#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:03:30 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304787 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064326.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_7064326 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 'C10 H7 F3 N2 O4' _chemical_formula_weight 276.18 _chemical_name_systematic (2Z)-3-amino-4,4,4-trifluoro-1-(2-hidroxy-5-nitrophenyl)but-2-en-1-one _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 difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2025-02-14 deposited with the CCDC. 2025-12-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.606(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.0511(3) _cell_length_b 15.3395(7) _cell_length_c 14.7473(11) _cell_measurement_reflns_used 1168 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.507<0 _cell_measurement_theta_min 3.8330 _cell_volume 1138.95(12) _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 0.845 _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 0.0262 _diffrn_reflns_av_unetI/netI 0.0373 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.845 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5157 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.845 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.652 _diffrn_reflns_theta_min 3.073 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86242 _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 1.611 _exptl_crystal_description fragment _exptl_crystal_F_000 560 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: petroleum ether:ethyl acetate (9:1)' _exptl_crystal_size_max 0.758 _exptl_crystal_size_mid 0.465 _exptl_crystal_size_min 0.138 _refine_diff_density_max 0.392 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2475 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0607 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.3884P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1612 _refine_ls_wR_factor_ref 0.1884 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1600 _reflns_number_total 2475 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04291g2.cif _cod_data_source_block shelx_CCDC1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7064326 _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. ; _oxdiff_exptl_absorpt_empirical_full_min 0.845 _oxdiff_exptl_absorpt_empirical_full_max 1.191 _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 P2(1)/n CELL 0.71073 5.0511 15.3395 14.7473 90.000 94.606 90.000 ZERR 4.00 0.0003 0.0007 0.0011 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O F UNIT 40 28 8 16 12 MERG 2 FMAP 2 PLAN -3 ACTA HTAB 2.00000 CONF L.S. 8 WGHT 0.090000 0.388400 FVAR 3.51863 F1 5 1.274664 0.886871 0.563698 11.00000 0.08433 0.06336 = 0.22105 -0.04058 -0.01913 -0.01715 F2 5 1.002441 0.908735 0.452311 11.00000 0.19930 0.04338 = 0.09322 0.01714 0.02688 -0.00289 F3 5 0.875818 0.906239 0.584270 11.00000 0.12713 0.04016 = 0.14451 -0.01619 0.07693 -0.00674 O1 4 0.683797 0.456648 0.587507 11.00000 0.06453 0.03303 = 0.07112 -0.00601 0.03513 0.00219 O2 4 0.897544 0.590580 0.524373 11.00000 0.05818 0.03758 = 0.05952 -0.00512 0.02973 -0.00050 O3 4 0.133967 0.751164 0.793953 11.00000 0.11535 0.04826 = 0.10177 -0.01509 0.05420 0.01182 O4 4 -0.047816 0.638943 0.847268 11.00000 0.09166 0.08269 = 0.08957 -0.00093 0.06068 0.01348 N1 3 1.146550 0.734279 0.463268 11.00000 0.06304 0.04012 = 0.06389 0.00058 0.02735 -0.00648 N2 3 0.105791 0.673009 0.798315 11.00000 0.05912 0.05841 = 0.04992 -0.00198 0.01852 0.01411 C1 1 0.581454 0.602694 