#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224849.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_2224849
loop_
_publ_author_name
'Yang, Zongwei'
_publ_section_title
;
 2-Nitro-p-phenylene dibenzenesulfonate
;
_journal_coeditor_code           BQ2192
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o482
_journal_paper_doi               10.1107/S1600536810002898
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H13 N O8 S2'
_chemical_formula_moiety         'C18 H13 N O8 S2'
_chemical_formula_sum            'C18 H13 N O8 S2'
_chemical_formula_weight         435.43
_chemical_name_systematic
;
2-Nitro-p-phenylene dibenzenesulfonate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.462(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.669(5)
_cell_length_b                   10.554(4)
_cell_length_c                   15.343(7)
_cell_measurement_reflns_used    6872
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.4
_cell_volume                     1851.9(14)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15174
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.495
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0422
_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)+(0.0646P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                3278
_reflns_number_total             4386
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2192.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224849
_cod_database_fobs_code          2224849
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 0.47624(5) 0.78506(4) 0.24585(3) 0.02226(14) Uani d . 1 . .
S S2 1.02988(5) 0.38180(5) 0.34494(3) 0.02633(15) Uani d . 1 . .
O O1 0.46295(13) 0.67436(12) 0.19112(9) 0.0252(3) Uani d . 1 . .
O O2 0.43170(13) 0.90467(13) 0.21175(10) 0.0290(4) Uani d . 1 . .
O O3 0.61466(13) 0.81300(12) 0.27823(10) 0.0248(3) Uani d . 1 . .
O O4 0.67578(15) 0.81516(13) 0.11784(10) 0.0337(4) Uani d . 1 . .
O O5 0.69050(14) 0.62624(13) 0.06595(9) 0.0302(4) Uani d . 1 . .
O O6 0.88958(13) 0.37990(13) 0.32927(10) 0.0271(3) Uani d . 1 . .
O O7 1.06055(15) 0.25648(14) 0.37645(10) 0.0369(4) Uani d . 1 . .
O O8 1.07180(14) 0.49022(15) 0.39729(10) 0.0346(4) Uani d . 1 . .
N N1 0.69459(15) 0.70129(15) 0.12753(11) 0.0233(4) Uani d . 1 . .
C C1 0.42957(18) 0.75292(18) 0.34514(13) 0.0224(4) Uani d . 1 . .
C C2 0.4055(2) 0.62808(19) 0.36603(14) 0.0281(5) Uani d . 1 . .
H H2 0.4156 0.5599 0.3278 0.034 Uiso calc R 1 . .
C C3 0.3661(2) 0.6070(2) 0.44472(15) 0.0341(6) Uani d . 1 . .
H H3 0.3498 0.5230 0.4610 0.041 Uiso calc R 1 . .
C C4 0.3503(2) 0.7068(2) 0.49945(15) 0.0334(5) Uani d . 1 . .
H H4 0.3208 0.6913 0.5519 0.040 Uiso calc R 1 . .
C C5 0.3772(2) 0.8296(2) 0.47808(15) 0.0336(6) Uani d . 1 . .
H H5 0.3686 0.8973 0.5171 0.040 Uiso calc R 1 . .
C C6 0.4165(2) 0.85408(19) 0.40072(14) 0.0274(5) Uani d . 1 . .
H H6 0.4343 0.9381 0.3856 0.033 Uiso calc R 1 . .
C C7 0.68888(17) 0.70745(17) 0.28997(13) 0.0212(4) Uani d . 1 . .
C C8 0.72464(18) 0.66007(18) 0.37471(14) 0.0236(4) Uani d . 1 . .
H H8 0.7001 0.6999 0.4235 0.028 Uiso calc R 1 . .
C C9 0.79652(18) 0.55410(19) 0.38883(14) 0.0242(4) Uani d . 1 . .
H H9 0.8229 0.5218 0.4472 0.029 Uiso calc R 1 . .
C C10 0.82902(17) 0.49626(18) 0.31632(13) 0.0218(4) Uani d . 1 . .
C C11 0.79618(17) 0.54331(17) 0.23077(13) 0.0212(4) Uani d . 1 . .
H H11 0.8203 0.5032 0.1820 0.025 Uiso calc R 1 . .
