#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/00/7050016.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_7050016
loop_
_publ_author_name
'Marion Giraud'
'Anne Léaustic'
'Marie-France Charlot'
'Pei Yu'
'Michèle Césario'
'Christian Philouze'
'Robert Pansu'
'Keitaro Nakatani'
'Eléna Ishow'
_publ_section_title
;
 Synthesis and photochromism of two new
 1,2-bis(thiazolyl)perfluorocyclopentenes with chelating sites
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              439
_journal_paper_doi               10.1039/b409274k
_journal_volume                  29
_journal_year                    2005
_chemical_compound_source        'chemical synthesis'
_chemical_formula_structural     'C23 H14 F6 N4 S2'
_chemical_formula_sum            'C23 H14 F6 N4 S2'
_chemical_formula_weight         524.50
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.52(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.492(6)
_cell_length_b                   8.379(3)
_cell_length_c                   16.790(7)
_cell_measurement_reflns_used    9136
_cell_measurement_temperature    293(2)
_cell_volume                     2315.8(15)
_computing_cell_refinement
;
'DENZO    (Otwinowski & Minor, 1997)    COLLECT  (Hooft,1998)'
;
_computing_data_collection
;
'DENZO    (Otwinowski & Minor, 1997)    COLLECT  (Hooft,1998)'
;
_computing_data_reduction        'HKL package  (Otwinowski & Minor,1997)'
_computing_molecular_graphics    'R3M (Riche,1983)   ORTEP   (Johnson,1965)'
_computing_publication_material  SHELXL-93)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius kappaCCD diffractometer'
_diffrn_measurement_method       'phi scans'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10909
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.869
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5694
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      0.893
_refine_ls_restrained_S_obs      0.879
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/esd_mean        0.049
_refine_ls_shift/su_max          1.100
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1028P)²+1.0702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1698
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                4078
_reflns_number_total             5695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b409274k.txt
_cod_data_source_block           photochromic_compound
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+1.0702P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+1.0702P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C23 H14 F6 N4  S2'
_cod_database_code               7050016
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1A S 0.25602(4) 0.00852(7) 0.89048(4) 0.0621(2) Uani 1 d . .
C2A C 0.31461(12) 0.1391(3) 0.83964(13) 0.0526(5) Uani 1 d . .
C3A C 0.34590(12) 0.2528(3) 0.89187(12) 0.0473(4) Uani 1 d . .
N4A N 0.32377(10) 0.2387(2) 0.96968(10) 0.0504(4) Uani 1 d . .
C5A C 0.27741(12) 0.1154(3) 0.97716(13) 0.0511(5) Uani 1 d . .
C9A C 0.3243(2) 0.1179(4) 0.75237(14) 0.0715(7) Uani 1 d . .
H9A1 H 0.2788 0.0590 0.7291 0.093 Uiso 1 calc R .
H9A2 H 0.3735 0.0604 0.74470 0.093 Uiso 1 calc R .
H9A3 H 0.3266 0.2206 0.7273 0.093 Uiso 1 calc R .
C10A C 0.24402(12) 0.0637(3) 1.05211(14) 0.0569(5) Uani 1 d . .
C11A C 0.25371(15) 0.1539(4) 1.12058(15) 0.0668(6) Uani 1 d . .
H11A H 0.28136 0.2506 1.12069 0.080 Uiso 1 calc R .
C12A C 0.2214(2) 0.0973(4) 1.1891(2) 0.0804(8) Uani 1 d . .
H12A H 0.2271 0.1551 1.2364 0.096 Uiso 1 calc R .
C13A C 0.1810(2) -0.0442(5) 1.1862(2) 0.0911(10) Uani 1 d . .
H13A H 0.1589 -0.0848 1.2316 0.109 Uiso 1 calc R .
C14A C 0.1735(2) -0.1257(4) 1.1159(2) 0.0935(10) Uani 1 d . .
