# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_mo_191101b_0m
_database_code_depnum_ccdc_archive 'CCDC 2039860'
_audit_update_record             
;
2020-10-21 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O3 S'
_chemical_formula_sum            'C16 H15 N O3 S'
_chemical_formula_weight         301.35
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3957(10)
_cell_length_b                   13.3926(15)
_cell_length_c                   11.5446(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.979(2)
_cell_angle_gamma                90
_cell_volume                     1426.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8013
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15074
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.028
_diffrn_reflns_theta_min         2.354
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.939
_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                3662
_reflns_number_total             4665
_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       'Bruker APEX2'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.074
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.028
_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)+(0.0868P)²+0.6812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1797
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C9(H9A,H9B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15) 
2.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.2182(3) 0.47940(17) 1.05784(18) 0.0591(5) Uani 1 1 d . . . . .
H1A H 0.1807 0.4420 1.1163 0.089 Uiso 1 1 calc GR . . . .
H1B H 0.1449 0.5242 1.0184 0.089 Uiso 1 1 calc GR . . . .
H1C H 0.3012 0.5171 1.0953 0.089 Uiso 1 1 calc GR . . . .
C2 C 0.2616(2) 0.40889(13) 0.96938(15) 0.0449(4) Uani 1 1 d . . . . .
C3 C 0.4017(2) 0.37105(16) 0.98451(16) 0.0515(4) Uani 1 1 d . . . . .
H3 H 0.4702 0.3906 1.0498 0.062 Uiso 1 1 calc R . . . .
C4 C 0.4412(2) 0.30471(15) 0.90412(17) 0.0504(4) Uani 1 1 d . . . . .
H4 H 0.5352 0.2797 0.9154 0.060 Uiso 1 1 calc R . . . .
C5 C 0.33889(19) 0.27597(13) 0.80647(14) 0.0419(3) Uani 1 1 d . . . . .
C6 C 0.1991(2) 0.31325(15) 0.78900(17) 0.0492(4) Uani 1 1 d . . . . .
H6 H 0.1309 0.2940 0.7234 0.059 Uiso 1 1 calc R . . . .
C7 C 0.1619(2) 0.37950(16) 0.87018(17) 0.0515(4) Uani 1 1 d . . . . .
H7 H 0.0681 0.4050 0.8582 0.062 Uiso 1 1 calc R . . . .
C8 C 0.5963(2) 0.30272(14) 0.63535(15) 0.0453(4) Uani 1 1 d . . . . .
C9 C 0.37258(19) 0.29062(15) 0.49505(15) 0.0462(4) Uani 1 1 d . . . . .
H9A H 0.2879 0.3290 0.5043 0.055 Uiso 1 1 calc R . . . .
H9B H 0.3424 0.2338 0.4442 0.055 Uiso 1 1 calc R . . . .
C10 C 0.48081(18) 0.35382(12) 0.44864(14) 0.0391(3) Uani 1 1 d . . . . .
C11 C 0.61023(17) 0.35995(12) 0.52872(13) 0.0375(3) Uani 1 1 d . . . . .
C12 C 0.72919(19) 0.41359(14) 0.50545(16) 0.0453(4) Uani 1 1 d . . . . .
C13 C 0.7079(2) 0.46267(14) 0.39683(17) 0.0520(4) Uani 1 1 d . . . . .
H13 H 0.7835 0.5001 0.3775 0.062 Uiso 1 1 calc R . . . .
C14 C 0.5784(2) 0.45757(15) 0.31707(17) 0.0542(5) Uani 1 1 d . . . . .
H14 H 0.5687 0.4916 0.2458 0.065 Uiso 1 1 calc R . . . .
C15 C 0.4628(2) 0.40284(16) 0.34117(16) 0.0515(4) Uani 1 1 d . . . . .
H15 H 0.3759 0.3990 0.2871 0.062 Uiso 1 1 calc R . . . .
C16 C 0.8701(3) 0.4175(2) 0.5909(2) 0.0761(7) Uani 1 1 d . . . . .
H16A H 0.8615 0.4619 0.6544 0.114 Uiso 1 1 calc GR . . . .
H16B H 0.9447 0.4413 0.5514 0.114 Uiso 1 1 calc GR . . . .
H16C H 0.8947 0.3519 0.6217 0.114 Uiso 1 1 calc GR . . . .
N1 N 0.45722(17) 0.25922(12) 0.60977(13) 0.0468(3) Uani 1 1 d . . . . .
O1 O 0.2525(2) 0.15379(12) 0.63285(15) 0.0694(5) Uani 1 1 d . . . . .
O2 O 0.4912(2) 0.12501(13) 0.76156(16) 0.0753(5) Uani 1 1 d . . . . .
O3 O 0.68076(18) 0.29359(15) 0.72762(13) 0.0710(5) Uani 1 1 d . . . . .
S1 S 0.38320(6) 0.19153(3) 0.70296(4) 0.05113(17) Uani 1 1 d . . . . .


