# Electronic Supplementary Material (ESI) 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_1
_database_code_depnum_ccdc_archive 'CCDC 2120465'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Guo'
;Shanxi University
China
;
_audit_update_record             
;
2021-11-06 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H45 N3 O6 S3'
_chemical_formula_weight         820.02

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.2283(6)
_cell_length_b                   14.9598(6)
_cell_length_c                   20.4993(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.1990(10)
_cell_angle_gamma                90
_cell_volume                     4351.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44821
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.723
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             10734
_reflns_number_gt                7389
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0539P)²+2.0407P] 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         10734
_refine_ls_number_parameters     520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.44325(13) 0.89622(14) 0.29553(9) 0.0477(4) Uani 1 1 d . . . . .
C2 C 0.41295(16) 0.8909(2) 0.35771(11) 0.0782(8) Uani 1 1 d . . . . .
H2 H 0.4563 0.8860 0.3937 0.094 Uiso 1 1 calc R U . . .
C3 C 0.31737(17) 0.8930(2) 0.36602(12) 0.0835(9) Uani 1 1 d . . . . .
H3 H 0.2976 0.8892 0.4082 0.100 Uiso 1 1 calc R U . . .
C4 C 0.25044(14) 0.90031(16) 0.31430(12) 0.0599(5) Uani 1 1 d . . . . .
C5 C 0.14643(16) 0.9012(2) 0.32452(15) 0.0838(8) Uani 1 1 d . . . . .
H5A H 0.1155 0.9452 0.2964 0.126 Uiso 1 1 calc R U . . .
H5B H 0.1376 0.9156 0.3693 0.126 Uiso 1 1 calc R U . . .
H5C H 0.1201 0.8433 0.3144 0.126 Uiso 1 1 calc R U . . .
C6 C 0.28227(14) 0.90606(16) 0.25276(11) 0.0597(5) Uani 1 1 d . . . . .
H6 H 0.2389 0.9115 0.2168 0.072 Uiso 1 1 calc R U . . .
C7 C 0.37718(14) 0.90388(16) 0.24311(10) 0.0558(5) Uani 1 1 d . . . . .
H7 H 0.3968 0.9076 0.2009 0.067 Uiso 1 1 calc R U . . .
C8 C 0.61587(13) 0.89047(13) 0.32375(9) 0.0458(4) Uani 1 1 d . . . . .
C9 C 0.81058(13) 0.89181(16) 0.34425(10) 0.0534(5) Uani 1 1 d . . . . .
C10 C 0.84919(16) 0.96417(16) 0.37791(12) 0.0647(6) Uani 1 1 d . . . . .
H10 H 0.8228 1.0206 0.3709 0.078 Uiso 1 1 calc R U . . .
C11 C 0.92634(16) 0.95391(15) 0.42175(12) 0.0644(6) Uani 1 1 d . . . . .
H11 H 0.9518 1.0033 0.4442 0.077 Uiso 1 1 calc R U . . .
C12 C 0.96602(13) 0.87051(14) 0.43253(10) 0.0486(4) Uani 1 1 d . . . . .
C13 C 0.92771(15) 0.79779(15) 0.39973(11) 0.0572(5) Uani 1 1 d . . . . .
H13 H 0.9535 0.7413 0.4072 0.069 Uiso 1 1 calc R U . . .
C14 C 0.85059(15) 0.80900(16) 0.35565(11) 0.0608(6) Uani 1 1 d . . . . .
H14 H 0.8251 0.7596 0.3332 0.073 Uiso 1 1 calc R U . . .
C15 C 1.09013(19) 0.7841(2) 0.48631(15) 0.0863(8) Uani 1 1 d . . . . .
H15A H 1.0482 0.7422 0.5045 0.129 Uiso 1 1 calc R U . . .
H15B H 1.1447 0.7923 0.5161 0.129 Uiso 1 1 calc R U . . .
H15C H 1.1092 0.7616 0.4454 0.129 Uiso 1 1 calc R U . . .
C16 C 0.75972(15) 0.75021(14) 0.50939(10) 0.0517(5) Uani 1 1 d . . . . .
C17 C 0.76637(18) 0.83833(16) 0.52870(12) 0.0651(6) Uani 1 1 d . . . . .
H17 H 0.7245 0.8803 0.5098 0.078 Uiso 1 1 calc R U . . .
