#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:22:02 +0300 (Mon, 04 May 2020) $
#$Revision: 251419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517569.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_4517569
loop_
_publ_author_name
'Jin, Jianqun'
'Wu, Shanyu'
'Ma, Yudong'
'Dong, Caiqiao'
'Wang, Wei'
'Liu, Xitong'
'Xu, Haixiao'
'Long, Guankui'
'Zhang, Mingtao'
'Zhang, Jing'
'Huang, Wei'
_publ_section_title
;
 Nucleation Control-Triggering Cocrystal Polymorphism of Charge-Transfer
 Complexes Differing in Physical and Electronic Properties.
;
_journal_issue                   17
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              19718
_journal_page_last               19726
_journal_paper_doi               10.1021/acsami.9b23590
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C36 H16 N4 S2'
_chemical_formula_sum            'C36 H16 N4 S2'
_chemical_formula_weight         568.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                72.698(4)
_cell_angle_beta                 87.979(5)
_cell_angle_gamma                70.408(5)
_cell_formula_units_Z            1
_cell_length_a                   7.3777(16)
_cell_length_b                   9.654(2)
_cell_length_c                   10.051(2)
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      36.26
_cell_measurement_theta_min      2.35
_cell_volume                     642.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4072
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.938
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     207
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0704
_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)+(0.1479P)²+1.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2104
_refine_ls_wR_factor_ref         0.2137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2034
_reflns_number_total             2211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b23590_si_002.cif
_cod_data_source_block           P-1
_cod_depositor_comments
'Adding full bibliography for 4517569--4517570.cif.'
_cod_database_code               4517569
_shelx_shelxl_version_number     2016/6
_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   0.905
_shelx_estimated_absorpt_t_max   0.953
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.7835(5) 0.6807(3) 0.4848(4) 0.0281(6) Uani 0.5 1 d . U P A 1
C8A C 0.353(3) 1.053(2) 0.779(3) 0.0643(9) Uani 0.5 1 d . U P B 1
H8A H 0.370018 0.992553 0.871749 0.077 Uiso 0.5 1 calc R U P B 1
C8B C 0.762(2) 0.7112(17) 0.4689(19) 0.0281(6) Uani 0.5 1 d . U P A 2
H8B H 0.823529 0.614681 0.532335 0.034 Uiso 0.5 1 calc R U P A 2
S1B S 0.3330(7) 1.0894(4) 0.7511(5) 0.0643(9) Uani 0.5 1 d . U P B 2
N1 N 0.5128(6) 0.7628(4) 1.0068(3) 0.0700(10) Uani 1 1 d . U . . .
N2 N 0.8393(6) 0.4794(4) 0.7968(4) 0.0816(13) Uani 1 1 d . U . . .
C4 C 0.5613(4) 0.8754(3) 0.6350(3) 0.0342(7) Uani 1 1 d . U . . .
C5 C 0.4296(4) 1.0301(3) 0.6249(3) 0.0344(7) Uani 1 1 d . U . . .
C6 C 0.6275(4) 0.8535(3) 0.5023(3) 0.0330(7) Uani 1 1 d . U . . .
C3 C 0.6151(5) 0.7587(4) 0.7601(3) 0.0413(7) Uani 1 1 d . U . . .
C7 C 0.7745(5) 0.7568(5) 0.3150(4) 0.0550(10) Uani 1 1 d . U . . .
H7 H 0.843958 0.692307 0.264417 0.066 Uiso 1 1 calc R U . A 1
C1 C 0.7413(6) 0.6051(4) 0.7746(4) 0.0531(9) Uani 1 1 d . U . . .
C2 C 0.5534(5) 0.7688(4) 0.8948(4) 0.0490(8) Uani 1 1 d . U . . .
C14 C 0.9550(4) 0.1076(4) 0.3621(3) 0.0374(7) Uani 1 1 d . U . . .
C15 C 1.0884(4) -0.0445(4) 0.3824(3) 0.0380(7) Uani 1 1 d . U . . .
C9 C 0.8661(4) 0.1550(4) 0.4775(3) 0.0379(7) Uani 1 1 d . U . . .
C13 C 0.9094(5) 0.2151(4) 0.2263(4) 0.0492(8) Uani 1 1 d . U . . .
C10 C 0.7388(5) 0.3046(4) 0.4509(4) 0.0506(9) Uani 1 1 d . U . . .
H10 H 0.680707 0.337043 0.525169 0.061 Uiso 1 1 calc R U . . .
