# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2220955'
loop_
_audit_author_name
_audit_author_address
'Vashchenko Alexander'
;Irkutsk Institute of Chemistry
Russia
;
#Added by publCIF



_audit_update_record             
;
2022-11-21 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  No
# publcif _publ_body_element loop end
_audit_creation_date             2021-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
(5R,7aS)-3-(4-Chlorophenyl)-7,7-dimethyl-7a-phenyl-5,6,7,7a-tetrahydropyrrolo[1,2-d][1,2,4]oxadiazol-5-ol
_chemical_formula_moiety         '2(C19 H19 Cl N2 O2)'
_chemical_formula_sum            'C38 H38 Cl2 N4 O4'
_chemical_formula_weight         685.62
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.286(6)
_cell_length_b                   21.161(16)
_cell_length_c                   18.146(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.84(2)
_cell_angle_gamma                90
_cell_volume                     3566(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1497 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.8715.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'colorless, prizm'
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.052
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            72219
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.075
_diffrn_reflns_theta_min         2.228
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   IuS
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3969
_reflns_number_total             7036
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0500
_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)+(0.0403P)²+1.2825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.86963(10) 0.02222(4) 0.07766(4) 0.0834(3) Uani 1 1 d . . . . .
Cl2 Cl 0.08824(8) 0.27734(4) 0.07129(5) 0.0769(3) Uani 1 1 d . . . . .
O1 O 0.62051(17) 0.31174(7) 0.33654(9) 0.0501(4) Uani 1 1 d . . . . .
O2 O 0.6225(2) 0.12559(8) 0.45142(9) 0.0564(5) Uani 1 1 d . . . . .
H2 H 0.588(3) 0.1007(14) 0.4213(16) 0.085 Uiso 1 1 d R . . . .
O3 O 0.68295(17) 0.55234(7) 0.14290(8) 0.0437(4) Uani 1 1 d . . . . .
O4 O 0.8171(2) 0.35254(8) 0.16909(11) 0.0589(5) Uani 1 1 d . . . . .
N1 N 0.59682(18) 0.20403(8) 0.35653(9) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.6672(2) 0.27787(10) 0.27298(11) 0.0483(5) Uani 1 1 d . . . . .
N3 N 0.67306(18) 0.44698(8) 0.17647(9) 0.0330(4) Uani 1 1 d . . . . .
N4 N 0.5424(2) 0.52748(9) 0.12561(10) 0.0423(5) Uani 1 1 d . . . . .
C1 C 0.8106(3) 0.07836(13) 0.14095(13) 0.0506(7) Uani 1 1 d . . . . .
C2 C 0.8791(3) 0.13611(13) 0.14510(14) 0.0542(7) Uani 1 1 d . . . . .
H2A H 0.9578 0.1445 0.1156 0.065 Uiso 1 1 calc R . . . .
C3 C 0.8300(3) 0.18146(13) 0.19336(13) 0.0484(6) Uani 1 1 d . . . . .
H3 H 0.8759 0.2205 0.1961 0.058 Uiso 1 1 calc R . . . .
C4 C 0.7126(2) 0.16930(12) 0.23789(12) 0.0403(6) Uani 1 1 d . . . . .
C5 C 0.6585(2) 0.21838(11) 0.28820(12) 0.0386(6) Uani 1 1 d . . . . .
C6 C 0.5463(2) 0.26600(10) 0.38397(12) 0.0384(6) Uani 1 1 d . . . . .
C7 C 0.3857(3) 0.27594(11) 0.37226(12) 0.0402(6) Uani 1 1 d . . . . .
C8 C 0.2914(3) 0.22545(13) 0.36370(14) 0.0529(7) Uani 1 1 d . . . . .
H8 H 0.3264 0.1843 0.3659 0.063 Uiso 1 1 calc R . . . .
C9 C 0.1449(3) 0.23594(15) 0.35185(17) 0.0674(8) Uani 1 1 d . . . . .
H9 H 0.0832 0.2017 0.3455 0.081 Uiso 1 1 calc R . . . .
C10 C 0.0904(3) 0.29634(15) 0.34942(17) 0.0696(9) Uani 1 1 d . . . . .
H10 H -0.0076 0.3031 0.3415 0.084 Uiso 1 1 calc R . . . .
