# Supplementary Information (SI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_TMC14
_database_code_depnum_ccdc_archive 'CCDC 2495663'
loop_
_audit_author_name
_audit_author_address
'MUNUGALA CHANDRAKANTH'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2026-02-20 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         'C22 H26 F N3 O3 S2'
_chemical_formula_sum            'C22 H26 F N3 O3 S2'
_chemical_formula_weight         463.58

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.9028(8)
_cell_length_b                   10.2282(8)
_cell_length_c                   12.4585(10)
_cell_angle_alpha                84.732(3)
_cell_angle_beta                 85.951(3)
_cell_angle_gamma                65.261(3)
_cell_volume                     1140.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)


_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.45
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5630
_exptl_absorpt_correction_T_max  0.7456


_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption 
 correction
 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer equipped with PHOTON II detector'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49337
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.846
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4476
_reflns_number_gt                3590
_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       'APEX4 (Bruker, v2021.4-0)'
_computing_cell_refinement       'APEX4 V8.40B (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012) '
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'

_refine_special_details          
;
  Isopropyl group is disordered over two positions with an occupancy 
  ratio of 81:19.The positions of disordered atoms were
  located from difference electron density peaks. DFIX
  restraint was used to attain target bond distances of 1.54 A 
  for C-C bonds and 1.48 A for C-O bonds. Anisotropic displacement 
  parameters(Uij) of atoms in the disordered groups were 
  restrained to be equal using SIMU restraint.
;




_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.6496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4476
_refine_ls_number_parameters     316
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.033
_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 -0.0108(3) 0.7478(3) 1.02596(18) 0.0497(6) Uani 1 1 d . . . . .
C2 C -0.0702(3) 0.7761(3) 1.1398(2) 0.0671(8) Uani 1 1 d . . . . .
H2A H -0.174735 0.794580 1.146695 0.081 Uiso 1 1 calc R U . . .
H2B H -0.056862 0.856759 1.164915 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0258(4) 0.6348(4) 1.2002(2) 0.0831(10) Uani 1 1 d . . . . .
H3A H -0.036497 0.589141 1.233626 0.100 Uiso 1 1 calc R U . . .
H3B H 0.076541 0.653597 1.256741 0.100 Uiso 1 1 calc R U . . .
C4 C 0.1409(3) 0.5335(3) 1.12192(18) 0.0547(6) Uani 1 1 d . . . . .
H4A H 0.241558 0.511718 1.141342 0.066 Uiso 1 1 calc R U . . .
H4B H 0.129380 0.444045 1.120395 0.066 Uiso 1 1 calc R U . . .
C5 C 0.1044(3) 0.6201(2) 1.01558(17) 0.0426(5) Uani 1 1 d . . . . .
C6 C 0.1618(2) 0.5992(2) 0.90660(16) 0.0399(5) Uani 1 1 d . . . . .
C7 C 0.0818(2) 0.7166(2) 0.83817(16) 0.0383(5) Uani 1 1 d . . . . .
C8 C 0.0507(2) 0.8242(2) 0.64918(17) 0.0379(5) Uani 1 1 d . . . . .
C9 C 0.1806(2) 0.6452(2) 0.51166(16) 0.0396(5) Uani 1 1 d . . . . .
C10 C 0.1445(2) 0.5306(2) 0.54583(17) 0.0435(5) Uani 1 1 d . . . . .
H10 H 0.064056 0.543636 0.593599 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2293(3) 0.3974(2) 0.50802(18) 0.0440(5) Uani 1 1 d . . . . .
C12 C 0.3468(2) 0.3714(2) 0.43245(17) 0.0406(5) Uani 1 1 d . . . . .
C13 C 0.3779(3) 0.4895(2) 0.39888(18) 0.0460(5) Uani 1 1 d . . . . .
H13 H 0.455074 0.477893 0.348295 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2974(3) 0.6247(2) 0.43851(18) 0.0457(5) Uani 1 1 d . . . . .
H14 H 0.322409 0.701063 0.415567 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3451(3) 0.1692(3) 0.3441(2) 0.0599(7) Uani 1 1 d . . . . .
H15A H 0.313813 0.221535 0.274860 0.072 Uiso 1 1 calc R U . . .
H15B H 0.256900 0.178023 0.387542 0.072 Uiso 1 1 calc R U . . .
C16 C 0.4414(3) 0.0117(3) 0.3278(3) 0.0712(8) Uani 1 1 d . . . . .
H16A H 0.466072 -0.041254 0.397523 0.085 Uiso 1 1 calc R U . . .
H16B H 0.385849 -0.027796 0.290245 0.085 Uiso 1 1 calc R U . . .
