# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1513070'
_audit_update_record             
;
2016-10-30 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 O P S'
_chemical_formula_weight         360.39

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   10.8152(5)
_cell_length_b                   8.5569(3)
_cell_length_c                   20.0431(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.275(4)
_cell_angle_gamma                90.00
_cell_volume                     1847.02(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2439
_cell_measurement_theta_min      3.1590
_cell_measurement_theta_max      28.0990

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_T_max  0.9483
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6978
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3241
_reflns_number_gt                2538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)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         3241
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
P1 P 0.71268(6) 0.32909(6) 0.16343(3) 0.0451(2) Uani 1 1 d . . .
S1 S 0.56372(6) 0.38688(8) 0.21862(3) 0.0600(2) Uani 1 1 d . . .
C1 C 0.4355(2) 0.3727(2) 0.15650(11) 0.0466(5) Uani 1 1 d . . .
C17 C 0.8316(2) 0.3023(2) 0.23148(10) 0.0459(5) Uani 1 1 d . . .
C11 C 0.6758(2) 0.1431(2) 0.12522(10) 0.0430(5) Uani 1 1 d . . .
C10 C 0.3447(2) 0.2657(3) 0.16512(10) 0.0476(5) Uani 1 1 d . . .
H10A H 0.3534 0.1986 0.2018 0.057 Uiso 1 1 calc R . .
C9 C 0.2381(2) 0.2552(2) 0.11928(10) 0.0449(5) Uani 1 1 d . . .
C4 C 0.2275(2) 0.3566(2) 0.06331(11) 0.0486(6) Uani 1 1 d . . .
C2 C 0.4245(2) 0.4730(3) 0.10082(12) 0.0593(6) Uani 1 1 d . . .
H2A H 0.4865 0.5457 0.0950 0.071 Uiso 1 1 calc R . .
C3 C 0.3238(3) 0.4640(3) 0.05556(12) 0.0605(7) Uani 1 1 d . . .
H3A H 0.3181 0.5302 0.0186 0.073 Uiso 1 1 calc R . .
C8 C 0.1430(2) 0.1442(3) 0.12616(13) 0.0610(7) Uani 1 1 d . . .
H8A H 0.1495 0.0758 0.1624 0.073 Uiso 1 1 calc R . .
C22 C 0.9483(2) 0.3602(3) 0.22297(13) 0.0588(6) Uani 1 1 d . . .
H22A H 0.9619 0.4125 0.1837 0.071 Uiso 1 1 calc R . .
C5 C 0.1209(3) 0.3458(3) 0.01724(13) 0.0649(7) Uani 1 1 d . . .
H5A H 0.1119 0.4129 -0.0194 0.078 Uiso 1 1 calc R . .
C7 C 0.0422(3) 0.1364(3) 0.08043(14) 0.0686(7) Uani 1 1 d . . .
H7A H -0.0196 0.0630 0.0856 0.082 Uiso 1 1 calc R . .
C18 C 0.8135(2) 0.2244(3) 0.29079(11) 0.0599(6) Uani 1 1 d . . .
H18A H 0.7356 0.1846 0.2976 0.072 Uiso 1 1 calc R . .
C21 C 1.0447(3) 0.3410(3) 0.27217(14) 0.0715(8) Uani 1 1 d . . .
H21A H 1.1229 0.3802 0.2657 0.086 Uiso 1 1 calc R . .
C12 C 0.6917(3) 0.1236(3) 0.05830(12) 0.0639(7) Uani 1 1 d . . .
H12A H 0.7178 0.2070 0.0334 0.077 Uiso 1 1 calc R . .
C16 C 0.6391(2) 0.0155(3) 0.16067(12) 0.0669(7) Uani 1 1 d . . .
H16A H 0.6284 0.0267 0.2059 0.080 Uiso 1 1 calc R . .
C6 C 0.0312(3) 0.2379(4) 0.02596(13) 0.0725(8) Uani 1 1 d . . .
H6A H -0.0384 0.2320 -0.0049 0.087 Uiso 1 1 calc R . .
C14 C 0.6323(3) -0.1433(3) 0.06403(16) 0.0801(9) Uani 1 1 d . . .
H14A H 0.6171 -0.2394 0.0432 0.096 Uiso 1 1 calc R . .
C19 C 0.9111(3) 0.2064(3) 0.33942(13) 0.0710(8) Uani 1 1 d . . .
H19A H 0.8988 0.1539 0.3789 0.085 Uiso 1 1 calc R . .
C15 C 0.6178(3) -0.1269(3) 0.13068(15) 0.0805(9) Uani 1 1 d . . .
H15A H 0.5938 -0.2118 0.1554 0.097 Uiso 1 1 calc R . .
C13 C 0.6687(3) -0.0203(4) 0.02823(14) 0.0837(9) Uani 1 1 d . . .
H13A H 0.6784 -0.0326 -0.0171 0.100 Uiso 1 1 calc R . .
C20 C 1.0262(3) 0.2654(3) 0.33002(14) 0.0722(7) Uani 1 1 d . . .
H20A H 1.0915 0.2535 0.3632 0.087 Uiso 1 1 calc R . .
O1 O 0.74487(16) 0.44583(18) 0.11379(8) 0.0617(5) 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
P1 O1 1.4740(15) . ?
P1 C11 1.795(2) . ?
P1 C17 1.801(2) . ?
P1 S1 2.0956(8) . ?
S1 C1 1.781(2) . ?
C1 C2 1.404(3) . ?
C1 C10 1.365(3) . ?
C17 C18 1.392(3) . ?
C17 C22 1.381(3) . ?
C11 C12 1.378(3) . ?
C11 C16 1.381(3) . ?
C10 C9 1.410(3) . ?
C10 H10A 0.9300 . ?
C9 C8 1.417(3) . ?
C9 C4 1.414(3) . ?
C4 C3 1.408(3) . ?
C4 C5 1.412(3) . ?
C2 C3 1.354(3) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C8 C7 1.359(3) . ?
C8 H8A 0.9300 . ?
C22 C21 1.377(3) . ?
C22 H22A 0.9300 . ?
C5 C6 1.362(4) . ?
C5 H5A 0.9300 . ?
C7 C6 1.392(4) . ?
C7 H7A 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18A 0.9300 . ?
C21 C20 1.359(4) . ?
C21 H21A 0.9300 . ?
C12 C13 1.383(4) . ?
C12 H12A 0.9300 . ?
C16 C15 1.369(3) . ?
C16 H16A 0.9300 . ?
C6 H6A 0.9300 . ?
C14 C13 1.353(4) . ?
C14 C15 1.367(4) . ?
C14 H14A 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H19A 0.9300 . ?
C15 H15A 0.9300 . ?
C13 H13A 0.9300 . ?
C20 H20A 0.9300 . ?

