#------------------------------------------------------------------------------ #$Date: 2018-01-10 07:45:33 +0200 (Wed, 10 Jan 2018) $ #$Revision: 205019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229934.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_7229934 loop_ _publ_author_name 'Yang, Wei' 'Lu, Huanchang' 'Liao, Longyu' 'Fan, Guijuan' 'Ma, Qing' 'Huang, Jinglun' _publ_section_title ; Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials ; _journal_issue 4 _journal_name_full 'RSC Advances' _journal_page_first 2203 _journal_paper_doi 10.1039/C7RA13346D _journal_volume 8 _journal_year 2018 _chemical_formula_sum 'C8 H2 N14 O4' _chemical_formula_weight 358.24 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2017-05-25 deposited with the CCDC. 2018-01-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.222(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5557(18) _cell_length_b 11.6416(19) _cell_length_c 11.1129(17) _cell_measurement_reflns_used 1571 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 46.558 _cell_measurement_theta_min 5.262 _cell_volume 1341.1(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_unetI/netI 0.0369 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7543 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.496 _diffrn_reflns_theta_min 1.964 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.774 _exptl_crystal_description prismatic _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.249 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2497 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0468 _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^)+(0.0555P)^2^+0.3625P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1089 _refine_ls_wR_factor_ref 0.1174 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1946 _reflns_number_total 2497 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra13346d2.cif _cod_data_source_block cd16194 _cod_database_code 7229934 _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 0.974 _shelx_estimated_absorpt_t_max 0.981 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd16194 in P2(1)/c CELL 0.71073 11.5557 11.6416 11.1129 90.000 116.222 90.000 ZERR 4.00 0.0018 0.0019 0.0017 0.000 0.003 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 32 8 56 16 OMIT -3.00 51.