#------------------------------------------------------------------------------
#$Date: 2021-11-04 03:45:49 +0200 (Thu, 04 Nov 2021) $
#$Revision: 270294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565119.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_1565119
loop_
_publ_author_name
'Hu, Chen'
'Wang, Meiyi'
'Han, Xiao'
'Fan, Jingyi'
'Wei, Donghui'
'Ding, Jie'
'Ma, Zhiwei'
'Xiao, Guanjun'
'Zou, Bo'
'Hou, Hongwei'
_publ_section_title
;
 Fascinating Supramolecular Assembly through Noncovalent Interactions
 Involving Anions in Organic Ionic Crystals
;
_journal_issue                   40
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              22346
_journal_page_last               22353
_journal_paper_doi               10.1021/acs.jpcc.1c07151
_journal_volume                  125
_journal_year                    2021
_chemical_formula_moiety         'C16 H14 N6 S, 2(Cl)'
_chemical_formula_sum            'C16 H14 Cl2 N6 S'
_chemical_formula_weight         393.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5351(3)
_cell_length_b                   14.6310(4)
_cell_length_c                   11.9513(3)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.26
_cell_volume                     1759.90(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44279
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.307
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0621 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.9692.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0439
_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)+(0.0462P)²+1.1074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3400
_reflns_number_total             4039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c07151_si_003.cif
_cod_data_source_block           mo_200824e_0m
_cod_database_code               1565119
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), N3(H3), C3(H3A), C4(H4), N4(H4A), N5(H5), N6(H6), C8(H8),
 C9(H9), C13(H13), C14(H14), C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
C1 C 0.8717(2) 0.42030(16) 0.67809(19) 0.0479(5) Uani 1 1 d . . . . .
H1 H 0.882697 0.458251 0.742695 0.058 Uiso 1 1 calc R . . . .
S1 S 0.34223(7) 0.45262(5) 0.53423(7) 0.0709(2) Uani 1 1 d . . . . .
N1 N 0.46368(18) 0.39112(14) 0.52081(17) 0.0536(5) Uani 1 1 d . . . . .
C2 C 0.9567(2) 0.42615(17) 0.6133(2) 0.0576(6) Uani 1 1 d . . . . .
H2 H 1.029020 0.465708 0.634515 0.069 Uiso 1 1 calc R . . . .
N2 N 0.27895(18) 0.38639(14) 0.61147(18) 0.0551(5) Uani 1 1 d . . . . .
N3 N 0.64924(18) 0.24158(13) 0.53559(17) 0.0499(4) Uani 1 1 d . . . . .
H3 H 0.646310 0.200565 0.483344 0.060 Uiso 1 1 calc R . . . .
C3 C 0.9335(2) 0.37113(17) 0.5133(2) 0.0589(6) Uani 1 1 d . . . . .
H3A H 0.989863 0.375327 0.466528 0.071 Uiso 1 1 calc R . . . .
C4 C 0.8298(2) 0.31177(17) 0.4838(2) 0.0531(5) Uani 1 1 d . . . . .
H4 H 0.813593 0.277030 0.415854 0.064 Uiso 1 1 calc R . . . .
N4 N 0.23816(19) 0.23274(13) 0.75552(17) 0.0519(5) Uani 1 1 d . . . . .
H4A H 0.185059 0.186701 0.740308 0.062 Uiso 1 1 calc R . . . .
C5 C 0.7469(2) 0.30310(14) 0.55673(18) 0.0433(4) Uani 1 1 d . . . . .
N5 N 0.76972(16) 0.35916(12) 0.64942(14) 0.0418(4) Uani 1 1 d . . . . .
H5 H 0.717537 0.356343 0.692706 0.050 Uiso 1 1 calc R . . . .
C6 C 0.46086(19) 0.31398(14) 0.58044(17) 0.0405(4) Uani 1 1 d . . . . .
N6 N 0.10662(18) 0.28998(13) 0.86171(16) 0.0493(4) Uani 1 1 d . . . . .
H6 H 0.052917 0.245493 0.834795 0.059 Uiso 1 1 calc R . . . .
C7 C 0.5498(2) 0.23957(14) 0.59390(18) 0.0435(4) Uani 1 1 d . . . . .
C8 C 0.5327(2) 0.16696(15) 0.6591(2) 0.0540(5) Uani 1 1 d . . . . .
H8 H 0.589897 0.117269 0.668450 0.065 Uiso 1 1 calc R . . . .
C9 C 0.4290(3) 0.16526(15) 0.7134(2) 0.0555(6) Uani 1 1 d . . . . .
