#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:03:30 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304787 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064325.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_7064325 loop_ _publ_author_name 'Jios, Eliana' 'Salvador Vallejo, Lorena E.' 'Echeverr\'ia, Gustavo A.' 'Piro, Oscar E.' 'Jios, Jorge L.' 'Naso, Luciana G.' 'Ulic, Sonia E.' _publ_section_title ; Hydrogen bonding and charge transfer in trifluoromethylated \b-aminoenones: a combined experimental and theoretical study ; _journal_issue 4 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1809 _journal_page_last 1823 _journal_paper_doi 10.1039/D5NJ04291G _journal_volume 50 _journal_year 2026 _chemical_formula_sum 'C14 H15 F3 N2 O4' _chemical_formula_weight 332.28 _chemical_name_systematic (Z)-3-(butylamino)-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one _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 _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2022-10-14 deposited with the CCDC. 2025-12-15 downloaded from the CCDC. ; _cell_angle_alpha 87.615(7) _cell_angle_beta 82.484(9) _cell_angle_gamma 78.659(8) _cell_formula_units_Z 2 _cell_length_a 5.3850(6) _cell_length_b 10.5397(9) _cell_length_c 14.0749(14) _cell_measurement_reflns_used 944 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 22.0970 _cell_measurement_theta_min 3.5000 _cell_volume 776.41(14) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'ORTEP for Windows (Farrugia, 2012)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 295(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0604 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.804 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_unetI/netI 0.0610 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.804 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5974 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.804 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.987 _diffrn_reflns_theta_min 3.497 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.421 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Petroleum ether' _exptl_crystal_size_max 0.779 _exptl_crystal_size_mid 0.430 _exptl_crystal_size_min 0.037 _refine_diff_density_max 0.390 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3328 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.1587 _refine_ls_R_factor_gt 0.0780 _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^)+(0.1364P)^2^+0.0945P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2149 _refine_ls_wR_factor_ref 0.2887 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1489 _reflns_number_total 3328 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04291g2.cif _cod_data_source_block shelx _cod_database_code 7064325 _shelx_shelxl_version_number 