# Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Nangia, Ashwini' _publ_contact_author_email ashwini.nangia@gmail.com _publ_section_title ; Form V of Tolbutamide and a high Z' crystal structure of form III. The role of cocrystal formers in the crystallization of polymorphs ; _publ_author_name 'Ashwini Nangia' # Attachment '- form III 100K.cif' data_Tolbutamide_formIII_100K _database_code_depnum_ccdc_archive 'CCDC 772453' #TrackingRef '- form III 100K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 N2 O3 S' _chemical_formula_weight 270.34 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.5613(17) _cell_length_b 27.189(4) _cell_length_c 13.556(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.803(2) _cell_angle_gamma 90.00 _cell_volume 4155.2(11) _cell_formula_units_Z 12 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5352 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9368 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39777 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.07 _reflns_number_total 7363 _reflns_number_gt 5713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+6.3729P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7363 _refine_ls_number_parameters 517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1505 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 S2 S 0.82968(7) 0.10211(3) 0.11806(6) 0.0146(2) Uani 1 1 d . . . S3 S 0.36700(7) 0.06862(3) 0.61439(6) 0.0148(2) Uani 1 1 d . . . O9 O 0.2869(2) 0.12025(8) 0.78615(16) 0.0179(5) Uani 1 1 d . . . O6 O 0.7570(2) 0.04942(8) 0.29088(17) 0.0202(5) Uani 1 1 d . . . O4 O 0.8061(2) 0.13787(8) 0.03865(16) 0.0193(5) Uani 1 1 d . . . O8 O 0.3511(2) 0.11991(8) 0.59650(16) 0.0191(5) Uani 1 1 d . . . O5 O 0.8052(2) 0.05159(8) 0.09376(17) 0.0203(5) Uani 1 1 d . . . O7 O 0.3419(2) 0.03516(8) 0.53081(16) 0.0203(5) Uani 1 1 d . . . C32 C 0.2701(3) 0.07548(11) 0.7773(2) 0.0139(7) Uani 1 1 d . . . N4 N 0.6850(2) 0.12028(11) 0.3446(2) 0.0177(6) Uani 1 1 d . . . N6 N 0.2396(2) 0.04657(10) 0.8462(2) 0.0182(6) Uani 1 1 d . . . N5 N 0.2801(2) 0.05074(11) 0.6884(2) 0.0162(6) Uani 1 1 d . . . C19 C 1.1390(3) 0.09299(12) 0.3237(2) 0.0204(8) Uani 1 1 d . . . H19 H 1.1668 0.0796 0.3877 0.024 Uiso 1 1 calc R . . N3 N 0.7508(2) 0.12014(11) 0.1977(2) 0.0162(6) Uani 1 1 d . . . C20 C 0.7317(3) 0.09331(11) 0.2812(2) 0.0158(7) Uani 1 1 d . . . C17 C 0.9799(3) 0.10784(11) 0.1812(2) 0.0156(7) Uani 1 1 d . . . C21 C 0.6642(3) 0.10096(12) 0.4399(3) 0.0205(7) Uani 1 1 d . . . H21A H 0.6609 0.0653 0.4363 0.025 Uiso 1 1 calc R . . H21B H 0.5879 0.1126 0.4489 0.025 Uiso 1 1 calc R . . C14 C 1.2173(3) 0.11861(12) 0.2773(3) 0.0198(7) Uani 1 1 d . . . C28 C 0.5813(3) 0.02266(12) 0.6495(3) 0.0219(8) Uani 1 1 d . . . H28 H 0.5500 0.0043 0.5919 0.026 Uiso 1 1 calc R . . C18 C 1.0220(3) 0.08715(12) 0.2767(2) 0.0172(7) Uani 1 1 d . . . H18 H 0.9713 0.0696 0.3081 0.021 Uiso 1 1 calc R . . C33 C 0.2256(3) 0.06459(12) 0.9449(3) 0.0207(8) Uani 1 1 d . . . H33A H 0.1532 0.0512 0.9590 0.025 Uiso 1 1 calc R . . H33B H 0.2183 0.1001 0.9425 0.025 Uiso 1 1 calc R . . C29 C 0.5131(3) 0.05820(12) 0.6832(2) 0.0156(7) Uani 1 1 d . . . C15 C 1.1736(3) 0.13829(13) 0.1812(3) 0.0242(8) Uani 1 1 d . . . H15 H 1.2249 0.1549 0.1486 0.029 Uiso 1 1 calc R . . C31 C 0.6725(3) 0.07598(13) 0.8234(3) 0.0236(8) Uani 1 1 d . . . H31 H 0.7025 0.0934 0.8826 0.028 Uiso 1 1 calc R . . C26 C 0.7433(3) 0.04091(13) 0.7905(3) 0.0206(8) Uani 1 1 d . . . C16 C 1.0552(3) 0.13352(12) 0.1336(3) 0.0221(8) Uani 1 1 d . . . H16 H 1.0266 0.1475 0.0702 0.027 Uiso 1 1 calc R . . C30 C 0.5592(3) 0.08521(12) 0.7699(3) 0.0216(8) Uani 1 1 d . . . H30 H 0.5136 0.1094 0.7916 0.026 Uiso 1 1 calc R . . C13 C 1.3457(3) 0.12443(14) 0.3285(3) 0.0275(9) Uani 1 1 d . . . H13A H 1.3882 0.0951 