#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228542.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228542
loop_
_publ_author_name
'Wang, Hong-Mei'
'Deng, Shou-Heng'
'Zeng, Xiao-Hua'
'Chen, Ping'
'Cao, Feng-Jun'
_publ_section_title
;
 Ethyl
 1-benzyl-5-{[(isopropylamino)(3-nitrophenoxy)methylidene]amino}-1H-1,2,3-triazole-4-carboxylate
;
_journal_coeditor_code           RZ2518
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3207
_journal_page_last               o3208
_journal_paper_doi               10.1107/S1600536810046659
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H24 N6 O5'
_chemical_formula_moiety         'C22 H24 N6 O5'
_chemical_formula_sum            'C22 H24 N6 O5'
_chemical_formula_weight         452.47
_chemical_name_systematic
;
Ethyl 1-benzyl-5-{[(isopropylamino)(3-nitrophenoxy)methylidene]amino}-
1H-1,2,3-triazole-4-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.3840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5019(7)
_cell_length_b                   14.5616(9)
_cell_length_c                   14.1758(9)
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.32
_cell_volume                     2277.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16973
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0702P)²+0.3769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                4276
_reflns_number_total             5620
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2518.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228542
_cod_database_fobs_code          2228542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.83494(16) 0.73129(13) 0.46761(13) 0.0443(4) Uani d . 1 . .
C C2 0.92546(19) 0.79033(16) 0.45953(18) 0.0607(6) Uani d . 1 . .
H H2 0.9053 0.8448 0.4245 0.073 Uiso calc R 1 . .
C C3 1.0448(2) 0.7693(2) 0.5027(2) 0.0778(8) Uani d . 1 . .
H H3 1.1051 0.8096 0.4969 0.093 Uiso calc R 1 . .
C C4 1.0756(2) 0.6893(3) 0.5545(2) 0.0880(10) Uani d . 1 . .
H H4 1.1565 0.6761 0.5855 0.106 Uiso calc R 1 . .
C C5 0.9865(3) 0.6285(2) 0.56061(19) 0.0858(9) Uani d . 1 . .
H H5 1.0073 0.5731 0.5936 0.103 Uiso calc R 1 . .
C C6 0.8662(2) 0.64966(17) 0.51778(17) 0.0634(6) Uani d . 1 . .
H H6 0.8061 0.6088 0.5227 0.076 Uiso calc R 1 . .
C C7 0.70362(17) 0.75548(14) 0.42216(15) 0.0496(5) Uani d . 1 . .
H H7A 0.6892 0.7643 0.3520 0.060 Uiso calc R 1 . .
H H7B 0.6531 0.7050 0.4318 0.060 Uiso calc R 1 . .
C C8 0.67486(14) 0.92697(13) 0.43699(12) 0.0386(4) Uani d . 1 . .
C C9 0.64906(14) 0.97754(13) 0.51172(12) 0.0374(4) Uani d . 1 . .
C C10 0.65826(15) 1.07626(14) 0.52721(13) 0.0428(4) Uani d . 1 . .
C C11 0.6438(2) 1.19830(17) 0.63312(18) 0.0666(6) Uani d . 1 . .
H H11A 0.5876 1.2347 0.5832 0.080 Uiso calc R 1 . .
H H11B 0.7256 1.2178 0.6369 0.080 Uiso calc R 1 . .
C C12 0.6194(3) 1.2108(2) 0.7301(2) 0.0843(8) Uani d . 1 . .
H H12A 0.5398 1.1884 0.7264 0.126 Uiso calc R 1 . .
H H12B 0.6244 1.2749 0.7468 0.126 Uiso calc R 1 . .
H H12C 0.6784 1.1773 0.7795 0.126 Uiso calc R 1 . .
C C13 0.65271(15) 1.00782(13) 0.29254(12) 0.0405(4) Uani d . 1 . .
C C14 0.48968(17) 1.11872(14) 0.21120(13) 0.0473(5) Uani d . 1 . .
