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

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

data_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1483048'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 O P2 S2'
_chemical_formula_weight         334.39

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.4559(4)
_cell_length_b                   12.3783(6)
_cell_length_c                   22.5131(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1799.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    8652
_cell_measurement_theta_min      3.175
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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            17444
_diffrn_reflns_av_R_equivalents  0.1234
_diffrn_reflns_av_sigmaI/netI    0.1069
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.43
_reflns_number_total             4104
_reflns_number_gt                2694
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR2002
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0408P)²+3.1411P] 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   0.38(18)
_refine_ls_number_reflns         4104
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C6 C 0.8891(5) 0.1234(2) 0.12773(15) 0.0319(12) Uani 1 1 d G . .
C10 C 0.6867(5) 0.1579(3) 0.13687(15) 0.0327(12) Uani 1 1 d G . .
H1 H 0.5954 0.1154 0.1586 0.039 Uiso 1 1 calc R . .
C11 C 0.6208(4) 0.2560(3) 0.11351(17) 0.0434(15) Uani 1 1 d G . .
H2 H 0.4854 0.2791 0.1196 0.052 Uiso 1 1 calc R . .
C13 C 0.7573(6) 0.3196(2) 0.08100(17) 0.0409(14) Uani 1 1 d G . .
C12 C 0.9597(5) 0.2851(3) 0.07185(16) 0.0420(15) Uani 1 1 d G . .
H3 H 1.0510 0.3277 0.0501 0.050 Uiso 1 1 calc R . .
C14 C 1.0256(4) 0.1870(3) 0.09521(16) 0.0401(14) Uani 1 1 d G . .
H4 H 1.1610 0.1639 0.0891 0.048 Uiso 1 1 calc R . .
P5 P 1.0322(2) 0.02317(11) 0.23372(7) 0.0312(3) Uani 1 1 d . . .
S2 S 1.0972(2) -0.17103(13) 0.05526(7) 0.0449(4) Uani 1 1 d . . .
P3 P 0.8212(2) -0.13836(11) 0.08375(6) 0.0308(3) Uani 1 1 d . . .
S3 S 1.2376(2) 0.13681(12) 0.24655(6) 0.0391(4) Uani 1 1 d . . .
O5 O 0.8190(6) -0.0710(3) 0.14580(14) 0.0286(8) Uani 1 1 d . . .
C7 C 0.9669(8) 0.0169(4) 0.1540(2) 0.0298(12) Uani 1 1 d . . .
H24 H 1.0936 -0.0028 0.1326 0.036 Uiso 1 1 calc R . .
C8 C 0.6661(10) -0.2513(4) 0.1039(2) 0.0423(15) Uani 1 1 d . . .
H5 H 0.7311 -0.2895 0.1360 0.063 Uiso 1 1 calc R . .
H6 H 0.6518 -0.2986 0.0703 0.063 Uiso 1 1 calc R . .
H7 H 0.5318 -0.2268 0.1162 0.063 Uiso 1 1 calc R . .
C9 C 0.7902(9) 0.0416(5) 0.2734(2) 0.0434(15) Uani 1 1 d . . .
H8 H 0.7239 0.1070 0.2592 0.052 Uiso 1 1 calc R . .
H9 H 0.6991 -0.0185 0.2643 0.052 Uiso 1 1 calc R . .
C15 C 1.1185(9) -0.1115(4) 0.2526(3) 0.0403(14) Uani 1 1 d . . .
H10 H 1.1464 -0.1146 0.2949 0.048 Uiso 1 1 calc R . .
H11 H 1.0078 -0.1622 0.2441 0.048 Uiso 1 1 calc R . .
C16 C 0.6699(10) -0.0616(4) 0.0323(2) 0.0443(16) Uani 1 1 d . . .
H12 H 0.5397 -0.0430 0.0502 0.066 Uiso 1 1 calc R . .
H13 H 0.6456 -0.1039 -0.0028 0.066 Uiso 1 1 calc R . .
H14 H 0.7431 0.0031 0.0218 0.066 Uiso 1 1 calc R . .
C17 C 1.3107(10) -0.1462(5) 0.2193(3) 0.0571(18) Uani 1 1 d . . .
