# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email taka.okuno@gmail.com _publ_contact_author_name 'Takahiro Okuno' _publ_author_name 'Takahiro Okuno' data_imai015Ver3_1 _database_code_depnum_ccdc_archive 'CCDC 828925' #TrackingRef 'IMAI015Ver3.CIF' #data_im8700a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O2' _chemical_formula_weight 319.39 _chemical_absolute_configuration rm 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 7.0066(6) _cell_length_b 6.2397(5) _cell_length_c 19.8205(17) _cell_angle_alpha 90.00 _cell_angle_beta 96.494(2) _cell_angle_gamma 90.00 _cell_volume 860.97(13) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 3343 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.87 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5354 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3619 _reflns_number_gt 3343 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0526P)^2^+0.0716P] 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 -1.4(12) _refine_ls_number_reflns 3619 _refine_ls_number_parameters 219 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.8654(2) 0.4115(3) 0.19082(8) 0.0201(4) Uani 1 1 d . . . C2 C 0.9006(3) 0.2706(3) 0.24546(9) 0.0238(4) Uani 1 1 d . . . H2 H 0.9388 0.1273 0.2378 0.029 Uiso 1 1 calc R . . C3 C 0.8799(3) 0.3385(3) 0.31074(9) 0.0236(4) Uani 1 1 d . . . H3 H 0.9075 0.2421 0.3477 0.028 Uiso 1 1 calc R . . C4 C 0.8193(2) 0.5457(3) 0.32310(8) 0.0200(4) Uani 1 1 d . . . C5 C 0.7856(2) 0.6870(3) 0.26838(8) 0.0216(4) Uani 1 1 d . . . H5 H 0.7447 0.8294 0.2759 0.026 Uiso 1 1 calc R . . C6 C 0.8114(2) 0.6214(3) 0.20331(8) 0.0207(4) Uani 1 1 d . . . H6 H 0.7921 0.7205 0.1668 0.025 Uiso 1 1 calc R . . C7 C 0.8871(2) 0.3327(3) 0.12051(9) 0.0218(4) Uani 1 1 d . . . O8 O 0.84962(18) 0.1403(2) 0.10742(6) 0.0281(3) Uani 1 1 d . . . O9 O 0.9419(2) 0.4658(2) 0.07834(6) 0.0316(3) Uani 1 1 d . . . C10 C 0.7909(2) 0.6147(3) 0.39302(8) 0.0209(4) Uani 1 1 d . . . C11 C 0.8575(3) 0.8129(3) 0.41781(9) 0.0244(4) Uani 1 1 d . . . H11 H 0.9191 0.9064 0.3893 0.029 Uiso 1 1 calc R . . C12 C 0.8352(3) 0.8759(3) 0.48354(9) 0.0267(4) Uani 1 1 d . . . H12 H 0.8806 1.0122 0.4996 0.032 Uiso 1 1 calc R . . C13 C 0.7470(2) 0.7405(3) 0.52564(9) 0.0275(4) Uani 1 1 d . . . H13 H 0.7330 0.7827 0.5709 0.033 Uiso 1 1 calc R . . C14 C 0.6787(3) 0.5425(3) 0.50169(9) 0.0297(4) Uani 1 1 d . . . H14 H 0.6168 0.4498 0.5304 0.036 Uiso 1 1 calc R . . C15 C 0.7009(2) 0.4803(3) 0.43608(9) 0.0254(4) Uani 1 1 d . . . H15 H 0.6543 0.3444 0.4201 0.031 Uiso 1 1 calc R . . C21 C 0.6776(2) 0.4398(3) 0.84111(9) 0.0267(4) Uani 1 1 d . . . C22 C 0.7249(3) 0.2705(4) 0.80051(9) 0.0307(4) Uani 1 1 d . . . H22 H 0.7694 0.1392 0.8208 0.037 Uiso 1 1 calc R . . C23 C 0.7073(3) 0.2926(4) 0.73042(10) 0.0377(5) Uani 1 1 d . . . H23 H 0.7410 0.1772 0.7028 0.045 Uiso 1 1 calc R . . C24 C 0.6403(3) 0.4841(4) 0.70080(10) 0.0431(6) Uani 1 1 d . . . H24 H 0.6280 0.4999 0.6528 0.052 Uiso 1 1 calc R . . C25 C 0.5920(3) 0.6495(4) 0.74061(11) 0.0423(5) Uani 1 1 d . . . H25 H 0.5454 0.7798 0.7201 0.051 Uiso 1 1 calc R . . C26 C 0.6102(3) 0.6291(4) 0.81038(11) 0.0346(5) Uani 1 1 d . . . H26 H 0.5764 0.7456 0.8375 0.041 Uiso 1 1 calc R . . C27 C 0.6991(3) 0.4198(3) 0.91773(9) 0.0296(4) Uani 1 1 d . . . H27 H 0.6685 0.5624 0.9369 0.036 Uiso 1 1 calc R . . C28 C 0.5677(3) 0.2552(5) 0.94438(10) 0.0455(6) Uani 1 1 d . . . H28A H 0.5916 0.1146 0.9250 0.068 Uiso 1 1 calc R . . H28B H 0.4336 0.2964 0.9315 0.068 Uiso 1 1 calc R . . H28C H 0.5930 0.2479 0.9940 0.068 Uiso 1 1 calc R . . N27 N 0.9036(2) 0.3667(2) 0.94314(7) 0.0228(3) Uani 1 1 d . . . H27A H 0.9195 0.3718 0.9893 0.034 Uiso 1 1 calc R . . H27B H 0.9833 0.4634 0.9264 0.034 Uiso 1 1 calc R . . H27C H 0.9320 0.2327 0.9291 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0188(8) 