# 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. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2169765'
loop_
_audit_author_name
_audit_author_address
'Da-Ming Du'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-05-01 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_1_a                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01067 Ang.  
RESPONSE: This is caused by the poor quality of the sample.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"(2'R,3S,4'S)-di-tert-butyl 6-chloro-4'-((3-methyl-4-nitroisoxazol-5-yl)methyl)-2-oxo-1'-tosyl-2',4'-dihydro-1'H-spiro[indoline-3,3'-quinoline]-1,2'-dicarboxylate"
_chemical_name_common            ?
_chemical_melting_point          439-441
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H39 Cl N4 O10 S'
_chemical_formula_weight         779.24

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'
Cl Cl 0.1484 0.1585 '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                   10.2003(6)
_cell_length_b                   9.9350(5)
_cell_length_c                   19.3125(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.1010(10)
_cell_angle_gamma                90
_cell_volume                     1942.12(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             816
_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    0.214
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.959
_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            29644
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         25.057
_diffrn_reflns_theta_full        25.057
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             6635
_reflns_number_gt                5162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.943

_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)+(0.1421P)²+1.8513P] 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 1933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6635
_refine_ls_number_parameters     485
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.2016
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.015
_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
C38 C 0.401(2) 0.616(2) 0.5742(9) 0.147(5) Uani 1 1 d . U . . .
H38A H 0.3637 0.6974 0.5900 0.220 Uiso 1 1 calc R U . . .
H38B H 0.3571 0.5398 0.5917 0.220 Uiso 1 1 calc R U . . .
H38C H 0.4934 0.6123 0.5909 0.220 Uiso 1 1 calc R U . . .
C1 C 0.4083(10) 0.4975(7) 0.3851(3) 0.093(4) Uani 1 1 d G . . . .
H1 H 0.4393 0.4243 0.3619 0.111 Uiso 1 1 calc R U . . .
C6 C 0.3422(9) 0.6014(7) 0.3472(3) 0.071(3) Uani 1 1 d G . . . .
C5 C 0.2958(11) 0.7109(7) 0.3819(4) 0.115(5) Uani 1 1 d G . . . .
H5 H 0.2516 0.7804 0.3565 0.139 Uiso 1 1 calc R U . . .
C4 C 0.3155(14) 0.7165(9) 0.4543(4) 0.164(9) Uani 1 1 d G . . . .
H4 H 0.2844 0.7897 0.4775 0.196 Uiso 1 1 calc R U . . .
C3 C 0.3815(15) 0.6126(11) 0.4922(3) 0.171(9) Uani 1 1 d G U . . .
C2 C 0.4280(12) 0.5031(10) 0.4576(3) 0.131(6) Uani 1 1 d G . . . .
H2 H 0.4722 0.4336 0.4829 0.157 Uiso 1 1 calc R U . . .
C7 C 0.5399(6) 0.5136(7) 0.2139(3) 0.0348(14) Uani 1 1 d . . . . .
H7 H 0.5114 0.4348 0.2386 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5212(6) 0.4793(7) 0.1364(3) 0.0362(15) Uani 1 1 d . . . . .
C9 C 0.5842(7) 0.3040(7) 0.0564(4) 0.0414(16) Uani 1 1 d . . . . .
C10 C 0.6642(10) 0.1791(9) 0.0719(4) 0.059(2) Uani 1 1 d . . . . .
H10A H 0.7491 0.2025 0.0960 0.089 Uiso 1 1 calc R U . . .
H10B H 0.6754 0.1342 0.0290 0.089 Uiso 1 1 calc R U . . .
H10C H 0.6193 0.1203 0.1007 0.089 Uiso 1 1 calc R U . . .
C11 C 0.6529(12) 0.3959(10) 0.0118(5) 0.072(3) Uani 1 1 d . . . . .
H11A H 0.6007 0.4756 0.0019 0.108 Uiso 1 1 calc R U . . .
H11B H 0.6646 0.3513 -0.0311 0.108 Uiso 1 1 calc R U . . .
H11C H 0.7376 0.4202 0.0359 0.108 Uiso 1 1 calc R U . . .