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
O1 P1 C11 111.71(9) . . ?
O1 P1 C17 113.64(10) . . ?
C11 P1 C17 108.98(10) . . ?
O1 P1 S1 115.92(8) . . ?
C11 P1 S1 106.45(7) . . ?
C17 P1 S1 99.22(7) . . ?
C1 S1 P1 101.65(7) . . ?
C2 C1 C10 120.1(2) . . ?
C2 C1 S1 121.19(18) . . ?
C10 C1 S1 118.68(17) . . ?
C18 C17 C22 118.6(2) . . ?
C18 C17 P1 124.13(18) . . ?
C22 C17 P1 117.26(17) . . ?
C12 C11 C16 118.2(2) . . ?
C12 C11 P1 118.68(17) . . ?
C16 C11 P1 122.98(16) . . ?
C9 C10 C1 120.97(19) . . ?
C9 C10 H10A 119.5 . . ?
C1 C10 H10A 119.5 . . ?
C8 C9 C10 122.49(19) . . ?
C8 C9 C4 118.8(2) . . ?
C10 C9 C4 118.67(19) . . ?
C3 C4 C5 122.5(2) . . ?
C3 C4 C9 118.8(2) . . ?
C5 C4 C9 118.7(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22A 119.7 . . ?
C17 C22 H22A 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C15 C16 C11 121.5(2) . . ?
C15 C16 H16A 119.3 . . ?
C11 C16 H16A 119.3 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040
