# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IIIA
_database_code_depnum_ccdc_archive 'CCDC 1062561'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
# internal code: dw0721
#===============================================================================
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H20 N2 P2 S2'
_chemical_formula_sum            'C8 H20 N2 P2 S2'
_chemical_formula_weight         270.32

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9112(2)
_cell_length_b                   9.9768(3)
_cell_length_c                   12.1132(3)
_cell_angle_alpha                85.594(2)
_cell_angle_beta                 88.593(2)
_cell_angle_gamma                79.0550(10)
_cell_volume                     699.27(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4860
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.580
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_exptl_special_details           ?

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6232
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.730
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3108
_reflns_number_gt                2952
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+0.2619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.049

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.44560(6) 0.84061(3) 0.64170(3) 0.02168(10) Uani 1 1 d . . . . .
H1 H 0.619(3) 0.8934(17) 0.5977(13) 0.029(4) Uiso 1 1 d . . . . .
P2 P 0.46670(6) 0.79081(3) 0.84694(3) 0.02267(10) Uani 1 1 d . . . . .
H2 H 0.651(3) 0.8196(19) 0.8909(14) 0.038(5) Uiso 1 1 d . . . . .
S1 S 0.22763(7) 0.82447(4) 0.53121(3) 0.03544(11) Uani 1 1 d . . . . .
S2 S 0.27342(8) 0.72131(4) 0.95755(3) 0.03807(12) Uani 1 1 d . . . . .
N1 N 0.5533(2) 0.70967(11) 0.73242(9) 0.0242(2) Uani 1 1 d . . . . .
N2 N 0.3656(2) 0.92345(11) 0.75626(8) 0.0226(2) Uani 1 1 d . . . . .
C1 C 0.6744(2) 0.56692(13) 0.71799(12) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.4994(3) 0.47219(17) 0.72461(17) 0.0451(4) Uani 1 1 d . . . . .
H2A H 0.4232 0.4750 0.7974 0.068 Uiso 1 1 calc R U . . .
H2B H 0.5785 0.3784 0.7140 0.068 Uiso 1 1 calc R U . . .
H2C H 0.3840 0.5023 0.6667 0.068 Uiso 1 1 calc R U . . .
C3 C 0.7950(3) 0.56442(17) 0.60524(14) 0.0415(4) Uani 1 1 d . . . . .
H3A H 0.6804 0.5939 0.5469 0.062 Uiso 1 1 calc R U . . .
H3B H 0.8768 0.4712 0.5944 0.062 Uiso 1 1 calc R U . . .
H3C H 0.9054 0.6266 0.6019 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8495(3) 0.52614(17) 0.81013(14) 0.0396(4) Uani 1 1 d . . . . .
H4A H 0.7695 0.5292 0.8820 0.059 Uiso 1 1 calc R U . . .
H4B H 0.9574 0.5898 0.8062 0.059 Uiso 1 1 calc R U . . .
H4C H 0.9345 0.4331 0.8016 0.059 Uiso 1 1 calc R U . . .
C5 C 0.2133(2) 1.05816(13) 0.77203(11) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.2841(3) 1.10923(16) 0.87925(12) 0.0341(3) Uani 1 1 d . . . . .
H6A H 0.2635 1.0437 0.9415 0.051 Uiso 1 1 calc R U . . .
H6B H 0.1881 1.1985 0.8913 0.051 Uiso 1 1 calc R U . . .
