#------------------------------------------------------------------------------
#$Date: 2025-06-03 22:27:53 +0300 (Tue, 03 Jun 2025) $
#$Revision: 299941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/34/2023485.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023485
loop_
_publ_author_name
'Kumaravel, R.'
'Stoeckli-Evans, Helen'
'Subashini, A.'
'Shankar, M. G.'
'Kučeráková, Monika'
'Dušek, Michal'
'Crochet, Aurélien'
'Ramamurthi, K.'
_publ_section_title
;
 Structure of
 (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)imino]-meth-yl}-1-methyl-2-phenyl-2,3-di-hydro-1H-pyrazol-3-one:
 aerial oxidation of 4-amino-anti-pyrine in di-methyl-formamide.
;
_journal_coeditor_code           HB8135
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              438
_journal_page_last               443
_journal_paper_doi               10.1107/S2056989025003676
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C22 H22 N6 O2'
_chemical_formula_moiety         'C22 H22 N6 O2'
_chemical_formula_sum            'C22 H22 N6 O2'
_chemical_formula_weight         402.45
_chemical_name_systematic
(E)-4-Amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 106.614(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.2393(11)
_cell_length_b                   10.6519(8)
_cell_length_c                   19.4225(11)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      73.06
_cell_measurement_theta_min      4.51
_cell_volume                     4012.4(4)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2019/3 (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;
Jana2020 (Petříček et al.,  2023)
;
_diffrn_ambient_temperature      95(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2027
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0932
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11696
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.371
_diffrn_reflns_theta_min         4.560
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0576
_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)+(0.0162P)²+0.9186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                2695
_reflns_number_total             3915
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8135.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023485.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2023485
_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.
;
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.26471(10) 0.82349(18) 0.71602(11) 0.0333(5) Uani d 1 . .
O O2 0.48785(10) 0.67524(17) 0.45511(10) 0.0270(4) Uani d 1 . .
N N1 0.28813(11) 0.6763(2) 0.80851(12) 0.0241(5) Uani d 1 . .
N N2 0.32274(11) 0.5621(2) 0.82181(12) 0.0239(5) Uani d 1 . .
N N3 0.36940(11) 0.6519(2) 0.66612(12) 0.0230(4) Uani d 1 . .
N N4 0.37734(11) 0.8631(2) 0.52073(12) 0.0241(5) Uani d 1 . .
N N5 0.41266(11) 0.8324(2) 0.46958(12) 0.0225(5) Uani d 1 . .
N N6 0.45817(12) 0.5646(2) 0.58278(13) 0.0264(5) Uani d 1 . .
H H6AN 0.4389(19) 0.534(4) 0.6156(19) 0.046(10) Uiso d 1 . .
H H6BN 0.4769(18) 0.506(3) 0.5546(18) 0.044(10) Uiso d 1 . .
C C1 0.29526(13) 0.7285(2) 0.74460(15) 0.0252(5) Uani d 1 . .
C C2 0.34215(12) 0.6435(2) 0.72408(14) 0.0220(5) Uani d 1 . .
C C3 0.35728(13) 0.5455(2) 0.77250(14) 0.0234(5) Uani d 1 . .
C C4 0.23438(14) 0.7031(3) 0.84031(14) 0.0258(5) Uani d 1 . .
C C5 0.23232(13) 0.8209(3) 0.86942(15) 0.0269(6) Uani d 1 . .
H H5 0.265495 0.882624 0.867108 0.032 Uiso calc 1 . .
C C6 0.18129(15) 0.8482(3) 0.90208(15) 0.0316(6) Uani d 1 . .
H H6 0.179484 0.929006 0.922122 0.038 Uiso calc 1 . .
C C7 0.13298(14) 0.7580(3) 0.90557(16) 0.0314(6) Uani d 1 . .
H H7 0.098412 0.776905 0.928336 0.038 Uiso calc 1 . .
C C8 0.13510(15) 0.6400(3) 0.87575(17) 0.0352(7) Uani d 1 . .
H H8 0.101978 0.578122 0.878016 0.042 Uiso calc 1 . .
C C9 0.18632(14) 0.6126(3) 0.84232(16) 0.0313(6) Uani d 1 . .
H H9 0.187874 0.532522 0.821286 0.038 Uiso calc 1 . .