C11 C 0.6055(3) 0.27189(11) 0.46511(13) 0.0438(6) Uani 1 1 d . . . . .
C12 C 0.6479(3) 0.34037(13) 0.48383(17) 0.0734(9) Uani 1 1 d . . . . .
H12A H 0.6850 0.3423 0.5334 0.110 Uiso 1 1 calc GR . . . .
H12B H 0.5647 0.3671 0.4793 0.110 Uiso 1 1 calc GR . . . .
H12C H 0.7204 0.3545 0.4505 0.110 Uiso 1 1 calc GR . . . .
C13 C 0.7355(3) 0.22716(12) 0.46340(14) 0.0495(7) Uani 1 1 d . . . . .
H13A H 0.8196 0.2491 0.4454 0.059 Uiso 1 1 calc R . . . .
H13B H 0.7572 0.2112 0.5124 0.059 Uiso 1 1 calc R . . . .
C14 C 0.6942(3) 0.17315(11) 0.41181(13) 0.0444(6) Uani 1 1 d . . . . .
H14 H 0.7797 0.1560 0.3879 0.053 Uiso 1 1 calc R . . . .
C15 C 0.4938(3) 0.24883(14) 0.52079(14) 0.0607(8) Uani 1 1 d . . . . .
H15A H 0.4644 0.2066 0.5084 0.091 Uiso 1 1 calc GR . . . .
H15B H 0.4116 0.2763 0.5193 0.091 Uiso 1 1 calc GR . . . .
H15C H 0.5358 0.2492 0.5694 0.091 Uiso 1 1 calc GR . . . .
C16 C 0.1826(3) 0.34677(15) 0.35879(16) 0.0650(8) Uani 1 1 d . . . . .
H16 H 0.1464 0.3877 0.3578 0.078 Uiso 1 1 calc R . . . .
C17 C 0.3289(3) 0.33706(12) 0.36975(13) 0.0531(7) Uani 1 1 d . . . . .
H17 H 0.3900 0.3716 0.3755 0.064 Uiso 1 1 calc R . . . .
C18 C 0.6461(3) 0.11028(12) 0.23402(14) 0.0501(7) Uani 1 1 d . . . . .
H18 H 0.5688 0.1014 0.2644 0.060 Uiso 1 1 calc R . . . .
C19 C 0.6945(3) 0.06471(13) 0.18510(15) 0.0579(7) Uani 1 1 d . . . . .
H19 H 0.6494 0.0255 0.1821 0.069 Uiso 1 1 calc R . . . .
C20 C 0.2153(2) 0.33482(13) 0.09452(15) 0.0481(6) Uani 1 1 d . . . . .
C21 C 0.2393(3) 0.38403(13) 0.04613(14) 0.0533(7) Uani 1 1 d . . . . .
H21 H 0.1852 0.3872 0.0027 0.064 Uiso 1 1 calc R . . . .
C22 C 0.3440(2) 0.42861(12) 0.06249(13) 0.0457(6) Uani 1 1 d . . . . .
H22 H 0.3600 0.4619 0.0301 0.055 Uiso 1 1 calc R . . . .
C23 C 0.4254(2) 0.42385(11) 0.12729(12) 0.0366(5) Uani 1 1 d . . . . .
C24 C 0.5443(2) 0.46831(11) 0.14298(11) 0.0352(5) Uani 1 1 d . . . . .
C25 C 0.7534(2) 0.50580(10) 0.19246(12) 0.0372(6) Uani 1 1 d . . . . .
C26 C 0.7312(2) 0.52835(11) 0.27130(12) 0.0399(6) Uani 1 1 d . . . . .
C27 C 0.6991(3) 0.48629(13) 0.32760(13) 0.0553(7) Uani 1 1 d . . . . .
H27 H 0.6895 0.4434 0.3173 0.066 Uiso 1 1 calc R . . . .
C28 C 0.6814(3) 0.50801(15) 0.39920(15) 0.0716(9) Uani 1 1 d . . . . .
H28 H 0.6600 0.4795 0.4364 0.086 Uiso 1 1 calc R . . . .
C29 C 0.6953(3) 0.57108(17) 0.41556(16) 0.0741(9) Uani 1 1 d . . . . .
