Structural and spectroscopic study and intermolecular chalcogen bonding interactions in 1,3-dicarbonyl compounds
Salvador Vallejo, L. E.; Jios, J. L.; Ulic, S. E.; Echeverría, G. A.; Piro, O. E.; Pis Diez, R.; Vázquez, C.; Merlo, C.; New Journal of Chemistry 48 (2024) 14420–14434; doi:10.1039/D4NJ02508C

data_7063365
_publ_section_title
;
 Structural and spectroscopic study and intermolecular chalcogen bonding
 interactions in 1,3-dicarbonyl compounds
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14420
_journal_page_last               14434
_journal_paper_doi               10.1039/D4NJ02508C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_sum            'C19 H13 Cl O3'
_chemical_formula_weight         324.74
_chemical_melting_point          391
_chemical_name_systematic
1-(5-chloro-2-hydroxyphenyl)-3-hydroxy-3-(naphthalen-1yl)prop-2-en-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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
;
2023-10-14 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.759(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2130(10)
_cell_length_b                   7.9744(9)
_cell_length_c                   17.7754(14)
_cell_measurement_reflns_used    926
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.6550
_cell_measurement_theta_min      4.2940
_cell_volume                     1521.9(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      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.906
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.905
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4349
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.457
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89260
_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    1.417
_exptl_crystal_description       fragment
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.708
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.015(2)
_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   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.2174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1658
_reflns_number_total             2505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02508c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7063365--7063366.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063365
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.949
_oxdiff_exptl_absorpt_empirical_full_min 0.885
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              4885
_shelx_hkl_checksum              5582