0.3188 0.041 Uiso 1 1 calc R . . H13B H 1.3525 0.1299 0.3995 0.041 Uiso 1 1 calc R . . H13C H 1.3784 0.1520 0.2998 0.041 Uiso 1 1 calc R . . C22 C 0.7594(3) 0.11614(12) 0.5307(3) 0.0202(7) Uani 1 1 d . . . H22A H 0.7320 0.1088 0.5917 0.024 Uiso 1 1 calc R . . H22B H 0.7705 0.1515 0.5284 0.024 Uiso 1 1 calc R . . C27 C 0.6965(3) 0.01503(13) 0.7028(3) 0.0238(8) Uani 1 1 d . . . H27 H 0.7435 -0.0080 0.6793 0.029 Uiso 1 1 calc R . . C35 C 0.4495(3) 0.07245(14) 1.0230(3) 0.0284(9) Uani 1 1 d . . . H35A H 0.5116 0.0574 1.0740 0.034 Uiso 1 1 calc R . . H35B H 0.4648 0.0644 0.9573 0.034 Uiso 1 1 calc R . . C23 C 0.8781(3) 0.09123(14) 0.5373(3) 0.0286(9) Uani 1 1 d . . . H23A H 0.9035 0.0966 0.4746 0.034 Uiso 1 1 calc R . . H23B H 0.8690 0.0561 0.5453 0.034 Uiso 1 1 calc R . . C25 C 0.8682(3) 0.03175(15) 0.8496(3) 0.0321(9) Uani 1 1 d . . . H25A H 0.9019 0.0048 0.8198 0.048 Uiso 1 1 calc R . . H25B H 0.8668 0.0239 0.9184 0.048 Uiso 1 1 calc R . . H25C H 0.9152 0.0608 0.8482 0.048 Uiso 1 1 calc R . . C34 C 0.3307(3) 0.05013(13) 1.0303(3) 0.0234(8) Uani 1 1 d . . . H34A H 0.3132 0.0600 1.0943 0.028 Uiso 1 1 calc R . . H34B H 0.3382 0.0146 1.0311 0.028 Uiso 1 1 calc R . . C24 C 0.9730(4) 0.11055(17) 0.6253(3) 0.0475(12) Uani 1 1 d . . . H24A H 0.9836 0.1452 0.6169 0.071 Uiso 1 1 calc R . . H24B H 1.0465 0.0938 0.6268 0.071 Uiso 1 1 calc R . . H24C H 0.9489 0.1048 0.6877 0.071 Uiso 1 1 calc R . . C36 C 0.4565(4) 0.12804(14) 1.0368(3) 0.0391(11) Uani 1 1 d . . . H36A H 0.3937 0.1433 0.9882 0.059 Uiso 1 1 calc R . . H36B H 0.5316 0.1396 1.0271 0.059 Uiso 1 1 calc R . . H36C H 0.4486 0.1362 1.1039 0.059 Uiso 1 1 calc R . . S1 S 0.10774(7) 0.23056(3) 0.87485(6) 0.0133(2) Uani 1 1 d . . . O3 O 0.17959(19) 0.28294(7) 0.70133(16) 0.0163(5) Uani 1 1 d . . . O2 O 0.13221(19) 0.28086(8) 0.90031(16) 0.0181(5) Uani 1 1 d . . . O1 O 0.12871(19) 0.19434(8) 0.95378(16) 0.0184(5) Uani 1 1 d . . . N1 N 0.1900(2) 0.21279(10) 0.7976(2) 0.0152(6) Uani 1 1 d . . . N2 N 0.2603(2) 0.21297(10) 0.6531(2) 0.0149(6) Uani 1 1 d . . . C6 C -0.0804(3) 0.24888(12) 0.7157(2) 0.0190(7) Uani 1 1 d . . . H6 H -0.0279 0.2672 0.6875 0.023 Uiso 1 1 calc R . . C8 C 0.2093(2) 0.23930(11) 0.7142(2) 0.0116(7) Uani 1 1 d . . . C4 C -0.1198(3) 0.19920(12) 0.8517(3) 0.0198(7) Uani 1 1 d . . . H4 H -0.0933 0.1833 0.9133 0.024 Uiso 1 1 calc R . . C9 C 0.2752(3) 0.23077(12) 0.5549(2) 0.0171(7) Uani 1 1 d . . . H9A H 0.3517 0.2202 0.5445 0.021 Uiso 1 1 calc R . . H9B H 0.2742 0.2664 0.5548 0.021 Uiso 1 1 calc R . . C5 C -0.0413(3) 0.22543(11) 0.8080(2) 0.0152(7) Uani 1 1 d . . . C2 C -0.2779(3) 0.21911(12) 0.7085(2) 0.0183(7) Uani 1 1 d . . . C7 C -0.1972(3) 0.24482(12) 0.6665(3) 0.0187(7) Uani 1 1 d . . . H7 H -0.2227 0.2596 0.6036 0.022 Uiso 1 1 calc R . . C11 C 0.0558(3) 0.23346(14) 0.4655(3) 0.0261(8) Uani 1 1 d . . . H11A H 0.0352 0.2279 0.5302 0.031 Uiso 1 1 calc R . . H11B H 0.0586 0.2687 0.4553 0.031 Uiso 1 1 calc R . . C3 C -0.2374(3) 0.19693(13) 0.8027(3) 0.0236(8) Uani 1 1 d . . . H3 H -0.2908 0.1803 0.8329 0.028 Uiso 1 1 calc R . . C1 C -0.4066(3) 0.21611(14) 0.6554(3) 0.0283(9) Uani 1 1 d . . . H1A H -0.4386 0.2487 0.6434 0.042 Uiso 1 1 calc R . . H1B H -0.4497 0.1984 0.6969 0.042 Uiso 1 1 calc R . . H1C H -0.4138 0.1993 0.5920 0.042 Uiso 1 1 calc R . . C10 C 0.1778(3) 0.21182(12) 0.4685(3) 0.0192(7) Uani 1 1 d . . . H10A H 0.1731 0.1763 0.4742 0.023 Uiso 1 1 calc R . . H10B H 0.1996 0.2191 0.4050 0.023 Uiso 1 1 calc R . . C12 C -0.0399(3) 0.21124(15) 0.3819(3) 0.0345(10) Uani 1 1 d . . . H12A H -0.0228 0.2186 0.3173 0.052 Uiso 1 1 calc R . . H12B H -0.1156 0.2249 0.3850 0.052 Uiso 1 1 calc R . . H12C H -0.0417 0.1762 0.3906 0.052 Uiso 1 1 calc R . . H5A H 0.269(3) 0.0228(13) 0.687(2) 0.006(9) Uiso 1 1 d . . . H2 H 0.277(3) 0.1820(13) 0.669(2) 