H29 H 0.6837 0.5852 0.4637 0.089 Uiso 1 1 calc R . . . .
C30 C 0.2926(3) 0.32969(12) 0.15971(14) 0.0511(7) Uani 1 1 d . . . . .
H30 H 0.2739 0.2971 0.1926 0.061 Uiso 1 1 calc R . . . .
C31 C 0.3989(3) 0.37400(12) 0.17522(13) 0.0460(6) Uani 1 1 d . . . . .
H31 H 0.4534 0.3703 0.2184 0.055 Uiso 1 1 calc R . . . .
C32 C 0.9100(2) 0.49352(11) 0.16703(13) 0.0421(6) Uani 1 1 d . . . . .
C33 C 1.0002(3) 0.46272(13) 0.22926(14) 0.0586(7) Uani 1 1 d . . . . .
H33A H 1.0935 0.4518 0.2111 0.088 Uiso 1 1 calc GR . . . .
H33B H 0.9525 0.4252 0.2460 0.088 Uiso 1 1 calc GR . . . .
H33C H 1.0107 0.4919 0.2695 0.088 Uiso 1 1 calc GR . . . .
C34 C 0.9878(3) 0.55377(13) 0.14193(17) 0.0658(8) Uani 1 1 d . . . . .
H34A H 1.0010 0.5816 0.1832 0.099 Uiso 1 1 calc GR . . . .
H34B H 0.9310 0.5745 0.1045 0.099 Uiso 1 1 calc GR . . . .
H34C H 1.0799 0.5427 0.1224 0.099 Uiso 1 1 calc GR . . . .
C35 C 0.8825(3) 0.44632(11) 0.10333(13) 0.0448(6) Uani 1 1 d . . . . .
H35A H 0.8550 0.4685 0.0585 0.054 Uiso 1 1 calc R . . . .
H35B H 0.9683 0.4216 0.0940 0.054 Uiso 1 1 calc R . . . .
C36 C 0.7608(2) 0.40410(11) 0.12895(13) 0.0414(6) Uani 1 1 d . . . . .
H36 H 0.7032 0.3892 0.0867 0.050 Uiso 1 1 calc R . . . .
C37 C 0.7266(3) 0.61338(14) 0.36036(17) 0.0667(8) Uani 1 1 d . . . . .
H37 H 0.7357 0.6562 0.3712 0.080 Uiso 1 1 calc R . . . .
C38 C 0.7447(3) 0.59244(12) 0.28851(15) 0.0537(7) Uani 1 1 d . . . . .
H38 H 0.7659 0.6213 0.2516 0.064 Uiso 1 1 calc R . . . .
H4 H 0.744(4) 0.3340(17) 0.1941(19) 0.114(13) Uiso 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
Cl1 C1 1.746(3) . ?
Cl2 C20 1.742(3) . ?
O1 N2 1.431(3) . ?
O1 C6 1.473(3) . ?
O2 H2 0.82(3) . ?
O2 C14 1.409(3) . ?
O3 N4 1.438(2) . ?
O3 C25 1.480(3) . ?
O4 C36 1.408(3) . ?
O4 H4 0.91(4) . ?
N1 C5 1.407(3) . ?
N1 C6 1.481(3) . ?
N1 C14 1.492(3) . ?
N2 C5 1.292(3) . ?
N3 C24 1.408(3) . ?
N3 C25 1.478(3) . ?
N3 C36 1.500(3) . ?
N4 C24 1.291(3) . ?
C1 C2 1.379(4) . ?
C1 C19 1.383(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C4 C5 1.476(3) . ?
C4 C18 1.394(3) . ?
C6 C7 1.518(3) . ?
C6 C11 1.569(3) . ?
C7 C8 1.389(3) . ?
C7 C17 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9300 . ?
C10 C16 1.377(4) . ?
C11 C12 1.538(4) . ?
C11 C13 1.535(3) . ?
C11 C15 1.538(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.523(3) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 C30 1.379(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(3) . ?
C23 C24 1.475(3) . ?
C23 C31 1.391(3) . ?
C25 C26 1.525(3) . ?
C25 C32 1.554(3) . ?
C26 C27 1.391(3) . ?
C26 C38 1.397(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.373(4) . ?
