#------------------------------------------------------------------------------
#$Date: 2022-03-15 12:22:50 +0200 (Tue, 15 Mar 2022) $
#$Revision: 273695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104758.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_8104758
loop_
_publ_author_name
'Yan, Wei-Hong'
'Liu, Xue-Guo'
'Shen, Ming-Le'
'Pan, Hui-Yan'
_publ_section_title
;
 Crystal structure of
 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium)
 bis(1,2-dicyanoethene-1,2-dithiolato-k2 S:S)zinc(II), C26H18N6ZnS4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              533
_journal_page_last               535
_journal_paper_doi               10.1515/ncrs-2020-0624
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C8 N4 S4 Zn, 2(C9 H9 N)'
_chemical_formula_sum            'C26 H18 N6 S4 Zn'
_chemical_formula_weight         608.07
_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
_cell_angle_alpha                102.907(3)
_cell_angle_beta                 102.302(3)
_cell_angle_gamma                110.419(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4677(13)
_cell_length_b                   12.0147(17)
_cell_length_c                   13.571(3)
_cell_measurement_reflns_used    5150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.300
_cell_measurement_theta_min      2.381
_cell_volume                     1336.7(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9681
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         1.624
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5260
_reflns_number_total             6567
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0624_suppl.cif
_cod_data_source_block           a
_cod_database_code               8104758
_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 C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26)
;
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
C1 C 0.9451(3) 0.2105(2) 0.05814(18) 0.0456(5) Uani 1 1 d . . . . .
C2 C 0.9456(2) 0.2330(2) 0.16656(17) 0.0416(4) Uani 1 1 d . . . . .
C3 C 0.8896(3) 0.3176(2) 0.20736(18) 0.0427(5) Uani 1 1 d . . . . .
C4 C 0.8312(3) 0.3768(2) 0.13851(19) 0.0517(6) Uani 1 1 d . . . . .
C5 C 1.1081(3) 0.1708(2) 0.70883(18) 0.0462(5) Uani 1 1 d . . . . .
C6 C 1.0242(3) 0.1611(2) 0.60428(16) 0.0398(4) Uani 1 1 d . . . . .
C7 C 0.8665(3) 0.08420(19) 0.55806(17) 0.0402(4) Uani 1 1 d . . . . .
C8 C 0.7812(3) 0.0135(2) 0.61560(19) 0.0456(5) Uani 1 1 d . . . . .
C9 C 0.8185(3) 0.3409(3) 0.6839(3) 0.0652(7) Uani 1 1 d . . . . .
H9 H 0.9070 0.3806 0.6648 0.078 Uiso 1 1 calc R . . . .
C10 C 0.8384(4) 0.3195(3) 0.7798(3) 0.0754(9) Uani 1 1 d . . . . .
H10 H 0.9401 0.3441 0.8256 0.090 Uiso 1 1 calc R . . . .
C11 C 0.7076(4) 0.2615(3) 0.8076(2) 0.0656(7) Uani 1 1 d . . . . .
H11 H 0.7197 0.2483 0.8733 0.079 Uiso 1 1 calc R . . . .
C12 C 0.5599(3) 0.2233(3) 0.7382(2) 0.0581(6) Uani 1 1 d . . . . .
H12 H 0.4700 0.1823 0.7553 0.070 Uiso 1 1 calc R . . . .
C13 C 0.5450(3) 0.2456(2) 0.6431(2) 0.0508(5) Uani 1 1 d . . . . .
H13 H 0.4442 0.2188 0.5952 0.061 Uiso 1 1 calc R . . . .
C14 C 0.6497(4) 0.3285(3) 0.5137(2) 0.0600(7) Uani 1 1 d . . . . .
H14A H 0.5848 0.2492 0.4569 0.072 Uiso 1 1 calc R . . . .
H14B H 0.7521 0.3634 0.5030 0.072 Uiso 1 1 calc R . . . .
C15 C 0.5708(3) 0.4173(2) 0.50768(19) 0.0458(5) Uani 1 1 d . . . . .
