#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:01:03 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266104 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/72/7707289.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_7707289
loop_
_publ_author_name
'Yang, Zhen-Li'
'Wu, Yue-Mei'
'He, Piao'
'Cao, Wen-Li'
'Manzoor, Saira'
'Zhang, Jian-Guo'
_publ_section_title
;
 Synthesis and characterization of promising insensitive energetic salts
 based on 3-amino-5-hydrazinopyrazole.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7456
_journal_page_last               7463
_journal_paper_doi               10.1039/d1dt00527h
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         '2(C6 H2 N3 O8), 5(H2 O), C3 H9 N5'
_chemical_formula_sum            'C15 H23 N11 O21'
_chemical_formula_weight         693.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-24 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.85(3)
_cell_angle_beta                 90.26(3)
_cell_angle_gamma                92.14(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4079(19)
_cell_length_b                   10.355(2)
_cell_length_c                   13.922(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1331.0(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14862
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.615
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0530
_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)+(0.0469P)²+1.0047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5477
_reflns_number_total             6075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00527h2.cif
_cod_data_source_block           bwn18435
_cod_depositor_comments
'Adding full bibliography for 7707286--7707290.cif.'
_cod_database_code               7707289
_shelx_shelxl_version_number     2018/3
_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_max   0.984
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H20A,H20B} of O20, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups, {H19A,H19B} of O19, {H17A,H17B} of O17, {H21A,H21B} of O21
2.a Riding coordinates:
 O20(H20A,H20B)
2.b Free rotating group:
 O17(H17A,H17B), O19(H19A,H19B), O21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), N3(H3A), N4(H4), C2(H2A), C11(H11)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.74079(16) 0.02172(14) 0.25345(11) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.62988(17) -0.09865(14) 0.34256(11) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.67439(16) 0.09151(14) 0.51316(10) 0.0246(3) Uani 1 1 d . . . . .
H3 H 0.675218 0.126121 0.572801 0.037 Uiso 1 1 calc GR . . . .
O4 O 0.61278(16) 0.27047(14) 0.66088(10) 0.0255(3) Uani 1 1 d . . . . .
O5 O 0.44720(17) 0.40717(15) 0.64974(10) 0.0282(3) Uani 1 1 d . . . . .
O6 O 0.25253(17) 0.45212(16) 0.35152(11) 0.0327(4) Uani 1 1 d . . . . .
O7 O 0.3260(2) 0.3506(2) 0.21466(11) 0.0579(6) Uani 1 1 d . . . . .
O8 O 0.48723(14) 0.14261(13) 0.20946(9) 0.0200(3) Uani 1 1 d . . . . .
N6 N 0.65482(18) 0.00645(16) 0.31684(11) 0.0201(3) Uani 1 1 d . . . . .
N7 N 0.52327(18) 0.31793(16) 0.61175(11) 0.0209(3) Uani 1 1 d . . . . .
N8 N 0.32681(18) 0.36932(17) 0.30352(12) 0.0228(4) Uani 1 1 d . . . . .
C4 C 0.5768(2) 0.12072(18) 0.36381(13) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.5899(2) 0.15790(18) 0.46420(13) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.5121(2) 0.26797(19) 0.50922(13) 0.0189(4) Uani 1 1 d . . . . .
C7 C 0.4259(2) 0.33169(19) 0.45377(13) 0.0191(4) Uani 1 1 d . . . . .
H7 H 0.372243 0.403204 0.485173 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4169(2) 0.29288(19) 0.35393(13) 0.0188(4) Uani 1 1 d . . . . .
C9 C 0.49349(19) 0.18352(18) 0.30051(13) 0.0169(4) Uani 1 1 d . . . . .
O9 O 0.15351(17) -0.00711(15) 0.15465(10) 0.0299(3) Uani 1 1 d . . . . .
O10 O 0.25082(17) -0.04255(15) 0.28709(11) 0.0302(3) Uani 1 1 d . . . . .
O11 O 0.07328(18) 0.13394(16) 0.59487(11) 0.0344(4) Uani 1 1 d . . . . .
O12 O -0.07442(17) 0.29209(16) 0.61578(11) 0.0326(4) Uani 1 1 d . . . . .
O13 O -0.15290(16) 0.40130(15) 0.47282(10) 0.0280(3) Uani 1 1 d . . . . .
H13 H -0.148413 0.395901 0.532205 0.042 Uiso 1 1 calc GR . . . .
O14 O -0.1045(2) 0.49684(19) 0.2769(2) 0.0745(8) Uani 1 1 d . . . . .
O15 O -0.27347(17) 0.35281(16) 0.24347(13) 0.0347(4) Uani 1 1 d . . . . .
O16 O -0.00759(15) 0.20151(13) 0.16212(10) 0.0223(3) Uani 1 1 d . . . . .
