#------------------------------------------------------------------------------ #$Date: 2024-11-04 03:32:33 +0200 (Mon, 04 Nov 2024) $ #$Revision: 295739 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160200.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_7160200 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 'C17 H15 F3 N2 O' _chemical_formula_sum 'C17 H15 F3 N2 O' _chemical_formula_weight 320.31 _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 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 90 _cell_angle_beta 94.244(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.2957(3) _cell_length_b 16.3601(12) _cell_length_c 18.4809(13) _cell_measurement_reflns_used 25874 _cell_measurement_temperature 139(2) _cell_measurement_theta_max 27.184 _cell_measurement_theta_min 2.490 _cell_volume 1596.76(19) _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 139(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 25874 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.184 _diffrn_reflns_theta_min 2.490 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.332 _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.368 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3538 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0559 _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^)+(0.0674P)^2^+0.5569P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1432 _refine_ls_wR_factor_ref 0.1588 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2590 _reflns_number_total 3538 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00844h2.cif _cod_data_source_block shelx_6a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7160200 _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_cf3_1_a_0m_a.res in P2(1)/c shelx.res created by SHELXL-2018/3 at 22:10:24 on 20-Apr-2024 CELL 0.71073 5.2957 16.3601 18.4809 90.000 94.244 90.000 ZERR 27.00 0.0003 0.0012 0.0013 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC O F N C H UNIT 4 12 8 68 60 MERG 2 MORE -1 FMAP 2 53 53 PLAN 20 ACTA BOND BOND $H CONF LIST 4 L.S. 20 TEMP -134.15 WGHT 0.067400 0.556900 FVAR 0.77651 O1 1 -0.120266 0.003557 0.370496 11.00000 0.07983 0.05898 = 0.09383 -0.00421 -0.01984 -0.02285 F1 2 0.558020 0.477767 0.349425 11.00000 0.25631 0.11119 = 0.17733 0.09058 -0.13694 -0.08970 F2 2 0.944356 0.465397 0.374652 11.00000 0.17790 0.14489 = 0.24314 0.08972 0.08967 -0.03150 F3 2 0.728928 0.518859 0.448338 11.00000 0.19655 0.05385 = 0.14169 0.00010 -0.02243 -0.02777 N1 3 0.495102 0.267261 0.456258 11.00000 0.05198 0.04514 = 0.04804 0.00476 -0.00639 -0.00847 N2 3 0.492845 0.335598 0.414411 11.00000 0.06336 0.04462 = 0.04683 0.00201 -0.00281 -0.00550 C1 4 0.685879 0.378949 0.434268 11.00000 0.06387 0.04731 = 0.04982 -0.00023 0.00127 -0.01102 C2 4 0.721964 0.459297 0.400395 11.00000 0.10702 0.06332 = 0.08063 0.01505 -0.02041 -0.03394 C3 4 0.855548 