C17 C 0.6560(3) 0.0487(3) 0.3235(3) 0.0767(9) Uani 1 1 d . . . . .
H17A H 0.748006 0.034314 0.283114 0.092 Uiso 1 1 calc R U . . .
H17B H 0.681262 -0.003418 0.393444 0.092 Uiso 1 1 calc R U . . .
C18 C 0.5682(3) 0.2079(3) 0.3385(2) 0.0621(7) Uani 1 1 d . . . . .
H18A H 0.626312 0.243070 0.377486 0.075 Uiso 1 1 calc R U . . .
H18B H 0.547153 0.261137 0.268678 0.075 Uiso 1 1 calc R U . . .
C19 C 0.2890(3) 0.4743(3) 0.86760(18) 0.0503(6) Uani 1 1 d . . . . .
N1 N 0.1090(2) 0.71784(19) 0.72712(14) 0.0436(5) Uani 1 1 d D . . . .
N2 N 0.0938(2) 0.78628(19) 0.54755(15) 0.0451(5) Uani 1 1 d D . . . .
N3 N 0.4297(2) 0.2309(2) 0.39827(16) 0.0457(5) Uani 1 1 d . . . . .
O1 O 0.3259(2) 0.4564(2) 0.77258(14) 0.0800(7) Uani 1 1 d . . . . .
O2 O 0.3631(2) 0.38254(19) 0.94692(13) 0.0627(5) Uani 1 1 d D . . . .
O3 O 0.5740(2) -0.0071(2) 0.26784(17) 0.0698(5) Uani 1 1 d . . . . .
S1 S -0.06519(7) 0.99418(6) 0.67450(5) 0.04836(18) Uani 1 1 d . . . . .
S2 S -0.05805(7) 0.85273(6) 0.90569(5) 0.05226(19) Uani 1 1 d . . . . .
F1 F 0.19475(18) 0.28705(15) 0.54753(13) 0.0678(5) Uani 1 1 d . . . . .
C20 C 0.4892(4) 0.2454(4) 0.9194(3) 0.0551(10) Uani 0.817(7) 1 d D U P A 1
H20 H 0.460324 0.201745 0.863369 0.066 Uiso 0.817(7) 1 calc R U P A 1
C21 C 0.6179(5) 0.2752(5) 0.8804(5) 0.0991(18) Uani 0.817(7) 1 d D U P A 1
H21A H 0.593870 0.336257 0.814947 0.149 Uiso 0.817(7) 1 calc R U P A 1
H21B H 0.642353 0.322631 0.934029 0.149 Uiso 0.817(7) 1 calc R U P A 1
H21C H 0.701440 0.186039 0.866783 0.149 Uiso 0.817(7) 1 calc R U P A 1
C22 C 0.5162(8) 0.1511(7) 1.0209(5) 0.171(5) Uani 0.817(7) 1 d D U P A 1
H22A H 0.428710 0.135597 1.042243 0.256 Uiso 0.817(7) 1 calc R U P A 1
H22B H 0.598207 0.060164 1.009349 0.256 Uiso 0.817(7) 1 calc R U P A 1
H22C H 0.539120 0.196755 1.076595 0.256 Uiso 0.817(7) 1 calc R U P A 1
C20' C 0.5315(17) 0.3084(19) 0.9305(12) 0.068(5) Uani 0.183(7) 1 d D U P A 2
H20' H 0.572513 0.371575 0.890673 0.081 Uiso 0.183(7) 1 calc R U P A 2
C21' C 0.530(3) 0.195(2) 0.863(2) 0.104(9) Uani 0.183(7) 1 d D U P A 2
H21D H 0.481368 0.239873 0.796698 0.156 Uiso 0.183(7) 1 calc R U P A 2
H21E H 0.630096 0.128118 0.846957 0.156 Uiso 0.183(7) 1 calc R U P A 2
H21F H 0.476848 0.144325 0.901555 0.156 Uiso 0.183(7) 1 calc R U P A 2
C22' C 0.6052(19) 0.246(2) 1.0342(13) 0.076(6) Uani 0.183(7) 1 d D U P A 2
H22D H 0.603968 0.321319 1.074889 0.113 Uiso 0.183(7) 1 calc R U P A 2
H22E H 0.553009 0.195423 1.074656 0.113 Uiso 0.183(7) 1 calc R U P A 2
H22F H 0.706257 0.179216 1.020058 0.113 Uiso 0.183(7) 1 calc R U P A 2
H2N H 0.069(3) 0.855(2) 0.4978(17) 0.050(7) Uiso 1 1 d D . . B 2
H1N H 0.182(2) 0.641(2) 0.7099(19) 0.048(7) Uiso 1 1 d D . . C 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 C5 1.337(3) . ?
