#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:06:16 +0000 (Tue, 22 Mar 2016) $
#$Revision: 178934 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/63/4116322.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4116322
loop_
_publ_author_name
'Seiya Kobatake'
'Taro Yamada'
'Kingo Uchida'
'Nobuo Kato'
'Masahiro Irie'
_publ_section_title
;
 Photochromism of 1,2-Bis(2,5-dimethyl-3-thienyl)perfluoro- cyclopentene
 in a Single Crystalline Phase
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2380
_journal_page_last               2386
_journal_paper_doi               10.1021/ja983717j
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C17 H14 F6 S2'
_chemical_formula_weight         396.40
_chemical_name_systematic
; 
8,8,9,9,10,10-hexafluoro-1,2,4,14-tetramethyl-3,15-dithiatetracyclo[10.3.0.0
<2,6>.0<7,11>]pentadeca-4,6(7),11(12),13-tetraene
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.891(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3533(15)
_cell_length_b                   24.750(6)
_cell_length_c                   11.460(3)
_cell_measurement_temperature    304(2)
_cell_volume                     1741.5(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      304(2)
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_sigmaI/netI    0.1194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12386
_diffrn_reflns_theta_full        27.74
_diffrn_reflns_theta_max         27.74
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.76229
_exptl_absorpt_correction_T_min  0.60594
_exptl_absorpt_correction_type   emprical
_exptl_absorpt_process_details
;
 Ellipsoidal absorption correction was applied empirically by using the
program XPREP (Bruker SHELXTL package)
 with the value mu*t = 0.162
;
_exptl_crystal_colour            'deep red'
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1811
_refine_ls_R_factor_gt           0.0840
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+4.0943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1923
_reflns_number_gt                1822
_reflns_number_total             3739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja983717j_2.cif
_cod_data_source_block           1b
_cod_original_cell_volume        1741.6(7)
_cod_database_code               4116322
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.3798(3) 0.58016(6) 0.52292(13) 0.0567(5) Uani 1 1 d .
S2 S 0.0253(3) 0.49038(6) 0.32045(14) 0.0596(5) Uani 1 1 d .
C1 C 0.1719(8) 0.5962(2) 0.3838(4) 0.0413(13) Uani 1 1 d .
C10 C 0.1470(8) 0.5533(2) 0.2861(4) 0.0408(13) Uani 1 1 d .
F6 F -0.1441(7) 0.62804(16) -0.0693(3) 0.0848(13) Uani 1 1 d .
F4 F 0.1953(8) 0.68898(17) -0.0319(4) 0.0907(13) Uani 1 1 d .
C5 C 0.1558(9) 0.6624(2) 0.2248(5) 0.0407(13) Uani 1 1 d .
C2 C 0.2514(8) 0.6490(2) 0.3399(5) 0.0368(12) Uani 1 1 d .
F1 F 0.0856(8) 0.75638(14) 0.2064(3) 0.0937(15) Uani 1 1 d .
F3 F -0.0506(8) 0.74816(17) -0.0250(4) 0.1065(17) Uani 1 1 d .
C3 C 0.4095(8) 0.6753(2) 0.4325(5) 0.0449(14) Uani 1 1 d .
H3A H 0.4556 0.7105 0.4250 0.054 Uiso 1 1 calc R
C9 C 0.0095(9) 0.6263(2) 0.1432(4) 0.0408(13) Uani 1 1 d .
F2 F 0.3828(7) 0.72990(17) 0.1705(4) 0.0972(15) Uani 1 1 d .
C13 C -0.1492(9) 0.4869(2) 0.1757(5) 0.0509(15) Uani 1 1 d .
C11 C -0.0091(8) 0.5738(2) 0.1711(4) 0.0406(13) Uani 1 1 d .
C14 C -0.0432(10) 0.6087(2) 0.4165(5) 0.0535(16) Uani 1 1 d .
