# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_LZQE-258
_database_code_depnum_ccdc_archive 'CCDC 1857986'
loop_
_audit_author_name
_audit_author_address
liuzhuqing
;QILU UNIVERSITY of TECHNOLOGY
China
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N O S'
_chemical_formula_weight         353.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.8280(10)
_cell_length_b                   19.5033(17)
_cell_length_c                   10.3158(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.118(12)
_cell_angle_gamma                90
_cell_volume                     1736.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2938
_cell_measurement_theta_min      3.994
_cell_measurement_theta_max      28.804

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5402
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9958
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.765
_diffrn_reflns_theta_max         25.994
_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 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.853
_reflns_number_total             5743
_reflns_number_gt                4629
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_max     0.673
_reflns_Friedel_fraction_full    0.699

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0692P)²] 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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.39(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5743
_refine_ls_number_parameters     474
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_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
S1 S 0.84927(14) 0.61114(6) 0.47728(12) 0.0479(3) Uani 1 1 d . . . . .
S2 S 0.12341(14) 0.38464(6) 0.96068(13) 0.0539(4) Uani 1 1 d . . . . .
N1 N 0.7206(5) 0.4462(2) 0.6379(4) 0.0490(10) Uani 1 1 d D . . . .
N2 N 0.2501(5) 0.5419(2) 0.7757(4) 0.0494(10) Uani 1 1 d D . . . .
H2A H 0.3258 0.5403 0.7352 0.059 Uiso 1 1 calc DR U . . .
O1 O 0.5432(4) 0.56787(17) 0.6941(4) 0.0599(10) Uani 1 1 d . . . . .
O2 O 0.4424(4) 0.42036(18) 0.7516(4) 0.0629(10) Uani 1 1 d . . . . .
C1 C 0.8133(5) 0.3903(3) 0.6210(5) 0.0458(10) Uani 1 1 d . . . . .
C2 C 0.8000(7) 0.3224(3) 0.6562(6) 0.0608(14) Uani 1 1 d . . . . .
H2 H 0.7251 0.3086 0.7021 0.073 Uiso 1 1 calc R U . . .
C3 C 0.9012(6) 0.2759(3) 0.6208(6) 0.0665(15) Uani 1 1 d . . . . .
H3 H 0.8934 0.2301 0.6431 0.080 Uiso 1 1 calc R U . . .
C4 C 1.0139(6) 0.2949(3) 0.5535(5) 0.0585(13) Uani 1 1 d . . . . .
H4 H 1.0803 0.2620 0.5311 0.070 Uiso 1 1 calc R U . . .
C5 C 1.0284(6) 0.3625(3) 0.5194(5) 0.0521(12) Uani 1 1 d . . . . .
H5 H 1.1054 0.3752 0.4749 0.063 Uiso 1 1 calc R U . . .
C6 C 0.9279(5) 0.4120(2) 0.5513(4) 0.0417(10) Uani 1 1 d . . . . .
C7 C 0.9018(5) 0.4838(2) 0.5265(4) 0.0420(10) Uani 1 1 d . . . . .
C8 C 0.7718(5) 0.5024(2) 0.5819(4) 0.0412(10) Uani 1 1 d . . . . .
C9 C 0.7271(5) 0.5700(2) 0.5653(5) 0.0426(10) Uani 1 1 d . . . . .
C10 C 0.9560(5) 0.5382(2) 0.4646(4) 0.0424(11) Uani 1 1 d . . . . .
C11 C 1.0860(5) 0.5432(2) 0.3962(5) 0.0435(11) Uani 1 1 d . . . . .
C12 C 1.2247(6) 0.5090(3) 0.4469(5) 0.0493(12) Uani 1 1 d . . . . .
H12 H 1.2331 0.4810 0.5211 0.059 Uiso 1 1 calc R U . . .
C13 C 1.3503(6) 0.5167(3) 0.3865(6) 0.0605(14) Uani 1 1 d . . . . .
H13 H 1.4426 0.4939 0.4205 0.073 Uiso 1 1 calc R U . . .