0.015(9) Uiso 1 1 d . . . H3A H 0.733(3) 0.1485(13) 0.193(2) 0.013(9) Uiso 1 1 d . . . H6A H 0.236(3) 0.0161(14) 0.836(3) 0.017(9) Uiso 1 1 d . . . H1 H 0.212(3) 0.1849(14) 0.804(3) 0.019(10) Uiso 1 1 d . . . H4A H 0.674(3) 0.1533(14) 0.331(3) 0.023(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S2 0.0179(4) 0.0124(4) 0.0121(4) -0.0008(3) 0.0007(3) -0.0012(3) S3 0.0185(4) 0.0137(4) 0.0114(4) 0.0004(3) 0.0014(3) 0.0026(3) O9 0.0240(13) 0.0124(12) 0.0174(13) 0.0009(9) 0.0049(10) 0.0016(9) O6 0.0247(13) 0.0150(13) 0.0217(13) -0.0013(10) 0.0067(10) -0.0001(10) O4 0.0215(13) 0.0185(12) 0.0160(12) 0.0022(9) 0.0002(10) -0.0015(9) O8 0.0250(13) 0.0159(12) 0.0158(12) 0.0034(10) 0.0036(10) 0.0036(9) O5 0.0290(14) 0.0164(12) 0.0153(12) -0.0032(10) 0.0048(10) -0.0027(10) O7 0.0250(13) 0.0219(13) 0.0123(12) -0.0017(10) 0.0008(10) 0.0012(10) C32 0.0096(15) 0.0160(18) 0.0155(17) 0.0008(13) 0.0014(13) 0.0033(12) N4 0.0209(15) 0.0155(15) 0.0171(15) 0.0007(12) 0.0048(12) 0.0037(12) N6 0.0252(16) 0.0108(15) 0.0186(16) -0.0002(12) 0.0050(12) -0.0032(12) N5 0.0203(15) 0.0099(15) 0.0181(16) -0.0014(12) 0.0035(12) -0.0001(12) C19 0.026(2) 0.0231(19) 0.0108(17) 0.0029(14) 0.0016(14) 0.0050(14) N3 0.0194(15) 0.0110(15) 0.0170(15) 0.0016(12) 0.0017(12) 0.0031(12) C20 0.0144(16) 0.0112(17) 0.0195(18) -0.0014(13) -0.0012(14) -0.0024(12) C17 0.0135(16) 0.0168(17) 0.0152(17) -0.0019(13) 0.0002(13) 0.0019(13) C21 0.0189(18) 0.0222(18) 0.0218(19) -0.0025(14) 0.0074(15) -0.0001(14) C14 0.0213(18) 0.0181(17) 0.0190(19) 0.0012(14) 0.0026(14) 0.0010(14) C28 0.025(2) 0.0213(18) 0.0184(19) -0.0034(14) 0.0035(15) 0.0019(14) C18 0.0187(18) 0.0194(17) 0.0149(17) 0.0024(13) 0.0066(14) 0.0005(13) C33 0.0253(19) 0.0177(18) 0.0226(19) 0.0003(14) 0.0125(15) -0.0004(14) C29 0.0168(17) 0.0169(16) 0.0135(17) 0.0040(13) 0.0046(13) 0.0007(13) C15 0.0194(19) 0.028(2) 0.024(2) 0.0075(15) 0.0019(15) -0.0005(15) C31 0.025(2) 0.0251(19) 0.0175(18) -0.0050(15) -0.0017(15) -0.0059(15) C26 0.0172(18) 0.0277(19) 0.0168(18) 0.0043(14) 0.0034(14) 0.0007(14) C16 0.0253(19) 0.0235(19) 0.0161(18) 0.0081(14) 0.0016(15) -0.0012(14) C30 0.026(2) 0.0170(18) 0.0210(19) -0.0038(14) 0.0030(15) 0.0028(14) C13 0.0176(19) 0.038(2) 0.025(2) 0.0061(17) 0.0001(15) -0.0005(16) C22 0.0250(19) 0.0173(17) 0.0177(18) 0.0020(14) 0.0033(15) 0.0036(14) C27 0.0233(19) 0.026(2) 0.024(2) -0.0002(15) 0.0079(16) 0.0059(15) C35 0.025(2) 0.037(2) 0.021(2) 0.0029(16) -0.0004(16) 0.0039(16) C23 0.025(2) 0.030(2) 0.030(2) 0.0043(16) 0.0029(16) 0.0053(16) C25 0.024(2) 0.044(2) 0.026(2) 0.0038(18) 0.0009(17) 0.0042(17) C34 0.033(2) 0.0190(18) 0.0174(18) 0.0008(14) 0.0041(15) -0.0005(15) C24 0.037(3) 0.061(3) 0.037(3) 0.001(2) -0.008(2) 0.007(2) C36 0.031(2) 0.038(2) 0.040(3) 0.0050(19) -0.0104(19) -0.0136(18) S1 0.0146(4) 0.0137(4) 0.0102(4) 0.0000(3) -0.0005(3) -0.0015(3) O3 0.0190(12) 0.0112(12) 0.0184(12) 0.0013(9) 0.0033(10) 0.0001(9) O2 0.0203(12) 0.0173(12) 0.0159(12) -0.0018(9) 0.0019(10) -0.0042(9) O1 0.0211(12) 0.0192(12) 0.0137(12) 0.0030(9) 0.0011(10) -0.0010(9) N1 0.0185(15) 0.0097(15) 0.0174(15) 0.0019(11) 0.0040(12) 0.0038(11) N2 0.0160(14) 0.0123(15) 0.0164(15) 0.0032(11) 0.0033(11) 0.0031(11) C6 0.0179(18) 0.0222(18) 0.0164(18) 0.0032(14) 0.0031(14) 0.0007(14) C8 0.0056(15) 0.0147(17) 0.0123(16) -0.0002(12) -0.0032(12) -0.0013(12) C4 0.0232(19) 0.0212(18) 0.0136(18) 0.0038(14) 0.0012(14) -0.0004(14) C9 0.0167(17) 0.0168(17) 0.0188(18) 0.0023(13) 0.0062(14) 0.0004(13) C5 0.0169(17) 0.0134(16) 0.0154(17) -0.0032(13) 0.0035(13) 0.0000(13) C2 0.0166(17) 0.0187(18) 0.0182(18) -0.0069(14) 0.0011(14) 0.0001(13) C7 0.0194(18) 0.0215(18) 0.0143(17) 0.0027(14) 0.0019(14) 0.0026(14) C11 0.0204(19) 0.030(2) 0.024(2) -0.0022(16) -0.0023(15) 0.0047(15) C3 0.0226(19) 0.0245(19) 