C12 C 0.4455(9) 0.2748(11) 0.0252(5) 0.065(2) Uani 1 1 d . . . . .
H12A H 0.4034 0.2190 0.0565 0.098 Uiso 1 1 calc R U . . .
H12B H 0.4465 0.2290 -0.0185 0.098 Uiso 1 1 calc R U . . .
H12C H 0.3976 0.3578 0.0176 0.098 Uiso 1 1 calc R U . . .
C13 C 0.6893(7) 0.5369(7) 0.2409(4) 0.0410(16) Uani 1 1 d . . . . .
C14 C 0.7456(7) 0.4017(7) 0.2668(4) 0.0428(17) Uani 1 1 d . . . . .
C15 C 0.8769(4) 0.4786(4) 0.1864(3) 0.0451(17) Uani 1 1 d G . . . .
C20 C 0.9739(4) 0.4940(5) 0.1424(3) 0.057(2) Uani 1 1 d G . . . .
H20 H 1.0411 0.4306 0.1428 0.069 Uiso 1 1 calc R U . . .
C19 C 0.9705(4) 0.6042(6) 0.0979(3) 0.063(2) Uani 1 1 d G . . . .
C18 C 0.8701(5) 0.6990(5) 0.0973(3) 0.058(2) Uani 1 1 d G . . . .
H18 H 0.8679 0.7727 0.0675 0.070 Uiso 1 1 calc R U . . .
C17 C 0.7731(4) 0.6835(4) 0.1413(3) 0.0520(19) Uani 1 1 d G . . . .
H17 H 0.7060 0.7469 0.1410 0.062 Uiso 1 1 calc R U . . .
C16 C 0.7765(4) 0.5733(5) 0.1859(2) 0.0421(16) Uani 1 1 d G . . . .
C21 C 0.9268(7) 0.2492(8) 0.2443(5) 0.0496(19) Uani 1 1 d . . . . .
C22 C 1.0920(7) 0.1115(8) 0.1970(5) 0.061(2) Uani 1 1 d . . . . .
C23 C 1.1806(9) 0.1036(12) 0.2657(5) 0.078(3) Uani 1 1 d . . . . .
H23A H 1.2268 0.1874 0.2742 0.116 Uiso 1 1 calc R U . . .
H23B H 1.2433 0.0321 0.2638 0.116 Uiso 1 1 calc R U . . .
H23C H 1.1280 0.0865 0.3027 0.116 Uiso 1 1 calc R U . . .
C24 C 1.0055(11) -0.0116(11) 0.1836(9) 0.107(5) Uani 1 1 d . . . . .
H24A H 0.9510 -0.0213 0.2204 0.160 Uiso 1 1 calc R U . . .
H24B H 1.0601 -0.0900 0.1820 0.160 Uiso 1 1 calc R U . . .
H24C H 0.9506 -0.0017 0.1398 0.160 Uiso 1 1 calc R U . . .
C25 C 1.1705(10) 0.1420(12) 0.1374(6) 0.085(3) Uani 1 1 d . . . . .
H25A H 1.1131 0.1387 0.0941 0.127 Uiso 1 1 calc R U . . .
H25B H 1.2395 0.0765 0.1367 0.127 Uiso 1 1 calc R U . . .
H25C H 1.2086 0.2302 0.1436 0.127 Uiso 1 1 calc R U . . .
C26 C 0.6993(8) 0.6399(8) 0.3026(4) 0.052(2) Uani 1 1 d . . . . .
H26 H 0.6489 0.6039 0.3385 0.063 Uiso 1 1 calc R U . . .
C27 C 0.6336(4) 0.7686(4) 0.2751(2) 0.0446(18) Uani 1 1 d G . . . .
C32 C 0.6928(4) 0.8945(5) 0.2835(3) 0.056(2) Uani 1 1 d G . . . .
H32 H 0.7755 0.9034 0.3094 0.067 Uiso 1 1 calc R U . . .
C31 C 0.6285(5) 1.0072(4) 0.2532(3) 0.058(2) Uani 1 1 d G . . . .
