Deciphering weak hydrogen bonds, halogen bonds, and π-stacking interactions in two fluorinated 2′-hydroxychalcones: insights from experimental and theoretical analysis
Cassará, María Lucrecia Arias; Pérez, Hiram; Davies, Lilian E.; Echeverría, Gustavo A.; Piro, Oscar E.; Gil, Diego M.; CrystEngComm 27 (2025) 6781–6796; doi:10.1039/D5CE00793C

data_7250903
_publ_section_title
;
 Deciphering weak hydrogen bonds, halogen bonds, and \p-stacking
 interactions in two fluorinated 2&#x2032;-hydroxychalcones: insights from
 experimental and theoretical analysis
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6781
_journal_page_last               6796
_journal_paper_doi               10.1039/D5CE00793C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C16 H11 F3 O2'
_chemical_formula_weight         292.25
_chemical_name_systematic
'(E)-1-(2-hidroxyphenyl)-3-[(4-trifluormethyl) phenyl]prop-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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.589(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6889(6)
_cell_length_b                   11.4309(9)
_cell_length_c                   30.912(2)
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.5920
_cell_measurement_theta_min      3.6550
_cell_volume                     2708.2(3)
_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      297(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 0.852
_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_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            6302
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.890
_diffrn_reflns_theta_min         3.187
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82650
_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    1.434
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         6302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.0915
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1915P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3229
_refine_ls_wR_factor_ref         0.3446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2878
_reflns_number_total             6302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00793c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7250903--7250904.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7250903
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.976
_oxdiff_exptl_absorpt_empirical_full_min 0.812
_oxdiff_exptl_absorpt_empirical_full_max 1.193
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              95598