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#$Date: 2023-02-02 11:49:10 +0200 (Thu, 02 Feb 2023) $
#$Revision: 280765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106675.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_8106675
loop_
_publ_author_name
'Ajayi, Tomilola J.'
'Van Zyl, Werner E.'
_publ_section_title
;
 Crystal structure of
 bis(2-hydroxyethyl(phenyl)carbamodithioate)nickel(II), C18H20N2NiO2S4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              779
_journal_page_last               780
_journal_paper_doi               10.1515/ncrs-2017-0030
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C18 H20 N2 Ni O2 S4'
_chemical_formula_sum            'C18 H20 N2 Ni O2 S4'
_chemical_formula_weight         483.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 93.7760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.65480(10)
_cell_length_b                   6.85280(10)
_cell_length_c                   19.2214(4)
_cell_measurement_reflns_used    7351
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      4.09
_cell_volume                     1006.10(3)
_computing_cell_refinement       'APEX2, Ver. 2011.4-1 [1]'
_computing_data_collection       'APEX2, Ver. 2011.4-1 [1]'
_computing_data_reduction        'APEX2, Ver. 2011.4-1 [1]'
_computing_molecular_graphics    'ORTEP-3 [3]'
_computing_publication_material  'SHELXL-2014/7 [2]'
_computing_structure_refinement  'SHELXL-2014/7 [2]'
_computing_structure_solution    'SHELXL-2014/7 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9405
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.274
_diffrn_reflns_theta_min         4.089
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0189
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0109P)²+0.9807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0458
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1775
_reflns_number_total             1824
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0030_suppl.cif
_cod_data_source_block           NiHEPCT
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106675
_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   0.672
_shelx_estimated_absorpt_t_max   0.818
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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 0.2822(2) 0.1377(2) 0.08990(8) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.0678(2) 0.3867(2) 0.11675(8) 0.0161(3) Uani 1 1 d . . . . .
H2A H 0.145621 0.474122 0.091857 0.019 Uiso 1 1 calc R U . . .
H2B H 0.049375 0.445753 0.162698 0.019 Uiso 1 1 calc R U . . .
C3 C -0.1067(2) 0.3682(3) 0.07510(8) 0.0184(4) Uani 1 1 d . . . . .
H3A H -0.189063 0.289584 0.101182 0.022 Uiso 1 1 calc R U . . .
H3B H -0.158740 0.498766 0.066139 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0684(2) 0.0601(2) 0.17256(8) 0.0147(3) Uani 1 1 d . . . . .
C5 C 0.0976(2) 0.0816(3) 0.24421(9) 0.0181(3) Uani 1 1 d . . . . .
H5 H 0.176319 0.178026 0.263091 0.022 Uiso 1 1 calc R U . . .
C6 C 0.0094(2) -0.0410(3) 0.28789(9) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.028410 -0.029068 0.337045 0.027 Uiso 1 1 calc R U . . .
C7 C -0.1063(2) -0.1804(3) 0.25979(10) 0.0245(4) Uani 1 1 d . . . . .
H7 H -0.165351 -0.264509 0.289764 0.029 Uiso 1 1 calc R U . . .
C8 C -0.1359(2) -0.1975(3) 0.18808(10) 0.0229(4) Uani 1 1 d . . . . .
H8 H -0.216725 -0.291627 0.169135 0.027 Uiso 1 1 calc R U . . .
C9 C -0.0477(2) -0.0774(3) 0.14382(9) 0.0187(3) Uani 1 1 d . . . . .
H9 H -0.066859 -0.089356 0.094669 0.022 Uiso 1 1 calc R U . . .
N1 N 0.15241(17) 0.1943(2) 0.12704(7) 0.0140(3) Uani 1 1 d . . . . .
O1 O -0.07447(16) 0.27501(19) 0.01115(6) 0.0224(3) Uani 1 1 d . . . . .
H1 H -0.169627 0.236407 -0.008396 0.034 Uiso 1 1 calc R U . . .
S1 S 0.37801(5) 0.27626(6) 0.02821(2) 0.01610(10) Uani 1 1 d . U . . .
S2 S 0.37971(5) -0.08952(6) 0.09633(2) 0.01537(10) Uani 1 1 d . U . . .
