# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1474645'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.	2020-02-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H13 N O3 S'
_chemical_formula_sum            'C16 H13 N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         299.33

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.518(7)
_cell_length_b                   9.118(9)
_cell_length_c                   11.293(11)
_cell_angle_alpha                70.671(10)
_cell_angle_beta                 71.668(11)
_cell_angle_gamma                78.323(11)
_cell_volume                     689.2(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4699
_cell_measurement_theta_min      2.3816
_cell_measurement_theta_max      25.1523
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312

_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8677
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_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.
;

_reflns_number_total             2461
_reflns_number_gt                2186
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1461
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         2461
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0917P)²+0.2923P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.494
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.13772(11) 0.32044(7) 0.20437(6) 0.0582(3) Uani d . 1 . .
O O1 0.55285(18) 0.90084(15) 0.19024(12) 0.0330(3) Uani d . 1 . .
O O2 0.7405(2) 1.05078(19) 0.02115(14) 0.0465(4) Uani d . 1 . .
O O3 0.1431(2) 0.56699(18) 0.53378(14) 0.0439(4) Uani d . 1 . .
H H4 0.1818 0.4744 0.542 0.066 Uiso calc R 1 . .
N N1 0.1233(2) 0.64578(19) 0.29057(15) 0.0314(4) Uani d . 1 . .
C C1 0.8495(3) 0.9363(3) 0.4453(2) 0.0417(5) Uani d . 1 . .
H H8 0.9457 1.0049 0.3969 0.063 Uiso calc R 1 . .
H H9 0.9063 0.8344 0.4836 0.063 Uiso calc R 1 . .
H H1 0.7628 0.9771 0.5128 0.063 Uiso calc R 1 . .
C C2 0.7457(3) 0.9245(2) 0.35581(19) 0.0326(4) Uani d . 1 . .
C C3 0.5921(3) 0.8301(2) 0.40559(18) 0.0301(4) Uani d . 1 . .
C C4 0.4992(3) 0.8221(2) 0.32006(17) 0.0282(4) Uani d . 1 . .
C C5 0.3454(3) 0.7333(2) 0.35835(17) 0.0295(4) Uani d . 1 . .
C C6 0.2593(3) 0.7293(2) 0.26502(17) 0.0292(4) Uani d . 1 . .
H H10 0.3027 0.7903 0.1797 0.035 Uiso calc R 1 . .
C C7 0.0397(3) 0.6416(2) 0.18987(18) 0.0322(4) Uani d . 1 . .
H H11 0.0439 0.7425 0.1244 0.039 Uiso calc R 1 . .
H H12 -0.0916 0.6236 0.2295 0.039 Uiso calc R 1 . .
C C8 0.1396(3) 0.5170(2) 0.12528(18) 0.0339(4) Uani d . 1 . .
C C9 0.2417(3) 0.5399(3) -0.0034(2) 0.0446(5) Uani d . 1 . .
H H13 0.2603 0.6379 -0.063 0.054 Uiso calc R 1 . .
C C10 0.3145(4) 0.3984(3) -0.0343(3) 0.0576(7) Uani d . 1 . .
H H2 0.3848 0.3937 -0.1173 0.069 Uiso calc R 1 . .
C C11 0.2736(4) 0.2717(3) 0.0663(3) 0.0606(7) Uani d . 1 . .
H H3 0.3135 0.1696 0.0622 0.073 Uiso calc R 1 . .
C C12 0.7036(3) 0.9910(2) 0.13770(19) 0.0338(4) Uani d . 1 . .
C C13 0.7962(3) 1.0013(2) 0.2269(2) 0.0365(5) Uani d . 1 . .
H H5 0.8948 1.0631 0.1954 0.044 Uiso calc R 1 . .
C C14 0.5266(3) 0.7423(2) 0.53902(19) 0.0368(5) Uani d . 1 . .
H H6 0.5871 0.7443 0.5986 0.044 Uiso calc R 1 . .
C C15 0.3796(3) 0.6565(2) 0.58146(18) 0.0387(5) Uani d . 1 . .
H H7 0.3413 0.6028 0.6695 0.046 Uiso calc R 1 . .
C C16 0.2806(3) 0.6454(2) 0.49480(18) 0.0329(4) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.718(3) ?
S1 C11 . 1.716(3) ?
O1 C4 . 1.370(2) ?
O1 C12 . 1.394(2) ?
O2 C12 . 1.210(3) ?
O3 C16 . 1.256(3) ?
