# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_mj21404_0m
_audit_block_doi                 10.5517/ccdc.csd.cc28sjwh
_database_code_depnum_ccdc_archive 'CCDC 2108957'
loop_
_audit_author_name
_audit_author_address
'hao lu'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2023-03-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Cl N4 O2'
_chemical_formula_sum            'C23 H21 Cl N4 O2'
_chemical_formula_weight         420.89
_chemical_absolute_configuration rmad
_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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.35740(10)
_cell_length_b                   17.1204(3)
_cell_length_c                   19.4098(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2112.59(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    212.99
_cell_measurement_theta_max      54.825
_cell_measurement_theta_min      2.995
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1599 before and 0.0777 after correction.
The Ratio of minimum to maximum transmission is 0.6993.
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    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12916
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.816
_diffrn_reflns_theta_min         2.994
_diffrn_ambient_temperature      212.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995994
_diffrn_source_voltage           69.79
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                3566
_reflns_number_total             3796
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.066(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.1790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0873
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
Cl1 Cl 0.69925(15) 0.21626(4) 0.62198(4) 0.0750(3) Uani 1 1 d . . . . .
O1 O 0.7392(3) 0.50172(12) 0.33558(8) 0.0525(5) Uani 1 1 d . . . . .
O2 O 0.5760(3) 0.64448(10) 0.54696(9) 0.0453(4) Uani 1 1 d . . . . .
N1 N 0.1602(3) 0.55788(11) 0.45468(10) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.3582(3) 0.55968(10) 0.49146(9) 0.0304(4) Uani 1 1 d . . . . .
N3 N 0.2760(3) 0.43463(12) 0.25384(11) 0.0491(5) Uani 1 1 d . . . . .
N4 N 0.5573(4) 0.48209(12) 0.20034(10) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.2237(3) 0.55016(12) 0.38087(11) 0.0322(4) Uani 1 1 d . . . . .
H1 H 0.106250 0.525687 0.355280 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4018(3) 0.48893(11) 0.38878(10) 0.0292(4) Uani 1 1 d . . . . .
H2 H 0.335406 0.436749 0.392068 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5080(3) 0.50657(11) 0.45888(11) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.641280 0.534936 0.450466 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4082(3) 0.63034(12) 0.51898(11) 0.0344(5) Uani 1 1 d . . . . .
C5 C 0.2209(4) 0.68292(13) 0.51004(13) 0.0460(6) Uani 1 1 d . . . . .
H5A H 0.255967 0.727652 0.480703 0.055 Uiso 1 1 calc R U . . .
H5B H 0.171311 0.702255 0.554700 0.055 Uiso 1 1 calc R U . . .
C6 C 0.0551(4) 0.63194(14) 0.47607(12) 0.0435(6) Uani 1 1 d . . . . .
H6A H -0.059096 0.620854 0.508560 0.052 Uiso 1 1 calc R U . . .
H6B H -0.004323 0.658566 0.435833 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2831(4) 0.62530(13) 0.34458(10) 0.0343(5) Uani 1 1 d . . . . .
C8 C 0.4773(4) 0.66212(13) 0.35105(12) 0.0410(5) Uani 1 1 d . . . . .
H8 H 0.580986 0.640125 0.379595 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5196(5) 0.73083(15) 0.31592(14) 0.0565(7) Uani 1 1 d . . . . .
H9 H 0.652253 0.754567 0.320143 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3682(6) 0.76440(17) 0.27491(15) 0.0679(9) Uani 1 1 d . . . . .
H10 H 0.397710 0.810715 0.250761 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1731(6) 0.73001(18) 0.26931(15) 0.0669(9) Uani 1 1 d . . . . .
H11 H 0.067673 0.753899 0.242690 0.080 Uiso 1 1 calc R U . . .
C12 C 0.1322(4) 0.66023(15) 0.30286(13) 0.0494(6) Uani 1 1 d . . . . .
H12 H 0.000390 0.636126 0.297335 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5544(3) 0.43422(11) 0.50068(10) 0.0320(5) Uani 1 1 d . . . . .
C14 C 0.7525(4) 0.40040(14) 0.49698(13) 0.0444(6) Uani 1 1 d . . . . .
H14 H 0.857066 0.423242 0.469311 0.053 Uiso 1 1 calc R U . . .
C15 C 0.7968(4) 0.33289(15) 0.53404(14) 0.0531(7) Uani 1 1 d . . . . .
H15 H 0.930991 0.309984 0.531453 0.064 Uiso 1 1 calc R U . . .
C16 C 0.6438(4) 0.29996(14) 0.57432(12) 0.0477(6) Uani 1 1 d . . . . .
C17 C 0.4454(4) 0.33251(14) 0.57854(13) 0.0469(6) Uani 1 1 d . . . . .