H9 H 0.420503 0.114386 0.757243 0.067 Uiso 1 1 calc R . . . .
C10 C 0.3425(2) 0.23557(14) 0.70296(18) 0.0444(5) Uani 1 1 d . . . . .
C11 C 0.35563(19) 0.31156(14) 0.63365(17) 0.0413(4) Uani 1 1 d . . . . .
C12 C 0.2173(2) 0.29776(14) 0.82774(17) 0.0413(4) Uani 1 1 d . . . . .
C13 C 0.3032(2) 0.36983(15) 0.87146(18) 0.0469(5) Uani 1 1 d . . . . .
H13 H 0.381170 0.376118 0.850664 0.056 Uiso 1 1 calc R . . . .
C14 C 0.2725(3) 0.43135(17) 0.9452(2) 0.0584(6) Uani 1 1 d . . . . .
H14 H 0.328919 0.480532 0.973115 0.070 Uiso 1 1 calc R . . . .
C15 C 0.1573(3) 0.42134(19) 0.9792(2) 0.0626(6) Uani 1 1 d . . . . .
H15 H 0.136669 0.463081 1.029873 0.075 Uiso 1 1 calc R . . . .
C16 C 0.0770(2) 0.35011(18) 0.9371(2) 0.0561(6) Uani 1 1 d . . . . .
H16 H 0.000573 0.341830 0.959719 0.067 Uiso 1 1 calc R . . . .
Cl2 Cl -0.03558(7) 0.12936(4) 0.71041(6) 0.06441(19) Uani 1 1 d . . . . .
Cl1 Cl 0.63377(7) 0.40279(4) 0.83612(5) 0.05859(18) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 H1 119.8 . . ?
C2 C1 N5 120.4(2) . . ?
N5 C1 H1 119.8 . . ?
N1 S1 N2 101.33(10) . . ?
C6 N1 S1 105.93(14) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.3(2) . . ?
C3 C2 H2 120.8 . . ?
C11 N2 S1 106.10(14) . . ?
C5 N3 H3 117.9 . . ?
C5 N3 C7 124.11(17) . . ?
C7 N3 H3 117.9 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C10 N4 H4A 118.0 . . ?
C12 N4 H4A 118.0 . . ?
C12 N4 C10 123.94(17) . . ?
N3 C5 C4 121.9(2) . . ?
N3 C5 N5 120.59(18) . . ?
N5 C5 C4 117.6(2) . . ?
C1 N5 H5 118.5 . . ?
C5 N5 C1 123.02(18) . . ?
C5 N5 H5 118.5 . . ?
N1 C6 C7 126.21(18) . . ?
N1 C6 C11 113.50(18) . . ?
C7 C6 C11 120.28(19) . . ?
C12 N6 H6 118.9 . . ?
C12 N6 C16 122.2(2) . . ?
C16 N6 H6 118.9 . . ?
C6 C7 N3 119.24(19) . . ?
C8 C7 N3 122.7(2) . . ?
C8 C7 C6 118.05(19) . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.0(2) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 N4 121.7(2) . . ?
C9 C10 C11 118.05(19) . . ?
C11 C10 N4 120.23(19) . . ?
N2 C11 C6 113.11(18) . . ?
N2 C11 C10 126.84(18) . . ?
C10 C11 C6 120.05(19) . . ?
N4 C12 N6 116.97(18) . . ?
N4 C12 C13 124.51(19) . . ?
N6 C12 C13 118.50(19) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.7 . . ?
N6 C16 H16 119.7 . . ?
C15 C16 N6 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
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 H1 0.9300 . ?
C1 C2 1.349(3) . ?
C1 N5 1.361(3) . ?
S1 N1 1.6105(19) . ?
S1 N2 1.6122(19) . ?
N1 C6 1.340(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(4) . ?
N2 C11 1.340(3) . ?
N3 H3 0.8600 . ?
N3 C5 1.334(3) . ?
N3 C7 1.419(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.358(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.410(3) . ?
N4 H4A 0.8600 . ?
N4 C10 1.419(3) . ?
N4 C12 1.346(3) . ?
C5 N5 1.342(3) . ?
N5 H5 0.8600 . ?
C6 C7 1.415(3) . ?
C6 C11 1.432(3) . ?
N6 H6 0.8600 . ?
N6 C12 1.348(3) . ?
N6 C16 1.360(3) . ?
C7 C8 1.361(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.426(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.355(3) . ?
C10 C11 1.417(3) . ?
C12 C13 1.388(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.397(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.343(4) . ?
C16 H16 0.9300 . ?
