#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227857.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227857
loop_
_publ_author_name
'Qin, Xiu-Ying'
'Liu, Han-Fu'
'Lin, Jia-Xun'
_publ_section_title
;
 4-Amino-3,5-dichlorobenzenesulfonamide
;
_journal_coeditor_code           NK2060
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2838
_journal_paper_doi               10.1107/S1600536810040584
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H6 Cl2 N2 O2 S'
_chemical_formula_moiety         'C6 H6 Cl2 N2 O2 S'
_chemical_formula_sum            'C6 H6 Cl2 N2 O2 S'
_chemical_formula_weight         241.09
_chemical_melting_point_gt       207.2
_chemical_melting_point_lt       207.5
_chemical_name_systematic
;
4-Amino-3,5-dichlorobenzenesulfonamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.809(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9544(17)
_cell_length_b                   13.387(3)
_cell_length_c                   7.5673(15)
_cell_measurement_reflns_used    2008
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.04
_cell_volume                     902.5(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5918
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_T_max  0.8880
_exptl_absorpt_correction_T_min  0.7708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0293
_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)+(0.0461P)²+0.2600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                1759
_reflns_number_total             2008
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nk2060.cif
_cod_data_source_block           I
_cod_original_cell_volume        902.4(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227857
_cod_database_fobs_code          2227857
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.24595(5) 0.01031(3) 0.45203(6) 0.01881(13) Uani d . 1 . .
Cl Cl2 0.00000(5) 0.37179(3) 0.29728(7) 0.02268(13) Uani d . 1 . .
S S1 0.57265(5) 0.34844(3) 0.58837(6) 0.01325(12) Uani d . 1 . .
O O1 0.53529(14) 0.43437(9) 0.68889(17) 0.0171(3) Uani d . 1 . .
O O2 0.67408(13) 0.27471(9) 0.67149(18) 0.0190(3) Uani d . 1 . .
N N1 0.00496(18) 0.15006(13) 0.3074(2) 0.0198(4) Uani d . 1 . .
N N2 0.64946(18) 0.39096(12) 0.4206(2) 0.0166(3) Uani d . 1 . .
C C1 0.40449(19) 0.28746(13) 0.5127(2) 0.0135(3) Uani d . 1 . .
C C2 0.39422(19) 0.18356(12) 0.5117(2) 0.0137(3) Uani d . 1 . .
H H2 0.4778 0.1437 0.5551 0.016 Uiso calc R 1 . .
C C3 0.26064(19) 0.13958(13) 0.4466(2) 0.0145(4) Uani d . 1 . .
C C4 0.13407(19) 0.19420(13) 0.3762(2) 0.0143(4) Uani d . 1 . .
C C5 0.15166(19) 0.29916(13) 0.3806(2) 0.0155(4) Uani d . 1 . .
C C6 0.28195(19) 0.34575(13) 0.4475(2) 0.0151(4) Uani d . 1 . .
H H6 0.2885 0.4166 0.4493 0.018 Uiso calc R 1 . .
H H1A -0.001(3) 0.0906(19) 0.305(3) 0.032(7) Uiso d . 1 . .
H H2A 0.604(3) 0.4378(17) 0.375(3) 0.022(6) Uiso d . 1 . .
H H1B -0.071(3) 0.1841(18) 0.277(3) 0.033(7) Uiso d . 1 . .