H31 H 0.6681 1.0915 0.2588 0.070 Uiso 1 1 calc R U . . .
C30 C 0.5049(4) 0.9940(4) 0.2144(3) 0.057(2) Uani 1 1 d G . . . .
H30 H 0.4619 1.0693 0.1941 0.068 Uiso 1 1 calc R U . . .
C29 C 0.4457(4) 0.8680(5) 0.2061(2) 0.0476(18) Uani 1 1 d G . . . .
H29 H 0.3630 0.8592 0.1802 0.057 Uiso 1 1 calc R U . . .
C28 C 0.5100(4) 0.7554(4) 0.2364(2) 0.0374(15) Uani 1 1 d G . . . .
C33 C 0.8455(11) 0.6545(10) 0.3353(6) 0.089(4) Uani 1 1 d . . . . .
H33A H 0.8817 0.5648 0.3436 0.107 Uiso 1 1 calc R U . . .
H33B H 0.8940 0.6970 0.3010 0.107 Uiso 1 1 calc R U . . .
C34 C 0.8694(14) 0.7269(12) 0.3971(6) 0.102(4) Uani 1 1 d . U . . .
C35 C 0.8576(13) 0.7077(11) 0.4593(6) 0.097(3) Uani 1 1 d D U . . .
C36 C 0.9029(17) 0.8090(15) 0.5053(7) 0.114(4) Uani 1 1 d . U . . .
C37 C 0.9081(19) 0.856(2) 0.5832(6) 0.158(9) Uani 1 1 d . . . . .
H37A H 0.9547 0.9402 0.5893 0.238 Uiso 1 1 calc R U . . .
H37B H 0.8198 0.8678 0.5946 0.238 Uiso 1 1 calc R U . . .
H37C H 0.9530 0.7897 0.6134 0.238 Uiso 1 1 calc R U . . .
Cl1 Cl 1.0916(3) 0.6252(4) 0.04598(19) 0.1069(12) Uani 1 1 d . . . . .
N1 N 0.4538(5) 0.6245(6) 0.2280(3) 0.0382(13) Uani 1 1 d . . . . .
N2 N 0.8588(6) 0.3743(6) 0.2345(3) 0.0464(15) Uani 1 1 d . . . . .
N3A N 0.7236(18) 0.662(2) 0.4659(10) 0.071(4) Uani 0.317(11) 1 d D U P A 1
O8A O 0.704(3) 0.540(2) 0.4550(15) 0.116(7) Uani 0.317(11) 1 d D U P A 1
O9A O 0.735(3) 0.717(2) 0.5249(9) 0.088(5) Uani 0.317(11) 1 d D U P A 1
N3B N 0.7958(14) 0.5880(12) 0.4847(5) 0.081(3) Uani 0.683(11) 1 d D U P A 2
O8B O 0.7766(14) 0.4919(9) 0.4421(5) 0.084(3) Uani 0.683(11) 1 d D U P A 2
O9B O 0.7702(14) 0.5871(15) 0.5448(5) 0.108(4) Uani 0.683(11) 1 d D U P A 2
N4 N 0.9760(14) 0.8914(14) 0.4585(6) 0.130(5) Uani 1 1 d . U . . .
O1 O 0.2847(6) 0.4544(6) 0.2368(3) 0.0605(15) Uani 1 1 d . . . . .
O2 O 0.2224(6) 0.6955(6) 0.2329(3) 0.0653(16) Uani 1 1 d . . . . .
O3 O 0.4607(5) 0.5481(5) 0.0921(2) 0.0496(13) Uani 1 1 d . . . . .
O4 O 0.5821(5) 0.3635(5) 0.1268(2) 0.0404(11) Uani 1 1 d . . . . .
O5 O 0.6997(6) 0.3323(5) 0.3084(3) 0.0529(14) Uani 1 1 d . . . . .
O6 O 0.9085(6) 0.1738(6) 0.2906(4) 0.0710(18) Uani 1 1 d . . . . .
O7 O 1.0070(5) 0.2342(6) 0.1970(3) 0.0583(15) Uani 1 1 d . . . . .
