#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/08/2220819.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_2220819
loop_
_publ_author_name
'Ghazisaeidi, Reza'
'Yousefi, Mohammad'
_publ_section_title
;
 3-(3-Aminophenylsulfonyl)aniline
;
_journal_coeditor_code           HK2599
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o222
_journal_paper_doi               10.1107/S1600536808043389
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H12 N2 O2 S'
_chemical_formula_moiety         'C12 H12 N2 O2 S'
_chemical_formula_sum            'C12 H12 N2 O2 S'
_chemical_formula_weight         248.30
_chemical_name_systematic
;
3-(3-Aminophenylsulfonyl)aniline
;
_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                 98.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6282(17)
_cell_length_b                   8.8017(18)
_cell_length_c                   16.052(3)
_cell_measurement_reflns_used    1532
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      2.38
_cell_volume                     1206.8(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18754
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         4145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0789P)²+0.6213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2175
_reflns_number_gt                2971
_reflns_number_total             4145
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2599.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220819
_cod_database_fobs_code          2220819
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
S S1 0.25722(7) 0.35241(8) 0.12847(4) 0.0538(2) Uani d . 1 . .
O O1 0.2448(2) 0.4691(2) 0.06463(15) 0.0705(6) Uani d . 1 . .
O O2 0.3825(2) 0.3662(3) 0.19740(15) 0.0734(6) Uani d . 1 . .
N N1 0.4728(5) -0.1878(5) 0.1176(3) 0.1187(14) Uani d . 1 . .
H H1A 0.4757 -0.2745 0.0933 0.142 Uiso calc R 1 . .
H H1B 0.5288 -0.1722 0.1656 0.142 Uiso calc R 1 . .
N N2 -0.3243(3) 0.4789(4) 0.1136(2) 0.0844(9) Uani d . 1 . .
H H2B -0.4113 0.4778 0.1340 0.101 Uiso calc R 1 . .
H H2A -0.3183 0.5252 0.0670 0.101 Uiso calc R 1 . .
C C1 0.3714(3) 0.0656(3) 0.11930(19) 0.0633(7) Uani d . 1 . .
H H1 0.4308 0.0854 0.1711 0.076 Uiso calc R 1 . .
C C2 0.3800(4) -0.0758(4) 0.0805(2) 0.0765(9) Uani d . 1 . .
C C3 0.2912(6) -0.1002(5) 0.0046(3) 0.0977(13) Uani d . 1 . .
H H3 0.2966 -0.1946 -0.0208 0.117 Uiso calc R 1 . .
C C4 0.1948(6) 0.0077(5) -0.0357(3) 0.0979(13) Uani d . 1 . .
H H4 0.1368 -0.0127 -0.0879 0.117 Uiso calc R 1 . .
C C5 0.1844(5) 0.1493(4) 0.0026(2) 0.0785(9) Uani d . 1 . .
H H5 0.1187 0.2244 -0.0234 0.094 Uiso calc R 1 . .
C C6 0.2733(3) 0.1754(3) 0.07936(18) 0.0558(6) Uani d . 1 . .
C C7 0.0781(3) 0.3441(3) 0.16923(16) 0.0498(5) Uani d . 1 . .
C C8 -0.0511(3) 0.4117(3) 0.12433(16) 0.0513(5) Uani d . 1 . .
H H8 -0.0433 0.4605 0.0737 0.062 Uiso calc R 1 . .
C C9 -0.1947(3) 0.4063(3) 0.15552(18) 0.0545(6) Uani d . 1 . .
C C10 -0.2009(4) 0.3306(4) 0.2309(2) 0.0645(7) Uani d . 1 . .
H H10 -0.2956 0.3251 0.2522 0.077 Uiso calc R 1 . .
C C11 -0.0704(4) 0.2637(4) 0.2746(2) 0.0735(8) Uani d . 1 . .
H H11 -0.0780 0.2140 0.3250 0.088 Uiso calc R 1 . .
C C12 0.0725(4) 0.2692(4) 0.24466(19) 0.0660(7) Uani d . 1 . .
H H12 0.1613 0.2242 0.2741 0.079 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 C6 . . 108.32(13) ?
O1 S1 C7 . . 108.16(12) ?
O2 S1 O1 . . 117.27(14) ?
O2 S1 C6 . . 108.72(14) ?
O2 S1 C7 . . 108.72(13) ?
C6 S1 C7 . . 104.97(12) ?
C2 N1 H1A . . 120.0 ?
C2 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C9 N2 H2A . . 120.0 ?
C9 N2 H2B . . 120.0 ?
H2B N2 H2A . . 120.0 ?
C6 C1 C2 . . 119.0(3) ?
