#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:53:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180403 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/72/7207210.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_7207210
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         'C20 H36 N4 O4 P2 S4'
_chemical_formula_sum            'C20 H36 N4 O4 P2 S4'
_chemical_formula_weight         586.71
_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                 98.54(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.695(9)
_cell_length_b                   8.371(3)
_cell_length_c                   15.078(6)
_cell_measurement_reflns_used    1281
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.55
_cell_measurement_theta_min      2.85
_cell_volume                     2958(2)
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12383
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8996
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0386
_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)+(0.0456P)²+0.2095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2437
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06244a.txt
_cod_data_source_block           saf64
_cod_original_cell_volume        2957.6(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7207210
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
S1 S 0.84043(2) 0.59954(7) 1.07043(4) 0.02834(15) Uani 1 1 d .
S2 S 1.03659(2) 0.65666(7) 0.91577(4) 0.02859(15) Uani 1 1 d .
P1 P 0.87230(2) 0.73278(7) 0.98730(4) 0.02103(14) Uani 1 1 d .
O1 O 0.84191(6) 0.72664(16) 0.88707(9) 0.0233(3) Uani 1 1 d .
O2 O 0.87524(6) 0.91882(17) 1.00340(10) 0.0259(3) Uani 1 1 d .
N1 N 0.94146(7) 0.6939(2) 0.98575(11) 0.0214(4) Uani 1 1 d .
H1A H 0.9573 0.6252 1.0261 0.026 Uiso 1 1 d R
N2 N 0.96090(7) 0.8966(2) 0.89151(11) 0.0219(4) Uani 1 1 d .
H2A H 0.9335 0.9464 0.9139 0.026 Uiso 1 1 d R
C1 C 0.97705(8) 0.7558(3) 0.92942(14) 0.0213(4) Uani 1 1 d .
C2 C 0.98222(8) 0.9774(2) 0.82002(13) 0.0191(4) Uani 1 1 d .
C3 C 1.0000 0.8929(3) 0.7500 0.0205(6) Uani 1 2 d S
H3B H 1.0000 0.7794 0.7500 0.025 Uiso 1 2 calc SR
C5 C 0.98144(9) 1.1428(2) 0.82044(15) 0.0254(5) Uani 1 1 d .
H5A H 0.9684 1.1991 0.8682 0.030 Uiso 1 1 calc R
C6 C 1.0000 1.2255(4) 0.7500 0.0292(7) Uani 1 2 d S
H6A H 1.0000 1.3389 0.7500 0.035 Uiso 1 2 calc SR
C8 C 0.82326(10) 0.5739(3) 0.84347(15) 0.0292(5) Uani 1 1 d .
H8A H 0.8063 0.5051 0.8869 0.035 Uiso 1 1 calc R
C9 C 0.77768(11) 0.6168(3) 0.76644(17) 0.0396(6) Uani 1 1 d .
H9A H 0.7477 0.6789 0.7889 0.059 Uiso 1 1 calc R
H9B H 0.7612 0.5189 0.7379 0.059 Uiso 1 1 calc R
H9C H 0.7945 0.6804 0.7225 0.059 Uiso 1 1 calc R
C10 C 0.87376(12) 0.4891(3) 0.81456(18) 0.0476(7) Uani 1 1 d .
H10A H 0.8608 0.3911 0.7823 0.071 Uiso 1 1 calc R
H10B H 0.9013 0.4621 0.8675 0.071 Uiso 1 1 calc R
H10C H 0.8920 0.5592 0.7751 0.071 Uiso 1 1 calc R
C11 C 0.82449(10) 1.0111(3) 1.0159(2) 0.0468(8) Uani 1 1 d .
H11A H 0.7896 0.9432 1.0019 0.056 Uiso 1 1 calc R
C12 C 0.83205(14) 1.0615(4) 1.1115(2) 0.0768(12) Uani 1 1 d .
H12A H 0.8394 0.9674 1.1501 0.115 Uiso 1 1 calc R
H12B H 0.7973 1.1151 1.1240 0.115 Uiso 1 1 calc R
H12C H 0.8644 1.1353 1.1233 0.115 Uiso 1 1 calc R
C13 C 0.82231(13) 1.1477(3) 0.9492(3) 0.0769(12) Uani 1 1 d .
