#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/42/2234220.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_2234220
loop_
_publ_author_name
'Al-Najjar, Belal O.'
'Tengku Muhammad, Tengku Sifzizul'
'Wahab, Habibah A.'
'Rosli, Mohd Mustaqim'
'Fun, Hoong-Kun'
_publ_section_title
;
 4-(4-Fluorobenzenesulfonamido)phenyl 4-fluorobenzenesulfonate
;
_journal_coeditor_code           HB6664
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1094
_journal_paper_doi               10.1107/S1600536812009877
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H13 F2 N O5 S2'
_chemical_formula_moiety         'C18 H13 F2 N O5 S2'
_chemical_formula_sum            'C18 H13 F2 N O5 S2'
_chemical_formula_weight         425.41
_chemical_name_common
;
4-{[(4-fluorophenyl)sulfonyl]amino}phenyl 4-fluorobenzenesulfonate
;
_chemical_name_systematic
;
4-(4-Fluorobenzenesulfonamido)phenyl 4-fluorobenzenesulfonate
;
_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                 102.3630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.96830(10)
_cell_length_b                   11.03230(10)
_cell_length_c                   9.33140(10)
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.63
_cell_measurement_theta_min      2.32
_cell_volume                     901.848(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12757
_diffrn_reflns_theta_full        32.63
_diffrn_reflns_theta_max         32.63
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9301
_exptl_absorpt_correction_T_min  0.8832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.387
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0355
_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)+(0.0442P)²+0.4073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2940
_reflns_number_total             3235
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6664.cif
_cod_data_source_block           I
_cod_original_cell_volume        901.848(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234220
_cod_database_fobs_code          2234220
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_symmetry_multiplicity
S S1 0.19643(3) 0.57696(3) 0.40553(3) 0.02189(8) Uani d . 1 1
F F1 0.48038(14) 0.10387(9) 0.39858(12) 0.0534(3) Uani d . 1 1
O O1 0.03218(11) 0.56620(9) 0.29564(11) 0.0265(2) Uani d P 0.50 1
N N1 0.03218(11) 0.56620(9) 0.29564(11) 0.0265(2) Uani d P 0.50 1
H H1N1 -0.0391 0.5177 0.3342 0.032 Uiso d PR 0.50 1
O O2 0.15869(11) 0.59542(9) 0.54583(10) 0.02712(18) Uani d . 1 1
O O3 0.28500(11) 0.66585(8) 0.34966(11) 0.0302(2) Uani d . 1 1
C C1 0.41366(16) 0.21362(12) 0.39786(15) 0.0318(3) Uani d . 1 1
C C2 0.29275(15) 0.22427(12) 0.46723(16) 0.0311(3) Uani d . 1 1
H H2A 0.2565 0.1562 0.5119 0.037 Uiso calc R 1 1
C C3 0.22599(13) 0.33732(11) 0.46964(14) 0.0269(2) Uani d . 1 1
H H3A 0.1428 0.3483 0.5166 0.032 Uiso calc R 1 1
C C4 0.28240(12) 0.43473(10) 0.40228(12) 0.01905(19) Uani d . 1 1