C29 H29 0.9300 . ?
C29 C37 1.377(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.387(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.541(3) . ?
C32 C34 1.538(3) . ?
C32 C35 1.546(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.519(3) . ?
C36 H36 0.9800 . ?
C37 H37 0.9300 . ?
C37 C38 1.390(4) . ?
C38 H38 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 C6 106.97(16) . . ?
C14 O2 H2 108(2) . . ?
N4 O3 C25 106.34(15) . . ?
C36 O4 H4 108(2) . . ?
C5 N1 C6 103.90(17) . . ?
C5 N1 C14 115.91(18) . . ?
C6 N1 C14 110.72(17) . . ?
C5 N2 O1 107.16(18) . . ?
C24 N3 C25 103.77(17) . . ?
C24 N3 C36 114.24(17) . . ?
C25 N3 C36 110.22(17) . . ?
C24 N4 O3 106.98(17) . . ?
C2 C1 Cl1 119.3(2) . . ?
C2 C1 C19 121.1(2) . . ?
C19 C1 Cl1 119.6(2) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 C18 119.1(2) . . ?
C18 C4 C5 120.5(2) . . ?
N1 C5 C4 122.7(2) . . ?
N2 C5 N1 115.3(2) . . ?
N2 C5 C4 122.0(2) . . ?
O1 C6 N1 103.42(17) . . ?
O1 C6 C7 107.12(18) . . ?
O1 C6 C11 109.60(18) . . ?
N1 C6 C7 113.02(18) . . ?
N1 C6 C11 106.10(18) . . ?
C7 C6 C11 116.77(19) . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 C17 118.1(2) . . ?
C17 C7 C6 120.2(2) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C16 119.2(3) . . ?
C16 C10 H10 120.4 . . ?
C12 C11 C6 111.5(2) . . ?
C13 C11 C6 101.37(19) . . ?
C13 C11 C12 112.7(2) . . ?
C13 C11 C15 110.8(2) . . ?
C15 C11 C6 111.2(2) . . ?
C15 C11 C12 109.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 110.4 . . ?
C11 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 C11 106.50(19) . . ?
C14 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
O2 C14 N1 111.68(19) . . ?
O2 C14 C13 109.8(2) . . ?
O2 C14 H14 110.6 . . ?
N1 C14 C13 103.26(19) . . ?
N1 C14 H14 110.6 . . ?
C13 C14 H14 110.6 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16 119.7 . . ?
C10 C16 C17 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C7 C17 H17 119.6 . . ?
C16 C17 C7 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C4 C18 H18 119.8 . . ?
C19 C18 C4 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C1 C19 C18 119.2(3) . . ?
C1 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 Cl2 119.1(2) . . ?
C30 C20 Cl2 119.7(2) . . ?
C30 C20 C21 121.2(2) . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.8(2) . . ?
C31 C23 C22 118.9(2) . . ?
C31 C23 C24 120.1(2) . . ?
N3 C24 C23 120.5(2) . . ?
N4 C24 N3 115.1(2) . . ?
N4 C24 C23 124.3(2) . . ?
O3 C25 C26 107.30(18) . . ?
O3 C25 C32 109.77(18) . . ?
N3 C25 O3 102.93(16) . . ?
N3 C25 C26 111.90(18) . . ?
N3 C25 C32 105.83(18) . . ?
C26 C25 C32 118.08(18) . . ?
C27 C26 C25 121.5(2) . . ?
C27 C26 C38 118.5(2) . . ?
C38 C26 C25 120.0(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.2 . . ?
C28 C29 C37 119.6(3) . . ?
C37 C29 H29 120.2 . . ?
C20 C30 H30 120.6 . . ?
C20 C30 C31 118.7(2) . . ?
C31 C30 H30 120.6 . . ?
C23 C31 H31 119.4 . . ?
C30 C31 C23 121.2(2) . . ?
C30 C31 H31 119.4 . . ?
C33 C32 C25 110.74(19) . . ?
C33 C32 C35 110.9(2) . . ?
C34 C32 C25 113.3(2) . . ?
C34 C32 C33 108.4(2) . . ?
C34 C32 C35 112.8(2) . . ?
C35 C32 C25 100.67(18) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 110.7 . . ?
C32 C35 H35B 110.7 . . ?