C6 C1 H1 . . 120.5 ?
C2 C1 H1 . . 120.5 ?
N1 C2 C3 . . 120.1(4) ?
N1 C2 C1 . . 121.2(4) ?
C3 C2 C1 . . 118.7(3) ?
C2 C3 C4 . . 122.9(4) ?
C2 C3 H3 . . 118.5 ?
C4 C3 H3 . . 118.5 ?
C3 C4 C5 . . 119.0(4) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C6 C5 C4 . . 118.7(4) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C5 C6 C1 . . 121.7(3) ?
C5 C6 S1 . . 118.7(2) ?
C1 C6 S1 . . 119.6(2) ?
C8 C7 C12 . . 122.6(2) ?
C8 C7 S1 . . 118.43(19) ?
C12 C7 S1 . . 119.0(2) ?
C7 C8 C9 . . 119.4(2) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
N2 C9 C10 . . 121.3(2) ?
N2 C9 C8 . . 120.5(3) ?
C10 C9 C8 . . 118.2(3) ?
C11 C10 C9 . . 121.4(3) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 120.9(3) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C7 C12 C11 . . 117.5(3) ?
C7 C12 H12 . . 121.2 ?
C11 C12 H12 . . 121.2 ?
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
O1 S1 . 1.444(2) ?
O2 S1 . 1.439(2) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
N2 H2B . 0.8600 ?
N2 H2A . 0.8600 ?
C1 C6 . 1.382(4) ?
C1 C2 . 1.398(4) ?
C1 H1 . 0.9300 ?
C2 N1 . 1.353(5) ?
C2 C3 . 1.361(6) ?
C3 C4 . 1.365(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.398(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(5) ?
C5 H5 . 0.9300 ?
C6 S1 . 1.760(3) ?
C7 C8 . 1.375(4) ?
C7 C12 . 1.386(4) ?
C7 S1 . 1.763(2) ?
C8 C9 . 1.401(3) ?
C8 H8 . 0.9300 ?
C9 N2 . 1.378(4) ?
C9 C10 . 1.390(4) ?
C10 C11 . 1.372(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.386(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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 H1B O2 2_645 0.86 2.25 3.091(5) 166.00 yes
N2 H2A O1 3_565 0.86 2.29 3.069(4) 151.00 yes
N2 H2B O2 1_455 0.86 2.38 3.187(4) 156.00 yes
C1 H1 O2 . 0.93 2.55 2.924(4) 104.00 yes
C8 H8 O1 . 0.93 2.51 2.895(3) 105.00 yes
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
C6 C1 C2 N1 . . . . -179.1(3) ?
C6 C1 C2 C3 . . . . 0.0(4) ?
N1 C2 C3 C4 . . . . 179.6(4) ?
C1 C2 C3 C4 . . . . 0.4(6) ?
C2 C3 C4 C5 . . . . -0.8(7) ?
C3 C4 C5 C6 . . . . 0.6(6) ?
C4 C5 C6 C1 . . . . -0.2(5) ?
C4 C5 C6 S1 . . . . -178.7(3) ?
C2 C1 C6 C5 . . . . -0.1(4) ?
C2 C1 C6 S1 . . . . 178.4(2) ?
C12 C7 C8 C9 . . . . 0.4(4) ?
S1 C7 C8 C9 . . . . 179.9(2) ?
C7 C8 C9 N2 . . . . 177.2(3) ?
C7 C8 C9 C10 . . . . -0.7(4) ?
N2 C9 C10 C11 . . . . -177.2(3) ?
C8 C9 C10 C11 . . . . 0.6(5) ?
C9 C10 C11 C12 . . . . -0.2(5) ?
C8 C7 C12 C11 . . . . 0.0(5) ?
S1 C7 C12 C11 . . . . -179.5(2) ?
C10 C11 C12 C7 . . . . -0.1(5) ?
C5 C6 S1 O2 . . . . -167.8(2) ?
C1 C6 S1 O2 . . . . 13.6(3) ?
C5 C6 S1 O1 . . . . -39.4(3) ?
C1 C6 S1 O1 . . . . 142.1(2) ?
C5 C6 S1 C7 . . . . 76.0(3) ?
C1 C6 S1 C7 . . . . -102.6(2) ?
C8 C7 S1 O2 . . . . 144.7(2) ?
C12 C7 S1 O2 . . . . -35.7(3) ?
C8 C7 S1 O1 . . . . 16.4(3) ?
C12 C7 S1 O1 . . . . -164.1(2) ?
C8 C7 S1 C6 . . . . -99.1(2) ?
C12 C7 S1 C6 . . . . 80.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11248
