# 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_3161f
_database_code_depnum_ccdc_archive 'CCDC 1423386'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N P S2'
_chemical_formula_sum            'C16 H14 N P S2'
_chemical_formula_weight         315.37

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   8.7273(9)
_cell_length_b                   9.6573(10)
_cell_length_c                   9.3479(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.287(4)
_cell_angle_gamma                90.00
_cell_volume                     756.24(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      29.95

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9005
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   'Bruker SADABS 2014/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13762
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.22
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3073
_reflns_number_gt                3011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_number_reflns         3073
_refine_ls_number_parameters     182
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0493
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

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
C1 C 0.79608(15) 0.11707(14) 0.58552(16) 0.0140(3) Uani 1 1 d . . .
C2 C 0.57818(15) 0.16891(14) 0.35037(16) 0.0147(3) Uani 1 1 d . . .
C3 C 0.69052(16) 0.01302(14) 0.53869(16) 0.0147(3) Uani 1 1 d . . .
H3A H 0.6984 -0.0730 0.5896 0.018 Uiso 1 1 calc R . .
C4 C 0.44190(17) -0.05554(16) 0.34180(18) 0.0221(3) Uani 1 1 d . . .
H4C H 0.4529 -0.1391 0.4033 0.027 Uiso 1 1 calc R . .
H4B H 0.4487 -0.0805 0.2422 0.027 Uiso 1 1 calc R . .
H4A H 0.3383 -0.0122 0.3338 0.027 Uiso 1 1 calc R . .
C5 C 1.09913(16) 0.23260(13) 0.69090(17) 0.0142(3) Uani 1 1 d . . .
C6 C 1.14770(16) 0.19402(14) 0.56612(16) 0.0176(3) Uani 1 1 d . . .
H6A H 1.1056 0.1124 0.5128 0.021 Uiso 1 1 calc R . .
C7 C 1.25718(18) 0.27416(16) 0.51930(18) 0.0201(3) Uani 1 1 d . . .
H7A H 1.2887 0.2477 0.4338 0.024 Uiso 1 1 calc R . .
C8 C 1.32035(17) 0.39296(15) 0.59796(18) 0.0217(3) Uani 1 1 d . . .
H8A H 1.3956 0.4476 0.5668 0.026 Uiso 1 1 calc R . .
C9 C 1.27316(17) 0.43130(16) 0.72175(18) 0.0211(3) Uani 1 1 d . . .
H9A H 1.3161 0.5127 0.7751 0.025 Uiso 1 1 calc R . .
C10 C 1.16305(16) 0.35160(14) 0.76912(17) 0.0181(3) Uani 1 1 d . . .
H10A H 1.1318 0.3786 0.8546 0.022 Uiso 1 1 calc R . .
C11 C 0.89490(16) 0.22228(13) 0.88219(17) 0.0151(3) Uani 1 1 d . . .
C12 C 0.99336(17) 0.22613(15) 1.02900(17) 0.0189(3) Uani 1 1 d . . .
H12A H 1.0904 0.1752 1.0553 0.023 Uiso 1 1 calc R . .
C13 C 0.94968(18) 0.30422(16) 1.13654(18) 0.0230(3) Uani 1 1 d . . .
H13A H 1.0178 0.3076 1.2355 0.028 Uiso 1 1 calc R . .
C14 C 0.80685(19) 0.37715(15) 1.09953(19) 0.0231(3) Uani 1 1 d . . .
H14A H 0.7772 0.4304 1.1730 0.028 Uiso 1 1 calc R . .
C15 C 0.70754(18) 0.37198(15) 0.95495(19) 0.0219(3) Uani 1 1 d . . .
H15A H 0.6091 0.4209 0.9299 0.026 Uiso 1 1 calc R . .
C16 C 0.75111(16) 0.29589(15) 0.84693(16) 0.0180(3) Uani 1 1 d . . .
H16A H 0.6827 0.2937 0.7480 0.022 Uiso 1 1 calc R . .
N N 0.57016(13) 0.04191(12) 0.41077(14) 0.0153(2) Uani 1 1 d . . .
P P 0.96376(4) 0.11459(3) 0.75148(4) 0.01383(8) Uani 1 1 d . . .
S1 S 0.74395(4) 0.25504(3) 0.46035(4) 0.01683(8) Uani 1 1 d . . .
S2 S 0.45110(4) 0.23339(4) 0.19706(4) 0.01922(8) Uani 1 1 d . . .


_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
C1 C3 1.3505(18) . ?
C1 S1 1.7472(14) . ?
C1 P 1.8098(13) . ?
C2 N 1.3601(18) . ?
C2 S2 1.6674(14) . ?
C2 S1 1.7343(14) . ?
C3 N 1.3808(18) . ?
C3 H3A 0.9500 . ?
C4 N 1.4662(17) . ?
C4 H4C 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4A 0.9800 . ?
C5 C10 1.3920(19) . ?
C5 C6 1.399(2) . ?
C5 P 1.8414(14) . ?
C6 C7 1.392(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.397(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.3989(19) . ?
C11 C12 1.401(2) . ?
C11 P 1.8297(15) . ?
C12 C13 1.393(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

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
C3 C1 S1 108.94(10) . . ?
C3 C1 P 125.60(11) . . ?
S1 C1 P 125.46(8) . . ?
N C2 S2 126.46(10) . . ?
N C2 S1 108.54(10) . . ?
S2 C2 S1 125.00(9) . . ?
C1 C3 N 114.48(12) . . ?
C1 C3 H3A 122.8 . . ?
N C3 H3A 122.8 . . ?
N C4 H4C 109.5 . . ?
N C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
N C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
C10 C5 C6 119.17(13) . . ?
C10 C5 P 123.13(12) . . ?
C6 C5 P 117.53(10) . . ?
C7 C6 C5 120.62(13) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C8 C7 C6 119.85(15) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C9 C8 C7 119.76(14) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.69(14) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C5 C10 C9 119.90(14) . . ?
C5 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C16 C11 C12 118.73(14) . . ?
C16 C11 P 124.92(11) . . ?
C12 C11 P 116.32(10) . . ?
C13 C12 C11 120.32(14) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 120.21(14) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.77(14) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C16 C15 C14 120.34(14) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C11 120.61(13) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
C2 N C3 115.25(11) . . ?
C2 N C4 121.20(12) . . ?
C3 N C4 123.55(12) . . ?
C1 P C11 103.11(6) . . ?
C1 P C5 99.35(6) . . ?
C11 P C5 102.29(6) . . ?
C2 S1 C1 92.78(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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C3 N -1.53(15) . . . . ?
P C1 C3 N 178.16(11) . . . . ?
C10 C5 C6 C7 -0.7(2) . . . . ?
P C5 C6 C7 -176.24(11) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C6 C5 C10 C9 0.5(2) . . . . ?
P C5 C10 C9 175.79(11) . . . . ?
C8 C9 C10 C5 -0.3(2) . . . . ?
C16 C11 C12 C13 -1.3(2) . . . . ?
P C11 C12 C13 -179.32(11) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C12 C11 C16 C15 0.5(2) . . . . ?
P C11 C16 C15 178.35(11) . . . . ?
S2 C2 N C3 179.98(10) . . . . ?
S1 C2 N C3 -0.27(15) . . . . ?
S2 C2 N C4 0.4(2) . . . . ?
S1 C2 N C4 -179.89(11) . . . . ?
C1 C3 N C2 1.22(18) . . . . ?
C1 C3 N C4 -179.16(13) . . . . ?
C3 C1 P C11 -103.53(13) . . . . ?
S1 C1 P C11 76.10(10) . . . . ?
C3 C1 P C5 151.41(13) . . . . ?
S1 C1 P C5 -28.96(11) . . . . ?
C16 C11 P C1 -5.50(13) . . . . ?
C12 C11 P C1 172.42(10) . . . . ?
C16 C11 P C5 97.29(12) . . . . ?
C12 C11 P C5 -84.78(11) . . . . ?
C10 C5 P C1 123.75(12) . . . . ?
C6 C5 P C1 -60.93(11) . . . . ?
C10 C5 P C11 18.02(13) . . . . ?
C6 C5 P C11 -166.66(10) . . . . ?
N C2 S1 C1 -0.51(11) . . . . ?
S2 C2 S1 C1 179.25(9) . . . . ?
C3 C1 S1 C2 1.16(11) . . . . ?
P C1 S1 C2 -178.53(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_3194
_database_code_depnum_ccdc_archive 'CCDC 1423387'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C16 H14 N P S2 Se), C7 H8'
_chemical_formula_sum            'C71 H64 N4 P4 S8 Se4'
_chemical_formula_weight         1669.46