H6C H 0.4463 1.1183 0.8738 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2527(3) 1.15621(15) 0.67370(12) 0.0323(3) Uani 1 1 d . . . . .
H7A H 0.2063 1.1225 0.6055 0.048 Uiso 1 1 calc R U . . .
H7B H 0.4164 1.1620 0.6687 0.048 Uiso 1 1 calc R U . . .
H7C H 0.1608 1.2472 0.6838 0.048 Uiso 1 1 calc R U . . .
C8 C -0.0378(3) 1.04136(17) 0.77856(14) 0.0369(3) Uani 1 1 d . . . . .
H8A H -0.0594 0.9776 0.8419 0.055 Uiso 1 1 calc R U . . .
H8B H -0.0783 1.0052 0.7102 0.055 Uiso 1 1 calc R U . . .
H8C H -0.1371 1.1304 0.7877 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 1.6785(11) . ?
P1 N2 1.6817(11) . ?
P1 S1 1.9167(5) . ?
P1 H1 1.322(17) . ?
P2 N1 1.6799(11) . ?
P2 N2 1.6804(11) . ?
P2 S2 1.9143(5) . ?
P2 H2 1.314(18) . ?
N1 C1 1.4888(16) . ?
N2 C5 1.4915(16) . ?
C1 C4 1.520(2) . ?
C1 C3 1.525(2) . ?
C1 C2 1.525(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
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 C7 1.5244(19) . ?
C5 C8 1.5245(19) . ?
C5 C6 1.5268(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
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_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
N1 P1 N2 83.88(5) . . ?
N1 P1 S1 122.22(4) . . ?
N2 P1 S1 121.81(4) . . ?
N1 P1 H1 108.3(7) . . ?
N2 P1 H1 106.0(7) . . ?
S1 P1 H1 111.2(7) . . ?
N1 P2 N2 83.88(5) . . ?
N1 P2 S2 122.49(5) . . ?
N2 P2 S2 122.09(5) . . ?
N1 P2 H2 107.0(8) . . ?
N2 P2 H2 106.4(8) . . ?
S2 P2 H2 111.4(8) . . ?
P1 P2 H2 113.8(8) . . ?
C1 N1 P1 132.50(9) . . ?
C1 N1 P2 131.27(9) . . ?
P1 N1 P2 96.17(6) . . ?
C5 N2 P2 131.34(9) . . ?
C5 N2 P1 131.51(9) . . ?
P2 N2 P1 96.03(6) . . ?
N1 C1 C4 107.73(11) . . ?
N1 C1 C3 108.26(11) . . ?
C4 C1 C3 110.48(13) . . ?
N1 C1 C2 109.36(12) . . ?
C4 C1 C2 110.52(14) . . ?
C3 C1 C2 110.43(14) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C7 107.63(11) . . ?
N2 C5 C8 109.86(11) . . ?
C7 C5 C8 110.71(12) . . ?
N2 C5 C6 107.65(11) . . ?
C7 C5 C6 110.22(12) . . ?
C8 C5 C6 110.66(12) . . ?
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 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
N2 P1 N1 C1 178.79(13) . . . . ?
S1 P1 N1 C1 54.81(14) . . . . ?
N2 P1 N1 P2 1.54(6) . . . . ?
S1 P1 N1 P2 -122.44(4) . . . . ?
N2 P2 N1 C1 -178.85(13) . . . . ?
S2 P2 N1 C1 -54.44(14) . . . . ?
N2 P2 N1 P1 -1.55(6) . . . . ?
S2 P2 N1 P1 122.87(5) . . . . ?
N1 P2 N2 C5 170.22(13) . . . . ?
S2 P2 N2 C5 45.44(13) . . . . ?
N1 P2 N2 P1 1.54(6) . . . . ?
S2 P2 N2 P1 -123.24(4) . . . . ?
N1 P1 N2 C5 -170.19(13) . . . . ?
S1 P1 N2 C5 -45.82(13) . . . . ?
N1 P1 N2 P2 -1.54(6) . . . . ?
S1 P1 N2 P2 122.83(4) . . . . ?
P1 N1 C1 C4 146.01(12) . . . . ?
P2 N1 C1 C4 -37.63(17) . . . . ?
P1 N1 C1 C3 26.52(18) . . . . ?
P2 N1 C1 C3 -157.11(12) . . . . ?
P1 N1 C1 C2 -93.84(16) . . . . ?
P2 N1 C1 C2 82.53(16) . . . . ?
P2 N2 C5 C7 158.57(11) . . . . ?
P1 N2 C5 C7 -36.54(16) . . . . ?
P2 N2 C5 C8 -80.80(15) . . . . ?
P1 N2 C5 C8 84.08(15) . . . . ?
P2 N2 C5 C6 39.78(16) . . . . ?
P1 N2 C5 C6 -155.34(11) . . . . ?