O17 O 0.09939(16) 0.40031(14) 0.07513(10) 0.0239(3) Uani 1 1 d . . . . .
H17A H 0.118124 0.472068 0.114737 0.036 Uiso 1 1 d G . . . .
H17B H 0.082226 0.344461 0.111613 0.036 Uiso 1 1 d G . . . .
O18 O 0.17012(18) 0.64506(16) 0.17491(11) 0.0294(3) Uani 1 1 d . . . . .
O19 O -0.08022(17) 0.77271(15) 0.18310(11) 0.0304(3) Uani 1 1 d . . . . .
H19A H -0.091449 0.824764 0.237298 0.046 Uiso 1 1 d G . . . .
H19B H -0.143970 0.711206 0.176203 0.046 Uiso 1 1 d G . . . .
O20 O 0.19249(16) 0.64547(14) -0.02368(10) 0.0256(3) Uani 1 1 d . . . . .
H20A H 0.106762 0.625334 -0.038362 0.031 Uiso 1 1 d R . . . .
H20B H 0.198592 0.661074 0.037668 0.031 Uiso 1 1 d R . . . .
O21 O 0.86419(17) -0.09772(15) 0.02376(11) 0.0298(3) Uani 1 1 d . . . . .
H21A H 0.903701 -0.132921 0.066930 0.045 Uiso 1 1 d G . . . .
H21B H 0.912768 -0.111013 -0.028237 0.045 Uiso 1 1 d G . . . .
N1 N 0.70419(17) 0.11257(16) 0.06778(11) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.766472 0.046938 0.065511 0.024 Uiso 1 1 calc GR . . . .
H1B H 0.644060 0.112091 0.118731 0.024 Uiso 1 1 calc GR . . . .
H1C H 0.753099 0.191447 0.075983 0.024 Uiso 1 1 calc GR . . . .
N2 N 0.62332(17) 0.09236(16) -0.02234(12) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.44985(17) 0.24502(16) 0.04199(11) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.446787 0.225067 0.100679 0.023 Uiso 1 1 calc R . . . .
N4 N 0.37130(18) 0.33791(16) 0.00981(12) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.311944 0.390471 0.045137 0.026 Uiso 1 1 calc R . . . .
N5 N 0.3292(2) 0.4099(2) -0.13809(14) 0.0283(4) Uani 1 1 d . . . . .
N9 N 0.16765(17) 0.01658(16) 0.24432(11) 0.0195(3) Uani 1 1 d . . . . .
N10 N 0.00320(19) 0.21445(17) 0.56267(12) 0.0245(4) Uani 1 1 d . . . . .
N11 N -0.15703(18) 0.38947(16) 0.27803(12) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.5316(2) 0.19038(18) -0.03137(13) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.5037(2) 0.24286(19) -0.11369(14) 0.0208(4) Uani 1 1 d . . . . .
H2A H 0.545859 0.220808 -0.176215 0.025 Uiso 1 1 calc R . . . .
C3 C 0.4007(2) 0.33469(19) -0.08508(14) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.0838(2) 0.11793(18) 0.30044(13) 0.0187(4) Uani 1 1 d . . . . .
C11 C 0.0857(2) 0.12657(19) 0.40032(14) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.142235 0.068856 0.428392 0.024 Uiso 1 1 calc R . . . .
C12 C 0.0066(2) 0.21794(19) 0.46030(13) 0.0207(4) Uani 1 1 d . . . . .
C13 C -0.0752(2) 0.30800(19) 0.42046(14) 0.0203(4) Uani 1 1 d . . . . .
C14 C -0.0737(2) 0.29688(18) 0.32079(14) 0.0197(4) Uani 1 1 d . . . . .
C15 C 0.0012(2) 0.20249(18) 0.25226(13) 0.0186(4) Uani 1 1 d . . . . .
H5A H 0.293(3) 0.484(3) -0.102(2) 0.036(7) Uiso 1 1 d . . . . .
H5B H 0.368(3) 0.417(3) -0.191(2) 0.040(8) Uiso 1 1 d . . . . .
H18A H 0.084(4) 0.692(3) 0.189(2) 0.053(9) Uiso 1 1 d . . . . .
H18B H 0.220(4) 0.651(4) 0.231(3) 0.081(12) Uiso 1 1 d . . . . .
H2 H 0.685(3) 0.080(2) -0.0710(18) 0.026(6) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 H3 109.5 . . ?
O1 N6 C4 117.98(16) . . ?
O2 N6 O1 123.88(17) . . ?
O2 N6 C4 118.14(16) . . ?
O4 N7 C6 118.60(16) . . ?
O5 N7 O4 121.55(16) . . ?
O5 N7 C6 119.84(17) . . ?
O6 N8 C8 119.15(16) . . ?
O7 N8 O6 121.21(18) . . ?
O7 N8 C8 119.64(16) . . ?