C16 C 1.1715(5) -0.0832(5) 0.2662(4) 0.0510(9) Uani 1 1 d . U . . .
H16 H 1.258618 -0.182046 0.277830 0.061 Uiso 1 1 calc R U . . .
C17 C 1.1274(6) 0.0225(6) 0.1328(4) 0.0614(10) Uani 1 1 d . U . . .
H17 H 1.185923 -0.006439 0.057160 0.074 Uiso 1 1 calc R U . . .
C18 C 1.0001(6) 0.1670(6) 0.1120(4) 0.0621(10) Uani 1 1 d . U . . .
H18 H 0.971481 0.235807 0.022069 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7773(6) 0.3646(5) 0.2055(4) 0.0591(10) Uani 1 1 d . U . . .
H12 H 0.746434 0.433790 0.115819 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6947(6) 0.4086(4) 0.3156(5) 0.0592(10) Uani 1 1 d . U . . .
H11 H 0.608469 0.508265 0.301316 0.071 Uiso 1 1 calc R U . . .
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'
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
C7 S1A C6 91.20(18) . . ?
C5 C8A C7 86.3(11) . 2_676 ?
C5 C8A H8A 136.8 . . ?
C7 C8A H8A 136.8 2_676 . ?
C7 C8B C6 106.5(9) . . ?
C7 C8B H8B 126.7 . . ?
C6 C8B H8B 126.7 . . ?
C7 S1B C5 102.8(3) 2_676 . ?
C3 C4 C6 122.8(3) . . ?
C3 C4 C5 122.5(3) . . ?
C6 C4 C5 114.6(3) . . ?
C6 C5 C4 122.2(3) 2_676 . ?
C6 C5 S1B 111.4(3) 2_676 . ?
C4 C5 S1B 126.4(3) . . ?
C6 C5 C8A 123.6(7) 2_676 . ?
C4 C5 C8A 114.1(7) . . ?
C5 C6 C4 123.2(3) 2_676 . ?
C5 C6 C8B 106.3(7) 2_676 . ?
C4 C6 C8B 130.6(7) . . ?
C5 C6 S1A 112.9(2) 2_676 . ?
C4 C6 S1A 124.0(3) . . ?
C4 C3 C1 124.5(3) . . ?
C4 C3 C2 126.6(3) . . ?
C1 C3 C2 108.9(3) . . ?
S1B C7 C8B 113.0(7) 2_676 . ?
S1A C7 C8A 126.0(9) . 2_676 ?
S1A C7 H7 117.0 . . ?
C8A C7 H7 117.0 2_676 . ?
N2 C1 C3 174.8(4) . . ?
N1 C2 C3 173.8(4) . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 C9 118.8(3) . . ?
C15 C14 C9 121.0(3) . . ?
C16 C15 C14 118.3(3) . . ?
C16 C15 C9 121.8(3) . 2_756 ?
C14 C15 C9 119.9(3) . 2_756 ?
C10 C9 C14 118.2(3) . . ?
C10 C9 C15 122.7(3) . 2_756 ?
C14 C9 C15 119.1(3) . 2_756 ?
C12 C13 C14 120.5(4) . . ?
C12 C13 C18 121.2(4) . . ?
C14 C13 C18 118.4(4) . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C15 C16 C17 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
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
S1A C7 1.639(5) . ?
S1A C6 1.735(4) . ?
C8A C5 1.68(3) . ?
C8A C7 1.734(19) 2_676 ?
C8A H8A 0.9300 . ?
C8B C7 1.485(19) . ?
C8B C6 1.523(16) . ?
C8B H8B 0.9300 . ?
S1B C7 1.392(5) 2_676 ?
S1B C5 1.594(6) . ?
N1 C2 1.145(5) . ?
N2 C1 1.144(5) . ?
C4 C3 1.378(5) . ?
C4 C6 1.454(4) . ?
C4 C5 1.459(4) . ?
C5 C6 1.393(5) 2_676 ?
C3 C1 1.429(5) . ?
C3 C2 1.434(5) . ?
C7 H7 0.9300 . ?
C14 C13 1.418(5) . ?
C14 C15 1.426(5) . ?
C14 C9 1.430(5) . ?
C15 C16 1.392(5) . ?
C15 C9 1.461(5) 2_756 ?
C9 C10 1.385(5) . ?
C13 C12 1.403(6) . ?
C13 C18 1.428(6) . ?
C10 C11 1.401(6) . ?
C10 H10 0.9300 . ?
C16 C17 1.393(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.354(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C12 C11 1.354(6) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
