# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1485881'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            PYP
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O2 S'
_chemical_formula_weight         256.31

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'
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)/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                   16.6972(12)
_cell_length_b                   7.7291(5)
_cell_length_c                   20.8746(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.503(2)
_cell_angle_gamma                90.00
_cell_volume                     2664.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  '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            17247
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.48
_reflns_number_total             4941
_reflns_number_gt                3584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0469P)²+0.7742P] 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         4941
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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 0.32597(4) 0.58358(8) 1.04406(3) 0.0775(2) Uani 1 1 d . . .
S2 S -0.09117(3) 0.31799(8) 0.04274(2) 0.06323(17) Uani 1 1 d . . .
O1 O 0.45020(8) 0.80132(18) 1.05361(7) 0.0629(4) Uani 1 1 d . . .
O2 O 0.52490(11) 0.7164(2) 0.66286(7) 0.0777(5) Uani 1 1 d . . .
H2 H 0.5152 0.6199 0.6473 0.116 Uiso 1 1 calc R . .
O3 O 0.00963(10) 0.1088(2) 0.11361(7) 0.0770(5) Uani 1 1 d . . .
O4 O 0.38653(9) 0.2356(2) -0.11178(7) 0.0696(4) Uani 1 1 d . . .
H4 H 0.4300 0.2088 -0.0904 0.104 Uiso 1 1 calc R . .
C1 C 0.40745(13) 0.6999(3) 1.01920(10) 0.0562(5) Uani 1 1 d . . .
C2 C 0.41514(13) 0.6627(3) 0.95158(10) 0.0610(5) Uani 1 1 d . . .
H2A H 0.3867 0.5699 0.9309 0.073 Uiso 1 1 calc R . .
C3 C 0.46154(12) 0.7577(3) 0.91910(10) 0.0578(5) Uani 1 1 d . . .
H3 H 0.4897 0.8466 0.9425 0.069 Uiso 1 1 calc R . .
C4 C 0.47468(11) 0.7426(3) 0.85172(9) 0.0537(5) Uani 1 1 d . . .
C5 C 0.43497(12) 0.6221(3) 0.80829(10) 0.0568(5) Uani 1 1 d . . .
H5 H 0.3973 0.5476 0.8221 0.068 Uiso 1 1 calc R . .
C6 C 0.45038(12) 0.6113(3) 0.74558(10) 0.0587(5) Uani 1 1 d . . .
H6 H 0.4229 0.5310 0.7173 0.070 Uiso 1 1 calc R . .
C7 C 0.50695(13) 0.7201(3) 0.72472(10) 0.0567(5) Uani 1 1 d . . .
C8 C 0.54659(14) 0.8416(3) 0.76662(11) 0.0649(6) Uani 1 1 d . . .
H8 H 0.5843 0.9156 0.7526 0.078 Uiso 1 1 calc R . .
C9 C 0.53008(13) 0.8528(3) 0.82899(10) 0.0623(5) Uani 1 1 d . . .
H9 H 0.5565 0.9359 0.8566 0.075 Uiso 1 1 calc R . .
C10 C 0.32016(14) 0.6623(3) 1.12269(10) 0.0608(5) Uani 1 1 d . . .
C11 C 0.24764(15) 0.7325(3) 1.13467(14) 0.0826(7) Uani 1 1 d . . .
H11 H 0.2042 0.7416 1.1014 0.099 Uiso 1 1 calc R . .
C12 C 0.2398(2) 0.7891(4) 1.19631(17) 0.1007(9) Uani 1 1 d . . .
H12 H 0.1913 0.8375 1.2043 0.121 Uiso 1 1 calc R . .
C13 C 0.3028(2) 0.7744(4) 1.24520(15) 0.0974(9) Uani 1 1 d . . .
H13 H 0.2972 0.8126 1.2866 0.117 Uiso 1 1 calc R . .
C14 C 0.3747(2) 0.7032(4) 1.23374(13) 0.0921(8) Uani 1 1 d . . .
H14 H 0.4176 0.6929 1.2675 0.111 Uiso 1 1 calc R . .
C15 C 0.38372(16) 0.6471(3) 1.17268(11) 0.0757(7) Uani 1 1 d . . .
H15 H 0.4325 0.5990 1.1651 0.091 Uiso 1 1 calc R . .
C16 C -0.00194(12) 0.1951(3) 0.06456(9) 0.0541(5) Uani 1 1 d . . .
C17 C 0.05548(12) 0.2142(3) 0.01873(9) 0.0561(5) Uani 1 1 d . . .
H17 H 0.0391 0.2690 -0.0207 0.067 Uiso 1 1 calc R . .
C18 C 0.13096(12) 0.1546(3) 0.03229(9) 0.0562(5) Uani 1 1 d . . .
H18 H 0.1431 0.0930 0.0708 0.067 Uiso 1 1 calc R . .
C19 C 0.19658(12) 0.1738(2) -0.00557(9) 0.0510(5) Uani 1 1 d . . .
C20 C 0.18662(12) 0.2571(3) -0.06575(9) 0.0551(5) Uani 1 1 d . . .
