#------------------------------------------------------------------------------
#$Date: 2024-03-07 05:10:42 +0200 (Thu, 07 Mar 2024) $
#$Revision: 290379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/11/1571169.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_1571169
loop_
_publ_author_name
'Khan, Sultana Shakila'
'Howlader, Md. Belayet Hossain'
'Sheikh, Md. Chanmiya'
'Miyatake, Ryuta'
'Zangrando, Ennio'
_publ_section_title
;
 Bis[S-octyl 3-(2-methylpropylidene)dithiocarbazato-κ2 N 3,S]nickel(II)
;
_journal_coeditor_code           WM4208
_journal_issue                   3
_journal_name_full               IUCrData
_journal_paper_doi               10.1107/S241431462400186X
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          '[Ni (C13 H25 N2 S2)2]'
_chemical_formula_moiety         'C26 H50 N4 Ni S4'
_chemical_formula_sum            'C26 H50 N4 Ni S4'
_chemical_formula_weight         605.65
_chemical_name_systematic
'Bis[S-octyl 3-(2-methylpropylidene)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                 106.532(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5962(4)
_cell_length_b                   18.4606(5)
_cell_length_c                   7.8973(2)
_cell_measurement_reflns_used    11425
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      1.83
_cell_volume                     1620.71(10)
_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
;
SHELXL (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 0.999
_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  0.0485
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15550
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.206
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Rigaku, 1995)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       platelet
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0359
_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)+(0.0305P)²+0.4396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                2920
_reflns_number_total             3702
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm4208.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1571169
_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   0.858
_shelx_estimated_absorpt_t_max   0.983
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 0.02167(9) Uani d 1 . .
S S1 0.60829(5) 0.43196(2) 0.71132(6) 0.02979(12) Uani d 1 . .
S S2 0.72948(5) 0.47341(3) 1.07771(6) 0.02978(12) Uani d 1 . .
N N1 0.50276(14) 0.56970(8) 0.68145(18) 0.0234(3) Uani d 1 . .
N N2 0.58197(14) 0.56067(8) 0.85404(18) 0.0256(3) Uani d 1 . .
C C1 0.3208(2) 0.71961(11) 0.7769(3) 0.0404(5) Uani d 1 . .
H H1A 0.324068 0.754490 0.871744 0.049 Uiso calc 1 . .
H H1B 0.258003 0.683641 0.773519 0.049 Uiso calc 1 . .
H H1C 0.302375 0.745114 0.663553 0.049 Uiso calc 1 . .
C C2 0.5430(2) 0.73600(11) 0.8188(3) 0.0428(5) Uani d 1 . .
H H2A 0.526392 0.761787 0.705932 0.051 Uiso calc 1 . .
H H2B 0.619737 0.710216 0.841194 0.051 Uiso calc 1 . .
H H2C 0.547434 0.770833 0.914072 0.051 Uiso calc 1 . .
C C3 0.44208(19) 0.68158(10) 0.8112(2) 0.0313(5) Uani d 1 . .
H H3 0.459840 0.655777 0.927134 0.038 Uiso calc 1 . .
C C4 0.43794(19) 0.62718(10) 0.6691(2) 0.0296(4) Uani d 1 . .
H H4 0.381339 0.636002 0.557753 0.035 Uiso calc 1 . .
C C5 0.63166(16) 0.49751(10) 0.8740(2) 0.0236(4) Uani d 1 . .
C C6 0.71997(18) 0.54982(10) 1.2175(2) 0.0284(4) Uani d 1 . .
H H6A 0.746134 0.594707 1.170536 0.034 Uiso calc 1 . .
H H6B 0.636015 0.556435 1.221253 0.034 Uiso calc 1 . .
C C7 0.80161(19) 0.53402(11) 1.4016(2) 0.0318(4) Uani d 1 . .
H H7A 0.774890 0.488545 1.445197 0.038 Uiso calc 1 . .
H H7B 0.884609 0.526391 1.394499 0.038 Uiso calc 1 . .
C C8 0.80273(18) 0.59419(11) 1.5335(2) 0.0318(4) Uani d 1 . .
H H8A 0.720371 0.600857 1.544146 0.038 Uiso calc 1 . .
H H8B 0.827396 0.640071 1.488945 0.038 Uiso calc 1 . .
C C9 0.88802(19) 0.57782(12) 1.7150(2) 0.0348(5) Uani d 1 . .
H H9A 0.864291 0.531126 1.756945 0.042 Uiso calc 1 . .
H H9B 0.970303 0.571941 1.703476 0.042 Uiso calc 1 . .
C C10 0.8907(2) 0.63547(11) 1.8535(2) 0.0351(5) Uani d 1 . .
H H10A 0.809207 0.640256 1.868614 0.042 Uiso calc 1 . .
H H10B 0.912217 0.682544 1.810629 0.042 Uiso calc 1 . .
C C11 0.97951(19) 0.61888(12) 2.0320(2) 0.0349(5) Uani d 1 . .
H H11A 0.956543 0.572383 2.075870 0.042 Uiso calc 1 . .
H H11B 1.060468 0.612554 2.015773 0.042 Uiso calc 1 . .
C C12 0.9864(2) 0.67654(12) 2.1710(3) 0.0391(5) Uani d 1 . .