H17 H 0.341136 0.309435 0.606208 0.056 Uiso 1 1 calc R U . . .
C18 C 0.4025(4) 0.39963(13) 0.54139(12) 0.0404(5) Uani 1 1 d . . . . .
H18 H 0.267745 0.422052 0.543895 0.048 Uiso 1 1 calc R U . . .
C19 C 0.5534(3) 0.48737(12) 0.32875(11) 0.0329(5) Uani 1 1 d . . . . .
C20 C 0.4622(4) 0.46866(13) 0.26186(11) 0.0364(5) Uani 1 1 d . . . . .
C21 C 0.2537(5) 0.42656(17) 0.18433(15) 0.0626(8) Uani 1 1 d . . . . .
H21 H 0.136740 0.403731 0.162597 0.075 Uiso 1 1 calc R U . . .
C22 C 0.4234(6) 0.45599(18) 0.15086(14) 0.0639(8) Uani 1 1 d . . . . .
H22 H 0.444179 0.457947 0.102944 0.077 Uiso 1 1 calc R U . . .
C23 C 0.7546(6) 0.5235(3) 0.18732(16) 0.0867(11) Uani 1 1 d . . . . .
H23A H 0.737729 0.578225 0.198884 0.130 Uiso 1 1 calc R U . . .
H23B H 0.791581 0.518600 0.139027 0.130 Uiso 1 1 calc R U . . .
H23C H 0.865314 0.500996 0.215418 0.130 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 C16 1.742(2) . ?
O1 C19 1.214(3) . ?
O2 C4 1.221(3) . ?
N1 N2 1.447(2) . ?
N1 C1 1.495(3) . ?
N1 C6 1.492(3) . ?
N2 C3 1.461(2) . ?
N2 C4 1.360(3) . ?
N3 C20 1.328(3) . ?
N3 C21 1.363(3) . ?
N4 C20 1.358(3) . ?
N4 C22 1.359(4) . ?
N4 C23 1.463(4) . ?
C1 H1 0.9900 . ?
C1 C2 1.550(3) . ?
C1 C7 1.514(3) . ?
C2 H2 0.9900 . ?
C2 C3 1.549(3) . ?
C2 C19 1.513(3) . ?
C3 H3 0.9900 . ?
C3 C13 1.510(3) . ?
C4 C5 1.503(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C6 1.519(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.392(3) . ?
C7 C12 1.391(3) . ?
C8 H8 0.9400 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9400 . ?
C9 C10 1.375(5) . ?
C10 H10 0.9400 . ?
C10 C11 1.377(5) . ?
C11 H11 0.9400 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.388(3) . ?
C13 C18 1.381(3) . ?
C14 H14 0.9400 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9400 . ?
C15 C16 1.370(4) . ?
C16 C17 1.382(4) . ?
C17 H17 0.9400 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9400 . ?
C19 C20 1.458(3) . ?
C21 H21 0.9400 . ?
C21 C22 1.356(5) . ?
C22 H22 0.9400 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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 N1 C1 103.86(14) . . ?
N2 N1 C6 103.53(17) . . ?
C6 N1 C1 117.57(17) . . ?
N1 N2 C3 109.90(15) . . ?
C4 N2 N1 114.58(16) . . ?
C4 N2 C3 124.83(17) . . ?
C20 N3 C21 104.7(2) . . ?
C20 N4 C22 106.7(2) . . ?
C20 N4 C23 128.0(2) . . ?
C22 N4 C23 125.1(2) . . ?
N1 C1 H1 108.3 . . ?
N1 C1 C2 99.33(15) . . ?
N1 C1 C7 115.99(17) . . ?
C2 C1 H1 108.3 . . ?
C7 C1 H1 108.3 . . ?
C7 C1 C2 116.01(17) . . ?
C1 C2 H2 107.8 . . ?
C3 C2 C1 105.88(15) . . ?
C3 C2 H2 107.8 . . ?
C19 C2 C1 113.63(16) . . ?
C19 C2 H2 107.8 . . ?
C19 C2 C3 113.72(16) . . ?
N2 C3 C2 102.55(15) . . ?
N2 C3 H3 108.9 . . ?
N2 C3 C13 113.91(17) . . ?
C2 C3 H3 108.9 . . ?
C13 C3 C2 113.41(16) . . ?
C13 C3 H3 108.9 . . ?
O2 C4 N2 123.7(2) . . ?
O2 C4 C5 128.7(2) . . ?
N2 C4 C5 107.59(18) . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
C4 C5 C6 104.82(17) . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
N1 C6 C5 107.36(18) . . ?
N1 C6 H6A 110.2 . . ?
N1 C6 H6B 110.2 . . ?
C5 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C8 C7 C1 124.3(2) . . ?
C12 C7 C1 117.7(2) . . ?
C12 C7 C8 118.0(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C3 119.45(19) . . ?
