# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_nb_0m
_database_code_depnum_ccdc_archive 'CCDC 2160456'
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_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         'C19 H19 N O4 S'
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41
_chemical_absolute_configuration rm
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.0585(9)
_cell_length_b                   6.5274(3)
_cell_length_c                   19.2202(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.051(2)
_cell_angle_gamma                90
_cell_volume                     1694.99(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2823
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.390
_cell_measurement_theta_min      3.015
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1081 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8958. 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    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7146
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 VENTURE'
_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         0.714
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                2604
_reflns_number_total             2980
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.330
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.079
_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)+(0.0390P)²+1.1273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0951
_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:
 C7(H7A,H7B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C18(H18), C14(H14), C2(H2), C4(H4), C17(H17), C5(H5), C3(H3), C15(H15)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_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 0.65326(7) 0.39845(15) 0.61861(5) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.7446(2) 0.3220(5) 0.66529(15) 0.0335(7) Uani 1 1 d . . . . .
O1 O 0.3835(2) 0.2618(4) 0.53369(14) 0.0292(7) Uani 1 1 d . . . . .
O2 O 0.5198(2) 0.7923(5) 0.69729(15) 0.0390(8) Uani 1 1 d . . . . .
O3 O 0.6457(3) 0.6138(4) 0.59987(15) 0.0336(8) Uani 1 1 d . . . . .
C1 C 0.3435(3) 0.6484(6) 0.4489(2) 0.0232(9) Uani 1 1 d . . . . .
C10 C 0.4081(3) 0.4306(6) 0.5587(2) 0.0226(9) Uani 1 1 d . . . . .
C13 C 0.6241(3) 0.2553(6) 0.5376(2) 0.0257(9) Uani 1 1 d . . . . .
N1 N 0.3909(2) 0.6148(5) 0.52407(16) 0.0228(8) Uani 1 1 d . . . . .
C7 C 0.4254(3) 0.7920(6) 0.5721(2) 0.0250(9) Uani 1 1 d . . . . .
H7A H 0.368964 0.877162 0.576228 0.030 Uiso 1 1 calc R . . . .
H7B H 0.471365 0.878062 0.553927 0.030 Uiso 1 1 calc R . . . .
C8 C 0.4775(3) 0.6967(6) 0.6437(2) 0.0271(9) Uani 1 1 d . . . . .
C6 C 0.3249(3) 0.4871(6) 0.3995(2) 0.0277(10) Uani 1 1 d . . . . .
H6 H 0.341670 0.350731 0.415460 0.033 Uiso 1 1 calc R . . . .
C12 C 0.5603(3) 0.3463(6) 0.6638(2) 0.0249(9) Uani 1 1 d . . . . .
H12A H 0.544313 0.198489 0.658258 0.030 Uiso 1 1 calc R . . . .
H12B H 0.589321 0.372796 0.716064 0.030 Uiso 1 1 calc R . . . .
C18 C 0.5745(3) 0.3454(7) 0.4723(2) 0.0297(10) Uani 1 1 d . . . . .
H18 H 0.556788 0.486136 0.470281 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3969(3) 0.3979(7) 0.6862(2) 0.0326(11) Uani 1 1 d . . . . .
H11A H 0.336455 0.480787 0.674103 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.432174 0.416767 0.737426 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.379571 0.253069 0.677040 0.049 Uiso 1 1 calc GR . . . .
C14 C 0.6517(3) 0.0506(6) 0.5412(2) 0.0290(10) Uani 1 1 d . . . . .
H14 H 0.686099 -0.009840 0.586041 0.035 Uiso 1 1 calc R . . . .
C2 C 0.3176(3) 0.8459(7) 0.4252(2) 0.0286(10) Uani 1 1 d . . . . .
H2 H 0.329143 0.956042 0.458778 0.034 Uiso 1 1 calc R . . . .
C4 C 0.2561(3) 0.7250(7) 0.3027(2) 0.0323(11) Uani 1 1 d . . . . .
H4 H 0.226039 0.751171 0.252864 0.039 Uiso 1 1 calc R . . . .
C9 C 0.4638(3) 0.4655(6) 0.6391(2) 0.0242(9) Uani 1 1 d . . . . .