O10 O 0.9595(14) 0.8481(8) 0.3947(4) 0.136(5) Uani 1 1 d . . . . .
S1 S 0.31222(18) 0.5910(2) 0.25672(10) 0.0488(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
C38 C3 1.572(17) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C1 H1 0.9300 . ?
C6 C5 1.3900 . ?
C6 S1 1.740(5) . ?
C5 C4 1.3900 . ?
C5 H5 0.9300 . ?
C4 C3 1.3900 . ?
C4 H4 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C7 N1 1.455(8) . ?
C7 C8 1.524(9) . ?
C7 C13 1.565(9) . ?
C7 H7 0.9800 . ?
C8 O3 1.204(8) . ?
C8 O4 1.333(8) . ?
C9 C11 1.489(12) . ?
C9 C12 1.496(12) . ?
C9 O4 1.484(8) . ?
C9 C10 1.495(11) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C16 1.513(8) . ?
C13 C14 1.521(10) . ?
C13 C26 1.564(10) . ?
C14 O5 1.198(9) . ?
C14 N2 1.405(10) . ?
C15 C20 1.3900 . ?
C15 C16 1.3900 . ?
C15 N2 1.419(7) . ?
C20 C19 1.3900 . ?
C20 H20 0.9300 . ?
C19 C18 1.3900 . ?
C19 Cl1 1.697(4) . ?
C18 C17 1.3900 . ?
C18 H18 0.9300 . ?
C17 C16 1.3900 . ?
C17 H17 0.9300 . ?
C21 O6 1.199(10) . ?
C21 O7 1.308(10) . ?
C21 N2 1.424(10) . ?
C22 C25 1.512(14) . ?
C22 O7 1.497(9) . ?
C22 C24 1.511(14) . ?
C22 C23 1.512(13) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.510(8) . ?
C26 C33 1.552(12) . ?
C26 H26 0.9800 . ?
C27 C32 1.3900 . ?
C27 C28 1.3900 . ?
C32 C31 1.3900 . ?
C32 H32 0.9300 . ?
C31 C30 1.3900 . ?
C31 H31 0.9300 . ?
C30 C29 1.3900 . ?
C30 H30 0.9300 . ?
C29 C28 1.3900 . ?
C29 H29 0.9300 . ?
C28 N1 1.422(6) . ?
C33 C34 1.389(15) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.237(16) . ?
C34 O10 1.518(18) . ?
C35 C36 1.385(17) . ?
C35 N3B 1.459(11) . ?
C35 N3A 1.460(13) . ?
C35 O9A 1.89(3) . ?
C36 N4 1.49(2) . ?
C36 C37 1.57(2) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
N1 S1 1.644(6) . ?
N3A O8A 1.248(13) . ?
N3A O9A 1.257(13) . ?
N3B O9B 1.222(10) . ?
N3B O8B 1.259(10) . ?
N4 O10 1.295(13) . ?
O1 S1 1.429(6) . ?
O2 S1 1.423(6) . ?

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
C3 C38 H38A 109.5 . . ?
C3 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C3 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C6 C1 C2 120.0 . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 S1 119.8(4) . . ?
C5 C6 S1 120.1(4) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 C38 119.5(10) . . ?
C4 C3 C38 120.4(10) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N1 C7 C8 110.4(5) . . ?
N1 C7 C13 114.2(5) . . ?
C8 C7 C13 111.1(5) . . ?
N1 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C13 C7 H7 106.9 . . ?
O3 C8 O4 126.8(6) . . ?
O3 C8 C7 124.2(6) . . ?
O4 C8 C7 109.0(6) . . ?
C11 C9 C12 112.0(8) . . ?
C11 C9 O4 110.3(6) . . ?
C12 C9 O4 109.0(6) . . ?
C11 C9 C10 110.0(7) . . ?
C12 C9 C10 112.7(7) . . ?
O4 C9 C10 102.5(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C13 C14 102.2(5) . . ?
C16 C13 C7 115.7(5) . . ?
C14 C13 C7 106.9(6) . . ?