C1 C2 1.502(3) . ?
C1 S2 1.732(2) . ?
C2 C3 1.520(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.538(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.501(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.433(3) . ?
C6 C7 1.381(3) . ?
C6 C19 1.462(3) . ?
C7 N1 1.391(3) . ?
C7 S2 1.732(2) . ?
C8 N2 1.346(3) . ?
C8 N1 1.349(3) . ?
C8 S1 1.679(2) . ?
C9 C14 1.376(3) . ?
C9 C10 1.386(3) . ?
C9 N2 1.431(3) . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 F1 1.353(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.389(3) . ?
C12 N3 1.413(3) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N3 1.468(3) . ?
C15 C16 1.514(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.412(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.416(4) . ?
C17 C18 1.513(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N3 1.452(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O1 1.221(3) . ?
C19 O2 1.324(3) . ?
N1 H1N 0.849(16) . ?
N2 H2N 0.855(16) . ?
O2 C20 1.485(4) . ?
O2 C20' 1.523(15) . ?
C20 C21 1.471(6) . ?
C20 C22 1.485(5) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20' C22' 1.484(15) . ?
C20' C21' 1.502(17) . ?
C20' H20' 0.9800 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 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
C5 C1 C2 114.3(2) . . ?
C5 C1 S2 113.50(17) . . ?
C2 C1 S2 132.1(2) . . ?
C1 C2 C3 101.5(2) . . ?
C1 C2 H2A 111.5 . . ?
C3 C2 H2A 111.5 . . ?
C1 C2 H2B 111.5 . . ?
C3 C2 H2B 111.5 . . ?
H2A C2 H2B 109.3 . . ?
C2 C3 C4 110.0(2) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 102.7(2) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C1 C5 C6 112.7(2) . . ?
C1 C5 C4 111.4(2) . . ?
C6 C5 C4 135.9(2) . . ?
C7 C6 C5 111.21(19) . . ?
C7 C6 C19 121.80(19) . . ?
C5 C6 C19 126.98(19) . . ?
C6 C7 N1 122.06(18) . . ?
C6 C7 S2 112.47(15) . . ?
N1 C7 S2 125.39(16) . . ?
N2 C8 N1 115.44(18) . . ?
N2 C8 S1 121.12(16) . . ?
N1 C8 S1 123.43(16) . . ?
C14 C9 C10 119.65(19) . . ?
C14 C9 N2 119.5(2) . . ?
C10 C9 N2 120.83(19) . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
F1 C11 C10 117.01(19) . . ?
F1 C11 C12 119.32(19) . . ?
C10 C11 C12 123.7(2) . . ?
C13 C12 C11 115.56(19) . . ?
C13 C12 N3 124.1(2) . . ?
C11 C12 N3 120.3(2) . . ?
C12 C13 C14 122.1(2) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C9 C14 C13 120.0(2) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N3 C15 C16 109.6(2) . . ?
N3 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N3 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O3 C16 C15 111.8(2) . . ?
O3 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
O3 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
O3 C17 C18 111.4(2) . . ?
O3 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
O3 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 C17 109.9(2) . . ?
N3 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
N3 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O1 C19 O2 123.0(2) . . ?
O1 C19 C6 124.3(2) . . ?
O2 C19 C6 112.66(19) . . ?
C8 N1 C7 130.55(18) . . ?
C8 N1 H1N 118.0(17) . . ?
C7 N1 H1N 111.0(17) . . ?
C8 N2 C9 128.12(18) . . ?
C8 N2 H2N 116.7(17) . . ?
C9 N2 H2N 115.1(17) . . ?
C12 N3 C18 116.0(2) . . ?
C12 N3 C15 115.53(18) . . ?
C18 N3 C15 110.34(19) . . ?
C19 O2 C20 118.7(2) . . ?
C19 O2 C20' 116.5(6) . . ?
C16 O3 C17 109.2(2) . . ?
C1 S2 C7 90.06(11) . . ?
C21 C20 C22 113.3(5) . . ?
C21 C20 O2 109.2(4) . . ?
C22 C20 O2 104.8(3) . . ?
C21 C20 H20 109.8 . . ?
C22 C20 H20 109.8 . . ?
O2 C20 H20 109.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C22' C20' C21' 112.1(16) . . ?
C22' C20' O2 111.4(12) . . ?
C21' C20' O2 95.1(17) . . ?
C22' C20' H20' 112.4 . . ?
C21' C20' H20' 112.4 . . ?
O2 C20' H20' 112.4 . . ?
C20' C21' H21D 109.5 . . ?
C20' C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20' C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C20' C22' H22D 109.5 . . ?
C20' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C20' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 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
C5 C1 C2 C3 -3.3(3) . . . . ?
