# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1821829'
_audit_update_record             
;
2018-02-04 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O2 S'
_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_weight         269.31

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'
N N 0.0061 0.0033 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   14.1337(16)
_cell_length_b                   10.2364(11)
_cell_length_c                   8.8680(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.306(2)
_cell_angle_gamma                90.00
_cell_volume                     1272.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8723
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.28

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9044
_exptl_absorpt_correction_T_max  0.9287
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      100(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  
'Bruker AXS APEX Duo area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8799
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2500
_reflns_number_gt                2383
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0536P)²+0.5636P] 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         2500
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_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 0.76574(2) 1.03577(3) 1.04385(4) 0.02013(13) Uani 1 1 d . . .
O1 O 0.67170(7) 1.04391(9) 0.59531(12) 0.0237(2) Uani 1 1 d . . .
O2 O 0.81372(7) 0.71590(9) 0.89546(11) 0.0226(2) Uani 1 1 d . . .
N1 N 0.76354(8) 0.89987(11) 0.75426(12) 0.0155(2) Uani 1 1 d . . .
C1 C 0.65821(9) 0.72690(13) 0.74092(14) 0.0158(3) Uani 1 1 d . . .
C2 C 0.61310(10) 0.60816(13) 0.75482(15) 0.0203(3) Uani 1 1 d . . .
H2 H 0.6424 0.5411 0.8143 0.024 Uiso 1 1 calc R . .
C3 C 0.52201(10) 0.59346(14) 0.67586(16) 0.0240(3) Uani 1 1 d . . .
H3 H 0.4902 0.5144 0.6814 0.029 Uiso 1 1 calc R . .
C4 C 0.47748(10) 0.69449(15) 0.58880(16) 0.0244(3) Uani 1 1 d . . .
H4 H 0.4161 0.6824 0.5392 0.029 Uiso 1 1 calc R . .
C5 C 0.52353(9) 0.81330(14) 0.57497(15) 0.0212(3) Uani 1 1 d . . .
H5 H 0.4943 0.8810 0.5165 0.025 Uiso 1 1 calc R . .
C6 C 0.61476(9) 0.82656(13) 0.65209(14) 0.0166(3) Uani 1 1 d . . .
C7 C 0.68177(9) 0.93917(13) 0.65779(15) 0.0167(3) Uani 1 1 d . . .
C8 C 0.75437(9) 0.77237(12) 0.80957(14) 0.0160(3) Uani 1 1 d . . .
C9 C 0.84532(9) 0.98276(12) 0.78952(15) 0.0156(3) Uani 1 1 d . . .
C10 C 0.85484(9) 1.05573(12) 0.92379(15) 0.0161(3) Uani 1 1 d . . .
C11 C 0.93458(9) 1.13692(13) 0.95474(15) 0.0186(3) Uani 1 1 d . . .
H11 H 0.9428 1.1861 1.0436 0.022 Uiso 1 1 calc R . .
C12 C 1.00126(9) 1.14424(13) 0.85337(16) 0.0203(3) Uani 1 1 d . . .
H12 H 1.0543 1.1979 0.8755 0.024 Uiso 1 1 calc R . .
C13 C 0.99020(10) 1.07275(14) 0.71919(16) 0.0214(3) Uani 1 1 d . . .
H13 H 1.0350 1.0791 0.6513 0.026 Uiso 1 1 calc R . .
C14 C 0.91116(10) 0.99137(13) 0.68739(15) 0.0190(3) Uani 1 1 d . . .
H14 H 0.9028 0.9431 0.5979 0.023 Uiso 1 1 calc R . .
C15 C 0.79766(12) 1.15499(16) 1.19108(18) 0.0299(3) Uani 1 1 d . . .
H15A H 0.8599 1.1353 1.2428 0.045 Uiso 1 1 calc R . .
H15B H 0.7519 1.1528 1.2623 0.045 Uiso 1 1 calc R . .
H15C H 0.7982 1.2404 1.1466 0.045 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 1.7614(14) . ?
S1 C15 1.8022(15) . ?
