# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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=S_15srv216
_database_code_depnum_ccdc_archive 'CCDC 1578844'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2015-07-31
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H21 P S4'
_chemical_formula_sum            'C21 H21 P S4'
_chemical_formula_weight         432.59
_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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.7372(7)
_cell_length_b                   19.6819(13)
_cell_length_c                   10.9938(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.163(2)
_cell_angle_gamma                90.00
_cell_volume                     2119.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      2.28
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8552.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32442
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.07
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4830
_reflns_number_total             5625
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+1.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0853
_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. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.42629(4) 0.37926(2) 0.86884(4) 0.01889(9) Uani 1 d . . .
S2 S 0.12466(4) 0.30601(2) 0.14345(4) 0.02286(10) Uani 1 d . . .
S3 S 0.34079(5) 0.73738(2) 0.64240(4) 0.02641(10) Uani 1 d . . .
S4 S -0.24641(5) 0.41937(2) 0.86414(5) 0.02879(11) Uani 1 d . . .
P1 P 0.27278(4) 0.422212(18) 0.72457(4) 0.01294(8) Uani 1 d . . .
C1 C 0.22979(15) 0.38177(7) 0.56528(14) 0.0145(3) Uani 1 d . . .
C2 C 0.09549(15) 0.36844(8) 0.47636(15) 0.0165(3) Uani 1 d . . .
C3 C 0.06804(16) 0.34323(8) 0.35018(15) 0.0185(3) Uani 1 d . . .
C4 C 0.17344(16) 0.33202(7) 0.30946(14) 0.0161(3) Uani 1 d . . .
C5 C 0.30832(16) 0.34327(8) 0.39932(15) 0.0190(3) Uani 1 d . . .
C6 C 0.33542(16) 0.36787(8) 0.52610(15) 0.0189(3) Uani 1 d . . .
C7 C 0.2836(2) 0.29661(10) 0.12758(18) 0.0266(4) Uani 1 d . . .
C8 C 0.30070(14) 0.50988(7) 0.69434(14) 0.0142(3) Uani 1 d . . .
C9 C 0.25307(16) 0.53678(8) 0.56621(15) 0.0187(3) Uani 1 d . . .
C10 C 0.26492(16) 0.60580(8) 0.54537(15) 0.0194(3) Uani 1 d . . .
C11 C 0.32427(15) 0.64931(8) 0.65384(15) 0.0169(3) Uani 1 d . . .
C12 C 0.37580(16) 0.62206(8) 0.78291(15) 0.0179(3) Uani 1 d . . .
C13 C 0.36416(15) 0.55364(8) 0.80282(15) 0.0158(3) Uani 1 d . . .
C14 C 0.2596(2) 0.75332(9) 0.46689(19) 0.0317(4) Uani 1 d . . .
C15 C 0.12060(14) 0.42391(7) 0.75660(14) 0.0139(3) Uani 1 d . . .
C16 C 0.05800(15) 0.48471(8) 0.76419(15) 0.0175(3) Uani 1 d . . .
C17 C -0.05255(16) 0.48550(8) 0.79910(16) 0.0193(3) Uani 1 d . . .
C18 C -0.10432(15) 0.42508(8) 0.82474(15) 0.0175(3) Uani 1 d . . .
C19 C -0.04145(15) 0.36349(8) 0.81718(15) 0.0175(3) Uani 1 d . . .
C20 C 0.06983(16) 0.36298(8) 0.78461(15) 0.0170(3) Uani 1 d . . .
C21 C -0.2923(2) 0.50663(10) 0.8692(2) 0.0304(4) Uani 1 d . . .
H2 H 0.0245(18) 0.3768(9) 0.5025(18) 0.015(4) Uiso 1 d . . .
H3 H -0.026(2) 0.3341(10) 0.2908(19) 0.023(5) Uiso 1 d . . .
H5 H 0.3783(19) 0.3342(9) 0.3768(17) 0.017(4) Uiso 1 d . . .
H6 H 0.426(2) 0.3771(9) 0.586(2) 0.023(5) Uiso 1 d . . .
H7A H 0.338(2) 0.2628(11) 0.190(2) 0.034(6) Uiso 1 d . . .
H7B H 0.254(2) 0.2820(11) 0.034(2) 0.039(6) Uiso 1 d . . .
H7C H 0.332(2) 0.3380(12) 0.144(2) 0.040(6) Uiso 1 d . . .
H9 H 0.213(2) 0.5091(10) 0.493(2) 0.028(5) Uiso 1 d . . .
H10 H 0.232(2) 0.6208(10) 0.458(2) 0.026(5) Uiso 1 d . . .
H12 H 0.416(2) 0.6511(10) 0.856(2) 0.026(5) Uiso 1 d . . .
H13 H 0.3949(18) 0.5376(9) 0.8865(19) 0.017(4) Uiso 1 d . . .
H14A H 0.258(2) 0.8017(12) 0.459(2) 0.037(6) Uiso 1 d . . .
H14B H 0.313(2) 0.7311(12) 0.424(2) 0.041(6) Uiso 1 d . . .
