Supramolecular assembly mediated by hydrogen bonds and weak noncovalent interactions in two eucalyptol derivatives with potential antineoplastic activity: crystal structure, Hirshfeld surface analysis, DFT calculations and molecular docking analysis
Galvez, Carolina E.; Piro, Oscar E.; Echeverría, Gustavo A.; Vignesh, Krishnan; Thamotharan, Subbiah; Loandos, María del H.; Gil, Diego M.; CrystEngComm 27 (2025) 3806–3822; doi:10.1039/D5CE00308C

data_7250352
_publ_section_title
;
 Supramolecular assembly mediated by hydrogen bonds and weak noncovalent
 interactions in two eucalyptol derivatives with potential antineoplastic
 activity: crystal structure, Hirshfeld surface analysis, DFT calculations
 and molecular docking analysis
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3806
_journal_page_last               3822
_journal_paper_doi               10.1039/D5CE00308C
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
_chemical_name_systematic
1,3,3-trimethyl-2-oxabicycle[2.2.2]octane-5-acetyl-8-oxo
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-03-19 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7247(3)
_cell_length_b                   8.6013(4)
_cell_length_c                   18.5304(8)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.4270
_cell_measurement_theta_min      4.1690
_cell_volume                     1231.21(9)
_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 0.873
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.689
_diffrn_reflns_theta_min         3.232
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87214
_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            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       fragment
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.0584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                2036
_reflns_number_total             2658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00308c2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7250351--7250352.cif.'
_cod_original_cell_volume        1231.20(9)
_cod_database_code               7250352
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.989
_oxdiff_exptl_absorpt_empirical_full_min 0.866
_oxdiff_exptl_absorpt_empirical_full_max 1.176
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              43111