#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/89/1508960.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_1508960
loop_
_publ_author_name
'Liu, Gang'
'Pu, Shouzhi'
'Wang, Renjie'
_publ_section_title
;
 Photochromism of asymmetrical diarylethenes with a pyrrole unit: effects
 of aromatic stabilization energies of aryl rings.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              980
_journal_page_last               983
_journal_paper_doi               10.1021/ol400188h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C17 H13 F6 N3 S'
_chemical_formula_weight         405.36
_chemical_name_systematic
;

1-(2,4-Dimethyl-5-thiazolyl)-2-(2-cyano-1,5-
dimethyl-4-pyrryl)perfluorocyclopentene 
;
_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                 98.0170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8095(18)
_cell_length_b                   13.1111(15)
_cell_length_c                   8.6534(10)
_cell_measurement_reflns_used    2572
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.22
_cell_measurement_theta_min      2.60
_cell_volume                     1776.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13351
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.9613
_exptl_absorpt_correction_T_min  0.9292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.356
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2074
_reflns_number_gt                2288
_reflns_number_total             3299
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400188h_si_001.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1508960
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
C1 C 0.2144(2) 0.5375(2) 0.2659(4) 0.0419(8) Uani 1 1 d .
C2 C 0.1832(3) 0.6057(3) 0.3858(5) 0.0601(10) Uani 1 1 d .
C3 C 0.2515(3) 0.6067(3) 0.5249(4) 0.0621(10) Uani 1 1 d .
C4 C 0.3100(2) 0.5191(3) 0.4982(4) 0.0548(9) Uani 1 1 d .
C5 C 0.2891(2) 0.4929(3) 0.3286(4) 0.0429(8) Uani 1 1 d .
C6 C 0.1642(2) 0.5277(2) 0.1131(4) 0.0395(7) Uani 1 1 d .
C7 C 0.1166(2) 0.6061(2) 0.0304(4) 0.0438(8) Uani 1 1 d .
H7 H 0.1109 0.6727 0.0646 0.053 Uiso 1 1 calc R
C8 C 0.0802(2) 0.5666(2) -0.1090(4) 0.0417(8) Uani 1 1 d .
C9 C 0.1542(2) 0.4408(2) 0.0193(4) 0.0408(8) Uani 1 1 d .
C10 C 0.1828(3) 0.3334(3) 0.0521(5) 0.0577(10) Uani 1 1 d .
H10A H 0.1371 0.2875 0.0150 0.087 Uiso 1 1 calc R
H10B H 0.1984 0.3244 0.1625 0.087 Uiso 1 1 calc R
H10C H 0.2312 0.3192 -0.0002 0.087 Uiso 1 1 calc R
C11 C 0.0808(2) 0.3984(3) -0.2491(4) 0.0576(10) Uani 1 1 d .
H11A H 0.1318 0.3720 -0.2827 0.086 Uiso 1 1 calc R
H11B H 0.0489 0.4362 -0.3326 0.086 Uiso 1 1 calc R
H11C H 0.0466 0.3429 -0.2200 0.086 Uiso 1 1 calc R
C12 C 0.0276(2) 0.6146(3) -0.2345(4) 0.0499(9) Uani 1 1 d .
C13 C 0.3480(2) 0.4281(3) 0.2577(4) 0.0456(8) Uani 1 1 d .
C14 C 0.3821(2) 0.4412(3) 0.1228(4) 0.0453(8) Uani 1 1 d .
C15 C 0.4548(2) 0.3030(3) 0.2114(4) 0.0572(10) Uani 1 1 d .
C16 C 0.3617(3) 0.5235(3) 0.0045(5) 0.0614(10) Uani 1 1 d .
H16A H 0.3259 0.4965 -0.0849 0.092 Uiso 1 1 calc R
H16B H 0.4136 0.5490 -0.0267 0.092 Uiso 1 1 calc R
H16C H 0.3323 0.5779 0.0489 0.092 Uiso 1 1 calc R
C17 C 0.5174(3) 0.2171(4) 0.2224(5) 0.0810(14) Uani 1 1 d .
