# Supplementary Information (SI) for ChemComm.
# 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_sm_29cc_a
_database_code_depnum_ccdc_archive 'CCDC 2347214'
loop_
_audit_author_name
_audit_author_address
'Indrajit Das'
;Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_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 H17 N O2 S'
_chemical_formula_sum            'C19 H17 N O2 S'
_chemical_formula_weight         323.39
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.7535(9)
_cell_length_b                   9.7512(10)
_cell_length_c                   11.0588(12)
_cell_angle_alpha                108.448(4)
_cell_angle_beta                 99.312(4)
_cell_angle_gamma                107.231(3)
_cell_volume                     820.53(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      5.32
_shelx_estimated_absorpt_T_max   0.735
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1503 before and 0.0852 after correction. The Ratio of minimum to maximum transmission is 0.7561. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21001
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.101
_diffrn_reflns_theta_min         5.323
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3036
_reflns_number_total             3125
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.053
_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)+(0.0566P)²+0.5030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1155
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C13(H13), C16(H16), C2(H2), C14(H14), C1(H1),
 C15(H15), C6(H6)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.84687(5) 0.37757(5) 0.27782(4) 0.02720(18) Uani 1 1 d . . . . .
O1 O 0.71099(17) 0.48202(14) 0.49308(13) 0.0318(3) Uani 1 1 d . . . . .
O2 O 0.77135(19) 0.13871(14) 0.35090(13) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.82331(17) 0.39406(15) 0.78806(13) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.7970(2) 0.26860(18) 0.66054(16) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.897287 0.296503 0.627745 0.023 Uiso 1 1 calc R . . . .
C11 C 0.6847(2) 0.55561(18) 0.89906(16) 0.0196(3) Uani 1 1 d . . . . .
C10 C 0.6969(2) 0.43389(17) 0.78437(16) 0.0190(3) Uani 1 1 d . . . . .
C18 C 0.7727(2) 0.26720(19) 0.36833(16) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.8159(2) 0.00367(18) 0.58984(16) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.865510 0.026424 0.524680 0.026 Uiso 1 1 calc R . . . .
C17 C 0.7057(2) 0.35202(18) 0.47841(16) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.5583(2) 0.34707(19) 0.65492(16) 0.0212(4) Uani 1 1 d . . . . .
H9A H 0.521551 0.419705 0.623553 0.025 Uiso 1 1 calc R . . . .
H9B H 0.461350 0.271443 0.664159 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6428(2) 0.26474(18) 0.56166(16) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.566497 0.155168 0.504557 0.023 Uiso 1 1 calc R . . . .
C4 C 0.76876(19) 0.11403(18) 0.67453(16) 0.0193(3) Uani 1 1 d . . . . .
C5 C 0.6960(2) 0.0785(2) 0.76879(17) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.663673 0.152647 0.826914 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5477(2) 0.59957(19) 0.88732(17) 0.0224(4) Uani 1 1 d . . . . .
H12 H 0.460301 0.549161 0.806563 0.027 Uiso 1 1 calc R . . . .
C13 C 0.5378(2) 0.7168(2) 0.99306(18) 0.0259(4) Uani 1 1 d . . . . .
H13 H 0.443693 0.746387 0.984388 0.031 Uiso 1 1 calc R . . . .
C16 C 0.8108(2) 0.6281(2) 1.01976(17) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.903436 0.596789 1.029917 0.031 Uiso 1 1 calc R . . . .
C2 C 0.7905(2) -0.13906(19) 0.60050(17) 0.0257(4) Uani 1 1 d . . . . .
H2 H 0.823418 -0.213263 0.542993 0.031 Uiso 1 1 calc R . . . .
C14 C 0.6648(2) 0.79104(19) 1.11135(18) 0.0277(4) Uani 1 1 d . . . . .
H14 H 0.659013 0.872676 1.183040 0.033 Uiso 1 1 calc R . . . .
C1 C 0.7174(2) -0.1735(2) 0.69467(18) 0.0284(4) Uani 1 1 d . . . . .
