#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/54/7215460.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_7215460
loop_
_publ_author_name
'Biet, Thomas'
'Avarvari, Narcis'
_publ_section_title
;
 Electroactive tetrathiafulvalene based pyridine-mono and
 -bis(1,2,3-triazoles) click ligands: synthesis, crystal structures and
 coordination chemistry
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              6612
_journal_paper_doi               10.1039/c4ce00736k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H14 N4 S4'
_chemical_formula_sum            'C16 H14 N4 S4'
_chemical_formula_weight         390.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.564(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0637(9)
_cell_length_b                   7.2056(6)
_cell_length_c                   22.927(2)
_cell_measurement_reflns_used    3865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      3.69
_cell_volume                     1790.7(3)
_computing_cell_refinement       'Dirax/1sq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  area_detector
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_sigmaI/netI    0.1166
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20966
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.69
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²+1.9248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                1899
_reflns_number_total             3865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00736k2.cif
_cod_data_source_block           2
_cod_depositor_comments
;Adding full bibliography for 7215460--7215464.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1790.6(3)
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7215460
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4738(3) 0.5110(6) 0.08189(16) 0.0438(10) Uani 1 1 d .
C2 C 0.5172(3) 0.3395(6) 0.08961(16) 0.0426(10) Uani 1 1 d .
C3 C 0.6923(4) 0.5475(5) 0.15002(16) 0.0417(10) Uani 1 1 d .
C4 C 0.7928(4) 0.6117(5) 0.18692(16) 0.0379(10) Uani 1 1 d .
C5 C 0.9340(3) 0.8066(5) 0.26832(16) 0.0368(9) Uani 1 1 d .
C6 C 0.9792(3) 0.6345(5) 0.27356(16) 0.0404(10) Uani 1 1 d .
H6 H 1.0433 0.6033 0.3049 0.049 Uiso 1 1 calc R
C7 C 0.9689(4) 0.9658(5) 0.30806(16) 0.0369(9) Uani 1 1 d .
C8 C 0.8981(4) 1.0968(6) 0.32830(18) 0.0503(11) Uani 1 1 d .
H8 H 0.8123 1.0998 0.3196 0.060 Uiso 1 1 calc R
C9 C 0.3511(4) 0.5712(7) 0.04598(18) 0.0586(12) Uani 1 1 d .
H9A H 0.3440 0.7037 0.0481 0.088 Uiso 1 1 calc R
H9B H 0.2861 0.5139 0.0617 0.088 Uiso 1 1 calc R
H9C H 0.3449 0.5344 0.0052 0.088 Uiso 1 1 calc R
C10 C 0.4551(4) 0.1651(6) 0.06275(19) 0.0600(12) Uani 1 1 d .
H10A H 0.5071 0.0604 0.0757 0.090 Uiso 1 1 calc R
H10B H 0.4406 0.1736 0.0201 0.090 Uiso 1 1 calc R
H10C H 0.3778 0.1502 0.0752 0.090 Uiso 1 1 calc R
C11 C 1.2051(3) 0.9365(5) 0.32817(17) 0.0436(10) Uani 1 1 d .
H11A H 1.2634 1.0339 0.3243 0.052 Uiso 1 1 calc R
H11B H 1.1949 0.8593 0.2929 0.052 Uiso 1 1 calc R
C12 C 1.2563(3) 0.8204(5) 0.38216(16) 0.0376(9) Uani 1 1 d .
C13 C 1.3674(4) 0.8618(6) 0.41906(19) 0.0506(11) Uani 1 1 d .
H13 H 1.4135 0.9635 0.4114 0.061 Uiso 1 1 calc R
C14 C 1.4091(4) 0.7490(7) 0.4678(2) 0.0584(13) Uani 1 1 d .
H14 H 1.4842 0.7734 0.4931 0.070 Uiso 1 1 calc R
C15 C 1.3389(4) 0.6017(6) 0.47835(19) 0.0539(12) Uani 1 1 d .
H15 H 1.3641 0.5254 0.5112 0.065 Uiso 1 1 calc R
C16 C 1.2301(4) 0.5697(6) 0.4390(2) 0.0584(12) Uani 1 1 d .
H16 H 1.1829 0.4682 0.4459 0.070 Uiso 1 1 calc R
N3 N 0.9706(4) 1.2209(5) 0.36270(15) 0.0572(10) Uani 1 1 d .
N2 N 1.0869(4) 1.1755(5) 0.36473(15) 0.0538(9) Uani 1 1 d .
N1 N 1.0866(3) 1.0201(4) 0.33173(13) 0.0408(8) Uani 1 1 d .
N4 N 1.1877(3) 0.6752(5) 0.39146(14) 0.0510(9) Uani 1 1 d .
S1 S 0.57086(10) 0.69212(16) 0.11562(5) 0.0538(3) Uani 1 1 d .
S2 S 0.81104(10) 0.84862(14) 0.20757(5) 0.0468(3) Uani 1 1 d .
S3 S 0.66729(10) 0.31105(15) 0.13212(5) 0.0500(3) Uani 1 1 d .
S4 S 0.91660(10) 0.47014(14) 0.22093(5) 0.0459(3) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C9 127.3(4)
C2 C1 S1 117.3(3)
C9 C1 S1 115.4(3)
C1 C2 C10 126.9(4)
C1 C2 S3 117.3(3)
C10 C2 S3 115.6(3)
C4 C3 S1 122.8(3)
C4 C3 S3 123.7(3)
S1 C3 S3 113.5(2)
C3 C4 S4 123.6(3)
C3 C4 S2 122.5(3)
S4 C4 S2 113.8(2)
C6 C5 C7 128.6(3)
C6 C5 S2 116.5(3)
C7 C5 S2 114.8(3)
C5 C6 S4 118.8(3)
N1 C7 C8 103.5(3)
N1 C7 C5 125.6(3)
C8 C7 C5 130.8(4)
N3 C8 C7 110.1(4)
N1 C11 C12 112.2(3)
N4 C12 C13 122.5(4)
N4 C12 C11 115.7(3)
C13 C12 C11 121.8(4)
C12 C13 C14 118.7(4)
C15 C14 C13 119.3(4)
C14 C15 C16 118.1(4)
N4 C16 C15 124.0(4)
N2 N3 C8 108.6(3)
N3 N2 N1 107.0(3)
N2 N1 C7 110.8(3)
N2 N1 C11 118.1(3)
C7 N1 C11 131.0(3)
C12 N4 C16 117.3(4)
C3 S1 C1 95.8(2)
C5 S2 C4 94.23(18)
C2 S3 C3 95.9(2)
C6 S4 C4 94.55(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.325(5)
C1 C9 1.504(5)
C1 S1 1.767(4)
C2 C10 1.504(5)
C2 S3 1.760(4)
C3 C4 1.337(5)
C3 S1 1.758(4)
C3 S3 1.761(4)
C4 S4 1.760(4)
C4 S2 1.772(4)
C5 C6 1.333(5)
C5 C7 1.468(5)
C5 S2 1.767(4)
C6 S4 1.733(4)
C7 N1 1.364(4)
C7 C8 1.366(5)
C8 N3 1.346(5)
C11 N1 1.460(4)
C11 C12 1.507(5)
C12 N4 1.334(5)
C12 C13 1.378(5)
C13 C14 1.384(6)
C14 C15 1.365(6)
C15 C16 1.371(6)
C16 N4 1.335(5)
N3 N2 1.319(5)
N2 N1 1.351(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198454