H35A C35 H35B 108.8 . . ?
C36 C35 C32 105.46(18) . . ?
C36 C35 H35A 110.7 . . ?
C36 C35 H35B 110.7 . . ?
O4 C36 N3 111.83(19) . . ?
O4 C36 C35 110.0(2) . . ?
O4 C36 H36 110.5 . . ?
N3 C36 C35 103.46(18) . . ?
N3 C36 H36 110.5 . . ?
C35 C36 H36 110.5 . . ?
C29 C37 H37 119.8 . . ?
C29 C37 C38 120.3(3) . . ?
C38 C37 H37 119.8 . . ?
C26 C38 H38 119.7 . . ?
C37 C38 C26 120.5(3) . . ?
C37 C38 H38 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
Cl1 C1 C2 C3 177.95(19) . . . . ?
Cl1 C1 C19 C18 -178.43(19) . . . . ?
Cl2 C20 C21 C22 -177.39(19) . . . . ?
Cl2 C20 C30 C31 176.43(19) . . . . ?
O1 N2 C5 N1 5.2(3) . . . . ?
O1 N2 C5 C4 -173.49(19) . . . . ?
O1 C6 C7 C8 136.0(2) . . . . ?
O1 C6 C7 C17 -43.9(3) . . . . ?
O1 C6 C11 C12 33.2(3) . . . . ?
O1 C6 C11 C13 -87.0(2) . . . . ?
O1 C6 C11 C15 155.1(2) . . . . ?
O3 N4 C24 N3 3.7(2) . . . . ?
O3 N4 C24 C23 -173.81(18) . . . . ?
O3 C25 C26 C27 139.6(2) . . . . ?
O3 C25 C26 C38 -41.2(3) . . . . ?
O3 C25 C32 C33 162.22(18) . . . . ?
O3 C25 C32 C34 40.2(3) . . . . ?
O3 C25 C32 C35 -80.4(2) . . . . ?
N1 C6 C7 C8 22.8(3) . . . . ?
N1 C6 C7 C17 -157.1(2) . . . . ?
N1 C6 C11 C12 144.2(2) . . . . ?
N1 C6 C11 C13 24.0(2) . . . . ?
N1 C6 C11 C15 -93.8(2) . . . . ?
N2 O1 C6 N1 18.3(2) . . . . ?
N2 O1 C6 C7 -101.32(19) . . . . ?
N2 O1 C6 C11 131.09(19) . . . . ?
N3 C25 C26 C27 27.4(3) . . . . ?
N3 C25 C26 C38 -153.4(2) . . . . ?
N3 C25 C32 C33 -87.3(2) . . . . ?
N3 C25 C32 C34 150.7(2) . . . . ?
N3 C25 C32 C35 30.0(2) . . . . ?
N4 O3 C25 N3 21.9(2) . . . . ?
N4 O3 C25 C26 -96.33(19) . . . . ?
N4 O3 C25 C32 134.19(18) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C1 C19 C18 0.4(4) . . . . ?
C2 C3 C4 C5 -178.6(2) . . . . ?
C2 C3 C4 C18 0.9(4) . . . . ?
C3 C4 C5 N1 -147.4(2) . . . . ?
C3 C4 C5 N2 31.2(3) . . . . ?
C3 C4 C18 C19 -1.4(4) . . . . ?
C4 C18 C19 C1 0.8(4) . . . . ?
C5 N1 C6 O1 -14.9(2) . . . . ?
C5 N1 C6 C7 100.6(2) . . . . ?
C5 N1 C6 C11 -130.21(18) . . . . ?
C5 N1 C14 O2 -140.4(2) . . . . ?
C5 N1 C14 C13 101.7(2) . . . . ?
C5 C4 C18 C19 178.1(2) . . . . ?
C6 O1 N2 C5 -15.0(2) . . . . ?
C6 N1 C5 N2 6.6(3) . . . . ?
C6 N1 C5 C4 -174.7(2) . . . . ?
C6 N1 C14 O2 101.7(2) . . . . ?
C6 N1 C14 C13 -16.3(2) . . . . ?
C6 C7 C8 C9 -179.0(2) . . . . ?
C6 C7 C17 C16 179.7(2) . . . . ?