H14A H 0.1453 -0.2218 1.1151 0.112 Uiso 1 calc R .
N15A N 0.20408(14) -0.0765(3) 1.04785(15) 0.0773(6) Uani 1 d . .
S1B S 0.57901(4) 0.04786(8) 0.73786(4) 0.0633(2) Uani 1 d . .
C2B C 0.53607(13) 0.1569(3) 0.81147(13) 0.0539(5) Uani 1 d . .
C3B C 0.49570(12) 0.2840(3) 0.77718(12) 0.0490(5) Uani 1 d . .
N4B N 0.49939(11) 0.2992(2) 0.69550(10) 0.0527(4) Uani 1 d . .
C5B C 0.54105(12) 0.1824(3) 0.66731(12) 0.0532(5) Uani 1 d . .
C9B C 0.5487(2) 0.1144(3) 0.89815(14) 0.0711(7) Uani 1 d . .
H9B1 H 0.5898 0.1822 0.9230 0.092 Uiso 1 calc R .
H9B2 H 0.5657 0.0051 0.90311 0.092 Uiso 1 calc R .
H9B3 H 0.4988 0.1287 0.9238 0.092 Uiso 1 calc R .
C10B C 0.55967(13) 0.1668(3) 0.58298(14) 0.0599(6) Uani 1 d . .
C11B C 0.5324(2) 0.2775(4) 0.52705(15) 0.0743(7) Uani 1 d . .
H11B H 0.4991 0.3616 0.54062 0.089 Uiso 1 calc R .
C12B C 0.5560(2) 0.2594(5) 0.4499(2) 0.0921(10) Uani 1 d . .
H12B H 0.5389 0.3322 0.4105 0.111 Uiso 1 calc R .
C13B C 0.6040(2) 0.1359(5) 0.4320(2) 0.1013(13) Uani 1 d . .
H13B H 0.6211 0.1233 0.3806 0.122 Uiso 1 calc R .
C14B C 0.6268(2) 0.0301(5) 0.4906(2) 0.0965(11) Uani 1 d . .
H14B H 0.6587 -0.0563 0.4771 0.116 Uiso 1 calc R .
N15B N 0.60639(14) 0.0421(3) 0.56677(15) 0.0781(7) Uani 1 d . .
C6A C 0.39427(12) 0.3920(2) 0.87198(11) 0.0451(4) Uani 1 d D .
C6B C 0.45327(12) 0.4075(3) 0.82061(11) 0.0464(4) Uani 1 d D .
C7A C 0.37796(13) 0.5497(3) 0.91107(12) 0.0515(5) Uani 1 d D .
F7A1 F 0.3003(4) 0.5840(10) 0.9144(4) 0.076(2) Uani 0.80 d PD .
F7A2 F 0.4137(2) 0.5561(3) 0.98552(14) 0.0693(6) Uani 0.80 d PD .
G7A1 F 0.3865(6) 0.5536(17) 0.9917(7) 0.067(3) Uiso 0.20 d PD .
G7A2 F 0.2941(14) 0.5821(33) 0.9099(13) 0.045(3) Uiso 0.20 d PD .
C7B C 0.47995(14) 0.5779(3) 0.81517(13) 0.0567(5) Uani 1 d D .
F7B1 F 0.48990(13) 0.6331(2) 0.74139(10) 0.0669(5) Uani 0.80 d PD .
F7B2 F 0.55655(10) 0.5976(2) 0.85392(14) 0.0707(5) Uani 0.80 d PD .
G7B1 F 0.4321(8) 0.6288(16) 0.7414(7) 0.120(4) Uiso 0.20 d PD .
G7B2 F 0.5460(7) 0.6101(15) 0.8083(8) 0.106(4) Uiso 0.20 d PD .
C8 C 0.4170(2) 0.6711(4) 0.8570(3) 0.0566(8) Uani 0.80 d PD .
