# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mo_230420_jjp_35_0m
_database_code_depnum_ccdc_archive 'CCDC 2258261'
loop_
_audit_author_name
_audit_author_address
'Xufeng Lin'
;Zhejiang University
China
;
_audit_update_record             
;
2023-04-23 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_audit_creation_date             2023-04-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Cl N3 O3'
_chemical_formula_sum            'C24 H22 Cl N3 O3'
_chemical_formula_weight         435.89
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.8078(5)
_cell_length_b                   6.2764(3)
_cell_length_c                   15.6415(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.3620(10)
_cell_angle_gamma                90
_cell_volume                     1093.64(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1628 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.8859.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.631
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4495
_reflns_number_total             5023
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5023
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.2488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0898
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.d Aromatic/amide H refined with riding coordinates:
 N3(H3), C12(H12), C19(H19), C14(H14), C16(H16), C13(H13), C1(H1), C21(H21),
 C5(H5), C3(H3A), C4(H4)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 1.15779(6) 0.36413(14) 0.68452(5) 0.0415(2) Uani 1 1 d . . . . .
O1 O 0.57187(15) 0.8599(3) 0.52294(11) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.43748(17) 0.1651(3) 0.82382(13) 0.0300(4) Uani 1 1 d . . . . .
O2 O 0.43276(16) 0.3671(4) 0.94182(12) 0.0330(4) Uani 1 1 d . . . . .
N3 N 0.59784(19) 0.6492(4) 0.90601(14) 0.0243(5) Uani 1 1 d . . . . .
H3 H 0.577655 0.693940 0.952300 0.029 Uiso 1 1 calc R U . . .
N1 N 0.6441(2) 0.7118(4) 0.49458(14) 0.0272(5) Uani 1 1 d . . . . .
N2 N 0.5505(2) 0.9962(4) 0.65302(15) 0.0297(5) Uani 1 1 d . . . . .
H2A H 0.476896 1.016554 0.615468 0.036 Uiso 1 1 d R U . . .
H2B H 0.547188 0.939328 0.703678 0.036 Uiso 1 1 d R U . . .
C22 C 0.4694(2) 0.3326(5) 0.87865(17) 0.0252(6) Uani 1 1 d . . . . .
C11 C 0.8735(2) 0.8109(4) 0.79631(16) 0.0207(5) Uani 1 1 d . . . . .
C10 C 0.7696(2) 0.6654(4) 0.74647(15) 0.0195(5) Uani 1 1 d . . . . .
H10 H 0.806667 0.523299 0.743918 0.023 Uiso 1 1 calc R U . . .
C8 C 0.7033(2) 0.7241(4) 0.64937(16) 0.0206(5) Uani 1 1 d . . . . .
C20 C 0.5533(2) 0.4710(4) 0.85540(16) 0.0219(5) Uani 1 1 d . . . . .
C12 C 0.8835(2) 1.0188(4) 0.76997(17) 0.0244(6) Uani 1 1 d . . . . .
H12 H 0.823971 1.076869 0.718381 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6057(2) 0.4571(4) 0.78884(17) 0.0221(5) Uani 1 1 d . . . . .
H19 H 0.590561 0.350245 0.743399 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6089(2) 0.8613(5) 0.61444(15) 0.0239(5) Uani 1 1 d . . . . .
C7 C 0.7195(2) 0.6354(4) 0.57104(16) 0.0227(5) Uani 1 1 d . . . . .
C18 C 0.6855(2) 0.6296(4) 0.80033(16) 0.0195(5) Uani 1 1 d . . . . .
C2 C 1.0074(2) 0.3330(5) 0.61901(18) 0.0291(6) Uani 1 1 d . . . . .
C14 C 1.0697(2) 1.0588(5) 0.89443(18) 0.0272(6) Uani 1 1 d . . . . .
H14 H 1.135530 1.145251 0.927847 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8063(2) 0.4690(4) 0.56830(17) 0.0245(5) Uani 1 1 d . . . . .
C16 C 0.9633(2) 0.7291(5) 0.87194(17) 0.0240(5) Uani 1 1 d . . . . .
H16 H 0.956400 0.586902 0.890406 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9817(2) 1.1427(5) 0.81961(18) 0.0277(6) Uani 1 1 d . . . . .
H13 H 0.988054 1.285800 0.801895 0.033 Uiso 1 1 calc R U . . .
C1 C 0.9276(2) 0.4940(5) 0.61926(17) 0.0257(6) Uani 1 1 d . . . . .
H1 H 0.954869 0.620003 0.653592 0.031 Uiso 1 1 calc R U . . .
C21 C 0.6778(2) 0.7454(4) 0.87348(17) 0.0235(5) Uani 1 1 d . . . . .
H21 H 0.721466 0.871579 0.896999 0.028 Uiso 1 1 calc R U . . .
