#------------------------------------------------------------------------------ #$Date: 2017-05-06 01:17:27 +0300 (Sat, 06 May 2017) $ #$Revision: 196478 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/60/7056071.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_7056071 loop_ _publ_author_name 'Hermann, Tobias S.' 'Klap\"otke, Thomas M.' 'Krumm, Burkhard' 'Stierstorfer, J\"org' _publ_section_title ; The energetic 3-trinitromethyl-5-nitramino-1H-1,2,4-triazole and nitrogen-rich salts ; _journal_issue 8 _journal_name_full 'New J. Chem.' _journal_page_first 3068 _journal_paper_doi 10.1039/C7NJ00695K _journal_volume 41 _journal_year 2017 _chemical_formula_moiety 'C3 H2 N8 O8' _chemical_formula_sum 'C3 H2 N8 O8' _chemical_formula_weight 278.13 _chemical_name_common 5-trinitromethyl-3-nitraminotriazole _chemical_name_systematic ; 5-trinitromethyl-3-nitraminotriazole ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _audit_creation_date ; 'Wed Oct 21 15:34:53 2015' ; _audit_creation_method SHELXL-2013 _audit_update_record ; 2016-08-31 deposited with the CCDC. 2017-03-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.110(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1597(7) _cell_length_b 10.5684(7) _cell_length_c 9.9433(7) _cell_measurement_reflns_used 2868 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 31.1480 _cell_measurement_theta_min 4.6330 _cell_volume 944.51(12) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 173(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9809 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -46.00 96.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 29.7932 -19.0000 60.0000 142 #__ type_ start__ end____ width___ exp.time_ 2 omega 53.00 81.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 29.7932 57.0000 0.0000 28 #__ type_ start__ end____ width___ exp.time_ 3 omega 40.00 109.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 29.7932 179.0000 -30.0000 69 #__ type_ start__ end____ width___ exp.time_ 4 omega -9.00 75.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 29.7932 -99.0000 -30.0000 84 #__ type_ start__ end____ width___ exp.time_ 5 omega 73.00 111.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 29.7932 -179.0000 -120.0000 38 #__ type_ start__ end____ width___ exp.time_ 6 omega -101.00 -3.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - -28.6994 -77.0000 60.0000 98 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0187817000 _diffrn_orient_matrix_UB_12 0.0055276000 _diffrn_orient_matrix_UB_13 -0.0656706000 _diffrn_orient_matrix_UB_21 -0.0073588000 _diffrn_orient_matrix_UB_22 -0.0664465000 _diffrn_orient_matrix_UB_23 -0.0088768000 _diffrn_orient_matrix_UB_31 -0.0762835000 _diffrn_orient_matrix_UB_32 0.0077825000 _diffrn_orient_matrix_UB_33 -0.0299429000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_av_unetI/netI 0.0193 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7214 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.498 _diffrn_reflns_theta_min 4.386 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_T_max 0.99999 _exptl_absorpt_correction_T_min 0.93286 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.956 _exptl_crystal_description block _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.344 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 1958 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0327 _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/[\s^2^(Fo^2^)+(0.0380P)^2^+0.3625P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.0836 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1746 _reflns_number_total 1958 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7nj00695k2.cif _cod_data_source_block kx389 _cod_depositor_comments 'Adding full bibliography for 7056071.cif.' _cod_original_sg_symbol_Hall ' -P 2yn' _cod_database_code 7056071 _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 0.963 _shelx_estimated_absorpt_t_max 0.981 _shelxl_version_number 2013-4 _shelx_res_file ; TITL V1 in P2(1)/n CELL 0.71073 9.1597 10.5684 9.9433 90.000 101.110 90.000 ZERR 4.00 0.0007 0.0007 0.0007 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 12 8 32 32 MERG 2 OMIT -2.00 53.00 EQIV $1 -x+1, -y, -z+1 EQIV $2 -x+1, -y, -z+2 HTAB N1 N2_$1 HTAB N4 N3_$2 HTAB N1 N2_$1 HTAB N4 N3_$2 FMAP 2 PLAN 20 SIZE 0.100 0.150 0.200 ACTA BOND $H CONF L.S. 5 TEMP -100.00 WGHT 0.038000 0.362500 FVAR 0.66256 O1 4 0.661397 -0.234533 0.737950 11.00000 0.04864 0.02939 = 0.02640 -0.00215 0.01779 0.00669 O2 4 0.664125 -0.304148 0.944595 11.00000 0.06545 0.02720 = 0.03206 0.00805 0.01754 0.01403 O3 4 0.539410 0.348855 0.527033 11.00000 0.04781 0.03844 = 0.03423 0.00815 0.01789 -0.00020 O4 4 0.307355 0.395129 0.525302 11.00000 0.03966 0.04537 = 0.03333 0.01129 -0.00651 0.00240 O5 4 0.289022 0.440274 0.808970 11.00000 0.04815 0.03235 = 0.04650 0.00158 0.01334 0.01714 O6 4 0.210952 0.247814 0.759062 11.00000 0.02761 0.04359 = 0.05494 0.00673 0.01184 -0.00034 O7 4 0.608050 0.477410 0.764593 11.00000 0.06841 0.03089 = 0.05188 0.00345 -0.00109 -0.01970 O8 4 0.608293 0.343118 0.929376 11.00000 0.04631 0.03963 = 0.02559 -0.00514 -0.00284 -0.00381 N1 3 0.535345 -0.014195 0.666103 11.00000 0.03319 0.02107 = 0.01671 -0.00132 0.00705 0.00289 N2 3 0.498854 0.103637 0.616967 11.00000 0.02812 0.02289 = 0.01828 0.00068 0.00492 0.00048 N3 3 0.502080 0.094860 0.844952 11.00000 0.02335 0.02126 = 0.01666 -0.00054 0.00311 0.00060 N4 3 0.566852 -0.118940 0.886913 11.00000 0.04102 0.02218 = 0.01739 0.00030 0.01044 0.00717 N5 3 0.634884 -0.226170 0.853835 11.00000 0.03420 0.02228 = 0.02369 -0.00092 0.00904 0.00161 N6 3 0.429150 0.354237 0.576934 11.00000 0.03702 0.02310 = 0.02393 0.00335 0.00286 -0.00262 N7 3 0.301595 0.332777 0.770101 11.00000 0.02886 0.03150 = 0.02941 0.00481 0.00667 0.00821 N8 3 0.567198 0.383087 0.815608 11.00000 0.03048 0.02236 = 0.03079 -0.00280 0.00188 -0.00144 C1 1 0.536925 -0.016976 0.800578 11.00000 0.02146 0.02240 = 0.01620 -0.00127 0.00386 -0.00038 C2 1 0.481436 0.164563 0.727792 11.00000 0.01889 0.02183 = 0.01766 0.00085 0.00255 -0.00134 C3 1 0.446893 0.302342 0.723157 11.00000 0.02417 0.02347 = 0.01910 0.00079 0.00237 0.00016 H1 2 0.550724 -0.073862 