C8' C 0.4387(10) 0.6640(22) 0.8807(10) 0.063(5) Uiso 0.20 d PD .
F81 F 0.4454(2) 0.8016(2) 0.8964(2) 0.0921(8) Uani 0.80 d PD .
F82 F 0.36117(12) 0.7282(2) 0.80071(13) 0.0784(6) Uani 0.80 d PD .
G81 F 0.4950(5) 0.7127(11) 0.9344(5) 0.082(2) Uiso 0.20 d PD .
G82 F 0.3977(7) 0.7870(16) 0.8506(7) 0.096(3) Uiso 0.20 d PD .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C2A S1A C5A 89.79(11) . . ?
C3A C2A C9A 130.6(2) . . ?
C3A C2A S1A 108.9(2) . . ?
C9A C2A S1A 120.5(2) . . ?
C2A C3A N4A 115.7(2) . . ?
C2A C3A C6A 126.6(2) . . ?
N4A C3A C6A 117.6(2) . . ?
C5A N4A C3A 110.6(2) . . ?
N4A C5A C10A 124.9(2) . . ?
N4A C5A S1A 115.0(2) . . ?
C10A C5A S1A 120.0(2) . . ?
N15A C10A C11A 123.7(2) . . ?
N15A C10A C5A 114.8(2) . . ?
C11A C10A C5A 121.5(2) . . ?
C10A C11A C12A 118.4(3) . . ?
C13A C12A C11A 118.9(3) . . ?
C12A C13A C14A 119.1(3) . . ?
N15A C14A C13A 124.4(3) . . ?
C14A N15A C10A 115.5(3) . . ?
C2B S1B C5B 89.89(11) . . ?
C3B C2B C9B 129.0(2) . . ?
C3B C2B S1B 108.8(2) . . ?
C9B C2B S1B 122.0(2) . . ?
C2B C3B N4B 116.1(2) . . ?
C2B C3B C6B 125.1(2) . . ?
N4B C3B C6B 118.7(2) . . ?
C5B N4B C3B 110.4(2) . . ?
N4B C5B C10B 124.2(2) . . ?
N4B C5B S1B 114.8(2) . . ?
C10B C5B S1B 120.9(2) . . ?
N15B C10B C11B 123.8(2) . . ?
N15B C10B C5B 115.0(2) . . ?
C11B C10B C5B 121.2(2) . . ?
C10B C11B C12B 117.8(3) . . ?
C13B C12B C11B 119.7(4) . . ?
C12B C13B C14B 118.7(3) . . ?
N15B C14B C13B 124.3(3) . . ?
C10B N15B C14B 115.7(3) . . ?
C6B C6A C3A 130.5(2) . . ?
C6B C6A C7A 110.5(2) . . ?
C3A C6A C7A 119.0(2) . . ?
C6A C6B C3B 129.5(2) . . ?
C6A C6B C7B 111.0(2) . . ?
C3B C6B C7B 119.4(2) . . ?
F7A1 C7A G7A1 89.6(6) . . ?
F7A1 C7A F7A2 108.8(4) . . ?
G7A1 C7A F7A2 19.9(5) . . ?
F7A1 C7A G7A2 3.6(13) . . ?
G7A1 C7A G7A2 92.9(10) . . ?
F7A2 C7A G7A2 112.2(9) . . ?
F7A1 C7A C8' 123.2(8) . . ?
G7A1 C7A C8' 107.1(8) . . ?
F7A2 C7A C8' 91.5(6) . . ?
G7A2 C7A C8' 123.3(13) . . ?
F7A1 C7A C6A 114.2(4) . . ?
G7A1 C7A C6A 116.6(6) . . ?
F7A2 C7A C6A 111.0(2) . . ?
G7A2 C7A C6A 111.4(12) . . ?
C8' C7A C6A 105.8(7) . . ?
F7A1 C7A C8 109.0(4) . . ?
G7A1 C7A C8 123.7(6) . . ?
