#------------------------------------------------------------------------------ #$Date: 2024-11-04 03:32:33 +0200 (Mon, 04 Nov 2024) $ #$Revision: 295739 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160202.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_7160202 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 'C16 H12 Cl F3 N2' _chemical_formula_sum 'C16 H12 Cl F3 N2' _chemical_formula_weight 324.73 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _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 106.588(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.9662(18) _cell_length_b 6.6425(8) _cell_length_c 16.868(2) _cell_measurement_reflns_used 19966 _cell_measurement_temperature 305(2) _cell_measurement_theta_max 27.125 _cell_measurement_theta_min 2.235 _cell_volume 1499.7(3) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_collection 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'SHELXL 2018/3 (Sheldrick, 2015)' _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 305(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_unetI/netI 0.0409 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 19966 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.125 _diffrn_reflns_theta_min 2.235 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.438 _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.262 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 3314 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0495 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.4689P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1281 _refine_ls_wR_factor_ref 0.1441 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2330 _reflns_number_total 3314 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00844h2.cif _cod_data_source_block shelx_6d _cod_original_cell_volume 1499.8(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7160202 _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_0m_a.res in P2(1)/n shelx.res created by SHELXL-2018/3 at 21:50:32 on 20-Apr-2024 CELL 0.71073 13.9662 6.6425 16.8685 90.000 106.588 90.000 ZERR 4.00 0.0018 0.0008 0.0022 0.000 0.005 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC CL F N C H UNIT 4 12 8 64 48 MERG 2 EQIV $1 x+1/2, -y+1/2, z+1/2 HTAB C16 F3_$1 HTAB C16 F3_$1 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 20 TEMP 31.85 WGHT 0.061100 0.468900 FVAR 0.78897 CL1 1 0.593103 0.790989 0.630583 11.00000 0.05790 0.12513 = 0.07386 -0.00940 0.00670 -0.01484 F1 2 0.185125 0.267468 0.249982 11.00000 0.09763 0.12740 = 0.08837 -0.01855 0.04781 -0.00753 F2 2 0.126493 0.029739 0.304735 11.00000 0.27559 0.05760 = 0.10332 -0.01577 0.07668 -0.00001 F3 2 0.031294 0.248246 0.233654 11.00000 0.08233 0.17269 = 0.07972 -0.05184 -0.00113 -0.00107 N1 3 0.126276 0.416613 0.486646 11.00000 0.06760 0.05279 = 0.05452 -0.00426 