# 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_KB1492_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2387322'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar N'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-09-27 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 N O2 S'
_chemical_formula_sum            'C19 H23 N O2 S'
_chemical_formula_weight         329.44

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6647(4)
_cell_length_b                   17.8621(5)
_cell_length_c                   7.4013(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.8140(10)
_cell_angle_gamma                90
_cell_volume                     1789.74(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4656
_cell_measurement_theta_min      3.003
_cell_measurement_theta_max      24.9545

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5911
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14932
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.280
_diffrn_reflns_theta_max         26.333
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3606
_reflns_number_gt                2434
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+3.4397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3606
_refine_ls_number_parameters     261
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1711
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.2428(3) 0.3253(2) 0.3560(6) 0.0439(10) Uani 1 1 d . . . . .
H1 H 0.252667 0.299168 0.468690 0.053 Uiso 1 1 calc R U . . .
C2 C 0.1543(3) 0.3167(3) 0.2393(6) 0.0536(12) Uani 1 1 d . . . . .
H2 H 0.104187 0.284930 0.273496 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1391(3) 0.3541(3) 0.0741(6) 0.0520(12) Uani 1 1 d . . . . .
H3 H 0.078691 0.348375 -0.004902 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2132(3) 0.4003(2) 0.0247(6) 0.0432(10) Uani 1 1 d . . . . .
H4 H 0.203273 0.426265 -0.088340 0.052 Uiso 1 1 calc R U . . .
C5 C 0.3014(3) 0.4085(2) 0.1398(5) 0.0346(9) Uani 1 1 d . . . . .
H5 H 0.352136 0.439230 0.103753 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3165(3) 0.3721(2) 0.3081(5) 0.0332(9) Uani 1 1 d . . . . .
C7 C 0.4083(3) 0.38403(19) 0.4387(5) 0.0286(8) Uani 1 1 d . . . . .
C8 C 0.4004(3) 0.4038(2) 0.6198(5) 0.0316(8) Uani 1 1 d . . . . .
H8 H 0.336529 0.406774 0.656600 0.038 Uiso 1 1 calc R U . . .
C9 C 0.4822(3) 0.4192(2) 0.7473(5) 0.0328(9) Uani 1 1 d . . . . .
H9 H 0.473598 0.433313 0.867913 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5760(3) 0.4140(2) 0.6991(5) 0.0324(9) Uani 1 1 d . . . . .
H10 H 0.632211 0.424950 0.785449 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5872(3) 0.3927(2) 0.5232(5) 0.0313(8) Uani 1 1 d . . . . .
C12 C 0.5044(3) 0.37855(19) 0.3937(4) 0.0279(8) Uani 1 1 d . . . . .
C13 C 0.4872(3) 0.2895(2) 0.1263(5) 0.0398(10) Uani 1 1 d . . . . .
H13A H 0.507050 0.286230 0.004145 0.060 Uiso 1 1 calc R U . . .
H13B H 0.414988 0.291067 0.116167 0.060 Uiso 1 1 calc R U . . .
H13C H 0.511920 0.245639 0.197920 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6841(3) 0.3816(3) 0.4542(5) 0.0519(11) Uani 1 1 d D U . . .
H14 H 0.703079 0.329113 0.490540 0.062 Uiso 1 1 calc R U . A 1
N1 N 0.5290(2) 0.35820(16) 0.2176(4) 0.0288(7) Uani 1 1 d . . . . .
O1 O 0.6583(2) 0.44862(15) 0.1337(4) 0.0408(7) Uani 1 1 d . . . . .
O2 O 0.6908(2) 0.31342(16) 0.1283(4) 0.0453(7) Uani 1 1 d . . . . .
S1 S 0.64843(7) 0.37605(6) 0.21149(12) 0.0342(3) Uani 1 1 d . . . . .