H20 H 0.1358 0.2992 -0.0830 0.066 Uiso 1 1 calc R . .
C21 C 0.25011(12) 0.2779(3) -0.09977(10) 0.0571(5) Uani 1 1 d . . .
H21 H 0.2424 0.3359 -0.1392 0.068 Uiso 1 1 calc R . .
C22 C 0.32590(12) 0.2123(2) -0.07535(10) 0.0539(5) Uani 1 1 d . . .
C23 C 0.33702(12) 0.1278(2) -0.01654(10) 0.0556(5) Uani 1 1 d . . .
H23 H 0.3875 0.0825 -0.0002 0.067 Uiso 1 1 calc R . .
C24 C 0.27349(12) 0.1107(3) 0.01777(10) 0.0573(5) Uani 1 1 d . . .
H24 H 0.2820 0.0554 0.0578 0.069 Uiso 1 1 calc R . .
C25 C -0.13686(12) 0.2980(2) 0.11370(9) 0.0501(5) Uani 1 1 d . . .
C26 C -0.20754(12) 0.2056(3) 0.11241(10) 0.0589(5) Uani 1 1 d . . .
H26 H -0.2306 0.1495 0.0747 0.071 Uiso 1 1 calc R . .
C27 C -0.24375(14) 0.1969(3) 0.16723(12) 0.0731(6) Uani 1 1 d . . .
H27 H -0.2916 0.1349 0.1667 0.088 Uiso 1 1 calc R . .
C28 C -0.20936(16) 0.2797(4) 0.22296(12) 0.0818(7) Uani 1 1 d . . .
H28 H -0.2343 0.2741 0.2599 0.098 Uiso 1 1 calc R . .
C29 C -0.13908(16) 0.3699(4) 0.22441(11) 0.0800(7) Uani 1 1 d . . .
H29 H -0.1159 0.4243 0.2624 0.096 Uiso 1 1 calc R . .
C30 C -0.10238(13) 0.3806(3) 0.16991(10) 0.0637(5) Uani 1 1 d . . .
H30 H -0.0546 0.4430 0.1707 0.076 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.766(2) . ?
S1 C1 1.771(2) . ?
S2 C16 1.769(2) . ?
S2 C25 1.7704(18) . ?
O1 C1 1.220(2) . ?
O2 C7 1.368(2) . ?
O2 H2 0.8200 . ?
O3 C16 1.213(2) . ?
O4 C22 1.365(2) . ?
O4 H4 0.8200 . ?
C1 C2 1.465(3) . ?
C2 C3 1.325(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.460(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.391(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.379(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.357(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.459(3) . ?
C17 C18 1.332(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.450(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.393(3) . ?
C19 C20 1.399(3) . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(3) . ?
C23 C24 1.371(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.376(3) . ?
C25 C30 1.384(3) . ?
C26 C27 1.373(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.361(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(3) . ?
C29 H29 0.9300 . ?
C30 H30 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
C10 S1 C1 104.33(10) . . ?
C16 S2 C25 100.86(9) . . ?
C7 O2 H2 109.5 . . ?
C22 O4 H4 109.5 . . ?
O1 C1 C2 124.5(2) . . ?
O1 C1 S1 124.16(16) . . ?
C2 C1 S1 111.30(15) . . ?
C3 C2 C1 121.71(19) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C2 C3 C4 129.2(2) . . ?
C2 C3 H3 115.4 . . ?
C4 C3 H3 115.4 . . ?
C9 C4 C5 117.54(18) . . ?
C9 C4 C3 118.82(18) . . ?
C5 C4 C3 123.63(19) . . ?
C6 C5 C4 121.43(19) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.74(19) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
O2 C7 C6 122.69(18) . . ?
O2 C7 C8 117.34(19) . . ?
C6 C7 C8 119.95(19) . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 121.45(19) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C15 C10 C11 119.5(2) . . ?
C15 C10 S1 122.14(18) . . ?
C11 C10 S1 118.23(19) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
O3 C16 C17 124.83(19) . . ?
O3 C16 S2 122.38(15) . . ?
C17 C16 S2 112.77(14) . . ?
C18 C17 C16 121.23(18) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 128.01(18) . . ?
C17 C18 H18 116.0 . . ?
C19 C18 H18 116.0 . . ?
C24 C19 C20 117.14(18) . . ?
C24 C19 C18 120.35(18) . . ?
C20 C19 C18 122.50(18) . . ?
C21 C20 C19 121.40(19) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 120.01(19) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
O4 C22 C23 123.03(19) . . ?
O4 C22 C21 117.27(18) . . ?
C23 C22 C21 119.69(18) . . ?
C24 C23 C22 119.86(19) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C19 121.88(19) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?
C26 C25 C30 120.26(18) . . ?
C26 C25 S2 120.21(15) . . ?
C30 C25 S2 119.50(16) . . ?
C27 C26 C25 119.4(2) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 120.1(2) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.1(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 119.6(2) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.034
_exptl_crystal_recrystallization_method 'liquid-liquid diffussion'
_exptl_crystal_preparation       ', C=C photodimerization'