H14C H 0.162(2) 0.7380(12) 0.431(2) 0.041(6) Uiso 1 d . . .
H16 H 0.0876(19) 0.5259(10) 0.7468(18) 0.022(5) Uiso 1 d . . .
H17 H -0.089(2) 0.5287(11) 0.809(2) 0.030(5) Uiso 1 d . . .
H19 H -0.0772(19) 0.3221(10) 0.8347(18) 0.020(5) Uiso 1 d . . .
H20 H 0.110(2) 0.3204(10) 0.7803(19) 0.025(5) Uiso 1 d . . .
H21A H -0.320(2) 0.5262(12) 0.778(2) 0.044(6) Uiso 1 d . . .
H21B H -0.214(2) 0.5342(12) 0.935(2) 0.043(6) Uiso 1 d . . .
H21C H -0.369(3) 0.5060(13) 0.891(2) 0.051(7) Uiso 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 P1 1.9511(5) . ?
S2 C4 1.7563(15) . ?
S2 C7 1.7952(19) . ?
S3 C11 1.7520(15) . ?
S3 C14 1.7901(19) . ?
S4 C18 1.7518(15) . ?
S4 C21 1.7939(19) . ?
P1 C1 1.8033(15) . ?
P1 C8 1.8054(15) . ?
P1 C15 1.8072(15) . ?
C1 C2 1.396(2) . ?
C1 C6 1.395(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.932(18) . ?
C3 C4 1.394(2) . ?
C3 H3 0.97(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.389(2) . ?
C5 H5 0.900(19) . ?
C6 H6 0.94(2) . ?
C7 H7A 0.96(2) . ?
C7 H7B 0.99(2) . ?
C7 H7C 0.95(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.401(2) . ?
C9 C10 1.392(2) . ?
C9 H9 0.92(2) . ?
C10 C11 1.393(2) . ?
C10 H10 0.92(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.378(2) . ?
C12 H12 0.94(2) . ?
C13 H13 0.898(18) . ?
C14 H14A 0.96(2) . ?
C14 H14B 0.98(2) . ?
C14 H14C 1.00(2) . ?
C15 C16 1.392(2) . ?
C15 C20 1.403(2) . ?
C16 C17 1.389(2) . ?
C16 H16 0.919(19) . ?
C17 C18 1.390(2) . ?
C17 H17 0.96(2) . ?
C18 C19 1.406(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.954(19) . ?
C20 H20 0.952(19) . ?
C21 H21A 1.00(2) . ?
C21 H21B 1.02(2) . ?
C21 H21C 0.95(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
C4 S2 C7 103.89(8) . . ?
C11 S3 C14 103.41(8) . . ?
C18 S4 C21 102.96(8) . . ?
C1 P1 S1 113.17(5) . . ?
C1 P1 C8 103.82(7) . . ?
C1 P1 C15 107.76(7) . . ?
C8 P1 S1 114.52(5) . . ?
C8 P1 C15 104.46(6) . . ?
C15 P1 S1 112.33(5) . . ?
C2 C1 P1 122.91(11) . . ?
C6 C1 P1 117.98(11) . . ?
C6 C1 C2 118.95(13) . . ?
C1 C2 H2 119.4(11) . . ?
C3 C2 C1 120.22(14) . . ?
C3 C2 H2 120.3(11) . . ?
C2 C3 C4 120.64(14) . . ?
C2 C3 H3 118.5(11) . . ?
C4 C3 H3 120.9(11) . . ?
C3 C4 S2 116.34(11) . . ?
C3 C4 C5 119.38(13) . . ?
C5 C4 S2 124.26(12) . . ?
C4 C5 H5 121.0(11) . . ?
C6 C5 C4 119.71(14) . . ?
C6 C5 H5 119.3(11) . . ?
C1 C6 H6 118.9(12) . . ?
C5 C6 C1 121.01(14) . . ?
C5 C6 H6 120.0(12) . . ?
S2 C7 H7A 109.1(13) . . ?
S2 C7 H7B 102.7(13) . . ?
S2 C7 H7C 111.5(14) . . ?
H7A C7 H7B 112.4(18) . . ?
H7A C7 H7C 109.6(19) . . ?
H7B C7 H7C 111.4(18) . . ?
C9 C8 P1 122.01(11) . . ?
C9 C8 C13 118.49(14) . . ?
C13 C8 P1 119.37(11) . . ?
C8 C9 C10 121.16(14) . . ?
C8 C9 H9 120.3(13) . . ?
C10 C9 H9 118.5(13) . . ?
C9 C10 C11 119.99(14) . . ?
C9 C10 H10 117.4(12) . . ?
C11 C10 H10 122.6(12) . . ?
C10 C11 S3 124.84(12) . . ?
C10 C11 C12 118.96(14) . . ?
C12 C11 S3 116.21(11) . . ?
C11 C12 H12 119.4(12) . . ?
C13 C12 C11 120.72(14) . . ?
C13 C12 H12 119.9(12) . . ?
