#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:39:45 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179856 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/52/7015236.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_7015236
loop_
_publ_author_name
'Babashkina, Maria G.'
'Safin, Damir A.'
'Bolte, Michael'
'Srebro, Monika'
'Mitoraj, Mariusz'
'Uthe, André'
'Klein, Axel'
'Köckerling, Martin'
_publ_section_title
;
 Intramolecular hydrogen bonding controls 1,3-N,S- vs.
 1,5-S,S'-coordination in Ni(II) complexes of N-thiophosphorylated
 thioureas RNHC(S)NHP(S)(OiPr)2.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3142
_journal_page_last               3153
_journal_paper_doi               10.1039/c0dt01382j
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C28 H44 N4 Ni O4 P2 S4'
_chemical_formula_sum            'C28 H44 N4 Ni O4 P2 S4'
_chemical_formula_weight         749.56
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_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                103.075(8)
_cell_angle_beta                 105.168(8)
_cell_angle_gamma                106.810(8)
_cell_formula_units_Z            1
_cell_length_a                   8.3222(8)
_cell_length_b                   9.3599(10)
_cell_length_c                   12.9907(13)
_cell_measurement_reflns_used    6386
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.4
_cell_volume                     883.61(18)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7372
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.59
_diffrn_reflns_theta_min         3.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.8676
_exptl_absorpt_correction_T_min  0.7285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0377
_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)+(0.0703P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2919
_reflns_number_total             3270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01382j.txt
_cod_data_source_block           safin42
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        883.60(18)
_cod_database_code               7015236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 1.0000 0.01744(15) Uani 1 2 d S . .
P1 P 0.53322(7) 0.60121(5) 0.78377(4) 0.01778(16) Uani 1 1 d . . .
S1 S 0.24073(7) 0.29658(6) 0.91200(4) 0.02357(16) Uani 1 1 d . . .
S2 S 0.43484(7) 0.53821(6) 0.62029(4) 0.02695(17) Uani 1 1 d . . .
N1 N 0.4395(2) 0.48004(19) 0.84389(14) 0.0203(4) Uani 1 1 d . . .
N2 N 0.1869(2) 0.28486(19) 0.69284(14) 0.0220(4) Uani 1 1 d D . .
H2 H 0.236(3) 0.331(3) 0.6493(19) 0.039(7) Uiso 1 1 d D . .
O1 O 0.52444(18) 0.76028(15) 0.84978(11) 0.0212(3) Uani 1 1 d . . .
O2 O 0.74080(18) 0.63464(15) 0.83018(11) 0.0211(3) Uani 1 1 d . . .
C1 C 0.2850(3) 0.3525(2) 0.80152(17) 0.0192(4) Uani 1 1 d . . .
C2 C 0.5925(3) 0.9062(2) 0.82275(18) 0.0249(4) Uani 1 1 d . . .
H2A H 0.5998 0.8782 0.7456 0.030 Uiso 1 1 calc R . .
C3 C 0.7766(3) 1.0049(3) 0.9078(2) 0.0428(6) Uani 1 1 d . . .
H3A H 0.8572 0.9477 0.9015 0.064 Uiso 1 1 calc R . .
H3B H 0.7709 1.0268 0.9839 0.064 Uiso 1 1 calc R . .
H3C H 0.8218 1.1047 0.8935 0.064 Uiso 1 1 calc R . .
C4 C 0.4569(4) 0.9829(3) 0.8236(3) 0.0441(6) Uani 1 1 d . . .
H4A H 0.3410 0.9119 0.7658 0.066 Uiso 1 1 calc R . .
H4B H 0.4969 1.0821 0.8076 0.066 Uiso 1 1 calc R . .
H4C H 0.4445 1.0049 0.8979 0.066 Uiso 1 1 calc R . .
C5 C 0.8249(3) 0.5360(2) 0.7776(2) 0.0287(5) Uani 1 1 d . . .
H5 H 0.7815 0.5171 0.6945 0.034 Uiso 1 1 calc R . .
C6 C 0.7731(4) 0.3793(3) 0.7971(3) 0.0529(8) Uani 1 1 d . . .
H6A H 0.6426 0.3251 0.7643 0.079 Uiso 1 1 calc R . .
H6B H 0.8132 0.3962 0.8784 0.079 Uiso 1 1 calc R . .
H6C H 0.8299 0.3145 0.7614 0.079 Uiso 1 1 calc R . .
C7 C 1.0222(3) 0.6307(3) 0.8253(3) 0.0477(7) Uani 1 1 d . . .