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IIIB
_database_code_depnum_ccdc_archive 'CCDC 1062562'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
# internal code: cb110
#===============================================================================
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H36 N2 P2 S2'
_chemical_formula_sum            'C24 H36 N2 P2 S2'
_chemical_formula_weight         478.61

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   8.3695(19)
_cell_length_b                   10.1458(17)
_cell_length_c                   15.541(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.646(7)
_cell_angle_gamma                90
_cell_volume                     1292.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1341
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      18.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       φ-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11418
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         22.776
_diffrn_reflns_theta_full        22.776
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1743
_reflns_number_gt                1231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.4487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1743
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36926(11) 0.23279(8) 0.48196(7) 0.0528(3) Uani 1 1 d . . . . .
P1 P 0.41782(10) 0.40691(8) 0.52149(5) 0.0330(3) Uani 1 1 d . . . . .
N1 N 0.6114(3) 0.4610(2) 0.54459(15) 0.0288(6) Uani 1 1 d . . . . .
H1 H 0.344(3) 0.436(2) 0.5887(17) 0.042(8) Uiso 1 1 d . . . . .
C11 C 0.7591(3) 0.3981(3) 0.58879(19) 0.0286(7) Uani 1 1 d . . . . .
C12 C 0.8438(4) 0.3165(3) 0.5418(2) 0.0315(7) Uani 1 1 d . . . . .
C13 C 0.9879(4) 0.2623(3) 0.5870(2) 0.0442(9) Uani 1 1 d . . . . .
H13 H 1.0511 0.2090 0.5562 0.053 Uiso 1 1 calc R U . . .
C14 C 1.0418(4) 0.2835(3) 0.6747(2) 0.0493(9) Uani 1 1 d . . . . .
H14 H 1.1410 0.2447 0.7045 0.059 Uiso 1 1 calc R U . . .
C15 C 0.9533(4) 0.3602(3) 0.7195(2) 0.0469(9) Uani 1 1 d . . . . .
H15 H 0.9901 0.3715 0.7810 0.056 Uiso 1 1 calc R U . . .
C16 C 0.8117(4) 0.4219(3) 0.67839(19) 0.0332(8) Uani 1 1 d . . . . .
C21 C 0.7907(4) 0.2852(3) 0.44544(19) 0.0375(8) Uani 1 1 d . . . . .
H21 H 0.6778 0.3204 0.4253 0.045 Uiso 1 1 calc R U . . .
C22 C 0.7854(4) 0.1370(3) 0.4292(2) 0.0603(11) Uani 1 1 d . . . . .
H22A H 0.8953 0.1003 0.4472 0.090 Uiso 1 1 calc R U . . .
H22B H 0.7449 0.1198 0.3665 0.090 Uiso 1 1 calc R U . . .
H22C H 0.7125 0.0957 0.4633 0.090 Uiso 1 1 calc R U . . .
C23 C 0.9008(4) 0.3529(3) 0.3923(2) 0.0543(10) Uani 1 1 d . . . . .
H23A H 0.9024 0.4479 0.4038 0.081 Uiso 1 1 calc R U . . .
H23B H 0.8593 0.3369 0.3296 0.081 Uiso 1 1 calc R U . . .
H23C H 1.0116 0.3176 0.4093 0.081 Uiso 1 1 calc R U . . .
C31 C 0.7185(4) 0.5077(3) 0.7299(2) 0.0411(8) Uani 1 1 d . . . . .
H31 H 0.6582 0.5754 0.6890 0.049 Uiso 1 1 calc R U . . .
C32 C 0.8301(5) 0.5791(3) 0.8043(2) 0.0629(11) Uani 1 1 d . . . . .
H32A H 0.8805 0.5151 0.8488 0.094 Uiso 1 1 calc R U . . .
H32B H 0.7665 0.6429 0.8308 0.094 Uiso 1 1 calc R U . . .
H32C H 0.9153 0.6255 0.7813 0.094 Uiso 1 1 calc R U . . .
C33 C 0.5941(4) 0.4275(3) 0.7665(2) 0.0594(11) Uani 1 1 d . . . . .
H33A H 0.5230 0.3802 0.7186 0.089 Uiso 1 1 calc R U . . .
H33B H 0.5282 0.4866 0.7951 0.089 Uiso 1 1 calc R U . . .
H33C H 0.6509 0.3639 0.8095 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1 P1 1.8875(12) . ?
P1 N1 1.676(2) 3_666 ?
P1 N1 1.679(2) . ?
P1 H1 1.35(3) . ?
N1 C11 1.437(3) . ?
N1 P1 1.676(2) 3_666 ?
C11 C12 1.389(4) . ?
C11 C16 1.394(4) . ?
C12 C13 1.382(4) . ?
C12 C21 1.507(4) . ?
C13 C14 1.364(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.359(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C31 1.503(4) . ?
C21 C23 1.519(4) . ?
C21 C22 1.523(4) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C31 C32 1.516(4) . ?
C31 C33 1.520(4) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

