#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228570.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_2228570
loop_
_publ_author_name
'Tecer, Elif'
'Dege, Necmi'
'Zülfikaroğlu, Ayşin'
'Şenyüz, Nuray'
'Batı, Hümeyra'
_publ_section_title
;
 N'-(2,3-Dihydroxybenzylidene)isonicotinohydrazide
;
_journal_coeditor_code           SU2224
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3369
_journal_page_last               o3370
_journal_paper_doi               10.1107/S1600536810048701
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H11 N3 O3'
_chemical_formula_moiety         'C13 H11 N3 O3'
_chemical_formula_sum            'C13 H11 N3 O3'
_chemical_formula_weight         257.25
_chemical_name_systematic
;
N'-(2,3-Dihydroxybenzylidene)isonicotinohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.551(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7781(2)
_cell_length_b                   30.0719(8)
_cell_length_c                   10.5116(3)
_cell_measurement_reflns_used    29970
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      1.35
_cell_volume                     2408.89(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Burnett & Johnson, 1996)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'w-scan rotation'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34859
_diffrn_reflns_theta_full        26.78
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.103
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0382
_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)+(0.0416P)²+0.0050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                3512
_reflns_number_total             5118
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2224.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228570
_cod_database_fobs_code          2228570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.34616(19) 0.51866(5) 0.32097(13) 0.0431(3) Uani d . 1 . .
C C2 0.35373(19) 0.56269(5) 0.36519(13) 0.0419(3) Uani d . 1 . .
C C3 0.4074(2) 0.59653(5) 0.29149(14) 0.0462(3) Uani d . 1 . .
C C4 0.4506(2) 0.58674(6) 0.17444(16) 0.0581(4) Uani d . 1 . .
C C5 0.4439(3) 0.54342(6) 0.12981(17) 0.0640(5) Uani d . 1 . .
C C6 0.3938(2) 0.50971(6) 0.20279(16) 0.0568(4) Uani d . 1 . .
C C7 0.2901(2) 0.48325(5) 0.39706(14) 0.0453(3) Uani d . 1 . .
C C8 0.14430(19) 0.47313(4) 0.68980(14) 0.0444(3) Uani d . 1 . .
C C9 0.08913(19) 0.43654(4) 0.77030(13) 0.0420(3) Uani d . 1 . .
C C10 0.0715(2) 0.39237(5) 0.73485(15) 0.0534(4) Uani d . 1 . .
C C11 0.0135(2) 0.36246(5) 0.81626(15) 0.0540(4) Uani d . 1 . .
C C12 -0.0071(3) 0.41568(5) 0.96253(16) 0.0599(4) Uani d . 1 . .
C C13 0.0503(2) 0.44791(5) 0.88844(15) 0.0547(4) Uani d . 1 . .
C C14 0.4163(2) 0.72836(5) 0.73128(14) 0.0449(3) Uani d . 1 . .
C C15 0.41093(19) 0.68485(4) 0.68380(13) 0.0422(3) Uani d . 1 . .
C C16 0.5024(2) 0.65111(5) 0.76002(14) 0.0480(4) Uani d . 1 . .
C C17 0.5992(2) 0.66094(6) 0.88134(16) 0.0566(4) Uani d . 1 . .
C C18 0.6080(3) 0.70385(6) 0.92819(17) 0.0643(5) Uani d . 1 . .
C C19 0.5175(2) 0.73716(6) 0.85442(16) 0.0585(4) Uani d . 1 . .
C C20 0.3177(2) 0.76380(5) 0.65502(15) 0.0484(4) Uani d . 1 . .
C C21 0.0455(2) 0.77429(5) 0.34901(14) 0.0464(4) Uani d . 1 . .
C C22 -0.0175(2) 0.81153(4) 0.25675(14) 0.0435(3) Uani d . 1 . .
C C23 0.0552(2) 0.85359(5) 0.26961(15) 0.0464(3) Uani d . 1 . .
C C24 -0.0049(2) 0.88488(5) 0.17529(15) 0.0525(4) Uani d . 1 . .
C C25 -0.1971(3) 0.83591(6) 0.05928(17) 0.0614(4) Uani d . 1 . .
C C26 -0.1452(2) 0.80275(5) 0.14845(16) 0.0558(4) Uani d . 1 . .
