# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_22019265_0m
_database_code_depnum_ccdc_archive 'CCDC 1904964'
loop_
_audit_author_name
_audit_author_address
' Tianzi Dai'
;Shanghai Institute of Materia Medica Chinese Academy of Science 
China
;
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_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         'C17 H13 N O2 S'
_chemical_formula_sum            'C17 H13 N O2 S'
_chemical_formula_weight         295.34
_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'
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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.6988(2)
_cell_length_b                   11.4847(3)
_cell_length_c                   30.9861(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2739.74(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9215
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.476
_cell_measurement_theta_min      2.954
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1342 before and 0.0714 after correction. The Ratio of minimum to maximum transmission is 0.8070. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            31015
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                2514
_reflns_number_total             3124
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.392
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.021
_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)+(0.0394P)²+3.2777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1082
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C9(H9), C4(H4), C17(H17), C2(H2A), C16(H16), C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.27496(6) 0.42073(4) 0.55624(2) 0.01572(14) Uani 1 1 d . . . . .
O1 O 0.41827(19) 0.37403(12) 0.64131(5) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.6197(2) 0.41168(13) 0.70684(5) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.565347 0.370547 0.688952 0.038 Uiso 1 1 calc GR . . . .
N1 N 0.3529(2) 0.62338(14) 0.52630(5) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.2248(3) 0.58292(17) 0.44013(6) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.273872 0.656732 0.446679 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2799(2) 0.52336(16) 0.51553(6) 0.0146(4) Uani 1 1 d . . . . .
C6 C 0.2114(2) 0.49841(16) 0.47240(6) 0.0142(4) Uani 1 1 d . . . . .
C12 C 0.4685(2) 0.56380(17) 0.66788(6) 0.0157(4) Uani 1 1 d . . . . .
C11 C 0.4181(2) 0.48071(17) 0.63397(6) 0.0158(4) Uani 1 1 d . . . . .
C1 C 0.1350(3) 0.39157(16) 0.46226(6) 0.0163(4) Uani 1 1 d . . . . .
H1 H 0.122366 0.333817 0.483985 0.020 Uiso 1 1 calc R . . . .
C9 C 0.4042(3) 0.62083(17) 0.56827(6) 0.0165(4) Uani 1 1 d . . . . .
H9 H 0.460444 0.685300 0.581452 0.020 Uiso 1 1 calc R . . . .
C10 C 0.3704(2) 0.52000(16) 0.59061(6) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.1670(3) 0.55985(17) 0.39863(6) 0.0174(4) Uani 1 1 d . . . . .
H4 H 0.177311 0.618089 0.377009 0.021 Uiso 1 1 calc R . . . .
C3 C 0.0941(3) 0.45246(17) 0.38819(6) 0.0172(4) Uani 1 1 d . . . . .
C17 C 0.4175(3) 0.68165(17) 0.66763(6) 0.0184(4) Uani 1 1 d . . . . .
H17 H 0.346194 0.709763 0.644884 0.022 Uiso 1 1 calc R . . . .
C2 C 0.0777(3) 0.36941(17) 0.42085(6) 0.0175(4) Uani 1 1 d . . . . .
H2A H 0.026208 0.296266 0.414447 0.021 Uiso 1 1 calc R . . . .
C13 C 0.5693(3) 0.52379(17) 0.70291(6) 0.0181(4) Uani 1 1 d . . . . .
C16 C 0.4692(3) 0.75673(18) 0.69979(6) 0.0218(4) Uani 1 1 d . . . . .
H16 H 0.431593 0.835504 0.699543 0.026 Uiso 1 1 calc R . . . .
C15 C 0.5771(3) 0.71656(19) 0.73273(7) 0.0229(5) Uani 1 1 d . . . . .
H15 H 0.617045 0.769098 0.754230 0.027 Uiso 1 1 calc R . . . .
C14 C 0.6261(3) 0.6015(2) 0.73434(6) 0.0225(5) Uani 1 1 d . . . . .
H14 H 0.699148 0.574948 0.757017 0.027 Uiso 1 1 calc R . . . .
C7 C 0.0327(3) 0.42627(19) 0.34309(7) 0.0246(5) Uani 1 1 d . . . . .
H7A H -0.094487 0.429542 0.342165 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.071654 0.348278 0.334669 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.080796 0.483928 0.323076 0.037 Uiso 1 1 calc GR . . . .


_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 C8 1.7267(19) . ?
S1 C10 1.7242(19) . ?
O1 C11 1.246(2) . ?
O2 H2 0.8400 . ?
O2 C13 1.350(2) . ?
N1 C8 1.322(2) . ?
N1 C9 1.359(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C5 C4 1.386(3) . ?
C8 C6 1.465(3) . ?
C6 C1 1.396(3) . ?
C12 C11 1.472(3) . ?
C12 C17 1.409(3) . ?
C12 C13 1.411(3) . ?
C11 C10 1.464(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.393(3) . ?
C3 C2 1.396(3) . ?
C3 C7 1.506(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.376(3) . ?
C2 H2A 0.9500 . ?
C13 C14 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.394(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.375(3) . ?
C14 H14 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 C8 89.45(9) . . ?
C13 O2 H2 109.5 . . ?
C8 N1 C9 110.26(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.48(18) . . ?
N1 C8 S1 114.72(14) . . ?
N1 C8 C6 123.60(17) . . ?
C6 C8 S1 121.67(14) . . ?
C5 C6 C8 119.36(17) . . ?
C1 C6 C5 118.73(18) . . ?
C1 C6 C8 121.91(17) . . ?
C17 C12 C11 123.05(18) . . ?
C17 C12 C13 118.04(18) . . ?
C13 C12 C11 118.89(17) . . ?
O1 C11 C12 120.47(17) . . ?
O1 C11 C10 118.08(17) . . ?
C10 C11 C12 121.43(17) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.36(18) . . ?
C2 C1 H1 119.8 . . ?
N1 C9 H9 121.8 . . ?
N1 C9 C10 116.42(18) . . ?
C10 C9 H9 121.8 . . ?
C11 C10 S1 118.02(14) . . ?
C9 C10 S1 109.09(14) . . ?
C9 C10 C11 132.40(18) . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 120.93(18) . . ?
C3 C4 H4 119.5 . . ?
C4 C3 C2 118.22(18) . . ?
C4 C3 C7 121.27(18) . . ?
C2 C3 C7 120.51(18) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.13(19) . . ?
C16 C17 H17 119.4 . . ?
C1 C2 C3 121.26(18) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
O2 C13 C12 122.55(18) . . ?
O2 C13 C14 117.25(18) . . ?
C14 C13 C12 120.16(19) . . ?
C17 C16 H16 120.2 . . ?
C17 C16 C15 119.66(19) . . ?
C15 C16 H16 120.2 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.53(19) . . ?
C14 C15 H15 119.7 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
