#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:34:53 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179507 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/04/4340476.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_4340476
loop_
_publ_author_name
'Amir, Aviran'
'Ezra, Alon'
'Shimon, Linda J. W.'
'Fischer, Bilha'
_publ_section_title
;
 Novel Cu(I)-Selective Chelators Based on a Bis(phosphorothioyl)amide
 Scaffold.
;
_journal_issue                   15
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7901
_journal_paper_doi               10.1021/ic500465z
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C6 H13 N P2 S6'
_chemical_formula_sum            'C6 H13 N P2 S6'
_chemical_formula_weight         353.47
_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                 106.102(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2348(4)
_cell_length_b                   16.6337(8)
_cell_length_c                   10.4261(5)
_cell_measurement_reflns_used    8014
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.35
_cell_volume                     1372.09(12)
_computing_cell_refinement       'Bruker Apex2'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker KappaApex2 CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10250
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.7539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0320P)²+0.6898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0633
_reflns_number_gt                3163
_reflns_number_total             3325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic500465z_si_004.cif
_cod_data_source_block           aa75
_cod_depositor_comments
'Adding full bibliography for 4340476--4340478.cif.'
_cod_original_cell_volume        1372.09(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4340476
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
S1 S 0.16338(5) 0.13884(2) 0.53817(4) 0.01232(9) Uani 1 1 d .
S2 S 0.36739(5) 0.22299(2) 0.81027(3) 0.01056(9) Uani 1 1 d .
S3 S 0.55814(5) 0.18455(2) 0.55510(4) 0.01406(9) Uani 1 1 d .
S4 S 0.62657(5) -0.05665(2) 0.94920(3) 0.01051(9) Uani 1 1 d .
S5 S 0.82584(5) -0.00430(2) 0.73947(4) 0.01117(9) Uani 1 1 d .
S6 S 0.73594(5) 0.14471(2) 0.92582(4) 0.01286(9) Uani 1 1 d .
P1 P 0.40974(5) 0.14844(2) 0.65918(3) 0.00708(9) Uani 1 1 d .
P2 P 0.65594(4) 0.04414(2) 0.83740(3) 0.00710(9) Uani 1 1 d .
C1 C 0.14496(19) 0.24523(10) 0.72935(15) 0.0133(3) Uani 1 1 d .
H1A H 0.0893 0.2639 0.7968 0.016 Uiso 1 1 calc R
H1B H 0.1365 0.2886 0.6628 0.016 Uiso 1 1 calc R
N1 N 0.46359(15) 0.05551(7) 0.72866(11) 0.0073(2) Uani 1 1 d .
C2 C 0.05704(19) 0.17056(10) 0.66102(16) 0.0148(3) Uani 1 1 d .
H2A H -0.0633 0.1823 0.6167 0.018 Uiso 1 1 calc R
H2B H 0.0626 0.1273 0.7274 0.018 Uiso 1 1 calc R
C3 C 0.8391(2) -0.10668(10) 0.80481(16) 0.0146(3) Uani 1 1 d .
H3A H 0.7471 -0.1398 0.7480 0.018 Uiso 1 1 calc R
H3B H 0.9484 -0.1311 0.8040 0.018 Uiso 1 1 calc R
C4 C 0.8238(2) -0.10453(10) 0.94631(16) 0.0149(3) Uani 1 1 d .
H4A H 0.9201 -0.0743 1.0042 0.018 Uiso 1 1 calc R
H4B H 0.8272 -0.1600 0.9814 0.018 Uiso 1 1 calc R
C5 C 0.39064(18) -0.01618(9) 0.64525(14) 0.0099(3) Uani 1 1 d .
H5A H 0.4789 -0.0581 0.6567 0.012 Uiso 1 1 calc R
H5B H 0.3559 -0.0003 0.5500 0.012 Uiso 1 1 calc R
C6 C 0.23948(19) -0.05099(10) 0.68216(17) 0.0155(3) Uani 1 1 d .