0.0214(9) 0.0203(8) -0.0007(7) 0.0031(6) -0.0022(7) C2 0.0293(9) 0.0170(8) 0.0254(9) 0.0000(7) 0.0042(7) 0.0004(7) C3 0.0311(9) 0.0204(9) 0.0193(8) 0.0061(7) 0.0031(7) -0.0015(7) C4 0.0197(8) 0.0210(8) 0.0190(8) 0.0004(7) 0.0016(6) -0.0032(7) C5 0.0216(8) 0.0195(9) 0.0238(9) 0.0006(7) 0.0023(7) 0.0013(7) C6 0.0221(8) 0.0201(8) 0.0197(8) 0.0033(7) 0.0011(6) -0.0001(7) C7 0.0212(8) 0.0235(9) 0.0206(8) -0.0001(7) 0.0018(7) 0.0013(7) O8 0.0343(7) 0.0232(7) 0.0274(7) -0.0050(5) 0.0061(5) -0.0015(6) O9 0.0461(8) 0.0296(7) 0.0200(6) -0.0012(6) 0.0074(6) -0.0094(6) C10 0.0200(8) 0.0223(9) 0.0199(8) 0.0021(7) 0.0004(7) 0.0023(7) C11 0.0273(9) 0.0213(9) 0.0245(9) 0.0020(7) 0.0017(7) 0.0013(7) C12 0.0287(9) 0.0235(9) 0.0267(9) -0.0044(7) -0.0019(7) 0.0026(7) C13 0.0257(9) 0.0385(11) 0.0184(8) -0.0066(8) 0.0024(7) 0.0026(8) C14 0.0283(10) 0.0390(11) 0.0224(9) 0.0045(8) 0.0056(7) -0.0068(8) C15 0.0267(9) 0.0273(10) 0.0221(8) 0.0006(7) 0.0022(7) -0.0070(8) C21 0.0212(9) 0.0367(11) 0.0223(8) 0.0029(8) 0.0034(7) 0.0026(8) C22 0.0248(9) 0.0409(11) 0.0267(9) 0.0019(8) 0.0033(7) 0.0035(8) C23 0.0254(10) 0.0634(15) 0.0249(10) -0.0095(10) 0.0052(8) -0.0069(10) C24 0.0300(11) 0.0763(18) 0.0221(9) 0.0134(11) -0.0017(8) -0.0148(11) C25 0.0323(11) 0.0517(14) 0.0407(12) 0.0208(11) -0.0061(9) -0.0045(10) C26 0.0279(10) 0.0368(11) 0.0383(11) 0.0053(9) 0.0007(8) 0.0036(9) C27 0.0281(9) 0.0387(11) 0.0221(8) 0.0002(8) 0.0033(7) 0.0065(8) C28 0.0329(11) 0.0774(18) 0.0267(10) 0.0050(11) 0.0055(8) -0.0132(12) N27 0.0294(8) 0.0218(7) 0.0173(7) 0.0014(6) 0.0028(6) -0.0011(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.393(2) . ? C1 C2 1.395(2) . ? C1 C7 1.502(2) . ? C2 C3 1.385(2) . ? C3 C4 1.391(2) . ? C4 C5 1.397(2) . ? C4 C10 1.486(2) . ? C5 C6 1.385(2) . ? C7 O8 1.250(2) . ? C7 O9 1.268(2) . ? C10 C11 1.392(2) . ? C10 C15 1.397(2) . ? C11 C12 1.387(2) . ? C12 C13 1.382(3) . ? C13 C14 1.389(3) . ? C14 C15 1.383(2) . ? C21 C26 1.387(3) . ? C21 C22 1.390(3) . ? C21 C27 1.514(2) . ? C22 C23 1.387(3) . ? C23 C24 1.390(3) . ? C24 C25 1.365(3) . ? C25 C26 1.380(3) . ? C27 N27 1.501(2) . ? C27 C28 1.514(3) . ? 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 C6 C1 C2 118.84(15) . . ? C6 C1 C7 122.07(15) . . ? C2 C1 C7 119.08(15) . . ? C3 C2 C1 120.29(17) . . ? C2 C3 C4 121.02(16) . . ? C3 C4 C5 118.56(15) . . ? C3 C4 C10 120.61(15) . . ? C5 C4 C10 120.84(16) . . ? C6 C5 C4 120.53(16) . . ? C5 C6 C1 120.70(16) . . ? O8 C7 O9 124.35(17) . . ? O8 C7 C1 117.82(16) . . ? O9 C7 C1 117.83(16) . . ? C11 C10 C15 118.32(16) . . ? C11 C10 C4 120.77(16) . . ? C15 C10 C4 120.89(16) . . ? C12 C11 C10 121.00(17) . . ? C13 C12 C11 119.96(17) . . ? C12 C13 C14 119.86(17) . . ? C15 C14 C13 120.02(17) . . ? C14 C15 C10 120.84(17) . . ? C26 C21 C22 118.97(18) . . ? C26 C21 C27 120.05(18) . . ? C22 C21 C27 120.98(18) . . ? C23 C22 C21 120.3(2) . . ? C22 C23 C24 119.7(2) . . ? C25 C24 C23 120.01(18) . . ? C24 C25 C26 120.6(2) . . ? C25 C26 C21 120.4(2) . . ? N27 C27 C28 109.14(17) . . ? N27 C27 C21 109.73(14) . . ? C28 C27 C21 114.24(16) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.240 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.038 #===END data_imai015ver3_2 _database_code_depnum_ccdc_archive 'CCDC 828926' #TrackingRef 'IMAI015Ver3.CIF' #data_im9169a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 N2 O4' _chemical_formula_weight 484.58 _chemical_absolute_configuration rm 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 7.0662(8) _cell_length_b 6.1893(7) _cell_length_c 29.342(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.006(2) _cell_angle_gamma 90.00 _cell_volume 1283.