F7A2 C7A C8 110.3(3) . . ?
G7A2 C7A C8 108.2(10) . . ?
C8' C7A C8 19.8(6) . . ?
C6A C7A C8 103.4(2) . . ?
G7B2 C7B F7B1 69.6(7) . . ?
G7B2 C7B F7B2 34.1(6) . . ?
F7B1 C7B F7B2 103.4(2) . . ?
G7B2 C7B C6B 121.4(7) . . ?
F7B1 C7B C6B 116.0(2) . . ?
F7B2 C7B C6B 110.2(2) . . ?
G7B2 C7B C8 128.1(7) . . ?
F7B1 C7B C8 112.2(3) . . ?
F7B2 C7B C8 110.6(2) . . ?
C6B C7B C8 104.6(2) . . ?
G7B2 C7B G7B1 108.0(9) . . ?
F7B1 C7B G7B1 38.9(5) . . ?
F7B2 C7B G7B1 140.6(6) . . ?
C6B C7B G7B1 100.4(6) . . ?
C8 C7B G7B1 83.9(6) . . ?
G7B2 C7B C8' 115.9(9) . . ?
F7B1 C7B C8' 126.4(7) . . ?
F7B2 C7B C8' 92.2(6) . . ?
C6B C7B C8' 105.3(7) . . ?
C8 C7B C8' 19.9(6) . . ?
G7B1 C7B C8' 103.3(8) . . ?
G7B1 F7B1 C7B 79.0(8) . . ?
G7B1 F7B1 G7B2 126.6(9) . . ?
C7B F7B1 G7B2 48.3(5) . . ?
G7B2 F7B2 C7B 54.4(9) . . ?
F7B1 G7B1 C7B 62.1(7) . . ?
F7B1 G7B1 F82 132.1(11) . . ?
C7B G7B1 F82 90.1(6) . . ?
F7B2 G7B2 C7B 91.5(12) . . ?
F7B2 G7B2 F7B1 152.4(14) . . ?
C7B G7B2 F7B1 62.1(6) . . ?
C8' C8 G82 112.5(24) . . ?
C8' C8 F81 61.1(22) . . ?
G82 C8 F81 51.7(7) . . ?
C8' C8 F82 165.8(23) . . ?
G82 C8 F82 53.4(8) . . ?
F81 C8 F82 104.8(3) . . ?
C8' C8 C7B 80.6(22) . . ?
G82 C8 C7B 131.3(7) . . ?
F81 C8 C7B 114.9(3) . . ?
F82 C8 C7B 108.3(3) . . ?
C8' C8 C7A 76.4(22) . . ?
G82 C8 C7A 123.5(7) . . ?
F81 C8 C7A 113.2(3) . . ?
F82 C8 C7A 110.7(3) . . ?
C7B C8 C7A 105.0(2) . . ?
C8' C8 G81 17.9(22) . . ?
G82 C8 G81 95.5(9) . . ?
F81 C8 G81 43.9(3) . . ?
F82 C8 G81 148.4(4) . . ?
C7B C8 G81 87.4(4) . . ?
C7A C8 G81 90.5(4) . . ?
C8 C8' F81 96.2(25) . . ?
C8 C8' G81 155.1(30) . . ?
F81 C8' G81 59.7(9) . . ?
C8 C8' G82 46.0(19) . . ?
F81 C8' G82 50.5(9) . . ?
G81 C8' G82 110.1(15) . . ?
C8 C8' C7A 83.7(22) . . ?
F81 C8' C7A 127.0(14) . . ?
G81 C8' C7A 115.1(12) . . ?
G82 C8' C7A 107.0(12) . . ?
C8 C8' C7B 79.4(21) . . ?
F81 C8' C7B 125.8(14) . . ?
G81 C8' C7B 108.4(12) . . ?
G82 C8' C7B 109.7(12) . . ?
C7A C8' C7B 106.4(11) . . ?
