# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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:\users\admini~1\desktop\ljf~1\ljf\b
_database_code_depnum_ccdc_archive 'CCDC 1409349'
_audit_update_record             
;
2015-06-28 deposited with the CCDC.
2015-08-11 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 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)/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                   8.1040(16)
_cell_length_b                   17.252(4)
_cell_length_c                   9.4860(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.24(3)
_cell_angle_gamma                90.00
_cell_volume                     1273.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9528
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            2339
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1116
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.43
_reflns_number_total             2339
_reflns_number_gt                1522
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0957P)²+1.5482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2339
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0968
_refine_ls_wR_factor_ref         0.2420
_refine_ls_wR_factor_gt          0.2209
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.073
_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
S S 0.4049(2) 0.32036(8) 0.96803(15) 0.0614(5) Uani 1 1 d . . .
C1 C 0.1390(6) 0.3661(3) 0.4766(5) 0.0407(11) Uani 1 1 d . . .
H1A H 0.1241 0.3157 0.5113 0.049 Uiso 1 1 calc R . .
O1 O 0.3452(8) 0.5472(2) 0.6237(4) 0.109(2) Uani 1 1 d . . .
C2 C 0.0789(7) 0.3811(3) 0.3266(5) 0.0498(12) Uani 1 1 d . . .
O2 O 0.4456(8) 0.6634(3) 0.6810(5) 0.110(2) Uani 1 1 d . . .
C3 C 0.1140(8) 0.4534(3) 0.2781(6) 0.0608(15) Uani 1 1 d . . .
H3A H 0.0786 0.4640 0.1757 0.073 Uiso 1 1 calc R . .
C4 C 0.1983(9) 0.5105(3) 0.3723(6) 0.0672(17) Uani 1 1 d . . .
C5 C 0.2566(13) 0.5888(4) 0.3245(7) 0.104(3) Uani 1 1 d U . .
H5 H 0.3712 0.5709 0.3170 0.125 Uiso 1 1 calc R . .
C6 C 0.3144(9) 0.6380(3) 0.4313(6) 0.0705(17) Uani 1 1 d U . .
H6A H 0.2225 0.6771 0.4212 0.085 Uiso 1 1 calc R . .
H6B H 0.4113 0.6652 0.4082 0.085 Uiso 1 1 calc R . .
C7 C 0.3741(8) 0.6194(3) 0.5887(6) 0.0624(15) Uani 1 1 d . . .
C8 C 0.2512(8) 0.4933(3) 0.5207(5) 0.0626(16) Uani 1 1 d . . .
C9 C 0.2197(6) 0.4221(3) 0.5774(5) 0.0454(11) Uani 1 1 d . . .
C10 C -0.0107(9) 0.3204(3) 0.2217(6) 0.0719(17) Uani 1 1 d . . .
H10A H -0.0442 0.3418 0.1220 0.108 Uiso 1 1 calc R . .
H10B H -0.1136 0.3033 0.2479 0.108 Uiso 1 1 calc R . .
H10C H 0.0665 0.2763 0.2259 0.108 Uiso 1 1 calc R . .
C11 C 0.1838(9) 0.6085(3) 0.1684(6) 0.0711(17) Uani 1 1 d . . .
H11A H 0.2341 0.6572 0.1471 0.107 Uiso 1 1 calc R . .
H11B H 0.0590 0.6143 0.1469 0.107 Uiso 1 1 calc R . .
H11C H 0.2100 0.5670 0.1074 0.107 Uiso 1 1 calc R . .
C12 C 0.2864(5) 0.4018(3) 0.7370(5) 0.0373(10) Uani 1 1 d . . .
C13 C 0.2968(7) 0.4504(3) 0.8562(5) 0.0588(14) Uani 1 1 d . . .
H13A H 0.2634 0.5034 0.8456 0.071 Uiso 1 1 calc R . .
C14 C 0.3607(7) 0.4146(3) 0.9929(5) 0.0560(14) Uani 1 1 d . . .