C16 C13 C26 113.0(6) . . ?
C14 C13 C26 109.9(6) . . ?
C7 C13 C26 108.7(5) . . ?
O5 C14 N2 126.7(7) . . ?
O5 C14 C13 124.5(7) . . ?
N2 C14 C13 108.8(6) . . ?
C20 C15 C16 120.0 . . ?
C20 C15 N2 129.9(4) . . ?
C16 C15 N2 110.1(4) . . ?
C15 C20 C19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 Cl1 120.1(3) . . ?
C20 C19 Cl1 119.9(3) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 C13 130.7(4) . . ?
C15 C16 C13 109.3(4) . . ?
O6 C21 O7 128.2(7) . . ?
O6 C21 N2 121.8(8) . . ?
O7 C21 N2 110.0(7) . . ?
C25 C22 O7 101.4(7) . . ?
C25 C22 C24 112.6(9) . . ?
O7 C22 C24 109.5(6) . . ?
C25 C22 C23 111.3(8) . . ?
O7 C22 C23 109.0(7) . . ?
C24 C22 C23 112.5(10) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C33 115.2(7) . . ?
C27 C26 C13 107.6(5) . . ?
C33 C26 C13 109.9(6) . . ?
C27 C26 H26 108.0 . . ?
C33 C26 H26 108.0 . . ?
C13 C26 H26 108.0 . . ?
C32 C27 C28 120.0 . . ?
C32 C27 C26 123.6(4) . . ?
C28 C27 C26 116.3(4) . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C29 C30 C31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 N1 121.7(3) . . ?
C27 C28 N1 118.3(3) . . ?
C34 C33 C26 117.1(10) . . ?
C34 C33 H33A 108.0 . . ?
C26 C33 H33A 108.0 . . ?
C34 C33 H33B 108.0 . . ?
C26 C33 H33B 108.0 . . ?
H33A C33 H33B 107.3 . . ?
C35 C34 C33 136.6(14) . . ?
C35 C34 O10 106.5(10) . . ?
C33 C34 O10 115.4(13) . . ?
C34 C35 C36 116.5(12) . . ?
C34 C35 N3B 123.4(11) . . ?
C36 C35 N3B 120.0(11) . . ?
C34 C35 N3A 109.7(14) . . ?
C36 C35 N3A 114.2(13) . . ?
C34 C35 O9A 142.7(14) . . ?
C36 C35 O9A 74.3(11) . . ?
N3A C35 O9A 41.6(8) . . ?
C35 C36 N4 99.3(11) . . ?
C35 C36 C37 143.3(15) . . ?
N4 C36 C37 117.3(12) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C28 N1 C7 118.0(5) . . ?
C28 N1 S1 120.3(4) . . ?
C7 N1 S1 119.1(5) . . ?
C14 N2 C21 121.6(7) . . ?
C14 N2 C15 109.3(5) . . ?
C21 N2 C15 128.6(6) . . ?
O8A N3A O9A 125(2) . . ?
O8A N3A C35 114.8(16) . . ?
O9A N3A C35 87.9(16) . . ?
N3A O9A C35 50.5(10) . . ?
O9B N3B O8B 125.5(13) . . ?
O9B N3B C35 118.5(10) . . ?
O8B N3B C35 115.9(9) . . ?
O10 N4 C36 112.3(11) . . ?
C8 O4 C9 122.1(5) . . ?
C21 O7 C22 120.3(7) . . ?
N4 O10 C34 104.1(11) . . ?
O2 S1 O1 120.6(4) . . ?
O2 S1 N1 107.5(3) . . ?
O1 S1 N1 104.7(3) . . ?
O2 S1 C6 107.9(4) . . ?
O1 S1 C6 109.3(4) . . ?
N1 S1 C6 105.9(4) . . ?

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
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 S1 -177.5(7) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
S1 C6 C5 C4 177.5(7) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C4 C3 C38 -178.3(14) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C38 C3 C2 C1 178.3(14) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
N1 C7 C8 O3 11.3(9) . . . . ?
C13 C7 C8 O3 -116.4(7) . . . . ?