0.613792 11.00000 0.03038 H2 2 0.549198 -0.117033 0.968547 11.00000 0.03427 HKLF 4 REM V1 in P2(1)/n REM R1 = 0.0327 for 1746 Fo > 4sig(Fo) and 0.0373 for all 1958 data REM 180 parameters refined using 0 restraints END WGHT 0.0380 0.3626 REM Highest difference peak 0.344, deepest hole -0.334, 1-sigma level 0.052 Q1 1 0.4607 0.2316 0.7214 11.00000 0.05 0.34 Q2 1 0.5219 0.5024 0.7979 11.00000 0.05 0.26 Q3 1 0.4993 0.3380 0.7601 11.00000 0.05 0.25 Q4 1 0.4375 0.3244 0.6528 11.00000 0.05 0.24 Q5 1 0.4849 0.1389 0.7806 11.00000 0.05 0.23 Q6 1 0.3826 0.3154 0.7366 11.00000 0.05 0.21 Q7 1 0.5160 0.1419 0.6876 11.00000 0.05 0.20 Q8 1 0.5464 -0.0219 0.7445 11.00000 0.05 0.17 Q9 1 0.5505 -0.0688 0.8377 11.00000 0.05 0.16 Q10 1 0.4720 0.6240 0.7392 11.00000 0.05 0.15 Q11 1 0.5075 0.1172 0.9108 11.00000 0.05 0.14 Q12 1 0.4585 0.0979 0.8596 11.00000 0.05 0.14 Q13 1 0.7709 0.5804 0.8036 11.00000 0.05 0.13 Q14 1 0.5721 -0.3219 0.9153 11.00000 0.05 0.13 Q15 1 0.2762 0.1781 0.7501 11.00000 0.05 0.13 Q16 1 0.4784 0.0288 0.8162 11.00000 0.05 0.13 Q17 1 0.4041 0.1198 0.8460 11.00000 0.05 0.13 Q18 1 0.7238 -0.3427 0.8070 11.00000 0.05 0.12 Q19 1 0.7556 -0.2831 0.7351 11.00000 0.05 0.12 Q20 1 0.6726 -0.2583 0.6045 11.00000 0.05 0.12 ; _shelx_res_checksum 60105 loop_ _space_group_symop_operation_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_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 O1 O 0.66140(13) -0.23453(10) 0.73795(11) 0.0334(3) Uani 1 1 d O2 O 0.66412(15) -0.30415(11) 0.94459(11) 0.0405(3) Uani 1 1 d O3 O 0.53941(13) 0.34885(12) 0.52703(11) 0.0388(3) Uani 1 1 d O4 O 0.30735(13) 0.39513(12) 0.52530(11) 0.0413(3) Uani 1 1 d O5 O 0.28902(14) 0.44027(11) 0.80897(12) 0.0418(3) Uani 1 1 d O6 O 0.21095(12) 0.24781(12) 0.75906(13) 0.0415(3) Uani 1 1 d O7 O 0.60805(16) 0.47741(12) 0.76459(14) 0.0521(4) Uani 1 1 d O8 O 0.60829(13) 0.34312(12) 0.92938(11) 0.0385(3) Uani 1 1 d N1 N 0.53535(13) -0.01420(12) 0.66610(12) 0.0234(3) Uani 1 1 d N2 N 0.49885(13) 0.10364(11) 0.61697(11) 0.0230(3) Uani 1 1 d N3 N 0.50208(12) 0.09486(11) 0.84495(11) 0.0205(3) Uani 1 1 d N4 N 0.56685(14) -0.11894(11) 0.88691(12) 0.0262(3) Uani 1 1 d N5 N 0.63488(14) -0.22617(11) 0.85383(12) 0.0263(3) Uani 1 1 d N6 N 0.42915(14) 0.35424(12) 0.57693(13) 0.0284(3) Uani 1 1 d N7 N 0.30160(14) 0.33278(13) 0.77010(13) 0.0298(3) Uani 1 1 d N8 N 0.56720(14) 0.38309(12) 0.81561(13) 0.0284(3) Uani 1 1 d C1 C 0.53693(14) -0.01698(13) 0.80058(13) 0.0200(3) Uani 1 1 d C2 C 0.48144(14) 0.16456(13) 0.72779(13) 0.0196(3) Uani 1 1 d C3 C 0.44689(15) 0.30234(13) 0.72316(13) 0.0225(3) Uani 1 1 d H1 H 0.5507(19) -0.0739(18) 0.6138(19) 0.030(4) Uiso 1 1 d H2 H 0.549(2) -0.1170(17) 0.969(2) 0.034(5) Uiso 1 1 d loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0486(7) 0.0294(6) 0.0264(5) -0.0021(4) 0.0178(5) 0.0067(5) O2 0.0655(8) 0.0272(6) 0.0321(6) 0.0081(5) 0.0175(6) 0.0140(5) O3 0.0478(7) 0.0384(7) 0.0342(6) 0.0082(5) 0.0179(5) -0.0002(5) O4 0.0397(7) 0.0454(7) 0.0333(6) 0.0113(5) -0.0065(5) 0.0024(5) O5 0.0482(7) 0.0323(6) 0.0465(7) 0.0016(6) 0.0133(6) 0.0171(5) O6 0.0276(6) 0.0436(7) 0.0549(8) 