H14A H -0.1537 0.6172 0.3443 0.080 Uiso 1 1 calc R
H14B H -0.0227 0.6391 0.4705 0.080 Uiso 1 1 calc R
H14C H -0.0873 0.5778 0.4550 0.080 Uiso 1 1 calc R
C15 C 0.6525(10) 0.6608(3) 0.6445(5) 0.0664(19) Uani 1 1 d .
H15A H 0.6982 0.6974 0.6378 0.100 Uiso 1 1 calc R
H15B H 0.7760 0.6372 0.6564 0.100 Uiso 1 1 calc R
H15C H 0.5896 0.6579 0.7119 0.100 Uiso 1 1 calc R
C16 C 0.3659(9) 0.5401(2) 0.2553(5) 0.0537(16) Uani 1 1 d .
H16A H 0.4312 0.5730 0.2373 0.081 Uiso 1 1 calc R
H16B H 0.3391 0.5166 0.1866 0.081 Uiso 1 1 calc R
H16C H 0.4625 0.5227 0.3232 0.081 Uiso 1 1 calc R
F5 F -0.2952(6) 0.6769(2) 0.0411(4) 0.1058(16) Uani 1 1 d .
C8 C -0.1022(10) 0.6566(3) 0.0341(5) 0.0578(17) Uani 1 1 d .
C4 C 0.4877(9) 0.6454(2) 0.5318(5) 0.0460(14) Uani 1 1 d .
C12 C -0.1496(9) 0.5318(2) 0.1109(5) 0.0498(15) Uani 1 1 d .
H12A H -0.2352 0.5354 0.0322 0.060 Uiso 1 1 calc R
C6 C 0.1788(11) 0.7150(2) 0.1615(5) 0.0547(16) Uani 1 1 d .
C17 C -0.2791(10) 0.4371(3) 0.1403(6) 0.0689(19) Uani 1 1 d .
H17A H -0.3677 0.4408 0.0591 0.103 Uiso 1 1 calc R
H17B H -0.3708 0.4315 0.1940 0.103 Uiso 1 1 calc R
H17C H -0.1829 0.4068 0.1449 0.103 Uiso 1 1 calc R
C7 C 0.0497(12) 0.7046(3) 0.0312(6) 0.0666(19) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0659(10) 0.0505(9) 0.0419(8) 0.0120(7) -0.0075(7) -0.0107(8)
S2 0.0698(11) 0.0439(8) 0.0555(9) 0.0067(7) -0.0015(8) -0.0150(8)
C1 0.041(3) 0.044(3) 0.035(3) 0.009(2) 0.003(2) -0.008(3)
C10 0.037(3) 0.038(3) 0.042(3) 0.006(2) 0.002(2) -0.006(3)
F6 0.108(3) 0.096(3) 0.038(2) 0.0108(19) -0.005(2) 0.004(2)
F4 0.120(4) 0.084(3) 0.086(3) 0.004(2) 0.060(3) -0.001(3)
C5 0.041(3) 0.040(3) 0.043(3) 0.012(2) 0.014(3) 0.012(3)
C2 0.036(3) 0.034(3) 0.043(3) 0.004(2) 0.015(2) 0.004(2)
F1 0.154(4) 0.050(2) 0.073(3) 0.0096(19) 0.022(3) 0.038(3)
F3 0.153(4) 0.076(3) 0.077(3) 0.041(2) 0.005(3) 0.039(3)
C3 0.044(3) 0.039(3) 0.050(3) 0.003(3) 0.009(3) -0.005(3)
C9 0.040(3) 0.051(3) 0.030(3) 0.010(2) 0.007(2) 0.013(3)
F2 0.088(3) 0.090(3) 0.115(4) 0.041(3) 0.030(3) -0.022(3)
