#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:53:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180403 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/72/7207213.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_7207213
loop_
_publ_author_name
'Babashkina, Maria G.'
'Safin, Damir A.'
'Robeyns, Koen'
'Brzuszkiewicz, Anna'
'Kozlowski, Henryk'
'Garcia, Yann'
_publ_section_title
;
 Thiophosphorylated bis-thioureas for competitive bulk liquid membrane
 transport of some metal ions
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1324
_journal_paper_doi               10.1039/c1ce06244a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety
'C26 H40 N4 O5 P2 S4, 0.24(C2 H4 Cl4), 0.36(C Cl2), 0.71(H)'
_chemical_formula_sum            'C26.83 H41.66 Cl1.67 N4 O5 P2 S4'
_chemical_formula_weight         749.58
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 131.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.051(11)
_cell_length_b                   15.013(8)
_cell_length_c                   15.837(8)
_cell_measurement_reflns_used    3797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.79
_cell_measurement_theta_min      3.07
_cell_volume                     3740(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Kuma KM4CCD κ-axis 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  0.0773
_diffrn_reflns_av_sigmaI/netI    0.1017
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15187
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9878
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1572
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4278
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0740
_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)+(0.1254P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2232
_reflns_number_gt                2283
_reflns_number_total             4278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06244a.txt
_cod_data_source_block           1
_cod_original_cell_volume        3740(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7207213
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S1 S 0.17476(8) -0.05610(9) 0.57486(11) 0.0396(4) Uani 1 1 d . . .
S2 S 0.16321(9) 0.29190(9) 0.51284(13) 0.0458(4) Uani 1 1 d . . .
P1 P 0.25478(8) 0.02492(9) 0.59624(10) 0.0307(3) Uani 1 1 d . . .
O1 O 0.3312(2) 0.0408(2) 0.7246(3) 0.0343(8) Uani 1 1 d . . .
O2 O 0.2976(2) -0.0020(2) 0.5482(3) 0.0344(8) Uani 1 1 d . B .
O3 O 0.0000 0.3191(3) 0.7500 0.0426(13) Uani 1 2 d S . .
N1 N 0.2153(2) 0.1262(3) 0.5369(3) 0.0305(9) Uani 1 1 d . . .
H1A H 0.2216 0.1429 0.4910 0.037 Uiso 1 1 d R . .
N2 N 0.1427(2) 0.1512(3) 0.5959(3) 0.0294(9) Uani 1 1 d . . .
H2A H 0.1457 0.0942 0.6034 0.035 Uiso 1 1 d R . .
C1 C 0.1735(3) 0.1855(3) 0.5518(4) 0.0318(11) Uani 1 1 d . . .
C2 C 0.1045(3) 0.1972(3) 0.6315(4) 0.0269(10) Uani 1 1 d . . .
C3 C 0.1380(3) 0.2761(3) 0.6930(4) 0.0343(11) Uani 1 1 d . . .
H3A H 0.1838 0.3035 0.7070 0.041 Uiso 1 1 calc R . .
C4 C 0.1026(3) 0.3126(3) 0.7325(4) 0.0379(12) Uani 1 1 d . . .
H4A H 0.1254 0.3650 0.7745 0.045 Uiso 1 1 calc R . .
C5 C 0.0337(3) 0.2736(3) 0.7116(4) 0.0325(11) Uani 1 1 d . . .
C6 C 0.0000(3) 0.1961(3) 0.6505(4) 0.0357(12) Uani 1 1 d . . .
H6A H -0.0460 0.1694 0.6367 0.043 Uiso 1 1 calc R . .
C7 C 0.0351(3) 0.1575(3) 0.6093(4) 0.0329(11) Uani 1 1 d . . .
H7A H 0.0120 0.1053 0.5670 0.039 Uiso 1 1 calc R . .
C8 C 0.4051(3) 0.0984(4) 0.7726(4) 0.0358(12) Uani 1 1 d . . .
H8A H 0.4028 0.1191 0.7118 0.043 Uiso 1 1 calc R . .
C9 C 0.4820(4) 0.0422(5) 0.8524(5) 0.0642(19) Uani 1 1 d . . .
H9A H 0.4806 -0.0067 0.8121 0.096 Uiso 1 1 calc R . .
H9B H 0.4831 0.0196 0.9101 0.096 Uiso 1 1 calc R . .
H9C H 0.5320 0.0773 0.8866 0.096 Uiso 1 1 calc R . .
C10 C 0.4004(4) 0.1771(5) 0.8267(6) 0.074(2) Uani 1 1 d . . .
H10A H 0.3455 0.2045 0.7734 0.112 Uiso 1 1 calc R . .
H10B H 0.4436 0.2194 0.8498 0.112 Uiso 1 1 calc R . .
H10C H 0.4091 0.1577 0.8915 0.112 Uiso 1 1 calc R . .
C11 C 0.2523(4) -0.0558(4) 0.4425(4) 0.0491(15) Uani 1 1 d . . .
H11A H 0.1924 -0.0672 0.4029 0.059 Uiso 1 1 calc R A 1
C12 C 0.2655(5) -0.0110(6) 0.3716(6) 0.089(3) Uani 1 1 d . B .