C8 C13 H13 120.2(12) . . ?
C12 C13 C8 120.64(14) . . ?
C12 C13 H13 119.1(12) . . ?
S3 C14 H14A 105.0(13) . . ?
S3 C14 H14B 108.7(14) . . ?
S3 C14 H14C 110.1(13) . . ?
H14A C14 H14B 112.9(19) . . ?
H14A C14 H14C 106.5(19) . . ?
H14B C14 H14C 113.3(19) . . ?
C16 C15 P1 121.66(11) . . ?
C16 C15 C20 118.78(13) . . ?
C20 C15 P1 119.38(11) . . ?
C15 C16 H16 122.0(12) . . ?
C17 C16 C15 120.96(14) . . ?
C17 C16 H16 117.1(12) . . ?
C16 C17 C18 120.30(14) . . ?
C16 C17 H17 118.3(12) . . ?
C18 C17 H17 121.3(12) . . ?
C17 C18 S4 124.49(12) . . ?
C17 C18 C19 118.95(14) . . ?
C19 C18 S4 116.55(11) . . ?
C18 C19 H19 118.9(11) . . ?
C20 C19 C18 120.59(14) . . ?
C20 C19 H19 120.6(11) . . ?
C15 C20 H20 121.2(12) . . ?
C19 C20 C15 120.40(14) . . ?
C19 C20 H20 118.3(12) . . ?
S4 C21 H21A 108.0(13) . . ?
S4 C21 H21B 112.0(13) . . ?
S4 C21 H21C 105.9(15) . . ?
H21A C21 H21B 109.3(19) . . ?
H21A C21 H21C 109.1(19) . . ?
H21B C21 H21C 112.3(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
C2 C1 P1 S1 136.58(11) . . . . ?
C2 C1 P1 C8 -98.65(13) . . . . ?
C2 C1 P1 C15 11.77(14) . . . . ?
C3 C4 S2 C7 -179.89(12) . . . . ?
C5 C4 S2 C7 1.65(15) . . . . ?
C6 C1 P1 S1 -48.16(13) . . . . ?
C6 C1 P1 C8 76.60(13) . . . . ?
C6 C1 P1 C15 -172.98(12) . . . . ?
C9 C8 P1 S1 141.75(11) . . . . ?
C9 C8 P1 C1 17.86(14) . . . . ?
C9 C8 P1 C15 -94.95(13) . . . . ?
C10 C11 S3 C14 2.25(17) . . . . ?
C12 C11 S3 C14 -177.92(13) . . . . ?
C13 C8 P1 S1 -42.58(13) . . . . ?
C13 C8 P1 C1 -166.47(11) . . . . ?
C13 C8 P1 C15 80.71(12) . . . . ?
C16 C15 P1 S1 119.90(11) . . . . ?
C16 C15 P1 C1 -114.78(12) . . . . ?
C16 C15 P1 C8 -4.80(14) . . . . ?
C17 C18 S4 C21 -2.75(16) . . . . ?
C19 C18 S4 C21 178.27(13) . . . . ?
C20 C15 P1 S1 -55.17(12) . . . . ?
C20 C15 P1 C1 70.15(13) . . . . ?
C20 C15 P1 C8 -179.87(11) . . . . ?

####################################################################### 
# 
# 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=Se_15srv218
_database_code_depnum_ccdc_archive 'CCDC 1578845'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2015-08-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H21 P S3 Se'
_chemical_formula_sum            'C21 H21 P S3 Se'
_chemical_formula_weight         479.49
_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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.8302(4)
_cell_length_b                   19.7686(8)
_cell_length_c                   10.9470(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.8736(13)
_cell_angle_gamma                90.00
_cell_volume                     2159.43(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.29
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0885 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.7935.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33209
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                5184
_reflns_number_total             5737
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0260P)²+1.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0631
_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. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.571345(16) 0.622891(8) 0.628697(16) 0.01797(5) Uani 1 d . . .
S1 S 0.66217(5) 0.26260(2) 0.86525(5) 0.02817(10) Uani 1 d . . .
S2 S 0.87286(5) 0.69733(2) 1.35648(4) 0.02353(9) Uani 1 d . . .
S3 S 1.24195(5) 0.57818(2) 0.62887(6) 0.02999(11) Uani 1 d . . .
P1 P 0.73238(4) 0.576076(19) 0.78109(4) 0.01244(8) Uani 1 d . . .
C1 C 0.70347(15) 0.48879(8) 0.81173(15) 0.0141(3) Uani 1 d . . .
C2 C 0.63812(16) 0.44568(8) 0.70489(15) 0.0164(3) Uani 1 d . . .
C3 C 0.62648(17) 0.37754(8) 0.72541(16) 0.0184(3) Uani 1 d . . .
C4 C 0.67915(16) 0.35028(8) 0.85330(16) 0.0170(3) Uani 1 d . . .
C5 C 0.74041(17) 0.39345(9) 0.96089(16) 0.0194(3) Uani 1 d . . .