S2 C1 C2 C3 180.0(2) . . . . ?
C1 C2 C3 C4 2.7(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C1 C5 C6 -177.7(2) . . . . ?
S2 C1 C5 C6 -0.4(3) . . . . ?
C2 C1 C5 C4 2.6(3) . . . . ?
S2 C1 C5 C4 179.98(17) . . . . ?
C3 C4 C5 C1 -0.7(3) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C1 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C1 C5 C6 C19 178.2(2) . . . . ?
C4 C5 C6 C19 -2.3(4) . . . . ?
C5 C6 C7 N1 -175.2(2) . . . . ?
C19 C6 C7 N1 5.7(4) . . . . ?
C5 C6 C7 S2 1.6(3) . . . . ?
C19 C6 C7 S2 -177.40(18) . . . . ?
C14 C9 C10 C11 1.9(3) . . . . ?
N2 C9 C10 C11 178.9(2) . . . . ?
C9 C10 C11 F1 176.8(2) . . . . ?
C9 C10 C11 C12 -3.2(4) . . . . ?
F1 C11 C12 C13 -177.9(2) . . . . ?
C10 C11 C12 C13 2.1(3) . . . . ?
F1 C11 C12 N3 -0.6(3) . . . . ?
C10 C11 C12 N3 179.4(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
N3 C12 C13 C14 -177.0(2) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
N2 C9 C14 C13 -176.8(2) . . . . ?
C12 C13 C14 C9 -1.4(4) . . . . ?
N3 C15 C16 O3 -57.4(3) . . . . ?
O3 C17 C18 N3 58.7(3) . . . . ?
C7 C6 C19 O1 -7.5(4) . . . . ?
C5 C6 C19 O1 173.6(3) . . . . ?
C7 C6 C19 O2 171.2(2) . . . . ?
C5 C6 C19 O2 -7.6(4) . . . . ?
N2 C8 N1 C7 -175.3(2) . . . . ?
S1 C8 N1 C7 5.9(4) . . . . ?
C6 C7 N1 C8 -174.9(2) . . . . ?
S2 C7 N1 C8 8.7(4) . . . . ?
N1 C8 N2 C9 7.1(3) . . . . ?
S1 C8 N2 C9 -174.11(19) . . . . ?
C14 C9 N2 C8 -133.1(2) . . . . ?
C10 C9 N2 C8 49.9(3) . . . . ?
C13 C12 N3 C18 10.1(3) . . . . ?
C11 C12 N3 C18 -167.0(2) . . . . ?
C13 C12 N3 C15 -121.3(3) . . . . ?
C11 C12 N3 C15 61.6(3) . . . . ?
C17 C18 N3 C12 170.8(2) . . . . ?
C17 C18 N3 C15 -55.5(3) . . . . ?
C16 C15 N3 C12 -171.3(2) . . . . ?
C16 C15 N3 C18 54.7(3) . . . . ?
O1 C19 O2 C20 -5.4(5) . . . . ?
C6 C19 O2 C20 175.8(3) . . . . ?
O1 C19 O2 C20' 35.3(9) . . . . ?
C6 C19 O2 C20' -143.5(9) . . . . ?
C15 C16 O3 C17 59.8(3) . . . . ?
C18 C17 O3 C16 -60.1(3) . . . . ?
C5 C1 S2 C7 1.1(2) . . . . ?
C2 C1 S2 C7 177.8(3) . . . . ?
C6 C7 S2 C1 -1.56(19) . . . . ?
N1 C7 S2 C1 175.2(2) . . . . ?
C19 O2 C20 C21 75.2(5) . . . . ?
C19 O2 C20 C22 -163.1(5) . . . . ?
C19 O2 C20' C22' 162.4(12) . . . . ?