H12A H 0.2455 -0.0488 0.3093 0.134 Uiso 1 1 calc R . .
H12B H 0.3250 0.0008 0.4164 0.134 Uiso 1 1 calc R . .
H12C H 0.2346 0.0442 0.3434 0.134 Uiso 1 1 calc R . .
C13A C 0.3079(15) -0.1433(9) 0.4843(11) 0.055(5) Uiso 0.52(4) 1 d P B 1
H13A H 0.3046 -0.1762 0.5333 0.083 Uiso 0.52(4) 1 calc PR B 1
H13B H 0.3660 -0.1274 0.5247 0.083 Uiso 0.52(4) 1 calc PR B 1
H13C H 0.2869 -0.1794 0.4203 0.083 Uiso 0.52(4) 1 calc PR B 1
C13B C 0.266(2) -0.1496(11) 0.4669(14) 0.067(6) Uiso 0.48(4) 1 d P B 2
H13D H 0.2180 -0.1748 0.4537 0.100 Uiso 0.48(4) 1 calc PR B 2
H13E H 0.3163 -0.1585 0.5446 0.100 Uiso 0.48(4) 1 calc PR B 2
H13F H 0.2724 -0.1783 0.4189 0.100 Uiso 0.48(4) 1 calc PR B 2
Cl1 Cl 0.0372(5) 0.0820(5) 0.2014(5) 0.083(3) Uiso 0.357(14) 1 d P C 3
C1S C 0.0000 0.1523(18) 0.2500 0.043(6) Uiso 0.357(14) 2 d SP . 3
H1SA H 0.0456 0.1900 0.3108 0.052 Uiso 0.178(7) 1 calc PR C 3
H1SB H -0.0456 0.1900 0.1892 0.052 Uiso 0.178(7) 1 calc PR C 3
Cl1S Cl 0.0141(6) 0.0478(6) 0.2153(7) 0.074(3) Uiso 0.238(8) 1 d PD . 4
Cl2S Cl -0.0629(6) 0.0916(5) 0.3079(6) 0.058(3) Uiso 0.238(8) 1 d PD . 4
C2S C -0.0122(13) 0.1324(13) 0.2643(17) 0.033(6) Uiso 0.238(8) 1 d PD . 4
H2SA H 0.0393 0.1630 0.3269 0.040 Uiso 0.238(8) 1 calc PR . 4
H2SB H -0.0488 0.1754 0.2043 0.040 Uiso 0.238(8) 1 calc PR . 4
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'
Cl Cl 0.1484 0.1585 '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
O1 P1 O2 104.16(19) . .
O1 P1 N1 106.68(19) . .
O2 P1 N1 101.01(19) . .
O1 P1 S1 110.58(15) . .
O2 P1 S1 118.12(15) . .
N1 P1 S1 115.06(16) . .
C8 O1 P1 125.6(3) . .
C11 O2 P1 122.4(3) . .
C5 O3 C5 120.9(5) 2_556 .
C1 N1 P1 128.4(3) . .
C1 N1 H1A 115.7 . .
P1 N1 H1A 115.9 . .
C1 N2 C2 128.1(4) . .
C1 N2 H2A 116.1 . .
C2 N2 H2A 115.8 . .
N2 C1 N1 115.4(4) . .
N2 C1 S2 125.0(4) . .
N1 C1 S2 119.6(3) . .
C7 C2 C3 120.0(4) . .
C7 C2 N2 117.7(4) . .
C3 C2 N2 122.1(4) . .
C4 C3 C2 119.1(4) . .
C4 C3 H3A 120.5 . .
C2 C3 H3A 120.5 . .
C3 C4 C5 121.6(5) . .
C3 C4 H4A 119.2 . .
C5 C4 H4A 119.2 . .
C6 C5 O3 123.5(4) . .
C6 C5 C4 119.8(4) . .
O3 C5 C4 116.6(4) . .
C5 C6 C7 119.7(4) . .
C5 C6 H6A 120.2 . .
C7 C6 H6A 120.2 . .
C2 C7 C6 119.9(4) . .
C2 C7 H7A 120.0 . .
C6 C7 H7A 120.0 . .
O1 C8 C9 106.6(4) . .
O1 C8 C10 107.9(4) . .
C9 C8 C10 114.2(5) . .
O1 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
C10 C8 H8A 109.4 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C13B C11 C12 122.9(11) . .
C13B C11 O2 111.3(8) . .
C12 C11 O2 107.4(5) . .
C13B C11 C13A 27.7(8) . .
C12 C11 C13A 103.5(9) . .
O2 C11 C13A 103.6(6) . .
C13B C11 H11A 86.8 . .
C12 C11 H11A 113.7 . .
O2 C11 H11A 113.7 . .
C13A C11 H11A 113.7 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13A H13A 109.5 . .
C11 C13A H13B 109.5 . .
H13A C13A H13B 109.5 . .
C11 C13A H13C 109.5 . .
H13A C13A H13C 109.5 . .
H13B C13A H13C 109.5 . .
C11 C13B H13D 109.5 . .