_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
C1 C2 1.503(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.384(3) . ?
C5 S1 1.7521(18) . ?
C6 C7 1.383(3) . ?
C8 C11 1.477(2) . ?
C8 N1 1.410(2) . ?
C8 O3 1.207(2) . ?
C9 C10 1.498(2) . ?
C9 N1 1.470(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.385(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.396(3) . ?
C12 C16 1.494(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.382(3) . ?
N1 S1 1.6577(15) . ?
O1 S1 1.4284(18) . ?
O2 S1 1.4213(17) . ?

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
C3 C2 C1 121.10(17) . . ?
C3 C2 C7 118.26(17) . . ?
C7 C2 C1 120.65(17) . . ?
C4 C3 C2 121.16(18) . . ?
C3 C4 C5 119.28(17) . . ?
C4 C5 S1 120.98(14) . . ?
C6 C5 C4 120.62(17) . . ?
C6 C5 S1 118.41(14) . . ?
C7 C6 C5 119.22(18) . . ?
C6 C7 C2 121.45(17) . . ?
N1 C8 C11 105.39(14) . . ?
O3 C8 C11 129.84(18) . . ?
O3 C8 N1 124.76(17) . . ?
N1 C9 C10 101.31(14) . . ?
C11 C10 C9 111.39(14) . . ?
C11 C10 C15 120.84(17) . . ?
C15 C10 C9 127.77(17) . . ?
C10 C11 C8 108.69(14) . . ?
C10 C11 C12 122.41(15) . . ?
C12 C11 C8 128.90(16) . . ?
C11 C12 C16 122.16(18) . . ?
C13 C12 C11 115.57(17) . . ?
C13 C12 C16 122.27(18) . . ?
C14 C13 C12 122.22(17) . . ?
C13 C14 C15 121.24(17) . . ?
C14 C15 C10 117.71(18) . . ?
C8 N1 C9 113.03(14) . . ?
C8 N1 S1 125.23(13) . . ?
C9 N1 S1 121.27(12) . . ?
N1 S1 C5 105.86(8) . . ?
O1 S1 C5 108.93(10) . . ?
O1 S1 N1 104.33(9) . . ?
O2 S1 C5 108.71(10) . . ?
O2 S1 N1 107.56(10) . . ?
O2 S1 O1 120.46(12) . . ?

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
C1 C2 C3 C4 178.86(18) . . . . ?
C1 C2 C7 C6 -178.77(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 S1 -179.51(15) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 S1 N1 -84.68(16) . . . . ?
C4 C5 S1 O1 163.64(15) . . . . ?
C4 C5 S1 O2 30.63(18) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C6 C5 S1 N1 95.57(15) . . . . ?
C6 C5 S1 O1 -16.12(17) . . . . ?
C6 C5 S1 O2 -149.13(16) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C8 C11 C12 C13 -178.32(17) . . . . ?
C8 C11 C12 C16 2.1(3) . . . . ?
C8 N1 S1 C5 72.53(18) . . . . ?
C8 N1 S1 O1 -172.59(16) . . . . ?
C8 N1 S1 O2 -43.56(19) . . . . ?
C9 C10 C11 C8 -1.08(19) . . . . ?
C9 C10 C11 C12 179.15(16) . . . . ?
C9 C10 C15 C14 179.79(18) . . . . ?
C9 N1 S1 C5 -99.08(16) . . . . ?
C9 N1 S1 O1 15.80(18) . . . . ?
C9 N1 S1 O2 144.83(16) . . . . ?
C10 C9 N1 C8 3.8(2) . . . . ?
C10 C9 N1 S1 176.32(12) . . . . ?
C10 C11 C12 C13 1.4(2) . . . . ?
C10 C11 C12 C16 -178.21(19) . . . . ?
C11 C8 N1 C9 -4.5(2) . . . . ?
C11 C8 N1 S1 -176.71(13) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 0.5(3) . . . . ?
C15 C10 C11 C8 178.63(16) . . . . ?
C15 C10 C11 C12 -1.1(3) . . . . ?
C16 C12 C13 C14 178.9(2) . . . . ?
N1 C8 C11 C10 3.34(19) . . . . ?
N1 C8 C11 C12 -176.91(17) . . . . ?
N1 C9 C10 C11 -1.50(19) . . . . ?
N1 C9 C10 C15 178.81(18) . . . . ?
O3 C8 C11 C10 -175.6(2) . . . . ?
O3 C8 C11 C12 4.2(3) . . . . ?
O3 C8 N1 C9 174.5(2) . . . . ?
O3 C8 N1 S1 2.3(3) . . . . ?
S1 C5 C6 C7 179.60(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