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 4718 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 27.85 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _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_000 516 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9556 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4961 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.85 _reflns_number_total 4961 _reflns_number_gt 4718 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0743P)^2^+0.0848P] 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 0.0(16) _refine_ls_number_reflns 4961 _refine_ls_number_parameters 330 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.7791(4) -0.2050(5) 0.72773(10) 0.0168(6) Uani 1 1 d . . . C2 C 0.7289(4) -0.0059(5) 0.70901(10) 0.0180(6) Uani 1 1 d . . . H2 H 0.6751 0.1017 0.7281 0.022 Uiso 1 1 calc R . . C3 C 0.7556(4) 0.0392(5) 0.66291(10) 0.0178(6) Uani 1 1 d . . . H3 H 0.7181 0.1751 0.6509 0.021 Uiso 1 1 calc R . . C4 C 0.8377(4) -0.1157(5) 0.63432(9) 0.0155(6) Uani 1 1 d . . . C5 C 0.8897(4) -0.3156(5) 0.65271(10) 0.0172(6) Uani 1 1 d . . . H5 H 0.9447 -0.4224 0.6336 0.021 Uiso 1 1 calc R . . C6 C 0.8620(4) -0.3593(5) 0.69819(10) 0.0164(6) Uani 1 1 d . . . H6 H 0.8991 -0.4958 0.7100 0.020 Uiso 1 1 calc R . . C7 C 0.7435(4) -0.2592(5) 0.77658(9) 0.0147(6) Uani 1 1 d . . . C8 C 0.6823(4) -0.4645(5) 0.78900(10) 0.0175(6) Uani 1 1 d . . . H8 H 0.6602 -0.5697 0.7660 0.021 Uiso 1 1 calc R . . C9 C 0.6530(4) -0.5186(5) 0.83436(10) 0.0184(6) Uani 1 1 d . . . H9 H 0.6139 -0.6605 0.8423 0.022 Uiso 1 1 calc R . . C10 C 0.6811(4) -0.3644(5) 0.86830(10) 0.0176(6) Uani 1 1 d . . . C11 C 0.7372(4) -0.1565(5) 0.85643(10) 0.0170(6) Uani 1 1 d . . . H11 H 0.7525 -0.0497 0.8794 0.020 Uiso 1 1 calc R . . C12 C 0.7710(4) -0.1048(5) 0.81109(9) 0.0161(6) Uani 1 1 d . . . H12 H 0.8132 0.0363 0.8033 0.019 Uiso 1 1 calc R . . C13 C 0.8686(4) -0.0618(5) 0.58444(9) 0.0155(6) Uani 1 1 d . . . O14 O 0.9607(3) -0.1989(4) 0.56053(7) 0.0223(5) Uani 1 1 d . . . O15 O 0.8095(3) 0.1128(4) 0.56950(7) 0.0204(5) Uani 1 1 d . . . C16 C 0.6480(4) -0.4302(5) 0.91755(10) 0.0190(7) Uani 1 1 d . . . O17 O 0.5951(4) -0.2869(4) 0.94575(8) 0.0291(6) Uani 1 1 d . . . O18 O 0.6744(3) -0.6255(4) 0.92793(7) 0.0240(5) Uani 1 1 d . . . C21 C 0.7884(4) -0.3336(6) 1.10472(11) 0.0243(7) Uani 1 1 d . . . C22 C 0.7272(5) -0.5061(7) 1.13191(11) 0.0299(8) Uani 1 1 d . . . H22 H 0.6816 -0.6349 1.1181 0.036 Uiso 1 1 calc R . . C23 C 0.7334(5) -0.4884(8) 1.17919(12) 0.0396(10) Uani 1 1 d . . . H23 H 0.6919 -0.6050 1.1977 0.047 Uiso 1 1 calc R . . C24 C 0.8005(5) -0.3002(9) 1.19918(12) 0.0473(13) Uani 1 1 d . . . H24 H 0.8056 -0.2882 1.2314 0.057 Uiso 1 1 calc R . . C25 C 0.8598(5) -0.1301(8) 1.17214(13) 0.0431(11) Uani 1 1 d . . . H25 H 0.9050 -0.0011 1.1859 0.052 Uiso 1 1 calc R . . C26 C 0.8537(5) -0.1469(7) 1.12592(13) 0.0328(8) Uani 1 1 d . . . H26 H 0.8948 -0.0288 1.1078 0.039 Uiso 1 1 calc R . . C27 C 0.7851(4) -0.3506(6) 1.05300(11) 0.0257(8) Uani 1 1 d . . . H27 H 0.8251 -0.2080 1.0402 0.031 Uiso 1 1 calc R . . C28 C 0.9194(5) -0.5238(8) 1.03458(12) 0.0433(11) Uani 1 1 d . . . H28A H 0.9120 -0.5269 1.0012 0.065 Uiso 1 1 calc R . . H28B H 0.8829 -0.6652 1.0468 0.065 Uiso 1 1 calc R . . H28C H 1.0493 -0.4903 1.0439 0.065 Uiso 1 1 calc R . . N27 N 0.5882(4) -0.3965(4) 1.03674(8) 0.0185(5) Uani 1 1 d . . . H27A H 0.5069 -0.2986 1.0491 0.028 Uiso 1 1 calc R . . H27B H 0.5538 -0.5320 1.0455 0.028 Uiso 1 1 calc R . . H27C H 0.5843 -0.3868 1.0058 0.028 Uiso 1 1 calc R . . C31 C 0.6962(4) -0.1169(6) 0.40507(9) 0.0177(6) Uani 1 1 d . . . C32 C 0.7461(4) -0.2805(5) 0.37478(10) 0.0196(6) Uani 1 1 d . . . H32 H 0.7928 -0.4136 0.3863 0.023 Uiso 1 1 calc R . . C33 C 0.7288(4) -0.2530(6) 0.32815(11) 0.0223(7) Uani 1 1 d . . . H33 H 0.7632 -0.3663 0.3080 0.027 Uiso 1 1 calc R . . C34 C 0.6614(4) -0.0599(6) 