#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200480.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_2200480
loop_
_publ_author_name
'Anwar Usman'
'Ibrahim Abdul Razak'
'Suchada Chantrapromma'
'Hoong-Kun Fun'
'Dipanjan Pan'
'Jayanta Kumar Ray'
_publ_section_title
;
 Bis[4-(5-methoxycarbonyl-2-thienyl)phenyl] sulfide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o842
_journal_page_last               o843
_journal_paper_doi               10.1107/S1600536801013034
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C24 H18 O4 S3'
_chemical_formula_moiety         'C24 H18 O4 S3'
_chemical_formula_sum            'C24 H18 O4 S3'
_chemical_formula_weight         466.56
_chemical_name_systematic
;
4,4'-Bis(5-Carbomethoxy-2-thienyl)phenyl sulfide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8692(3)
_cell_length_b                   6.0255(2)
_cell_length_c                   29.7783(6)
_cell_measurement_reflns_used    4461
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      1.37
_cell_volume                     2123.90(10)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .971
_diffrn_measured_fraction_theta_max .971
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0615
_diffrn_reflns_av_sigmaI/netI    .0634
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7327
_diffrn_reflns_theta_full        28.59
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .379
_exptl_absorpt_correction_T_max  .9349
_exptl_absorpt_correction_T_min  .8390
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .44
_exptl_crystal_size_min          .18
_refine_diff_density_max         .268
_refine_diff_density_min         -.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          .0743
_refine_ls_R_factor_gt           .0528
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0803P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1505
_reflns_number_gt                1895
_reflns_number_total             2620
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6050.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2200480
_cod_database_fobs_code          2200480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
S1 .0000 -.16957(14) .7500 .0505(3) Uani d S 1 . . S
S2 .40061(5) .32091(10) .61642(2) .0497(2) Uani d . 1 . . S
O1 .52659(15) .7968(3) .54722(6) .0589(5) Uani d . 1 . . O
O2 .58680(18) .4490(4) .55765(8) .0805(7) Uani d . 1 . . O
C1 .08103(18) .0117(4) .71879(7) .0416(5) Uani d . 1 . . C
C2 .0359(2) .2012(4) .69829(10) .0587(7) Uani d . 1 . . C
H2A -.0382 .2417 .7025 .070 Uiso calc R 1 . . H
C3 .0995(2) .3296(4) .67184(9) .0569(7) Uani d . 1 . . C
H3A .0683 .4585 .6590 .068 Uiso calc R 1 . . H
C4 .20864(18) .2725(3) .66372(7) .0385(5) Uani d . 1 . . C
C5 .25295(19) .0836(4) .68444(8) .0461(5) Uani d . 1 . . C
H5A .3268 .0425 .6800 .055 Uiso calc R 1 . . H
C6 .19001(19) -.0460(4) .71161(8) .0458(5) Uani d . 1 . . C
H6A .2217 -.1729 .7251 .055 Uiso calc R 1 . . H
C7 .27439(18) .4104(4) .63471(7) .0405(5) Uani d . 1 . . C
C8 .2482(2) .6151(4) .61736(8) .0493(6) Uani d . 1 . . C
H8A .1823 .6903 .6229 .059 Uiso calc R 1 . . H
C9 .3288(2) .7012(4) .59064(9) .0497(6) Uani d . 1 . . C
H9A .3227 .8393 .5767 .060 Uiso calc R 1 . . H
C10 .4173(2) .5621(4) .58709(7) .0442(5) Uani d . 1 . . C
C11 .51936(19) .5915(4) .56306(8) .0489(6) Uani d . 1 . . C
C12 .6210(2) .8446(5) .52157(10) .0701(8) Uani d . 1 . . C
H12C .6315 1.0023 .5201 .105 Uiso calc R 1 . . H
H12A .6070 .7863 .4917 .105 Uiso calc R 1 . . H
H12B .6877 .7772 .5357 .105 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C1 2_556 103.51(14) yes
C10 S2 C7 . 91.82(11) yes
C11 O1 C12 . 116.8(2) ?
C6 C1 C2 . 118.7(2) ?
C6 C1 S1 . 118.83(17) yes
C2 C1 S1 . 122.31(17) ?
C3 C2 C1 . 120.5(2) ?
C3 C2 H2A . 119.8 ?
C1 C2 H2A . 119.8 ?
C2 C3 C4 . 121.6(2) ?
C2 C3 H3A . 119.2 ?