C6 C 0.75266(17) 0.46210(8) 0.93943(16) 0.0188(3) Uani 1 d . . .
C7 C 0.7460(3) 0.24628(11) 1.0392(2) 0.0335(5) Uani 1 d . . .
C8 C 0.77348(16) 0.61690(7) 0.93982(15) 0.0141(3) Uani 1 d . . .
C9 C 0.66899(17) 0.63034(8) 0.98092(17) 0.0186(3) Uani 1 d . . .
C10 C 0.69493(18) 0.65590(9) 1.10643(16) 0.0194(3) Uani 1 d . . .
C11 C 0.82667(17) 0.66896(8) 1.19288(15) 0.0161(3) Uani 1 d . . .
C12 C 0.93104(17) 0.65770(8) 1.14999(16) 0.0182(3) Uani 1 d . . .
C13 C 0.90447(16) 0.63167(8) 1.02486(16) 0.0168(3) Uani 1 d . . .
C14 C 0.7163(2) 0.70546(10) 1.37590(19) 0.0266(4) Uani 1 d . . .
C15 C 0.88166(15) 0.57413(8) 0.74538(14) 0.0135(3) Uani 1 d . . .
C16 C 0.94265(16) 0.51343(8) 0.73648(16) 0.0167(3) Uani 1 d . . .
C17 C 1.05130(17) 0.51246(8) 0.69864(17) 0.0189(3) Uani 1 d . . .
C18 C 1.10209(16) 0.57257(8) 0.67130(16) 0.0169(3) Uani 1 d . . .
C19 C 1.04082(17) 0.63396(8) 0.68035(16) 0.0176(3) Uani 1 d . . .
C20 C 0.93145(16) 0.63473(8) 0.71561(16) 0.0165(3) Uani 1 d . . .
C21 C 1.2888(2) 0.49136(10) 0.6255(2) 0.0303(4) Uani 1 d . . .
H2 H 0.607(2) 0.4620(11) 0.623(2) 0.021(5) Uiso 1 d . . .
H3 H 0.583(2) 0.3491(13) 0.654(2) 0.034(6) Uiso 1 d . . .
H5 H 0.777(2) 0.3766(10) 1.048(2) 0.022(5) Uiso 1 d . . .
H6 H 0.799(2) 0.4895(12) 1.013(2) 0.032(6) Uiso 1 d . . .
H7A H 0.840(3) 0.2612(13) 1.067(2) 0.040(7) Uiso 1 d . . .
H7B H 0.742(3) 0.1983(15) 1.046(3) 0.055(8) Uiso 1 d . . .
H7C H 0.696(3) 0.2669(14) 1.086(3) 0.050(8) Uiso 1 d . . .
H9 H 0.582(2) 0.6205(10) 0.925(2) 0.022(5) Uiso 1 d . . .
H10 H 0.628(2) 0.6627(10) 1.132(2) 0.019(5) Uiso 1 d . . .
H12 H 1.023(2) 0.6673(11) 1.205(2) 0.030(6) Uiso 1 d . . .
H13 H 0.975(2) 0.6234(10) 1.001(2) 0.019(5) Uiso 1 d . . .
H14A H 0.673(2) 0.6643(12) 1.364(2) 0.027(5) Uiso 1 d . . .
H14B H 0.744(2) 0.7210(12) 1.463(3) 0.038(6) Uiso 1 d . . .
H14C H 0.664(3) 0.7376(13) 1.313(3) 0.041(7) Uiso 1 d . . .
H16 H 0.912(2) 0.4725(11) 0.757(2) 0.020(5) Uiso 1 d . . .
H17 H 1.085(2) 0.4713(11) 0.693(2) 0.022(5) Uiso 1 d . . .
H19 H 1.0752(19) 0.6744(11) 0.663(2) 0.019(5) Uiso 1 d . . .
H20 H 0.893(2) 0.6768(11) 0.721(2) 0.022(5) Uiso 1 d . . .
H21A H 1.316(2) 0.4733(12) 0.716(2) 0.036(6) Uiso 1 d . . .
H21B H 1.214(3) 0.4632(13) 0.561(3) 0.040(7) Uiso 1 d . . .
H21C H 1.360(3) 0.4918(13) 0.599(3) 0.045(7) Uiso 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
Se1 P1 2.1022(4) . ?
S1 C4 1.7533(16) . ?
S1 C7 1.791(2) . ?
S2 C11 1.7538(15) . ?
S2 C14 1.797(2) . ?
S3 C18 1.7520(16) . ?
S3 C21 1.794(2) . ?
P1 C1 1.8082(16) . ?
P1 C8 1.8076(15) . ?
P1 C15 1.8054(15) . ?
C1 C2 1.397(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.89(2) . ?
C3 C4 1.398(2) . ?
C3 H3 0.93(2) . ?
C4 C5 1.396(2) . ?
C5 C6 1.392(2) . ?
C5 H5 0.94(2) . ?
C6 H6 0.94(2) . ?
C7 H7A 0.98(3) . ?
C7 H7B 0.95(3) . ?
C7 H7C 0.97(3) . ?
