#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220702.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_2220702
loop_
_publ_author_name
'Sato, Kazuyuki'
'Shima, Hideki'
'Mizuguchi, Jin'
_publ_section_title
;
 2-(4-Hydroxyphenylsulfonyl)phenol
;
_journal_coeditor_code           BH2215
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o391
_journal_paper_doi               10.1107/S160053680900258X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H10 O4 S'
_chemical_formula_moiety         'C12 H10 O4 S'
_chemical_formula_sum            'C12 H10 O4 S'
_chemical_formula_weight         250.27
_chemical_name_systematic
;
2-(4-Hydroxyphenylsulfonyl)phenol
;
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.8147(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.9525(2)
_cell_length_b                   14.4404(3)
_cell_length_c                   7.03610(10)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.1
_cell_volume                     1110.35(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2006)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.154
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9436
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    2.619
_exptl_absorpt_correction_T_max  0.468
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520.00
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.66
_refine_ls_extinction_coef       0.0078(10)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    0
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.078P)²+1.2611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                1830
_reflns_number_total             1998
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            bh2215.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220702
_cod_database_fobs_code          2220702
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+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
S S1 0.27104(6) 0.93583(5) 0.66743(9) 0.0192(2) Uani d . 1.00 . .
O O1 0.30244(18) 1.03113(13) 0.7107(3) 0.0240(5) Uani d . 1.00 . .
O O2 0.23614(19) 0.91341(15) 0.4710(2) 0.0272(5) Uani d . 1.00 . .
O O3 0.25813(18) 0.94202(14) 1.0879(2) 0.0217(4) Uani d . 1.00 . .
O O4 0.70235(18) 0.71229(14) 0.9019(3) 0.0253(5) Uani d . 1.00 . .
C C1 0.1463(2) 0.90270(18) 0.7994(3) 0.0184(5) Uani d . 1.00 . .
C C2 0.1531(2) 0.91128(18) 0.9972(4) 0.0201(6) Uani d . 1.00 . .
C C3 0.0508(2) 0.8876(2) 1.0952(4) 0.0222(6) Uani d . 1.00 . .
C C4 -0.0549(2) 0.8560(2) 0.9967(4) 0.0243(6) Uani d . 1.00 . .
C C5 -0.0613(2) 0.8473(2) 0.7997(4) 0.0265(6) Uani d . 1.00 . .
C C6 0.0399(2) 0.8704(2) 0.7008(4) 0.0243(6) Uani d . 1.00 . .
C C7 0.3959(2) 0.86727(19) 0.7456(3) 0.0192(5) Uani d . 1.00 . .
C C8 0.5037(2) 0.90989(19) 0.8143(4) 0.0209(6) Uani d . 1.00 . .
C C9 0.6055(2) 0.85644(19) 0.8666(4) 0.0218(6) Uani d . 1.00 . .
C C10 0.5990(2) 0.76019(19) 0.8485(3) 0.0199(6) Uani d . 1.00 . .
C C11 0.4904(2) 0.71764(18) 0.7819(3) 0.0204(6) Uani d . 1.00 . .
C C12 0.3887(2) 0.77072(19) 0.7286(3) 0.0213(6) Uani d . 1.00 . .
H H3O 0.257(3) 0.940(2) 1.212(5) 0.023(8) Uiso d . 1.00 . .
H H4O 0.695(4) 0.653(3) 0.862(6) 0.058(12) Uiso d . 1.00 . .
H H3 0.0535 0.8933 1.2300 0.025 Uiso c R 1.00 . .
H H4 -0.1237 0.8395 1.0653 0.027 Uiso c R 1.00 . .
H H5 -0.1341 0.8255 0.7318 0.028 Uiso c R 1.00 . .
H H6 0.0369 0.8644 0.5664 0.027 Uiso c R 1.00 . .
H H8 0.5071 0.9755 0.8264 0.022 Uiso c R 1.00 . .
H H9 0.6792 0.8851 0.9143 0.025 Uiso c R 1.00 . .
H H11 0.4865 0.6518 0.7720 0.023 Uiso c R 1.00 . .
H H12 0.3143 0.7422 0.6813 0.024 Uiso c R 1.00 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.333 0.557
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . . 117.29(12) ?
O1 S1 C1 . . . 109.16(12) ?
O1 S1 C7 . . . 107.63(12) ?
O2 S1 C1 . . . 106.08(12) ?
O2 S1 C7 . . . 108.99(12) ?
C1 S1 C7 . . . 107.30(12) ?
C2 O3 H3O . . . 113(2) ?
C10 O4 H4O . . . 110(2) ?
S1 C1 C2 . . . 120.6(2) ?
S1 C1 C6 . . . 118.6(2) ?
C2 C1 C6 . . . 120.9(2) ?
O3 C2 C1 . . . 119.1(2) ?
O3 C2 C3 . . . 122.2(2) ?
C1 C2 C3 . . . 118.7(2) ?
C2 C3 C4 . . . 120.3(2) ?
C2 C3 H3 . . . 119.9 ?
C4 C3 H3 . . . 119.8 ?
C3 C4 C5 . . . 120.9(2) ?
C3 C4 H4 . . . 119.4 ?
C5 C4 H4 . . . 119.6 ?
C4 C5 C6 . . . 119.3(2) ?
