#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/80/2008069.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2008069 loop_ _publ_author_name 'Parvez, Masood' 'Arayne, M. Saeed' 'Zaman, M. Kamran' 'Sultana, Najma' _publ_section_title ; Gliclazide ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 74 _journal_page_last 75 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C15 H21 N3 O3 S' _chemical_formula_sum 'C15 H21 N3 O3 S' _chemical_formula_weight 323.41 _chemical_name_common Gliclazide _chemical_name_systematic ; N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-p-toluenesulfonamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 107.026(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.8326(7) _cell_length_b 14.3281(15) _cell_length_c 10.976(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293.0(10) _cell_measurement_theta_max 30 _cell_measurement_theta_min 20 _cell_volume 1628.9(5) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1994)' _computing_molecular_graphics TEXSAN _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _diffrn_ambient_temperature 293.0(10) _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 ' _diffrn_measurement_method '\w/2\q ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a ' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3018 _diffrn_reflns_theta_max 68.0 _diffrn_reflns_theta_min 5.0 _diffrn_standards_decay_% 1.48 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.906 _exptl_absorpt_correction_T_max 0.710 _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_type '\y scans (North et al., 1968) ' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_meas 'not measured ' _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.605 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment 'H atoms constrained' _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2871 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.053 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.09P)^2^+0.65P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref 0.149 _reflns_number_gt 2345 _reflns_number_total 2871 _reflns_threshold_expression 'I>2\s(I) ' _[local]_cod_data_source_file fg1499.cif _[local]_cod_data_source_block Gliclazide _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 1628.9(4) _cod_database_code 2008069 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.64937(6) 0.41765(4) 0.15696(6) 0.0407(2) Uani d . 1 . . S O1 0.77119(17) 0.41482(14) 0.25121(18) 0.0532(5) Uani d . 1 . . O O2 0.64109(18) 0.45144(13) 0.03249(17) 0.0510(5) Uani d . 1 . . O O3 0.57675(19) 0.42224(13) 0.39950(17) 0.0519(5) Uani d . 1 . . O N1 0.5549(2) 0.48845(14) 0.20505(19) 0.0436(5) Uani d . 1 . . N N2 0.4693(3) 0.55798(16) 0.3499(2) 0.0558(6) Uani d . 1 . . N N3 0.4543(2) 0.64183(15) 0.2792(2) 0.0467(5) Uani d . 1 . . N C1 0.5373(2) 0.4865(2) 0.3258(2) 0.0427(6) Uani d . 1 . . C C2 0.5795(2) 0.3060(2) 0.1426(2) 0.0414(6) Uani d . 1 . . C C3 0.4885(3) 0.2809(2) 0.0320(3) 0.0568(7) Uani d . 