C16 C 0.6505(3) 0.5423(2) 0.5690(2) 0.0504(5) Uani 1 1 d . . . . .
H16 H 0.7525 0.5712 0.6161 0.060 Uiso 1 1 calc R . . . .
C17 C 0.4190(3) 0.3753(2) 0.4385(2) 0.0494(5) Uani 1 1 d . . . . .
H17 H 0.3636 0.2911 0.3969 0.059 Uiso 1 1 calc R . . . .
C18 C 0.3202(3) 0.3055(3) 0.0460(2) 0.0557(6) Uani 1 1 d . . . . .
H18 H 0.2415 0.2608 -0.0198 0.067 Uiso 1 1 calc R . . . .
C19 C 0.3896(4) 0.4352(3) 0.0796(3) 0.0688(8) Uani 1 1 d . . . . .
H19 H 0.3565 0.4782 0.0372 0.083 Uiso 1 1 calc R . . . .
C20 C 0.5072(3) 0.4997(3) 0.1754(3) 0.0641(7) Uani 1 1 d . . . . .
H20 H 0.5559 0.5869 0.1986 0.077 Uiso 1 1 calc R . . . .
C21 C 0.5525(3) 0.4348(3) 0.2370(2) 0.0611(6) Uani 1 1 d . . . . .
H21 H 0.6326 0.4774 0.3025 0.073 Uiso 1 1 calc R . . . .
C22 C 0.4805(3) 0.3087(2) 0.20223(18) 0.0516(5) Uani 1 1 d . . . . .
H22 H 0.5109 0.2649 0.2448 0.062 Uiso 1 1 calc R . . . .
C23 C 0.2920(3) 0.1048(2) 0.0721(2) 0.0613(7) Uani 1 1 d . . . . .
H23A H 0.1937 0.0736 0.0139 0.074 Uiso 1 1 calc R . . . .
H23B H 0.2664 0.0767 0.1303 0.074 Uiso 1 1 calc R . . . .
C24 C 0.4017(3) 0.0515(2) 0.0355(2) 0.0462(5) Uani 1 1 d . . . . .
C25 C 0.4100(3) 0.0389(2) -0.0667(2) 0.0539(6) Uani 1 1 d . . . . .
H25 H 0.3491 0.0643 -0.1124 0.065 Uiso 1 1 calc R . . . .
C26 C 0.4905(3) 0.0118(2) 0.1012(2) 0.0540(6) Uani 1 1 d . . . . .
H26 H 0.4841 0.0188 0.1696 0.065 Uiso 1 1 calc R . . . .
N1 N 0.6731(2) 0.30538(17) 0.61782(15) 0.0449(4) Uani 1 1 d . . . . .
N2 N 0.3663(2) 0.24471(17) 0.10803(14) 0.0407(4) Uani 1 1 d . . . . .
N3 N 0.7826(3) 0.4239(3) 0.0834(2) 0.0769(8) Uani 1 1 d . . . . .
N4 N 0.9460(3) 0.1911(3) -0.02791(18) 0.0636(6) Uani 1 1 d . . . . .
N5 N 0.7066(3) -0.0423(2) 0.6590(2) 0.0623(6) Uani 1 1 d . . . . .
N6 N 1.1847(3) 0.1848(2) 0.79231(17) 0.0673(6) Uani 1 1 d . . . . .
S1 S 1.01499(8) 0.14502(6) 0.23146(5) 0.04983(15) Uani 1 1 d . . . . .
S2 S 0.88203(8) 0.35786(6) 0.33647(5) 0.05154(16) Uani 1 1 d . . . . .
S3 S 1.14199(6) 0.25819(6) 0.54831(5) 0.04838(15) Uani 1 1 d . . . . .
S4 S 0.75176(7) 0.06525(6) 0.43227(5) 0.04942(15) Uani 1 1 d . . . . .
Zn1 Zn 0.95002(3) 0.20276(2) 0.38601(2) 0.04353(10) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
N4 C1 C2 178.7(3) . .