N N1 0.24130(16) 0.49326(4) 0.50259(11) 0.0446(3) Uani d . 1 . .
N N2 0.18813(17) 0.46034(4) 0.57653(12) 0.0458(3) Uani d . 1 . .
N N3 -0.02774(18) 0.37320(4) 0.92838(12) 0.0526(3) Uani d . 1 . .
N N4 0.22153(17) 0.75411(4) 0.54531(11) 0.0472(3) Uani d . 1 . .
N N5 0.13318(18) 0.78684(4) 0.46848(12) 0.0494(3) Uani d . 1 . .
N N6 -0.12988(19) 0.87675(4) 0.07101(12) 0.0563(3) Uani d . 1 . .
O O1 0.30926(15) 0.57472(3) 0.47939(9) 0.0522(3) Uani d . 1 . .
O O2 0.41509(17) 0.63953(3) 0.33438(11) 0.0598(3) Uani d . 1 . .
O O3 0.14895(16) 0.51167(3) 0.72583(10) 0.0587(3) Uani d . 1 . .
O O4 0.31740(15) 0.67309(3) 0.56449(9) 0.0512(3) Uani d . 1 . .
O O5 0.49762(18) 0.60853(4) 0.71623(12) 0.0666(3) Uani d . 1 . .
O O6 0.02582(17) 0.73564(3) 0.31578(10) 0.0636(3) Uani d . 1 . .
H H1O 0.276(3) 0.5475(7) 0.5152(19) 0.090(6) Uiso d . 1 . .
H H2N 0.180(2) 0.4320(6) 0.5448(15) 0.057(5) Uiso d . 1 . .
H H2O 0.375(3) 0.6411(7) 0.415(2) 0.099(7) Uiso d . 1 . .
H H4 0.486(2) 0.6103(6) 0.1235(15) 0.061(5) Uiso d . 1 . .
H H4O 0.260(3) 0.7006(8) 0.531(2) 0.095(7) Uiso d . 1 . .
H H5 0.472(2) 0.5371(6) 0.0478(18) 0.077(5) Uiso d . 1 . .
H H5N 0.128(2) 0.8148(6) 0.4980(16) 0.059(5) Uiso d . 1 . .
H H5O 0.427(3) 0.6065(8) 0.636(2) 0.106(8) Uiso d . 1 . .
H H6 0.390(2) 0.4797(6) 0.1748(15) 0.060(5) Uiso d . 1 . .
H H7 0.294(2) 0.4536(5) 0.3685(14) 0.051(4) Uiso d . 1 . .
H H10 0.096(2) 0.3824(6) 0.6532(17) 0.066(5) Uiso d . 1 . .
H H11 0.003(2) 0.3318(6) 0.7931(15) 0.061(5) Uiso d . 1 . .
H H12 -0.034(2) 0.4237(6) 1.0435(18) 0.074(5) Uiso d . 1 . .
H H13 0.060(2) 0.4793(6) 0.9133(16) 0.068(5) Uiso d . 1 . .
H H17 0.661(2) 0.6365(6) 0.9290(16) 0.064(5) Uiso d . 1 . .
H H18 0.679(2) 0.7098(6) 1.0143(18) 0.073(5) Uiso d . 1 . .
H H19 0.522(2) 0.7674(6) 0.8835(16) 0.071(5) Uiso d . 1 . .
H H20 0.325(2) 0.7937(6) 0.6894(15) 0.060(5) Uiso d . 1 . .
H H23 0.151(2) 0.8611(5) 0.3421(15) 0.052(4) Uiso d . 1 . .
H H24 0.043(2) 0.9140(6) 0.1819(16) 0.064(5) Uiso d . 1 . .
H H25 -0.286(3) 0.8311(6) -0.0207(19) 0.082(6) Uiso d . 1 . .
H H26 -0.199(2) 0.7732(6) 0.1373(16) 0.064(5) Uiso 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
C6 C1 C2 . . 118.56(13) ?
C6 C1 C7 . . 120.89(14) ?
C2 C1 C7 . . 120.56(13) ?
O1 C2 C3 . . 116.93(12) ?
O1 C2 C1 . . 122.82(12) ?