1 . . C C4 0.4347(3) 0.1929(2) 0.0200(3) 0.0627(8) Uani d . 1 . . C C5 0.4709(3) 0.1285(2) 0.1163(3) 0.0520(7) Uani d . 1 . . C C6 0.5633(3) 0.1549(2) 0.2264(3) 0.0707(9) Uani d . 1 . . C C7 0.6175(3) 0.2425(2) 0.2406(3) 0.0639(9) Uani d . 1 . . C C8 0.4083(3) 0.0343(2) 0.1022(4) 0.0709(9) Uani d . 1 . . C C9 0.3215(3) 0.6766(2) 0.2481(3) 0.0558(7) Uani d . 1 . . C C10 0.3327(3) 0.7791(2) 0.2197(3) 0.0617(8) Uani d . 1 . . C C11 0.2432(4) 0.8421(3) 0.2675(5) 0.0842(12) Uani d . 1 . . C C12 0.3172(5) 0.8669(3) 0.4001(5) 0.1016(14) Uani d . 1 . . C C13 0.4545(4) 0.8781(3) 0.3988(4) 0.0852(11) Uani d . 1 . . C C14 0.4707(3) 0.8061(2) 0.3006(3) 0.0623(8) Uani d . 1 . . C C15 0.5321(3) 0.7162(2) 0.3581(3) 0.0628(8) Uani d . 1 . . C H1 0.5132 0.5298 0.1521 0.094(3) Uiso calc R 1 . . H H2 0.4336 0.5530 0.4101 0.094(3) Uiso calc R 1 . . H H3 0.4631 0.3231 -0.0350 0.094(3) Uiso calc R 1 . . H H4 0.3723 0.1769 -0.0552 0.094(3) Uiso calc R 1 . . H H6 0.5898 0.1123 0.2930 0.094(3) Uiso calc R 1 . . H H7 0.6796 0.2587 0.3160 0.094(3) Uiso calc R 1 . . H H8A 0.3444 0.0334 0.1470 0.094(3) Uiso calc R 1 . . H H8B 0.4725 -0.0124 0.1369 0.094(3) Uiso calc R 1 . . H H8C 0.3679 0.0217 0.0135 0.094(3) Uiso calc R 1 . . H H9A 0.2868 0.6684 0.3195 0.094(3) Uiso calc R 1 . . H H9B 0.2662 0.6444 0.1745 0.094(3) Uiso calc R 1 . . H H10 0.3213 0.7893 0.1287 0.094(3) Uiso calc R 1 . . H H11A 0.2210 0.8977 0.2152 0.094(3) Uiso calc R 1 . . H H11B 0.1643 0.8094 0.2659 0.094(3) Uiso calc R 1 . . H H12A 0.3103 0.8179 0.4587 0.094(3) Uiso calc R 1 . . H H12B 0.2851 0.9246 0.4258 0.094(3) Uiso calc R 1 . . H H13A 0.5139 0.8653 0.4823 0.094(3) Uiso calc R 1 . . H H13B 0.4699 0.9408 0.3735 0.094(3) Uiso calc R 1 . . H H14 0.5188 0.8334 0.2464 0.094(3) Uiso calc R 1 . . H H15A 0.6210 0.7130 0.3561 0.094(3) Uiso calc R 1 . . H H15B 0.5308 0.7108 0.4457 0.094(3) Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0408(3) 0.0439(4) 0.0376(4) 0.0053(2) 0.0117(2) 0.0045(2) O1 0.0400(10) 0.0624(12) 0.0512(11) 0.0022(8) 0.0040(8) 0.0053(9) O2 0.0574(11) 0.0569(11) 0.0438(10) 0.0058(9) 0.0227(8) 0.0111(9) O3 0.0684(12) 0.0479(11) 0.0407(10) 0.0112(9) 0.0181(9) 0.0080(8) N1 0.0522(12) 0.0419(11) 0.0375(11) 0.0117(9) 0.0141(9) 0.0055(9) N2 0.0827(17) 0.0439(12) 0.0508(14) 0.0154(12) 0.0350(13) 0.0106(10) N3 0.0564(13) 0.0390(11) 0.0463(12) 0.0061(9) 0.0175(10) 0.0049(9) C1 0.0508(14) 0.0412(13) 0.0366(13) 0.0002(11) 0.0136(11) 0.0014(10) C2 0.0449(13) 0.0408(13) 0.0391(14) 0.0088(10) 0.0131(10) 0.0028(10) C3 0.0702(19) 0.0505(16) 0.0411(15) 0.0009(14) 0.0025(13) 0.0070(12) C4 0.073(2) 0.0567(18) 0.0468(16) -0.0037(15) -0.0013(14) -0.0026(14) C5 0.0563(16) 0.0429(15) 0.0581(17) 0.0054(12) 0.0189(13) -0.0033(12) C6 0.084(2) 0.0527(18) 0.062(2) -0.0016(16) 0.0002(17) 0.0186(15) C7 0.074(2) 0.0526(17) 0.0499(17) -0.0029(15) -0.0054(14) 0.0128(13) C8 0.077(2) 0.0487(17) 0.087(2) 0.0014(16) 0.0244(19) -0.0016(16) C9 0.0481(15) 0.0522(17) 0.0641(18) -0.0002(12) 