#------------------------------------------------------------------------------ #$Date: 2026-06-27 02:19:08 +0100 (Sat, 27 Jun 2026) $ #$Revision: 306667 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/44/7064455.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_7064455 loop_ _publ_author_name 'Dogra, Sunanda' 'Harsha, Priyasha' 'Roy Choudhury, Angshuman' _publ_section_title ; Mechanical Behaviour Modulation through Substituent Reversal in Schiff Base Molecular Crystals ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D6NJ01952H _journal_year 2026 _chemical_formula_moiety 'C14 H9 N3 O2' _chemical_formula_sum 'C14 H9 N3 O2' _chemical_formula_weight 251.24 _chemical_name_systematic E24-LT _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 geom _atom_sites_solution_primary dual _audit_creation_date 2026-05-02 _audit_creation_method ; Olex2 1.5 (compiled 2026.04.10 svn.r48fbca5a for OlexSys, GUI svn.r7537) ; _audit_update_record ; 2026-05-20 deposited with the CCDC. 2026-06-26 downloaded from the CCDC. ; _cell_angle_alpha 84.812(5) _cell_angle_beta 77.336(5) _cell_angle_gamma 78.531(4) _cell_formula_units_Z 2 _cell_length_a 7.3161(4) _cell_length_b 8.5269(5) _cell_length_c 10.0286(6) _cell_measurement_reflns_used 2228 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 25.2580 _cell_measurement_theta_min 3.1900 _cell_volume 597.49(6) _computing_cell_refinement 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -69.00 118.20 0.30 10.00 -- 29.89 54.00 30.00 624 2 \w -69.00 118.20 0.30 10.00 -- 29.89 54.00-180.00 624 3 \w 77.00 102.80 0.30 10.00 -- 29.89 54.00-180.00 86 4 \w 27.00 114.00 0.30 10.00 -- 29.89 54.00 -90.00 290 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0336471000 _diffrn_orient_matrix_UB_12 -0.0573945000 _diffrn_orient_matrix_UB_13 0.0502668000 _diffrn_orient_matrix_UB_21 0.0952857000 _diffrn_orient_matrix_UB_22 -0.0384648000 _diffrn_orient_matrix_UB_23 0.0001928000 _diffrn_orient_matrix_UB_31 0.0030548000 _diffrn_orient_matrix_UB_32 0.0494779000 _diffrn_orient_matrix_UB_33 0.0523535000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_unetI/netI 0.0237 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4828 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.349 _diffrn_reflns_theta_min 2.903 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear whiteish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whiteish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.396 _exptl_crystal_description block _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.299 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2178 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0461 _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^)+(0.0785P)^2^+0.1258P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1210 _refine_ls_wR_factor_ref 0.1324 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1878 _reflns_number_total 2178 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj01952h2.cif _cod_data_source_block e24-lt _cod_original_cell_volume 597.50(6) _cod_database_code 7064455 _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. ; _cell_oxdiff_angle_alpha 84.812(5) _cell_oxdiff_angle_beta 77.336(5) _cell_oxdiff_angle_gamma 78.531(4) _cell_oxdiff_length_a 7.3161(4) _cell_oxdiff_length_b 8.5269(5) _cell_oxdiff_length_c 10.0286(6) _cell_oxdiff_measurement_reflns_used 2228 _cell_oxdiff_volume 597.49(6) _shelx_estimated_absorpt_t_max 0.981 _shelx_estimated_absorpt_t_min 0.971 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C13(H13), C9(H9), C10(H10), C12(H12), C7(H7), C1(H1), C6(H6), C3(H3), C4(H4) ; _shelx_res_file ; TITL e24-lt_a.res in P-1 e24-lt.res created by SHELXL-2018/3 at 11:54:14 on 02-May-2026 REM Old TITL E24-LT in P-1 REM SHELXT solution in P-1: R1 0.155, Rweak 0.002, Alpha 0.015 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N2 O2 CELL 0.71073 7.3161 8.5269 10.0286 84.812 77.336 78.531 ZERR 2 0.0004 0.0005 0.0006 0.005 0.005 0.004 LATT 1 SFAC C H N O UNIT 28 18 6 4 L.S. 10 PLAN 10 SIZE 0.2 0.3 0.2 TEMP -173.15 CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.078500 0.125800 FVAR 0.85219 O1 4 0.851788 -0.397146 0.428738 11.00000 0.04713 0.02030 = 0.03298 -0.00198 -0.00930 -0.00301 O2 4 1.004474 -0.272150 0.255322 11.00000 0.03390 0.03571 = 0.03198 -0.01544 0.00509 -0.00766 N1 3 0.482501 0.324806 0.744501 11.00000 0.02548 0.01916 = 0.02232 -0.00361 -0.00458 -0.00281 N2 3 0.895970 -0.274170 0.367816 11.00000 0.02427 0.02651 = 0.02475 -0.00703 -0.00663 -0.00209 N3 3 0.215905 1.032353 1.057482 11.00000 0.02925 0.02626 = 0.03752 -0.00937 -0.00471 -0.00382 C8 1 0.429496 0.473542 0.807811 11.00000 0.02875 0.01699 = 0.01807 0.00045 -0.00498 -0.00272 C13 1 0.236385 0.530307 0.861009 11.00000 0.02591 0.02173 = 0.02101 -0.00109 -0.00446 -0.00638 AFIX 43 H13 2 0.143776 0.469724 0.853076 11.00000 -1.20000 AFIX 0 C2 1 0.676015 0.162287 0.563335 11.00000 0.02073 0.02260 = 0.02122 -0.00243 -0.00656 -0.00378 C11 1 0.317656 0.760855 0.939365 11.00000 0.03003 0.01793 = 0.01734 -0.00158 -0.00437 -0.00235 C9 1 0.566905 0.559716 0.824116 11.00000 0.02602 0.02140 = 0.02017 -0.00044 -0.00351 -0.00256 AFIX 43 H9 2 0.698196 0.520193 0.789631 11.00000 -1.20000 AFIX 0 C10 1 0.511555 0.702496 0.890469 11.00000 0.02698 0.02140 = 0.01945 0.00012 -0.00464 -0.00622 AFIX 43 H10 2 0.604589 0.760342 0.902672 11.00000 -1.20000 AFIX 0 C12 1 0.179714 0.674250 0.925102 11.00000 0.02613 