# 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_151108e
_database_code_depnum_ccdc_archive 'CCDC 1471518'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O2 S'
_chemical_formula_weight         304.35

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1090(6)
_cell_length_b                   7.6441(7)
_cell_length_c                   15.5179(14)
_cell_angle_alpha                98.759(2)
_cell_angle_beta                 99.355(2)
_cell_angle_gamma                96.6270(10)
_cell_volume                     699.34(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    995
_cell_measurement_theta_min      2.702
_cell_measurement_theta_max      23.81

_exptl_crystal_description       ?
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            3535
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2387
_reflns_number_gt                1549
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.2000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2387
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.1030
_refine_ls_wR_factor_ref         0.2914
_refine_ls_wR_factor_gt          0.2690
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
O1 O 1.0486(7) 1.6728(7) 0.8972(3) 0.0827(15) Uani 1 1 d . . .
O2 O 0.0099(6) 0.9587(6) 0.3635(2) 0.0624(11) Uani 1 1 d . . .
S1 S 0.8296(2) 1.49629(19) 0.71612(8) 0.0506(6) Uani 1 1 d . . .
C1 C 0.7395(10) 1.6510(9) 0.9711(4) 0.0713(18) Uani 1 1 d . . .
H1A H 0.7245 1.5419 0.9945 0.107 Uiso 1 1 calc R . .
H1B H 0.5940 1.6847 0.9545 0.107 Uiso 1 1 calc R . .
H1C H 0.8302 1.7439 1.0155 0.107 Uiso 1 1 calc R . .
C2 C 0.8475(9) 1.6242(8) 0.8921(4) 0.0546(14) Uani 1 1 d . . .
C3 C 0.7104(9) 1.5305(7) 0.8084(3) 0.0503(13) Uani 1 1 d . . .
C4 C 0.4906(8) 1.4537(8) 0.7905(3) 0.0532(14) Uani 1 1 d . . .
H4 H 0.3975 1.4575 0.8324 0.064 Uiso 1 1 calc R . .
C5 C 0.4218(8) 1.3691(7) 0.7022(3) 0.0521(14) Uani 1 1 d . . .
H5 H 0.2772 1.3103 0.6796 0.063 Uiso 1 1 calc R . .
C6 C 0.5835(8) 1.3803(7) 0.6526(3) 0.0428(12) Uani 1 1 d . . .
C7 C 0.5713(8) 1.3088(6) 0.5589(3) 0.0426(12) Uani 1 1 d . . .
C8 C 0.3746(8) 1.2048(7) 0.5075(3) 0.0443(12) Uani 1 1 d . . .
H8 H 0.2491 1.1791 0.5326 0.053 Uiso 1 1 calc R . .
C9 C 0.3724(8) 1.1424(7) 0.4196(3) 0.0438(12) Uani 1 1 d . . .
C10 C 0.1924(8) 1.0266(7) 0.3520(3) 0.0489(13) Uani 1 1 d . . .
C11 C 0.2804(8) 1.0056(7) 0.2684(3) 0.0489(13) Uani 1 1 d . . .
C12 C 0.1818(9) 0.9163(8) 0.1845(4) 0.0568(15) Uani 1 1 d . . .
H12 H 0.0360 0.8563 0.1737 0.068 Uiso 1 1 calc R . .
C13 C 0.3026(10) 0.9175(8) 0.1174(4) 0.0637(16) Uani 1 1 d . . .
H13 H 0.2388 0.8572 0.0606 0.076 Uiso 1 1 calc R . .
C14 C 0.5225(10) 1.0094(8) 0.1340(4) 0.0607(15) Uani 1 1 d . . .
H14 H 0.6034 1.0088 0.0881 0.073 Uiso 1 1 calc R . .
C15 C 0.6183(9) 1.0997(7) 0.2171(3) 0.0551(14) Uani 1 1 d . . .
H15 H 0.7626 1.1623 0.2275 0.066 Uiso 1 1 calc R . .
C16 C 0.5002(8) 1.0972(7) 0.2846(3) 0.0456(12) Uani 1 1 d . . .
C17 C 0.5569(8) 1.1812(6) 0.3792(3) 0.0429(12) Uani 1 1 d . . .
C18 C 0.7501(8) 1.2806(7) 0.4286(3) 0.0498(13) Uani 1 1 d . . .
H18 H 0.8750 1.3054 0.4030 0.060 Uiso 1 1 calc R . .
C19 C 0.7551(8) 1.3435(7) 0.5179(3) 0.0499(13) Uani 1 1 d . . .
H19 H 0.8858 1.4111 0.5516 0.060 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
O1 C2 1.228(6) . ?
O2 C10 1.227(6) . ?
S1 C3 1.708(5) . ?
S1 C6 1.721(5) . ?
C1 C2 1.482(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.458(8) . ?
C3 C4 1.368(7) . ?
C4 C5 1.397(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.351(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(7) . ?
C7 C19 1.396(7) . ?
C7 C8 1.409(7) . ?
C8 C9 1.372(7) . ?
C8 H8 0.9300 . ?
C9 C17 1.400(7) . ?
C9 C10 1.487(7) . ?
C10 C11 1.476(8) . ?
C11 C12 1.380(7) . ?
C11 C16 1.406(7) . ?
C12 C13 1.371(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.407(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.478(7) . ?
C17 C18 1.371(7) . ?
C18 C19 1.390(7) . ?
C18 H18 0.9300 . ?
C19 H19 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
C3 S1 C6 92.2(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 120.5(5) . . ?
O1 C2 C1 121.3(5) . . ?
C3 C2 C1 118.2(5) . . ?
C4 C3 C2 129.5(5) . . ?
C4 C3 S1 111.0(4) . . ?
C2 C3 S1 119.4(4) . . ?
C3 C4 C5 112.4(5) . . ?
C3 C4 H4 123.8 . . ?
C5 C4 H4 123.8 . . ?
C6 C5 C4 114.1(5) . . ?
C6 C5 H5 122.9 . . ?
C4 C5 H5 122.9 . . ?
C5 C6 C7 129.0(5) . . ?
C5 C6 S1 110.3(4) . . ?
C7 C6 S1 120.7(4) . . ?
C19 C7 C8 118.4(5) . . ?
C19 C7 C6 120.4(4) . . ?
C8 C7 C6 121.1(4) . . ?
C9 C8 C7 118.6(5) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C17 122.2(4) . . ?
C8 C9 C10 129.6(4) . . ?
C17 C9 C10 108.1(4) . . ?
O2 C10 C11 126.9(5) . . ?
O2 C10 C9 127.1(5) . . ?
C11 C10 C9 106.0(4) . . ?
C12 C11 C16 120.5(5) . . ?
C12 C11 C10 130.6(5) . . ?
C16 C11 C10 108.9(4) . . ?
C13 C12 C11 118.8(5) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 120.4(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.5(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.5(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 120.2(5) . . ?
C15 C16 C17 131.8(5) . . ?
C11 C16 C17 107.9(4) . . ?
C18 C17 C9 119.8(4) . . ?
C18 C17 C16 131.2(5) . . ?
C9 C17 C16 109.0(4) . . ?
C17 C18 C19 118.5(5) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C7 122.4(4) . . ?
C18 C19 H19 118.8 . . ?
C7 C19 H19 118.8 . . ?