C3 C2 C1 . . 120.24(13) ?
O2 C3 C4 . . 119.77(13) ?
O2 C3 C2 . . 120.41(13) ?
C4 C3 C2 . . 119.81(14) ?
C3 C4 C5 . . 120.50(15) ?
C3 C4 H4 . . 119.4(10) ?
C5 C4 H4 . . 120.1(10) ?
C6 C5 C4 . . 120.10(16) ?
C6 C5 H5 . . 120.2(11) ?
C4 C5 H5 . . 119.7(11) ?
C5 C6 C1 . . 120.77(16) ?
C5 C6 H6 . . 121.7(10) ?
C1 C6 H6 . . 117.6(10) ?
N1 C7 C1 . . 118.68(13) ?
N1 C7 H7 . . 122.3(9) ?
C1 C7 H7 . . 119.0(9) ?
O3 C8 N2 . . 123.06(13) ?
O3 C8 C9 . . 121.07(13) ?
N2 C8 C9 . . 115.87(12) ?
C13 C9 C10 . . 117.05(14) ?
C13 C9 C8 . . 117.67(13) ?
C10 C9 C8 . . 125.28(13) ?
C11 C10 C9 . . 119.21(14) ?
C11 C10 H10 . . 119.9(10) ?
C9 C10 H10 . . 120.9(10) ?
N3 C11 C10 . . 124.20(15) ?
N3 C11 H11 . . 116.2(10) ?
C10 C11 H11 . . 119.6(10) ?
N3 C12 C13 . . 124.13(15) ?
N3 C12 H12 . . 116.8(11) ?
C13 C12 H12 . . 119.1(11) ?
C12 C13 C9 . . 119.38(15) ?
C12 C13 H13 . . 123.0(10) ?
C9 C13 H13 . . 117.5(10) ?
C15 C14 C19 . . 118.58(14) ?
C15 C14 C20 . . 120.91(13) ?
C19 C14 C20 . . 120.51(14) ?
O4 C15 C16 . . 117.12(12) ?
O4 C15 C14 . . 122.88(13) ?
C16 C15 C14 . . 119.99(13) ?
O5 C16 C17 . . 119.26(14) ?
O5 C16 C15 . . 120.95(13) ?
C17 C16 C15 . . 119.80(14) ?
C16 C17 C18 . . 120.71(16) ?
C16 C17 H17 . . 116.3(10) ?
C18 C17 H17 . . 123.0(10) ?
C19 C18 C17 . . 119.92(16) ?
C19 C18 H18 . . 121.4(11) ?
C17 C18 H18 . . 118.7(11) ?
C18 C19 C14 . . 120.99(16) ?
C18 C19 H19 . . 122.2(11) ?
C14 C19 H19 . . 116.8(11) ?
N4 C20 C14 . . 118.63(13) ?
N4 C20 H20 . . 122.1(10) ?
C14 C20 H20 . . 119.3(10) ?
O6 C21 N5 . . 122.91(14) ?
O6 C21 C22 . . 121.54(14) ?
N5 C21 C22 . . 115.46(12) ?
C26 C22 C23 . . 118.00(14) ?
C26 C22 C21 . . 118.68(13) ?
C23 C22 C21 . . 123.15(14) ?
C24 C23 C22 . . 118.79(15) ?
C24 C23 H23 . . 119.8(9) ?
C22 C23 H23 . . 121.4(9) ?
N6 C24 C23 . . 123.50(15) ?
N6 C24 H24 . . 116.1(10) ?
C23 C24 H24 . . 120.4(10) ?
N6 C25 C26 . . 123.41(17) ?
N6 C25 H25 . . 114.1(11) ?
C26 C25 H25 . . 122.5(11) ?
C25 C26 C22 . . 119.33(16) ?
C25 C26 H26 . . 121.2(10) ?
C22 C26 H26 . . 119.4(10) ?
C7 N1 N2 . . 119.80(12) ?
C8 N2 N1 . . 116.67(12) ?
C8 N2 H2N . . 125.0(10) ?
N1 N2 H2N . . 118.2(10) ?
C11 N3 C12 . . 116.00(13) ?
C20 N4 N5 . . 120.22(12) ?
C21 N5 N4 . . 116.50(12) ?
