#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/62/7226267.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_7226267
loop_
_publ_author_name
'Angeloski, Alexander'
'Hook, James M.'
'Bhadbhade, Mohan'
'Baker, Anthony T.'
'McDonagh, Andrew M.'
_publ_section_title
;
 Intramolecular H⋯S interactions in metal
 di-(isopropyl)dithiocarbamate complexes
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7070
_journal_paper_doi               10.1039/C6CE01475E
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C7 H14 N S2), H20 Na2 O10'
_chemical_formula_sum            'C14 H48 N2 Na2 O10 S4'
_chemical_formula_weight         578.76
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-28 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                92.183(8)
_cell_angle_beta                 95.095(8)
_cell_angle_gamma                106.851(8)
_cell_formula_units_Z            1
_cell_length_a                   5.9472(11)
_cell_length_b                   7.7189(16)
_cell_length_c                   17.425(3)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.808
_cell_measurement_theta_min      3.075
_cell_volume                     760.8(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0601
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18709
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.006
_diffrn_reflns_theta_min         2.763
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1663 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.9019. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0323
_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)+(0.0277P)²+0.0641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2666
_reflns_number_total             3304
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01475e2.cif
_cod_data_source_block           fulldata_a
_cod_depositor_comments          'Adding full bibliography for 7226267.cif.'
_cod_database_code               7226267
_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
;
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method 'Diethy Ether, Methanol'
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
S1 S 0.27350(7) 0.08607(6) 0.68550(2) 0.01877(11) Uani 1 1 d .
S2 S 0.50966(7) 0.41117(6) 0.79143(2) 0.02235(12) Uani 1 1 d .
N1 N 0.1825(2) 0.12109(17) 0.83280(7) 0.0145(3) Uani 1 1 d .
C2 C 0.0042(3) -0.0613(2) 0.81991(9) 0.0170(3) Uani 1 1 d .
C1 C 0.3083(3) 0.2000(2) 0.77642(9) 0.0154(3) Uani 1 1 d .
C5 C 0.1995(3) 0.2059(2) 0.91255(9) 0.0183(4) Uani 1 1 d .
C3 C -0.2434(3) -0.0514(3) 0.83059(12) 0.0257(4) Uani 1 1 d .
C7 C 0.4393(3) 0.2350(3) 0.95854(11) 0.0255(4) Uani 1 1 d .
C6 C 0.1139(3) 0.3735(3) 0.91434(12) 0.0261(4) Uani 1 1 d .
C4 C 0.0755(3) -0.1983(3) 0.86943(12) 0.0260(4) Uani 1 1 d .
Na1 Na 0.50427(10) 0.66450(8) 0.57169(3) 0.01882(16) Uani 1 1 d .
O4 O 0.2188(2) 0.73175(19) 0.48176(7) 0.0242(3) Uani 1 1 d D
O1 O 0.2567(2) 0.65208(18) 0.67762(7) 0.0228(3) Uani 1 1 d D
O2 O 0.7667(2) 0.51553(18) 0.63652(7) 0.0246(3) Uani 1 1 d D
O5 O 0.7095(2) 0.97031(17) 0.61655(7) 0.0240(3) Uani 1 1 d D
O3 O 0.7188(2) 0.64975(16) 0.46333(7) 0.0200(3) Uani 1 1 d D
H2 H 0.004(3) -0.099(2) 0.7645(10) 0.017(4) Uiso 1 1 d .
H7A H 0.557(3) 0.325(2) 0.9404(10) 0.023(5) Uiso 1 1 d .
H3A H -0.265(3) -0.025(2) 0.8840(11) 0.030(5) Uiso 1 1 d .
H6A H 0.226(3) 0.474(3) 0.8984(10) 0.025(5) Uiso 1 1 d .
H7B H 0.426(3) 0.268(2) 1.0114(11) 0.024(5) Uiso 1 1 d .
H5 H 0.085(3) 0.112(2) 0.9385(9) 0.016(4) Uiso 1 1 d .
H6B H -0.044(4) 0.348(3) 0.8828(11) 0.037(5) Uiso 1 1 d .
H4A H 0.079(3) -0.171(2) 0.9233(11) 0.029(5) Uiso 1 1 d .
H3B H -0.352(3) -0.168(3) 0.8159(11) 0.033(5) Uiso 1 1 d .
