#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/55/2015505.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_2015505
loop_
_publ_author_name
'Gelbrich, Thomas'
'Threlfall, Terence L.'
'Hursthouse, Michael B.'
_publ_section_title
;
 The anilinium chloride adduct of
 4-bromo-N-phenylbenzenesulfonamide
;
_journal_coeditor_code           JZ3025
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o470
_journal_page_last               o472
_journal_paper_doi               10.1107/S0108270106022104
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H8 N + , Cl -, C12 H10 Br N O2 S'
_chemical_formula_moiety         'C6 H8 N + , Cl -, C12 H10 Br N O2 S'
_chemical_formula_sum            'C18 H18 Br Cl N2 O2 S'
_chemical_formula_weight         441.76
_chemical_name_systematic
;
Anilinium chloride--N-phenyl-4-bromobenzenesulfonamide (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.137(4)
_cell_angle_beta                 81.655(4)
_cell_angle_gamma                77.163(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6705(4)
_cell_length_b                   9.9954(7)
_cell_length_c                   17.3234(12)
_cell_measurement_reflns_used    3083
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      1.00
_cell_volume                     943.31(12)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics
'XP (Bruker, 1998) and MERCURY (Macrae et al.,  2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8226
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  0.6149
_exptl_absorpt_correction_T_min  0.3594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.545
_refine_ls_extinction_coef       0.0060(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0344
_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)+(0.045P)²+0.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                2646
_reflns_number_total             3286
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz3025.cif
_cod_data_source_block           III
_cod_original_cell_volume        943.31(11)
_cod_database_code               2015505
_cod_database_fobs_code          2015505
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Br Br1 1.07484(6) -0.26420(3) -0.008944(19) 0.04259(15) Uani d . 1
S S1 0.39401(13) 0.02539(7) 0.27817(4) 0.02599(19) Uani d . 1
O O1 0.4416(4) -0.0549(2) 0.35095(11) 0.0334(5) Uani d . 1
O O2 0.1515(4) 0.0633(2) 0.25729(12) 0.0314(5) Uani d . 1
N N1 0.4972(5) 0.1629(2) 0.28214(13) 0.0261(5) Uani d D 1
H H1 0.610(4) 0.149(3) 0.3144(14) 0.028(8) Uiso d D 1
C C1 0.5774(5) -0.0621(3) 0.20042(16) 0.0250(6) Uani d . 1
C C2 0.4852(6) -0.0578(3) 0.12992(17) 0.0292(7) Uani d . 1
H H2A 0.3230 -0.0108 0.1239 0.037(9) Uiso calc R 1
C C3 0.6324(6) -0.1227(3) 0.06868(18) 0.0314(7) Uani d . 1
H H3A 0.5708 -0.1228 0.0206 0.042(9) Uiso calc R 1
C C4 0.8693(5) -0.1871(3) 0.07796(17) 0.0290(7) Uani d . 1
C C5 0.9591(6) -0.1950(3) 0.14920(18) 0.0338(7) Uani d . 1
H H5 1.1206 -0.2431 0.1554 0.047(10) Uiso calc R 1
C C6 0.8114(6) -0.1324(3) 0.21064(18) 0.0320(7) Uani d . 1
H H6 0.8700 -0.1375 0.2598 0.049(10) Uiso calc R 1
C C7 0.5082(5) 0.2736(3) 0.22341(16) 0.0231(6) Uani d . 1
C C8 0.3512(5) 0.3086(3) 0.16661(17) 0.0272(6) Uani d . 1
H H8 0.2354 0.2544 0.1636 0.033(8) Uiso calc R 1
C C9 0.3650(6) 0.4240(3) 0.11402(17) 0.0306(7) Uani d . 1
H H9 0.2582 0.4483 0.0748 0.024(7) Uiso calc R 1
C C10 0.5334(6) 0.5041(3) 0.11825(18) 0.0316(7) Uani d . 1
H H10 0.5413 0.5829 0.0822 0.040(9) Uiso calc R 1
C C11 0.6885(6) 0.4683(3) 0.17500(18) 0.0326(7) Uani d . 1