C18 C 0.83460(19) 0.86460(17) 0.57572(13) 0.0735(7) Uani 1 1 d . . . . .
H18 H 0.8380 0.9244 0.5881 0.088 Uiso 1 1 calc R U . . .
C19 C 0.89838(17) 0.80461(17) 0.60515(11) 0.0640(6) Uani 1 1 d . . . . .
C20 C 0.9753(2) 0.8330(2) 0.65603(15) 0.0907(9) Uani 1 1 d . . . . .
H20A H 0.9728 0.7963 0.6943 0.136 Uiso 1 1 calc R U . . .
H20B H 0.9661 0.8944 0.6676 0.136 Uiso 1 1 calc R U . . .
H20C H 1.0356 0.8264 0.6385 0.136 Uiso 1 1 calc R U . . .
C21 C 0.89128(17) 0.71715(17) 0.58488(11) 0.0650(6) Uani 1 1 d . . . . .
H21 H 0.9338 0.6755 0.6035 0.078 Uiso 1 1 calc R U . . .
C22 C 0.82321(16) 0.68896(16) 0.53787(11) 0.0611(5) Uani 1 1 d . . . . .
H22 H 0.8200 0.6292 0.5254 0.073 Uiso 1 1 calc R U . . .
C23 C 0.65794(15) 0.64582(15) 0.44212(10) 0.0546(5) Uani 1 1 d . . . . .
C24 C 0.54016(17) 0.53939(18) 0.36265(12) 0.0683(6) Uani 1 1 d . . . . .
C25 C 0.57382(16) 0.48944(19) 0.31264(12) 0.0676(6) Uani 1 1 d . . . . .
H25 H 0.6171 0.5143 0.2860 0.081 Uiso 1 1 calc R U . . .
C26 C 0.54343(16) 0.40328(19) 0.30217(11) 0.0663(6) Uani 1 1 d . . . . .
H26 H 0.5668 0.3700 0.2686 0.080 Uiso 1 1 calc R U . . .
C27 C 0.47833(15) 0.36495(18) 0.34096(11) 0.0632(6) Uani 1 1 d . . . . .
C28 C 0.44436(18) 0.4150(2) 0.39097(12) 0.0757(7) Uani 1 1 d . . . . .
H28 H 0.4008 0.3903 0.4175 0.091 Uiso 1 1 calc R U . . .
C29 C 0.47515(19) 0.5008(2) 0.40130(13) 0.0800(8) Uani 1 1 d . . . . .
H29 H 0.4520 0.5340 0.4350 0.096 Uiso 1 1 calc R U . . .
C30 C 0.3893(2) 0.2364(3) 0.36660(16) 0.1007(10) Uani 1 1 d . . . . .
H30A H 0.4148 0.2382 0.4112 0.151 Uiso 1 1 calc R U . . .
H30B H 0.3807 0.1754 0.3530 0.151 Uiso 1 1 calc R U . . .
H30C H 0.3297 0.2667 0.3629 0.151 Uiso 1 1 calc R U . . .
C31 C 0.72822(13) 0.33762(13) 0.41502(10) 0.0490(4) Uani 1 1 d . . . . .
C32 C 0.73747(16) 0.26787(15) 0.37154(12) 0.0604(5) Uani 1 1 d . . . . .
H32 H 0.7752 0.2740 0.3366 0.072 Uiso 1 1 calc R U . . .
C33 C 0.68951(19) 0.18856(16) 0.38098(14) 0.0725(7) Uani 1 1 d . . . . .
H33 H 0.6952 0.1419 0.3515 0.087 Uiso 1 1 calc R U . . .
C34 C 0.63357(19) 0.17667(17) 0.43263(15) 0.0760(7) Uani 1 1 d . . . . .
C35 C 0.5828(3) 0.0884(2) 0.4416(2) 0.1193(13) Uani 1 1 d . . . . .
H35A H 0.5392 0.0951 0.4749 0.179 Uiso 1 1 calc R U . . .
H35B H 0.6281 0.0430 0.4546 0.179 Uiso 1 1 calc R U . . .
H35C H 0.5493 0.0716 0.4012 0.179 Uiso 1 1 calc R U . . .
C36 C 0.62579(19) 0.24676(18) 0.47504(14) 0.0742(7) Uani 1 1 d . . . . .
