#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/52/7015233.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_7015233
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         'C14 H23 N2 O2 P S2'
_chemical_formula_sum            'C14 H23 N2 O2 P S2'
_chemical_formula_weight         346.43
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.187(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9075(7)
_cell_length_b                   15.1449(7)
_cell_length_c                   12.9257(8)
_cell_measurement_reflns_used    8900
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.4
_cell_volume                     1808.4(2)
_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_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9964
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         3.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.8827
_exptl_absorpt_correction_T_min  0.8572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0328
_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)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                2717
_reflns_number_total             3372
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0dt01382j.txt
_cod_data_source_block           safin43
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        1808.38(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7015233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
P1 P 0.63052(5) 0.46319(3) 0.77343(4) 0.02682(13) Uani 1 1 d . . .
S1 S 0.71938(5) 0.35502(3) 0.83979(4) 0.03667(14) Uani 1 1 d . . .
S2 S 0.38285(5) 0.61488(3) 0.92180(4) 0.03057(13) Uani 1 1 d . . .
N1 N 0.53724(16) 0.50659(10) 0.84669(14) 0.0280(3) Uani 1 1 d . . .
H1 H 0.542(2) 0.4783(14) 0.9003(19) 0.034(6) Uiso 1 1 d . . .
N2 N 0.47678(19) 0.64130(11) 0.75755(14) 0.0362(4) Uani 1 1 d . . .
H2 H 0.526(3) 0.6270(17) 0.722(2) 0.058(8) Uiso 1 1 d . . .
O1 O 0.52301(14) 0.46261(8) 0.64963(11) 0.0347(3) Uani 1 1 d . . .
O2 O 0.72980(12) 0.53988(8) 0.75844(10) 0.0282(3) Uani 1 1 d . . .
C1 C 0.46908(17) 0.58740(11) 0.83687(14) 0.0264(4) Uani 1 1 d . . .
C2 C 0.4208(2) 0.39039(15) 0.60328(18) 0.0486(6) Uani 1 1 d . . .
H2A H 0.4141 0.3523 0.6645 0.058 Uiso 1 1 calc R . .
C3 C 0.4759(4) 0.33779(17) 0.5297(2) 0.0773(9) Uani 1 1 d . . .
H3A H 0.5691 0.3113 0.5740 0.116 Uiso 1 1 calc R . .
H3B H 0.4883 0.3764 0.4730 0.116 Uiso 1 1 calc R . .
H3C H 0.4064 0.2910 0.4938 0.116 Uiso 1 1 calc R . .
C4 C 0.2759(3) 0.4337(2) 0.5422(2) 0.0775(9) Uani 1 1 d . . .
H4A H 0.2451 0.4668 0.5949 0.116 Uiso 1 1 calc R . .
H4B H 0.2038 0.3882 0.5063 0.116 Uiso 1 1 calc R . .
H4C H 0.2850 0.4740 0.4858 0.116 Uiso 1 1 calc R . .
C5 C 0.87486(18) 0.55863(12) 0.84195(16) 0.0328(4) Uani 1 1 d . . .
H5 H 0.9320 0.5026 0.8601 0.039 Uiso 1 1 calc R . .
C6 C 0.8626(2) 0.59529(15) 0.94587(18) 0.0458(5) Uani 1 1 d . . .
H6A H 0.8170 0.5514 0.9785 0.069 Uiso 1 1 calc R . .
H6B H 0.8033 0.6490 0.9281 0.069 Uiso 1 1 calc R . .
H6C H 0.9593 0.6095 0.9990 0.069 Uiso 1 1 calc R . .
C7 C 0.9443(2) 0.62073(14) 0.7854(2) 0.0459(5) Uani 1 1 d . . .
H7A H 0.9493 0.5925 0.7187 0.069 Uiso 1 1 calc R . .
H7B H 1.0423 0.6353 0.8361 0.069 Uiso 1 1 calc R . .
H7C H 0.8867 0.6749 0.7646 0.069 Uiso 1 1 calc R . .
C11 C 0.4248(2) 0.73134(13) 0.74428(17) 0.0358(4) Uani 1 1 d . . .
C12 C 0.2848(2) 0.75019(15) 0.67588(18) 0.0440(5) Uani 1 1 d . . .
C13 C 0.2433(3) 0.84012(18) 0.6652(2) 0.0565(7) Uani 1 1 d . . .
H13 H 0.1481 0.8561 0.6182 0.068 Uiso 1 1 calc R . .
C14 C 0.3394(3) 0.90476(16) 0.7223(2) 0.0588(7) Uani 1 1 d . . .
H14 H 0.3093 0.9647 0.7145 0.071 Uiso 1 1 calc R . .
C15 C 0.4759(3) 0.88401(15) 0.7891(2) 0.0576(6) Uani 1 1 d . . .