0.31115(10) 0.0250(8) Uani 1 1 d . . . H34 H 0.6509 -0.0400 0.2791 0.030 Uiso 1 1 calc R . . C35 C 0.6085(4) 0.1064(6) 0.34072(11) 0.0239(7) Uani 1 1 d . . . H35 H 0.5611 0.2388 0.3290 0.029 Uiso 1 1 calc R . . C36 C 0.6258(4) 0.0766(6) 0.38704(11) 0.0226(7) Uani 1 1 d . . . H36 H 0.5893 0.1894 0.4071 0.027 Uiso 1 1 calc R . . C37 C 0.7218(4) -0.1408(6) 0.45621(10) 0.0223(7) Uani 1 1 d . . . H37 H 0.6479 -0.0235 0.4714 0.027 Uiso 1 1 calc R . . C38 C 0.6539(4) -0.3545(6) 0.47483(11) 0.0314(8) Uani 1 1 d . . . H38A H 0.6656 -0.3544 0.5081 0.047 Uiso 1 1 calc R . . H38B H 0.7310 -0.4716 0.4621 0.047 Uiso 1 1 calc R . . H38C H 0.5212 -0.3764 0.4664 0.047 Uiso 1 1 calc R . . N37 N 0.9287(3) -0.1085(4) 0.46769(8) 0.0173(5) Uani 1 1 d . . . H37A H 0.9671 0.0233 0.4575 0.026 Uiso 1 1 calc R . . H37B H 0.9988 -0.2135 0.4541 0.026 Uiso 1 1 calc R . . H37C H 0.9446 -0.1157 0.4984 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0117(13) 0.0216(17) 0.0170(14) -0.0033(11) 0.0010(11) -0.0011(12) C2 0.0212(15) 0.0153(16) 0.0174(14) -0.0044(11) 0.0025(12) -0.0003(13) C3 0.0179(14) 0.0137(16) 0.0219(15) 0.0019(11) -0.0005(12) -0.0023(12) C4 0.0123(12) 0.0164(15) 0.0178(13) -0.0026(12) 0.0017(10) -0.0059(12) C5 0.0131(13) 0.0187(16) 0.0197(14) -0.0041(12) 0.0023(11) 0.0015(12) C6 0.0176(14) 0.0121(15) 0.0196(14) 0.0020(11) 0.0011(11) 0.0059(13) C7 0.0094(13) 0.0178(16) 0.0169(14) 0.0028(12) 0.0036(10) 0.0014(12) C8 0.0169(14) 0.0200(16) 0.0157(14) -0.0060(11) 0.0038(11) 0.0011(12) C9 0.0186(14) 0.0127(16) 0.0241(15) 0.0017(12) 0.0032(11) -0.0010(13) C10 0.0131(14) 0.0214(17) 0.0184(14) -0.0018(12) 0.0032(11) 0.0036(13) C11 0.0189(14) 0.0163(15) 0.0157(13) -0.0046(11) 0.0005(11) 0.0023(13) C12 0.0147(13) 0.0139(15) 0.0197(14) -0.0002(11) 0.0019(11) -0.0014(12) C13 0.0129(13) 0.0178(16) 0.0156(13) -0.0024(11) 0.0018(11) -0.0039(12) O14 0.0297(12) 0.0254(13) 0.0117(10) -0.0007(8) 0.0053(9) 0.0032(10) O15 0.0204(11) 0.0200(12) 0.0209(11) 0.0056(9) 0.0041(8) 0.0008(9) C16 0.0161(14) 0.0240(18) 0.0170(15) -0.0008(13) -0.0011(11) -0.0015(13) O17 0.0393(13) 0.0310(15) 0.0171(11) 0.0036(10) 0.0068(10) 0.0080(12) O18 0.0270(12) 0.0244(13) 0.0208(11) 0.0055(10) 0.0030(9) 0.0022(10) C21 0.0130(14) 0.035(2) 0.0250(16) -0.0039(14) 0.0040(12) 0.0010(14) C22 0.0213(16) 0.045(2) 0.0237(16) 0.0013(15) 0.0023(13) 0.0005(16) C23 0.0197(17) 0.070(3) 0.0287(19) 0.010(2) 0.0071(14) 0.0149(19) C24 0.0246(18) 0.097(4) 0.0206(18) -0.017(2) -0.0031(14) 0.024(2) C25 0.0244(18) 0.058(3) 0.047(2) -0.026(2) -0.0068(16) 0.009(2) C26 0.0195(16) 0.036(2) 0.043(2) -0.0109(17) -0.0015(14) -0.0011(16) C27 0.0215(15) 0.033(2) 0.0224(15) -0.0004(14) 0.0038(12) -0.0034(15) C28 0.0301(19) 0.076(3) 0.0242(18) -0.010(2) 0.0071(15) 0.016(2) N27 0.0263(13) 0.0184(14) 0.0107(11) -0.0002(10) 0.0050(10) 0.0012(11) C31 0.0085(13) 0.0273(17) 0.0174(14) 0.0000(13) 0.0015(10) -0.0019(13) C32 0.0143(14) 0.0189(16) 0.0255(16) 0.0014(12) 0.0007(11) -0.0001(13) C33 0.0162(15) 0.0249(18) 0.0257(16) -0.0080(13) 0.0018(12) -0.0021(14) C34 0.0162(14) 0.039(2) 0.0199(15) 0.0015(15) -0.0026(12) -0.0050(15) C35 0.0172(14) 0.0235(18) 0.0308(17) 0.0058(14) -0.0049(12) 0.0015(14) C36 0.0136(14) 0.0226(17) 0.0315(17) -0.0041(13) 0.0005(12) 0.0034(13) C37 0.0148(14) 0.034(2) 0.0177(15) -0.0021(14) 0.0028(10) 0.0005(15) C38 0.0192(16) 0.051(2) 0.0240(16) 0.0090(15) 0.0013(12) -0.0137(17) N37 0.0172(12) 0.0205(14) 0.0142(12) 0.0001(10) 0.0010(9) -0.0005(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.395(4) . ? C1 C6 1.417(4) . ? C1 C7 1.494(4) . ? C2 C3 1.394(4) . ? C3 C4 1.400(4) . ? C4 C5 1.399(4) . ? C4 C13 1.517(4) . ? C5 C6 1.376(4) . ? C7 C8 1.391(4) . ? C7 C12 1.406(4) . ? C8 C9 1.388(4) . ? C9 C10 1.393(4) . ? C10 C11 1.391(4) . ? C10 C16 1.519(4) . ? C11 C12 1.389(4) . ? C13 O15 1.239(4) . ? C13 O14 1.279(3) . ? C16 O18 1.260(4) . ? C16 O17 1.269(4) . ? C21 C26 1.391(5) . ? C21 C22 1.401(5) . ? C21 C27 1.521(4) . ? C22 C23 1.392(5) . ? C23 C24 1.388(7) . ? C24 C25 1.384(7) . ? C25 C26 1.361(5) . ? C27 N27 1.498(4) . ? C27 C28 1.531(5) . ? C31 C32 1.393(4) . ? C31 C36 1.400(5) . ? C31 C37 1.519(4) . ? C32 C33 1.384(4) . ? C33 C34 1.379(5) . ? C34 C35 1.397(5) . ? C35 C36 1.377(4) . ? C37 C38 1.509(5) . ? C37 N37 1.514(4) . ? 