C19 O2 C20' C21' -81.5(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15B F1 0.97 2.29 2.936(3) 123.0 . yes
C21^a H21A^a O1 0.96 2.49 3.035(5) 116.2 . yes
C21'^b H21D^b O1 0.96 2.11 2.78(2) 125.7 . yes
N2 H2N^b S1 0.855(16) 2.521(18) 3.3487(19) 163(2) 2_576 yes
N1 H1N^b O1 0.849(16) 1.96(2) 2.677(2) 142(2) . yes

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_TMC1-12
_database_code_depnum_ccdc_archive 'CCDC 2495664'
loop_
_audit_author_name
_audit_author_address
'MUNUGALA CHANDRAKANTH'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2026-02-20 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         'C22 H27 N3 O3 S2'
_chemical_formula_sum            'C22 H27 N3 O3 S2'
_chemical_formula_weight         445.58

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.6883(8)
_cell_length_b                   9.9058(7)
_cell_length_c                   12.6922(10)
_cell_angle_alpha                84.153(3)
_cell_angle_beta                 82.661(3)
_cell_angle_gamma                68.325(3)
_cell_volume                     1120.70(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9843
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.78
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.266
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5318
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption 
 correction
 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer equipped with PHOTON II detector'
_diffrn_measurement_method       'omega and phi scans'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45385
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         25.992
_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             4394
_reflns_number_gt                3619
_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       'APEX4 (Bruker, v2021.4-0)'
_computing_cell_refinement       'APEX4 V8.40B (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'

_refine_special_details          
;
  cyclohexyl group is disordered over two positions with an occupancy 
  ratio of 62:38.The positions of disordered atoms were
  located from difference electron density peaks. DFIX
  restraint was used to attain target bond distances of 1.52 A 
  for C-C bonds. Anisotropic displacement 
  parameters(Uij) of atoms in the disordered groups were 
  restrained to be equal using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0783P)²+0.7887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4394
_refine_ls_number_parameters     307
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.095
_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 0.3852(3) 0.8767(3) -0.01544(19) 0.0401(5) Uani 1 1 d . U . . .
C2 C 0.4855(4) 0.8146(3) -0.1139(2) 0.0559(7) Uani 1 1 d D U . . .
H2A H 0.513308 0.709690 -0.110448 0.067 Uiso 1 1 calc R U . A 1
H2B H 0.575788 0.836617 -0.119010 0.067 Uiso 1 1 calc R U . A 1
C3 C 0.3975(13) 0.8848(9) -0.2134(4) 0.090(3) Uani 0.624(13) 1 d D U P B 1
H3A H 0.467062 0.913832 -0.263760 0.108 Uiso 0.624(13) 1 calc R U P B 1
H3B H 0.385089 0.804527 -0.243874 0.108 Uiso 0.624(13) 1 calc R U P B 1
C4 C 0.2880(8) 0.9767(12) -0.2183(4) 0.073(2) Uani 0.624(13) 1 d D U P B 1
H4A H 0.221041 0.936344 -0.242315 0.087 Uiso 0.624(13) 1 calc R U P B 1
H4B H 0.304132 1.043740 -0.275476 0.087 Uiso 0.624(13) 1 calc R U P B 1
C5 C 0.2014(18) 1.069(2) -0.1268(8) 0.059(3) Uani 0.624(13) 1 d D U P B 1
H5A H 0.096344 1.084307 -0.125199 0.070 Uiso 0.624(13) 1 calc R U P B 1
H5B H 0.212059 1.163074 -0.136646 0.070 Uiso 0.624(13) 1 calc R U P B 1
C3' C 0.4582(9) 0.9200(10) -0.2083(6) 0.044(2) Uani 0.376(13) 1 d D U P B 2
H3'1 H 0.471012 0.864952 -0.270079 0.053 Uiso 0.376(13) 1 calc R U P B 2
H3'2 H 0.536697 0.960096 -0.217036 0.053 Uiso 0.376(13) 1 calc R U P B 2
C4' C 0.3066(11) 1.0507(11) -0.2120(6) 0.051(2) Uani 0.376(13) 1 d D U P B 2
H4'1 H 0.330703 1.137444 -0.230440 0.061 Uiso 0.376(13) 1 calc R U P B 2
H4'2 H 0.259777 1.037612 -0.271408 0.061 Uiso 0.376(13) 1 calc R U P B 2
C5' C 0.187(3) 1.086(4) -0.1177(13) 0.052(4) Uani 0.376(13) 1 d D U P B 2
H5'1 H 0.152126 1.188279 -0.104720 0.062 Uiso 0.376(13) 1 calc R U P B 2
H5'2 H 0.102545 1.062134 -0.131729 0.062 Uiso 0.376(13) 1 calc R U P B 2
C6 C 0.2588(3) 0.9940(3) -0.02257(19) 0.0442(6) Uani 1 1 d D U . . .
C7 C 0.4089(3) 0.8238(3) 0.09389(18) 0.0367(5) Uani 1 1 d . U . . .
C8 C 0.2955(2) 0.9066(3) 0.16476(18) 0.0349(5) Uani 1 1 d . U . . .
C9 C 0.1874(3) 0.9415(3) 0.35241(18) 0.0370(5) Uani 1 1 d . U . . .
C10 C 0.3654(3) 0.8101(3) 0.48704(18) 0.0388(5) Uani 1 1 d . U . . .
C11 C 0.4916(3) 0.8441(3) 0.4576(2) 0.0439(6) Uani 1 1 d . U . . .
H11 H 0.486514 0.923674 0.410451 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6252(3) 0.7610(3) 0.4977(2) 0.0443(6) Uani 1 1 d . U . . .
