#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224506.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_2224506
loop_
_publ_author_name
'Miao, Wen-Juan'
'Li, Liang-Hua'
'Lu, Shan'
'Liu, Gang'
'Fan, Cong-Bin'
_publ_section_title
;
 1,2-Bis(2-methyl-5-phenyl-3-thienyl)benzene
;
_journal_coeditor_code           XU2660
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3003
_journal_paper_doi               10.1107/S1600536809045917
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C28 H22 S2'
_chemical_formula_moiety         'C28 H22 S2'
_chemical_formula_sum            'C28 H22 S2'
_chemical_formula_weight         422.58
_chemical_name_systematic
;
1,2-Bis(2-methyl-5-phenyl-3-thienyl)benzene
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.8030(10)
_cell_angle_beta                 67.7690(10)
_cell_angle_gamma                86.3620(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0934(12)
_cell_length_b                   10.0945(12)
_cell_length_c                   11.9565(15)
_cell_measurement_reflns_used    2224
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.62
_cell_volume                     1120.7(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8610
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.9067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.006
_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+0.2296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2920
_reflns_number_total             4136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2660.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               2224506
_cod_database_fobs_code          2224506
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8690(3) 0.1761(2) 0.33341(19) 0.0593(6) Uani d . 1 . .
C C2 1.0178(3) 0.1571(2) 0.27841(19) 0.0632(6) Uani d . 1 . .
C C3 1.0724(3) 0.0279(3) 0.2524(2) 0.0837(8) Uani d . 1 . .
H H3 1.1708 0.0137 0.2160 0.100 Uiso calc R 1 . .
C C4 0.9833(5) -0.0781(3) 0.2798(3) 0.1002(11) Uani d . 1 . .
H H4 1.0217 -0.1633 0.2634 0.120 Uiso calc R 1 . .
C C5 0.8382(5) -0.0587(3) 0.3312(3) 0.0994(11) Uani d . 1 . .
H H5 0.7780 -0.1303 0.3478 0.119 Uiso calc R 1 . .
C C6 0.7806(3) 0.0679(2) 0.3587(2) 0.0803(7) Uani d . 1 . .
H H6 0.6819 0.0803 0.3944 0.096 Uiso calc R 1 . .
C C7 0.8057(2) 0.3112(2) 0.36380(18) 0.0534(5) Uani d . 1 . .
C C8 0.8183(2) 0.3757(2) 0.45372(19) 0.0564(5) Uani d . 1 . .
C C9 0.6907(2) 0.5132(2) 0.33745(18) 0.0517(5) Uani d . 1 . .
C C10 0.7318(2) 0.3902(2) 0.29899(19) 0.0563(5) Uani d . 1 . .
H H10 0.7133 0.3602 0.2357 0.068 Uiso calc R 1 . .
C C11 0.8878(3) 0.3254(3) 0.5415(2) 0.0791(7) Uani d . 1 . .
H H11A 0.9079 0.2315 0.5370 0.119 Uiso calc R 1 . .
H H11B 0.8245 0.3414 0.6223 0.119 Uiso calc R 1 . .
H H11C 0.9755 0.3712 0.5214 0.119 Uiso calc R 1 . .
C C12 0.6259(2) 0.6253(2) 0.28537(19) 0.0535(5) Uani d . 1 . .
C C13 0.6640(2) 0.6476(2) 0.1601(2) 0.0626(6) Uani d . 1 . .
H H13 0.7277 0.5890 0.1095 0.075 Uiso calc R 1 . .
C C14 0.6079(3) 0.7558(3) 0.1111(3) 0.0798(7) Uani d . 1 . .
H H14 0.6339 0.7703 0.0274 0.096 Uiso calc R 1 . .
C C15 0.5132(3) 0.8426(3) 0.1857(3) 0.0821(8) Uani d . 1 . .
H H15 0.4765 0.9163 0.1523 0.099 Uiso calc R 1 . .
C C16 0.4735(3) 0.8211(3) 0.3071(3) 0.0855(8) Uani d . 1 . .
H H16 0.4077 0.8791 0.3568 0.103 Uiso calc R 1 . .
C C17 0.5293(2) 0.7141(2) 0.3585(2) 0.0692(6) Uani d . 1 . .
H H17 0.5022 0.7013 0.4424 0.083 Uiso calc R 1 . .
C C18 1.1146(2) 0.2710(2) 0.24104(19) 0.0586(6) Uani d . 1 . .
C C19 1.2360(3) 0.2804(2) 0.2660(2) 0.0659(6) Uani d . 1 . .
C C20 1.1898(2) 0.4834(2) 0.14581(18) 0.0552(5) Uani d . 1 . .
C C21 1.0915(2) 0.3879(2) 0.17170(18) 0.0554(5) Uani d . 1 . .
H H21 1.0148 0.3978 0.1462 0.066 Uiso calc R 1 . .
C C22 1.2975(3) 0.1831(3) 0.3393(3) 0.0933(9) Uani d . 1 . .
H H22A 1.2255 0.1213 0.3891 0.140 Uiso calc R 1 . .
H H22B 1.3286 0.2306 0.3899 0.140 Uiso calc R 1 . .