H1 H 0.699750 -0.271390 0.701550 0.034 Uiso 1 1 calc R . . . .
C15 C 0.7997(2) 0.7457(2) 1.12442(18) 0.0303(4) Uani 1 1 d . . . . .
H15 H 0.885875 0.795570 1.205882 0.036 Uiso 1 1 calc R . . . .
C6 C 0.6700(2) -0.0648(2) 0.77898(18) 0.0300(4) Uani 1 1 d . . . . .
H6 H 0.619859 -0.088178 0.843671 0.036 Uiso 1 1 calc R . . . .
C19 C 0.8975(3) 0.2359(2) 0.15890(19) 0.0351(5) Uani 1 1 d . . . . .
H19A H 0.935136 0.277246 0.094331 0.053 Uiso 1 1 calc GR . . . .
H19B H 0.798446 0.140121 0.112564 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.986457 0.213251 0.205015 0.053 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 C18 1.7492(17) . ?
S1 C19 1.7986(19) . ?
O1 C17 1.212(2) . ?
O2 C18 1.202(2) . ?
N1 C7 1.4747(19) . ?
N1 C10 1.276(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.577(2) . ?
C7 C4 1.515(2) . ?
C11 C10 1.482(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.401(2) . ?
C10 C9 1.516(2) . ?
C18 C17 1.546(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(2) . ?
C3 C2 1.389(2) . ?
C17 C8 1.503(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.526(2) . ?
C8 H8 1.0000 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C1 H1 0.9500 . ?
C1 C6 1.388(3) . ?
C15 H15 0.9500 . ?
C6 H6 0.9500 . ?
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
C18 S1 C19 98.45(9) . . ?
C10 N1 C7 109.69(13) . . ?
N1 C7 H7 109.0 . . ?
N1 C7 C8 105.42(12) . . ?
N1 C7 C4 111.72(13) . . ?
C8 C7 H7 109.0 . . ?
C4 C7 H7 109.0 . . ?
C4 C7 C8 112.48(12) . . ?
C12 C11 C10 119.98(15) . . ?
C12 C11 C16 119.33(15) . . ?
C16 C11 C10 120.68(15) . . ?
N1 C10 C11 122.47(14) . . ?
N1 C10 C9 115.55(14) . . ?
C11 C10 C9 121.97(14) . . ?
O2 C18 S1 125.86(14) . . ?
O2 C18 C17 121.15(15) . . ?
C17 C18 S1 112.99(11) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.33(16) . . ?
O1 C17 C18 118.83(15) . . ?
O1 C17 C8 125.38(15) . . ?
C8 C17 C18 115.77(13) . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C10 C9 C8 102.12(13) . . ?
H9A C9 H9B 109.2 . . ?
C8 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C7 C8 H8 111.0 . . ?
C17 C8 C7 108.62(13) . . ?
C17 C8 C9 112.14(13) . . ?
C17 C8 H8 111.0 . . ?
C9 C8 C7 102.90(12) . . ?
C9 C8 H8 111.0 . . ?
C3 C4 C7 119.35(14) . . ?
C5 C4 C7 121.66(14) . . ?
C5 C4 C3 118.99(15) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.61(16) . . ?
C6 C5 H5 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.31(16) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.19(16) . . ?
C14 C13 H13 119.9 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.73(16) . . ?
C15 C16 H16 120.1 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.22(16) . . ?
C1 C2 H2 119.9 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.72(16) . . ?
C15 C14 H14 120.1 . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.83(16) . . ?
C6 C1 H1 120.1 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.68(17) . . ?
C14 C15 H15 119.7 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.02(17) . . ?