0.633151 11.00000 0.04114 0.03278 = 0.03845 0.00039 0.01041 0.00229 C2 1 0.546683 0.511276 0.636590 11.00000 0.04697 0.03346 = 0.04561 -0.00207 0.01335 0.00343 C3 1 0.366282 0.475242 0.693202 11.00000 0.05994 0.03529 = 0.06156 0.00582 0.02506 0.00103 C4 1 0.222846 0.527083 0.746320 11.00000 0.05450 0.04879 = 0.05295 0.00889 0.02273 0.00435 C5 1 0.257965 0.616469 0.742601 11.00000 0.04730 0.04544 = 0.03948 -0.00027 0.01218 0.01008 C6 1 0.432346 0.654215 0.687552 11.00000 0.04791 0.03388 = 0.04401 -0.00078 0.01025 0.00408 C7 1 0.772954 0.640819 0.572934 11.00000 0.04300 0.03640 = 0.04343 -0.00059 0.01273 0.00125 C8 1 0.818151 0.732117 0.573037 11.00000 0.04673 0.03481 = 0.05178 -0.00146 0.01398 0.00195 C9 1 0.994458 0.771575 0.520837 11.00000 0.04551 0.03401 = 0.04947 0.00117 0.00535 0.00062 C10 1 1.034545 0.868723 0.531008 11.00000 0.06159 0.03901 = 0.06934 0.00152 0.01886 -0.00479 H1O 2 0.795530 0.489940 0.554663 11.00000 0.07848 H1N 2 1.129822 0.675344 0.455736 11.00000 0.06813 H2N 2 1.246514 0.764981 0.433976 11.00000 0.06614 H3 2 0.350367 0.412972 0.695697 11.00000 0.06278 H4 2 0.107973 0.504687 0.790948 11.00000 0.06775 H6 2 0.452660 0.714584 0.687923 11.00000 0.04884 H8 2 0.729601 0.769558 0.610941 11.00000 0.05067 HKLF 4 REM shelxt_a.res in P2(1)/n REM R1 = 0.0607 for 1600 Fo > 4sig(Fo) and 0.0938 for all 2475 data REM 200 parameters refined using 0 restraints END WGHT 0.0826 0.4460 REM Instructions for potential hydrogen bonds HTAB O1 O2 EQIV $1 -x+2, -y+1, -z+1 HTAB O1 O2_$1 HTAB N1 O1_$1 HTAB N1 O2 EQIV $2 x+3/2, -y+3/2, z-1/2 HTAB N1 O4_$2 EQIV $3 -x+1/2, y-1/2, -z+3/2 HTAB C3 O3_$3 REM Highest difference peak 0.392, deepest hole -0.311, 1-sigma level 0.051 Q1 1 1.1752 0.9019 0.4896 11.00000 0.05 0.39 Q2 1 0.8010 0.9064 0.4944 11.00000 0.05 0.32 Q3 1 1.0918 0.8874 0.6081 11.00000 0.05 0.30 ; _shelx_res_checksum 56121 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 F1 F 1.2747(5) 0.88687(13) 0.5637(2) 0.1246(11) Uani 1 1 d . . . . . F2 F 1.0024(6) 0.90873(12) 0.45231(16) 0.1112(9) Uani 1 1 d . . . . . F3 F 0.8758(5) 0.90624(11) 0.58427(18) 0.1004(8) Uani 1 1 d . . . . . O1 O 0.6838(4) 0.45665(11) 0.58751(14) 0.0546(6) Uani 1 1 d . . . . . O2 O 0.8975(4) 0.59058(11) 0.52437(13) 0.0504(5) Uani 1 1 d . . . . . O3 O 0.1340(5) 0.75116(14) 0.79395(18) 0.0860(8) Uani 1 1 d . . . . . O4 O -0.0478(5) 0.63894(17) 0.84727(17) 0.0851(8) Uani 1 1 d . . . . . N1 N 1.1466(5) 0.73428(17) 0.46327(18) 0.0545(7) Uani 1 1 d . . . . . N2 N 0.1058(5) 0.67301(17) 0.79832(16) 0.0551(6) Uani 1 1 d . . . . . C1 C 0.5815(5) 0.60269(15) 0.63315(16) 0.0371(5) Uani 1 1 d . . . . . C2 C 0.5467(5) 0.51128(15) 0.63659(17) 0.0415(6) Uani 1 1 d . . . . . C3 C 0.3663(6) 0.47524(18) 0.69320(19) 0.0512(7) Uani 1 1 d . . . . . C4 C 0.2228(6) 0.52708(18) 0.74632(19) 0.0511(7) Uani 1 1 d . . . . . C5 C 0.2580(5) 0.61647(17) 0.74260(17) 0.0436(6) Uani 1 1 d . . . . . C6 C 0.4323(5) 0.65421(16) 0.68755(17) 0.0416(6) Uani 1 1 d . . . . . C7 C 0.7730(5) 0.64082(15) 0.57293(16) 0.0404(6) Uani 1 1 d . . . . . C8 C 0.8182(5) 0.73212(16) 0.57304(18) 0.0439(6) Uani 1 1 d . . . . . C9 C 0.9945(5) 0.77158(15) 0.52084(17) 0.0429(6) Uani 1 1 d . . . . . C10 C 1.0345(6) 0.86872(18) 0.5310(2) 0.0559(7) Uani 1 1 d . . . . . H1O H 0.796(7) 0.490(2) 0.555(2) 0.078(11) Uiso 1 1 d . . . . . H1N H 1.130(6) 0.675(2) 0.456(2) 0.068(9) Uiso 1 1 d . . . . . H2N H 1.247(6) 0.765(2) 0.434(2) 0.066(10) Uiso 1 1 d . . . . . H3 H 0.350(6) 0.413(2) 0.696(2) 0.063(9) Uiso 1 1 d . . . . . H4 H 0.108(6) 0.505(2) 0.791(2) 0.068(9) Uiso 1 1 d . . . . . H6 H 0.453(5) 0.7146(19) 