C14 C 1.3389(7) 0.5573(3) 0.2780(6) 0.0676(16) Uani 1 1 d . . . . .
H14 H 1.4240 0.5625 0.2388 0.081 Uiso 1 1 calc R U . . .
C15 C 1.2019(7) 0.5912(3) 0.2252(6) 0.0660(16) Uani 1 1 d . . . . .
H15 H 1.1945 0.6189 0.1508 0.079 Uiso 1 1 calc R U . . .
C16 C 1.0760(6) 0.5834(3) 0.2846(5) 0.0542(13) Uani 1 1 d . . . . .
H16 H 0.9834 0.6056 0.2487 0.065 Uiso 1 1 calc R U . . .
C17 C 0.6132(5) 0.6031(3) 0.6267(5) 0.0449(11) Uani 1 1 d . . . . .
C18 C 0.5873(5) 0.6783(2) 0.6162(5) 0.0431(10) Uani 1 1 d . . . . .
C19 C 0.5887(6) 0.7162(3) 0.5036(5) 0.0557(13) Uani 1 1 d . . . . .
H19 H 0.5996 0.6943 0.4259 0.067 Uiso 1 1 calc R U . . .
C20 C 0.5738(7) 0.7874(3) 0.5061(6) 0.0700(16) Uani 1 1 d . . . . .
H20 H 0.5790 0.8130 0.4312 0.084 Uiso 1 1 calc R U . . .
C21 C 0.5514(7) 0.8198(3) 0.6189(7) 0.0759(18) Uani 1 1 d . . . . .
H21 H 0.5387 0.8671 0.6192 0.091 Uiso 1 1 calc R U . . .
C22 C 0.5477(7) 0.7827(3) 0.7305(6) 0.0721(16) Uani 1 1 d . . . . .
H22 H 0.5332 0.8048 0.8069 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5657(6) 0.7121(3) 0.7297(5) 0.0575(13) Uani 1 1 d . . . . .
H23 H 0.5633 0.6870 0.8060 0.069 Uiso 1 1 calc R U . . .
C24 C 0.1610(5) 0.5998(2) 0.7877(4) 0.0464(11) Uani 1 1 d . . . . .
C25 C 0.1738(6) 0.6653(3) 0.7386(5) 0.0566(13) Uani 1 1 d . . . . .
H25 H 0.2475 0.6755 0.6890 0.068 Uiso 1 1 calc R U . . .
C26 C 0.0736(6) 0.7144(3) 0.7659(6) 0.0610(13) Uani 1 1 d . . . . .
H26 H 0.0783 0.7584 0.7324 0.073 Uiso 1 1 calc R U . . .
C27 C -0.0346(6) 0.6999(3) 0.8424(6) 0.0635(14) Uani 1 1 d . . . . .
H27 H -0.0972 0.7349 0.8629 0.076 Uiso 1 1 calc R U . . .
C28 C -0.0507(6) 0.6347(3) 0.8883(5) 0.0563(13) Uani 1 1 d . . . . .
H28 H -0.1262 0.6253 0.9366 0.068 Uiso 1 1 calc R U . . .
C29 C 0.0476(5) 0.5825(2) 0.8617(5) 0.0444(11) Uani 1 1 d . . . . .
C30 C 0.0692(5) 0.5100(2) 0.8937(5) 0.0445(11) Uani 1 1 d . . . . .
C31 C 0.1971(6) 0.4881(3) 0.8389(5) 0.0474(11) Uani 1 1 d . . . . .
C32 C 0.2415(5) 0.4207(3) 0.8638(5) 0.0479(11) Uani 1 1 d . . . . .
C33 C 0.0173(5) 0.4586(2) 0.9636(5) 0.0469(11) Uani 1 1 d . . . . .
C34 C -0.1146(5) 0.4573(2) 1.0319(5) 0.0444(11) Uani 1 1 d . . . . .
C35 C -0.2477(6) 0.4936(3) 0.9804(5) 0.0509(12) Uani 1 1 d . . . . .
H35 H -0.2527 0.5206 0.9053 0.061 Uiso 1 1 calc R U . . .