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 C6 117.4(3) . . ? C2 C1 C7 122.3(2) . . ? C6 C1 C7 120.3(3) . . ? C3 C2 C1 121.6(3) . . ? C2 C3 C4 120.1(3) . . ? C5 C4 C3 118.9(2) . . ? C5 C4 C13 121.9(3) . . ? C3 C4 C13 119.2(3) . . ? C6 C5 C4 120.7(3) . . ? C5 C6 C1 121.3(3) . . ? C8 C7 C12 118.4(3) . . ? C8 C7 C1 120.6(3) . . ? C12 C7 C1 121.0(3) . . ? C9 C8 C7 121.2(3) . . ? C8 C9 C10 120.0(3) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 C16 122.0(3) . . ? C9 C10 C16 118.3(3) . . ? C12 C11 C10 120.2(3) . . ? C11 C12 C7 120.6(3) . . ? O15 C13 O14 123.8(3) . . ? O15 C13 C4 119.0(3) . . ? O14 C13 C4 117.2(3) . . ? O18 C16 O17 123.8(3) . . ? O18 C16 C10 117.7(3) . . ? O17 C16 C10 118.5(3) . . ? C26 C21 C22 118.7(3) . . ? C26 C21 C27 120.6(3) . . ? C22 C21 C27 120.7(3) . . ? C23 C22 C21 119.8(4) . . ? C24 C23 C22 119.9(4) . . ? C25 C24 C23 120.0(3) . . ? C26 C25 C24 120.2(4) . . ? C25 C26 C21 121.3(4) . . ? N27 C27 C21 110.2(2) . . ? N27 C27 C28 109.3(3) . . ? C21 C27 C28 113.0(3) . . ? C32 C31 C36 118.1(3) . . ? C32 C31 C37 122.0(3) . . ? C36 C31 C37 119.9(3) . . ? C33 C32 C31 121.2(3) . . ? C34 C33 C32 119.7(3) . . ? C33 C34 C35 120.4(3) . . ? C36 C35 C34 119.4(3) . . ? C35 C36 C31 121.3(3) . . ? C38 C37 N37 110.0(3) . . ? C38 C37 C31 113.9(3) . . ? N37 C37 C31 108.8(2) . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.400 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.058 #===END data_imai015ver3_3 _database_code_depnum_ccdc_archive 'CCDC 828927' #TrackingRef 'IMAI015Ver3.CIF' #data_im1629a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O3 S' _chemical_formula_weight 355.44 _chemical_absolute_configuration rm 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' S S 0.1246 0.1234 '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 7.357(2) _cell_length_b 6.1288(17) _cell_length_c 20.081(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.129(5) _cell_angle_gamma 90.00 _cell_volume 905.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4708 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 30.89 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9218 _exptl_absorpt_correction_T_max 0.9654 _exptl_absorpt_process_details Multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8105 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 30.89 _reflns_number_total 4796 _reflns_number_gt 4708 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0609P)^2^+0.1811P] 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 -0.05(5) _refine_ls_number_reflns 4796 _refine_ls_number_parameters 228 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.003 _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 0.7404(2) 1.2403(3) 1.02654(7) 0.0267(3) Uani 1 1 d . . . H1 H 0.7144 1.2818 1.0709 0.032 Uiso 1 1 calc R . . C2 C 0.6832(2) 1.0390(3) 1.00244(7) 0.0282(3) Uani 1 1 d . . . H2 H 0.6181 0.9426 1.0303 0.034 Uiso 1 1 calc R . . C3 C 0.7212(2) 0.9781(3) 0.93740(7) 0.0245(3) Uani 1 1 d . . . H3 H 0.6822 0.8398 0.9213 0.029 Uiso 1 1 calc R . . C4 C 0.81580(18) 1.1175(2) 0.89571(6) 0.0183(2) Uani 1 1 d . . . C5 C 0.87242(19) 1.3200(3) 0.92025(6) 0.0226(2) Uani 1 1 d . . . H5 H 0.9364 1.4170 0.8922 0.027 Uiso 1 1 calc R . . C6 C 0.8358(2) 1.3813(2) 0.98566(7) 0.0261(3) Uani 1 1 d . . . H6 H 0.8759 1.5187 1.0022 