C15 C 0.7715(4) 0.4257(3) 0.5238(9) 0.0363(15) Uani 0.595(5) 1 d D U P B 1
H15C H 0.759163 0.449062 0.639923 0.044 Uiso 0.595(5) 1 calc R U P B 1
H15D H 0.777496 0.466830 0.436288 0.044 Uiso 0.595(5) 1 calc R U P B 1
C16 C 0.8715(6) 0.3854(5) 0.5584(10) 0.0555(17) Uani 0.595(5) 1 d D U P B 1
C17 C 0.9396(7) 0.4461(6) 0.6599(17) 0.071(3) Uani 0.595(5) 1 d D U P B 1
H17A H 0.943491 0.489263 0.579417 0.106 Uiso 0.595(5) 1 calc R U P B 1
H17B H 1.005854 0.425309 0.694659 0.106 Uiso 0.595(5) 1 calc R U P B 1
H17C H 0.912392 0.462017 0.769584 0.106 Uiso 0.595(5) 1 calc R U P B 1
C18 C 0.9203(8) 0.3142(5) 0.6392(15) 0.082(2) Uani 0.595(5) 1 d D U P B 1
H18A H 0.903659 0.272522 0.554525 0.123 Uiso 0.595(5) 1 calc R U P B 1
H18B H 0.896496 0.303241 0.755421 0.123 Uiso 0.595(5) 1 calc R U P B 1
H18C H 0.992086 0.321037 0.659680 0.123 Uiso 0.595(5) 1 calc R U P B 1
C19 C 0.8984(6) 0.3878(5) 0.3647(10) 0.060(2) Uani 0.595(5) 1 d D U P B 1
H19A H 0.875588 0.341770 0.300157 0.089 Uiso 0.595(5) 1 calc R U P B 1
H19B H 0.970202 0.392001 0.369805 0.089 Uiso 0.595(5) 1 calc R U P B 1
H19C H 0.866564 0.431098 0.300034 0.089 Uiso 0.595(5) 1 calc R U P B 1
C15D C 0.7699(7) 0.3451(6) 0.5492(15) 0.055(2) Uani 0.405(5) 1 d D U P B 2
H15A H 0.792261 0.308436 0.463264 0.066 Uiso 0.405(5) 1 calc R U P B 2
H15B H 0.747202 0.315796 0.649220 0.066 Uiso 0.405(5) 1 calc R U P B 2
C16D C 0.8606(8) 0.3882(7) 0.6320(14) 0.058(2) Uani 0.405(5) 1 d D U P B 2
C17D C 0.9059(11) 0.4593(8) 0.694(2) 0.068(3) Uani 0.405(5) 1 d D U P B 2
H17D H 0.916695 0.489615 0.588048 0.102 Uiso 0.405(5) 1 calc R U P B 2
H17E H 0.969415 0.449815 0.769292 0.102 Uiso 0.405(5) 1 calc R U P B 2
H17F H 0.862159 0.486186 0.766018 0.102 Uiso 0.405(5) 1 calc R U P B 2
C18D C 0.8367(9) 0.3578(7) 0.8080(14) 0.058(3) Uani 0.405(5) 1 d D U P B 2
H18D H 0.782733 0.321498 0.784210 0.086 Uiso 0.405(5) 1 calc R U P B 2
H18E H 0.816367 0.398890 0.882552 0.086 Uiso 0.405(5) 1 calc R U P B 2
H18F H 0.895122 0.333170 0.873242 0.086 Uiso 0.405(5) 1 calc R U P B 2
C19D C 0.9087(10) 0.3343(8) 0.5186(18) 0.067(2) Uani 0.405(5) 1 d D U P B 2
H19D H 0.861431 0.295070 0.473594 0.100 Uiso 0.405(5) 1 calc R U P B 2
H19E H 0.965974 0.311568 0.592580 0.100 Uiso 0.405(5) 1 calc R U P B 2
H19F H 0.930351 0.360718 0.415006 0.100 Uiso 0.405(5) 1 calc R U P B 2


_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 C6 1.391(6) . ?
C1 C2 1.395(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.491(5) . ?
C7 C12 1.401(5) . ?
C7 C8 1.405(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(5) . ?
C11 C14 1.496(5) . ?
C12 N1 1.436(4) . ?
C13 N1 1.477(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15D 1.438(8) . ?
C14 C15 1.464(6) . ?
C14 S1 1.799(4) . ?
C14 H14 1.0000 . ?
N1 S1 1.670(3) . ?
O1 S1 1.432(3) . ?
O2 S1 1.436(3) . ?
C15 C16 1.536(7) . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C16 C18 1.519(8) . ?
C16 C19 1.527(8) . ?
C16 C17 1.554(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C15D C16D 1.516(9) . ?
C15D C19D 1.950(16) . ?
C15D C18D 2.019(15) . ?
C15D H15A 0.9900 . ?
C15D H15B 0.9900 . ?
C16D C17D 1.460(9) . ?
C16D C19D 1.487(9) . ?
C16D C18D 1.488(9) . ?
C17D H17D 0.9800 . ?
C17D H17E 0.9800 . ?
C17D H17F 0.9800 . ?
C18D H18D 0.9800 . ?
C18D H18E 0.9800 . ?
C18D H18F 0.9800 . ?
C19D H19D 0.9800 . ?
C19D H19E 0.9800 . ?