0.6879(18) 0.049(7) Uiso 1 1 d . . . . . H8 H 0.730(5) 0.7696(18) 0.6109(19) 0.051(8) 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 F1 0.0843(16) 0.0634(13) 0.221(3) -0.0406(16) -0.0191(18) -0.0171(11) F2 0.199(3) 0.0434(10) 0.0932(16) 0.0171(10) 0.0269(17) -0.0029(13) F3 0.1271(19) 0.0402(10) 0.145(2) -0.0162(11) 0.0769(16) -0.0067(10) O1 0.0645(12) 0.0330(9) 0.0711(13) -0.0060(9) 0.0351(10) 0.0022(8) O2 0.0582(11) 0.0376(9) 0.0595(11) -0.0051(8) 0.0297(9) -0.0005(8) O3 0.115(2) 0.0483(13) 0.1018(18) -0.0151(12) 0.0542(16) 0.0118(12) O4 0.0917(17) 0.0827(17) 0.0896(17) -0.0009(13) 0.0607(15) 0.0135(13) N1 0.0630(16) 0.0401(13) 0.0639(16) 0.0006(11) 0.0273(13) -0.0065(11) N2 0.0591(15) 0.0584(15) 0.0499(13) -0.0020(11) 0.0185(12) 0.0141(11) C1 0.0411(13) 0.0328(11) 0.0384(12) 0.0004(10) 0.0104(10) 0.0023(9) C2 0.0470(14) 0.0335(12) 0.0456(13) -0.0021(10) 0.0133(11) 0.0034(10) C3 0.0599(17) 0.0353(13) 0.0616(17) 0.0058(12) 0.0251(14) 0.0010(12) C4 0.0545(16) 0.0488(15) 0.0529(15) 0.0089(13) 0.0227(13) 0.0044(12) C5 0.0473(14) 0.0454(14) 0.0395(13) -0.0003(11) 0.0122(11) 0.0101(11) C6 0.0479(14) 0.0339(13) 0.0440(14) -0.0008(11) 0.0103(11) 0.0041(10) C7 0.0430(13) 0.0364(12) 0.0434(13) -0.0006(11) 0.0127(11) 0.0013(10) C8 0.0467(14) 0.0348(12) 0.0518(15) -0.0015(11) 0.0140(12) 0.0020(10) C9 0.0455(13) 0.0340(12) 0.0495(15) 0.0012(11) 0.0054(12) 0.0006(10) C10 0.0616(18) 0.0390(14) 0.0693(19) 0.0015(14) 0.0189(15) -0.0048(13) 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 O4 N2 O3 122.7(2) . . ? O4 N2 C5 118.0(2) . . ? O3 N2 C5 119.4(2) . . ? C6 C1 C2 117.9(2) . . ? C6 C1 C7 122.0(2) . . ? C2 C1 C7 120.0(2) . . ? O1 C2 C3 117.8(2) . . ? O1 C2 C1 122.1(2) . . ? C3 C2 C1 120.1(2) . . ? C4 C3 C2 120.9(3) . . ? C3 C4 C5 118.6(2) . . ? C6 C5 C4 122.1(2) . . ? C6 C5 N2 118.4(2) . . ? C4 C5 N2 119.5(2) . . ? C5 C6 C1 120.3(2) . . ? O2 C7 C8 121.2(2) . . ? O2 C7 C1 118.7(2) . . ? C8 C7 C1 120.0(2) . . ? C9 C8 C7 123.3(2) . . ? N1 C9 C8 127.6(2) . . ? N1 C9 C10 114.3(2) . . ? C8 C9 C10 118.0(2) . . ? F1 C10 F3 106.5(3) . . ? F1 C10 F2 105.9(3) . . ? F3 C10 F2 106.8(3) . . ? F1 C10 C9 111.2(2) . . ? F3 C10 C9 114.4(2) . . ? F2 C10 C9 111.6(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 1.299(4) . ? F2 C10 1.311(3) . ? F3 C10 1.301(3) . ? O1 C2 1.337(3) . ? O2 C7 1.255(3) . ? O3 N2 1.210(3) . ? O4 N2 1.219(3) . ? N1 C9 1.320(3) . ? N2 C5 1.456(3) . ? C1 C6 1.390(3) . ? C1 C2 1.415(3) . ? C1 C7 1.485(3) . ? C2 C3 1.398(3) . ? C3 C4 1.365(4) . ? C4 C5 1.384(4) . ? C5 C6 1.373(4) . ? C7 C8 1.419(3) . ? C8 C9 1.365(3) . ? C9 C10 1.510(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 C6 C1 C2 O1 -179.2(2) . . . . ? C7 C1 C2 O1 0.7(4) . . . . ? C6 C1 C2 C3 0.2(4) . . . . ? C7 C1 C2 C3 -179.9(2) . . . . ? O1 C2 C3 C4 178.9(3) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C3 C4 C5 N2 179.6(2) . . . . ? O4 N2 C5 C6 -179.7(3) . . . . ? O3 N2 C5 C6 0.9(4) . . . . ? O4 N2 C5 C4 0.5(4) . . . . ? O3 N2 C5 C4 -178.9(3) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? N2 C5 C6 C1 -179.9(2) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? C7 C1 C6 C5 -179.8(2) . . . . ? C6 C1 C7 O2 -178.7(2) . . . . ? C2 C1 C7 O2 1.4(3) . . . . ? C6 C1 C7 C8 3.2(4) . . . . ? C2 C1 C7 C8 -176.7(2) . . . . ? O2 C7 C8 C9 0.7(4) . . . . ? C1 C7 C8 C9 178.8(2) . . . . ? C7 C8 C9 N1 0.4(4) . . . . ? C7 C8 C9 C10 -176.8(2) . . . . ? N1 C9 C10 F1 -62.5(4) . . . . ? C8 C9 C10 F1 115.0(3) . . . . ? N1 C9 C10 F3 176.8(3) . . . . ? C8 C9 C10 F3 -5.7(4) . . . . ? N1 C9 C10 F2 55.5(3) . . . . ? C8 C9 C10 F2 -127.0(3) . . . . ?