#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180166 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/62/7106200.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_7106200
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                   11.0597(8)
_cell_length_b                   29.913(2)
_cell_length_c                   9.2876(7)
_cell_measurement_reflns_used    8404
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.30
_cell_volume                     3072.6(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      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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23470
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.36
_diffrn_standards_decay_%        0.7
_diffrn_standards_number         237
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS; Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_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         0.647
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0576
_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)+(0.0785P)²+2.6229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                2959
_reflns_number_total             3136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05729k.txt
_cod_data_source_block           1o
_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               7106200
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
C1 C 0.71840(18) 0.05681(7) 0.1571(2) 0.0281(4) Uani 1 1 d . . .
C2 C 0.79406(17) 0.05141(6) 0.2733(2) 0.0242(4) Uani 1 1 d . A .
C3 C 0.89848(18) 0.07941(6) 0.2661(2) 0.0254(4) Uani 1 1 d . . .
H3 H 0.9591 0.0799 0.3385 0.030 Uiso 1 1 calc R . .
C4 C 0.90286(18) 0.10528(6) 0.1456(2) 0.0264(4) Uani 1 1 d . . .
C5 C 0.77096(18) 0.02130(7) 0.3943(2) 0.0260(4) Uani 1 1 d . . .
C7 C 0.7500 0.0000 0.6441(3) 0.0355(7) Uani 1 2 d S . .
C8 C 0.59903(19) 0.03568(8) 0.1243(3) 0.0361(5) Uani 1 1 d . . .
H8A H 0.6115 0.0093 0.0637 0.054 Uiso 1 1 calc R . .
H8B H 0.5476 0.0572 0.0734 0.054 Uiso 1 1 calc R . .
H8C H 0.5597 0.0267 0.2144 0.054 Uiso 1 1 calc R . .
C9 C 0.99202(18) 0.13925(6) 0.1054(2) 0.0293(5) Uani 1 1 d . . .
C10 C 1.0800(2) 0.15261(7) 0.2039(3) 0.0358(5) Uani 1 1 d . . .
H10 H 1.0847 0.1383 0.2951 0.043 Uiso 1 1 calc R . .
C11 C 1.1603(2) 0.18640(8) 0.1704(3) 0.0421(6) Uani 1 1 d . . .
H11 H 1.2193 0.1950 0.2394 0.051 Uiso 1 1 calc R . .
C12 C 1.1569(2) 0.20791(7) 0.0395(3) 0.0407(6) Uani 1 1 d . . .
C13 C 1.0709(2) 0.19460(9) -0.0586(3) 0.0508(7) Uani 1 1 d . . .
H13 H 1.0669 0.2091 -0.1495 0.061 Uiso 1 1 calc R . .
C14 C 0.9897(2) 0.16043(8) -0.0275(3) 0.0428(6) Uani 1 1 d . . .
H14 H 0.9322 0.1515 -0.0978 0.051 Uiso 1 1 calc R . .
C15 C 1.2411(3) 0.24546(9) 0.0085(4) 0.0592(9) Uani 1 1 d . . .
C16 C 1.3887(3) 0.29638(10) 0.0313(5) 0.0780(13) Uani 1 1 d . . .
H16A H 1.4774 0.2922 0.0266 0.094 Uiso 1 1 calc R . .
H16B H 1.3708 0.3237 0.0877 0.094 Uiso 1 1 calc R . .
C6A C 0.7746(6) 0.04068(19) 0.5448(5) 0.0294(13) Uiso 0.50 1 d P A 1
F1A F 0.6883(4) 0.07181(11) 0.5691(3) 0.0484(8) Uani 0.50 1 d P A 1
F2A F 0.8806(4) 0.05931(13) 0.5781(3) 0.0480(8) Uani 0.50 1 d P A 1
C6B C 0.8093(6) 0.03429(19) 0.5452(6) 0.0327(14) Uiso 0.50 1 d P A 2
F1B F 0.7732(4) 0.07702(10) 0.5748(3) 0.0511(9) Uani 0.50 1 d P A 2
F2B F 0.9313(3) 0.03413(15) 0.5633(3) 0.0491(8) Uani 0.50 1 d P A 2
C17 C 1.3359(5) 0.29920(15) -0.1146(6) 0.1088(17) Uani 1 1 d . . .
H17A H 1.3118 0.3303 -0.1372 0.131 Uiso 1 1 calc R . .
H17B H 1.3946 0.2889 -0.1879 0.131 Uiso 1 1 calc R . .
F3 F 0.6442(3) 0.01710(14) 0.6929(4) 0.0495(9) Uani 0.50 1 d P . .
F4 F 0.8184(4) -0.00939(14) 0.7586(4) 0.0514(10) Uani 0.50 1 d P . .
N1 N 1.3292(2) 0.25697(8) 0.0947(5) 0.0652(10) Uani 1 1 d . . .
N2 N 1.2293(3) 0.26963(10) -0.1107(4) 0.0762(10) Uani 1 1 d . . .
S1 S 0.77635(5) 0.095798(18) 0.03991(6) 0.0321(2) Uani 1 1 d . . .
H52 H 1.241(5) 0.251(2) -0.181(6) 0.044(18) Uiso 0.50 1 d P . .
H51 H 1.328(8) 0.257(3) 0.174(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
C2 C1 C8 130.36(19) . . ?
C2 C1 S1 110.47(15) . . ?
C8 C1 S1 119.13(16) . . ?
C1 C2 C3 112.73(18) . . ?