O1 C7 1.2069(17) . ?
O2 C8 1.2064(16) . ?
N1 C8 1.4061(17) . ?
N1 C7 1.4064(16) . ?
N1 C9 1.4359(16) . ?
C1 C6 1.3840(18) . ?
C1 C2 1.3853(18) . ?
C1 C8 1.4913(17) . ?
C2 C3 1.393(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3873(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4887(18) . ?
C9 C14 1.3815(19) . ?
C9 C10 1.3974(19) . ?
C10 C11 1.3991(18) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3933(19) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 C15 103.12(7) . . ?
C8 N1 C7 111.88(10) . . ?
C8 N1 C9 125.44(10) . . ?
C7 N1 C9 122.67(11) . . ?
C6 C1 C2 121.44(12) . . ?
C6 C1 C8 108.52(11) . . ?
C2 C1 C8 130.04(12) . . ?
C1 C2 C3 117.15(13) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.48(13) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.96(13) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 117.24(13) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C1 C6 C5 121.72(12) . . ?
C1 C6 C7 108.49(11) . . ?
C5 C6 C7 129.79(12) . . ?
O1 C7 N1 124.97(12) . . ?
O1 C7 C6 129.41(12) . . ?
N1 C7 C6 105.61(11) . . ?
O2 C8 N1 125.27(12) . . ?
O2 C8 C1 129.25(12) . . ?
N1 C8 C1 105.48(10) . . ?
C14 C9 C10 121.64(12) . . ?
C14 C9 N1 119.05(12) . . ?
C10 C9 N1 119.28(12) . . ?
C9 C10 C11 118.20(12) . . ?
C9 C10 S1 117.01(10) . . ?
C11 C10 S1 124.77(11) . . ?
C12 C11 C10 120.16(12) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.07(12) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 119.24(13) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 119.67(12) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C6 C1 C2 C3 -0.17(19) . . . . ?
C8 C1 C2 C3 -179.82(13) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C8 C1 C6 C5 -179.13(12) . . . . ?
C2 C1 C6 C7 -178.74(11) . . . . ?
C8 C1 C6 C7 0.98(14) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 179.04(13) . . . . ?
C8 N1 C7 O1 -179.78(13) . . . . ?
C9 N1 C7 O1 0.2(2) . . . . ?
C8 N1 C7 C6 0.23(14) . . . . ?
C9 N1 C7 C6 -179.76(11) . . . . ?
C1 C6 C7 O1 179.25(14) . . . . ?
C5 C6 C7 O1 -0.6(2) . . . . ?
C1 C6 C7 N1 -0.76(14) . . . . ?
C5 C6 C7 N1 179.36(13) . . . . ?
C7 N1 C8 O2 -179.19(13) . . . . ?
C9 N1 C8 O2 0.8(2) . . . . ?
C7 N1 C8 C1 0.34(14) . . . . ?
C9 N1 C8 C1 -179.67(11) . . . . ?
C6 C1 C8 O2 178.68(13) . . . . ?
C2 C1 C8 O2 -1.6(2) . . . . ?
C6 C1 C8 N1 -0.83(14) . . . . ?
C2 C1 C8 N1 178.86(13) . . . . ?
C8 N1 C9 C14 98.56(15) . . . . ?
C7 N1 C9 C14 -81.46(16) . . . . ?
C8 N1 C9 C10 -83.41(16) . . . . ?
C7 N1 C9 C10 96.58(15) . . . . ?
C14 C9 C10 C11 -1.29(19) . . . . ?
N1 C9 C10 C11 -179.27(11) . . . . ?
C14 C9 C10 S1 179.88(10) . . . . ?
N1 C9 C10 S1 1.90(16) . . . . ?
C15 S1 C10 C9 -174.91(10) . . . . ?
C15 S1 C10 C11 6.35(13) . . . . ?
C9 C10 C11 C12 0.40(19) . . . . ?
S1 C10 C11 C12 179.13(10) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C10 C9 C14 C13 1.2(2) . . . . ?
N1 C9 C14 C13 179.15(12) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.068