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9952(5)
_cell_length_b                   13.8074(4)
_cell_length_c                   14.1857(6)
_cell_angle_alpha                107.357(2)
_cell_angle_beta                 104.864(2)
_cell_angle_gamma                94.068(2)
_cell_volume                     1782.84(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6561
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             842
_exptl_absorpt_coefficient_mu    2.427
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_T_max  0.9092
_exptl_absorpt_process_details   
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21839
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7728
_reflns_number_gt                5612
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0164P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7728
_refine_ls_number_parameters     433
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.0569(3) -0.38123(16) -0.3161(2) 0.0181(6) Uani 1 1 d . . .
C2 C 0.3151(3) -0.37923(16) -0.2432(2) 0.0190(6) Uani 1 1 d . . .
C3 C 0.1383(3) -0.35191(16) -0.3691(2) 0.0199(6) Uani 1 1 d . . .
H3 H 0.1010 -0.3342 -0.4293 0.024 Uiso 1 1 calc R . .
C4 C 0.3830(3) -0.3243(2) -0.3776(2) 0.0284(7) Uani 1 1 d . . .
H4A H 0.4674 -0.2826 -0.3242 0.043 Uiso 1 1 calc R . .
H4B H 0.3438 -0.2854 -0.4229 0.043 Uiso 1 1 calc R . .
H4C H 0.4072 -0.3877 -0.4184 0.043 Uiso 1 1 calc R . .
C5 C -0.1915(3) -0.51932(16) -0.3483(2) 0.0179(6) Uani 1 1 d . . .
C6 C -0.3256(3) -0.53756(17) -0.3401(2) 0.0233(6) Uani 1 1 d . . .
H6 H -0.3804 -0.4838 -0.3323 0.028 Uiso 1 1 calc R . .
C7 C -0.3799(3) -0.63426(18) -0.3431(2) 0.0297(7) Uani 1 1 d . . .
H7 H -0.4722 -0.6472 -0.3384 0.036 Uiso 1 1 calc R . .
C8 C -0.2983(3) -0.71181(18) -0.3529(2) 0.0309(7) Uani 1 1 d . . .
H8 H -0.3348 -0.7778 -0.3543 0.037 Uiso 1 1 calc R . .
C9 C -0.1648(3) -0.69384(17) -0.3607(2) 0.0267(7) Uani 1 1 d . . .
H9 H -0.1097 -0.7475 -0.3671 0.032 Uiso 1 1 calc R . .
C10 C -0.1100(3) -0.59751(17) -0.3591(2) 0.0210(6) Uani 1 1 d . . .
H10 H -0.0184 -0.5853 -0.3654 0.025 Uiso 1 1 calc R . .
C11 C -0.1667(3) -0.30494(16) -0.2376(2) 0.0181(6) Uani 1 1 d . . .
C12 C -0.2260(3) -0.21857(17) -0.2472(2) 0.0223(6) Uani 1 1 d . . .
H12 H -0.2518 -0.2078 -0.3122 0.027 Uiso 1 1 calc R . .
C13 C -0.2469(3) -0.14825(17) -0.1606(2) 0.0266(7) Uani 1 1 d . . .
H13 H -0.2860 -0.0887 -0.1661 0.032 Uiso 1 1 calc R . .
C14 C -0.2110(3) -0.16506(18) -0.0675(2) 0.0277(7) Uani 1 1 d . . .
H14 H -0.2248 -0.1166 -0.0087 0.033 Uiso 1 1 calc R . .
C15 C -0.1546(3) -0.25203(18) -0.0579(2) 0.0256(6) Uani 1 1 d . . .
H15 H -0.1312 -0.2634 0.0068 0.031 Uiso 1 1 calc R . .
C16 C -0.1329(3) -0.32205(17) -0.1438(2) 0.0221(6) Uani 1 1 d . . .
H16 H -0.0947 -0.3818 -0.1380 0.027 Uiso 1 1 calc R . .
C17 C 0.0258(3) 0.00197(17) 0.3104(2) 0.0196(6) Uani 1 1 d . . .
C18 C 0.2647(3) -0.03478(17) 0.2972(2) 0.0215(6) Uani 1 1 d . . .
C19 C 0.1328(3) 0.06370(17) 0.3884(2) 0.0211(6) Uani 1 1 d . . .
H19 H 0.1192 0.1168 0.4440 0.025 Uiso 1 1 calc R . .
C20 C 0.3929(3) 0.10316(19) 0.4621(2) 0.0311(7) Uani 1 1 d . . .
H20A H 0.4070 0.0783 0.5213 0.047 Uiso 1 1 calc R . .
H20B H 0.3841 0.1762 0.4842 0.047 Uiso 1 1 calc R . .
H20C H 0.4732 0.0942 0.4345 0.047 Uiso 1 1 calc R . .
C21 C -0.2175(3) 0.06097(16) 0.1938(2) 0.0191(6) Uani 1 1 d . . .
C22 C -0.1340(3) 0.08040(17) 0.1345(2) 0.0225(6) Uani 1 1 d . . .
H22 H -0.0403 0.0668 0.1483 0.027 Uiso 1 1 calc R . .
C23 C -0.1864(3) 0.11920(17) 0.0559(2) 0.0258(7) Uani 1 1 d . . .
H23 H -0.1287 0.1316 0.0156 0.031 Uiso 1 1 calc R . .
C24 C -0.3213(3) 0.14005(17) 0.0353(2) 0.0274(7) Uani 1 1 d . . .
H24 H -0.3568 0.1664 -0.0193 0.033 Uiso 1 1 calc R . .
C25 C -0.4056(3) 0.12251(18) 0.0945(2) 0.0269(7) Uani 1 1 d . . .
H25 H -0.4987 0.1373 0.0808 0.032 Uiso 1 1 calc R . .
C26 C -0.3540(3) 0.08365(17) 0.1732(2) 0.0244(6) Uani 1 1 d . . .
H26 H -0.4118 0.0721 0.2138 0.029 Uiso 1 1 calc R . .
C27 C -0.2358(3) -0.12590(16) 0.2481(2) 0.0174(6) Uani 1 1 d . . .
C28 C -0.1905(3) -0.18593(18) 0.3105(2) 0.0247(6) Uani 1 1 d . . .
H28 H -0.1196 -0.1569 0.3747 0.030 Uiso 1 1 calc R . .
C29 C -0.2510(3) -0.28898(19) 0.2771(2) 0.0304(7) Uani 1 1 d . . .
H29 H -0.2214 -0.3302 0.3191 0.036 Uiso 1 1 calc R . .
C30 C -0.3527(3) -0.33149(18) 0.1842(2) 0.0279(7) Uani 1 1 d . . .
H30 H -0.3929 -0.4018 0.1625 0.033 Uiso 1 1 calc R . .
C31 C -0.3970(3) -0.27275(18) 0.1220(2) 0.0289(7) Uani 1 1 d . . .
H31 H -0.4670 -0.3025 0.0575 0.035 Uiso 1 1 calc R . .
C32 C -0.3380(3) -0.16941(17) 0.1547(2) 0.0219(6) Uani 1 1 d . . .
H32 H -0.3684 -0.1287 0.1123 0.026 Uiso 1 1 calc R . .
N1 N 0.2788(2) -0.35002(13) -0.32858(17) 0.0187(5) Uani 1 1 d . . .
N2 N 0.2646(2) 0.04445(14) 0.38180(17) 0.0210(5) Uani 1 1 d . . .
P1 P -0.13008(7) -0.39308(4) -0.34883(5) 0.01782(16) Uani 1 1 d . . .
P2 P -0.15646(7) 0.00842(4) 0.29645(5) 0.01908(16) Uani 1 1 d . . .
S1 S 0.16414(7) -0.40702(5) -0.21076(6) 0.02327(16) Uani 1 1 d . . .
S2 S 0.47477(7) -0.38793(5) -0.17828(6) 0.02613(17) Uani 1 1 d . . .
S3 S 0.09203(7) -0.08736(4) 0.22536(6) 0.02433(17) Uani 1 1 d . . .
S4 S 0.40260(8) -0.07714(5) 0.26368(6) 0.03002(18) Uani 1 1 d . . .
Se1 Se -0.21696(3) -0.368105(18) -0.49009(2) 0.02470(8) Uani 1 1 d . . .
Se2 Se -0.18762(3) 0.094871(18) 0.43690(2) 0.02509(8) Uani 1 1 d . . .
C33 C -0.1174(5) -0.5222(6) -0.0155(6) 0.0375(18) Uani 0.50 1 d PGDU A -1
C34 C -0.0355(6) -0.4384(6) 0.0662(6) 0.0315(18) Uani 0.50 1 d PGDU A -1
H34 H -0.0777 -0.3946 0.1118 0.038 Uiso 0.50 1 calc PR A -1
C35 C 0.1081(6) -0.4185(7) 0.0814(7) 0.057(2) Uani 0.50 1 d PGU A -1
H35 H 0.1640 -0.3612 0.1373 0.068 Uiso 0.50 1 calc PR A -1
C36 C 0.1698(5) -0.4824(8) 0.0148(8) 0.056(2) Uani 0.50 1 d PGU A -1
H36 H 0.2679 -0.4688 0.0251 0.067 Uiso 0.50 1 calc PR A -1
C37 C 0.0880(7) -0.5663(7) -0.0670(7) 0.049(2) Uani 0.50 1 d PGU A -1
H37 H 0.1302 -0.6100 -0.1125 0.059 Uiso 0.50 1 calc PR A -1
C38 C -0.0556(7) -0.5862(6) -0.0821(6) 0.042(2) Uani 0.50 1 d PGDU A -1
H38 H -0.1116 -0.6435 -0.1380 0.051 Uiso 0.50 1 calc PR A -1
C39 C -0.2735(6) -0.5418(6) -0.0343(6) 0.071(2) Uani 0.50 1 d PDU A -1
H39A H -0.2935 -0.5471 0.0283 0.106 Uiso 0.50 1 calc PR A -1
H39B H -0.3138 -0.6062 -0.0914 0.106 Uiso 0.50 1 calc PR A -1
H39C H -0.3148 -0.4850 -0.0520 0.106 Uiso 0.50 1 calc PR A -1


