#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:21:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180258 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/44/7114409.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_7114409
loop_
_publ_author_name
'Kobatake, Seiya'
'Uchida, Kingo'
'Tsuchida, Eriko'
'Irie, Masahiro'
_publ_section_title
;
 Single-crystalline photochromism of diarylethenes: reactivity???structure
 relationshipElectronic supplementary information (ESI) available: X-ray
 crystallographic data for 2a, 3a and 4a. See
 http://www.rsc.org/suppdata/cc/b2/b208419h/
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_page_first              2804
_journal_paper_doi               10.1039/b208419h
_journal_year                    2002
_chemical_formula_sum            'C33 H30 F6 S2'
_chemical_formula_weight         604.69
_chemical_name_systematic
;
1,2-Bis(2-isopropyl-4-methyl-3-thienyl)perfluorocyclopentene
;
_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                 127.235(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.546(4)
_cell_length_b                   8.3164(15)
_cell_length_c                   19.233(4)
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.25
_cell_measurement_theta_min      2.17
_cell_volume                     2998.5(10)
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6489
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        1.1
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0440
_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)+(0.0745P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1622
_reflns_number_total             2151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b208419h.txt
_cod_data_source_block           compd3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2998.4(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7114409
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.07535(3) 0.94600(7) 0.16571(4) 0.0516(2) Uani 1 1 d . . .
F1A F 0.1014(3) 0.3641(8) 0.2535(4) 0.0727(17) Uani 0.50 1 d PD A 1
F2A F -0.0063(3) 0.3614(8) 0.1364(4) 0.0709(14) Uani 0.50 1 d PD B 1
C6A C 0.0305(4) 0.3922(8) 0.2186(5) 0.042(2) Uiso 0.50 1 d PD . 1
F1B F 0.0340(4) 0.3757(8) 0.1582(5) 0.100(3) Uani 0.50 1 d PD . 2
F2B F 0.1092(4) 0.3487(8) 0.2990(5) 0.094(2) Uani 0.50 1 d PD . 2
C6B C 0.0456(4) 0.3962(9) 0.2375(5) 0.048(3) Uiso 0.50 1 d PD . 2
F3 F 0.0160(7) 0.1494(4) 0.2712(8) 0.110(5) Uani 0.50 1 d P . .
F4 F 0.0674(2) 0.2592(6) 0.3485(3) 0.0938(12) Uani 0.50 1 d P . .
C1 C 0.02116(12) 0.7928(3) 0.15418(15) 0.0433(6) Uani 1 1 d . . .
C2 C 0.05569(11) 0.7036(3) 0.22879(14) 0.0410(6) Uani 1 1 d . . .
C3 C 0.12723(12) 0.7559(3) 0.29574(15) 0.0458(6) Uani 1 1 d . . .
C4 C 0.14435(12) 0.8892(3) 0.27025(15) 0.0482(6) Uani 1 1 d . . .
C5 C 0.02297(11) 0.5634(3) 0.24019(14) 0.0400(5) Uani 1 1 d . . .
C7 C 0.0117(3) 0.2883(5) 0.2664(4) 0.0499(14) Uiso 0.50 1 d P . .
C8 C -0.05101(13) 0.7695(3) 0.06930(15) 0.0512(6) Uani 1 1 d . . .
H8 H -0.0747 0.6828 0.0773 0.061 Uiso 1 1 calc R . .
C9 C -0.04557(18) 0.7174(4) -0.00298(19) 0.0804(9) Uani 1 1 d . . .
H9A H -0.0236 0.8015 -0.0133 0.121 Uiso 1 1 calc R . .
H9B H -0.0925 0.6965 -0.0556 0.121 Uiso 1 1 calc R . .
H9C H -0.0172 0.6215 0.0148 0.121 Uiso 1 1 calc R . .
C10 C -0.09727(15) 0.9190(4) 0.0413(2) 0.0805(9) Uani 1 1 d . . .
H10A H -0.1022 0.9475 0.0857 0.121 Uiso 1 1 calc R . .
