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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500090.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_4500090
loop_
_publ_author_name
'Lago, Ana Belén'
'Carballo, Rosa'
'García-Martínez, Emilia'
'Vázquez-López, Ezequiel M.'
_publ_section_title
;
 Metal to Ligand Interactions and Hydrogen Bonding in the Design of
 Metallosupramolecular Compounds: Effect of pH and Aprotic Solvents on the
 Nature of Materials Based on Bis(4-pyridylthio)methane and Copper(II)
 Chloride
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              59
_journal_paper_doi               10.1021/cg1004566
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C22 H21 Cl3 Cu N4 S4'
_chemical_formula_weight         639.56
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 97.209(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2421(8)
_cell_length_b                   25.079(2)
_cell_length_c                   13.4368(12)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.088
_cell_measurement_theta_min      5.240
_cell_volume                     2755.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.944
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.805122
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                1668
_reflns_number_total             3162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1004566_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4500090
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.5000 0.57200(2) 0.7500 0.03916(16) Uani 1 2 d S
Cl1 Cl 0.5000 0.47905(5) 0.7500 0.0835(5) Uani 1 2 d S
Cl2 Cl 0.63270(10) 0.62750(3) 0.64163(6) 0.0509(2) Uani 1 1 d .
S11 S -0.23556(12) 0.67282(4) 0.41143(7) 0.0632(3) Uani 1 1 d .
C1 C -0.2563(3) 0.60179(12) 0.4070(2) 0.0460(8) Uani 1 1 d .
H1A H -0.3518 0.5931 0.3599 0.055 Uiso 1 1 calc R
H1B H -0.2777 0.5896 0.4726 0.055 Uiso 1 1 calc R
S1 S -0.08616(10) 0.56461(3) 0.37210(6) 0.0509(2) Uani 1 1 d .
N1 N 0.3087(3) 0.56937(9) 0.64034(18) 0.0379(6) Uani 1 1 d .
C2 C 0.3304(4) 0.54858(11) 0.5515(3) 0.0452(8) Uani 1 1 d .
H2 H 0.4325 0.5343 0.5443 0.054 Uiso 1 1 calc R
C3 C 0.2134(4) 0.54690(11) 0.4708(2) 0.0436(8) Uani 1 1 d .
H3 H 0.2363 0.5318 0.4110 0.052 Uiso 1 1 calc R
C4 C 0.0590(4) 0.56794(11) 0.4781(2) 0.0376(7) Uani 1 1 d .
C5 C 0.0347(4) 0.58923(12) 0.5701(2) 0.0460(9) Uani 1 1 d .
H5 H -0.0660 0.6039 0.5794 0.055 Uiso 1 1 calc R
C6 C 0.1604(4) 0.58863(12) 0.6478(2) 0.0469(9) Uani 1 1 d .
H6 H 0.1405 0.6026 0.7092 0.056 Uiso 1 1 calc R
N11 N -0.2541(5) 0.73097(15) 0.0929(3) 0.0750(10) Uani 1 1 d .
C12 C -0.2889(4) 0.68058(15) 0.1085(3) 0.0637(11) Uani 1 1 d .
H12 H -0.3178 0.6586 0.0533 0.076 Uiso 1 1 calc R
C13 C -0.2840(4) 0.65913(13) 0.2030(3) 0.0542(9) Uani 1 1 d .
H13 H -0.3068 0.6232 0.2111 0.065 Uiso 1 1 calc R
C14 C -0.2449(4) 0.69149(13) 0.2858(3) 0.0514(9) Uani 1 1 d .
C15 C -0.2125(5) 0.74399(15) 0.2687(3) 0.0866(14) Uani 1 1 d .
H15 H -0.1872 0.7672 0.3224 0.104 Uiso 1 1 calc R
C16 C -0.2173(6) 0.76215(16) 0.1725(4) 0.0988(16) Uani 1 1 d .
H16 H -0.1938 0.7979 0.1623 0.119 Uiso 1 1 calc R
H11 H -0.253(17) 0.745(5) 0.032(6) 0.119 Uiso 0.50 1 d P
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
N1 Cu1 N1 176.26(14) 2_656 .