C5 C4 N6 117.37(16) . . ?
C5 C4 C9 126.18(17) . . ?
C9 C4 N6 116.45(15) . . ?
O3 C5 C4 119.33(17) . . ?
O3 C5 C6 123.77(17) . . ?
C4 C5 C6 116.89(17) . . ?
C5 C6 N7 121.32(17) . . ?
C7 C6 N7 118.08(17) . . ?
C7 C6 C5 120.58(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.86(18) . . ?
C8 C7 H7 119.6 . . ?
N8 C8 C9 121.05(16) . . ?
C7 C8 N8 115.89(17) . . ?
C7 C8 C9 123.06(17) . . ?
O8 C9 C4 121.96(17) . . ?
O8 C9 C8 125.62(17) . . ?
C4 C9 C8 112.38(16) . . ?
C13 O13 H13 109.5 . . ?
H17A O17 H17B 104.5 . . ?
H18A O18 H18B 108(3) . . ?
H19A O19 H19B 109.5 . . ?
H20A O20 H20B 107.0 . . ?
H21A O21 H21B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N2 N1 H1A 109.5 . . ?
N2 N1 H1B 109.5 . . ?
N2 N1 H1C 109.5 . . ?
N1 N2 H2 107.4(16) . . ?
C1 N2 N1 115.41(15) . . ?
C1 N2 H2 111.5(16) . . ?
N4 N3 H3A 126.0 . . ?
C1 N3 H3A 126.0 . . ?
C1 N3 N4 107.92(15) . . ?
N3 N4 H4 125.9 . . ?
C3 N4 N3 108.19(15) . . ?
C3 N4 H4 125.9 . . ?
C3 N5 H5A 114.3(17) . . ?
C3 N5 H5B 113.5(19) . . ?
H5A N5 H5B 118(3) . . ?
O9 N9 C10 118.54(16) . . ?
O10 N9 O9 122.11(16) . . ?
O10 N9 C10 119.35(16) . . ?
O11 N10 O12 122.19(17) . . ?
O11 N10 C12 119.62(17) . . ?
O12 N10 C12 118.17(17) . . ?
O14 N11 O15 123.38(19) . . ?
O14 N11 C14 118.12(18) . . ?
O15 N11 C14 118.47(17) . . ?
N2 C1 C2 128.00(17) . . ?
N3 C1 N2 122.16(17) . . ?
N3 C1 C2 109.78(17) . . ?
C1 C2 H2A 127.4 . . ?
C1 C2 C3 105.16(16) . . ?
C3 C2 H2A 127.4 . . ?
N4 C3 N5 120.85(18) . . ?
N4 C3 C2 108.87(17) . . ?
N5 C3 C2 130.22(18) . . ?
C11 C10 N9 116.40(17) . . ?
C11 C10 C15 122.85(17) . . ?
C15 C10 N9 120.73(16) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.95(18) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 N10 118.26(18) . . ?
C11 C12 C13 120.62(17) . . ?
C13 C12 N10 121.04(17) . . ?
O13 C13 C12 124.87(17) . . ?
O13 C13 C14 118.42(18) . . ?
C14 C13 C12 116.71(17) . . ?
C13 C14 N11 117.64(17) . . ?
C13 C14 C15 126.70(18) . . ?
C15 C14 N11 115.66(16) . . ?
O16 C15 C10 127.34(17) . . ?
O16 C15 C14 120.53(17) . . ?
C14 C15 C10 112.12(16) . . ?
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
O1 N6 1.228(2) . ?
O2 N6 1.223(2) . ?
O3 H3 0.8400 . ?
O3 C5 1.335(2) . ?
O4 N7 1.253(2) . ?
O5 N7 1.231(2) . ?
O6 N8 1.226(2) . ?
O7 N8 1.216(2) . ?
O8 C9 1.259(2) . ?
N6 C4 1.464(2) . ?
N7 C6 1.426(2) . ?
N8 C8 1.446(2) . ?
C4 C5 1.382(3) . ?
C4 C9 1.436(3) . ?
C5 C6 1.423(3) . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(3) . ?
C8 C9 1.450(3) . ?
O9 N9 1.232(2) . ?
O10 N9 1.229(2) . ?
O11 N10 1.229(2) . ?
O12 N10 1.246(2) . ?
O13 H13 0.8400 . ?
O13 C13 1.339(2) . ?
O14 N11 1.202(2) . ?
O15 N11 1.213(2) . ?
O16 C15 1.255(2) . ?
O17 H17A 0.8499 . ?
O17 H17B 0.8501 . ?
O18 H18A 0.96(3) . ?
O18 H18B 0.90(4) . ?
O19 H19A 0.8503 . ?
O19 H19B 0.8499 . ?
O20 H20A 0.8400 . ?
O20 H20B 0.8402 . ?
