# Electronic Supplementary Material (ESI) for Green 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_x
_database_code_depnum_ccdc_archive 'CCDC 1437629'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '(Z)-Diphenyl(styryl)phosphine sulfide'
_chemical_name_common            ?
_chemical_melting_point          '377.0--378.0 '
_chemical_formula_moiety         'C20 H17 P S'
_chemical_formula_sum            'C20 H17 P S'
_chemical_formula_weight         320.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n'

loop_
_symmetry_equiv_pos_as_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                   14.697(3)
_cell_length_b                   6.6112(11)
_cell_length_c                   17.826(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.960(4)
_cell_angle_gamma                90.00
_cell_volume                     1719.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(1)
_cell_measurement_reflns_used    3190
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      23.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8468
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(1)
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13993
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3025
_reflns_number_gt                2399
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART V5.625'
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0544P)²+0.3423P] 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         3025
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.37793(3) 0.25219(8) 0.18031(3) 0.04313(17) Uani 1 1 d . . .
S1 S 0.38131(4) -0.03387(9) 0.20907(4) 0.0615(2) Uani 1 1 d . . .
C1 C 0.36745(14) 0.4196(3) 0.25780(11) 0.0485(5) Uani 1 1 d . . .
H1 H 0.3074 0.4519 0.2645 0.058 Uiso 1 1 calc R . .
C2 C 0.43027(15) 0.5057(3) 0.30736(12) 0.0530(5) Uani 1 1 d . . .
H2 H 0.4074 0.5895 0.3426 0.064 Uiso 1 1 calc R . .
C3 C 0.53075(14) 0.4883(3) 0.31497(11) 0.0514(5) Uani 1 1 d . . .
C4 C 0.57499(15) 0.3085(4) 0.30337(12) 0.0586(6) Uani 1 1 d . . .
H4 H 0.5409 0.1918 0.2916 0.070 Uiso 1 1 calc R . .
C5 C 0.66992(18) 0.3010(5) 0.30917(14) 0.0746(7) Uani 1 1 d . . .
H5 H 0.6993 0.1792 0.3017 0.090 Uiso 1 1 calc R . .
C6 C 0.72012(19) 0.4717(5) 0.32574(16) 0.0860(9) Uani 1 1 d . . .
H6 H 0.7836 0.4671 0.3281 0.103 Uiso 1 1 calc R . .
C7 C 0.6778(2) 0.6490(5) 0.33889(17) 0.0913(9) Uani 1 1 d . . .
H7 H 0.7125 0.7646 0.3510 0.110 Uiso 1 1 calc R . .
C8 C 0.58334(18) 0.6578(4) 0.33431(14) 0.0730(7) Uani 1 1 d . . .
H8 H 0.5549 0.7788 0.3443 0.088 Uiso 1 1 calc R . .
C9 C 0.27793(13) 0.3142(3) 0.11357(11) 0.0463(5) Uani 1 1 d . . .
C10 C 0.23962(15) 0.5055(4) 0.11004(13) 0.0603(6) Uani 1 1 d . . .
H10 H 0.2641 0.6056 0.1432 0.072 Uiso 1 1 calc R . .
C11 C 0.16474(17) 0.5485(5) 0.05716(15) 0.0771(8) Uani 1 1 d . . .
H11 H 0.1388 0.6769 0.0552 0.092 Uiso 1 1 calc R . .
C12 C 0.12908(17) 0.4016(5) 0.00780(14) 0.0795(8) Uani 1 1 d . . .
H12 H 0.0793 0.4310 -0.0279 0.095 Uiso 1 1 calc R . .
C13 C 0.16639(18) 0.2126(5) 0.01088(14) 0.0768(8) Uani 1 1 d . . .
H13 H 0.1419 0.1134 -0.0226 0.092 Uiso 1 1 calc R . .
C14 C 0.24066(15) 0.1678(4) 0.06377(12) 0.0601(6) Uani 1 1 d . . .
H14 H 0.2656 0.0383 0.0658 0.072 Uiso 1 1 calc R . .
C15 C 0.47473(12) 0.3270(3) 0.13250(10) 0.0417(4) Uani 1 1 d . . .
C16 C 0.50200(14) 0.5268(3) 0.12915(12) 0.0517(5) Uani 1 1 d . . .
H16 H 0.4710 0.6271 0.1524 0.062 Uiso 1 1 calc R . .
C17 C 0.57515(15) 0.5769(4) 0.09126(13) 0.0629(6) Uani 1 1 d . . .
H17 H 0.5938 0.7111 0.0897 0.076 Uiso 1 1 calc R . .
C18 C 0.62046(15) 0.4323(4) 0.05604(14) 0.0675(7) Uani 1 1 d . . .
H18 H 0.6702 0.4676 0.0311 0.081 Uiso 1 1 calc R . .
C19 C 0.59264(16) 0.2341(4) 0.05745(14) 0.0692(7) Uani 1 1 d . . .
H19 H 0.6224 0.1359 0.0321 0.083 Uiso 1 1 calc R . .
C20 C 0.52062(14) 0.1803(4) 0.09634(12) 0.0560(5) Uani 1 1 d . . .
H20 H 0.5029 0.0456 0.0983 0.067 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.791(2) . ?
P1 C15 1.8135(19) . ?
P1 C9 1.822(2) . ?
P1 S1 1.9585(8) . ?
C1 C2 1.326(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.471(3) . ?
C2 H2 0.9300 . ?
C3 C8 1.381(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.381(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.384(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20 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
C1 P1 C15 109.85(9) . . ?
C1 P1 C9 103.10(9) . . ?
C15 P1 C9 104.38(9) . . ?
C1 P1 S1 113.37(7) . . ?
C15 P1 S1 112.95(7) . . ?
C9 P1 S1 112.40(7) . . ?
C2 C1 P1 131.37(16) . . ?
C2 C1 H1 114.3 . . ?
P1 C1 H1 114.3 . . ?
C1 C2 C3 129.63(19) . . ?
C1 C2 H2 115.2 . . ?
C3 C2 H2 115.2 . . ?
C8 C3 C4 118.4(2) . . ?
C8 C3 C2 119.0(2) . . ?
C4 C3 C2 122.6(2) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.6(3) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C14 C9 C10 119.0(2) . . ?
C14 C9 P1 119.21(17) . . ?
C10 C9 P1 121.82(16) . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.4(2) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C20 C15 C16 119.25(19) . . ?
C20 C15 P1 118.82(16) . . ?
C16 C15 P1 121.90(15) . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane-ethyl acetate'