0.024(2) 0.0041(15) 0.0055(16) -0.0065(15) C1 0.0203(19) 0.036(2) 0.026(2) 0.0036(17) 0.0017(16) -0.0008(16) C10 0.0197(18) 0.0193(18) 0.0178(18) -0.0020(14) 0.0023(14) 0.0009(14) C12 0.026(2) 0.041(2) 0.031(2) -0.0047(18) -0.0050(17) 0.0053(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S2 O5 1.426(2) . ? S2 O4 1.431(2) . ? S2 N3 1.636(3) . ? S2 C17 1.764(3) . ? S3 O8 1.420(2) . ? S3 O7 1.432(2) . ? S3 N5 1.643(3) . ? S3 C29 1.762(3) . ? O9 C32 1.234(4) . ? O6 C20 1.229(4) . ? C32 N6 1.326(4) . ? C32 N5 1.407(4) . ? N4 C20 1.331(4) . ? N4 C21 1.464(4) . ? N4 H4A 0.92(4) . ? N6 C33 1.467(4) . ? N6 H6A 0.84(4) . ? N5 H5A 0.77(3) . ? C19 C18 1.370(5) . ? C19 C14 1.397(5) . ? C19 H19 0.9300 . ? N3 C20 1.405(4) . ? N3 H3A 0.80(3) . ? C17 C16 1.382(5) . ? C17 C18 1.397(4) . ? C21 C22 1.515(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C14 C15 1.395(5) . ? C14 C13 1.501(5) . ? C28 C29 1.387(5) . ? C28 C27 1.383(5) . ? C28 H28 0.9300 . ? C18 H18 0.9300 . ? C33 C34 1.533(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C29 C30 1.388(5) . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C31 C30 1.373(5) . ? C31 C26 1.393(5) . ? C31 H31 0.9300 . ? C26 C27 1.384(5) . ? C26 C25 1.508(5) . ? C16 H16 0.9300 . ? C30 H30 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C22 C23 1.515(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C27 H27 0.9300 . ? C35 C36 1.523(5) . ? C35 C34 1.525(5) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C23 C24 1.525(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? S1 O2 1.423(2) . ? S1 O1 1.435(2) . ? S1 N1 1.635(3) . ? S1 C5 1.765(3) . ? O3 C8 1.237(4) . ? N1 C8 1.400(4) . ? N1 H1 0.80(4) . ? N2 C8 1.328(4) . ? N2 C9 1.462(4) . ? N2 H2 0.88(3) . ? C6 C7 1.372(5) . ? C6 C5 1.387(4) . ? C6 H6 0.9300 . ? C4 C3 1.376(5) . ? C4 C5 1.386(5) . ? C4 H4 0.9300 . ? C9 C10 1.523(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C2 C7 1.385(5) . ? C2 C3 1.396(5) . ? C2 C1 1.505(5) . ? C7 H7 0.9300 . ? C11 C12 1.523(5) . ? C11 C10 1.520(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C3 H3 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 O5 S2 O4 119.05(14) . . ? O5 S2 N3 109.26(14) . . ? O4 S2 N3 104.58(14) . . ? O5 S2 C17 108.72(14) . . ? O4 S2 C17 107.94(14) . . ? N3 S2 C17 106.62(15) . . ? O8 S3 O7 119.52(14) . . ? O8 S3 N5 108.73(14) . . ? O7 S3 N5 104.53(14) . . ? O8 S3 C29 108.73(14) . . ? O7 S3 C29 108.61(15) . . ? N5 S3 C29 105.88(15) . . ? O9 C32 N6 125.2(3) . . ? O9 C32 N5 120.9(3) . . ? N6 C32 N5 113.9(3) . . ? C20 N4 C21 122.8(3) . . ? C20 N4 H4A 118(2) . . ? C21 N4 H4A 119(2) . . ? C32 N6 C33 123.0(3) . . ? C32 N6 H6A 118(2) . . ? C33 N6 H6A 118(2) . . ? C32 N5 S3 124.0(2) . . ? C32 N5 H5A 117(2) . . ? S3 N5 H5A 113(2) . . ? C18 C19 C14 121.3(3) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? C20 N3 S2 125.9(2) . . ? C20 N3 H3A 119(2) . . ? S2 N3 H3A 114(2) . . ? O6 C20 N4 126.0(3) . . ? O6 C20 N3 120.9(3) . . ? N4 C20 N3 113.1(3) . . ? C16 C17 C18 120.6(3) . . ? C16 C17 S2 118.2(3) . . ? C18 C17 S2 121.2(2) . . ? N4 C21 C22 112.8(3) . . ? N4 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? N4 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C15 C14 C19 118.4(3) . . ? C15 C14 C13 120.4(3) . . ? C19 C14 C13 121.2(3) . . ? C29 C28 C27 118.9(3) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C19 C18 C17 119.3(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? N6 C33 C34 112.0(3) . . ? N6 C33 H33A 109.2 . . ? C34 C33 H33A 109.2 . . ? N6 C33 H33B 109.2 . . ? C34 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? C28 C29 C30 120.5(3) . . ? C28 C29 S3 119.1(3) . . ? C30 C29 S3 120.4(3) . . ? C16 C15 C14 121.0(3) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C30 C31 C26 121.0(3) . . ? C30 C31 H31 119.5 . . ? C26 C31 H31 119.5 . . ? C27 C26 C31 118.5(3) . . ? C27 C26 C25 121.2(3) . . ? C31 C26 C25 120.3(3) . . ? C17 C16 C15 119.3(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C31 C30 C29 119.5(3) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C21 C22 C23 114.3(3) . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22B 108.7 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C26 C27 C28 121.4(3) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C36 C35 C34 114.3(3) . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35B 108.7 . . ? C34 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C22 C23 C24 112.2(3) . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C35 C34 C33 115.0(3) . . ? C35 C34 H34A 108.5 . . ? C33 C34 H34A 108.5 . . ? C35 C34 H34B 108.5 . . ? C33 C34 H34B 108.5 . . ? H34A C34 H34B 107.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O2 S1 O1 119.14(13) . . ? O2 S1 N1 109.06(14) . . ? O1 S1 N1 104.39(14) . . ? O2 S1 C5 108.61(14) . . ? O1 S1 C5 108.25(14) . . ? N1 S1 C5 106.71(15) . . ? C8 N1 S1 125.8(2) . . ? C8 N1 H1 119(3) . . ? S1 N1 H1 115(3) . . ? C8 N2 C9 123.2(3) . . ? C8 N2 H2 118(2) . . ? C9 N2 H2 118(2) . . ? C7 C6 C5 119.4(3) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O3 C8 N2 125.3(3) . . ? O3 C8 N1 121.2(3) . . ? N2 C8 N1 113.5(3) . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N2 C9 C10 111.8(3) . . ? N2 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N2 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 S1 118.6(3) . . ? C6 C5 S1 120.9(2) . . ? C7 C2 C3 118.3(3) . . ? C7 C2 C1 121.0(3) . . ? C3 C2 C1 120.6(3) . . ? C6 C7 C2 121.4(3) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? C12 C11 C10 112.5(3) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C9 C10 C11 114.4(3) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.717 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.077 # Attachment '- form III rt.cif' data_Tolbutamide_formIII_rt _database_code_depnum_ccdc_archive 'CCDC 772454' #TrackingRef '- form III rt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 N2 O3 S' _chemical_formula_weight 270.34 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.787(5) _cell_length_b 9.043(4) _cell_length_c 13.955(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.644(7) _cell_angle_gamma 90.00 _cell_volume 1439.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2622 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 21.63 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9288 _exptl_absorpt_correction_T_max 0.9710 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14600 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.06 _reflns_number_total 2846 _reflns_number_gt 2304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.9244P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2846 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1783 _refine_ls_wR_factor_gt 0.1679 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.021 _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 C2 C 0.2602(3) 0.1321(5) 0.2081(3) 0.0734(10) Uani 1 1 d . . . C7 C 0.3352(3) 0.2190(4) 0.1714(3) 0.0734(10) Uani 1 1 d . . . H7 H 0.3074 0.2648 0.1102 0.088 Uiso 1 1 calc R . . C6 C 0.4484(3) 0.2399(4) 0.2216(2) 0.0669(9) Uani 1 1 d . . . H6 H 0.4967 0.3013 0.1959 0.080 Uiso 1 1 calc R . . C5 C 0.4920(3) 0.1694(3) 0.3114(2) 0.0538(8) Uani 1 1 d . . . C4 C 0.4191(3) 0.0809(5) 0.3494(3) 0.0772(11) Uani 1 1 d . . . H4 H 0.4474 0.0320 0.4093 0.093 Uiso 1 1 calc R . . C3 C 0.3049(4) 0.0658(5) 0.2981(3) 0.0896(13) Uani 1 1 d . . . H3 H 0.2554 0.0084 0.3252 0.107 Uiso 1 1 calc R . . C1 C 0.1346(4) 0.1130(7) 0.1529(3) 0.1086(16) Uani 1 1 d . . . H1A H 0.0998 0.0360 0.1834 0.163 Uiso 1 1 calc R . . H1B H 0.1303 0.0867 0.0854 