Ni1 Ni 0.500000 0.000000 0.000000 0.01322(9) Uani 1 2 d S U 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'
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'
Ni Ni 0.3393 1.1124 '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 C1 S1 125.52(13) . .
N1 C1 S2 124.29(12) . .
S1 C1 S2 110.19(9) . .
N1 C2 C3 111.05(13) . .
N1 C2 H2A 109.4 . .
C3 C2 H2A 109.4 . .
N1 C2 H2B 109.4 . .
C3 C2 H2B 109.4 . .
H2A C2 H2B 108.0 . .
O1 C3 C2 107.27(13) . .
O1 C3 H3A 110.3 . .
C2 C3 H3A 110.3 . .
O1 C3 H3B 110.3 . .
C2 C3 H3B 110.3 . .
H3A C3 H3B 108.5 . .
C9 C4 C5 121.68(15) . .
C9 C4 N1 119.32(14) . .
C5 C4 N1 118.85(15) . .
C4 C5 C6 118.73(16) . .
C4 C5 H5 120.6 . .
C6 C5 H5 120.6 . .
C7 C6 C5 120.19(16) . .
C7 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C8 C7 C6 120.19(16) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C8 C9 120.30(17) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C4 C9 C8 118.89(16) . .
C4 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
C1 N1 C4 121.34(14) . .
C1 N1 C2 121.96(13) . .
C4 N1 C2 116.08(12) . .
C3 O1 H1 109.5 . .
C1 S1 NI1 84.36(6) . .
C1 S2 NI1 83.78(5) . .
S1 NI1 S1 180.0 . 3_655
S1 NI1 S2 100.090(15) . 3_655
S1 NI1 S2 79.910(15) 3_655 3_655
S1 NI1 S2 79.911(15) . .
S1 NI1 S2 100.090(15) 3_655 .
S2 NI1 S2 180.0 3_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.319(2) .
C1 S1 1.7204(16) .
C1 S2 1.7276(16) .
C2 N1 1.476(2) .
C2 C3 1.517(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 O1 1.421(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C9 1.385(2) .
C4 C5 1.388(2) .
C4 N1 1.449(2) .
C5 C6 1.394(2) .
C5 H5 0.9500 .
C6 C7 1.388(3) .
C6 H6 0.9500 .
C7 C8 1.387(3) .
C7 H7 0.9500 .
C8 C9 1.390(2) .
C8 H8 0.9500 .
C9 H9 0.9500 .
O1 H1 0.8400 .
S1 NI1 2.1947(4) .
S2 NI1 2.2084(4) .
NI1 S1 2.1947(4) 3_655
NI1 S2 2.2084(4) 3_655
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 H2A S1 0.99 2.61 3.1048(16) 111.3 .
C3 H3B S1 0.99 2.84 3.6946(17) 145 3_565
O1 H1 S2 0.84 2.47 3.2721(12) 160 3
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
N1 C2 C3 O1 -56.52(17) . . . .
C9 C4 C5 C6 1.0(2) . . . .
N1 C4 C5 C6 176.60(14) . . . .
C4 C5 C6 C7 -0.5(2) . . . .
C5 C6 C7 C8 -0.6(3) . . . .
C6 C7 C8 C9 1.1(3) . . . .
C5 C4 C9 C8 -0.5(2) . . . .
N1 C4 C9 C8 -176.06(15) . . . .
C7 C8 C9 C4 -0.6(3) . . . .
S1 C1 N1 C4 173.49(12) . . . .
S2 C1 N1 C4 -6.1(2) . . . .
S1 C1 N1 C2 2.9(2) . . . .
S2 C1 N1 C2 -176.72(11) . . . .
C9 C4 N1 C1 -75.7(2) . . . .
C5 C4 N1 C1 108.62(18) . . . .
C9 C4 N1 C2 95.44(17) . . . .
C5 C4 N1 C2 -80.23(18) . . . .
C3 C2 N1 C1 102.27(17) . . . .
C3 C2 N1 C4 -68.82(17) . . . .
N1 C1 S1 NI1 -167.96(14) . . . .
S2 C1 S1 NI1 11.67(7) . . . .
N1 C1 S2 NI1 168.03(14) . . . .
S1 C1 S2 NI1 -11.61(7) . . . .
