#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:43:45 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311658.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_2311658
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                99.315(4)
_cell_angle_beta                 98.447(3)
_cell_angle_gamma                112.821(3)
_cell_formula_units_Z            1
_cell_length_a                   9.5505(8)
_cell_length_b                   9.8010(8)
_cell_length_c                   14.2026(12)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.44
_cell_volume                     1176.64(17)
_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    'SHELXS-97 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18873
_diffrn_reflns_theta_full        27.32
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6450
_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    1.338
_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          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.4175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                4503
_reflns_number_total             5246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bp5066sup1.cif
_cod_data_source_block           35etpy_0m
_cod_database_code               2311658
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 0.5327(2) 0.20782(19) 0.42517(14) 0.0427(4) Uani d . 1 1
H H1 0.4292 0.1635 0.4296 0.051 Uiso calc R 1 1
C C2 0.6013(2) 0.1133(2) 0.39513(15) 0.0475(4) Uani d . 1 1
H H2 0.5443 0.0080 0.3798 0.057 Uiso calc R 1 1
C C3 0.7557(2) 0.1754(2) 0.38771(13) 0.0422(4) Uani d . 1 1
C C4 0.83193(19) 0.3330(2) 0.41028(13) 0.0405(4) Uani d . 1 1
H H4 0.9350 0.3802 0.4055 0.049 Uiso calc R 1 1
C C5 0.75535(18) 0.41989(19) 0.43978(12) 0.0364(3) Uani d . 1 1
H H5 0.8093 0.5255 0.4545 0.044 Uiso calc R 1 1
C C6 0.8352(2) 0.0752(2) 0.35582(18) 0.0592(5) Uani d . 1 1
H H6A 0.9446 0.1390 0.3618 0.071 Uiso calc R 1 1
H H6B 0.8293 0.0079 0.3997 0.071 Uiso calc R 1 1
C C7 0.7654(3) -0.0195(3) 0.25259(18) 0.0709(6) Uani d . 1 1
H H7A 0.6573 -0.0840 0.2461 0.106 Uiso calc R 1 1
H H7B 0.8200 -0.0814 0.2373 0.106 Uiso calc R 1 1
H H7C 0.7744 0.0462 0.2083 0.106 Uiso calc R 1 1
C C8 0.59751(19) 0.44665(19) 0.17368(12) 0.0378(3) Uani d . 1 1
C C9 0.6932(2) 0.3718(2) 0.17712(13) 0.0413(4) Uani d . 1 1
H H9 0.6734 0.2922 0.2084 0.050 Uiso calc R 1 1
C C10 0.8199(2) 0.4161(2) 0.13342(13) 0.0456(4) Uani d . 1 1
C C11 0.8462(2) 0.5349(2) 0.08748(14) 0.0485(4) Uani d . 1 1
H H11 0.9319 0.5662 0.0594 0.058 Uiso calc R 1 1
C C12 0.7482(2) 0.6085(2) 0.08213(13) 0.0463(4) Uani d . 1 1