H H11 0.8027 0.5233 0.1784 0.044(9) Uiso calc R 1
C C12 0.6793(5) 0.3522(3) 0.22734(17) 0.0258(6) Uani d . 1
H H12 0.7894 0.3267 0.2656 0.024(8) Uiso calc R 1
C C13 0.1287(5) 0.2780(3) 0.55967(15) 0.0213(6) Uani d . 1
C C14 -0.0960(5) 0.2865(3) 0.60540(17) 0.0302(7) Uani d . 1
H H14 -0.1875 0.2172 0.6065 0.042(9) Uiso calc R 1
C C15 -0.1834(6) 0.3980(3) 0.64914(18) 0.0370(7) Uani d . 1
H H15 -0.3357 0.4051 0.6812 0.052(10) Uiso calc R 1
C C16 -0.0513(6) 0.4987(3) 0.64662(19) 0.0386(8) Uani d . 1
H H16 -0.1130 0.5752 0.6767 0.042(9) Uiso calc R 1
C C17 0.1702(6) 0.4888(3) 0.60061(19) 0.0340(7) Uani d . 1
H H17 0.2601 0.5590 0.5989 0.041(9) Uiso calc R 1
C C18 0.2628(5) 0.3779(3) 0.55700(17) 0.0268(6) Uani d . 1
H H18 0.4164 0.3707 0.5257 0.044(9) Uiso calc R 1
N N2 0.2194(4) 0.1614(2) 0.51242(14) 0.0252(5) Uani d . 1
H H2 0.3644 0.1702 0.4842 0.030(8) Uiso calc R 1
H H3 0.1098 0.1597 0.4792 0.035(9) Uiso calc R 1
H H4 0.2405 0.0817 0.5444 0.052(11) Uiso calc R 1
Cl Cl1 0.76523(12) 0.15174(6) 0.43098(4) 0.02355(18) Uani 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 0.33 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'
Br Br -0.2901 2.4595 '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
O2 S1 O1 120.29(12)
O2 S1 N1 109.66(13)
O1 S1 N1 104.16(12)
O2 S1 C1 106.73(13)
O1 S1 C1 108.79(13)
N1 S1 C1 106.49(12)
C7 N1 S1 127.8(2)
C7 N1 H1 114.6(19)
S1 N1 H1 112.3(19)
C6 C1 C2 121.1(3)
C6 C1 S1 119.3(2)
C2 C1 S1 119.6(2)
C3 C2 C1 119.2(3)
C3 C2 H2A 120.4
C1 C2 H2A 120.4
C4 C3 C2 119.5(3)
C4 C3 H3A 120.3
C2 C3 H3A 120.3
C3 C4 C5 121.3(3)
C3 C4 Br1 118.8(2)
C5 C4 Br1 119.9(2)
C6 C5 C4 119.2(3)
C6 C5 H5 120.4
C4 C5 H5 120.4
C5 C6 C1 119.6(3)
C5 C6 H6 120.2
C1 C6 H6 120.2
C8 C7 C12 120.4(2)
C8 C7 N1 123.0(2)
C12 C7 N1 116.6(3)
C7 C8 C9 119.2(3)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.7(3)
C10 C9 H9 119.6
C8 C9 H9 119.6
C11 C10 C9 119.5(3)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 120.5(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C7 119.7(3)
C11 C12 H12 120.2
C7 C12 H12 120.2
C18 C13 C14 121.4(2)
C18 C13 N2 119.9(2)
C14 C13 N2 118.6(2)
C15 C14 C13 118.6(3)
C15 C14 H14 120.7
C13 C14 H14 120.7
C16 C15 C14 120.5(3)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C17 120.1(3)
C15 C16 H16 119.9
C17 C16 H16 119.9
C16 C17 C18 120.6(3)
C16 C17 H17 119.7
C18 C17 H17 119.7
C13 C18 C17 118.8(3)
C13 C18 H18 120.6
C17 C18 H18 120.6
C13 N2 H2 109.5
C13 N2 H3 109.5
H2 N2 H3 109.5
C13 N2 H4 109.5
H2 N2 H4 109.5
H3 N2 H4 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.894(3)
S1 O2 1.430(2)
S1 O1 1.438(2)
S1 N1 1.621(2)
S1 C1 1.769(3)
N1 C7 1.417(3)
N1 H1 0.878(14)
C1 C6 1.382(4)
C1 C2 1.389(4)
C2 C3 1.382(4)
C2 H2A 0.9500
C3 C4 1.378(4)
C3 H3A 0.9500
C4 C5 1.389(4)
C5 C6 1.376(4)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.384(4)
C7 C12 1.391(4)
C8 C9 1.391(4)
C8 H8 0.9500
C9 C10 1.390(4)
C9 H9 0.9500
C10 C11 1.377(4)
C10 H10 0.9500
C11 C12 1.390(4)
C11 H11 0.9500
C12 H12 0.9500
C13 C18 1.377(4)
C13 C14 1.390(4)
C13 N2 1.460(3)
C14 C15 1.381(4)
C14 H14 0.9500
C15 C16 1.375(4)
C15 H15 0.9500
C16 C17 1.377(4)
C16 H16 0.9500
C17 C18 1.378(4)
C17 H17 0.9500
C18 H18 0.9500
N2 H2 0.9100
N2 H3 0.9100
N2 H4 0.9100
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 Cl1 . 0.878(14) 2.332(18) 3.157(3) 157(3)
N2 H2 Cl1 . 0.91 2.30 3.196(2) 167.4
N2 H3 Cl1 1_455 0.91 2.25 3.135(3) 162.9
N2 H4 Cl1 2_656 0.91 2.33 3.152(2) 150.6
C14 H14 O1 2_556 0.95 2.39 3.307(3) 163.2
C17 H17 Cl1 2_666 0.95 2.85 3.661(3) 143.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133461