N1 C7 C8 O4 -168.8(5) . . . . ?
C13 C7 C8 O4 63.4(7) . . . . ?
N1 C7 C13 C16 -103.7(6) . . . . ?
C8 C7 C13 C16 21.9(8) . . . . ?
N1 C7 C13 C14 143.3(6) . . . . ?
C8 C7 C13 C14 -91.1(7) . . . . ?
N1 C7 C13 C26 24.7(8) . . . . ?
C8 C7 C13 C26 150.3(6) . . . . ?
C16 C13 C14 O5 -175.3(7) . . . . ?
C7 C13 C14 O5 -53.3(9) . . . . ?
C26 C13 C14 O5 64.5(9) . . . . ?
C16 C13 C14 N2 5.2(7) . . . . ?
C7 C13 C14 N2 127.2(6) . . . . ?
C26 C13 C14 N2 -115.0(7) . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
N2 C15 C20 C19 178.4(6) . . . . ?
C15 C20 C19 C18 0.0 . . . . ?
C15 C20 C19 Cl1 178.2(5) . . . . ?
C20 C19 C18 C17 0.0 . . . . ?
Cl1 C19 C18 C17 -178.2(5) . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C18 C17 C16 C13 176.2(6) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
N2 C15 C16 C17 -178.7(5) . . . . ?
C20 C15 C16 C13 -176.9(5) . . . . ?
N2 C15 C16 C13 4.3(5) . . . . ?
C14 C13 C16 C17 177.7(4) . . . . ?
C7 C13 C16 C17 62.0(7) . . . . ?
C26 C13 C16 C17 -64.2(7) . . . . ?
C14 C13 C16 C15 -5.8(5) . . . . ?
C7 C13 C16 C15 -121.5(5) . . . . ?
C26 C13 C16 C15 112.3(5) . . . . ?
C16 C13 C26 C27 70.5(7) . . . . ?
C14 C13 C26 C27 -176.1(6) . . . . ?
C7 C13 C26 C27 -59.4(8) . . . . ?
C16 C13 C26 C33 -55.6(9) . . . . ?
C14 C13 C26 C33 57.8(10) . . . . ?
C7 C13 C26 C33 174.5(8) . . . . ?
C33 C26 C27 C32 -5.8(10) . . . . ?
C13 C26 C27 C32 -128.7(5) . . . . ?
C33 C26 C27 C28 170.6(7) . . . . ?
C13 C26 C27 C28 47.7(8) . . . . ?
C28 C27 C32 C31 0.0 . . . . ?
C26 C27 C32 C31 176.3(6) . . . . ?
C27 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C31 C30 C29 C28 0.0 . . . . ?
C30 C29 C28 C27 0.0 . . . . ?
C30 C29 C28 N1 -178.8(5) . . . . ?
C32 C27 C28 C29 0.0 . . . . ?
C26 C27 C28 C29 -176.6(6) . . . . ?
C32 C27 C28 N1 178.9(5) . . . . ?
C26 C27 C28 N1 2.3(6) . . . . ?
C27 C26 C33 C34 67.5(14) . . . . ?
C13 C26 C33 C34 -170.8(10) . . . . ?
C26 C33 C34 C35 75.3(19) . . . . ?
C26 C33 C34 O10 -121.6(12) . . . . ?
C33 C34 C35 C36 176.1(15) . . . . ?
O10 C34 C35 C36 12.0(17) . . . . ?
C33 C34 C35 N3B -6(3) . . . . ?
O10 C34 C35 N3B -170.0(12) . . . . ?
C33 C34 C35 N3A -52(2) . . . . ?
O10 C34 C35 N3A 143.8(13) . . . . ?
C33 C34 C35 O9A -85(2) . . . . ?
O10 C34 C35 O9A 111(2) . . . . ?
C34 C35 C36 N4 -11.6(17) . . . . ?
N3B C35 C36 N4 170.3(12) . . . . ?
N3A C35 C36 N4 -141.3(15) . . . . ?
O9A C35 C36 N4 -153.2(13) . . . . ?