H15 H 1.2733 -0.1685 0.1799 0.086 Uiso 1 1 calc R . .
H16 H 1.3749 -0.2054 0.2398 0.086 Uiso 1 1 calc R . .
H17 H 1.4059 -0.0868 0.2171 0.086 Uiso 1 1 calc R . .
C18 C 0.8145(11) 0.0494(6) 0.3404(3) 0.0577(18) Uani 1 1 d . . .
H18 H 0.8738 -0.0164 0.3553 0.087 Uiso 1 1 calc R . .
H19 H 0.6813 0.0606 0.3583 0.087 Uiso 1 1 calc R . .
H20 H 0.9039 0.1089 0.3500 0.087 Uiso 1 1 calc R . .
C19 C 0.6864(12) 0.4290(5) 0.0575(3) 0.063(2) Uani 1 1 d . . .
H21 H 0.6986 0.4822 0.0884 0.095 Uiso 1 1 calc R . .
H22 H 0.5445 0.4242 0.0450 0.095 Uiso 1 1 calc R . .
H23 H 0.7713 0.4495 0.0244 0.095 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C6 0.046(3) 0.025(3) 0.024(3) -0.002(2) -0.005(2) -0.004(3)
C10 0.021(3) 0.037(3) 0.040(3) 0.002(3) 0.002(2) 0.000(2)
C11 0.048(4) 0.041(3) 0.042(4) -0.001(3) -0.013(3) 0.003(3)
C13 0.055(4) 0.033(3) 0.035(3) 0.002(3) -0.007(3) -0.002(3)
C12 0.043(3) 0.040(3) 0.043(4) 0.004(3) 0.002(3) -0.005(3)
C14 0.053(4) 0.033(3) 0.034(3) 0.004(3) 0.004(3) -0.003(3)
P5 0.0278(7) 0.0327(8) 0.0332(8) -0.0028(6) -0.0029(6) 0.0000(6)
S2 0.0452(9) 0.0514(9) 0.0380(8) -0.0123(7) 0.0058(7) 0.0013(8)
P3 0.0392(8) 0.0286(7) 0.0247(7) -0.0029(6) -0.0026(6) -0.0016(7)
S3 0.0358(8) 0.0382(7) 0.0434(9) -0.0101(7) -0.0045(6) -0.0043(7)
O5 0.033(2) 0.0299(18) 0.0230(18) -0.0083(15) -0.0002(16) -0.0075(16)
C7 0.017(2) 0.035(3) 0.037(3) -0.006(2) 0.000(2) -0.007(2)
C8 0.066(4) 0.027(3) 0.034(3) 0.003(2) -0.002(3) -0.011(3)
C9 0.039(3) 0.063(4) 0.028(3) -0.004(3) 0.006(3) 0.000(3)
C15 0.039(3) 0.043(3) 0.039(3) -0.001(3) -0.004(3) -0.001(3)
C16 0.067(4) 0.035(3) 0.031(3) 0.007(3) -0.015(3) -0.002(3)
C17 0.068(5) 0.041(3) 0.063(4) -0.003(3) -0.008(4) 0.016(4)
C18 0.059(4) 0.074(5) 0.041(4) -0.006(3) 0.013(3) 0.000(4)
C19 0.074(5) 0.051(4) 0.065(5) 0.021(4) -0.010(4) 0.000(4)

_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
C6 C10 1.3900 . ?
C6 C14 1.3900 . ?
C6 C7 1.530(5) . ?
C10 C11 1.3900 . ?
C10 H1 0.9300 . ?
C11 C13 1.3900 . ?
C11 H2 0.9300 . ?
C13 C12 1.3900 . ?
C13 C19 1.524(6) . ?
C12 C14 1.3900 . ?
C12 H3 0.9300 . ?
C14 H4 0.9300 . ?
P5 C9 1.815(6) . ?
P5 C15 1.808(5) . ?
P5 C7 1.846(5) . ?
P5 S3 1.955(2) . ?
S2 P3 1.937(2) . ?
P3 O5 1.627(3) . ?
P3 C16 1.789(6) . ?
P3 C8 1.778(5) . ?
O5 C7 1.459(6) . ?