C19D H19F 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
C6 C1 C2 120.4(4) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.9(4) . . ?
C1 C6 C7 119.7(3) . . ?
C5 C6 C7 121.4(3) . . ?
C12 C7 C8 116.2(3) . . ?
C12 C7 C6 124.6(3) . . ?
C8 C7 C6 119.2(3) . . ?
C9 C8 C7 122.6(4) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 C14 125.0(3) . . ?
C12 C11 C14 114.4(3) . . ?
C7 C12 C11 121.3(3) . . ?
C7 C12 N1 125.2(3) . . ?
C11 C12 N1 113.5(3) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15D C14 C11 126.4(6) . . ?
C15 C14 C11 121.7(4) . . ?
C15D C14 S1 123.7(6) . . ?
C15 C14 S1 118.6(4) . . ?
C11 C14 S1 102.4(3) . . ?
C15 C14 H14 104.0 . . ?
C11 C14 H14 104.0 . . ?
S1 C14 H14 104.0 . . ?
C12 N1 C13 120.1(3) . . ?
C12 N1 S1 109.0(2) . . ?
C13 N1 S1 117.7(3) . . ?
O1 S1 O2 117.84(17) . . ?
O1 S1 N1 109.26(16) . . ?
O2 S1 N1 108.38(17) . . ?
O1 S1 C14 108.9(2) . . ?
O2 S1 C14 113.6(2) . . ?
N1 S1 C14 96.73(17) . . ?
C14 C15 C16 118.1(6) . . ?
C14 C15 H15C 107.8 . . ?
C16 C15 H15C 107.8 . . ?
C14 C15 H15D 107.8 . . ?
C16 C15 H15D 107.8 . . ?
H15C C15 H15D 107.1 . . ?
C18 C16 C19 104.1(7) . . ?
C18 C16 C15 142.2(8) . . ?
C19 C16 C15 98.8(6) . . ?
C18 C16 C17 101.1(7) . . ?
C19 C16 C17 103.3(7) . . ?
C15 C16 C17 102.4(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C15D C16D 122.3(9) . . ?
C14 C15D C19D 136.8(9) . . ?
C16D C15D C19D 48.9(5) . . ?
C14 C15D C18D 130.2(9) . . ?
C16D C15D C18D 47.2(5) . . ?
C19D C15D C18D 78.5(6) . . ?
C14 C15D H15A 106.8 . . ?
C16D C15D H15A 106.8 . . ?
C19D C15D H15A 58.0 . . ?
C18D C15D H15A 123.0 . . ?
C14 C15D H15B 106.8 . . ?
C16D C15D H15B 106.8 . . ?
C19D C15D H15B 116.3 . . ?
C18D C15D H15B 59.8 . . ?
H15A C15D H15B 106.6 . . ?
C17D C16D C19D 122.6(11) . . ?
C17D C16D C18D 100.2(11) . . ?
C19D C16D C18D 115.2(11) . . ?
C17D C16D C15D 149.0(12) . . ?
C19D C16D C15D 81.0(9) . . ?
C18D C16D C15D 84.5(8) . . ?
C16D C17D H17D 109.5 . . ?
C16D C17D H17E 109.5 . . ?
H17D C17D H17E 109.5 . . ?
C16D C17D H17F 109.5 . . ?
H17D C17D H17F 109.5 . . ?
H17E C17D H17F 109.5 . . ?
C16D C18D C15D 48.3(5) . . ?
C16D C18D H18D 109.5 . . ?
C15D C18D H18D 61.5 . . ?
C16D C18D H18E 109.5 . . ?
C15D C18D H18E 119.5 . . ?
H18D C18D H18E 109.5 . . ?
C16D C18D H18F 109.5 . . ?
C15D C18D H18F 130.5 . . ?
H18D C18D H18F 109.5 . . ?
H18E C18D H18F 109.5 . . ?
C16D C19D C15D 50.2(5) . . ?
C16D C19D H19D 109.5 . . ?
C15D C19D H19D 60.3 . . ?
C16D C19D H19E 109.5 . . ?
C15D C19D H19E 133.8 . . ?
H19D C19D H19E 109.5 . . ?
C16D C19D H19F 109.5 . . ?
C15D C19D H19F 116.4 . . ?
H19D C19D H19F 109.5 . . ?
H19E C19D H19F 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
C6 C1 C2 C3 0.4(7) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C2 C1 C6 C5 -1.6(6) . . . . ?
C2 C1 C6 C7 176.6(4) . . . . ?
C4 C5 C6 C1 2.1(6) . . . . ?