C8 C9 1.396(2) . ?
C8 C13 1.392(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.92(2) . ?
C10 C11 1.396(2) . ?
C10 H10 0.88(2) . ?
C11 C12 1.400(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.96(2) . ?
C13 H13 0.92(2) . ?
C14 H14A 0.92(2) . ?
C14 H14B 0.93(3) . ?
C14 H14C 0.95(3) . ?
C15 C16 1.391(2) . ?
C15 C20 1.403(2) . ?
C16 C17 1.391(2) . ?
C16 H16 0.94(2) . ?
C17 C18 1.390(2) . ?
C17 H17 0.91(2) . ?
C18 C19 1.405(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.93(2) . ?
C20 H20 0.94(2) . ?
C21 H21A 0.98(2) . ?
C21 H21B 1.01(3) . ?
C21 H21C 0.92(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
C4 S1 C7 103.46(9) . . ?
C11 S2 C14 103.99(9) . . ?
C18 S3 C21 103.05(9) . . ?
C1 P1 Se1 114.66(5) . . ?
C8 P1 Se1 112.62(5) . . ?
C8 P1 C1 104.09(7) . . ?
C15 P1 Se1 111.97(5) . . ?
C15 P1 C1 104.72(7) . . ?
C15 P1 C8 108.12(7) . . ?
C2 C1 P1 119.65(12) . . ?
C6 C1 P1 121.45(12) . . ?
C6 C1 C2 118.76(14) . . ?
C1 C2 H2 119.7(14) . . ?
C3 C2 C1 120.52(15) . . ?
C3 C2 H2 119.7(14) . . ?
C2 C3 C4 120.79(15) . . ?
C2 C3 H3 120.3(15) . . ?
C4 C3 H3 118.9(15) . . ?
C3 C4 S1 116.23(12) . . ?
C5 C4 S1 124.81(13) . . ?
C5 C4 C3 118.97(15) . . ?
C4 C5 H5 120.9(12) . . ?
C6 C5 C4 119.92(15) . . ?
C6 C5 H5 119.1(13) . . ?
C1 C6 C5 120.97(15) . . ?
C1 C6 H6 120.7(14) . . ?
C5 C6 H6 118.3(14) . . ?
S1 C7 H7A 108.3(15) . . ?
S1 C7 H7B 103.8(17) . . ?
S1 C7 H7C 109.2(16) . . ?
H7A C7 H7B 110(2) . . ?
H7A C7 H7C 115(2) . . ?
H7B C7 H7C 109(2) . . ?
C9 C8 P1 117.85(12) . . ?
C13 C8 P1 122.87(12) . . ?
C13 C8 C9 119.18(14) . . ?
C8 C9 H9 119.5(13) . . ?
C10 C9 C8 120.75(16) . . ?
C10 C9 H9 119.7(13) . . ?
C9 C10 C11 119.96(15) . . ?
C9 C10 H10 119.9(13) . . ?
C11 C10 H10 120.1(13) . . ?
C10 C11 S2 124.21(12) . . ?
C10 C11 C12 119.27(14) . . ?
C12 C11 S2 116.50(12) . . ?
C11 C12 H12 122.3(13) . . ?
C13 C12 C11 120.42(15) . . ?
C13 C12 H12 117.3(13) . . ?
C8 C13 H13 121.2(13) . . ?
C12 C13 C8 120.36(15) . . ?
C12 C13 H13 118.4(13) . . ?
S2 C14 H14A 110.9(14) . . ?
S2 C14 H14B 101.7(15) . . ?
S2 C14 H14C 107.6(15) . . ?
H14A C14 H14B 112(2) . . ?
H14A C14 H14C 111(2) . . ?
H14B C14 H14C 113(2) . . ?
C16 C15 P1 121.53(12) . . ?
C16 C15 C20 118.97(14) . . ?
C20 C15 P1 119.31(11) . . ?
C15 C16 H16 120.3(12) . . ?
C17 C16 C15 120.82(15) . . ?
C17 C16 H16 118.9(12) . . ?
C16 C17 H17 116.6(13) . . ?
C18 C17 C16 120.24(15) . . ?
C18 C17 H17 123.2(13) . . ?
C17 C18 S3 124.51(12) . . ?
C17 C18 C19 119.07(14) . . ?
C19 C18 S3 116.41(12) . . ?
C18 C19 H19 119.3(12) . . ?
C20 C19 C18 120.61(15) . . ?
C20 C19 H19 120.0(12) . . ?
C15 C20 H20 121.5(13) . . ?
C19 C20 C15 120.28(14) . . ?
C19 C20 H20 118.2(13) . . ?
S3 C21 H21A 107.7(14) . . ?
S3 C21 H21B 112.8(14) . . ?
S3 C21 H21C 106.0(16) . . ?
H21A C21 H21B 110(2) . . ?
H21A C21 H21C 111(2) . . ?
H21B C21 H21C 109(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
C2 C1 P1 Se1 40.97(14) . . . . ?
C2 C1 P1 C8 164.45(13) . . . . ?
