#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220437.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_2220437
loop_
_publ_author_name
'Krainova, Julia'
'Dares, Christopher'
'Lever, A. B. P.'
_publ_section_title
;
 4,4'-Dichloro-N,N'-(o-phenylene)dibenzenesulfonamide
;
_journal_coeditor_code           BX2184
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o178
_journal_paper_doi               10.1107/S1600536808039718
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H14 Cl2 N2 O4 S2'
_chemical_formula_moiety         'C18 H14 Cl2 N2 O4 S2'
_chemical_formula_sum            'C18 H14 Cl2 N2 O4 S2'
_chemical_formula_weight         457.33
_chemical_name_systematic
;
4,4'-Dichloro-N,N'-(o-phenylene)dibenzenesulfonamide
;
_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
_cell_angle_alpha                109.669(2)
_cell_angle_beta                 91.420(2)
_cell_angle_gamma                101.782(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7225(4)
_cell_length_b                   11.1920(4)
_cell_length_c                   11.9325(5)
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     945.79(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0321
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8650
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.690
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0459
_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)+(0.06P)²+0.6434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                3386
_reflns_number_total             4235
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2184.cif
_cod_data_source_block           I
_cod_database_code               2220437
_cod_database_fobs_code          2220437
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1732(3) 0.8391(2) 0.77764(19) 0.0171(4) Uani d . 1 . .
C C2 -0.0029(3) 0.8152(2) 0.72753(19) 0.0171(4) Uani d . 1 . .
C C3 -0.1000(3) 0.9105(2) 0.7632(2) 0.0222(5) Uani d . 1 . .
H H3 -0.2178 0.8935 0.7273 0.027 Uiso calc R 1 . .
C C4 -0.0274(3) 1.0303(2) 0.8506(2) 0.0262(5) Uani d . 1 . .
H H4 -0.0940 1.0957 0.8744 0.031 Uiso calc R 1 . .
C C5 0.1440(3) 1.0528(2) 0.9026(2) 0.0257(5) Uani d . 1 . .
H H5 0.1934 1.1333 0.9646 0.031 Uiso calc R 1 . .
C C6 0.2444(3) 0.9599(2) 0.8657(2) 0.0225(5) Uani d . 1 . .
H H6 0.3630 0.9785 0.9008 0.027 Uiso calc R 1 . .
C C7 0.3601(3) 0.6325(2) 0.8929(2) 0.0195(5) Uani d . 1 . .
C C8 0.3196(3) 0.4973(2) 0.8469(2) 0.0270(5) Uani d . 1 . .
H H8 0.3392 0.4524 0.7669 0.032 Uiso calc R 1 . .
C C9 0.2500(4) 0.4285(3) 0.9191(2) 0.0314(6) Uani d . 1 . .
H H9 0.2220 0.3360 0.8891 0.038 Uiso calc R 1 . .
C C10 0.2220(3) 0.4956(3) 1.0349(2) 0.0284(6) Uani d . 1 . .
C C11 0.2637(4) 0.6307(3) 1.0819(2) 0.0310(6) Uani d . 1 . .
H H11 0.2448 0.6752 1.1622 0.037 Uiso calc R 1 . .
C C12 0.3334(3) 0.7000(2) 1.0100(2) 0.0266(5) Uani d . 1 . .
H H12 0.3625 0.7925 1.0405 0.032 Uiso calc R 1 . .
C C13 -0.2243(3) 0.7466(2) 0.45683(19) 0.0189(4) Uani d . 1 . .
C C14 -0.4080(3) 0.7072(2) 0.4534(2) 0.0210(5) Uani d . 1 . .
H H14 -0.4581 0.6378 0.4801 0.025 Uiso calc R 1 . .
C C15 -0.5169(3) 0.7697(2) 0.4109(2) 0.0225(5) Uani d . 1 . .
H H15 -0.6425 0.7440 0.4078 0.027 Uiso calc R 1 . .
C C16 -0.4392(3) 0.8706(2) 0.3730(2) 0.0236(5) Uani d . 1 . .
C C17 -0.2571(3) 0.9119(2) 0.3774(2) 0.0264(5) Uani d . 1 . .
H H17 -0.2077 0.9826 0.3523 0.032 Uiso calc R 1 . .
C C18 -0.1476(3) 0.8486(2) 0.4190(2) 0.0233(5) Uani d . 1 . .
H H18 -0.0221 0.8745 0.4217 0.028 Uiso calc R 1 . .
N N1 0.2723(3) 0.7422(2) 0.73182(17) 0.0203(4) Uani d . 1 . .
H H1 0.222(4) 0.673(3) 0.672(3) 0.024 Uiso d . 1 . .
N N2 -0.0870(3) 0.68766(18) 0.64404(17) 0.0191(4) Uani d . 1 . .
H H2 -0.188(4) 0.654(3) 0.660(2) 0.023 Uiso d . 1 . .
O O1 0.5452(2) 0.84388(16) 0.87507(14) 0.0235(4) Uani d . 1 . .
