# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1439936'
_audit_update_record             
;
2015-12-01 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H16 N P S2'
_chemical_formula_moiety         'C14 H16 N P S2'
_chemical_formula_weight         293.38
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.666(2)
_cell_length_b                   13.325(3)
_cell_length_c                   14.112(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1441.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2462
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      25.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.00
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  0.982

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            17514
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_theta_max         25.373
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2643
_reflns_number_gt                2138
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1348
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     165
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0873P)²+0.6328P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.26
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.21604(19) 0.18425(13) 0.21100(12) 0.0423(5) Uani 1 1 d . . . . .
S9 S -0.1413(2) 0.23027(14) 0.10719(12) 0.0469(5) Uani 1 1 d . . . . .
P1 P -0.0532(2) 0.16681(13) 0.23657(12) 0.0425(5) Uani 1 1 d . . . . .
N1 N -0.0831(7) 0.2576(4) 0.3147(4) 0.0457(13) Uani 1 1 d . . . . .
C1 C 0.2427(8) 0.1101(5) 0.1081(5) 0.0374(14) Uani 1 1 d . . . . .
C2 C 0.4066(8) 0.0662(5) 0.1022(5) 0.0434(16) Uani 1 1 d . . . . .
H2 H 0.4884 0.0763 0.1519 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4529(9) 0.0070(6) 0.0235(5) 0.0515(18) Uani 1 1 d . . . . .
H3 H 0.5662 -0.0216 0.0201 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3399(9) -0.0092(6) -0.0459(5) 0.0529(18) Uani 1 1 d . . . . .
H4 H 0.3725 -0.0509 -0.0975 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1712(8) 0.0346(5) -0.0447(5) 0.0403(15) Uani 1 1 d . . . . .
C6 C 0.0572(10) 0.0170(5) -0.1226(5) 0.0498(17) Uani 1 1 d . . . . .
H6 H 0.0936 -0.0249 -0.1734 0.060 Uiso 1 1 calc R U . . .
C7 C -0.1043(10) 0.0601(5) -0.1244(5) 0.0555(19) Uani 1 1 d . . . . .
H7 H -0.1804 0.0485 -0.1763 0.067 Uiso 1 1 calc R U . . .
C8 C -0.1566(9) 0.1209(5) -0.0500(5) 0.0455(16) Uani 1 1 d . . . . .
H8 H -0.2697 0.1500 -0.0522 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0529(9) 0.1408(4) 0.0258(4) 0.0379(14) Uani 1 1 d . . . . .
C10 C 0.1183(7) 0.0972(5) 0.0328(4) 0.0362(14) Uani 1 1 d . . . . .
C11 C -0.0232(9) 0.3628(5) 0.3041(5) 0.0508(18) Uani 1 1 d . . . . .
H11A H -0.1229 0.4086 0.3149 0.061 Uiso 1 1 calc R U . . .
H11B H 0.0187 0.3734 0.2385 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1210(9) 0.3883(6) 0.3724(6) 0.0559(19) Uani 1 1 d . . . . .
H12A H 0.2183 0.3415 0.3635 0.067 Uiso 1 1 calc R U . . .
H12B H 0.0774 0.3829 0.4375 0.067 Uiso 1 1 calc R U . . .
H12C H 0.1612 0.4570 0.3607 0.067 Uiso 1 1 calc R U . . .
C13 C -0.2140(9) 0.2398(6) 0.3885(5) 0.0544(18) Uani 1 1 d . . . . .
H13A H -0.1854 0.2817 0.4442 0.065 Uiso 1 1 calc R U . . .
H13B H -0.2074 0.1686 0.4084 0.065 Uiso 1 1 calc R U . . .
C14 C -0.3995(9) 0.2627(7) 0.3576(6) 0.069(2) Uani 1 1 d . . . . .
H14A H -0.4793 0.2514 0.4108 0.083 Uiso 1 1 calc R U . . .
H14B H -0.4318 0.2186 0.3048 0.083 Uiso 1 1 calc R U . . .
H14C H -0.4074 0.3329 0.3372 0.083 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.769(7) . ?
S1 P1 2.109(2) . ?
S9 C9 1.789(6) . ?
S9 P1 2.122(2) . ?
P1 N1 1.652(6) . ?
