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#$Date: 2016-03-05 12:35:44 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177895 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/51/7055190.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_7055190
loop_
_publ_author_name
'Mamada, Masashi'
'Fujita, Harunori'
'Kakita, Kazuaki'
'Shima, Hidetaka'
'Yoneda, Yasuhiro'
'Tanaka, Yasuhiro'
'Tokito, Shizuo'
_publ_section_title
;
 Crystal structure and modeled charge carrier mobility of
 benzobis(thiadiazole) derivatives
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              1403
_journal_paper_doi               10.1039/C5NJ02302E
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C28 H12 F6 N4 S4'
_chemical_formula_sum            'C28 H12 F6 N4 S4'
_chemical_formula_weight         646.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-10-16 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                93.915(15)
_cell_angle_beta                 97.142(13)
_cell_angle_gamma                102.709(14)
_cell_formula_units_Z            1
_cell_length_a                   5.0599(8)
_cell_length_b                   6.4683(13)
_cell_length_c                   20.014(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      25.8
_cell_volume                     630.93(19)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5134
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.989
_diffrn_reflns_theta_min         2.236
_diffrn_standards_decay_%        -0.97
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.134
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1029P)²+1.0937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.1872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1877
_reflns_number_total             2285
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj02302e2.cif
_cod_data_source_block           2-mCF3
_cod_depositor_comments
'Adding full bibliography for 7055189--7055194.cif.'
_cod_database_code               7055190
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.232
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.8264(2) 0.12469(16) 0.06330(5) 0.0444(3) Uani 1 1 d . .
S2 S 0.1497(2) 0.77357(16) 0.15098(5) 0.0424(3) Uani 1 1 d . .
F1 F -0.4560(18) 0.5397(10) 0.4268(3) 0.201(4) Uani 1 1 d . .
F2 F -0.1048(13) 0.6853(16) 0.4787(3) 0.202(4) Uani 1 1 d . .
F3 F -0.4241(19) 0.8182(12) 0.4781(3) 0.211(4) Uani 1 1 d . .
N1 N 0.6595(7) 0.2681(5) 0.10059(17) 0.0417(8) Uani 1 1 d . .
N2 N 0.8017(7) 0.2002(5) -0.01129(17) 0.0411(8) Uani 1 1 d . .
C1 C 0.5696(7) 0.3911(6) 0.05430(19) 0.0355(8) Uani 1 1 d . .
C2 C 0.6518(8) 0.3511(6) -0.01105(19) 0.0357(8) Uani 1 1 d . .
C3 C 0.4139(7) 0.5424(6) 0.06834(18) 0.0345(8) Uani 1 1 d . .
C4 C 0.3312(8) 0.5811(6) 0.1339(2) 0.0387(8) Uani 1 1 d . .
C5 C 0.3684(10) 0.4739(8) 0.1903(2) 0.0487(10) Uani 1 1 d . .
H5 H 0.4610 0.3646 0.1918 0.058 Uiso 1 1 calc R U
C6 C 0.2536(10) 0.5452(7) 0.2451(2) 0.0494(11) Uani 1 1 d . .
H6 H 0.2629 0.4875 0.2864 0.059 Uiso 1 1 calc R U
C7 C 0.1271(8) 0.7066(7) 0.2324(2) 0.0406(9) Uani 1 1 d . .
C8 C -0.0185(9) 0.8155(7) 0.2777(2) 0.0426(9) Uani 1 1 d . .
C9 C -0.0787(9) 0.7331(7) 0.3379(2) 0.0466(10) Uani 1 1 d . .
H9 H -0.0205 0.6122 0.3499 0.056 Uiso 1 1 calc R U
C10 C -0.2235(10) 0.8280(8) 0.3800(2) 0.0515(11) Uani 1 1 d . .
C11 C -0.3090(11) 1.0101(8) 0.3640(2) 0.0573(12) Uani 1 1 d . .
H11 H -0.4052 1.0747 0.3926 0.069 Uiso 1 1 calc R U
C12 C -0.2481(12) 1.0930(8) 0.3047(3) 0.0607(13) Uani 1 1 d . .
H12 H -0.3035 1.2155 0.2934 0.073 Uiso 1 1 calc R U
C13 C -0.1065(10) 0.9982(7) 0.2618(2) 0.0532(11) Uani 1 1 d . .
H13 H -0.0694 1.0566 0.2218 0.064 Uiso 1 1 calc R U
C14 C -0.2980(13) 0.7259(10) 0.4416(3) 0.0668(14) 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 S1 N2 101.64(17) . .
C7 S2 C4 92.49(19) . .
C1 N1 S1 107.0(3) . .
C2 N2 S1 106.8(3) . .
N1 C1 C3 124.1(4) . .
N1 C1 C2 112.3(3) . .
C3 C1 C2 123.5(3) . .
N2 C2 C3 123.8(4) . 2_665
N2 C2 C1 112.2(3) . .
C3 C2 C1 124.1(4) 2_665 .
C2 C3 C1 112.4(3) 2_665 .
C2 C3 C4 124.3(4) 2_665 .
C1 C3 C4 123.3(4) . .