0.163 Uiso 1 1 calc R . . H1C H 0.0930 0.2039 0.1545 0.163 Uiso 1 1 calc R . . C8 C 0.7361(3) 0.2189(3) 0.2250(2) 0.0523(7) Uani 1 1 d . . . C9 C 0.7978(4) 0.1969(4) 0.0719(3) 0.0744(10) Uani 1 1 d . . . H9A H 0.8695 0.1545 0.0618 0.089 Uiso 1 1 calc R . . H9B H 0.8088 0.3030 0.0786 0.089 Uiso 1 1 calc R . . C10 C 0.7000(6) 0.1657(9) -0.0169(4) 0.146(3) Uani 1 1 d . B . H10A H 0.7236 0.2065 -0.0731 0.175 Uiso 1 1 calc R . . H10B H 0.6978 0.0592 -0.0254 0.175 Uiso 1 1 calc R . . N1 N 0.7186(3) 0.1405(3) 0.3064(2) 0.0571(7) Uani 1 1 d . . . N2 N 0.7776(3) 0.1384(3) 0.1627(2) 0.0616(7) Uani 1 1 d . . . O1 O 0.6575(2) 0.3460(2) 0.40000(17) 0.0703(7) Uani 1 1 d . . . O2 O 0.6615(2) 0.0895(3) 0.45844(15) 0.0698(7) Uani 1 1 d . . . O3 O 0.7147(2) 0.3512(2) 0.21534(17) 0.0657(6) Uani 1 1 d . . . S1 S 0.63762(8) 0.19351(8) 0.37901(5) 0.0553(3) Uani 1 1 d . . . C11 C 0.5887(9) 0.2090(13) -0.0264(6) 0.196(4) Uani 1 1 d . . . H11A H 0.5896 0.3147 -0.0147 0.235 Uiso 1 1 calc R A 1 H11B H 0.5613 0.1623 0.0261 0.235 Uiso 1 1 calc R A 1 C12A C 0.5061(8) 0.1815(13) -0.1148(7) 0.174(5) Uani 0.725(11) 1 d P B 1 H12A H 0.5178 0.2489 -0.1646 0.261 Uiso 0.725(11) 1 calc PR B 1 H12B H 0.4288 0.1949 -0.1054 0.261 Uiso 0.725(11) 1 calc PR B 1 H12C H 0.5145 0.0818 -0.1356 0.261 Uiso 0.725(11) 1 calc PR B 1 C12B C 0.545(2) 0.375(2) -0.058(2) 0.166(13) Uani 0.275(11) 1 d P B 2 H12D H 0.5567 0.3971 -0.1218 0.248 Uiso 0.275(11) 1 calc PR B 2 H12E H 0.5898 0.4436 -0.0100 0.248 Uiso 0.275(11) 1 calc PR B 2 H12F H 0.4636 0.3842 -0.0594 0.248 Uiso 0.275(11) 1 calc PR B 2 H1 H 0.730(3) 0.060(4) 0.307(2) 0.052(10) Uiso 1 1 d . . . H2 H 0.784(3) 0.048(4) 0.172(2) 0.062(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.071(2) 0.085(3) 0.065(2) -0.004(2) 0.0180(18) -0.0007(19) C7 0.071(2) 0.089(3) 0.057(2) 0.0184(19) 0.0115(18) 0.010(2) C6 0.072(2) 0.072(2) 0.0572(19) 0.0178(17) 0.0175(17) 0.0029(18) C5 0.072(2) 0.0443(17) 0.0470(15) -0.0008(13) 0.0185(15) 0.0031(14) C4 0.084(3) 0.086(3) 0.058(2) 0.0211(19) 0.0112(19) -0.014(2) C3 0.082(3) 0.107(3) 0.079(3) 0.023(2) 0.020(2) -0.021(2) C1 0.075(3) 0.151(5) 0.093(3) 0.010(3) 0.009(2) -0.010(3) C8 0.0551(18) 0.0394(16) 0.0603(19) -0.0021(14) 0.0109(15) -0.0042(13) C9 0.093(3) 0.061(2) 0.077(2) 0.0032(18) 0.038(2) 0.0025(19) C10 0.137(5) 0.209(7) 0.095(4) 0.058(4) 0.036(4) 0.043(5) N1 0.0719(18) 0.0343(15) 0.0639(17) 0.0038(12) 0.0147(14) 0.0020(13) N2 0.082(2) 0.0401(15) 0.0661(17) 0.0026(13) 0.0242(15) 0.0047(13) O1 0.1029(19) 0.0463(13) 0.0615(13) -0.0125(11) 0.0201(13) -0.0112(12) O2 0.0890(17) 0.0652(15) 0.0489(12) 0.0082(11) 0.0055(11) -0.0018(12) O3 0.0916(17) 0.0363(12) 0.0736(15) 0.0018(10) 0.0290(13) -0.0016(10) S1 0.0756(6) 0.0422(4) 0.0445(4) -0.0014(3) 0.0088(4) -0.0034(4) C11 0.166(8) 0.305(13) 0.103(5) 0.030(6) 0.010(5) 0.014(8) C12A 0.110(6) 0.237(13) 0.138(8) 0.005(8) -0.038(6) 0.041(7) C12B 0.15(2) 0.095(17) 0.25(3) 0.057(19) 0.03(2) 0.056(14) _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 C2 C3 1.371(5) . ? C2 C7 1.375(5) . ? C2 C1 1.496(5) . ? C7 C6 1.355(5) . ? C7 H7 0.9300 . ? C6 C5 1.384(4) . ? C6 H6 0.9300 . ? C5 C4 1.375(5) . ? C5 S1 1.750(3) . ? C4 C3 1.362(5) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C8 O3 1.223(4) . ? C8 N2 1.319(4) . ? C8 N1 1.398(4) . ? C9 N2 1.447(5) . ? C9 C10 1.490(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.343(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N1 S1 1.630(3) . ? N1 H1 0.74(3) . ? N2 H2 0.83(4) . ? O1 S1 1.417(2) . ? O2 S1 1.426(2) . ? C11 C12A 1.386(11) . ? C11 C12B 1.61(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? C12B H12D 0.9600 . ? C12B H12E 0.9600 . ? C12B H12F 0.9600 . ? 