H13A H 0.8215 1.1045 0.8886 0.115 Uiso 1 1 calc R
H13B H 0.8562 1.2152 0.9644 0.115 Uiso 1 1 calc R
H13C H 0.7879 1.2115 0.9516 0.115 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
O1 P1 O2 100.57(8) .
O1 P1 N1 106.80(9) .
O2 P1 N1 99.97(8) .
O1 P1 S1 116.13(7) .
O2 P1 S1 119.18(6) .
N1 P1 S1 112.20(7) .
C8 O1 P1 121.33(13) .
C11 O2 P1 121.50(14) .
C1 N1 P1 128.53(15) .
C1 N1 H1A 115.7 .
P1 N1 H1A 115.8 .
C1 N2 C2 128.93(17) .
C1 N2 H2A 115.7 .
C2 N2 H2A 115.4 .
N2 C1 N1 115.45(17) .
N2 C1 S2 125.11(16) .
N1 C1 S2 119.41(16) .
C5 C2 C3 121.3(2) .
C5 C2 N2 117.67(18) .
C3 C2 N2 120.95(19) .
C2 C3 C2 118.7(3) 2_756
C2 C3 H3B 120.7 2_756
C2 C3 H3B 120.7 .
C2 C5 C6 119.2(2) .
C2 C5 H5A 120.4 .
C6 C5 H5A 120.4 .
C5 C6 C5 120.4(3) 2_756
C5 C6 H6A 119.8 2_756
C5 C6 H6A 119.8 .
O1 C8 C9 105.68(18) .
O1 C8 C10 109.77(19) .
C9 C8 C10 113.4(2) .
O1 C8 H8A 109.3 .
C9 C8 H8A 109.3 .
C10 C8 H8A 109.3 .
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 .
O2 C11 C12 106.9(2) .
O2 C11 C13 105.1(2) .
C12 C11 C13 114.5(3) .
O2 C11 H11A 110.0 .
C12 C11 H11A 110.0 .
C13 C11 H11A 110.0 .
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 C13 H13A 109.5 .
C11 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C11 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 P1 1.9148(9) .
S2 C1 1.676(2) .
P1 O1 1.5754(17) .
P1 O2 1.5760(16) .
P1 N1 1.6745(18) .
O1 C8 1.475(3) .
O2 C11 1.465(3) .
N1 C1 1.383(3) .
N1 H1A 0.8801 .
N2 C1 1.340(3) .
N2 C2 1.427(2) .
N2 H2A 0.8801 .
C2 C5 1.384(3) .
C2 C3 1.387(2) .
C3 C2 1.387(2) 2_756
C3 H3B 0.9500 .
C5 C6 1.393(3) .
C5 H5A 0.9500 .
C6 C5 1.393(3) 2_756
C6 H6A 0.9500 .
C8 C9 1.507(3) .
C8 C10 1.510(3) .
C8 H8A 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.487(4) .
C11 C13 1.518(4) .
C11 H11A 1.0000 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 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 H1A S2 0.88 2.51 3.295(2) 148.4 5_767
N2 H2A O2 0.88 2.08 2.832(2) 142.6 .
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_4
O2 P1 O1 C8 -172.82(14) .
N1 P1 O1 C8 83.27(16) .
S1 P1 O1 C8 -42.73(16) .
O1 P1 O2 C11 74.60(19) .
N1 P1 O2 C11 -176.04(18) .
S1 P1 O2 C11 -53.5(2) .
O1 P1 N1 C1 45.6(2) .
O2 P1 N1 C1 -58.69(19) .
S1 P1 N1 C1 173.98(16) .
C2 N2 C1 N1 -168.27(19) .
C2 N2 C1 S2 13.7(3) .
P1 N1 C1 N2 23.0(3) .
P1 N1 C1 S2 -158.90(12) .
C1 N2 C2 C5 -148.7(2) .
C1 N2 C2 C3 35.0(3) .
C5 C2 C3 C2 0.67(14) 2_756
N2 C2 C3 C2 176.9(2) 2_756
C3 C2 C5 C6 -1.3(3) .
N2 C2 C5 C6 -177.70(16) .
C2 C5 C6 C5 0.65(14) 2_756
P1 O1 C8 C9 158.29(15) .
P1 O1 C8 C10 -79.1(2) .
P1 O2 C11 C12 109.6(2) .
P1 O2 C11 C13 -128.29(19) .