C1 C6 H6 120.0 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
S1 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'
####################################################################### 
# 
# 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_jay_3_125c_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2347215'
loop_
_audit_author_name
_audit_author_address
'Indrajit Das'
;Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2024-01-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O2 S'
_chemical_formula_sum            'C23 H17 N O2 S'
_chemical_formula_weight         371.43
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.4754(5)
_cell_length_b                   9.5803(7)
_cell_length_c                   25.2169(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1805.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9053
_cell_measurement_temperature    130.00
_cell_measurement_theta_max      74.48
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.723
_exptl_absorpt_coefficient_mu    1.734
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1399 before and 0.0900 after correction.
The Ratio of minimum to maximum transmission is 0.5777.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            33742
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.468
_diffrn_reflns_theta_min         5.800
_diffrn_ambient_temperature      130.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                3548
_reflns_number_total             3606
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.090
_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)+(0.0636P)²+0.4995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C8(H8), C10(H10), C7(H7), C20(H20), C19(H19), C17(H17),
 C18(H18), C16(H16), C3(H3), C1(H1A), C6(H6), C2(H2)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.32633(9) 1.04482(8) 0.66892(3) 0.0336(2) Uani 1 1 d . . . . .
O1 O 0.4198(3) 0.97671(19) 0.56455(7) 0.0292(4) Uani 1 1 d . . . . .
O2 O 0.5877(3) 0.8644(2) 0.68456(8) 0.0406(5) Uani 1 1 d . . . . .
N1 N 0.6929(3) 0.5994(2) 0.52276(8) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.733569 0.555679 0.494533 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6313(3) 0.7317(3) 0.52270(10) 0.0233(5) Uani 1 1 d . . . . .
C21 C 0.4932(3) 0.8886(3) 0.59292(10) 0.0249(5) Uani 1 1 d . . . . .
C9 C 0.6398(3) 0.8163(3) 0.47400(10) 0.0253(5) Uani 1 1 d . . . . .
C12 C 0.5795(3) 0.7634(3) 0.57519(10) 0.0238(5) Uani 1 1 d . . . . .
C22 C 0.4874(4) 0.9180(3) 0.65295(10) 0.0280(5) Uani 1 1 d . . . . .
C15 C 0.7439(3) 0.3987(3) 0.58424(10) 0.0248(5) Uani 1 1 d . . . . .
C13 C 0.6152(3) 0.6409(3) 0.60606(10) 0.0247(5) Uani 1 1 d . . . . .
H13 H 0.594592 0.630637 0.643035 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6841(3) 0.5412(3) 0.57292(9) 0.0241(5) Uani 1 1 d . . . . .
C8 C 0.7132(3) 0.9526(3) 0.47575(10) 0.0294(5) Uani 1 1 d . . . . .
H8 H 0.747859 0.991698 0.508801 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5867(3) 0.7613(3) 0.42613(10) 0.0265(5) Uani 1 1 d . . . . .
H10 H 0.537018 0.670034 0.425074 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7345(4) 1.0285(3) 0.43001(11) 0.0310(6) Uani 1 1 d . . . . .
H7 H 0.786437 1.118860 0.431691 0.037 Uiso 1 1 calc R U . . .
C20 C 0.6977(4) 0.3364(3) 0.63235(10) 0.0306(6) Uani 1 1 d . . . . .
H20 H 0.621052 0.384447 0.656230 0.037 Uiso 1 1 calc R U . . .
C19 C 0.7620(4) 0.2053(3) 0.64580(12) 0.0359(6) Uani 1 1 d . . . . .
H19 H 0.729138 0.164357 0.678706 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9181(4) 0.1934(3) 0.56342(13) 0.0364(6) Uani 1 1 d . . . . .
H17 H 0.993800 0.144056 0.539660 0.044 Uiso 1 1 calc R U . . .
C18 C 0.8734(4) 0.1341(3) 0.61166(13) 0.0374(7) Uani 1 1 d . . . . .
H18 H 0.919156 0.045001 0.621168 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8536(4) 0.3244(3) 0.54930(11) 0.0299(6) Uani 1 1 d . . . . .
H16 H 0.884163 0.363430 0.515876 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6047(3) 0.8378(3) 0.37845(10) 0.0279(5) Uani 1 1 d . . . . .