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 wpdb -1 size 0.18 0.16 0.13 mpla c7 c8 n12 n13 n14 mpla c1 > c6 htab conf WGHT 0.055500 0.362500 FVAR 0.17306 MOLE 1 O1 4 0.535016 1.030174 0.163385 11.00000 0.07729 0.07242 = 0.04733 0.00151 0.03587 -0.01984 O2 4 0.633973 1.103279 0.358457 11.00000 0.05548 0.04285 = 0.06766 -0.00677 0.02732 -0.01507 O3 4 0.682178 0.650576 0.584738 11.00000 0.05118 0.06310 = 0.07770 0.01105 0.01865 0.02542 O4 4 0.625115 0.747316 0.713566 11.00000 0.07203 0.08067 = 0.03327 0.00858 0.01383 0.00395 N1 3 0.304046 0.999244 0.168657 11.00000 0.03392 0.04625 = 0.04390 0.01251 0.01639 0.00535 N2 3 0.197988 1.031217 0.158282 11.00000 0.04365 0.04724 = 0.04120 0.01019 0.01365 0.00728 N3 3 0.101831 1.069531 0.135042 11.00000 0.05395 0.09191 = 0.08231 0.03109 0.02723 0.03365 N4 3 0.562547 1.032735 0.281506 11.00000 0.03454 0.03706 = 0.04037 -0.00233 0.01954 -0.00233 N5 3 0.725993 0.889538 0.521183 11.00000 0.02512 0.06017 = 0.04072 0.00587 0.01068 -0.00601 N6 3 0.791044 0.923460 0.464697 11.00000 0.02575 0.05309 = 0.04648 0.00382 0.01189 -0.00262 N7 3 0.862296 0.951241 0.428987 11.00000 0.03728 0.09149 = 0.07380 0.01222 0.02919 -0.00447 N8 3 0.620905 0.724595 0.605351 11.00000 0.02825 0.04508 = 0.04115 0.00534 0.00927 -0.00193 N9 3 0.364605 0.682748 0.487888 11.00000 0.03194 0.03967 = 0.03491 0.00320 0.01083 -0.00517 N10 3 0.266088 0.629413 0.414792 11.00000 0.03574 0.03539 = 0.04260 0.00503 0.01989 -0.00086 N11 3 0.181149 0.571660 0.364972 11.00000 0.04721 0.04793 = 0.06697 0.00625 0.01395 -0.01366 N12 3 0.191256 0.818136 0.258884 11.00000 0.02410 0.03748 = 0.03367 0.00012 0.01096 -0.00027 N13 3 0.116592 0.846387 0.321644 11.00000 0.02842 0.05471 = 0.04820 -0.00215 0.01860 0.00342 N14 3 -0.002167 0.765480 0.120100 11.00000 0.02982 0.06734 = 0.05370 -0.00105 0.00653 -0.00963 C1 1 0.377326 0.925815 0.275294 11.00000 0.03105 0.03243 = 0.02679 -0.00150 0.01230 0.00257 C2 1 0.510927 0.942908 0.335611 11.00000 0.03059 0.03188 = 0.03162 -0.00261 0.01739 -0.00291 C3 1 0.592455 0.878560 0.445568 11.00000 0.02769 0.03793 = 0.03133 -0.00399 0.01449 -0.00163 C4 1 0.535895 0.795297 0.491277 11.00000 0.02728 0.03604 = 0.02901 0.00129 0.01139 0.00300 C5 1 0.404982 0.771633 0.430329 11.00000 0.02900 0.03341 = 0.03042 -0.00153 0.01574 -0.00030 C6 1 0.326015 0.839059 0.321392 11.00000 0.02378 0.03190 = 0.03008 -0.00131 0.01145 -0.00026 C7 1 0.003073 0.812908 0.233091 11.00000 0.02745 0.06612 = 0.06475 0.00195 0.01964 0.00105 AFIX 43 H7 2 -0.070110 0.821268 0.247072 11.00000 -1.20000 AFIX 0 C8 1 0.117009 0.769933 0.139778 11.00000 0.03286 0.05148 = 0.03678 -0.00338 0.00848 -0.00744 AFIX 43 H8 