#------------------------------------------------------------------------------ #$Date: 2024-11-04 03:32:33 +0200 (Mon, 04 Nov 2024) $ #$Revision: 295739 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160201.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_7160201 loop_ _publ_author_name 'Panda, Tarun K.' 'Devadkar , Ajitaro' 'Paul, Ishita' 'Dey, Soumyadip' 'Sau, Abhijit' _publ_section_title ; Facile access to trifluoromethyl propargyl alcohol by metal free transfer hydrogenation and cyanation of alkynyl Ketone ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB00844H _journal_year 2024 _chemical_formula_moiety 'C18 H14 F3 N3' _chemical_formula_sum 'C18 H14 F3 N3' _chemical_formula_weight 329.32 _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-04-21 deposited with the CCDC. 2024-11-01 downloaded from the CCDC. ; _cell_angle_alpha 105.651(2) _cell_angle_beta 105.770(2) _cell_angle_gamma 101.840(2) _cell_formula_units_Z 2 _cell_length_a 7.0003(5) _cell_length_b 10.2027(7) _cell_length_c 12.3065(8) _cell_measurement_reflns_used 23404 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.188 _cell_measurement_theta_min 2.173 _cell_volume 776.85(9) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_collection 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'ORTEP III and WINGX' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 23404 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.188 _diffrn_reflns_theta_min 2.173 _diffrn_source 'Bruker APEX-II CCD' _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_description plates _exptl_crystal_F_000 340 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.258 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3427 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0370 _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^)+(0.0464P)^2^+0.2291P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0959 _refine_ls_wR_factor_ref 0.0990 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3087 _reflns_number_total 3427 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00844h2.cif _cod_data_source_block shelx_6b _cod_database_code 7160201 _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. ; _shelx_res_file ; TITL mo_TKP_AD_CF32_0m_a.res in P-1 shelx.res created by SHELXL-2018/3 at 21:45:14 on 07-Mar-2024 CELL 0.71073 7.0003 10.2027 12.3065 105.651 105.770 101.840 ZERR 2.00 0.0005 0.0007 0.0008 0.002 0.002 0.002 LATT 1 SFAC N F C H UNIT 6 6 36 28 MERG 2 MORE -1 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 20 TEMP -100.15 WGHT 0.046400 0.229100 FVAR 1.61221 N1 1 0.527738 0.670464 0.212026 11.00000 0.02570 0.02210 = 0.03068 0.00601 0.00344 0.00718 N2 1 0.202898 -0.044595 -0.068993 11.00000 0.04774 0.02748 = 0.05086 0.00307 0.01042 0.01066 N3 1 0.388002 0.746566 0.208970 11.00000 0.02921 0.02322 = 0.02397 0.00783 0.00642 0.00884 F1 2 0.172538 0.932826 0.215470 11.00000 0.03025 0.03283 = 0.06132 0.00563 0.00056 0.01101 F2 2 0.395034 1.043815 0.393837 11.00000 0.05485 0.03549 = 0.03794 0.00611 0.01770 0.01862 F3 2 0.451228 1.095240 0.245320 