Uani 1 1 d . . . H4 H 0.2095 0.2432 0.2342 0.034 Uiso 1 1 calc R . . C5 C 0.27449(12) 0.35977(12) 0.1050(2) 0.0347(4) Uani 1 1 d . . . H5 H 0.3409 0.3502 0.1541 0.042 Uiso 1 1 calc R . . C6 C 0.25602(13) 0.43678(12) -0.0150(2) 0.0407(4) Uani 1 1 d . . . H6 H 0.3098 0.4797 -0.0493 0.049 Uiso 1 1 calc R . . C7 C 0.15950(14) 0.45086(12) -0.0843(2) 0.0426(4) Uani 1 1 d . . . H7 H 0.1467 0.5035 -0.1670 0.051 Uiso 1 1 calc R . . C8 C 0.08073(12) 0.38845(10) -0.0340(2) 0.0328(4) Uani 1 1 d . . . H8 H 0.0142 0.3991 -0.0818 0.039 Uiso 1 1 calc R . . N1 N 0.0000 0.08327(11) 0.2500 0.0260(4) Uani 1 2 d S . . H1 H 0.0000 0.0187 0.2500 0.031 Uiso 1 2 calc SR . . O1 O 0.05121(8) 0.10528(7) -0.05094(13) 0.0325(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0204(7) 0.0229(7) 0.0256(7) -0.0025(6) 0.0013(5) -0.0012(5) C2 0.0210(7) 0.0207(7) 0.0210(7) 0.0000(5) -0.0002(5) 0.0013(5) C3 0.0278(7) 0.0198(7) 0.0196(6) -0.0028(5) 0.0033(5) -0.0020(5) C4 0.0281(8) 0.0299(8) 0.0263(7) -0.0004(6) 0.0026(6) 0.0004(6) C5 0.0281(8) 0.0433(9) 0.0325(8) -0.0122(7) 0.0058(6) -0.0066(7) C6 0.0448(10) 0.0344(9) 0.0429(9) -0.0073(7) 0.0193(8) -0.0167(7) C7 0.0543(11) 0.0316(9) 0.0421(9) 0.0126(7) 0.0106(8) -0.0052(7) C8 0.0374(9) 0.0306(8) 0.0305(8) 0.0072(7) 0.0009(6) -0.0002(6) N1 0.0314(9) 0.0165(8) 0.0301(9) 0.000 0.0039(7) 0.000 O1 0.0390(6) 0.0287(6) 0.0297(6) -0.0078(4) 0.0077(4) -0.0014(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 C1 O1 1.2109(15) . ? C1 N1 1.3777(15) . ? C1 C2 1.5219(18) . ? C2 C3 1.5092(18) . ? C2 C2 1.549(2) 3 ? C2 H2 1.0000 . ? C3 C8 1.3835(19) . ? C3 C4 1.3927(19) . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 C7 1.375(2) . ? C6 H6 0.9500 . ? C7 C8 1.387(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? N1 C1 1.3777(15) 3 ? N1 H1 0.8800 . ? 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 O1 C1 N1 125.32(12) . . ? O1 C1 C2 126.46(12) . . ? N1 C1 C2 108.18(11) . . ? C3 C2 C1 114.05(10) . . ? C3 C2 C2 114.96(11) . 3 ? C1 C2 C2 104.28(7) . 3 ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C2 C2 H2 107.7 3 . ? C8 C3 C4 118.74(13) . . ? C8 C3 C2 120.19(12) . . ? C4 C3 C2 121.03(12) . . ? C5 C4 C3 120.50(14) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 120.07(15) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 119.74(14) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.26(15) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C3 C8 C7 120.68(15) . . ? C3 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C1 N1 C1 114.15(15) 3 . ? C1 N1 H1 122.9 3 . ? C1 N1 H1 122.9 . . ? 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 C1 C2 C3 -47.96(18) . . . . ? N1 C1 C2 C3 134.18(10) . . . . ? O1 C1 C2 C2 -174.15(14) . . . 3 ? N1 C1 C2 C2 7.98(15) . . . 3 ? C1 C2 C3 C8 121.41(13) . . . . ? C2 C2 C3 C8 -118.20(14) 3 . . . ? C1 C2 C3 C4 -61.11(16) . . . . ? C2 C2 C3 C4 59.28(15) 3 . . . ? C8 C3 C4 C5 0.8(2) . . . . ? C2 C3 C4 C5 -176.67(12) . . . . ? C3 C4 C5 C6 -1.1(2) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C4 C3 C8 C7 0.0(2) . . . . ? C2 C3 C8 C7 177.52(13) . . . . ? C6 C7 C8 C3 -0.5(2) . . . . ? O1 C1 N1 C1 178.89(16) . . . 3 ? C2 C1 N1 C1 -3.21(6) . . . 3 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.187 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.041 data_sakacu002_p21212_2 _database_code_depnum_ccdc_archive 'CCDC 927188' #TrackingRef '18153_web_deposit_cif_file_1_MasamiSakamoto_1362111942.trans-N-isopropyl-3,4-diphenylsuccinimide3e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration ad _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 17.0588(3) _cell_length_b 5.30480(10) _cell_length_c 8.58540(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 776.92(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 3230 _cell_measurement_theta_min 5.15 _cell_measurement_theta_max 66.03 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8820 _exptl_absorpt_correction_T_max 0.9384 _exptl_absorpt_process_details 'SADABS Sheldrick 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 3621 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 66.39 _reflns_number_total 1267 _reflns_number_gt 1248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.0451P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 1267 _refine_ls_number_parameters 177 _refine_ls_number_restraints 289 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.064 _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 0.4258(2) 0.3043(7) 0.7367(5) 0.0513(8) Uani 0.50 1 d PDU A -1 C1 C 0.5479(3) -0.2049(11) 0.6610(8) 0.0361(12) Uani 0.50 1 d PDU A -1 C2 C 0.5285(4) -0.1332(17) 0.4898(7) 0.0350(12) Uani 0.50 1 d PDU A -1 H2 H 0.4955 -0.2687 0.4423 0.042 Uiso 0.50 1 calc PR A -1 C3 C 0.6044(4) -0.1093(15) 0.3987(8) 0.0460(16) Uani 0.50 1 d PGDU A -1 C4 C 0.6554(5) 0.0910(14) 0.4242(10) 0.0440(14) Uani 0.50 1 d PGDU A -1 H4 H 0.6419 0.2196 0.4964 0.053 Uiso 0.50 1 calc PR A -1 C5 C 0.7261(5) 