C21 N5 H5N . . 122.0(11) ?
N4 N5 H5N . . 121.4(11) ?
C25 N6 C24 . . 116.96(14) ?
C2 O1 H1O . . 104.8(12) ?
C3 O2 H2O . . 109.8(13) ?
C15 O4 H4O . . 103.7(12) ?
C16 O5 H5O . . 110.2(15) ?
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 C6 . 1.392(2) ?
C1 C2 . 1.4005(19) ?
C1 C7 . 1.450(2) ?
C2 O1 . 1.3630(17) ?
C2 C3 . 1.3925(19) ?
C3 O2 . 1.3669(18) ?
C3 C4 . 1.371(2) ?
C4 C5 . 1.382(2) ?
C4 H4 . 0.961(17) ?
C5 C6 . 1.374(2) ?
C5 H5 . 0.951(19) ?
C6 H6 . 0.949(17) ?
C7 N1 . 1.2782(18) ?
C7 H7 . 0.943(16) ?
C8 O3 . 1.2174(16) ?
C8 N2 . 1.3582(18) ?
C8 C9 . 1.5023(19) ?
C9 C13 . 1.379(2) ?
C9 C10 . 1.379(2) ?
C10 C11 . 1.378(2) ?
C10 H10 . 0.964(17) ?
C11 N3 . 1.322(2) ?
C11 H11 . 0.952(17) ?
C12 N3 . 1.328(2) ?
C12 C13 . 1.373(2) ?
C12 H12 . 0.946(18) ?
C13 H13 . 0.977(18) ?
C14 C15 . 1.3981(19) ?
C14 C19 . 1.399(2) ?
C14 C20 . 1.456(2) ?
C15 O4 . 1.3644(17) ?
C15 C16 . 1.396(2) ?
C16 O5 . 1.3589(18) ?
C16 C17 . 1.377(2) ?
C17 C18 . 1.378(2) ?
C17 H17 . 0.961(18) ?
C18 C19 . 1.372(3) ?
C18 H18 . 0.979(19) ?
C19 H19 . 0.958(19) ?
C20 N4 . 1.276(2) ?
C20 H20 . 0.967(17) ?
C21 O6 . 1.2145(17) ?
C21 N5 . 1.3571(19) ?
C21 C22 . 1.498(2) ?
C22 C26 . 1.378(2) ?
C22 C23 . 1.381(2) ?
C23 C24 . 1.379(2) ?
C23 H23 . 0.979(16) ?
C24 N6 . 1.334(2) ?
C24 H24 . 0.950(18) ?
C25 N6 . 1.331(2) ?
C25 C26 . 1.373(2) ?
C25 H25 . 0.99(2) ?
C26 H26 . 0.977(18) ?
N1 N2 . 1.3726(15) ?
N2 H2N . 0.912(17) ?
N4 N5 . 1.3679(16) ?
N5 H5N . 0.901(17) ?
O1 H1O . 0.96(2) ?
O2 H2O . 0.96(2) ?
O4 H4O . 0.97(2) ?
O5 H5O . 0.91(2) ?
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
O1 H1O N1 . 0.96(2) 1.65(2) 2.5281(15) 149.7(18) yes
N2 H2N N6 2_545 0.913(18) 2.051(17) 2.9407(17) 164.7(15) yes
O2 H2O O1 . 0.96(2) 2.20(2) 2.7022(14) 111.3(15) yes
O2 H2O O4 . 0.96(2) 1.97(2) 2.8605(15) 153.3(18) yes
O4 H4O N4 . 0.97(2) 1.65(2) 2.5441(15) 151.2(19) yes
N5 H5N N3 2_556 0.900(18) 2.129(17) 2.9914(18) 160.2(14) yes
O5 H5O O1 . 0.91(2) 1.96(2) 2.8138(16) 154(2) yes
O5 H5O O4 . 0.91(2) 2.25(2) 2.7171(16) 111.6(18) yes
C10 H10 N6 2_545 0.964(17) 2.429(17) 3.369(2) 164.8(15) yes
C11 H11 O6 3_566 0.953(18) 2.317(18) 3.2485(18) 165.4(13) yes
C20 H20 O2 4_576 0.967(18) 2.533(17) 3.4652(18) 162.0(13) yes
C24 H24 O3 4_575 0.949(18) 2.395(18) 3.3373(18) 172.1(14) 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_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 O1 . . . . 179.80(14) ?
