#------------------------------------------------------------------------------
#$Date: 2016-05-06 03:56:11 +0300 (Fri, 06 May 2016) $
#$Revision: 182653 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/47/7224775.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_7224775
loop_
_publ_author_name
'Huo, Peng'
'Xue, Li-Jun'
'Li, Yan-Hong'
'Chen, Ting'
'Yu, Lei'
'Zhu, Qin-Yu'
'Dai, Jie'
_publ_section_title
;
 Effects of alkyl chain length on film morphologies and photocurrent
 responses of tetrathiafulvalene-bipyridinium charge-transfer salts: a
 study in terms of structures
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2894
_journal_paper_doi               10.1039/C5CE02479J
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H22 N O5 S6'
_chemical_formula_weight         536.77
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-18 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                93.153(6)
_cell_angle_beta                 94.366(6)
_cell_angle_gamma                99.411(7)
_cell_formula_units_Z            2
_cell_length_a                   5.3407(4)
_cell_length_b                   10.8805(9)
_cell_length_c                   20.8512(12)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      3.3
_cell_volume                     1189.07(15)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8192
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.946
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication '
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.059
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0792
_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)+(0.0500P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2979
_reflns_number_total             4200
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce02479j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7224775--7224777.cif.'
_cod_database_code               7224775
_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   0.888
_shelx_estimated_absorpt_t_max   0.970
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 0.2988(3) 0.89553(12) 0.21196(7) 0.0412(4) Uani 1 1 d . .
S2 S 0.3905(3) 0.64358(12) 0.24478(7) 0.0403(4) Uani 1 1 d . .
S3 S -0.0894(3) 0.89572(15) 0.32355(7) 0.0512(4) Uani 1 1 d . .
S4 S -0.0014(3) 0.64400(15) 0.35677(8) 0.0549(4) Uani 1 1 d . .
S5 S -0.4256(5) 0.9159(3) 0.43349(11) 0.0992(9) Uani 1 1 d . .
S6 S -0.3365(4) 0.6358(2) 0.46695(9) 0.0816(7) Uani 1 1 d . .
O1 O 0.5599(8) 1.0149(4) 0.1167(2) 0.0581(12) Uani 1 1 d . .
O2 O 0.7884(8) 0.8744(4) 0.08366(19) 0.0526(10) Uani 1 1 d . .
O3 O 0.8711(7) 0.6708(4) 0.11138(18) 0.0472(10) Uani 1 1 d . .
O4 O 0.7330(7) 0.5296(3) 0.17985(19) 0.0454(9) Uani 1 1 d . .
N1 N 0.2195(9) 0.3047(4) 0.1129(2) 0.0425(11) Uani 1 1 d . .
C1 C 0.5185(10) 0.8297(5) 0.1692(2) 0.0352(11) Uani 1 1 d . .
C2 C 0.5632(9) 0.7141(5) 0.1843(2) 0.0338(11) Uani 1 1 d . .
C3 C 0.2309(10) 0.7697(5) 0.2610(2) 0.0360(12) Uani 1 1 d . .
C4 C 0.0693(11) 0.7697(5) 0.3077(3) 0.0422(13) Uani 1 1 d . .
C5 C -0.2323(14) 0.8332(7) 0.3908(3) 0.0639(19) Uani 1 1 d . .
C6 C -0.1919(14) 0.7192(7) 0.4054(3) 0.0634(19) Uani 1 1 d . .
C7 C -0.399(3) 1.0540(10) 0.4002(7) 0.196(8) Uani 1 1 d . .
H7A H -0.2400 1.1049 0.4161 0.294 Uiso 1 1 calc R U
H7B H -0.5370 1.0953 0.4112 0.294 Uiso 1 1 calc R U
H7C H -0.4048 1.0406 0.3541 0.294 Uiso 1 1 calc R U
C8 C -0.076(2) 0.6522(13) 0.5255(5) 0.138(5) Uani 1 1 d . .
H8A H 0.0611 0.6183 0.5078 0.208 Uiso 1 1 calc R U
H8B H -0.1262 0.6082 0.5623 0.208 Uiso 1 1 calc R U
H8C H -0.0202 0.7391 0.5384 0.208 Uiso 1 1 calc R U
C9 C 0.6316(10) 0.9126(5) 0.1192(3) 0.0399(13) Uani 1 1 d . .
C10 C 0.7331(10) 0.6326(5) 0.1569(3) 0.0378(12) Uani 1 1 d . .
C11 C 0.1478(10) 0.4163(5) 0.1056(3) 0.0415(13) Uani 1 1 d . .
