# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_mo_210929_nc_1784_0m
_database_code_depnum_ccdc_archive 'CCDC 2120491'
loop_
_audit_author_name
_audit_author_address
'Da-Ming Du'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-11-06 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;
_audit_creation_date             2021-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-2-(2-nitro-1-(4-nitrophenyl)ethyl)benzo[b]thiophen-3-yl benzoate'
_chemical_formula_moiety         C23H16N2O6S
_chemical_formula_sum            448.44
_chemical_formula_weight         448.44
_chemical_absolute_configuration ad
_chemical_melting_point          411-412
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.8028(7)
_cell_length_b                   8.2847(3)
_cell_length_c                   17.6240(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.031(2)
_cell_angle_gamma                90
_cell_volume                     2055.20(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0812 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9367.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'white solid'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40374
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.148
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                8182
_reflns_number_total             9048
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 3429 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         9048
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.4055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C42(H42),
 C43(H43), C45(H45), C46(H46)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.09262(5) 0.52742(8) 0.09442(4) 0.03127(16) Uani 1 1 d . . . . .
O1 O -0.19332(17) 0.2524(3) 0.29050(14) 0.0447(5) Uani 1 1 d . . . . .
O2 O -0.12251(14) 0.1352(2) 0.20811(12) 0.0314(4) Uani 1 1 d . . . . .
O3 O 0.0598(2) -0.0505(3) 0.17982(17) 0.0664(7) Uani 1 1 d . . . . .
O4 O 0.10314(17) 0.1449(3) 0.11848(16) 0.0550(6) Uani 1 1 d . . . . .
O5 O 0.0802(3) 0.7910(4) 0.52616(18) 0.0879(11) Uani 1 1 d . . . . .
O6 O 0.1464(5) 0.9489(6) 0.4638(3) 0.189(3) Uani 1 1 d . . . . .
N1 N 0.08204(19) 0.0881(4) 0.17462(17) 0.0436(7) Uani 1 1 d . . . . .
N2 N 0.1107(3) 0.8210(6) 0.4707(2) 0.0841(13) Uani 1 1 d . . . . .
C1 C -0.31007(19) 0.2531(4) 0.09366(18) 0.0316(6) Uani 1 1 d . . . . .
H1 H -0.317858 0.160132 0.122541 0.038 Uiso 1 1 calc R . . . .
C2 C -0.3870(2) 0.3189(4) 0.03565(19) 0.0370(7) Uani 1 1 d . . . . .
H2 H -0.448124 0.271651 0.025187 0.044 Uiso 1 1 calc R . . . .
C3 C -0.3753(2) 0.4545(4) -0.00760(18) 0.0387(7) Uani 1 1 d . . . . .
H3 H -0.428774 0.498575 -0.046995 0.046 Uiso 1 1 calc R . . . .
C4 C -0.2871(2) 0.5256(4) 0.00595(17) 0.0357(6) Uani 1 1 d . . . . .
H4 H -0.279153 0.615483 -0.024848 0.043 Uiso 1 1 calc R . . . .
C5 C -0.21022(18) 0.4622(4) 0.06580(16) 0.0285(5) Uani 1 1 d . . . . .
C6 C -0.22059(18) 0.3255(3) 0.10923(15) 0.0264(5) Uani 1 1 d . . . . .
C7 C -0.13101(19) 0.2782(3) 0.16455(16) 0.0259(5) Uani 1 1 d . . . . .
C8 C -0.05610(18) 0.3718(3) 0.16479(15) 0.0267(5) Uani 1 1 d . . . . .
C9 C -0.1634(2) 0.1326(4) 0.26787(17) 0.0309(6) Uani 1 1 d . . . . .
C10 C -0.16525(19) -0.0337(4) 0.29827(17) 0.0312(6) Uani 1 1 d . . . . .
C11 C -0.1921(2) -0.0540(5) 0.36713(19) 0.0451(8) Uani 1 1 d . . . . .