H12 H 0.709576 0.784056 0.475579 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6362(3) 0.6432(3) 0.57051(19) 0.0388(5) Uani 1 1 d . U . . .
C14 C 0.5080(3) 0.6099(3) 0.5991(2) 0.0463(6) Uani 1 1 d . U . . .
H14 H 0.512013 0.531256 0.646973 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3746(3) 0.6922(3) 0.5574(2) 0.0456(6) Uani 1 1 d . U . . .
H15 H 0.290673 0.667577 0.577013 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8562(4) 0.6423(4) 0.6458(3) 0.0651(9) Uani 1 1 d . U . . .
H16A H 0.803076 0.690840 0.709616 0.078 Uiso 1 1 calc R U . . .
H16B H 0.862368 0.716338 0.591160 0.078 Uiso 1 1 calc R U . . .
C17 C 1.0112(4) 0.5436(4) 0.6688(4) 0.0833(11) Uani 1 1 d . U . . .
H17A H 1.067666 0.503049 0.603355 0.100 Uiso 1 1 calc R U . . .
H17B H 1.061228 0.599708 0.695776 0.100 Uiso 1 1 calc R U . . .
C18 C 0.9349(5) 0.3482(4) 0.7057(4) 0.0998(15) Uani 1 1 d . U . . .
H18A H 0.934073 0.269236 0.757402 0.120 Uiso 1 1 calc R U . . .
H18B H 0.990183 0.305753 0.640503 0.120 Uiso 1 1 calc R U . . .
C19 C 0.7774(4) 0.4386(4) 0.6843(3) 0.0748(10) Uani 1 1 d . U . . .
H19A H 0.733390 0.379120 0.654769 0.090 Uiso 1 1 calc R U . . .
H19B H 0.718945 0.473752 0.750484 0.090 Uiso 1 1 calc R U . . .
C20 C 0.5332(3) 0.6995(3) 0.1336(2) 0.0455(6) Uani 1 1 d . U . . .
C21 C 0.7531(5) 0.4947(6) 0.0916(4) 0.1124(18) Uani 1 1 d D U . . .
H21A H 0.824336 0.526861 0.118743 0.135 Uiso 1 1 calc R U . . .
H21B H 0.717894 0.438656 0.148509 0.135 Uiso 1 1 calc R U . . .
C22 C 0.8231(8) 0.4071(7) 0.0057(5) 0.167(3) Uani 1 1 d D U . . .
H22A H 0.905407 0.324412 0.028890 0.251 Uiso 1 1 calc R U . . .
H22B H 0.752668 0.374423 -0.020359 0.251 Uiso 1 1 calc R U . . .
H22C H 0.858877 0.462435 -0.050060 0.251 Uiso 1 1 calc R U . . .
N1 N 0.2968(2) 0.8840(2) 0.27449(15) 0.0382(5) Uani 1 1 d D U . . .
N2 N 0.2239(2) 0.9001(3) 0.45200(16) 0.0462(5) Uani 1 1 d D U . . .
N3 N 0.7737(3) 0.5610(2) 0.61044(19) 0.0486(5) Uani 1 1 d . U . . .
O1 O 0.5519(2) 0.6663(2) 0.22660(15) 0.0589(5) Uani 1 1 d . U . . .
O2 O 0.6262(2) 0.6223(3) 0.05710(17) 0.0766(7) Uani 1 1 d . U . . .
O3 O 1.0080(3) 0.4290(3) 0.7443(2) 0.0878(8) Uani 1 1 d . U . . .
S1 S 0.16089(7) 1.04447(7) 0.10041(5) 0.0466(2) Uani 1 1 d . U . . .
S2 S 0.01495(7) 1.05571(8) 0.32846(5) 0.0492(2) Uani 1 1 d . U . . .
H1N H 0.377(2) 0.820(2) 0.290(2) 0.045(7) Uiso 1 1 d D . . . .
H2N H 0.154(3) 0.922(3) 0.502(2) 0.056(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.346(4) . ?
C1 C7 1.448(3) . ?
C1 C2 1.513(3) . ?
C2 C3' 1.489(8) . ?
C2 C3 1.570(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.117(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.513(13) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.514(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3' C4' 1.561(11) . ?
C3' H3'1 0.9700 . ?
C3' H3'2 0.9700 . ?
C4' C5' 1.526(17) . ?
C4' H4'1 0.9700 . ?
C4' H4'2 0.9700 . ?
C5' C6 1.514(17) . ?
C5' H5'1 0.9700 . ?
C5' H5'2 0.9700 . ?
C6 S1 1.737(3) . ?
C7 C8 1.386(3) . ?
C7 C20 1.467(3) . ?
C8 N1 1.389(3) . ?