C4 C5 C6 C7 -176.1(3) . . . . ?
C1 C6 C7 C12 131.3(4) . . . . ?
C5 C6 C7 C12 -50.5(5) . . . . ?
C1 C6 C7 C8 -50.1(5) . . . . ?
C5 C6 C7 C8 128.1(4) . . . . ?
C12 C7 C8 C9 1.7(5) . . . . ?
C6 C7 C8 C9 -177.0(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 1.8(5) . . . . ?
C9 C10 C11 C14 -177.3(4) . . . . ?
C8 C7 C12 C11 -0.5(5) . . . . ?
C6 C7 C12 C11 178.1(3) . . . . ?
C8 C7 C12 N1 179.1(3) . . . . ?
C6 C7 C12 N1 -2.3(5) . . . . ?
C10 C11 C12 C7 -1.3(5) . . . . ?
C14 C11 C12 C7 177.9(4) . . . . ?
C10 C11 C12 N1 179.1(3) . . . . ?
C14 C11 C12 N1 -1.8(5) . . . . ?
C10 C11 C14 C15D 42.2(9) . . . . ?
C12 C11 C14 C15D -136.9(7) . . . . ?
C10 C11 C14 C15 -32.0(7) . . . . ?
C12 C11 C14 C15 148.9(4) . . . . ?
C10 C11 C14 S1 -167.4(3) . . . . ?
C12 C11 C14 S1 13.5(4) . . . . ?
C7 C12 N1 C13 -51.7(5) . . . . ?
C11 C12 N1 C13 127.9(4) . . . . ?
C7 C12 N1 S1 168.1(3) . . . . ?
C11 C12 N1 S1 -12.3(4) . . . . ?
C12 N1 S1 O1 -94.8(2) . . . . ?
C13 N1 S1 O1 123.9(3) . . . . ?
C12 N1 S1 O2 135.6(2) . . . . ?
C13 N1 S1 O2 -5.7(3) . . . . ?
C12 N1 S1 C14 17.9(3) . . . . ?
C13 N1 S1 C14 -123.4(3) . . . . ?
C15D C14 S1 O1 -113.4(6) . . . . ?
C15 C14 S1 O1 -42.0(5) . . . . ?
C11 C14 S1 O1 95.2(3) . . . . ?
C15D C14 S1 O2 20.1(7) . . . . ?
C15 C14 S1 O2 91.5(4) . . . . ?
C11 C14 S1 O2 -131.3(3) . . . . ?
C15D C14 S1 N1 133.6(6) . . . . ?
C15 C14 S1 N1 -155.0(4) . . . . ?
C11 C14 S1 N1 -17.8(3) . . . . ?
C11 C14 C15 C16 139.1(6) . . . . ?
S1 C14 C15 C16 -92.2(6) . . . . ?
C14 C15 C16 C18 -43.6(15) . . . . ?
C14 C15 C16 C19 83.5(7) . . . . ?
C14 C15 C16 C17 -170.7(7) . . . . ?
C11 C14 C15D C16D -106.3(10) . . . . ?
S1 C14 C15D C16D 109.2(10) . . . . ?
C11 C14 C15D C19D -168.7(9) . . . . ?
S1 C14 C15D C19D 46.8(14) . . . . ?
C11 C14 C15D C18D -47.6(12) . . . . ?
S1 C14 C15D C18D 167.9(6) . . . . ?
C14 C15D C16D C17D 17(3) . . . . ?
C19D C15D C16D C17D 143(2) . . . . ?
C18D C15D C16D C17D -101(2) . . . . ?
C14 C15D C16D C19D -126.3(11) . . . . ?
C18D C15D C16D C19D 116.6(11) . . . . ?
C14 C15D C16D C18D 117.1(11) . . . . ?
C19D C15D C16D C18D -116.6(11) . . . . ?
C17D C16D C18D C15D 149.1(12) . . . . ?
C19D C16D C18D C15D -77.3(10) . . . . ?
C17D C16D C19D C15D -158.3(15) . . . . ?
C18D C16D C19D C15D 79.5(9) . . . . ?

_refine_diff_density_max         0.666
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_KB1601_0m
_database_code_depnum_ccdc_archive 'CCDC 2387323'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar N'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-09-27 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2 O2 S'
_chemical_formula_sum            'C20 H22 N2 O2 S'
_chemical_formula_weight         354.45

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   14.3600(4)
_cell_length_b                   9.5280(3)
_cell_length_c                   28.4766(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3896.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6018
_cell_measurement_theta_min      2.1635
_cell_measurement_theta_max      21.7415

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6413
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28438
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4854
_reflns_number_gt                2413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1307P)²+0.7962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4854
_refine_ls_number_parameters     288
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2536
_refine_ls_wR_factor_gt          0.2042
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.4232(3) 0.8596(4) 0.67878(13) 0.0905(11) Uani 1 1 d . . . . .