2 0.146879 0.743388 0.079652 11.00000 -1.20000 AFIX 0 HKLF 4 REM cd16194 in P2(1)/c REM R1 = 0.0468 for 1946 Fo > 4sig(Fo) and 0.0620 for all 2497 data REM 235 parameters refined using 0 restraints END WGHT 0.0550 0.3485 REM Instructions for potential hydrogen bonds EQIV $1 x-1, -y+3/2, z-1/2 HTAB C7 O3_$1 REM Highest difference peak 0.249, deepest hole -0.181, 1-sigma level 0.046 Q1 1 0.3642 0.8599 0.2752 11.00000 0.05 0.25 Q2 1 0.4404 0.9514 0.3256 11.00000 0.05 0.24 Q3 1 0.6196 0.6219 0.5996 11.00000 0.05 0.22 Q4 1 0.5404 0.9342 0.4153 11.00000 0.05 0.21 Q5 1 0.2664 0.8237 0.2922 11.00000 0.05 0.20 Q6 1 0.5584 0.8212 0.4385 11.00000 0.05 0.20 Q7 1 0.6562 0.8892 0.4776 11.00000 0.05 0.20 Q8 1 0.4425 1.0596 0.1796 11.00000 0.05 0.19 Q9 1 0.6349 1.0854 0.2671 11.00000 0.05 0.19 Q10 1 0.3321 0.9284 0.3258 11.00000 0.05 0.19 Q11 1 0.6808 0.7704 0.6834 11.00000 0.05 0.18 Q12 1 0.4722 0.8140 0.5003 11.00000 0.05 0.18 Q13 1 0.5799 1.0929 0.1269 11.00000 0.05 0.17 Q14 1 0.3792 1.0575 0.1804 11.00000 0.05 0.17 Q15 1 0.4634 0.7769 0.4467 11.00000 0.05 0.17 Q16 1 0.4181 0.6408 0.5648 11.00000 0.05 0.16 Q17 1 0.3365 0.9349 0.2046 11.00000 0.05 0.16 Q18 1 0.3631 0.7817 0.3484 11.00000 0.05 0.16 Q19 1 0.3592 0.8165 0.3818 11.00000 0.05 0.16 Q20 1 0.1410 0.8702 0.2689 11.00000 0.05 0.16 ; _shelx_res_checksum 29124 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1 O 0.53502(19) 1.03017(17) 0.16339(18) 0.0626(6) Uani 1 1 d . . O2 O 0.63397(17) 1.10328(16) 0.35846(19) 0.0553(5) Uani 1 1 d . . O3 O 0.68218(18) 0.65058(18) 0.5847(2) 0.0676(6) Uani 1 1 d . . O4 O 0.62511(18) 0.74732(19) 0.71357(17) 0.0654(6) Uani 1 1 d . . N1 N 0.30405(18) 0.99924(17) 0.16866(19) 0.0416(5) Uani 1 1 d . . N2 N 0.1980(2) 1.03122(18) 0.15828(19) 0.0459(5) Uani 1 1 d . . N3 N 0.1018(2) 1.0695(3) 0.1350(3) 0.0771(8) Uani 1 1 d . . N4 N 0.56255(17) 1.03274(16) 0.28151(19) 0.0362(4) Uani 1 1 d . . N5 N 0.72599(17) 0.88954(18) 0.52118(19) 0.0434(5) Uani 1 1 d . . N6 N 0.79104(17) 0.92346(18) 0.46470(19) 0.0433(5) Uani 1 1 d . . N7 N 0.8623(2) 0.9512(2) 0.4290(2) 0.0658(7) Uani 1 1 d . . N8 N 0.62090(17) 0.72459(18) 0.60535(19) 0.0404(5) Uani 1 1 d . . N9 N 0.36461(17) 0.68275(16) 0.48789(17) 0.0369(4) Uani 1 1 d . . N10 N 0.26609(18) 0.62941(16) 0.41479(19) 0.0370(4) Uani 1 1 d . . N11 N 0.1811(2) 0.5717(2) 0.3650(2) 0.0582(6) Uani 1 1 d . . N12 N 0.19126(15) 0.81814(16) 0.25888(17) 0.0324(4) Uani 1 1 d . . N13 N 0.11659(17) 0.84639(18) 0.32164(19) 0.0432(5) Uani 1 1 d . . N14 