C8 S1 1.721(2) . ?
C9 N2 1.339(3) . ?
C9 N1 1.352(3) . ?
C9 S2 1.682(2) . ?
C10 C15 1.379(4) . ?
C10 C11 1.382(4) . ?
C10 N2 1.429(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(4) . ?
C13 N3 1.408(3) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N3 1.460(4) . ?
C16 C17 1.505(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.416(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O3 1.403(5) . ?
C18 C19 1.500(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N3 1.447(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O1 1.211(3) . ?
C20 O2 1.326(3) . ?
C21 C22 1.404(6) . ?
C21 O2 1.476(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 H1N 0.831(17) . ?
N2 H2N 0.847(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C7 112.0(2) . . ?
C6 C1 C2 121.2(2) . . ?
C7 C1 C2 126.8(2) . . ?
C3' C2 C1 112.6(4) . . ?
C1 C2 C3 108.0(4) . . ?
C1 C2 H2A 110.1 . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C3 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C4 C3 C2 129.4(6) . . ?
C4 C3 H3A 104.9 . . ?
C2 C3 H3A 104.9 . . ?
C4 C3 H3B 104.9 . . ?
C2 C3 H3B 104.9 . . ?
H3A C3 H3B 105.8 . . ?
C3 C4 C5 124.6(7) . . ?
C3 C4 H4A 106.2 . . ?
C5 C4 H4A 106.2 . . ?
C3 C4 H4B 106.2 . . ?
C5 C4 H4B 106.2 . . ?
H4A C4 H4B 106.4 . . ?
C4 C5 C6 110.1(8) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C2 C3' C4' 120.2(6) . . ?
C2 C3' H3'1 107.3 . . ?
C4' C3' H3'1 107.3 . . ?
C2 C3' H3'2 107.3 . . ?
C4' C3' H3'2 107.3 . . ?
H3'1 C3' H3'2 106.9 . . ?
C5' C4' C3' 122.8(10) . . ?
C5' C4' H4'1 106.6 . . ?
C3' C4' H4'1 106.6 . . ?
C5' C4' H4'2 106.6 . . ?
C3' C4' H4'2 106.6 . . ?
H4'1 C4' H4'2 106.6 . . ?
C6 C5' C4' 106.6(12) . . ?
C6 C5' H5'1 110.4 . . ?
C4' C5' H5'1 110.4 . . ?
C6 C5' H5'2 110.4 . . ?
C4' C5' H5'2 110.4 . . ?
H5'1 C5' H5'2 108.6 . . ?
C1 C6 C5 123.9(5) . . ?
C1 C6 C5' 131.6(8) . . ?
C1 C6 S1 113.03(18) . . ?
C5 C6 S1 122.9(5) . . ?
C5' C6 S1 115.4(7) . . ?
C8 C7 C1 111.9(2) . . ?
C8 C7 C20 120.1(2) . . ?
C1 C7 C20 128.1(2) . . ?
C7 C8 N1 123.1(2) . . ?
C7 C8 S1 111.93(17) . . ?
N1 C8 S1 124.89(17) . . ?
N2 C9 N1 115.6(2) . . ?
N2 C9 S2 121.11(18) . . ?
N1 C9 S2 123.28(18) . . ?
C15 C10 C11 119.0(2) . . ?
C15 C10 N2 119.4(2) . . ?
C11 C10 N2 121.4(2) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 117.4(2) . . ?
C12 C13 N3 120.0(2) . . ?
C14 C13 N3 122.5(2) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C10 C15 C14 120.6(2) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
N3 C16 C17 111.3(3) . . ?
N3 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O3 C17 C16 111.4(3) . . ?
O3 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
O3 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
O3 C18 C19 112.7(3) . . ?
O3 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
O3 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
N3 C19 C18 110.7(3) . . ?
N3 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
O1 C20 O2 121.4(2) . . ?
O1 C20 C7 125.0(2) . . ?
O2 C20 C7 113.6(2) . . ?
C22 C21 O2 110.0(4) . . ?
C22 C21 H21A 109.7 . . ?
O2 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
O2 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 N1 C8 129.6(2) . . ?
C9 N1 H1N 119.5(19) . . ?
C8 N1 H1N 110.6(19) . . ?
C9 N2 C10 128.7(2) . . ?
C9 N2 H2N 117(2) . . ?
C10 N2 H2N 114(2) . . ?
C13 N3 C19 117.0(2) . . ?
C13 N3 C16 116.8(2) . . ?
C19 N3 C16 110.9(2) . . ?
C20 O2 C21 116.4(3) . . ?
C18 O3 C17 109.4(3) . . ?
C8 S1 C6 91.14(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3' 18.9(5) . . . . ?