C C5 0.40364(13) 0.42142(11) 0.33233(13) 0.0248(2) Uani d . 1 1
H H5A 0.4402 0.4889 0.2868 0.030 Uiso calc R 1 1
C C6 0.47055(16) 0.30807(13) 0.32990(15) 0.0323(3) Uani d . 1 1
H H6A 0.5533 0.2962 0.2826 0.039 Uiso calc R 1 1
C C7 0.08657(15) 0.60289(12) 0.05220(15) 0.0299(3) Uani d . 1 1
H H7A 0.1450 0.6725 0.0882 0.036 Uiso calc R 1 1
C C8 0.02046(14) 0.53190(11) 0.14551(13) 0.0258(2) Uani d . 1 1
C C9 -0.06539(15) 0.43016(12) 0.09444(15) 0.0300(3) Uani d . 1 1
H H9A -0.1097 0.3831 0.1597 0.036 Uiso calc R 1 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'
F F 0.0171 0.0103 '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
O3 S1 O2 . . 119.57(6)
O3 S1 O1 . . 108.83(6)
O2 S1 O1 . . 103.25(5)
O3 S1 C4 . . 109.11(5)
O2 S1 C4 . . 109.49(5)
O1 S1 C4 . . 105.62(5)
C8 O1 S1 . . 120.53(7)
C8 O1 H1N1 . . 107.7
S1 O1 H1N1 . . 113.2
F1 C1 C6 . . 118.34(13)
F1 C1 C2 . . 117.73(13)
C6 C1 C2 . . 123.93(12)
C1 C2 C3 . . 117.99(12)
C1 C2 H2A . . 121.0
C3 C2 H2A . . 121.0
C2 C3 C4 . . 119.13(11)
C2 C3 H3A . . 120.4
C4 C3 H3A . . 120.4
C5 C4 C3 . . 121.74(11)
C5 C4 S1 . . 119.61(9)
C3 C4 S1 . . 118.64(8)
C6 C5 C4 . . 119.12(12)
C6 C5 H5A . . 120.4
C4 C5 H5A . . 120.4
C1 C6 C5 . . 118.09(12)
C1 C6 H6A . . 121.0
C5 C6 H6A . . 121.0
C9 C7 C8 3_565 . 118.74(13)
C9 C7 H7A 3_565 . 120.6
C8 C7 H7A . . 120.6
C9 C8 C7 . . 121.28(12)
C9 C8 O1 . . 117.95(10)
C7 C8 O1 . . 120.67(13)
C8 C9 C7 . 3_565 119.98(11)
C8 C9 H9A . . 120.0
C7 C9 H9A 3_565 . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O3 . 1.4289(9)
S1 O2 . 1.4351(9)
S1 O1 . 1.6089(11)
S1 C4 . 1.7515(11)
F1 C1 . 1.3499(15)
O1 C8 . 1.4332(16)
O1 H1N1 . 0.9606
C1 C6 . 1.374(2)
C1 C2 . 1.382(2)
C2 C3 . 1.3858(18)
C2 H2A . 0.9500
C3 C4 . 1.3936(16)
C3 H3A . 0.9500
C4 C5 . 1.3905(15)
C5 C6 . 1.3893(17)
C5 H5A . 0.9500
C6 H6A . 0.9500
C7 C9 3_565 1.389(2)
C7 C8 . 1.3943(16)
C7 H7A . 0.9500
C8 C9 . 1.387(2)
C9 C7 3_565 1.389(2)
C9 H9A . 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
_geom_hbond_publ_flag
N1 H1N1 O2 3_566 0.96 2.12 3.0630(14) 169 yes
C5 H5A F1 2_655 0.95 2.37 3.2766(16) 159 yes
C6 H6A O3 2_645 0.95 2.54 3.4130(17) 152 yes
C7 H7A O2 4_575 0.95 2.60 3.3936(17) 142 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_4
_geom_torsion
O3 S1 O1 C8 . . 59.87(10)
O2 S1 O1 C8 . . -172.10(9)
C4 S1 O1 C8 . . -57.16(10)
F1 C1 C2 C3 . . 178.60(12)
C6 C1 C2 C3 . . -0.7(2)
C1 C2 C3 C4 . . 0.23(19)
C2 C3 C4 C5 . . 0.18(18)
C2 C3 C4 S1 . . 179.75(10)
O3 S1 C4 C5 . . -8.66(11)
O2 S1 C4 C5 . . -141.24(9)
O1 S1 C4 C5 . . 108.18(10)
O3 S1 C4 C3 . . 171.77(9)
O2 S1 C4 C3 . . 39.18(11)
O1 S1 C4 C3 . . -71.39(10)
C3 C4 C5 C6 . . -0.18(18)
S1 C4 C5 C6 . . -179.74(10)
F1 C1 C6 C5 . . -178.59(12)
C2 C1 C6 C5 . . 0.7(2)
C4 C5 C6 C1 . . -0.25(19)
C9 C7 C8 C9 3_565 . -0.15(19)
C9 C7 C8 O1 3_565 . -176.54(11)
S1 O1 C8 C9 . . 122.24(11)
S1 O1 C8 C7 . . -61.25(13)
C7 C8 C9 C7 . 3_565 0.2(2)
O1 C8 C9 C7 . 3_565 176.64(11)