H3C H -0.280(3) 0.043(3) 0.8003(11) 0.034(5) Uiso 1 1 d .
H4B H -0.037(3) -0.317(3) 0.8566(11) 0.036(5) Uiso 1 1 d .
H4C H 0.236(3) -0.208(2) 0.8602(10) 0.033(5) Uiso 1 1 d .
H6C H 0.098(3) 0.405(3) 0.9679(12) 0.038(5) Uiso 1 1 d .
H2A H 0.709(3) 0.470(3) 0.6766(10) 0.041(6) Uiso 1 1 d D
H5A H 0.640(4) 1.016(3) 0.6473(11) 0.046(7) Uiso 1 1 d D
H3D H 0.862(3) 0.668(3) 0.4732(11) 0.036(6) Uiso 1 1 d D
H3E H 0.703(4) 0.709(3) 0.4248(10) 0.047(7) Uiso 1 1 d D
H5B H 0.849(3) 0.999(3) 0.6391(12) 0.063(8) Uiso 1 1 d D
H1A H 0.313(4) 0.602(3) 0.7126(11) 0.056(8) Uiso 1 1 d D
H1B H 0.273(4) 0.759(2) 0.6959(11) 0.044(7) Uiso 1 1 d D
H7C H 0.490(3) 0.121(3) 0.9581(11) 0.041(6) Uiso 1 1 d .
H2B H 0.912(3) 0.561(3) 0.6505(12) 0.050(7) Uiso 1 1 d D
H4D H 0.219(4) 0.661(3) 0.4448(11) 0.056(8) Uiso 1 1 d D
H4E H 0.250(4) 0.834(2) 0.4638(12) 0.051(7) Uiso 1 1 d 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'
Na Na 0.0362 0.0249 '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'
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
C2 N1 C5 113.38(12) . .
C1 N1 C2 122.01(13) . .
C1 N1 C5 124.59(14) . .
N1 C2 C3 111.51(13) . .
N1 C2 C4 111.23(13) . .
N1 C2 H2 105.3(10) . .
C3 C2 H2 106.9(9) . .
C4 C2 C3 112.74(15) . .
C4 C2 H2 108.7(9) . .
S2 C1 S1 118.11(9) . .
N1 C1 S1 120.25(12) . .
N1 C1 S2 121.63(12) . .
N1 C5 C7 113.60(13) . .
N1 C5 C6 113.02(13) . .
N1 C5 H5 103.2(9) . .
C7 C5 H5 105.9(9) . .
C6 C5 C7 113.36(15) . .
C6 C5 H5 106.6(9) . .
C2 C3 H3A 113.2(10) . .
C2 C3 H3B 108.1(11) . .
C2 C3 H3C 110.6(11) . .
H3A C3 H3B 105.7(16) . .
H3A C3 H3C 107.4(15) . .
H3B C3 H3C 111.8(16) . .
C5 C7 H7A 112.5(11) . .
C5 C7 H7B 108.0(10) . .
C5 C7 H7C 112.1(11) . .
H7A C7 H7B 109.0(15) . .
H7A C7 H7C 107.8(15) . .
H7B C7 H7C 107.4(15) . .
C5 C6 H6A 111.3(11) . .
C5 C6 H6B 110.4(11) . .
C5 C6 H6C 108.1(11) . .
H6A C6 H6B 112.2(15) . .
H6A C6 H6C 105.2(16) . .
H6B C6 H6C 109.4(15) . .
C2 C4 H4A 113.1(11) . .
C2 C4 H4B 109.1(11) . .
C2 C4 H4C 112.1(11) . .
H4A C4 H4B 107.8(16) . .
H4A C4 H4C 107.1(15) . .
H4B C4 H4C 107.4(15) . .
O4 Na1 O1 92.33(5) . .
O4 Na1 O2 162.67(5) . .
O4 Na1 O3 84.60(5) . 2_666
O4 Na1 H4D 18.0(4) . .
O1 Na1 H4D 104.8(4) . .
O2 Na1 O1 95.54(5) . .
O2 Na1 O3 80.40(5) . 2_666
O2 Na1 H4D 145.1(4) . .
O5 Na1 O4 96.85(5) . .
O5 Na1 O1 88.03(5) . .
O5 Na1 O2 98.83(5) . .
O5 Na1 O3 97.38(5) . .