H36 H 0.5885 0.2405 0.5101 0.089 Uiso 1 1 calc R U . . .
C37 C 0.67242(16) 0.32670(15) 0.46660(12) 0.0601(5) Uani 1 1 d . . . . .
H37 H 0.6660 0.3733 0.4959 0.072 Uiso 1 1 calc R U . . .
C38 C 0.85142(14) 0.44069(13) 0.38051(9) 0.0481(4) Uani 1 1 d . . . . .
C39 C 0.99125(16) 0.56657(14) 0.36525(11) 0.0574(5) Uani 1 1 d . . . . .
C40 C 1.01879(18) 0.61268(17) 0.31143(12) 0.0677(6) Uani 1 1 d . . . . .
H40 H 0.9737 0.6327 0.2796 0.081 Uiso 1 1 calc R U . . .
C41 C 1.11445(18) 0.62938(17) 0.30465(13) 0.0695(6) Uani 1 1 d . . . . .
H41 H 1.1329 0.6617 0.2690 0.083 Uiso 1 1 calc R U . . .
C42 C 1.18068(17) 0.59793(16) 0.35075(13) 0.0665(6) Uani 1 1 d . . . . .
C43 C 1.1538(2) 0.55099(18) 0.40392(12) 0.0728(7) Uani 1 1 d . . . . .
H43 H 1.1991 0.5290 0.4348 0.087 Uiso 1 1 calc R U . . .
C44 C 1.0606(2) 0.53675(17) 0.41116(12) 0.0696(6) Uani 1 1 d . . . . .
H44 H 1.0430 0.5062 0.4479 0.084 Uiso 1 1 calc R U . . .
C45 C 1.3083(2) 0.6506(3) 0.2917(2) 0.1177(13) Uani 1 1 d . . . . .
H45A H 1.2809 0.6212 0.2533 0.177 Uiso 1 1 calc R U . . .
H45B H 1.3757 0.6461 0.2929 0.177 Uiso 1 1 calc R U . . .
H45C H 1.2902 0.7124 0.2909 0.177 Uiso 1 1 calc R U . . .
N1 N 0.53932(11) 0.89662(13) 0.28152(8) 0.0548(4) Uani 1 1 d . . . . .
H1 H 0.5500 0.9014 0.2409 0.066 Uiso 1 1 calc R U . . .
N2 N 0.68971(13) 0.72730(12) 0.45954(9) 0.0581(4) Uani 1 1 d . . . . .
H2A H 0.6644 0.7713 0.4377 0.070 Uiso 1 1 calc R U . . .
N3 N 0.77098(12) 0.42245(11) 0.40793(9) 0.0516(4) Uani 1 1 d . . . . .
H3A H 0.7418 0.4674 0.4230 0.062 Uiso 1 1 calc R U . . .
O1 O 0.61609(10) 0.87692(10) 0.38204(7) 0.0540(3) Uani 1 1 d . . . . .
O2 O 1.04324(11) 0.86741(12) 0.47573(8) 0.0691(4) Uani 1 1 d . . . . .
O3 O 0.68130(10) 0.57561(10) 0.46877(7) 0.0575(4) Uani 1 1 d . . . . .
O4 O 0.45263(13) 0.27949(14) 0.32596(9) 0.0829(5) Uani 1 1 d . . . . .
O5 O 0.90484(10) 0.38694(10) 0.35834(7) 0.0550(4) Uani 1 1 d . . . . .
O6 O 1.27592(13) 0.60933(15) 0.34795(12) 0.0980(7) Uani 1 1 d . . . . .
S1 S 0.72046(4) 0.90774(6) 0.28188(3) 0.0817(2) Uani 1 1 d . . . . .
S2 S 0.57422(6) 0.65262(5) 0.37282(4) 0.0965(3) Uani 1 1 d . . . . .
S3 S 0.87070(5) 0.55905(4) 0.37888(5) 0.0864(3) Uani 1 1 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 C2 1.377(3) . ?
C1 C7 1.380(3) . ?
C1 N1 1.417(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.374(3) . ?
C4 C5 1.510(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.212(2) . ?
C8 N1 1.344(2) . ?
C8 S1 1.790(2) . ?
C9 C14 1.376(3) . ?
C9 C10 1.376(3) . ?
C9 S1 1.759(2) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 O2 1.361(2) . ?
C12 C13 1.371(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O2 1.422(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.378(3) . ?