H11 H 0.0254 0.4412 0.1305 0.050 Uiso 1 1 calc R U
C12 C 0.2547(10) 0.4938(5) 0.0616(3) 0.0397(12) Uani 1 1 d . .
H12 H 0.2026 0.5705 0.0567 0.048 Uiso 1 1 calc R U
C13 C 0.4409(10) 0.4590(5) 0.0239(2) 0.0353(12) Uani 1 1 d . .
C14 C 0.5087(10) 0.3421(5) 0.0334(3) 0.0422(13) Uani 1 1 d . .
H14 H 0.6319 0.3150 0.0095 0.051 Uiso 1 1 calc R U
C15 C 0.3961(11) 0.2671(5) 0.0773(3) 0.0453(14) Uani 1 1 d . .
H15 H 0.4424 0.1893 0.0826 0.054 Uiso 1 1 calc R U
C16 C 0.0921(13) 0.2193(6) 0.1597(3) 0.0564(16) Uani 1 1 d . .
H16A H 0.1424 0.1380 0.1539 0.068 Uiso 1 1 calc R U
H16B H -0.0911 0.2087 0.1502 0.068 Uiso 1 1 calc R U
C17 C 0.1589(14) 0.2684(6) 0.2290(3) 0.0640(18) Uani 1 1 d . .
H17A H 0.1114 0.3505 0.2342 0.077 Uiso 1 1 calc R U
H17B H 0.0575 0.2141 0.2561 0.077 Uiso 1 1 calc R U
C18 C 0.4329(15) 0.2782(7) 0.2524(3) 0.072(2) Uani 1 1 d . .
H18A H 0.5357 0.3333 0.2259 0.086 Uiso 1 1 calc R U
H18B H 0.4819 0.1964 0.2475 0.086 Uiso 1 1 calc R U
C19 C 0.488(2) 0.3281(9) 0.3230(4) 0.110(3) Uani 1 1 d . .
H19A H 0.4402 0.4092 0.3280 0.165 Uiso 1 1 calc R U
H19B H 0.6664 0.3342 0.3356 0.165 Uiso 1 1 calc R U
H19C H 0.3916 0.2722 0.3497 0.165 Uiso 1 1 calc R U
O5 O 1.1547(9) 0.8649(4) -0.0110(2) 0.0601(12) 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'
O O 0.0106 0.0060 '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_3
C1 S1 C3 95.2(2) .
C2 S2 C3 95.3(2) .
C4 S3 C5 95.0(3) .
C6 S4 C4 94.9(3) .
C7 S5 C5 104.2(4) .
C6 S6 C8 100.1(4) .
C15 N1 C11 120.7(5) .
C15 N1 C16 120.0(5) .
C11 N1 C16 119.3(5) .
C2 C1 C9 129.4(5) .
C2 C1 S1 117.7(4) .
C9 C1 S1 112.9(4) .
C1 C2 C10 131.1(5) .
C1 C2 S2 116.7(4) .
C10 C2 S2 112.2(4) .
C4 C3 S2 122.3(4) .
C4 C3 S1 122.7(4) .
S2 C3 S1 115.0(3) .
C3 C4 S3 122.1(4) .
C3 C4 S4 123.1(4) .
S3 C4 S4 114.8(3) .
C6 C5 S5 122.5(5) .
C6 C5 S3 117.1(5) .
S5 C5 S3 120.3(4) .
C5 C6 S4 117.9(5) .
C5 C6 S6 124.0(5) .
S4 C6 S6 117.9(4) .
S5 C7 H7A 109.5 .
S5 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
S5 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
S6 C8 H8A 109.5 .
S6 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
S6 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
O1 C9 O2 124.9(5) .
O1 C9 C1 115.8(5) .
O2 C9 C1 119.3(5) .
O4 C10 O3 123.4(5) .
O4 C10 C2 117.0(5) .
O3 C10 C2 119.6(5) .
N1 C11 C12 120.3(5) .
N1 C11 H11 119.9 .
C12 C11 H11 119.9 .
C11 C12 C13 121.0(5) .
C11 C12 H12 119.5 .
C13 C12 H12 119.5 .
C14 C13 C12 116.4(5) .
C14 C13 C13 121.6(6) 2_665
C12 C13 C13 121.9(6) 2_665
C15 C14 C13 120.8(5) .
C15 C14 H14 119.6 .
C13 C14 H14 119.6 .
N1 C15 C14 120.7(5) .
N1 C15 H15 119.6 .
C14 C15 H15 119.6 .
N1 C16 C17 112.8(5) .
N1 C16 H16A 109.0 .
C17 C16 H16A 109.0 .
N1 C16 H16B 109.0 .