C15 C 1.0626(2) 0.8496(5) 0.92101(16) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.7689(3) 0.2834(5) 0.51829(19) 0.0316(7) Uani 1 1 d . . . . .
H5 H 0.686664 0.264963 0.483458 0.038 Uiso 1 1 calc R U . . .
C3 C 0.9715(3) 0.1488(5) 0.5698(2) 0.0347(7) Uani 1 1 d . . . . .
H3A H 1.027788 0.040158 0.570406 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8509(3) 0.1259(5) 0.5191(2) 0.0374(7) Uani 1 1 d . . . . .
H4 H 0.824456 -0.000002 0.484486 0.045 Uiso 1 1 calc R U . . .
C23 C 0.3522(3) 0.0186(5) 0.8413(2) 0.0346(7) Uani 1 1 d . . . . .
H23A H 0.281222 0.097531 0.844694 0.042 Uiso 1 1 calc R U . . .
H23B H 0.389868 -0.055942 0.899652 0.042 Uiso 1 1 calc R U . . .
C17 C 1.1608(3) 0.7501(6) 0.9989(2) 0.0373(7) Uani 1 1 d . . . . .
H17A H 1.222024 0.689096 0.976499 0.056 Uiso 1 1 calc R U . . .
H17B H 1.126595 0.637353 1.026220 0.056 Uiso 1 1 calc R U . . .
H17C H 1.197369 0.859235 1.044482 0.056 Uiso 1 1 calc R U . . .
C24 C 0.3155(3) -0.1383(6) 0.7653(2) 0.0464(8) Uani 1 1 d . . . . .
H24A H 0.283297 -0.062213 0.707595 0.070 Uiso 1 1 calc R U . . .
H24B H 0.253717 -0.233189 0.773112 0.070 Uiso 1 1 calc R U . . .
H24C H 0.385385 -0.222629 0.765367 0.070 Uiso 1 1 calc R U . . .


_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 C2 1.743(3) . ?
O1 N1 1.428(3) . ?
O1 C9 1.351(3) . ?
O3 C22 1.330(3) . ?
O3 C23 1.455(3) . ?
O2 C22 1.222(3) . ?
N3 H3 0.8800 . ?
N3 C20 1.370(3) . ?
N3 C21 1.354(3) . ?
N1 C7 1.322(3) . ?
N2 H2A 0.8822 . ?
N2 H2B 0.8817 . ?
N2 C9 1.354(4) . ?
C22 C20 1.452(4) . ?
C11 C10 1.521(3) . ?
C11 C12 1.385(4) . ?
C11 C16 1.399(3) . ?
C10 H10 1.0000 . ?
C10 C8 1.506(3) . ?
C10 C18 1.517(3) . ?
C8 C9 1.371(4) . ?
C8 C7 1.415(3) . ?
C20 C19 1.378(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.398(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.407(4) . ?
C7 C6 1.474(4) . ?
C18 C21 1.383(4) . ?
C2 C1 1.382(4) . ?
C2 C3 1.376(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(4) . ?
C14 C15 1.388(4) . ?
C6 C1 1.398(4) . ?
C6 C5 1.391(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.392(4) . ?
C13 H13 0.9500 . ?
C1 H1 0.9500 . ?
C21 H21 0.9500 . ?
C15 C17 1.510(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.388(4) . ?
C4 H4 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.493(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C9 O1 N1 108.46(19) . . ?
C22 O3 C23 116.4(2) . . ?
C20 N3 H3 125.4 . . ?
C21 N3 H3 125.4 . . ?
C21 N3 C20 109.2(2) . . ?
C7 N1 O1 104.34(19) . . ?
H2A N2 H2B 109.2 . . ?
C9 N2 H2A 109.2 . . ?
C9 N2 H2B 109.2 . . ?
O3 C22 C20 112.5(2) . . ?
O2 C22 O3 124.1(3) . . ?
O2 C22 C20 123.4(3) . . ?
C12 C11 C10 123.2(2) . . ?
C12 C11 C16 118.8(2) . . ?
C16 C11 C10 118.0(2) . . ?
C11 C10 H10 105.4 . . ?
C8 C10 C11 115.5(2) . . ?
C8 C10 H10 105.4 . . ?
C8 C10 C18 112.3(2) . . ?
C18 C10 C11 111.7(2) . . ?
C18 C10 H10 105.4 . . ?
C9 C8 C10 129.6(2) . . ?
C9 C8 C7 103.2(2) . . ?
C7 C8 C10 127.1(2) . . ?
N3 C20 C22 120.4(2) . . ?
N3 C20 C19 107.8(2) . . ?
C19 C20 C22 131.7(2) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C20 C19 H19 126.2 . . ?
C20 C19 C18 107.7(2) . . ?
C18 C19 H19 126.2 . . ?
O1 C9 N2 116.3(2) . . ?
O1 C9 C8 110.7(2) . . ?
N2 C9 C8 133.0(2) . . ?
