#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:03:13 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304786 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064324.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_7064324 loop_ _publ_author_name 'Sithole, Sibusiso A.' 'Mansour, Ahmed M.' 'Malan, Frederick P.' 'Manikandan, Gurusamy' 'Katerere, David R.' 'Shehab, Ola R.' 'Manicum, Amanda-Lee E.' _publ_section_title ; Structural and antimicrobial studies on a tricarbonyl rhenium(i) complex with the 6,7-dimethyl-2-(pyridin-2-yl)quinoxaline ligand ; _journal_issue 4 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1844 _journal_page_last 1856 _journal_paper_doi 10.1039/D5NJ04125B _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C15 H13 N3' _chemical_formula_sum 'C15 H13 N3' _chemical_formula_weight 235.28 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-03-25 _audit_creation_method ; Olex2 1.5-alpha (compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188) ; _audit_update_record ; 2025-10-11 deposited with the CCDC. 2025-12-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 11.9662(4) _cell_length_b 7.4448(3) _cell_length_c 26.0051(9) _cell_measurement_reflns_used 12440 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 31.1200 _cell_measurement_theta_min 3.2750 _cell_volume 2316.69(15) _computing_cell_refinement 'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.834 _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 -79.00 8.00 0.50 2.00 -- -6.23 -48.00 -66.00 174 2 \w -18.00 27.00 0.50 2.00 -- -6.23 -99.00 -60.00 90 3 \w -37.00 31.00 0.50 2.00 -- 4.59 -85.00 84.00 136 4 \w -18.00 27.00 0.50 2.00 -- -6.23 -99.00 150.00 90 5 \w -19.00 28.00 0.50 2.00 -- -6.23 37.00 -90.00 94 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0423849000 _diffrn_orient_matrix_UB_12 -0.0557849000 _diffrn_orient_matrix_UB_13 -0.0104082000 _diffrn_orient_matrix_UB_21 -0.0307750000 _diffrn_orient_matrix_UB_22 -0.0075923000 _diffrn_orient_matrix_UB_23 -0.0232108000 _diffrn_orient_matrix_UB_31 0.0277417000 _diffrn_orient_matrix_UB_32 0.0768536000 _diffrn_orient_matrix_UB_33 -0.0098490000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0218 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.834 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 22431 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.834 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.155 _diffrn_reflns_theta_min 3.133 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.51523 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.349 _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.234 _exptl_crystal_size_mid 0.198 _exptl_crystal_size_min 0.175 _refine_diff_density_max 0.337 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 3121 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0406 _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^)+(0.0653P)^2^+0.6124P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1159 _refine_ls_wR_factor_ref 0.1222 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2578 _reflns_number_total 3121 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04125b2.cif _cod_data_source_block am108_lt_auto _cod_database_code 7064324 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C12 H12 N2 O' _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. ; _diffrn_oxdiff_digest_hkl ; 01bdab8654b1cc1e6ef9e3deef26b717792387 ; _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1.a Aromatic/amide H refined with riding coordinates: C5(H5), C8(H8), C3(H3), C10(H10), C11(H11), C13(H13), C12(H12) 1.b Idealised Me refined as rotating group: C7A1(H7AA,H7AB,H7AC), C6A1(H6AA,H6AB,H6AC) ; _shelx_res_file ; TITL am108_lt_auto_a.res in Pbca am108_lt_auto.res created by SHELXL-2018/3 at 02:21:19 on 25-Mar-2025 REM Old TITL AM108_LT_auto in Pbca REM SHELXT solution in Pbca REM R1 0.101, Rweak 0.007, Alpha 0.015, Orientation as input REM Formula found by SHELXT: C13 N3 CELL 0.71073 11.9662 7.4448 26.0051 90 90 90 ZERR 8 0.0004 0.0003 0.0009 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N UNIT 120 104 24 L.S. 10 PLAN 5 TEMP -123 CONF fmap 2 acta MORE -1 BOND $H REM REM REM WGHT 0.065300 0.612400 FVAR 1.99661 N2 3 0.726222 0.389715 0.366944 11.00000 0.01774 0.02055 = 0.01910 -0.00027 0.00022 -0.00005 N3 3 0.506904 0.535689 0.365387 11.00000 0.01857 0.02398 = 0.02032 -0.00092 0.00182 0.00264 N1 3 0.655417 0.350495 0.498980 11.00000 0.02098 0.03188 = 0.02034 0.00179 0.00109 0.00202 C5 1 0.512186 0.533174 0.272763 11.00000 0.01712 0.01903 = 0.02144 0.00020 -0.00081 0.00146 AFIX 43 H5 2 0.439658 0.585000 0.271981 11.00000 -1.20000 AFIX 0 C9 1 0.673196 0.426430 0.321638 11.00000 0.01730 0.01671 = 0.01859 0.00000 0.00000 -0.00081 C4 1 0.563877 0.500203 0.320663 11.00000 0.01729 0.01679 = 0.01944 -0.00068 0.00130 -0.00009 C2 1 0.669794 0.423448 0.409431 11.00000 0.01790 0.01940 = 0.01894 -0.00005 0.00020 -0.00042 C1 1 0.724134 0.381768 0.459262 11.00000 0.02023 0.01886 = 0.01819 -0.00064 0.00022 0.00074 C7 1 0.674486 0.414930 0.228308 11.00000 0.02022 0.01601 = 0.01879 -0.00121 0.00162 -0.00197 C6 1 0.564584 0.491877 0.227287 11.00000 0.02085 0.01593 = 0.01958 0.00031 -0.00141 -0.00196 C8 1 0.726435 0.384698 0.274595 11.00000 0.01664 0.01899 = 0.02079 -0.00157 0.00110 0.00020 AFIX 43 H8 2 0.799502 0.334816 0.275013 11.00000 -1.20000 AFIX 0 C3 1 0.559269 0.495953 0.408301 11.00000 0.01898 0.02358 = 0.01926 -0.00106 0.00209 0.00169 AFIX 43 H3 2 0.521967 0.516344 0.440016 11.00000 -1.20000 AFIX 0 C10 1 0.840131 0.372481 0.463265 11.00000 0.02011 0.02802 = 0.02259 0.00112 0.00087 0.00054 AFIX 43 H10 2 0.886257 0.398796 0.434503 11.00000 -1.20000 AFIX 0 