C C12 0.72676(17) 0.65101(17) 0.21879(13) 0.0199(4) Uani d . 1 . .
C C13 1.05739(19) 0.40052(19) 0.23713(13) 0.0255(5) Uani d . 1 . .
C C14 1.1317(2) 0.4954(2) 0.22087(16) 0.0348(5) Uani d . 1 . .
H H14 1.1657 0.5524 0.2667 0.042 Uiso calc R 1 . .
C C15 1.1561(2) 0.5059(2) 0.13575(18) 0.0460(7) Uani d . 1 . .
H H15 1.2078 0.5700 0.1233 0.055 Uiso calc R 1 . .
C C16 1.1054(3) 0.4237(3) 0.06989(16) 0.0470(7) Uani d . 1 . .
H H16 1.1222 0.4314 0.0120 0.056 Uiso calc R 1 . .
C C17 1.0300(3) 0.3298(3) 0.08698(16) 0.0451(7) Uani d . 1 . .
H H17 0.9949 0.2740 0.0407 0.054 Uiso calc R 1 . .
C C18 1.0057(2) 0.3169(2) 0.17063(16) 0.0352(6) Uani d . 1 . .
H H18 0.9547 0.2521 0.1828 0.042 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
O2 S1 O1 . . 121.30(9) ?
O2 S1 O3 . . 102.71(8) ?
O1 S1 O3 . . 108.31(8) ?
O2 S1 C1 . . 109.73(9) ?
O1 S1 C1 . . 109.68(9) ?
O3 S1 C1 . . 103.42(9) ?
O8 S2 O7 . . 121.12(10) ?
O8 S2 O6 . . 108.61(9) ?
O7 S2 O6 . . 102.61(9) ?
O8 S2 C13 . . 109.46(10) ?
O7 S2 C13 . . 110.01(10) ?
O6 S2 C13 . . 103.41(9) ?
C7 O3 S1 . . 116.62(12) ?
C10 O6 S2 . . 118.49(12) ?
O4 N1 O5 . . 124.14(17) ?
O4 N1 C12 . . 118.28(17) ?
O5 N1 C12 . . 117.56(16) ?
C6 C1 C2 . . 122.0(2) ?
C6 C1 S1 . . 118.36(16) ?
C2 C1 S1 . . 119.60(16) ?
C3 C2 C1 . . 117.77(19) ?
C3 C2 H2 . . 121.1 ?
C1 C2 H2 . . 121.1 ?
C4 C3 C2 . . 120.8(2) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.3(2) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.6(2) ?
C5 C6 H6 . . 120.7 ?
C1 C6 H6 . . 120.7 ?
C8 C7 C12 . . 120.10(18) ?
C8 C7 O3 . . 118.26(18) ?
C12 C7 O3 . . 121.64(17) ?
C7 C8 C9 . . 120.0(2) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C10 C9 C8 . . 118.85(19) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C11 C10 C9 . . 122.31(19) ?
C11 C10 O6 . . 118.83(18) ?
C9 C10 O6 . . 118.65(17) ?
C10 C11 C12 . . 117.65(19) ?
C10 C11 H11 . . 121.2 ?
C12 C11 H11 . . 121.2 ?
C11 C12 C7 . . 121.03(18) ?
C11 C12 N1 . . 116.91(18) ?
C7 C12 N1 . . 122.06(17) ?
C14 C13 C18 . . 121.6(2) ?
C14 C13 S2 . . 119.40(17) ?
C18 C13 S2 . . 118.99(18) ?
C13 C14 C15 . . 118.7(2) ?
C13 C14 H14 . . 120.7 ?
C15 C14 H14 . . 120.7 ?
C16 C15 C14 . . 120.0(3) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.7(2) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.3(2) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C13 . . 118.8(2) ?
C17 C18 H18 . . 120.6 ?
C13 C18 H18 . . 120.6 ?
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
S1 O2 . 1.4246(14) ?
S1 O1 . 1.4291(15) ?
S1 O3 . 1.6198(16) ?
S1 C1 . 1.750(2) ?
S2 O8 . 1.4274(16) ?
S2 O7 . 1.4291(15) ?
S2 O6 . 1.6069(17) ?
S2 C13 . 1.758(2) ?
O3 C7 . 1.401(2) ?
O4 N1 . 1.225(2) ?