H17A H 0.4871 0.1534 0.2119 0.122 Uiso 1 1 calc R
H17B H 0.5529 0.2193 0.3218 0.122 Uiso 1 1 calc R
H17C H 0.5523 0.2232 0.1406 0.122 Uiso 1 1 calc R
F1 F 0.11138(17) 0.5649(3) 0.4333(4) 0.1182(13) Uani 1 1 d .
F2 F 0.1597(3) 0.6962(2) 0.3356(3) 0.1439(18) Uani 1 1 d .
F3 F 0.2957(2) 0.6944(2) 0.5185(5) 0.1255(13) Uani 1 1 d .
F4 F 0.2238(2) 0.6063(3) 0.6601(3) 0.1246(14) Uani 1 1 d .
F5 F 0.39265(15) 0.5430(2) 0.5415(3) 0.0906(9) Uani 1 1 d .
F6 F 0.2940(2) 0.4388(2) 0.5906(3) 0.0911(9) Uani 1 1 d .
N1 N 0.44281(18) 0.3690(2) 0.0994(4) 0.0533(8) Uani 1 1 d .
N2 N 0.10357(16) 0.46560(19) -0.1146(3) 0.0402(6) Uani 1 1 d .
N3 N -0.0146(3) 0.6551(3) -0.3340(4) 0.0741(11) Uani 1 1 d .
S1 S 0.39180(7) 0.32200(8) 0.35575(11) 0.0612(4) Uani 1 1 d .
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'
N N 0.0061 0.0033 '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
C5 C1 C6 131.3(3)
C5 C1 C2 109.3(3)
C6 C1 C2 119.4(3)
F2 C2 F1 104.2(4)
F2 C2 C1 114.7(3)
F1 C2 C1 109.9(3)
F2 C2 C3 113.6(4)
F1 C2 C3 107.3(3)
C1 C2 C3 106.9(3)
F4 C3 F3 106.3(4)
F4 C3 C2 115.1(4)
F3 C3 C2 107.1(4)
F4 C3 C4 115.0(4)
F3 C3 C4 108.0(3)
C2 C3 C4 104.9(3)
F5 C4 F6 105.5(3)
F5 C4 C5 113.6(3)
F6 C4 C5 111.3(3)
F5 C4 C3 111.8(3)
F6 C4 C3 109.1(3)
C5 C4 C3 105.5(3)
C1 C5 C13 130.8(3)
C1 C5 C4 110.6(3)
C13 C5 C4 118.6(3)
C9 C6 C7 107.0(3)
C9 C6 C1 127.3(3)
C7 C6 C1 125.8(3)
C8 C7 C6 107.5(3)
C8 C7 H7 126.2
C6 C7 H7 126.2
C7 C8 N2 108.3(3)
C7 C8 C12 129.6(3)
N2 C8 C12 122.1(3)
N2 C9 C6 107.8(3)
N2 C9 C10 121.1(3)
C6 C9 C10 130.8(3)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N3 C12 C8 178.6(4)
C14 C13 C5 129.8(3)
C14 C13 S1 110.1(3)
C5 C13 S1 120.0(3)
C13 C14 N1 113.9(3)
C13 C14 C16 127.2(3)
N1 C14 C16 118.9(3)
N1 C15 C17 125.4(4)
N1 C15 S1 114.1(3)
C17 C15 S1 120.5(3)
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 N1 C14 112.3(3)
C9 N2 C8 109.3(3)
C9 N2 C11 125.9(3)
C8 N2 C11 124.7(3)
C15 S1 C13 89.59(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.361(5)
C1 C6 1.450(5)
C1 C2 1.503(5)
C2 F2 1.300(5)
C2 F1 1.369(5)
C2 C3 1.501(6)
C3 F4 1.306(5)
C3 F3 1.351(5)
C3 C4 1.512(5)