_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
C1 C3 1.357(3) . ?
C1 S1 1.748(3) . ?
C1 P1 1.789(3) . ?
C2 N1 1.359(3) . ?
C2 S2 1.658(3) . ?
C2 S1 1.736(2) . ?
C3 N1 1.369(3) . ?
C3 H3 0.9500 . ?
C4 N1 1.470(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.387(3) . ?
C5 C10 1.394(3) . ?
C5 P1 1.809(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.383(4) . ?
C11 C12 1.395(3) . ?
C11 P1 1.821(2) . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C19 1.340(4) . ?
C17 S3 1.748(2) . ?
C17 P2 1.793(3) . ?
C18 N2 1.362(3) . ?
C18 S4 1.659(2) . ?
C18 S3 1.739(3) . ?
C19 N2 1.383(3) . ?
C19 H19 0.9500 . ?
C20 N2 1.467(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.392(3) . ?
C21 C26 1.399(4) . ?
C21 P2 1.805(3) . ?
C22 C23 1.379(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.380(4) . ?
C27 C28 1.400(3) . ?
C27 P2 1.814(2) . ?
C28 C29 1.394(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.371(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.394(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
P1 Se1 2.1098(8) . ?
P2 Se2 2.1079(7) . ?
C33 C34 1.3900 . ?
C33 C38 1.3900 . ?
C33 C39 1.504(5) . ?
C34 C35 1.3900 . ?
C34 H34 0.9500 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36 0.9500 . ?
C37 C38 1.3900 . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
C3 C1 S1 109.0(2) . . ?
C3 C1 P1 125.8(2) . . ?
S1 C1 P1 125.27(13) . . ?
N1 C2 S2 127.23(18) . . ?
N1 C2 S1 108.58(19) . . ?
S2 C2 S1 124.19(16) . . ?
C1 C3 N1 114.4(2) . . ?
C1 C3 H3 122.8 . . ?
N1 C3 H3 122.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 120.4(2) . . ?
C6 C5 P1 117.74(16) . . ?
C10 C5 P1 121.86(18) . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.0(2) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
C16 C11 C12 120.2(2) . . ?
C16 C11 P1 120.28(17) . . ?
C12 C11 P1 119.5(2) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C11 C16 C15 120.1(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C19 C17 S3 109.12(19) . . ?
C19 C17 P2 125.55(18) . . ?
S3 C17 P2 125.32(16) . . ?
N2 C18 S4 127.6(2) . . ?
N2 C18 S3 108.66(17) . . ?
S4 C18 S3 123.71(16) . . ?
C17 C19 N2 115.0(2) . . ?
C17 C19 H19 122.5 . . ?
N2 C19 H19 122.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.6(2) . . ?
C22 C21 P2 122.7(2) . . ?
C26 C21 P2 118.73(18) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C32 C27 C28 119.8(2) . . ?
C32 C27 P2 122.87(19) . . ?
C28 C27 P2 117.3(2) . . ?
C29 C28 C27 119.0(3) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.5(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C32 119.5(3) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
C27 C32 C31 120.5(2) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C2 N1 C3 115.6(2) . . ?
C2 N1 C4 122.0(2) . . ?
C3 N1 C4 122.3(2) . . ?
C18 N2 C19 114.7(2) . . ?
C18 N2 C20 123.3(2) . . ?
C19 N2 C20 122.0(2) . . ?
C1 P1 C5 105.77(11) . . ?
C1 P1 C11 105.44(12) . . ?
C5 P1 C11 104.25(10) . . ?
C1 P1 Se1 112.09(8) . . ?
C5 P1 Se1 113.66(9) . . ?
C11 P1 Se1 114.78(9) . . ?
C17 P2 C21 106.75(11) . . ?
C17 P2 C27 102.95(11) . . ?
C21 P2 C27 107.12(12) . . ?
C17 P2 Se2 111.21(9) . . ?
C21 P2 Se2 113.14(7) . . ?
C27 P2 Se2 114.88(8) . . ?
C2 S1 C1 92.46(12) . . ?
C18 S3 C17 92.48(12) . . ?
C34 C33 C38 120.0 . . ?
C34 C33 C39 120.1(4) . . ?
C38 C33 C39 119.8(4) . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C33 120.0 . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?

