#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/52/7015235.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_7015235
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         'C8 H19 N2 O2 P S2'
_chemical_formula_sum            'C8 H19 N2 O2 P S2'
_chemical_formula_weight         270.34
_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                80.832(7)
_cell_angle_beta                 76.351(7)
_cell_angle_gamma                70.632(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4084(7)
_cell_length_b                   9.7510(8)
_cell_length_c                   10.2595(9)
_cell_measurement_reflns_used    4695
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      4.0
_cell_volume                     676.79(11)
_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 0.993
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5904
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.58
_diffrn_reflns_theta_min         3.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.8452
_exptl_absorpt_correction_T_min  0.8036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0294
_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)+(0.0414P)²+0.2951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                2413
_reflns_number_total             2507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0dt01382j.txt
_cod_data_source_block           safin34
_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        676.79(10)
_cod_database_code               7015235
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
P1 P 0.64982(5) 0.67401(4) 0.29149(4) 0.01670(13) Uani 1 1 d . . .
S1 S 0.70331(6) 0.67312(4) 0.46559(4) 0.02663(14) Uani 1 1 d . . .
S2 S 1.02809(6) 0.29115(4) 0.10595(4) 0.02465(14) Uani 1 1 d . . .
O1 O 0.64978(16) 0.81163(11) 0.18798(10) 0.0218(2) Uani 1 1 d . . .
O2 O 0.44663(15) 0.64818(12) 0.30766(10) 0.0211(2) Uani 1 1 d . . .
N1 N 0.81190(19) 0.54755(14) 0.19411(13) 0.0203(3) Uani 1 1 d . . .
H1 H 0.855(3) 0.577(2) 0.123(2) 0.027(5) Uiso 1 1 d . . .
N2 N 0.8202(2) 0.34779(15) 0.34987(14) 0.0284(3) Uani 1 1 d . . .
H2 H 0.756(3) 0.407(2) 0.408(2) 0.039(6) Uiso 1 1 d . . .
C1 C 0.8791(2) 0.39901(16) 0.22511(15) 0.0191(3) Uani 1 1 d . . .
C2 C 0.8781(3) 0.19467(18) 0.39952(18) 0.0339(4) Uani 1 1 d . . .
H2A H 0.8719 0.1356 0.3328 0.051 Uiso 1 1 calc R . .
H2B H 0.7896 0.1796 0.4842 0.051 Uiso 1 1 calc R . .
H2C H 1.0118 0.1655 0.4150 0.051 Uiso 1 1 calc R . .
C3 C 0.6414(2) 0.95371(16) 0.22492(16) 0.0232(3) Uani 1 1 d . . .
H3 H 0.7354 0.9385 0.2855 0.028 Uiso 1 1 calc R . .
C4 C 0.7039(3) 1.03712(19) 0.09469(19) 0.0330(4) Uani 1 1 d . . .
H4A H 0.8307 0.9785 0.0475 0.050 Uiso 1 1 calc R . .
H4B H 0.7149 1.1290 0.1140 0.050 Uiso 1 1 calc R . .
H4C H 0.6069 1.0580 0.0379 0.050 Uiso 1 1 calc R . .
C5 C 0.4381(3) 1.0294(2) 0.2964(2) 0.0403(5) Uani 1 1 d . . .
H5A H 0.4020 0.9683 0.3774 0.060 Uiso 1 1 calc R . .
H5B H 0.3464 1.0460 0.2364 0.060 Uiso 1 1 calc R . .
H5C H 0.4337 1.1233 0.3220 0.060 Uiso 1 1 calc R . .
C6 C 0.3647(2) 0.64976(18) 0.18883(15) 0.0240(3) Uani 1 1 d . . .
H6 H 0.4476 0.6819 0.1056 0.029 Uiso 1 1 calc R . .
C7 C 0.1637(3) 0.7589(2) 0.2096(2) 0.0372(4) Uani 1 1 d . . .