0.02266 = 0.02041 -0.00184 -0.00407 -0.00234 AFIX 43 H12 2 0.048365 0.714016 0.959149 11.00000 -1.20000 AFIX 0 C7 1 0.788696 0.161756 0.431924 11.00000 0.02412 0.02180 = 0.02208 -0.00037 -0.00558 -0.00457 AFIX 43 H7 2 0.816664 0.259860 0.387241 11.00000 -1.20000 AFIX 0 C1 1 0.603962 0.314914 0.631840 11.00000 0.02479 0.02001 = 0.02089 -0.00068 -0.00656 -0.00435 AFIX 43 H1 2 0.649430 0.408455 0.590774 11.00000 -1.20000 AFIX 0 C6 1 0.860969 0.019213 0.365103 11.00000 0.02273 0.02776 = 0.01792 -0.00312 -0.00263 -0.00489 AFIX 43 H6 2 0.937399 0.018078 0.275298 11.00000 -1.20000 AFIX 0 C3 1 0.634862 0.017867 0.630477 11.00000 0.01996 0.02505 = 0.01799 -0.00184 -0.00295 -0.00328 AFIX 43 H3 2 0.558940 0.018005 0.720427 11.00000 -1.20000 AFIX 0 C4 1 0.705009 -0.124809 0.565507 11.00000 0.02435 0.02051 = 0.02254 0.00021 -0.00640 -0.00530 AFIX 43 H4 2 0.677103 -0.223267 0.609448 11.00000 -1.20000 AFIX 0 C5 1 0.817041 -0.120650 0.434695 11.00000 0.01917 0.02200 = 0.02367 -0.00631 -0.00690 -0.00029 C14 1 0.260869 0.911372 1.005769 11.00000 0.02475 0.02391 = 0.02386 -0.00228 -0.00435 -0.00445 HKLF 4 REM e24-lt_a.res in P-1 REM wR2 = 0.1324, GooF = S = 1.080, Restrained GooF = 1.080 for all data REM R1 = 0.0461 for 1878 Fo > 4sig(Fo) and 0.0534 for all 2178 data REM 172 parameters refined using 0 restraints END WGHT 0.0785 0.1258 REM Highest difference peak 0.299, deepest hole -0.280, 1-sigma level 0.057 Q1 1 1.0629 -0.4186 0.1851 11.00000 0.05 0.23 Q2 1 0.9094 -0.5349 0.3662 11.00000 0.05 0.23 Q3 1 0.4761 0.5362 0.7809 11.00000 0.05 0.19 Q4 1 0.3784 0.7415 0.9215 11.00000 0.05 0.18 Q5 1 -0.0276 0.5563 0.7522 11.00000 0.05 0.17 Q6 1 0.1069 0.4997 0.8234 11.00000 0.05 0.16 Q7 1 0.3748 0.2505 0.7403 11.00000 0.05 0.16 Q8 1 1.0882 -0.1859 0.2457 11.00000 0.05 0.16 Q9 1 0.5993 -0.3837 0.5957 11.00000 0.05 0.16 Q10 1 0.6401 0.4396 0.5476 11.00000 0.05 0.15 ; _shelx_res_checksum 56533 _olex2_submission_original_sample_id E24-LT _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.524 _oxdiff_exptl_absorpt_empirical_full_min 0.781 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 0.85179(16) -0.39715(12) 0.42874(11) 0.0337(3) Uani 1 1 d . . . . . O2 O 1.00447(15) -0.27215(14) 0.25532(11) 0.0347(3) Uani 1 1 d . . . . . N1 N 0.48250(16) 0.32481(14) 0.74450(12) 0.0224(3) Uani 1 1 d . . . . . N2 N 0.89597(17) -0.27417(15) 0.36782(12) 0.0249(3) Uani 1 1 d . . . . . N3 N 0.21590(18) 1.03235(15) 1.05748(14) 0.0310(3) Uani 1 1 d . . . . . C8 C 0.4295(2) 0.47354(17) 0.80781(14) 0.0215(3) Uani 1 1 d . . . . . C13 C 0.2364(2) 0.53031(17) 0.86101(13) 0.0227(3) Uani 1 1 d . . . . . H13 H 0.143776 0.469724 0.853076 0.027 Uiso 1 1 calc R U . . . C2 C 0.67602(19) 0.16229(17) 0.56334(14) 0.0211(3) Uani 