#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209722.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_2209722
loop_
_publ_author_name
'Seferoğlu, Zeynel'
'Hökelek, Tuncer'
'Şahin, Ertan'
'Nuralın, Fatma'
_publ_section_title
;
 2-Amino-5-(p-nitrophenylsulfonyl)-1,3-thiazole
;
_journal_coeditor_code           YM2010
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2634
_journal_page_last               o2636
_journal_paper_doi               10.1107/S1600536806020162
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H7 N3 O4 S2'
_chemical_formula_moiety         'C9 H7 N3 O4 S2'
_chemical_formula_sum            'C9 H7 N3 O4 S2'
_chemical_formula_weight         285.30
_chemical_name_systematic
;
2-Amino-5-(p-nitrophenylsulfonyl)-1,3-thiazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 110.874(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6310(2)
_cell_length_b                   12.4943(3)
_cell_length_c                   11.4911(4)
_cell_measurement_reflns_used    5980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.5214
_cell_measurement_theta_min      2.0501
_cell_volume                     1157.85(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22950
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.432
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.042P)²+0.3858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                3314
_reflns_number_total             3543
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ym2010.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209722
_cod_database_fobs_code          2209722
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S S1 0.34542(5) 0.31628(3) 0.71182(4) 0.03790(12) Uani d . 1
S S2 0.40853(5) 0.12202(3) 0.57648(3) 0.03312(11) Uani d . 1
O O1 0.58132(15) 0.13928(10) 0.64556(13) 0.0457(3) Uani d . 1
O O2 0.35521(17) 0.08579(10) 0.44973(11) 0.0450(3) Uani d . 1
O O3 0.2490(2) -0.18866(15) 0.98565(16) 0.0708(5) Uani d . 1
O O4 0.08179(19) -0.26177(14) 0.81838(17) 0.0658(4) Uani d . 1
N N 0.1498(2) 0.49068(13) 0.67542(16) 0.0481(4) Uani d D 1
N N1 0.1849(2) -0.19488(14) 0.87233(16) 0.0490(4) Uani d . 1
C C2 0.19032(17) 0.40406(12) 0.62471(15) 0.0336(3) Uani d . 1
N N3 0.11720(17) 0.37688(11) 0.50598(13) 0.0380(3) Uani d . 1
C C4 0.18200(19) 0.28385(13) 0.48162(15) 0.0364(3) Uani d . 1
C C5 0.30465(18) 0.23931(12) 0.57884(14) 0.0332(3) Uani d . 1
C C6 0.33786(19) 0.02858(12) 0.66269(14) 0.0339(3) Uani d . 1
C C7 0.3783(2) 0.04535(14) 0.78999(16) 0.0436(4) Uani d . 1
C C8 0.3247(2) -0.02768(16) 0.85822(16) 0.0451(4) Uani d . 1
C C9 0.2370(2) -0.11637(14) 0.79797(16) 0.0395(3) Uani d . 1
C C10 0.1995(2) -0.13523(16) 0.67283(18) 0.0446(4) Uani d . 1
C C11 0.2500(2) -0.06080(15) 0.60365(16) 0.0412(4) Uani d . 1
H H1 0.082(3) 0.535(2) 0.624(2) 0.062(7) Uiso d . 1
H H2 0.212(3) 0.513(2) 0.7503(17) 0.067(7) Uiso d D 1
H H4 0.140(2) 0.2543(16) 0.4044(19) 0.037(5) Uiso d . 1
H H7 0.430(3) 0.109(2) 0.832(2) 0.070(7) Uiso d . 1
H H8 0.346(3) -0.0129(19) 0.943(2) 0.055(6) Uiso d . 1
H H10 0.146(3) -0.1983(18) 0.638(2) 0.052(6) Uiso d . 1
H H11 0.224(3) -0.076(2) 0.515(2) 0.060(6) Uiso d . 1
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'
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
C5 S1 C2 88.26(7) y
O1 S2 O2 120.21(8) y
O1 S2 C5 107.92(8) y
O2 S2 C5 107.68(7) y
O1 S2 C6 106.64(8) y
O2 S2 C6 108.02(8) y
C5 S2 C6 105.46(8) y
C2 N H1 116.3(16) ?
