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_7064325
_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_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_checksum              54847