#------------------------------------------------------------------------------ #$Date: 2023-11-11 03:01:43 +0200 (Sat, 11 Nov 2023) $ #$Revision: 287534 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247703.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_7247703 loop_ _publ_author_name 'Han, Wei' 'Chen, Yu-Lan' 'Tang, Xi' 'Zhou, Jie' 'Ma, Mengtao' 'Shen, Zhi-Liang' 'Chu, Xue-Qiang' _publ_section_title ; Water-Promoted Defluorinative Synthesis of Fluoroalkylated 1,5-Diazapentadienes by Using (NH4)2CO3 as NH2 and NH Sources ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03717G _journal_year 2023 _chemical_formula_moiety 'C13 H8 F7 N3' _chemical_formula_sum 'C13 H8 F7 N3' _chemical_formula_weight 339.22 _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' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2023-02-20 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2023-02-21 deposited with the CCDC. 2023-11-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.132(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5372(11) _cell_length_b 11.7335(9) _cell_length_c 10.3893(9) _cell_measurement_reflns_used 2802 _cell_measurement_temperature 199.99(10) _cell_measurement_theta_max 28.2740 _cell_measurement_theta_min 2.6640 _cell_volume 1363.9(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (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 199.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -9.00 77.00 1.00 2.50 -- 12.05 38.00-120.00 86 2 \w -57.00 39.00 1.00 2.50 -- 12.05 -57.00 60.00 96 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0139191000 _diffrn_orient_matrix_UB_12 0.0556314000 _diffrn_orient_matrix_UB_13 -0.0179349000 _diffrn_orient_matrix_UB_21 -0.0463054000 _diffrn_orient_matrix_UB_22 -0.0034920000 _diffrn_orient_matrix_UB_23 -0.0591042000 _diffrn_orient_matrix_UB_31 -0.0410781000 _diffrn_orient_matrix_UB_32 0.0229764000 _diffrn_orient_matrix_UB_33 0.0340383000 _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 0.0239 _diffrn_reflns_av_unetI/netI 0.0324 _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 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5493 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 2.515 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.652 _exptl_crystal_description block _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.194 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 2399 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0395 _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^)+(0.0560P)^2^+0.0775P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.1047 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1991 _reflns_number_total 2399 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03717g2.cif _cod_data_source_block 1023-1 _cod_database_code 7247703 