0.01679 -0.01278 N2 3 0.118052 0.268125 0.429187 11.00000 0.05528 0.04971 = 0.05653 -0.00401 0.01409 -0.00530 C1 4 0.468516 0.738356 0.581111 11.00000 0.05306 0.07533 = 0.04300 -0.00359 0.01460 -0.00530 C2 4 0.402559 0.892518 0.552358 11.00000 0.06798 0.05147 = 0.07801 -0.00217 0.01573 -0.01090 AFIX 43 H2 5 0.424303 1.025472 0.558425 11.00000 -1.20000 AFIX 0 C3 4 0.303479 0.848364 0.514285 11.00000 0.06233 0.04388 = 0.07352 0.00494 0.01264 0.00132 AFIX 43 H3 5 0.258583 0.952699 0.494591 11.00000 -1.20000 AFIX 0 C4 4 0.270034 0.652243 0.504992 11.00000 0.05538 0.04142 = 0.04422 0.00008 0.01531 0.00121 C5 4 0.161647 0.608065 0.460058 11.00000 0.05610 0.04199 = 0.06006 -0.00020 0.01084 -0.00073 C6 4 0.124747 0.367904 0.566610 11.00000 0.04217 0.06749 = 0.05542 -0.00055 0.01678 -0.00149 C7 4 0.142768 0.514871 0.627446 11.00000 0.06418 0.08506 = 0.06762 -0.01167 0.02787 -0.00856 AFIX 43 H7 5 0.155241 0.646739 0.614736 11.00000 -1.20000 AFIX 0 C8 4 0.142235 0.465876 0.706854 11.00000 0.07007 0.12875 = 0.06767 -0.01980 0.03160 -0.00534 AFIX 43 H8 5 0.154837 0.565032 0.747449 11.00000 -1.20000 AFIX 0 C9 4 0.123284 0.272200 0.726472 11.00000 0.08990 0.14141 = 0.07294 0.01827 0.04693 0.01803 AFIX 43 H9 5 0.123416 0.239788 0.780138 11.00000 -1.20000 AFIX 0 C10 4 0.144358 0.568825 0.366977 11.00000 0.07009 0.05458 = 0.05453 0.00789 0.00321 -0.00405 AFIX 23 H10A 5 0.085965 0.639862 0.333749 11.00000 -1.20000 H10B 5 0.202118 0.606688 0.349265 11.00000 -1.20000 AFIX 0 C11 4 0.128717 0.346824 0.363125 11.00000 0.05286 0.05143 = 0.05193 0.00169 0.00855 0.00017 C12 4 0.118699 0.221203 0.289224 11.00000 0.07527 0.06379 = 0.05881 -0.00453 0.01825 -0.00047 C13 4 0.104067 0.126299 0.665921 11.00000 0.09657 0.09734 = 0.09485 0.02416 0.05684 0.01257 AFIX 43 H13 5 0.090646 -0.004836 0.678861 11.00000 -1.20000 AFIX 0 C14 4 0.104512 0.172496 0.586467 11.00000 0.06517 0.07070 = 0.07098 0.00676 0.03209 0.00175 AFIX 43 H14 5 0.091263 0.072859 0.546058 11.00000 -1.20000 AFIX 0 C15 4 0.338222 0.500420 0.534384 11.00000 0.06130 0.04383 = 0.06016 0.00009 0.01497 0.00364 AFIX 43 H15 5 0.316847 0.367214 0.528641 11.00000 -1.20000 AFIX 0 C16 4 0.437282 0.542133 0.572046 11.00000 0.06118 0.06279 = 0.05331 0.00525 0.01442 0.01163 AFIX 43 H16 5 0.482566 0.438113 0.591153 11.00000 -1.20000 AFIX 0 H5 5 0.119079 0.720964 0.469520 11.00000 0.05753 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM mo_TKP_AD_CF3_0m_a.res in P2(1)/n REM wR2 = 0.1441, GooF = S = 1.040, Restrained GooF = 1.040 for all data REM R1 = 0.0495 for 2330 Fo > 4sig(Fo) and 0.0728 for all 3314 data REM 203 parameters refined using 0 restraints END WGHT 0.0607 0.4729 REM Highest difference peak 0.262, deepest hole -0.247, 1-sigma level 0.044 Q1 1 0.1945 0.1218 0.2915 11.00000 0.05 0.26 Q2 1 0.0947 0.3014 0.2128 11.00000 0.05 0.23 Q3 1 0.0525 0.0992 0.2760 