0.1030(16) 0.3439(12) 0.0500(16) Uani 0.50 1 d PGU A -1 H5 H 0.7609 0.2399 0.3613 0.060 Uiso 0.50 1 calc PR A -1 C6 C 0.7457(4) -0.0851(19) 0.2382(10) 0.0529(13) Uani 0.50 1 d PGU A -1 H6 H 0.7940 -0.0768 0.1834 0.064 Uiso 0.50 1 calc PR A -1 C7 C 0.6948(4) -0.2854(18) 0.2128(9) 0.0488(13) Uani 0.50 1 d PGU A -1 H7 H 0.7082 -0.4140 0.1406 0.059 Uiso 0.50 1 calc PR A -1 C8 C 0.6241(4) -0.2975(15) 0.2931(9) 0.0404(11) Uani 0.50 1 d PGU A -1 H8 H 0.5893 -0.4343 0.2757 0.048 Uiso 0.50 1 calc PR A -1 C9 C 0.51340(16) -0.0582(4) 0.9301(2) 0.0419(6) Uani 0.50 1 d PDU A -1 H9 H 0.5518 -0.1944 0.9556 0.050 Uiso 0.50 1 calc PR A -1 C10 C 0.4342(3) -0.1388(14) 0.9933(12) 0.0501(13) Uani 0.50 1 d PDU A -1 H10A H 0.4195 -0.3016 0.9478 0.075 Uiso 0.50 1 calc PR A -1 H10B H 0.3947 -0.0122 0.9660 0.075 Uiso 0.50 1 calc PR A -1 H10C H 0.4372 -0.1548 1.1068 0.075 Uiso 0.50 1 calc PR A -1 N1 N 0.5104(3) -0.0347(9) 0.7580(3) 0.0351(9) Uani 0.50 1 d PDU A -1 O1 O 0.5881(2) -0.3785(6) 0.7041(5) 0.0480(7) Uani 0.50 1 d PDU A -1 C1A C 0.4671(3) 0.1429(10) 0.6787(7) 0.0365(13) Uani 0.50 1 d PDU A -1 C2A C 0.4792(5) 0.1096(17) 0.5063(8) 0.0395(15) Uani 0.50 1 d PDU A -1 H2A H 0.5125 0.2530 0.4700 0.047 Uiso 0.50 1 calc PR A -1 C3A C 0.4039(4) 0.1151(12) 0.4103(7) 0.0319(10) Uani 0.50 1 d PGDU A -1 C4A C 0.3458(5) -0.0618(12) 0.4408(9) 0.0389(13) Uani 0.50 1 d PGDU A -1 H4A H 0.3531 -0.1833 0.5208 0.047 Uiso 0.50 1 calc PR A -1 C5A C 0.2770(5) -0.0611(16) 0.3542(11) 0.0454(13) Uani 0.50 1 d PGU A -1 H5A H 0.2373 -0.1820 0.3750 0.055 Uiso 0.50 1 calc PR A -1 C6A C 0.2662(4) 0.117(2) 0.2371(10) 0.0539(14) Uani 0.50 1 d PGU A -1 H6A H 0.2192 0.1172 0.1779 0.065 Uiso 0.50 1 calc PR A -1 C7A C 0.3243(4) 0.2936(19) 0.2067(9) 0.0523(15) Uani 0.50 1 d PGU A -1 H7A H 0.3170 0.4150 0.1267 0.063 Uiso 0.50 1 calc PR A -1 C8A C 0.3932(4) 0.2928(14) 0.2933(9) 0.0452(14) Uani 0.50 1 d PGU A -1 H8A H 0.4329 0.4138 0.2724 0.054 Uiso 0.50 1 calc PR A -1 C10A C 0.5440(4) 0.1852(13) 1.0005(12) 0.0509(14) Uani 0.50 1 d PDU A -1 H10D H 0.5043 0.3174 0.9899 0.076 Uiso 0.50 1 calc PR A -1 H10E H 0.5919 0.2366 0.9461 0.076 Uiso 0.50 1 calc PR A -1 H10F H 0.5557 0.1586 1.1111 0.076 Uiso 0.50 1 calc PR A -1 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 0.0673(18) 0.0445(18) 0.0422(17) -0.0130(14) -0.0061(13) 0.0180(13) C1 0.044(2) 0.026(2) 0.038(2) -0.0018(18) 0.0046(16) -0.0011(17) C2 0.056(2) 0.0256(18) 0.0237(17) -0.0003(14) -0.0072(17) 0.0021(15) C3 0.056(2) 0.047(3) 0.035(2) 0.007(2) 0.0021(19) 0.004(2) C4 0.060(3) 0.037(2) 0.0352(19) 0.0068(18) -0.0025(19) -0.0031(18) C5 0.057(2) 0.039(3) 0.054(3) 0.010(2) 0.005(2) -0.0027(17) C6 0.058(2) 0.053(3) 0.048(2) 0.0082(19) 0.0035(18) -0.002(2) C7 0.054(3) 0.051(2) 0.0415(19) -0.0060(18) 0.0024(17) 0.005(2) C8 0.051(3) 0.0343(18) 0.036(2) -0.0052(17) -0.0072(16) -0.0003(16) C9 0.0583(17) 0.0360(16) 0.0314(8) 0.0026(8) -0.0010(9) 0.0015(11) C10 0.067(3) 0.044(3) 0.0396(19) -0.0093(19) 0.011(2) -0.002(2) N1 0.042(2) 0.031(3) 0.0320(8) -0.0009(11) -0.0001(10) 0.0077(16) O1 0.0585(15) 0.0403(16) 0.0453(17) 0.0107(12) 0.0061(12) 0.0115(12) C1A 0.047(2) 0.027(3) 0.035(2) -0.0070(19) -0.0041(16) 0.0025(19) C2A 0.052(2) 0.029(2) 0.038(2) 0.0070(15) -0.0081(16) -0.0107(17) C3A 0.0507(19) 0.0215(18) 0.0236(18) -0.0023(16) 0.0075(17) -0.0031(16) C4A 0.055(2) 0.0275(18) 0.035(2) -0.0019(18) 0.0051(17) -0.0026(16) C5A 0.056(2) 0.033(2) 0.047(2) -0.0088(18) 0.006(2) -0.0074(15) C6A 0.052(2) 0.058(3) 0.052(3) -0.004(2) -0.0102(19) 0.001(2) C7A 0.057(3) 0.051(2) 0.049(2) 0.0079(18) 0.000(2) 0.004(2) C8A 0.052(2) 0.040(2) 0.044(2) -0.0007(19) 0.0017(18) 0.0006(18) C10A 0.070(3) 0.041(3) 0.0416(18) 0.002(2) -0.014(3) -0.007(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 O1A C1A 1.215(7) . ? C1 O1 1.206(7) . ? C1 N1 1.385(5) . ? C1 C2 1.553(8) . ? C2 C3 1.518(7) . ? C2 C2A 1.545(4) . ? C2 H2 1.0000 . ? C3 C4 1.3900 . ? C3 C8 1.3900 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.3900 . ? C6 H6 0.9500 . ? C7 C8 1.3900 . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N1 1.483(3) . ? C9 C10 1.517(7) . ? C9 C10A 1.518(7) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N1 C1A 1.378(5) . ? C1A C2A 1.505(8) . ? C2A C3A 1.526(7) . ? C2A H2A 1.0000 . ? C3A C4A 1.3900 . ? C3A C8A 1.3900 . ? C4A C5A 1.3900 . ? C4A H4A 0.9500 . ? C5A C6A 1.3900 . ? C5A H5A 0.9500 . ? C6A C7A 1.3900 . ? C6A H6A 0.9500 . ? C7A C8A 1.3900 . ? C7A H7A 0.9500 . ? C8A H8A 0.9500 . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 125.1(5) . . ? O1 C1 C2 126.7(5) . . ? N1 C1 C2 108.1(5) . . ? C3 C2 C2A 116.2(5) . . ? C3 C2 C1 109.0(5) . . ? C2A C2 C1 103.5(6) . . ? C3 C2 H2 109.3 . . ? C2A C2 H2 109.3 . . ? C1 C2 H2 109.3 . . ? C4 C3 C8 120.0 . . ? C4 C3 C2 121.1(4) . . ? C8 C3 C2 118.8(5) . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 120.0 . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? N1 C9 C10 110.5(5) . . ? N1 C9 C10A 109.7(5) . . ? C10 C9 C10A 113.8(3) . . ? N1 C9 H9 107.5 . . ? C10 C9 H9 107.5 . . ? C10A C9 H9 107.5 . . ? C1A N1 C1 113.3(2) . . ? C1A N1 C9 124.6(4) . . ? C1 N1 C9 121.9(4) . . ? O1A C1A N1 126.2(5) . . ? O1A C1A C2A 124.4(5) . . ? N1 C1A C2A 109.4(5) . . ? C1A C2A C3A 114.4(6) . . ? C1A C2A C2 105.2(6) . . ? C3A C2A C2 115.1(6) . . ? C1A C2A H2A 107.2 . . ? C3A C2A H2A 107.2 . . ? C2 C2A H2A 107.2 . . ? C4A C3A C8A 120.0 . . ? C4A C3A C2A 119.0(4) . . ? C8A C3A C2A 121.0(4) . . ? C3A C4A C5A 120.0 . . ? C3A C4A H4A 120.0 . . ? C5A C4A H4A 120.0 . . ? C6A C5A C4A 120.0 . . ? C6A C5A H5A 120.0 . . ? C4A C5A H5A 120.0 . . ? C5A C6A C7A 120.0 . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? C8A C7A C6A 120.0 . . ? C8A C7A H7A 120.0 . . ? C6A C7A H7A 120.0 . . ? C7A C8A C3A 120.0 . . ? C7A C8A H8A 120.0 . . ? C3A C8A H8A 120.0 . . ? 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 C1 C2 C3 -52.8(8) . . . . ? N1 C1 C2 C3 127.5(6) . . . . ? O1 C1 C2 C2A -177.1(5) . . . . ? N1 C1 C2 C2A 3.2(5) . . . . ? C2A C2 C3 C4 45.4(8) . . . . ? C1 C2 C3 C4 -71.0(7) . . . . ? C2A C2 C3 C8 -137.2(6) . . . . ? C1 C2 C3 C8 106.3(6) . . . . ? C8 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C5 177.3(7) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C6 C7 C8 C3 0.0 . . . . ? C4 C3 C8 C7 0.0 . . . . ? C2 C3 C8 C7 -177.4(7) . . . . ? O1 C1 N1 C1A -178.9(4) . . . . ? C2 C1 N1 C1A 0.8(8) . . . . ? O1 C1 N1 C9 -3.0(9) . . . . ? C2 C1 N1 C9 176.7(5) . . . . ? C10 C9 N1 C1A 66.6(6) . . . . ? C10A C9 N1 C1A -59.7(6) . . . . ? C10 C9 N1 C1 -108.9(6) . . . . ? C10A C9 N1 C1 124.9(5) . . . . ? C1 N1 C1A O1A 176.1(4) . . . . ? C9 N1 C1A O1A 0.3(9) . . . . ? C1 N1 C1A C2A -4.6(8) . . . . ? C9 N1 C1A C2A 179.6(5) . . . . ? O1A C1A C2A C3A -46.9(8) . . . . ? N1 C1A C2A C3A 133.8(6) . . . . ? O1A C1A C2A C2 -174.3(5) . . . . ? N1 C1A C2A C2 6.4(5) . . . . ? C3 C2 C2A C1A -125.1(7) . . . . ? C1 C2 C2A C1A -5.61(19) . . . . ? C3 C2 C2A C3A 107.9(2) . . . . ? C1 C2 C2A C3A -132.6(6) . . . . ? C1A C2A C3A C4A -59.5(8) . . . . ? C2 C2A C3A C4A 62.7(7) . . . . ? C1A C2A C3A C8A 120.9(6) . . . . ? C2 C2A C3A C8A -117.0(6) . . . . ? C8A C3A C4A C5A 0.0 . . . . ? C2A C3A C4A C5A -179.7(7) . . . . ? C3A C4A C5A C6A 0.0 . . . . ? C4A C5A C6A C7A 0.0 . . . . ? C5A C6A C7A C8A 0.0 . . . . ? C6A C7A C8A C3A 0.0 . . . . ? C4A C3A C8A C7A 0.0 . . . . ? C2A C3A C8A C7A 179.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 66.39 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.094 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.031 data_saka416_bca_y _database_code_depnum_ccdc_archive 'CCDC 927189' #TrackingRef '18154_web_deposit_cif_file_2_MasamiSakamoto_1362111942.trans-N-phenethyl-3,4-diphenylsuccinimide3g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 N O2' _chemical_formula_weight 355.42 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.729(4) _cell_length_b 8.588(3) _cell_length_c 37.580(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3785(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173 _cell_measurement_reflns_used 1101 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 18.10 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 17200 _diffrn_reflns_av_R_equivalents 0.1039 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.80 _reflns_number_total 3613 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+9.8338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3613 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1671 _refine_ls_R_factor_gt 0.1009 _refine_ls_wR_factor_ref 0.2534 _refine_ls_wR_factor_gt 0.2307 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 C1 C 0.9568(4) -0.0491(6) 0.65292(16) 0.0452(13) Uani 1 1 d . . . C2 C 0.9286(4) -0.0134(5) 0.61466(14) 0.0404(13) Uani 1 1 d . . . H2 H 0.8926 -0.1075 0.6037 0.048 Uiso 1 1 calc R . . C3 C 0.8373(4) 0.1182(5) 0.61732(13) 0.0362(11) Uani 1 1 d . . . H3 H 0.8764 0.2181 0.6112 0.043 Uiso 1 1 calc R . . C4 C 0.8084(4) 0.1253(6) 0.65654(14) 0.0401(12) Uani 1 1 d . . . C5 C 1.0326(4) 0.0320(6) 0.59277(14) 0.0401(12) Uani 1 1 d . . . C6 C 1.1145(4) 0.1322(6) 0.60672(15) 0.0451(13) Uani 1 1 d . . . H6 H 1.1069 0.1684 0.6305 0.054 Uiso 1 1 calc R . . C7 C 1.2066(4) 0.1798(7) 0.58666(17) 0.0568(16) Uani 1 1 d . . . H7 H 1.2618 0.2480 0.5966 0.068 Uiso 1 1 calc R . . C8 C 1.2180(5) 0.1285(8) 0.55232(18) 0.0693(19) Uani 1 1 d . . . H8 H 1.2808 0.1622 0.5383 0.083 Uiso 1 1 calc R . . C9 C 1.1370(6) 0.0260(8) 0.53771(17) 0.0700(19) Uani 1 1 d . . . H9 H 1.1457 -0.0127 0.5142 0.084 Uiso 1 1 calc R . . C10 C 1.0454(5) -0.0168(6) 0.55808(16) 0.0527(15) Uani 1 1 d . . . H10 H 0.9888 -0.0823 0.5479 0.063 Uiso 1 1 calc R . . C11 C 0.7361(4) 0.1026(5) 0.59227(13) 0.0379(12) Uani 1 1 d . . . C12 C 0.6330(4) 0.0364(6) 0.60387(14) 0.0410(12) Uani 1 1 d . . . H12 H 0.6256 0.0029 0.6279 0.049 Uiso 1 1 calc R . . C13 C 0.5416(4) 0.0193(6) 0.58045(16) 0.0485(14) Uani 1 1 d . . . H13 H 0.4718 -0.0239 0.5886 0.058 Uiso 1 1 calc R . . C14 C 0.5526(5) 0.0652(7) 0.54546(16) 0.0530(15) Uani 1 1 d . . . H14 H 0.4908 0.0523 0.5294 0.064 Uiso 1 1 calc R . . C15 C 0.6547(5) 0.1307(8) 0.53369(15) 0.0594(16) Uani 1 1 d . . . H15 H 0.6622 0.1617 0.5095 0.071 Uiso 1 1 calc R . . C16 C 0.7461(5) 0.1511(6) 0.55712(14) 0.0499(14) Uani 1 1 d . . . H16 H 0.8148 0.1979 0.5491 0.060 Uiso 1 1 calc R . . C17 C 0.8863(5) 0.0224(7) 0.71370(15) 0.0554(15) Uani 1 1 d . . . H17A H 0.9453 -0.0540 0.7208 0.066 Uiso 1 1 calc R . . H17B H 0.8119 -0.0162 0.7225 0.066 Uiso 1 1 calc R . . C18 C 0.9124(5) 0.1790(7) 0.73157(15) 0.0539(15) Uani 1 1 d . . . H18A H 0.8426 0.2438 0.7315 0.065 Uiso 1 1 calc R . . H18B H 0.9340 0.1604 0.7567 0.065 Uiso 1 1 calc R . . C19 C 1.0071(4) 0.2673(6) 0.71331(13) 0.0394(12) Uani 1 1 d . . . C20 C 1.1200(4) 0.2141(6) 0.71477(14) 0.0443(13) Uani 1 1 d . . . H20 H 1.1375 0.1237 0.7283 0.053 Uiso 1 1 calc R . . C21 C 1.2063(4) 0.2906(6) 0.69693(15) 0.0504(14) Uani 1 1 d . . . H21 H 1.2819 0.2513 0.6980 0.060 Uiso 1 1 calc R . . C22 C 1.1835(4) 0.4249(6) 0.67743(15) 0.0479(14) Uani 1 1 d . . . H22 H 1.2430 0.4770 0.6651 0.058 Uiso 1 1 calc R . . C23 C 1.0727(5) 0.4820(6) 0.67620(15) 0.0542(15) Uani 1 1 d . . . H23 H 1.0562 0.5742 0.6632 0.065 Uiso 1 1 calc R . . C24 C 0.9850(5) 0.4026(6) 0.69426(15) 0.0491(14) Uani 1 1 d . . . H24 H 0.9094 0.4423 0.6934 0.059 Uiso 1 1 calc R . . N1 N 0.8828(3) 0.0316(5) 0.67527(11) 0.0403(10) Uani 1 1 d . . . O1 O 1.0331(3) -0.1334(4) 0.66420(11) 0.0572(11) Uani 1 1 d . . . O2 O 0.7314(3) 0.2023(4) 0.67027(10) 0.0535(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.039(3) 0.026(3) 0.071(4) 0.007(3) 0.004(3) -0.009(2) C2 0.028(2) 0.026(2) 0.066(4) -0.006(2) -0.005(2) 0.001(2) C3 0.031(2) 0.023(2) 0.055(3) 0.003(2) -0.001(2) 0.002(2) C4 0.024(2) 0.035(3) 0.062(4) 0.001(3) -0.003(2) 0.001(2) C5 0.028(2) 0.032(3) 0.060(3) -0.002(2) -0.004(2) 0.002(2) C6 0.036(3) 0.042(3) 0.057(3) 0.001(3) -0.001(3) -0.002(2) C7 0.034(3) 0.059(4) 0.077(4) 0.012(3) -0.006(3) -0.003(3) C8 0.050(4) 0.082(5) 0.076(5) 0.024(4) 0.018(3) 0.011(4) C9 0.075(5) 0.077(5) 0.059(4) -0.007(4) 0.008(4) 0.017(4) C10 0.052(3) 0.045(3) 0.061(4) -0.014(3) 0.001(3) 0.008(3) C11 0.039(3) 0.027(2) 0.047(3) -0.005(2) -0.002(2) 0.003(2) C12 0.040(3) 0.031(3) 0.052(3) 0.002(2) -0.002(2) -0.001(2) C13 0.039(3) 0.040(3) 0.067(4) -0.004(3) -0.004(3) 0.004(3) C14 0.040(3) 0.062(4) 0.058(4) -0.015(3) -0.013(3) 0.015(3) C15 0.053(3) 0.079(4) 0.047(3) 0.007(3) 0.000(3) 0.011(3) C16 0.044(3) 0.052(3) 0.054(3) 0.007(3) 0.005(3) 0.011(3) C17 0.044(3) 0.061(4) 0.062(4) 0.020(3) 0.002(3) -0.015(3) C18 0.052(3) 0.065(4) 0.044(3) 0.003(3) 0.002(3) 0.009(3) C19 0.034(3) 0.043(3) 0.041(3) -0.003(2) 0.001(2) 0.007(2) C20 0.036(3) 0.036(3) 0.062(4) -0.002(3) -0.008(3) 0.007(2) C21 0.038(3) 0.048(3) 0.066(4) -0.011(3) -0.007(3) -0.002(3) C22 0.043(3) 0.034(3) 0.067(4) -0.006(3) -0.010(3) -0.008(2) C23 0.064(4) 0.036(3) 0.063(4) 0.002(3) -0.014(3) -0.001(3) C24 0.050(3) 0.039(3) 0.058(4) -0.008(3) -0.016(3) 0.009(3) N1 0.036(2) 0.034(2) 0.051(3) 0.009(2) -0.004(2) -0.0006(19) O1 0.041(2) 0.036(2) 0.095(3) 0.023(2) -0.008(2) 0.0070(18) O2 0.0345(19) 0.056(2) 0.070(3) -0.012(2) -0.0039(18) 0.0049(18) _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 C1 O1 1.227(6) . ? C1 N1 1.392(6) . ? C1 C2 1.507(7) . ? C2 C5 1.522(7) . ? C2 C3 1.560(6) . ? C2 H2 1.0000 . ? C3 C4 1.514(7) . ? C3 C11 1.521(6) . ? C3 H3 1.0000 . ? C4 O2 1.233(5) . ? C4 N1 1.380(6) . ? C5 C10 1.378(7) . ? C5 C6 1.393(7) . ? C6 C7 1.379(7) . ? C6 H6 0.9500 . ? C7 C8 1.370(8) . ? C7 H7 0.9500 . ? C8 C9 1.406(9) . ? C8 H8 0.9500 . ? C9 C10 1.370(8) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.390(7) . ? C11 C12 1.405(7) . ? C12 C13 1.395(7) . ? C12 H12 0.9500 . ? C13 C14 1.379(8) . ? C13 H13 0.9500 . ? C14 C15 1.394(8) . ? C14 H14 0.9500 . ? C15 C16 1.399(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N1 1.447(7) . ? C17 C18 1.534(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.510(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.390(7) . ? C19 C20 1.401(6) . ? C20 C21 1.380(7) . ? C20 H20 0.9500 . ? C21 C22 1.392(7) . ? C21 H21 0.9500 . ? C22 C23 1.390(7) . ? C22 H22 0.9500 . ? C23 C24 1.408(8) . ? C23 H23 0.9500 . ? C24 H24 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 O1 C1 N1 122.7(5) . . ? O1 C1 C2 127.6(5) . . ? N1 C1 C2 109.7(4) . . ? C1 C2 C5 113.1(4) . . ? C1 C2 C3 103.7(4) . . ? C5 C2 C3 113.5(4) . . ? C1 C2 H2 108.8 . . ? C5 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C4 C3 C11 115.5(4) . . ? C4 C3 C2 104.2(4) . . ? C11 C3 C2 115.6(4) . . ? C4 C3 H3 107.0 . . ? C11 C3 H3 107.0 . . ? C2 C3 H3 107.0 . . ? O2 C4 N1 124.3(5) . . ? O2 C4 C3 126.4(4) . . ? N1 C4 C3 109.3(4) . . ? C10 C5 C6 118.0(5) . . ? C10 C5 C2 121.4(5) . . ? C6 C5 C2 120.5(5) . . ? C7 C6 C5 121.2(5) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 119.8(6) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.2(6) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 118.7(6) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C9 C10 C5 122.2(6) . . ? C9 C10 H10 118.9 . . ? C5 C10 H10 118.9 . . ? C16 C11 C12 119.3(5) . . ? C16 C11 C3 119.7(5) . . ? C12 C11 C3 121.0(5) . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.0(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.9(5) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.6(5) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.7(5) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? N1 C17 C18 113.2(4) . . ? N1 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? N1 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 112.8(4) . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C24 C19 C20 118.0(5) . . ? C24 C19 C18 121.1(5) . . ? C20 C19 C18 120.9(5) . . ? C21 C20 C19 121.2(5) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 120.6(5) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 119.3(5) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 119.8(5) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C19 C24 C23 121.1(5) . . ? C19 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C4 N1 C1 112.1(4) . . ? C4 N1 C17 124.0(4) . . ? C1 N1 C17 123.8(4) . . ? 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 C1 C2 C5 -48.3(7) . . . . ? N1 C1 C2 C5 130.8(4) . . . . ? O1 C1 C2 C3 -171.7(4) . . . . ? N1 C1 C2 C3 7.4(5) . . . . ? C1 C2 C3 C4 -9.2(5) . . . . ? C5 C2 C3 C4 -132.2(4) . . . . ? C1 C2 C3 C11 -137.1(4) . . . . ? C5 C2 C3 C11 99.8(5) . . . . ? C11 C3 C4 O2 -44.1(7) . . . . ? C2 C3 C4 O2 -172.1(5) . . . . ? C11 C3 C4 N1 136.3(4) . . . . ? C2 C3 C4 N1 8.3(5) . . . . ? C1 C2 C5 C10 141.3(5) . . . . ? C3 C2 C5 C10 -100.9(5) . . . . ? C1 C2 C5 C6 -42.5(6) . . . . ? C3 C2 C5 C6 75.3(6) . . . . ? C10 C5 C6 C7 -0.8(7) . . . . ? C2 C5 C6 C7 -177.1(5) . . . . ? C5 C6 C7 C8 0.2(8) . . . . ? C6 C7 C8 C9 -0.8(9) . . . . ? C7 C8 C9 C10 2.0(9) . . . . ? C8 C9 C10 C5 -2.7(9) . . . . ? C6 C5 C10 C9 2.1(8) . . . . ? C2 C5 C10 C9 178.4(5) . . . . ? C4 C3 C11 C16 156.4(4) . . . . ? C2 C3 C11 C16 -81.5(6) . . . . ? C4 C3 C11 C12 -25.0(6) . . . . ? C2 C3 C11 C12 97.0(5) . . . . ? C16 C11 C12 C13 0.0(7) . . . . ? C3 C11 C12 C13 -178.5(4) . . . . ? C11 C12 C13 C14 1.1(8) . . . . ? C12 C13 C14 C15 -0.9(8) . . . . ? C13 C14 C15 C16 -0.3(9) . . . . ? C12 C11 C16 C15 -1.2(8) . . . . ? C3 C11 C16 C15 177.3(5) . . . . ? C14 C15 C16 C11 1.4(9) . . . . ? N1 C17 C18 C19 -43.6(6) . . . . ? C17 C18 C19 C24 110.0(6) . . . . ? C17 C18 C19 C20 -69.3(6) . . . . ? C24 C19 C20 C21 -2.0(8) . . . . ? C18 C19 C20 C21 177.3(5) . . . . ? C19 C20 C21 C22 1.1(8) . . . . ? C20 C21 C22 C23 0.3(8) . . . . ? C21 C22 C23 C24 -0.8(8) . . . . ? C20 C19 C24 C23 1.6(8) . . . . ? C18 C19 C24 C23 -177.8(5) . . . . ? C22 C23 C24 C19 -0.2(8) . . . . ? O2 C4 N1 C1 176.4(4) . . . . ? C3 C4 N1 C1 -3.9(5) . . . . ? O2 C4 N1 C17 -5.7(7) . . . . ? C3 C4 N1 C17 174.0(4) . . . . ? O1 C1 N1 C4 176.7(4) . . . . ? C2 C1 N1 C4 -2.5(5) . . . . ? O1 C1 N1 C17 -1.2(7) . . . . ? C2 C1 N1 C17 179.6(4) . . . . ? C18 C17 N1 C4 -59.9(6) . . . . ? C18 C17 N1 C1 117.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.261 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.062 data_sakacu021_pbcn _database_code_depnum_ccdc_archive 'CCDC 927190' #TrackingRef '18155_web_deposit_cif_file_3_MasamiSakamoto_1362111942.trans-N-phenyl-3,4-diphenylsuccinimide3h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 N O2' _chemical_formula_weight 327.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.1516(3) _cell_length_b 11.5890(2) _cell_length_c 8.4053(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1670.72(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 6061 _cell_measurement_theta_min 4.60 _cell_measurement_theta_max 70.73 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.663 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8788 _exptl_absorpt_correction_T_max 0.9676 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 7880 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 70.73 _reflns_number_total 1498 _reflns_number_gt 1433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.3625P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1498 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1 C 0.5000 0.62257(13) 0.2500 0.0307(3) Uani 1 2 d S . . C2 C 0.42991(7) 0.68192(10) 0.25667(13) 0.0382(3) Uani 1 1 d . . . H2 H 0.3820 0.6410 0.2617 0.046 Uiso 1 1 calc R . . C3 C 0.43048(8) 0.80122(11) 0.25600(15) 0.0495(4) Uani 1 1 d . . . H3 H 0.3826 0.8423 0.2597 0.059 Uiso 1 1 calc R . . C4 C 0.5000 0.86138(16) 0.2500 0.0534(5) Uani 1 2 d S . . H4 H 0.5000 0.9434 0.2500 0.064 Uiso 1 2 calc SR . . C5 C 0.44789(6) 0.43190(9) 0.16170(12) 0.0308(3) Uani 1 1 d . . . C6 C 0.46585(6) 0.30517(9) 0.18925(12) 0.0300(3) Uani 1 1 d . . . H6 H 0.4850 