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
O1 C2 C3 C4 174.3(6) . . . . ?
C1 C2 C3 C4 -2.9(10) . . . . ?
O1 C2 C3 S1 -2.5(8) . . . . ?
C1 C2 C3 S1 -179.7(4) . . . . ?
C6 S1 C3 C4 0.6(4) . . . . ?
C6 S1 C3 C2 177.9(5) . . . . ?
C2 C3 C4 C5 -177.3(6) . . . . ?
S1 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C4 C5 C6 C7 -179.8(5) . . . . ?
C4 C5 C6 S1 0.6(6) . . . . ?
C3 S1 C6 C5 -0.7(4) . . . . ?
C3 S1 C6 C7 179.8(4) . . . . ?
C5 C6 C7 C19 176.3(5) . . . . ?
S1 C6 C7 C19 -4.2(7) . . . . ?
C5 C6 C7 C8 -3.2(9) . . . . ?
S1 C6 C7 C8 176.3(4) . . . . ?
C19 C7 C8 C9 0.0(8) . . . . ?
C6 C7 C8 C9 179.5(4) . . . . ?
C7 C8 C9 C17 -1.1(8) . . . . ?
C7 C8 C9 C10 177.8(5) . . . . ?
C8 C9 C10 O2 -2.7(10) . . . . ?
C17 C9 C10 O2 176.4(5) . . . . ?
C8 C9 C10 C11 178.9(5) . . . . ?
C17 C9 C10 C11 -2.1(6) . . . . ?
O2 C10 C11 C12 3.6(10) . . . . ?
C9 C10 C11 C12 -178.0(6) . . . . ?
O2 C10 C11 C16 -176.8(5) . . . . ?
C9 C10 C11 C16 1.7(6) . . . . ?
C16 C11 C12 C13 0.5(8) . . . . ?
C10 C11 C12 C13 -179.9(6) . . . . ?
C11 C12 C13 C14 -0.5(9) . . . . ?
C12 C13 C14 C15 -0.4(9) . . . . ?
C13 C14 C15 C16 1.3(9) . . . . ?
C14 C15 C16 C11 -1.3(9) . . . . ?
C14 C15 C16 C17 -179.5(6) . . . . ?
C12 C11 C16 C15 0.4(8) . . . . ?
C10 C11 C16 C15 -179.3(5) . . . . ?
C12 C11 C16 C17 179.0(5) . . . . ?
C10 C11 C16 C17 -0.7(6) . . . . ?
C8 C9 C17 C18 1.8(8) . . . . ?
C10 C9 C17 C18 -177.3(5) . . . . ?
C8 C9 C17 C16 -179.1(5) . . . . ?
C10 C9 C17 C16 1.7(6) . . . . ?
C15 C16 C17 C18 -3.4(10) . . . . ?
C11 C16 C17 C18 178.2(5) . . . . ?
C15 C16 C17 C9 177.7(6) . . . . ?
C11 C16 C17 C9 -0.7(6) . . . . ?
C9 C17 C18 C19 -1.3(8) . . . . ?
C16 C17 C18 C19 180.0(5) . . . . ?
C17 C18 C19 C7 0.1(8) . . . . ?
C8 C7 C19 C18 0.5(8) . . . . ?
C6 C7 C19 C18 -179.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.141