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
N1 P1 N1 83.38(12) 3_666 . ?
N1 P1 S1 123.63(10) 3_666 . ?
N1 P1 S1 120.70(9) . . ?
N1 P1 H1 105.6(10) 3_666 . ?
N1 P1 H1 109.8(11) . . ?
S1 P1 H1 110.5(10) . . ?
P1 P1 H1 114.0(10) 3_666 . ?
C11 N1 P1 130.77(19) . 3_666 ?
C11 N1 P1 131.06(18) . . ?
P1 N1 P1 96.62(12) 3_666 . ?
C12 C11 C16 122.5(3) . . ?
C12 C11 N1 119.6(3) . . ?
C16 C11 N1 117.9(2) . . ?
C13 C12 C11 117.1(3) . . ?
C13 C12 C21 118.2(3) . . ?
C11 C12 C21 124.6(3) . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C11 116.9(3) . . ?
C15 C16 C31 120.4(3) . . ?
C11 C16 C31 122.6(3) . . ?
C12 C21 C23 110.8(2) . . ?
C12 C21 C22 111.4(3) . . ?
C23 C21 C22 110.9(3) . . ?
C12 C21 H21 107.9 . . ?
C23 C21 H21 107.9 . . ?
C22 C21 H21 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C31 C32 112.1(3) . . ?
C16 C31 C33 111.0(3) . . ?
C32 C31 C33 109.4(3) . . ?
C16 C31 H31 108.0 . . ?
C32 C31 H31 108.0 . . ?
C33 C31 H31 108.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
N1 P1 N1 C11 -166.6(3) 3_666 . . . ?
S1 P1 N1 C11 -41.2(3) . . . . ?
N1 P1 N1 P1 -0.001(1) 3_666 . . 3_666 ?
S1 P1 N1 P1 125.41(10) . . . 3_666 ?
P1 N1 C11 C12 -77.6(3) 3_666 . . . ?
P1 N1 C11 C12 84.8(3) . . . . ?
P1 N1 C11 C16 102.5(3) 3_666 . . . ?
P1 N1 C11 C16 -95.1(3) . . . . ?
C16 C11 C12 C13 -2.3(4) . . . . ?
N1 C11 C12 C13 177.8(3) . . . . ?
C16 C11 C12 C21 178.7(3) . . . . ?
N1 C11 C12 C21 -1.2(4) . . . . ?
C11 C12 C13 C14 2.6(5) . . . . ?
C21 C12 C13 C14 -178.4(3) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 -2.3(5) . . . . ?
C14 C15 C16 C11 2.5(5) . . . . ?
C14 C15 C16 C31 -179.1(3) . . . . ?
C12 C11 C16 C15 -0.1(4) . . . . ?
N1 C11 C16 C15 179.7(3) . . . . ?
C12 C11 C16 C31 -178.6(3) . . . . ?
N1 C11 C16 C31 1.3(4) . . . . ?
C13 C12 C21 C23 -70.5(4) . . . . ?
C11 C12 C21 C23 108.5(3) . . . . ?
C13 C12 C21 C22 53.5(4) . . . . ?
C11 C12 C21 C22 -127.6(3) . . . . ?
C15 C16 C31 C32 33.4(4) . . . . ?
C11 C16 C31 C32 -148.2(3) . . . . ?
C15 C16 C31 C33 -89.4(4) . . . . ?
C11 C16 C31 C33 89.0(4) . . . . ?

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IIIC
_database_code_depnum_ccdc_archive 'CCDC 1062563'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
#internal code: cb113
#===============================================================================
_audit_creation_method           SHELXL-2013

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 N2 P2 S2'
_chemical_formula_sum            'C18 H24 N2 P2 S2'
_chemical_formula_weight         394.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4215(3)
_cell_length_b                   11.0475(3)
_cell_length_c                   9.3492(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.462(2)
_cell_angle_gamma                90
_cell_volume                     1014.89(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8186
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      66.59

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.878
_shelx_estimated_absorpt_T_min   0.526
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4950
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           ?

