Experimental and theoretical insights into the formation of weak hydrogen bonds and H⋯H bonding interactions in the solid-state structure of two eucalyptol derivatives
Galvez, Carolina E.; Piro, Oscar E.; Echeverría, Gustavo A.; Robles, Norma Lis; Lezama, José O. G.; Sankaran, Sankaran Venkatachalam; Thamotharan, Subbiah; Villecco, Margarita B.; Loandos, María del H.; Gil, Diego M.; New Journal of Chemistry 46 (2022) 5690–5704; doi:10.1039/D2NJ00428C

data_7061320
_publ_section_title
;
 Experimental and theoretical insights into the formation of weak hydrogen
 bonds and H&#x22EF;H bonding interactions in the solid-state structure of
 two eucalyptol derivatives
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5690
_journal_page_last               5704
_journal_paper_doi               10.1039/D2NJ00428C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C12 H20 O3'
_chemical_formula_weight         212.28
_chemical_name_systematic
'1,3,3-trimethyl-2-oxabicycle[2.2.2]oct-5-yl acetate'
_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
;
2021-08-21 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                88.056(7)
_cell_angle_beta                 87.341(7)
_cell_angle_gamma                70.216(8)
_cell_formula_units_Z            2
_cell_length_a                   5.9803(5)
_cell_length_b                   7.9085(7)
_cell_length_c                   13.5905(12)
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.0140
_cell_measurement_theta_min      3.8660
_cell_volume                     604.06(10)
_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 0.824
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4757
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.909
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75917
_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    1.167
_exptl_crystal_description       fragment
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.110(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.0103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1637
_reflns_number_total             2630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00428c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7061320--7061321.cif.'
_cod_database_code               7061320
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.983
_oxdiff_exptl_absorpt_empirical_full_min 0.707
_oxdiff_exptl_absorpt_empirical_full_max 1.514
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              14295