C16 C22 1.385(3) . ?
C16 N2 1.416(3) . ?
C17 C18 1.374(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C21 1.374(3) . ?
C19 C20 1.516(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O3 1.219(2) . ?
C23 N2 1.339(3) . ?
C23 S2 1.789(2) . ?
C24 C25 1.382(3) . ?
C24 C29 1.387(4) . ?
C24 S2 1.770(3) . ?
C25 C26 1.371(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9300 . ?
C27 O4 1.359(3) . ?
C27 C28 1.385(3) . ?
C28 C29 1.368(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 O4 1.425(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C37 1.378(3) . ?
C31 C32 1.385(3) . ?
C31 N3 1.419(3) . ?
C32 C33 1.389(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.382(4) . ?
C33 H33 0.9300 . ?
C34 C36 1.372(4) . ?
C34 C35 1.522(4) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.385(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 O5 1.217(2) . ?
C38 N3 1.340(3) . ?
C38 S3 1.792(2) . ?
C39 C40 1.382(3) . ?
C39 C44 1.387(3) . ?
C39 S3 1.761(2) . ?
C40 C41 1.401(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.368(3) . ?
C41 H41 0.9300 . ?
C42 O6 1.371(3) . ?
C42 C43 1.374(4) . ?
C43 C44 1.362(4) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 O6 1.414(4) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?

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
C2 C1 C7 118.94(19) . . ?
C2 C1 N1 124.03(18) . . ?
C7 C1 N1 117.01(17) . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 122.5(2) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C6 C4 C3 117.1(2) . . ?
C6 C4 C5 121.3(2) . . ?
C3 C4 C5 121.6(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 121.5(2) . . ?
C4 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C1 120.58(19) . . ?
C6 C7 H7 119.7 . . ?
C1 C7 H7 119.7 . . ?
O1 C8 N1 126.17(18) . . ?
O1 C8 S1 123.69(15) . . ?
N1 C8 S1 110.13(14) . . ?
C14 C9 C10 118.55(19) . . ?
C14 C9 S1 121.05(17) . . ?
C10 C9 S1 120.05(18) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O2 C12 C13 124.43(19) . . ?
O2 C12 C11 115.86(18) . . ?
C13 C12 C11 119.70(19) . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 121.3(2) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C22 118.9(2) . . ?
C17 C16 N2 117.96(19) . . ?
C22 C16 N2 123.1(2) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.9(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C21 C19 C18 117.0(2) . . ?
C21 C19 C20 120.6(2) . . ?
C18 C19 C20 122.4(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 C22 122.3(2) . . ?
C19 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C21 C22 C16 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C16 C22 H22 120.2 . . ?
O3 C23 N2 126.1(2) . . ?
O3 C23 S2 123.29(18) . . ?
N2 C23 S2 110.61(15) . . ?
C25 C24 C29 118.7(3) . . ?
C25 C24 S2 119.9(2) . . ?
C29 C24 S2 121.3(2) . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
O4 C27 C28 125.0(2) . . ?
O4 C27 C26 116.0(2) . . ?
C28 C27 C26 119.0(3) . . ?
C29 C28 C27 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C24 121.4(2) . . ?
C28 C29 H29 119.3 . . ?
C24 C29 H29 119.3 . . ?
O4 C30 H30A 109.5 . . ?
O4 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O4 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C37 C31 C32 119.5(2) . . ?
C37 C31 N3 117.39(18) . . ?
C32 C31 N3 123.1(2) . . ?
C31 C32 C33 118.9(2) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 H32 120.6 . . ?
C34 C33 C32 122.2(2) . . ?
C34 C33 H33 118.9 . . ?
C32 C33 H33 118.9 . . ?
C36 C34 C33 117.7(2) . . ?
C36 C34 C35 121.7(3) . . ?
C33 C34 C35 120.6(3) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 C37 121.3(3) . . ?
C34 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C31 C37 C36 120.4(2) . . ?
C31 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
O5 C38 N3 126.74(19) . . ?
O5 C38 S3 123.03(17) . . ?
N3 C38 S3 110.22(14) . . ?
C40 C39 C44 118.2(2) . . ?
C40 C39 S3 119.66(19) . . ?
C44 C39 S3 121.65(18) . . ?
C39 C40 C41 120.2(2) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
C42 C41 C40 119.7(2) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C41 C42 O6 124.1(2) . . ?
