#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180166 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/62/7106201.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_7106201
loop_
_publ_author_name
'Masakazu Morimoto'
'Masahiro Irie'
_publ_section_title
;
 Photochemical control of dielectric properties based on intermolecular
 proton transfer in a hydrogen-bonded diarylethene crystal
;
_journal_name_full               Chem.Commun.
_journal_page_first              4186
_journal_paper_doi               10.1039/c0cc05729k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C33 H26 F6 N4 S2'
_chemical_formula_weight         656.70
_chemical_name_systematic
;
?
;
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0788(12)
_cell_length_b                   29.771(3)
_cell_length_c                   9.3271(10)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.74
_cell_volume                     3076.3(6)
_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      93(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22712
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0.2
_diffrn_standards_number         184
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.8893
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS; Scheldrick 1996
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0849P)²+3.2241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                2784
_reflns_number_total             3036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05729k.txt
_cod_data_source_block           1o-UV
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      Pnna
_cod_database_code               7106201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.7946(2) 0.05131(8) 0.2745(3) 0.0303(5) Uani 1 1 d . . .
C3 C 0.8981(2) 0.07968(7) 0.2670(3) 0.0297(5) Uani 1 1 d . C .
H3 H 0.9579 0.0808 0.3400 0.036 Uiso 1 1 calc R . .
C4 C 0.9032(2) 0.10503(8) 0.1456(3) 0.0322(6) Uani 1 1 d . . .
C5 C 0.7712(2) 0.02140(8) 0.3945(3) 0.0323(6) Uani 1 1 d . . .
C7 C 0.7500 0.0000 0.6436(4) 0.0429(9) Uani 1 2 d S . .
C8 C 0.5997(2) 0.03602(10) 0.1252(4) 0.0451(7) Uani 1 1 d . . .
H8A H 0.6116 0.0096 0.0641 0.068 Uiso 1 1 calc R A 3
H8B H 0.5481 0.0578 0.0756 0.068 Uiso 1 1 calc R A 3
H8C H 0.5611 0.0269 0.2151 0.068 Uiso 1 1 calc R A 3
C9 C 0.9922(2) 0.13917(8) 0.1057(3) 0.0339(6) Uani 1 1 d . C .
C10 C 1.0803(3) 0.15235(9) 0.2029(3) 0.0418(7) Uani 1 1 d . . .
H10 H 1.0854 0.1379 0.2935 0.050 Uiso 1 1 calc R C .
C11 C 1.1604(3) 0.18624(10) 0.1694(4) 0.0487(8) Uani 1 1 d . C .
H11 H 1.2196 0.1947 0.2379 0.058 Uiso 1 1 calc R . .
C12 C 1.1568(3) 0.20788(9) 0.0402(4) 0.0477(8) Uani 1 1 d . . .
C13 C 1.0705(3) 0.19491(12) -0.0567(4) 0.0617(10) Uani 1 1 d . C .
H13 H 1.0662 0.2096 -0.1470 0.074 Uiso 1 1 calc R . .
C14 C 0.9892(3) 0.16069(11) -0.0258(4) 0.0519(8) Uani 1 1 d . . .
H14 H 0.9311 0.1520 -0.0954 0.062 Uiso 1 1 calc R C .
C15 C 1.2413(3) 0.24569(11) 0.0091(5) 0.0687(12) Uani 1 1 d . C .
C16 C 1.3874(4) 0.29693(13) 0.0319(7) 0.0914(18) Uani 1 1 d . C .
H16A H 1.3690 0.3245 0.0873 0.110 Uiso 1 1 calc R . .
H16B H 1.4761 0.2929 0.0281 0.110 Uiso 1 1 calc R . .
C6A C 0.7759(7) 0.0407(2) 0.5435(7) 0.0346(16) Uiso 0.50 1 d P B 1
F1A F 0.6880(5) 0.07192(13) 0.5686(4) 0.0573(10) Uani 0.50 1 d P B 1
F2A F 0.8798(5) 0.05996(17) 0.5786(4) 0.0565(11) Uani 0.50 1 d P B 1
C6B C 0.8106(8) 0.0339(3) 0.5466(8) 0.044(2) Uiso 0.50 1 d P B 2
F1B F 0.7735(6) 0.07757(13) 0.5744(5) 0.0627(12) Uani 0.50 1 d P B 2
F2B F 0.9309(4) 0.03414(18) 0.5632(4) 0.0586(11) Uani 0.50 1 d P B 2
C17 C 1.3365(6) 0.29955(19) -0.1123(8) 0.126(2) Uani 1 1 d . C .