O5 Na1 O3 175.04(5) . 2_666
O5 Na1 H4D 109.7(5) . .
O3 Na1 O4 85.89(5) . .
O3 Na1 O1 87.17(5) 2_666 .
O3 Na1 O1 174.47(5) . .
O3 Na1 O2 84.83(5) . .
O3 Na1 O3 87.45(5) . 2_666
O3 Na1 H4D 72.3(4) . .
O3 Na1 H4D 72.8(5) 2_666 .
Na1 O4 H4D 99.6(16) . .
Na1 O4 H4E 119.5(15) . .
H4D O4 H4E 105(2) . .
Na1 O1 H1A 106.2(16) . .
Na1 O1 H1B 109.4(15) . .
H1A O1 H1B 106(2) . .
Na1 O2 H2A 109.3(14) . .
Na1 O2 H2B 126.9(15) . .
H2A O2 H2B 105(2) . .
Na1 O5 H5A 114.4(16) . .
Na1 O5 H5B 121.6(16) . .
H5A O5 H5B 102(2) . .
Na1 O3 Na1 92.55(5) . 2_666
Na1 O3 H3D 115.9(14) . .
Na1 O3 H3D 114.6(14) 2_666 .
Na1 O3 H3E 120.5(14) . .
Na1 O3 H3E 107.2(15) 2_666 .
H3D O3 H3E 106(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7484(16) .
S2 C1 1.7145(17) .
N1 C2 1.492(2) .
N1 C1 1.345(2) .
N1 C5 1.496(2) .
C2 C3 1.524(2) .
C2 C4 1.519(2) .
C2 H2 0.998(16) .
C5 C7 1.525(2) .
C5 C6 1.522(2) .
C5 H5 0.995(17) .
C3 H3A 0.971(19) .
C3 H3B 0.95(2) .
C3 H3C 0.98(2) .
C7 H7A 0.921(19) .
C7 H7B 0.963(18) .
C7 H7C 1.01(2) .
C6 H6A 0.938(19) .
C6 H6B 1.01(2) .
C6 H6C 0.98(2) .
C4 H4A 0.951(19) .
C4 H4B 0.97(2) .
C4 H4C 1.004(19) .
Na1 O4 2.3891(13) .
Na1 O1 2.4492(14) .
Na1 O2 2.4207(13) .
Na1 O5 2.3859(15) .
Na1 O3 2.3879(14) .
Na1 O3 2.4278(14) 2_666
Na1 H4D 2.66(2) .
O4 H4D 0.831(16) .
O4 H4E 0.834(16) .
O1 H1A 0.832(16) .
O1 H1B 0.849(15) .
O2 H2A 0.849(15) .
O2 H2B 0.844(16) .
O5 H5A 0.832(15) .
O5 H5B 0.849(13) .
O3 Na1 2.4278(14) 2_666
O3 H3D 0.825(15) .
O3 H3E 0.839(15) .
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
C2 H2 S1 0.998(16) 2.392(16) 3.0264(17) 120.8(12) .
C7 H7A S2 0.921(19) 2.714(17) 3.270(2) 119.7(13) .
C6 H6A S2 0.938(19) 2.741(17) 3.280(2) 117.4(13) .
O2 H2A S2 0.849(15) 2.406(16) 3.2336(15) 165.0(19) .
O5 H5A S1 0.832(15) 2.530(17) 3.2831(14) 151.1(19) 1_565
O3 H3D O4 0.825(15) 2.023(15) 2.8407(18) 171.0(19) 1_655
O2 H2B O1 0.844(16) 1.970(16) 2.8123(18) 175(2) 1_655
O4 H4D O2 0.831(16) 1.950(16) 2.7796(19) 176(2) 2_666
O4 H4E O5 0.834(16) 2.078(17) 2.8751(19) 160(2) 2_676
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
C2 N1 C1 S1 -2.19(18)
C2 N1 C1 S2 179.00(10)
C2 N1 C5 C7 116.30(15)
C2 N1 C5 C6 -112.71(16)
C1 N1 C2 C3 -117.20(16)
C1 N1 C2 C4 116.01(16)
C1 N1 C5 C7 -65.41(19)
C1 N1 C5 C6 65.6(2)
C5 N1 C2 C3 61.13(17)
C5 N1 C2 C4 -65.66(17)
C5 N1 C1 S1 179.67(10)
C5 N1 C1 S2 0.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202606