H10B H -0.1435 0.8977 -0.0124 0.121 Uiso 1 1 calc R . .
H10C H -0.0753 1.0061 0.0328 0.121 Uiso 1 1 calc R . .
C11 C 0.17879(14) 0.6707(3) 0.38067(17) 0.0641(7) Uani 1 1 d . . .
H11A H 0.1934 0.5717 0.3702 0.096 Uiso 1 1 calc R . .
H11B H 0.1562 0.6482 0.4077 0.096 Uiso 1 1 calc R . .
H11C H 0.2198 0.7376 0.4186 0.096 Uiso 1 1 calc R . .
C12 C 0.21162(13) 0.9839(3) 0.31995(17) 0.0536(7) Uani 1 1 d . . .
C13 C 0.23645(15) 1.0539(4) 0.39858(19) 0.0732(9) Uani 1 1 d . . .
H13 H 0.2108 1.0415 0.4207 0.088 Uiso 1 1 calc R . .
C14 C 0.29874(16) 1.1423(4) 0.4450(2) 0.0861(10) Uani 1 1 d . . .
H14 H 0.3148 1.1886 0.4981 0.103 Uiso 1 1 calc R . .
C15 C 0.33676(17) 1.1620(4) 0.4134(2) 0.0831(10) Uani 1 1 d . . .
H15 H 0.3786 1.2219 0.4447 0.100 Uiso 1 1 calc R . .
C16 C 0.31308(17) 1.0932(4) 0.3357(2) 0.0849(10) Uani 1 1 d . . .
H16 H 0.3391 1.1062 0.3142 0.102 Uiso 1 1 calc R . .
C17 C 0.25081(15) 1.0047(4) 0.28890(19) 0.0706(8) Uani 1 1 d . . .
H17 H 0.2351 0.9586 0.2360 0.085 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 S1 C1 92.85(11) . .
F2A C6A C7 95.2(6) . 2
F2A C6A F1A 106.2(6) . .
C7 C6A F1A 124.2(6) 2 .
F2A C6A C5 114.7(6) . .
C7 C6A C5 107.0(5) 2 .
F1A C6A C5 109.2(5) . .
F2A C6A C7 114.0(6) . .
F1A C6A C7 108.6(6) . .
C5 C6A C7 104.1(5) . .
F2B C6B F1B 108.5(7) . .
F2B C6B C7 110.8(6) . 2
F1B C6B C7 106.4(6) . 2
F2B C6B C5 119.5(6) . .
F1B C6B C5 108.3(6) . .
C7 C6B C5 102.5(5) 2 .
F2B C6B C7 93.5(6) . .
F1B C6B C7 122.3(6) . .
C5 C6B C7 105.0(5) . .
C2 C1 C8 129.7(2) . .
C2 C1 S1 110.11(17) . .
C8 C1 S1 120.08(17) . .
C1 C2 C3 114.1(2) . .
C1 C2 C5 123.4(2) . .
C3 C2 C5 122.53(19) . .
C4 C3 C2 111.4(2) . .
C4 C3 C11 123.6(2) . .
C2 C3 C11 124.9(2) . .
C3 C4 C12 129.0(2) . .
C3 C4 S1 111.53(17) . .
C12 C4 S1 119.49(18) . .
C5 C5 C2 128.26(12) 2 .
C5 C5 C6B 111.9(3) 2 .
C2 C5 C6B 119.7(3) . .
C5 C5 C6A 108.8(3) 2 .
C2 C5 C6A 122.5(3) . .
F3 C7 C6A 127.4(11) . 2
F3 C7 C6A 117.3(9) 2 2
F3 C7 F4 107.4(5) 2 .
C6A C7 F4 100.0(5) 2 .
F3 C7 C6B 126.9(10) . 2
F3 C7 C6B 110.5(8) 2 2
F4 C7 C6B 111.2(5) . 2
F3 C7 C6A 125.0(10) . .
F3 C7 C6A 113.5(9) 2 .
C6A C7 C6A 105.4(6) 2 .
F4 C7 C6A 112.6(5) . .
