# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2254460'
loop_
_audit_author_name
_audit_author_address
'Da-Ming Du'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-04-06 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(S)-4-((4-oxo-6-tosyl-1,2,3,4,6,11c-hexahydrobenzo[4,5]thieno[2,3-c]isoquinolin-5-yl)methyl)benzonitrile
_chemical_name_common            ?
_chemical_melting_point          447-448
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 N2 O3 S2'
_chemical_formula_weight         524.63

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.378(2)
_cell_length_b                   13.432(3)
_cell_length_c                   18.562(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2587.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8856
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      20.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58680
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.480
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_full        25.104
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4590
_reflns_number_gt                3016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0615P)²] 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_abs_structure_details 
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4590
_refine_ls_number_parameters     345
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_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
C19A C 0.7299(10) 0.6036(9) 0.9272(6) 0.073(3) Uani 0.704(16) 1 d D U P A 1
H19A H 0.7546 0.5955 0.9773 0.087 Uiso 0.704(16) 1 calc R U P A 1
H19B H 0.7688 0.5498 0.9000 0.087 Uiso 0.704(16) 1 calc R U P A 1
C19B C 0.686(2) 0.659(2) 0.9550(11) 0.077(5) Uani 0.296(16) 1 d D U P A 2
H19C H 0.7318 0.6196 0.9902 0.093 Uiso 0.296(16) 1 calc R U P A 2
H19D H 0.6458 0.7146 0.9802 0.093 Uiso 0.296(16) 1 calc R U P A 2
C1 C 0.8363(8) 1.0483(5) 0.9017(4) 0.098(3) Uani 1 1 d . . . . .
H1A H 0.8263 1.0829 0.9466 0.148 Uiso 1 1 calc R U . . .
H1B H 0.8660 1.0939 0.8655 0.148 Uiso 1 1 calc R U . . .
H1C H 0.8981 0.9957 0.9074 0.148 Uiso 1 1 calc R U . . .
C2 C 0.7088(6) 1.0050(4) 0.8792(3) 0.0581(16) Uani 1 1 d . . . . .
C3 C 0.6225(7) 0.9679(4) 0.9294(3) 0.0682(19) Uani 1 1 d . . . . .
H3 H 0.6432 0.9711 0.9781 0.082 Uiso 1 1 calc R U . . .
C4 C 0.5066(6) 0.9262(4) 0.9090(3) 0.0573(16) Uani 1 1 d . . . . .
H4 H 0.4502 0.9010 0.9434 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4755(5) 0.9225(3) 0.8367(3) 0.0412(13) Uani 1 1 d . . . . .
C6 C 0.5595(5) 0.9596(3) 0.7858(3) 0.0418(13) Uani 1 1 d . . . . .
H6 H 0.5386 0.9568 0.7371 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6747(5) 1.0010(3) 0.8077(3) 0.0510(14) Uani 1 1 d . . . . .
H7 H 0.7305 1.0268 0.7732 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4507(5) 0.7354(3) 0.7287(3) 0.0395(13) Uani 1 1 d . . . . .
C9 C 0.5685(5) 0.6915(3) 0.7293(3) 0.0368(12) Uani 1 1 d . . . . .
C10 C 0.6152(6) 0.6761(3) 0.6577(3) 0.0424(13) Uani 1 1 d . . . . .
C11 C 0.5314(6) 0.7128(4) 0.6055(3) 0.0510(15) Uani 1 1 d . . . . .
C12 C 0.5596(8) 0.7060(5) 0.5317(3) 0.0693(18) Uani 1 1 d . . . . .
H12 H 0.5041 0.7319 0.4972 0.083 Uiso 1 1 calc R U . . .
C13 C 0.6714(9) 0.6600(5) 0.5126(4) 0.082(2) Uani 1 1 d . . . . .
H13 H 0.6911 0.6539 0.4639 0.098 Uiso 1 1 calc R U . . .
C14 C 0.7568(7) 0.6221(4) 0.5627(4) 0.0707(19) Uani 1 1 d . . . . .
H14 H 0.8323 0.5913 0.5475 0.085 Uiso 1 1 calc R U . . .
C15 C 0.7299(6) 0.6299(4) 0.6354(3) 0.0530(15) Uani 1 1 d . . . . .
H15 H 0.7873 0.6049 0.6693 0.064 Uiso 1 1 calc R U . . .
C16 C 0.6301(5) 0.6582(3) 0.7977(3) 0.0425(13) Uani 1 1 d . . . . .
H16 H 0.6638 0.5912 0.7888 0.051 Uiso 1 1 calc R U . . .
C17 C 0.7447(5) 0.7215(4) 0.8229(3) 0.0552(15) Uani 1 1 d . . . . .
H17A H 0.8184 0.7082 0.7923 0.066 Uiso 1 1 calc R U . . .