H1 H 0.379717 0.802381 0.663938 0.109 Uiso 1 1 calc R U . A 1
C4 C 0.5441(5) 1.0257(6) 0.73019(17) 0.1291(19) Uani 1 1 d . . . . .
H4 H 0.588165 1.076940 0.746903 0.155 Uiso 1 1 calc R U . B 1
C5 C 0.5741(3) 0.9593(4) 0.68968(12) 0.0881(11) Uani 1 1 d . . . . .
H5 H 0.635590 0.969540 0.680014 0.106 Uiso 1 1 calc R U . . .
C6 C 0.5136(2) 0.8778(3) 0.66334(11) 0.0659(8) Uani 1 1 d . . . . .
C7 C 0.54263(19) 0.8176(3) 0.61752(10) 0.0563(7) Uani 1 1 d . . . . .
C8 C 0.48727(19) 0.8386(3) 0.57812(11) 0.0609(7) Uani 1 1 d . . . . .
H8 H 0.431508 0.887236 0.581361 0.073 Uiso 1 1 calc R U . . .
C9 C 0.51222(19) 0.7899(3) 0.53474(11) 0.0612(8) Uani 1 1 d . . . . .
H9 H 0.473334 0.805293 0.509130 0.073 Uiso 1 1 calc R U . . .
C10 C 0.59474(18) 0.7182(3) 0.52878(10) 0.0547(7) Uani 1 1 d . . . . .
C11 C 0.65072(17) 0.6915(3) 0.56786(10) 0.0543(7) Uani 1 1 d . . . . .
C12 C 0.62547(18) 0.7395(3) 0.61210(10) 0.0562(7) Uani 1 1 d . . . . .
C13 C 0.6789(2) 0.7026(4) 0.65259(12) 0.0741(9) Uani 1 1 d . . . . .
C14 C 0.6367(2) 0.6655(4) 0.48341(11) 0.0710(9) Uani 1 1 d . . . . .
H14 H 0.670808 0.742108 0.468186 0.085 Uiso 1 1 calc R U . C 1
C15 C 0.8203(2) 0.6240(4) 0.57760(14) 0.0928(12) Uani 1 1 d . . . . .
H15A H 0.865677 0.579942 0.557715 0.139 Uiso 1 1 calc R U . . .
H15B H 0.820967 0.580085 0.607937 0.139 Uiso 1 1 calc R U . . .
H15C H 0.834923 0.721821 0.580879 0.139 Uiso 1 1 calc R U . . .
C17 C 0.5978(3) 0.6425(4) 0.39450(12) 0.0768(9) Uani 1 1 d . U . . .
N1 N 0.7215(2) 0.6697(5) 0.68510(12) 0.1178(13) Uani 1 1 d . . . . .
N2 N 0.72940(15) 0.6092(3) 0.55703(9) 0.0660(7) Uani 1 1 d . . . . .
O1 O 0.67472(19) 0.4040(2) 0.50925(10) 0.0954(8) Uani 1 1 d . . . . .
O2 O 0.80598(16) 0.5408(2) 0.48154(10) 0.0855(7) Uani 1 1 d . . . . .
S1 S 0.71772(5) 0.53728(8) 0.50434(3) 0.0676(3) Uani 1 1 d . . . . .