C2 C1 P1 C15 -82.13(14) . . . . ?
C3 C4 S1 C7 177.59(15) . . . . ?
C5 C4 S1 C7 -2.44(18) . . . . ?
C6 C1 P1 Se1 -143.32(12) . . . . ?
C6 C1 P1 C8 -19.84(15) . . . . ?
C6 C1 P1 C15 93.57(14) . . . . ?
C9 C8 P1 Se1 49.13(13) . . . . ?
C9 C8 P1 C1 -75.67(14) . . . . ?
C9 C8 P1 C15 173.37(12) . . . . ?
C10 C11 S2 C14 -1.12(16) . . . . ?
C12 C11 S2 C14 -179.67(13) . . . . ?
C13 C8 P1 Se1 -134.67(12) . . . . ?
C13 C8 P1 C1 100.53(14) . . . . ?
C13 C8 P1 C15 -10.43(15) . . . . ?
C16 C15 P1 Se1 -120.27(12) . . . . ?
C16 C15 P1 C1 4.56(15) . . . . ?
C16 C15 P1 C8 115.09(13) . . . . ?
C17 C18 S3 C21 2.12(18) . . . . ?
C19 C18 S3 C21 -179.30(14) . . . . ?
C20 C15 P1 Se1 54.63(13) . . . . ?
C20 C15 P1 C1 179.46(12) . . . . ?
C20 C15 P1 C8 -70.00(14) . . . . ?

####################################################################### 
# 
# 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=O_16srv361
_database_code_depnum_ccdc_archive 'CCDC 1578846'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_audit_creation_date             2016-09-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 O P S3'
_chemical_formula_sum            'C21 H21 O P S3'
_chemical_formula_weight         416.53
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1402(5)
_cell_length_b                   20.3778(10)
_cell_length_c                   10.7202(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.9689(16)
_cell_angle_gamma                90
_cell_volume                     2008.13(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.25
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.9309.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44040
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.320
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4855
_reflns_number_total             5855
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.76216(4) 0.02171(2) 1.01097(4) 0.01828(9) Uani 1 1 d . . . . .
S2 S 0.06864(4) 0.43134(2) 0.93085(4) 0.01975(9) Uani 1 1 d . . . . .
S3 S 0.09426(4) 0.21820(2) 0.05571(4) 0.01920(9) Uani 1 1 d . . . . .
P1 P 0.16689(4) 0.16765(2) 0.66656(4) 0.01064(8) Uani 1 1 d . . . . .
O1 O 0.05344(11) 0.11982(5) 0.66192(10) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.34808(14) 0.13778(6) 0.76786(14) 0.0122(3) Uani 1 1 d . . . . .
C2 C 0.43553(15) 0.11349(7) 0.70661(15) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.56216(16) 0.07974(7) 0.78421(15) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.60538(15) 0.06955(7) 0.92490(15) 0.0134(3) Uani 1 1 d . . . . .
C5 C 0.52207(16) 0.09618(7) 0.98797(15) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.39413(15) 0.12951(7) 0.90928(15) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.78070(18) 0.01925(8) 1.18529(16) 0.0207(3) Uani 1 1 d . . . . .
C8 C 0.14912(15) 0.24485(7) 0.73922(14) 0.0120(3) Uani 1 1 d . . . . .
C9 C 0.26771(15) 0.28223(7) 0.82547(15) 0.0138(3) Uani 1 1 d . . . . .
C10 C 0.24798(15) 0.33959(7) 0.88611(15) 0.0136(3) Uani 1 1 d . . . . .
C11 C 0.10765(15) 0.36068(7) 0.85863(14) 0.0124(3) Uani 1 1 d . . . . .
C12 C -0.01181(15) 0.32431(7) 0.76961(15) 0.0142(3) Uani 1 1 d . . . . .
C13 C 0.00869(15) 0.26689(7) 0.71160(14) 0.0133(3) Uani 1 1 d . . . . .
C14 C 0.24365(19) 0.46800(9) 1.02771(19) 0.0248(3) Uani 1 1 d . . . . .
C15 C 0.15325(14) 0.18296(7) 0.49614(14) 0.0118(2) Uani 1 1 d . . . . .
C16 C 0.19499(16) 0.24176(7) 0.45614(15) 0.0158(3) Uani 1 1 d . . . . .
C17 C 0.17621(16) 0.25049(7) 0.32149(15) 0.0165(3) Uani 1 1 d . . . . .
C18 C 0.11519(15) 0.20083(7) 0.22365(14) 0.0138(3) Uani 1 1 d . . . . .
C19 C 0.07510(16) 0.14193(7) 0.26339(15) 0.0145(3) Uani 1 1 d . . . . .
C20 C 0.09417(15) 0.13333(7) 0.39880(14) 0.0131(3) Uani 1 1 d . . . . .
C21 C 0.0192(2) 0.14350(9) -0.03545(17) 0.0252(3) Uani 1 1 d . . . . .
H2 H 0.4103(18) 0.1189(8) 0.6120(18) 0.013(4) Uiso 1 1 d . . . . .