H17A H 1.3961 0.2895 -0.1846 0.151 Uiso 1 1 calc R . .
H17B H 1.3121 0.3307 -0.1350 0.151 Uiso 1 1 calc R . .
F3 F 0.6443(4) 0.01768(19) 0.6909(5) 0.0594(12) Uani 0.50 1 d P . .
F4 F 0.8178(5) -0.00944(19) 0.7566(5) 0.0618(13) Uani 0.50 1 d P . .
N1 N 1.3286(3) 0.25746(10) 0.0965(6) 0.0764(12) Uani 1 1 d . . .
N2 N 1.2305(4) 0.26951(13) -0.1110(6) 0.0905(14) Uani 1 1 d . . .
C1A C 0.7187(2) 0.05702(9) 0.1570(3) 0.0299(6) Uani 0.913(3) 1 d P C 3
S1A S 0.77694(6) 0.09606(2) 0.04008(8) 0.0346(3) Uani 0.913(3) 1 d P C 3
C1B C 0.754(4) 0.0284(14) 0.184(4) 0.050(9) Uiso 0.087(3) 1 d P . 4
S1B S 0.8355(11) 0.0533(4) 0.0399(13) 0.068(4) Uiso 0.087(3) 1 d P C 4
H52 H 1.246(7) 0.247(3) -0.177(7) 0.07(3) Uiso 0.50 1 d P . .
H51 H 1.321(8) 0.249(4) 0.181(8) 0.08(3) Uiso 0.50 1 d P . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1B C2 C3 128.3(18) . . ?
C1A C2 C3 112.0(2) . . ?
C1B C2 C5 97.4(19) . . ?
C1A C2 C5 125.0(2) . . ?
C3 C2 C5 122.9(2) . . ?
C4 C3 C2 113.7(2) . . ?
C4 C3 H3 123.1 . . ?
C2 C3 H3 123.1 . . ?
C3 C4 C9 128.6(2) . . ?
C3 C4 S1A 110.69(18) . . ?
C9 C4 S1A 120.4(2) . . ?
C3 C4 S1B 88.1(4) . . ?
C9 C4 S1B 132.1(4) . . ?
C5 C5 C2 129.53(14) 2_655 . ?
C5 C5 C6A 111.8(3) 2_655 . ?
C2 C5 C6A 118.1(3) . . ?
C5 C5 C6B 109.0(3) 2_655 . ?
C2 C5 C6B 121.0(3) . . ?
F4 C7 F4 74.5(6) 2_655 . ?
F4 C7 F3 108.2(5) 2_655 2_655 ?
F4 C7 F3 108.2(5) . . ?
F3 C7 F3 142.1(6) 2_655 . ?
F4 C7 C6B 125.9(4) 2_655 . ?
F4 C7 C6B 111.4(4) . . ?
F3 C7 C6B 94.0(4) 2_655 . ?
F3 C7 C6B 108.6(4) . . ?
F4 C7 C6B 111.4(4) 2_655 2_655 ?
F4 C7 C6B 125.9(4) . 2_655 ?
F3 C7 C6B 108.6(4) 2_655 2_655 ?
F3 C7 C6B 94.0(4) . 2_655 ?
C6B C7 C6B 106.5(6) . 2_655 ?
F4 C7 C6A 114.6(4) 2_655 . ?
F4 C7 C6A 122.5(3) . . ?
F3 C7 C6A 109.7(4) 2_655 . ?
F3 C7 C6A 93.0(4) . . ?
C6B C7 C6A 104.0(3) 2_655 . ?
F4 C7 C6A 122.5(3) 2_655 2_655 ?
F4 C7 C6A 114.6(4) . 2_655 ?
F3 C7 C6A 93.0(4) 2_655 2_655 ?