11.00000 0.05 0.22 Q4 1 0.5534 0.8883 0.6594 11.00000 0.05 0.16 Q5 1 0.4333 0.8134 0.5932 11.00000 0.05 0.15 Q6 1 0.1599 0.6927 0.7455 11.00000 0.05 0.14 Q7 1 0.1769 0.7694 0.7421 11.00000 0.05 0.13 Q8 1 0.4315 1.0285 0.6066 11.00000 0.05 0.13 Q9 1 0.1256 -0.0060 0.3172 11.00000 0.05 0.12 Q10 1 0.5984 0.9524 0.6102 11.00000 0.05 0.12 Q11 1 0.1578 0.3488 0.3841 11.00000 0.05 0.12 Q12 1 0.4419 0.6387 0.5995 11.00000 0.05 0.12 Q13 1 0.2268 0.9590 0.5408 11.00000 0.05 0.12 Q14 1 0.1810 0.3753 0.5010 11.00000 0.05 0.11 Q15 1 0.1987 0.6100 0.7503 11.00000 0.05 0.11 Q16 1 0.1051 0.6534 0.7121 11.00000 0.05 0.11 Q17 1 0.3895 0.9966 0.5971 11.00000 0.05 0.11 Q18 1 0.1345 0.7369 0.5779 11.00000 0.05 0.11 Q19 1 0.6001 0.7451 0.7213 11.00000 0.05 0.11 Q20 1 0.4664 0.9891 0.5028 11.00000 0.05 0.11 ; _shelx_res_checksum 88604 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 Cl1 Cl 0.59310(5) 0.79099(13) 0.63058(4) 0.0881(3) Uani 1 1 d . . . . . F1 F 0.18513(13) 0.2675(3) 0.24998(11) 0.1001(6) Uani 1 1 d . . . . . F2 F 0.1265(2) 0.0297(2) 0.30474(12) 0.1408(10) Uani 1 1 d . . . . . F3 F 0.03129(13) 0.2482(3) 0.23365(11) 0.1166(7) Uani 1 1 d . . . . . N1 N 0.12628(14) 0.4166(3) 0.48665(11) 0.0584(4) Uani 1 1 d . . . . . N2 N 0.11805(13) 0.2681(2) 0.42919(11) 0.0542(4) Uani 1 1 d . . . . . C1 C 0.46852(16) 0.7384(3) 0.58111(13) 0.0569(5) Uani 1 1 d . . . . . C2 C 0.40256(18) 0.8925(3) 0.55236(15) 0.0669(6) Uani 1 1 d . . . . . H2 H 0.424303 1.025472 0.558425 0.080 Uiso 1 1 calc R U . . . C3 C 0.30348(17) 0.8484(3) 0.51428(14) 0.0613(5) Uani 1 1 d . . . . . H3 H 0.258583 0.952699 0.494591 0.074 Uiso 1 1 calc R U . . . C4 C 0.27003(14) 0.6522(3) 0.50499(11) 0.0468(4) Uani 1 1 d . . . . . C5 C 0.16165(16) 0.6081(3) 0.46006(13) 0.0539(5) Uani 1 1 d . . . . . C6 C 0.12475(14) 0.3679(3) 0.56661(13) 0.0544(5) Uani 1 1 d . . . . . C7 C 0.14277(17) 0.5149(4) 0.62745(15) 0.0704(6) Uani 1 1 d . . . . . H7 H 0.155241 0.646739 0.614736 0.084 Uiso 1 1 calc R U . . . C8 C 0.1422(2) 0.4659(5) 0.70685(17) 0.0864(8) Uani 1 1 d . . . . . H8 H 0.154837 0.565032 0.747449 0.104 Uiso 1 1 calc R U . . . C9 C 0.1233(2) 0.2722(6) 0.7265(2) 0.0965(10) Uani 1 1 d . . . . . H9 H 0.123416 0.239788 0.780138 0.116 Uiso 1 1 calc R U . . . C10 C 0.14436(18) 0.5688(3) 0.36698(13) 0.0628(6) Uani 1 1 d . . . . . H10A H 0.085965 0.639862 0.333749 0.075 Uiso 1 1 calc R U . . . H10B H 0.202118 0.606688 0.349265 0.075 Uiso 1 1 calc R U . . . C11 C 0.12872(15) 0.3468(3) 0.36312(13) 0.0534(5) Uani 1 1 d . . . . . C12 C 0.11870(19) 0.2212(4) 0.28922(14) 0.0661(6) Uani 1 1 d . . . . . C13 C 0.1041(2) 0.1263(5) 0.6659(2) 0.0901(9) Uani 1 1 d . . . . . H13 H 0.090646 -0.004836 0.678861 0.108 Uiso 1 1 calc R U . . . C14 C 0.10451(17) 0.1725(4) 0.58647(15) 0.0663(6) Uani 1 1 d . . . . . H14 H 0.091263 0.072859 0.546058 0.080 Uiso 1 1 calc R U . . . C15 C 