C6 C11 C13 C14 -34.6(2) . . . . ?
C7 C6 C11 C12 -88.8(3) . . . . ?
C7 C6 C11 C13 151.0(2) . . . . ?
C7 C6 C11 C15 33.1(3) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C7 C17 C16 -0.2(4) . . . . ?
C8 C9 C10 C16 0.1(5) . . . . ?
C9 C10 C16 C17 0.7(5) . . . . ?
C10 C16 C17 C7 -0.7(4) . . . . ?
C11 C6 C7 C8 -100.7(3) . . . . ?
C11 C6 C7 C17 79.4(3) . . . . ?
C11 C13 C14 O2 -87.2(2) . . . . ?
C11 C13 C14 N1 32.0(2) . . . . ?
C12 C11 C13 C14 -153.9(2) . . . . ?
C14 N1 C5 N2 -115.1(2) . . . . ?
C14 N1 C5 C4 63.6(3) . . . . ?
C14 N1 C6 O1 110.22(19) . . . . ?
C14 N1 C6 C7 -134.31(19) . . . . ?
C14 N1 C6 C11 -5.1(2) . . . . ?
C15 C11 C13 C14 83.5(2) . . . . ?
C17 C7 C8 C9 1.0(4) . . . . ?
C18 C4 C5 N1 33.0(3) . . . . ?
C18 C4 C5 N2 -148.4(2) . . . . ?
C19 C1 C2 C3 -0.9(4) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C20 C30 C31 C23 1.7(4) . . . . ?
C21 C20 C30 C31 -1.9(4) . . . . ?
C21 C22 C23 C24 175.6(2) . . . . ?
C21 C22 C23 C31 -0.5(3) . . . . ?
C22 C23 C24 N3 -141.0(2) . . . . ?
C22 C23 C24 N4 36.4(3) . . . . ?
C22 C23 C31 C30 -0.5(3) . . . . ?
C24 N3 C25 O3 -19.1(2) . . . . ?
C24 N3 C25 C26 95.8(2) . . . . ?
C24 N3 C25 C32 -134.35(17) . . . . ?
C24 N3 C36 O4 -137.7(2) . . . . ?
C24 N3 C36 C35 104.0(2) . . . . ?
C24 C23 C31 C30 -176.6(2) . . . . ?
C25 O3 N4 C24 -16.4(2) . . . . ?
C25 N3 C24 N4 10.4(2) . . . . ?
C25 N3 C24 C23 -171.95(18) . . . . ?
C25 N3 C36 O4 106.0(2) . . . . ?
C25 N3 C36 C35 -12.3(2) . . . . ?
C25 C26 C27 C28 179.1(2) . . . . ?
C25 C26 C38 C37 -179.1(2) . . . . ?
C25 C32 C35 C36 -38.1(2) . . . . ?
C26 C25 C32 C33 38.9(3) . . . . ?
C26 C25 C32 C34 -83.1(3) . . . . ?
C26 C25 C32 C35 156.2(2) . . . . ?
C26 C27 C28 C29 0.0(5) . . . . ?
C27 C26 C38 C37 0.1(4) . . . . ?
C27 C28 C29 C37 0.2(5) . . . . ?
C28 C29 C37 C38 -0.3(5) . . . . ?
C29 C37 C38 C26 0.1(4) . . . . ?
C30 C20 C21 C22 1.0(4) . . . . ?
C31 C23 C24 N3 35.0(3) . . . . ?
C31 C23 C24 N4 -147.6(2) . . . . ?
C32 C25 C26 C27 -95.9(3) . . . . ?
C32 C25 C26 C38 83.4(3) . . . . ?
C32 C35 C36 O4 -87.9(2) . . . . ?
C32 C35 C36 N3 31.7(2) . . . . ?
C33 C32 C35 C36 79.2(2) . . . . ?
C34 C32 C35 C36 -159.1(2) . . . . ?
C36 N3 C24 N4 -109.6(2) . . . . ?
C36 N3 C24 C23 68.0(2) . . . . ?
C36 N3 C25 O3 103.58(19) . . . . ?
C36 N3 C25 C26 -141.51(18) . . . . ?
C36 N3 C25 C32 -11.6(2) . . . . ?
C38 C26 C27 C28 -0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
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;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