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C4(H4), C5(H5), C8(H8) ; _shelx_res_file ; TITL 1023-1_a.res in P2(1)/c 1023-1.res created by SHELXL-2018/3 at 21:12:52 on 20-Feb-2023 REM Old TITL 1023-1 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.172, Rweak 0.265, Alpha 0.025 REM 0.807 for 145 systematic absences, Orientation as input REM Formula found by SHELXT: C13 N2 O3 F5 CELL 0.71073 11.5372 11.7335 10.3893 90 104.132 90 ZERR 4 0.0011 0.0009 0.0009 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N UNIT 52 32 28 12 L.S. 20 PLAN 8 TEMP -120 CONF BOND list 4 fmap 2 53 MORE -1 ACTA BOND $H OMIT -3 50 REM REM REM WGHT 0.056000 0.077500 EXTI 0.017132 FVAR 0.65263 F1 3 -0.016982 0.491501 0.782026 11.00000 0.03797 0.06122 = 0.05156 -0.00373 0.02198 -0.00538 F2 3 0.049298 0.627799 0.678849 11.00000 0.05320 0.04416 = 0.04099 0.00868 0.01555 0.01835 F3 3 0.186912 0.478154 0.964659 11.00000 0.08341 0.04891 = 0.04025 0.00095 -0.00210 0.02395 F4 3 0.273757 0.599818 0.859177 11.00000 0.03392 0.06861 = 0.08209 -0.02850 0.01203 -0.00279 F5 3 0.022693 0.648906 0.980811 11.00000 0.07353 0.05782 = 0.06856 -0.00212 0.03976 0.00843 F6 3 0.207747 0.681724 1.075202 11.00000 0.09809 0.08614 = 0.05903 -0.03515 -0.02028 0.03690 F7 3 0.125460 0.764155 0.893561 11.00000 0.06482 0.03555 = 0.07681 -0.00715 0.01608 -0.00016 N1 4 0.560394 0.652876 0.085586 11.00000 0.06095 0.04104 = 0.04434 0.00292 0.02471 -0.00466 N2 4 0.254975 0.305188 0.518706 11.00000 0.05242 0.02673 = 0.04056 0.00038 0.02407 -0.00139 H2A 2 0.216956 0.277871 0.575599 11.00000 0.05534 H2B 2 0.301126 0.265837 0.479478 11.00000 0.04423 N3 4 0.131843 0.337680 0.706355 11.00000 0.04913 0.03363 = 0.04123 0.00132 0.02075 -0.00730 H3 2 0.087553 0.326410 0.764441 11.00000 0.04764 C1 1 0.332014 0.411259 0.305124 11.00000 0.04105 0.02666 = 0.02964 -0.00047 0.00731 -0.00293 AFIX 43 H1 2 0.296497 0.338144 0.286562 11.00000 -1.20000 AFIX 0 C2 1 0.395596 0.456814 0.221136 11.00000 0.04384 0.03428 = 0.02519 -0.00104 0.00984 0.00152 AFIX 43 H2 2 0.404808 0.414758 0.146129 11.00000 -1.20000 AFIX 0 C3 1 0.446113 0.564256 0.246419 11.00000 0.03214 0.03066 = 0.02913 0.00504 0.00853 0.00289 C4 1 0.432068 0.625457 0.356010 11.00000 0.03273 0.02765 = 0.03594 0.00027 0.00856 -0.00218 AFIX 43 H4 2 0.465167 0.699718 0.372519 11.00000 -1.20000 AFIX 0 C5 1 0.370364 0.578642 0.440457 11.00000 0.03564 0.02754 = 0.02975 -0.00318 0.01008 0.00058 AFIX 43 H5 2 0.362491 0.620367 0.516225 11.00000 -1.20000 AFIX 0 C6 1 0.318976 0.470522 0.416586 11.00000 0.02855 0.02766 = 0.02684 0.00173 0.00584 0.00318 C7 1 0.254313 0.419463 0.510055 11.00000 0.03084 0.02754 = 0.02818 0.00205 0.00549 -0.00105 C8 1 0.197181 0.486100 0.582679 11.00000 0.03887 0.02559 = 0.03398 0.00163 0.01317 0.00048 AFIX 43 H8 2 0.197098 0.566126 0.568772 11.00000 -1.20000 AFIX 0 C9 1 0.137490 0.443967 0.678147 