H17B H 0.7231 0.7915 0.8183 0.066 Uiso 1 1 calc R U . . .
C18 C 0.7800(7) 0.6993(5) 0.9005(4) 0.0809(19) Uani 1 1 d D U . . .
H18A H 0.8731 0.6991 0.9049 0.097 Uiso 0.704(16) 1 calc R U P A 1
H18B H 0.7471 0.7523 0.9308 0.097 Uiso 0.704(16) 1 calc R U P A 1
H18C H 0.8511 0.6525 0.8989 0.097 Uiso 0.296(16) 1 calc R U P A 2
H18D H 0.8140 0.7606 0.9204 0.097 Uiso 0.296(16) 1 calc R U P A 2
C20 C 0.5820(6) 0.5964(4) 0.9210(3) 0.0622(17) Uani 1 1 d D . . . .
C21 C 0.5301(5) 0.6480(3) 0.8567(3) 0.0435(13) Uani 1 1 d . . . . .
C22 C 0.4100(6) 0.6855(3) 0.8521(3) 0.0428(13) Uani 1 1 d . . . . .
C23 C 0.3026(6) 0.6601(4) 0.9048(3) 0.0527(15) Uani 1 1 d . . . . .
H23A H 0.3395 0.6442 0.9514 0.063 Uiso 1 1 calc R U . . .
H23B H 0.2468 0.7174 0.9107 0.063 Uiso 1 1 calc R U . . .
C24 C 0.2244(6) 0.5728(3) 0.8782(3) 0.0432(14) Uani 1 1 d . . . . .
C25 C 0.2638(6) 0.4760(3) 0.8895(3) 0.0491(14) Uani 1 1 d . . . . .
H25 H 0.3419 0.4644 0.9125 0.059 Uiso 1 1 calc R U . . .
C26 C 0.1910(6) 0.3965(3) 0.8678(3) 0.0513(15) Uani 1 1 d . . . . .
H26 H 0.2191 0.3320 0.8771 0.062 Uiso 1 1 calc R U . . .
C27 C 0.0767(6) 0.4117(4) 0.8323(3) 0.0555(16) Uani 1 1 d . . . . .
C28 C 0.0352(6) 0.5083(4) 0.8188(3) 0.0650(17) Uani 1 1 d . . . . .
H28 H -0.0412 0.5195 0.7939 0.078 Uiso 1 1 calc R U . . .
C29 C 0.1088(6) 0.5877(4) 0.8425(3) 0.0594(16) Uani 1 1 d . . . . .
H29 H 0.0800 0.6523 0.8344 0.071 Uiso 1 1 calc R U . . .
C30 C 0.0027(6) 0.3266(5) 0.8100(4) 0.0696(18) Uani 1 1 d . . . . .
N1 N 0.3714(4) 0.7466(3) 0.7915(2) 0.0404(10) Uani 1 1 d . . . . .
N2 N -0.0498(6) 0.2558(4) 0.7929(4) 0.099(2) Uani 1 1 d . . . . .
O1 O 0.2926(4) 0.9092(2) 0.7422(2) 0.0580(10) Uani 1 1 d . . . . .
O2 O 0.2434(4) 0.8663(3) 0.8688(2) 0.0662(11) Uani 1 1 d . . . . .
O3 O 0.5256(5) 0.5413(4) 0.9606(3) 0.0989(17) Uani 1 1 d . . . . .
S1 S 0.39309(15) 0.76313(10) 0.64305(8) 0.0550(4) Uani 1 1 d . . . . .
S2 S 0.33112(13) 0.86705(9) 0.80974(8) 0.0477(4) 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
C19A C18 1.472(11) . ?
C19A C20 1.543(11) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19B C20 1.505(19) . ?
C19B C18 1.507(19) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C1 C2 1.505(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.375(7) . ?
C2 C3 1.387(9) . ?
C3 C4 1.379(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(7) . ?
C5 S2 1.746(5) . ?
C6 C7 1.380(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.358(7) . ?
C8 N1 1.434(6) . ?
C8 S1 1.740(5) . ?
C9 C10 1.431(7) . ?
C9 C16 1.490(7) . ?
C10 C11 1.392(7) . ?
C10 C15 1.405(7) . ?
C11 C12 1.403(8) . ?
C11 S1 1.733(6) . ?
C12 C13 1.361(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.515(7) . ?
C16 C17 1.535(7) . ?
C16 H16 0.9800 . ?
C17 C18 1.514(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C18 H18D 0.9700 . ?
C20 O3 1.196(7) . ?
C20 C21 1.482(8) . ?
C21 C22 1.346(7) . ?
C22 N1 1.451(6) . ?
C22 C23 1.521(7) . ?
C23 C24 1.509(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.379(7) . ?
C24 C29 1.385(8) . ?
C25 C26 1.368(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.371(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.391(7) . ?
C27 C30 1.438(9) . ?