H7A H 0.1735 0.8554 0.2155 0.056 Uiso 1 1 calc R . .
H7B H 0.0842 0.7293 0.2932 0.056 Uiso 1 1 calc R . .
H7C H 0.1025 0.7629 0.1336 0.056 Uiso 1 1 calc R . .
C8 C 0.3646(3) 0.4972(2) 0.1795(2) 0.0395(4) Uani 1 1 d . . .
H8A H 0.4984 0.4309 0.1699 0.059 Uiso 1 1 calc R . .
H8B H 0.3112 0.4959 0.1011 0.059 Uiso 1 1 calc R . .
H8C H 0.2840 0.4656 0.2614 0.059 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 107.11(6) . . ?
O1 P1 N1 97.97(6) . . ?
O2 P1 N1 106.25(6) . . ?
O1 P1 S1 118.71(5) . . ?
O2 P1 S1 109.71(4) . . ?
N1 P1 S1 115.86(5) . . ?
C3 O1 P1 123.90(10) . . ?
C6 O2 P1 121.26(9) . . ?
C1 N1 P1 128.21(11) . . ?
C1 N1 H1 116.2(15) . . ?
P1 N1 H1 115.6(15) . . ?
C1 N2 C2 124.42(14) . . ?
C1 N2 H2 118.8(15) . . ?
C2 N2 H2 116.3(15) . . ?
N2 C1 N1 117.32(14) . . ?
N2 C1 S2 122.92(12) . . ?
N1 C1 S2 119.76(11) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C5 109.76(13) . . ?
O1 C3 C4 105.77(13) . . ?
C5 C3 C4 112.75(15) . . ?
O1 C3 H3 109.5 . . ?
C5 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 C7 106.44(13) . . ?
O2 C6 C8 108.20(13) . . ?
C7 C6 C8 113.40(15) . . ?
O2 C6 H6 109.6 . . ?
C7 C6 H6 109.6 . . ?
C8 C6 H6 109.6 . . ?
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 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 1.5730(11) . ?
P1 O2 1.5739(11) . ?
P1 N1 1.6748(13) . ?
P1 S1 1.9169(5) . ?
S2 C1 1.6799(15) . ?
O1 C3 1.4717(17) . ?
O2 C6 1.4805(18) . ?
N1 C1 1.377(2) . ?
N1 H1 0.78(2) . ?
N2 C1 1.325(2) . ?
N2 C2 1.452(2) . ?
N2 H2 0.84(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C5 1.505(2) . ?
C3 C4 1.508(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.505(2) . ?
C6 C8 1.506(2) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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 0.78(2) 2.59(2) 3.3656(14) 172.4(19) 2_765
N2 H2 S1 0.84(2) 2.63(2) 3.3341(15) 141.6(19) .
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
O2 P1 O1 C3 109.54(12) . . . . ?
N1 P1 O1 C3 -140.66(12) . . . . ?
S1 P1 O1 C3 -15.28(13) . . . . ?
O1 P1 O2 C6 47.32(12) . . . . ?
N1 P1 O2 C6 -56.62(12) . . . . ?
S1 P1 O2 C6 177.42(10) . . . . ?
O1 P1 N1 C1 -179.70(14) . . . . ?
O2 P1 N1 C1 -69.20(15) . . . . ?
S1 P1 N1 C1 52.93(15) . . . . ?
C2 N2 C1 N1 -179.53(16) . . . . ?
C2 N2 C1 S2 1.0(2) . . . . ?
P1 N1 C1 N2 -4.9(2) . . . . ?
P1 N1 C1 S2 174.65(8) . . . . ?
P1 O1 C3 C5 -74.47(17) . . . . ?
P1 O1 C3 C4 163.63(11) . . . . ?
P1 O2 C6 C7 -125.92(12) . . . . ?
P1 O2 C6 C8 111.88(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652803
