#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:43:45 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311659.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_2311659
loop_
_publ_author_name
'Kumar, Sandeep'
'Khajuria, Ruchi'
'Jassal, Amanpreet Kaur'
'Hundal, Geeta'
'Hundal, Maninder S.'
'Pandey, Sushil K.'
_publ_section_title
;
 Synthesis and structural characterization of donor-stabilized
 disubstituted diphenyldithiophosphates of nickel(II).
;
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              761
_journal_page_last               767
_journal_paper_doi               10.1107/S2052520614014966
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C46 H54 N2 Ni O4 P2 S4'
_chemical_formula_sum            'C46 H54 N2 Ni O4 P2 S4'
_chemical_formula_weight         947.82
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.744(3)
_cell_angle_beta                 94.409(3)
_cell_angle_gamma                103.785(3)
_cell_formula_units_Z            1
_cell_length_a                   6.9327(6)
_cell_length_b                   11.2267(10)
_cell_length_c                   15.5768(14)
_cell_measurement_reflns_used    7562
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.03
_cell_measurement_theta_min      2.61
_cell_volume                     1137.67(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21578
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.694
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.694
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+1.7604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                4830
_reflns_number_total             6067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bp5066sup1.cif
_cod_data_source_block           34ETPY_LT_0m
_cod_database_code               2311659
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.0677(3) 0.28190(18) 0.58147(13) 0.0196(4) Uani d . 1 1
H H1 0.2021 0.2777 0.5934 0.024 Uiso calc R 1 1
C C2 0.0261(3) 0.39810(18) 0.60615(13) 0.0204(4) Uani d . 1 1
H H2 0.1308 0.4711 0.6346 0.025 Uiso calc R 1 1
C C3 -0.1682(3) 0.40885(18) 0.58952(13) 0.0185(4) Uani d . 1 1
C C4 -0.3132(3) 0.29777(19) 0.54879(14) 0.0220(4) Uani d . 1 1
H H4 -0.4486 0.2994 0.5360 0.026 Uiso calc R 1 1
C C5 -0.2605(3) 0.18473(18) 0.52689(13) 0.0197(4) Uani d . 1 1
H H5 -0.3633 0.1099 0.4999 0.024 Uiso calc R 1 1
C C6 -0.2117(3) 0.53688(19) 0.61347(15) 0.0254(4) Uani d . 1 1
H H6A -0.1779 0.5799 0.5654 0.030 Uiso calc R 1 1
H H6B -0.1220 0.5883 0.6683 0.030 Uiso calc R 1 1
C C7 -0.4272(3) 0.5349(2) 0.62813(16) 0.0306(5) Uani d . 1 1
H H7A -0.5175 0.4885 0.5732 0.046 Uiso calc R 1 1
H H7B -0.4398 0.6218 0.6448 0.046 Uiso calc R 1 1
H H7C -0.4629 0.4930 0.6758 0.046 Uiso calc R 1 1