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 C1 C3 N1 0.1(2) . . . . ?
P1 C1 C3 N1 -179.31(16) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
P1 C5 C6 C7 177.7(2) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C5 0.8(4) . . . . ?
C6 C5 C10 C9 -0.5(4) . . . . ?
P1 C5 C10 C9 -178.4(2) . . . . ?
C16 C11 C12 C13 1.9(4) . . . . ?
P1 C11 C12 C13 -176.54(19) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C12 C11 C16 C15 -1.6(4) . . . . ?
P1 C11 C16 C15 176.84(19) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
S3 C17 C19 N2 1.5(3) . . . . ?
P2 C17 C19 N2 -179.41(16) . . . . ?
C26 C21 C22 C23 -1.3(4) . . . . ?
P2 C21 C22 C23 179.03(19) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 -0.4(4) . . . . ?
C22 C21 C26 C25 1.2(4) . . . . ?
P2 C21 C26 C25 -179.08(19) . . . . ?
C32 C27 C28 C29 -0.6(3) . . . . ?
P2 C27 C28 C29 178.70(18) . . . . ?
C27 C28 C29 C30 0.5(4) . . . . ?
C28 C29 C30 C31 0.0(4) . . . . ?
C29 C30 C31 C32 -0.4(4) . . . . ?
C28 C27 C32 C31 0.3(3) . . . . ?
P2 C27 C32 C31 -179.01(18) . . . . ?
C30 C31 C32 C27 0.2(4) . . . . ?
S2 C2 N1 C3 178.37(17) . . . . ?
S1 C2 N1 C3 -1.7(2) . . . . ?
S2 C2 N1 C4 2.0(3) . . . . ?
S1 C2 N1 C4 -178.09(17) . . . . ?
C1 C3 N1 C2 1.1(3) . . . . ?
C1 C3 N1 C4 177.5(2) . . . . ?
S4 C18 N2 C19 178.62(18) . . . . ?
S3 C18 N2 C19 -1.0(2) . . . . ?
S4 C18 N2 C20 -3.4(3) . . . . ?
S3 C18 N2 C20 176.97(18) . . . . ?
C17 C19 N2 C18 -0.3(3) . . . . ?
C17 C19 N2 C20 -178.3(2) . . . . ?
C3 C1 P1 C5 129.3(2) . . . . ?
S1 C1 P1 C5 -50.00(18) . . . . ?
C3 C1 P1 C11 -120.6(2) . . . . ?
S1 C1 P1 C11 60.09(17) . . . . ?
C3 C1 P1 Se1 4.9(2) . . . . ?
S1 C1 P1 Se1 -174.37(11) . . . . ?
C6 C5 P1 C1 160.8(2) . . . . ?
C10 C5 P1 C1 -21.2(3) . . . . ?
C6 C5 P1 C11 49.9(2) . . . . ?
C10 C5 P1 C11 -132.2(2) . . . . ?
C6 C5 P1 Se1 -75.8(2) . . . . ?
C10 C5 P1 Se1 102.1(2) . . . . ?
C16 C11 P1 C1 -65.3(2) . . . . ?
C12 C11 P1 C1 113.1(2) . . . . ?
C16 C11 P1 C5 45.9(2) . . . . ?
C12 C11 P1 C5 -135.7(2) . . . . ?
C16 C11 P1 Se1 170.83(18) . . . . ?
C12 C11 P1 Se1 -10.8(2) . . . . ?
C19 C17 P2 C21 107.1(2) . . . . ?
S3 C17 P2 C21 -73.95(17) . . . . ?
C19 C17 P2 C27 -140.3(2) . . . . ?
S3 C17 P2 C27 38.67(19) . . . . ?
C19 C17 P2 Se2 -16.8(2) . . . . ?
S3 C17 P2 Se2 162.19(13) . . . . ?
C22 C21 P2 C17 5.7(2) . . . . ?
C26 C21 P2 C17 -173.93(19) . . . . ?
C22 C21 P2 C27 -104.0(2) . . . . ?
C26 C21 P2 C27 76.3(2) . . . . ?
C22 C21 P2 Se2 128.39(18) . . . . ?
C26 C21 P2 Se2 -51.3(2) . . . . ?
C32 C27 P2 C17 -120.4(2) . . . . ?
C28 C27 P2 C17 60.3(2) . . . . ?
C32 C27 P2 C21 -8.1(2) . . . . ?
C28 C27 P2 C21 172.63(18) . . . . ?
C32 C27 P2 Se2 118.50(18) . . . . ?
C28 C27 P2 Se2 -60.8(2) . . . . ?
N1 C2 S1 C1 1.43(17) . . . . ?
S2 C2 S1 C1 -178.62(15) . . . . ?
C3 C1 S1 C2 -0.88(17) . . . . ?
P1 C1 S1 C2 178.52(15) . . . . ?
N2 C18 S3 C17 1.53(17) . . . . ?
S4 C18 S3 C17 -178.10(16) . . . . ?
C19 C17 S3 C18 -1.72(19) . . . . ?
P2 C17 S3 C18 179.18(16) . . . . ?
C38 C33 C34 C35 0.0 . . . . ?
C39 C33 C34 C35 -177.9(6) . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C36 C37 C38 C33 0.0 . . . . ?
C34 C33 C38 C37 0.0 . . . . ?
C39 C33 C38 C37 177.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_3195-twin5
_database_code_depnum_ccdc_archive 'CCDC 1423389'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N P S3'
_chemical_formula_sum            'C16 H14 N P S3'
_chemical_formula_weight         347.43