H3 H 0.622(2) 0.0636(9) 0.7403(19) 0.019(5) Uiso 1 1 d . . . . .
H5 H 0.5496(18) 0.0908(8) 1.0825(18) 0.013(4) Uiso 1 1 d . . . . .
H6 H 0.334(2) 0.1457(9) 0.9529(19) 0.023(5) Uiso 1 1 d . . . . .
H7A H 0.689(2) 0.0016(10) 1.1879(19) 0.024(5) Uiso 1 1 d . . . . .
H7B H 0.805(2) 0.0625(10) 1.226(2) 0.028(5) Uiso 1 1 d . . . . .
H7C H 0.858(2) -0.0113(10) 1.231(2) 0.031(5) Uiso 1 1 d . . . . .
H9 H 0.364(2) 0.2679(9) 0.8454(18) 0.017(4) Uiso 1 1 d . . . . .
H10 H 0.3285(19) 0.3635(9) 0.9466(18) 0.016(4) Uiso 1 1 d . . . . .
H12 H -0.1087(19) 0.3388(8) 0.7484(18) 0.015(4) Uiso 1 1 d . . . . .
H13 H -0.071(2) 0.2426(9) 0.6555(19) 0.019(4) Uiso 1 1 d . . . . .
H14A H 0.224(2) 0.5074(10) 1.071(2) 0.029(5) Uiso 1 1 d . . . . .
H14B H 0.312(3) 0.4380(11) 1.102(2) 0.042(6) Uiso 1 1 d . . . . .
H14C H 0.288(2) 0.4810(10) 0.966(2) 0.035(6) Uiso 1 1 d . . . . .
H16 H 0.237(2) 0.2764(9) 0.5206(19) 0.020(5) Uiso 1 1 d . . . . .
H17 H 0.200(2) 0.2908(9) 0.293(2) 0.023(5) Uiso 1 1 d . . . . .
H19 H 0.0349(19) 0.1079(9) 0.2005(18) 0.017(4) Uiso 1 1 d . . . . .
H20 H 0.0643(18) 0.0942(9) 0.4244(17) 0.013(4) Uiso 1 1 d . . . . .
H21A H 0.086(2) 0.1077(11) 0.008(2) 0.036(6) Uiso 1 1 d . . . . .
H21B H 0.005(2) 0.1498(10) -0.130(2) 0.034(6) Uiso 1 1 d . . . . .
H21C H -0.075(2) 0.1331(11) -0.035(2) 0.038(6) Uiso 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 C4 1.7581(14) . ?
S1 C7 1.7982(17) . ?
S2 C11 1.7572(14) . ?
S2 C14 1.7972(18) . ?
S3 C18 1.7576(14) . ?
S3 C21 1.7953(18) . ?
P1 O1 1.4925(10) . ?
P1 C1 1.8003(14) . ?
P1 C8 1.7979(14) . ?
P1 C15 1.8002(14) . ?
C1 C2 1.3979(19) . ?
C1 C6 1.395(2) . ?
C2 C3 1.383(2) . ?
C2 H2 0.942(17) . ?
C3 C4 1.397(2) . ?
C3 H3 0.969(18) . ?
C4 C5 1.396(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.937(17) . ?
C6 H6 0.968(19) . ?
C7 H7A 1.01(2) . ?
C7 H7B 0.97(2) . ?
C7 H7C 0.96(2) . ?
C8 C9 1.3937(19) . ?
C8 C13 1.4005(19) . ?
C9 C10 1.3923(19) . ?
C9 H9 0.956(18) . ?
C10 C11 1.3937(19) . ?
C10 H10 0.936(18) . ?
C11 C12 1.397(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.957(18) . ?
C13 H13 0.924(19) . ?
C14 H14A 0.99(2) . ?
C14 H14B 1.01(2) . ?
C14 H14C 0.98(2) . ?
C15 C16 1.397(2) . ?
C15 C20 1.3938(19) . ?
C16 C17 1.386(2) . ?
C16 H16 0.952(19) . ?
C17 C18 1.400(2) . ?
C17 H17 0.943(19) . ?
C18 C19 1.390(2) . ?
C19 C20 1.3922(19) . ?
C19 H19 0.933(18) . ?
C20 H20 0.935(17) . ?
C21 H21A 0.97(2) . ?
C21 H21B 0.97(2) . ?
C21 H21C 0.99(2) . ?

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
C4 S1 C7 103.63(7) . . ?
C11 S2 C14 104.14(7) . . ?
C18 S3 C21 103.12(7) . . ?
O1 P1 C1 112.04(6) . . ?
O1 P1 C8 111.66(6) . . ?
O1 P1 C15 110.57(6) . . ?
C8 P1 C1 107.33(6) . . ?
C8 P1 C15 108.01(6) . . ?
C15 P1 C1 107.00(6) . . ?
C2 C1 P1 121.64(11) . . ?
C6 C1 P1 118.98(11) . . ?
C6 C1 C2 118.68(13) . . ?