H6A H 0.2710 -0.0632 0.7779 0.023 Uiso 1 1 calc R
H6B H 0.2029 -0.1004 0.6312 0.023 Uiso 1 1 calc R
H6C H 0.1469 -0.0119 0.6613 0.023 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'
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
C2 S1 P1 97.46(5)
C1 S2 P1 97.26(5)
C4 S4 P2 95.74(5)
C3 S5 P2 98.90(5)
N1 P1 S3 112.74(5)
N1 P1 S1 106.40(4)
S3 P1 S1 110.16(2)
N1 P1 S2 106.97(4)
S3 P1 S2 119.73(2)
S1 P1 S2 99.38(2)
N1 P2 S6 110.86(5)
N1 P2 S4 103.44(5)
S6 P2 S4 120.24(2)
N1 P2 S5 110.10(5)
S6 P2 S5 112.17(2)
S4 P2 S5 99.11(2)
C2 C1 S2 109.78(11)
C2 C1 H1A 109.7
S2 C1 H1A 109.7
C2 C1 H1B 109.7
S2 C1 H1B 109.7
H1A C1 H1B 108.2
C5 N1 P2 116.86(9)
C5 N1 P1 117.22(9)
P2 N1 P1 118.11(7)
C1 C2 S1 107.99(10)
C1 C2 H2A 110.1
S1 C2 H2A 110.1
C1 C2 H2B 110.1
S1 C2 H2B 110.1
H2A C2 H2B 108.4
C4 C3 S5 109.19(11)
C4 C3 H3A 109.8
S5 C3 H3A 109.8
C4 C3 H3B 109.8
S5 C3 H3B 109.8
H3A C3 H3B 108.3
C3 C4 S4 110.03(11)
C3 C4 H4A 109.7
S4 C4 H4A 109.7
C3 C4 H4B 109.7
S4 C4 H4B 109.7
H4A C4 H4B 108.2
N1 C5 C6 112.43(12)
N1 C5 H5A 109.1
C6 C5 H5A 109.1
N1 C5 H5B 109.1
C6 C5 H5B 109.1
H5A C5 H5B 107.9
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.8188(16)
S1 P1 2.0768(5)
S2 C1 1.8294(16)
S2 P1 2.1085(5)
S3 P1 1.9410(5)
S4 C4 1.8167(15)
S4 P2 2.0938(5)
S5 C3 1.8261(16)
S5 P2 2.1075(5)
S6 P2 1.9353(5)
P1 N1 1.7124(13)
P2 N1 1.6835(12)
C1 C2 1.513(2)
C1 H1A 0.9900
C1 H1B 0.9900
N1 C5 1.4998(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.515(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.516(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
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
C2 S1 P1 N1 92.77(7)
C2 S1 P1 S3 -144.73(6)
C2 S1 P1 S2 -18.14(6)
C1 S2 P1 N1 -118.28(7)
C1 S2 P1 S3 111.95(6)
C1 S2 P1 S1 -7.82(6)
C4 S4 P2 N1 135.77(7)
C4 S4 P2 S6 -99.97(6)
C4 S4 P2 S5 22.42(6)
C3 S5 P2 N1 -105.66(7)
C3 S5 P2 S6 130.38(6)
C3 S5 P2 S4 2.36(6)
P1 S2 C1 C2 39.46(11)
S6 P2 N1 C5 175.70(9)
S4 P2 N1 C5 -54.12(10)
S5 P2 N1 C5 50.99(11)
S6 P2 N1 P1 27.28(9)
S4 P2 N1 P1 157.46(6)
S5 P2 N1 P1 -97.43(7)
S3 P1 N1 C5 -87.08(10)
S1 P1 N1 C5 33.77(11)
S2 P1 N1 C5 139.28(9)
S3 P1 N1 P2 61.23(8)
S1 P1 N1 P2 -177.92(6)
S2 P1 N1 P2 -72.41(8)
S2 C1 C2 S1 -59.49(12)
P1 S1 C2 C1 46.55(11)
P2 S5 C3 C4 -33.62(12)
S5 C3 C4 S4 57.53(14)
P2 S4 C4 C3 -49.20(12)
P2 N1 C5 C6 111.27(12)
P1 N1 C5 C6 -100.02(13)