C28 C29 1.384(8) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N2 1.141(7) . ?
N1 S2 1.705(4) . ?
O1 S2 1.432(4) . ?
O2 S2 1.425(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 C19A C20 112.3(8) . . ?
C18 C19A H19A 109.1 . . ?
C20 C19A H19A 109.1 . . ?
C18 C19A H19B 109.1 . . ?
C20 C19A H19B 109.1 . . ?
H19A C19A H19B 107.9 . . ?
C20 C19B C18 112.5(15) . . ?
C20 C19B H19C 109.1 . . ?
C18 C19B H19C 109.1 . . ?
C20 C19B H19D 109.1 . . ?
C18 C19B H19D 109.1 . . ?
H19C C19B H19D 107.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.0(6) . . ?
C7 C2 C1 120.7(6) . . ?
C3 C2 C1 121.4(6) . . ?
C4 C3 C2 121.6(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 S2 120.0(4) . . ?
C4 C5 S2 119.6(4) . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 121.6(5) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 N1 123.8(4) . . ?
C9 C8 S1 114.2(4) . . ?
N1 C8 S1 121.5(4) . . ?
C8 C9 C10 111.1(5) . . ?
C8 C9 C16 121.6(5) . . ?
C10 C9 C16 127.1(5) . . ?
C11 C10 C15 118.8(5) . . ?
C11 C10 C9 112.6(5) . . ?
C15 C10 C9 128.6(5) . . ?
C10 C11 C12 121.7(6) . . ?
C10 C11 S1 112.0(4) . . ?
C12 C11 S1 126.3(5) . . ?
C13 C12 C11 117.5(6) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 122.6(6) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C13 C14 C15 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 119.4(6) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C9 C16 C21 110.4(4) . . ?
C9 C16 C17 115.2(4) . . ?
C21 C16 C17 111.2(4) . . ?
C9 C16 H16 106.5 . . ?
C21 C16 H16 106.5 . . ?
C17 C16 H16 106.5 . . ?
C18 C17 C16 111.6(5) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19A C18 C17 114.1(6) . . ?
C19B C18 C17 123.4(9) . . ?
C19A C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19A C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19B C18 H18C 106.5 . . ?
C17 C18 H18C 106.5 . . ?
C19B C18 H18D 106.5 . . ?
C17 C18 H18D 106.5 . . ?
H18C C18 H18D 106.5 . . ?
O3 C20 C21 127.3(6) . . ?
O3 C20 C19B 116.1(9) . . ?
C21 C20 C19B 109.6(10) . . ?
O3 C20 C19A 118.6(6) . . ?
C21 C20 C19A 113.2(6) . . ?
C22 C21 C20 124.2(5) . . ?
C22 C21 C16 123.7(5) . . ?
C20 C21 C16 112.0(5) . . ?
C21 C22 N1 121.1(5) . . ?
C21 C22 C23 123.7(5) . . ?
N1 C22 C23 115.0(5) . . ?
C24 C23 C22 111.0(4) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C29 117.8(5) . . ?
C25 C24 C23 121.6(5) . . ?
C29 C24 C23 120.6(5) . . ?
C26 C25 C24 121.8(5) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 119.5(5) . . ?
C26 C27 C30 118.8(5) . . ?
C28 C27 C30 121.6(6) . . ?
C29 C28 C27 119.4(6) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C24 121.2(5) . . ?
C28 C29 H29 119.4 . . ?
C24 C29 H29 119.4 . . ?
N2 C30 C27 176.0(7) . . ?
C8 N1 C22 114.3(4) . . ?
C8 N1 S2 113.7(3) . . ?
C22 N1 S2 116.8(3) . . ?
C11 S1 C8 90.0(3) . . ?
O2 S2 O1 119.8(2) . . ?
O2 S2 N1 107.6(2) . . ?
O1 S2 N1 105.6(2) . . ?
O2 S2 C5 109.4(2) . . ?
O1 S2 C5 108.8(2) . . ?
N1 S2 C5 104.5(2) . . ?

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 C2 C3 C4 1.2(9) . . . . ?
C1 C2 C3 C4 -178.6(6) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C3 C4 C5 S2 178.3(4) . . . . ?
C4 C5 C6 C7 -0.3(7) . . . . ?
S2 C5 C6 C7 -178.4(3) . . . . ?
C3 C2 C7 C6 -1.3(8) . . . . ?
C1 C2 C7 C6 178.5(5) . . . . ?
C5 C6 C7 C2 0.9(7) . . . . ?
N1 C8 C9 C10 170.3(4) . . . . ?
S1 C8 C9 C10 -1.7(5) . . . . ?
N1 C8 C9 C16 -5.1(7) . . . . ?
S1 C8 C9 C16 -177.1(3) . . . . ?
C8 C9 C10 C11 2.1(6) . . . . ?