C2 C 0.4030(12) 0.9445(17) 0.7231(6) 0.097(4) Uani 0.525(7) 1 d . U P D 1
H2 H 0.343345 0.942960 0.735788 0.116 Uiso 0.525(7) 1 calc R U P D 1
C3 C 0.4707(9) 1.0232(18) 0.7449(5) 0.096(3) Uani 0.525(7) 1 d . U P D 1
H3 H 0.456187 1.074560 0.771655 0.115 Uiso 0.525(7) 1 calc R U P D 1
C16 C 0.5737(11) 0.6018(12) 0.4497(6) 0.072(3) Uani 0.525(7) 1 d . U P D 1
H16A H 0.510661 0.631505 0.456791 0.086 Uiso 0.525(7) 1 calc R U P D 1
H16B H 0.576346 0.500650 0.453287 0.086 Uiso 0.525(7) 1 calc R U P D 1
C18 C 0.6477(8) 0.7651(10) 0.3735(4) 0.121(2) Uani 0.525(7) 1 d . U P D 1
H18A H 0.646853 0.757524 0.339929 0.182 Uiso 0.525(7) 1 calc R U P D 1
H18B H 0.710974 0.766200 0.384389 0.182 Uiso 0.525(7) 1 calc R U P D 1
H18C H 0.617232 0.850397 0.382846 0.182 Uiso 0.525(7) 1 calc R U P D 1
C19 C 0.5070(11) 0.6230(15) 0.3704(6) 0.114(3) Uani 0.525(7) 1 d . U P D 1
H19A H 0.514678 0.638187 0.337337 0.172 Uiso 0.525(7) 1 calc R U P D 1
H19B H 0.462682 0.689031 0.382655 0.172 Uiso 0.525(7) 1 calc R U P D 1
H19C H 0.484938 0.529270 0.375777 0.172 Uiso 0.525(7) 1 calc R U P D 1
C20 C 0.6628(7) 0.5119(10) 0.3837(3) 0.090(2) Uani 0.525(7) 1 d . U P D 1
H20A H 0.670383 0.502361 0.350338 0.136 Uiso 0.525(7) 1 calc R U P D 1
H20B H 0.634698 0.428264 0.396078 0.136 Uiso 0.525(7) 1 calc R U P D 1
H20C H 0.722496 0.525868 0.398068 0.136 Uiso 0.525(7) 1 calc R U P D 1
C2D C 0.3823(15) 0.900(2) 0.7158(7) 0.101(4) Uani 0.475(7) 1 d . U P D 2
H2D H 0.321677 0.873138 0.723033 0.121 Uiso 0.475(7) 1 calc R U P D 2
C3D C 0.4332(10) 0.9848(19) 0.7443(7) 0.102(4) Uani 0.475(7) 1 d . U P D 2
H3D H 0.406807 1.020507 0.771598 0.123 Uiso 0.475(7) 1 calc R U P D 2
C16D C 0.5700(15) 0.6415(17) 0.4429(7) 0.088(3) Uani 0.475(7) 1 d . U P D 2
H16C H 0.540851 0.551129 0.448406 0.106 Uiso 0.475(7) 1 calc R U P D 2
H16D H 0.521286 0.711387 0.445936 0.106 Uiso 0.475(7) 1 calc R U P D 2
C18D C 0.5846(7) 0.8041(9) 0.3902(4) 0.094(2) Uani 0.475(7) 1 d . U P D 2
H18D H 0.600432 0.833486 0.358929 0.140 Uiso 0.475(7) 1 calc R U P D 2
H18E H 0.624248 0.850739 0.412343 0.140 Uiso 0.475(7) 1 calc R U P D 2
H18F H 0.520805 0.827622 0.396538 0.140 Uiso 0.475(7) 1 calc R U P D 2
C19D C 0.5197(11) 0.5689(12) 0.3649(5) 0.088(3) Uani 0.475(7) 1 d . U P D 2
H19D H 0.459896 0.603903 0.374472 0.132 Uiso 0.475(7) 1 calc R U P D 2
H19E H 0.522186 0.469427 0.370058 0.132 Uiso 0.475(7) 1 calc R U P D 2
H19F H 0.529115 0.588466 0.332215 0.132 Uiso 0.475(7) 1 calc R U P D 2
C20D C 0.6884(7) 0.5940(13) 0.3810(4) 0.099(2) Uani 0.475(7) 1 d . U P D 2
H20D H 0.697982 0.612223 0.348208 0.149 Uiso 0.475(7) 1 calc R U P D 2
H20E H 0.692881 0.494944 0.386733 0.149 Uiso 0.475(7) 1 calc R U P D 2
H20F H 0.734873 0.642302 0.399034 0.149 Uiso 0.475(7) 1 calc R U P D 2


_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 C2D 1.266(19) . ?
C1 C6 1.382(5) . ?
C1 C2 1.528(17) . ?
C1 H1 0.9300 . ?
C4 C3 1.135(12) . ?
C4 C5 1.384(6) . ?
C4 C3D 1.688(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.485(4) . ?
C7 C8 1.389(4) . ?
C7 C12 1.412(4) . ?
C8 C9 1.367(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(4) . ?
C10 C14 1.511(4) . ?
C11 C12 1.388(4) . ?
C11 N2 1.409(3) . ?
C12 C13 1.429(4) . ?
C13 N1 1.153(4) . ?
C14 C16 1.451(18) . ?
C14 C16D 1.52(2) . ?
C14 S1 1.790(3) . ?
C14 H14 0.9800 . ?
C15 N2 1.437(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C20D 1.432(10) . ?