C C8 0.1830(3) -0.16216(17) 0.77341(12) 0.0177(4) Uani d . 1 1
C C9 0.3586(3) -0.18614(19) 0.74746(13) 0.0216(4) Uani d . 1 1
H H9 0.3820 -0.1958 0.6873 0.026 Uiso calc R 1 1
C C10 0.5008(3) -0.19576(19) 0.81221(14) 0.0236(4) Uani d . 1 1
H H10 0.6232 -0.2115 0.7956 0.028 Uiso calc R 1 1
C C11 0.4683(3) -0.18297(18) 0.90031(14) 0.0211(4) Uani d . 1 1
C C12 0.2893(3) -0.15597(18) 0.92535(13) 0.0207(4) Uani d . 1 1
C C13 0.1482(3) -0.14537(18) 0.86079(13) 0.0195(4) Uani d . 1 1
H H13 0.0275 -0.1265 0.8770 0.023 Uiso calc R 1 1
C C14 0.2461(3) -0.1430(2) 1.01967(14) 0.0272(4) Uani d . 1 1
H H14A 0.1231 -0.1152 1.0260 0.041 Uiso calc R 1 1
H H14B 0.3582 -0.0804 1.0599 0.041 Uiso calc R 1 1
H H14C 0.2288 -0.2249 1.0346 0.041 Uiso calc R 1 1
C C15 0.6215(3) -0.1992(2) 0.96817(15) 0.0277(4) Uani d . 1 1
H H15A 0.7320 -0.2224 0.9388 0.042 Uiso calc R 1 1
H H15B 0.5583 -0.2661 0.9960 0.042 Uiso calc R 1 1
H H15C 0.6736 -0.1196 1.0138 0.042 Uiso calc R 1 1
C C16 -0.2481(3) 0.17716(19) 0.76843(13) 0.0202(4) Uani d . 1 1
H H23 -0.3591 0.1086 0.7391 0.024 Uiso calc R 1 1
C C17 -0.0633(3) 0.15749(17) 0.78973(12) 0.0163(3) Uani d . 1 1
C C18 0.1008(3) 0.25634(18) 0.83133(12) 0.0199(4) Uani d . 1 1
H H18 0.2268 0.2403 0.8445 0.024 Uiso calc R 1 1
C C19 0.0807(3) 0.37952(19) 0.85387(13) 0.0239(4) Uani d . 1 1
C C20 0.2612(4) 0.4870(2) 0.89871(18) 0.0368(5) Uani d . 1 1
H H20A 0.2937 0.5450 0.8601 0.055 Uiso calc R 1 1
H H20B 0.3757 0.4529 0.9100 0.055 Uiso calc R 1 1
H H20C 0.2311 0.5327 0.9552 0.055 Uiso calc R 1 1
C C21 -0.1064(3) 0.40187(19) 0.83379(13) 0.0237(4) Uani d . 1 1
C C22 -0.2671(3) 0.3004(2) 0.79108(13) 0.0231(4) Uani d . 1 1
H H22 -0.3935 0.3156 0.7770 0.028 Uiso calc R 1 1
C C23 -0.1330(4) 0.5345(2) 0.85876(17) 0.0358(5) Uani d . 1 1
H H23A -0.2727 0.5323 0.8407 0.054 Uiso calc R 1 1
H H23B -0.0445 0.5886 0.8285 0.054 Uiso calc R 1 1
H H23C -0.0993 0.5686 0.9232 0.054 Uiso calc R 1 1
N N1 -0.0728(2) 0.17447(14) 0.54145(10) 0.0156(3) Uani d . 1 1
O O1 0.02722(19) -0.16540(12) 0.70848(9) 0.0184(3) Uani d . 1 1
O O2 -0.0423(2) 0.03328(12) 0.77571(8) 0.0178(3) Uani d . 1 1
P P1 -0.00316(7) -0.04123(4) 0.68072(3) 0.01443(11) Uani d . 1 1
S S1 -0.24247(6) -0.09581(4) 0.59044(3) 0.01681(10) Uani d . 1 1
S S2 0.23636(6) 0.05391(4) 0.64104(3) 0.01646(10) Uani d . 1 1
Ni Ni1 0.0000 0.0000 0.5000 0.01306(9) Uani d S 1 2
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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 123.15(17)
N1 C1 H1 . . 118.4
C2 C1 H1 . . 118.4
C1 C2 C3 . . 120.40(17)
C1 C2 H2 . . 119.8
C3 C2 H2 . . 119.8
C4 C3 C2 . . 116.37(17)
C4 C3 C6 . . 123.37(17)
C2 C3 C6 . . 120.24(17)
C5 C4 C3 . . 119.92(17)
C5 C4 H4 . . 120.0
C3 C4 H4 . . 120.0
N1 C5 C4 . . 123.81(17)
N1 C5 H5 . . 118.1
