#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/68/2016887.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_2016887
loop_
_publ_author_name
'Drebushchak, Tatiana N.'
'Chukanov, Nikita V.'
'Boldyreva, Elena V.'
_publ_section_title
;
 Two polymorphs of chlorpropamide: the δ-form and the high-temperature
 ε-form
;
_journal_coeditor_code           TR3050
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o623
_journal_page_last               o625
_journal_paper_doi               10.1107/S0108270108034550
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H13 Cl N2 O3 S'
_chemical_formula_moiety         'C10 H13 Cl N2 O3 S'
_chemical_formula_sum            'C10 H13 Cl N2 O3 S'
_chemical_formula_weight         276.73
_chemical_melting_point
;
Kinetic phase transition (Drebushchak <i>et al.</i>, 2008)
;
_chemical_name_common            'chlorpropamide, δ-form'
_chemical_name_systematic
;
4-chloro-N-(propylaminocarbonyl)benzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.3198(4)
_cell_length_b                   10.3218(3)
_cell_length_c                   26.2663(10)
_cell_measurement_reflns_used    1546
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.9990
_cell_measurement_theta_min      4.2706
_cell_volume                     2526.74(16)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and publCIF
(Westrip, 2007)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Oxford Diffraction KM4 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6522
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         5.82
_exptl_absorpt_coefficient_mu    4.235
_exptl_absorpt_correction_T_max  0.8828
_exptl_absorpt_correction_T_min  0.4321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.378
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1038P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                1318
_reflns_number_total             2159
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tr3050.cif
_cod_data_source_block           d-form
_cod_database_code               2016887
_cod_database_fobs_code          2016887
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_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
C C1 0.1637(6) 0.6441(5) 0.29327(18) 0.0748(14) Uani d . 1
C C2 0.0520(6) 0.7283(6) 0.2962(2) 0.0883(17) Uani d . 1
H H2 -0.0166 0.7316 0.2705 0.106 Uiso calc R 1
C C3 0.0419(5) 0.8098(5) 0.33845(19) 0.0723(13) Uani d . 1
H H3 -0.0332 0.8687 0.3411 0.087 Uiso calc R 1
C C4 0.1438(4) 0.8024(4) 0.37608(14) 0.0489(9) Uani d . 1
C C5 0.2565(5) 0.7192(4) 0.37148(16) 0.0622(11) Uani d . 1
H H5 0.3262 0.7163 0.3968 0.075 Uiso calc R 1
C C6 0.2684(6) 0.6392(5) 0.32948(18) 0.0743(14) Uani d . 1
H H6 0.3460 0.5833 0.3260 0.089 Uiso calc R 1
C C7 0.1512(4) 0.7253(4) 0.50360(14) 0.0478(9) Uani d . 1
C C8 0.1343(5) 0.5476(5) 0.56420(18) 0.0658(12) Uani d . 1
H H8A 0.2368 0.5440 0.5580 0.079 Uiso calc R 1
H H8B 0.0940 0.4643 0.5548 0.079 Uiso calc R 1
C C9 0.1095(9) 0.5695(7) 0.6193(3) 0.126(3) Uani d D 1
H H9A 0.0089 0.5527 0.6260 0.151 Uiso calc R 1
H H9B 0.1639 0.5045 0.6377 0.151 Uiso calc R 1
C C10 0.1437(10) 0.6939(8) 0.6413(3) 0.192(5) Uani d D 1
H H10A 0.2441 0.7114 0.6369 0.231 Uiso calc R 1
H H10B 0.1212 0.6929 0.6770 0.231 Uiso calc R 1
H H10C 0.0885 0.7601 0.6248 0.231 Uiso calc R 1
N N1 0.0706(3) 0.8150(3) 0.47570(12) 0.0522(9) Uani d . 1
H H1N -0.0185 0.8230 0.4836 0.063 Uiso calc R 1
N N2 0.0718(3) 0.6471(3) 0.53210(13) 0.0558(9) Uani d . 1
H H2N -0.0199 0.6557 0.5315 0.067 Uiso calc R 1
O O1 0.0195(3) 0.9955(3) 0.41986(11) 0.0597(8) Uani d . 1
O O2 0.2709(3) 0.9501(3) 0.44145(11) 0.0563(8) Uani d . 1