0.343529 0.494037 11.00000 0.05005 0.05553 = 0.05821 -0.00038 0.00138 -0.00969 AFIX 23 H3A 5 0.856972 0.377303 0.538515 11.00000 -1.20000 H3B 5 1.030886 0.337417 0.479596 11.00000 -1.20000 AFIX 0 C4 4 0.729974 0.259512 0.504835 11.00000 0.04265 0.04690 = 0.04856 -0.00189 0.00077 -0.00170 AFIX 13 H4 5 0.838876 0.215240 0.486566 11.00000 -1.20000 AFIX 0 C5 4 0.681873 0.243042 0.582722 11.00000 0.04423 0.04745 = 0.04445 -0.00494 -0.00171 -0.00720 C6 4 0.828342 0.186430 0.622520 11.00000 0.06079 0.06107 = 0.05880 0.00434 -0.00292 0.00156 AFIX 43 H6 5 0.954496 0.156337 0.600033 11.00000 -1.20000 AFIX 0 C7 4 0.791350 0.173544 0.695138 11.00000 0.09778 0.07841 = 0.05786 0.01670 -0.01075 -0.00574 AFIX 43 H7 5 0.893538 0.134888 0.722178 11.00000 -1.20000 AFIX 0 C8 4 0.609891 0.215752 0.728158 11.00000 0.10200 0.09615 = 0.04540 0.00042 0.00282 -0.02425 AFIX 43 H8 5 0.585918 0.206589 0.777946 11.00000 -1.20000 AFIX 0 C9 4 0.463001 0.271191 0.689328 11.00000 0.08817 0.09966 = 0.05951 -0.01378 0.02211 0.00065 AFIX 43 H9 5 0.335668 0.300337 0.712175 11.00000 -1.20000 AFIX 0 C10 4 0.498065 0.285392 0.616625 11.00000 0.06582 0.07702 = 0.05541 -0.00447 0.00492 0.01077 AFIX 43 H10 5 0.395338 0.324347 0.590127 11.00000 -1.20000 AFIX 0 C11 4 0.343726 0.200412 0.431413 11.00000 0.04439 0.04640 = 0.04157 -0.00301 0.00416 -0.00345 C12 4 0.360636 0.126256 0.467775 11.00000 0.05255 0.05119 = 0.05382 0.00156 -0.00763 -0.00343 AFIX 43 H12 5 0.480330 0.119524 0.508220 11.00000 -1.20000 AFIX 0 C13 4 0.204058 0.062123 0.445403 11.00000 0.06207 0.04493 = 0.06828 0.00616 -0.00396 -0.00618 AFIX 43 H13 5 0.217666 0.011544 0.470642 11.00000 -1.20000 AFIX 0 C14 4 0.028521 0.070420 0.387053 11.00000 0.05377 0.05005 = 0.06037 -0.00783 -0.00093 -0.00952 C15 4 0.011578 0.144017 0.350341 11.00000 0.05304 0.06090 = 0.04734 -0.00252 -0.00524 -0.00645 AFIX 43 H15 5 -0.108590 0.150438 0.309966 11.00000 -1.20000 AFIX 0 C16 4 0.168902 0.208483 0.372104 11.00000 0.05439 0.05091 = 0.04265 0.00357 0.00004 -0.00466 AFIX 43 H16 5 0.157020 0.258659 0.346202 11.00000 -1.20000 AFIX 0 C17 4 -0.303534 0.009837 0.310721 11.00000 0.08798 0.08904 = 0.09929 -0.01454 -0.02689 -0.03289 AFIX 137 H17A 5 -0.421436 0.054329 0.319423 11.00000 -1.50000 H17B 5 -0.397185 -0.041703 0.304987 11.00000 -1.50000 H17C 5 -0.218530 0.021221 0.266477 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_tkp_ad_cf3_1_a_0m_a.res in P2(1)/c REM wR2 = 0.1588, GooF = S = 1.046, Restrained GooF = 1.046 for all data REM R1 = 0.0559 for 2590 Fo > 4sig(Fo) and 0.0764 for all 3538 data REM 209 parameters refined using 0 restraints END WGHT 0.0673 0.5563 REM Highest difference peak 0.368, deepest hole -0.339, 1-sigma level 0.044 Q1 1 0.4896 0.4977 0.4070 11.00000 0.05 0.37 Q2 1 0.7678 0.4612 0.3396 11.00000 0.05 0.31 Q3 1 1.0080 0.4773 0.3794 11.00000 0.05 0.17 Q4 1 0.9278 0.4862 0.4306 11.00000 0.05 0.16 Q5 1 0.8119 0.2990 