C4 C5 H5 . . . 120.9 ?
C6 C5 H5 . . . 119.7 ?
C1 C6 C5 . . . 119.9(2) ?
C1 C6 H6 . . . 119.9 ?
C5 C6 H6 . . . 120.2 ?
S1 C7 C8 . . . 119.2(2) ?
S1 C7 C12 . . . 119.9(2) ?
C8 C7 C12 . . . 120.8(2) ?
C7 C8 C9 . . . 119.7(2) ?
C7 C8 H8 . . . 120.0 ?
C9 C8 H8 . . . 120.3 ?
C8 C9 C10 . . . 119.6(2) ?
C8 C9 H9 . . . 120.1 ?
C10 C9 H9 . . . 120.2 ?
O4 C10 C9 . . . 116.4(2) ?
O4 C10 C11 . . . 123.1(2) ?
C9 C10 C11 . . . 120.5(2) ?
C10 C11 C12 . . . 120.1(2) ?
C10 C11 H11 . . . 119.8 ?
C12 C11 H11 . . . 120.1 ?
C7 C12 C11 . . . 119.3(2) ?
C7 C12 H12 . . . 120.1 ?
C11 C12 H12 . . . 120.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . . 1.446(2) ?
S1 O2 . . 1.446(2) ?
S1 C1 . . 1.768(2) ?
S1 C7 . . 1.747(2) ?
O3 C2 . . 1.353(3) ?
O3 H3O . . 0.87(3) ?
O4 C10 . . 1.358(3) ?
O4 H4O . . 0.90(4) ?
C1 C2 . . 1.395(3) ?
C1 C6 . . 1.396(3) ?
C2 C3 . . 1.397(4) ?
C3 C4 . . 1.386(3) ?
C3 H3 . . 0.950 ?
C4 C5 . . 1.389(4) ?
C4 H4 . . 0.952 ?
C5 C6 . . 1.388(4) ?
C5 H5 . . 0.955 ?
C6 H6 . . 0.948 ?
C7 C8 . . 1.389(3) ?
C7 C12 . . 1.401(3) ?
C8 C9 . . 1.386(3) ?
C8 H8 . . 0.951 ?
C9 C10 . . 1.397(3) ?
C9 H9 . . 0.948 ?
C10 C11 . . 1.392(3) ?
C11 C12 . . 1.383(3) ?
C11 H11 . . 0.953 ?
C12 H12 . . 0.953 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O4 2.733(2) . 2_656 ?
O1 H4O 1.84(4) . 2_656 ?
O1 H9 2.898 . 3_677 ?
O1 H11 2.891 . 2_656 ?
O2 O3 2.753(2) . 1_554 ?
O2 H3O 1.89(3) . 1_554 ?
O2 H3 2.552 . 1_554 ?
O3 O2 2.753(2) . 1_556 ?
O3 H8 2.862 . 3_677 ?
O3 H9 2.590 . 3_677 ?
O3 H12 2.799 . 4_565 ?
O4 O1 2.733(2) . 2_646 ?
O4 H4 2.835 . 1_655 ?
O4 H5 2.757 . 1_655 ?
O4 H5 2.888 . 4_665 ?
C4 H9 2.962 . 1_455 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
O3 H3O O2 . . 1_556 0.87(3) 1.90(3) 2.753(2) 168(3) yes
O4 H4O O1 . . 2_646 0.88(4) 1.85(4) 2.733(2) 173(3) 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . -55.8(2) ?
O1 S1 C1 C6 . . . . 122.4(2) ?
O1 S1 C7 C8 . . . . -6.2(2) ?
O1 S1 C7 C12 . . . . 177.4(2) ?
O2 S1 C1 C2 . . . . 177.0(2) ?
O2 S1 C1 C6 . . . . -4.9(2) ?
O2 S1 C7 C8 . . . . 122.0(2) ?
O2 S1 C7 C12 . . . . -54.5(2) ?
C1 S1 C7 C8 . . . . -123.5(2) ?
C1 S1 C7 C12 . . . . 60.0(2) ?
C7 S1 C1 C2 . . . . 60.6(2) ?
C7 S1 C1 C6 . . . . -121.3(2) ?
S1 C1 C2 O3 . . . . -2.5(3) ?
S1 C1 C2 C3 . . . . 177.6(2) ?
S1 C1 C6 C5 . . . . -177.5(2) ?
C2 C1 C6 C5 . . . . 0.6(4) ?
C6 C1 C2 O3 . . . . 179.4(2) ?
C6 C1 C2 C3 . . . . -0.5(3) ?
O3 C2 C3 C4 . . . . -179.7(2) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C4 C5 C6 C1 . . . . -0.4(4) ?
S1 C7 C8 C9 . . . . -176.4(2) ?
S1 C7 C12 C11 . . . . 176.7(2) ?
C8 C7 C12 C11 . . . . 0.3(4) ?
C12 C7 C8 C9 . . . . 0.1(3) ?
C7 C8 C9 C10 . . . . 0.4(4) ?
C8 C9 C10 O4 . . . . 179.8(2) ?
C8 C9 C10 C11 . . . . -1.3(4) ?
O4 C10 C11 C12 . . . . -179.6(2) ?
C9 C10 C11 C12 . . . . 1.6(4) ?
C10 C11 C12 C7 . . . . -1.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 71700