C17 C16D 1.43(2) . ?
C17 C19 1.485(16) . ?
C17 C18 1.494(10) . ?
C17 C18D 1.556(9) . ?
C17 C19D 1.568(14) . ?
C17 C20 1.585(9) . ?
C17 C16 1.657(17) . ?
N2 S1 1.658(3) . ?
O1 S1 1.419(3) . ?
O2 S1 1.424(2) . ?
C2 C3 1.374(16) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C2D C3D 1.358(19) . ?
C2D H2D 0.9300 . ?
C3D H3D 0.9300 . ?
C16D H16C 0.9700 . ?
C16D H16D 0.9700 . ?
C18D H18D 0.9600 . ?
C18D H18E 0.9600 . ?
C18D H18F 0.9600 . ?
C19D H19D 0.9600 . ?
C19D H19E 0.9600 . ?
C19D H19F 0.9600 . ?
C20D H20D 0.9600 . ?
C20D H20E 0.9600 . ?
C20D H20F 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
C2D C1 C6 131.5(10) . . ?
C6 C1 C2 112.0(7) . . ?
C6 C1 H1 124.0 . . ?
C2 C1 H1 124.0 . . ?
C3 C4 C5 125.9(10) . . ?
C5 C4 C3D 112.7(9) . . ?
C3 C4 H4 117.1 . . ?
C5 C4 H4 117.1 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 119.6(3) . . ?
C5 C6 C7 121.1(3) . . ?
C8 C7 C12 118.0(3) . . ?
C8 C7 C6 119.6(3) . . ?
C12 C7 C6 122.4(3) . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 C14 127.8(3) . . ?
C11 C10 C14 113.1(2) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 N2 126.2(2) . . ?
C10 C11 N2 112.8(2) . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 C13 120.7(3) . . ?
C7 C12 C13 119.6(3) . . ?
N1 C13 C12 178.5(5) . . ?
C16 C14 C10 117.1(7) . . ?
C10 C14 C16D 116.7(9) . . ?
C16 C14 S1 109.8(6) . . ?
C10 C14 S1 101.6(2) . . ?
C16D C14 S1 124.1(7) . . ?
C16 C14 H14 109.3 . . ?
C10 C14 H14 109.3 . . ?
S1 C14 H14 109.3 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20D C17 C16D 120.6(10) . . ?
C19 C17 C18 109.5(8) . . ?
C20D C17 C18D 114.2(6) . . ?
C16D C17 C18D 92.8(8) . . ?
C20D C17 C19D 111.2(7) . . ?
C16D C17 C19D 108.2(11) . . ?
C18D C17 C19D 108.2(6) . . ?
C19 C17 C20 109.2(6) . . ?
C18 C17 C20 104.8(6) . . ?
C19 C17 C16 103.0(9) . . ?
C18 C17 C16 131.5(7) . . ?
C20 C17 C16 97.1(6) . . ?
C11 N2 C15 125.8(3) . . ?
C11 N2 S1 110.31(19) . . ?
C15 N2 S1 120.1(2) . . ?
O1 S1 O2 116.96(15) . . ?
O1 S1 N2 108.97(16) . . ?
O2 S1 N2 108.23(15) . . ?
O1 S1 C14 111.15(17) . . ?
O2 S1 C14 114.24(16) . . ?
N2 S1 C14 94.86(13) . . ?
C3 C2 C1 121.8(12) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 120.2(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C14 C16 C17 113.5(8) . . ?
C14 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C14 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 C2D C3D 115.3(18) . . ?
C1 C2D H2D 122.3 . . ?
C3D C2D H2D 122.3 . . ?
C2D C3D C4 120.2(16) . . ?
C2D C3D H3D 119.9 . . ?
C4 C3D H3D 119.9 . . ?
C17 C16D C14 123.6(15) . . ?
C17 C16D H16C 106.4 . . ?
C14 C16D H16C 106.4 . . ?
C17 C16D H16D 106.4 . . ?
C14 C16D H16D 106.4 . . ?
H16C C16D H16D 106.5 . . ?
C17 C18D H18D 109.5 . . ?
C17 C18D H18E 109.5 . . ?
H18D C18D H18E 109.5 . . ?
C17 C18D H18F 109.5 . . ?
H18D C18D H18F 109.5 . . ?
H18E C18D H18F 109.5 . . ?
C17 C19D H19D 109.5 . . ?
C17 C19D H19E 109.5 . . ?
H19D C19D H19E 109.5 . . ?
C17 C19D H19F 109.5 . . ?
H19D C19D H19F 109.5 . . ?