C C10 0.34044(15) 0.5069(3) 0.89333(14) 0.0300(6) Uani d 1 . .
H H10A 0.306959 0.534045 0.918095 0.045 Uiso calc 0.5 . .
H H10B 0.339565 0.415177 0.889350 0.045 Uiso calc 0.5 . .
H H10C 0.386706 0.534382 0.920692 0.045 Uiso calc 0.5 . .
H H10D 0.381861 0.455024 0.900663 0.045 Uiso calc 0.5 . .
H H10E 0.349255 0.573892 0.929408 0.045 Uiso calc 0.5 . .
H H10F 0.302114 0.454687 0.898065 0.045 Uiso calc 0.5 . .
C C11 0.40348(15) 0.4365(3) 0.77530(15) 0.0290(6) Uani d 1 . .
H H11A 0.427737 0.446143 0.738586 0.043 Uiso calc 1 . .
H H11B 0.376096 0.359208 0.766291 0.043 Uiso calc 1 . .
H H11C 0.437139 0.432114 0.822884 0.043 Uiso calc 1 . .
C C12 0.35777(13) 0.7508(2) 0.62549(14) 0.0222(5) Uani d 1 . .
H H12 0.330612 0.818076 0.634577 0.027 Uiso calc 1 . .
C C13 0.38717(13) 0.7557(2) 0.56620(14) 0.0237(5) Uani d 1 . .
C C14 0.42913(13) 0.6708(2) 0.54780(13) 0.0212(5) Uani d 1 . .
C C15 0.44761(13) 0.7201(2) 0.48601(14) 0.0236(5) Uani d 1 . .
C C16 0.42297(13) 0.9285(2) 0.42269(14) 0.0239(5) Uani d 1 . .
C C17 0.43325(16) 0.8949(3) 0.35769(15) 0.0341(6) Uani d 1 . .
H H17 0.433488 0.809000 0.344528 0.041 Uiso calc 1 . .
C C18 0.44319(18) 0.9885(3) 0.31212(17) 0.0408(7) Uani d 1 . .
H H18 0.450361 0.966070 0.267463 0.049 Uiso calc 1 . .
C C19 0.44287(15) 1.1135(3) 0.33029(17) 0.0343(7) Uani d 1 . .
H H19 0.450448 1.176686 0.298891 0.041 Uiso calc 1 . .
C C20 0.43135(14) 1.1456(3) 0.39494(15) 0.0283(6) Uani d 1 . .
H H20 0.429285 1.231722 0.406967 0.034 Uiso calc 1 . .
C C21 0.42279(13) 1.0542(2) 0.44233(14) 0.0252(5) Uani d 1 . .
H H21 0.416884 1.076869 0.487512 0.030 Uiso calc 1 . .
C C22 0.30443(14) 0.8929(3) 0.48461(18) 0.0376(7) Uani d 1 . .
H H22A 0.279979 0.907024 0.520799 0.056 Uiso calc 1 . .
H H22B 0.283073 0.822685 0.453602 0.056 Uiso calc 1 . .
H H22C 0.301822 0.968835 0.455445 0.056 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 109.7(2) ?
N2 N1 C4 . . 120.1(2) ?
C1 N1 C4 . . 126.0(2) ?
C3 N2 N1 . . 108.5(2) ?
C3 N2 C10 . . 126.1(2) ?
N1 N2 C10 . . 120.3(2) ?
C12 N3 C2 . . 120.0(2) ?
N5 N4 C13 . . 103.86(19) ?
N5 N4 C22 . . 110.6(2) ?
C13 N4 C22 . . 114.3(2) ?
C15 N5 N4 . . 111.5(2) ?
C15 N5 C16 . . 127.7(2) ?
N4 N5 C16 . . 118.5(2) ?
C14 N6 H6AN . . 116(2) ?
C14 N6 H6BN . . 116(2) ?
H6AN N6 H6BN . . 119(3) ?
O1 C1 N1 . . 123.9(2) ?
O1 C1 C2 . . 132.3(3) ?
N1 C1 C2 . . 103.7(2) ?
C3 C2 N3 . . 122.6(2) ?
C3 C2 C1 . . 108.7(2) ?
N3 C2 C1 . . 128.7(2) ?
