# 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_mo_2015637_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1m8tzp
_database_code_depnum_ccdc_archive 'CCDC 1498043'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-12-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H6 O2 S'
_chemical_formula_sum            'C11 H6 O2 S'
_chemical_formula_weight         202.22
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.1145(11)
_cell_length_b                   8.2023(8)
_cell_length_c                   18.5724(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.188(5)
_cell_angle_gamma                90
_cell_volume                     1772.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2169
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0575 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.8817.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5234
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.590
_diffrn_reflns_theta_min         2.284
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1603
_reflns_number_total             2023
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.5721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C10(H10), C9(H9), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20097(3) 0.75403(6) 0.70643(2) 0.03373(15) Uani 1 1 d . . . . .
O1 O 0.25617(9) 0.46890(15) 0.54567(6) 0.0335(3) Uani 1 1 d . . . . .
O2 O 0.34374(10) 0.46535(18) 0.66706(6) 0.0484(4) Uani 1 1 d . . . . .
C1 C 0.08843(13) 0.8762(2) 0.66229(9) 0.0349(4) Uani 1 1 d . . . . .
H1 H 0.0565 0.9563 0.6876 0.042 Uiso 1 1 calc R . . . .
C2 C 0.04897(13) 0.8477(2) 0.58739(9) 0.0313(4) Uani 1 1 d . . . . .
H2 H -0.0135 0.9045 0.5548 0.038 Uiso 1 1 calc R . . . .
C3 C 0.11196(12) 0.72321(19) 0.56373(8) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.09854(12) 0.65358(19) 0.49001(8) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.17244(12) 0.5278(2) 0.48395(8) 0.0265(3) Uani 1 1 d . . . . .
C11 C 0.16652(15) 0.4520(2) 0.41655(9) 0.0336(4) Uani 1 1 d . . . . .
H11 H 0.2179 0.3661 0.4139 0.040 Uiso 1 1 calc R . . . .
C10 C 0.08431(15) 0.5037(2) 0.35308(9) 0.0371(4) Uani 1 1 d . . . . .
H10 H 0.0790 0.4531 0.3062 0.044 Uiso 1 1 calc R . . . .
C4 C 0.19745(12) 0.6612(2) 0.62294(8) 0.0273(3) Uani 1 1 d . . . . .
C5 C 0.27103(13) 0.5293(2) 0.61675(8) 0.0323(4) Uani 1 1 d . . . . .
C9 C 0.00974(14) 0.6285(2) 0.35711(9) 0.0364(4) Uani 1 1 d . . . . .
H9 H -0.0462 0.6633 0.3130 0.044 Uiso 1 1 calc R . . . .
C8 C 0.01591(14) 0.7031(2) 0.42490(8) 0.0302(4) Uani 1 1 d . . . . .
H8 H -0.0362 0.7882 0.4272 0.036 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
S1 0.0325(2) 0.0447(3) 0.0235(2) -0.00152(17) 0.00690(15) -0.0007(2)
O1 0.0369(6) 0.0338(7) 0.0297(6) 0.0058(5) 0.0094(5) 0.0139(5)
O2 0.0445(7) 0.0656(10) 0.0338(6) 0.0159(6) 0.0086(5) 0.0250(7)
C1 0.0345(8) 0.0378(10) 0.0342(8) -0.0066(7) 0.0126(7) 0.0006(8)
C2 0.0301(8) 0.0315(10) 0.0312(8) -0.0009(7) 0.0065(6) 0.0037(7)
C3 0.0245(7) 0.0219(8) 0.0270(7) 0.0005(6) 0.0081(6) -0.0014(6)
C7 0.0278(7) 0.0215(8) 0.0255(7) 0.0018(6) 0.0085(6) -0.0021(7)
C6 0.0289(7) 0.0236(8) 0.0275(7) 0.0058(6) 0.0087(6) 0.0002(7)
C11 0.0413(9) 0.0265(9) 0.0366(8) -0.0025(7) 0.0170(7) 0.0022(8)
C10 0.0465(9) 0.0374(10) 0.0276(8) -0.0063(7) 0.0109(7) -0.0063(9)
C4 0.0273(7) 0.0309(9) 0.0245(7) 0.0031(6) 0.0084(6) 0.0005(7)
C5 0.0316(8) 0.0377(10) 0.0285(8) 0.0077(7) 0.0097(6) 0.0038(8)
C9 0.0400(9) 0.0391(10) 0.0266(8) 0.0010(7) 0.0034(7) -0.0007(9)
C8 0.0316(8) 0.0270(9) 0.0298(8) 0.0026(7) 0.0047(6) 0.0026(7)

_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 C1 1.7067(18) . ?