C4 C5 H5 . . 118.1
C3 C6 C7 . . 115.49(17)
C3 C6 H6A . . 108.4
C7 C6 H6A . . 108.4
C3 C6 H6B . . 108.4
C7 C6 H6B . . 108.4
H6A C6 H6B . . 107.5
C6 C7 H7A . . 109.5
C6 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C6 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C9 C8 C13 . . 121.77(17)
C9 C8 O1 . . 119.49(17)
C13 C8 O1 . . 118.51(16)
C8 C9 C10 . . 117.97(18)
C8 C9 H9 . . 121.0
C10 C9 H9 . . 121.0
C11 C10 C9 . . 121.78(18)
C11 C10 H10 . . 119.1
C9 C10 H10 . . 119.1
C10 C11 C12 . . 119.05(18)
C10 C11 C15 . . 120.55(18)
C12 C11 C15 . . 120.39(19)
C13 C12 C11 . . 119.09(18)
C13 C12 C14 . . 119.86(18)
C11 C12 C14 . . 121.02(18)
C8 C13 C12 . . 120.30(18)
C8 C13 H13 . . 119.9
C12 C13 H13 . . 119.9
C12 C14 H14A . . 109.5
C12 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C12 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C11 C15 H15A . . 109.5
C11 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C11 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C17 C16 C22 . . 118.06(18)
C17 C16 H23 . . 121.0
C22 C16 H23 . . 121.0
C16 C17 C18 . . 121.83(17)
C16 C17 O2 . . 119.81(16)
C18 C17 O2 . . 118.16(16)
C17 C18 C19 . . 119.82(18)
C17 C18 H18 . . 120.1
C19 C18 H18 . . 120.1
C18 C19 C21 . . 119.45(18)
C18 C19 C20 . . 119.43(19)
C21 C19 C20 . . 121.1(2)
C19 C20 H20A . . 109.5
C19 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
C19 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
C22 C21 C19 . . 119.09(18)
C22 C21 C23 . . 120.38(19)
C19 C21 C23 . . 120.5(2)
C21 C22 C16 . . 121.74(18)
C21 C22 H22 . . 119.1
C16 C22 H22 . . 119.1
C21 C23 H23A . . 109.5
C21 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C21 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
C5 N1 C1 . . 116.34(16)
C5 N1 Ni1 . . 121.84(12)
C1 N1 Ni1 . . 121.80(12)
C8 O1 P1 . . 122.88(11)
C17 O2 P1 . . 121.25(11)
O1 P1 O2 . . 97.93(7)
O1 P1 S1 . . 106.94(5)
O2 P1 S1 . . 112.91(5)
O1 P1 S2 . . 113.24(6)
O2 P1 S2 . . 111.66(6)
S1 P1 S2 . . 113.15(3)
P1 S1 Ni1 . . 82.34(2)
P1 S2 Ni1 . . 81.66(2)
N1 Ni1 N1 2_556 . 180.00(7)
N1 Ni1 S1 2_556 2_556 90.12(4)
N1 Ni1 S1 . 2_556 89.88(4)
N1 Ni1 S1 2_556 . 89.88(4)
N1 Ni1 S1 . . 90.12(4)
S1 Ni1 S1 2_556 . 180.0
N1 Ni1 S2 2_556 . 90.58(4)
N1 Ni1 S2 . . 89.42(4)
S1 Ni1 S2 2_556 . 97.335(16)
S1 Ni1 S2 . . 82.666(16)
N1 Ni1 S2 2_556 2_556 89.42(4)
N1 Ni1 S2 . 2_556 90.58(4)
S1 Ni1 S2 2_556 2_556 82.665(16)
S1 Ni1 S2 . 2_556 97.335(16)
S2 Ni1 S2 . 2_556 180.00(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.344(2)
C1 C2 . 1.381(3)
C1 H1 . 0.9500
C2 C3 . 1.390(2)
C2 H2 . 0.9500
C3 C4 . 1.387(3)
C3 C6 . 1.511(3)
C4 C5 . 1.382(3)
C4 H4 . 0.9500
C5 N1 . 1.340(2)
C5 H5 . 0.9500
C6 C7 . 1.524(3)
C6 H6A . 0.9900
C6 H6B . 0.9900
C7 H7A . 0.9800
C7 H7B . 0.9800