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 C3 C2 C7 117.2(4) . . ? C3 C2 C1 121.5(4) . . ? C7 C2 C1 121.3(4) . . ? C6 C7 C2 121.9(3) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C4 C5 C6 119.5(3) . . ? C4 C5 S1 119.2(3) . . ? C6 C5 S1 121.3(3) . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C3 C2 122.5(4) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O3 C8 N2 124.6(3) . . ? O3 C8 N1 121.1(3) . . ? N2 C8 N1 114.3(3) . . ? N2 C9 C10 113.3(4) . . ? N2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 124.0(7) . . ? C11 C10 H10A 106.3 . . ? C9 C10 H10A 106.3 . . ? C11 C10 H10B 106.3 . . ? C9 C10 H10B 106.3 . . ? H10A C10 H10B 106.4 . . ? C8 N1 S1 125.9(2) . . ? C8 N1 H1 116(3) . . ? S1 N1 H1 115(3) . . ? C8 N2 C9 123.1(3) . . ? C8 N2 H2 119(2) . . ? C9 N2 H2 118(2) . . ? O1 S1 O2 119.42(14) . . ? O1 S1 N1 108.81(15) . . ? O2 S1 N1 104.94(15) . . ? O1 S1 C5 108.74(15) . . ? O2 S1 C5 108.08(15) . . ? N1 S1 C5 106.07(15) . . ? C10 C11 C12A 119.0(9) . . ? C10 C11 C12B 122.3(13) . . ? C12A C11 C12B 79.9(11) . . ? C10 C11 H11A 107.6 . . ? C12A C11 H11A 107.6 . . ? C12B C11 H11A 27.7 . . ? C10 C11 H11B 107.6 . . ? C12A C11 H11B 107.6 . . ? C12B C11 H11B 117.8 . . ? H11A C11 H11B 107.0 . . ? C11 C12A H12A 109.5 . . ? C11 C12A H12B 109.5 . . ? C11 C12A H12C 109.5 . . ? C11 C12B H12D 109.5 . . ? C11 C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11 C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.491 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.053 # Attachment '- form V rt.cif' data_Tolbutamide_formV_rt _database_code_depnum_ccdc_archive 'CCDC 772455' #TrackingRef '- form V rt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 N2 O3 S' _chemical_formula_weight 270.34 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 '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 15.851(6) _cell_length_b 9.288(4) _cell_length_c 19.691(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2899.2(19) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3063 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 18.24 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9171 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25042 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.14 _reflns_number_total 2568 _reflns_number_gt 1647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1178P)^2^+1.3240P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2568 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2362 _refine_ls_wR_factor_gt 0.2086 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 S1 S 0.10542(7) 0.17314(12) 0.39584(6) 0.0843(5) Uani 1 1 d . . . O3 O 0.26888(19) 0.0347(3) 0.42887(16) 0.0904(9) Uani 1 1 d . . . C8 C 0.2671(3) 0.1661(4) 0.43365(18) 0.0736(11) Uani 1 1 d . . . N2 N 0.3333(3) 0.2469(5) 0.4466(2) 0.0838(11) Uani 1 1 d . . . O2 O 0.0471(2) 0.2891(4) 0.3984(2) 0.1150(12) Uani 1 1 d . . . O1 O 0.0867(2) 0.0431(3) 0.42988(15) 0.0950(10) Uani 1 1 d . . . N1 N 0.1924(3) 0.2409(5) 0.4274(2) 0.0870(12) Uani 1 1 d . . . C5 C 0.1271(3) 0.1341(5) 0.3112(2) 0.0817(12) Uani 1 1 d . . . C9 C 0.4170(4) 0.1898(6) 0.4538(3) 0.1080(16) Uani 1 1 d . . . H9A H 0.4140 0.0967 0.4759 0.130 Uiso 1 1 calc R . . H9B H 0.4498 0.2534 0.4826 0.130 Uiso 1 1 calc R . . C2 C 0.1559(4) 0.0717(9) 0.1752(3) 0.119(2) Uani 1 1 d . . . C10 C 0.4609(4) 0.1733(6) 0.3866(4) 0.126(2) Uani 1 1 d . . . H10A H 0.4298 0.1048 0.3591 0.151 Uiso 1 1 calc R . . H10B H 0.4600 0.2651 0.3632 0.151 Uiso 1 1 calc R . . C4 C 0.1150(5) 0.2310(8) 0.2618(4) 0.154(3) Uani 1 1 d . . . H4 H 0.0941 0.3217 0.2726 0.185 Uiso 1 1 calc R . . C1 C 0.1722(6) 0.0344(11) 0.1003(3) 0.189(4) Uani 1 1 d . . . H1A H 0.1259 0.0679 0.0731 0.283 Uiso 1 1 calc R . . H1B H 0.1774 -0.0681 0.0955 0.283 Uiso 1 1 calc R . . H1C H 0.2233 0.0799 0.0855 0.283 Uiso 1 1 calc R . . C6 C 0.1573(5) 0.0002(7) 0.2913(3) 