C13 0.045(3) 0.057(4) 0.050(3) -0.008(3) 0.010(3) -0.004(3)
C11 0.039(3) 0.052(3) 0.032(3) 0.002(3) 0.009(2) 0.001(3)
C14 0.062(4) 0.051(4) 0.051(4) 0.004(3) 0.020(3) 0.000(3)
C15 0.065(4) 0.067(4) 0.054(4) -0.010(3) -0.008(3) -0.006(4)
C16 0.053(4) 0.049(3) 0.058(4) -0.002(3) 0.011(3) 0.012(3)
F5 0.065(3) 0.150(4) 0.101(3) 0.051(3) 0.019(2) 0.057(3)
C8 0.055(4) 0.075(4) 0.040(3) 0.012(3) 0.006(3) 0.030(4)
C4 0.041(3) 0.046(3) 0.048(3) -0.003(3) 0.007(3) -0.005(3)
C12 0.039(3) 0.070(4) 0.036(3) -0.005(3) 0.001(2) 0.008(3)
C6 0.064(4) 0.045(3) 0.057(4) 0.016(3) 0.019(3) 0.017(3)
C17 0.055(4) 0.065(4) 0.085(5) -0.026(4) 0.016(4) -0.010(3)
C7 0.096(5) 0.056(4) 0.052(4) 0.023(3) 0.026(4) 0.025(4)
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
C4 S1 C1 92.0(2)
C13 S2 C10 92.1(3)
C10 C1 C2 109.6(4)
C10 C1 C14 112.9(4)
C2 C1 C14 107.2(4)
C10 C1 S1 113.9(4)
C2 C1 S1 104.2(3)
C14 C1 S1 108.6(4)
C11 C10 C1 109.1(4)
C11 C10 C16 107.2(4)
C1 C10 C16 112.5(4)
C11 C10 S2 104.7(3)
C1 C10 S2 114.0(4)
C16 C10 S2 108.9(4)
C2 C5 C9 122.4(5)
C2 C5 C6 127.3(5)
C9 C5 C6 110.3(4)
C5 C2 C3 132.6(5)
C5 C2 C1 115.3(4)
C3 C2 C1 112.1(4)
C4 C3 C2 114.8(5)
C11 C9 C5 121.5(4)
C11 C9 C8 129.7(5)
C5 C9 C8 108.8(5)
C12 C13 C17 128.2(5)
C12 C13 S2 113.5(4)
C17 C13 S2 118.3(5)
C9 C11 C12 132.0(5)
C9 C11 C10 116.7(4)
C12 C11 C10 111.4(5)
F5 C8 F6 105.7(5)
F5 C8 C9 112.7(5)
F6 C8 C9 114.9(5)
F5 C8 C7 107.5(5)
F6 C8 C7 111.8(5)
C9 C8 C7 104.1(5)
C3 C4 C15 128.2(5)
C3 C4 S1 114.0(4)
C15 C4 S1 117.8(4)
C13 C12 C11 115.2(5)
F2 C6 F1 105.9(5)
F2 C6 C5 114.5(5)
F1 C6 C5 111.3(5)
F2 C6 C7 113.0(6)
F1 C6 C7 108.8(5)
C5 C6 C7 103.3(5)
F3 C7 F4 106.1(5)
F3 C7 C6 114.0(5)
F4 C7 C6 107.3(6)
F3 C7 C8 114.3(6)
F4 C7 C8 107.9(5)
C6 C7 C8 106.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.746(6)
S1 C1 1.834(5)
S2 C13 1.744(6)
S2 C10 1.826(5)
C1 C10 1.521(7)
C1 C2 1.533(7)
C1 C14 1.538(8)
C10 C11 1.519(7)
C10 C16 1.554(8)
F6 C8 1.346(7)
F4 C7 1.368(7)
C5 C2 1.344(7)
C5 C9 1.446(7)
C5 C6 1.515(7)
C2 C3 1.418(7)
F1 C6 1.350(7)
