#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/37/2233705.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_2233705
loop_
_publ_author_name
'Asahara, Haruyasu'
'Mayer, Peter'
'Mayr, Herbert'
_publ_section_title
;
 1-[2,2-Bis(phenylsulfonyl)ethenyl]-4-methoxybenzene
;
_journal_coeditor_code           ZJ2048
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o470
_journal_paper_doi               10.1107/S1600536812001961
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C21 H18 O5 S2'
_chemical_formula_moiety         'C21 H18 O5 S2'
_chemical_formula_sum            'C21 H18 O5 S2'
_chemical_formula_weight         414.497
_chemical_name_systematic
;
1-[2,2-bis(phenylsulfonyl)ethenyl]-4-methoxybenzene
;
_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           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.8449(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.82910(10)
_cell_length_b                   21.6666(4)
_cell_length_c                   12.0332(2)
_cell_measurement_reflns_used    7909
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1942.99(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 2004)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15675
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.41699(4)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0330
_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)+(0.0310P)²+1.0861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                3908
_reflns_number_total             4445
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zj2048.cif
_cod_data_source_block           I
_cod_original_cell_volume        1942.99(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233705
_cod_database_fobs_code          2233705
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 0.20814(5) 0.197024(16) 0.62810(3) 0.02090(9) Uani d . 1 1
S S2 0.18614(5) 0.089334(17) 0.46455(3) 0.02332(10) Uani d . 1 1
O O1 0.07863(14) 0.21777(5) 0.68234(10) 0.0292(2) Uani d . 1 1
O O2 0.20435(14) 0.22512(5) 0.51907(9) 0.0278(2) Uani d . 1 1
O O3 0.17420(16) 0.02302(5) 0.46677(9) 0.0313(3) Uani d . 1 1
O O4 0.33662(14) 0.11588(5) 0.43740(9) 0.0305(3) Uani d . 1 1
O O5 0.25877(18) 0.04667(6) 1.16063(9) 0.0365(3) Uani d . 1 1
C C1 0.18455(19) 0.11624(7) 0.60485(12) 0.0214(3) Uani d . 1 1
C C2 0.1764(2) 0.07226(7) 0.68278(13) 0.0245(3) Uani d . 1 1
H H2 0.1564 0.0325 0.6481 0.029 Uiso calc R 1 1
C C3 0.1902(2) 0.07015(7) 0.80624(12) 0.0242(3) Uani d . 1 1
C C4 0.18860(19) 0.12011(7) 0.88083(13) 0.0243(3) Uani d . 1 1
H H4 0.1734 0.1609 0.8506 0.029 Uiso calc R 1 1
C C5 0.2090(2) 0.11019(7) 0.99738(13) 0.0276(3) Uani d . 1 1
H H5 0.2058 0.1443 1.0464 0.033 Uiso calc R 1 1
C C6 0.2341(2) 0.05075(7) 1.04444(13) 0.0274(3) Uani d . 1 1
C C7 0.2320(2) 0.00049(8) 0.97225(14) 0.0338(4) Uani d . 1 1