C7 H24 0.9800 . ?
C8 H5 0.9600 . ?
C8 H6 0.9600 . ?
C8 H7 0.9600 . ?
C9 C18 1.520(8) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C15 C17 1.512(8) . ?
C15 H10 0.9700 . ?
C15 H11 0.9700 . ?
C16 H12 0.9600 . ?
C16 H13 0.9600 . ?
C16 H14 0.9600 . ?
C17 H15 0.9600 . ?
C17 H16 0.9600 . ?
C17 H17 0.9600 . ?
C18 H18 0.9600 . ?
C18 H19 0.9600 . ?
C18 H20 0.9600 . ?
C19 H21 0.9600 . ?
C19 H22 0.9600 . ?
C19 H23 0.9600 . ?

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
C10 C6 C14 120.0 . . ?
C10 C6 C7 121.1(3) . . ?
C14 C6 C7 118.9(3) . . ?
C6 C10 C11 120.0 . . ?
C6 C10 H1 120.0 . . ?
C11 C10 H1 120.0 . . ?
C13 C11 C10 120.0 . . ?
C13 C11 H2 120.0 . . ?
C10 C11 H2 120.0 . . ?
C11 C13 C12 120.0 . . ?
C11 C13 C19 119.7(4) . . ?
C12 C13 C19 120.3(4) . . ?
C13 C12 C14 120.0 . . ?
C13 C12 H3 120.0 . . ?
C14 C12 H3 120.0 . . ?
C12 C14 C6 120.0 . . ?
C12 C14 H4 120.0 . . ?
C6 C14 H4 120.0 . . ?
C9 P5 C15 105.4(3) . . ?
C9 P5 C7 106.7(2) . . ?
C15 P5 C7 105.0(2) . . ?
C9 P5 S3 114.9(2) . . ?
C15 P5 S3 114.8(2) . . ?
C7 P5 S3 109.21(18) . . ?
O5 P3 C16 106.2(2) . . ?
O5 P3 C8 100.3(2) . . ?
C16 P3 C8 106.0(3) . . ?
O5 P3 S2 113.54(16) . . ?
C16 P3 S2 113.5(2) . . ?
C8 P3 S2 116.0(2) . . ?
C7 O5 P3 119.0(3) . . ?
O5 C7 C6 112.3(4) . . ?
O5 C7 P5 107.7(3) . . ?
C6 C7 P5 114.5(3) . . ?
O5 C7 H24 107.4 . . ?
C6 C7 H24 107.4 . . ?
P5 C7 H24 107.4 . . ?
P3 C8 H5 109.5 . . ?
P3 C8 H6 109.5 . . ?
H5 C8 H6 109.5 . . ?
P3 C8 H7 109.5 . . ?
H5 C8 H7 109.5 . . ?
H6 C8 H7 109.5 . . ?
C18 C9 P5 114.1(4) . . ?
C18 C9 H8 108.7 . . ?
P5 C9 H8 108.7 . . ?
C18 C9 H9 108.7 . . ?
P5 C9 H9 108.7 . . ?
H8 C9 H9 107.6 . . ?
C17 C15 P5 113.5(4) . . ?
C17 C15 H10 108.9 . . ?
P5 C15 H10 108.9 . . ?
C17 C15 H11 108.9 . . ?
P5 C15 H11 108.9 . . ?
H10 C15 H11 107.7 . . ?
P3 C16 H12 109.5 . . ?
P3 C16 H13 109.5 . . ?
H12 C16 H13 109.5 . . ?
P3 C16 H14 109.5 . . ?
H12 C16 H14 109.5 . . ?
H13 C16 H14 109.5 . . ?
C15 C17 H15 109.5 . . ?
C15 C17 H16 109.5 . . ?
H15 C17 H16 109.5 . . ?
C15 C17 H17 109.5 . . ?
H15 C17 H17 109.5 . . ?
H16 C17 H17 109.5 . . ?
C9 C18 H18 109.5 . . ?
C9 C18 H19 109.5 . . ?
H18 C18 H19 109.5 . . ?
C9 C18 H20 109.5 . . ?
H18 C18 H20 109.5 . . ?
H19 C18 H20 109.5 . . ?