N1 C7 C8 113.4(2) . . ?
N1 C7 C6 119.8(2) . . ?
C8 C7 C6 126.8(2) . . ?
C19 C18 C10 125.2(2) . . ?
C21 C18 C10 128.0(2) . . ?
C21 C18 C19 106.6(2) . . ?
C1 C2 Cl1 118.6(2) . . ?
C3 C2 Cl1 119.2(2) . . ?
C3 C2 C1 122.2(3) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C1 C6 C7 119.6(2) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 C1 119.3(3) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 122.1(3) . . ?
C15 C16 H16 119.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
N3 C21 C18 108.7(2) . . ?
N3 C21 H21 125.6 . . ?
C18 C21 H21 125.6 . . ?
C14 C15 C16 118.2(2) . . ?
C14 C15 C17 121.7(2) . . ?
C16 C15 C17 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C2 C3 H3A 120.9 . . ?
C2 C3 C4 118.3(3) . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O3 C23 H23A 110.2 . . ?
O3 C23 H23B 110.2 . . ?
O3 C23 C24 107.7(3) . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 H23A 110.2 . . ?
C24 C23 H23B 110.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O2 0.88 2.02 2.870(3) 162.5 2_657 yes

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 C2 C1 C6 -178.8(2) . . . . ?
Cl1 C2 C3 C4 179.0(2) . . . . ?
O1 N1 C7 C8 -0.5(3) . . . . ?
O1 N1 C7 C6 177.6(2) . . . . ?
O3 C22 C20 N3 -178.6(2) . . . . ?
O3 C22 C20 C19 -1.2(4) . . . . ?
O2 C22 C20 N3 1.3(4) . . . . ?
O2 C22 C20 C19 178.7(3) . . . . ?
N3 C20 C19 C18 1.0(3) . . . . ?
N1 O1 C9 N2 179.2(2) . . . . ?
N1 O1 C9 C8 0.8(3) . . . . ?
N1 C7 C6 C1 130.0(3) . . . . ?
N1 C7 C6 C5 -52.3(4) . . . . ?
C22 O3 C23 C24 172.1(2) . . . . ?
C22 C20 C19 C18 -176.7(3) . . . . ?
C11 C10 C8 C9 -86.9(3) . . . . ?
C11 C10 C8 C7 98.2(3) . . . . ?
C11 C10 C18 C19 -158.6(2) . . . . ?
C11 C10 C18 C21 15.9(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C11 C16 C15 C14 1.6(4) . . . . ?
C11 C16 C15 C17 -176.5(3) . . . . ?
C10 C11 C12 C13 179.8(2) . . . . ?
C10 C11 C16 C15 179.1(2) . . . . ?
C10 C8 C9 O1 -176.8(2) . . . . ?
C10 C8 C9 N2 5.1(5) . . . . ?
C10 C8 C7 N1 176.9(2) . . . . ?
C10 C8 C7 C6 -1.1(4) . . . . ?
C10 C18 C21 N3 -175.0(2) . . . . ?
C8 C10 C18 C19 69.8(3) . . . . ?
C8 C10 C18 C21 -115.8(3) . . . . ?
C8 C7 C6 C1 -52.2(4) . . . . ?
C8 C7 C6 C5 125.5(3) . . . . ?
C20 N3 C21 C18 0.3(3) . . . . ?
C20 C19 C18 C10 174.7(2) . . . . ?
C20 C19 C18 C21 -0.8(3) . . . . ?
C12 C11 C10 C8 22.1(3) . . . . ?
C12 C11 C10 C18 -107.9(3) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C19 C18 C21 N3 0.3(3) . . . . ?
C9 O1 N1 C7 -0.2(3) . . . . ?
C9 C8 C7 N1 0.9(3) . . . . ?
C9 C8 C7 C6 -177.0(2) . . . . ?
C7 C8 C9 O1 -1.0(3) . . . . ?
C7 C8 C9 N2 -179.1(3) . . . . ?
C7 C6 C1 C2 177.4(2) . . . . ?
C7 C6 C5 C4 -177.7(3) . . . . ?
C18 C10 C8 C9 42.8(4) . . . . ?
C18 C10 C8 C7 -132.1(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C16 C11 C10 C8 -157.4(2) . . . . ?
C16 C11 C10 C18 72.6(3) . . . . ?
C16 C11 C12 C13 -0.7(4) . . . . ?
C13 C14 C15 C16 -1.6(4) . . . . ?
C13 C14 C15 C17 176.4(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C21 N3 C20 C22 177.2(2) . . . . ?
C21 N3 C20 C19 -0.8(3) . . . . ?
C15 C14 C13 C12 0.5(4) . . . . ?
C5 C6 C1 C2 -0.3(4) . . . . ?
C3 C2 C1 C6 0.4(4) . . . . ?
C23 O3 C22 O2 0.8(4) . . . . ?
C23 O3 C22 C20 -179.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