C36 C -0.3747(6) 0.4900(3) 1.0408(6) 0.0588(14) Uani 1 1 d . . . . .
H36 H -0.4646 0.5143 1.0054 0.071 Uiso 1 1 calc R U . . .
C37 C -0.3674(7) 0.4507(3) 1.1524(6) 0.0638(15) Uani 1 1 d . . . . .
H37 H -0.4516 0.4490 1.1934 0.077 Uiso 1 1 calc R U . . .
C38 C -0.2373(7) 0.4143(3) 1.2030(5) 0.0631(15) Uani 1 1 d . . . . .
H38 H -0.2337 0.3868 1.2772 0.076 Uiso 1 1 calc R U . . .
C39 C -0.1096(6) 0.4181(3) 1.1444(5) 0.0533(12) Uani 1 1 d . . . . .
H39 H -0.0200 0.3940 1.1812 0.064 Uiso 1 1 calc R U . . .
C40 C 0.3684(5) 0.3877(3) 0.8218(5) 0.0491(11) Uani 1 1 d . . . . .
C41 C 0.4139(6) 0.3162(3) 0.8629(5) 0.0459(11) Uani 1 1 d . . . . .
C42 C 0.3103(6) 0.2623(3) 0.8526(5) 0.0564(13) Uani 1 1 d . . . . .
H42 H 0.2049 0.2702 0.8220 0.068 Uiso 1 1 calc R U . . .
C43 C 0.3629(8) 0.1970(3) 0.8876(6) 0.0645(15) Uani 1 1 d . . . . .
H43 H 0.2932 0.1607 0.8774 0.077 Uiso 1 1 calc R U . . .
C44 C 0.5172(8) 0.1852(3) 0.9374(5) 0.0665(15) Uani 1 1 d . . . . .
H44 H 0.5514 0.1411 0.9627 0.080 Uiso 1 1 calc R U . . .
C45 C 0.6203(7) 0.2379(3) 0.9497(6) 0.0659(15) Uani 1 1 d . . . . .
H45 H 0.7249 0.2296 0.9836 0.079 Uiso 1 1 calc R U . . .
C46 C 0.5711(6) 0.3032(3) 0.9124(5) 0.0542(12) Uani 1 1 d . . . . .
H46 H 0.6425 0.3388 0.9201 0.065 Uiso 1 1 calc R U . . .
H1A H 0.652(5) 0.447(3) 0.679(5) 0.063(16) 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
S1 C10 1.726(5) . ?
S1 C9 1.745(4) . ?
S2 C33 1.723(5) . ?
S2 C32 1.737(4) . ?
N1 C8 1.360(6) . ?
N1 C1 1.396(6) . ?
N1 H1A 0.81(2) . ?
N2 C31 1.368(6) . ?
N2 C24 1.397(6) . ?
N2 H2A 0.8600 . ?
O1 C17 1.232(5) . ?
O2 C40 1.247(6) . ?
C1 C2 1.384(7) . ?
C1 C6 1.423(6) . ?
C2 C3 1.374(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.434(6) . ?
C7 C10 1.375(6) . ?
C7 C8 1.432(6) . ?
C8 C9 1.375(6) . ?
C9 C17 1.448(6) . ?
C10 C11 1.471(6) . ?
C11 C16 1.381(7) . ?
C11 C12 1.396(7) . ?
C12 C13 1.389(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.485(7) . ?
C18 C19 1.380(7) . ?
C18 C23 1.391(7) . ?
C19 C20 1.395(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(8) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.387(7) . ?
C24 C29 1.422(6) . ?
C25 C26 1.373(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.390(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.402(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.455(7) . ?
C30 C33 1.369(7) . ?
C30 C31 1.430(6) . ?
C31 C32 1.381(7) . ?
C32 C40 1.436(6) . ?
C33 C34 1.482(6) . ?
C34 C35 1.380(7) . ?
C34 C39 1.383(7) . ?
C35 C36 1.394(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.374(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.357(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.388(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.487(7) . ?
C41 C42 1.383(7) . ?
C41 C46 1.398(7) . ?
C42 C43 1.378(8) . ?