O21 H21A 0.8502 . ?
O21 H21B 0.8498 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 N2 1.441(2) . ?
N2 C1 1.379(2) . ?
N2 H2 0.89(3) . ?
N3 H3A 0.8800 . ?
N3 N4 1.373(2) . ?
N3 C1 1.333(2) . ?
N4 H4 0.8800 . ?
N4 C3 1.346(2) . ?
N5 C3 1.362(3) . ?
N5 H5A 0.91(3) . ?
N5 H5B 0.83(3) . ?
N9 C10 1.447(2) . ?
N10 C12 1.433(2) . ?
N11 C14 1.468(2) . ?
C1 C2 1.386(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.390(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.445(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 C13 1.419(3) . ?
C13 C14 1.371(3) . ?
C14 C15 1.439(3) . ?
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
O1 N6 C4 C5 -121.84(19) . . . . ?
O1 N6 C4 C9 58.2(2) . . . . ?
O2 N6 C4 C5 58.6(2) . . . . ?
O2 N6 C4 C9 -121.32(19) . . . . ?
O3 C5 C6 N7 1.9(3) . . . . ?
O3 C5 C6 C7 -179.68(18) . . . . ?
O4 N7 C6 C5 6.2(3) . . . . ?
O4 N7 C6 C7 -172.18(17) . . . . ?
O5 N7 C6 C5 -174.81(18) . . . . ?
O5 N7 C6 C7 6.8(3) . . . . ?
O6 N8 C8 C7 -8.2(3) . . . . ?
O6 N8 C8 C9 172.59(18) . . . . ?
O7 N8 C8 C7 171.7(2) . . . . ?
O7 N8 C8 C9 -7.5(3) . . . . ?
N6 C4 C5 O3 1.7(3) . . . . ?
N6 C4 C5 C6 -179.20(16) . . . . ?
N6 C4 C9 O8 0.2(3) . . . . ?
N6 C4 C9 C8 178.23(16) . . . . ?
N7 C6 C7 C8 176.36(17) . . . . ?
N8 C8 C9 O8 -2.1(3) . . . . ?
N8 C8 C9 C4 179.94(16) . . . . ?
C4 C5 C6 N7 -177.15(17) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C4 C9 O8 -179.74(18) . . . . ?
C5 C4 C9 C8 -1.7(3) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C6 C7 C8 N8 -178.18(17) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 O8 178.77(18) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C9 C4 C5 O3 -178.38(17) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
O9 N9 C10 C11 169.87(17) . . . . ?
O9 N9 C10 C15 -8.9(3) . . . . ?
O10 N9 C10 C11 -10.5(3) . . . . ?
O10 N9 C10 C15 170.73(17) . . . . ?
O11 N10 C12 C11 2.2(3) . . . . ?
O11 N10 C12 C13 178.78(18) . . . . ?
O12 N10 C12 C11 -176.09(18) . . . . ?
O12 N10 C12 C13 0.5(3) . . . . ?
O13 C13 C14 N11 0.5(3) . . . . ?
O13 C13 C14 C15 -179.15(18) . . . . ?
O14 N11 C14 C13 82.6(3) . . . . ?
O14 N11 C14 C15 -97.6(3) . . . . ?
O15 N11 C14 C13 -99.2(2) . . . . ?
O15 N11 C14 C15 80.5(2) . . . . ?
N1 N2 C1 N3 -43.2(3) . . . . ?
N1 N2 C1 C2 139.9(2) . . . . ?
N2 C1 C2 C3 178.02(19) . . . . ?
N3 N4 C3 N5 174.90(18) . . . . ?
N3 N4 C3 C2 -2.5(2) . . . . ?
N3 C1 C2 C3 0.8(2) . . . . ?
N4 N3 C1 N2 -179.74(17) . . . . ?
N4 N3 C1 C2 -2.4(2) . . . . ?
N9 C10 C11 C12 -178.46(17) . . . . ?
N9 C10 C15 O16 -1.0(3) . . . . ?
N9 C10 C15 C14 -179.71(16) . . . . ?
N10 C12 C13 O13 4.8(3) . . . . ?
N10 C12 C13 C14 -174.98(18) . . . . ?
N11 C14 C15 O16 -0.6(3) . . . . ?
N11 C14 C15 C10 178.22(16) . . . . ?
C1 N3 N4 C3 3.0(2) . . . . ?
C1 C2 C3 N4 1.0(2) . . . . ?
C1 C2 C3 N5 -176.0(2) . . . . ?
C10 C11 C12 N10 174.62(18) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
C11 C10 C15 O16 -179.67(19) . . . . ?
C11 C10 C15 C14 1.6(3) . . . . ?
C11 C12 C13 O13 -178.73(18) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 N11 -179.70(17) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 O16 179.08(19) . . . . ?
C13 C14 C15 C10 -2.1(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