N2 C3 C2 . . 109.0(2) ?
N2 C3 C11 . . 121.7(2) ?
C2 C3 C11 . . 129.3(3) ?
C9 C4 C5 . . 121.3(3) ?
C9 C4 N1 . . 120.3(2) ?
C5 C4 N1 . . 118.4(2) ?
C4 C5 C6 . . 119.4(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C7 C6 C5 . . 120.3(3) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 120.0(3) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C7 C8 C9 . . 119.7(3) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C4 C9 C8 . . 119.3(3) ?
C4 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
H10D C10 H10E . . 109.5 ?
H10D C10 H10F . . 109.5 ?
H10E C10 H10F . . 109.5 ?
C3 C11 H11A . . 109.5 ?
C3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N3 C12 C13 . . 118.1(2) ?
N3 C12 H12 . . 120.9 ?
C13 C12 H12 . . 120.9 ?
C14 C13 N4 . . 111.0(2) ?
C14 C13 C12 . . 128.2(2) ?
N4 C13 C12 . . 120.6(2) ?
C13 C14 N6 . . 129.4(3) ?
C13 C14 C15 . . 107.8(2) ?
N6 C14 C15 . . 122.4(2) ?
O2 C15 N5 . . 126.0(2) ?
O2 C15 C14 . . 128.4(2) ?
N5 C15 C14 . . 105.5(2) ?
C17 C16 C21 . . 120.8(3) ?
C17 C16 N5 . . 119.0(2) ?
C21 C16 N5 . . 120.2(2) ?
C16 C17 C18 . . 118.9(3) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C19 C18 C17 . . 121.3(3) ?
C19 C18 H18 . . 119.3 ?
C17 C18 H18 . . 119.3 ?
C18 C19 C20 . . 119.1(3) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
C19 C20 C21 . . 121.0(3) ?
C19 C20 H20 . . 119.5 ?
C21 C20 H20 . . 119.5 ?
C20 C21 C16 . . 118.9(3) ?
C20 C21 H21 . . 120.5 ?
C16 C21 H21 . . 120.5 ?
N4 C22 H22A . . 109.5 ?
N4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.232(3) ?
O2 C15 . 1.237(3) ?
N1 N2 . 1.390(3) ?
N1 C1 . 1.405(3) ?
N1 C4 . 1.425(3) ?
N2 C3 . 1.349(4) ?
N2 C10 . 1.455(3) ?
N3 C12 . 1.297(3) ?
N3 C2 . 1.391(3) ?
N4 N5 . 1.418(3) ?
N4 C13 . 1.424(3) ?
N4 C22 . 1.476(3) ?
N5 C15 . 1.379(3) ?
N5 C16 . 1.425(3) ?
N6 C14 . 1.364(3) ?
N6 H6AN . 0.90(4) ?
N6 H6BN . 0.98(4) ?
C1 C2 . 1.447(4) ?
C2 C3 . 1.379(4) ?
C3 C11 . 1.482(4) ?
C4 C9 . 1.378(4) ?
C4 C5 . 1.382(4) ?
C5 C6 . 1.389(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.386(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.390(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.402(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C10 H10D . 0.9800 ?
C10 H10E . 0.9800 ?
C10 H10F . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.441(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.357(4) ?
C14 C15 . 1.454(4) ?
C16 C17 . 1.384(4) ?
C16 C21 . 1.393(4) ?
C17 C18 . 1.386(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.378(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.384(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.385(4) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N6 H6AN N3 . 0.90(4) 2.30(4) 2.894(3) 123(3)
N6 H6BN O2 5_666 0.98(3) 2.09(3) 2.953(3) 147(3)
C7 H7 O2 8_466 0.95 2.49 3.417(4) 165
C10 H10D O2 6_566 0.98 2.52 3.472(4) 164
C12 H12 O1 . 0.95 2.34 3.022(3) 128
C17 H17 O2 . 0.95 2.55 3.013(4) 110
C11 H11B Cg1 6_566 0.98 2.96 3.645(3) 128
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C3 . . . . 5.9(3) ?
C4 N1 N2 C3 . . . . 164.2(2) ?
C1 N1 N2 C10 . . . . 162.1(2) ?
C4 N1 N2 C10 . . . . -39.7(3) ?