C41 C42 C43 120.4(2) . . ?
O6 C42 C43 115.5(2) . . ?
C44 C43 C42 119.7(2) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C39 121.7(2) . . ?
C43 C44 H44 119.1 . . ?
C39 C44 H44 119.1 . . ?
O6 C45 H45A 109.5 . . ?
O6 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O6 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C8 N1 C1 128.13(16) . . ?
C8 N1 H1 115.9 . . ?
C1 N1 H1 115.9 . . ?
C23 N2 C16 128.20(18) . . ?
C23 N2 H2A 115.9 . . ?
C16 N2 H2A 115.9 . . ?
C38 N3 C31 127.65(17) . . ?
C38 N3 H3A 116.2 . . ?
C31 N3 H3A 116.2 . . ?
C12 O2 C15 118.46(19) . . ?
C27 O4 C30 117.7(2) . . ?
C42 O6 C45 118.0(2) . . ?
C9 S1 C8 102.66(9) . . ?
C24 S2 C23 101.53(11) . . ?
C39 S3 C38 102.61(10) . . ?

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
C7 C1 C2 C3 0.3(4) . . . . ?
N1 C1 C2 C3 178.6(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C6 -0.3(5) . . . . ?
C2 C3 C4 C5 179.2(3) . . . . ?
C3 C4 C6 C7 0.5(4) . . . . ?
C5 C4 C6 C7 -179.0(2) . . . . ?
C4 C6 C7 C1 -0.3(4) . . . . ?
C2 C1 C7 C6 -0.1(4) . . . . ?
N1 C1 C7 C6 -178.5(2) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
S1 C9 C10 C11 -172.92(19) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 O2 178.7(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
O2 C12 C13 C14 -178.3(2) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
S1 C9 C14 C13 173.16(17) . . . . ?
C12 C13 C14 C9 -0.6(3) . . . . ?
C22 C16 C17 C18 -0.4(4) . . . . ?
N2 C16 C17 C18 -178.4(2) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C21 0.6(4) . . . . ?
C17 C18 C19 C20 178.7(3) . . . . ?
C18 C19 C21 C22 -0.8(4) . . . . ?
C20 C19 C21 C22 -178.9(2) . . . . ?
C19 C21 C22 C16 0.4(4) . . . . ?
C17 C16 C22 C21 0.2(3) . . . . ?
N2 C16 C22 C21 178.1(2) . . . . ?
C29 C24 C25 C26 -0.4(4) . . . . ?
S2 C24 C25 C26 -176.23(18) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
C25 C26 C27 O4 179.5(2) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
O4 C27 C28 C29 -179.7(2) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C27 C28 C29 C24 0.0(4) . . . . ?
C25 C24 C29 C28 0.2(4) . . . . ?
S2 C24 C29 C28 176.0(2) . . . . ?
C37 C31 C32 C33 0.4(3) . . . . ?
N3 C31 C32 C33 -177.15(19) . . . . ?
C31 C32 C33 C34 -0.6(4) . . . . ?
C32 C33 C34 C36 0.5(4) . . . . ?
C32 C33 C34 C35 -179.4(3) . . . . ?
C33 C34 C36 C37 -0.1(4) . . . . ?
C35 C34 C36 C37 179.8(3) . . . . ?
C32 C31 C37 C36 0.0(3) . . . . ?
N3 C31 C37 C36 177.6(2) . . . . ?
C34 C36 C37 C31 -0.1(4) . . . . ?
C44 C39 C40 C41 -0.9(3) . . . . ?
S3 C39 C40 C41 171.48(19) . . . . ?
C39 C40 C41 C42 1.6(4) . . . . ?
C40 C41 C42 O6 178.8(2) . . . . ?
C40 C41 C42 C43 -0.7(4) . . . . ?
C41 C42 C43 C44 -0.9(4) . . . . ?
O6 C42 C43 C44 179.6(2) . . . . ?
C42 C43 C44 C39 1.6(4) . . . . ?
C40 C39 C44 C43 -0.7(4) . . . . ?
S3 C39 C44 C43 -172.9(2) . . . . ?
O1 C8 N1 C1 5.7(4) . . . . ?
S1 C8 N1 C1 -173.07(18) . . . . ?
C2 C1 N1 C8 1.4(4) . . . . ?