C42 H42 0.9300 . ?
C43 C44 1.370(9) . ?
C43 H43 0.9300 . ?
C44 C45 1.361(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.375(8) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?

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
C10 S1 C9 93.8(2) . . ?
C33 S2 C32 93.8(2) . . ?
C8 N1 C1 108.7(3) . . ?
C8 N1 H1A 125(4) . . ?
C1 N1 H1A 127(4) . . ?
C31 N2 C24 108.8(3) . . ?
C31 N2 H2A 125.6 . . ?
C24 N2 H2A 125.6 . . ?
C2 C1 N1 129.1(4) . . ?
C2 C1 C6 121.7(4) . . ?
N1 C1 C6 109.1(4) . . ?
C3 C2 C1 117.7(5) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 122.4(5) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 117.9(4) . . ?
C5 C6 C7 136.0(4) . . ?
C1 C6 C7 106.1(4) . . ?
C10 C7 C8 112.1(4) . . ?
C10 C7 C6 141.1(4) . . ?
C8 C7 C6 106.8(4) . . ?
N1 C8 C9 135.5(4) . . ?
N1 C8 C7 109.3(4) . . ?
C9 C8 C7 115.2(4) . . ?
C8 C9 C17 125.5(4) . . ?
C8 C9 S1 108.3(3) . . ?
C17 C9 S1 125.7(3) . . ?
C7 C10 C11 131.0(4) . . ?
C7 C10 S1 110.6(3) . . ?
C11 C10 S1 118.4(3) . . ?
C16 C11 C12 118.7(4) . . ?
C16 C11 C10 121.2(4) . . ?
C12 C11 C10 120.1(4) . . ?
C13 C12 C11 120.1(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.3(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 121.0(5) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
O1 C17 C9 118.4(4) . . ?
O1 C17 C18 120.2(4) . . ?
C9 C17 C18 121.3(4) . . ?
C19 C18 C23 118.9(5) . . ?
C19 C18 C17 124.2(4) . . ?
C23 C18 C17 116.9(4) . . ?
C18 C19 C20 120.0(5) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.9(5) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C18 120.7(5) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C25 C24 N2 128.4(4) . . ?
C25 C24 C29 122.4(4) . . ?
N2 C24 C29 109.2(4) . . ?
C26 C25 C24 117.5(5) . . ?
C26 C25 H25 121.2 . . ?
C24 C25 H25 121.2 . . ?
C25 C26 C27 121.6(5) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C28 C27 C26 121.1(5) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 119.5(5) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C28 C29 C24 117.8(4) . . ?
C28 C29 C30 135.9(4) . . ?
C24 C29 C30 106.2(4) . . ?
C33 C30 C31 111.7(4) . . ?
C33 C30 C29 142.0(4) . . ?
C31 C30 C29 106.1(4) . . ?
N2 C31 C32 135.0(4) . . ?
N2 C31 C30 109.7(4) . . ?
C32 C31 C30 115.3(4) . . ?
C31 C32 C40 125.4(4) . . ?
C31 C32 S2 108.1(3) . . ?
C40 C32 S2 126.4(4) . . ?
C30 C33 C34 130.3(4) . . ?
C30 C33 S2 111.1(3) . . ?
C34 C33 S2 118.6(3) . . ?
C35 C34 C39 118.8(4) . . ?
C35 C34 C33 120.0(4) . . ?
C39 C34 C33 121.2(4) . . ?
C34 C35 C36 120.2(5) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C37 C36 C35 120.1(5) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C38 C37 C36 120.1(4) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C39 120.3(5) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C34 C39 C38 120.6(5) . . ?
C34 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
O2 C40 C32 118.9(5) . . ?
O2 C40 C41 120.1(4) . . ?
C32 C40 C41 121.0(4) . . ?
C42 C41 C46 118.7(5) . . ?
C42 C41 C40 123.8(5) . . ?
C46 C41 C40 117.5(4) . . ?
C43 C42 C41 120.1(5) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C44 C43 C42 120.5(6) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C45 C44 C43 120.0(5) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.5(5) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C45 C46 C41 120.1(5) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?