0.031 Uiso 1 1 calc R . . C7 C 0.91457(16) 0.9149(2) 0.69594(6) 0.0159(2) Uani 1 1 d . . . C8 C 0.96307(19) 0.7786(2) 0.74879(7) 0.0202(2) Uani 1 1 d . . . H8 H 1.0164 0.6402 0.7407 0.024 Uiso 1 1 calc R . . C9 C 0.93258(19) 0.8474(2) 0.81358(6) 0.0207(2) Uani 1 1 d . . . H9 H 0.9648 0.7545 0.8498 0.025 Uiso 1 1 calc R . . C10 C 0.85522(17) 1.0514(2) 0.82631(6) 0.0171(2) Uani 1 1 d . . . C11 C 0.81408(17) 1.1894(2) 0.77263(6) 0.0184(2) Uani 1 1 d . . . H11 H 0.7662 1.3307 0.7807 0.022 Uiso 1 1 calc R . . C12 C 0.84275(18) 1.1215(2) 0.70736(6) 0.0175(2) Uani 1 1 d . . . H12 H 0.8136 1.2154 0.6710 0.021 Uiso 1 1 calc R . . C21 C 0.3991(2) 1.4805(3) 0.80451(8) 0.0306(3) Uani 1 1 d . . . H21 H 0.4050 1.4905 0.8517 0.037 Uiso 1 1 calc R . . C22 C 0.3298(2) 1.2942(3) 0.77421(7) 0.0282(3) Uani 1 1 d . . . H22 H 0.2878 1.1769 0.8007 0.034 Uiso 1 1 calc R . . C23 C 0.32133(18) 1.2784(2) 0.70473(7) 0.0212(3) Uani 1 1 d . . . H23 H 0.2759 1.1494 0.6842 0.025 Uiso 1 1 calc R . . C24 C 0.37958(16) 1.4519(2) 0.66568(6) 0.0170(2) Uani 1 1 d . . . C25 C 0.44955(19) 1.6383(2) 0.69677(7) 0.0233(3) Uani 1 1 d . . . H25 H 0.4904 1.7569 0.6705 0.028 Uiso 1 1 calc R . . C26 C 0.4600(2) 1.6522(3) 0.76591(8) 0.0291(3) Uani 1 1 d . . . H26 H 0.5088 1.7792 0.7867 0.035 Uiso 1 1 calc R . . C27 C 0.37357(16) 1.4441(2) 0.59046(6) 0.0159(2) Uani 1 1 d . . . H27 H 0.3750 1.5978 0.5738 0.019 Uiso 1 1 calc R . . C28 C 0.53443(17) 1.3259(3) 0.56055(6) 0.0229(2) Uani 1 1 d . . . H28A H 0.5252 1.3332 0.5118 0.034 Uiso 1 1 calc R . . H28B H 0.5339 1.1729 0.5747 0.034 Uiso 1 1 calc R . . H28C H 0.6478 1.3955 0.5758 0.034 Uiso 1 1 calc R . . N1 N 0.20143(14) 1.33923(19) 0.56497(5) 0.01701(19) Uani 1 1 d . . . H1A H 0.1040 1.4093 0.5823 0.026 Uiso 1 1 calc R . . H1B H 0.1998 1.1965 0.5774 0.026 Uiso 1 1 calc R . . H1C H 0.1961 1.3483 0.5197 0.026 Uiso 1 1 calc R . . O1 O 0.81245(17) 0.9332(2) 0.57207(5) 0.0347(3) Uani 1 1 d . . . O2 O 1.13478(14) 0.89070(17) 0.59658(5) 0.0232(2) Uani 1 1 d . . . O3 O 0.92900(14) 0.58895(17) 0.61504(5) 0.0234(2) Uani 1 1 d . . . S1 S 0.95028(4) 0.82572(5) 0.613529(14) 0.01755(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0287(7) 0.0338(8) 0.0175(6) -0.0043(5) 0.0011(5) 0.0022(6) C2 0.0301(7) 0.0385(8) 0.0163(6) 0.0008(6) 0.0046(5) -0.0086(6) C3 0.0280(6) 0.0268(6) 0.0187(6) -0.0013(5) 0.0023(5) -0.0077(5) C4 0.0207(6) 0.0200(5) 0.0142(5) 0.0013(4) -0.0007(4) 0.0005(5) C5 0.0309(6) 0.0190(5) 0.0179(6) 0.0016(6) 0.0006(4) -0.0018(6) C6 0.0346(7) 0.0239(6) 0.0196(6) -0.0042(5) -0.0030(5) 0.0016(5) C7 0.0167(5) 0.0168(5) 0.0143(5) -0.0003(4) 0.0002(4) 0.0012(4) C8 0.0253(6) 0.0161(5) 0.0191(6) 0.0018(4) -0.0011(4) 0.0027(4) C9 0.0285(6) 0.0167(6) 0.0167(5) 0.0025(5) -0.0018(4) 0.0013(5) C10 0.0176(5) 0.0176(5) 0.0161(6) 0.0015(4) 0.0005(4) -0.0014(4) C11 0.0201(5) 0.0171(5) 0.0178(6) 0.0014(4) 0.0007(4) 0.0038(4) C12 0.0209(6) 0.0162(5) 0.0152(5) 0.0014(4) 0.0001(4) 0.0037(4) C21 0.0277(7) 0.0480(9) 0.0159(6) -0.0062(6) -0.0014(5) 0.0113(7) C22 0.0253(6) 0.0407(9) 0.0187(6) 0.0055(6) 0.0018(5) 0.0037(6) C23 0.0204(5) 0.0259(6) 0.0171(6) 0.0018(5) -0.0007(4) -0.0014(5) C24 0.0157(5) 0.0199(5) 0.0154(6) -0.0018(4) -0.0004(4) 0.0024(4) C25 0.0227(6) 0.0221(6) 0.0250(7) -0.0052(5) -0.0026(5) 0.0014(5) C26 0.0273(7) 0.0338(8) 0.0257(7) -0.0122(6) -0.0080(5) 0.0065(6) C27 0.0162(5) 0.0164(5) 0.0150(5) -0.0016(4) 0.0008(4) 0.0003(4) C28 0.0190(5) 0.0302(6) 0.0196(5) -0.0036(6) 0.0021(4) 0.0068(6) N1 0.0167(4) 0.0194(5) 0.0148(4) -0.0002(4) -0.0012(3) 0.0018(4) O1 0.0397(6) 0.0466(7) 0.0173(5) -0.0077(5) -0.0088(4) 0.0281(6) O2 0.0277(5) 0.0192(4) 0.0230(5) -0.0010(3) 0.0074(4) -0.0001(4) O3 0.0225(5) 0.0192(5) 0.0287(5) -0.0068(4) 0.0037(4) -0.0019(4) S1 0.01921(13) 0.01858(13) 0.01478(13) -0.00199(11) -0.00161(9) 