C7 C1 N1 C8 179.7(2) . . . . ?
O3 C23 N2 C16 3.6(4) . . . . ?
S2 C23 N2 C16 -176.43(17) . . . . ?
C17 C16 N2 C23 -165.6(2) . . . . ?
C22 C16 N2 C23 16.6(3) . . . . ?
O5 C38 N3 C31 -2.7(3) . . . . ?
S3 C38 N3 C31 176.18(16) . . . . ?
C37 C31 N3 C38 152.5(2) . . . . ?
C32 C31 N3 C38 -30.0(3) . . . . ?
C13 C12 O2 C15 2.4(3) . . . . ?
C11 C12 O2 C15 -176.8(2) . . . . ?
C28 C27 O4 C30 -3.1(4) . . . . ?
C26 C27 O4 C30 177.1(2) . . . . ?
C41 C42 O6 C45 -4.7(4) . . . . ?
C43 C42 O6 C45 174.9(3) . . . . ?
C14 C9 S1 C8 91.62(19) . . . . ?
C10 C9 S1 C8 -95.35(19) . . . . ?
O1 C8 S1 C9 3.9(2) . . . . ?
N1 C8 S1 C9 -177.34(16) . . . . ?
C25 C24 S2 C23 -104.4(2) . . . . ?
C29 C24 S2 C23 79.8(2) . . . . ?
O3 C23 S2 C24 2.5(2) . . . . ?
N2 C23 S2 C24 -177.40(17) . . . . ?
C40 C39 S3 C38 122.26(19) . . . . ?
C44 C39 S3 C38 -65.6(2) . . . . ?
O5 C38 S3 C39 -18.1(2) . . . . ?
N3 C38 S3 C39 163.04(15) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2120466'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Guo'
;Shanxi University
China
;
_audit_update_record             
;
2021-11-06 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O2 S'
_chemical_formula_weight         259.31

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                   13.3641(8)
_cell_length_b                   11.7805(7)
_cell_length_c                   8.6325(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.970(2)
_cell_angle_gamma                90
_cell_volume                     1292.77(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7183
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.35

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12988
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3196
_reflns_number_gt                2717
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0556P)²+0.3874P] 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         3196
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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 0.81893(12) 0.70200(14) 1.07557(17) 0.0402(3) Uani 1 1 d . . . . .
C2 C 0.86713(15) 0.79769(17) 1.0419(3) 0.0575(5) Uani 1 1 d . . . . .
H2 H 0.8288 0.8643 1.0106 0.069 Uiso 1 1 calc R U . . .
C3 C 0.97294(17) 0.7947(2) 1.0548(3) 0.0712(6) Uani 1 1 d . . . . .
H3 H 1.0057 0.8588 1.0301 0.085 Uiso 1 1 calc R U . . .
C4 C 1.02916(16) 0.6966(2) 1.1043(3) 0.0700(6) Uani 1 1 d . . . . .
H4 H 1.1006 0.6947 1.1156 0.084 Uiso 1 1 calc R U . . .
C5 C 0.98035(15) 0.6012(2) 1.1373(2) 0.0647(5) Uani 1 1 d . . . . .
H5 H 1.0196 0.5354 1.1706 0.078 Uiso 1 1 calc R U . . .
C6 C 0.87358(13) 0.60057(16) 1.1221(2) 0.0490(4) Uani 1 1 d . . . . .
C7 C 0.82002(19) 0.49531(19) 1.1535(3) 0.0751(6) Uani 1 1 d . . . . .
H7A H 0.7933 0.5081 1.2433 0.113 Uiso 1 1 calc R U . . .
H7B H 0.8695 0.4338 1.1791 0.113 Uiso 1 1 calc R U . . .
H7C H 0.7629 0.4766 1.0581 0.113 Uiso 1 1 calc R U . . .
C8 C 0.63442(11) 0.67837(11) 0.92559(17) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.42692(11) 0.63754(13) 0.75326(17) 0.0360(3) Uani 1 1 d . . . . .
C10 C 0.44405(12) 0.53148(13) 0.69589(19) 0.0403(3) Uani 1 1 d . . . . .
H10 H 0.4962 0.4844 0.7605 0.048 Uiso 1 1 calc R U . . .
C11 C 0.38401(12) 0.49561(12) 0.54348(19) 0.0397(3) Uani 1 1 d . . . . .