F3 C7 C6A 109.7(4) . 2_655 ?
C6B C7 C6A 104.0(3) . 2_655 ?
C6A C7 C6A 106.3(5) . 2_655 ?
C14 C9 C10 117.7(2) . . ?
C14 C9 C4 122.0(3) . . ?
C10 C9 C4 120.2(2) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 C15 120.5(3) . . ?
C13 C12 C15 121.5(3) . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 120.5(3) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N1 C15 N2 116.5(4) . . ?
N1 C15 C12 122.9(4) . . ?
N2 C15 C12 120.5(4) . . ?
C17 C16 N1 104.4(4) . . ?
C17 C16 H16A 110.9 . . ?
N1 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
N1 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
F2A C6A F1A 106.4(6) . . ?
F2A C6A C5 115.0(5) . . ?
F1A C6A C5 113.2(5) . . ?
F2A C6A C7 110.4(5) . . ?
F1A C6A C7 107.1(5) . . ?
C5 C6A C7 104.5(4) . . ?
F2B C6B F1B 105.5(6) . . ?
F2B C6B C7 112.1(6) . . ?
F1B C6B C7 112.4(6) . . ?
F2B C6B C5 113.1(6) . . ?
F1B C6B C5 108.4(6) . . ?
C7 C6B C5 105.4(5) . . ?
C16 C17 N2 105.5(4) . . ?
C16 C17 H17A 110.6 . . ?
N2 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
N2 C17 H17B 110.6 . . ?
H17A C17 H17B 108.8 . . ?
F4 F3 C7 70.8(7) 2_655 . ?
F3 F4 C7 75.3(6) 2_655 . ?
F3 F4 F4 127.7(6) 2_655 2_655 ?
C7 F4 F4 52.7(3) . 2_655 ?
C15 N1 C16 106.6(4) . . ?
C15 N1 H51 116(7) . . ?
C16 N1 H51 132(7) . . ?
C15 N2 C17 105.0(5) . . ?
C15 N2 H52 99(5) . . ?
C17 N2 H52 107(5) . . ?
C2 C1A C8 129.8(2) . . ?
C2 C1A S1A 110.84(18) . . ?
C8 C1A S1A 119.3(2) . . ?
C1A S1A C4 92.69(13) . . ?
C2 C1B C1B 127(3) . 2_655 ?
C2 C1B S1B 96(2) . . ?
C1B C1B S1B 116(2) 2_655 . ?
C1B S1B C4 98.1(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
C2 C1B 1.18(4) . ?
C2 C1A 1.391(4) . ?
C2 C3 1.426(3) . ?
C2 C5 1.453(4) . ?
C3 C4 1.362(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.464(3) . ?
C4 S1A 1.731(3) . ?
C4 S1B 1.977(12) . ?
C5 C5 1.358(5) 2_655 ?
C5 C6A 1.505(7) . ?
C5 C6B 1.531(8) . ?
C7 F4 1.325(6) 2_655 ?
C7 F4 1.325(6) . ?
C7 F3 1.357(5) 2_655 ?
C7 F3 1.357(5) . ?
C7 C6B 1.512(8) . ?
C7 C6B 1.512(8) 2_655 ?
C7 C6A 1.557(7) . ?
C7 C6A 1.557(7) 2_655 ?
C8 C1A 1.489(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.384(4) . ?
C9 C10 1.389(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(5) . ?
C12 C15 1.492(4) . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N1 1.312(6) . ?
C15 N2 1.331(6) . ?
C16 C17 1.461(8) . ?
C16 N1 1.472(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6A F2A 1.326(8) . ?
C6A F1A 1.366(9) . ?
C6B F2B 1.341(10) . ?
C6B F1B 1.389(9) . ?
C17 N2 1.476(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
F3 F4 0.782(5) 2_655 ?
F4 F3 0.782(5) 2_655 ?
F4 F4 1.604(12) 2_655 ?
N1 H51 0.83(7) . ?
N2 H52 0.92(8) . ?
C1A S1A 1.719(3) . ?
C1B C1B 1.69(8) 2_655 ?
C1B S1B 1.78(4) . ?