C5 C 0.6803(3) 0.9739(3) 0.38039(10) 0.0292(5) Uani 1 1 d . . . . .
C3 C 0.5510(4) 0.7826(3) 0.32884(11) 0.0345(6) Uani 1 1 d . . . . .
H3 H 0.498919 0.692198 0.327217 0.041 Uiso 1 1 calc R U . . .
C1 C 0.6483(4) 0.9928(4) 0.28506(12) 0.0425(7) Uani 1 1 d . . . . .
H1A H 0.662938 1.044526 0.253222 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7001(4) 1.0497(3) 0.33244(12) 0.0375(6) Uani 1 1 d . . . . .
H6 H 0.749985 1.140842 0.333195 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5733(4) 0.8579(4) 0.28324(12) 0.0423(7) Uani 1 1 d . . . . .
H2 H 0.537994 0.819153 0.250179 0.051 Uiso 1 1 calc R U . . .
C23 C 0.3600(5) 1.0492(4) 0.73967(12) 0.0498(8) Uani 1 1 d . . . . .
H23A H 0.488443 1.051698 0.747361 0.075 Uiso 1 1 calc R U . . .
H23B H 0.307138 0.965631 0.755705 0.075 Uiso 1 1 calc R U . . .
H23C H 0.302661 1.132604 0.754405 0.075 Uiso 1 1 calc R U . . .


_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 C22 1.757(3) . ?
S1 C23 1.802(3) . ?
O1 C21 1.235(3) . ?
O2 C22 1.209(3) . ?
N1 H1 0.8800 . ?
N1 C11 1.349(3) . ?
N1 C14 1.384(3) . ?
C11 C9 1.473(3) . ?
C11 C12 1.412(3) . ?
C21 C12 1.433(3) . ?
C21 C22 1.540(3) . ?
C9 C8 1.416(4) . ?
C9 C10 1.376(4) . ?
C12 C13 1.434(4) . ?
C15 C14 1.465(3) . ?
C15 C20 1.396(4) . ?
C15 C16 1.399(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.370(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.373(4) . ?
C10 H10 0.9500 . ?
C10 C4 1.415(4) . ?
C7 H7 0.9500 . ?
C7 C5 1.415(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(5) . ?
C17 C16 1.391(4) . ?
C18 H18 0.9500 . ?
C16 H16 0.9500 . ?
C4 C5 1.422(4) . ?
C4 C3 1.417(4) . ?
C5 C6 1.418(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.368(4) . ?
C1 H1A 0.9500 . ?
C1 C6 1.369(5) . ?
C1 C2 1.409(5) . ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C22 S1 C23 98.47(14) . . ?
C11 N1 H1 124.3 . . ?
C11 N1 C14 111.3(2) . . ?
C14 N1 H1 124.3 . . ?
N1 C11 C9 120.2(2) . . ?
N1 C11 C12 107.1(2) . . ?
C12 C11 C9 132.4(2) . . ?
O1 C21 C12 126.2(2) . . ?
O1 C21 C22 115.6(2) . . ?
C12 C21 C22 118.2(2) . . ?
C8 C9 C11 119.9(2) . . ?
C10 C9 C11 120.5(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C12 C21 126.6(2) . . ?
C11 C12 C13 106.4(2) . . ?
C21 C12 C13 126.8(2) . . ?
O2 C22 S1 124.6(2) . . ?
O2 C22 C21 123.5(2) . . ?
C21 C22 S1 111.78(18) . . ?
C20 C15 C14 119.5(2) . . ?
C20 C15 C16 118.4(2) . . ?
C16 C15 C14 122.1(2) . . ?
C12 C13 H13 126.0 . . ?
C14 C13 C12 108.0(2) . . ?
C14 C13 H13 126.0 . . ?
N1 C14 C15 122.6(2) . . ?
C13 C14 N1 107.1(2) . . ?
C13 C14 C15 130.2(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C4 121.3(2) . . ?
C4 C10 H10 119.4 . . ?