11.00000 0.03122 0.03271 = 0.02917 0.00010 0.00778 -0.00089 C10 1 0.082703 0.532963 0.752272 11.00000 0.03149 0.03672 = 0.03330 0.00672 0.01132 0.00086 C11 1 0.168095 0.569469 0.883574 11.00000 0.03980 0.03927 = 0.04089 -0.00103 0.00769 0.00739 C12 1 0.129254 0.667620 0.959743 11.00000 0.05055 0.04745 = 0.04662 -0.00707 0.00456 0.00992 C13 1 0.510588 0.612924 0.157176 11.00000 0.04151 0.03184 = 0.03379 0.00090 0.01171 0.00053 HKLF 4 REM 1023-1_a.res in P2(1)/c REM wR2 = 0.1047, GooF = S = 1.069, Restrained GooF = 1.069 for all data REM R1 = 0.0395 for 1991 Fo > 4sig(Fo) and 0.0479 for all 2399 data REM 221 parameters refined using 0 restraints END WGHT 0.0555 0.1559 REM Highest difference peak 0.194, deepest hole -0.280, 1-sigma level 0.046 Q1 1 0.3617 0.4275 0.3930 11.00000 0.05 0.19 Q2 1 0.1759 0.6205 1.1020 11.00000 0.05 0.19 Q3 1 0.2611 0.4448 0.4452 11.00000 0.05 0.19 Q4 1 0.1041 0.6166 1.0357 11.00000 0.05 0.18 Q5 1 0.2544 0.6786 1.0191 11.00000 0.05 0.18 Q6 1 0.2568 0.5128 0.9381 11.00000 0.05 0.17 Q7 1 0.3036 0.5225 0.3999 11.00000 0.05 0.17 Q8 1 0.3847 0.4996 0.4573 11.00000 0.05 0.16 ; _shelx_res_checksum 34449 _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 1.336 _oxdiff_exptl_absorpt_empirical_full_min 0.736 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.01698(10) 0.49150(10) 0.78203(11) 0.0483(3) Uani 1 1 d . . . . . F2 F 0.04930(10) 0.62780(8) 0.67885(10) 0.0454(3) Uani 1 1 d . . . . . F3 F 0.18691(12) 0.47815(10) 0.96466(11) 0.0605(4) Uani 1 1 d . . . . . F4 F 0.27376(10) 0.59982(11) 0.85918(13) 0.0619(4) Uani 1 1 d . . . . . F5 F 0.02269(12) 0.64891(10) 0.98081(13) 0.0628(4) Uani 1 1 d . . . . . F6 F 0.20775(14) 0.68172(13) 1.07520(14) 0.0879(5) Uani 1 1 d . . . . . F7 F 0.12546(11) 0.76416(9) 0.89356(12) 0.0593(4) Uani 1 1 d . . . . . N1 N 0.56039(16) 0.65288(13) 0.08559(16) 0.0467(4) Uani 1 1 d . . . . . N2 N 0.25497(16) 0.30519(13) 0.51871(17) 0.0377(4) Uani 1 1 d . . . . . H2A H 0.217(2) 0.2779(18) 0.576(2) 0.055(6) Uiso 1 1 d . . . . . H2B H 0.3011(18) 0.2658(17) 0.4795(19) 0.044(6) Uiso 1 1 d . . . . . N3 N 0.13184(15) 0.33768(12) 0.70635(16) 0.0396(4) Uani 1 1 d . . . . . H3 H 0.0876(18) 0.3264(16) 0.764(2) 0.048(6) Uiso 1 1 d . . . . . C1 C 0.33201(16) 0.41126(14) 0.30512(16) 0.0327(4) Uani 1 1 d . . . . . H1 H 0.296497 0.338144 0.286562 0.039 Uiso 1 1 calc R U . . . C2 C 0.39560(16) 0.45681(14) 0.22114(17) 0.0342(4) Uani 1 1 d . . . . . H2 H 0.404808 0.414758 0.146129 0.041 Uiso 1 1 calc R U . . . C3 C 0.44611(15) 0.56426(14) 0.24642(16) 0.0305(4) Uani 1 1 d . . . . . C4 C 0.43207(15) 0.62546(14) 0.35601(17) 0.0321(4) Uani 1 1 d . . . . . H4 H 0.465167 0.699718 0.372519 0.038 Uiso 1 1 calc R U . . . C5 C 0.37036(15) 0.57864(13) 0.44046(16) 0.0306(4) Uani 1 1 d . . . . . H5 H 0.362491 0.620367 0.516225 0.037 Uiso 1 1 calc R U . . . C6 C 0.31898(14) 