C C13 0.6222(2) 0.5631(2) 0.12594(13) 0.0446(4) Uani d . 1 1
H H13 0.5550 0.6109 0.1232 0.053 Uiso calc R 1 1
C C14 0.9271(3) 0.3357(3) 0.1372(2) 0.0672(6) Uani d . 1 1
H H14A 0.9671 0.3400 0.2043 0.101 Uiso calc R 1 1
H H14B 1.0122 0.3850 0.1083 0.101 Uiso calc R 1 1
H H14C 0.8698 0.2311 0.1016 0.101 Uiso calc R 1 1
C C15 0.7780(3) 0.7351(3) 0.02916(16) 0.0630(6) Uani d . 1 1
H H15A 0.6994 0.7728 0.0323 0.094 Uiso calc R 1 1
H H15B 0.7747 0.6968 -0.0382 0.094 Uiso calc R 1 1
H H15C 0.8790 0.8164 0.0597 0.094 Uiso calc R 1 1
C C16 0.2901(2) 0.6754(2) 0.22377(13) 0.0412(4) Uani d . 1 1
C C17 0.2095(2) 0.6937(2) 0.29398(15) 0.0517(5) Uani d . 1 1
H H17 0.1899 0.6302 0.3371 0.062 Uiso calc R 1 1
C C18 0.1576(3) 0.8090(3) 0.29934(16) 0.0615(6) Uani d . 1 1
C C19 0.1929(3) 0.9038(2) 0.23628(17) 0.0644(6) Uani d . 1 1
H H19 0.1606 0.9823 0.2410 0.077 Uiso calc R 1 1
C C20 0.2745(3) 0.8863(2) 0.16629(17) 0.0603(6) Uani d . 1 1
C C21 0.3221(2) 0.7679(2) 0.15923(15) 0.0505(4) Uani d . 1 1
H H21 0.3747 0.7518 0.1115 0.061 Uiso calc R 1 1
C C22 0.0592(4) 0.8241(4) 0.3709(2) 0.1077(12) Uani d . 1 1
H H22A -0.0492 0.7726 0.3379 0.161 Uiso calc R 1 1
H H22B 0.0855 0.9301 0.3964 0.161 Uiso calc R 1 1
H H22C 0.0787 0.7793 0.4238 0.161 Uiso calc R 1 1
C C23 0.3114(4) 0.9920(3) 0.0974(2) 0.0979(10) Uani d . 1 1
H H23A 0.3577 1.0960 0.1347 0.147 Uiso calc R 1 1
H H23B 0.2169 0.9729 0.0522 0.147 Uiso calc R 1 1
H H23C 0.3830 0.9741 0.0617 0.147 Uiso calc R 1 1
P P1 0.41869(5) 0.49726(5) 0.28995(3) 0.03376(10) Uani d . 1 1
S S1 0.27203(5) 0.36042(5) 0.35399(3) 0.03779(11) Uani d . 1 1
S S2 0.59665(5) 0.66697(5) 0.38503(3) 0.03848(11) Uani d . 1 1
Ni Ni1 0.5000 0.5000 0.5000 0.03037(8) Uani d S 1 2
N N1 0.60740(15) 0.36043(15) 0.44840(10) 0.0343(3) Uani d . 1 1
O O1 0.47024(14) 0.39259(13) 0.21748(9) 0.0414(3) Uani d . 1 1
O O2 0.33424(15) 0.55433(14) 0.20882(9) 0.0439(3) Uani d . 1 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'
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'
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'
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 . . 123.48(16)
N1 C1 H1 . . 118.3
C2 C1 H1 . . 118.3
C1 C2 C3 . . 119.82(16)
C1 C2 H2 . . 120.1
C3 C2 H2 . . 120.1
C4 C3 C2 . . 116.63(15)
C4 C3 C6 . . 122.09(16)
C2 C3 C6 . . 121.27(17)
C5 C4 C3 . . 120.11(15)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
N1 C5 C4 . . 123.41(15)
N1 C5 H5 . . 118.3
C4 C5 H5 . . 118.3
C7 C6 C3 . . 113.64(18)
C7 C6 H6A . . 108.8
C3 C6 H6A . . 108.8
C7 C6 H6B . . 108.8
C3 C6 H6B . . 108.8
H6A C6 H6B . . 107.7
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 . . 121.48(16)