O3 H4 . 0.82 ?
N1 C6 . 1.301(3) ?
N1 C7 . 1.476(2) ?
C1 C2 . 1.498(3) ?
C1 H8 . 0.96 ?
C1 H9 . 0.96 ?
C1 H1 . 0.96 ?
C2 C13 . 1.356(3) ?
C2 C3 . 1.437(3) ?
C3 C4 . 1.385(3) ?
C3 C14 . 1.431(3) ?
C4 C5 . 1.418(3) ?
C5 C6 . 1.413(3) ?
C5 C16 . 1.457(3) ?
C6 H10 . 0.93 ?
C7 C8 . 1.498(3) ?
C7 H11 . 0.97 ?
C7 H12 . 0.97 ?
C8 C9 . 1.381(3) ?
C9 C10 . 1.406(4) ?
C9 H13 . 0.93 ?
C10 C11 . 1.332(4) ?
C10 H2 . 0.93 ?
C11 H3 . 0.93 ?
C12 C13 . 1.428(3) ?
C13 H5 . 0.93 ?
C14 C15 . 1.353(3) ?
C14 H6 . 0.93 ?
C15 C16 . 1.441(3) ?
C15 H7 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C11 . . 92.10(13) ?
C4 O1 C12 . . 121.98(14) ?
C16 O3 H4 . . 109.5 ?
C6 N1 C7 . . 122.80(16) ?
C2 C1 H8 . . 109.5 ?
C2 C1 H9 . . 109.5 ?
H8 C1 H9 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H8 C1 H1 . . 109.5 ?
H9 C1 H1 . . 109.5 ?
C13 C2 C3 . . 119.12(17) ?
C13 C2 C1 . . 120.65(18) ?
C3 C2 C1 . . 120.23(18) ?
C4 C3 C14 . . 116.83(18) ?
C4 C3 C2 . . 118.65(18) ?
C14 C3 C2 . . 124.51(17) ?
O1 C4 C3 . . 121.11(17) ?
O1 C4 C5 . . 115.37(15) ?
C3 C4 C5 . . 123.53(17) ?
C6 C5 C4 . . 120.25(17) ?
C6 C5 C16 . . 121.06(17) ?
C4 C5 C16 . . 118.68(16) ?
N1 C6 C5 . . 124.29(17) ?
N1 C6 H10 . . 117.9 ?
C5 C6 H10 . . 117.9 ?
N1 C7 C8 . . 112.65(16) ?
N1 C7 H11 . . 109.1 ?
C8 C7 H11 . . 109.1 ?
N1 C7 H12 . . 109.1 ?
C8 C7 H12 . . 109.1 ?
H11 C7 H12 . . 107.8 ?
C9 C8 C7 . . 126.54(19) ?
C9 C8 S1 . . 110.08(16) ?
C7 C8 S1 . . 123.37(16) ?
C8 C9 C10 . . 112.5(2) ?
C8 C9 H13 . . 123.7 ?
C10 C9 H13 . . 123.7 ?
C11 C10 C9 . . 113.8(2) ?
C11 C10 H2 . . 123.1 ?
C9 C10 H2 . . 123.1 ?
C10 C11 S1 . . 111.5(2) ?
C10 C11 H3 . . 124.2 ?
S1 C11 H3 . . 124.3 ?
O2 C12 O1 . . 115.57(17) ?
O2 C12 C13 . . 127.85(18) ?
O1 C12 C13 . . 116.58(17) ?
C2 C13 C12 . . 122.53(18) ?
C2 C13 H5 . . 118.7 ?
C12 C13 H5 . . 118.7 ?
C15 C14 C3 . . 122.29(17) ?
C15 C14 H6 . . 118.9 ?
C3 C14 H6 . . 118.9 ?
C14 C15 C16 . . 122.17(18) ?
C14 C15 H7 . . 118.9 ?
C16 C15 H7 . . 118.9 ?
O3 C16 C15 . . 122.47(18) ?
O3 C16 C5 . . 121.03(17) ?
C15 C16 C5 . . 116.49(18) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C2 C3 C4 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 179.90(17) ?
C13 C2 C3 C14 . . . . 179.37(19) ?
C1 C2 C3 C14 . . . . -0.1(3) ?
C12 O1 C4 C3 . . . . 0.7(3) ?
C12 O1 C4 C5 . . . . -178.95(16) ?
C14 C3 C4 O1 . . . . -179.36(16) ?
C2 C3 C4 O1 . . . . 0.7(3) ?
C14 C3 C4 C5 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . -179.73(16) ?
O1 C4 C5 C6 . . . . 0.5(3) ?
C3 C4 C5 C6 . . . . -179.17(17) ?
O1 C4 C5 C16 . . . . 179.64(16) ?
C3 C4 C5 C16 . . . . 0.0(3) ?
C7 N1 C6 C5 . . . . -178.53(17) ?
C4 C5 C6 N1 . . . . 176.90(17) ?
C16 C5 C6 N1 . . . . -2.3(3) ?
C6 N1 C7 C8 . . . . 89.1(2) ?
N1 C7 C8 C9 . . . . -114.0(2) ?
N1 C7 C8 S1 . . . . 67.2(2) ?
C11 S1 C8 C9 . . . . 0.43(17) ?
C11 S1 C8 C7 . . . . 179.37(16) ?
C7 C8 C9 C10 . . . . -178.67(19) ?
S1 C8 C9 C10 . . . . 0.2(2) ?
C8 C9 C10 C11 . . . . -1.0(3) ?
C9 C10 C11 S1 . . . . 1.3(3) ?
C8 S1 C11 C10 . . . . -1.0(2) ?
C4 O1 C12 O2 . . . . 177.83(17) ?
C4 O1 C12 C13 . . . . -1.9(3) ?
C3 C2 C13 C12 . . . . -0.7(3) ?
C1 C2 C13 C12 . . . . 178.77(18) ?
O2 C12 C13 C2 . . . . -177.8(2) ?
O1 C12 C13 C2 . . . . 1.9(3) ?
C4 C3 C14 C15 . . . . -0.8(3) ?
C2 C3 C14 C15 . . . . 179.22(19) ?
C3 C14 C15 C16 . . . . 1.0(3) ?
C14 C15 C16 O3 . . . . -179.38(19) ?
C14 C15 C16 C5 . . . . -0.7(3) ?
C6 C5 C16 O3 . . . . -1.9(3) ?
C4 C5 C16 O3 . . . . 178.88(17) ?
C6 C5 C16 C15 . . . . 179.36(17) ?
C4 C5 C16 C15 . . . . 0.2(3) ?