11.00000 0.05087 0.02777 = 0.04968 0.02062 0.01176 0.01294 C1 3 0.779670 0.654416 0.654434 11.00000 0.08665 0.06159 = 0.04141 0.02942 0.03416 0.04118 AFIX 137 H1A 4 0.808600 0.572328 0.674787 11.00000 -1.50000 H1B 4 0.628890 0.635567 0.619935 11.00000 -1.50000 H1C 4 0.837346 0.739501 0.727324 11.00000 -1.50000 AFIX 0 C2 3 0.878131 0.678738 0.564309 11.00000 0.04858 0.02645 = 0.02833 0.00880 0.01240 0.01521 C3 3 0.769965 0.703493 0.462588 11.00000 0.03174 0.03012 = 0.03091 0.01116 0.01314 0.01472 AFIX 43 H3 4 0.630653 0.705477 0.449744 11.00000 -1.20000 AFIX 0 C4 3 0.861848 0.725367 0.379432 11.00000 0.02472 0.01933 = 0.02602 0.00520 0.00667 0.00564 C5 3 0.747332 0.761244 0.273323 11.00000 0.02631 0.02395 = 0.02753 0.00892 0.00897 0.00585 AFIX 13 H5 4 0.822122 0.752400 0.214328 11.00000 -1.20000 AFIX 0 C6 3 0.459446 0.524886 0.150441 11.00000 0.03349 0.02159 = 0.01894 0.00776 0.00756 0.00753 C7 3 0.604151 0.448636 0.144276 11.00000 0.03139 0.02766 = 0.02776 0.00764 0.00751 0.00899 AFIX 43 H7 4 0.749009 0.497619 0.179996 11.00000 -1.20000 AFIX 0 C8 3 0.536311 0.302456 0.086349 11.00000 0.04079 0.02783 = 0.02798 0.00864 0.01119 0.01532 AFIX 43 H8 4 0.634812 0.251285 0.082461 11.00000 -1.20000 AFIX 0 C9 3 0.324239 0.229781 0.033640 11.00000 0.04343 0.02220 = 0.02240 0.00628 0.00948 0.00889 C10 3 0.255324 0.076818 -0.023277 11.00000 0.04284 0.02751 = 0.03167 0.00679 0.00930 0.01105 C11 3 0.489943 0.879081 0.262287 11.00000 0.02994 0.02260 = 0.02426 0.00913 0.00717 0.00682 C12 3 0.721435 0.912845 0.310411 11.00000 0.02926 0.02289 = 0.03511 0.01104 0.00668 0.00580 AFIX 23 H12A 4 0.778115 0.960810 0.398870 11.00000 -1.20000 H12B 4 0.789475 0.973356 0.272560 11.00000 -1.20000 AFIX 0 C13 3 1.081526 0.675912 0.580712 11.00000 0.04332 0.02797 = 0.03343 0.00912 -0.00255 0.01105 AFIX 43 H13 4 1.158383 0.659871 0.649843 11.00000 -1.20000 AFIX 0 C14 3 1.172938 0.695935 0.498586 11.00000 0.02439 0.03158 = 0.05165 0.01265 0.00191 0.00776 AFIX 43 H14 4 1.311871 0.693141 0.511205 11.00000 -1.20000 AFIX 0 C15 3 1.063924 0.720276 0.397066 11.00000 0.02510 0.02677 = 0.04159 0.01093 0.01156 0.00533 AFIX 43 H15 4 1.127537 0.733337 0.340137 11.00000 -1.20000 AFIX 0 C16 3 0.375900 0.986788 0.278040 11.00000 0.03116 0.02296 = 0.03244 0.00769 0.00490 0.00652 C17 3 0.246190 0.451605 0.095163 11.00000 0.03153 0.02511 = 0.02523 0.00793 0.00758 0.00931 AFIX 43 H17 4 0.147304 0.502735 0.097189 11.00000 -1.20000 AFIX 0 C18 3 0.179305 0.305619 0.037854 11.00000 0.03457 0.02581 = 0.02528 0.00598 0.00657 0.00516 AFIX 43 H18 4 0.034587 0.256435 0.001167 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_TKP_AD_CF32_0m_a.res in P-1 REM wR2 = 0.0990, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0370 for 3087 Fo > 4sig(Fo) and 0.0409 for all 3427 data REM 218 parameters refined using 0 restraints END WGHT 0.0464 0.2291 REM Highest difference peak 0.258, deepest hole -0.212, 1-sigma level 0.039 Q1 1 0.4325 0.9295 0.2665 11.00000 0.05 0.26 Q2 1 0.7940 0.7331 0.3239 11.00000 0.05 0.23 Q3 1 0.7462 0.8383 0.2967 11.00000 0.05 0.23 Q4 1 0.2571 0.2637 0.0436 