C1 C2 C5 124.68(18) . . ?
C3 C2 C5 122.58(18) . . ?
C4 C3 C2 113.61(19) . . ?
C4 C3 H3 123.2 . . ?
C2 C3 H3 123.2 . . ?
C3 C4 C9 128.9(2) . . ?
C3 C4 S1 110.12(15) . . ?
C9 C4 S1 120.86(16) . . ?
C5 C5 C2 129.68(11) 2_655 . ?
C5 C5 C6A 111.7(2) 2_655 . ?
C2 C5 C6A 118.0(2) . . ?
C5 C5 C6B 109.7(2) 2_655 . ?
C2 C5 C6B 120.3(3) . . ?
F4 C7 F4 74.4(4) 2_655 . ?
F4 C7 F3 107.6(4) . . ?
F4 C7 F3 107.6(4) 2_655 2_655 ?
F3 C7 F3 140.9(4) . 2_655 ?
F4 C7 C6B 125.6(3) 2_655 . ?
F4 C7 C6B 112.2(3) . . ?
F3 C7 C6B 108.6(3) . . ?
F3 C7 C6B 94.8(3) 2_655 . ?
F4 C7 C6B 112.2(3) 2_655 2_655 ?
F4 C7 C6B 125.6(3) . 2_655 ?
F3 C7 C6B 94.8(3) . 2_655 ?
F3 C7 C6B 108.6(3) 2_655 2_655 ?
C6B C7 C6B 105.9(4) . 2_655 ?
F4 C7 C6A 114.1(3) 2_655 . ?
F4 C7 C6A 122.7(3) . . ?
F3 C7 C6A 93.1(3) . . ?
F3 C7 C6A 110.1(3) 2_655 . ?
C6B C7 C6A 104.1(3) 2_655 . ?
F4 C7 C6A 122.7(3) 2_655 2_655 ?
F4 C7 C6A 114.1(3) . 2_655 ?
F3 C7 C6A 110.1(3) . 2_655 ?
F3 C7 C6A 93.1(3) 2_655 2_655 ?
C6B C7 C6A 104.1(3) . 2_655 ?
C6A C7 C6A 107.0(4) . 2_655 ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 117.8(2) . . ?
C14 C9 C4 122.1(2) . . ?
C10 C9 C4 120.1(2) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 118.0(2) . . ?
C13 C12 C15 121.6(3) . . ?
C11 C12 C15 120.4(3) . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 120.5(3) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 N2 116.1(3) . . ?
N1 C15 C12 123.2(3) . . ?
N2 C15 C12 120.7(3) . . ?
N1 C16 C17 103.6(3) . . ?
N1 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
N1 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
F2A C6A F1A 107.1(5) . . ?
F2A C6A C5 113.4(4) . . ?
F1A C6A C5 113.5(4) . . ?
F2A C6A C7 110.1(4) . . ?
F1A C6A C7 108.5(4) . . ?
C5 C6A C7 104.1(3) . . ?
F2B C6B F1B 105.5(5) . . ?
F2B C6B C5 113.0(4) . . ?
F1B C6B C5 110.2(4) . . ?
F2B C6B C7 110.5(4) . . ?
F1B C6B C7 112.4(4) . . ?
C5 C6B C7 105.4(4) . . ?
N2 C17 C16 105.1(3) . . ?
N2 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
N2 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
F4 F3 C7 71.9(5) 2_655 . ?
F3 F4 C7 74.8(4) 2_655 . ?
F3 F4 F4 127.3(5) 2_655 2_655 ?
C7 F4 F4 52.8(2) . 2_655 ?
C15 N1 C16 107.4(4) . . ?
C15 N1 H51 127(7) . . ?
C16 N1 H51 115(7) . . ?
C15 N2 C17 105.5(4) . . ?
C15 N2 H52 106(4) . . ?
C17 N2 H52 104(4) . . ?
C1 S1 C4 93.06(10) . . ?
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
C1 C2 1.375(3) . ?
C1 C8 1.495(3) . ?
C1 S1 1.719(2) . ?
C2 C3 1.428(3) . ?
C2 C5 1.462(3) . ?
C3 C4 1.362(3) . ?
C3 H3 0.9500 . ?
C4 C9 1.464(3) . ?
C4 S1 1.733(2) . ?
C5 C5 1.356(4) 2_655 ?
C5 C6A 1.513(5) . ?
C5 C6B 1.514(6) . ?
C7 F4 1.334(4) 2_655 ?
C7 F4 1.334(4) . ?
C7 F3 1.355(4) . ?
C7 F3 1.355(4) 2_655 ?
C7 C6B 1.525(6) . ?
C7 C6B 1.526(6) 2_655 ?
C7 C6A 1.551(5) . ?
C7 C6A 1.551(5) 2_655 ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.387(3) . ?
C9 C10 1.393(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(4) . ?
C12 C15 1.487(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N1 1.307(5) . ?
C15 N2 1.329(5) . ?
C16 N1 1.473(4) . ?
C16 C17 1.478(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6A F2A 1.334(6) . ?
C6A F1A 1.353(7) . ?
C6B F2B 1.361(8) . ?
C6B F1B 1.367(7) . ?
C17 N2 1.474(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
F3 F4 0.772(4) 2_655 ?
F4 F3 0.772(4) 2_655 ?
F4 F4 1.614(9) 2_655 ?
N1 H51 0.74(7) . ?
N2 H52 0.86(6) . ?