H7A H 1.0450 0.7310 0.8097 0.072 Uiso 1 1 calc R . .
H7B H 1.0846 0.5714 0.7903 0.072 Uiso 1 1 calc R . .
H7C H 1.0661 0.6518 0.9070 0.072 Uiso 1 1 calc R . .
C11 C 0.0209(3) 0.1525(2) 0.64232(16) 0.0204(4) Uani 1 1 d . . .
C12 C -0.1126(3) 0.1592(2) 0.55417(17) 0.0242(4) Uani 1 1 d . . .
C13 C -0.2732(3) 0.0282(3) 0.50304(19) 0.0312(5) Uani 1 1 d . . .
H13 H -0.3661 0.0300 0.4431 0.037 Uiso 1 1 calc R . .
C14 C -0.3011(3) -0.1039(3) 0.5369(2) 0.0332(5) Uani 1 1 d . . .
H14 H -0.4122 -0.1909 0.5010 0.040 Uiso 1 1 calc R . .
C15 C -0.1660(3) -0.1087(2) 0.62360(19) 0.0291(5) Uani 1 1 d . . .
H15 H -0.1840 -0.1992 0.6472 0.035 Uiso 1 1 calc R . .
C16 C -0.0041(3) 0.0195(2) 0.67582(17) 0.0239(4) Uani 1 1 d . . .
H16 H 0.0894 0.0160 0.7344 0.029 Uiso 1 1 calc R . .
C17 C -0.0864(3) 0.3011(3) 0.5151(2) 0.0344(5) Uani 1 1 d . . .
H17A H -0.0415 0.3970 0.5804 0.052 Uiso 1 1 calc R . .
H17B H -0.2010 0.2915 0.4631 0.052 Uiso 1 1 calc R . .
H17C H 0.0005 0.3073 0.4763 0.052 Uiso 1 1 calc R . .
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'
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'
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
_geom_angle_publ_flag
N1 Ni1 N1 180.00(10) . 2_667 ?
N1 Ni1 S1 105.73(5) . 2_667 ?
N1 Ni1 S1 74.28(5) 2_667 2_667 ?
N1 Ni1 S1 74.28(5) . . ?
N1 Ni1 S1 105.72(5) 2_667 . ?
S1 Ni1 S1 180.0 2_667 . ?
N1 Ni1 C1 32.09(6) . . ?
N1 Ni1 C1 147.91(7) 2_667 . ?
S1 Ni1 C1 137.80(5) 2_667 . ?
S1 Ni1 C1 42.20(5) . . ?
N1 Ni1 C1 147.91(7) . 2_667 ?
N1 Ni1 C1 32.09(6) 2_667 2_667 ?
S1 Ni1 C1 42.20(5) 2_667 2_667 ?
S1 Ni1 C1 137.80(5) . 2_667 ?
C1 Ni1 C1 180.00(9) . 2_667 ?
O1 P1 O2 102.07(8) . . ?
O1 P1 N1 101.20(8) . . ?
O2 P1 N1 106.14(8) . . ?
O1 P1 S2 115.72(6) . . ?
O2 P1 S2 112.80(6) . . ?
N1 P1 S2 117.15(7) . . ?
C1 S1 Ni1 77.89(7) . . ?
C1 N1 P1 130.86(14) . . ?
C1 N1 Ni1 99.31(12) . . ?
P1 N1 Ni1 129.17(10) . . ?
C1 N2 C11 127.53(17) . . ?
C1 N2 H2 112.6(18) . . ?
C11 N2 H2 119.9(18) . . ?
C2 O1 P1 120.96(12) . . ?
C5 O2 P1 123.47(13) . . ?
N2 C1 N1 124.45(17) . . ?
N2 C1 S1 127.06(15) . . ?
N1 C1 S1 108.49(14) . . ?
N2 C1 Ni1 172.93(15) . . ?
N1 C1 Ni1 48.60(9) . . ?
S1 C1 Ni1 59.92(6) . . ?
O1 C2 C3 108.23(17) . . ?
O1 C2 C4 106.05(17) . . ?
C3 C2 C4 114.3(2) . . ?
O1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C4 C2 H2A 109.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 C7 106.21(19) . . ?
O2 C5 C6 110.29(18) . . ?
C7 C5 C6 114.3(2) . . ?
O2 C5 H5 108.6 . . ?
C7 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C11 C12 121.20(19) . . ?
C16 C11 N2 121.31(18) . . ?
C12 C11 N2 117.42(17) . . ?
C13 C12 C11 117.37(19) . . ?
C13 C12 C17 120.7(2) . . ?