C13 C19 H21 109.5 . . ?
C13 C19 H22 109.5 . . ?
H21 C19 H22 109.5 . . ?
C13 C19 H23 109.5 . . ?
H21 C19 H23 109.5 . . ?
H22 C19 H23 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
C14 C6 C10 C11 0.0 . . . . ?
C7 C6 C10 C11 178.8(4) . . . . ?
C6 C10 C11 C13 0.0 . . . . ?
C10 C11 C13 C12 0.0 . . . . ?
C10 C11 C13 C19 -177.7(4) . . . . ?
C11 C13 C12 C14 0.0 . . . . ?
C19 C13 C12 C14 177.7(4) . . . . ?
C13 C12 C14 C6 0.0 . . . . ?
C10 C6 C14 C12 0.0 . . . . ?
C7 C6 C14 C12 -178.8(3) . . . . ?
C16 P3 O5 C7 -83.7(4) . . . . ?
C8 P3 O5 C7 166.2(4) . . . . ?
S2 P3 O5 C7 41.7(4) . . . . ?
P3 O5 C7 C6 85.0(4) . . . . ?
P3 O5 C7 P5 -148.1(3) . . . . ?
C10 C6 C7 O5 44.7(5) . . . . ?
C14 C6 C7 O5 -136.5(3) . . . . ?
C10 C6 C7 P5 -78.4(4) . . . . ?
C14 C6 C7 P5 100.4(3) . . . . ?
C9 P5 C7 O5 -57.1(4) . . . . ?
C15 P5 C7 O5 54.5(4) . . . . ?
S3 P5 C7 O5 178.1(3) . . . . ?
C9 P5 C7 C6 68.5(4) . . . . ?
C15 P5 C7 C6 -179.9(3) . . . . ?
S3 P5 C7 C6 -56.3(3) . . . . ?
C15 P5 C9 C18 69.1(5) . . . . ?
C7 P5 C9 C18 -179.6(5) . . . . ?
S3 P5 C9 C18 -58.4(5) . . . . ?
C9 P5 C15 C17 174.9(4) . . . . ?
C7 P5 C15 C17 62.4(5) . . . . ?
S3 P5 C15 C17 -57.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.110
_chemical_absolute_configuration ad
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1486721'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 P2 S2'
_chemical_formula_weight         338.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   9.3474(7)
_cell_length_b                   7.1672(4)
_cell_length_c                   13.3103(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.490(2)
_cell_angle_gamma                90.00
_cell_volume                     873.85(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    6061
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS Rapid'
_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            8196
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.43
_reflns_number_total             1989
_reflns_number_gt                1658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SHELX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0559P)²+0.3664P] 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         1989
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_restrained_S_all      1.268
_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
C5 C 0.68100(18) -0.1699(2) 0.72411(9) 0.0424(6) Uani 1 1 d G . .
H1 H 0.6899 -0.1874 0.6549 0.051 Uiso 1 1 calc R . .
C2 C 0.78396(14) -0.0642(2) 0.78996(10) 0.0300(5) Uani 1 1 d G . .
H2 H 0.8632 -0.0095 0.7657 0.036 Uiso 1 1 calc R . .
C1 C 0.77091(13) -0.03869(19) 0.89126(9) 0.0255(4) Uani 1 1 d G . .
C3 C 0.65490(16) -0.1188(2) 0.92672(10) 0.0348(5) Uani 1 1 d G . .
H3 H 0.6460 -0.1013 0.9960 0.042 Uiso 1 1 calc R . .
C4 C 0.55195(14) -0.2245(2) 0.86087(14) 0.0465(7) Uani 1 1 d G . .
H4 H 0.4727 -0.2792 0.8851 0.056 Uiso 1 1 calc R . .
C6 C 0.56499(16) -0.2500(2) 0.75956(13) 0.0482(7) Uani 1 1 d G . .
H5 H 0.4946 -0.3223 0.7146 0.058 Uiso 1 1 calc R . .
P3 P 0.90480(6) 0.09631(7) 0.97957(4) 0.02312(18) Uani 1 1 d . . .
S1 S 0.83794(7) 0.18348(10) 1.10120(4) 0.0394(2) Uani 1 1 d . . .