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.358(3)
_cell_length_b                   8.8787(15)
_cell_length_c                   12.973(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.891(7)
_cell_angle_gamma                90.00
_cell_volume                     1618.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4222
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      30.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8936
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_process_details   'Bruker TWINABS 2014/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2802
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2802
_reflns_number_gt                2462
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+3.7158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2810
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2065(3) -0.0200(4) 0.2008(4) 0.0149(9) Uani 1 1 d . . .
C2 C 0.0537(3) -0.1671(5) 0.1761(4) 0.0176(9) Uani 1 1 d . . .
C3 C 0.1962(3) -0.0996(5) 0.2853(3) 0.0177(10) Uani 1 1 d . . .
H3A H 0.2426 -0.1007 0.3491 0.021 Uiso 1 1 calc R . .
C4 C 0.0893(3) -0.2737(6) 0.3561(4) 0.0310(12) Uani 1 1 d . . .
H4A H 0.0595 -0.3676 0.3263 0.037 Uiso 1 1 calc R . .
H4B H 0.0453 -0.2192 0.3913 0.037 Uiso 1 1 calc R . .
H4C H 0.1479 -0.2969 0.4073 0.037 Uiso 1 1 calc R . .
C5 C 0.3470(3) -0.0015(5) 0.0752(3) 0.0144(9) Uani 1 1 d . . .
C6 C 0.2990(3) 0.0395(5) -0.0255(4) 0.0211(10) Uani 1 1 d . . .
H6A H 0.2501 0.1133 -0.0337 0.025 Uiso 1 1 calc R . .
C7 C 0.3220(3) -0.0262(5) -0.1132(4) 0.0232(10) Uani 1 1 d . . .
H7A H 0.2888 0.0020 -0.1816 0.028 Uiso 1 1 calc R . .
C8 C 0.3943(4) -0.1346(5) -0.1014(4) 0.0252(11) Uani 1 1 d . . .
H8A H 0.4101 -0.1809 -0.1616 0.030 Uiso 1 1 calc R . .
C9 C 0.4422(3) -0.1734(5) -0.0018(4) 0.0220(10) Uani 1 1 d . . .
H9A H 0.4920 -0.2456 0.0064 0.026 Uiso 1 1 calc R . .
C10 C 0.4188(3) -0.1086(5) 0.0863(4) 0.0187(10) Uani 1 1 d . . .
H10A H 0.4518 -0.1375 0.1546 0.022 Uiso 1 1 calc R . .
C11 C 0.2787(3) 0.2699(5) 0.1528(4) 0.0175(10) Uani 1 1 d . . .
C12 C 0.1875(3) 0.3262(5) 0.1491(4) 0.0236(10) Uani 1 1 d . . .
H12A H 0.1394 0.2628 0.1660 0.028 Uiso 1 1 calc R . .
C13 C 0.1671(3) 0.4746(5) 0.1209(4) 0.0289(12) Uani 1 1 d . . .
H13A H 0.1049 0.5127 0.1182 0.035 Uiso 1 1 calc R . .
C14 C 0.2365(4) 0.5677(5) 0.0965(4) 0.0276(11) Uani 1 1 d . . .
H14A H 0.2220 0.6695 0.0770 0.033 Uiso 1 1 calc R . .
C15 C 0.3274(4) 0.5123(5) 0.1007(4) 0.0295(12) Uani 1 1 d . . .
H15A H 0.3752 0.5766 0.0843 0.035 Uiso 1 1 calc R . .
C16 C 0.3489(3) 0.3652(5) 0.1282(4) 0.0224(11) Uani 1 1 d . . .
H16A H 0.4113 0.3279 0.1306 0.027 Uiso 1 1 calc R . .
N N 0.1120(2) -0.1803(4) 0.2717(3) 0.0182(8) Uani 1 1 d . . .
P P 0.31360(8) 0.07898(12) 0.19051(9) 0.0141(2) Uani 1 1 d . . .
S1 S 0.40896(8) 0.06035(13) 0.32011(9) 0.0218(3) Uani 1 1 d . . .
S2 S 0.10666(8) -0.04666(12) 0.09929(9) 0.0172(2) Uani 1 1 d . . .
S3 S -0.05054(8) -0.25197(15) 0.13417(12) 0.0263(3) Uani 1 1 d . . .


_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
C1 C3 1.338(6) . ?
C1 S2 1.751(4) . ?
C1 P 1.800(4) . ?
C2 N 1.352(6) . ?
C2 S3 1.663(4) . ?
C2 S2 1.740(4) . ?
C3 N 1.385(5) . ?
C3 H3A 0.9500 . ?
C4 N 1.463(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.388(6) . ?
C5 C6 1.393(6) . ?
C5 P 1.810(5) . ?
C6 C7 1.378(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.401(7) . ?
C7 H7A 0.9500 . ?
C8 C9 1.376(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.383(6) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.393(6) . ?
C11 C16 1.402(6) . ?
C11 P 1.807(4) . ?
C12 C13 1.382(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.380(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.372(6) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
P S1 1.9442(16) . ?