H14A H 0.3769 0.4393 1.0853 0.067 Uiso 1 1 calc R . .
C15 C 0.3421(7) 0.3294(3) 0.7813(6) 0.0521(13) Uani 1 1 d . . .
H15B H 0.3458 0.2882 0.7157 0.062 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
S 0.0820(10) 0.0504(8) 0.0493(8) 0.0140(6) 0.0142(7) 0.0050(7)
C1 0.037(2) 0.040(2) 0.044(3) 0.003(2) 0.010(2) 0.002(2)
O1 0.202(6) 0.057(3) 0.040(2) 0.0130(19) -0.015(3) -0.054(3)
C2 0.053(3) 0.047(3) 0.046(3) -0.001(2) 0.010(2) 0.002(2)
O2 0.182(6) 0.059(3) 0.063(3) 0.004(2) -0.009(3) -0.047(3)
C3 0.089(4) 0.056(3) 0.036(3) 0.004(2) 0.015(3) 0.007(3)
C4 0.097(5) 0.051(3) 0.044(3) 0.011(3) 0.006(3) -0.018(3)
C5 0.154(7) 0.083(5) 0.062(4) 0.014(3) 0.009(4) -0.039(5)
C6 0.084(4) 0.057(3) 0.057(3) 0.010(3) -0.003(3) -0.023(3)
C7 0.076(4) 0.045(3) 0.059(3) 0.008(3) 0.008(3) -0.019(3)
C8 0.094(5) 0.040(3) 0.043(3) 0.002(2) 0.001(3) -0.006(3)
C9 0.055(3) 0.043(3) 0.039(2) 0.004(2) 0.014(2) 0.007(2)
C10 0.095(5) 0.048(3) 0.063(4) -0.013(3) 0.008(3) -0.008(3)
C11 0.101(5) 0.063(3) 0.052(3) 0.016(3) 0.026(3) -0.010(3)
C12 0.029(2) 0.042(2) 0.043(2) 0.010(2) 0.0140(18) -0.0006(19)
C13 0.075(4) 0.048(3) 0.044(3) 0.007(2) 0.001(3) 0.014(3)
C14 0.077(4) 0.049(3) 0.041(3) 0.002(2) 0.015(3) 0.006(3)
C15 0.073(3) 0.036(3) 0.050(3) 0.006(2) 0.022(3) 0.004(2)

_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
S C14 1.696(5) . ?
S C15 1.708(5) . ?
C1 C9 1.387(6) . ?
C1 C2 1.393(6) . ?
C1 H1A 0.9500 . ?
O1 C7 1.326(6) . ?
O1 C8 1.408(6) . ?
C2 C3 1.387(7) . ?
C2 C10 1.486(7) . ?
O2 C7 1.182(6) . ?
C3 C4 1.377(7) . ?
C3 H3A 0.9500 . ?
C4 C8 1.384(7) . ?
C4 C5 1.539(8) . ?
C5 C6 1.304(8) . ?
C5 C11 1.472(8) . ?
C5 H5 1.0000 . ?
C6 C7 1.470(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.393(7) . ?
C9 C12 1.500(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C15 1.356(6) . ?
C12 C13 1.391(7) . ?
C13 C14 1.399(7) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15B 0.9500 . ?

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
C14 S C15 92.5(2) . . ?
C9 C1 C2 122.5(4) . . ?
C9 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C7 O1 C8 123.0(4) . . ?
C3 C2 C1 117.4(4) . . ?
C3 C2 C10 121.2(5) . . ?
C1 C2 C10 121.3(5) . . ?
C4 C3 C2 122.6(5) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C3 C4 C8 117.6(5) . . ?
C3 C4 C5 125.0(5) . . ?
C8 C4 C5 117.0(5) . . ?
C6 C5 C11 125.9(6) . . ?
C6 C5 C4 114.6(6) . . ?
C11 C5 C4 115.4(6) . . ?