C6B C7 C6A 101.7(3) 2 .
F3 C7 C6B 125.4(11) . .
F3 C7 C6B 121.1(10) 2 .
C6A C7 C6B 107.1(3) 2 .
F4 C7 C6B 100.5(5) . .
C6B C7 C6B 105.7(6) 2 .
F3 C7 F4 86.6(6) . 2
C6A C7 F4 90.0(4) 2 2
C6B C7 F4 78.7(4) 2 2
C6A C7 F4 78.6(4) . 2
C6B C7 F4 90.7(4) . 2
C1 C8 C10 112.3(2) . .
C1 C8 C9 111.3(2) . .
C10 C8 C9 110.2(2) . .
C13 C12 C17 118.1(2) . .
C13 C12 C4 120.6(2) . .
C17 C12 C4 121.3(2) . .
C12 C13 C14 121.0(3) . .
C15 C14 C13 120.2(3) . .
C14 C15 C16 119.7(3) . .
C15 C16 C17 120.5(3) . .
C12 C17 C16 120.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.718(2) .
S1 C1 1.720(2) .
F1A C6A 1.392(8) .
F2A C6A 1.287(9) .
C6A C7 1.470(9) 2
C6A C5 1.524(7) .
C6A C7 1.511(9) .
F1B C6B 1.388(9) .
F2B C6B 1.286(10) .
C6B C7 1.582(10) 2
C6B C5 1.502(8) .
C6B C7 1.513(10) .
F3 C7 1.159(5) .
F3 C7 1.309(8) 2
F4 C7 1.329(6) .
F4 C7 1.852(7) 2
C1 C2 1.363(3) .
C1 C8 1.494(3) .
C2 C3 1.435(3) .
C2 C5 1.485(3) .
C3 C4 1.368(3) .
C3 C11 1.498(3) .
C4 C12 1.486(3) .
C5 C5 1.344(4) 2
C7 C7 0.531(11) 2
C7 F3 1.309(8) 2
C7 C6A 1.470(9) 2
C7 C6B 1.582(10) 2
C7 F4 1.852(7) 2
C8 C10 1.520(4) .
C8 C9 1.534(4) .
C12 C13 1.378(4) .
C12 C17 1.380(4) .
C13 C14 1.380(4) .
C14 C15 1.362(4) .
C15 C16 1.365(5) .
C16 C17 1.381(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 S1 C1 C2 0.38(18) . .
C4 S1 C1 C8 -176.92(19) . .
C8 C1 C2 C3 175.6(2) . .
S1 C1 C2 C3 -1.4(3) . .
C8 C1 C2 C5 -3.8(4) . .
S1 C1 C2 C5 179.21(17) . .
C1 C2 C3 C4 1.9(3) . .
C5 C2 C3 C4 -178.6(2) . .
C1 C2 C3 C11 -174.4(2) . .
C5 C2 C3 C11 5.0(4) . .
C2 C3 C4 C12 178.4(2) . .
C11 C3 C4 C12 -5.3(4) . .
C2 C3 C4 S1 -1.6(3) . .
C11 C3 C4 S1 174.8(2) . .
C1 S1 C4 C3 0.71(19) . .
C1 S1 C4 C12 -179.2(2) . .
C1 C2 C5 C5 -80.0(4) . 2
C3 C2 C5 C5 100.6(3) . 2
C1 C2 C5 C6B 105.4(4) . .
C3 C2 C5 C6B -73.9(4) . .
C1 C2 C5 C6A 91.6(4) . .
C3 C2 C5 C6A -87.8(4) . .
F2B C6B C5 C5 -107.7(7) . 2
F1B C6B C5 C5 127.4(6) . 2
C7 C6B C5 C5 15.2(6) 2 2
C7 C6B C5 C5 -4.8(6) . 2
F2B C6B C5 C2 67.7(7) . .
F1B C6B C5 C2 -57.2(7) . .
C7 C6B C5 C2 -169.4(3) 2 .
C7 C6B C5 C2 170.6(3) . .
F2B C6B C5 C6A 174(3) . .