H11 H 0.3970 0.4253 0.5046 0.048 Uiso 1 1 calc R U . . .
C12 C 0.30434(11) 0.56423(13) 0.44816(18) 0.0371(3) Uani 1 1 d . . . . .
C13 C 0.28322(12) 0.66785(13) 0.50844(19) 0.0408(3) Uani 1 1 d . . . . .
H13 H 0.2272 0.7121 0.4475 0.049 Uiso 1 1 calc R U . . .
C14 C 0.34564(12) 0.70509(13) 0.65935(19) 0.0393(3) Uani 1 1 d . . . . .
H14 H 0.3331 0.7756 0.6980 0.047 Uiso 1 1 calc R U . . .
N1 N 0.70921(10) 0.70680(12) 1.06269(15) 0.0425(3) Uani 1 1 d . . . . .
H1 H 0.6913 0.7286 1.1455 0.051 Uiso 1 1 calc R U . . .
O1 O 0.65209(8) 0.64979(10) 0.80032(12) 0.0417(3) Uani 1 1 d . . . . .
O2 O 0.24513(9) 0.53429(11) 0.29476(14) 0.0520(3) Uani 1 1 d . . . . .
H2A H 0.2701 0.4772 0.2666 0.078 Uiso 1 1 calc R U . . .
S1 S 0.50556(3) 0.68722(4) 0.94594(5) 0.04477(14) Uani 1 1 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 C2 1.373(3) . ?
C1 C6 1.394(2) . ?
C1 N1 1.4371(19) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O1 1.2231(17) . ?
C8 N1 1.3350(18) . ?
C8 S1 1.7871(14) . ?
C9 C10 1.389(2) . ?
C9 C14 1.388(2) . ?
C9 S1 1.7706(15) . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C12 O2 1.3629(18) . ?
C12 C13 1.390(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 H1 0.8600 . ?
O2 H2A 0.8200 . ?

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
C2 C1 C6 121.78(16) . . ?
C2 C1 N1 119.04(15) . . ?
C6 C1 N1 119.17(15) . . ?
C1 C2 C3 119.76(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.30(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.58(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 116.96(18) . . ?
C5 C6 C7 121.38(18) . . ?
C1 C6 C7 121.67(16) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 123.84(13) . . ?
O1 C8 S1 123.90(11) . . ?
N1 C8 S1 112.26(10) . . ?
C10 C9 C14 119.53(13) . . ?
C10 C9 S1 121.13(11) . . ?
C14 C9 S1 119.33(11) . . ?
C11 C10 C9 120.29(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.11(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O2 C12 C11 122.34(14) . . ?
O2 C12 C13 117.85(13) . . ?
C11 C12 C13 119.82(14) . . ?
C14 C13 C12 119.86(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.26(14) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C8 N1 C1 121.71(12) . . ?
C8 N1 H1 119.1 . . ?
C1 N1 H1 119.1 . . ?
C12 O2 H2A 109.5 . . ?
C9 S1 C8 101.48(6) . . ?

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 -0.3(3) . . . . ?
N1 C1 C2 C3 179.56(17) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
N1 C1 C6 C5 -178.23(15) . . . . ?
C2 C1 C6 C7 -177.98(19) . . . . ?
N1 C1 C6 C7 2.2(2) . . . . ?
C14 C9 C10 C11 3.0(2) . . . . ?
S1 C9 C10 C11 -178.09(11) . . . . ?
C9 C10 C11 C12 -1.6(2) . . . . ?
C10 C11 C12 O2 177.80(14) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
O2 C12 C13 C14 -175.87(14) . . . . ?
C11 C12 C13 C14 3.7(2) . . . . ?
C12 C13 C14 C9 -2.3(2) . . . . ?
C10 C9 C14 C13 -1.1(2) . . . . ?
S1 C9 C14 C13 -179.97(11) . . . . ?
O1 C8 N1 C1 -2.3(2) . . . . ?
S1 C8 N1 C1 177.86(12) . . . . ?
C2 C1 N1 C8 92.71(19) . . . . ?
C6 C1 N1 C8 -87.44(19) . . . . ?
C10 C9 S1 C8 56.72(13) . . . . ?
C14 C9 S1 C8 -124.40(12) . . . . ?
O1 C8 S1 C9 3.44(14) . . . . ?
N1 C8 S1 C9 -176.72(11) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.039

