#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:22:02 +0300 (Mon, 04 May 2020) $
#$Revision: 251419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517570.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_4517570
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_sum            'C36.16 H16 N4 S2'
_chemical_formula_weight         570.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.673(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9205(18)
_cell_length_b                   16.126(2)
_cell_length_c                   13.885(2)
_cell_measurement_reflns_used    5646
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.19
_cell_volume                     2543.1(6)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0350
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7738
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.080
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       block
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0486
_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)+(0.0639P)²+1.5124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1675
_reflns_number_total             2186
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b23590_si_003.cif
_cod_data_source_block           t3_a
_cod_depositor_comments
'Adding full bibliography for 4517569--4517570.cif.'
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4517570
_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   0.941
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, 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_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
S1 S -0.1283(4) 0.4170(2) 0.0271(3) 0.0334(7) Uani 0.453(4) 1 d . . P A 1
S2 S -0.1286(4) 0.0722(3) 0.0222(4) 0.0391(8) Uani 0.453(4) 1 d . . P A 1
C1 C -0.1548(11) 0.4053(8) 0.0206(11) 0.043(4) Uani 0.547(4) 1 d . . P A 2
H1 H -0.076727 0.422363 0.037267 0.052 Uiso 0.547(4) 1 calc R U P A 2
C2 C -0.1538(12) 0.0834(9) 0.0186(13) 0.044(4) Uani 0.547(4) 1 d . . P A 2
H2 H -0.075932 0.066201 0.032945 0.053 Uiso 0.547(4) 1 calc R U P A 2
N1 N 0.14046(18) 0.36920(14) 0.08535(19) 0.0703(7) Uani 1 1 d . . . . .
N2 N 0.13852(19) 0.11911(14) 0.10758(19) 0.0760(7) Uani 1 1 d . . . . .
C3 C -0.250000 0.4612(2) 0.000000 0.0562(9) Uani 1 2 d S T P . .
H3 H -0.250000 0.518877 -0.000001 0.067 Uiso 1 2 calc R U P A 1
C4 C -0.18881(17) 0.32047(12) 0.01370(13) 0.0327(5) Uani 1 1 d . . . . .
C5 C -0.12034(17) 0.24450(11) 0.02957(13) 0.0331(5) Uani 1 1 d . . . . .
C6 C -0.18909(17) 0.16875(11) 0.01309(14) 0.0341(5) Uani 1 1 d . . . . .
C7 C -0.250000 0.0284(2) 0.000000 0.0617(10) Uani 1 2 d S T P . .
H7 H -0.249999 -0.029254 -0.000001 0.074 Uiso 1 2 calc R U P A 1
C8 C 0.07358(19) 0.31629(15) 0.07338(17) 0.0482(6) Uani 1 1 d . . . . .
C9 C 0.00063(18) 0.24456(12) 0.06008(16) 0.0396(5) Uani 1 1 d . . . . .
C10 C 0.07306(19) 0.17240(15) 0.08448(18) 0.0515(6) Uani 1 1 d . . . . .
C11 C 0.0608(2) 0.3242(2) 0.32726(19) 0.0660(8) Uani 1 1 d . . . . .
H11 H 0.124859 0.360146 0.343796 0.079 Uiso 1 1 calc R U . . .
C12 C -0.0529(2) 0.35621(17) 0.30047(16) 0.0541(6) Uani 1 1 d . . . . .
H12 H -0.063668 0.413365 0.299341 0.065 Uiso 1 1 calc R U . . .
C13 C -0.15008(17) 0.30494(14) 0.27555(13) 0.0389(5) Uani 1 1 d . . . . .
C14 C -0.13312(17) 0.21794(14) 0.27767(13) 0.0385(5) Uani 1 1 d . . . . .
C15 C -0.22978(18) 0.16173(13) 0.25337(13) 0.0390(5) Uani 1 1 d . . . . .
C16 C -0.2068(2) 0.07789(15) 0.25784(16) 0.0519(6) Uani 1 1 d . . . . .
H16 H -0.269223 0.040609 0.242031 0.062 Uiso 1 1 calc R U . . .
C17 C -0.0911(3) 0.04759(17) 0.28571(18) 0.0632(7) Uani 1 1 d . . . . .
H17 H -0.077891 -0.009319 0.288619 0.076 Uiso 1 1 calc R U . . .
C18 C 0.0009(2) 0.10004(18) 0.30829(18) 0.0634(7) Uani 1 1 d . . . . .
H18 H 0.077006 0.078863 0.325958 0.076 Uiso 1 1 calc R U . . .
C19 C -0.01604(19) 0.18606(16) 0.30563(15) 0.0493(6) Uani 1 1 d . . . . .
C20 C 0.0788(2) 0.24200(19) 0.32945(19) 0.0635(8) Uani 1 1 d . . . . .
H20 H 0.155369 0.221692 0.347035 0.076 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
C3 S1 C4 93.4(3) . . ?
C7 S2 C6 93.0(3) . . ?
C3 C1 C4 114.0(8) . . ?
C3 C1 H1 123.0 . . ?
C4 C1 H1 123.0 . . ?
C7 C2 C6 112.6(9) . . ?
C7 C2 H2 123.7 . . ?
C6 C2 H2 123.7 . . ?
C1 C3 C1 100.4(9) 2_455 . ?
S1 C3 S1 125.5(4) 2_455 . ?
S1 C3 H3 117.3 2_455 . ?
S1 C3 H3 117.3 . . ?
C4 C4 C1 105.8(5) 2_455 . ?
C4 C4 C5 122.42(11) 2_455 . ?
C1 C4 C5 131.8(6) . . ?
C4 C4 S1 113.84(15) 2_455 . ?