C6 C5 H5 96.8 . . ?
C11 C5 H5 96.8 . . ?
C4 C5 H5 96.8 . . ?
C5 C6 C7 126.2(6) . . ?
C5 C6 H6A 105.8 . . ?
C7 C6 H6A 105.8 . . ?
C5 C6 H6B 105.8 . . ?
C7 C6 H6B 105.8 . . ?
H6A C6 H6B 106.2 . . ?
O2 C7 O1 120.1(5) . . ?
O2 C7 C6 124.5(5) . . ?
O1 C7 C6 115.4(5) . . ?
C4 C8 C9 122.9(5) . . ?
C4 C8 O1 121.2(5) . . ?
C9 C8 O1 115.9(4) . . ?
C1 C9 C8 116.8(4) . . ?
C1 C9 C12 120.0(4) . . ?
C8 C9 C12 122.8(4) . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C13 111.4(4) . . ?
C15 C12 C9 121.5(4) . . ?
C13 C12 C9 127.1(4) . . ?
C12 C13 C14 114.2(5) . . ?
C12 C13 H13A 122.9 . . ?
C14 C13 H13A 122.9 . . ?
C13 C14 S 109.4(4) . . ?
C13 C14 H14A 125.3 . . ?
S C14 H14A 125.3 . . ?
C12 C15 S 112.5(4) . . ?
C12 C15 H15B 123.8 . . ?
S C15 H15B 123.8 . . ?

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
C9 C1 C2 C3 4.8(7) . . . . ?
C9 C1 C2 C10 -178.6(5) . . . . ?
C1 C2 C3 C4 -2.7(9) . . . . ?
C10 C2 C3 C4 -179.3(6) . . . . ?
C2 C3 C4 C8 1.1(10) . . . . ?
C2 C3 C4 C5 173.7(7) . . . . ?
C3 C4 C5 C6 171.7(8) . . . . ?
C8 C4 C5 C6 -15.6(12) . . . . ?
C3 C4 C5 C11 13.2(12) . . . . ?
C8 C4 C5 C11 -174.1(7) . . . . ?
C11 C5 C6 C7 174.6(7) . . . . ?
C4 C5 C6 C7 18.7(13) . . . . ?
C8 O1 C7 O2 175.8(7) . . . . ?
C8 O1 C7 C6 -5.3(10) . . . . ?
C5 C6 C7 O2 170.0(9) . . . . ?
C5 C6 C7 O1 -8.9(12) . . . . ?
C3 C4 C8 C9 -1.4(10) . . . . ?
C5 C4 C8 C9 -174.6(7) . . . . ?
C3 C4 C8 O1 177.0(6) . . . . ?
C5 C4 C8 O1 3.8(10) . . . . ?
C7 O1 C8 C4 6.9(11) . . . . ?
C7 O1 C8 C9 -174.6(6) . . . . ?
C2 C1 C9 C8 -5.0(7) . . . . ?
C2 C1 C9 C12 -178.1(4) . . . . ?
C4 C8 C9 C1 3.3(9) . . . . ?
O1 C8 C9 C1 -175.2(5) . . . . ?
C4 C8 C9 C12 176.1(6) . . . . ?
O1 C8 C9 C12 -2.3(8) . . . . ?
C1 C9 C12 C15 30.1(7) . . . . ?
C8 C9 C12 C15 -142.5(6) . . . . ?
C1 C9 C12 C13 -148.3(5) . . . . ?
C8 C9 C12 C13 39.1(8) . . . . ?
C15 C12 C13 C14 -0.1(7) . . . . ?
C9 C12 C13 C14 178.4(5) . . . . ?
C12 C13 C14 S -0.4(6) . . . . ?
C15 S C14 C13 0.6(5) . . . . ?
C13 C12 C15 S 0.6(6) . . . . ?
C9 C12 C15 S -178.0(3) . . . . ?
C14 S C15 C12 -0.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.068