C11 C13B H13E 109.5 . .
H13D C13B H13E 109.5 . .
C11 C13B H13F 109.5 . .
H13D C13B H13F 109.5 . .
H13E C13B H13F 109.5 . .
Cl1 C1S Cl1 106.6(15) 2 .
Cl1 C1S H1SA 110.4 2 .
Cl1 C1S H1SA 110.4 . .
Cl1 C1S H1SB 110.4 2 .
Cl1 C1S H1SB 110.4 . .
H1SA C1S H1SB 108.6 . .
C2S Cl1S Cl2S 76.6(9) 2 2
C2S Cl1S Cl1S 74.9(9) 2 2
Cl2S Cl1S Cl1S 147.2(6) 2 2
C2S Cl1S C2S 29.0(11) 2 .
Cl2S Cl1S C2S 105.4(9) 2 .
Cl1S Cl1S C2S 46.4(7) 2 .
Cl1S Cl2S C2S 48.1(7) 2 .
Cl2S C2S Cl1S 112.3(12) . .
Cl2S C2S H2SA 109.1 . .
Cl1S C2S H2SA 109.1 . .
Cl2S C2S H2SB 109.1 . .
Cl1S C2S H2SB 109.1 . .
H2SA C2S H2SB 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 P1 1.917(2) .
S2 C1 1.674(5) .
P1 O1 1.559(4) .
P1 O2 1.570(3) .
P1 N1 1.688(4) .
O1 C8 1.475(6) .
O2 C11 1.497(6) .
O3 C5 1.383(5) 2_556
O3 C5 1.383(5) .
N1 C1 1.376(6) .
N1 H1A 0.8591 .
N2 C1 1.332(6) .
N2 C2 1.429(6) .
N2 H2A 0.8598 .
C2 C7 1.391(6) .
C2 C3 1.391(7) .
C3 C4 1.367(7) .
C3 H3A 0.9300 .
C4 C5 1.386(7) .
C4 H4A 0.9300 .
C5 C6 1.371(7) .
C6 C7 1.397(7) .
C6 H6A 0.9300 .
C7 H7A 0.9300 .
C8 C9 1.487(8) .
C8 C10 1.501(8) .
C8 H8A 0.9800 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C13B 1.438(16) .
C11 C12 1.486(9) .
C11 C13A 1.583(16) .
C11 H11A 0.9800 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13A H13A 0.9600 .
C13A H13B 0.9600 .
C13A H13C 0.9600 .
C13B H13D 0.9600 .
C13B H13E 0.9600 .
C13B H13F 0.9600 .
Cl1 C1S 1.766(17) .
C1S Cl1 1.766(17) 2
C1S H1SA 0.9700 .
C1S H1SB 0.9700 .
Cl1S C2S 1.32(2) 2
Cl1S Cl2S 1.457(17) 2
Cl1S Cl1S 1.56(2) 2
Cl1S C2S 1.758(15) .
Cl2S Cl1S 1.457(17) 2
Cl2S C2S 1.724(16) .
C2S H2SA 0.9700 .
C2S H2SB 0.9700 .
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 H1A S2 0.86 2.65 3.370(4) 141.7 7_556
N2 H2A S1 0.86 2.46 3.248(4) 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
O2 P1 O1 C8 51.4(4) .
N1 P1 O1 C8 -54.9(4) .
S1 P1 O1 C8 179.3(3) .
O1 P1 O2 C11 156.0(4) .
N1 P1 O2 C11 -93.5(4) .
S1 P1 O2 C11 32.9(4) .
O1 P1 N1 C1 -68.3(4) .
O2 P1 N1 C1 -176.8(4) .
S1 P1 N1 C1 54.8(4) .
C2 N2 C1 N1 173.0(4) .
C2 N2 C1 S2 -8.1(7) .
P1 N1 C1 N2 -17.5(6) .
P1 N1 C1 S2 163.6(3) .
C1 N2 C2 C7 141.2(5) .
C1 N2 C2 C3 -43.1(7) .
C7 C2 C3 C4 1.1(7) .
N2 C2 C3 C4 -174.5(4) .
C2 C3 C4 C5 -0.8(8) .
C5 O3 C5 C6 37.4(4) 2_556
C5 O3 C5 C4 -145.9(5) 2_556
C3 C4 C5 C6 0.5(8) .
C3 C4 C5 O3 -176.4(4) .
O3 C5 C6 C7 176.2(4) .
C4 C5 C6 C7 -0.5(8) .
C3 C2 C7 C6 -1.1(7) .
N2 C2 C7 C6 174.7(4) .
C5 C6 C7 C2 0.8(7) .
P1 O1 C8 C9 -125.5(4) .
P1 O1 C8 C10 111.5(5) .
P1 O2 C11 C13B -90.2(15) .
P1 O2 C11 C12 132.6(5) .
P1 O2 C11 C13A -118.2(9) .
Cl1S Cl2S C2S Cl1S 15.1(9) 2
C2S Cl1S C2S Cl2S 178(4) 2
Cl2S Cl1S C2S Cl2S -174.9(9) 2
Cl1S Cl1S C2S Cl2S -14.5(9) 2
