#------------------------------------------------------------------------------
#$Date: 2023-07-12 05:08:47 +0300 (Wed, 12 Jul 2023) $
#$Revision: 285171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022815.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_2022815
loop_
_publ_author_name
'Khan, Sultana Shakila'
'Howlader, Md. Belayet Hossain'
'Sheikh, Md. Chanmiya'
'Miyatake, Ryuta'
'Zangrando, Ennio'
_publ_section_title
;
 Crystal structure of
 bis{S-octyl-3-[(thiophen-2-yl)methylidene]dithiocarbazato-κ2 N
 3,S}nickel(II)
;
_journal_coeditor_code           PK2690
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023005935
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '[Ni (C14 H21 N2 S3)2]'
_chemical_formula_moiety         'C28 H42 N4 Ni S6'
_chemical_formula_sum            'C28 H42 N4 Ni S6'
_chemical_formula_weight         685.72
_chemical_name_systematic
Bis{S-octyl-3-[(thiophen-2-yl)methylidene]dithiocarbazato-κ²N³,S}nickel(II)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_cell_angle_alpha                90
_cell_angle_beta                 103.675(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.5444(6)
_cell_length_b                   5.5388(3)
_cell_length_c                   20.1592(8)
_cell_measurement_reflns_used    10434
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.08
_cell_volume                     1686.45(14)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2018)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2018)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2018)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15791
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.697
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Rigaku, 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       needle
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0446
_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)+(0.0329P)²+0.0128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                2621
_reflns_number_total             3850
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2690sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1686.44(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022815
_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   0.926
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.500000 0.500000 0.500000 0.02461(12) Uani d 1 . .
S S1 0.43249(4) 0.34173(13) 0.57239(3) 0.03295(17) Uani d 1 . .
S S2 0.30020(4) -0.04469(12) 0.55073(3) 0.03283(17) Uani d 1 . .
S S3 0.33321(4) -0.17114(13) 0.33566(3) 0.03364(17) Uani d 1 . .
N N1 0.43677(12) 0.2681(4) 0.43617(10) 0.0263(5) Uani d 1 . .
N N2 0.37776(13) 0.1034(4) 0.45452(10) 0.0274(5) Uani d 1 . .
C C1 0.32299(17) -0.2689(5) 0.25377(13) 0.0364(7) Uani d 1 . .
H H1 0.290649 -0.408991 0.235505 0.044 Uiso calc 1 . .
C C2 0.36579(17) -0.1259(5) 0.21773(13) 0.0384(7) Uani d 1 . .
H H2 0.366185 -0.152919 0.171263 0.046 Uiso calc 1 . .
C C3 0.40956(16) 0.0668(5) 0.25668(12) 0.0331(6) Uani d 1 . .
H H3 0.443110 0.184342 0.239444 0.040 Uiso calc 1 . .
C C4 0.39872(15) 0.0677(4) 0.32296(12) 0.0273(6) Uani d 1 . .
C C5 0.44139(15) 0.2400(5) 0.37290(12) 0.0289(6) Uani d 1 . .
H H5 0.478965 0.351305 0.357540 0.035 Uiso calc 1 . .
C C6 0.37280(14) 0.1323(4) 0.51739(12) 0.0255(5) Uani d 1 . .
C C7 0.25455(16) -0.2377(5) 0.47858(12) 0.0317(6) Uani d 1 . .
H H7A 0.228117 -0.136545 0.438453 0.038 Uiso calc 1 . .
H H7B 0.302730 -0.334361 0.467263 0.038 Uiso calc 1 . .
C C8 0.18415(17) -0.4070(5) 0.49347(13) 0.0338(6) Uani d 1 . .
H H8A 0.210547 -0.512821 0.532553 0.041 Uiso calc 1 . .
H H8B 0.136169 -0.311795 0.505600 0.041 Uiso calc 1 . .
C C9 0.14665(17) -0.5596(5) 0.43057(13) 0.0364(7) Uani d 1 . .