C13 N4 N5 C15 . . . . -5.6(3) ?
C22 N4 N5 C15 . . . . -128.7(2) ?
C13 N4 N5 C16 . . . . -169.6(2) ?
C22 N4 N5 C16 . . . . 67.3(3) ?
N2 N1 C1 O1 . . . . 173.0(3) ?
C4 N1 C1 O1 . . . . 16.3(4) ?
N2 N1 C1 C2 . . . . -5.3(3) ?
C4 N1 C1 C2 . . . . -162.0(2) ?
C12 N3 C2 C3 . . . . -174.6(2) ?
C12 N3 C2 C1 . . . . 5.8(4) ?
O1 C1 C2 C3 . . . . -175.1(3) ?
N1 C1 C2 C3 . . . . 2.9(3) ?
O1 C1 C2 N3 . . . . 4.5(5) ?
N1 C1 C2 N3 . . . . -177.4(2) ?
N1 N2 C3 C2 . . . . -3.9(3) ?
C10 N2 C3 C2 . . . . -158.3(2) ?
N1 N2 C3 C11 . . . . 175.5(2) ?
C10 N2 C3 C11 . . . . 21.1(4) ?
N3 C2 C3 N2 . . . . -179.1(2) ?
C1 C2 C3 N2 . . . . 0.5(3) ?
N3 C2 C3 C11 . . . . 1.5(4) ?
C1 C2 C3 C11 . . . . -178.9(3) ?
N2 N1 C4 C9 . . . . -42.8(4) ?
C1 N1 C4 C9 . . . . 111.6(3) ?
N2 N1 C4 C5 . . . . 136.5(3) ?
C1 N1 C4 C5 . . . . -69.0(4) ?
C9 C4 C5 C6 . . . . 0.7(4) ?
N1 C4 C5 C6 . . . . -178.6(3) ?
C4 C5 C6 C7 . . . . 0.1(4) ?
C5 C6 C7 C8 . . . . -0.5(4) ?
C6 C7 C8 C9 . . . . 0.1(5) ?
C5 C4 C9 C8 . . . . -1.2(4) ?
N1 C4 C9 C8 . . . . 178.2(3) ?
C7 C8 C9 C4 . . . . 0.7(5) ?
C2 N3 C12 C13 . . . . 179.8(2) ?
N5 N4 C13 C14 . . . . 4.3(3) ?
C22 N4 C13 C14 . . . . 124.9(3) ?
N5 N4 C13 C12 . . . . -179.4(2) ?
C22 N4 C13 C12 . . . . -58.8(3) ?
N3 C12 C13 C14 . . . . -3.0(4) ?
N3 C12 C13 N4 . . . . -178.6(2) ?
N4 C13 C14 N6 . . . . 170.8(3) ?
C12 C13 C14 N6 . . . . -5.2(5) ?
N4 C13 C14 C15 . . . . -1.5(3) ?
C12 C13 C14 C15 . . . . -177.4(3) ?
N4 N5 C15 O2 . . . . -172.9(2) ?
C16 N5 C15 O2 . . . . -10.8(4) ?
N4 N5 C15 C14 . . . . 4.9(3) ?
C16 N5 C15 C14 . . . . 167.0(2) ?
C13 C14 C15 O2 . . . . 175.7(3) ?
N6 C14 C15 O2 . . . . 2.8(4) ?
C13 C14 C15 N5 . . . . -2.0(3) ?
N6 C14 C15 N5 . . . . -174.9(2) ?
C15 N5 C16 C17 . . . . 42.4(4) ?
N4 N5 C16 C17 . . . . -156.5(2) ?
C15 N5 C16 C21 . . . . -137.4(3) ?
N4 N5 C16 C21 . . . . 23.7(3) ?
C21 C16 C17 C18 . . . . -0.2(4) ?
N5 C16 C17 C18 . . . . 179.9(3) ?
C16 C17 C18 C19 . . . . -0.1(5) ?
C17 C18 C19 C20 . . . . -1.0(5) ?
C18 C19 C20 C21 . . . . 2.4(4) ?
C19 C20 C21 C16 . . . . -2.7(4) ?
C17 C16 C21 C20 . . . . 1.6(4) ?
N5 C16 C21 C20 . . . . -178.5(2) ?