H H7 0.2464 -0.0403 1.0027 0.041 Uiso calc R 1 1
C C8 0.2085(2) 0.01103(7) 0.85489(14) 0.0322(4) Uani d . 1 1
H H8 0.2045 -0.0234 0.8054 0.039 Uiso calc R 1 1
C C9 0.2945(3) -0.01316(9) 1.21382(15) 0.0435(4) Uani d . 1 1
H H9A 0.1915 -0.0403 1.1800 0.065 Uiso calc R 1 1
H H9B 0.3150 -0.0094 1.2981 0.065 Uiso calc R 1 1
H H9C 0.4014 -0.0307 1.1998 0.065 Uiso calc R 1 1
C C10 0.42503(19) 0.20496(7) 0.72786(13) 0.0227(3) Uani d . 1 1
C C11 0.4505(2) 0.23657(7) 0.83213(13) 0.0284(3) Uani d . 1 1
H H11 0.3517 0.2532 0.8523 0.034 Uiso calc R 1 1
C C12 0.6252(2) 0.24312(8) 0.90616(14) 0.0365(4) Uani d . 1 1
H H12 0.6463 0.2645 0.9780 0.044 Uiso calc R 1 1
C C13 0.7677(2) 0.21894(9) 0.87638(15) 0.0394(4) Uani d . 1 1
H H13 0.8863 0.2241 0.9275 0.047 Uiso calc R 1 1
C C14 0.7396(2) 0.18709(9) 0.77248(16) 0.0368(4) Uani d . 1 1
H H14 0.8387 0.1701 0.7531 0.044 Uiso calc R 1 1
C C15 0.5677(2) 0.17990(8) 0.69699(14) 0.0283(3) Uani d . 1 1
H H15 0.5474 0.1583 0.6254 0.034 Uiso calc R 1 1
C C16 -0.0154(2) 0.11649(7) 0.36510(12) 0.0231(3) Uani d . 1 1
C C17 -0.0075(2) 0.14543(7) 0.26401(13) 0.0298(3) Uani d . 1 1
H H17 0.1047 0.1546 0.2526 0.036 Uiso calc R 1 1
C C18 -0.1677(2) 0.16064(8) 0.17987(14) 0.0361(4) Uani d . 1 1
H H18 -0.1656 0.1801 0.1096 0.043 Uiso calc R 1 1
C C19 -0.3298(2) 0.14774(8) 0.19744(15) 0.0355(4) Uani d . 1 1
H H19 -0.4383 0.1582 0.1390 0.043 Uiso calc R 1 1
C C20 -0.3363(2) 0.11958(8) 0.29952(15) 0.0323(4) Uani d . 1 1
H H20 -0.4487 0.1113 0.3112 0.039 Uiso calc R 1 1
C C21 -0.1780(2) 0.10357(7) 0.38461(14) 0.0270(3) Uani d . 1 1
H H21 -0.1806 0.0842 0.4549 0.032 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'
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
O1 S1 O2 117.52(7)
O1 S1 C10 109.09(7)
O2 S1 C10 109.05(7)
O1 S1 C1 109.08(7)
O2 S1 C1 107.57(7)
C10 S1 C1 103.64(7)
O4 S2 O3 117.79(7)
O4 S2 C16 109.75(7)
O3 S2 C16 107.20(7)
O4 S2 C1 109.11(7)
O3 S2 C1 106.75(7)
C16 S2 C1 105.54(7)
C6 O5 C9 117.78(13)
C2 C1 S1 127.66(11)
C2 C1 S2 116.11(11)
S1 C1 S2 116.10(8)
C1 C2 C3 136.46(14)
C1 C2 H2 111.8
C3 C2 H2 111.8
C8 C3 C4 117.20(14)
C8 C3 C2 114.97(14)
C4 C3 C2 127.82(14)
C5 C4 C3 120.49(14)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.95(14)
C4 C5 H5 119.5
C6 C5 H5 119.5
O5 C6 C7 124.39(15)
O5 C6 C5 115.88(14)
C7 C6 C5 119.73(14)
C8 C7 C6 118.70(15)
C8 C7 H7 120.7
C6 C7 H7 120.7
C7 C8 C3 122.86(15)
C7 C8 H8 118.6
C3 C8 H8 118.6
O5 C9 H9A 109.5
O5 C9 H9B 109.5
H9A C9 H9B 109.5
O5 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 121.94(14)
C11 C10 S1 120.33(12)
C15 C10 S1 117.71(11)
C10 C11 C12 117.97(15)
C10 C11 H11 121.0
C12 C11 H11 121.0
C13 C12 C11 120.72(16)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 120.50(15)
C12 C13 H13 119.8
C14 C13 H13 119.8
C15 C14 C13 120.17(17)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C10 118.70(15)