H11 H -0.207271 0.036847 0.393775 0.054 Uiso 1 1 calc R . . . .
C12 C -0.1963(3) -0.2100(5) 0.3961(2) 0.0526(9) Uani 1 1 d . . . . .
H12 H -0.213807 -0.225176 0.443170 0.063 Uiso 1 1 calc R . . . .
C13 C -0.1754(2) -0.3417(4) 0.3571(2) 0.0474(8) Uani 1 1 d . . . . .
H13 H -0.178641 -0.447149 0.377240 0.057 Uiso 1 1 calc R . . . .
C14 C -0.1497(2) -0.3215(4) 0.2891(2) 0.0422(8) Uani 1 1 d . . . . .
H14 H -0.136398 -0.413135 0.261958 0.051 Uiso 1 1 calc R . . . .
C15 C -0.1432(2) -0.1675(4) 0.25975(19) 0.0351(6) Uani 1 1 d . . . . .
H15 H -0.123845 -0.153816 0.213570 0.042 Uiso 1 1 calc R . . . .
C16 C 0.04779(19) 0.3658(4) 0.21457(16) 0.0313(6) Uani 1 1 d . . . . .
H16 H 0.085249 0.405737 0.179907 0.038 Uiso 1 1 calc R . . . .
C17 C 0.0847(2) 0.1990(4) 0.24268(18) 0.0387(7) Uani 1 1 d . . . . .
H17A H 0.150911 0.207707 0.278362 0.046 Uiso 1 1 calc R . . . .
H17B H 0.045850 0.152110 0.273910 0.046 Uiso 1 1 calc R . . . .
C18 C 0.06809(19) 0.4802(4) 0.28560(17) 0.0316(6) Uani 1 1 d . . . . .
C19 C 0.1095(3) 0.6277(4) 0.2809(2) 0.0476(8) Uani 1 1 d . . . . .
H19 H 0.127468 0.653259 0.235009 0.057 Uiso 1 1 calc R . . . .
C20 C 0.1251(3) 0.7390(5) 0.3425(2) 0.0614(10) Uani 1 1 d . . . . .
H20 H 0.153245 0.840719 0.339163 0.074 Uiso 1 1 calc R . . . .
C21 C 0.0991(3) 0.6992(5) 0.4081(2) 0.0507(9) Uani 1 1 d . . . . .
C22 C 0.0590(2) 0.5525(5) 0.41583(19) 0.0465(8) Uani 1 1 d . . . . .
H22 H 0.041903 0.527433 0.462185 0.056 Uiso 1 1 calc R . . . .
C23 C 0.0444(2) 0.4425(4) 0.35382(18) 0.0404(7) Uani 1 1 d . . . . .
H23 H 0.017698 0.339847 0.358100 0.048 Uiso 1 1 calc R . . . .
S2 S 0.40456(5) 0.46746(8) 0.09988(4) 0.02949(16) Uani 1 1 d . . . . .
O7 O 0.32769(18) 0.7501(3) 0.29902(14) 0.0459(6) Uani 1 1 d . . . . .
O8 O 0.36365(14) 0.8721(2) 0.19845(11) 0.0314(4) Uani 1 1 d . . . . .
O9 O 0.58364(19) 0.9445(3) 0.17675(15) 0.0540(6) Uani 1 1 d . . . . .
O10 O 0.6281(2) 0.8349(3) 0.08451(15) 0.0649(7) Uani 1 1 d . . . . .
O11 O 0.5819(3) 0.1468(5) 0.51077(18) 0.0893(11) Uani 1 1 d . . . . .
O12 O 0.5993(3) -0.0162(4) 0.4211(2) 0.0918(12) Uani 1 1 d . . . . .
N3 N 0.60669(17) 0.8268(3) 0.14560(14) 0.0368(6) Uani 1 1 d . . . . .