C16 C9 C10 C11 177.3(4) . . . . ?
C8 C9 C10 C15 -177.5(5) . . . . ?
C16 C9 C10 C15 -2.3(8) . . . . ?
C15 C10 C11 C12 -0.9(7) . . . . ?
C9 C10 C11 C12 179.5(5) . . . . ?
C15 C10 C11 S1 178.0(3) . . . . ?
C9 C10 C11 S1 -1.7(5) . . . . ?
C10 C11 C12 C13 1.4(8) . . . . ?
S1 C11 C12 C13 -177.3(5) . . . . ?
C11 C12 C13 C14 -1.0(9) . . . . ?
C12 C13 C14 C15 0.1(10) . . . . ?
C13 C14 C15 C10 0.4(8) . . . . ?
C11 C10 C15 C14 0.0(7) . . . . ?
C9 C10 C15 C14 179.6(5) . . . . ?
C8 C9 C16 C21 19.1(6) . . . . ?
C10 C9 C16 C21 -155.6(4) . . . . ?
C8 C9 C16 C17 -107.8(5) . . . . ?
C10 C9 C16 C17 77.5(6) . . . . ?
C9 C16 C17 C18 165.8(5) . . . . ?
C21 C16 C17 C18 39.3(6) . . . . ?
C20 C19A C18 C17 -57.5(12) . . . . ?
C20 C19B C18 C17 29(3) . . . . ?
C16 C17 C18 C19A 18.9(9) . . . . ?
C16 C17 C18 C19B -25.7(18) . . . . ?
C18 C19B C20 O3 160.6(14) . . . . ?
C18 C19B C20 C21 -46(2) . . . . ?
C18 C19A C20 O3 -155.4(8) . . . . ?
C18 C19A C20 C21 34.5(12) . . . . ?
O3 C20 C21 C22 37.3(9) . . . . ?
C19B C20 C21 C22 -111.8(14) . . . . ?
C19A C20 C21 C22 -153.6(7) . . . . ?
O3 C20 C21 C16 -145.6(7) . . . . ?
C19B C20 C21 C16 65.4(14) . . . . ?
C19A C20 C21 C16 23.5(8) . . . . ?
C9 C16 C21 C22 -14.1(6) . . . . ?
C17 C16 C21 C22 115.1(5) . . . . ?
C9 C16 C21 C20 168.7(4) . . . . ?
C17 C16 C21 C20 -62.1(5) . . . . ?
C20 C21 C22 N1 171.6(4) . . . . ?
C16 C21 C22 N1 -5.3(7) . . . . ?
C20 C21 C22 C23 -14.4(8) . . . . ?
C16 C21 C22 C23 168.8(4) . . . . ?
C21 C22 C23 C24 -92.1(6) . . . . ?
N1 C22 C23 C24 82.3(5) . . . . ?
C22 C23 C24 C25 83.0(6) . . . . ?
C22 C23 C24 C29 -98.1(6) . . . . ?
C29 C24 C25 C26 -1.3(8) . . . . ?
C23 C24 C25 C26 177.6(5) . . . . ?
C24 C25 C26 C27 1.5(8) . . . . ?
C25 C26 C27 C28 -0.2(8) . . . . ?
C25 C26 C27 C30 179.8(5) . . . . ?
C26 C27 C28 C29 -1.3(8) . . . . ?
C30 C27 C28 C29 178.8(5) . . . . ?
C27 C28 C29 C24 1.4(8) . . . . ?
C25 C24 C29 C28 -0.2(8) . . . . ?
C23 C24 C29 C28 -179.1(5) . . . . ?
C9 C8 N1 C22 -15.2(6) . . . . ?
S1 C8 N1 C22 156.2(3) . . . . ?
C9 C8 N1 S2 122.4(4) . . . . ?
S1 C8 N1 S2 -66.2(4) . . . . ?
C21 C22 N1 C8 20.1(6) . . . . ?
C23 C22 N1 C8 -154.4(4) . . . . ?
C21 C22 N1 S2 -116.1(4) . . . . ?
C23 C22 N1 S2 69.3(4) . . . . ?
C10 C11 S1 C8 0.6(4) . . . . ?
C12 C11 S1 C8 179.4(5) . . . . ?
C9 C8 S1 C11 0.6(4) . . . . ?
N1 C8 S1 C11 -171.6(4) . . . . ?
C8 N1 S2 O2 174.7(3) . . . . ?
C22 N1 S2 O2 -48.7(4) . . . . ?
C8 N1 S2 O1 45.6(4) . . . . ?
C22 N1 S2 O1 -177.8(4) . . . . ?
C8 N1 S2 C5 -69.1(4) . . . . ?
C22 N1 S2 C5 67.5(4) . . . . ?
C6 C5 S2 O2 -160.0(4) . . . . ?
C4 C5 S2 O2 21.8(5) . . . . ?
