#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/05/2210589.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_2210589
loop_
_publ_author_name
'Li Wu'
'Fu-Xia Liang'
'Xiao-Ai Sun'
'Wen-Qin Zhang'
_publ_section_title
;
 p-Phenylene bis(benzenesulfonate)
;
_journal_coeditor_code           FB2021
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4288
_journal_page_last               o4290
_journal_paper_doi               10.1107/S1600536806035173
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H14 O6 S2'
_chemical_formula_moiety         'C18 H14 O6 S2'
_chemical_formula_sum            'C18 H14 O6 S2'
_chemical_formula_weight         390.41
_chemical_melting_point          .388E-305
_chemical_name_systematic
;
p-Phenylene bis(benzenesulfonate)
;
_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                101.125(4)
_cell_angle_beta                 109.046(4)
_cell_angle_gamma                110.346(4)
_cell_formula_units_Z            2
_cell_length_a                   8.225(2)
_cell_length_b                   10.664(3)
_cell_length_c                   12.493(3)
_cell_measurement_reflns_used    2006
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.60
_cell_measurement_theta_min      2.30
_cell_volume                     911.3(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1000'
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4642
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.316
_refine_ls_extinction_coef       0.179(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0564P)²+0.3203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2346
_reflns_number_total             3191
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2021.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2210589
_cod_database_fobs_code          2210589
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
S S1 0.02464(11) 0.98717(8) 0.79836(6) 0.0627(3) Uani d . 1
S S2 0.39752(10) 0.64022(8) 0.32249(6) 0.0608(3) Uani d . 1
O O1 0.2428(3) 1.09633(18) 0.88713(16) 0.0611(5) Uani d . 1
O O2 -0.0563(4) 1.0777(3) 0.7634(2) 0.0963(8) Uani d . 1
O O3 -0.0533(3) 0.8953(3) 0.85588(19) 0.0841(7) Uani d . 1
O O4 0.1719(2) 0.54401(19) 0.24340(16) 0.0580(5) Uani d . 1
O O5 0.4517(3) 0.7681(2) 0.2965(2) 0.0824(6) Uani d . 1
O O6 0.4199(3) 0.6432(3) 0.44020(18) 0.0849(7) Uani d . 1
C C1 0.0422(3) 0.8883(3) 0.6770(2) 0.0508(6) Uani d . 1
C C2 -0.0415(4) 0.7427(3) 0.6443(3) 0.0678(8) Uani d . 1
H H2 -0.1000 0.6991 0.6882 0.081 Uiso calc R 1
C C3 -0.0380(5) 0.6633(4) 0.5474(4) 0.0927(11) Uani d . 1
H H3 -0.0965 0.5644 0.5240 0.111 Uiso calc R 1
C C4 0.0488(6) 0.7255(5) 0.4848(3) 0.0952(13) Uani d . 1
H H4 0.0486 0.6689 0.4179 0.114 Uiso calc R 1
C C5 0.1387(6) 0.8723(5) 0.5179(3) 0.0952(12) Uani d . 1
H H5 0.2016 0.9142 0.4751 0.114 Uiso calc R 1
C C6 0.1341(4) 0.9567(3) 0.6162(3) 0.0701(8) Uani d . 1
H H6 0.1911 1.0556 0.6397 0.084 Uiso calc R 1
C C7 0.3697(4) 1.0426(2) 0.9433(2) 0.0506(6) Uani d . 1
C C8 0.3581(4) 0.9974(3) 1.0375(2) 0.0571(7) Uani d . 1
H H8 0.2626 0.9965 1.0621 0.069 Uiso calc R 1
C C9 0.4908(4) 0.9535(3) 1.0948(2) 0.0565(7) Uani d . 1
H H9 0.4857 0.9218 1.1585 0.068 Uiso calc R 1
C C10 0.4988(4) 0.5378(3) 0.2687(2) 0.0557(7) Uani d . 1
C C11 0.5723(4) 0.5687(4) 0.1873(3) 0.0761(9) Uani d . 1
H H11 0.5698 0.6442 0.1611 0.091 Uiso calc R 1
C C12 0.6498(5) 0.4845(6) 0.1456(3) 0.0983(13) Uani d . 1
H H12 0.6976 0.5025 0.0893 0.118 Uiso calc R 1
C C13 0.6569(5) 0.3753(5) 0.1860(4) 0.0958(12) Uani d . 1
H H13 0.7111 0.3206 0.1580 0.115 Uiso calc R 1
C C14 0.5847(5) 0.3461(4) 0.2673(3) 0.0821(10) Uani d . 1
H H14 0.5893 0.2714 0.2942 0.099 Uiso calc R 1
C C15 0.5055(4) 0.4269(3) 0.3090(3) 0.0628(7) Uani d . 1
H H15 0.4564 0.4072 0.3643 0.075 Uiso calc R 1
C C16 0.0898(3) 0.5244(3) 0.1190(2) 0.0490(6) Uani d . 1
C C17 0.0601(4) 0.6317(3) 0.0835(2) 0.0539(6) Uani d . 1
H H17 0.1009 0.7196 0.1403 0.065 Uiso calc R 1
C C18 -0.0313(4) 0.6066(3) -0.0381(3) 0.0542(7) Uani d . 1
H H18 -0.0529 0.6774 -0.0648 0.065 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'
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
_geom_angle_publ_flag
O2 S1 O3 . 119.80(16) ?