C17 C 0.5513(4) 0.2265(7) 0.4100(2) 0.0343(11) Uani 1 1 d . . . . .
H17 H 0.517416 0.287138 0.365029 0.041 Uiso 1 1 calc R . . . .
C5 C 0.2815(3) 0.5275(7) 0.3266(2) 0.0320(11) Uani 1 1 d . . . . .
H5 H 0.269198 0.417964 0.292705 0.038 Uiso 1 1 calc R . . . .
C3 C 0.2747(4) 0.8831(7) 0.3518(2) 0.0362(11) Uani 1 1 d . . . . .
H3 H 0.258028 1.019304 0.335515 0.043 Uiso 1 1 calc R . . . .
C15 C 0.6281(4) -0.0643(7) 0.4779(2) 0.0329(10) Uani 1 1 d . . . . .
H15 H 0.647641 -0.203950 0.479544 0.039 Uiso 1 1 calc R . . . .
C16 C 0.5765(3) 0.0215(7) 0.4122(2) 0.0310(10) Uani 1 1 d . . . . .
C19 C 0.5465(4) -0.1116(8) 0.3450(2) 0.0403(12) Uani 1 1 d . . . . .
H19A H 0.479292 -0.163654 0.338879 0.060 Uiso 1 1 calc GR . . . .
H19B H 0.592541 -0.227015 0.350271 0.060 Uiso 1 1 calc GR . . . .
H19C H 0.548319 -0.030260 0.302578 0.060 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 O4 1.438(3) . ?
S1 O3 1.448(3) . ?
S1 C13 1.764(4) . ?
S1 C12 1.790(4) . ?
O1 C10 1.213(5) . ?
O2 C8 1.210(5) . ?
C1 N1 1.430(5) . ?
C1 C6 1.394(6) . ?
C1 C2 1.382(6) . ?
C10 N1 1.363(5) . ?
C10 C9 1.545(5) . ?
C13 C18 1.387(6) . ?
C13 C14 1.388(6) . ?
N1 C7 1.476(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.503(5) . ?
C8 C9 1.521(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C9 1.521(6) . ?
C18 H18 0.9500 . ?
C18 C17 1.389(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C9 1.538(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(6) . ?
C4 C3 1.373(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.382(7) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(6) . ?
C16 C19 1.516(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O4 S1 O3 118.93(19) . . ?
O4 S1 C13 108.43(19) . . ?
O4 S1 C12 106.12(18) . . ?
O3 S1 C13 108.16(18) . . ?
O3 S1 C12 106.98(19) . . ?
C13 S1 C12 107.74(19) . . ?
C6 C1 N1 121.3(3) . . ?
C2 C1 N1 118.9(3) . . ?
C2 C1 C6 119.8(3) . . ?
O1 C10 N1 128.0(4) . . ?
O1 C10 C9 122.7(3) . . ?
N1 C10 C9 109.3(3) . . ?
C18 C13 S1 120.7(3) . . ?
C18 C13 C14 121.1(4) . . ?
C14 C13 S1 118.3(3) . . ?
C1 N1 C7 119.5(3) . . ?
C10 N1 C1 126.8(3) . . ?
C10 N1 C7 113.7(3) . . ?
N1 C7 H7A 111.0 . . ?
N1 C7 H7B 111.0 . . ?
N1 C7 C8 104.0(3) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
O2 C8 C7 124.5(4) . . ?
O2 C8 C9 125.9(4) . . ?
C7 C8 C9 109.6(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
S1 C12 H12A 108.0 . . ?
S1 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C9 C12 S1 117.4(3) . . ?
C9 C12 H12A 108.0 . . ?
C9 C12 H12B 108.0 . . ?
C13 C18 H18 120.5 . . ?
C13 C18 C17 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(4) . . ?
C15 C14 H14 120.6 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C8 C9 C10 103.0(3) . . ?
C8 C9 C12 113.6(4) . . ?
C8 C9 C11 109.8(3) . . ?
C12 C9 C10 113.4(3) . . ?
C12 C9 C11 107.9(3) . . ?
C11 C9 C10 108.9(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 C19 121.4(4) . . ?
C15 C16 C19 119.7(4) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