C18 C13 C3 121.52(18) . . ?
C18 C13 C14 119.0(2) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 Cl1 119.87(19) . . ?
C15 C16 C17 121.1(2) . . ?
C17 C16 Cl1 119.0(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.9(2) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 121.1(2) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O1 C19 C2 122.17(19) . . ?
O1 C19 C20 121.95(19) . . ?
C20 C19 C2 115.87(18) . . ?
N3 C20 N4 111.6(2) . . ?
N3 C20 C19 123.7(2) . . ?
N4 C20 C19 124.7(2) . . ?
N3 C21 H21 124.6 . . ?
C22 C21 N3 110.7(3) . . ?
C22 C21 H21 124.6 . . ?
N4 C22 H22 126.8 . . ?
C21 C22 N4 106.4(2) . . ?
C21 C22 H22 126.8 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 C16 C17 C18 179.11(19) . . . . ?
O1 C19 C20 N3 163.0(2) . . . . ?
O1 C19 C20 N4 -15.5(4) . . . . ?
O2 C4 C5 C6 -176.2(2) . . . . ?
N1 N2 C3 C2 13.98(19) . . . . ?
N1 N2 C3 C13 -108.97(18) . . . . ?
N1 N2 C4 O2 -174.01(19) . . . . ?
N1 N2 C4 C5 7.7(2) . . . . ?
N1 C1 C2 C3 -34.11(18) . . . . ?
N1 C1 C2 C19 -159.63(16) . . . . ?
N1 C1 C7 C8 79.6(3) . . . . ?
N1 C1 C7 C12 -99.4(2) . . . . ?
N2 N1 C1 C2 42.34(18) . . . . ?
N2 N1 C1 C7 -82.7(2) . . . . ?
N2 N1 C6 C5 14.2(2) . . . . ?
N2 C3 C13 C14 -147.9(2) . . . . ?
N2 C3 C13 C18 33.7(3) . . . . ?
N2 C4 C5 C6 1.9(2) . . . . ?
N3 C21 C22 N4 1.0(3) . . . . ?
C1 N1 N2 C3 -37.1(2) . . . . ?
C1 N1 N2 C4 109.33(18) . . . . ?
C1 N1 C6 C5 -99.6(2) . . . . ?
C1 C2 C3 N2 13.37(18) . . . . ?
C1 C2 C3 C13 136.65(17) . . . . ?
C1 C2 C19 O1 118.6(2) . . . . ?
C1 C2 C19 C20 -60.6(2) . . . . ?
C1 C7 C8 C9 179.9(2) . . . . ?
C1 C7 C12 C11 178.4(2) . . . . ?
C2 C1 C7 C8 -36.4(3) . . . . ?
C2 C1 C7 C12 144.6(2) . . . . ?
C2 C3 C13 C14 95.3(2) . . . . ?
C2 C3 C13 C18 -83.1(2) . . . . ?
C2 C19 C20 N3 -17.9(3) . . . . ?
C2 C19 C20 N4 163.6(2) . . . . ?
C3 N2 C4 O2 -33.3(3) . . . . ?
C3 N2 C4 C5 148.5(2) . . . . ?
C3 C2 C19 O1 -2.7(3) . . . . ?
C3 C2 C19 C20 178.22(18) . . . . ?
C3 C13 C14 C15 -178.7(2) . . . . ?
C3 C13 C18 C17 178.8(2) . . . . ?
C4 N2 C3 C2 -128.28(19) . . . . ?
C4 N2 C3 C13 108.8(2) . . . . ?
C4 C5 C6 N1 -10.3(3) . . . . ?
C6 N1 N2 C3 -160.48(17) . . . . ?
C6 N1 N2 C4 -14.0(2) . . . . ?
C6 N1 C1 C2 155.96(17) . . . . ?
C6 N1 C1 C7 30.9(3) . . . . ?
C7 C1 C2 C3 90.9(2) . . . . ?
C7 C1 C2 C19 -34.6(2) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C8 C7 C12 C11 -0.7(4) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 -2.4(5) . . . . ?
C10 C11 C12 C7 2.4(4) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C14 C15 C16 Cl1 -179.0(2) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
C19 C2 C3 N2 138.83(17) . . . . ?
C19 C2 C3 C13 -97.89(19) . . . . ?
C20 N3 C21 C22 -0.5(3) . . . . ?
C20 N4 C22 C21 -1.0(3) . . . . ?
C21 N3 C20 N4 -0.1(3) . . . . ?
C21 N3 C20 C19 -178.8(2) . . . . ?
C22 N4 C20 N3 0.7(3) . . . . ?
C22 N4 C20 C19 179.4(2) . . . . ?
C23 N4 C20 N3 175.0(3) . . . . ?
C23 N4 C20 C19 -6.4(4) . . . . ?
C23 N4 C22 C21 -175.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