N4 N 0.5883(2) 0.1184(4) 0.4445(2) 0.0590(9) Uani 1 1 d . . . . .
C24 C 0.1808(2) 0.7387(4) 0.08392(18) 0.0336(6) Uani 1 1 d . . . . .
H24 H 0.170396 0.836572 0.108017 0.040 Uiso 1 1 calc R . . . .
C25 C 0.1066(2) 0.6609(4) 0.0290(2) 0.0407(7) Uani 1 1 d . . . . .
H25 H 0.044214 0.704032 0.016566 0.049 Uiso 1 1 calc R . . . .
C26 C 0.1217(2) 0.5198(4) -0.00863(19) 0.0411(7) Uani 1 1 d . . . . .
H26 H 0.069426 0.468085 -0.046145 0.049 Uiso 1 1 calc R . . . .
C27 C 0.2115(2) 0.4541(4) 0.00785(18) 0.0359(6) Uani 1 1 d . . . . .
H27 H 0.221984 0.360148 -0.019214 0.043 Uiso 1 1 calc R . . . .
C28 C 0.28654(18) 0.5292(4) 0.06524(16) 0.0273(5) Uani 1 1 d . . . . .
C29 C 0.27181(19) 0.6710(3) 0.10358(16) 0.0272(6) Uani 1 1 d . . . . .
C30 C 0.35850(19) 0.7253(3) 0.15871(16) 0.0263(5) Uani 1 1 d . . . . .
C31 C 0.43525(18) 0.6296(3) 0.16617(15) 0.0256(5) Uani 1 1 d . . . . .
C32 C 0.34093(19) 0.8718(4) 0.26796(16) 0.0281(6) Uani 1 1 d . . . . .
C33 C 0.33567(18) 1.0388(4) 0.29742(16) 0.0277(5) Uani 1 1 d . . . . .
C34 C 0.3291(2) 1.0565(4) 0.37397(17) 0.0355(6) Uani 1 1 d . . . . .
H34 H 0.328633 0.964069 0.405760 0.043 Uiso 1 1 calc R . . . .
C35 C 0.3233(2) 1.2103(4) 0.40377(18) 0.0429(8) Uani 1 1 d . . . . .
H35 H 0.319880 1.222950 0.456401 0.051 Uiso 1 1 calc R . . . .
C36 C 0.3223(2) 1.3452(4) 0.35705(19) 0.0404(7) Uani 1 1 d . . . . .
H36 H 0.318269 1.449930 0.377748 0.048 Uiso 1 1 calc R . . . .
C37 C 0.3273(2) 1.3281(4) 0.2808(2) 0.0377(7) Uani 1 1 d . . . . .
H37 H 0.325252 1.420656 0.248462 0.045 Uiso 1 1 calc R . . . .
C38 C 0.3354(2) 1.1739(4) 0.25082(18) 0.0309(6) Uani 1 1 d . . . . .
H38 H 0.340658 1.161914 0.198744 0.037 Uiso 1 1 calc R . . . .
C39 C 0.53319(19) 0.6484(4) 0.22458(16) 0.0301(6) Uani 1 1 d . . . . .
H39 H 0.533466 0.749902 0.255364 0.036 Uiso 1 1 calc R . . . .
C40 C 0.61027(19) 0.6653(4) 0.18378(17) 0.0333(6) Uani 1 1 d . . . . .
H40A H 0.673468 0.649778 0.223763 0.040 Uiso 1 1 calc R . . . .
H40B H 0.601570 0.580126 0.142708 0.040 Uiso 1 1 calc R . . . .
C41 C 0.55548(18) 0.5087(3) 0.28421(16) 0.0285(6) Uani 1 1 d . . . . .
C42 C 0.5444(2) 0.5317(4) 0.35906(16) 0.0345(6) Uani 1 1 d . . . . .
H42 H 0.528562 0.635683 0.373852 0.041 Uiso 1 1 calc R . . . .