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
C3 C1 S2 109.4(3) . . ?
C3 C1 P 124.0(3) . . ?
S2 C1 P 126.1(3) . . ?
N C2 S3 127.3(3) . . ?
N C2 S2 108.5(3) . . ?
S3 C2 S2 124.2(3) . . ?
C1 C3 N 114.2(4) . . ?
C1 C3 H3A 122.9 . . ?
N C3 H3A 122.9 . . ?
N C4 H4A 109.5 . . ?
N C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 119.4(4) . . ?
C10 C5 P 120.1(3) . . ?
C6 C5 P 120.5(3) . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C9 C10 C5 120.1(4) . . ?
C9 C10 H10A 120.0 . . ?
C5 C10 H10A 120.0 . . ?
C12 C11 C16 119.4(4) . . ?
C12 C11 P 123.5(3) . . ?
C16 C11 P 117.1(3) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C11 120.0(4) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
C2 N C3 115.6(4) . . ?
C2 N C4 123.0(4) . . ?
C3 N C4 121.4(4) . . ?
C1 P C11 106.53(19) . . ?
C1 P C5 104.14(19) . . ?
C11 P C5 104.7(2) . . ?
C1 P S1 110.77(16) . . ?
C11 P S1 114.87(16) . . ?
C5 P S1 114.96(15) . . ?
C2 S2 C1 92.3(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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C1 C3 N 0.0(5) . . . . ?
P C1 C3 N -173.1(3) . . . . ?
C10 C5 C6 C7 0.4(7) . . . . ?
P C5 C6 C7 -177.4(4) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C6 C7 C8 C9 -0.5(7) . . . . ?
C7 C8 C9 C10 1.1(7) . . . . ?
C8 C9 C10 C5 -0.9(7) . . . . ?
C6 C5 C10 C9 0.1(6) . . . . ?
P C5 C10 C9 178.0(3) . . . . ?
C16 C11 C12 C13 0.3(7) . . . . ?
P C11 C12 C13 179.1(4) . . . . ?
C11 C12 C13 C14 -0.2(8) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C16 0.4(8) . . . . ?
C14 C15 C16 C11 -0.3(8) . . . . ?
C12 C11 C16 C15 0.0(7) . . . . ?
P C11 C16 C15 -178.9(4) . . . . ?
S3 C2 N C3 178.5(3) . . . . ?
S2 C2 N C3 -0.3(5) . . . . ?
S3 C2 N C4 -1.2(6) . . . . ?
S2 C2 N C4 -180.0(4) . . . . ?
C1 C3 N C2 0.2(5) . . . . ?
C1 C3 N C4 179.9(4) . . . . ?
C3 C1 P C11 -127.8(4) . . . . ?
S2 C1 P C11 60.3(3) . . . . ?
C3 C1 P C5 121.9(4) . . . . ?
S2 C1 P C5 -50.0(3) . . . . ?
C3 C1 P S1 -2.2(4) . . . . ?
S2 C1 P S1 -174.1(2) . . . . ?
C12 C11 P C1 8.2(5) . . . . ?
C16 C11 P C1 -172.9(4) . . . . ?
C12 C11 P C5 118.2(4) . . . . ?
C16 C11 P C5 -63.0(4) . . . . ?
C12 C11 P S1 -114.8(4) . . . . ?
C16 C11 P S1 64.0(4) . . . . ?
C10 C5 P C1 -101.1(4) . . . . ?
C6 C5 P C1 76.7(4) . . . . ?
C10 C5 P C11 147.2(3) . . . . ?
C6 C5 P C11 -35.0(4) . . . . ?
C10 C5 P S1 20.2(4) . . . . ?
C6 C5 P S1 -161.9(3) . . . . ?
N C2 S2 C1 0.3(3) . . . . ?
S3 C2 S2 C1 -178.6(3) . . . . ?
C3 C1 S2 C2 -0.2(3) . . . . ?
P C1 S2 C2 172.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.109
####################################################################### 
# 
# 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_3280
_database_code_depnum_ccdc_archive 'CCDC 1423391'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N O P S2'
_chemical_formula_sum            'C16 H14 N O P S2'
_chemical_formula_weight         331.37

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9328(4)
_cell_length_b                   16.3881(10)
_cell_length_c                   12.0195(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.457(3)
_cell_angle_gamma                90.00
_cell_volume                     1532.09(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3412
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      29.13

_exptl_crystal_description       rod
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8624
_exptl_absorpt_correction_T_max  0.9357
_exptl_absorpt_process_details   
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10424
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3307
_reflns_number_gt                2694
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.2867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3307
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 -0.25024(5) -0.15247(3) 0.10978(4) 0.01972(12) Uani 1 1 d . . .
S2 S 0.03798(6) -0.05098(3) 0.31153(4) 0.02897(13) Uani 1 1 d . . .
P P -0.54379(5) -0.27620(3) 0.04003(4) 0.01482(11) Uani 1 1 d . . .
O O -0.51496(15) -0.29798(7) -0.06829(10) 0.0203(3) Uani 1 1 d . . .
N N -0.18202(18) -0.15038(8) 0.34039(12) 0.0184(3) Uani 1 1 d . . .
C1 C -0.3728(2) -0.21343(10) 0.15397(15) 0.0162(3) Uani 1 1 d . . .
C2 C -0.3166(2) -0.20402(10) 0.27992(15) 0.0177(3) Uani 1 1 d . . .
H2A H -0.3659 -0.2322 0.3232 0.021 Uiso 1 1 calc R . .
C3 C -0.1241(2) -0.11573(10) 0.26525(15) 0.0192(4) Uani 1 1 d . . .
C4 C -0.1034(2) -0.13182(13) 0.47712(15) 0.0311(5) Uani 1 1 d . . .
H4A H 0.0167 -0.1498 0.5209 0.047 Uiso 1 1 calc R . .
H4B H -0.1663 -0.1604 0.5131 0.047 Uiso 1 1 calc R . .
H4C H -0.1082 -0.0729 0.4887 0.047 Uiso 1 1 calc R . .
C5 C -0.5438(2) -0.36281(10) 0.13227(14) 0.0157(3) Uani 1 1 d . . .
C6 C -0.6149(2) -0.36074(11) 0.21301(16) 0.0214(4) Uani 1 1 d . . .
H6A H -0.6718 -0.3130 0.2178 0.026 Uiso 1 1 calc R . .
C7 C -0.6024(2) -0.42864(11) 0.28631(16) 0.0231(4) Uani 1 1 d . . .
H7A H -0.6499 -0.4271 0.3418 0.028 Uiso 1 1 calc R . .
C8 C -0.5210(2) -0.49853(11) 0.27880(16) 0.0221(4) Uani 1 1 d . . .
H8A H -0.5121 -0.5447 0.3295 0.027 Uiso 1 1 calc R . .
C9 C -0.4522(2) -0.50146(11) 0.19734(16) 0.0223(4) Uani 1 1 d . . .
H9A H -0.3982 -0.5499 0.1911 0.027 Uiso 1 1 calc R . .
C10 C -0.4626(2) -0.43342(10) 0.12519(15) 0.0189(4) Uani 1 1 d . . .
H10A H -0.4139 -0.4351 0.0705 0.023 Uiso 1 1 calc R . .
C11 C -0.7370(2) -0.21750(10) -0.00882(14) 0.0153(3) Uani 1 1 d . . .
C12 C -0.8610(2) -0.21675(10) -0.13832(15) 0.0187(4) Uani 1 1 d . . .
H12A H -0.8461 -0.2494 -0.1975 0.022 Uiso 1 1 calc R . .
C13 C -1.0060(2) -0.16798(11) -0.18002(16) 0.0231(4) Uani 1 1 d . . .
H13A H -1.0892 -0.1666 -0.2683 0.028 Uiso 1 1 calc R . .
C14 C -1.0303(2) -0.12145(11) -0.09426(16) 0.0241(4) Uani 1 1 d . . .
H14A H -1.1301 -0.0885 -0.1236 0.029 Uiso 1 1 calc R . .
C15 C -0.9086(2) -0.12287(11) 0.03496(16) 0.0218(4) Uani 1 1 d . . .
H15A H -0.9260 -0.0915 0.0941 0.026 Uiso 1 1 calc R . .
C16 C -0.7621(2) -0.17008(10) 0.07731(15) 0.0177(3) Uani 1 1 d . . .
H16A H -0.6782 -0.1703 0.1654 0.021 Uiso 1 1 calc R . .