C7A1 1 0.730354 0.361061 0.178833 11.00000 0.02548 0.02439 = 0.01950 -0.00238 0.00246 0.00090 AFIX 137 H7AA 2 0.686108 0.267337 0.161930 11.00000 -1.50000 H7AB 2 0.805381 0.314981 0.186197 11.00000 -1.50000 H7AC 2 0.735966 0.465774 0.156143 11.00000 -1.50000 AFIX 0 C11 1 0.886847 0.324170 0.509964 11.00000 0.01993 0.03319 = 0.02762 -0.00050 -0.00303 0.00305 AFIX 43 H11 2 0.965645 0.316535 0.513844 11.00000 -1.20000 AFIX 0 C6A1 1 0.505929 0.521443 0.176718 11.00000 0.02411 0.02664 = 0.02035 0.00143 -0.00213 -0.00021 AFIX 137 H6AA 2 0.497642 0.406325 0.158844 11.00000 -1.50000 H6AB 2 0.550046 0.603736 0.155434 11.00000 -1.50000 H6AC 2 0.431952 0.573498 0.182987 11.00000 -1.50000 AFIX 0 C13 1 0.702303 0.303881 0.543716 11.00000 0.02561 0.03633 = 0.01959 0.00349 0.00209 0.00306 AFIX 43 H13 2 0.654572 0.280929 0.572159 11.00000 -1.20000 AFIX 0 C12 1 0.816512 0.287176 0.550923 11.00000 0.02893 0.03068 = 0.02059 0.00044 -0.00434 0.00501 AFIX 43 H12 2 0.845960 0.251145 0.583242 11.00000 -1.20000 AFIX 0 HKLF 4 REM am108_lt_auto_a.res in Pbca REM wR2 = 0.1222, GooF = S = 1.049, Restrained GooF = 1.049 for all data REM R1 = 0.0406 for 2578 Fo > 4sig(Fo) and 0.0499 for all 3121 data REM 165 parameters refined using 0 restraints END WGHT 0.0653 0.6124 REM Highest difference peak 0.337, deepest hole -0.197, 1-sigma level 0.045 Q1 1 0.7045 0.4145 0.2975 11.00000 0.05 0.34 Q2 1 0.6990 0.3917 0.4356 11.00000 0.05 0.33 Q3 1 0.5429 0.5255 0.2501 11.00000 0.05 0.32 Q4 1 0.5367 0.5194 0.3430 11.00000 0.05 0.31 Q5 1 0.6231 0.4608 0.3206 11.00000 0.05 0.31 ; _shelx_res_checksum 19350 _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 1.897 _oxdiff_exptl_absorpt_empirical_full_min 0.624 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 N2 N 0.72622(7) 0.38971(12) 0.36694(3) 0.01913(19) Uani 1 1 d . . . . . N3 N 0.50690(7) 0.53569(12) 0.36539(3) 0.0210(2) Uani 1 1 d . . . . . N1 N 0.65542(8) 0.35049(13) 0.49898(3) 0.0244(2) Uani 1 1 d . . . . . C5 C 0.51219(8) 0.53317(13) 0.27276(4) 0.0192(2) Uani 1 1 d . . . . . H5 H 0.439658 0.585000 0.271981 0.023 Uiso 1 1 calc R U . . . C9 C 0.67320(8) 0.42643(13) 0.32164(4) 0.0175(2) Uani 1 1 d . . . . . C4 C 0.56388(8) 0.50020(13) 0.32066(4) 0.0178(2) Uani 1 1 d . . . . . C2 C 0.66979(8) 0.42345(13) 0.40943(4) 0.0187(2) Uani 1 1 d . . . . . C1 C 0.72413(8) 0.38177(13) 0.45926(4) 0.0191(2) Uani 1 1 d . . . . . C7 C 0.67449(8) 0.41493(13) 0.22831(4) 0.0183(2) Uani 1 1 d . . . . . C6 C 0.56458(8) 0.49188(13) 0.22729(4) 0.0188(2) Uani 1 1 d . . . . . C8 C 0.72644(8) 0.38470(14) 0.27459(4) 0.0188(2) Uani 1 1 d . . . . . H8 H 0.799502 0.334816 0.275013 0.023 Uiso 1 1 calc R U . . . C3 C 0.55927(8) 0.49595(14) 0.40830(4) 0.0206(2) Uani 1 1 d . . . . . H3 H 0.521967 0.516344 0.440016 0.025 Uiso 1 1 calc R U . . . C10 C 0.84013(9) 0.37248(15) 0.46327(4) 0.0236(2) Uani 1 1 d . . . . . H10 H 0.886257 0.398796 0.434503 0.028 Uiso 1 1 calc R U . . . C7A1 C 0.73035(9) 0.36106(15) 0.17883(4) 0.0231(2) Uani 1 1 d . . . . . H7AA H 0.686108 0.267337 0.161930 0.035 Uiso 1 1 calc R U . . . H7AB H 0.805381 0.314981 0.186197 0.035 Uiso 1 1 calc R U . . . H7AC H 0.735966 0.465774 0.156143 0.035 Uiso 1 1 calc R U . . . C11 C 0.88685(9) 0.32417(15) 0.50996(4) 0.0269(2) Uani 1 1 d . . . . . H11 H 0.965645 0.316535 0.513844 0.032 Uiso 1 1 calc R U . . . C6A1 C 0.50593(9) 0.52144(15) 0.17672(4) 0.0237(2) Uani 1 1 d . . . . . H6AA H 0.497642 0.406325 0.158844 0.036 Uiso 1 1 calc R U . . . H6AB H 0.550046 0.603736 0.155434 0.036 Uiso 1 1 calc R U . . . H6AC H 0.431952 0.573498 0.182987 0.036 Uiso 1 1 calc R U . . . C13 C 0.70230(9) 0.30388(16) 0.54372(4) 0.0272(3) Uani 1 1 d . . . . . H13 H 0.654572 0.280929 0.572159 0.033 Uiso 1 1 calc R U . . . C12 C 0.81651(10) 0.28718(15) 0.55092(4) 0.0267(2) Uani 1 1 d . . . . . H12 H 0.845960 0.251145 0.583242 0.032 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 N2 0.0177(4) 0.0206(4) 0.0191(4) -0.0003(3) 0.0002(3) -0.0001(3) N3 0.0186(4) 0.0240(5) 0.0203(4) -0.0009(3) 0.0018(3) 0.0026(3) N1 0.0210(4) 0.0319(5) 0.0203(4) 0.0018(4) 0.0011(3) 0.0020(4) C5 0.0171(5) 0.0190(5) 0.0214(5) 0.0002(3) -0.0008(3) 0.0015(3) C9 0.0173(5) 0.0167(4) 0.0186(5) 0.0000(3) 0.0000(3) -0.0008(3) C4 0.0173(5) 0.0168(4) 0.0194(5) -0.0007(3) 0.0013(3) -0.0001(3) C2 0.0179(5) 0.0194(5) 0.0189(5) -0.0001(3) 0.0002(3) -0.0004(3) C1 0.0202(5) 0.0189(5) 0.0182(5) -0.0006(4) 0.0002(3) 0.0007(3) C7 0.0202(5) 0.0160(4) 0.0188(5) -0.0012(3) 0.0016(3) -0.0020(3) C6 0.0208(5) 0.0159(4) 0.0196(5) 0.0003(3) -0.0014(3) -0.0020(3) C8 0.0166(5) 0.0190(5) 0.0208(5) -0.0016(3) 0.0011(3) 0.0002(3) C3 0.0190(5) 0.0236(5) 0.0193(5) -0.0011(4) 0.0021(3) 0.0017(4) C10 0.0201(5) 0.0280(5) 0.0226(5) 0.0011(4) 0.0009(4) 0.0005(4) C7A1 0.0255(5) 0.0244(5) 0.0195(5) -0.0024(4) 0.0025(4) 0.0009(4) C11 0.0199(5) 0.0332(6) 0.0276(5) -0.0005(4) -0.0030(4) 0.0030(4) C6A1 0.0241(5) 0.0266(5) 0.0204(5) 0.0014(4) -0.0021(4) -0.0002(4) C13 0.0256(5) 0.0363(6) 0.0196(5) 0.0035(4) 0.0021(4) 0.0031(4) C12 0.0289(6) 0.0307(6) 0.0206(5) 0.0004(4) -0.0043(4) 0.0050(4) 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' 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 C2 N2 C9 116.53(8) . . ? C3 N3 C4 116.05(9) . . ? C13 N1 C1 117.26(9) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C6 C5 C4 121.37(9) . . ? N2 C9 C4 121.41(8) . . ? N2 C9 C8 119.54(9) . . ? C8 C9 C4 119.01(8) . . ? N3 C4 C5 119.73(9) . . ? N3 C4 C9 121.12(8) . . ? C5 C4 C9 119.13(8) . . ? N2 C2 C1 117.89(8) . . ? N2 C2 C3 121.91(9) . . ? C3 C2 C1 120.20(8) . . ? N1 C1 C2 116.15(8) . . ? N1 C1 C10 123.01(9) . . ? C10 C1 C2 120.83(9) . . ? C6 C7 C7A1 119.87(8) . . ? C8 C7 C6 119.77(8) . . ? C8 C7 C7A1 120.32(9) . . ? C5 C6 C7 