C6 C5 S2 O1 -27.5(4) . . . . ?
C4 C5 S2 O1 154.4(4) . . . . ?
C6 C5 S2 N1 85.0(4) . . . . ?
C4 C5 S2 N1 -93.2(4) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/petroleum ether'
####################################################################### 
# 
# 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 2270502'
loop_
_audit_author_name
_audit_author_address
'Da-Ming Du'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-17 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"(5bS,12cS,Z)-6-benzylidene-7-tosyl-5b,6,7,12c,13,14-hexahydro-5H-benzo[4',5']thieno- [3',2':5,6]pyrido[3,4-a]carbazole"
_chemical_name_common            ?
_chemical_melting_point          442-443
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H28 N2 O2 S2'
_chemical_formula_weight         572.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.6474(14)
_cell_length_b                   13.1696(19)
_cell_length_c                   22.923(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2912.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      66.31

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.931
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30681
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.857
_diffrn_reflns_theta_max         67.366
_diffrn_reflns_theta_full        67.366
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5189
_reflns_number_gt                3761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.985

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1428P)²] 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_abs_structure_details 
;
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.090(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5189
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.2164
_refine_ls_wR_factor_gt          0.1865
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
C1 C 0.8221(5) 0.5719(3) 0.83521(19) 0.089(2) Uani 1 1 d G . . . .
H1 H 0.8551 0.6287 0.8155 0.107 Uiso 1 1 calc R U . . .
C2 C 0.8765(5) 0.5461(4) 0.8894(2) 0.102(3) Uani 1 1 d G . . . .
H2 H 0.9459 0.5857 0.9059 0.123 Uiso 1 1 calc R U . . .
C3 C 0.8271(6) 0.4612(5) 0.91876(16) 0.103(3) Uani 1 1 d G . . . .
H3 H 0.8635 0.4440 0.9550 0.124 Uiso 1 1 calc R U . . .
C4 C 0.7234(6) 0.4020(3) 0.89400(18) 0.086(2) Uani 1 1 d G . . . .
H4 H 0.6904 0.3452 0.9137 0.103 Uiso 1 1 calc R U . . .
C5 C 0.6690(5) 0.4278(3) 0.83984(18) 0.0723(17) Uani 1 1 d G . . . .
C6 C 0.7183(5) 0.5127(3) 0.81044(14) 0.0700(16) Uani 1 1 d G . . . .
C7 C 0.6469(7) 0.5272(5) 0.7548(2) 0.0654(15) Uani 1 1 d . . . . .
C8 C 0.5506(7) 0.4541(5) 0.7469(3) 0.0630(14) Uani 1 1 d . . . . .
C9 C 0.5337(7) 0.5005(4) 0.6466(2) 0.0616(14) Uani 1 1 d . . . . .
C10 C 0.5634(7) 0.6088(5) 0.6629(3) 0.0638(15) Uani 1 1 d . . . . .
H10 H 0.4777 0.6372 0.6791 0.077 Uiso 1 1 calc R U . . .
C11 C 0.6744(7) 0.6116(5) 0.7123(2) 0.0631(15) Uani 1 1 d . . . . .
H11 H 0.6627 0.6758 0.7333 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8212(7) 0.6117(5) 0.6858(3) 0.0709(16) Uani 1 1 d . . . . .
H12A H 0.8892 0.6042 0.7166 0.085 Uiso 1 1 calc R U . . .
H12B H 0.8309 0.5546 0.6594 0.085 Uiso 1 1 calc R U . . .
C13 C 0.8485(7) 0.7108(5) 0.6526(3) 0.0711(16) Uani 1 1 d . . . . .
H13A H 0.8560 0.7669 0.6798 0.085 Uiso 1 1 calc R U . . .
H13B H 0.9349 0.7058 0.6311 0.085 Uiso 1 1 calc R U . . .
C14 C 0.7311(7) 0.7290(5) 0.6113(3) 0.0659(15) Uani 1 1 d . . . . .
C15 C 0.6081(7) 0.6767(5) 0.6153(3) 0.0644(15) Uani 1 1 d . . . . .
C16 C 0.5873(4) 0.7808(3) 0.53805(17) 0.0697(16) Uani 1 1 d G . . . .
C17 C 0.7168(5) 0.7987(3) 0.56258(15) 0.0710(16) Uani 1 1 d G . . . .
C18 C 0.8036(4) 0.8720(3) 0.5387(2) 0.0810(19) Uani 1 1 d G . . . .
H18 H 0.8903 0.8840 0.5551 0.097 Uiso 1 1 calc R U . . .
C19 C 0.7610(5) 0.9274(3) 0.4903(2) 0.088(2) Uani 1 1 d G . . . .
H19 H 0.8191 0.9764 0.4744 0.106 Uiso 1 1 calc R U . . .
