#------------------------------------------------------------------------------
#$Date: 2022-07-06 23:17:07 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022631.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022631
loop_
_publ_author_name
'Jotani, Mukesh M.'
'Arman, Hadi D.'
'Poplaukhin, Pavel'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Bis(N,N-diethyldithiocarbamato-κ2S,S')(3-hydroxypyridine-\kN)zinc and
 bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ2S,S'](3-hydroxypyridine-\kN)zinc:
 crystal structures and Hirshfeld surface analysis
;
_journal_coden_ASTM              ACSECI
_journal_coeditor_code           HB7628
_journal_issue                   12
_journal_name_full
;
 Acta Crystallographica, Section E: Crystallographic Communications
;
_journal_page_first              1700
_journal_page_last               1709
_journal_paper_doi               10.1107/S205698901601728X
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          '[Zn (C4 H8 N O S2)2 (C5 H5 N O)]'
_chemical_formula_moiety         'C13 H21 N3 O3 S4 Zn'
_chemical_formula_sum            'C13 H21 N3 O3 S4 Zn'
_chemical_formula_weight         460.94
_chemical_name_systematic
Bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ²S,S'](3-hydroxypyridine-κN)zinc
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                102.154(4)
_cell_angle_beta                 106.989(4)
_cell_angle_gamma                93.466(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8645(19)
_cell_length_b                   9.956(2)
_cell_length_c                   11.473(3)
_cell_measurement_reflns_used    4145
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.57
_cell_measurement_theta_min      2.49
_cell_volume                     938.6(4)
_computing_cell_refinement
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_data_collection
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_data_reduction
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku AFC12κ/SATURN724'
_diffrn_measurement_method       ω
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6836
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        27.499
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.423
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       slab
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0316
_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)+(0.0370P)²+0.6872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                4133
_reflns_number_total             4249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7628sup1_II.cif
_cod_data_source_block           II
_cod_database_code               2022631
_publcif_datablock.id            {da9ee6d5-6e6c-4a13-80c9-1434e53164c0}
_shelx_shelxl_version_number     2014/7
_iucr_geom_hbonds_special_details
;
Cg1 is the centroid of the (Zn,S3,S4,C5) chelate ring.
;
_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   0.560
_shelx_estimated_absorpt_t_max   0.666
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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
Zn Zn 0.76357(3) 0.49975(2) 0.25271(2) 0.01863(8) Uani 1 1 d . . . . .
S1 S 0.97385(5) 0.65936(5) 0.26357(4) 0.01674(11) Uani 1 1 d . . . . .
S2 S 0.69910(6) 0.58080(5) 0.03011(5) 0.01835(11) Uani 1 1 d . . . . .
S3 S 0.64889(6) 0.27205(5) 0.14638(4) 0.01739(11) Uani 1 1 d . . . . .
S4 S 0.90377(6) 0.34805(5) 0.38990(4) 0.01782(11) Uani 1 1 d . . . . .
O1 O 0.74043(18) 0.85049(17) -0.09808(15) 0.0260(3) Uani 1 1 d D . . . .
H1O H 0.695(3) 0.783(2) -0.083(3) 0.039 Uiso 1 1 d D U . . .
O2 O 0.45844(17) 0.01078(16) 0.24736(13) 0.0218(3) Uani 1 1 d D . . . .
H2O H 0.413(3) 0.051(3) 0.193(2) 0.033 Uiso 1 1 d D U . . .
O3 O 0.67339(19) 0.91603(16) 0.57620(15) 0.0285(3) Uani 1 1 d D . . . .
H3O H 0.624(3) 0.945(3) 0.627(2) 0.043 Uiso 1 1 d D U . . .
N1 N 0.98304(19) 0.70602(17) 0.04700(15) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.78664(19) 0.08741(16) 0.26777(15) 0.0161(3) Uani 1 1 d . . . . .
N3 N 0.62518(19) 0.59446(17) 0.35049(15) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.8924(2) 0.65371(18) 0.10539(18) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.9350(2) 0.6846(2) -0.09003(18) 0.0191(4) Uani 1 1 d . . . . .
H2A H 0.8502 0.6046 -0.1285 0.023 Uiso 1 1 calc R U . . .
H2B H 1.0271 0.6612 -0.1190 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8749(2) 0.8097(2) -0.1355(2) 0.0221(4) Uani 1 1 d . . . . .
H3A H 0.9619 0.8882 -0.1017 0.027 Uiso 1 1 calc R U . . .
H3B H 0.8450 0.7881 -0.2282 0.027 Uiso 1 1 calc R U . . .
C4 C 1.1446(2) 0.7770(2) 0.1154(2) 0.0252(4) Uani 1 1 d . . . . .