H H22C 1.3775 0.1354 0.2855 0.140 Uiso calc R 1 . .
C C23 1.1947(2) 0.6143(2) 0.07776(19) 0.0567(5) Uani d . 1 . .
C C24 1.3183(3) 0.6851(3) 0.0253(3) 0.0844(8) Uani d . 1 . .
H H24 1.4020 0.6492 0.0327 0.101 Uiso calc R 1 . .
C C25 1.3216(4) 0.8071(3) -0.0376(3) 0.1023(10) Uani d . 1 . .
H H25 1.4068 0.8529 -0.0719 0.123 Uiso calc R 1 . .
C C26 1.2003(4) 0.8618(3) -0.0504(2) 0.0908(9) Uani d . 1 . .
H H26 1.2025 0.9452 -0.0926 0.109 Uiso calc R 1 . .
C C27 1.0761(4) 0.7937(3) -0.0010(2) 0.0833(8) Uani d . 1 . .
H H27 0.9936 0.8298 -0.0108 0.100 Uiso calc R 1 . .
C C28 1.0726(3) 0.6706(2) 0.0638(2) 0.0664(6) Uani d . 1 . .
H H28 0.9871 0.6252 0.0984 0.080 Uiso calc R 1 . .
S S1 0.74075(6) 0.53246(6) 0.45767(5) 0.06329(19) Uani d . 1 . .
S S2 1.31728(6) 0.43038(7) 0.20603(6) 0.0720(2) Uani d . 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'
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
_geom_angle_publ_flag
C6 C1 C2 . . 119.4(2) ?
C6 C1 C7 . . 120.1(2) ?
C2 C1 C7 . . 120.50(19) ?
C1 C2 C3 . . 118.4(2) ?
C1 C2 C18 . . 121.09(18) ?
C3 C2 C18 . . 120.4(2) ?
C4 C3 C2 . . 121.2(3) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 120.2(3) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.1(3) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C1 C6 C5 . . 120.7(3) ?
C1 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C8 C7 C10 . . 112.25(19) ?
C8 C7 C1 . . 123.57(19) ?
C10 C7 C1 . . 124.11(19) ?
C7 C8 C11 . . 128.1(2) ?
C7 C8 S1 . . 110.85(16) ?
C11 C8 S1 . . 121.04(16) ?
C10 C9 C12 . . 129.5(2) ?
C10 C9 S1 . . 109.77(16) ?
C12 C9 S1 . . 120.54(15) ?
C9 C10 C7 . . 114.25(19) ?
C9 C10 H10 . . 122.9 ?
C7 C10 H10 . . 122.9 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 118.3(2) ?
C17 C12 C9 . . 121.3(2) ?
C13 C12 C9 . . 120.39(19) ?
C14 C13 C12 . . 120.4(2) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.0(2) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C16 C15 C14 . . 120.3(2) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.8(2) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C16 C17 C12 . . 120.1(2) ?
C16 C17 H17 . . 119.9 ?
C12 C17 H17 . . 119.9 ?
C19 C18 C21 . . 111.2(2) ?
C19 C18 C2 . . 126.3(2) ?
C21 C18 C2 . . 122.4(2) ?
C18 C19 C22 . . 129.2(2) ?
C18 C19 S2 . . 111.29(17) ?
C22 C19 S2 . . 119.5(2) ?
C21 C20 C23 . . 127.9(2) ?
C21 C20 S2 . . 109.85(16) ?
C23 C20 S2 . . 122.28(18) ?
C20 C21 C18 . . 114.9(2) ?
C20 C21 H21 . . 122.5 ?
C18 C21 H21 . . 122.5 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C24 C23 C28 . . 117.4(2) ?
C24 C23 C20 . . 122.3(2) ?
C28 C23 C20 . . 120.3(2) ?
C25 C24 C23 . . 121.8(3) ?
C25 C24 H24 . . 119.1 ?
C23 C24 H24 . . 119.1 ?
C26 C25 C24 . . 120.3(3) ?
C26 C25 H25 . . 119.9 ?
C24 C25 H25 . . 119.9 ?
C27 C26 C25 . . 119.6(3) ?
C27 C26 H26 . . 120.2 ?
C25 C26 H26 . . 120.2 ?
C26 C27 C28 . . 120.0(3) ?
C26 C27 H27 . . 120.0 ?
C28 C27 H27 . . 120.0 ?
C23 C28 C27 . . 120.9(2) ?
C23 C28 H28 . . 119.6 ?
C27 C28 H28 . . 119.6 ?
C8 S1 C9 . . 92.87(10) ?
C19 S2 C20 . . 92.73(11) ?
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
C1 C6 . 1.389(3) ?
C1 C2 . 1.403(3) ?
C1 C7 . 1.490(3) ?
C2 C3 . 1.403(3) ?
C2 C18 . 1.475(3) ?
C3 C4 . 1.373(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.364(3) ?
C7 C10 . 1.422(3) ?
C8 C11 . 1.500(3) ?
C8 S1 . 1.718(2) ?
C9 C10 . 1.356(3) ?
C9 C12 . 1.469(3) ?