C17 C16 H16B 109.0 .
H16A C16 H16B 107.8 .
C18 C17 C16 115.1(6) .
C18 C17 H17A 108.5 .
C16 C17 H17A 108.5 .
C18 C17 H17B 108.5 .
C16 C17 H17B 108.5 .
H17A C17 H17B 107.5 .
C17 C18 C19 112.5(7) .
C17 C18 H18A 109.1 .
C19 C18 H18A 109.1 .
C17 C18 H18B 109.1 .
C19 C18 H18B 109.1 .
H18A C18 H18B 107.8 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.746(5) .
S1 C3 1.761(5) .
S2 C2 1.756(5) .
S2 C3 1.760(5) .
S3 C4 1.755(6) .
S3 C5 1.764(6) .
S4 C6 1.753(7) .
S4 C4 1.761(6) .
S5 C7 1.679(11) .
S5 C5 1.738(7) .
S6 C6 1.765(6) .
S6 C8 1.760(10) .
O1 C9 1.237(6) .
O2 C9 1.265(7) .
O3 C10 1.291(6) .
O4 C10 1.243(6) .
N1 C15 1.344(7) .
N1 C11 1.345(7) .
N1 C16 1.508(7) .
C1 C2 1.367(7) .
C1 C9 1.511(7) .
C2 C10 1.490(7) .
C3 C4 1.350(7) .
C5 C6 1.341(9) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C11 C12 1.373(7) .
C11 H11 0.9300 .
C12 C13 1.399(7) .
C12 H12 0.9300 .
C13 C14 1.398(7) .
C13 C13 1.483(10) 2_665
C14 C15 1.368(8) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.507(9) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.491(10) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.532(11) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C3 S1 C1 C2 0.7(5) . .
C3 S1 C1 C9 -179.6(4) . .
C9 C1 C2 C10 -0.5(10) . .
S1 C1 C2 C10 179.1(4) . .
C9 C1 C2 S2 -178.8(4) . .
S1 C1 C2 S2 0.7(6) . .
C3 S2 C2 C1 -1.8(5) . .
C3 S2 C2 C10 179.6(4) . .
C2 S2 C3 C4 -177.6(5) . .
C2 S2 C3 S1 2.2(3) . .
C1 S1 C3 C4 177.9(5) . .
C1 S1 C3 S2 -1.9(3) . .
S2 C3 C4 S3 -180.0(3) . .
S1 C3 C4 S3 0.3(7) . .
S2 C3 C4 S4 -0.6(7) . .
S1 C3 C4 S4 179.7(3) . .
C5 S3 C4 C3 -175.6(5) . .
C5 S3 C4 S4 4.9(4) . .
C6 S4 C4 C3 175.7(5) . .
C6 S4 C4 S3 -4.8(4) . .
C7 S5 C5 C6 176.5(9) . .
C7 S5 C5 S3 -6.0(8) . .
C4 S3 C5 C6 -3.1(7) . .
C4 S3 C5 S5 179.2(5) . .
S5 C5 C6 S4 177.9(4) . .
S3 C5 C6 S4 0.2(9) . .
S5 C5 C6 S6 2.5(10) . .
S3 C5 C6 S6 -175.1(4) . .
C4 S4 C6 C5 2.8(7) . .
C4 S4 C6 S6 178.4(4) . .
C8 S6 C6 C5 -105.8(8) . .
C8 S6 C6 S4 78.8(6) . .
C2 C1 C9 O1 -178.6(5) . .
S1 C1 C9 O1 1.8(6) . .
C2 C1 C9 O2 1.5(9) . .
S1 C1 C9 O2 -178.1(4) . .
C1 C2 C10 O4 -179.1(5) . .
S2 C2 C10 O4 -0.7(6) . .
C1 C2 C10 O3 1.0(9) . .
S2 C2 C10 O3 179.4(4) . .
C15 N1 C11 C12 0.0(8) . .
C16 N1 C11 C12 -177.7(5) . .
N1 C11 C12 C13 -0.5(8) . .
C11 C12 C13 C14 0.4(8) . .
C11 C12 C13 C13 -180.0(6) . 2_665
C12 C13 C14 C15 0.2(8) . .
C13 C13 C14 C15 -179.4(6) 2_665 .
C11 N1 C15 C14 0.6(8) . .
C16 N1 C15 C14 178.3(5) . .
C13 C14 C15 N1 -0.7(9) . .
C15 N1 C16 C17 113.6(6) . .
C11 N1 C16 C17 -68.7(7) . .
N1 C16 C17 C18 -64.2(8) . .
C16 C17 C18 C19 -179.8(6) . .