0.47052(13) 0.41659(16) 0.0278(4) Uani 1 1 d . . . . . C7 C 0.25431(15) 0.41946(14) 0.51005(16) 0.0292(4) Uani 1 1 d . . . . . C8 C 0.19718(16) 0.48610(14) 0.58268(17) 0.0321(4) Uani 1 1 d . . . . . H8 H 0.197098 0.566126 0.568772 0.038 Uiso 1 1 calc R U . . . C9 C 0.13749(15) 0.44397(14) 0.67815(16) 0.0310(4) Uani 1 1 d . . . . . C10 C 0.08270(15) 0.53296(14) 0.75227(17) 0.0332(4) Uani 1 1 d . . . . . C11 C 0.16810(17) 0.56947(16) 0.88357(18) 0.0404(5) Uani 1 1 d . . . . . C12 C 0.1293(2) 0.66762(17) 0.9597(2) 0.0495(5) Uani 1 1 d . . . . . C13 C 0.51059(17) 0.61292(15) 0.15718(17) 0.0353(4) 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 F1 0.0380(7) 0.0612(7) 0.0516(7) -0.0037(5) 0.0220(5) -0.0054(5) F2 0.0532(7) 0.0442(6) 0.0410(6) 0.0087(5) 0.0155(5) 0.0183(5) F3 0.0834(10) 0.0489(7) 0.0402(7) 0.0009(5) -0.0021(6) 0.0239(6) F4 0.0339(7) 0.0686(8) 0.0821(9) -0.0285(7) 0.0120(6) -0.0028(6) F5 0.0735(10) 0.0578(8) 0.0686(9) -0.0021(6) 0.0398(7) 0.0084(6) F6 0.0981(12) 0.0861(10) 0.0590(9) -0.0351(8) -0.0203(8) 0.0369(9) F7 0.0648(9) 0.0356(6) 0.0768(9) -0.0071(6) 0.0161(7) -0.0002(5) N1 0.0610(12) 0.0410(9) 0.0443(10) 0.0029(8) 0.0247(9) -0.0047(8) N2 0.0524(11) 0.0267(8) 0.0406(9) 0.0004(7) 0.0241(8) -0.0014(7) N3 0.0491(10) 0.0336(9) 0.0412(9) 0.0013(7) 0.0208(8) -0.0073(7) C1 0.0410(11) 0.0267(8) 0.0296(9) -0.0005(8) 0.0073(8) -0.0029(8) C2 0.0438(11) 0.0343(9) 0.0252(9) -0.0010(8) 0.0098(8) 0.0015(8) C3 0.0321(10) 0.0307(9) 0.0291(9) 0.0050(7) 0.0085(7) 0.0029(7) C4 0.0327(10) 0.0276(8) 0.0359(10) 0.0003(8) 0.0086(8) -0.0022(7) C5 0.0356(10) 0.0275(9) 0.0297(9) -0.0032(7) 0.0101(8) 0.0006(7) C6 0.0285(9) 0.0277(8) 0.0268(9) 0.0017(7) 0.0058(7) 0.0032(7) C7 0.0308(10) 0.0275(8) 0.0282(9) 0.0021(7) 0.0055(7) -0.0010(7) C8 0.0389(10) 0.0256(8) 0.0340(10) 0.0016(7) 0.0132(8) 0.0005(7) C9 0.0312(10) 0.0327(9) 0.0292(9) 0.0001(8) 0.0078(7) -0.0009(7) C10 0.0315(10) 0.0367(9) 0.0333(10) 0.0067(8) 0.0113(8) 0.0009(8) C11 0.0398(11) 0.0393(10) 0.0409(11) -0.0010(9) 0.0077(9) 0.0074(8) C12 0.0505(14) 0.0475(12) 0.0466(12) -0.0071(10) 0.0046(10) 0.0099(10) C13 0.0415(11) 0.0318(9) 0.0338(9) 0.0009(8) 0.0117(9) 0.0005(8) 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' F F 0.0171 0.0103 '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 H2A N2 H2B 125.5(19) . . ? C7 N2 H2A 114.4(14) . . ? C7 N2 H2B 119.2(13) . . ? C9 N3 H3 111.6(13) . . ? C2 C1 H1 119.5 . . ? C2 C1 C6 121.08(16) . . ? C6 C1 H1 119.5 . . ? C1 C2 H2 120.1 . . ? C1 C2 C3 119.80(16) . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 119.84(15) . . ? C2 C3 C13 119.84(15) . . ? C4 C3 C13 120.30(15) . . ? C3 C4 H4 120.0 . . ? C5 C4 C3 119.99(15) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 119.5 . . ? C4 C5 C6 120.93(15) . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 118.34(15) . . ? C1 C6 C7 121.06(15) . . ? C5 C6 C7 120.58(14) . . ? N2 C7 C6 116.75(14) . . ? N2 C7 C8 122.07(15) . . ? C8 C7 C6 121.18(15) . . ? C7 C8 H8 117.7 . . ? C7 C8 C9 124.52(15) . . ? C9 C8 H8 117.7 . . ? N3 C9 C8 123.65(16) . . ? N3 C9 C10 119.94(15) . . ? C8 C9 C10 116.37(14) . . ? F1 C10 C9 110.49(14) . . ? F1 C10 C11 107.11(14) . . ? F2 C10 F1 106.51(14) . . ? F2 C10 C9 112.06(13) . . ? F2 C10 C11 107.73(14) . . ? C9 C10 C11 112.63(14) . . ? F3 C11 F4 108.16(15) . . ? F3 C11 C10 107.70(15) . . ? F3 C11 C12 107.39(16) . . ? F4 C11 C10 108.61(15) . . ? F4 C11 C12 106.91(16) . . ? C12 C11 C10 117.74(16) . . ? F5 C12 F6 109.23(18) . . ? F5 C12 F7 108.40(16) . . ? F5 C12 C11 111.36(17) . . ? F6 C12 C11 109.97(17) . . ? F7 C12 F6 107.02(18) . . ? F7 C12 C11 110.74(17) . . ? N1 C13 C3 178.9(2) . . ? 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 F1 C10 1.3522(19) . ? F2 C10 1.3510(19) . ? F3 C11 1.347(2) . ? F4 C11 1.352(2) . ? F5 C12 1.319(2) . ? F6 C12 1.325(2) . ? F7 C12 1.320(2) . ? N1 C13 1.145(2) . ? N2 H2A 0.88(2) . ? N2 H2B 0.88(2) . ? N2 C7 1.344(2) . ? N3 H3 0.89(2) . ? N3 C9 1.286(2) . ? C1 H1 0.9500 . ? C1 C2 1.378(2) . ? C1 C6 1.390(2) . ? C2 H2 0.9500 . ? C2 C3 1.387(2) . ? C3 C4 1.389(2) . ? C3 C13 1.441(2) . ? C4 H4 0.9500 . ? C4 C5 1.372(2) . ? C5 H5 0.9500 . ? C5 C6 1.397(2) . ? C6 C7 1.487(2) . ? C7 C8 1.363(2) . ? C8 H8 0.9500 . ? C8 C9 1.427(2) . ? C9 C10 1.523(2) . ? C10 C11 1.536(3) . ? C11 C12 1.525(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 F1 C10 C11 F3 56.52(18) . . . . ? F1 C10 C11 F4 173.43(13) . . . . ? F1 C10 C11 C12 -65.0(2) . . . . ? F2 C10 C11 F3 170.76(13) . . . . ? F2 C10 C11 F4 -72.33(17) . . . . ? F2 C10 C11 C12 49.3(2) . . . . ? F3 C11 C12 F5 -68.2(2) . . . . ? F3 C11 C12 F6 53.1(2) . . . . ? F3 C11 C12 F7 171.14(16) . . . . ? F4 C11 C12 F5 175.96(16) . . . . ? F4 C11 C12 F6 -62.8(2) . . . . ? F4 C11 C12 F7 55.3(2) . . . . ? N2 C7 C8 C9 2.8(3) . . . . ? N3 C9 C10 F1 -34.5(2) . . . . ? N3 C9 C10 F2 -153.13(16) . . . . ? N3 C9 C10 C11 85.2(2) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C1 C2 C3 C13 -178.76(16) . . . . ? C1 C6 C7 N2 28.0(2) . . . . ? C1 C6 C7 C8 -151.87(17) . . . . ? C2 C1 C6 C5 1.0(3) . . . . ? C2 C1 C6 C7 -177.63(15) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C4 C5 C6 C7 178.78(15) . . . . ? C5 C6 C7 N2 -150.68(16) . . . . ? C5 C6 C7 C8 29.5(2) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C6 C7 C8 C9 -177.33(16) . . . . ? C7 C8 C9 N3 0.4(3) . . . . ? C7 C8 C9 C10 177.97(16) . . . . ? C8 C9 C10 F1 147.76(15) . . . . ? C8 C9 C10 F2 29.2(2) . . . . ? C8 C9 C10 C11 -92.50(18) . . . . ? C9 C10 C11 F3 -65.16(19) . . . . ? C9 C10 C11 F4 51.76(19) . . . . ? C9 C10 C11 C12 173.35(16) . . . . ? C10 C11 C12 F5 53.5(2) . . . . ? C10 C11 C12 F6 174.71(17) . . . . ? C10 C11 C12 F7 -67.2(2) . . . . ? C13 C3 C4 C5 179.88(16) . . . . ?