F3 C7 1.332(6)
C3 C4 1.342(7)
C9 C11 1.350(7)
C9 C8 1.476(7)
F2 C6 1.326(7)
C13 C12 1.335(8)
C13 C17 1.481(8)
C11 C12 1.426(7)
C15 C4 1.488(7)
F5 C8 1.347(7)
C8 C7 1.535(9)
C6 C7 1.530(9)
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
C4 S1 C1 C10 134.3(4)
C4 S1 C1 C2 15.0(4)
C4 S1 C1 C14 -98.9(4)
C2 C1 C10 C11 -57.2(5)
C14 C1 C10 C11 62.2(6)
S1 C1 C10 C11 -173.4(3)
C2 C1 C10 C16 61.7(5)
C14 C1 C10 C16 -179.0(4)
S1 C1 C10 C16 -54.6(5)
C2 C1 C10 S2 -173.8(3)
C14 C1 C10 S2 -54.4(5)
S1 C1 C10 S2 70.0(4)
C13 S2 C10 C11 15.3(4)
C13 S2 C10 C1 134.4(4)
C13 S2 C10 C16 -99.1(4)
C9 C5 C2 C3 174.6(5)
C6 C5 C2 C3 -6.1(10)
C9 C5 C2 C1 -7.7(7)
C6 C5 C2 C1 171.6(5)
C10 C1 C2 C5 42.3(6)
C14 C1 C2 C5 -80.5(6)
S1 C1 C2 C5 164.5(4)
C10 C1 C2 C3 -139.5(5)
C14 C1 C2 C3 97.6(5)
S1 C1 C2 C3 -17.3(5)
C5 C2 C3 C4 -171.0(6)
C1 C2 C3 C4 11.3(7)
C2 C5 C9 C11 -12.1(8)
C6 C5 C9 C11 168.5(5)
C2 C5 C9 C8 168.1(5)
C6 C5 C9 C8 -11.3(6)
C10 S2 C13 C12 -9.7(5)
C10 S2 C13 C17 171.5(5)
C5 C9 C11 C12 175.1(6)
C8 C9 C11 C12 -5.1(10)
C5 C9 C11 C10 -5.9(8)
C8 C9 C11 C10 173.8(5)
C1 C10 C11 C9 40.4(6)
C16 C10 C11 C9 -81.7(6)
S2 C10 C11 C9 162.7(4)
C1 C10 C11 C12 -140.5(5)
C16 C10 C11 C12 97.4(5)
S2 C10 C11 C12 -18.1(5)
C11 C9 C8 F5 86.9(8)
C5 C9 C8 F5 -93.3(6)
C11 C9 C8 F6 -34.3(9)
C5 C9 C8 F6 145.5(5)
C11 C9 C8 C7 -156.9(6)
C5 C9 C8 C7 22.9(6)
C2 C3 C4 C15 -179.5(6)
C2 C3 C4 S1 1.2(7)
C1 S1 C4 C3 -10.4(5)
C1 S1 C4 C15 170.3(5)
C17 C13 C12 C11 178.6(6)
S2 C13 C12 C11 0.0(7)
C9 C11 C12 C13 -168.4(6)
C10 C11 C12 C13 12.6(7)
C2 C5 C6 F2 52.1(8)
C9 C5 C6 F2 -128.5(5)
C2 C5 C6 F1 -68.1(8)
C9 C5 C6 F1 111.3(5)
C2 C5 C6 C7 175.3(6)
C9 C5 C6 C7 -5.3(6)
F2 C6 C7 F3 -89.3(7)
F1 C6 C7 F3 28.0(8)
C5 C6 C7 F3 146.4(6)
F2 C6 C7 F4 27.9(7)
F1 C6 C7 F4 145.2(5)
C5 C6 C7 F4 -96.4(6)
F2 C6 C7 C8 143.4(5)
F1 C6 C7 C8 -99.2(6)
C5 C6 C7 C8 19.1(6)
F5 C8 C7 F3 -33.3(7)
F6 C8 C7 F3 82.3(7)
C9 C8 C7 F3 -153.1(5)
F5 C8 C7 F4 -151.1(5)
F6 C8 C7 F4 -35.5(6)
C9 C8 C7 F4 89.1(6)
F5 C8 C7 C6 93.8(5)
F6 C8 C7 C6 -150.7(5)
C9 C8 C7 C6 -26.0(6)