#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/67/2206705.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_2206705
loop_
_publ_author_name
'Pu, Shou-Zhi'
'Liu, Gang'
'Yan, Liu-Shui'
_publ_section_title
3,3,4,4,5,5-Hexafluoro-1,2-bis{3-methyl-5-[3-(trifluoromethyl)phenyl]-2-thienyl}cyclopent-1-ene
_journal_coeditor_code           HG6218
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2856
_journal_page_last               o2858
_journal_paper_doi               10.1107/S1600536805025134
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C29 H16 F12 S2'
_chemical_formula_moiety         'C29 H16 F12 S2'
_chemical_formula_sum            'C29 H16 F12 S2'
_chemical_formula_weight         656.54
_chemical_name_systematic
;
3,3,4,4,5,5-Hexafluoro-1,2-bis{3-methyl-5-[3-(trifluoromethyl)phenyl}-
2-thienyl]cyclopent-1-ene
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.498(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.011(2)
_cell_length_b                   8.6936(8)
_cell_length_c                   16.3481(16)
_cell_measurement_reflns_used    37
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.47
_cell_measurement_theta_min      4.80
_cell_volume                     2765.5(5)
_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_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2996
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.483
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0754
_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+ 13P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1876
_reflns_number_total             2422
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6218.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2206705
_cod_database_fobs_code          2206705
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_type_symbol
S1 0.38674(6) 1.08574(13) 0.58465(7) 0.0694(3) Uani d . 1 S
F1 0.4928(2) 1.4229(4) 0.6099(2) 0.1144(12) Uani d . 1 F
F2 0.40109(18) 1.4168(4) 0.6513(3) 0.1323(14) Uani d . 1 F
F3 0.5443(4) 1.5833(6) 0.7316(3) 0.307(6) Uani d . 1 F
F4 0.2878(2) 0.3479(5) 0.4435(4) 0.179(2) Uani d . 1 F
F5 0.2978(4) 0.3801(6) 0.3227(3) 0.233(3) Uani d . 1 F
F6 0.3843(2) 0.3753(4) 0.4253(3) 0.1250(12) Uani d . 1 F
C1 0.4842(2) 1.2295(4) 0.7086(2) 0.0601(10) Uani d . 1 C
C2 0.4683(3) 1.3908(5) 0.6771(3) 0.0762(13) Uani d . 1 C
C3 0.5000 1.4928(8) 0.7500 0.122(4) Uani d S 1 C
C4 0.4670(2) 1.0995(5) 0.6516(2) 0.0595(10) Uani d . 1 C
C5 0.5084(2) 0.9765(5) 0.6420(2) 0.0587(10) Uani d . 1 C
C6 0.4728(2) 0.8730(5) 0.5801(3) 0.0640(11) Uani d . 1 C
H6A 0.4930 0.7842 0.5652 0.077 Uiso calc R 1 H
C7 0.4068(2) 0.9134(5) 0.5443(2) 0.0612(10) Uani d . 1 C
C8 0.3548(2) 0.8310(5) 0.4808(2) 0.0624(10) Uani d . 1 C
C9 0.3626(2) 0.6754(5) 0.4659(3) 0.0675(11) Uani d . 1 C
H9A 0.4013 0.6231 0.4957 0.081 Uiso calc R 1 H
C10 0.3136(2) 0.5982(6) 0.4072(3) 0.0713(12) Uani d . 1 C
C11 0.2567(3) 0.6720(7) 0.3621(3) 0.0830(14) Uani d . 1 C
