# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_yanrl_0405
_audit_block_doi                 10.5517/ccdc.csd.cc1zvds0
_database_code_depnum_ccdc_archive 'CCDC 1842633'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2016-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H19 N O2 S'
_chemical_formula_sum            'C18 H19 N O2 S'
_chemical_formula_weight         313.40
_chemical_absolute_configuration ad
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.0792(9)
_cell_length_b                   7.9190(4)
_cell_length_c                   11.2172(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.357(11)
_cell_angle_gamma                90.00
_cell_volume                     809.07(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    842
_cell_measurement_temperature    290.83(10)
_cell_measurement_theta_max      24.5950
_cell_measurement_theta_min      4.0190
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3222
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.41
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   74.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   24.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000    0.0000 16

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   38.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   88.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -180.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0764875000
_diffrn_orient_matrix_UB_12      0.0161541000
_diffrn_orient_matrix_UB_13      0.0302498000
_diffrn_orient_matrix_UB_21      -0.0040408000
_diffrn_orient_matrix_UB_22      0.0194801000
_diffrn_orient_matrix_UB_23      0.0601501000
_diffrn_orient_matrix_UB_31      0.0134619000
_diffrn_orient_matrix_UB_32      -0.0859443000
_diffrn_orient_matrix_UB_33      0.0192924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2088
_reflns_number_total             2566
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(11)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0348P)²+0.0695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1104
_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. 
;
_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:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.79411(10) 0.43162(11) 0.21792(9) 0.0438(2) Uani 1 d . . .
O1 O 0.8381(3) 0.5420(3) 0.3310(3) 0.0599(8) Uani 1 d . . .
O2 O 0.6657(3) 0.4770(3) 0.0994(3) 0.0570(8) Uani 1 d . . .
N1 N 0.6700(3) -0.0219(4) 0.2521(3) 0.0480(8) Uani 1 d . . .
C1 C 1.0732(4) 0.5025(5) 0.2534(4) 0.0530(11) Uani 1 d . . .
H1 H 1.0814 0.5638 0.3269 0.064 Uiso 1 calc . . R
C2 C 1.1903(4) 0.4955(6) 0.2194(5) 0.0611(11) Uani 1 d . . .
H2 H 1.2769 0.5518 0.2714 0.073 Uiso 1 calc . . R
C3 C 1.1813(4) 0.4076(5) 0.1110(4) 0.0549(10) Uani 1 d . . .
C4 C 1.0512(5) 0.3226(6) 0.0366(4) 0.0604(12) Uani 1 d . . .
H4 H 1.0429 0.2607 -0.0368 0.073 Uiso 1 calc . . R
C5 C 0.9346(4) 0.3283(5) 0.0695(4) 0.0522(10) Uani 1 d . . .
H5 H 0.8482 0.2711 0.0182 0.063 Uiso 1 calc . . R
C6 C 0.9454(3) 0.4185(5) 0.1783(3) 0.0383(8) Uani 1 d . . .
C7 C 0.7708(4) 0.2321(5) 0.2619(4) 0.0425(9) Uani 1 d . . .
C8 C 0.8789(4) 0.1359(5) 0.3768(4) 0.0539(10) Uani 1 d . . .
H8A H 0.9679 0.1133 0.3664 0.065 Uiso 1 calc . . R
H8B H 0.9039 0.1968 0.4587 0.065 Uiso 1 calc . . R
C9 C 0.7999(4) -0.0212(6) 0.3738(4) 0.0636(12) Uani 1 d . . .
H9A H 0.8607 -0.1183 0.3786 0.076 Uiso 1 calc . . R
H9B H 0.7745 -0.0252 0.4479 0.076 Uiso 1 calc . . R
C10 C 0.6541(4) 0.1316(5) 0.1947(3) 0.0407(9) Uani 1 d . . .
H10 H 0.5731 0.1639 0.1185 0.049 Uiso 1 calc . . R
C11 C 0.5544(4) -0.1485(5) 0.2191(4) 0.0549(11) Uani 1 d . . .
H11A H 0.5989 -0.2598 0.2374 0.066 Uiso 1 calc . . R
H11B H 0.4911 -0.1424 0.1254 0.066 Uiso 1 calc . . R
C12 C 0.4624(4) -0.1268(4) 0.2945(4) 0.0435(9) Uani 1 d . . .
C13 C 0.5017(5) -0.2018(6) 0.4164(5) 0.0690(13) Uani 1 d . . .
H13 H 0.5864 -0.2670 0.4528 0.083 Uiso 1 calc . . R
C14 C 0.4165(7) -0.1810(7) 0.4854(4) 0.0840(17) Uani 1 d . . .
H14 H 0.4439 -0.2321 0.5672 0.101 Uiso 1 calc . . R
C15 C 0.2907(6) -0.0836(8) 0.4311(5) 0.0814(15) Uani 1 d . . .