N1 C13 1.466(8) . ?
N1 C11 1.483(9) . ?
C1 C2 1.388(9) . ?
C1 C10 1.437(9) . ?
C2 C3 1.408(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.325(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.423(10) . ?
C5 C10 1.435(9) . ?
C6 C7 1.365(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.360(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.439(9) . ?
C11 C12 1.506(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C1 S1 P1 101.1(2) . . ?
C9 S9 P1 99.6(2) . . ?
N1 P1 S1 99.7(2) . . ?
N1 P1 S9 103.8(2) . . ?
S1 P1 S9 96.91(9) . . ?
C13 N1 C11 115.9(5) . . ?
C13 N1 P1 116.8(5) . . ?
C11 N1 P1 125.6(4) . . ?
C2 C1 C10 120.4(6) . . ?
C2 C1 S1 112.9(5) . . ?
C10 C1 S1 126.6(4) . . ?
C1 C2 C3 120.8(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.9(6) . . ?
C4 C5 C10 120.4(6) . . ?
C6 C5 C10 120.7(6) . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.7(7) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 122.7(7) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C8 C9 C10 120.6(6) . . ?
C8 C9 S9 114.4(5) . . ?
C10 C9 S9 124.8(5) . . ?
C5 C10 C1 116.4(5) . . ?
C5 C10 C9 116.1(6) . . ?
C1 C10 C9 127.4(6) . . ?
N1 C11 C12 112.1(6) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
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 . . ?
N1 C13 C14 113.9(6) . . ?
N1 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
S1 P1 N1 C13 -146.5(4) . . . . ?
S9 P1 N1 C13 113.9(5) . . . . ?
S1 P1 N1 C11 49.3(6) . . . . ?
S9 P1 N1 C11 -50.4(6) . . . . ?
P1 S1 C1 C2 -149.0(4) . . . . ?
P1 S1 C1 C10 34.3(6) . . . . ?
C10 C1 C2 C3 -1.1(10) . . . . ?
S1 C1 C2 C3 -178.1(5) . . . . ?
C1 C2 C3 C4 -1.0(11) . . . . ?
C2 C3 C4 C5 1.8(11) . . . . ?
C3 C4 C5 C6 178.2(7) . . . . ?
C3 C4 C5 C10 -0.6(10) . . . . ?
C4 C5 C6 C7 -178.4(7) . . . . ?
C10 C5 C6 C7 0.3(10) . . . . ?
C5 C6 C7 C8 -0.1(11) . . . . ?
C6 C7 C8 C9 0.4(11) . . . . ?
C7 C8 C9 C10 -1.0(10) . . . . ?
C7 C8 C9 S9 174.6(6) . . . . ?
P1 S9 C9 C8 143.0(5) . . . . ?
P1 S9 C9 C10 -41.6(5) . . . . ?
C4 C5 C10 C1 -1.4(9) . . . . ?
C6 C5 C10 C1 179.8(6) . . . . ?
C4 C5 C10 C9 177.9(6) . . . . ?
C6 C5 C10 C9 -0.8(9) . . . . ?
C2 C1 C10 C5 2.2(9) . . . . ?
S1 C1 C10 C5 178.7(5) . . . . ?
C2 C1 C10 C9 -177.0(6) . . . . ?
S1 C1 C10 C9 -0.6(9) . . . . ?
C8 C9 C10 C5 1.1(9) . . . . ?
S9 C9 C10 C5 -173.9(5) . . . . ?
C8 C9 C10 C1 -179.6(6) . . . . ?
S9 C9 C10 C1 5.3(9) . . . . ?
C13 N1 C11 C12 84.5(7) . . . . ?
P1 N1 C11 C12 -111.2(6) . . . . ?
C11 N1 C13 C14 82.6(8) . . . . ?
P1 N1 C13 C14 -83.2(7) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1439937'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-02
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H12 P2 S4'
_chemical_formula_moiety         'C20 H12 P2 S4'
_chemical_formula_weight         442.50
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5926(8)
_cell_length_b                   7.7769(11)
_cell_length_c                   9.5253(19)
_cell_angle_alpha                100.330(18)
_cell_angle_beta                 112.832(12)
_cell_angle_gamma                105.952(16)
_cell_volume                     471.75(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226.00
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.400
_exptl_absorpt_correction_T_max  0.973

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            7771
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1727
_reflns_number_gt                1538
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0953
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1727
_refine_ls_number_parameters     118
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.37489(9) 0.04112(8) 0.64037(7) 0.0312(2) Uani 1 1 d . . . . .