H H9A 0.123844 -0.450452 0.391478 0.044 Uiso calc 1 . .
H H9B 0.195365 -0.655482 0.419806 0.044 Uiso calc 1 . .
C C10 0.07291(17) -0.7307(5) 0.43757(13) 0.0368(6) Uani d 1 . .
H H10A 0.025185 -0.637168 0.450618 0.044 Uiso calc 1 . .
H H10B 0.096283 -0.847621 0.474588 0.044 Uiso calc 1 . .
C C11 0.03444(17) -0.8679(5) 0.37195(13) 0.0393(7) Uani d 1 . .
H H11A 0.011898 -0.749798 0.335090 0.047 Uiso calc 1 . .
H H11B 0.082584 -0.960448 0.359172 0.047 Uiso calc 1 . .
C C12 -0.03979(17) -1.0408(5) 0.37605(14) 0.0403(7) Uani d 1 . .
H H12A -0.016871 -1.163148 0.411632 0.048 Uiso calc 1 . .
H H12B -0.087282 -0.949827 0.390228 0.048 Uiso calc 1 . .
C C13 -0.0790(2) -1.1686(7) 0.30929(15) 0.0569(9) Uani d 1 . .
H H13A -0.102651 -1.046174 0.273913 0.068 Uiso calc 1 . .
H H13B -0.031228 -1.257274 0.294768 0.068 Uiso calc 1 . .
C C14 -0.1521(2) -1.3442(7) 0.31334(18) 0.0693(11) Uani d 1 . .
H H14A -0.128788 -1.469718 0.347054 0.083 Uiso calc 1 . .
H H14B -0.174872 -1.418856 0.268549 0.083 Uiso calc 1 . .
H H14C -0.200158 -1.257687 0.327044 0.083 Uiso calc 1 . .
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'
Ni Ni 0.3393 1.1124 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Ni1 N1 3_666 . 180.0 ?
N1 Ni1 S1 3_666 3_666 85.88(6) ?
N1 Ni1 S1 . 3_666 94.12(6) ?
N1 Ni1 S1 3_666 3_666 85.88(6) ?
N1 Ni1 S1 . 3_666 94.12(6) ?
S1 Ni1 S1 3_666 3_666 0.00(2) ?
N1 Ni1 S1 3_666 . 94.12(6) ?
N1 Ni1 S1 . . 85.88(6) ?
S1 Ni1 S1 3_666 . 180.0 ?
S1 Ni1 S1 3_666 . 180.0 ?
C6 S1 Ni1 . . 96.42(8) ?
C6 S2 C7 . . 100.88(12) ?
C1 S3 C4 . . 91.32(13) ?
C5 N1 N2 . . 111.8(2) ?
C5 N1 Ni1 . . 126.77(17) ?
N2 N1 Ni1 . . 121.46(14) ?
C6 N2 N1 . . 111.74(19) ?
C2 C1 S3 . . 112.9(2) ?
C2 C1 H1 . . 123.6 ?
S3 C1 H1 . . 123.6 ?
C1 C2 C3 . . 112.4(2) ?
C1 C2 H2 . . 123.8 ?
C3 C2 H2 . . 123.8 ?
C4 C3 C2 . . 112.9(2) ?
C4 C3 H3 . . 123.5 ?
C2 C3 H3 . . 123.5 ?
C3 C4 C5 . . 122.6(2) ?
C3 C4 S3 . . 110.53(18) ?
C5 C4 S3 . . 126.78(19) ?
N1 C5 C4 . . 130.1(2) ?
N1 C5 H5 . . 115.0 ?
C4 C5 H5 . . 115.0 ?
N2 C6 S1 . . 124.49(19) ?
N2 C6 S2 . . 119.99(18) ?
S1 C6 S2 . . 115.51(14) ?
C8 C7 S2 . . 111.63(17) ?
C8 C7 H7A . . 109.3 ?