2014/7 _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_estimated_absorpt_t_min 0.907 _shelx_estimated_absorpt_t_max 0.995 _oxdiff_exptl_absorpt_empirical_full_min 0.767 _oxdiff_exptl_absorpt_empirical_full_max 1.199 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL shelxt_a.res in P-1 CELL 0.71073 5.3850 10.5397 14.0749 87.615 82.484 78.659 ZERR 2.00 0.0006 0.0009 0.0014 0.007 0.009 0.008 LATT 1 SFAC C H N O F UNIT 28 30 4 8 6 MERG 2 SIZE 0.037 0.430 0.779 TEMP 22 REM Crystal shape/color: plate/yellow MPLA 16 C1 > C10 O1 > O4 N1 N2 F1 F2 F3 SADI C11 C12 C12 C13 C13 C14 FMAP 2 PLAN -5 ACTA HTAB O1 O2 EQIV $1 -x+1, -y+1, -z+1 HTAB O1 O2_$1 HTAB N1 O2 HTAB N1 O1_$1 EQIV $2 -x-1, -y, -z+1 HTAB C4 O4_$2 HTAB C11 F2 HTAB C11 F1 CONF L.S. 10 WGHT 0.136400 0.094500 FVAR 7.57382 C1 1 0.189933 0.289673 0.408152 11.00000 0.04903 0.04538 = 0.04959 0.00433 -0.01066 -0.00915 C2 1 0.094926 0.312493 0.505279 11.00000 0.05242 0.04770 = 0.05856 0.00446 -0.01086 -0.01102 C3 1 -0.093920 0.248960 0.550739 11.00000 0.05591 0.06179 = 0.06163 0.00127 -0.00271 -0.01357 AFIX 43 H3 2 -0.156101 0.265360 0.614747 11.00000 -1.20000 AFIX 0 C4 1 -0.187804 0.163433 0.502457 11.00000 0.05503 0.05284 = 0.07594 0.01367 -0.00685 -0.01495 AFIX 43 H4 2 -0.313866 0.121406 0.532667 11.00000 -1.20000 AFIX 0 C5 1 -0.090972 0.140228 0.406829 11.00000 0.05358 0.04110 = 0.08070 0.00487 -0.01795 -0.00971 C6 1 0.092651 0.201179 0.360013 11.00000 0.05346 0.04949 = 0.05908 -0.00111 -0.00983 -0.00858 AFIX 43 H6 2 0.152665 0.183564 0.295997 11.00000 -1.20000 AFIX 0 C7 1 0.384833 0.361589 0.359008 11.00000 0.05456 0.04631 = 0.05231 0.00356 -0.01061 -0.01133 C8 1 0.495042 0.331479 0.263781 11.00000 0.05642 0.06289 = 0.05362 -0.00152 -0.00944 -0.01824 AFIX 43 H8 2 0.447694 0.264205 0.234174 11.00000 -1.20000 AFIX 0 C9 1 0.668781 0.396510 0.212565 11.00000 0.05997 0.06831 = 0.05342 0.00384 -0.01184 -0.01383 C10 1 0.780886 0.351551 0.113025 11.00000 0.08870 0.11557 = 0.05549 -0.00961 -0.00167 -0.03798 C11 1 0.921445 0.577355 0.199555 11.00000 0.08455 0.08603 = 0.08494 0.01200 -0.00262 -0.03224 AFIX 23 H11A 2 1.067669 0.570248 0.234398 11.00000 -1.20000 H11B 2 0.983739 0.546647 0.135162 11.00000 -1.20000 AFIX 0 C12 1 0.797735 0.713034 0.194199 11.00000 0.11848 0.13586 = 0.21497 0.07654 -0.02392 -0.03880 AFIX 23 H12A 2 0.761578 0.742985 0.259712 11.00000 -1.20000 H12B 2 0.926605 0.758348 0.162443 11.00000 -1.20000 AFIX 0 C13 1 0.586214 0.757678 0.153550 11.00000 0.12495 0.13629 = 0.30082 0.03798 -0.04133 -0.01941 AFIX 23 H13A 2 0.449444 0.724358 0.192051 11.00000 -1.20000 H13B 2 0.610586 0.716712 0.091687 11.00000 -1.20000 AFIX 0 C14 1 0.487430 0.897360 0.136702 11.00000 0.19739 0.13478 = 0.19059 0.01225 -0.07226 0.00854 AFIX 137 H14A 2 0.442273 0.940468 0.197047 11.00000 -1.50000 H14B 2 0.339344 0.907355 