C9 C8 O1 . . 115.96(15)
C13 C8 O1 . . 122.50(15)
C8 C9 C10 . . 119.56(17)
C8 C9 H9 . . 120.2
C10 C9 H9 . . 120.2
C11 C10 C9 . . 118.79(17)
C11 C10 C14 . . 120.98(18)
C9 C10 C14 . . 120.23(18)
C10 C11 C12 . . 121.81(17)
C10 C11 H11 . . 119.1
C12 C11 H11 . . 119.1
C11 C12 C13 . . 118.81(18)
C11 C12 C15 . . 120.43(18)
C13 C12 C15 . . 120.76(18)
C8 C13 C12 . . 119.53(17)
C8 C13 H13 . . 120.2
C12 C13 H13 . . 120.2
C10 C14 H14A . . 109.5
C10 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C10 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C12 C15 H15A . . 109.5
C12 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C12 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C21 C16 C17 . . 122.07(17)
C21 C16 O2 . . 115.83(17)
C17 C16 O2 . . 121.93(16)
C16 C17 C18 . . 118.9(2)
C16 C17 H17 . . 120.5
C18 C17 H17 . . 120.5
C19 C18 C17 . . 118.9(2)
C19 C18 C22 . . 121.2(2)
C17 C18 C22 . . 119.8(2)
C18 C19 C20 . . 122.21(19)
C18 C19 H19 . . 118.9
C20 C19 H19 . . 118.9
C19 C20 C21 . . 118.7(2)
C19 C20 C23 . . 121.2(2)
C21 C20 C23 . . 120.2(2)
C16 C21 C20 . . 119.2(2)
C16 C21 H21 . . 120.4
C20 C21 H21 . . 120.4
C18 C22 H22A . . 109.5
C18 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C18 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C20 C23 H23A . . 109.5
C20 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C20 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
O1 P1 O2 . . 97.83(7)
O1 P1 S2 . . 113.19(5)
O2 P1 S2 . . 112.47(5)
O1 P1 S1 . . 106.59(5)
O2 P1 S1 . . 113.14(5)
S2 P1 S1 . . 112.61(3)
P1 S1 Ni1 . . 81.477(19)
P1 S2 Ni1 . . 81.675(19)
N1 Ni1 N1 . 2_666 180.00(5)
N1 Ni1 S2 . . 90.85(4)
N1 Ni1 S2 2_666 . 89.15(4)
N1 Ni1 S2 . 2_666 89.15(4)
N1 Ni1 S2 2_666 2_666 90.85(4)
S2 Ni1 S2 . 2_666 180.0
N1 Ni1 S1 . 2_666 90.04(4)
N1 Ni1 S1 2_666 2_666 89.96(4)
S2 Ni1 S1 . 2_666 98.666(15)
S2 Ni1 S1 2_666 2_666 81.334(15)
N1 Ni1 S1 . . 89.96(4)
N1 Ni1 S1 2_666 . 90.04(4)
S2 Ni1 S1 . . 81.333(15)
S2 Ni1 S1 2_666 . 98.667(15)
S1 Ni1 S1 2_666 . 180.0
C5 N1 C1 . . 116.54(14)
C5 N1 Ni1 . . 121.50(11)
C1 N1 Ni1 . . 121.94(11)
C8 O1 P1 . . 125.11(11)
C16 O2 P1 . . 127.77(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.341(2)
C1 C2 . 1.376(2)
C1 H1 . 0.9300
C2 C3 . 1.389(2)
C2 H2 . 0.9300
C3 C4 . 1.384(2)
C3 C6 . 1.511(2)
C4 C5 . 1.376(2)
C4 H4 . 0.9300
C5 N1 . 1.337(2)
C5 H5 . 0.9300
C6 C7 . 1.499(3)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 C9 . 1.376(2)
C8 C13 . 1.381(3)
C8 O1 . 1.405(2)
C9 C10 . 1.392(2)
C9 H9 . 0.9300
C10 C11 . 1.383(3)
C10 C14 . 1.515(3)
C11 C12 . 1.386(3)
C11 H11 . 0.9300
C12 C13 . 1.388(3)