H11A 0.2243 0.6193 0.3217 0.100 Uiso calc R 1 H
C12 0.2478(3) 0.8249(7) 0.3770(3) 0.0878(15) Uani d . 1 C
H12A 0.2086 0.8750 0.3470 0.105 Uiso calc R 1 H
C13 0.2943(2) 0.9036(6) 0.4340(3) 0.0716(12) Uani d . 1 C
H13A 0.2869 1.0072 0.4429 0.086 Uiso calc R 1 H
C14 0.3219(3) 0.4310(7) 0.3949(4) 0.0998(18) Uani d . 1 C
C15 0.5817(2) 0.9549(5) 0.6877(3) 0.0737(12) Uani d . 1 C
H15A 0.6022 1.0534 0.7040 0.110 Uiso calc R 1 H
H15B 0.6062 0.9042 0.6515 0.110 Uiso calc R 1 H
H15C 0.5837 0.8932 0.7369 0.110 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 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
_geom_angle_publ_flag
C7 S1 C4 . . 92.2(2) yes
C1 C1 C4 2_656 . 128.7(2) no
C1 C1 C2 2_656 . 110.8(2) yes
C4 C1 C2 . . 120.5(4) no
F2 C2 F1 . . 104.0(4) yes
F2 C2 C3 . . 111.1(4) yes
F1 C2 C3 . . 111.2(4) no
F2 C2 C1 . . 112.6(4) no
F1 C2 C1 . . 112.8(4) no
C3 C2 C1 . . 105.2(4) yes
F3 C3 F3 . 2_656 103.6(9) yes
F3 C3 C2 . . 111.5(3) no
F3 C3 C2 2_656 . 111.3(4) no
F3 C3 C2 . 2_656 111.3(4) no
F3 C3 C2 2_656 2_656 111.5(3) no
C2 C3 C2 . 2_656 107.7(6) yes
C5 C4 C1 . . 128.0(4) no
C5 C4 S1 . . 111.6(3) yes
C1 C4 S1 . . 120.4(3) yes
C4 C5 C6 . . 111.0(4) yes
C4 C5 C15 . . 125.7(4) no
C6 C5 C15 . . 123.3(4) no
C7 C6 C5 . . 114.8(4) no
C7 C6 H6A . . 122.6 no
C5 C6 H6A . . 122.6 no
C6 C7 C8 . . 129.3(4) yes
C6 C7 S1 . . 110.4(3) yes
C8 C7 S1 . . 120.3(3) yes
C9 C8 C13 . . 117.0(4) no
C9 C8 C7 . . 120.5(4) no
C13 C8 C7 . . 122.5(4) no
C10 C9 C8 . . 120.4(4) no
C10 C9 H9A . . 119.8 no
C8 C9 H9A . . 119.8 no
C11 C10 C9 . . 121.2(5) no
C11 C10 C14 . . 119.6(5) yes
C9 C10 C14 . . 119.2(5) no
C10 C11 C12 . . 119.1(5) no
C10 C11 H11A . . 120.4 no
C12 C11 H11A . . 120.4 no
C13 C12 C11 . . 121.3(5) no
C13 C12 H12A . . 119.3 no
C11 C12 H12A . . 119.3 no
C12 C13 C8 . . 120.9(5) yes
C12 C13 H13A . . 119.5 no
C8 C13 H13A . . 119.5 no
F5 C14 F6 . . 110.4(6) yes
F5 C14 F4 . . 103.1(6) yes
F6 C14 F4 . . 98.2(5) yes
F5 C14 C10 . . 116.5(6) no
F6 C14 C10 . . 115.7(5) no
F4 C14 C10 . . 110.7(5) no
C5 C15 H15A . . 109.5 no
C5 C15 H15B . . 109.5 no
H15A C15 H15B . . 109.5 no
C5 C15 H15C . . 109.5 no
H15A C15 H15C . . 109.5 no
H15B C15 H15C . . 109.5 no
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 . 1.721(4) yes
S1 C4 . 1.724(4) no
F1 C2 . 1.334(5) no
F2 C2 . 1.331(6) no
F3 C3 . 1.272(6) no
F4 C14 . 1.368(8) no
F5 C14 . 1.247(7) no
F6 C14 . 1.324(6) no
C1 C1 2_656 1.354(8) yes
C1 C4 . 1.454(5) no
C1 C2 . 1.502(6) yes
C2 C3 . 1.502(6) yes
C3 F3 2_656 1.272(6) no
C3 C2 2_656 1.502(6) no
C4 C5 . 1.384(5) no
C5 C6 . 1.415(6) no
C5 C15 . 1.495(5) no
C6 C7 . 1.360(5) no
C6 H6A . 0.9300 no
C7 C8 . 1.472(6) no
C8 C9 . 1.390(6) yes
C8 C13 . 1.420(6) yes
C9 C10 . 1.376(6) no
C9 H9A . 0.9300 no
C10 C11 . 1.364(6) no
C10 C14 . 1.482(7) no
C11 C12 . 1.370(7) no
C11 H11A . 0.9300 no
C12 C13 . 1.341(7) no
C12 H12A . 0.9300 no
C13 H13A . 0.9300 no
C15 H15A . 0.9600 no
C15 H15B . 0.9600 no
C15 H15C . 0.9600 no