C4 C3 H3A . 119.2 ?
C3 C4 C5 . 117.4(2) ?
C3 C4 C7 . 120.7(2) ?
C5 C4 C7 . 121.96(19) ?
C4 C5 C6 . 121.5(2) ?
C4 C5 H5A . 119.2 ?
C6 C5 H5A . 119.2 ?
C1 C6 C5 . 120.3(2) ?
C1 C6 H6A . 119.8 ?
C5 C6 H6A . 119.8 ?
C8 C7 C4 . 128.3(2) ?
C8 C7 S2 . 110.07(17) yes
C4 C7 S2 . 121.60(16) ?
C7 C8 C9 . 114.1(2) ?
C7 C8 H8A . 123.0 ?
C9 C8 H8A . 123.0 ?
C10 C9 C8 . 112.6(2) ?
C10 C9 H9A . 123.7 ?
C8 C9 H9A . 123.7 ?
C9 C10 C11 . 129.7(2) ?
C9 C10 S2 . 111.44(18) yes
C11 C10 S2 . 118.88(18) ?
O2 C11 O1 . 124.1(2) ?
O2 C11 C10 . 124.5(2) yes
O1 C11 C10 . 111.4(2) yes
O1 C12 H12C . 109.5 ?
O1 C12 H12A . 109.5 ?
H12C C12 H12A . 109.5 ?
O1 C12 H12B . 109.5 ?
H12C C12 H12B . 109.5 ?
H12A C12 H12B . 109.5 ?
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 C1 . 1.765(2) yes
S1 C1 2_556 1.765(2) ?
S2 C10 . 1.715(2) yes
S2 C7 . 1.718(2) yes
O1 C11 . 1.329(3) ?
O1 C12 . 1.431(3) yes
O2 C11 . 1.193(3) ?
C1 C6 . 1.371(3) ?
C1 C2 . 1.384(3) yes
C2 C3 . 1.370(3) ?
C2 H2A . .9300 ?
C3 C4 . 1.379(3) ?
C3 H3A . .9300 ?
C4 C5 . 1.380(3) ?
C4 C7 . 1.464(3) yes
C5 C6 . 1.382(3) ?
C5 H5A . .9300 ?
C6 H6A . .9300 ?
C7 C8 . 1.364(3) yes
C8 C9 . 1.389(3) yes
C8 H8A . .9300 ?
C9 C10 . 1.354(3) yes
C9 H9A . .9300 ?
C10 C11 . 1.462(3) yes
C12 H12C . .9600 ?
C12 H12A . .9600 ?
C12 H12B . .9600 ?
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
_geom_torsion_publ_flag
C1 S1 C1 C6 2_556 143.3(2) yes
C1 S1 C1 C2 2_556 -41.89(19) yes
C6 C1 C2 C3 . -.8(4) ?
S1 C1 C2 C3 . -175.6(2) ?
C1 C2 C3 C4 . 1.8(4) ?
C2 C3 C4 C5 . -1.9(4) ?
C2 C3 C4 C7 . 178.9(2) ?
C3 C4 C5 C6 . 1.2(4) ?
C7 C4 C5 C6 . -179.7(2) ?
C2 C1 C6 C5 . .1(4) ?
S1 C1 C6 C5 . 175.03(18) ?
C4 C5 C6 C1 . -.3(4) ?
C3 C4 C7 C8 . 9.2(4) ?
C5 C4 C7 C8 . -169.9(2) ?
C3 C4 C7 S2 . -169.0(2) ?
C5 C4 C7 S2 . 11.9(3) yes
C10 S2 C7 C8 . 1.38(19) ?
C10 S2 C7 C4 . 179.85(19) ?
C4 C7 C8 C9 . -179.6(2) ?
S2 C7 C8 C9 . -1.3(3) ?
C7 C8 C9 C10 . .4(3) ?
C8 C9 C10 C11 . -178.8(2) ?
C8 C9 C10 S2 . .7(3) ?
C7 S2 C10 C9 . -1.2(2) ?
C7 S2 C10 C11 . 178.4(2) ?
C12 O1 C11 O2 . 1.0(4) ?
C12 O1 C11 C10 . -177.8(2) ?
C9 C10 C11 O2 . -171.0(3) ?
S2 C10 C11 O2 . 9.5(4) yes
C9 C10 C11 O1 . 7.8(4) yes
S2 C10 C11 O1 . -171.65(17) ?