O O2 0.5228(2) 0.63638(16) 0.70620(14) 0.0232(4) Uani d . 1 . .
O O3 0.0908(2) 0.70716(18) 0.48023(15) 0.0289(4) Uani d . 1 . .
O O4 -0.1729(2) 0.52320(16) 0.44441(16) 0.0311(4) Uani d . 1 . .
S S1 0.44267(7) 0.71968(5) 0.79949(5) 0.01842(15) Uani d . 1 . .
S S2 -0.08688(7) 0.65782(5) 0.50003(5) 0.02006(15) Uani d . 1 . .
Cl Cl1 0.13235(9) 0.40953(8) 1.12463(7) 0.0420(2) Uani d . 1 . .
Cl Cl2 -0.57712(9) 0.94836(6) 0.31859(6) 0.03448(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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
C6 C1 C2 . . 118.0(2) ?
C6 C1 N1 . . 123.3(2) ?
C2 C1 N1 . . 118.56(19) ?
C3 C2 C1 . . 120.5(2) ?
C3 C2 N2 . . 119.54(19) ?
C1 C2 N2 . . 119.79(19) ?
C2 C3 C4 . . 120.8(2) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 118.7(2) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C6 C5 C4 . . 121.1(2) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 120.7(2) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
C8 C7 C12 . . 121.3(2) ?
C8 C7 S1 . . 119.10(18) ?
C12 C7 S1 . . 119.63(18) ?
C9 C8 C7 . . 119.2(2) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C10 C9 C8 . . 119.5(2) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C9 C10 C11 . . 121.6(2) ?
C9 C10 Cl1 . . 119.4(2) ?
C11 C10 Cl1 . . 119.0(2) ?
C12 C11 C10 . . 119.1(2) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C11 C12 C7 . . 119.3(2) ?
C11 C12 H12 . . 120.3 ?
C7 C12 H12 . . 120.3 ?
C14 C13 C18 . . 121.3(2) ?
C14 C13 S2 . . 119.09(17) ?
C18 C13 S2 . . 119.43(18) ?
C15 C14 C13 . . 119.5(2) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 118.7(2) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C17 C16 C15 . . 122.4(2) ?
C17 C16 Cl2 . . 119.05(19) ?
C15 C16 Cl2 . . 118.53(19) ?
C16 C17 C18 . . 119.0(2) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C17 C18 C13 . . 119.1(2) ?
C17 C18 H18 . . 120.5 ?
C13 C18 H18 . . 120.5 ?
C1 N1 S1 . . 127.72(16) ?
C1 N1 H1 . . 117.6(18) ?
S1 N1 H1 . . 112.0(18) ?
C2 N2 S2 . . 119.94(15) ?
C2 N2 H2 . . 115.3(19) ?
S2 N2 H2 . . 110.4(18) ?
O1 S1 O2 . . 119.90(10) ?
O1 S1 N1 . . 108.49(10) ?
O2 S1 N1 . . 105.21(10) ?
O1 S1 C7 . . 107.30(10) ?
O2 S1 C7 . . 107.80(11) ?
N1 S1 C7 . . 107.61(10) ?
O3 S2 O4 . . 121.51(12) ?
O3 S2 N2 . . 106.60(10) ?
O4 S2 N2 . . 105.45(11) ?
O3 S2 C13 . . 107.47(11) ?
O4 S2 C13 . . 106.22(10) ?
N2 S2 C13 . . 109.20(10) ?
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
C1 C6 . 1.395(3) ?
C1 C2 . 1.408(3) ?
C1 N1 . 1.422(3) ?
C2 C3 . 1.385(3) ?
C2 N2 . 1.443(3) ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.385(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.388(3) ?
C7 C12 . 1.390(3) ?
C7 S1 . 1.764(2) ?
C8 C9 . 1.387(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.388(4) ?
C10 Cl1 . 1.735(3) ?
C11 C12 . 1.388(4) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.392(3) ?
C13 C18 . 1.393(3) ?
C13 S2 . 1.769(2) ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.381(4) ?
C16 Cl2 . 1.743(2) ?
C17 C18 . 1.387(3) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
N1 S1 . 1.6329(18) ?
N1 H1 . 0.87(3) ?
N2 S2 . 1.637(2) ?
N2 H2 . 0.85(3) ?
O1 S1 . 1.4296(17) ?
O2 S1 . 1.4359(17) ?
O3 S2 . 1.4278(18) ?
O4 S2 . 1.4312(17) ?
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 H1 O4 2_566 0.87(3) 2.12(3) 2.936(3) 157(2) y
N2 H2 O2 1_455 0.85(3) 2.30(3) 3.107(3) 159(2) y
N1 H1 N2 1_555 0.87(3) 2.45(3) 2.811(3) 106(2) y
C6 H6 O1 1_555 0.95 2.22 2.900(3) 127.9 y
C8 H8 O2 1_555 0.95 2.58 2.931(3) 102.5 y
C18 H18 O3 1_555 0.95 2.50 2.887(3) 104.1 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 910846