0.5020 11.00000 0.05 0.12 Q6 1 0.0462 0.2640 0.3610 11.00000 0.05 0.10 Q7 1 1.1778 0.2213 0.5951 11.00000 0.05 0.10 Q8 1 0.7829 0.4172 0.5646 11.00000 0.05 0.10 Q9 1 0.7135 0.5289 0.4682 11.00000 0.05 0.10 Q10 1 0.6984 0.2419 0.5430 11.00000 0.05 0.10 Q11 1 1.1381 0.1597 0.5794 11.00000 0.05 0.10 Q12 1 -0.0674 0.2222 0.4040 11.00000 0.05 0.09 Q13 1 -0.5372 -0.0627 0.3440 11.00000 0.05 0.09 Q14 1 0.4205 0.1248 0.5443 11.00000 0.05 0.09 Q15 1 0.5871 0.2000 0.3759 11.00000 0.05 0.09 Q16 1 -0.1030 0.0377 0.2406 11.00000 0.05 0.09 Q17 1 0.7251 0.2542 0.8437 11.00000 0.05 0.09 Q18 1 0.1343 0.2424 0.6830 11.00000 0.05 0.09 Q19 1 0.6401 0.5643 0.5213 11.00000 0.05 0.09 Q20 1 0.8040 0.2207 0.4400 11.00000 0.05 0.09 ; _shelx_res_checksum 81029 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 O1 O -0.1203(3) 0.00356(10) 0.37050(9) 0.0788(5) Uani 1 1 d . . . . . F1 F 0.5580(6) 0.47777(13) 0.34942(13) 0.1892(15) Uani 1 1 d . . . . . F2 F 0.9444(5) 0.46540(16) 0.37465(17) 0.1850(13) Uani 1 1 d . . . . . F3 F 0.7289(5) 0.51886(10) 0.44834(12) 0.1324(8) Uani 1 1 d . . . . . N1 N 0.4951(3) 0.26726(9) 0.45626(8) 0.0489(4) Uani 1 1 d . . . . . N2 N 0.4928(3) 0.33560(9) 0.41441(8) 0.0519(4) Uani 1 1 d . . . . . C1 C 0.6859(4) 0.37895(12) 0.43427(10) 0.0538(5) Uani 1 1 d . . . . . C2 C 0.7220(6) 0.45930(16) 0.40039(15) 0.0850(8) Uani 1 1 d . . . . . C3 C 0.8555(4) 0.34353(12) 0.49404(11) 0.0547(5) Uani 1 1 d . . . . . H3A H 0.856972 0.377303 0.538515 0.066 Uiso 1 1 calc R U . . . H3B H 1.030886 0.337417 0.479596 0.066 Uiso 1 1 calc R U . . . C4 C 0.7300(3) 0.25951(11) 0.50483(10) 0.0462(4) Uani 1 1 d . . . . . H4 H 0.838876 0.215240 0.486566 0.055 Uiso 1 1 calc R U . . . C5 C 0.6819(3) 0.24304(11) 0.58272(9) 0.0456(4) Uani 1 1 d . . . . . C6 C 0.8283(4) 0.18643(13) 0.62252(11) 0.0606(5) Uani 1 1 d . . . . . H6 H 0.954496 0.156337 0.600033 0.073 Uiso 1 1 calc R U . . . C7 C 0.7914(5) 0.17354(17) 0.69514(13) 0.0788(7) Uani 1 1 d . . . . . H7 H 0.893538 0.134888 0.722178 0.095 Uiso 1 1 calc R U . . . C8 C 0.6099(5) 0.21575(18) 0.72816(13) 0.0813(7) Uani 1 1 d . . . . . H8 H 0.585918 0.206589 0.777946 0.098 Uiso 1 1 calc R U . . . C9 C 0.4630(5) 0.27119(18) 0.68933(13) 0.0816(7) Uani 1 1 d . . . . . H9 H 0.335668 0.300337 0.712175 0.098 Uiso 1 1 calc R U . . . C10 C 0.4981(4) 0.28539(15) 0.61663(12) 0.0661(6) Uani 1 1 d . . . . . H10 H 0.395338 0.324347 0.590127 0.079 Uiso 1 1 calc R U . . . C11 C 0.3437(3) 0.20041(11) 0.43141(9) 0.0441(4) Uani 1 1 d . . . . . C12 C 0.3606(4) 0.12626(12) 0.46777(10) 0.0531(5) Uani 1 1 d . . . . . H12 H 0.480330 0.119524 0.508220 0.064 Uiso 1 1 calc R U . . . C13 C 0.2041(4) 0.06212(12) 0.44540(11) 0.0589(5) Uani 1 1 d . . . . . H13 H 0.217666 0.011544 0.470642 0.071 Uiso 1 1 calc R U . . . C14 C 0.0285(4) 0.07042(12) 0.38705(11) 0.0550(5) Uani 1 1 d . . . . . C15 C 0.0116(4) 0.14402(12) 0.35034(10) 0.0542(5) Uani 1 1 d . . . . . H15 H -0.108590 0.150438 0.309966 0.065 Uiso 1 1 calc R U . . . C16 C 0.1689(3) 0.20848(12) 0.37210(10) 0.0495(4) Uani 1 1 d . . . . . H16 H 0.157020 0.258659 0.346202 0.059 Uiso 1 1 calc R U . . . C17 C -0.3035(5) 0.00984(18) 0.31072(16) 0.0938(9) Uani 1 1 d . . . . . H17A H -0.421436 0.054329 0.319423 0.141 Uiso 1 1 calc R U . . . H17B H -0.397185 -0.041703 0.304987 0.141 Uiso 1 1 calc R U . . . H17C H -0.218530 0.021221 0.266477 0.141 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 0.0798(10) 0.0590(9) 0.0938(12) -0.0042(8) -0.0198(9) -0.0229(8) F1 0.256(3) 0.1112(15) 0.177(2) 0.0906(15) -0.137(2) -0.0897(17) F2 0.178(2) 0.145(2) 0.243(3) 0.090(2) 0.090(2) -0.0315(17) F3 0.197(2) 0.0539(9) 0.1417(16) 0.0001(10) -0.0224(15) -0.0278(11) N1 0.0520(8) 0.0451(8) 0.0480(8) 0.0048(6) -0.0064(7) -0.0085(6) N2 0.0634(10) 0.0446(8) 0.0468(8) 0.0020(7) -0.0028(7) -0.0055(7) C1 0.0639(12) 0.0473(10) 0.0498(10) -0.0002(8) 0.0013(9) -0.0110(8) C2 0.107(2) 0.0633(15) 0.0806(16) 0.0151(13) -0.0204(15) -0.0339(14) C3 0.0501(10) 0.0555(11) 0.0582(11) -0.0004(9) 0.0014(8) -0.0097(8) C4 0.0427(9) 0.0469(9) 0.0486(10) -0.0019(8) 0.0008(7) -0.0017(7) C5 0.0442(9) 0.0474(9) 0.0444(9) -0.0049(7) -0.0017(7) -0.0072(7) C6 0.0608(12) 0.0611(12) 0.0588(12) 0.0043(9) -0.0029(9) 0.0016(9) C7 0.0978(18) 0.0784(16) 0.0579(13) 0.0167(12) -0.0107(13) -0.0057(14) C8 0.1020(19) 0.0961(19) 0.0454(12) 0.0004(12) 0.0028(12) -0.0242(16) C9 0.0882(17) 0.0997(19) 0.0595(14) -0.0138(13) 0.0221(13) 0.0006(15) C10 0.0658(13) 0.0770(14) 0.0554(12) -0.0045(10) 0.0049(10) 0.0108(11) C11 0.0444(9) 0.0464(9) 0.0416(9) -0.0030(7) 0.0042(7) -0.0034(7) C12 0.0525(10) 0.0512(11) 0.0538(11) 0.0016(8) -0.0076(8) -0.0034(8) C13 0.0621(12) 0.0449(10) 0.0683(12) 0.0062(9) -0.0040(10) -0.0062(9) C14 0.0538(11) 0.0500(10) 0.0604(11) -0.0078(9) -0.0009(9) -0.0095(8) C15 0.0530(10) 0.0609(12) 0.0473(10) -0.0025(8) -0.0052(8) -0.0065(9) C16 0.0544(10) 0.0509(10) 0.0426(9) 0.0036(8) 0.0000(8) -0.0047(8) C17 0.0880(18) 0.0890(19) 0.0993(19) -0.0145(15) -0.0269(15) -0.0329(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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 C14 O1 C17 117.72(18) . . ? N2 N1 C11 118.11(14) . . ? N2 N1 C4 112.71(14) . . ? C11 N1 C4 124.09(14) . . ? C1 N2 N1 108.70(15) . . ? N2 C1 C2 119.99(19) . . ? N2 C1 C3 115.08(17) . . ? C2 C1 C3 124.89(18) . . ? F1 C2 F2 107.3(3) . . ? F1 C2 F3 107.9(3) . . ? F2 C2 F3 102.0(2) . . ? F1 C2 C1 115.1(2) . . ? F2 C2 C1 111.8(3) . . ? F3 C2 C1 111.9(2) . . ? C1 C3 C4 101.54(14) . . ? C1 C3 H3A 111.5 . . ? C4 C3 H3A 111.5 . . ? C1 C3 H3B 111.5 . . ? C4 C3 H3B 111.5 . . ? H3A C3 H3B 109.3 . . ? N1 C4 C5 113.59(14) . . ? N1 C4 C3 101.25(14) . . ? C5 C4 C3 112.80(15) . . ? N1 C4 H4 109.6 . . ? C5 C4 H4 109.6 . . ? C3 C4 H4 109.6 . . ? C10 C5 C6 118.70(19) . . ? C10 C5 C4 121.24(17) . . ? C6 C5 C4 120.02(17) . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.7(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.6(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C10 120.5(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 120.2(2) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C16 118.78(16) . . ? C12 C11 N1 120.34(16) . . ? C16 C11 N1 120.83(16) . . ? C13 C12 C11 120.24(18) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.99(19) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? O1 C14 C13 116.11(18) . . ? O1 C14 C15 124.82(18) . . ? C13 C14 C15 119.07(17) . . ? C14 C15 C16 120.34(17) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.58(18) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? O1 C17 H17A 109.5 . . ? O1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C14 1.369(2) . ? O1 C17 1.419(3) . ? F1 C2 1.269(3) . ? F2 C2 1.306(4) . ? F3 C2 1.316(3) . ? N1 N2 1.359(2) . ? N1 C11 1.412(2) . ? N1 C4 1.485(2) . ? N2 C1 1.276(2) . ? C1 C2 1.474(3) . ? C1 C3 1.489(3) . ? C3 C4 1.546(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.505(2) . ? C4 H4 1.0000 . ? C5 C10 1.382(3) . ? C5 C6 1.384(3) . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C7 C8 1.364(4) . ? C7 H7 0.9500 . ? C8 C9 1.364(4) . ? C8 H8 0.9500 . ? C9 C10 1.389(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 C16 1.388(2) . ? C12 C13 1.382(3) . ? C12 H12 0.9500 . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C11 N1 N2 C1 -162.41(16) . . . . ? C4 N1 N2 C1 -6.6(2) . . . . ? N1 N2 C1 C2 -176.5(2) . . . . ? N1 N2 C1 C3 1.2(2) . . . . ? N2 C1 C2 F1 -3.6(4) . . . . ? C3 C1 C2 F1 179.0(3) . . . . ? N2 C1 C2 F2 -126.4(3) . . . . ? C3 C1 C2 F2 56.2(3) . . . . ? N2 C1 C2 F3 120.0(3) . . . . ? C3 C1 C2 F3 -57.4(4) . . . . ? N2 C1 C3 C4 4.2(2) . . . . ? C2 C1 C3 C4 -178.3(2) . . . . ? N2 N1 C4 C5 129.90(16) . . . . ? C11 N1 C4 C5 -76.0(2) . . . . ? N2 N1 C4 C3 8.70(19) . . . . ? C11 N1 C4 C3 162.84(16) . . . . ? C1 C3 C4 N1 -7.08(18) . . . . ? C1 C3 C4 C5 -128.84(17) . . . . ? N1 C4 C5 C10 -44.1(2) . . . . ? C3 C4 C5 C10 70.4(2) . . . . ? N1 C4 C5 C6 138.00(17) . . . . ? C3 C4 C5 C6 -107.5(2) . . . . ? C10 C5 C6 C7 -0.6(3) . . . . ? C4 C5 C6 C7 177.36(19) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C6 C5 C10 C9 0.2(3) . . . . ? C4 C5 C10 C9 -177.7(2) . . . . ? C8 C9 C10 C5 0.3(4) . . . . ? N2 N1 C11 C12 172.76(17) . . . . ? C4 N1 C11 C12 19.9(3) . . . . ? N2 N1 C11 C16 -9.8(2) . . . . ? C4 N1 C11 C16 -162.62(16) . . . . ? C16 C11 C12 C13 -0.6(3) . . . . ? N1 C11 C12 C13 176.98(18) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C17 O1 C14 C13 180.0(2) . . . . ? C17 O1 C14 C15 0.8(3) . . . . ? C12 C13 C14 O1 -178.71(19) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? O1 C14 C15 C16 179.06(19) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 -0.7(3) . . . . ? C12 C11 C16 C15 1.0(3) . . . . ? N1 C11 C16 C15 -176.55(17) . . . . ?