O2 S1 O1 . 102.82(13) ?
O3 S1 O1 . 109.63(12) ?
O2 S1 C1 . 110.41(13) ?
O3 S1 C1 . 109.39(14) ?
O1 S1 C1 . 103.39(11) yes
O6 S2 O5 . 120.76(15) ?
O6 S2 O4 . 102.61(12) ?
O5 S2 O4 . 108.61(12) ?
O6 S2 C10 . 110.20(13) ?
O5 S2 C10 . 109.64(14) ?
O4 S2 C10 . 103.41(11) yes
C7 O1 S1 . 118.97(15) ?
C16 O4 S2 . 119.64(14) ?
C2 C1 C6 . 122.1(3) ?
C2 C1 S1 . 117.9(2) ?
C6 C1 S1 . 120.0(2) ?
C3 C2 C1 . 119.3(3) ?
C3 C2 H2 . 120.4 ?
C1 C2 H2 . 120.4 ?
C4 C3 C2 . 120.7(4) ?
C4 C3 H3 . 119.6 ?
C2 C3 H3 . 119.6 ?
C3 C4 C5 . 121.1(3) ?
C3 C4 H4 . 119.4 ?
C5 C4 H4 . 119.4 ?
C4 C5 C6 . 119.3(3) ?
C4 C5 H5 . 120.4 ?
C6 C5 H5 . 120.4 ?
C1 C6 C5 . 117.5(3) ?
C1 C6 H6 . 121.2 ?
C5 C6 H6 . 121.2 ?
C9 C7 C8 2_677 122.3(2) ?
C9 C7 O1 2_677 117.5(2) ?
C8 C7 O1 . 120.1(2) ?
C7 C8 C9 . 118.7(2) ?
C7 C8 H8 . 120.6 ?
C9 C8 H8 . 120.6 ?
C7 C9 C8 2_677 119.0(2) ?
C7 C9 H9 2_677 120.5 ?
C8 C9 H9 . 120.5 ?
C11 C10 C15 . 120.6(3) ?
C11 C10 S2 . 119.8(2) ?
C15 C10 S2 . 119.6(2) ?
C10 C11 C12 . 118.3(3) ?
C10 C11 H11 . 120.8 ?
C12 C11 H11 . 120.8 ?
C13 C12 C11 . 120.8(3) ?
C13 C12 H12 . 119.6 ?
C11 C12 H12 . 119.6 ?
C14 C13 C12 . 120.3(4) ?
C14 C13 H13 . 119.8 ?
C12 C13 H13 . 119.8 ?
C13 C14 C15 . 119.9(4) ?
C13 C14 H14 . 120.0 ?
C15 C14 H14 . 120.0 ?
C14 C15 C10 . 119.9(3) ?
C14 C15 H15 . 120.0 ?
C10 C15 H15 . 120.0 ?
C18 C16 C17 2_565 122.4(2) ?
C18 C16 O4 2_565 117.6(2) ?
C17 C16 O4 . 119.9(2) ?
C16 C17 C18 . 118.7(2) ?
C16 C17 H17 . 120.6 ?
C18 C17 H17 . 120.6 ?