H4A H 1.1454 0.8372 0.1951 0.038 Uiso 1 1 calc R U . . .
H4B H 1.1789 0.8330 0.0647 0.038 Uiso 1 1 calc R U . . .
H4C H 1.2175 0.7081 0.1321 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7800(2) 0.22057(19) 0.26907(17) 0.0143(3) Uani 1 1 d . . . . .
C6 C 0.6826(2) -0.02451(19) 0.16625(18) 0.0181(4) Uani 1 1 d . . . . .
H6A H 0.7468 -0.0971 0.1421 0.022 Uiso 1 1 calc R U . . .
H6B H 0.6353 0.0126 0.0920 0.022 Uiso 1 1 calc R U . . .
C7 C 0.5502(2) -0.0887(2) 0.20439(18) 0.0193(4) Uani 1 1 d . . . . .
H7A H 0.4796 -0.1595 0.1316 0.023 Uiso 1 1 calc R U . . .
H7B H 0.5972 -0.1359 0.2718 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8976(2) 0.0451(2) 0.3718(2) 0.0232(4) Uani 1 1 d . . . . .
H8A H 1.0069 0.0797 0.3796 0.035 Uiso 1 1 calc R U . . .
H8B H 0.8852 -0.0562 0.3554 0.035 Uiso 1 1 calc R U . . .
H8C H 0.8751 0.0837 0.4499 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6861(2) 0.7161(2) 0.43240(18) 0.0175(4) Uani 1 1 d . . . . .
H9 H 0.7921 0.7530 0.4436 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6007(2) 0.7911(2) 0.50204(18) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.4471(2) 0.7342(2) 0.48828(19) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.3855 0.7818 0.5347 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3863(2) 0.6063(2) 0.4053(2) 0.0249(4) Uani 1 1 d . . . . .
H12 H 0.2826 0.5646 0.3953 0.030 Uiso 1 1 calc R U . . .
C13 C 0.4768(2) 0.5400(2) 0.33723(19) 0.0221(4) Uani 1 1 d . . . . .
H13 H 0.4331 0.4534 0.2794 0.027 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'
O O 0.0106 0.0060 '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
N3 Zn S1 109.72(5) . .
N3 Zn S3 110.80(5) . .
S1 Zn S3 139.04(2) . .
N3 Zn S4 103.07(5) . .
S1 Zn S4 102.00(2) . .
S3 Zn S4 74.41(2) . .
N3 Zn S2 107.89(5) . .
S1 Zn S2 70.825(18) . .
S3 Zn S2 91.20(2) . .
S4 Zn S2 148.839(18) . .
C1 S1 Zn 90.54(6) . .
C1 S2 Zn 77.85(7) . .
C5 S3 Zn 86.67(6) . .
C5 S4 Zn 81.43(7) . .
C3 O1 H1O 109(2) . .
C7 O2 H2O 113(2) . .
C10 O3 H3O 110(2) . .
C1 N1 C4 121.53(17) . .
C1 N1 C2 122.52(16) . .
C4 N1 C2 115.68(16) . .
C5 N2 C8 120.74(16) . .
C5 N2 C6 122.91(16) . .
C8 N2 C6 116.33(15) . .
C9 N3 C13 118.73(17) . .
C9 N3 Zn 118.04(13) . .
C13 N3 Zn 123.22(14) . .
N1 C1 S2 122.54(15) . .
N1 C1 S1 118.66(14) . .
S2 C1 S1 118.79(11) . .
N1 C2 C3 113.44(16) . .
N1 C2 H2A 108.9 . .
C3 C2 H2A 108.9 . .
N1 C2 H2B 108.9 . .
C3 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
O1 C3 C2 112.64(16) . .
O1 C3 H3A 109.1 . .
C2 C3 H3A 109.1 . .
O1 C3 H3B 109.1 . .
C2 C3 H3B 109.1 . .
H3A C3 H3B 107.8 . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N2 C5 S4 121.34(14) . .
N2 C5 S3 121.19(14) . .
S4 C5 S3 117.46(11) . .
N2 C6 C7 112.02(16) . .
N2 C6 H6A 109.2 . .
C7 C6 H6A 109.2 . .
N2 C6 H6B 109.2 . .
C7 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
O2 C7 C6 112.50(16) . .
O2 C7 H7A 109.1 . .
C6 C7 H7A 109.1 . .
O2 C7 H7B 109.1 . .
C6 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
N2 C8 H8A 109.5 . .
N2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N3 C9 C10 122.79(18) . .
N3 C9 H9 118.6 . .
C10 C9 H9 118.6 . .