C1 C2 S1 114.87(16) . .
C3 C2 C1 118.40(19) . .
C3 C2 S1 126.71(17) . .
C2 C3 C4 117.8(2) . .
C2 C3 S2 125.06(16) . .
C4 C3 S2 117.13(17) . .
N3 C4 C3 179.2(3) . .
N6 C5 C6 175.2(3) . .
C5 C6 S3 113.29(17) . .
C7 C6 C5 121.0(2) . .
C7 C6 S3 125.72(16) . .
C6 C7 C8 120.0(2) . .
C6 C7 S4 125.20(17) . .
C8 C7 S4 114.77(16) . .
N5 C8 C7 176.6(2) . .
N1 C9 C10 120.3(3) . .
C9 C10 C11 119.6(3) . .
C12 C11 C10 119.3(3) . .
C11 C12 C13 119.4(3) . .
N1 C13 C12 121.0(2) . .
N1 C14 C15 112.17(19) . .
C16 C15 C14 120.5(2) . .
C16 C15 C17 119.0(2) . .
C17 C15 C14 120.5(2) . .
C17 C16 C15 120.8(2) 2_666 .
C16 C17 C15 120.2(2) 2_666 .
N2 C18 C19 119.9(2) . .
C20 C19 C18 119.4(2) . .
C21 C20 C19 119.3(3) . .
C22 C21 C20 119.4(3) . .
N2 C22 C21 121.7(2) . .
N2 C23 C24 111.28(18) . .
C25 C24 C23 119.9(2) . .
C26 C24 C23 120.9(2) . .
C26 C24 C25 119.2(2) . .
C24 C25 C26 120.0(2) . 2_655
C24 C26 C25 120.8(2) . 2_655
C9 N1 C13 120.4(2) . .
C9 N1 C14 120.9(2) . .
C13 N1 C14 118.6(2) . .
C18 N2 C22 120.2(2) . .
C18 N2 C23 120.1(2) . .
C22 N2 C23 119.7(2) . .
C2 S1 Zn1 97.20(8) . .
C3 S2 Zn1 97.07(7) . .
C6 S3 Zn1 97.95(8) . .
C7 S4 Zn1 98.05(8) . .
S1 Zn1 S2 92.76(2) . .
S3 Zn1 S1 117.32(3) . .
S3 Zn1 S2 119.53(3) . .
S3 Zn1 S4 93.05(2) . .
S4 Zn1 S1 123.67(3) . .
S4 Zn1 S2 112.85(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.434(3) .
C1 N4 1.141(3) .
C2 C3 1.368(3) .
C2 S1 1.726(2) .
C3 C4 1.427(3) .
C3 S2 1.734(2) .
C4 N3 1.146(3) .
C5 C6 1.428(3) .
C5 N6 1.148(3) .
C6 C7 1.363(3) .
C6 S3 1.741(2) .
C7 C8 1.438(3) .
C7 S4 1.735(2) .
C8 N5 1.149(3) .
C9 C10 1.369(4) .
C9 N1 1.332(3) .
C10 C11 1.370(4) .
C11 C12 1.361(4) .
C12 C13 1.364(3) .
C13 N1 1.335(3) .
C14 C15 1.508(3) .
C14 N1 1.485(3) .
C15 C16 1.379(3) .
C15 C17 1.382(3) .
C16 C17 1.377(3) 2_666
C17 C16 1.377(3) 2_666
C18 C19 1.381(4) .
C18 N2 1.332(3) .
C19 C20 1.365(4) .
C20 C21 1.365(4) .
C21 C22 1.343(4) .
C22 N2 1.337(3) .
C23 C24 1.509(3) .
C23 N2 1.491(3) .
C24 C25 1.384(3) .
C24 C26 1.371(3) .
C25 C26 1.393(3) 2_655
C26 C25 1.393(3) 2_655
S1 Zn1 2.3359(7) .
S2 Zn1 2.3561(6) .
S3 Zn1 2.3222(7) .
S4 Zn1 2.3342(7) .