0.103761 11.00000 -1.50000 H14C 2 0.616772 0.934610 0.098400 11.00000 -1.50000 AFIX 0 N1 3 0.752682 0.494604 0.246384 11.00000 0.07352 0.08189 = 0.05280 0.00014 0.00185 -0.03257 AFIX 43 H1 2 0.698319 0.511889 0.305521 11.00000 -1.20000 AFIX 0 N2 3 -0.191789 0.049476 0.353321 11.00000 0.07415 0.05813 = 0.09417 -0.00415 -0.01267 -0.02318 O1 4 0.179770 0.394584 0.557357 11.00000 0.07776 0.07253 = 0.05562 -0.00453 -0.00587 -0.03442 AFIX 147 H1A 2 0.291301 0.425183 0.524242 11.00000 -1.50000 AFIX 0 O2 4 0.447872 0.447363 0.404521 11.00000 0.07174 0.05971 = 0.05952 -0.00629 -0.00094 -0.02763 O3 4 -0.094936 0.025829 0.271400 11.00000 0.14253 0.11907 = 0.10841 -0.04215 0.01175 -0.07744 O4 4 -0.365933 0.001318 0.391672 11.00000 0.08380 0.08876 = 0.12792 -0.00670 -0.01046 -0.04747 F1 5 0.735177 0.443347 0.046496 11.00000 0.14442 0.15867 = 0.05522 0.01965 -0.01378 -0.04711 F2 5 1.033935 0.313963 0.105517 11.00000 0.08601 0.15969 = 0.09028 -0.02671 0.01396 -0.01825 F3 5 0.689881 0.252598 0.086946 11.00000 0.14909 0.15406 = 0.07082 -0.03559 0.01434 -0.07827 HKLF 4 REM shelxt_a.res in P-1 REM R1 = 0.0780 for 1489 Fo > 4sig(Fo) and 0.1587 for all 3328 data REM 210 parameters refined using 3 restraints END WGHT 0.1197 0.1736 REM Highest difference peak 0.390, deepest hole -0.250, 1-sigma level 0.050 Q1 1 0.7669 0.8174 0.1225 11.00000 0.05 0.39 Q2 1 0.6068 0.7709 0.2237 11.00000 0.05 0.31 Q3 1 0.6099 0.7287 0.1390 11.00000 0.05 0.27 Q4 1 0.7985 0.6852 0.1206 11.00000 0.05 0.26 Q5 1 0.4143 0.2345 0.2124 11.00000 0.05 0.19 ; _shelx_res_checksum 54847 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 C1 C 0.1899(6) 0.2897(3) 0.4082(2) 0.0477(8) Uani 1 1 d . . . . . C2 C 0.0949(6) 0.3125(3) 0.5053(3) 0.0525(9) Uani 1 1 d . . . . . C3 C -0.0939(7) 0.2490(4) 0.5507(3) 0.0600(10) Uani 1 1 d . . . . . H3 H -0.1561 0.2654 0.6147 0.072 Uiso 1 1 calc R U . . . C4 C -0.1878(7) 0.1634(4) 0.5025(3) 0.0612(10) Uani 1 1 d . . . . . H4 H -0.3139 0.1214 0.5327 0.073 Uiso 1 1 calc R U . . . C5 C -0.0910(7) 0.1402(3) 0.4068(3) 0.0577(10) Uani 1 1 d . . . . . C6 C 0.0927(6) 0.2012(3) 0.3600(3) 0.0539(9) Uani 1 1 d . . . . . H6 H 0.1527 0.1836 0.2960 0.065 Uiso 1 1 calc R U . . . C7 C 0.3848(6) 0.3616(3) 0.3590(3) 0.0506(9) Uani 1 1 d . . . . . C8 C 0.4950(6) 0.3315(4) 0.2638(3) 0.0565(9) Uani 1 1 d . . . . . H8 H 0.4477 0.2642 0.2342 0.068 Uiso 1 1 calc R U . . . C9 C 0.6688(7) 0.3965(4) 0.2126(3) 0.0601(10) Uani 1 1 d . . . . . C10 C 0.7809(9) 0.3516(5) 0.1130(3) 0.0845(14) Uani 1 1 d . . . . . C11 C 0.9214(9) 0.5774(5) 0.1996(4) 0.0841(13) Uani 1 1 d D . . . . H11A H 1.0677 0.5702 0.2344 0.101 Uiso 1 1 calc R U . . . H11B H 0.9837 0.5466 0.1352 0.101 Uiso 1 1 calc R U . . . C12 C 0.7977(13) 0.7130(7) 0.1942(7) 0.156(3) Uani 1 1 d D . . . . H12A H 0.7616 0.7430 0.2597 0.188 Uiso 1 1 calc R U . . . H12B H 0.9266 0.7583 0.1624 0.188 Uiso 1 1 calc R U . . . C13 C 0.5862(15) 0.7577(8) 0.1536(8) 0.188(4) Uani 1 1 d D . . . . H13A H 0.4494 0.7244 0.1921 0.226 Uiso 1 1 calc R U . . . H13B H 0.6106 0.7167 0.0917 0.226 Uiso 1 1 calc R U . . . C14 C 0.4874(16) 0.8974(8) 0.1367(6) 0.176(3) Uani 1 1 d D . . . . H14A H 0.4423 0.9405 0.1970 0.264 Uiso 1 1 calc R U . . . H14B H 0.3393 0.9074 0.1038 0.264 Uiso 1 1 calc R U . . . H14C H 0.6168 0.9346 0.0984 0.264 Uiso 1 1 calc R U . . . N1 N 0.7527(6) 0.4946(3) 0.2464(2) 0.0679(9) Uani 1 1 d . . . . . H1 H 0.6983 0.5119 0.3055 0.081 Uiso 1 1 calc R U . . . N2 N -0.1918(7) 0.0495(3) 0.3533(3) 0.0738(10) Uani 1 1 d . . . . . O1 O 0.1798(5) 0.3946(3) 0.55736(18) 0.0660(8) Uani 1 1 d . . . . . H1A H 0.2913 0.4252 0.5242 0.099 Uiso 1 1 calc R U . . . O2 O 0.4479(5) 0.4474(2) 0.40452(18) 0.0621(8) Uani 1 1 d . . . . . O3 O -0.0949(7) 0.0258(4) 0.2714(3) 0.1175(15) Uani 1 1 d . . . . . O4 O -0.3659(6) 0.0013(3) 0.3917(3) 0.0960(11) Uani 1 1 d . . . . . F1 F 0.7352(6) 0.4433(4) 0.04650(19) 0.1175(11) Uani 1 1 d . . . . . F2 F 1.0339(5) 0.3140(3) 0.1055(2) 0.1143(12) Uani 1 1 d . . . . . F3 F 0.6899(6) 0.2526(3) 0.08695(19) 0.1195(12) 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 C1 0.0490(18) 0.045(2) 0.050(2) 0.0043(16) -0.0107(16) -0.0091(15) C2 0.0524(19) 0.048(2) 0.059(2) 0.0045(17) -0.0109(17) -0.0110(16) C3 0.056(2) 0.062(2) 0.062(2) 0.0013(19) -0.0027(18) -0.0136(18) C4 0.055(2) 0.053(2) 0.076(3) 0.014(2) -0.007(2) -0.0149(18) C5 0.054(2) 0.041(2) 0.081(3) 0.0049(18) -0.018(2) -0.0097(16) C6 0.0535(19) 0.049(2) 0.059(2) -0.0011(17) -0.0098(17) -0.0086(17) C7 0.0546(19) 0.046(2) 0.052(2) 0.0036(16) -0.0106(16) -0.0113(16) C8 0.056(2) 0.063(2) 0.054(2) -0.0015(18) -0.0094(17) -0.0182(18) C9 0.060(2) 0.068(3) 0.053(2) 0.0038(19) -0.0118(18) -0.0138(19) C10 0.089(3) 0.116(4) 0.055(3) -0.010(3) -0.002(2) -0.038(3) C11 0.085(3) 0.086(3) 0.085(3) 0.012(3) -0.003(2) -0.032(3) C12 0.118(5) 0.136(7) 0.215(8) 0.077(6) -0.024(5) -0.039(5) C13 0.125(6) 0.136(7) 0.301(13) 0.038(7) -0.041(7) -0.019(5) C14 0.197(8) 0.135(7) 0.191(9) 0.012(6) -0.072(7) 0.009(6) N1 0.074(2) 0.082(2) 0.0528(19) 0.0001(17) 0.0018(16) -0.0326(18) N2 0.074(2) 0.058(2) 0.094(3) -0.004(2) -0.013(2) -0.0232(18) O1 0.0778(18) 0.0725(18) 0.0556(16) -0.0045(14) -0.0059(13) -0.0344(14) O2 0.0717(16) 0.0597(16) 0.0595(16) -0.0063(13) -0.0009(13) -0.0276(13) O3 0.143(3) 0.119(3) 0.108(3) -0.042(3) 0.012(3) -0.077(3) O4 0.084(2) 0.089(2) 0.128(3) -0.007(2) -0.010(2) -0.0475(18) F1 0.144(3) 0.159(3) 0.0552(16) 0.0197(18) -0.0138(17) -0.047(2) F2 0.0860(19) 0.160(3) 0.090(2) -0.027(2) 0.0140(15) -0.0182(19) F3 0.149(3) 0.154(3) 0.0708(18) -0.0356(19) 0.0143(17) -0.078(2) 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' 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' 