C43 C 0.5563(2) 0.4044(4) 0.41212(17) 0.0411(7) Uani 1 1 d . . . . .
H43 H 0.548595 0.419647 0.463175 0.049 Uiso 1 1 calc R . . . .
C44 C 0.5797(2) 0.2552(4) 0.38922(18) 0.0401(7) Uani 1 1 d . . . . .
C45 C 0.5923(2) 0.2278(4) 0.31629(19) 0.0422(7) Uani 1 1 d . . . . .
H45 H 0.608571 0.123486 0.302277 0.051 Uiso 1 1 calc R . . . .
C46 C 0.5806(2) 0.3561(4) 0.26364(17) 0.0376(7) Uani 1 1 d . . . . .
H46 H 0.589767 0.340122 0.213147 0.045 Uiso 1 1 calc R . . . .


_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 C5 1.742(3) . ?
S1 C8 1.754(3) . ?
O1 C9 1.204(4) . ?
O2 C7 1.395(3) . ?
O2 C9 1.368(3) . ?
O3 N1 1.206(4) . ?
O4 N1 1.221(4) . ?
O5 N2 1.223(5) . ?
O6 N2 1.207(6) . ?
N1 C17 1.502(4) . ?
N2 C21 1.466(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(4) . ?
C1 C6 1.402(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(4) . ?
C5 C6 1.401(4) . ?
C6 C7 1.436(4) . ?
C7 C8 1.352(4) . ?
C8 C16 1.517(4) . ?
C9 C10 1.482(4) . ?
C10 C11 1.399(4) . ?
C10 C15 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(4) . ?
C15 H15 0.9500 . ?
C16 H16 1.0000 . ?
C16 C17 1.512(4) . ?
C16 C18 1.524(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.381(5) . ?
C18 C23 1.389(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.366(5) . ?
C21 C22 1.378(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(5) . ?
C23 H23 0.9500 . ?
S2 C28 1.740(3) . ?
S2 C31 1.746(3) . ?
O7 C32 1.192(4) . ?
O8 C30 1.394(3) . ?
O8 C32 1.367(3) . ?
O9 N3 1.218(4) . ?
O10 N3 1.214(3) . ?
O11 N4 1.224(4) . ?
O12 N4 1.218(5) . ?
N3 C40 1.492(4) . ?
N4 C44 1.474(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(5) . ?
C24 C29 1.400(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.396(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.395(4) . ?
C28 C29 1.405(4) . ?
C29 C30 1.422(4) . ?
C30 C31 1.358(4) . ?
C31 C39 1.504(4) . ?
C32 C33 1.488(4) . ?
C33 C34 1.390(4) . ?
C33 C38 1.388(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.392(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.386(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.376(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.401(4) . ?
C38 H38 0.9500 . ?
C39 H39 1.0000 . ?
C39 C40 1.532(4) . ?
C39 C41 1.529(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.392(4) . ?
C41 C46 1.397(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.384(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.377(5) . ?
C44 C45 1.373(4) . ?
C45 H45 0.9500 . ?
C45 C46 1.386(4) . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C8 92.20(13) . . ?
C9 O2 C7 116.8(2) . . ?
O3 N1 O4 125.0(3) . . ?
O3 N1 C17 117.5(3) . . ?
O4 N1 C17 117.5(3) . . ?
O5 N2 C21 118.4(4) . . ?
O6 N2 O5 122.7(4) . . ?
O6 N2 C21 118.8(4) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.2(3) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 S1 127.7(2) . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 S1 111.2(2) . . ?
C1 C6 C7 129.3(3) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 110.9(2) . . ?
O2 C7 C6 120.8(2) . . ?
C8 C7 O2 123.4(2) . . ?
C8 C7 C6 115.4(2) . . ?
C7 C8 S1 110.3(2) . . ?
C7 C8 C16 131.8(3) . . ?
C16 C8 S1 117.9(2) . . ?