119.47(9) . . ? C5 C6 C6A1 120.41(9) . . ? C7 C6 C6A1 120.10(9) . . ? C9 C8 H8 119.4 . . ? C7 C8 C9 121.23(9) . . ? C7 C8 H8 119.4 . . ? N3 C3 C2 122.96(9) . . ? N3 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C1 C10 H10 120.6 . . ? C11 C10 C1 118.72(9) . . ? C11 C10 H10 120.6 . . ? C7 C7A1 H7AA 109.5 . . ? C7 C7A1 H7AB 109.5 . . ? C7 C7A1 H7AC 109.5 . . ? H7AA C7A1 H7AB 109.5 . . ? H7AA C7A1 H7AC 109.5 . . ? H7AB C7A1 H7AC 109.5 . . ? C10 C11 H11 120.6 . . ? C10 C11 C12 118.74(10) . . ? C12 C11 H11 120.6 . . ? C6 C6A1 H6AA 109.5 . . ? C6 C6A1 H6AB 109.5 . . ? C6 C6A1 H6AC 109.5 . . ? H6AA C6A1 H6AB 109.5 . . ? H6AA C6A1 H6AC 109.5 . . ? H6AB C6A1 H6AC 109.5 . . ? N1 C13 H13 118.1 . . ? N1 C13 C12 123.71(10) . . ? C12 C13 H13 118.1 . . ? C11 C12 H12 120.7 . . ? C13 C12 C11 118.53(10) . . ? C13 C12 H12 120.7 . . ? 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 N2 C9 1.3658(12) . ? N2 C2 1.3190(12) . ? N3 C4 1.3738(12) . ? N3 C3 1.3136(13) . ? N1 C1 1.3406(13) . ? N1 C13 1.3374(13) . ? C5 H5 0.9500 . ? C5 C4 1.4123(13) . ? C5 C6 1.3734(13) . ? C9 C4 1.4190(14) . ? C9 C8 1.4139(13) . ? C2 C1 1.4827(13) . ? C2 C3 1.4288(14) . ? C1 C10 1.3937(14) . ? C7 C6 1.4347(14) . ? C7 C8 1.3733(13) . ? C7 C7A1 1.5043(13) . ? C6 C6A1 1.5068(13) . ? C8 H8 0.9500 . ? C3 H3 0.9500 . ? C10 H10 0.9500 . ? C10 C11 1.3844(14) . ? C7A1 H7AA 0.9800 . ? C7A1 H7AB 0.9800 . ? C7A1 H7AC 0.9800 . ? C11 H11 0.9500 . ? C11 C12 1.3852(15) . ? C6A1 H6AA 0.9800 . ? C6A1 H6AB 0.9800 . ? C6A1 H6AC 0.9800 . ? C13 H13 0.9500 . ? C13 C12 1.3850(15) . ? C12 H12 0.9500 . ? 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 N2 C9 C4 N3 -0.68(15) . . . . ? N2 C9 C4 C5 -179.08(9) . . . . ? N2 C9 C8 C7 178.14(9) . . . . ? N2 C2 C1 N1 -155.19(9) . . . . ? N2 C2 C1 C10 23.42(14) . . . . ? N2 C2 C3 N3 -0.77(16) . . . . ? N1 C1 C10 C11 1.76(16) . . . . ? N1 C13 C12 C11 1.38(18) . . . . ? C9 N2 C2 C1 178.83(8) . . . . ? C9 N2 C2 C3 -0.48(14) . . . . ? C4 N3 C3 C2 1.24(15) . . . . ? C4 C5 C6 C7 -0.50(15) . . . . ? C4 C5 C6 C6A1 177.55(9) . . . . ? C4 C9 C8 C7 0.26(15) . . . . ? C2 N2 C9 C4 1.15(14) . . . . ? C2 N2 C9 C8 -176.68(9) . . . . ? C2 C1 C10 C11 -176.75(10) . . . . ? C1 N1 C13 C12 0.21(17) . . . . ? C1 C2 C3 N3 179.93(9) . . . . ? C1 C10 C11 C12 -0.09(16) . . . . ? C6 C5 C4 N3 -177.05(9) . . . . ? C6 C5 C4 C9 1.37(15) . . . . ? C6 C7 C8 C9 0.62(15) . . . . ? C8 C9 C4 N3 177.16(9) . . . . ? C8 C9 C4 C5 -1.24(14) . . . . ? C8 C7 C6 C5 -0.51(15) . . . . ? C8 C7 C6 C6A1 -178.56(9) . . . . ? C3 N3 C4 C5 177.85(9) . . . . ? C3 N3 C4 C9 -0.54(14) . . . . ? C3 C2 C1 N1 24.14(14) . . . . ? C3 C2 C1 C10 -157.25(10) . . . . ? C10 C11 C12 C13 -1.37(17) . . . . ? C7A1 C7 C6 C5 177.08(9) . . . . ? C7A1 C7 C6 C6A1 -0.98(14) . . . . ? C7A1 C7 C8 C9 -176.96(9) . . . . ? C13 N1 C1 C2 176.77(10) . . . . ? C13 N1 C1 C10 -1.80(15) . . . . ?