O5 N1 . 1.226(2) ?
O6 C10 . 1.411(2) ?
N1 C12 . 1.474(2) ?
C1 C6 . 1.394(3) ?
C1 C2 . 1.398(3) ?
C2 C3 . 1.393(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.383(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.388(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.378(3) ?
C7 C12 . 1.391(3) ?
C8 C9 . 1.389(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.386(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.384(3) ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9500 ?
C13 C14 . 1.380(3) ?
C13 C18 . 1.393(3) ?
C14 C15 . 1.395(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.373(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.385(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.375(4) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
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
C3 H3 O4 2_645 0.9500 2.49 3.234(3) 134.7
C9 H9 O8 3_766 0.9500 2.46 3.368(3) 159.7
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
O2 S1 O3 C7 . . . . -161.01(14) ?
O1 S1 O3 C7 . . . . -31.54(16) ?
C1 S1 O3 C7 . . . . 84.81(15) ?
O8 S2 O6 C10 . . . . 37.06(17) ?
O7 S2 O6 C10 . . . . 166.41(14) ?
C13 S2 O6 C10 . . . . -79.15(16) ?
O2 S1 C1 C6 . . . . -33.48(19) ?
O1 S1 C1 C6 . . . . -169.09(16) ?
O3 S1 C1 C6 . . . . 75.54(18) ?
O2 S1 C1 C2 . . . . 145.86(17) ?
O1 S1 C1 C2 . . . . 10.3(2) ?
O3 S1 C1 C2 . . . . -105.11(17) ?
C6 C1 C2 C3 . . . . 0.7(3) ?
S1 C1 C2 C3 . . . . -178.60(17) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
C2 C3 C4 C5 . . . . -2.1(4) ?
C3 C4 C5 C6 . . . . 2.1(4) ?
C4 C5 C6 C1 . . . . -0.6(3) ?
C2 C1 C6 C5 . . . . -0.8(3) ?
S1 C1 C6 C5 . . . . 178.57(17) ?
S1 O3 C7 C8 . . . . -97.86(18) ?
S1 O3 C7 C12 . . . . 82.4(2) ?
C12 C7 C8 C9 . . . . -1.4(3) ?
O3 C7 C8 C9 . . . . 178.82(17) ?
C7 C8 C9 C10 . . . . -1.3(3) ?
C8 C9 C10 C11 . . . . 2.6(3) ?
C8 C9 C10 O6 . . . . -172.13(17) ?
S2 O6 C10 C11 . . . . 89.2(2) ?
S2 O6 C10 C9 . . . . -95.9(2) ?
C9 C10 C11 C12 . . . . -1.1(3) ?
O6 C10 C11 C12 . . . . 173.68(17) ?
C10 C11 C12 C7 . . . . -1.8(3) ?
C10 C11 C12 N1 . . . . 178.80(17) ?
C8 C7 C12 C11 . . . . 3.0(3) ?
O3 C7 C12 C11 . . . . -177.22(17) ?
C8 C7 C12 N1 . . . . -177.57(18) ?
O3 C7 C12 N1 . . . . 2.2(3) ?
O4 N1 C12 C11 . . . . -151.69(18) ?
O5 N1 C12 C11 . . . . 27.0(3) ?
O4 N1 C12 C7 . . . . 28.9(3) ?
O5 N1 C12 C7 . . . . -152.42(19) ?
O8 S2 C13 C14 . . . . 12.8(2) ?
O7 S2 C13 C14 . . . . -122.56(18) ?
O6 S2 C13 C14 . . . . 128.44(17) ?
O8 S2 C13 C18 . . . . -168.81(16) ?
O7 S2 C13 C18 . . . . 55.8(2) ?
O6 S2 C13 C18 . . . . -53.20(18) ?
C18 C13 C14 C15 . . . . -0.7(3) ?
S2 C13 C14 C15 . . . . 177.62(17) ?
C13 C14 C15 C16 . . . . 0.7(3) ?
C14 C15 C16 C17 . . . . -0.1(4) ?
C15 C16 C17 C18 . . . . -0.6(4) ?
C16 C17 C18 C13 . . . . 0.6(3) ?
C14 C13 C18 C17 . . . . 0.0(3) ?
S2 C13 C18 C17 . . . . -178.28(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744370