H15 H 0.2335 -0.0678 0.4769 0.098 Uiso 1 calc . . R
C16 C 0.2513(5) -0.0120(6) 0.3127(5) 0.0739(14) Uani 1 d . . .
H16 H 0.1657 0.0518 0.2760 0.089 Uiso 1 calc . . R
C17 C 0.3361(4) -0.0316(5) 0.2440(4) 0.0562(11) Uani 1 d . . .
H17 H 0.3072 0.0204 0.1624 0.067 Uiso 1 calc . . R
C18 C 1.3088(5) 0.4029(7) 0.0729(5) 0.0894(16) Uani 1 d . . .
H18A H 1.3339 0.5159 0.0595 0.134 Uiso 1 calc . . GR
H18B H 1.2811 0.3393 -0.0071 0.134 Uiso 1 calc . . GR
H18C H 1.3919 0.3504 0.1422 0.134 Uiso 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 O1 1.445(3) . ?
S1 O2 1.449(3) . ?
S1 C6 1.765(3) . ?
S1 C7 1.702(4) . ?
N1 C9 1.431(5) . ?
N1 C10 1.353(5) . ?
N1 C11 1.459(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(5) . ?
C1 C6 1.372(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(6) . ?
C3 C4 1.390(5) . ?
C3 C18 1.518(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C7 C8 1.492(5) . ?
C7 C10 1.351(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.469(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(5) . ?
C12 C13 1.384(5) . ?
C12 C17 1.376(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.339(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(5) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 O2 118.24(18) . . ?
O1 S1 C6 106.46(17) . . ?
O1 S1 C7 109.63(18) . . ?
O2 S1 C6 108.16(15) . . ?
O2 S1 C7 108.47(17) . . ?
C7 S1 C6 105.09(17) . . ?
C9 N1 C11 123.4(3) . . ?
C10 N1 C9 108.9(3) . . ?
C10 N1 C11 125.3(3) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.8(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(4) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 117.8(4) . . ?
C2 C3 C18 121.3(4) . . ?
C4 C3 C18 120.9(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 S1 120.1(3) . . ?
C1 C6 C5 119.6(3) . . ?
C5 C6 S1 120.3(3) . . ?
C8 C7 S1 125.7(3) . . ?
C10 C7 S1 125.5(3) . . ?
C10 C7 C8 108.7(3) . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 C7 102.9(3) . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
N1 C9 C8 106.9(3) . . ?
N1 C9 H9A 110.3 . . ?
N1 C9 H9B 110.3 . . ?
C8 C9 H9A 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N1 C10 H10 124.3 . . ?
C7 C10 N1 111.5(3) . . ?
C7 C10 H10 124.3 . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
N1 C11 C12 113.3(3) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 121.4(4) . . ?
C17 C12 C11 120.9(3) . . ?
C17 C12 C13 117.7(4) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.1(5) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 121.1(4) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 C7 C8 C9 176.3(3) . . . . ?
S1 C7 C10 N1 177.8(3) . . . . ?
O1 S1 C6 C1 1.4(3) . . . . ?
O1 S1 C6 C5 -176.7(3) . . . . ?
O1 S1 C7 C8 -51.0(4) . . . . ?
O1 S1 C7 C10 132.5(3) . . . . ?
O2 S1 C6 C1 129.4(3) . . . . ?
O2 S1 C6 C5 -48.6(4) . . . . ?
O2 S1 C7 C8 178.6(3) . . . . ?
O2 S1 C7 C10 2.0(4) . . . . ?
N1 C11 C12 C13 -88.4(4) . . . . ?
N1 C11 C12 C17 91.6(4) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C1 C2 C3 C18 178.9(4) . . . . ?
C2 C1 C6 S1 -178.2(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 S1 178.0(3) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C6 S1 C7 C8 63.1(4) . . . . ?
C6 S1 C7 C10 -113.4(3) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C7 S1 C6 C1 -114.9(3) . . . . ?
C7 S1 C6 C5 67.1(3) . . . . ?
C7 C8 C9 N1 9.8(4) . . . . ?
C8 C7 C10 N1 0.8(5) . . . . ?
C9 N1 C10 C7 5.8(4) . . . . ?
C9 N1 C11 C12 73.2(5) . . . . ?
C10 N1 C9 C8 -10.0(4) . . . . ?
C10 N1 C11 C12 -87.0(4) . . . . ?
C10 C7 C8 C9 -6.7(5) . . . . ?
C11 N1 C9 C8 -173.0(4) . . . . ?
C11 N1 C10 C7 168.4(3) . . . . ?
C11 C12 C13 C14 179.9(4) . . . . ?
C11 C12 C17 C16 179.8(4) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 C12 C17 C16 -0.2(5) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C17 -1.1(8) . . . . ?
C15 C16 C17 C12 0.8(7) . . . . ?
C17 C12 C13 C14 -0.1(6) . . . . ?
C18 C3 C4 C5 -179.1(4) . . . . ?

_olex2_date_sample_data_collection 2016-04-05
_olex2_submission_special_instructions 'No special instructions were received'