C20 C 0.6315(5) 0.9095(3) 0.46579(16) 0.084(2) Uani 1 1 d G . . . .
H20 H 0.6030 0.9466 0.4334 0.101 Uiso 1 1 calc R U . . .
C21 C 0.5447(4) 0.8362(3) 0.48965(17) 0.080(2) Uani 1 1 d G . . . .
H21 H 0.4581 0.8243 0.4732 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5720(8) 0.4551(5) 0.5970(3) 0.0703(16) Uani 1 1 d . . . . .
H22 H 0.6111 0.4990 0.5698 0.084 Uiso 1 1 calc R U . . .
C23 C 0.5641(6) 0.3483(3) 0.5768(2) 0.0786(19) Uani 1 1 d G . . . .
C28 C 0.4841(6) 0.2733(4) 0.6031(2) 0.097(2) Uani 1 1 d G . . . .
H28 H 0.4310 0.2887 0.6358 0.117 Uiso 1 1 calc R U . . .
C27 C 0.4834(7) 0.1754(3) 0.5804(3) 0.115(3) Uani 1 1 d G . . . .
H27 H 0.4299 0.1252 0.5980 0.138 Uiso 1 1 calc R U . . .
C26 C 0.5627(9) 0.1524(4) 0.5316(3) 0.139(4) Uani 1 1 d G . . . .
H26 H 0.5623 0.0869 0.5164 0.166 Uiso 1 1 calc R U . . .
C25 C 0.6428(9) 0.2274(5) 0.5053(3) 0.154(5) Uani 1 1 d G . . . .
H25 H 0.6958 0.2120 0.4726 0.185 Uiso 1 1 calc R U . . .
C24 C 0.6434(8) 0.3253(4) 0.5280(2) 0.123(4) Uani 1 1 d G . . . .
H24 H 0.6970 0.3754 0.5104 0.147 Uiso 1 1 calc R U . . .
C29 C 0.2445(5) 0.5481(3) 0.73764(18) 0.0709(16) Uani 1 1 d G . . . .
C34 C 0.1993(5) 0.6330(4) 0.70704(16) 0.0807(18) Uani 1 1 d G . . . .
H34 H 0.1980 0.6322 0.6665 0.097 Uiso 1 1 calc R U . . .
C33 C 0.1561(5) 0.7190(3) 0.7371(3) 0.092(2) Uani 1 1 d G . . . .
H33 H 0.1259 0.7758 0.7166 0.110 Uiso 1 1 calc R U . . .
C32 C 0.1582(6) 0.7202(4) 0.7977(3) 0.100(3) Uani 1 1 d G . . . .
C31 C 0.2034(6) 0.6353(5) 0.82830(16) 0.101(3) Uani 1 1 d G . . . .
H31 H 0.2047 0.6361 0.8689 0.121 Uiso 1 1 calc R U . . .
C30 C 0.2466(6) 0.5492(4) 0.79826(18) 0.091(2) Uani 1 1 d G . . . .
H30 H 0.2768 0.4924 0.8187 0.109 Uiso 1 1 calc R U . . .
C35 C 0.1090(13) 0.8141(9) 0.8291(6) 0.143(4) Uani 1 1 d . . . . .
H35A H 0.0535 0.8544 0.8031 0.215 Uiso 1 1 calc R U . . .
H35B H 0.1877 0.8530 0.8417 0.215 Uiso 1 1 calc R U . . .
H35C H 0.0546 0.7948 0.8623 0.215 Uiso 1 1 calc R U . . .
N1 N 0.4718(5) 0.4435(4) 0.69418(19) 0.0638(12) Uani 1 1 d . . . . .
N2 N 0.5199(6) 0.7091(4) 0.5706(2) 0.0721(14) Uani 1 1 d . . . . .
H2A H 0.4370 0.6875 0.5645 0.087 Uiso 1 1 calc R U . . .
O1 O 0.2688(5) 0.3532(3) 0.7348(2) 0.0804(13) Uani 1 1 d . . . . .
O2 O 0.2474(5) 0.4458(4) 0.64093(19) 0.0799(13) Uani 1 1 d . . . . .
S1 S 0.29846(17) 0.44027(13) 0.69973(7) 0.0683(4) Uani 1 1 d . . . . .
S2 S 0.5385(2) 0.36561(13) 0.80264(7) 0.0747(5) 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 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 S2 1.727(4) . ?
C6 C7 1.462(7) . ?
C7 C8 1.350(9) . ?
C7 C11 1.502(8) . ?
C8 N1 1.434(7) . ?
C8 S2 1.734(6) . ?
C9 C22 1.336(9) . ?
C9 N1 1.453(7) . ?
C9 C10 1.503(8) . ?
C10 C15 1.477(8) . ?
C10 C11 1.558(9) . ?
C10 H10 0.9800 . ?
C11 C12 1.542(9) . ?
C11 H11 0.9800 . ?