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
C8 N1 C1 C2 -176.7(5) . . . . ?
C8 N1 C1 C6 -0.1(6) . . . . ?
N1 C1 C2 C3 175.9(5) . . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
C1 C2 C3 C4 0.5(9) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
C3 C4 C5 C6 -0.8(8) . . . . ?
C4 C5 C6 C1 0.9(7) . . . . ?
C4 C5 C6 C7 -175.6(5) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
N1 C1 C6 C5 -177.2(4) . . . . ?
C2 C1 C6 C7 177.1(5) . . . . ?
N1 C1 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C10 -0.4(11) . . . . ?
C1 C6 C7 C10 -177.2(6) . . . . ?
C5 C6 C7 C8 176.5(5) . . . . ?
C1 C6 C7 C8 -0.2(5) . . . . ?
C1 N1 C8 C9 178.5(5) . . . . ?
C1 N1 C8 C7 -0.1(5) . . . . ?
C10 C7 C8 N1 178.1(4) . . . . ?
C6 C7 C8 N1 0.2(5) . . . . ?
C10 C7 C8 C9 -0.8(6) . . . . ?
C6 C7 C8 C9 -178.7(4) . . . . ?
N1 C8 C9 C17 10.0(9) . . . . ?
C7 C8 C9 C17 -171.4(4) . . . . ?
N1 C8 C9 S1 -178.2(5) . . . . ?
C7 C8 C9 S1 0.4(5) . . . . ?
C10 S1 C9 C8 0.1(4) . . . . ?
C10 S1 C9 C17 171.9(4) . . . . ?
C8 C7 C10 C11 179.3(5) . . . . ?
C6 C7 C10 C11 -3.9(11) . . . . ?
C8 C7 C10 S1 0.8(5) . . . . ?
C6 C7 C10 S1 177.6(6) . . . . ?
C9 S1 C10 C7 -0.5(4) . . . . ?
C9 S1 C10 C11 -179.2(4) . . . . ?
C7 C10 C11 C16 143.4(5) . . . . ?
S1 C10 C11 C16 -38.2(6) . . . . ?
C7 C10 C11 C12 -39.1(8) . . . . ?
S1 C10 C11 C12 139.3(4) . . . . ?
C16 C11 C12 C13 1.1(7) . . . . ?
C10 C11 C12 C13 -176.5(5) . . . . ?
C11 C12 C13 C14 -0.1(8) . . . . ?
C12 C13 C14 C15 -0.6(9) . . . . ?
C13 C14 C15 C16 0.2(9) . . . . ?
C12 C11 C16 C15 -1.5(8) . . . . ?
C10 C11 C16 C15 176.0(5) . . . . ?
C14 C15 C16 C11 0.9(9) . . . . ?
C8 C9 C17 O1 -4.2(8) . . . . ?
S1 C9 C17 O1 -174.6(4) . . . . ?
C8 C9 C17 C18 172.1(5) . . . . ?
S1 C9 C17 C18 1.6(7) . . . . ?
O1 C17 C18 C19 -145.0(5) . . . . ?
C9 C17 C18 C19 38.8(7) . . . . ?
O1 C17 C18 C23 37.2(7) . . . . ?
C9 C17 C18 C23 -139.0(5) . . . . ?
C23 C18 C19 C20 2.1(8) . . . . ?
C17 C18 C19 C20 -175.6(5) . . . . ?
C18 C19 C20 C21 -2.6(9) . . . . ?
C19 C20 C21 C22 1.7(10) . . . . ?
C20 C21 C22 C23 -0.4(10) . . . . ?
C21 C22 C23 C18 -0.1(9) . . . . ?
C19 C18 C23 C22 -0.8(8) . . . . ?
C17 C18 C23 C22 177.1(5) . . . . ?
C31 N2 C24 C25 -179.8(5) . . . . ?
C31 N2 C24 C29 0.3(6) . . . . ?
N2 C24 C25 C26 -178.8(5) . . . . ?
C29 C24 C25 C26 1.2(7) . . . . ?
C24 C25 C26 C27 1.4(8) . . . . ?