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13746
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.500
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_full        66.593
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1755
_reflns_number_gt                1462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+2.2748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1755
_refine_ls_number_parameters     125
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.068

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30257(10) 0.37827(9) 0.24117(12) 0.0493(3) Uani 0.923(3) 1 d D . P A 1
P1 P 0.43173(8) 0.49243(8) 0.36014(10) 0.0294(3) Uani 0.923(3) 1 d D . P A 1
H1 H 0.451(3) 0.577(3) 0.273(4) 0.029(8) Uiso 0.923(3) 1 d . . P A 1
S1A S 0.361(2) 0.449(2) 0.195(2) 0.105(8) Uiso 0.077(3) 1 d D . P A 2
P1A P 0.4125(19) 0.4223(16) 0.4071(18) 0.077(6) Uiso 0.077(3) 1 d D . P A 2
H1A H 0.3668 0.3243 0.4502 0.116 Uiso 0.077(3) 1 d R U P A 2
N1 N 0.4166(3) 0.5540(2) 0.5181(3) 0.0350(6) Uani 1 1 d D . . . .
C11 C 0.3091(3) 0.6226(3) 0.5442(3) 0.0311(7) Uani 1 1 d . . . . .
C12 C 0.2172(3) 0.5637(3) 0.5995(4) 0.0360(8) Uani 1 1 d . . . . .
C13 C 0.1168(3) 0.6326(3) 0.6279(4) 0.0398(8) Uani 1 1 d . . . . .
H13 H 0.0531 0.5938 0.6653 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1072(3) 0.7564(3) 0.6033(4) 0.0411(8) Uani 1 1 d . . . . .
C15 C 0.1989(3) 0.8116(3) 0.5462(4) 0.0388(8) Uani 1 1 d . . . . .
H15 H 0.1911 0.8961 0.5263 0.047 Uiso 1 1 calc R U . . .
C16 C 0.3024(3) 0.7473(3) 0.5169(3) 0.0349(7) Uani 1 1 d . . . . .
C17 C 0.0004(4) 0.8293(4) 0.6417(5) 0.0583(11) Uani 1 1 d . . . . .
H17A H -0.0389 0.8893 0.5618 0.087 Uiso 1 1 calc R U . . .
H17B H 0.0424 0.8709 0.7387 0.087 Uiso 1 1 calc R U . . .
H17C H -0.0714 0.7752 0.6495 0.087 Uiso 1 1 calc R U . . .
C21 C 0.2282(4) 0.4297(3) 0.6336(5) 0.0517(10) Uani 1 1 d . . . . .
H21A H 0.2523 0.3869 0.5543 0.077 Uiso 1 1 calc R U . . .
H21B H 0.1407 0.3995 0.6366 0.077 Uiso 1 1 calc R U . . .
H21C H 0.2987 0.4156 0.7320 0.077 Uiso 1 1 calc R U . . .
C31 C 0.4035(4) 0.8115(3) 0.4611(4) 0.0436(9) Uani 1 1 d . . . . .
H31A H 0.3909 0.8991 0.4654 0.065 Uiso 1 1 calc R U . . .
H31B H 0.3896 0.7873 0.3561 0.065 Uiso 1 1 calc R U . . .
H31C H 0.4960 0.7899 0.5252 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1 P1 1.9084(13) . ?
P1 N1 1.680(3) . ?
P1 N1 1.691(3) 3_666 ?
P1 H1 1.30(3) . ?
S1A P1A 1.899(17) . ?
P1A N1 1.703(19) 3_666 ?
P1A N1 1.779(14) . ?
P1A H1A 1.3000 . ?
N1 C11 1.439(4) . ?
N1 P1 1.691(3) 3_666 ?
N1 P1A 1.703(19) 3_666 ?
C11 C12 1.392(4) . ?
C11 C16 1.398(4) . ?
C12 C13 1.390(4) . ?
C12 C21 1.511(5) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(5) . ?
C14 C17 1.511(5) . ?
C15 C16 1.393(4) . ?
C15 H15 0.9500 . ?
C16 C31 1.500(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

