#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/29/2202980.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_2202980
loop_
_publ_author_name
'Sun, Fan'
'Zhang, Fushi'
'Wang, Ruji'
'Zhao, Fuqun'
'Pu, Shouzhi'
_publ_section_title
3,3,4,4,5,5-Hexafluoro-1,2-bis(3-methylbenzo[b]-2-thienyl)cyclopentene
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o981
_journal_page_last               o982
_journal_paper_doi               10.1107/S1600536803013126
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C23 H14 F6 S2'
_chemical_formula_moiety         'C23 H14 F6 S2'
_chemical_formula_sum            'C23 H14 F6 S2'
_chemical_formula_weight         468.46
_chemical_melting_point          465
_chemical_name_common
;
1,2-bis(3-methylbenzothien-2-yl)perfluorocyclopentene
;
_chemical_name_systematic
;
3,3,4,4,5,5-Hexafluoro-1,2-bis(3-methylbenzo[b]-2-thienyl)cyclopentene
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.653(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.8350(18)
_cell_length_b                   9.3507(9)
_cell_length_c                   11.643(2)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.6
_cell_measurement_theta_min      3.8
_cell_volume                     2043.8(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2244
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.484
_refine_ls_extinction_coef       0.00043(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.001P)²+7P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1198
_reflns_number_total             1644
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6092.cif
_cod_data_source_block           I
_cod_original_cell_volume        2043.8(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2202980
_cod_database_fobs_code          2202980
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 0.13825(6) 0.25372(13) 0.41799(9) 0.0768(4) Uani d . 1 . . S
F1 0.1163(2) -0.0506(4) 0.2268(6) 0.216(3) Uani d . 1 . . F
F2 0.0830(3) -0.0508(4) 0.3958(4) 0.178(2) Uani d . 1 . . F
F3 0.0143(3) -0.2008(6) 0.1690(5) 0.276(4) Uani d . 1 . . F
C1 0.0350(2) 0.1263(4) 0.2693(4) 0.0696(11) Uani d . 1 . . C
C2 0.0614(3) -0.0235(5) 0.2882(6) 0.0996(16) Uani d . 1 . . C
C3 0.0000 -0.1180(8) 0.2500 0.111(3) Uani d S 1 . . C
C4 0.0826(2) 0.2478(4) 0.2899(3) 0.0637(9) Uani d . 1 . . C
C5 0.09140(19) 0.3622(4) 0.2213(3) 0.0612(9) Uani d . 1 . . C
C6 0.14380(19) 0.4607(4) 0.2717(3) 0.0598(9) Uani d . 1 . . C
C7 0.17473(19) 0.4144(4) 0.3788(3) 0.0662(10) Uani d . 1 . . C
C8 0.2282(2) 0.4931(5) 0.4399(4) 0.0818(13) Uani d . 1 . . C
H8A 0.2484 0.4611 0.5108 0.098 Uiso calc R 1 . . H
C9 0.2502(2) 0.6172(6) 0.3939(4) 0.0897(14) Uani d . 1 . . C
H9A 0.2867 0.6692 0.4330 0.108 Uiso calc R 1 . . H
C10 0.2193(2) 0.6679(5) 0.2893(4) 0.0865(13) Uani d . 1 . . C
H10A 0.2342 0.7545 0.2602 0.104 Uiso calc R 1 . . H
C11 0.1667(2) 0.5907(5) 0.2288(4) 0.0741(11) Uani d . 1 . . C