C16 C18 C17 2_565 118.9(2) ?
C16 C18 H18 2_565 120.5 ?
C17 C18 H18 . 120.5 ?
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 . 1.409(2) ?
S1 O3 . 1.423(2) ?
S1 O1 . 1.599(2) yes
S1 C1 . 1.750(3) yes
S2 O6 . 1.414(2) ?
S2 O5 . 1.417(2) ?
S2 O4 . 1.6001(19) yes
S2 C10 . 1.748(3) yes
O1 C7 . 1.415(3) ?
O4 C16 . 1.417(3) ?
C1 C2 . 1.371(4) ?
C1 C6 . 1.372(4) ?
C2 C3 . 1.351(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.341(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.396(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C9 2_677 1.370(4) ?
C7 C8 . 1.373(3) ?
C8 C9 . 1.377(4) ?
C8 H8 . 0.9300 ?
C9 C7 2_677 1.370(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.379(4) ?
C10 C15 . 1.382(4) ?
C11 C12 . 1.386(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.367(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.367(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.370(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C18 2_565 1.369(4) ?
C16 C17 . 1.373(3) ?
C17 C18 . 1.379(4) ?
C17 H17 . 0.9300 ?
C18 C16 2_565 1.369(4) ?
C18 H18 . 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
C2 H2 O3 . 0.93 2.48 2.875(4) 105.9
C11 H11 O5 . 0.93 2.58 2.932(4) 103.0
C17 H17 O2 2_576 0.93 2.468 3.329(5) 154.1
C15 H15 O6 2_666 0.93 2.560 3.274(5) 134.0
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_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 O1 C7 . . 178.48(18) ?
O3 S1 O1 C7 . . 50.0(2) ?
C1 S1 O1 C7 . . -66.6(2) yes
O6 S2 O4 C16 . . 175.39(19) ?
O5 S2 O4 C16 . . 46.5(2) ?
C10 S2 O4 C16 . . -70.0(2) yes
O2 S1 C1 C2 . . -124.9(2) ?
O3 S1 C1 C2 . . 8.9(3) ?
O1 S1 C1 C2 . . 125.7(2) ?
O2 S1 C1 C6 . . 53.7(3) ?
O3 S1 C1 C6 . . -172.5(2) ?
O1 S1 C1 C6 . . -55.7(2) ?
C6 C1 C2 C3 . . -1.6(4) ?
S1 C1 C2 C3 . . 176.9(2) ?
C1 C2 C3 C4 . . 1.1(5) ?
C2 C3 C4 C5 . . 0.6(6) ?
C3 C4 C5 C6 . . -1.8(6) ?
C2 C1 C6 C5 . . 0.4(4) ?
S1 C1 C6 C5 . . -178.1(2) ?
C4 C5 C6 C1 . . 1.3(5) ?
S1 O1 C7 C9 . 2_677 109.3(2) ?
S1 O1 C7 C8 . . -74.8(3) ?
C9 C7 C8 C9 2_677 . -0.5(4) ?
O1 C7 C8 C9 . . -176.3(2) ?
C7 C8 C9 C7 . 2_677 0.5(4) ?
O6 S2 C10 C11 . . -150.7(2) ?
O5 S2 C10 C11 . . -15.4(3) ?
O4 S2 C10 C11 . . 100.2(2) ?
O6 S2 C10 C15 . . 28.9(3) ?
O5 S2 C10 C15 . . 164.2(2) ?
O4 S2 C10 C15 . . -80.1(2) ?
C15 C10 C11 C12 . . 1.0(4) ?
S2 C10 C11 C12 . . -179.4(2) ?
C10 C11 C12 C13 . . -1.3(5) ?
C11 C12 C13 C14 . . 1.0(6) ?
C12 C13 C14 C15 . . -0.3(5) ?
C13 C14 C15 C10 . . 0.0(5) ?
C11 C10 C15 C14 . . -0.4(4) ?
S2 C10 C15 C14 . . 180.0(2) ?
S2 O4 C16 C18 . 2_565 107.8(2) ?
S2 O4 C16 C17 . . -76.4(3) ?
C18 C16 C17 C18 2_565 . -0.2(4) ?
O4 C16 C17 C18 . . -175.8(2) ?
C16 C17 C18 C16 . 2_565 0.2(4) ?