N1 Cu1 Cl1 88.13(7) 2_656 .
N1 Cu1 Cl1 88.13(7) . .
N1 Cu1 Cl2 87.10(7) 2_656 2_656
N1 Cu1 Cl2 95.10(7) . 2_656
Cl1 Cu1 Cl2 125.83(2) . 2_656
N1 Cu1 Cl2 95.09(7) 2_656 .
N1 Cu1 Cl2 87.10(7) . .
Cl1 Cu1 Cl2 125.83(2) . .
Cl2 Cu1 Cl2 108.34(4) 2_656 .
C14 S11 C1 104.03(15) . .
S11 C1 S1 116.83(15) . .
C4 S1 C1 103.90(14) . .
C6 N1 C2 115.9(3) . .
C6 N1 Cu1 125.1(2) . .
C2 N1 Cu1 119.0(2) . .
N1 C2 C3 124.3(3) . .
C2 C3 C4 119.7(3) . .
C5 C4 C3 116.4(3) . .
C5 C4 S1 126.0(2) . .
C3 C4 S1 117.6(2) . .
C6 C5 C4 119.6(3) . .
N1 C6 C5 124.0(3) . .
C12 N11 C16 118.0(3) . .
N11 C12 C13 122.7(4) . .
C12 C13 C14 119.4(3) . .
C15 C14 C13 117.4(3) . .
C15 C14 S11 115.8(3) . .
C13 C14 S11 126.8(3) . .
C16 C15 C14 119.8(4) . .
N11 C16 C15 122.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.020(2) 2_656
Cu1 N1 2.020(2) .
Cu1 Cl1 2.3312(13) .
Cu1 Cl2 2.3777(8) 2_656
Cu1 Cl2 2.3778(8) .
S11 C14 1.744(3) .
S11 C1 1.790(3) .
C1 S1 1.795(3) .
S1 C4 1.743(3) .
N1 C6 1.329(3) .
N1 C2 1.336(4) .
C2 C3 1.358(4) .
C3 C4 1.393(4) .
C4 C5 1.384(4) .
C5 C6 1.375(4) .
N11 C12 1.318(4) .
N11 C16 1.329(5) .
C12 C13 1.375(4) .
C13 C14 1.382(4) .
C14 C15 1.369(4) .
C15 C16 1.366(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N11 0.88(7) 1.80(7) 2.682(6) 177(13) 7_465
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
C14 S11 C1 S1 71.0(2) .
S11 C1 S1 C4 74.16(19) .
N1 Cu1 N1 C6 117.9(2) 2_656
Cl1 Cu1 N1 C6 117.9(2) .
Cl2 Cu1 N1 C6 -8.0(2) 2_656
Cl2 Cu1 N1 C6 -116.1(2) .
N1 Cu1 N1 C2 -64.6(2) 2_656
Cl1 Cu1 N1 C2 -64.6(2) .
Cl2 Cu1 N1 C2 169.6(2) 2_656
Cl2 Cu1 N1 C2 61.4(2) .
C6 N1 C2 C3 0.9(4) .
Cu1 N1 C2 C3 -176.8(2) .
N1 C2 C3 C4 0.2(5) .
C2 C3 C4 C5 -0.6(4) .
C2 C3 C4 S1 -180.0(2) .
C1 S1 C4 C5 7.0(3) .
C1 S1 C4 C3 -173.7(2) .
C3 C4 C5 C6 0.0(4) .
S1 C4 C5 C6 179.3(2) .
C2 N1 C6 C5 -1.6(4) .
Cu1 N1 C6 C5 176.0(2) .
C4 C5 C6 N1 1.2(5) .
C16 N11 C12 C13 -1.8(6) .
N11 C12 C13 C14 1.5(6) .
C12 C13 C14 C15 -0.1(5) .
C12 C13 C14 S11 178.8(3) .
C1 S11 C14 C15 -172.5(3) .
C1 S11 C14 C13 8.6(4) .
C13 C14 C15 C16 -0.9(6) .
S11 C14 C15 C16 -179.9(3) .
C12 N11 C16 C15 0.7(7) .
C14 C15 C16 N11 0.7(7) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144304
