# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_xj
_database_code_depnum_ccdc_archive 'CCDC 1953274'
loop_
_audit_author_name
_audit_author_address
YYY
;aaa
China
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2018-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O2 S'
_chemical_formula_sum            'C16 H13 N O2 S'
_chemical_formula_weight         283.33
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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      triclinic
_space_group_IT_number           2
_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                   6.4036(12)
_cell_length_b                   7.8241(19)
_cell_length_c                   14.538(3)
_cell_angle_alpha                85.370(3)
_cell_angle_beta                 89.441(2)
_cell_angle_gamma                70.995(2)
_cell_volume                     686.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2572
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0584 before and 0.0279 after correction. The Ratio of minimum to maximum transmission is 0.8908. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5484
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.763
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             2928
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.28936(7) 0.19851(5) 0.16111(3) 0.04184(19) Uani 1 1 d . . . . .
O1 O 0.1192(2) 0.11766(17) 0.17615(10) 0.0578(4) Uani 1 1 d . . . . .
O2 O 0.4607(2) 0.12600(18) 0.09700(9) 0.0591(4) Uani 1 1 d . . . . .
N1 N 0.2905(3) 0.2423(2) 0.33855(10) 0.0440(4) Uani 1 1 d . . . . .
C1 C 0.4235(3) 0.1939(2) 0.26967(12) 0.0382(4) Uani 1 1 d . . . . .
C2 C 0.3855(3) 0.2472(2) 0.42194(12) 0.0423(4) Uani 1 1 d . . . . .
C3 C 0.6169(3) 0.2001(3) 0.43414(13) 0.0464(5) Uani 1 1 d . . . . .
C4 C 0.7487(3) 0.1514(3) 0.35676(15) 0.0594(5) Uani 1 1 d . . . . .
H4 H 0.901186 0.122214 0.362063 0.071 Uiso 1 1 calc R . . . .
C5 C 0.6543(3) 0.1467(3) 0.27368(13) 0.0511(5) Uani 1 1 d . . . . .
H5 H 0.739557 0.113575 0.221821 0.061 Uiso 1 1 calc R . . . .
C6 C 0.6992(4) 0.2118(3) 0.52307(15) 0.0607(6) Uani 1 1 d . . . . .
H6 H 0.851190 0.178410 0.532283 0.073 Uiso 1 1 calc R . . . .
C7 C 0.5653(4) 0.2695(3) 0.59511(14) 0.0598(6) Uani 1 1 d . . . . .
C8 C 0.3345(5) 0.3164(3) 0.58096(15) 0.0686(6) Uani 1 1 d . . . . .
H8 H 0.240301 0.356122 0.629558 0.082 Uiso 1 1 calc R . . . .
C9 C 0.2478(4) 0.3044(3) 0.49761(15) 0.0644(6) Uani 1 1 d . . . . .
H9 H 0.095600 0.334416 0.490388 0.077 Uiso 1 1 calc R . . . .
C10 C 0.6547(6) 0.2890(3) 0.68798(16) 0.0840(8) Uani 1 1 d . . . . .
H10A H 0.622337 0.205780 0.733552 0.126 Uiso 1 1 calc GR . . . .
H10B H 0.586794 0.410842 0.704667 0.126 Uiso 1 1 calc GR . . . .
H10C H 0.811675 0.262894 0.684771 0.126 Uiso 1 1 calc GR . . . .
C11 C 0.1643(3) 0.4325(2) 0.13020(10) 0.0354(4) Uani 1 1 d . . . . .
C12 C 0.2914(3) 0.5312(2) 0.09241(12) 0.0472(4) Uani 1 1 d . . . . .
H12 H 0.440984 0.475296 0.082292 0.057 Uiso 1 1 calc R . . . .
C13 C 0.1918(4) 0.7166(3) 0.06957(14) 0.0543(5) Uani 1 1 d . . . . .
H13 H 0.275781 0.785929 0.045194 0.065 Uiso 1 1 calc R . . . .
C14 C -0.0284(4) 0.7963(3) 0.08290(13) 0.0548(5) Uani 1 1 d . . . . .
H14 H -0.094168 0.919530 0.066442 0.066 Uiso 1 1 calc R . . . .
C15 C -0.1535(4) 0.6975(3) 0.12006(16) 0.0604(6) Uani 1 1 d . . . . .
H15 H -0.303457 0.753905 0.129075 0.073 Uiso 1 1 calc R . . . .
C16 C -0.0583(3) 0.5131(2) 0.14454(14) 0.0507(5) Uani 1 1 d . . . . .