C7 C1 C2 C3' -160.7(4) . . . . ?
C6 C1 C2 C3 -12.9(6) . . . . ?
C7 C1 C2 C3 167.5(5) . . . . ?
C1 C2 C3 C4 9.0(14) . . . . ?
C2 C3 C4 C5 6(2) . . . . ?
C3 C4 C5 C6 -16(2) . . . . ?
C1 C2 C3' C4' -21.3(7) . . . . ?
C2 C3' C4' C5' 6(2) . . . . ?
C3' C4' C5' C6 12(4) . . . . ?
C7 C1 C6 C5 -177.2(13) . . . . ?
C2 C1 C6 C5 3.2(14) . . . . ?
C7 C1 C6 C5' -180(2) . . . . ?
C2 C1 C6 C5' 1(2) . . . . ?
C7 C1 C6 S1 -1.0(3) . . . . ?
C2 C1 C6 S1 179.3(2) . . . . ?
C4 C5 C6 C1 11(2) . . . . ?
C4 C5 C6 S1 -164.6(9) . . . . ?
C4' C5' C6 C1 -16(4) . . . . ?
C4' C5' C6 S1 165.3(16) . . . . ?
C6 C1 C7 C8 0.1(3) . . . . ?
C2 C1 C7 C8 179.7(2) . . . . ?
C6 C1 C7 C20 -179.8(2) . . . . ?
C2 C1 C7 C20 -0.2(4) . . . . ?
C1 C7 C8 N1 -175.7(2) . . . . ?
C20 C7 C8 N1 4.2(4) . . . . ?
C1 C7 C8 S1 0.9(3) . . . . ?
C20 C7 C8 S1 -179.17(19) . . . . ?
C15 C10 C11 C12 0.3(4) . . . . ?
N2 C10 C11 C12 175.9(2) . . . . ?
C10 C11 C12 C13 -1.6(4) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
C11 C12 C13 N3 -179.6(2) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
N3 C13 C14 C15 -179.3(2) . . . . ?
C11 C10 C15 C14 0.8(4) . . . . ?
N2 C10 C15 C14 -174.9(2) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
N3 C16 C17 O3 -56.0(4) . . . . ?
O3 C18 C19 N3 56.6(5) . . . . ?
C8 C7 C20 O1 -5.1(4) . . . . ?
C1 C7 C20 O1 174.8(3) . . . . ?
C8 C7 C20 O2 174.2(2) . . . . ?
C1 C7 C20 O2 -5.9(4) . . . . ?
N2 C9 N1 C8 -178.8(2) . . . . ?
S2 C9 N1 C8 2.1(4) . . . . ?
C7 C8 N1 C9 -170.1(2) . . . . ?
S1 C8 N1 C9 13.6(4) . . . . ?
N1 C9 N2 C10 4.0(4) . . . . ?
S2 C9 N2 C10 -176.9(2) . . . . ?
C15 C10 N2 C9 -128.0(3) . . . . ?
C11 C10 N2 C9 56.4(4) . . . . ?
C12 C13 N3 C19 -178.9(3) . . . . ?
C14 C13 N3 C19 -0.4(4) . . . . ?
C12 C13 N3 C16 46.3(4) . . . . ?
C14 C13 N3 C16 -135.2(3) . . . . ?
C18 C19 N3 C13 170.8(3) . . . . ?
C18 C19 N3 C16 -51.8(4) . . . . ?
C17 C16 N3 C13 -170.3(3) . . . . ?
C17 C16 N3 C19 52.2(4) . . . . ?
O1 C20 O2 C21 -0.2(5) . . . . ?
C7 C20 O2 C21 -179.4(3) . . . . ?
C22 C21 O2 C20 167.7(5) . . . . ?
C19 C18 O3 C17 -59.4(5) . . . . ?
C16 C17 O3 C18 58.7(5) . . . . ?
C7 C8 S1 C6 -1.27(19) . . . . ?
N1 C8 S1 C6 175.3(2) . . . . ?
C1 C6 S1 C8 1.3(2) . . . . ?
C5 C6 S1 C8 177.5(13) . . . . ?
C5' C6 S1 C8 -179.9(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14 O1 0.93 2.61 3.511(3) 164.6 2_666 yes
N1 H1N O1 0.831(17) 1.96(2) 2.660(3) 141(3) . yes
N2 H2N S2 0.847(17) 2.509(19) 3.341(2) 168(3) 2_576 yes
C14 H14 O1 0.93 2.61 3.511(3) 164.6 2_666 yes
N1 H1N O1 0.831(17) 1.96(2) 2.660(3) 141(3) . yes
N2 H2N S2 0.847(17) 2.509(19) 3.341(2) 168(3) 2_576 yes

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.057