O1 C9 O2 122.6(3) . . ?
O1 C9 C10 126.6(3) . . ?
O2 C9 C10 110.8(2) . . ?
C11 C10 C9 117.9(3) . . ?
C15 C10 C9 122.1(3) . . ?
C15 C10 C11 120.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.8(3) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C8 C16 H16 106.9 . . ?
C8 C16 C18 111.2(2) . . ?
C17 C16 C8 114.7(2) . . ?
C17 C16 H16 106.9 . . ?
C17 C16 C18 109.9(2) . . ?
C18 C16 H16 106.9 . . ?
N1 C17 C16 112.3(2) . . ?
N1 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C16 118.6(3) . . ?
C19 C18 C23 119.2(3) . . ?
C23 C18 C16 122.2(3) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.7(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(3) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 N2 118.2(4) . . ?
C20 C21 C22 122.6(3) . . ?
C22 C21 N2 119.1(3) . . ?
C21 C22 H22 121.0 . . ?
C21 C22 C23 117.9(3) . . ?
C23 C22 H22 121.0 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C28 S2 C31 91.93(13) . . ?
C32 O8 C30 117.3(2) . . ?
O9 N3 C40 119.4(2) . . ?
O10 N3 O9 122.8(3) . . ?
O10 N3 C40 117.8(3) . . ?
O11 N4 C44 117.9(3) . . ?
O12 N4 O11 123.8(3) . . ?
O12 N4 C44 118.3(3) . . ?
C25 C24 H24 120.6 . . ?
C25 C24 C29 118.9(3) . . ?
C29 C24 H24 120.6 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.0(3) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 120.8 . . ?
C26 C27 C28 118.3(3) . . ?
C28 C27 H27 120.8 . . ?
C27 C28 S2 127.6(2) . . ?
C27 C28 C29 120.9(3) . . ?
C29 C28 S2 111.4(2) . . ?
C24 C29 C28 119.8(3) . . ?
C24 C29 C30 129.6(3) . . ?
C28 C29 C30 110.6(2) . . ?
O8 C30 C29 121.1(2) . . ?
C31 C30 O8 123.1(2) . . ?
C31 C30 C29 115.6(2) . . ?
C30 C31 S2 110.4(2) . . ?
C30 C31 C39 127.3(3) . . ?
C39 C31 S2 122.3(2) . . ?
O7 C32 O8 122.3(3) . . ?
O7 C32 C33 126.3(3) . . ?
O8 C32 C33 111.4(2) . . ?
C34 C33 C32 117.6(3) . . ?
C38 C33 C32 122.3(2) . . ?
C38 C33 C34 120.1(3) . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.6(3) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 119.9 . . ?
C37 C36 C35 120.2(3) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 120.0 . . ?
C36 C37 C38 119.9(3) . . ?
C38 C37 H37 120.0 . . ?
C33 C38 C37 119.8(3) . . ?
C33 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C31 C39 H39 107.4 . . ?
C31 C39 C40 112.9(2) . . ?
C31 C39 C41 110.4(2) . . ?
C40 C39 H39 107.4 . . ?
C41 C39 H39 107.4 . . ?
C41 C39 C40 111.0(2) . . ?
N3 C40 C39 111.5(2) . . ?
N3 C40 H40A 109.3 . . ?
N3 C40 H40B 109.3 . . ?
C39 C40 H40A 109.3 . . ?
C39 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C42 C41 C39 118.9(3) . . ?
C42 C41 C46 119.3(3) . . ?
C46 C41 C39 121.6(2) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 C41 120.5(3) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 120.8 . . ?
C44 C43 C42 118.5(3) . . ?
C44 C43 H43 120.8 . . ?
C43 C44 N4 118.3(3) . . ?
C45 C44 N4 118.8(3) . . ?
C45 C44 C43 122.8(3) . . ?
C44 C45 H45 120.8 . . ?