C2 N H2 121.8(17) ?
H1 N H2 119(2) ?
O4 N1 O3 123.89(18) y
O4 N1 C9 118.74(17) y
O3 N1 C9 117.37(17) y
N3 C2 N 123.66(14) y
N3 C2 S1 114.56(11) y
N C2 S1 121.78(13) y
C2 N3 C4 110.50(13) y
C5 C4 N3 116.02(14) y
C5 C4 H4 124.2(12) ?
N3 C4 H4 119.7(12) ?
C4 C5 S2 126.47(12) y
C4 C5 S1 110.66(12) y
S2 C5 S1 122.87(9) y
C11 C6 C7 121.64(15) ?
C11 C6 S2 119.64(12) y
C7 C6 S2 118.68(13) y
C8 C7 C6 119.06(17) ?
C8 C7 H7 117.1(16) ?
C6 C7 H7 123.4(16) ?
C9 C8 C7 118.60(16) ?
C9 C8 H8 123.0(14) ?
C7 C8 H8 118.4(14) ?
C10 C9 C8 122.93(16) y
C10 C9 N1 119.03(17) y
C8 C9 N1 118.03(16) y
C9 C10 C11 118.52(17) ?
C9 C10 H10 119.6(14) ?
C11 C10 H10 121.8(14) ?
C6 C11 C10 119.21(16) ?
C6 C11 H11 123.0(15) ?
C10 C11 H11 117.8(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.7442(15) y
S1 C5 1.7322(15) y
S2 O1 1.4343(13) y
S2 O2 1.4354(12) y
S2 C5 1.7231(15) y
S2 C6 1.7740(16) y
N H1 0.87(2) ?
N H2 0.883(16) ?
N1 O3 1.223(2) y
N1 O4 1.217(2) y
C2 N 1.333(2) y
N3 C2 1.327(2) y
N3 C4 1.361(2) y
C4 H4 0.91(2) ?
C5 C4 1.355(2) ?
C6 C7 1.393(2) ?
C6 C11 1.384(2) ?
C7 H7 0.95(3) ?
C8 C7 1.386(3) ?
C8 H8 0.95(2) ?
C9 N1 1.472(2) y
C9 C8 1.381(3) ?
C9 C10 1.377(2) ?
C10 H10 0.93(2) ?
C11 C10 1.391(3) ?
C11 H11 0.98(2) ?
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
C2 S1 C5 C4 0.26(13) y
C2 S1 C5 S2 -179.14(11) ?
C5 S1 C2 N3 -0.62(13) y
C5 S1 C2 N 178.99(16) ?
O1 S2 C5 C4 137.55(16) ?
O2 S2 C5 C4 6.39(18) ?
C6 S2 C5 C4 -108.76(16) ?
O1 S2 C5 S1 -43.15(13) ?
O2 S2 C5 S1 -174.31(10) ?
C6 S2 C5 S1 70.54(12) ?
O1 S2 C6 C11 -129.60(14) ?
O2 S2 C6 C11 0.91(16) ?
C5 S2 C6 C11 115.83(14) ?
O1 S2 C6 C7 47.92(15) ?
O2 S2 C6 C7 178.43(13) ?
C5 S2 C6 C7 -66.66(15) ?
C2 N3 C4 C5 -0.6(2) y
C4 N3 C2 N -178.80(17) ?
C4 N3 C2 S1 0.80(18) y
S2 C5 C4 N3 179.51(12) ?
S1 C5 C4 N3 0.1(2) y
C7 C6 C11 C10 0.6(3) ?
S2 C6 C11 C10 178.08(14) ?
S2 C6 C7 C8 -179.51(14) ?
C11 C6 C7 C8 -2.0(3) ?
C9 C8 C7 C6 1.9(3) ?
C8 C9 C10 C11 -1.0(3) ?
N1 C9 C10 C11 -179.69(16) ?
C10 C9 C8 C7 -0.4(3) ?
N1 C9 C8 C7 178.30(16) ?
C10 C9 N1 O4 -15.2(2) ?
C8 C9 N1 O4 166.04(17) ?
C10 C9 N1 O3 164.65(18) ?
C8 C9 N1 O3 -14.1(2) ?
C6 C11 C10 C9 0.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1481
