Keto–enol equilibrium: stable tautomers of ortho-, meta-, and para-hydroquinones in large aromatics
Silber, Vincent; Gourlaouen, Christophe; Ruppert, Romain; RSC Advances 14 (2024) 11969–11976; doi:10.1039/D4RA02202E

data_7248416
_publ_section_title
;
 Keto--enol equilibrium: stable tautomers of ortho-, meta-, and
 para-hydroquinones in large aromatics
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              11969
_journal_page_last               11976
_journal_paper_doi               10.1039/D4RA02202E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C28 H19 Br O2'
_chemical_formula_sum            'C28 H19 Br O2'
_chemical_formula_weight         467.34
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc287sx7
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-07 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.4410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6897(5)
_cell_length_b                   14.0457(6)
_cell_length_c                   20.6528(7)
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.43
_cell_volume                     4126.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            91304
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.924
_diffrn_reflns_theta_min         2.036
_exptl_absorpt_coefficient_mu    2.016
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+3.7757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8445
_reflns_number_total             9892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02202e2.cif
_cod_data_source_block           mo_JWVS210111_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248416
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.689
_shelx_estimated_absorpt_t_max   0.752
_shelx_res_checksum              70141
_shelx_hkl_checksum              7740