C1 C2 H2 121.7(10) . . ?
C3 C2 C1 120.37(13) . . ?
C3 C2 H2 117.9(10) . . ?
C2 C3 C4 120.79(13) . . ?
C2 C3 H3 119.3(11) . . ?
C4 C3 H3 119.9(11) . . ?
C3 C4 S1 116.81(11) . . ?
C5 C4 S1 124.03(11) . . ?
C5 C4 C3 119.15(13) . . ?
C4 C5 H5 120.9(11) . . ?
C6 C5 C4 119.79(13) . . ?
C6 C5 H5 119.3(10) . . ?
C1 C6 H6 119.6(11) . . ?
C5 C6 C1 121.13(13) . . ?
C5 C6 H6 119.3(11) . . ?
S1 C7 H7A 110.2(11) . . ?
S1 C7 H7B 109.8(12) . . ?
S1 C7 H7C 104.8(12) . . ?
H7A C7 H7B 112.1(16) . . ?
H7A C7 H7C 108.7(16) . . ?
H7B C7 H7C 111.0(17) . . ?
C9 C8 P1 123.33(11) . . ?
C9 C8 C13 118.72(13) . . ?
C13 C8 P1 117.90(10) . . ?
C8 C9 H9 119.8(11) . . ?
C10 C9 C8 120.98(13) . . ?
C10 C9 H9 119.2(11) . . ?
C9 C10 C11 119.69(13) . . ?
C9 C10 H10 120.3(11) . . ?
C11 C10 H10 120.0(11) . . ?
C10 C11 S2 124.00(11) . . ?
C10 C11 C12 119.63(13) . . ?
C12 C11 S2 116.37(11) . . ?
C11 C12 H12 120.4(11) . . ?
C13 C12 C11 120.34(13) . . ?
C13 C12 H12 119.3(11) . . ?
C8 C13 H13 120.2(11) . . ?
C12 C13 C8 120.62(13) . . ?
C12 C13 H13 119.2(11) . . ?
S2 C14 H14A 105.5(12) . . ?
S2 C14 H14B 112.7(13) . . ?
S2 C14 H14C 110.1(13) . . ?
H14A C14 H14B 109.2(17) . . ?
H14A C14 H14C 109.8(17) . . ?
H14B C14 H14C 109.5(18) . . ?
C16 C15 P1 123.83(11) . . ?
C20 C15 P1 117.30(10) . . ?
C20 C15 C16 118.86(13) . . ?
C15 C16 H16 120.7(11) . . ?
C17 C16 C15 120.25(13) . . ?
C17 C16 H16 119.0(11) . . ?
C16 C17 C18 120.71(13) . . ?
C16 C17 H17 120.5(12) . . ?
C18 C17 H17 118.7(12) . . ?
C17 C18 S3 116.48(11) . . ?
C19 C18 S3 124.28(11) . . ?
C19 C18 C17 119.24(13) . . ?
C18 C19 C20 119.88(13) . . ?
C18 C19 H19 121.0(11) . . ?
C20 C19 H19 119.1(11) . . ?
C15 C20 H20 119.3(10) . . ?
C19 C20 C15 121.06(13) . . ?
C19 C20 H20 119.6(10) . . ?
S3 C21 H21A 109.1(13) . . ?
S3 C21 H21B 107.4(13) . . ?
S3 C21 H21C 111.6(13) . . ?
H21A C21 H21B 111.7(18) . . ?
H21A C21 H21C 108.5(18) . . ?
H21B C21 H21C 108.6(17) . . ?

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
C2 C1 P1 O1 103.87(12) . . . . ?
C2 C1 P1 C8 -133.22(12) . . . . ?
C2 C1 P1 C15 -17.49(13) . . . . ?
C3 C4 S1 C7 -179.44(11) . . . . ?
C5 C4 S1 C7 -0.76(14) . . . . ?
C6 C1 P1 O1 -66.39(12) . . . . ?
C6 C1 P1 C8 56.52(13) . . . . ?
C6 C1 P1 C15 172.26(11) . . . . ?
C9 C8 P1 O1 142.16(12) . . . . ?
C9 C8 P1 C1 19.01(14) . . . . ?
C9 C8 P1 C15 -96.06(13) . . . . ?
C10 C11 S2 C14 4.44(14) . . . . ?
C12 C11 S2 C14 -176.10(12) . . . . ?
C13 C8 P1 O1 -35.23(13) . . . . ?
C13 C8 P1 C1 -158.38(11) . . . . ?
C13 C8 P1 C15 86.55(12) . . . . ?
C16 C15 P1 O1 151.47(12) . . . . ?
C16 C15 P1 C1 -86.25(13) . . . . ?
C16 C15 P1 C8 29.02(14) . . . . ?
C17 C18 S3 C21 178.48(12) . . . . ?
C19 C18 S3 C21 -1.65(15) . . . . ?
C20 C15 P1 O1 -26.95(13) . . . . ?
C20 C15 P1 C1 95.32(11) . . . . ?
C20 C15 P1 C8 -149.40(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