0.0120(13) 0.0029(14) C10 0.0614(18) 0.0615(19) 0.0637(19) 0.0097(15) 0.0208(15) 0.0136(15) C11 0.068(2) 0.065(2) 0.131(4) 0.0230(18) 0.046(2) 0.024(2) C12 0.121(4) 0.085(3) 0.118(4) 0.025(3) 0.066(3) -0.010(3) C13 0.106(3) 0.053(2) 0.101(3) -0.001(2) 0.039(2) -0.0119(19) C14 0.0647(19) 0.0517(17) 0.076(2) -0.0027(14) 0.0287(16) 0.0041(15) C15 0.0507(16) 0.0532(17) 0.077(2) 0.0005(13) 0.0076(14) -0.0003(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 . 1.419(2) y S1 O2 . 1.427(2) y S1 N1 . 1.634(2) y S1 C2 . 1.758(3) y O3 C1 . 1.218(3) y N1 C1 . 1.394(3) y N2 C1 . 1.333(3) y N2 N3 . 1.414(3) y N3 C9 . 1.465(3) y N3 C15 . 1.473(4) y C2 C3 . 1.369(4) n C2 C7 . 1.376(4) n C3 C4 . 1.378(4) n C4 C5 . 1.371(4) n C5 C6 . 1.377(4) n C5 C8 . 1.497(4) n C6 C7 . 1.375(4) n C9 C10 . 1.514(4) n C10 C11 . 1.526(5) n C10 C14 . 1.547(4) n C11 C12 . 1.484(6) n C12 C13 . 1.501(6) n C13 C14 . 1.538(5) n C14 C15 . 1.501(4) n loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O1 S1 O2 119.46(12) y O1 S1 N1 108.59(12) y O2 S1 N1 103.22(11) y O1 S1 C2 108.88(12) y O2 S1 C2 108.56(12) y N1 S1 C2 107.48(11) y C1 N1 S1 124.6(2) y C1 N2 N3 121.6(2) y N2 N3 C9 111.3(2) y N2 N3 C15 109.8(2) y C9 N3 C15 104.1(2) y O3 C1 N2 123.8(2) n O3 C1 N1 121.8(2) n N2 C1 N1 114.3(2) n C3 C2 C7 119.5(3) n C3 C2 S1 119.9(2) n C7 C2 S1 120.6(2) n C2 C3 C4 119.9(3) n C5 C4 C3 121.6(3) n C4 C5 C6 117.5(3) n C4 C5 C8 120.5(3) n C6 C5 C8 121.9(3) n C7 C6 C5 121.8(3) n C6 C7 C2 119.6(3) n N3 C9 C10 104.2(2) n C9 C10 C11 113.9(3) n C9 C10 C14 104.3(2) n C11 C10 C14 105.0(3) n C12 C11 C10 105.3(3) n C11 C12 C13 105.6(3) n C12 C13 C14 104.6(3) n C15 C14 C13 114.0(3) n C15 C14 C10 105.2(2) n C13 C14 C10 106.3(3) n N3 C15 C14 105.5(2) n loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 O2 3_665 0.86 2.23 2.967(3) 143 N2 H2 O3 3_666 0.86 2.15 2.949(3) 153 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O1 S1 N1 C1 -48.4(2) n O2 S1 N1 C1 -176.2(2) n C2 S1 N1 C1 69.2(2) n C1 N2 N3 C9 137.7(3) n C1 N2 N3 C15 -107.5(3) n N3 N2 C1 O3 163.2(3) n N3 N2 C1 N1 -19.8(4) n S1 N1 C1 O3 -11.2(4) n S1 N1 C1 N2 171.73(19) n O1 S1 C2 C3 -156.5(2) n O2 S1 C2 C3 -24.9(3) n N1 S1 C2 C3 86.1(2) n O1 S1 C2 C7 22.0(3) n O2 S1 C2 C7 153.6(2) n N1 S1 C2 C7 -95.4(3) n C7 C2 C3 C4 0.8(5) n S1 C2 C3 C4 179.3(3) n C2 C3 C4 C5 -0.7(5) n C3 C4 C5 C6 0.2(5) n C3 C4 C5 C8 178.3(3) n C4 C5 C6 C7 0.3(5) n C8 C5 C6 C7 -177.8(3) n C5 C6 C7 C2 -0.2(6) n C3 C2 C7 C6 -0.3(5) n S1 C2 C7 C6 -178.8(3) n N2 N3 C9 C10 159.4(2) n C15 N3 C9 C10 41.1(3) n N3 C9 C10 C11 -142.3(3) n N3 C9 C10 C14 -28.4(3) n C9 C10 C11 C12 88.4(4) n C14 C10 C11 C12 -25.0(4) n C10 C11 C12 C13 36.9(4) n C11 C12 C13 C14 -33.7(4) n C12 C13 C14 C15 -97.9(4) n C12 C13 C14 C10 17.5(4) n C9 C10 C14 C15 5.5(3) n C11 C10 C14 C15 125.6(3) n C9 C10 C14 C13 -115.8(3) n C11 C10 C14 C13 4.4(3) n N2 N3 C15 C14 -157.0(2) n C9 N3 C15 C14 -37.7(3) n C13 C14 C15 N3 135.3(3) n C10 C14 C15 N3 19.2(3) n _journal_paper_doi 10.1107/S0108270198009883