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
N1 P1 N1 82.63(13) . 3_666 ?
N1 P1 S1 121.68(11) . . ?
N1 P1 S1 120.77(11) 3_666 . ?
N1 P1 H1 110.0(14) . . ?
N1 P1 H1 109.7(14) 3_666 . ?
S1 P1 H1 109.4(14) . . ?
N1 P1A N1 79.4(7) 3_666 . ?
N1 P1A S1A 107.4(13) 3_666 . ?
N1 P1A S1A 115.2(12) . . ?
N1 P1A H1A 116.2 3_666 . ?
N1 P1A H1A 116.2 . . ?
S1A P1A H1A 116.6 . . ?
C11 N1 P1 132.0(2) . . ?
C11 N1 P1 130.7(2) . 3_666 ?
P1 N1 P1 97.38(13) . 3_666 ?
C11 N1 P1A 128.1(5) . 3_666 ?
C11 N1 P1A 131.4(6) . . ?
P1A N1 P1A 100.6(7) 3_666 . ?
C12 C11 C16 122.0(3) . . ?
C12 C11 N1 119.2(3) . . ?
C16 C11 N1 118.8(3) . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 C21 120.4(3) . . ?
C11 C12 C21 121.6(3) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 C17 121.0(3) . . ?
C13 C14 C17 120.3(3) . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C11 117.5(3) . . ?
C15 C16 C31 120.4(3) . . ?
C11 C16 C31 122.1(3) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C31 H31A 109.5 . . ?
C16 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C16 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

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
N1 P1 N1 C11 -179.1(4) 3_666 . . . ?
S1 P1 N1 C11 -57.3(3) . . . . ?
N1 P1 N1 P1 0.002(0) 3_666 . . 3_666 ?
S1 P1 N1 P1 121.75(12) . . . 3_666 ?
N1 P1 N1 P1A 31.9(6) 3_666 . . 3_666 ?
S1 P1 N1 P1A 153.7(6) . . . 3_666 ?
N1 P1 N1 P1A -75.6(11) 3_666 . . . ?
S1 P1 N1 P1A 46.2(11) . . . . ?
N1 P1A N1 C11 -178.5(4) 3_666 . . . ?
S1A P1A N1 C11 77.1(15) . . . . ?
P1A P1A N1 C11 -178.5(4) 3_666 . . . ?
N1 P1A N1 P1 75.9(10) 3_666 . . . ?
S1A P1A N1 P1 -28.5(9) . . . . ?
N1 P1A N1 P1 -30.3(5) 3_666 . . 3_666 ?
S1A P1A N1 P1 -134.6(13) . . . 3_666 ?
N1 P1A N1 P1A 0.000(1) 3_666 . . 3_666 ?
S1A P1A N1 P1A -104.3(15) . . . 3_666 ?
P1 N1 C11 C12 97.9(4) . . . . ?
P1 N1 C11 C12 -80.9(4) 3_666 . . . ?
P1A N1 C11 C12 -122.9(9) 3_666 . . . ?
P1A N1 C11 C12 55.2(9) . . . . ?
P1 N1 C11 C16 -83.8(4) . . . . ?
P1 N1 C11 C16 97.5(3) 3_666 . . . ?
P1A N1 C11 C16 55.4(9) 3_666 . . . ?
P1A N1 C11 C16 -126.4(9) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?
N1 C11 C12 C13 178.1(3) . . . . ?
C16 C11 C12 C21 -177.9(3) . . . . ?
N1 C11 C12 C21 0.4(5) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C21 C12 C13 C14 177.6(3) . . . . ?
C12 C13 C14 C15 1.2(5) . . . . ?
C12 C13 C14 C17 -177.4(3) . . . . ?
C13 C14 C15 C16 -1.8(5) . . . . ?
C17 C14 C15 C16 176.8(3) . . . . ?
C14 C15 C16 C11 1.4(5) . . . . ?
C14 C15 C16 C31 -177.4(3) . . . . ?
C12 C11 C16 C15 -0.4(5) . . . . ?
N1 C11 C16 C15 -178.7(3) . . . . ?
C12 C11 C16 C31 178.4(3) . . . . ?
N1 C11 C16 C31 0.1(5) . . . . ?

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/THF'