S2 C7 H7A . . 109.3 ?
C8 C7 H7B . . 109.3 ?
S2 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
C9 C8 C7 . . 109.2(2) ?
C9 C8 H8A . . 109.8 ?
C7 C8 H8A . . 109.8 ?
C9 C8 H8B . . 109.8 ?
C7 C8 H8B . . 109.8 ?
H8A C8 H8B . . 108.3 ?
C10 C9 C8 . . 114.7(2) ?
C10 C9 H9A . . 108.6 ?
C8 C9 H9A . . 108.6 ?
C10 C9 H9B . . 108.6 ?
C8 C9 H9B . . 108.6 ?
H9A C9 H9B . . 107.6 ?
C9 C10 C11 . . 112.4(2) ?
C9 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
C9 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 114.6(2) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
C13 C12 C11 . . 113.4(2) ?
C13 C12 H12A . . 108.9 ?
C11 C12 H12A . . 108.9 ?
C13 C12 H12B . . 108.9 ?
C11 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.7 ?
C14 C13 C12 . . 113.7(3) ?
C14 C13 H13A . . 108.8 ?
C12 C13 H13A . . 108.8 ?
C14 C13 H13B . . 108.8 ?
C12 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N1 3_666 1.9168(19) ?
Ni1 N1 . 1.9168(19) ?
Ni1 S1 3_666 2.1735(7) ?
Ni1 S1 3_666 2.1735(7) ?
Ni1 S1 . 2.1735(7) ?
S1 C6 . 1.717(2) ?
S2 C6 . 1.745(2) ?
S2 C7 . 1.809(2) ?
S3 C1 . 1.709(3) ?
S3 C4 . 1.725(3) ?
N1 C5 . 1.304(3) ?
N1 N2 . 1.404(3) ?
N2 C6 . 1.298(3) ?
C1 C2 . 1.351(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.402(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.431(3) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.524(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.521(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.519(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.520(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.516(4) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.515(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.513(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 S1 4_565 0.95 3.00 3.684(3) 130.5 yes
C2 H2 S2 4 0.95 2.93 3.752(3) 145.6 yes
C5 H5 S1 3_666 0.95 2.42 3.067(3) 125.0 yes
C7 H7A S3 . 0.99 2.93 3.406(3) 110.3 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C6 . . . . -179.6(2) ?
Ni1 N1 N2 C6 . . . . 0.4(3) ?
C4 S3 C1 C2 . . . . -1.0(2) ?
S3 C1 C2 C3 . . . . 0.9(3) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C2 C3 C4 C5 . . . . 176.5(2) ?
C2 C3 C4 S3 . . . . -0.5(3) ?
C1 S3 C4 C3 . . . . 0.8(2) ?
C1 S3 C4 C5 . . . . -176.0(2) ?
N2 N1 C5 C4 . . . . -2.1(4) ?
Ni1 N1 C5 C4 . . . . 177.9(2) ?
C3 C4 C5 N1 . . . . 178.5(3) ?
S3 C4 C5 N1 . . . . -5.1(4) ?
N1 N2 C6 S1 . . . . -1.3(3) ?
N1 N2 C6 S2 . . . . 177.52(15) ?
Ni1 S1 C6 N2 . . . . 1.4(2) ?
Ni1 S1 C6 S2 . . . . -177.45(11) ?
C7 S2 C6 N2 . . . . 2.3(2) ?
C7 S2 C6 S1 . . . . -178.84(14) ?
C6 S2 C7 C8 . . . . -177.36(18) ?
S2 C7 C8 C9 . . . . 178.55(18) ?
C7 C8 C9 C10 . . . . -177.8(2) ?
C8 C9 C10 C11 . . . . 176.7(2) ?
C9 C10 C11 C12 . . . . -179.8(2) ?
C10 C11 C12 C13 . . . . 178.0(3) ?
C11 C12 C13 C14 . . . . 179.1(3) ?

_cod_database_fobs_code 2022815