O O3 0.2821(3) 0.7228(3) 0.50048(11) 0.0575(8) Uani d . 1
S S1 0.13079(10) 0.90580(9) 0.42946(4) 0.0487(4) Uani d . 1
Cl Cl1 0.1775(2) 0.54007(18) 0.24117(6) 0.1281(8) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.094(4) 0.076(3) 0.054(3) -0.013(3) 0.003(3) -0.006(2)
C2 0.073(4) 0.118(4) 0.074(3) -0.006(3) -0.018(3) -0.020(3)
C3 0.051(3) 0.096(3) 0.070(3) 0.007(3) -0.009(2) -0.008(3)
C4 0.041(2) 0.056(2) 0.049(2) -0.0021(19) 0.0012(19) 0.0094(18)
C5 0.065(3) 0.069(3) 0.053(2) 0.013(2) -0.006(2) 0.002(2)
C6 0.093(4) 0.071(3) 0.059(3) 0.017(3) 0.002(3) 0.000(2)
C7 0.037(2) 0.060(2) 0.046(2) 0.003(2) 0.0002(18) -0.0057(18)
C8 0.063(3) 0.068(2) 0.066(3) 0.001(2) -0.003(2) 0.012(2)
C9 0.152(6) 0.149(6) 0.076(4) 0.039(6) -0.027(4) 0.030(4)
C10 0.203(9) 0.232(10) 0.142(7) 0.117(8) -0.090(7) -0.098(8)
N1 0.0331(17) 0.067(2) 0.056(2) 0.0077(16) 0.0051(15) 0.0059(16)
N2 0.0381(18) 0.071(2) 0.059(2) 0.0010(17) 0.0028(16) 0.0101(18)
O1 0.0481(16) 0.0558(14) 0.0752(19) 0.0118(14) 0.0052(14) 0.0082(14)
O2 0.0383(16) 0.0602(15) 0.0705(18) -0.0106(13) 0.0000(13) -0.0031(14)
O3 0.0322(15) 0.0715(18) 0.0687(18) 0.0010(13) 0.0008(13) 0.0111(15)
S1 0.0384(6) 0.0532(5) 0.0544(6) 0.0019(5) 0.0027(5) 0.0028(5)
Cl1 0.1794(19) 0.1276(13) 0.0775(10) -0.0071(13) -0.0020(10) -0.0391(10)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.0000 '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
C2 C1 C6 122.1(5)
C2 C1 Cl1 119.7(4)
C6 C1 Cl1 118.2(4)
C1 C2 C3 118.8(5)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 119.5(4)
C4 C3 H3 120.2
C2 C3 H3 120.2
C5 C4 C3 120.3(4)
C5 C4 S1 120.2(3)
C3 C4 S1 119.4(3)
C4 C5 C6 120.6(4)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.5(5)
C1 C6 H6 120.7
C5 C6 H6 120.7
O3 C7 N2 125.5(4)
O3 C7 N1 120.9(4)
N2 C7 N1 113.5(3)
N2 C8 C9 113.4(4)
N2 C8 H8A 108.9
C9 C8 H8A 108.9
N2 C8 H8B 108.9
C9 C8 H8B 108.9
H8A C8 H8B 107.7
C10 C9 C8 119.5(7)
C10 C9 H9A 107.4
C8 C9 H9A 107.4
C10 C9 H9B 107.4
C8 C9 H9B 107.4
H9A C9 H9B 107.0
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 N1 S1 125.8(3)
C7 N1 H1N 117.1
S1 N1 H1N 117.1
C7 N2 C8 122.4(3)
C7 N2 H2N 118.8
C8 N2 H2N 118.8
O1 S1 O2 120.26(17)
O1 S1 N1 104.88(16)
O2 S1 N1 109.63(17)
O1 S1 C4 107.72(18)
O2 S1 C4 107.93(17)
N1 S1 C4 105.49(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.359(7)
C1 C6 1.363(7)
C1 Cl1 1.744(5)
C2 C3 1.395(7)
C2 H2 0.9300
C3 C4 1.372(6)
C3 H3 0.9300
C4 C5 1.363(5)
C4 S1 1.766(4)
C5 C6 1.383(6)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.223(4)
C7 N2 1.326(5)
C7 N1 1.399(5)
C8 N2 1.450(5)
C8 C9 1.483(8)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.444(9)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
N1 S1 1.634(3)
N1 H1N 0.8600
N2 H2N 0.8600
O1 S1 1.413(3)
O2 S1 1.419(3)
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
_geom_hbond_publ_flag
N1 H1N O3 4_466 0.86 1.96 2.788(4) 160 no
N2 H2N O2 4_466 0.86 2.34 3.058(4) 141 no
N2 H2N O3 4_466 0.86 2.38 3.135(4) 146 no
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
C6 C1 C2 C3 -1.9(8) ?
Cl1 C1 C2 C3 179.3(4) ?
C1 C2 C3 C4 -0.6(8) ?
C2 C3 C4 C5 2.2(7) ?
C2 C3 C4 S1 180.0(4) ?
C3 C4 C5 C6 -1.4(6) ?
S1 C4 C5 C6 -179.2(4) ?
C2 C1 C6 C5 2.7(8) ?
Cl1 C1 C6 C5 -178.5(4) ?
C4 C5 C6 C1 -1.0(7) ?
N2 C8 C9 C10 -50.9(8) no
O3 C7 N1 S1 11.8(5) no
N2 C7 N1 S1 -167.8(3) no
O3 C7 N2 C8 0.7(6) no
N1 C7 N2 C8 -179.6(4) no
C9 C8 N2 C7 115.4(6) no
C7 N1 S1 O1 -169.5(3) no
C7 N1 S1 O2 -39.1(4) no
C7 N1 S1 C4 76.9(3) no
C5 C4 S1 O1 169.9(3) no
C3 C4 S1 O1 -7.9(4) no
C5 C4 S1 O2 38.6(4) no
C3 C4 S1 O2 -139.2(3) no
C5 C4 S1 N1 -78.5(4) no
C3 C4 S1 N1 103.7(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2626