0.00561(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.388(2) . ? C1 C6 1.391(2) . ? C2 C3 1.392(2) . ? C3 C4 1.3919(19) . ? C4 C5 1.396(2) . ? C4 C10 1.4852(18) . ? C5 C6 1.3975(19) . ? C7 C8 1.3915(18) . ? C7 C12 1.3930(17) . ? C7 S1 1.7673(14) . ? C8 C9 1.3902(19) . ? C9 C10 1.3992(18) . ? C10 C11 1.3987(18) . ? C11 C12 1.3953(18) . ? C21 C26 1.387(3) . ? C21 C22 1.386(3) . ? C22 C23 1.399(2) . ? C23 C24 1.3938(18) . ? C24 C25 1.3955(19) . ? C24 C27 1.5110(18) . ? C25 C26 1.392(2) . ? C27 N1 1.5010(16) . ? C27 C28 1.5211(17) . ? O1 S1 1.4566(11) . ? O2 S1 1.4611(11) . ? O3 S1 1.4599(11) . ? 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 C6 119.96(13) . . ? C1 C2 C3 120.03(14) . . ? C4 C3 C2 120.80(14) . . ? C3 C4 C5 118.84(12) . . ? C3 C4 C10 120.41(13) . . ? C5 C4 C10 120.75(12) . . ? C4 C5 C6 120.62(13) . . ? C1 C6 C5 119.75(14) . . ? C8 C7 C12 120.83(12) . . ? C8 C7 S1 119.21(10) . . ? C12 C7 S1 119.94(10) . . ? C9 C8 C7 119.22(12) . . ? C8 C9 C10 121.04(12) . . ? C11 C10 C9 118.83(12) . . ? C11 C10 C4 120.99(12) . . ? C9 C10 C4 120.18(12) . . ? C12 C11 C10 120.61(12) . . ? C7 C12 C11 119.38(12) . . ? C26 C21 C22 119.99(14) . . ? C21 C22 C23 120.24(15) . . ? C24 C23 C22 120.02(14) . . ? C23 C24 C25 119.19(13) . . ? C23 C24 C27 122.33(12) . . ? C25 C24 C27 118.46(12) . . ? C26 C25 C24 120.59(14) . . ? C21 C26 C25 119.95(15) . . ? N1 C27 C24 111.25(10) . . ? N1 C27 C28 108.62(10) . . ? C24 C27 C28 113.72(10) . . ? O1 S1 O3 112.80(8) . . ? O1 S1 O2 112.52(8) . . ? O3 S1 O2 112.10(6) . . ? O1 S1 C7 106.31(6) . . ? O3 S1 C7 105.66(6) . . ? O2 S1 C7 106.84(6) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.324 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.050 #===END data_imai015ver3_4 _database_code_depnum_ccdc_archive 'CCDC 828928' #TrackingRef 'IMAI015Ver3.CIF' #data_im9146a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N O3 S' _chemical_formula_weight 278.34 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21212 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 29.1775(14) _cell_length_b 6.2427(3) _cell_length_c 7.2407(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1318.87(10) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2975 _cell_measurement_theta_min 1.40 _cell_measurement_theta_max 27.90 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8753 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11683 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.90 _reflns_number_total 3065 _reflns_number_gt 2975 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0510P)^2^+0.3189P] 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 0.02(6) _refine_ls_number_reflns 3065 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.002 _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 0.38726(5) 0.2941(3) 0.0633(2) 0.0140(3) Uani 1 1 d . . . C2 C 0.42335(5) 0.1701(3) -0.0031(2) 0.0170(3) Uani 1 1 d . . . H2 H 0.4178 0.0309 -0.0513 0.020 Uiso 1 1 calc R . . C3 C 0.46742(5) 0.2520(2) 0.0019(2) 0.0183(3) Uani 1 1 d . . . H3 H 0.4921 0.1669 -0.0417 0.022 Uiso 1 1 calc R . . C4 C 0.47621(5) 0.4569(2) 0.0699(2) 0.0154(3) Uani 1 1 d . . . C5 C 0.43945(5) 0.5798(3) 0.1333(2) 0.0167(3) Uani 1 1 d . . . H5 H 0.4448 0.7204 0.1784 0.020 Uiso 1 1 calc R . . C6 C 0.39507(6) 0.4989(3) 0.1313(2) 0.0171(3) Uani 1 1 d . . . H6 H 0.3703 0.5829 0.1760 0.021 Uiso 1 1 calc R . . S7 S 0.330457(12) 0.19536(6) 0.04614(5) 0.01393(10) Uani 1 1 d . . . O8 O 0.31274(4) 0.26930(19) -0.13131(17) 0.0198(3) Uani 1 1 d . . . O9 O 0.30522(4) 0.2857(2) 0.20124(17) 0.0234(3) Uani 1 1 d . . . O10 O 0.33390(4) -0.03741(17) 0.05508(16) 0.0184(2) Uani 1 1 d . . . C11 C 0.35819(5) -0.1866(3) 0.6037(2) 0.0159(3) Uani 1 1 d . . . C12 C 0.38390(6) -0.3654(3) 0.6533(2) 0.0191(3) Uani 