C44 C45 C46 118.3(3) . . ?
C46 C45 H45 120.8 . . ?
C41 C46 H46 119.7 . . ?
C45 C46 C41 120.6(3) . . ?
C45 C46 H46 119.7 . . ?

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
S1 C5 C6 C1 -178.8(2) . . . . ?
S1 C5 C6 C7 -0.3(3) . . . . ?
S1 C8 C16 C17 -152.0(2) . . . . ?
S1 C8 C16 C18 82.6(3) . . . . ?
O1 C9 C10 C11 -9.4(5) . . . . ?
O1 C9 C10 C15 169.2(3) . . . . ?
O2 C7 C8 S1 173.08(19) . . . . ?
O2 C7 C8 C16 -8.3(5) . . . . ?
O2 C9 C10 C11 170.9(3) . . . . ?
O2 C9 C10 C15 -10.4(4) . . . . ?
O3 N1 C17 C16 -141.3(3) . . . . ?
O4 N1 C17 C16 39.1(4) . . . . ?
O5 N2 C21 C20 173.8(4) . . . . ?
O5 N2 C21 C22 -3.5(6) . . . . ?
O6 N2 C21 C20 -3.1(7) . . . . ?
O6 N2 C21 C22 179.6(6) . . . . ?
N2 C21 C22 C23 176.8(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C6 C7 O2 5.2(4) . . . . ?
C1 C6 C7 C8 178.8(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C3 C4 C5 S1 179.6(2) . . . . ?
C3 C4 C5 C6 2.7(4) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
C4 C5 C6 C7 177.0(2) . . . . ?
C5 S1 C8 C7 0.1(2) . . . . ?
C5 S1 C8 C16 -178.7(2) . . . . ?
C5 C6 C7 O2 -173.2(2) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C7 C8 S1 -0.4(3) . . . . ?
C6 C7 C8 C16 178.2(3) . . . . ?
C7 O2 C9 O1 -10.6(4) . . . . ?
C7 O2 C9 C10 169.1(2) . . . . ?
C7 C8 C16 C17 29.5(4) . . . . ?
C7 C8 C16 C18 -95.9(4) . . . . ?
C8 S1 C5 C4 -177.0(3) . . . . ?
C8 S1 C5 C6 0.1(2) . . . . ?
C8 C16 C17 N1 63.7(3) . . . . ?
C8 C16 C18 C19 -100.7(3) . . . . ?
C8 C16 C18 C23 77.8(3) . . . . ?
C9 O2 C7 C6 -71.8(3) . . . . ?
C9 O2 C7 C8 115.1(3) . . . . ?
C9 C10 C11 C12 178.7(3) . . . . ?
C9 C10 C15 C14 -177.5(3) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C10 C15 C14 1.2(4) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C10 -1.7(5) . . . . ?
C15 C10 C11 C12 0.0(5) . . . . ?
C16 C18 C19 C20 176.9(3) . . . . ?
C16 C18 C23 C22 -176.5(3) . . . . ?
C17 C16 C18 C19 131.2(3) . . . . ?
C17 C16 C18 C23 -50.3(4) . . . . ?
C18 C16 C17 N1 -170.2(2) . . . . ?
C18 C19 C20 C21 0.4(6) . . . . ?
C19 C18 C23 C22 2.0(5) . . . . ?
C19 C20 C21 N2 -176.5(4) . . . . ?
C19 C20 C21 C22 0.7(6) . . . . ?
C20 C21 C22 C23 -0.4(6) . . . . ?
C21 C22 C23 C18 -1.0(5) . . . . ?
C23 C18 C19 C20 -1.7(5) . . . . ?
S2 C28 C29 C24 -179.6(2) . . . . ?
S2 C28 C29 C30 1.3(3) . . . . ?
S2 C31 C39 C40 61.3(3) . . . . ?
S2 C31 C39 C41 -63.6(3) . . . . ?