_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 1.7465(15) . ?
S1 C3 1.7474(16) . ?
S2 C3 1.6552(17) . ?
P O 1.4895(11) . ?
P C1 1.7914(17) . ?
P C5 1.8012(16) . ?
P C11 1.8033(16) . ?
N C3 1.366(2) . ?
N C2 1.373(2) . ?
N C4 1.467(2) . ?
C1 C2 1.349(2) . ?
C2 H2A 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.391(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.389(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.398(2) . ?
C11 C16 1.398(2) . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.391(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

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 C3 92.45(7) . . ?
O P C1 110.91(7) . . ?
O P C5 113.68(7) . . ?
C1 P C5 103.90(7) . . ?
O P C11 113.10(7) . . ?
C1 P C11 105.21(7) . . ?
C5 P C11 109.32(7) . . ?
C3 N C2 115.69(13) . . ?
C3 N C4 121.77(14) . . ?
C2 N C4 122.54(13) . . ?
C2 C1 S1 109.43(12) . . ?
C2 C1 P 129.08(12) . . ?
S1 C1 P 121.48(9) . . ?
C1 C2 N 114.40(14) . . ?
C1 C2 H2A 122.8 . . ?
N C2 H2A 122.8 . . ?
N C3 S2 126.69(12) . . ?
N C3 S1 108.01(12) . . ?
S2 C3 S1 125.29(9) . . ?
N C4 H4A 109.5 . . ?
N C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 119.46(15) . . ?
C10 C5 P 117.38(11) . . ?
C6 C5 P 123.11(13) . . ?
C7 C6 C5 119.91(16) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 C6 120.19(15) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 120.24(15) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 119.72(16) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C5 120.47(14) . . ?
C9 C10 H10A 119.8 . . ?
C5 C10 H10A 119.8 . . ?
C12 C11 C16 119.46(15) . . ?
C12 C11 P 118.33(12) . . ?
C16 C11 P 122.13(12) . . ?
C13 C12 C11 119.63(15) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 C12 120.58(15) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 120.03(16) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 119.91(15) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C11 120.36(15) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?

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
C3 S1 C1 C2 0.19(13) . . . . ?
C3 S1 C1 P -179.80(11) . . . . ?
O P C1 C2 -154.45(15) . . . . ?
C5 P C1 C2 -31.93(17) . . . . ?
C11 P C1 C2 82.92(17) . . . . ?
O P C1 S1 25.53(12) . . . . ?
C5 P C1 S1 148.05(10) . . . . ?
C11 P C1 S1 -97.09(11) . . . . ?
S1 C1 C2 N 0.32(18) . . . . ?
P C1 C2 N -179.69(12) . . . . ?
C3 N C2 C1 -0.9(2) . . . . ?
C4 N C2 C1 179.80(16) . . . . ?
C2 N C3 S2 -178.45(13) . . . . ?
C4 N C3 S2 0.9(2) . . . . ?
C2 N C3 S1 0.96(18) . . . . ?
C4 N C3 S1 -179.71(13) . . . . ?
C1 S1 C3 N -0.64(12) . . . . ?
C1 S1 C3 S2 178.78(12) . . . . ?
O P C5 C10 21.34(15) . . . . ?
C1 P C5 C10 -99.33(14) . . . . ?
C11 P C5 C10 148.77(13) . . . . ?
O P C5 C6 -161.27(13) . . . . ?
C1 P C5 C6 78.06(15) . . . . ?
C11 P C5 C6 -33.84(16) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
P C5 C6 C7 -176.66(13) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C5 -1.1(2) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
P C5 C10 C9 177.61(13) . . . . ?
O P C11 C12 16.91(15) . . . . ?
C1 P C11 C12 138.12(12) . . . . ?
C5 P C11 C12 -110.84(13) . . . . ?
O P C11 C16 -159.90(12) . . . . ?
C1 P C11 C16 -38.70(15) . . . . ?
C5 P C11 C16 72.34(14) . . . . ?
C16 C11 C12 C13 1.0(2) . . . . ?
P C11 C12 C13 -175.89(12) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
P C11 C16 C15 176.91(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_4194f
_database_code_depnum_ccdc_archive 'CCDC 1423392'
_audit_update_record             
;
2015-09-10 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        IB-26
_chemical_formula_moiety         'C16 H15 N O P S, H O4 S'
_chemical_formula_sum            'C16 H16 N O5 P S2'
_chemical_formula_weight         397.39
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3334(7)
_cell_length_b                   13.5214(10)
_cell_length_c                   30.503(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3437.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15094
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.785
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3327
_reflns_number_total             4119
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0409P)²+4.0321P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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 -0.05765(8) 0.78849(5) 0.10787(2) 0.02887(16) Uani 1 1 d . . . . .
P P 0.12824(6) 0.61892(4) 0.07074(2) 0.01424(13) Uani 1 1 d . . . . .
O1 O 0.03331(18) 0.65006(11) 0.03186(5) 0.0200(3) Uani 1 1 d . . . . .
N N 0.1189(2) 0.80987(13) 0.17353(6) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.1077(2) 0.71306(15) 0.11273(7) 0.0161(4) Uani 1 1 d . . . . .
C2 C -0.0128(3) 0.84523(18) 0.15529(8) 0.0265(5) Uani 1 1 d . . . . .
H2 H -0.0753 0.8970 0.1676 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1887(3) 0.73419(15) 0.15018(7) 0.0178(4) Uani 1 1 d . . . . .
H3 H 0.2831 0.7005 0.1592 0.021 Uiso 1 1 calc R . . . .
C4 C 0.1831(3) 0.84765(19) 0.21524(8) 0.0289(5) Uani 1 1 d . . . . .
H4A H 0.2143 0.9171 0.2117 0.043 Uiso 1 1 calc GR . . . .
H4B H 0.2771 0.8086 0.2238 0.043 Uiso 1 1 calc GR . . . .
H4C H 0.1006 0.8425 0.2380 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.0575(2) 0.50732(16) 0.09648(7) 0.0159(4) Uani 1 1 d . . . . .
C6 C 0.0298(3) 0.42641(16) 0.06885(7) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.0505 0.4316 0.0383 0.023 Uiso 1 1 calc R . . . .
C7 C -0.0278(3) 0.33882(16) 0.08625(8) 0.0236(5) Uani 1 1 d . . . . .
H7 H -0.0458 0.2837 0.0676 0.028 Uiso 1 1 calc R . . . .
C8 C -0.0596(3) 0.33101(17) 0.13086(8) 0.0253(5) Uani 1 1 d . . . . .
H8 H -0.0978 0.2704 0.1427 0.030 Uiso 1 1 calc R . . . .
C9 C -0.0356(3) 0.41133(18) 0.15799(8) 0.0273(5) Uani 1 1 d . . . . .
H9 H -0.0598 0.4063 0.1883 0.033 Uiso 1 1 calc R . . . .
C10 C 0.0239(3) 0.49961(17) 0.14109(7) 0.0238(5) Uani 1 1 d . . . . .
H10 H 0.0417 0.5545 0.1599 0.029 Uiso 1 1 calc R . . . .
C11 C 0.3378(2) 0.60445(15) 0.05948(7) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.4423(3) 0.56576(16) 0.09062(7) 0.0204(4) Uani 1 1 d . . . . .
H12 H 0.4025 0.5449 0.1183 0.024 Uiso 1 1 calc R . . . .
C13 C 0.6046(3) 0.55762(17) 0.08123(8) 0.0242(5) Uani 1 1 d . . . . .
H13 H 0.6766 0.5326 0.1026 0.029 Uiso 1 1 calc R . . . .
C14 C 0.6612(3) 0.58631(17) 0.04031(8) 0.0243(5) Uani 1 1 d . . . . .
H14 H 0.7722 0.5802 0.0337 0.029 Uiso 1 1 calc R . . . .
C15 C 0.5568(3) 0.62385(17) 0.00904(8) 0.0233(5) Uani 1 1 d . . . . .
H15 H 0.5963 0.6428 -0.0189 0.028 Uiso 1 1 calc R . . . .
C16 C 0.3951(3) 0.63376(16) 0.01853(7) 0.0184(4) Uani 1 1 d . . . . .
H16 H 0.3237 0.6603 -0.0027 0.022 Uiso 1 1 calc R . . . .
S2 S 0.59134(7) 0.59400(4) 0.22372(2) 0.02106(14) Uani 1 1 d . . . . .
O2 O 0.7356(2) 0.66287(13) 0.20985(6) 0.0304(4) Uani 1 1 d . . . . .
H2A H 0.8205 0.6425 0.2216 0.046 Uiso 1 1 calc GR . . . .
O3 O 0.4721(2) 0.61129(15) 0.19017(6) 0.0388(5) Uani 1 1 d . . . . .
O4 O 0.6508(2) 0.49378(13) 0.22403(7) 0.0384(5) Uani 1 1 d . . . . .
O5 O 0.5379(2) 0.62769(15) 0.26661(5) 0.0350(4) Uani 1 1 d . . . . .