H15 H 0.5409 0.9292 0.8280 0.069 Uiso 1 1 calc R . .
C16 C 0.5206(2) 0.79650(14) 0.8007(2) 0.0463(5) Uani 1 1 d . . .
H16 H 0.6165 0.7815 0.8472 0.056 Uiso 1 1 calc R . .
C17 C 0.1840(3) 0.6798(2) 0.6156(2) 0.0669(7) Uani 1 1 d . . .
H17A H 0.2234 0.6492 0.5660 0.100 Uiso 1 1 calc R . .
H17B H 0.0901 0.7059 0.5719 0.100 Uiso 1 1 calc R . .
H17C H 0.1714 0.6376 0.6689 0.100 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'
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
O1 P1 O2 95.88(7) . . ?
O1 P1 N1 105.57(8) . . ?
O2 P1 N1 106.01(7) . . ?
O1 P1 S1 119.07(5) . . ?
O2 P1 S1 118.66(5) . . ?
N1 P1 S1 109.94(6) . . ?
C1 N1 P1 130.23(14) . . ?
C1 N1 H1 115.5(15) . . ?
P1 N1 H1 113.8(15) . . ?
C1 N2 C11 123.46(16) . . ?
C1 N2 H2 119.2(18) . . ?
C11 N2 H2 116.4(18) . . ?
C2 O1 P1 122.40(12) . . ?
C5 O2 P1 122.39(11) . . ?
N2 C1 N1 116.81(16) . . ?
N2 C1 S2 122.53(14) . . ?
N1 C1 S2 120.66(13) . . ?
O1 C2 C3 107.6(2) . . ?
O1 C2 C4 106.0(2) . . ?
C3 C2 C4 113.3(2) . . ?
O1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C4 C2 H2A 109.9 . . ?
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 C6 110.65(15) . . ?
O2 C5 C7 105.08(15) . . ?
C6 C5 C7 113.84(18) . . ?
O2 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C7 C5 H5 109.0 . . ?
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 . . ?
C12 C11 C16 122.09(19) . . ?
C12 C11 N2 120.3(2) . . ?
C16 C11 N2 117.62(17) . . ?
C11 C12 C13 116.9(2) . . ?
C11 C12 C17 121.4(2) . . ?
C13 C12 C17 121.7(2) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 119.5(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
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
P1 O1 1.5695(13) . ?
P1 O2 1.5786(12) . ?
P1 N1 1.6779(16) . ?
P1 S1 1.9102(7) . ?
S2 C1 1.6691(18) . ?
N1 C1 1.381(2) . ?
N1 H1 0.80(2) . ?
N2 C1 1.334(2) . ?
N2 C11 1.446(2) . ?
N2 H2 0.81(3) . ?
O1 C2 1.464(2) . ?
O2 C5 1.480(2) . ?
C2 C3 1.487(4) . ?
C2 C4 1.515(4) . ?
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 C6 1.499(3) . ?
C5 C7 1.502(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 C12 1.378(3) . ?
C11 C16 1.381(3) . ?
C12 C13 1.415(3) . ?
C12 C17 1.476(4) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.352(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(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
N1 H1 S2 0.80(2) 2.57(2) 3.3545(17) 167.6(19) 3_667
N2 H2 O1 0.81(3) 2.66(3) 3.153(2) 121(2) .
N2 H2 O1 0.81(3) 2.66(3) 3.153(2) 121(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
O1 P1 N1 C1 -57.87(17) . . . . ?
O2 P1 N1 C1 43.11(17) . . . . ?
S1 P1 N1 C1 172.52(14) . . . . ?
O2 P1 O1 C2 165.85(15) . . . . ?
N1 P1 O1 C2 -85.70(16) . . . . ?
S1 P1 O1 C2 38.35(17) . . . . ?
O1 P1 O2 C5 -165.23(13) . . . . ?
N1 P1 O2 C5 86.70(13) . . . . ?
S1 P1 O2 C5 -37.43(14) . . . . ?
C11 N2 C1 N1 -173.16(17) . . . . ?
C11 N2 C1 S2 6.5(3) . . . . ?
P1 N1 C1 N2 -0.2(3) . . . . ?
P1 N1 C1 S2 -179.83(10) . . . . ?
P1 O1 C2 C3 -106.02(19) . . . . ?
P1 O1 C2 C4 132.44(17) . . . . ?
P1 O2 C5 C6 -69.05(18) . . . . ?
P1 O2 C5 C7 167.65(12) . . . . ?
C1 N2 C11 C12 -91.4(2) . . . . ?
C1 N2 C11 C16 89.6(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
N2 C11 C12 C13 -178.51(17) . . . . ?
C16 C11 C12 C17 179.6(2) . . . . ?
N2 C11 C12 C17 0.7(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C17 C12 C13 C14 -179.9(2) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
N2 C11 C16 C15 179.07(19) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652801