0.129(2) Uani 1 1 d . . . H6 H 0.1674 -0.0704 0.3238 0.155 Uiso 1 1 calc R . . C7 C 0.1723(5) -0.0288(8) 0.2238(3) 0.152(3) Uani 1 1 d . . . H7 H 0.1939 -0.1180 0.2113 0.183 Uiso 1 1 calc R . . C11 C 0.5499(5) 0.1238(9) 0.3923(5) 0.169(3) Uani 1 1 d . . . H11A H 0.5518 0.0348 0.4181 0.203 Uiso 1 1 calc R . . H11B H 0.5826 0.1953 0.4167 0.203 Uiso 1 1 calc R . . C3 C 0.1330(6) 0.1983(10) 0.1953(4) 0.167(3) Uani 1 1 d . . . H3 H 0.1285 0.2711 0.1631 0.201 Uiso 1 1 calc R . . C12 C 0.5881(6) 0.0998(12) 0.3238(6) 0.225(5) Uani 1 1 d . . . H12A H 0.5592 0.0226 0.3014 0.337 Uiso 1 1 calc R . . H12B H 0.6466 0.0755 0.3289 0.337 Uiso 1 1 calc R . . H12C H 0.5831 0.1861 0.2973 0.337 Uiso 1 1 calc R . . H2 H 0.191(3) 0.318(5) 0.428(2) 0.069(14) Uiso 1 1 d . . . H1 H 0.330(3) 0.328(5) 0.444(2) 0.075(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0835(8) 0.0663(7) 0.1032(9) 0.0015(6) 0.0124(6) 0.0008(6) O3 0.102(2) 0.0520(17) 0.117(2) -0.0016(15) -0.0030(17) 0.0017(15) C8 0.103(3) 0.055(2) 0.063(2) -0.0004(18) 0.000(2) 0.000(2) N2 0.103(3) 0.062(2) 0.086(3) -0.001(2) -0.0195(19) -0.006(2) O2 0.094(2) 0.090(2) 0.162(4) -0.003(2) 0.017(2) 0.0169(19) O1 0.107(2) 0.0773(19) 0.101(2) 0.0005(16) 0.0230(17) -0.0137(17) N1 0.101(3) 0.050(2) 0.111(3) -0.006(2) 0.000(2) 0.006(2) C5 0.078(3) 0.070(3) 0.098(3) 0.020(2) -0.004(2) -0.003(2) C9 0.112(4) 0.093(3) 0.119(4) 0.009(3) -0.030(3) -0.006(3) C2 0.133(5) 0.143(5) 0.080(4) 0.019(4) -0.023(3) -0.041(4) C10 0.105(4) 0.090(4) 0.183(7) 0.017(4) 0.000(4) 0.012(3) C4 0.218(8) 0.120(5) 0.124(6) 0.039(4) 0.018(5) 0.038(5) C1 0.240(9) 0.249(10) 0.077(4) 0.005(5) -0.017(5) -0.053(8) C6 0.214(7) 0.093(4) 0.081(3) 0.005(3) 0.005(4) -0.027(4) C7 0.249(9) 0.119(5) 0.089(4) -0.013(4) 0.016(5) -0.042(5) C11 0.121(6) 0.125(5) 0.261(11) 0.026(6) 0.007(6) 0.010(4) C3 0.250(10) 0.136(6) 0.115(6) 0.058(5) -0.006(6) 0.004(6) C12 0.158(8) 0.184(8) 0.332(15) -0.017(9) 0.091(8) 0.001(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.413(3) . ? S1 O2 1.420(3) . ? S1 N1 1.638(4) . ? S1 C5 1.741(5) . ? O3 C8 1.224(5) . ? C8 N2 1.315(6) . ? C8 N1 1.379(6) . ? N2 C9 1.436(6) . ? N2 H1 0.76(5) . ? N1 H2 0.72(5) . ? C5 C4 1.339(7) . ? C5 C6 1.389(7) . ? C9 C10 1.502(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C2 C3 1.293(9) . ? C2 C7 1.363(9) . ? C2 C1 1.536(8) . ? C10 C11 1.487(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C4 C3 1.374(10) . ? C4 H4 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C6 C7 1.377(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C11 C12 1.495(11) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C3 H3 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 S1 O2 119.7(2) . . ? O1 S1 N1 109.0(2) . . ? O2 S1 N1 104.1(2) . . ? O1 S1 C5 108.5(2) . . ? O2 S1 C5 108.6(2) . . ? N1 S1 C5 106.1(2) . . ? O3 C8 N2 124.5(4) . . ? O3 C8 N1 121.0(4) . . ? N2 C8 N1 114.5(4) . . ? C8 N2 C9 123.0(4) . . ? C8 N2 H1 120(3) . . ? C9 N2 H1 115(3) . . ? C8 N1 S1 124.3(3) . . ? C8 N1 H2 121(4) . . ? S1 N1 H2 112(4) . . ? C4 C5 C6 116.6(6) . . ? C4 C5 S1 121.8(5) . . ? C6 C5 S1 121.6(4) . . ? N2 C9 C10 112.3(5) . . ? N2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C3 C2 C7 117.4(6) . . ? C3 C2 C1 123.1(7) . . ? C7 C2 C1 119.3(8) . . ? C11 C10 C9 113.9(6) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C5 C4 C3 120.9(7) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C6 C5 120.4(6) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C2 C7 C6 120.8(7) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C10 C11 C12 111.2(8) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C2 C3 C4 123.5(6) . . ? C2 C3 H3 118.3 . . ? C4 C3 H3 118.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.412 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.055