_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 1.721(2) . ?
S1 C2 1.679(2) . ?
P O1 1.4863(15) . ?
P C1 1.814(2) . ?
P C5 1.801(2) . ?
P C11 1.791(2) . ?
N C2 1.320(3) . ?
N C3 1.376(3) . ?
N C4 1.472(3) . ?
C1 C3 1.357(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.400(3) . ?
C5 C10 1.393(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 C16 1.395(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
S2 O2 1.5787(18) . ?
S2 O3 1.4454(18) . ?
S2 O4 1.4428(18) . ?
S2 O5 1.4553(18) . ?
O2 H2A 0.8400 . ?

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
C2 S1 C1 91.06(11) . . ?
O1 P C1 108.33(9) . . ?
O1 P C5 114.27(9) . . ?
O1 P C11 113.40(9) . . ?
C5 P C1 104.43(9) . . ?
C11 P C1 107.69(9) . . ?
C11 P C5 108.15(10) . . ?
C2 N C3 113.75(19) . . ?
C2 N C4 122.7(2) . . ?
C3 N C4 123.5(2) . . ?
S1 C1 P 115.50(12) . . ?
C3 C1 S1 110.24(16) . . ?
C3 C1 P 134.05(17) . . ?
S1 C2 H2 123.8 . . ?
N C2 S1 112.49(17) . . ?
N C2 H2 123.8 . . ?
N C3 H3 123.8 . . ?
C1 C3 N 112.46(19) . . ?
C1 C3 H3 123.8 . . ?
N C4 H4A 109.5 . . ?
N C4 H4B 109.5 . . ?
N C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 P 116.50(16) . . ?
C10 C5 P 123.67(17) . . ?
C10 C5 C6 119.8(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C12 C11 P 121.39(16) . . ?
C12 C11 C16 120.28(19) . . ?
C16 C11 P 118.33(16) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
O3 S2 O2 103.80(11) . . ?
O3 S2 O5 112.04(12) . . ?
O4 S2 O2 107.12(11) . . ?
O4 S2 O3 113.11(12) . . ?
O4 S2 O5 113.16(12) . . ?
O5 S2 O2 106.82(10) . . ?
S2 O2 H2A 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 C1 C3 N -0.7(2) . . . . ?
P C1 C3 N -175.03(17) . . . . ?
P C5 C6 C7 -178.69(17) . . . . ?
P C5 C10 C9 177.81(18) . . . . ?
P C11 C12 C13 -178.53(18) . . . . ?
P C11 C16 C15 179.69(17) . . . . ?
O1 P C1 S1 21.30(15) . . . . ?
O1 P C1 C3 -164.6(2) . . . . ?
O1 P C5 C6 49.50(19) . . . . ?
O1 P C5 C10 -127.89(19) . . . . ?
O1 P C11 C12 -173.14(17) . . . . ?
O1 P C11 C16 7.3(2) . . . . ?
C1 S1 C2 N 0.28(19) . . . . ?
C1 P C5 C6 167.68(16) . . . . ?
C1 P C5 C10 -9.7(2) . . . . ?
C1 P C11 C12 67.01(19) . . . . ?
C1 P C11 C16 -112.51(17) . . . . ?
C2 S1 C1 P 175.73(14) . . . . ?
C2 S1 C1 C3 0.26(18) . . . . ?
C2 N C3 C1 1.0(3) . . . . ?
C3 N C2 S1 -0.8(3) . . . . ?
C4 N C2 S1 179.90(17) . . . . ?
C4 N C3 C1 -179.7(2) . . . . ?
C5 P C1 S1 -100.86(13) . . . . ?
C5 P C1 C3 73.2(2) . . . . ?
C5 P C11 C12 -45.3(2) . . . . ?
C5 P C11 C16 135.16(16) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C5 C10 C9 0.5(3) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C8 C9 C10 C5 0.8(4) . . . . ?
C10 C5 C6 C7 -1.2(3) . . . . ?
C11 P C1 S1 144.32(12) . . . . ?
C11 P C1 C3 -41.6(2) . . . . ?
C11 P C5 C6 -77.83(18) . . . . ?
C11 P C5 C10 104.8(2) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 -0.9(3) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