S9 S 0.07771(9) 0.09752(8) 0.79216(6) 0.0321(2) Uani 1 1 d . . . . .
P1 P 0.06432(9) -0.07129(8) 0.58784(7) 0.0281(2) Uani 1 1 d . . . . .
C1 C 0.4479(3) 0.2893(3) 0.6911(2) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.6059(3) 0.3737(3) 0.6578(3) 0.0304(5) Uani 1 1 d . . . . .
H2 H 0.6552 0.2967 0.6061 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6950(4) 0.5705(4) 0.6985(3) 0.0346(6) Uani 1 1 d . . . . .
H3 H 0.8070 0.6258 0.6782 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6210(3) 0.6819(3) 0.7671(3) 0.0315(5) Uani 1 1 d . . . . .
H4 H 0.6794 0.8150 0.7919 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4578(3) 0.6020(3) 0.8021(2) 0.0252(5) Uani 1 1 d . . . . .
C6 C 0.3866(4) 0.7232(3) 0.8752(3) 0.0314(5) Uani 1 1 d . . . . .
H6 H 0.4489 0.8558 0.8994 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2310(4) 0.6534(4) 0.9113(3) 0.0354(6) Uani 1 1 d . . . . .
H7 H 0.1852 0.7366 0.9607 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1387(3) 0.4590(3) 0.8755(3) 0.0306(5) Uani 1 1 d . . . . .
H8 H 0.0270 0.4109 0.8982 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2048(3) 0.3354(3) 0.8084(2) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.3674(3) 0.4023(3) 0.7666(2) 0.0220(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.771(2) . ?
S1 P1 2.0903(9) . ?
S9 C9 1.782(2) . ?
S9 P1 2.0924(10) . ?
P1 P1 2.2307(12) 2_556 ?
C1 C2 1.382(3) . ?
C1 C10 1.439(3) . ?
C2 C3 1.402(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(3) . ?
C5 C10 1.430(3) . ?
C6 C7 1.355(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.434(3) . ?

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
C1 S1 P1 106.53(8) . . ?
C9 S9 P1 105.74(8) . . ?
S1 P1 S9 99.71(4) . . ?
S1 P1 P1 99.52(4) . 2_556 ?
S9 P1 P1 99.48(4) . 2_556 ?
C2 C1 C10 120.5(2) . . ?
C2 C1 S1 112.55(16) . . ?
C10 C1 S1 126.90(16) . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 C10 120.1(2) . . ?
C4 C5 C10 120.9(2) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 S9 112.78(17) . . ?
C10 C9 S9 126.44(17) . . ?
C5 C10 C9 116.64(19) . . ?
C5 C10 C1 116.51(19) . . ?
C9 C10 C1 126.84(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
P1 S1 C1 C2 -152.29(15) . . . . ?
P1 S1 C1 C10 30.86(19) . . . . ?
C10 C1 C2 C3 1.2(3) . . . . ?
S1 C1 C2 C3 -175.90(18) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 179.3(2) . . . . ?
C3 C4 C5 C10 0.2(3) . . . . ?
C4 C5 C6 C7 -179.9(2) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 1.9(3) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C7 C8 C9 S9 174.47(18) . . . . ?
P1 S9 C9 C8 148.74(14) . . . . ?
P1 S9 C9 C10 -34.48(19) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C4 C5 C10 C9 179.23(19) . . . . ?
C6 C5 C10 C1 179.53(18) . . . . ?
C4 C5 C10 C1 -1.4(3) . . . . ?
C8 C9 C10 C5 1.5(3) . . . . ?
S9 C9 C10 C5 -175.08(15) . . . . ?
C8 C9 C10 C1 -177.9(2) . . . . ?
S9 C9 C10 C1 5.6(3) . . . . ?
C2 C1 C10 C5 0.7(3) . . . . ?
S1 C1 C10 C5 177.31(15) . . . . ?
C2 C1 C10 C9 -180.0(2) . . . . ?
S1 C1 C10 C9 -3.4(3) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