0.2712 0.0871 0.036 Uiso 1 1 calc R . . C7 C 0.39487(6) 0.23763(9) 0.24318(12) 0.0302(3) Uani 1 1 d . . . C8 C 0.37566(7) 0.13329(9) 0.17262(14) 0.0374(3) Uani 1 1 d . . . H8 H 0.4056 0.1054 0.0857 0.045 Uiso 1 1 calc R . . C9 C 0.31267(7) 0.06915(10) 0.22836(17) 0.0461(3) Uani 1 1 d . . . H9 H 0.2998 -0.0020 0.1789 0.055 Uiso 1 1 calc R . . C10 C 0.26907(7) 0.10824(11) 0.35468(16) 0.0470(3) Uani 1 1 d . . . H10 H 0.2268 0.0635 0.3937 0.056 Uiso 1 1 calc R . . C11 C 0.28700(7) 0.21267(12) 0.42440(16) 0.0480(3) Uani 1 1 d . . . H11 H 0.2566 0.2404 0.5108 0.058 Uiso 1 1 calc R . . C12 C 0.34935(7) 0.27737(10) 0.36852(14) 0.0398(3) Uani 1 1 d . . . H12 H 0.3610 0.3496 0.4164 0.048 Uiso 1 1 calc R . . N1 N 0.5000 0.49876(11) 0.2500 0.0290(3) Uani 1 2 d S . . O1 O 0.39799(4) 0.47046(7) 0.07590(10) 0.0415(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0340(8) 0.0352(8) 0.0230(7) 0.000 0.0002(5) 0.000 C2 0.0362(6) 0.0434(7) 0.0350(6) 0.0003(5) -0.0006(4) 0.0047(5) C3 0.0567(8) 0.0454(7) 0.0463(7) -0.0028(5) -0.0080(6) 0.0150(6) C4 0.0779(14) 0.0347(9) 0.0477(11) 0.000 -0.0143(9) 0.000 C5 0.0266(5) 0.0389(6) 0.0269(5) 0.0011(4) -0.0009(4) -0.0016(4) C6 0.0260(5) 0.0368(6) 0.0271(5) -0.0016(4) -0.0028(4) 0.0011(4) C7 0.0252(5) 0.0333(5) 0.0323(6) 0.0018(4) -0.0058(4) 0.0015(4) C8 0.0374(6) 0.0333(6) 0.0415(6) -0.0019(5) -0.0053(4) 0.0033(4) C9 0.0447(7) 0.0325(6) 0.0612(8) 0.0051(5) -0.0155(6) -0.0052(5) C10 0.0301(6) 0.0504(7) 0.0605(8) 0.0179(6) -0.0070(5) -0.0069(5) C11 0.0340(6) 0.0606(8) 0.0495(7) 0.0034(6) 0.0067(5) 0.0003(5) C12 0.0347(6) 0.0428(6) 0.0418(6) -0.0061(5) 0.0017(5) -0.0027(5) N1 0.0250(6) 0.0345(6) 0.0276(6) 0.000 -0.0003(4) 0.000 O1 0.0388(4) 0.0429(5) 0.0428(5) 0.0048(3) -0.0157(3) 0.0006(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 C1 C2 1.3861(13) . ? C1 C2 1.3861(13) 3_655 ? C1 N1 1.435(2) . ? C2 C3 1.3826(18) . ? C2 H2 0.9500 . ? C3 C4 1.3822(17) . ? C3 H3 0.9500 . ? C4 C3 1.3822(17) 3_655 ? C4 H4 0.9500 . ? C5 O1 1.2052(12) . ? C5 N1 1.3964(12) . ? C5 C6 1.5184(15) . ? C6 C7 1.5167(14) . ? C6 C6 1.5540(19) 3_655 ? C6 H6 1.0000 . ? C7 C8 1.3865(15) . ? C7 C12 1.3899(16) . ? C8 C9 1.3926(17) . ? C8 H8 0.9500 . ? C9 C10 1.375(2) . ? C9 H9 0.9500 . ? C10 C11 1.379(2) . ? C10 H10 0.9500 . ? C11 C12 1.3880(17) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? N1 C5 1.3964(12) 3_655 ? 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 C2 C1 C2 120.51(14) . 3_655 ? C2 C1 N1 119.75(7) . . ? C2 C1 N1 119.75(7) 3_655 . ? C3 C2 C1 119.33(12) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C4 C3 C2 120.71(12) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C3 119.41(16) . 3_655 ? C3 C4 H4 120.3 . . ? C3 C4 H4 120.3 3_655 . ? O1 C5 N1 124.53(10) . . ? O1 C5 C6 126.44(9) . . ? N1 C5 C6 109.01(8) . . ? C7 C6 C5 112.45(8) . . ? C7 C6 C6 114.11(9) . 3_655 ? C5 C6 C6 104.67(5) . 3_655 ? C7 C6 H6 108.5 . . ? C5 C6 H6 108.5 . . ? C6 C6 H6 108.5 3_655 . ? C8 C7 C12 118.67(10) . . ? C8 C7 C6 120.86(10) . . ? C12 C7 C6 120.43(9) . . ? C7 C8 C9 120.40(11) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.38(11) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.71(11) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.14(12) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.68(11) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C5 N1 C5 112.60(12) . 3_655 ? C5 N1 C1 123.70(6) . . ? C5 N1 C1 123.70(6) 3_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 C3 0.25(8) 3_655 . . . ? N1 C1 C2 C3 -179.75(8) . . . . ? C1 C2 C3 C4 -0.50(16) . . . . ? C2 C3 C4 C3 0.25(8) . . . 3_655 ? O1 C5 C6 C7 -54.97(14) . . . . ? N1 C5 C6 C7 126.26(8) . . . . ? O1 C5 C6 C6 -179.38(11) . . . 3_655 ? N1 C5 C6 C6 1.85(12) . . . 3_655 ? C5 C6 C7 C8 132.32(10) . . . . ? C6 C6 C7 C8 -108.66(11) 3_655 . . . ? C5 C6 C7 C12 -49.99(13) . . . . ? C6 C6 C7 C12 69.03(11) 3_655 . . . ? C12 C7 C8 C9 -0.98(16) . . . . ? C6 C7 C8 C9 176.75(9) . . . . ? C7 C8 C9 C10 -0.38(18) . . . . ? C8 C9 C10 C11 1.26(18) . . . . ? C9 C10 C11 C12 -0.76(19) . . . . ? C10 C11 C12 C7 -0.62(19) . . . . ? C8 C7 C12 C11 1.48(17) . . . . ? C6 C7 C12 C11 -176.26(10) . . . . ? O1 C5 N1 C5 -179.54(12) . . . 3_655 ? C6 C5 N1 C5 -0.75(5) . . . 3_655 ? O1 C5 N1 C1 0.46(12) . . . . ? C6 C5 N1 C1 179.25(5) . . . . ? C2 C1 N1 C5 42.38(7) . . . . ? C2 C1 N1 C5 -137.62(7) 3_655 . . . ? C2 C1 N1 C5 -137.62(7) . . . 3_655 ? C2 C1 N1 C5 42.38(7) 3_655 . . 3_655 ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.256 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.035 data_saka328_p21c _database_code_depnum_ccdc_archive 'CCDC 927191' #TrackingRef '18156_web_deposit_cif_file_4_MasamiSakamoto_1362111942.trans-N-(3-methylphenyl)-3,4-diphenylsuccinimide3j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N O2' _chemical_formula_weight 341.39 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8218(6) _cell_length_b 17.4333(12) _cell_length_c 11.8783(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.3140(10) _cell_angle_gamma 90.00 _cell_volume 1797.