H H12A 0.905293 0.683647 2.185985 0.047 Uiso calc 1 . .
H H12B 1.011361 0.722853 2.128801 0.047 Uiso calc 1 . .
C C13 1.0734(2) 0.65819(14) 2.3487(3) 0.0470(6) Uani d 1 . .
H H13A 1.153265 0.648814 2.334234 0.056 Uiso calc 1 . .
H H13B 1.045122 0.614956 2.396874 0.056 Uiso calc 1 . .
H H13C 1.078151 0.698927 2.429976 0.056 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 93.95(4) ?
N1 Ni1 S1 3_666 3_666 86.05(4) ?
N1 Ni1 S1 . . 86.05(4) ?
N1 Ni1 S1 3_666 . 93.95(4) ?
S1 Ni1 S1 3_666 . 180.00(2) ?
C5 S1 Ni1 . . 95.74(6) ?
C5 S2 C6 . . 103.11(8) ?
C4 N1 N2 . . 111.92(14) ?
C4 N1 Ni1 . . 127.63(13) ?
N2 N1 Ni1 . . 120.45(11) ?
C5 N2 N1 . . 111.59(14) ?
C3 C1 H1A . . 109.5 ?
C3 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C3 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C3 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 C1 . . 110.15(16) ?
C4 C3 C2 . . 109.32(17) ?
C1 C3 C2 . . 111.16(17) ?
C4 C3 H3 . . 108.7 ?
C1 C3 H3 . . 108.7 ?
C2 C3 H3 . . 108.7 ?
N1 C4 C3 . . 127.07(17) ?
N1 C4 H4 . . 116.5 ?
C3 C4 H4 . . 116.5 ?
N2 C5 S1 . . 124.84(14) ?
N2 C5 S2 . . 119.66(13) ?
S1 C5 S2 . . 115.50(10) ?
C7 C6 S2 . . 107.68(13) ?
C7 C6 H6A . . 110.2 ?
S2 C6 H6A . . 110.2 ?
C7 C6 H6B . . 110.2 ?
S2 C6 H6B . . 110.2 ?
H6A C6 H6B . . 108.5 ?
C8 C7 C6 . . 113.37(16) ?
C8 C7 H7A . . 108.9 ?
C6 C7 H7A . . 108.9 ?
C8 C7 H7B . . 108.9 ?
C6 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.7 ?
C7 C8 C9 . . 112.13(16) ?
C7 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
C7 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C10 C9 C8 . . 114.43(17) ?
C10 C9 H9A . . 108.7 ?
C8 C9 H9A . . 108.7 ?
C10 C9 H9B . . 108.7 ?
C8 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
C9 C10 C11 . . 113.32(17) ?
C9 C10 H10A . . 108.9 ?
C11 C10 H10A . . 108.9 ?
C9 C10 H10B . . 108.9 ?
C11 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C10 . . 114.35(17) ?
C12 C11 H11A . . 108.7 ?
C10 C11 H11A . . 108.7 ?
C12 C11 H11B . . 108.7 ?
C10 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
C11 C12 C13 . . 113.45(18) ?
C11 C12 H12A . . 108.9 ?
C13 C12 H12A . . 108.9 ?
C11 C12 H12B . . 108.9 ?
C13 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.7 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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 . 1.9193(14) ?
Ni1 N1 3_666 1.9193(14) ?
Ni1 S1 3_666 2.1788(5) ?
Ni1 S1 . 2.1788(5) ?
S1 C5 . 1.7295(18) ?
S2 C5 . 1.7416(18) ?
S2 C6 . 1.8138(19) ?
N1 C4 . 1.288(2) ?
N1 N2 . 1.420(2) ?
N2 C5 . 1.290(2) ?
C1 C3 . 1.526(3) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.530(3) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 C4 . 1.496(2) ?
C3 H3 . 1.0000 ?
C4 H4 . 0.9500 ?
C6 C7 . 1.521(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.520(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.522(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.520(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.521(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.514(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.516(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
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
C4 N1 N2 C5 . . . . 169.13(17) ?
Ni1 N1 N2 C5 . . . . -10.2(2) ?
N2 N1 C4 C3 . . . . 1.5(3) ?
Ni1 N1 C4 C3 . . . . -179.19(15) ?
C1 C3 C4 N1 . . . . -154.1(2) ?
C2 C3 C4 N1 . . . . 83.5(2) ?
N1 N2 C5 S1 . . . . 1.2(2) ?
N1 N2 C5 S2 . . . . -178.29(12) ?
Ni1 S1 C5 N2 . . . . 6.18(17) ?
Ni1 S1 C5 S2 . . . . -174.28(9) ?
C6 S2 C5 N2 . . . . 5.12(18) ?
C6 S2 C5 S1 . . . . -174.45(11) ?
C5 S2 C6 C7 . . . . 179.27(14) ?
S2 C6 C7 C8 . . . . 179.81(15) ?
C6 C7 C8 C9 . . . . -178.30(18) ?
C7 C8 C9 C10 . . . . -178.72(18) ?
C8 C9 C10 C11 . . . . -178.20(19) ?
C9 C10 C11 C12 . . . . 178.39(19) ?
C10 C11 C12 C13 . . . . 178.8(2) ?