C7 C 0.9687(2) 0.2788(3) 0.90441(17) 0.0279(5) Uani 1 1 d . . .
H6 H 1.0522 0.3445 0.9474 0.034 Uiso 1 1 calc R . .
H7 H 1.0031 0.2219 0.8457 0.034 Uiso 1 1 calc R . .
C8 C 0.8473(3) 0.4192(3) 0.86457(19) 0.0371(6) Uani 1 1 d . . .
H8 H 0.7730 0.3599 0.8119 0.056 Uiso 1 1 calc R . .
H9 H 0.8885 0.5269 0.8349 0.056 Uiso 1 1 calc R . .
H10 H 0.8026 0.4608 0.9214 0.056 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C5 0.0403(14) 0.0376(13) 0.0440(14) -0.0134(11) -0.0045(11) 0.0036(11)
C2 0.0283(11) 0.0277(11) 0.0317(11) -0.0025(9) 0.0003(9) 0.0012(9)
C1 0.0205(10) 0.0241(10) 0.0304(11) 0.0027(8) 0.0012(8) 0.0030(8)
C3 0.0239(11) 0.0330(12) 0.0475(14) 0.0097(10) 0.0073(10) 0.0035(9)
C4 0.0247(13) 0.0339(13) 0.079(2) 0.0073(13) 0.0061(13) -0.0042(10)
C6 0.0320(14) 0.0296(12) 0.074(2) -0.0113(13) -0.0121(13) -0.0019(10)
P3 0.0201(3) 0.0274(3) 0.0218(3) 0.0000(2) 0.0039(2) 0.0036(2)
S1 0.0352(4) 0.0567(4) 0.0277(3) -0.0061(3) 0.0101(2) 0.0126(3)
C7 0.0292(11) 0.0245(10) 0.0285(11) -0.0007(9) 0.0020(9) -0.0035(8)
C8 0.0416(14) 0.0298(12) 0.0366(13) 0.0028(10) 0.0002(11) 0.0048(10)

_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
C5 C2 1.3900 . ?
C5 C6 1.3900 . ?
C5 H1 0.9500 . ?
C2 C1 1.3900 . ?
C2 H2 0.9500 . ?
C1 C3 1.3900 . ?
C1 P3 1.8161(12) . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C6 1.3900 . ?
C4 H4 0.9500 . ?
C6 H5 0.9500 . ?
P3 C7 1.818(2) . ?
P3 S1 1.9507(8) . ?
P3 P3 2.2323(10) 3_757 ?
C7 C8 1.531(3) . ?
C7 H6 0.9900 . ?
C7 H7 0.9900 . ?
C8 H8 0.9800 . ?
C8 H9 0.9800 . ?
C8 H10 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
C2 C5 C6 120.0 . . ?
C2 C5 H1 120.0 . . ?
C6 C5 H1 120.0 . . ?
C1 C2 C5 120.0 . . ?
C1 C2 H2 120.0 . . ?
C5 C2 H2 120.0 . . ?
C2 C1 C3 120.0 . . ?
C2 C1 P3 121.05(8) . . ?
C3 C1 P3 118.95(8) . . ?
C4 C3 C1 120.0 . . ?
C4 C3 H3 120.0 . . ?
C1 C3 H3 120.0 . . ?
C3 C4 C6 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C4 H4 120.0 . . ?
C4 C6 C5 120.0 . . ?
C4 C6 H5 120.0 . . ?
C5 C6 H5 120.0 . . ?
C1 P3 C7 106.66(9) . . ?
C1 P3 S1 114.48(6) . . ?
C7 P3 S1 114.90(8) . . ?
C1 P3 P3 103.97(6) . 3_757 ?
C7 P3 P3 104.21(8) . 3_757 ?
S1 P3 P3 111.57(4) . 3_757 ?
C8 C7 P3 111.18(16) . . ?
C8 C7 H6 109.4 . . ?
P3 C7 H6 109.4 . . ?
C8 C7 H7 109.4 . . ?
P3 C7 H7 109.4 . . ?
H6 C7 H7 108.0 . . ?
C7 C8 H8 109.5 . . ?