0.33822(16) 0.5004(3) 0.53438(13) 0.0556(5) Uani 1 1 d . . . . . H15 H 0.316847 0.367214 0.528641 0.067 Uiso 1 1 calc R U . . . C16 C 0.43728(16) 0.5421(3) 0.57205(13) 0.0595(5) Uani 1 1 d . . . . . H16 H 0.482566 0.438113 0.591153 0.071 Uiso 1 1 calc R U . . . H5 H 0.1191(16) 0.721(3) 0.4695(13) 0.058(6) Uiso 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 Cl1 0.0579(4) 0.1251(6) 0.0739(4) -0.0094(4) 0.0067(3) -0.0148(3) F1 0.0976(12) 0.1274(14) 0.0884(11) -0.0186(9) 0.0478(10) -0.0075(10) F2 0.276(3) 0.0576(10) 0.1033(13) -0.0158(9) 0.0767(17) 0.0000(13) F3 0.0823(11) 0.1727(19) 0.0797(11) -0.0518(11) -0.0011(9) -0.0011(11) N1 0.0676(11) 0.0528(10) 0.0545(10) -0.0043(8) 0.0168(8) -0.0128(8) N2 0.0553(9) 0.0497(9) 0.0565(10) -0.0040(8) 0.0141(8) -0.0053(7) C1 0.0531(11) 0.0753(14) 0.0430(10) -0.0036(9) 0.0146(9) -0.0053(10) C2 0.0680(14) 0.0515(12) 0.0780(15) -0.0022(11) 0.0157(12) -0.0109(10) C3 0.0623(13) 0.0439(11) 0.0735(14) 0.0049(10) 0.0126(11) 0.0013(9) C4 0.0554(10) 0.0414(10) 0.0442(10) 0.0001(8) 0.0153(8) 0.0012(8) C5 0.0561(11) 0.0420(10) 0.0601(12) -0.0002(9) 0.0108(10) -0.0007(9) C6 0.0422(10) 0.0675(13) 0.0554(12) -0.0005(10) 0.0168(9) -0.0015(9) C7 0.0642(13) 0.0851(16) 0.0676(15) -0.0117(12) 0.0279(12) -0.0086(12) C8 0.0701(16) 0.129(3) 0.0677(16) -0.0198(17) 0.0316(13) -0.0053(16) C9 0.090(2) 0.141(3) 0.0729(18) 0.0183(19) 0.0469(16) 0.0180(19) C10 0.0701(13) 0.0546(12) 0.0545(12) 0.0079(10) 0.0032(10) -0.0040(10) C11 0.0529(11) 0.0514(11) 0.0519(11) 0.0017(9) 0.0086(9) 0.0002(9) C12 0.0753(15) 0.0638(14) 0.0588(13) -0.0045(10) 0.0183(12) -0.0005(11) C13 0.097(2) 0.097(2) 0.095(2) 0.0242(17) 0.0568(17) 0.0126(16) C14 0.0652(13) 0.0707(14) 0.0710(14) 0.0068(12) 0.0321(11) 0.0017(11) C15 0.0613(12) 0.0438(10) 0.0602(12) 0.0001(9) 0.0150(10) 0.0036(9) C16 0.0612(12) 0.0628(13) 0.0533(12) 0.0052(10) 0.0144(10) 0.0116(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.1484 0.1585 '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 N2 N1 C6 119.89(17) . . ? N2 N1 C5 111.94(16) . . ? C6 N1 C5 126.29(17) . . ? C11 N2 N1 108.46(16) . . ? C16 C1 C2 120.8(2) . . ? C16 C1 Cl1 119.26(17) . . ? C2 C1 Cl1 119.98(18) . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C15 118.29(19) . . ? C3 C4 C5 119.85(18) . . ? C15 C4 C5 121.81(17) . . ? N1 C5 C4 112.77(16) . . ? N1 C5 C10 101.23(16) . . ? C4 C5 C10 112.70(18) . . ? N1 C5 H5 109.4(12) . . ? C4 C5 H5 109.3(12) . . ? C10 C5 H5 111.3(13) . . ? C7 C6 C14 119.1(2) . . ? C7 C6 N1 120.2(2) . . ? C14 C6 N1 120.7(2) . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C13 119.4(3) . . ? C8 C9 H9 120.3 . . ? C13 C9 H9 120.3 . . ? C11 C10 C5 100.97(17) . . ? C11 C10 H10A 111.6 . . ? C5 C10 H10A 111.6 . . ? C11 C10 H10B 111.6 . . ? C5 C10 H10B 111.6 . . ? H10A C10 H10B 109.4 . . ? N2 C11 C12 119.99(19) . . ? N2 C11 C10 114.79(19) . . ? C12 C11 C10 125.10(19) . . ? F2 C12 F1 107.4(2) . . ? F2 C12 F3 106.5(2) . . ? F1 C12 F3 104.6(2) . . ? F2 C12 C11 113.7(2) . . ? F1 C12 C11 112.4(2) . . ? F3 C12 C11 111.6(2) . . ? C14 C13 C9 120.7(3) . . ? C14 C13 H13 119.6 . . ? C9 C13 H13 119.6 . . ? C13 C14 C6 120.0(3) . . ? C13 C14 H14 120.0 . . ? C6 C14 H14 120.0 . . ? C16 C15 C4 121.28(19) . . ? C16 C15 H15 119.4 . . ? C4 C15 H15 119.4 . . ? C1 C16 C15 119.3(2) . . ? C1 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? 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 Cl1 C1 1.737(2) . ? F1 C12 1.321(3) . ? F2 C12 1.297(3) . ? F3 C12 1.322(3) . ? N1 N2 1.365(2) . ? N1 C6 1.393(3) . ? N1 C5 1.480(3) . ? N2 C11 1.278(3) . ? C1 C16 1.369(3) . ? C1 C2 1.370(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9300 . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C15 1.378(3) . ? C4 C5 1.516(3) . ? C5 C10 1.541(3) . ? C5 H5 1.00(2) . ? C6 C7 1.386(3) . ? C6 C14 1.390(3) . ? C7 C8 1.381(4) . ? C7 H7 0.9300 . ? C8 C9 1.373(5) . ? C8 H8 0.9300 . ? C9 C13 1.378(5) . ? C9 H9 0.9300 . ? C10 C11 1.489(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.473(3) . ? C13 C14 1.377(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.376(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C16 H16 F3 0.93 2.62 3.291(3) 130.0 4_666 yes C16 H16 F3 0.93 2.62 3.291(3) 130.0 4_666 yes 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 N2 C11 -175.29(18) . . . . ? C5 N1 N2 C11 -9.9(2) . . . . ? C16 C1 C2 C3 0.4(3) . . . . ? Cl1 C1 C2 C3 -179.03(18) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C15 -0.3(3) . . . . ? C2 C3 C4 C5 -177.7(2) . . . . ? N2 N1 C5 C4 -104.91(19) . . . . ? C6 N1 C5 C4 59.3(3) . . . . ? N2 N1 C5 C10 15.8(2) . . . . ? C6 N1 C5 C10 179.99(19) . . . . ? C3 C4 C5 N1 -153.76(18) . . . . ? C15 C4 C5 N1 28.9(3) . . . . ? C3 C4 C5 C10 92.4(2) . . . . ? C15 C4 C5 C10 -84.9(2) . . . . ? N2 N1 C6 C7 173.71(19) . . . . ? C5 N1 C6 C7 10.6(3) . . . . ? N2 N1 C6 C14 -6.8(3) . . . . ? C5 N1 C6 C14 -169.9(2) . . . . ? C14 C6 C7 C8 1.1(3) . . . . ? N1 C6 C7 C8 -179.3(2) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C13 -0.4(4) . . . . ? N1 C5 C10 C11 -14.5(2) . . . . ? C4 C5 C10 C11 106.23(19) . . . . ? N1 N2 C11 C12 -177.25(19) . . . . ? N1 N2 C11 C10 -1.1(2) . . . . ? C5 C10 C11 N2 10.7(2) . . . . ? C5 C10 C11 C12 -173.4(2) . . . . ? N2 C11 C12 F2 -17.9(3) . . . . ? C10 C11 C12 F2 166.4(2) . . . . ? N2 C11 C12 F1 -140.2(2) . . . . ? C10 C11 C12 F1 44.1(3) . . . . ? N2 C11 C12 F3 102.6(3) . . . . ? C10 C11 C12 F3 -73.1(3) . . . . ? C8 C9 C13 C14 0.5(5) . . . . ? C9 C13 C14 C6 0.2(4) . . . . ? C7 C6 C14 C13 -1.0(3) . . . . ? N1 C6 C14 C13 179.5(2) . . . . ? C3 C4 C15 C16 -0.1(3) . . . . ? C5 C4 C15 C16 177.28(19) . . . . ? C2 C1 C16 C15 -0.7(3) . . . . ? Cl1 C1 C16 C15 178.68(16) . . . . ? C4 C15 C16 C1 0.6(3) . . . . ?