H H14 0.5274 1.1187 0.1572 0.057 Uiso calc R 1 . .
C C15 0.35540(19) 1.09763(18) 0.16922(17) 0.0655(6) Uani d . 1 . .
H H15A 0.3457 1.0371 0.1413 0.098 Uiso calc R 1 . .
H H15B 0.3194 1.1417 0.1191 0.098 Uiso calc R 1 . .
H H15C 0.3164 1.1008 0.2207 0.098 Uiso calc R 1 . .
C C16 0.5115(3) 1.21091(17) 0.26153(18) 0.0714(7) Uani d . 1 . .
H H16A 0.4759 1.2116 0.3152 0.107 Uiso calc R 1 . .
H H16B 0.4754 1.2582 0.2153 0.107 Uiso calc R 1 . .
H H16C 0.5971 1.2216 0.2861 0.107 Uiso calc R 1 . .
C C17 0.82682(16) 1.01845(14) 0.23484(13) 0.0435(4) Uani d . 1 . .
C C18 0.85824(16) 0.97580(13) 0.15946(13) 0.0432(4) Uani d . 1 . .
H H18 0.7997 0.9553 0.1038 0.052 Uiso calc R 1 . .
C C19 0.98042(18) 0.96439(14) 0.16946(15) 0.0496(5) Uani d . 1 . .
C C20 1.06905(19) 0.99366(19) 0.25005(19) 0.0682(7) Uani d . 1 . .
H H20 1.1505 0.9845 0.2549 0.082 Uiso calc R 1 . .
C C21 1.0339(2) 1.0371(2) 0.32389(19) 0.0785(8) Uani d . 1 . .
H H21 1.0926 1.0580 0.3792 0.094 Uiso calc R 1 . .
C C22 0.9133(2) 1.04989(19) 0.31693(16) 0.0652(6) Uani d . 1 . .
H H22 0.8903 1.0794 0.3670 0.078 Uiso calc R 1 . .
N N1 0.66986(13) 0.83894(11) 0.46539(11) 0.0430(4) Uani d . 1 . .
N N2 0.64102(15) 0.83418(12) 0.55231(12) 0.0498(4) Uani d . 1 . .
N N3 0.62788(13) 0.91804(12) 0.57907(11) 0.0447(4) Uani d . 1 . .
N N4 0.70987(13) 0.94745(12) 0.35461(11) 0.0455(4) Uani d . 1 . .
N N5 0.54469(13) 1.04458(12) 0.28047(11) 0.0439(4) Uani d . 1 . .
H H5A 0.5090(19) 1.0317(14) 0.3220(16) 0.053 Uiso d . 1 . .
N N6 1.0155(2) 0.91968(15) 0.08856(18) 0.0698(6) Uani d . 1 . .
O O1 0.69213(14) 1.12893(11) 0.47476(11) 0.0593(4) Uani d . 1 . .
O O2 0.62878(12) 1.10169(9) 0.60849(10) 0.0500(3) Uani d . 1 . .
O O3 0.70407(11) 1.03569(10) 0.22136(9) 0.0528(4) Uani d . 1 . .
O O4 0.9375(2) 0.89508(16) 0.01765(16) 0.1013(7) Uani d . 1 . .
O O5 1.1227(2) 0.91031(17) 0.09688(19) 0.1151(8) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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
C2 C1 C6 . . 119.1(2) ?
C2 C1 C7 . . 120.50(19) ?
C6 C1 C7 . . 120.38(19) ?
C3 C2 C1 . . 120.5(2) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 120.3(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 119.8(2) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.1(3) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 120.2(2) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
N1 C7 C1 . . 111.57(16) ?
N1 C7 H7A . . 109.3 ?
C1 C7 H7A . . 109.3 ?
N1 C7 H7B . . 109.3 ?
C1 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
N1 C8 N4 . . 120.53(16) ?
N1 C8 C9 . . 103.88(14) ?
N4 C8 C9 . . 135.35(18) ?
N3 C9 C8 . . 108.45(16) ?
N3 C9 C10 . . 122.91(15) ?