C11 C12 C17 121.94(19) . . ?
C14 C13 C12 122.0(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.0(2) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.9082(16) . ?
Ni1 N1 1.9082(16) 2_667 ?
Ni1 S1 2.2217(6) 2_667 ?
Ni1 S1 2.2217(6) . ?
Ni1 C1 2.510(2) . ?
Ni1 C1 2.510(2) 2_667 ?
P1 O1 1.5733(14) . ?
P1 O2 1.5819(15) . ?
P1 N1 1.6468(16) . ?
P1 S2 1.9423(7) . ?
S1 C1 1.725(2) . ?
N1 C1 1.351(3) . ?
N2 C1 1.324(3) . ?
N2 C11 1.429(3) . ?
N2 H2 0.896(10) . ?
O1 C2 1.478(2) . ?
O2 C5 1.466(2) . ?
C2 C3 1.502(3) . ?
C2 C4 1.503(3) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C7 1.498(3) . ?
C5 C6 1.503(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C16 1.388(3) . ?
C11 C12 1.398(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.506(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
N2 H2 S2 0.896(10) 2.333(15) 3.1571(17) 153(2) .
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
_geom_torsion_publ_flag
N1 Ni1 S1 C1 1.12(8) . . . . ?
N1 Ni1 S1 C1 -178.88(8) 2_667 . . . ?
C1 Ni1 S1 C1 180.0 2_667 . . . ?
O1 P1 N1 C1 114.82(19) . . . . ?
O2 P1 N1 C1 -138.96(18) . . . . ?
S2 P1 N1 C1 -12.0(2) . . . . ?
O1 P1 N1 Ni1 -53.98(14) . . . . ?
O2 P1 N1 Ni1 52.23(14) . . . . ?
S2 P1 N1 Ni1 179.24(9) . . . . ?
S1 Ni1 N1 C1 178.59(11) 2_667 . . . ?
S1 Ni1 N1 C1 -1.41(11) . . . . ?
C1 Ni1 N1 C1 179.999(2) 2_667 . . . ?
S1 Ni1 N1 P1 -9.97(14) 2_667 . . . ?
S1 Ni1 N1 P1 170.03(14) . . . . ?
C1 Ni1 N1 P1 171.4(2) . . . . ?
C1 Ni1 N1 P1 -8.6(2) 2_667 . . . ?
O2 P1 O1 C2 71.57(15) . . . . ?
N1 P1 O1 C2 -179.03(14) . . . . ?
S2 P1 O1 C2 -51.31(15) . . . . ?
O1 P1 O2 C5 -166.33(14) . . . . ?
N1 P1 O2 C5 88.08(16) . . . . ?
S2 P1 O2 C5 -41.49(15) . . . . ?
C11 N2 C1 N1 -178.49(19) . . . . ?
C11 N2 C1 S1 1.3(3) . . . . ?
P1 N1 C1 N2 10.4(3) . . . . ?
Ni1 N1 C1 N2 -178.36(17) . . . . ?
P1 N1 C1 S1 -169.38(13) . . . . ?
Ni1 N1 C1 S1 1.85(14) . . . . ?
P1 N1 C1 Ni1 -171.2(2) . . . . ?
Ni1 S1 C1 N2 178.61(19) . . . . ?
Ni1 S1 C1 N1 -1.60(12) . . . . ?
N1 Ni1 C1 N1 180.0 2_667 . . . ?
S1 Ni1 C1 N1 -2.02(15) 2_667 . . . ?
S1 Ni1 C1 N1 177.98(15) . . . . ?
N1 Ni1 C1 S1 -177.98(15) . . . . ?
N1 Ni1 C1 S1 2.02(15) 2_667 . . . ?
S1 Ni1 C1 S1 180.0 2_667 . . . ?
P1 O1 C2 C3 -99.46(19) . . . . ?
P1 O1 C2 C4 137.43(17) . . . . ?
P1 O2 C5 C7 164.32(17) . . . . ?
P1 O2 C5 C6 -71.3(2) . . . . ?
C1 N2 C11 C16 -44.4(3) . . . . ?
C1 N2 C11 C12 138.6(2) . . . . ?
C16 C11 C12 C13 1.4(3) . . . . ?
N2 C11 C12 C13 178.49(18) . . . . ?
C16 C11 C12 C17 -178.7(2) . . . . ?
N2 C11 C12 C17 -1.6(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C17 C12 C13 C14 179.9(2) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C12 C11 C16 C15 -1.8(3) . . . . ?
N2 C11 C16 C15 -178.76(18) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