C4 F5 1.344(4)
C4 F6 1.367(4)
C4 C5 1.498(5)
C5 C13 1.458(5)
C6 C9 1.395(4)
C6 C7 1.408(4)
C7 C8 1.364(5)
C7 H7 0.9300
C8 N2 1.377(4)
C8 C12 1.420(5)
C9 N2 1.353(4)
C9 C10 1.493(5)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 N2 1.464(4)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 N3 1.144(5)
C13 C14 1.364(5)
C13 S1 1.724(3)
C14 N1 1.382(4)
C14 C16 1.492(5)
C15 N1 1.293(5)
C15 C17 1.494(5)
C15 S1 1.721(4)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C5 C1 C2 F2 132.5(4)
C6 C1 C2 F2 -48.5(5)
C5 C1 C2 F1 -110.5(4)
C6 C1 C2 F1 68.5(4)
C5 C1 C2 C3 5.6(4)
C6 C1 C2 C3 -175.4(3)
F2 C2 C3 F4 91.1(5)
F1 C2 C3 F4 -23.5(5)
C1 C2 C3 F4 -141.3(4)
F2 C2 C3 F3 -26.7(5)
F1 C2 C3 F3 -141.3(3)
C1 C2 C3 F3 100.8(4)
F2 C2 C3 C4 -141.4(4)
F1 C2 C3 C4 104.0(4)
C1 C2 C3 C4 -13.8(4)
F4 C3 C4 F5 -91.9(4)
F3 C3 C4 F5 26.6(4)
C2 C3 C4 F5 140.5(3)
F4 C3 C4 F6 24.5(5)
F3 C3 C4 F6 143.0(3)
C2 C3 C4 F6 -103.1(4)
F4 C3 C4 C5 144.1(4)
F3 C3 C4 C5 -97.4(4)
C2 C3 C4 C5 16.6(4)
C6 C1 C5 C13 7.0(6)
C2 C1 C5 C13 -174.2(4)
C6 C1 C5 C4 -173.6(3)
C2 C1 C5 C4 5.3(4)
F5 C4 C5 C1 -136.8(3)
F6 C4 C5 C1 104.2(3)
C3 C4 C5 C1 -14.0(4)
F5 C4 C5 C13 42.7(5)
F6 C4 C5 C13 -76.2(4)
C3 C4 C5 C13 165.5(3)
C5 C1 C6 C9 33.7(6)
C2 C1 C6 C9 -145.0(4)
C5 C1 C6 C7 -145.5(4)
C2 C1 C6 C7 35.7(5)
C9 C6 C7 C8 -0.6(4)
C1 C6 C7 C8 178.8(3)
C6 C7 C8 N2 0.4(4)
C6 C7 C8 C12 -179.0(3)
C7 C6 C9 N2 0.6(4)
C1 C6 C9 N2 -178.8(3)
C7 C6 C9 C10 -173.5(3)
C1 C6 C9 C10 7.1(6)
C7 C8 C12 N3 7(18)
N2 C8 C12 N3 -172(100)
C1 C5 C13 C14 48.2(6)
C4 C5 C13 C14 -131.2(4)
C1 C5 C13 S1 -137.4(3)
C4 C5 C13 S1 43.2(4)
C5 C13 C14 N1 173.8(3)
S1 C13 C14 N1 -1.0(4)
C5 C13 C14 C16 -5.3(6)
S1 C13 C14 C16 180.0(3)
C17 C15 N1 C14 -178.6(4)
S1 C15 N1 C14 0.8(4)
C13 C14 N1 C15 0.1(4)
C16 C14 N1 C15 179.3(3)
C6 C9 N2 C8 -0.3(4)
C10 C9 N2 C8 174.4(3)
C6 C9 N2 C11 176.3(3)
C10 C9 N2 C11 -9.0(5)
C7 C8 N2 C9 0.0(4)
C12 C8 N2 C9 179.4(3)
C7 C8 N2 C11 -176.7(3)
C12 C8 N2 C11 2.7(5)
N1 C15 S1 C13 -1.1(3)
C17 C15 S1 C13 178.2(3)
C14 C13 S1 C15 1.1(3)
C5 C13 S1 C15 -174.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30652131 ChemSpider