C8 C9 C10 . . 128.12(16) ?
O1 C10 O2 . . 123.88(19) ?
O1 C10 C9 . . 123.91(17) ?
O2 C10 C9 . . 112.17(15) ?
O2 C11 C12 . . 107.5(2) ?
O2 C11 H11A . . 110.2 ?
C12 C11 H11A . . 110.2 ?
O2 C11 H11B . . 110.2 ?
C12 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N4 C13 N5 . . 130.36(16) ?
N4 C13 O3 . . 117.65(15) ?
N5 C13 O3 . . 111.79(15) ?
N5 C14 C16 . . 110.70(16) ?
N5 C14 C15 . . 108.05(16) ?
C16 C14 C15 . . 112.33(19) ?
N5 C14 H14 . . 108.6 ?
C16 C14 H14 . . 108.6 ?
C15 C14 H14 . . 108.6 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 C22 . . 121.54(18) ?
C18 C17 O3 . . 117.06(16) ?
C22 C17 O3 . . 121.18(17) ?
C17 C18 C19 . . 117.32(18) ?
C17 C18 H18 . . 121.3 ?
C19 C18 H18 . . 121.3 ?
C20 C19 C18 . . 123.04(19) ?
C20 C19 N6 . . 119.04(19) ?
C18 C19 N6 . . 117.92(19) ?
C19 C20 C21 . . 117.96(19) ?
C19 C20 H20 . . 121.0 ?
C21 C20 H20 . . 121.0 ?
C22 C21 C20 . . 120.9(2) ?
C22 C21 H21 . . 119.5 ?
C20 C21 H21 . . 119.5 ?
C21 C22 C17 . . 119.2(2) ?
C21 C22 H22 . . 120.4 ?
C17 C22 H22 . . 120.4 ?
C8 N1 N2 . . 111.03(15) ?
C8 N1 C7 . . 128.74(15) ?
N2 N1 C7 . . 119.81(16) ?
N3 N2 N1 . . 107.07(15) ?
N2 N3 C9 . . 109.55(14) ?
C13 N4 C8 . . 121.01(14) ?
C13 N5 C14 . . 126.48(15) ?
C13 N5 H5A . . 117.0(15) ?
C14 N5 H5A . . 115.6(15) ?
O4 N6 O5 . . 123.3(2) ?
O4 N6 C19 . . 118.8(2) ?
O5 N6 C19 . . 118.0(2) ?
C10 O2 C11 . . 115.68(16) ?
C13 O3 C17 . . 118.53(14) ?
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
C1 C2 . 1.380(3) ?
C1 C6 . 1.380(3) ?
C1 C7 . 1.507(3) ?
C2 C3 . 1.371(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.370(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.379(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.462(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.350(2) ?
C8 N4 . 1.371(2) ?
C8 C9 . 1.389(2) ?
C9 N3 . 1.361(2) ?
C9 C10 . 1.454(3) ?
C10 O1 . 1.207(2) ?
C10 O2 . 1.342(2) ?
C11 O2 . 1.448(3) ?
C11 C12 . 1.489(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 N4 . 1.286(2) ?
C13 N5 . 1.319(2) ?
C13 O3 . 1.367(2) ?
C14 N5 . 1.476(2) ?
C14 C16 . 1.508(3) ?
C14 C15 . 1.522(3) ?
C14 H14 . 0.9800 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.370(3) ?
C17 C22 . 1.378(3) ?
C17 O3 . 1.393(2) ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.367(3) ?
C19 N6 . 1.471(3) ?
C20 C21 . 1.377(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.376(3) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
N1 N2 . 1.365(2) ?
N2 N3 . 1.300(2) ?
N5 H5A . 0.83(2) ?
N6 O4 . 1.198(3) ?
N6 O5 . 1.212(3) ?