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 C6 C1 C2 118.0(3) . . ? C6 C1 C7 121.9(3) . . ? C2 C1 C7 120.1(3) . . ? O1 C2 C1 122.0(3) . . ? O1 C2 C3 117.5(3) . . ? C1 C2 C3 120.4(3) . . ? C4 C3 C2 120.8(4) . . ? C3 C4 C5 118.5(3) . . ? C4 C5 C6 122.3(3) . . ? C4 C5 N2 119.3(3) . . ? C6 C5 N2 118.4(4) . . ? C1 C6 C5 120.0(3) . . ? O2 C7 C8 121.6(3) . . ? O2 C7 C1 118.3(3) . . ? C8 C7 C1 120.1(3) . . ? C9 C8 C7 123.5(3) . . ? N1 C9 C8 124.3(3) . . ? N1 C9 C10 117.2(3) . . ? C8 C9 C10 118.5(4) . . ? F2 C10 F3 106.7(4) . . ? F2 C10 F1 106.2(4) . . ? F3 C10 F1 106.2(4) . . ? F2 C10 C9 111.9(4) . . ? F3 C10 C9 112.6(4) . . ? F1 C10 C9 112.8(4) . . ? C12 C11 N1 113.3(4) . . ? C13 C12 C11 125.1(8) . . ? C12 C13 C14 123.4(8) . . ? C9 N1 C11 130.6(4) . . ? O4 N2 O3 122.7(4) . . ? O4 N2 C5 119.3(4) . . ? O3 N2 C5 118.0(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 C1 C6 1.393(4) . ? C1 C2 1.409(5) . ? C1 C7 1.495(5) . ? C2 O1 1.338(4) . ? C2 C3 1.398(5) . ? C3 C4 1.360(5) . ? C4 C5 1.392(5) . ? C5 C6 1.367(5) . ? C5 N2 1.466(5) . ? C7 O2 1.252(4) . ? C7 C8 1.415(5) . ? C8 C9 1.378(5) . ? C9 N1 1.334(5) . ? C9 C10 1.508(6) . ? C10 F2 1.334(5) . ? C10 F3 1.320(5) . ? C10 F1 1.328(6) . ? C11 C12 1.457(8) . ? C11 N1 1.459(5) . ? C12 C13 1.335(8) . ? C13 C14 1.484(9) . ? N2 O4 1.208(4) . ? N2 O3 1.216(4) . ? 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 O1 H1A O2 0.82 1.81 2.535(3) 146.5 . O1 H1A O2 0.82 2.45 2.959(3) 121.1 2_666 N1 H1 O2 0.86 2.00 2.678(4) 134.5 . N1 H1 O1 0.86 2.42 3.135(4) 140.5 2_666 C4 H4 O4 0.93 2.46 3.391(5) 176.7 2_456 C11 H11B F2 0.97 2.46 3.043(6) 118.3 . C11 H11B F1 0.97 2.38 3.003(6) 121.6 . 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 C1 C2 O1 179.1(3) . . . . ? C7 C1 C2 O1 -2.3(5) . . . . ? C6 C1 C2 C3 -0.9(5) . . . . ? C7 C1 C2 C3 177.7(3) . . . . ? O1 C2 C3 C4 -179.5(3) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C3 C4 C5 N2 -179.3(3) . . . . ? C2 C1 C6 C5 0.5(5) . . . . ? C7 C1 C6 C5 -178.1(3) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? N2 C5 C6 C1 178.9(3) . . . . ? C6 C1 C7 O2 174.2(3) . . . . ? C2 C1 C7 O2 -4.4(5) . . . . ? C6 C1 C7 C8 -6.4(5) . . . . ? C2 C1 C7 C8 175.0(3) . . . . ? O2 C7 C8 C9 -3.0(6) . . . . ? C1 C7 C8 C9 177.6(3) . . . . ? C7 C8 C9 N1 0.0(6) . . . . ? C7 C8 C9 C10 177.5(4) . . . . ? N1 C9 C10 F2 58.5(6) . . . . ? C8 C9 C10 F2 -119.2(4) . . . . ? N1 C9 C10 F3 178.7(4) . . . . ? C8 C9 C10 F3 1.0(6) . . . . ? N1 C9 C10 F1 -61.2(5) . . . . ? C8 C9 C10 F1 121.2(4) . . . . ? N1 C11 C12 C13 -56.7(11) . . . . ? C11 C12 C13 C14 -170.6(8) . . . . ? C8 C9 N1 C11 -175.6(4) . . . . ? C10 C9 N1 C11 6.9(6) . . . . ? C12 C11 N1 C9 116.9(6) . . . . ? C4 C5 N2 O4 3.7(5) . . . . ? C6 C5 N2 O4 -175.1(3) . . . . ? C4 C5 N2 O3 -176.3(4) . . . . ? C6 C5 N2 O3 4.9(6) . . . . ?