C12 C13 1.533(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.495(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.374(9) . ?
C14 C17 1.453(7) . ?
C15 N2 1.399(8) . ?
C16 N2 1.368(6) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.482(7) . ?
C22 H22 0.9300 . ?
C23 C28 1.3900 . ?
C23 C24 1.3900 . ?
C28 C27 1.3900 . ?
C28 H28 0.9300 . ?
C27 C26 1.3900 . ?
C27 H27 0.9300 . ?
C26 C25 1.3900 . ?
C26 H26 0.9300 . ?
C25 C24 1.3900 . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C29 C34 1.3900 . ?
C29 C30 1.3900 . ?
C29 S1 1.744(4) . ?
C34 C33 1.3900 . ?
C34 H34 0.9300 . ?
C33 C32 1.3900 . ?
C33 H33 0.9300 . ?
C32 C31 1.3900 . ?
C32 C35 1.507(11) . ?
C31 C30 1.3900 . ?
C31 H31 0.9300 . ?
C30 H30 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
N1 S1 1.677(6) . ?
N2 H2A 0.8600 . ?
O1 S1 1.429(4) . ?
O2 S1 1.437(5) . ?

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 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 S2 126.9(2) . . ?
C6 C5 S2 113.1(2) . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 111.5(4) . . ?
C1 C6 C7 128.5(4) . . ?
C8 C7 C6 110.4(5) . . ?
C8 C7 C11 124.2(5) . . ?
C6 C7 C11 125.4(5) . . ?
C7 C8 N1 123.2(5) . . ?
C7 C8 S2 115.3(5) . . ?
N1 C8 S2 121.3(4) . . ?
C22 C9 N1 121.4(6) . . ?
C22 C9 C10 125.8(6) . . ?
N1 C9 C10 112.4(5) . . ?
C15 C10 C9 116.5(5) . . ?
C15 C10 C11 108.8(5) . . ?
C9 C10 C11 109.6(5) . . ?
C15 C10 H10 107.2 . . ?
C9 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C7 C11 C12 114.8(6) . . ?
C7 C11 C10 109.4(5) . . ?
C12 C11 C10 110.2(5) . . ?
C7 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C10 C11 H11 107.4 . . ?
C13 C12 C11 110.8(6) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 108.7(5) . . ?
C14 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?
C15 C14 C17 106.6(5) . . ?
C15 C14 C13 122.2(6) . . ?
C17 C14 C13 131.2(5) . . ?
C14 C15 N2 109.0(5) . . ?
C14 C15 C10 127.2(6) . . ?
N2 C15 C10 123.3(6) . . ?
N2 C16 C17 108.9(4) . . ?
N2 C16 C21 131.0(4) . . ?
C17 C16 C21 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 C14 133.2(4) . . ?
C16 C17 C14 106.8(4) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C9 C22 C23 132.5(6) . . ?
C9 C22 H22 113.8 . . ?
C23 C22 H22 113.8 . . ?
C28 C23 C24 120.0 . . ?
C28 C23 C22 124.6(4) . . ?
C24 C23 C22 115.4(4) . . ?
C23 C28 C27 120.0 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C34 C29 C30 120.0 . . ?
C34 C29 S1 119.8(3) . . ?
C30 C29 S1 120.2(3) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 C35 118.8(6) . . ?
C31 C32 C35 121.2(6) . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C8 N1 C9 111.4(5) . . ?
C8 N1 S1 117.8(4) . . ?
C9 N1 S1 118.7(4) . . ?
C16 N2 C15 108.6(5) . . ?
C16 N2 H2A 125.7 . . ?
C15 N2 H2A 125.7 . . ?
O1 S1 O2 119.9(3) . . ?
O1 S1 N1 105.2(3) . . ?
O2 S1 N1 105.6(3) . . ?
O1 S1 C29 108.3(3) . . ?
O2 S1 C29 108.9(3) . . ?
N1 S1 C29 108.3(3) . . ?
C5 S2 C8 89.8(3) . . ?

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 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 S2 -178.8(4) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
S2 C5 C6 C1 178.9(4) . . . . ?
C4 C5 C6 C7 -179.4(5) . . . . ?
S2 C5 C6 C7 -0.4(4) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C7 179.3(6) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C1 C6 C7 C8 -178.9(5) . . . . ?
C5 C6 C7 C11 179.8(5) . . . . ?
C1 C6 C7 C11 0.5(9) . . . . ?
C6 C7 C8 N1 -174.7(6) . . . . ?
C11 C7 C8 N1 5.9(10) . . . . ?
C6 C7 C8 S2 -0.3(7) . . . . ?
C11 C7 C8 S2 -179.7(5) . . . . ?
C22 C9 C10 C15 15.4(10) . . . . ?
N1 C9 C10 C15 -171.7(5) . . . . ?
C22 C9 C10 C11 -108.5(7) . . . . ?