N -0.00217(18) 0.7655(2) 0.1201(2) 0.0546(6) Uani 1 1 d . . C1 C 0.37733(19) 0.92582(18) 0.27529(19) 0.0303(5) Uani 1 1 d . . C2 C 0.51093(19) 0.94291(18) 0.3356(2) 0.0300(5) Uani 1 1 d . . C3 C 0.59245(19) 0.87856(19) 0.4456(2) 0.0318(5) Uani 1 1 d . . C4 C 0.53589(19) 0.79530(18) 0.49128(19) 0.0312(5) Uani 1 1 d . . C5 C 0.40498(19) 0.77163(18) 0.43033(19) 0.0300(5) Uani 1 1 d . . C6 C 0.32601(18) 0.83906(18) 0.3214(2) 0.0287(5) Uani 1 1 d . . C7 C 0.0031(2) 0.8129(2) 0.2331(3) 0.0530(7) Uani 1 1 d . . H7 H -0.0701 0.8213 0.2471 0.064 Uiso 1 1 calc R U C8 C 0.1170(2) 0.7699(2) 0.1398(2) 0.0429(6) Uani 1 1 d . . H8 H 0.1469 0.7434 0.0797 0.051 Uiso 1 1 calc R U 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 0.0773(14) 0.0724(14) 0.0473(11) 0.0015(9) 0.0359(10) -0.0198(10) O2 0.0555(11) 0.0428(11) 0.0677(12) -0.0068(9) 0.0273(10) -0.0151(9) O3 0.0512(11) 0.0631(13) 0.0777(14) 0.0111(10) 0.0187(10) 0.0254(10) O4 0.0720(13) 0.0807(15) 0.0333(10) 0.0086(9) 0.0138(9) 0.0039(11) N1 0.0339(11) 0.0462(12) 0.0439(11) 0.0125(9) 0.0164(9) 0.0053(9) N2 0.0436(13) 0.0472(13) 0.0412(12) 0.0102(9) 0.0136(10) 0.0073(10) N3 0.0540(15) 0.092(2) 0.0823(19) 0.0311(15) 0.0272(14) 0.0337(15) N4 0.0345(10) 0.0371(11) 0.0404(11) -0.0023(9) 0.0195(9) -0.0023(8) N5 0.0251(9) 0.0602(13) 0.0407(11) 0.0059(9) 0.0107(9) -0.0060(9) N6 0.0258(10) 0.0531(13) 0.0465(12) 0.0038(9) 0.0119(9) -0.0026(9) N7 0.0373(12) 0.091(2) 0.0738(17) 0.0122(14) 0.0292(12) -0.0045(12) N8 0.0282(10) 0.0451(12) 0.0411(12) 0.0053(9) 0.0093(9) -0.0019(9) N9 0.0319(10) 0.0397(11) 0.0349(10) 0.0032(8) 0.0108(8) -0.0052(8) N10 0.0357(11) 0.0354(11) 0.0426(11) 0.0050(9) 0.0199(9) -0.0009(9) N11 0.0472(13) 0.0479(14) 0.0670(15) 0.0062(11) 0.0140(12) -0.0137(11) N12 0.0241(9) 0.0375(11) 0.0337(10) 0.0001(8) 0.0110(8) -0.0003(7) N13 0.0284(10) 0.0547(13) 0.0482(12) -0.0022(9) 0.0186(9) 0.0034(9) N14 0.0298(11) 0.0673(16) 0.0537(14) -0.0010(11) 0.0065(10) -0.0096(10) C1 0.0310(11) 0.0324(12) 0.0268(11) -0.0015(8) 0.0123(9) 0.0026(9) C2 0.0306(11) 0.0319(11) 0.0316(11) -0.0026(9) 0.0174(9) -0.0029(9) C3 0.0277(11) 0.0379(12) 0.0313(11) -0.0040(9) 0.0145(9) -0.0016(9) C4 0.0273(11) 0.0360(12) 0.0290(11) 0.0013(9) 0.0114(9) 0.0030(9) C5 0.0290(10) 0.0334(12) 0.0304(11) -0.0015(9) 0.0157(9) -0.0003(9) C6 0.0238(10) 0.0319(11) 0.0301(10) -0.0013(9) 0.0114(9) -0.0003(9) C7 0.0275(12) 0.0661(19) 0.0648(17) 0.0019(14) 0.0196(12) 0.0010(11) C8 0.0329(12) 0.0515(16) 0.0368(13) -0.0034(11) 0.0085(10) -0.0074(10) 