S1 C4 1.7173(15) . ?
O1 C6 1.3885(17) . ?
O1 C5 1.3741(19) . ?
O2 C5 1.2105(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.359(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.416(2) . ?
C3 C7 1.450(2) . ?
C3 C4 1.381(2) . ?
C7 C6 1.391(2) . ?
C7 C8 1.398(2) . ?
C6 C11 1.382(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.381(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.381(3) . ?
C4 C5 1.426(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.383(2) . ?
C8 H8 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
C1 S1 C4 90.65(8) . . ?
C5 O1 C6 122.52(12) . . ?
S1 C1 H1 123.3 . . ?
C2 C1 S1 113.34(13) . . ?
C2 C1 H1 123.3 . . ?
C1 C2 H2 124.0 . . ?
C1 C2 C3 112.08(14) . . ?
C3 C2 H2 124.0 . . ?
C2 C3 C7 130.45(14) . . ?
C4 C3 C2 111.59(13) . . ?
C4 C3 C7 117.95(14) . . ?
C6 C7 C3 117.60(13) . . ?
C6 C7 C8 117.85(14) . . ?
C8 C7 C3 124.55(14) . . ?
O1 C6 C7 121.98(13) . . ?
C11 C6 O1 115.66(14) . . ?
C11 C6 C7 122.35(14) . . ?
C6 C11 H11 120.7 . . ?
C10 C11 C6 118.56(16) . . ?
C10 C11 H11 120.7 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.57(15) . . ?
C9 C10 H10 119.7 . . ?
C3 C4 S1 112.34(12) . . ?
C3 C4 C5 124.20(14) . . ?
C5 C4 S1 123.39(11) . . ?
O1 C5 C4 115.69(13) . . ?
O2 C5 O1 117.22(15) . . ?
O2 C5 C4 127.08(16) . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.47(15) . . ?
C8 C9 H9 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.20(15) . . ?
C9 C8 H8 119.9 . . ?

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
S1 C1 C2 C3 -0.51(19) . . . . ?
S1 C4 C5 O1 179.65(11) . . . . ?
S1 C4 C5 O2 0.2(3) . . . . ?
O1 C6 C11 C10 179.39(14) . . . . ?
C1 S1 C4 C3 -0.13(13) . . . . ?
C1 S1 C4 C5 -177.14(15) . . . . ?
C1 C2 C3 C7 179.23(15) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C7 C6 -178.36(15) . . . . ?
C2 C3 C7 C8 1.0(3) . . . . ?
C2 C3 C4 S1 -0.12(17) . . . . ?
C2 C3 C4 C5 176.85(15) . . . . ?
C3 C7 C6 O1 0.3(2) . . . . ?
C3 C7 C6 C11 179.47(14) . . . . ?
C3 C7 C8 C9 -179.76(14) . . . . ?
C3 C4 C5 O1 3.0(2) . . . . ?
C3 C4 C5 O2 -176.49(16) . . . . ?
C7 C3 C4 S1 -179.12(11) . . . . ?
C7 C3 C4 C5 -2.1(2) . . . . ?
C7 C6 C11 C10 0.2(2) . . . . ?
C6 O1 C5 O2 177.35(14) . . . . ?
C6 O1 C5 C4 -2.2(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C6 C11 C10 C9 -0.1(3) . . . . ?
C11 C10 C9 C8 -0.3(3) . . . . ?
C10 C9 C8 C7 0.5(3) . . . . ?
C4 S1 C1 C2 0.37(14) . . . . ?
C4 C3 C7 C6 0.4(2) . . . . ?
C4 C3 C7 C8 179.79(14) . . . . ?
C5 O1 C6 C7 0.7(2) . . . . ?
C5 O1 C6 C11 -178.55(14) . . . . ?
C8 C7 C6 O1 -179.12(13) . . . . ?
C8 C7 C6 C11 0.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