C8 C8' F82 10.3(17) . . ?
F81 C8' F82 86.0(10) . . ?
G81 C8' F82 145.2(14) . . ?
G82 C8' F82 35.8(8) . . ?
C7A C8' F82 89.2(8) . . ?
C7B C8' F82 86.1(7) . . ?
G82 F81 C8' 71.1(9) . . ?
G82 F81 G81 136.5(8) . . ?
C8' F81 G81 65.4(8) . . ?
G82 F81 C8 48.5(6) . . ?
C8' F81 C8 22.7(7) . . ?
G81 F81 C8 87.9(5) . . ?
G82 F82 C8 47.5(6) . . ?
G82 F82 G7B1 106.4(7) . . ?
C8 F82 G7B1 77.7(4) . . ?
G82 F82 C8' 43.6(8) . . ?
C8 F82 C8' 3.9(6) . . ?
G7B1 F82 C8' 79.9(7) . . ?
F81 G81 C8' 54.9(9) . . ?
F81 G81 C8 48.2(3) . . ?
C8' G81 C8 7.0(9) . . ?
C8 G82 F81 79.8(8) . . ?
C8 G82 F82 79.1(11) . . ?
F81 G82 F82 157.9(13) . . ?
C8 G82 C8' 21.5(8) . . ?
F81 G82 C8' 58.4(9) . . ?
F82 G82 C8' 100.6(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C2A 1.721(2) . ?
S1A C5A 1.727(2) . ?
C2A C3A 1.374(3) . ?
C2A C9A 1.494(3) . ?
C3A N4A 1.383(3) . ?
C3A C6A 1.463(3) . ?
N4A C5A 1.296(3) . ?
C5A C10A 1.470(3) . ?
C10A N15A 1.347(3) . ?
C10A C11A 1.377(4) . ?
C11A C12A 1.381(4) . ?
C12A C13A 1.359(5) . ?
C13A C14A 1.362(5) . ?
C14A N15A 1.342(4) . ?
S1B C2B 1.724(2) . ?
S1B C5B 1.725(3) . ?
C2B C3B 1.364(3) . ?
C2B C9B 1.500(3) . ?
C3B N4B 1.382(3) . ?
C3B C6B 1.468(3) . ?
N4B C5B 1.301(3) . ?
C5B C10B 1.473(3) . ?
C10B N15B 1.336(3) . ?
C10B C11B 1.375(4) . ?
C11B C12B 1.385(3) . ?
C12B C13B 1.347(6) . ?
C13B C14B 1.360(6) . ?
C14B N15B 1.347(4) . ?
C6A C6B 1.346(3) . ?
C6A C7A 1.507(3) . ?
C6B C7B 1.498(3) . ?
C7A F7A1 1.317(7) . ?
C7A G7A1 1.353(12) . ?
C7A F7A2 1.350(3) . ?
C7A G7A2 1.41(2) . ?
C7A C8' 1.50(2) . ?
C7A C8 1.532(4) . ?
C7B G7B2 1.135(12) . ?
C7B F7B1 1.342(3) . ?
C7B F7B2 1.395(3) . ?
C7B C8 1.507(4) . ?
C7B G7B1 1.490(12) . ?
C7B C8' 1.51(2) . ?
F7B1 G7B1 0.954(13) . ?
F7B1 G7B2 1.423(13) . ?
F7B2 G7B2 0.782(12) . ?
G7B1 F82 1.788(14) . ?
C8 C8' 0.522(15) . ?
C8 G82 1.025(12) . ?
C8 F81 1.347(4) . ?
C8 F82 1.365(5) . ?
C8 G81 1.805(9) . ?
C8' F81 1.19(2) . ?
C8' G81 1.32(2) . ?
C8' G82 1.32(2) . ?
C8' F82 1.88(2) . ?
F81 G82 1.073(12) . ?
F81 G81 1.251(9) . ?
F82 G82 1.116(13) . ?