1 1 d . . . H12 H 0.3692 -0.4888 0.7019 0.023 Uiso 1 1 calc R . . C13 C 0.43120(6) -0.3625(3) 0.6315(3) 0.0234(4) Uani 1 1 d . . . H13 H 0.4488 -0.4837 0.6668 0.028 Uiso 1 1 calc R . . C14 C 0.45276(6) -0.1839(3) 0.5586(2) 0.0255(4) Uani 1 1 d . . . H14 H 0.4852 -0.1819 0.5456 0.031 Uiso 1 1 calc R . . C15 C 0.42708(6) -0.0085(3) 0.5050(2) 0.0249(4) Uani 1 1 d . . . H15 H 0.4417 0.1126 0.4517 0.030 Uiso 1 1 calc R . . C16 C 0.38006(6) -0.0093(3) 0.5288(2) 0.0200(3) Uani 1 1 d . . . H16 H 0.3626 0.1125 0.4936 0.024 Uiso 1 1 calc R . . C17 C 0.30678(5) -0.1813(3) 0.6205(2) 0.0152(3) Uani 1 1 d . . . H17 H 0.2973 -0.0276 0.6276 0.018 Uiso 1 1 calc R . . C18 C 0.28300(5) -0.2789(3) 0.4542(2) 0.0201(3) Uani 1 1 d . . . H18A H 0.2924 -0.2026 0.3422 0.030 Uiso 1 1 calc R . . H18B H 0.2497 -0.2667 0.4693 0.030 Uiso 1 1 calc R . . H18C H 0.2915 -0.4303 0.4437 0.030 Uiso 1 1 calc R . . N17 N 0.29088(4) -0.2888(2) 0.79507(18) 0.0159(3) Uani 1 1 d . . . H17A H 0.2989 -0.4296 0.7924 0.024 Uiso 1 1 calc R . . H17B H 0.2599 -0.2773 0.8043 0.024 Uiso 1 1 calc R . . H17C H 0.3042 -0.2244 0.8941 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0099(7) 0.0156(7) 0.0165(7) -0.0002(7) -0.0005(5) -0.0017(5) C2 0.0158(8) 0.0120(7) 0.0233(8) -0.0017(6) 0.0004(6) 0.0002(6) C3 0.0141(7) 0.0141(7) 0.0268(9) -0.0003(6) 0.0034(6) 0.0029(6) C4 0.0123(7) 0.0167(7) 0.0173(8) 0.0028(6) -0.0009(6) -0.0009(6) C5 0.0159(8) 0.0138(7) 0.0204(8) -0.0026(7) 0.0002(6) -0.0007(6) C6 0.0143(7) 0.0182(7) 0.0188(7) -0.0031(6) 0.0015(6) 0.0012(6) S7 0.01042(17) 0.01402(17) 0.01734(18) -0.00206(15) 0.00086(14) -0.00124(14) O8 0.0158(5) 0.0187(6) 0.0249(6) 0.0002(5) -0.0041(5) -0.0011(5) O9 0.0128(5) 0.0290(6) 0.0283(7) -0.0114(6) 0.0054(5) -0.0039(5) O10 0.0170(5) 0.0155(5) 0.0227(6) 0.0006(4) -0.0016(5) -0.0025(4) C11 0.0139(7) 0.0187(7) 0.0152(7) -0.0024(6) -0.0007(5) -0.0006(6) C12 0.0171(8) 0.0211(8) 0.0191(8) 0.0025(6) 0.0025(6) 0.0005(6) C13 0.0162(8) 0.0311(9) 0.0228(8) 0.0028(7) 0.0000(7) 0.0056(7) C14 0.0123(7) 0.0407(10) 0.0235(8) -0.0017(9) 0.0008(6) -0.0034(7) C15 0.0208(8) 0.0298(9) 0.0241(10) 0.0018(7) 0.0013(7) -0.0085(7) C16 0.0186(8) 0.0194(7) 0.0220(8) 0.0003(7) -0.0027(7) -0.0026(6) C17 0.0134(7) 0.0139(7) 0.0182(7) 0.0008(6) -0.0004(6) -0.0005(6) C18 0.0167(7) 0.0236(8) 0.0200(8) -0.0049(8) -0.0029(7) -0.0033(6) N17 0.0115(6) 0.0176(6) 0.0186(6) -0.0011(6) 0.0016(5) -0.0005(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.388(2) . ? C1 C2 1.393(2) . ? C1 S7 1.7726(15) . ? C2 C3 1.384(2) . ? C3 C4 1.394(2) . ? C4 C5 1.396(2) . ? C4 C4 1.489(3) 2_665 ? C5 C6 1.390(2) . ? S7 O9 1.4565(12) . ? S7 O10 1.4580(11) . ? S7 O8 1.4598(12) . ? C11 C16 1.388(2) . ? C11 C12 1.392(2) . ? C11 C17 1.505(2) . ? C12 C13 1.389(2) . ? C13 C14 1.385(3) . ? C14 C15 1.383(3) . ? C15 C16 1.383(3) . ? C17 N17 1.504(2) . ? C17 C18 1.517(2) . ? 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 C6 C1 C2 120.66(14) . . ? C6 C1 S7 119.91(12) . . ? C2 C1 S7 119.29(12) . . ? C3 C2 C1 119.20(14) . . ? C2 C3 C4 121.27(14) . . ? C3 C4 C5 118.59(14) . . ? C3 C4 C4 120.22(16) . 2_665 ? C5 C4 C4 121.17(16) . 2_665 ? C6 C5 C4 120.83(15) . . ? C1 C6 C5 119.42(15) . . ? O9 S7 O10 112.73(8) . . ? O9 S7 O8 112.16(7) . . ? O10 S7 O8 112.25(7) . . ? O9 S7 C1 106.49(7) . . ? O10 S7 C1 106.21(7) . . ? O8 S7 C1 106.43(7) . . ? C16 C11 C12 119.52(15) . . ? C16 C11 C17 118.18(15) . . ? C12 C11 C17 122.24(16) . . ? C13 C12 C11 119.72(16) . . ? C14 C13 C12 120.32(16) . . ? C15 C14 C13 119.92(16) . . ? C14 C15 C16 119.98(16) . . ? C15 C16 C11 120.50(16) . . ? N17 C17 C11 111.45(13) . . ? N17 C17 C18 110.29(13) . . ? C11 C17 C18 112.50(14) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.453 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.053 #===END