0.0067(6) 0.0118(5) -0.0003(5) O7 0.0684(9) 0.0309(7) 0.0519(8) 0.0034(6) -0.0011(7) -0.0197(6) O8 0.0463(7) 0.0396(7) 0.0256(5) -0.0051(5) -0.0028(5) -0.0038(5) N1 0.0332(6) 0.0211(6) 0.0167(6) -0.0013(5) 0.0071(5) 0.0029(5) N2 0.0281(6) 0.0229(6) 0.0183(5) 0.0007(5) 0.0049(5) 0.0005(5) N3 0.0233(6) 0.0213(6) 0.0167(5) -0.0005(4) 0.0031(4) 0.0006(4) N4 0.0410(7) 0.0222(6) 0.0174(6) 0.0003(5) 0.0104(5) 0.0072(5) N5 0.0342(6) 0.0223(6) 0.0237(6) -0.0009(5) 0.0090(5) 0.0016(5) N6 0.0370(7) 0.0231(6) 0.0239(6) 0.0033(5) 0.0029(5) -0.0026(5) N7 0.0289(7) 0.0315(7) 0.0294(6) 0.0048(6) 0.0067(5) 0.0082(5) N8 0.0305(7) 0.0224(6) 0.0308(7) -0.0028(5) 0.0019(5) -0.0014(5) C1 0.0215(6) 0.0224(7) 0.0162(6) -0.0013(5) 0.0039(5) -0.0004(5) C2 0.0189(6) 0.0218(7) 0.0177(6) 0.0008(5) 0.0026(5) -0.0013(5) C3 0.0242(7) 0.0235(7) 0.0191(6) 0.0008(5) 0.0024(5) 0.0002(5) 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 C1 N1 N2 109.61(11) C1 N1 H1 128.9(12) N2 N1 H1 121.4(12) C2 N2 N1 102.09(11) C1 N3 C2 101.59(11) N5 N4 C1 123.18(12) N5 N4 H2 115.2(12) C1 N4 H2 121.5(12) O2 N5 O1 126.51(13) O2 N5 N4 115.51(12) O1 N5 N4 117.98(12) O3 N6 O4 127.96(13) O3 N6 C3 115.34(12) O4 N6 C3 116.69(12) O5 N7 O6 128.08(13) O5 N7 C3 115.89(13) O6 N7 C3 115.97(12) O8 N8 O7 128.31(14) O8 N8 C3 115.11(12) O7 N8 C3 116.57(12) N3 C1 N1 110.97(12) N3 C1 N4 121.69(12) N1 C1 N4 127.33(12) N2 C2 N3 115.73(12) N2 C2 C3 120.89(12) N3 C2 C3 123.35(12) C2 C3 N7 112.90(11) C2 C3 N6 111.24(11) N7 C3 N6 105.97(11) C2 C3 N8 113.45(11) N7 C3 N8 105.36(11) N6 C3 N8 107.41(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N5 1.2257(15) O2 N5 1.2133(16) O3 N6 1.2094(17) O4 N6 1.2142(17) O5 N7 1.2126(18) O6 N7 1.2135(17) O7 N8 1.2100(17) O8 N8 1.1982(17) N1 C1 1.3347(17) N1 N2 1.3558(16) N1 H1 0.85(2) N2 C2 1.3123(17) N3 C1 1.3220(17) N3 C2 1.3604(17) N4 N5 1.3637(17) N4 C1 1.3721(18) N4 H2 0.858(19) N6 C3 1.5330(18) N7 C3 1.5271(18) N8 C3 1.5483(18) C2 C3 1.4889(19) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N2 0.85(2) 2.273(19) 2.9282(17) 134.3(15) 3_656 N4 H2 N3 0.858(19) 2.01(2) 2.8671(17) 174.0(17) 3_657 N1 H1 N2 0.85(2) 2.273(19) 2.9282(17) 134.3(15) 3_656 N4 H2 N3 0.858(19) 2.01(2) 2.8671(17) 174.0(17) 3_657 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 C1 N1 N2 C2 0.28(14) C1 N4 N5 O2 174.55(13) C1 N4 N5 O1 -4.9(2) C2 N3 C1 N1 -0.69(15) C2 N3 C1 N4 -179.62(12) N2 N1 C1 N3 0.28(16) N2 N1 C1 N4 179.14(13) N5 N4 C1 N3 -164.68(13) N5 N4 C1 N1 16.6(2) N1 N2 C2 N3 -0.77(15) N1 N2 C2 C3 177.04(12) C1 N3 C2 N2 0.93(15) C1 N3 C2 C3 -176.82(12) N2 C2 C3 N7 121.62(13) N3 C2 C3 N7 -60.75(17) N2 C2 C3 N6 2.63(17) N3 C2 C3 N6 -179.74(11) N2 C2 C3 N8 -118.60(13) N3 C2 C3 N8 59.03(17) O5 N7 C3 C2 158.14(12) O6 N7 C3 C2 -24.50(17) O5 N7 C3 N6 -79.86(14) O6 N7 C3 N6 97.50(14) O5 N7 C3 N8 33.80(15) O6 N7 C3 N8 -148.84(12) O3 N6 C3 C2 -63.36(16) O4 N6 C3 C2 116.45(14) O3 N6 C3 N7 173.58(12) O4 N6 C3 N7 -6.61(16) O3 N6 C3 N8 61.34(15) O4 N6 C3 N8 -118.85(13) O8 N8 C3 C2 -46.76(17) O7 N8 C3 C2 133.00(14) O8 N8 C3 N7 77.23(15) O7 N8 C3 N7 -103.02(15) O8 N8 C3 N6 -170.11(12) O7 N8 C3 N6 9.64(17)