N1 C9 C10 C11 64.3(7) . . . . ?
C8 C7 C11 C12 -117.3(7) . . . . ?
C6 C7 C11 C12 63.4(8) . . . . ?
C8 C7 C11 C10 7.1(9) . . . . ?
C6 C7 C11 C10 -172.2(6) . . . . ?
C15 C10 C11 C7 -167.9(5) . . . . ?
C9 C10 C11 C7 -39.5(7) . . . . ?
C15 C10 C11 C12 -40.9(7) . . . . ?
C9 C10 C11 C12 87.5(6) . . . . ?
C7 C11 C12 C13 -169.1(5) . . . . ?
C10 C11 C12 C13 66.9(7) . . . . ?
C11 C12 C13 C14 -50.7(7) . . . . ?
C12 C13 C14 C15 14.2(8) . . . . ?
C12 C13 C14 C17 -166.4(6) . . . . ?
C17 C14 C15 N2 1.3(7) . . . . ?
C13 C14 C15 N2 -179.1(6) . . . . ?
C17 C14 C15 C10 -170.0(6) . . . . ?
C13 C14 C15 C10 9.6(10) . . . . ?
C9 C10 C15 C14 -119.8(7) . . . . ?
C11 C10 C15 C14 4.6(9) . . . . ?
C9 C10 C15 N2 70.1(9) . . . . ?
C11 C10 C15 N2 -165.5(6) . . . . ?
N2 C16 C17 C18 -177.4(4) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
N2 C16 C17 C14 3.2(4) . . . . ?
C21 C16 C17 C14 -179.4(4) . . . . ?
C15 C14 C17 C18 178.0(4) . . . . ?
C13 C14 C17 C18 -1.5(10) . . . . ?
C15 C14 C17 C16 -2.7(6) . . . . ?
C13 C14 C17 C16 177.7(6) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C14 C17 C18 C19 179.2(6) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
N2 C16 C21 C20 176.7(5) . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
N1 C9 C22 C23 0.5(12) . . . . ?
C10 C9 C22 C23 172.8(7) . . . . ?
C9 C22 C23 C28 14.9(11) . . . . ?
C9 C22 C23 C24 -165.5(8) . . . . ?
C24 C23 C28 C27 0.0 . . . . ?
C22 C23 C28 C27 179.6(6) . . . . ?
C23 C28 C27 C26 0.0 . . . . ?
C28 C27 C26 C25 0.0 . . . . ?
C27 C26 C25 C24 0.0 . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C28 C23 C24 C25 0.0 . . . . ?
C22 C23 C24 C25 -179.6(6) . . . . ?
C30 C29 C34 C33 0.0 . . . . ?
S1 C29 C34 C33 179.9(4) . . . . ?
C29 C34 C33 C32 0.0 . . . . ?
C34 C33 C32 C31 0.0 . . . . ?
C34 C33 C32 C35 -179.2(7) . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C35 C32 C31 C30 179.2(7) . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
S1 C29 C30 C31 -179.9(4) . . . . ?
C7 C8 N1 C9 15.8(9) . . . . ?
S2 C8 N1 C9 -158.3(5) . . . . ?
C7 C8 N1 S1 -126.3(6) . . . . ?
S2 C8 N1 S1 59.6(6) . . . . ?
C22 C9 N1 C8 122.3(7) . . . . ?
C10 C9 N1 C8 -50.9(7) . . . . ?
C22 C9 N1 S1 -96.0(7) . . . . ?
C10 C9 N1 S1 90.9(6) . . . . ?
C17 C16 N2 C15 -2.5(5) . . . . ?
C21 C16 N2 C15 -179.5(4) . . . . ?
C14 C15 N2 C16 0.7(7) . . . . ?
C10 C15 N2 C16 172.3(5) . . . . ?
C8 N1 S1 O1 -61.2(5) . . . . ?
C9 N1 S1 O1 159.5(4) . . . . ?
C8 N1 S1 O2 171.0(4) . . . . ?
C9 N1 S1 O2 31.7(5) . . . . ?
C8 N1 S1 C29 54.5(5) . . . . ?
C9 N1 S1 C29 -84.9(5) . . . . ?
C34 C29 S1 O1 -149.5(3) . . . . ?
C30 C29 S1 O1 30.4(4) . . . . ?
C34 C29 S1 O2 -17.6(4) . . . . ?
C30 C29 S1 O2 162.4(3) . . . . ?
C34 C29 S1 N1 96.8(3) . . . . ?
C30 C29 S1 N1 -83.2(3) . . . . ?
C4 C5 S2 C8 179.1(4) . . . . ?
C6 C5 S2 C8 0.2(3) . . . . ?
C7 C8 S2 C5 0.0(5) . . . . ?
N1 C8 S2 C5 174.6(5) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Perroleum ether/chloroform 1:1'