11.00000 0.05 0.20 Q5 1 0.9599 0.6471 0.5636 11.00000 0.05 0.19 Q6 1 0.6822 0.5731 0.6193 11.00000 0.05 0.18 Q7 1 0.5936 0.9053 0.2849 11.00000 0.05 0.17 Q8 1 0.4229 0.2575 0.0856 11.00000 0.05 0.17 Q9 1 0.5246 0.4831 0.1587 11.00000 0.05 0.16 Q10 1 0.9459 0.7017 0.3774 11.00000 0.05 0.16 Q11 1 0.9681 0.7495 0.3933 11.00000 0.05 0.16 Q12 1 0.8431 0.7582 0.4358 11.00000 0.05 0.15 Q13 1 0.6605 0.7157 0.6567 11.00000 0.05 0.15 Q14 1 0.4440 0.8238 0.2037 11.00000 0.05 0.15 Q15 1 0.3493 0.4782 0.1415 11.00000 0.05 0.15 Q16 1 0.4890 0.5983 0.1975 11.00000 0.05 0.15 Q17 1 0.2145 0.3783 0.0441 11.00000 0.05 0.15 Q18 1 0.5561 0.3709 0.1397 11.00000 0.05 0.14 Q19 1 0.5479 0.3836 0.0879 11.00000 0.05 0.14 Q20 1 0.2884 0.1618 0.0125 11.00000 0.05 0.14 ; _shelx_res_checksum 58650 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 N1 N 0.52774(15) 0.67046(10) 0.21203(9) 0.0282(2) Uani 1 1 d . . . . . N2 N 0.2029(2) -0.04460(12) -0.06899(12) 0.0459(3) Uani 1 1 d . . . . . N3 N 0.38800(15) 0.74657(10) 0.20897(8) 0.0260(2) Uani 1 1 d . . . . . F1 F 0.17254(12) 0.93283(8) 0.21547(8) 0.0469(2) Uani 1 1 d . . . . . F2 F 0.39503(13) 1.04381(8) 0.39384(7) 0.0430(2) Uani 1 1 d . . . . . F3 F 0.45123(13) 1.09524(8) 0.24532(7) 0.0423(2) Uani 1 1 d . . . . . C1 C 0.7797(3) 0.65442(19) 0.65443(14) 0.0550(4) Uani 1 1 d . . . . . H1A H 0.808600 0.572328 0.674787 0.083 Uiso 1 1 calc R U . . . H1B H 0.628890 0.635567 0.619935 0.083 Uiso 1 1 calc R U . . . H1C H 0.837346 0.739501 0.727324 0.083 Uiso 1 1 calc R U . . . C2 C 0.8781(2) 0.67874(13) 0.56431(11) 0.0342(3) Uani 1 1 d . . . . . C3 C 0.76996(19) 0.70349(12) 0.46259(11) 0.0294(2) Uani 1 1 d . . . . . H3 H 0.630653 0.705477 0.449744 0.035 Uiso 1 1 calc R U . . . C4 C 0.86185(17) 0.72537(11) 0.37943(10) 0.0246(2) Uani 1 1 d . . . . . C5 C 0.74733(17) 0.76124(12) 0.27332(10) 0.0263(2) Uani 1 1 d . . . . . H5 H 0.822122 0.752400 0.214328 0.032 Uiso 1 1 calc R U . . . C6 C 0.45945(18) 0.52489(11) 0.15044(9) 0.0250(2) Uani 1 1 d . . . . . C7 C 0.60415(19) 0.44864(13) 0.14428(10) 0.0299(2) Uani 1 1 d . . . . . H7 H 0.749009 0.497619 0.179996 0.036 Uiso 1 1 calc R U . . . C8 C 0.5363(2) 0.30246(13) 0.08635(11) 0.0318(3) Uani 1 1 d . . . . . H8 H 0.634812 0.251285 0.082461 0.038 Uiso 1 1 calc R U . . . C9 C 0.3242(2) 0.22978(12) 0.03364(10) 0.0302(3) Uani 1 1 d . . . . . C10 C 0.2553(2) 0.07682(13) -0.02328(11) 0.0355(3) Uani 1 1 d . . . . . C11 C 0.48994(18) 0.87908(12) 0.26229(10) 0.0260(2) Uani 1 1 d . . . . . C12 C 0.72144(18) 0.91285(12) 0.31041(11) 0.0302(3) Uani 1 1 d . . . . . H12A H 0.778115 0.960810 0.398870 0.036 Uiso 1 1 calc R U . . . H12B H 0.789475 0.973356 0.272560 0.036 Uiso 1 1 calc R U . . . C13 C 1.0815(2) 0.67591(13) 0.58071(12) 0.0386(3) Uani 1 1 d . . . . . H13 H 1.158383 0.659871 0.649843 0.046 Uiso 1 1 calc R U . . . C14 C 1.17294(19) 0.69593(14) 0.49859(13) 0.0388(3) Uani 1 1 d . . . . . H14 H 1.311871 0.693141 0.511205 0.047 Uiso 1 1 calc R U . . . C15 C 1.06392(18) 0.72028(12) 0.39707(12) 0.0318(3) Uani 1 1 d . . . . . H15 H 1.127537 0.733337 0.340137 0.038 Uiso 1 1 calc R U . . . C16 C 0.37590(19) 0.98679(12) 0.27804(11) 0.0309(3) Uani 1 1 d . . . . . C17 C 0.24619(18) 0.45160(12) 0.09516(10) 0.0278(2) Uani 1 1 d . . . . . H17 H 0.147304 0.502735 0.097189 0.033 Uiso 1 1 calc R U . . . C18 C 0.17931(19) 0.30562(12) 0.03785(10) 0.0306(3) Uani 1 1 d . . . . . H18 H 0.034587 0.256435 0.001167 0.037 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 N1 0.0257(5) 0.0221(5) 0.0307(5) 0.0060(4) 0.0034(4) 0.0072(4) N2 0.0477(7) 0.0275(6) 0.0509(7) 0.0031(5) 0.0104(6) 0.0107(5) N3 0.0292(5) 0.0232(5) 0.0240(4) 0.0078(4) 0.0064(4) 0.0088(4) F1 0.0303(4) 0.0328(4) 0.0613(5) 0.0056(4) 0.0006(4) 0.0110(3) F2 0.0548(5) 0.0355(4) 0.0379(4) 0.0061(3) 0.0177(4) 0.0186(4) F3 0.0509(5) 0.0278(4) 0.0497(5) 0.0206(3) 0.0118(4) 0.0129(3) C1 0.0866(12) 0.0616(10) 0.0414(8) 0.0294(7) 0.0342(8) 0.0412(9) C2 0.0486(7) 0.0265(6) 0.0283(6) 0.0088(5) 0.0124(5) 0.0152(5) C3 0.0317(6) 0.0301(6) 0.0309(6) 0.0112(5) 0.0131(5) 0.0147(5) C4 0.0247(5) 0.0193(5) 0.0260(5) 0.0052(4) 0.0067(4) 0.0056(4) C5 0.0263(5) 0.0239(5) 0.0275(5) 0.0089(4) 0.0090(4) 0.0059(4) C6 0.0335(6) 0.0216(5) 0.0189(5) 0.0078(4) 0.0076(4) 0.0075(4) C7 0.0314(6) 0.0277(6) 0.0278(6) 0.0076(5) 0.0075(5) 0.0090(5) C8 0.0408(7) 0.0278(6) 0.0280(6) 0.0086(5) 0.0112(5) 0.0153(5) C9 0.0434(7) 0.0222(5) 0.0224(5) 0.0063(4) 0.0095(5) 0.0089(5) C10 0.0428(7) 0.0275(6) 0.0317(6) 0.0068(5) 0.0093(5) 0.0110(5) C11 0.0299(6) 0.0226(5) 0.0243(5) 0.0091(4) 0.0072(4) 0.0068(4) C12 0.0293(6) 0.0229(5) 0.0351(6) 0.0110(5) 0.0067(5) 0.0058(4) C13 0.0433(7) 0.0280(6) 0.0334(6) 0.0091(5) -0.0026(5) 0.0111(5) C14 0.0244(6) 0.0316(6) 0.0516(8) 0.0127(6) 0.0019(5) 0.0078(5) C15 0.0251(5) 0.0268(6) 0.0416(7) 0.0109(5) 0.0116(5) 0.0053(4) C16 0.0312(6) 0.0230(5) 0.0324(6) 0.0077(5) 0.0049(5) 0.0065(4) C17 0.0315(6) 0.0251(5) 0.0252(5) 0.0079(4) 0.0076(4) 0.0093(4) C18 0.0346(6) 0.0258(6) 0.0253(5) 0.0060(4) 0.0066(4) 0.0052(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' 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' 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 N3 N1 C6 119.87(9) . . ? N3 N1 C5 113.38(9) . . ? C6 N1 C5 126.39(9) . . ? C11 N3 N1 108.07(9) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C13 C2 C3 118.18(12) . . ? C13 C2 C1 120.19(12) . . ? C3 C2 C1 121.63(13) . . ? C4 C3 C2 121.28(11) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C15 C4 C3 119.42(11) . . ? C15 C4 C5 119.78(10) . . ? C3 C4 C5 120.74(10) . . ? N1 C5 C4 113.08(9) . . ? N1 C5 C12 101.58(9) . . ? C4 C5 C12 112.99(9) . . ? N1 C5 H5 109.6 . . ? C4 C5 H5 109.6 . . ? C12 C5 H5 109.6 . . ? N1 C6 C17 120.70(10) . . ? N1 C6 C7 119.99(10) . . ? C17 C6 C7 119.31(10) . . ? C8 C7 C6 120.13(11) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.33(11) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C18 119.77(11) . . ? C8 C9 C10 119.82(11) . . ? C18 C9 C10 120.41(12) . . ? N2 C10 C9 179.06(15) . . ? N3 C11 C16 119.70(10) . . ? N3 C11 C12 115.70(10) . . ? C16 C11 C12 124.52(10) . . ? C11 C12 C5 101.26(9) . . ? C11 C12 H12A 111.5 . . ? C5 C12 H12A 111.5 . . ? C11 C12 H12B 111.5 . . ? C5 C12 H12B 111.5 . . ? H12A C12 H12B 109.3 . . ? C14 C13 C2 121.00(12) . . ? C14 C13 H13 119.5 . . ? C2 C13 H13 119.5 . . ? C13 C14 C15 120.53(12) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C4 C15 C14 119.57(12) . . ? C4 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? F1 C16 F3 107.76(10) . . ? F1 C16 F2 106.60(10) . . ? F3 C16 F2 106.35(9) . . ? F1 C16 C11 113.11(10) . . ? F3 C16 C11 111.45(10) . . ? F2 C16 C11 111.22(10) . . ? C18 C17 C6 120.31(11) . . ? C18 C17 H17 119.8 . . ? C6 C17 H17 119.8 . . ? C17 C18 C9 120.14(11) . . ? C17 C18 H18 119.9 . . ? C9 C18 H18 119.9 . . ? 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 N1 N3 1.3670(13) . ? N1 C6 1.3832(14) . ? N1 C5 1.4827(14) . ? N2 C10 1.1449(17) . ? N3 C11 1.2801(14) . ? F1 C16 1.3328(14) . ? F2 C16 1.3432(15) . ? F3 C16 1.3345(14) . ? C1 C2 1.5035(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C13 1.390(2) . ? C2 C3 1.3921(17) . ? C3 C4 1.3903(16) . ? C3 H3 0.9500 . ? C4 C15 1.3857(16) . ? C4 C5 1.5136(15) . ? C5 C12 1.5533(16) . ? C5 H5 1.0000 . ? C6 C17 1.4021(16) . ? C6 C7 1.4037(16) . ? C7 C8 1.3819(16) . ? C7 H7 0.9500 . ? C8 C9 1.3928(18) . ? C8 H8 0.9500 . ? C9 C18 1.3999(18) . ? C9 C10 1.4410(16) . ? C11 C16 1.4872(16) . ? C11 C12 1.4949(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.372(2) . ? C13 H13 0.9500 . ? C14 C15 1.3899(19) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C17 C18 1.3794(16) . ? C17 H17 0.9500 . ? C18 H18 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 C6 N1 N3 C11 -173.87(10) . . . . ? C5 N1 N3 C11 -0.34(13) . . . . ? C13 C2 C3 C4 -0.21(18) . . . . ? C1 C2 C3 C4 -179.76(12) . . . . ? C2 C3 C4 C15 1.01(17) . . . . ? C2 C3 C4 C5 -176.18(10) . . . . ? N3 N1 C5 C4 121.72(10) . . . . ? C6 N1 C5 C4 -65.25(14) . . . . ? N3 N1 C5 C12 0.34(12) . . . . ? C6 N1 C5 C12 173.37(10) . . . . ? C15 C4 C5 N1 137.70(11) . . . . ? C3 C4 C5 N1 -45.13(14) . . . . ? C15 C4 C5 C12 -107.60(12) . . . . ? C3 C4 C5 C12 69.58(13) . . . . ? N3 N1 C6 C17 -6.72(16) . . . . ? C5 N1 C6 C17 -179.34(10) . . . . ? N3 N1 C6 C7 174.19(10) . . . . ? C5 N1 C6 C7 1.57(17) . . . . ? N1 C6 C7 C8 177.79(10) . . . . ? C17 C6 C7 C8 -1.31(17) . . . . ? C6 C7 C8 C9 0.05(18) . . . . ? C7 C8 C9 C18 0.97(17) . . . . ? C7 C8 C9 C10 -178.09(11) . . . . ? N1 N3 C11 C16 -176.81(10) . . . . ? N1 N3 C11 C12 0.19(13) . . . . ? N3 C11 C12 C5 0.02(13) . . . . ? C16 C11 C12 C5 176.86(10) . . . . ? N1 C5 C12 C11 -0.20(11) . . . . ? C4 C5 C12 C11 -121.64(10) . . . . ? C3 C2 C13 C14 -0.45(19) . . . . ? C1 C2 C13 C14 179.10(13) . . . . ? C2 C13 C14 C15 0.3(2) . . . . ? C3 C4 C15 C14 -1.14(17) . . . . ? C5 C4 C15 C14 176.07(10) . . . . ? C13 C14 C15 C4 0.49(19) . . . . ? N3 C11 C16 F1 -10.48(16) . . . . ? C12 C11 C16 F1 172.80(10) . . . . ? N3 C11 C16 F3 -132.07(11) . . . . ? C12 C11 C16 F3 51.21(15) . . . . ? N3 C11 C16 F2 109.45(12) . . . . ? C12 C11 C16 F2 -67.27(14) . . . . ? N1 C6 C17 C18 -177.53(10) . . . . ? C7 C6 C17 C18 1.56(16) . . . . ? C6 C17 C18 C9 -0.55(17) . . . . ? C8 C9 C18 C17 -0.72(17) . . . . ? C10 C9 C18 C17 178.33(11) . . . . ?