O7 C32 C33 C34 10.5(4) . . . . ?
O7 C32 C33 C38 -168.3(3) . . . . ?
O8 C30 C31 S2 -173.58(19) . . . . ?
O8 C30 C31 C39 9.4(4) . . . . ?
O8 C32 C33 C34 -169.4(2) . . . . ?
O8 C32 C33 C38 11.8(4) . . . . ?
O9 N3 C40 C39 34.1(4) . . . . ?
O10 N3 C40 C39 -146.6(3) . . . . ?
O11 N4 C44 C43 -5.9(5) . . . . ?
O11 N4 C44 C45 176.1(3) . . . . ?
O12 N4 C44 C43 172.6(4) . . . . ?
O12 N4 C44 C45 -5.3(5) . . . . ?
N4 C44 C45 C46 177.6(3) . . . . ?
C24 C25 C26 C27 -0.2(5) . . . . ?
C24 C29 C30 O8 -5.2(4) . . . . ?
C24 C29 C30 C31 178.2(3) . . . . ?
C25 C24 C29 C28 2.3(4) . . . . ?
C25 C24 C29 C30 -178.7(3) . . . . ?
C25 C26 C27 C28 2.2(4) . . . . ?
C26 C27 C28 S2 177.2(2) . . . . ?
C26 C27 C28 C29 -2.0(4) . . . . ?
C27 C28 C29 C24 -0.3(4) . . . . ?
C27 C28 C29 C30 -179.4(2) . . . . ?
C28 S2 C31 C30 -1.8(2) . . . . ?
C28 S2 C31 C39 175.4(2) . . . . ?
C28 C29 C30 O8 173.8(2) . . . . ?
C28 C29 C30 C31 -2.8(3) . . . . ?
C29 C24 C25 C26 -2.1(4) . . . . ?
C29 C30 C31 S2 2.9(3) . . . . ?
C29 C30 C31 C39 -174.1(2) . . . . ?
C30 O8 C32 O7 8.4(4) . . . . ?
C30 O8 C32 C33 -171.6(2) . . . . ?
C30 C31 C39 C40 -122.0(3) . . . . ?
C30 C31 C39 C41 113.1(3) . . . . ?
C31 S2 C28 C27 -179.0(3) . . . . ?
C31 S2 C28 C29 0.3(2) . . . . ?
C31 C39 C40 N3 73.1(3) . . . . ?
C31 C39 C41 C42 -98.6(3) . . . . ?
C31 C39 C41 C46 77.2(3) . . . . ?
C32 O8 C30 C29 86.6(3) . . . . ?
C32 O8 C30 C31 -97.1(3) . . . . ?
C32 C33 C34 C35 -179.5(3) . . . . ?
C32 C33 C38 C37 178.0(3) . . . . ?
C33 C34 C35 C36 1.1(5) . . . . ?
C34 C33 C38 C37 -0.8(4) . . . . ?
C34 C35 C36 C37 -0.1(5) . . . . ?
C35 C36 C37 C38 -1.4(5) . . . . ?
C36 C37 C38 C33 1.8(4) . . . . ?
C38 C33 C34 C35 -0.7(4) . . . . ?
C39 C41 C42 C43 174.7(3) . . . . ?
C39 C41 C46 C45 -174.3(3) . . . . ?
C40 C39 C41 C42 135.5(3) . . . . ?
C40 C39 C41 C46 -48.7(4) . . . . ?
C41 C39 C40 N3 -162.4(2) . . . . ?
C41 C42 C43 C44 0.3(5) . . . . ?
C42 C41 C46 C45 1.5(4) . . . . ?
C42 C43 C44 N4 -177.4(3) . . . . ?
C42 C43 C44 C45 0.5(5) . . . . ?
C43 C44 C45 C46 -0.2(5) . . . . ?
C44 C45 C46 C41 -0.8(5) . . . . ?
C46 C41 C42 C43 -1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/petroleum ether'