C25 C26 C27 C28 -3.3(9) . . . . ?
C26 C27 C28 C29 2.4(8) . . . . ?
C27 C28 C29 C24 0.1(7) . . . . ?
C27 C28 C29 C30 178.6(6) . . . . ?
C25 C24 C29 C28 -1.9(7) . . . . ?
N2 C24 C29 C28 178.0(4) . . . . ?
C25 C24 C29 C30 179.2(4) . . . . ?
N2 C24 C29 C30 -0.9(5) . . . . ?
C28 C29 C30 C33 -3.5(12) . . . . ?
C24 C29 C30 C33 175.0(7) . . . . ?
C28 C29 C30 C31 -177.4(6) . . . . ?
C24 C29 C30 C31 1.1(5) . . . . ?
C24 N2 C31 C32 -177.2(6) . . . . ?
C24 N2 C31 C30 0.5(6) . . . . ?
C33 C30 C31 N2 -177.0(4) . . . . ?
C29 C30 C31 N2 -1.0(5) . . . . ?
C33 C30 C31 C32 1.2(7) . . . . ?
C29 C30 C31 C32 177.2(4) . . . . ?
N2 C31 C32 C40 -1.0(10) . . . . ?
C30 C31 C32 C40 -178.5(5) . . . . ?
N2 C31 C32 S2 176.2(5) . . . . ?
C30 C31 C32 S2 -1.3(6) . . . . ?
C33 S2 C32 C31 0.9(4) . . . . ?
C33 S2 C32 C40 178.0(5) . . . . ?
C31 C30 C33 C34 -177.4(5) . . . . ?
C29 C30 C33 C34 9.0(11) . . . . ?
C31 C30 C33 S2 -0.5(6) . . . . ?
C29 C30 C33 S2 -174.2(6) . . . . ?
C32 S2 C33 C30 -0.2(4) . . . . ?
C32 S2 C33 C34 177.1(4) . . . . ?
C30 C33 C34 C35 33.8(8) . . . . ?
S2 C33 C34 C35 -142.9(4) . . . . ?
C30 C33 C34 C39 -148.6(6) . . . . ?
S2 C33 C34 C39 34.7(6) . . . . ?
C39 C34 C35 C36 -0.6(7) . . . . ?
C33 C34 C35 C36 177.0(5) . . . . ?
C34 C35 C36 C37 0.6(8) . . . . ?
C35 C36 C37 C38 -1.1(9) . . . . ?
C36 C37 C38 C39 1.7(9) . . . . ?
C35 C34 C39 C38 1.2(8) . . . . ?
C33 C34 C39 C38 -176.4(5) . . . . ?
C37 C38 C39 C34 -1.8(8) . . . . ?
C31 C32 C40 O2 -3.6(8) . . . . ?
S2 C32 C40 O2 179.7(4) . . . . ?
C31 C32 C40 C41 175.3(5) . . . . ?
S2 C32 C40 C41 -1.4(7) . . . . ?
O2 C40 C41 C42 -132.2(5) . . . . ?
C32 C40 C41 C42 48.9(7) . . . . ?
O2 C40 C41 C46 46.6(7) . . . . ?
C32 C40 C41 C46 -132.3(5) . . . . ?
C46 C41 C42 C43 -1.6(7) . . . . ?
C40 C41 C42 C43 177.2(5) . . . . ?
C41 C42 C43 C44 2.4(8) . . . . ?
C42 C43 C44 C45 -1.5(8) . . . . ?
C43 C44 C45 C46 -0.1(8) . . . . ?
C44 C45 C46 C41 0.8(8) . . . . ?
C42 C41 C46 C45 0.1(7) . . . . ?
C40 C41 C46 C45 -178.9(4) . . . . ?

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
N1 H1A O2 0.81(2) 2.20(3) 2.979(5) 163(5) .
N1 H1A O1 0.81(2) 2.57(5) 2.967(5) 112(5) .
N2 H2A O2 0.86 2.55 2.956(5) 110.2 .
N2 H2A O1 0.86 2.12 2.928(5) 156.4 .

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