C7 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
C7 C8 H10 109.5 . . ?
H8 C8 H10 109.5 . . ?
H9 C8 H10 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
C6 C5 C2 C1 0.0 . . . . ?
C5 C2 C1 C3 0.0 . . . . ?
C5 C2 C1 P3 179.26(11) . . . . ?
C2 C1 C3 C4 0.0 . . . . ?
P3 C1 C3 C4 -179.28(11) . . . . ?
C1 C3 C4 C6 0.0 . . . . ?
C3 C4 C6 C5 0.0 . . . . ?
C2 C5 C6 C4 0.0 . . . . ?
C2 C1 P3 C7 32.96(12) . . . . ?
C3 C1 P3 C7 -147.77(10) . . . . ?
C2 C1 P3 S1 161.20(8) . . . . ?
C3 C1 P3 S1 -19.53(10) . . . . ?
C2 C1 P3 P3 -76.83(9) . . . 3_757 ?
C3 C1 P3 P3 102.44(8) . . . 3_757 ?
C1 P3 C7 C8 67.26(17) . . . . ?
S1 P3 C7 C8 -60.75(17) . . . . ?
P3 P3 C7 C8 176.87(14) 3_757 . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.188
_chemical_absolute_configuration ad
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1498142'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 P2 S2'
_chemical_formula_weight         324.35

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_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                   9.1542(14)
_cell_length_b                   16.9650(15)
_cell_length_c                   10.682(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1658.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    5475
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS Rapid'
_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            14974
_diffrn_reflns_av_R_equivalents  0.1710
_diffrn_reflns_av_sigmaI/netI    0.0960
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.42
_reflns_number_total             1880
_reflns_number_gt                967
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SHELX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.2000P)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         1880
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2095
_refine_ls_R_factor_gt           0.1403
_refine_ls_wR_factor_ref         0.4216
_refine_ls_wR_factor_gt          0.3766
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_restrained_S_all      1.310
_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
S1 S 0.0391(3) 0.56844(13) 0.2881(2) 0.0681(9) Uani 1 1 d . . .
P1 P 0.0937(3) 0.50708(14) 0.4359(2) 0.0659(9) Uani 1 1 d . . .
C1 C 0.0818(11) 0.3664(6) 0.2990(9) 0.077(3) Uani 1 1 d . . .
H1 H 0.0116 0.3932 0.2492 0.092 Uiso 1 1 calc R A .
C2 C 0.1198(13) 0.2905(5) 0.2691(10) 0.080(3) Uani 1 1 d . . .
H2 H 0.0784 0.2651 0.1982 0.096 Uiso 1 1 calc R . .
C3 C 0.2759(12) 0.2857(6) 0.4479(12) 0.083(3) Uani 1 1 d . . .
H3 H 0.3418 0.2566 0.4988 0.100 Uiso 1 1 calc R . .
C4 C 0.1451(10) 0.4057(6) 0.4028(8) 0.068(2) Uani 1 1 d . . .
C5 C 0.2390(12) 0.3634(6) 0.4828(10) 0.088(3) Uani 1 1 d . . .
H4 H 0.2760 0.3863 0.5575 0.105 Uiso 1 1 calc R A .
C6 C 0.2205(14) 0.2515(6) 0.3446(12) 0.090(4) Uani 1 1 d . . .
H5 H 0.2507 0.1997 0.3228 0.108 Uiso 1 1 calc R A .