C9 S1 . 1.727(2) ?
C10 H10 . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C17 . 1.390(3) ?
C12 C13 . 1.394(3) ?
C13 C14 . 1.375(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.376(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.348(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.380(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 C19 . 1.377(3) ?
C18 C21 . 1.427(3) ?
C19 C22 . 1.505(3) ?
C19 S2 . 1.720(3) ?
C20 C21 . 1.354(3) ?
C20 C23 . 1.468(3) ?
C20 S2 . 1.730(2) ?
C21 H21 . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 C24 . 1.373(3) ?
C23 C28 . 1.384(3) ?
C24 C25 . 1.367(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.366(4) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.362(4) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.388(3) ?
C27 H27 . 0.9300 ?
C28 H28 . 0.9300 ?
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
C6 C1 C2 C3 . . . . -1.0(3) ?
C7 C1 C2 C3 . . . . 179.48(19) ?
C6 C1 C2 C18 . . . . 175.0(2) ?
C7 C1 C2 C18 . . . . -4.6(3) ?
C1 C2 C3 C4 . . . . 0.0(3) ?
C18 C2 C3 C4 . . . . -176.0(2) ?
C2 C3 C4 C5 . . . . 1.3(4) ?
C3 C4 C5 C6 . . . . -1.6(4) ?
C2 C1 C6 C5 . . . . 0.7(3) ?
C7 C1 C6 C5 . . . . -179.8(2) ?
C4 C5 C6 C1 . . . . 0.6(4) ?
C6 C1 C7 C8 . . . . 110.3(3) ?
C2 C1 C7 C8 . . . . -70.1(3) ?
C6 C1 C7 C10 . . . . -73.0(3) ?
C2 C1 C7 C10 . . . . 106.6(2) ?
C10 C7 C8 C11 . . . . 179.6(2) ?
C1 C7 C8 C11 . . . . -3.3(4) ?
C10 C7 C8 S1 . . . . -0.4(2) ?
C1 C7 C8 S1 . . . . 176.70(17) ?
C12 C9 C10 C7 . . . . 173.27(19) ?
S1 C9 C10 C7 . . . . -1.0(2) ?
C8 C7 C10 C9 . . . . 0.9(3) ?
C1 C7 C10 C9 . . . . -176.1(2) ?
C10 C9 C12 C17 . . . . 147.8(2) ?
S1 C9 C12 C17 . . . . -38.5(3) ?
C10 C9 C12 C13 . . . . -34.4(3) ?
S1 C9 C12 C13 . . . . 139.39(18) ?
C17 C12 C13 C14 . . . . 0.7(3) ?
C9 C12 C13 C14 . . . . -177.3(2) ?
C12 C13 C14 C15 . . . . -0.2(4) ?
C13 C14 C15 C16 . . . . -0.9(4) ?
C14 C15 C16 C17 . . . . 1.6(4) ?
C15 C16 C17 C12 . . . . -1.1(4) ?
C13 C12 C17 C16 . . . . 0.0(3) ?
C9 C12 C17 C16 . . . . 177.9(2) ?
C1 C2 C18 C19 . . . . 131.3(2) ?
C3 C2 C18 C19 . . . . -52.8(3) ?
C1 C2 C18 C21 . . . . -48.9(3) ?
C3 C2 C18 C21 . . . . 126.9(2) ?
C21 C18 C19 C22 . . . . 177.8(2) ?
C2 C18 C19 C22 . . . . -2.4(4) ?
C21 C18 C19 S2 . . . . 0.5(2) ?
C2 C18 C19 S2 . . . . -179.78(16) ?
C23 C20 C21 C18 . . . . -179.37(19) ?
S2 C20 C21 C18 . . . . 0.6(2) ?
C19 C18 C21 C20 . . . . -0.7(3) ?
C2 C18 C21 C20 . . . . 179.54(18) ?
C21 C20 C23 C24 . . . . -159.5(2) ?
S2 C20 C23 C24 . . . . 20.6(3) ?
C21 C20 C23 C28 . . . . 20.2(3) ?
S2 C20 C23 C28 . . . . -159.79(17) ?
C28 C23 C24 C25 . . . . 0.5(4) ?
C20 C23 C24 C25 . . . . -179.8(3) ?
C23 C24 C25 C26 . . . . -0.3(5) ?
C24 C25 C26 C27 . . . . -0.6(5) ?
C25 C26 C27 C28 . . . . 1.2(4) ?
C24 C23 C28 C27 . . . . 0.1(3) ?
C20 C23 C28 C27 . . . . -179.5(2) ?
C26 C27 C28 C23 . . . . -1.0(4) ?
C7 C8 S1 C9 . . . . -0.15(17) ?
C11 C8 S1 C9 . . . . 179.88(19) ?
C10 C9 S1 C8 . . . . 0.66(17) ?
C12 C9 S1 C8 . . . . -174.21(17) ?
C18 C19 S2 C20 . . . . -0.12(17) ?
C22 C19 S2 C20 . . . . -177.74(19) ?
C21 C20 S2 C19 . . . . -0.27(16) ?
C23 C20 S2 C19 . . . . 179.69(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743762