C14 C15 H15 120.7
C10 C15 H15 120.7
C17 C16 C21 121.88(14)
C17 C16 S2 118.33(12)
C21 C16 S2 119.53(11)
C16 C17 C18 118.24(15)
C16 C17 H17 120.9
C18 C17 H17 120.9
C19 C18 C17 120.58(16)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C20 120.75(15)
C18 C19 H19 119.6
C20 C19 H19 119.6
C19 C20 C21 119.75(16)
C19 C20 H20 120.1
C21 C20 H20 120.1
C20 C21 C16 118.78(15)
C20 C21 H21 120.6
C16 C21 H21 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4359(11)
S1 O2 1.4383(11)
S1 C10 1.7620(15)
S1 C1 1.7731(15)
S2 O4 1.4357(11)
S2 O3 1.4405(12)
S2 C16 1.7638(15)
S2 C1 1.7897(14)
O5 C6 1.3544(18)
O5 C9 1.435(2)
C1 C2 1.352(2)
C2 C3 1.457(2)
C2 H2 0.9500
C3 C8 1.397(2)
C3 C4 1.409(2)
C4 C5 1.379(2)
C4 H4 0.9500
C5 C6 1.396(2)
C5 H5 0.9500
C6 C7 1.390(2)
C7 C8 1.386(2)
C7 H7 0.9500
C8 H8 0.9500
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.389(2)
C10 C15 1.391(2)
C11 C12 1.392(2)
C11 H11 0.9500
C12 C13 1.375(3)
C12 H12 0.9500
C13 C14 1.385(3)
C13 H13 0.9500
C14 C15 1.382(2)
C14 H14 0.9500
C15 H15 0.9500
C16 C17 1.387(2)
C16 C21 1.392(2)
C17 C18 1.389(2)
C17 H17 0.9500
C18 C19 1.377(3)
C18 H18 0.9500
C19 C20 1.386(2)
C19 H19 0.9500
C20 C21 1.388(2)
C20 H20 0.9500
C21 H21 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
C8 H8 Cg1 3_556 0.95 2.56 3.4835(17) 164 y
C14 H14 O1 1_655 0.95 2.51 3.229(2) 133 y
C21 H21 O3 3_556 0.95 2.50 3.2695(19) 138 y
C20 H20 O4 1_455 0.95 2.59 3.453(2) 151 y
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
O1 S1 C1 C2 -49.65(15)
O2 S1 C1 C2 -178.13(13)
C10 S1 C1 C2 66.46(15)
O1 S1 C1 S2 134.70(8)
O2 S1 C1 S2 6.22(10)
C10 S1 C1 S2 -109.19(9)
O4 S2 C1 C2 -127.17(12)
O3 S2 C1 C2 1.12(13)
C16 S2 C1 C2 114.95(12)
O4 S2 C1 S1 49.00(10)
O3 S2 C1 S1 177.29(8)
C16 S2 C1 S1 -68.88(9)
S1 C1 C2 C3 -3.5(3)
S2 C1 C2 C3 172.18(15)
C1 C2 C3 C8 -167.66(18)
C1 C2 C3 C4 11.9(3)
C8 C3 C4 C5 1.6(2)
C2 C3 C4 C5 -177.91(14)
C3 C4 C5 C6 0.9(2)
C9 O5 C6 C7 3.5(2)
C9 O5 C6 C5 -176.81(16)
C4 C5 C6 O5 177.80(14)
C4 C5 C6 C7 -2.4(2)
O5 C6 C7 C8 -178.93(16)
C5 C6 C7 C8 1.3(3)
C6 C7 C8 C3 1.3(3)
C4 C3 C8 C7 -2.8(3)
C2 C3 C8 C7 176.83(16)
O1 S1 C10 C11 -9.58(14)
O2 S1 C10 C11 119.97(12)
C1 S1 C10 C11 -125.68(12)
O1 S1 C10 C15 171.88(12)
O2 S1 C10 C15 -58.57(13)
C1 S1 C10 C15 55.78(13)
C15 C10 C11 C12 0.4(2)
S1 C10 C11 C12 -178.05(12)
C10 C11 C12 C13 0.0(2)
C11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 0.7(3)
C13 C14 C15 C10 -0.3(3)
C11 C10 C15 C14 -0.3(2)
S1 C10 C15 C14 178.21(12)
O4 S2 C16 C17 14.62(14)
O3 S2 C16 C17 -114.41(12)
C1 S2 C16 C17 132.07(12)
O4 S2 C16 C21 -171.11(12)
O3 S2 C16 C21 59.86(13)
C1 S2 C16 C21 -53.66(13)
C21 C16 C17 C18 -1.1(2)
S2 C16 C17 C18 172.98(13)
C16 C17 C18 C19 0.6(3)
C17 C18 C19 C20 0.3(3)
C18 C19 C20 C21 -0.7(2)
C19 C20 C21 C16 0.2(2)
C17 C16 C21 C20 0.8(2)
S2 C16 C21 C20 -173.31(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657460