C8 C 0.377(2) 0.5517(14) 0.479(2) 0.089(6) Uiso 0.50 1 d P A -2
H6 H 0.4293 0.5081 0.5187 0.133 Uiso 0.50 1 calc PR A -2
H7 H 0.4214 0.6018 0.5033 0.133 Uiso 0.50 1 calc PR A -2
H8 H 0.3821 0.5459 0.3875 0.133 Uiso 0.50 1 calc PR A -2
C9 C 0.243(2) 0.5506(12) 0.513(2) 0.059(6) Uiso 0.50 1 d P A -2
H9 H 0.2159 0.6066 0.5246 0.070 Uiso 0.50 1 calc PR A -2
H10 H 0.2439 0.5271 0.5980 0.070 Uiso 0.50 1 calc PR A -2
C10 C 0.220(2) 0.5508(11) 0.5537(19) 0.050(5) Uiso 0.50 1 d P A -1
H11 H 0.3033 0.5748 0.5109 0.074 Uiso 0.50 1 calc PR A -1
H12 H 0.2545 0.5094 0.6104 0.074 Uiso 0.50 1 calc PR A -1
H13 H 0.1679 0.5912 0.6020 0.074 Uiso 0.50 1 calc PR A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0799(19) 0.0560(14) 0.0682(15) 0.0144(10) -0.0016(12) 0.0051(11)
P1 0.0707(18) 0.0605(15) 0.0665(16) 0.0037(11) -0.0133(12) -0.0011(11)
C1 0.085(7) 0.079(6) 0.066(6) -0.003(5) -0.015(5) 0.015(5)
C2 0.108(8) 0.056(5) 0.076(6) -0.017(5) 0.003(6) 0.001(6)
C3 0.090(8) 0.054(5) 0.105(8) 0.017(6) 0.021(6) 0.021(5)
C4 0.071(6) 0.066(5) 0.066(5) -0.001(5) 0.005(5) 0.007(5)
C5 0.095(8) 0.080(7) 0.088(7) -0.005(6) -0.029(6) 0.020(6)
C6 0.127(10) 0.051(5) 0.093(8) -0.007(6) 0.026(7) 0.012(6)

_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 1.956(3) . ?
P1 C9 1.76(2) . ?
P1 C4 1.818(10) . ?
P1 C10 1.861(19) . ?
P1 P1 2.208(6) 5_566 ?
C1 C2 1.372(13) . ?
C1 C4 1.417(13) . ?
C2 C6 1.392(16) . ?
C3 C6 1.345(16) . ?
C3 C5 1.411(14) . ?
C4 C5 1.410(13) . ?
C8 C9 1.28(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
C9 P1 C4 106.7(8) . . ?
C9 P1 C10 15.0(8) . . ?
C4 P1 C10 110.4(7) . . ?
C9 P1 S1 110.7(7) . . ?
C4 P1 S1 114.3(3) . . ?
C10 P1 S1 119.5(6) . . ?
C9 P1 P1 111.1(7) . 5_566 ?
C4 P1 P1 102.7(3) . 5_566 ?
C10 P1 P1 96.1(7) . 5_566 ?
S1 P1 P1 111.08(19) . 5_566 ?
C2 C1 C4 121.3(9) . . ?
C6 C2 C1 118.6(10) . . ?
C6 C3 C5 121.9(10) . . ?
C5 C4 C1 119.0(9) . . ?
C5 C4 P1 121.5(7) . . ?
C1 C4 P1 119.4(7) . . ?
C4 C5 C3 117.5(10) . . ?
C3 C6 C2 121.3(9) . . ?
C8 C9 P1 127.9(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
C4 C1 C2 C6 1.4(17) . . . . ?
C2 C1 C4 C5 -5.7(16) . . . . ?
C2 C1 C4 P1 178.6(9) . . . . ?
C9 P1 C4 C5 31.8(12) . . . . ?
C10 P1 C4 C5 16.5(12) . . . . ?
S1 P1 C4 C5 154.6(8) . . . . ?
P1 P1 C4 C5 -85.0(9) 5_566 . . . ?
C9 P1 C4 C1 -152.6(10) . . . . ?
C10 P1 C4 C1 -168.0(9) . . . . ?
S1 P1 C4 C1 -29.9(9) . . . . ?
P1 P1 C4 C1 90.5(8) 5_566 . . . ?
C1 C4 C5 C3 6.0(16) . . . . ?
P1 C4 C5 C3 -178.4(8) . . . . ?
C6 C3 C5 C4 -2.3(17) . . . . ?
C5 C3 C6 C2 -2.1(18) . . . . ?
C1 C2 C6 C3 2.6(17) . . . . ?
C4 P1 C9 C8 52(2) . . . . ?
C10 P1 C9 C8 158(6) . . . . ?
S1 P1 C9 C8 -73(2) . . . . ?
P1 P1 C9 C8 163(2) 5_566 . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.381
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.151
_chemical_absolute_configuration ad