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
_geom_hbond_publ_flag
N5 H5A N3 3_676 0.83(2) 2.50(2) 3.230(2) 148(2) y
C3 H3 O1 3_776 0.93 2.42 3.303(3) 157.7 y
C21 H21 Cg1 3_776 0.93 2.98 3.829(3) 153 y
C14 H14 Cg2 2_655 0.98 2.78 3.625(2) 145 y
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
C6 C1 C2 C3 . . . . -1.6(3) ?
C7 C1 C2 C3 . . . . 178.52(19) ?
C1 C2 C3 C4 . . . . 0.0(4) ?
C2 C3 C4 C5 . . . . 2.0(4) ?
C3 C4 C5 C6 . . . . -2.4(4) ?
C4 C5 C6 C1 . . . . 0.8(4) ?
C2 C1 C6 C5 . . . . 1.1(3) ?
C7 C1 C6 C5 . . . . -179.0(2) ?
C2 C1 C7 N1 . . . . -62.2(2) ?
C6 C1 C7 N1 . . . . 117.9(2) ?
N1 C8 C9 N3 . . . . -1.17(17) ?
N4 C8 C9 N3 . . . . -175.21(18) ?
N1 C8 C9 C10 . . . . 170.66(17) ?
N4 C8 C9 C10 . . . . -3.4(3) ?
N3 C9 C10 O1 . . . . 170.10(17) ?
C8 C9 C10 O1 . . . . -0.7(3) ?
N3 C9 C10 O2 . . . . -7.7(2) ?
C8 C9 C10 O2 . . . . -178.49(15) ?
C22 C17 C18 C19 . . . . 0.8(3) ?
O3 C17 C18 C19 . . . . 175.51(16) ?
C17 C18 C19 C20 . . . . -0.1(3) ?
C17 C18 C19 N6 . . . . -179.29(18) ?
C18 C19 C20 C21 . . . . -0.5(4) ?
N6 C19 C20 C21 . . . . 178.6(2) ?
C19 C20 C21 C22 . . . . 0.5(4) ?
C20 C21 C22 C17 . . . . 0.2(4) ?
C18 C17 C22 C21 . . . . -0.8(4) ?
O3 C17 C22 C21 . . . . -175.3(2) ?
N4 C8 N1 N2 . . . . 175.89(14) ?
C9 C8 N1 N2 . . . . 0.76(18) ?
N4 C8 N1 C7 . . . . 3.4(3) ?
C9 C8 N1 C7 . . . . -171.70(16) ?
C1 C7 N1 C8 . . . . 89.8(2) ?
C1 C7 N1 N2 . . . . -82.1(2) ?
C8 N1 N2 N3 . . . . -0.05(19) ?
C7 N1 N2 N3 . . . . 173.18(15) ?
N1 N2 N3 C9 . . . . -0.72(19) ?
C8 C9 N3 N2 . . . . 1.21(19) ?
C10 C9 N3 N2 . . . . -171.13(16) ?
N5 C13 N4 C8 . . . . -16.3(3) ?
O3 C13 N4 C8 . . . . 169.37(17) ?
N1 C8 N4 C13 . . . . 136.47(19) ?
C9 C8 N4 C13 . . . . -50.3(3) ?
N4 C13 N5 C14 . . . . 175.4(2) ?
O3 C13 N5 C14 . . . . -10.0(3) ?
C16 C14 N5 C13 . . . . -94.9(2) ?
C15 C14 N5 C13 . . . . 141.7(2) ?
C20 C19 N6 O4 . . . . -179.2(2) ?
C18 C19 N6 O4 . . . . 0.0(3) ?
C20 C19 N6 O5 . . . . 0.2(3) ?
C18 C19 N6 O5 . . . . 179.4(2) ?
O1 C10 O2 C11 . . . . -2.0(3) ?
C9 C10 O2 C11 . . . . 175.81(16) ?
C12 C11 O2 C10 . . . . -174.08(18) ?
N4 C13 O3 C17 . . . . -17.6(3) ?
N5 C13 O3 C17 . . . . 166.98(17) ?
C18 C17 O3 C13 . . . . 128.60(19) ?
C22 C17 O3 C13 . . . . -56.7(3) ?