O3 C10 C9 116.64(18) . .
O3 C10 C11 125.07(18) . .
C9 C10 C11 118.27(19) . .
C12 C11 C10 118.52(19) . .
C12 C11 H11 120.7 . .
C10 C11 H11 120.7 . .
C13 C12 C11 119.77(19) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
N3 C13 C12 121.87(19) . .
N3 C13 H13 119.1 . .
C12 C13 H13 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn N3 2.0375(16) .
Zn S1 2.3319(6) .
Zn S3 2.3437(7) .
Zn S4 2.5275(6) .
Zn S2 2.7514(8) .
S1 C1 1.733(2) .
S2 C1 1.7119(19) .
S3 C5 1.7364(19) .
S4 C5 1.7140(19) .
O1 C3 1.433(2) .
O1 H1O 0.833(10) .
O2 C7 1.418(2) .
O2 H2O 0.833(10) .
O3 C10 1.350(2) .
O3 H3O 0.834(10) .
N1 C1 1.333(2) .
N1 C4 1.468(2) .
N1 C2 1.468(2) .
N2 C5 1.328(2) .
N2 C8 1.464(2) .
N2 C6 1.466(2) .
N3 C9 1.337(3) .
N3 C13 1.345(3) .
C2 C3 1.516(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 C7 1.518(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.393(3) .
C9 H9 0.9500 .
C10 C11 1.394(3) .
C11 C12 1.387(3) .
C11 H11 0.9500 .
C12 C13 1.379(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
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
O1 H1O S2 0.84(2) 2.61(2) 3.371(2) 152(3) .
O2 H2O O1 0.83(3) 1.94(3) 2.734(2) 161(3) 2_665
O3 H3O O2 0.84(3) 1.79(2) 2.619(2) 170(3) 2_666
C2 H2B Cg1 0.99 2.76 3.689(2) 156 2_765
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
C4 N1 C1 S2 175.51(15) . . . .
C2 N1 C1 S2 -10.8(2) . . . .
C4 N1 C1 S1 -4.7(2) . . . .
C2 N1 C1 S1 169.02(14) . . . .
Zn S2 C1 N1 167.26(16) . . . .
Zn S2 C1 S1 -12.55(9) . . . .
Zn S1 C1 N1 -165.30(14) . . . .
Zn S1 C1 S2 14.52(10) . . . .
C1 N1 C2 C3 102.8(2) . . . .
C4 N1 C2 C3 -83.2(2) . . . .
N1 C2 C3 O1 -58.9(2) . . . .
C8 N2 C5 S4 1.6(3) . . . .
C6 N2 C5 S4 179.87(14) . . . .
C8 N2 C5 S3 -179.97(15) . . . .
C6 N2 C5 S3 -1.7(3) . . . .
Zn S4 C5 N2 176.79(16) . . . .
Zn S4 C5 S3 -1.66(9) . . . .
Zn S3 C5 N2 -176.68(15) . . . .
Zn S3 C5 S4 1.77(10) . . . .
C5 N2 C6 C7 -103.9(2) . . . .
C8 N2 C6 C7 74.4(2) . . . .
N2 C6 C7 O2 55.4(2) . . . .
C13 N3 C9 C10 -2.0(3) . . . .
Zn N3 C9 C10 178.55(14) . . . .
N3 C9 C10 O3 -176.43(17) . . . .
N3 C9 C10 C11 2.1(3) . . . .
O3 C10 C11 C12 177.9(2) . . . .
C9 C10 C11 C12 -0.5(3) . . . .
C10 C11 C12 C13 -1.1(3) . . . .
C9 N3 C13 C12 0.2(3) . . . .
Zn N3 C13 C12 179.67(16) . . . .
C11 C12 C13 N3 1.3(3) . . . .
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{687b4131-b9e9-4956-8180-319fb9f745f5} '_geom_extra_table_headA'
{687b4131-b9e9-4956-8180-319fb9f745f5} '_geom_hbond_atom_site_label_D'
{da9ee6d5-6e6c-4a13-80c9-1434e53164c0} '_geom_hbond_atom_site_label_D'
{687b4131-b9e9-4956-8180-319fb9f745f5} '_geom_extra_table_headB'
{687b4131-b9e9-4956-8180-319fb9f745f5} '_geom_extra_table_headC'
{92d4c804-1fc9-4242-84e8-84b0d42cfb38} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{687b4131-b9e9-4956-8180-319fb9f745f5} y y y
{da9ee6d5-6e6c-4a13-80c9-1434e53164c0} y y y
{92d4c804-1fc9-4242-84e8-84b0d42cfb38} ? ? ?
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

_cod_database_fobs_code 2022631