C7 H7C . 0.9800
C8 C9 . 1.379(3)
C8 C13 . 1.380(3)
C8 O1 . 1.410(2)
C9 C10 . 1.395(3)
C9 H9 . 0.9500
C10 C11 . 1.390(3)
C10 H10 . 0.9500
C11 C12 . 1.409(3)
C11 C15 . 1.511(3)
C12 C13 . 1.393(3)
C12 C14 . 1.505(3)
C13 H13 . 0.9500
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C15 H15A . 0.9800
C15 H15B . 0.9800
C15 H15C . 0.9800
C16 C17 . 1.379(3)
C16 C22 . 1.391(3)
C16 H23 . 0.9500
C17 C18 . 1.383(3)
C17 O2 . 1.408(2)
C18 C19 . 1.393(3)
C18 H18 . 0.9500
C19 C21 . 1.403(3)
C19 C20 . 1.511(3)
C20 H20A . 0.9800
C20 H20B . 0.9800
C20 H20C . 0.9800
C21 C22 . 1.389(3)
C21 C23 . 1.513(3)
C22 H22 . 0.9500
C23 H23A . 0.9800
C23 H23B . 0.9800
C23 H23C . 0.9800
N1 Ni1 . 2.1146(15)
O1 P1 . 1.6020(13)
O2 P1 . 1.6081(13)
P1 S1 . 1.9704(6)
P1 S2 . 1.9708(7)
S1 Ni1 . 2.4775(5)
S2 Ni1 . 2.5031(5)
Ni1 N1 2_556 2.1146(15)
Ni1 S1 2_556 2.4775(5)
Ni1 S2 2_556 2.5031(5)
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_4
_geom_torsion
N1 C1 C2 C3 . -0.4(3)
C1 C2 C3 C4 . 0.8(3)
C1 C2 C3 C6 . -177.69(19)
C2 C3 C4 C5 . -0.2(3)
C6 C3 C4 C5 . 178.32(19)
C3 C4 C5 N1 . -1.0(3)
C4 C3 C6 C7 . 25.3(3)
C2 C3 C6 C7 . -156.3(2)
C13 C8 C9 C10 . 1.3(3)
O1 C8 C9 C10 . -173.18(17)
C8 C9 C10 C11 . 0.6(3)
C9 C10 C11 C12 . -1.8(3)
C9 C10 C11 C15 . 177.48(19)
C10 C11 C12 C13 . 1.3(3)
C15 C11 C12 C13 . -178.05(18)
C10 C11 C12 C14 . 179.17(19)
C15 C11 C12 C14 . -0.2(3)
C9 C8 C13 C12 . -1.9(3)
O1 C8 C13 C12 . 172.67(17)
C11 C12 C13 C8 . 0.5(3)
C14 C12 C13 C8 . -177.40(18)
C22 C16 C17 C18 . -0.9(3)
C22 C16 C17 O2 . 173.95(17)
C16 C17 C18 C19 . 0.9(3)
O2 C17 C18 C19 . -173.99(17)
C17 C18 C19 C21 . -0.2(3)
C17 C18 C19 C20 . -179.57(19)
C18 C19 C21 C22 . -0.6(3)
C20 C19 C21 C22 . 178.8(2)
C18 C19 C21 C23 . 179.1(2)
C20 C19 C21 C23 . -1.5(3)
C19 C21 C22 C16 . 0.6(3)
C23 C21 C22 C16 . -179.1(2)
C17 C16 C22 C21 . 0.1(3)
C4 C5 N1 C1 . 1.4(3)
C4 C5 N1 Ni1 . -176.64(16)
C2 C1 N1 C5 . -0.7(3)
C2 C1 N1 Ni1 . 177.38(15)
C9 C8 O1 P1 . -95.39(19)
C13 C8 O1 P1 . 89.96(19)
C16 C17 O2 P1 . 85.35(19)
C18 C17 O2 P1 . -99.65(18)
C8 O1 P1 O2 . -61.83(15)
C8 O1 P1 S1 . -178.78(13)
C8 O1 P1 S2 . 55.90(15)
C17 O2 P1 O1 . 174.94(13)
C17 O2 P1 S1 . -72.83(13)
C17 O2 P1 S2 . 56.00(14)
O1 P1 S1 Ni1 . -121.63(6)
O2 P1 S1 Ni1 . 131.80(6)
S2 P1 S1 Ni1 . 3.74(3)
O1 P1 S2 Ni1 . 118.20(6)
O2 P1 S2 Ni1 . -132.42(6)
S1 P1 S2 Ni1 . -3.71(3)
C5 N1 Ni1 S1 2_556 121.70(15)
C1 N1 Ni1 S1 2_556 -56.26(14)
C5 N1 Ni1 S1 . -58.30(15)
C1 N1 Ni1 S1 . 123.74(14)
C5 N1 Ni1 S2 . -140.96(15)
C1 N1 Ni1 S2 . 41.07(14)
C5 N1 Ni1 S2 2_556 39.04(15)
C1 N1 Ni1 S2 2_556 -138.93(14)
P1 S1 Ni1 N1 2_556 87.87(4)
P1 S1 Ni1 N1 . -92.13(4)
P1 S1 Ni1 S2 . -2.73(2)
P1 S1 Ni1 S2 2_556 177.27(2)
P1 S2 Ni1 N1 2_556 -87.07(5)
P1 S2 Ni1 N1 . 92.93(5)
P1 S2 Ni1 S1 2_556 -177.27(2)
P1 S2 Ni1 S1 . 2.73(2)