C12 C15 . 1.510(3)
C13 H13 . 0.9300
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
C16 C21 . 1.375(3)
C16 C17 . 1.377(3)
C16 O2 . 1.401(2)
C17 C18 . 1.395(3)
C17 H17 . 0.9300
C18 C19 . 1.376(3)
C18 C22 . 1.509(3)
C19 C20 . 1.379(3)
C19 H19 . 0.9300
C20 C21 . 1.395(3)
C20 C23 . 1.517(3)
C21 H21 . 0.9300
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
C23 H23A . 0.9600
C23 H23B . 0.9600
C23 H23C . 0.9600
P1 O1 . 1.5978(12)
P1 O2 . 1.6051(12)
P1 S2 . 1.9709(6)
P1 S1 . 1.9748(6)
S1 Ni1 . 2.5213(5)
S2 Ni1 . 2.5164(4)
Ni1 N1 . 2.1083(13)
Ni1 N1 2_666 2.1083(13)
Ni1 S2 2_666 2.5164(4)
Ni1 S1 2_666 2.5213(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_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 0.0(3)
C1 C2 C3 C4 . . -1.0(3)
C1 C2 C3 C6 . . 179.47(19)
C2 C3 C4 C5 . . 1.0(3)
C6 C3 C4 C5 . . -179.48(18)
C3 C4 C5 N1 . . 0.0(3)
C4 C3 C6 C7 . . -115.1(2)
C2 C3 C6 C7 . . 64.5(3)
C13 C8 C9 C10 . . 1.4(3)
O1 C8 C9 C10 . . 178.54(15)
C8 C9 C10 C11 . . 0.0(3)
C8 C9 C10 C14 . . 179.53(18)
C9 C10 C11 C12 . . -1.4(3)
C14 C10 C11 C12 . . 179.14(19)
C10 C11 C12 C13 . . 1.3(3)
C10 C11 C12 C15 . . -178.44(19)
C9 C8 C13 C12 . . -1.4(3)
O1 C8 C13 C12 . . -178.39(15)
C11 C12 C13 C8 . . 0.1(3)
C15 C12 C13 C8 . . 179.82(18)
C21 C16 C17 C18 . . 0.4(3)
O2 C16 C17 C18 . . -174.57(18)
C16 C17 C18 C19 . . -2.0(3)
C16 C17 C18 C22 . . 175.7(2)
C17 C18 C19 C20 . . 1.7(3)
C22 C18 C19 C20 . . -176.0(2)
C18 C19 C20 C21 . . 0.2(3)
C18 C19 C20 C23 . . 179.8(2)
C17 C16 C21 C20 . . 1.5(3)
O2 C16 C21 C20 . . 176.76(16)
C19 C20 C21 C16 . . -1.8(3)
C23 C20 C21 C16 . . 178.7(2)
O1 P1 S1 Ni1 . . 109.59(5)
O2 P1 S1 Ni1 . . -144.04(5)
S2 P1 S1 Ni1 . . -15.11(2)
O1 P1 S2 Ni1 . . -105.86(5)
O2 P1 S2 Ni1 . . 144.41(5)
S1 P1 S2 Ni1 . . 15.13(2)
P1 S2 Ni1 N1 . . 78.82(4)
P1 S2 Ni1 N1 . 2_666 -101.18(4)
P1 S2 Ni1 S1 . 2_666 168.993(18)
P1 S2 Ni1 S1 . . -11.006(18)
P1 S1 Ni1 N1 . . -79.87(4)
P1 S1 Ni1 N1 . 2_666 100.13(4)
P1 S1 Ni1 S2 . . 10.991(18)
P1 S1 Ni1 S2 . 2_666 -169.009(18)
C4 C5 N1 C1 . . -1.0(2)
C4 C5 N1 Ni1 . . 177.26(13)
C2 C1 N1 C5 . . 0.9(3)
C2 C1 N1 Ni1 . . -177.25(15)
S2 Ni1 N1 C5 . . 47.95(12)
S2 Ni1 N1 C5 2_666 . -132.05(12)
S1 Ni1 N1 C5 2_666 . -50.72(12)
S1 Ni1 N1 C5 . . 129.28(12)
S2 Ni1 N1 C1 . . -133.94(13)
S2 Ni1 N1 C1 2_666 . 46.06(13)
S1 Ni1 N1 C1 2_666 . 127.40(13)
S1 Ni1 N1 C1 . . -52.61(13)
C9 C8 O1 P1 . . 133.96(14)
C13 C8 O1 P1 . . -48.9(2)
O2 P1 O1 C8 . . 77.40(14)
S2 P1 O1 C8 . . -41.20(14)
S1 P1 O1 C8 . . -165.54(12)
C21 C16 O2 P1 . . 136.57(15)
C17 C16 O2 P1 . . -48.1(2)
O1 P1 O2 C16 . . -165.41(14)
S2 P1 O2 C16 . . -46.26(16)
S1 P1 O2 C16 . . 82.74(15)
