Hydrogen bonding and charge transfer in trifluoromethylated β-aminoenones: a combined experimental and theoretical study
Jios, Eliana; Salvador Vallejo, Lorena E.; Echeverría, Gustavo A.; Piro, Oscar E.; Jios, Jorge L.; Naso, Luciana G.; Ulic, Sonia E.; New Journal of Chemistry 50 (2026) 1809–1823; doi:10.1039/D5NJ04291G

data_7064326
_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
_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_checksum              56121