C5 C4 S1 123.7(2) . . ?
C9 C5 C6 122.63(18) . . ?
C9 C5 C4 122.37(18) . . ?
C6 C5 C4 114.99(17) . . ?
C6 C6 C2 106.3(6) 2_455 . ?
C6 C6 C5 122.57(11) 2_455 . ?
C2 C6 C5 131.1(6) . . ?
C6 C6 S2 113.91(17) 2_455 . ?
C5 C6 S2 123.5(2) . . ?
S2 C7 S2 126.0(4) 2_455 . ?
S2 C7 H7 117.0 2_455 . ?
S2 C7 H7 117.0 . . ?
N1 C8 C9 173.9(2) . . ?
C5 C9 C8 125.63(19) . . ?
C5 C9 C10 125.12(19) . . ?
C8 C9 C10 109.25(18) . . ?
N2 C10 C9 174.3(3) . . ?
C20 C11 C12 120.5(2) . . ?
C20 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 C15 121.7(2) . 7_455 ?
C14 C13 C15 119.33(18) . 7_455 ?
C13 C14 C15 121.70(17) . . ?
C13 C14 C19 119.0(2) . . ?
C15 C14 C19 119.3(2) . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 C13 122.5(2) . 7_455 ?
C14 C15 C13 118.96(19) . 7_455 ?
C15 C16 C17 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 122.0(2) . . ?
C18 C19 C14 119.0(2) . . ?
C20 C19 C14 118.9(2) . . ?
C11 C20 C19 121.2(2) . . ?
C11 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
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
S1 C3 1.557(4) . ?
S1 C4 1.702(4) . ?
S2 C7 1.554(5) . ?
S2 C6 1.705(5) . ?
C1 C3 1.409(14) . ?
C1 C4 1.422(12) . ?
C1 H1 0.9300 . ?
C2 C7 1.410(16) . ?
C2 C6 1.435(13) . ?
C2 H2 0.9300 . ?
N1 C8 1.145(3) . ?
N2 C10 1.140(3) . ?
C3 H3 0.9300 . ?
C4 C4 1.391(4) 2_455 ?
C4 C5 1.451(3) . ?
C5 C9 1.374(3) . ?
C5 C6 1.450(3) . ?
C6 C6 1.386(4) 2_455 ?
C7 H7 0.9300 . ?
C8 C9 1.425(3) . ?
C9 C10 1.427(3) . ?
C11 C20 1.342(4) . ?
C11 C12 1.391(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.417(3) . ?
C13 C15 1.467(3) 7_455 ?
C14 C15 1.424(3) . ?
C14 C19 1.426(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.402(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.344(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.405(4) . ?
C20 H20 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 C3 C1 -0.3(4) . . . 2_455 ?
C4 S1 C3 S1 -0.04(9) . . . 2_455 ?
C3 C1 C4 C4 0.7(11) . . . 2_455 ?
C3 C1 C4 C5 -179.4(4) . . . . ?
C3 S1 C4 C4 0.1(3) . . . 2_455 ?
C3 S1 C4 C5 -179.61(16) . . . . ?
C4 C4 C5 C9 -177.7(2) 2_455 . . . ?
C1 C4 C5 C9 2.4(8) . . . . ?
S1 C4 C5 C9 2.1(3) . . . . ?
C4 C4 C5 C6 1.0(3) 2_455 . . . ?
C1 C4 C5 C6 -178.9(8) . . . . ?
S1 C4 C5 C6 -179.3(2) . . . . ?
C7 C2 C6 C6 -2.0(13) . . . 2_455 ?
C7 C2 C6 C5 178.0(5) . . . . ?
C9 C5 C6 C6 176.9(2) . . . 2_455 ?
C4 C5 C6 C6 -1.7(3) . . . 2_455 ?
C9 C5 C6 C2 -3.2(10) . . . . ?
C4 C5 C6 C2 178.2(9) . . . . ?
C9 C5 C6 S2 -4.0(4) . . . . ?
C4 C5 C6 S2 177.3(3) . . . . ?
C7 S2 C6 C6 -2.9(4) . . . 2_455 ?
C7 S2 C6 C5 177.99(17) . . . . ?
C6 C2 C7 C2 0.8(5) . . . 2_455 ?
C6 S2 C7 S2 0.90(11) . . . 2_455 ?
C6 C5 C9 C8 177.05(19) . . . . ?
C4 C5 C9 C8 -4.4(3) . . . . ?
C6 C5 C9 C10 -3.6(3) . . . . ?
C4 C5 C9 C10 174.91(19) . . . . ?
C20 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C12 C13 C15 -179.61(19) . . . 7_455 ?
C12 C13 C14 C15 179.59(17) . . . . ?
C15 C13 C14 C15 -0.6(3) 7_455 . . . ?
C12 C13 C14 C19 0.1(3) . . . . ?
C15 C13 C14 C19 179.85(16) 7_455 . . . ?
C13 C14 C15 C16 -179.45(17) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
C13 C14 C15 C13 0.6(3) . . . 7_455 ?
C19 C14 C15 C13 -179.85(16) . . . 7_455 ?
C14 C15 C16 C17 0.1(3) . . . . ?
C13 C15 C16 C17 -179.99(19) 7_455 . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C17 C18 C19 C20 179.7(2) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C13 C14 C19 C18 179.66(19) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C13 C14 C19 C20 -0.5(3) . . . . ?
C15 C14 C19 C20 179.98(19) . . . . ?
C12 C11 C20 C19 -0.5(4) . . . . ?
C18 C19 C20 C11 -179.4(2) . . . . ?
C14 C19 C20 C11 0.7(3) . . . . ?