F1B C6B C5 C6A 50(2) . .
C7 C6B C5 C6A -63(2) 2 .
C7 C6B C5 C6A -83(2) . .
F2A C6A C5 C5 100.2(5) . 2
C7 C6A C5 C5 -4.0(6) 2 2
F1A C6A C5 C5 -140.8(5) . 2
C7 C6A C5 C5 -25.0(6) . 2
F2A C6A C5 C2 -72.9(6) . .
C7 C6A C5 C2 -177.1(3) 2 .
F1A C6A C5 C2 46.1(7) . .
C7 C6A C5 C2 161.9(3) . .
F2A C6A C5 C6B -153(3) . .
C7 C6A C5 C6B 103(3) 2 .
F1A C6A C5 C6B -34(2) . .
C7 C6A C5 C6B 82(2) . .
F2A C6A C7 F3 60.1(10) . .
F1A C6A C7 F3 -58.0(10) . .
C5 C6A C7 F3 -174.3(8) . .
F2A C6A C7 F3 25.4(9) . 2
F1A C6A C7 F3 -92.7(9) . 2
C5 C6A C7 F3 151.0(7) . 2
F2A C6A C7 C6A -104.3(7) . 2
F1A C6A C7 C6A 137.6(7) . 2
C5 C6A C7 C6A 21.4(4) . 2
F2A C6A C7 F4 147.7(6) . .
F1A C6A C7 F4 29.6(8) . .
C5 C6A C7 F4 -86.7(6) . .
F2A C6A C7 C6B -93.3(6) . 2
F1A C6A C7 C6B 148.6(6) . 2
C5 C6A C7 C6B 32.4(6) . 2
F2A C6A C7 C6B 156(3) . .
F1A C6A C7 C6B 38(2) . .
C5 C6A C7 C6B -78(2) . .
F2A C6A C7 F4 -17.5(6) . 2
F1A C6A C7 F4 -135.6(6) . 2
C5 C6A C7 F4 108.2(4) . 2
F2B C6B C7 F3 -59.7(10) . .
F1B C6B C7 F3 54.9(12) . .
C5 C6B C7 F3 178.5(8) . .
F2B C6B C7 F3 -98.0(8) . 2
F1B C6B C7 F3 16.5(12) . 2
C5 C6B C7 F3 140.2(7) . 2
F2B C6B C7 C6A 123.8(6) . 2
F1B C6B C7 C6A -121.6(8) . 2
C5 C6B C7 C6A 2.0(7) . 2
F2B C6B C7 F4 19.8(6) . .
F1B C6B C7 F4 134.3(7) . .
C5 C6B C7 F4 -102.0(5) . .
F2B C6B C7 C6B 135.5(6) . 2
F1B C6B C7 C6B -109.9(9) . 2
C5 C6B C7 C6B 13.8(4) . 2
F2B C6B C7 C6A -152(3) . .
F1B C6B C7 C6A -38(2) . .
C5 C6B C7 C6A 86(2) . .
F2B C6B C7 F4 -146.0(5) . 2
F1B C6B C7 F4 -31.4(8) . 2
C7 C6B C7 F4 7.1(8) 2 2
C5 C6B C7 F4 92.2(5) . 2
C2 C1 C8 C10 126.1(3) . .
S1 C1 C8 C10 -57.2(3) . .
C2 C1 C8 C9 -109.9(3) . .
S1 C1 C8 C9 66.8(3) . .
C3 C4 C12 C13 -58.5(4) . .
S1 C4 C12 C13 121.4(3) . .
C3 C4 C12 C17 121.7(3) . .
S1 C4 C12 C17 -58.4(3) . .
C17 C12 C13 C14 0.0(4) . .
C4 C12 C13 C14 -179.8(3) . .
C12 C13 C14 C15 0.1(5) . .
C13 C14 C15 C16 -0.2(5) . .
C14 C15 C16 C17 0.2(5) . .
C13 C12 C17 C16 0.0(5) . .
C4 C12 C17 C16 179.8(3) . .
C15 C16 C17 C12 -0.1(5) . .