1 1 d . . . . . C11 C 0.3177(2) 0.76085(16) 0.93937(14) 0.0221(3) Uani 1 1 d . . . . . C9 C 0.5669(2) 0.55972(17) 0.82412(14) 0.0230(3) Uani 1 1 d . . . . . H9 H 0.698196 0.520193 0.789631 0.028 Uiso 1 1 calc R U . . . C10 C 0.5116(2) 0.70250(17) 0.89047(13) 0.0225(3) Uani 1 1 d . . . . . H10 H 0.604589 0.760342 0.902672 0.027 Uiso 1 1 calc R U . . . C12 C 0.1797(2) 0.67425(17) 0.92510(14) 0.0234(3) Uani 1 1 d . . . . . H12 H 0.048365 0.714016 0.959149 0.028 Uiso 1 1 calc R U . . . C7 C 0.7887(2) 0.16176(17) 0.43192(14) 0.0225(3) Uani 1 1 d . . . . . H7 H 0.816664 0.259860 0.387241 0.027 Uiso 1 1 calc R U . . . C1 C 0.60396(19) 0.31491(16) 0.63184(14) 0.0216(3) Uani 1 1 d . . . . . H1 H 0.649430 0.408455 0.590774 0.026 Uiso 1 1 calc R U . . . C6 C 0.8610(2) 0.01921(17) 0.36510(14) 0.0229(3) Uani 1 1 d . . . . . H6 H 0.937399 0.018078 0.275298 0.027 Uiso 1 1 calc R U . . . C3 C 0.63486(19) 0.01787(17) 0.63048(14) 0.0212(3) Uani 1 1 d . . . . . H3 H 0.558940 0.018005 0.720427 0.025 Uiso 1 1 calc R U . . . C4 C 0.7050(2) -0.12481(17) 0.56551(14) 0.0221(3) Uani 1 1 d . . . . . H4 H 0.677103 -0.223267 0.609448 0.027 Uiso 1 1 calc R U . . . C5 C 0.81704(19) -0.12065(17) 0.43470(14) 0.0214(3) Uani 1 1 d . . . . . C14 C 0.26087(19) 0.91137(17) 1.00577(14) 0.0242(3) Uani 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 0.0471(7) 0.0203(6) 0.0330(6) -0.0020(5) -0.0093(5) -0.0030(5) O2 0.0339(6) 0.0357(7) 0.0320(6) -0.0154(5) 0.0051(5) -0.0077(5) N1 0.0255(6) 0.0192(6) 0.0223(6) -0.0036(5) -0.0046(5) -0.0028(5) N2 0.0243(6) 0.0265(7) 0.0247(7) -0.0070(5) -0.0066(5) -0.0021(5) N3 0.0293(7) 0.0263(7) 0.0375(8) -0.0094(6) -0.0047(6) -0.0038(6) C8 0.0287(7) 0.0170(7) 0.0181(7) 0.0005(5) -0.0050(5) -0.0027(6) C13 0.0259(7) 0.0217(7) 0.0210(7) -0.0011(6) -0.0045(6) -0.0064(6) C2 0.0207(7) 0.0226(7) 0.0212(7) -0.0024(6) -0.0066(5) -0.0038(6) C11 0.0300(7) 0.0179(7) 0.0173(7) -0.0016(5) -0.0044(5) -0.0024(6) C9 0.0260(7) 0.0214(7) 0.0202(7) -0.0004(6) -0.0035(5) -0.0026(6) C10 0.0270(7) 0.0214(7) 0.0195(7) 0.0001(6) -0.0046(5) -0.0062(6) C12 0.0261(7) 0.0227(7) 0.0204(7) -0.0018(6) -0.0041(5) -0.0023(6) C7 0.0241(7) 0.0218(7) 0.0221(7) -0.0004(6) -0.0056(6) -0.0046(6) C1 0.0248(7) 0.0200(7) 0.0209(7) -0.0007(6) -0.0066(6) -0.0043(6) C6 0.0227(7) 0.0278(8) 0.0179(7) -0.0031(6) -0.0026(5) -0.0049(6) C3 0.0200(7) 0.0250(7) 0.0180(7) -0.0018(6) -0.0030(5) -0.0033(6) C4 0.0243(7) 0.0205(7) 0.0225(7) 0.0002(5) -0.0064(5) -0.0053(6) C5 0.0192(7) 0.0220(8) 0.0237(7) -0.0063(6) -0.0069(5) -0.0003(6) C14 0.0248(7) 0.0239(8) 0.0239(7) -0.0023(6) -0.0044(6) -0.0044(6) 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 C1 N1 C8 118.25(12) . . ? O1 N2 O2 123.61(12) . . ? O1 N2 C5 118.12(12) . . ? O2 N2 C5 118.26(12) . . ? C13 C8 N1 118.77(12) . . ? C13 C8 C9 119.88(13) . . ? C9 C8 N1 121.26(13) . . ? C8 C13 H13 119.8 . . ? C12 C13 C8 120.32(13) . . ? C12 C13 H13 119.8 . . ? C7 C2 C1 119.50(12) . . ? C7 C2 C3 119.98(13) . . ? C3 C2 C1 120.52(12) . . ? C10 C11 C12 120.64(13) . . ? C10 C11 C14 119.22(12) . . ? C12 C11 C14 120.14(12) . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.11(13) . . ? C10 C9 H9 119.9 . . ? C11 C10 H10 120.2 . . ? C9 C10 C11 119.54(12) . . ? C9 C10 H10 120.2 . . ? C13 C12 C11 119.45(13) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C2 C7 H7 119.6 . . ? C2 C7 C6 120.88(13) . . ? C6 C7 H7 119.6 . . ? N1 C1 C2 121.82(12) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C7 C6 H6 121.3 . . ? C5 C6 C7 117.40(13) . . ? C5 C6 H6 121.3 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 119.93(13) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 120.8 . . ? C3 C4 C5 118.45(13) . . ? C5 C4 H4 120.8 . . ? C6 C5 N2 118.60(12) . . ? C6 C5 C4 123.36(13) . . ? C4 C5 N2 118.03(12) . . ? N3 C14 C11 179.29(15) . . ? 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 N2 1.2287(17) . ? O2 N2 1.2298(16) . ? N1 C8 1.4156(18) . ? N1 C1 1.2730(18) . ? N2 C5 1.4783(17) . ? N3 C14 1.1525(19) . ? C8 C13 1.400(2) . ? C8 C9 1.402(2) . ? C13 H13 0.9500 . ? C13 C12 1.3838(19) . ? C2 C7 1.393(2) . ? C2 C1 1.4743(19) . ? C2 C3 1.403(2) . ? C11 C10 1.400(2) . ? C11 C12 1.401(2) . ? C11 C14 1.4438(18) . ? C9 H9 0.9500 . ? C9 C10 1.3861(19) . ? C10 H10 0.9500 . ? C12 H12 0.9500 . ? C7 H7 0.9500 . ? C7 C6 1.394(2) . ? C1 H1 0.9500 . ? C6 H6 0.9500 . ? C6 C5 1.384(2) . ? C3 H3 0.9500 . ? C3 C4 1.384(2) . ? C4 H4 0.9500 . ? C4 C5 1.388(2) . ? 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 N2 C5 C6 -177.96(12) . . . . ? O1 N2 C5 C4 3.14(18) . . . . ? O2 N2 C5 C6 3.15(18) . . . . ? O2 N2 C5 C4 -175.75(12) . . . . ? N1 C8 C13 C12 179.18(11) . . . . ? N1 C8 C9 C10 -177.88(11) . . . . ? C8 N1 C1 C2 176.16(11) . . . . ? C8 C13 C12 C11 -1.6(2) . . . . ? C8 C9 C10 C11 -0.8(2) . . . . ? C13 C8 C9 C10 -1.2(2) . . . . ? C2 C7 C6 C5 -0.3(2) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C9 C8 C13 C12 2.5(2) . . . . ? C10 C11 C12 C13 -0.5(2) . . . . ? C12 C11 C10 C9 1.7(2) . . . . ? C7 C2 C1 N1 171.45(13) . . . . ? C7 C2 C3 C4 -0.6(2) . . . . ? C7 C6 C5 N2 -178.39(11) . . . . ? C7 C6 C5 C4 0.4(2) . . . . ? C1 N1 C8 C13 135.63(14) . . . . ? C1 N1 C8 C9 -47.70(18) . . . . ? C1 C2 C7 C6 179.18(11) . . . . ? C1 C2 C3 C4 -179.35(11) . . . . ? C3 C2 C7 C6 0.4(2) . . . . ? C3 C2 C1 N1 -9.7(2) . . . . ? C3 C4 C5 N2 178.22(11) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C14 C11 C10 C9 -178.68(12) . . . . ? C14 C11 C12 C13 179.89(12) . . . . ?