H11A 0.1463 0.6251 0.1588 0.089 Uiso calc R 1 . . H
C12 0.0551(2) 0.3857(5) 0.1035(3) 0.0806(13) Uani d . 1 . . C
H12A 0.0224 0.3088 0.0849 0.121 Uiso calc R 1 . . H
H12B 0.0901 0.3886 0.0480 0.121 Uiso calc R 1 . . H
H12C 0.0296 0.4746 0.1020 0.121 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0858(7) 0.0741(7) 0.0690(7) 0.0105(6) -0.0024(5) 0.0156(6)
F1 0.176(4) 0.077(2) 0.421(8) 0.041(2) 0.175(5) 0.042(4)
F2 0.229(5) 0.077(2) 0.210(4) -0.004(3) -0.098(4) 0.048(3)
F3 0.227(5) 0.249(6) 0.333(7) 0.138(5) -0.090(6) -0.193(5)
C1 0.085(3) 0.055(2) 0.071(3) 0.0069(19) 0.017(2) 0.007(2)
C2 0.102(4) 0.061(3) 0.139(5) 0.011(3) 0.029(4) 0.014(3)
C3 0.146(7) 0.054(4) 0.136(7) 0.000 0.025(6) 0.000
C4 0.068(2) 0.058(2) 0.065(2) 0.0081(19) 0.0069(18) 0.0049(19)
C5 0.064(2) 0.062(2) 0.058(2) 0.0079(19) 0.0046(17) 0.0036(18)
C6 0.059(2) 0.058(2) 0.062(2) 0.0074(18) 0.0067(16) 0.0030(18)
C7 0.062(2) 0.070(3) 0.067(2) 0.010(2) 0.0043(18) 0.000(2)
C8 0.069(3) 0.097(4) 0.078(3) 0.006(3) -0.001(2) -0.010(3)
C9 0.071(3) 0.101(4) 0.097(4) -0.011(3) 0.010(2) -0.022(3)
C10 0.079(3) 0.079(3) 0.104(4) -0.012(3) 0.020(3) -0.003(3)
C11 0.074(3) 0.072(3) 0.076(3) 0.002(2) 0.008(2) 0.008(2)
C12 0.088(3) 0.089(3) 0.064(2) -0.011(3) -0.001(2) 0.015(2)
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'
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
C7 S1 C4 . . 91.48(19)
C1 C1 C4 2 . 128.5(2)
C1 C1 C2 2 . 110.5(3)
C4 C1 C2 . . 121.0(4)
F2 C2 F1 . . 106.4(5)
F2 C2 C3 . . 110.0(4)
F1 C2 C3 . . 110.1(5)
F2 C2 C1 . . 113.3(5)
F1 C2 C1 . . 111.3(4)
C3 C2 C1 . . 105.7(5)
F3 C3 F3 2 . 104.6(9)
F3 C3 C2 2 . 110.3(3)
F3 C3 C2 . . 112.1(4)
F3 C3 C2 2 2 112.1(4)
F3 C3 C2 . 2 110.3(3)
C2 C3 C2 . 2 107.5(6)
C5 C4 C1 . . 128.6(4)
C5 C4 S1 . . 112.6(3)
C1 C4 S1 . . 118.8(3)
C4 C5 C6 . . 112.2(3)
C4 C5 C12 . . 126.0(4)
C6 C5 C12 . . 121.7(3)
C11 C6 C7 . . 118.0(4)
C11 C6 C5 . . 129.3(4)
C7 C6 C5 . . 112.8(3)
C8 C7 C6 . . 121.4(4)
C8 C7 S1 . . 127.6(3)
C6 C7 S1 . . 111.0(3)
C9 C8 C7 . . 118.8(4)
C9 C8 H8A . . 120.6
C7 C8 H8A . . 120.6
C8 C9 C10 . . 121.1(5)
C8 C9 H9A . . 119.4
C10 C9 H9A . . 119.4
C11 C10 C9 . . 120.3(5)
C11 C10 H10A . . 119.9
C9 C10 H10A . . 119.9
C10 C11 C6 . . 120.4(4)
C10 C11 H11A . . 119.8
C6 C11 H11A . . 119.8
C5 C12 H12A . . 109.5
C5 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C5 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 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 C7 . 1.728(4) ?
S1 C4 . 1.753(4) ?
F1 C2 . 1.328(6) ?
F2 C2 . 1.311(7) ?
F3 C3 . 1.266(5) ?
C1 C1 2 1.359(8) ?
C1 C4 . 1.455(5) ?
C1 C2 . 1.496(6) ?
C2 C3 . 1.494(6) ?
C3 F3 2 1.266(5) ?
C3 C2 2 1.494(6) ?
C4 C5 . 1.353(5) ?
C5 C6 . 1.440(5) ?
C5 C12 . 1.498(5) ?
C6 C11 . 1.396(5) ?
C6 C7 . 1.402(5) ?
C7 C8 . 1.395(5) ?
C8 C9 . 1.356(6) ?
C8 H8A . 0.93 ?
C9 C10 . 1.391(6) ?
C9 H9A . 0.93 ?
C10 C11 . 1.372(6) ?
C10 H10A . 0.93 ?
C11 H11A . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