C8 C7 H7 119.5 . . ?
C8 C7 C5 120.9(2) . . ?
C5 C7 H7 119.5 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C18 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 120.0 . . ?
C10 C4 C5 118.9(2) . . ?
C10 C4 C3 122.0(3) . . ?
C3 C4 C5 119.1(2) . . ?
C7 C5 C4 118.9(2) . . ?
C7 C5 C6 122.4(3) . . ?
C6 C5 C4 118.8(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C6 C1 H1A 119.8 . . ?
C6 C1 C2 120.4(3) . . ?
C2 C1 H1A 119.8 . . ?
C5 C6 H6 119.6 . . ?
C1 C6 C5 120.7(3) . . ?
C1 C6 H6 119.6 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C21 C12 C11 14.8(4) . . . . ?
O1 C21 C12 C13 -159.0(3) . . . . ?
O1 C21 C22 S1 16.2(3) . . . . ?
O1 C21 C22 O2 -160.6(3) . . . . ?
N1 C11 C9 C8 -130.2(3) . . . . ?
N1 C11 C9 C10 46.0(3) . . . . ?
N1 C11 C12 C21 -174.7(2) . . . . ?
N1 C11 C12 C13 0.1(3) . . . . ?
C11 N1 C14 C15 -179.5(2) . . . . ?
C11 N1 C14 C13 -0.4(3) . . . . ?
C11 C9 C8 C7 175.0(2) . . . . ?
C11 C9 C10 C4 -175.9(2) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C21 C12 C13 C14 174.4(2) . . . . ?
C9 C11 C12 C21 10.2(4) . . . . ?
C9 C11 C12 C13 -175.0(3) . . . . ?
C9 C8 C7 C5 1.4(4) . . . . ?
C9 C10 C4 C5 0.4(4) . . . . ?
C9 C10 C4 C3 179.9(3) . . . . ?
C12 C11 C9 C8 44.4(4) . . . . ?
C12 C11 C9 C10 -139.4(3) . . . . ?
C12 C21 C22 S1 -163.12(19) . . . . ?
C12 C21 C22 O2 20.1(4) . . . . ?
C12 C13 C14 N1 0.5(3) . . . . ?
C12 C13 C14 C15 179.4(2) . . . . ?
C22 C21 C12 C11 -166.0(2) . . . . ?
C22 C21 C12 C13 20.3(4) . . . . ?
C15 C20 C19 C18 0.0(4) . . . . ?
C14 N1 C11 C9 176.0(2) . . . . ?
C14 N1 C11 C12 0.2(3) . . . . ?
C14 C15 C20 C19 -175.7(2) . . . . ?
C14 C15 C16 C17 175.2(2) . . . . ?
C8 C9 C10 C4 0.3(4) . . . . ?
C8 C7 C5 C4 -0.7(4) . . . . ?
C8 C7 C5 C6 179.9(3) . . . . ?
C10 C9 C8 C7 -1.2(4) . . . . ?
C10 C4 C5 C7 -0.2(3) . . . . ?
C10 C4 C5 C6 179.2(2) . . . . ?
C10 C4 C3 C2 -178.7(3) . . . . ?
C7 C5 C6 C1 179.1(3) . . . . ?
C20 C15 C14 N1 -166.7(2) . . . . ?
C20 C15 C14 C13 14.5(4) . . . . ?
C20 C15 C16 C17 -1.8(4) . . . . ?
C20 C19 C18 C17 -1.1(4) . . . . ?
C18 C17 C16 C15 0.8(4) . . . . ?
C16 C15 C14 N1 16.4(4) . . . . ?
C16 C15 C14 C13 -162.5(3) . . . . ?
C16 C15 C20 C19 1.4(4) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C3 C2 C1 -0.8(4) . . . . ?
C5 C4 C3 C2 0.8(4) . . . . ?
C3 C4 C5 C7 -179.7(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C23 S1 C22 O2 -3.2(3) . . . . ?
C23 S1 C22 C21 180.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