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 1859 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 23.77 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9763 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details 'SADABS Sheldrick 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 8491 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3190 _reflns_number_gt 2512 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.1468P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3190 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.037 _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 C1 C 0.83880(17) 0.05093(9) 0.95807(14) 0.0280(4) Uani 1 1 d . . . C2 C 0.78460(17) 0.04682(9) 0.82984(13) 0.0267(4) Uani 1 1 d . . . H2 H 0.8708 0.0260 0.7946 0.032 Uiso 1 1 calc R . . C3 C 0.65264(18) -0.01312(9) 0.81306(13) 0.0280(4) Uani 1 1 d . . . H3 H 0.5540 0.0144 0.7837 0.034 Uiso 1 1 calc R . . C4 C 0.64617(18) -0.04146(9) 0.93226(14) 0.0291(4) Uani 1 1 d . . . C5 C 0.73946(17) 0.12430(9) 0.77673(13) 0.0262(4) Uani 1 1 d . . . C6 C 0.81391(19) 0.15430(9) 0.69376(14) 0.0328(4) Uani 1 1 d . . . H6 H 0.8993 0.1277 0.6738 0.039 Uiso 1 1 calc R . . C7 C 0.7657(2) 0.22279(10) 0.63916(15) 0.0411(5) Uani 1 1 d . . . H7 H 0.8179 0.2428 0.5823 0.049 Uiso 1 1 calc R . . C8 C 0.6418(2) 0.26173(10) 0.66768(17) 0.0433(5) Uani 1 1 d . . . H8 H 0.6066 0.3079 0.6292 0.052 Uiso 1 1 calc R . . C9 C 0.5692(2) 0.23323(10) 0.75245(17) 0.0436(5) Uani 1 1 d . . . H9 H 0.4855 0.2606 0.7735 0.052 Uiso 1 1 calc R . . C10 C 0.61720(19) 0.16501(10) 0.80730(15) 0.0365(4) Uani 1 1 d . . . H10 H 0.5667 0.1460 0.8658 0.044 Uiso 1 1 calc R . . C11 C 0.67056(18) -0.07647(9) 0.72939(14) 0.0292(4) Uani 1 1 d . . . C12 C 0.57385(19) -0.07921(10) 0.62363(14) 0.0346(4) Uani 1 1 d . . . H12 H 0.4943 -0.0422 0.6050 0.041 Uiso 1 1 calc R . . C13 C 0.5924(2) -0.13568(11) 0.54470(15) 0.0438(5) Uani 1 1 d . . . H13 H 0.5257 -0.1370 0.4724 0.053 Uiso 1 1 calc R . . C14 C 0.7067(2) -0.18962(11) 0.57070(16) 0.0446(5) Uani 1 1 d . . . H14 H 0.7184 -0.2285 0.5168 0.053 Uiso 1 1 calc R . . C15 C 0.8047(2) -0.18729(10) 0.67546(16) 0.0422(5) Uani 1 1 d . . . H15 H 0.8844 -0.2243 0.6932 0.051 Uiso 1 1 calc R . . C16 C 0.78675(19) -0.13100(10) 0.75472(15) 0.0366(4) Uani 1 1 d . . . H16 H 0.8542 -0.1297 0.8267 0.044 Uiso 1 1 calc R . . C17 C 0.77798(17) -0.01462(9) 1.13235(13) 0.0290(4) Uani 1 1 d . . . C18 C 0.80095(18) 0.04759(10) 1.20589(14) 0.0325(4) Uani 1 1 d . . . H18 H 0.8042 0.0979 1.1756 0.039 Uiso 1 1 calc R . . C19 C 0.81924(18) 0.03726(11) 1.32353(15) 0.0378(4) Uani 1 1 d . . . C20 C 0.8101(2) -0.03699(12) 1.36525(16) 0.0438(5) Uani 1 1 d . . . H20 H 0.8193 -0.0451 1.4453 0.053 Uiso 1 1 calc R . . C21 C 0.7878(2) -0.09887(12) 1.29182(16) 0.0449(5) Uani 1 1 d . . . H21 H 0.7824 -0.1491 1.3219 0.054 Uiso 1 1 calc R . . C22 C 0.77328(19) -0.08871(10) 1.17449(15) 0.0366(4) Uani 1 1 d . . . H22 H 0.7604 -0.1315 1.1241 0.044 Uiso 1 1 calc R . . C23 C 0.8432(2) 0.10504(13) 1.40288(16) 0.0520(5) Uani 1 1 d . . . H23A H 0.9537 0.1125 1.4304 0.078 Uiso 1 1 calc R . . H23B H 0.7916 0.0958 1.4682 0.078 Uiso 1 1 calc R . . H23C H 0.7998 0.1511 1.3619 0.078 Uiso 1 1 calc R . . N1 N 0.75592(14) -0.00219(7) 1.01109(11) 0.0271(3) Uani 1 1 d . . . O1 O 0.93930(13) 0.09191(6) 1.00797(10) 0.0378(3) Uani 1 1 d . . . O2 O 0.55842(13) -0.08889(7) 0.95822(10) 0.0405(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0258(8) 0.0272(9) 0.0296(9) 0.0004(7) 0.0014(7) 0.0028(7) C2 0.0263(8) 0.0277(9) 0.0260(9) -0.0025(7) 0.0043(6) 0.0001(6) C3 0.0252(8) 0.0291(9) 0.0283(9) -0.0021(7) 0.0012(7) -0.0019(7) C4 0.0271(8) 0.0281(9) 0.0319(9) -0.0043(7) 0.0049(7) 0.0004(7) C5 0.0271(8) 0.0280(8) 0.0222(8) -0.0039(6) 0.0009(6) -0.0011(6) C6 0.0340(9) 0.0360(9) 0.0285(9) -0.0005(7) 0.0062(7) 0.0022(7) C7 0.0481(11) 0.0403(10) 0.0344(10) 0.0063(8) 0.0056(8) -0.0049(9) C8 0.0469(11) 0.0288(10) 0.0485(12) 0.0027(8) -0.0071(9) -0.0004(8) C9 0.0398(10) 0.0342(10) 0.0562(13) -0.0066(9) 0.0071(9) 0.0097(8) C10 0.0374(9) 0.0348(10) 0.0392(10) -0.0028(8) 0.0119(8) 0.0027(8) C11 0.0310(9) 0.0294(9) 0.0271(9) -0.0027(7) 0.0054(7) -0.0058(7) C12 0.0360(9) 0.0388(10) 0.0283(10) -0.0003(7) 0.0038(7) -0.0062(8) C13 0.0529(12) 0.0515(12) 0.0270(10) -0.0058(8) 0.0069(8) -0.0138(10) C14 0.0602(12) 0.0401(11) 0.0380(11) -0.0131(8) 0.0214(9) -0.0144(10) C15 0.0456(11) 0.0327(10) 0.0511(12) -0.0062(9) 0.0161(9) -0.0034(8) C16 0.0366(9) 0.0350(10) 0.0369(10) -0.0044(8) 0.0033(8) -0.0028(8) C17 0.0244(8) 0.0360(10) 0.0265(9) 0.0009(7) 0.0042(6) 0.0044(7) C18 0.0280(9) 0.0393(10) 0.0294(9) -0.0001(7) 0.0032(7) 0.0045(7) C19 0.0274(9) 0.0559(12) 0.0295(10) -0.0022(8) 0.0034(7) 0.0063(8) C20 0.0343(10) 0.0690(14) 0.0283(10) 0.0102(9) 0.0058(8) 0.0089(9) C21 0.0424(10) 0.0519(12) 0.0408(11) 0.0152(9) 0.0090(8) 0.0079(9) C22 0.0350(9) 0.0374(10) 0.0374(10) 0.0044(8) 0.0062(8) 0.0036(8) C23 0.0481(12) 0.0756(15) 0.0314(11) -0.0126(10) 0.0049(9) 0.0012(10) N1 0.0260(7) 0.0293(7) 0.0254(7) 0.0005(6) 0.0026(5) 0.0005(6) O1 0.0366(7) 0.0406(7) 0.0331(7) -0.0003(5) -0.0022(5) -0.0110(5) O2 0.0423(7) 0.0425(8) 0.0375(7) -0.0024(6) 0.0093(6) -0.0158(6) _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 C1 O1 1.2082(18) . ? C1 N1 1.398(2) . ? C1 C2 1.514(2) . ? C2 C5 1.514(2) . ? C2 C3 1.550(2) . ? C2 H2 1.0000 . ? C3 C4 1.510(2) . ? C3 C11 1.513(2) . ? C3 H3 1.0000 . ? C4 O2 1.2098(19) . ? C4 N1 1.3994(19) . ? C5 C6 1.381(2) . ? C5 C10 1.392(2) . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C8 1.379(3) . ? C7 H7 0.9500 . ? C8 C9 1.379(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 C16 1.391(2) . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 C14 1.373(3) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.385(2) . ? C17 C22 1.388(2) . ? C17 N1 1.435(2) . ? C18 C19 1.389(2) . ? C18 H18 0.9500 . ? C19 C20 1.393(3) . ? C19 C23 1.503(3) . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 124.60(15) . . ? O1 C1 C2 126.40(15) . . ? N1 C1 C2 108.99(13) . . ? C5 C2 C1 112.89(12) . . ? C5 C2 C3 114.36(12) . . ? C1 C2 C3 104.82(12) . . ? C5 C2 H2 108.2 . . ? C1 C2 H2 108.2 . . ? C3 C2 H2 108.2 . . ? C4 C3 C11 113.77(13) . . ? C4 C3 C2 104.69(12) . . ? C11 C3 C2 114.33(13) . . ? C4 C3 H3 107.9 . . ? C11 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? O2 C4 N1 124.16(15) . . ? O2 C4 C3 126.57(14) . . ? N1 C4 C3 109.24(13) . . ? C6 C5 C10 118.85(15) . . ? C6 C5 C2 120.80(14) . . ? C10 C5 C2 120.29(14) . . ? C5 C6 C7 120.91(16) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 119.90(17) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 119.58(17) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.68(17) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C5 120.04(16) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? C12 C11 C16 118.83(15) . . ? C12 C11 C3 120.03(14) . . ? C16 C11 C3 121.10(14) . . ? C11 C12 C13 120.54(16) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.26(17) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.87(17) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.14(18) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.36(16) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C18 C17 C22 120.77(16) . . ? C18 C17 N1 119.55(14) . . ? C22 C17 N1 119.67(14) . . ? C17 C18 C19 120.70(16) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C20 118.32(17) . . ? C18 C19 C23 120.46(17) . . ? C20 C19 C23 121.20(17) . . ? C21 C20 C19 120.83(17) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 120.82(17) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C17 118.52(17) . . ? C21 C22 H22 120.7 . . ? C17 C22 H22 120.7 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 N1 C4 112.19(13) . . ? C1 N1 C17 124.37(13) . . ? C4 N1 C17 123.43(13) . . ? 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 C1 C2 C5 -53.7(2) . . . . ? N1 C1 C2 C5 127.69(13) . . . . ? O1 C1 C2 C3 -178.80(15) . . . . ? N1 C1 C2 C3 2.60(16) . . . . ? C5 C2 C3 C4 -126.71(13) . . . . ? C1 C2 C3 C4 -2.54(16) . . . . ? C5 C2 C3 C11 108.13(15) . . . . ? C1 C2 C3 C11 -127.70(14) . . . . ? C11 C3 C4 O2 -54.7(2) . . . . ? C2 C3 C4 O2 179.80(15) . . . . ? C11 C3 C4 N1 127.23(14) . . . . ? C2 C3 C4 N1 1.72(16) . . . . ? C1 C2 C5 C6 120.00(16) . . . . ? C3 C2 C5 C6 -120.26(16) . . . . ? C1 C2 C5 C10 -62.86(18) . . . . ? C3 C2 C5 C10 56.88(19) . . . . ? C10 C5 C6 C7 -1.8(2) . . . . ? C2 C5 C6 C7 175.42(14) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C6 C7 C8 C9 1.7(3) . . . . ? C7 C8 C9 C10 -1.5(3) . . . . ? C8 C9 C10 C5 -0.2(3) . . . . ? C6 C5 C10 C9 1.9(2) . . . . ? C2 C5 C10 C9 -175.32(14) . . . . ? C4 C3 C11 C12 130.59(16) . . . . ? C2 C3 C11 C12 -109.19(16) . . . . ? C4 C3 C11 C16 -51.8(2) . . . . ? C2 C3 C11 C16 68.41(19) . . . . ? C16 C11 C12 C13 0.3(2) . . . . ? C3 C11 C12 C13 177.95(15) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C3 C11 C16 C15 -177.92(15) . . . . ? C22 C17 C18 C19 -0.2(2) . . . . ? N1 C17 C18 C19 178.59(14) . . . . ? C17 C18 C19 C20 -1.5(2) . . . . ? C17 C18 C19 C23 -179.63(15) . . . . ? C18 C19 C20 C21 1.8(3) . . . . ? C23 C19 C20 C21 179.88(16) . . . . ? C19 C20 C21 C22 -0.3(3) . . . . ? C20 C21 C22 C17 -1.5(3) . . . . ? C18 C17 C22 C21 1.8(2) . . . . ? N1 C17 C22 C21 -177.06(15) . . . . ? O1 C1 N1 C4 179.74(15) . . . . ? C2 C1 N1 C4 -1.64(17) . . . . ? O1 C1 N1 C17 0.7(2) . . . . ? C2 C1 N1 C17 179.34(13) . . . . ? O2 C4 N1 C1 -178.24(15) . . . . ? C3 C4 N1 C1 -0.10(17) . . . . ? O2 C4 N1 C17 0.8(2) . . . . ? C3 C4 N1 C17 178.94(13) . . . . ? C18 C17 N1 C1 41.0(2) . . . . ? C22 C17 N1 C1 -140.21(16) . . . . ? C18 C17 N1 C4 -137.97(16) . . . . ? C22 C17 N1 C4 40.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.243 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.057