H19E C19D H19F 109.5 . . ?
C17 C20D H20D 109.5 . . ?
C17 C20D H20E 109.5 . . ?
H20D C20D H20E 109.5 . . ?
C17 C20D H20F 109.5 . . ?
H20D C20D H20F 109.5 . . ?
H20E C20D H20F 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
C3 C4 C5 C6 -1.7(13) . . . . ?
C3D C4 C5 C6 4.4(9) . . . . ?
C2D C1 C6 C5 -3.9(15) . . . . ?
C2 C1 C6 C5 3.6(9) . . . . ?
C2D C1 C6 C7 180.0(14) . . . . ?
C2 C1 C6 C7 -172.5(8) . . . . ?
C4 C5 C6 C1 -2.0(5) . . . . ?
C4 C5 C6 C7 174.0(4) . . . . ?
C1 C6 C7 C8 47.9(4) . . . . ?
C5 C6 C7 C8 -128.2(3) . . . . ?
C1 C6 C7 C12 -132.5(3) . . . . ?
C5 C6 C7 C12 51.5(4) . . . . ?
C12 C7 C8 C9 -2.0(4) . . . . ?
C6 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 2.3(4) . . . . ?
C8 C9 C10 C14 -175.5(3) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C14 C10 C11 C12 176.4(3) . . . . ?
C9 C10 C11 N2 175.9(2) . . . . ?
C14 C10 C11 N2 -6.0(4) . . . . ?
C10 C11 C12 C7 -0.7(4) . . . . ?
N2 C11 C12 C7 -178.0(3) . . . . ?
C10 C11 C12 C13 174.9(3) . . . . ?
N2 C11 C12 C13 -2.4(5) . . . . ?
C8 C7 C12 C11 2.5(4) . . . . ?
C6 C7 C12 C11 -177.1(3) . . . . ?
C8 C7 C12 C13 -173.2(3) . . . . ?
C6 C7 C12 C13 7.2(4) . . . . ?
C9 C10 C14 C16 -41.7(7) . . . . ?
C11 C10 C14 C16 140.4(6) . . . . ?
C9 C10 C14 C16D -23.3(8) . . . . ?
C11 C10 C14 C16D 158.8(7) . . . . ?
C9 C10 C14 S1 -161.3(3) . . . . ?
C11 C10 C14 S1 20.8(3) . . . . ?
C12 C11 N2 C15 -38.8(5) . . . . ?
C10 C11 N2 C15 143.7(3) . . . . ?
C12 C11 N2 S1 163.6(2) . . . . ?
C10 C11 N2 S1 -13.9(3) . . . . ?
C11 N2 S1 O1 -90.9(2) . . . . ?
C15 N2 S1 O1 110.0(3) . . . . ?
C11 N2 S1 O2 140.9(2) . . . . ?
C15 N2 S1 O2 -18.2(3) . . . . ?
C11 N2 S1 C14 23.4(2) . . . . ?
C15 N2 S1 C14 -135.7(3) . . . . ?
C16 C14 S1 O1 -36.7(7) . . . . ?
C10 C14 S1 O1 87.9(2) . . . . ?
C16D C14 S1 O1 -45.9(10) . . . . ?
C16 C14 S1 O2 98.3(7) . . . . ?
C10 C14 S1 O2 -137.1(2) . . . . ?
C16D C14 S1 O2 89.1(9) . . . . ?
C16 C14 S1 N2 -149.2(7) . . . . ?
C10 C14 S1 N2 -24.6(2) . . . . ?
C16D C14 S1 N2 -158.4(9) . . . . ?
C6 C1 C2 C3 -2.6(15) . . . . ?
C5 C4 C3 C2 2.9(18) . . . . ?
C1 C2 C3 C4 -0.6(19) . . . . ?
C10 C14 C16 C17 141.1(7) . . . . ?
S1 C14 C16 C17 -103.7(8) . . . . ?
C19 C17 C16 C14 -155.8(10) . . . . ?
C18 C17 C16 C14 -24.3(16) . . . . ?
C20 C17 C16 C14 92.6(10) . . . . ?
C6 C1 C2D C3D 6(2) . . . . ?
C1 C2D C3D C4 -2(2) . . . . ?
C5 C4 C3D C2D -2.7(14) . . . . ?
C20D C17 C16D C14 33.0(18) . . . . ?
C18D C17 C16D C14 -87.3(13) . . . . ?
C19D C17 C16D C14 162.5(12) . . . . ?
C10 C14 C16D C17 156.3(10) . . . . ?
S1 C14 C16D C17 -76.0(14) . . . . ?

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.048