C7 C1 C2 O1 . . . . -0.3(2) ?
C6 C1 C2 C3 . . . . 0.2(2) ?
C7 C1 C2 C3 . . . . -179.86(13) ?
O1 C2 C3 O2 . . . . 0.5(2) ?
C1 C2 C3 O2 . . . . -179.93(14) ?
O1 C2 C3 C4 . . . . -178.75(14) ?
C1 C2 C3 C4 . . . . 0.9(2) ?
O2 C3 C4 C5 . . . . 179.84(16) ?
C2 C3 C4 C5 . . . . -0.9(3) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C4 C5 C6 C1 . . . . 1.1(3) ?
C2 C1 C6 C5 . . . . -1.2(2) ?
C7 C1 C6 C5 . . . . 178.86(16) ?
C6 C1 C7 N1 . . . . -177.40(15) ?
C2 C1 C7 N1 . . . . 2.7(2) ?
O3 C8 C9 C13 . . . . -2.3(2) ?
N2 C8 C9 C13 . . . . 177.47(14) ?
O3 C8 C9 C10 . . . . 176.64(16) ?
N2 C8 C9 C10 . . . . -3.5(2) ?
C13 C9 C10 C11 . . . . 1.4(2) ?
C8 C9 C10 C11 . . . . -177.64(16) ?
C9 C10 C11 N3 . . . . 0.1(3) ?
N3 C12 C13 C9 . . . . 0.4(3) ?
C10 C9 C13 C12 . . . . -1.6(2) ?
C8 C9 C13 C12 . . . . 177.49(16) ?
C19 C14 C15 O4 . . . . -179.38(14) ?
C20 C14 C15 O4 . . . . 1.2(2) ?
C19 C14 C15 C16 . . . . 1.3(2) ?
C20 C14 C15 C16 . . . . -178.15(14) ?
O4 C15 C16 O5 . . . . 0.0(2) ?
C14 C15 C16 O5 . . . . 179.39(14) ?
O4 C15 C16 C17 . . . . 179.97(14) ?
C14 C15 C16 C17 . . . . -0.7(2) ?
O5 C16 C17 C18 . . . . 179.45(16) ?
C15 C16 C17 C18 . . . . -0.5(2) ?
C16 C17 C18 C19 . . . . 1.0(3) ?
C17 C18 C19 C14 . . . . -0.3(3) ?
C15 C14 C19 C18 . . . . -0.8(2) ?
C20 C14 C19 C18 . . . . 178.64(16) ?
C15 C14 C20 N4 . . . . 2.2(2) ?
C19 C14 C20 N4 . . . . -177.30(15) ?
O6 C21 C22 C26 . . . . 20.5(2) ?
N5 C21 C22 C26 . . . . -162.84(14) ?
O6 C21 C22 C23 . . . . -154.54(15) ?
N5 C21 C22 C23 . . . . 22.1(2) ?
C26 C22 C23 C24 . . . . 1.0(2) ?
C21 C22 C23 C24 . . . . 176.10(14) ?
C22 C23 C24 N6 . . . . -0.3(2) ?
N6 C25 C26 C22 . . . . 0.3(3) ?
C23 C22 C26 C25 . . . . -1.0(2) ?
C21 C22 C26 C25 . . . . -176.33(15) ?
C1 C7 N1 N2 . . . . -179.80(13) ?
O3 C8 N2 N1 . . . . 0.7(2) ?
C9 C8 N2 N1 . . . . -179.09(12) ?
C7 N1 N2 C8 . . . . 177.63(14) ?
C10 C11 N3 C12 . . . . -1.3(3) ?
C13 C12 N3 C11 . . . . 1.0(3) ?
C14 C20 N4 N5 . . . . -177.10(13) ?
O6 C21 N5 N4 . . . . 9.1(2) ?
C22 C21 N5 N4 . . . . -167.49(12) ?
C20 N4 N5 C21 . . . . 174.77(14) ?
C26 C25 N6 C24 . . . . 0.5(3) ?
C23 C24 N6 C25 . . . . -0.5(2) ?