H H2B 0.665(3) 0.3444(19) 0.346(4) 0.039(7) Uiso 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
Cl1 0.0172(2) 0.0123(2) 0.0260(2) -0.00223(16) -0.00262(17) -0.00010(16)
Cl2 0.0118(2) 0.0194(2) 0.0355(3) 0.00248(17) -0.00420(18) 0.00595(19)
S1 0.0103(2) 0.0123(2) 0.0165(2) -0.00140(15) -0.00131(16) 0.00062(15)
O1 0.0175(7) 0.0159(6) 0.0177(6) -0.0018(5) 0.0006(5) -0.0024(5)
O2 0.0132(7) 0.0156(6) 0.0267(7) -0.0008(5) -0.0049(5) 0.0048(5)
N1 0.0123(9) 0.0168(8) 0.0287(9) -0.0024(7) -0.0059(7) 0.0018(7)
N2 0.0154(8) 0.0138(7) 0.0207(8) -0.0003(6) 0.0027(6) -0.0002(6)
C1 0.0112(9) 0.0153(8) 0.0137(8) -0.0015(6) 0.0005(7) -0.0005(7)
C2 0.0120(9) 0.0142(8) 0.0146(8) 0.0005(7) 0.0003(7) 0.0006(7)
C3 0.0152(9) 0.0123(8) 0.0160(8) -0.0006(7) 0.0017(7) 0.0008(6)
C4 0.0113(9) 0.0174(8) 0.0140(8) -0.0019(7) 0.0003(7) 0.0004(7)
C5 0.0123(9) 0.0168(8) 0.0172(9) 0.0036(7) 0.0007(7) 0.0036(7)
C6 0.0138(9) 0.0120(8) 0.0195(9) 0.0004(6) 0.0020(7) 0.0008(7)
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 119.15(8) n
O1 S1 N2 . . 106.00(8) n
O2 S1 N2 . . 106.61(8) n
O1 S1 C1 . . 107.86(8) n
O2 S1 C1 . . 107.78(8) n
N2 S1 C1 . . 109.15(8) n
C4 N1 H1A . . 119.6(18) n
C4 N1 H1B . . 120.7(17) n
H1A N1 H1B . . 119(2) n
S1 N2 H2A . . 112.2(16) n
S1 N2 H2B . . 111.9(17) n
H2A N2 H2B . . 113(2) n
C2 C1 C6 . . 120.47(16) n
C2 C1 S1 . . 121.28(13) n
C6 C1 S1 . . 118.21(13) n
C3 C2 C1 . . 118.85(16) n
C3 C2 H2 . . 120.6 n
C1 C2 H2 . . 120.6 n
C2 C3 C4 . . 123.34(16) n
C2 C3 Cl1 . . 118.83(13) n
C4 C3 Cl1 . . 117.83(13) n
N1 C4 C3 . . 122.82(17) n
N1 C4 C5 . . 122.09(16) n
C3 C4 C5 . . 115.08(15) n
C6 C5 C4 . . 123.25(16) n
C6 C5 Cl2 . . 118.92(14) n
C4 C5 Cl2 . . 117.83(13) n
C5 C6 C1 . . 118.99(16) n
C5 C6 H6 . . 120.5 n
C1 C6 H6 . . 120.5 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
Cl1 C3 . 1.7363(18) n
Cl2 C5 . 1.7360(17) n
S1 O1 . 1.4370(13) n
S1 O2 . 1.4419(13) n
S1 N2 . 1.6078(16) n
S1 C1 . 1.7571(18) n
N1 C4 . 1.355(2) n
N1 H1A . 0.80(2) n
N1 H1B . 0.83(3) n
N2 H2A . 0.81(2) n
N2 H2B . 0.86(3) n
C1 C2 . 1.394(2) n
C1 C6 . 1.395(2) n
C2 C3 . 1.379(2) n
C2 H2 . 0.9500 n
C3 C4 . 1.407(2) n
C4 C5 . 1.414(2) n
C5 C6 . 1.374(2) n
C6 H6 . 0.9500 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 H1A Cl1 . 0.80(2) 2.60(2) 2.9793(18) 111(2)
N2 H2A O1 3_666 0.81(2) 2.14(2) 2.935(2) 167(2)
N1 H1B O2 4_465 0.83(3) 2.40(3) 3.199(2) 160(2)
N2 H2B O2 4_565 0.86(3) 2.08(3) 2.934(2) 172(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . -140.05(14) n
O2 S1 C1 C2 . . . . -10.20(17) n
N2 S1 C1 C2 . . . . 105.21(15) n
O1 S1 C1 C6 . . . . 42.09(16) n
O2 S1 C1 C6 . . . . 171.94(13) n
N2 S1 C1 C6 . . . . -72.65(16) n
C6 C1 C2 C3 . . . . -0.5(3) n
S1 C1 C2 C3 . . . . -178.35(13) n
C1 C2 C3 C4 . . . . 1.7(3) n
C1 C2 C3 Cl1 . . . . -177.91(13) n
C2 C3 C4 N1 . . . . 177.82(17) n
Cl1 C3 C4 N1 . . . . -2.6(2) n
C2 C3 C4 C5 . . . . -1.5(3) n
Cl1 C3 C4 C5 . . . . 178.10(13) n
N1 C4 C5 C6 . . . . -179.13(17) n
C3 C4 C5 C6 . . . . 0.2(3) n
N1 C4 C5 Cl2 . . . . 1.0(2) n
C3 C4 C5 Cl2 . . . . -179.65(13) n
C4 C5 C6 C1 . . . . 0.8(3) n
Cl2 C5 C6 C1 . . . . -179.29(13) n
C2 C1 C6 C5 . . . . -0.7(3) n
S1 C1 C6 C5 . . . . 177.19(13) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 80876
