#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/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_paper_doi               10.1107/S0108270198009883
_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       'ω/2θ '
_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      ?
_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_details
'w = 1/[σ²(Fo²)+(0.09P)²+0.65P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.149
_reflns_number_gt                2345
_reflns_number_total             2871
_reflns_threshold_expression     'I>2σ(I) '
_cod_data_source_file            fg1499.cif
_cod_data_source_block           Gliclazide
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured ' was changed to
'?' - the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.09P)^2^+0.65P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.09P)^2^+0.65P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1628.9(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_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_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_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_
_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3356