C5 C4 C3 127.8(4) . .
C5 C4 S2 109.4(3) . .
C3 C4 S2 122.7(3) . .
C4 C5 C6 113.6(4) . .
C4 C5 H5 123.2 . .
C6 C5 H5 123.2 . .
C7 C6 C5 113.9(4) . .
C7 C6 H6 123.1 . .
C5 C6 H6 123.1 . .
C6 C7 C8 128.2(4) . .
C6 C7 S2 110.6(3) . .
C8 C7 S2 121.2(3) . .
C9 C8 C13 117.9(4) . .
C9 C8 C7 119.9(4) . .
C13 C8 C7 122.2(4) . .
C10 C9 C8 121.0(4) . .
C10 C9 H9 119.5 . .
C8 C9 H9 119.5 . .
C9 C10 C11 120.8(4) . .
C9 C10 C14 118.9(4) . .
C11 C10 C14 120.2(4) . .
C12 C11 C10 118.3(4) . .
C12 C11 H11 120.8 . .
C10 C11 H11 120.8 . .
C11 C12 C13 121.4(5) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C12 C13 C8 120.6(4) . .
C12 C13 H13 119.7 . .
C8 C13 H13 119.7 . .
F3 C14 F2 107.2(7) . .
F3 C14 F1 103.4(7) . .
F2 C14 F1 101.1(7) . .
F3 C14 C10 116.5(5) . .
F2 C14 C10 115.1(5) . .
F1 C14 C10 111.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N1 1.593(3) .
S1 N2 1.601(3) .
S2 C7 1.725(4) .
S2 C4 1.741(4) .
F1 C14 1.283(8) .
F2 C14 1.239(7) .
F3 C14 1.233(7) .
N1 C1 1.361(5) .
N2 C2 1.362(5) .
C1 C3 1.419(5) .
C1 C2 1.445(5) .
C2 C3 1.419(5) 2_665
C3 C2 1.419(5) 2_665
C3 C4 1.448(5) .
C4 C5 1.380(6) .
C5 C6 1.400(6) .
C5 H5 0.9300 .
C6 C7 1.362(6) .
C6 H6 0.9300 .
C7 C8 1.473(6) .
C8 C9 1.391(6) .
C8 C13 1.394(6) .
C9 C10 1.381(6) .
C9 H9 0.9300 .
C10 C11 1.385(7) .
C10 C14 1.488(7) .
C11 C12 1.377(7) .
C11 H11 0.9300 .
C12 C13 1.379(7) .
C12 H12 0.9300 .
C13 H13 0.9300 .
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
N2 S1 N1 C1 -0.1(3) . .
N1 S1 N2 C2 -0.1(3) . .
S1 N1 C1 C3 -179.5(3) . .
S1 N1 C1 C2 0.2(4) . .
S1 N2 C2 C3 179.8(3) . 2_665
S1 N2 C2 C1 0.2(4) . .
N1 C1 C2 N2 -0.3(5) . .
C3 C1 C2 N2 179.4(3) . .
N1 C1 C2 C3 -179.9(4) . 2_665
C3 C1 C2 C3 -0.2(7) . 2_665
N1 C1 C3 C2 179.8(4) . 2_665
C2 C1 C3 C2 0.2(6) . 2_665
N1 C1 C3 C4 -0.6(6) . .
C2 C1 C3 C4 179.7(4) . .
C2 C3 C4 C5 174.6(4) 2_665 .
C1 C3 C4 C5 -4.9(7) . .
C2 C3 C4 S2 -2.6(6) 2_665 .
C1 C3 C4 S2 177.8(3) . .
C7 S2 C4 C5 -0.1(3) . .
C7 S2 C4 C3 177.6(3) . .
C3 C4 C5 C6 -177.4(4) . .
S2 C4 C5 C6 0.1(5) . .
C4 C5 C6 C7 0.0(6) . .
C5 C6 C7 C8 178.7(4) . .
C5 C6 C7 S2 -0.1(5) . .
C4 S2 C7 C6 0.1(4) . .
C4 S2 C7 C8 -178.7(4) . .
C6 C7 C8 C9 -10.8(7) . .
S2 C7 C8 C9 167.9(3) . .
C6 C7 C8 C13 170.9(5) . .
S2 C7 C8 C13 -10.4(6) . .
C13 C8 C9 C10 0.7(7) . .
C7 C8 C9 C10 -177.7(4) . .
C8 C9 C10 C11 -1.0(7) . .
C8 C9 C10 C14 176.2(5) . .
C9 C10 C11 C12 0.5(8) . .
C14 C10 C11 C12 -176.6(5) . .
C10 C11 C12 C13 0.3(8) . .
C11 C12 C13 C8 -0.6(8) . .
C9 C8 C13 C12 0.1(7) . .
C7 C8 C13 C12 178.4(5) . .
C9 C10 C14 F3 179.1(7) . .
C11 C10 C14 F3 -3.7(10) . .
C9 C10 C14 F2 52.4(9) . .
C11 C10 C14 F2 -130.4(7) . .
C9 C10 C14 F1 -62.2(8) . .
C11 C10 C14 F1 115.0(7) . .