C34 C35 C36 C37 173(2) . . . . ?
N3B C35 C36 C37 -6(3) . . . . ?
N3A C35 C36 C37 43(3) . . . . ?
O9A C35 C36 C37 31(2) . . . . ?
C29 C28 N1 C7 136.8(5) . . . . ?
C27 C28 N1 C7 -42.0(7) . . . . ?
C29 C28 N1 S1 -61.6(6) . . . . ?
C27 C28 N1 S1 119.5(4) . . . . ?
C8 C7 N1 C28 -100.6(6) . . . . ?
C13 C7 N1 C28 25.4(8) . . . . ?
C8 C7 N1 S1 97.6(6) . . . . ?
C13 C7 N1 S1 -136.4(5) . . . . ?
O5 C14 N2 C21 5.6(11) . . . . ?
C13 C14 N2 C21 -174.9(6) . . . . ?
O5 C14 N2 C15 177.5(7) . . . . ?
C13 C14 N2 C15 -3.0(7) . . . . ?
O6 C21 N2 C14 -15.5(11) . . . . ?
O7 C21 N2 C14 164.7(6) . . . . ?
O6 C21 N2 C15 174.3(7) . . . . ?
O7 C21 N2 C15 -5.5(10) . . . . ?
C20 C15 N2 C14 -179.4(4) . . . . ?
C16 C15 N2 C14 -0.8(6) . . . . ?
C20 C15 N2 C21 -8.2(9) . . . . ?
C16 C15 N2 C21 170.3(6) . . . . ?
C34 C35 N3A O8A 82(2) . . . . ?
C36 C35 N3A O8A -145(2) . . . . ?
O9A C35 N3A O8A -128(3) . . . . ?
C34 C35 N3A O9A -150.3(17) . . . . ?
C36 C35 N3A O9A -17(2) . . . . ?
O8A N3A O9A C35 119(3) . . . . ?
C34 C35 O9A N3A 50(3) . . . . ?
C36 C35 O9A N3A 163.6(19) . . . . ?
C34 C35 N3B O9B -168.8(15) . . . . ?
C36 C35 N3B O9B 9(2) . . . . ?
C34 C35 N3B O8B 13(2) . . . . ?
C36 C35 N3B O8B -169.1(14) . . . . ?
C35 C36 N4 O10 6.3(17) . . . . ?
C37 C36 N4 O10 -176.5(14) . . . . ?
O3 C8 O4 C9 1.0(10) . . . . ?
C7 C8 O4 C9 -178.8(5) . . . . ?
C11 C9 O4 C8 62.0(9) . . . . ?
C12 C9 O4 C8 -61.3(9) . . . . ?
C10 C9 O4 C8 179.1(6) . . . . ?
O6 C21 O7 C22 -0.9(13) . . . . ?
N2 C21 O7 C22 178.9(6) . . . . ?
C25 C22 O7 C21 -177.0(8) . . . . ?
C24 C22 O7 C21 63.9(11) . . . . ?
C23 C22 O7 C21 -59.5(9) . . . . ?
C36 N4 O10 C34 -0.3(16) . . . . ?
C35 C34 O10 N4 -6.7(15) . . . . ?
C33 C34 O10 N4 -174.7(11) . . . . ?
C28 N1 S1 O2 48.3(6) . . . . ?
C7 N1 S1 O2 -150.4(5) . . . . ?
C28 N1 S1 O1 177.6(5) . . . . ?
C7 N1 S1 O1 -21.0(6) . . . . ?
C28 N1 S1 C6 -66.9(5) . . . . ?
C7 N1 S1 C6 94.5(5) . . . . ?
C1 C6 S1 O2 168.8(5) . . . . ?
C5 C6 S1 O2 -8.7(7) . . . . ?
C1 C6 S1 O1 36.0(6) . . . . ?
C5 C6 S1 O1 -141.5(6) . . . . ?
C1 C6 S1 N1 -76.3(6) . . . . ?
C5 C6 S1 N1 106.2(6) . . . . ?

_refine_diff_density_max         0.826
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether/ethyl acetate'