H16 H -0.142963 0.445330 0.170095 0.061 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 O1 1.4345(14) . ?
S1 O2 1.4334(14) . ?
S1 C1 1.7964(18) . ?
S1 C11 1.7649(16) . ?
N1 C1 1.306(2) . ?
N1 C2 1.370(2) . ?
C1 C5 1.403(3) . ?
C2 C3 1.415(3) . ?
C2 C9 1.411(3) . ?
C3 C4 1.401(3) . ?
C3 C6 1.422(3) . ?
C4 C5 1.364(3) . ?
C6 C7 1.357(3) . ?
C7 C8 1.415(4) . ?
C7 C10 1.509(3) . ?
C8 C9 1.360(3) . ?
C11 C12 1.376(2) . ?
C11 C16 1.380(2) . ?
C12 C13 1.395(3) . ?
C13 C14 1.362(3) . ?
C14 C15 1.363(3) . ?
C15 C16 1.388(3) . ?

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
O1 S1 C1 108.76(8) . . ?
O1 S1 C11 108.66(8) . . ?
O2 S1 O1 119.60(9) . . ?
O2 S1 C1 106.70(9) . . ?
O2 S1 C11 108.71(8) . . ?
C11 S1 C1 103.18(7) . . ?
C1 N1 C2 116.92(16) . . ?
N1 C1 S1 115.00(13) . . ?
N1 C1 C5 125.74(17) . . ?
C5 C1 S1 119.23(14) . . ?
N1 C2 C3 122.13(17) . . ?
N1 C2 C9 118.92(18) . . ?
C9 C2 C3 118.94(18) . . ?
C2 C3 C6 117.85(19) . . ?
C4 C3 C2 117.62(17) . . ?
C4 C3 C6 124.49(19) . . ?
C5 C4 C3 120.31(18) . . ?
C4 C5 C1 117.28(18) . . ?
C7 C6 C3 122.8(2) . . ?
C6 C7 C8 118.19(19) . . ?
C6 C7 C10 122.2(2) . . ?
C8 C7 C10 119.6(2) . . ?
C9 C8 C7 121.3(2) . . ?
C8 C9 C2 120.9(2) . . ?
C12 C11 S1 119.17(13) . . ?
C12 C11 C16 121.27(16) . . ?
C16 C11 S1 119.56(13) . . ?
C11 C12 C13 118.73(18) . . ?
C14 C13 C12 120.13(18) . . ?
C13 C14 C15 120.79(18) . . ?
C14 C15 C16 120.37(19) . . ?
C11 C16 C15 118.70(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
_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 C5 C4 177.65(15) . . . . ?
S1 C11 C12 C13 -179.00(14) . . . . ?
S1 C11 C16 C15 179.78(15) . . . . ?
O1 S1 C1 N1 -44.51(15) . . . . ?
O1 S1 C1 C5 137.67(15) . . . . ?
O1 S1 C11 C12 -165.48(13) . . . . ?
O1 S1 C11 C16 14.70(17) . . . . ?
O2 S1 C1 N1 -174.79(12) . . . . ?
O2 S1 C1 C5 7.39(18) . . . . ?
O2 S1 C11 C12 -33.81(16) . . . . ?
O2 S1 C11 C16 146.37(15) . . . . ?
N1 C1 C5 C4 0.1(3) . . . . ?
N1 C2 C3 C4 1.5(3) . . . . ?
N1 C2 C3 C6 179.21(15) . . . . ?
N1 C2 C9 C8 -178.09(19) . . . . ?
C1 S1 C11 C12 79.20(15) . . . . ?
C1 S1 C11 C16 -100.62(16) . . . . ?
C1 N1 C2 C3 -0.8(3) . . . . ?
C1 N1 C2 C9 177.93(16) . . . . ?
C2 N1 C1 S1 -177.67(12) . . . . ?
C2 N1 C1 C5 0.0(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C6 C7 -1.5(3) . . . . ?
C3 C2 C9 C8 0.7(3) . . . . ?
C3 C4 C5 C1 0.6(3) . . . . ?
C3 C6 C7 C8 1.3(3) . . . . ?
C3 C6 C7 C10 -177.23(18) . . . . ?
C4 C3 C6 C7 176.08(19) . . . . ?
C6 C3 C4 C5 -178.95(18) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C2 -0.9(4) . . . . ?
C9 C2 C3 C4 -177.25(18) . . . . ?
C9 C2 C3 C6 0.5(3) . . . . ?
C10 C7 C8 C9 178.5(2) . . . . ?
C11 S1 C1 N1 70.74(14) . . . . ?
C11 S1 C1 C5 -107.08(15) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