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 N2 N1 C1 117.77(18) N3 N2 N1 170.4(3) O1 N4 O2 123.7(2) O1 N4 C2 118.12(18) O2 N4 C2 118.09(18) N6 N5 C3 118.71(18) N7 N6 N5 171.2(2) O3 N8 O4 125.3(2) O3 N8 C4 117.7(2) O4 N8 C4 117.0(2) N10 N9 C5 117.87(18) N11 N10 N9 169.8(2) C8 N12 N13 109.34(17) C8 N12 C6 129.82(18) N13 N12 C6 120.83(16) C7 N13 N12 101.20(19) C8 N14 C7 102.7(2) C6 C1 C2 119.38(19) C6 C1 N1 124.21(19) C2 C1 N1 116.41(19) C3 C2 C1 121.42(19) C3 C2 N4 120.53(18) C1 C2 N4 118.04(18) C4 C3 C2 117.01(18) C4 C3 N5 114.68(19) C2 C3 N5 128.3(2) C5 C4 C3 123.40(19) C5 C4 N8 118.76(18) C3 C4 N8 117.75(18) C4 C5 C6 117.89(19) C4 C5 N9 115.85(18) C6 C5 N9 126.24(18) C1 C6 C5 120.77(18) C1 C6 N12 120.20(18) C5 C6 N12 119.02(18) N13 C7 N14 116.2(2) N13 C7 H7 121.9 N14 C7 H7 121.9 N14 C8 N12 110.6(2) N14 C8 H8 124.7 N12 C8 H8 124.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N4 1.207(2) O2 N4 1.210(2) O3 N8 1.200(3) O4 N8 1.211(2) N1 N2 1.237(3) N1 C1 1.402(3) N2 N3 1.117(3) N4 C2 1.459(3) N5 N6 1.238(3) N5 C3 1.399(3) N6 N7 1.109(3) N8 C4 1.466(3) N9 N10 1.235(3) N9 C5 1.400(3) N10 N11 1.114(3) N12 C8 1.341(3) N12 N13 1.368(2) N12 C6 1.418(3) N13 C7 1.304(3) N14 C8 1.297(3) N14 C7 1.348(3) C1 C6 1.379(3) C1 C2 1.399(3) C2 C3 1.387(3) C3 C4 1.385(3) C4 C5 1.385(3) C5 C6 1.392(3) C7 H7 0.9300 C8 H8 0.9300 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 C5 N9 N10 N11 176.4(13) C8 N12 N13 C7 -0.4(3) C6 N12 N13 C7 -179.4(2) N2 N1 C1 C6 37.8(3) N2 N1 C1 C2 -143.0(2) C6 C1 C2 C3 -3.5(3) N1 C1 C2 C3 177.3(2) C6 C1 C2 N4 177.90(18) N1 C1 C2 N4 -1.3(3) O1 N4 C2 C3 126.8(2) O2 N4 C2 C3 -50.7(3) O1 N4 C2 C1 -54.6(3) O2 N4 C2 C1 127.8(2) C1 C2 C3 C4 1.2(3) N4 C2 C3 C4 179.70(18) C1 C2 C3 N5 -176.1(2) N4 C2 C3 N5 2.5(3) N6 N5 C3 C4 151.4(2) N6 N5 C3 C2 -31.4(3) C2 C3 C4 C5 2.2(3) N5 C3 C4 C5 179.83(19) C2 C3 C4 N8 178.55(19) N5 C3 C4 N8 -3.8(3) O3 N8 C4 C5 101.1(2) O4 N8 C4 C5 -80.2(3) O3 N8 C4 C3 -75.4(3) O4 N8 C4 C3 103.3(2) C3 C4 C5 C6 -3.1(3) N8 C4 C5 C6 -179.42(19) C3 C4 C5 N9 178.50(19) N8 C4 C5 N9 2.2(3) N10 N9 C5 C4 -152.95(19) N10 N9 C5 C6 28.9(3) C2 C1 C6 C5 2.6(3) N1 C1 C6 C5 -178.27(19) C2 C1 C6 N12 -178.06(18) N1 C1 C6 N12 1.1(3) C4 C5 C6 C1 0.6(3) N9 C5 C6 C1 178.80(19) C4 C5 C6 N12 -178.73(18) N9 C5 C6 N12 -0.6(3) C8 N12 C6 C1 73.4(3) N13 N12 C6 C1 -107.8(2) C8 N12 C6 C5 -107.3(3) N13 N12 C6 C5 71.5(3) N12 N13 C7 N14 0.3(3) C8 N14 C7 N13 -0.1(3) C7 N14 C8 N12 -0.2(3) N13 N12 C8 N14 0.4(3) C6 N12 C8 N14 179.3(2)