Diphenoquinhydrones and Related Hydrogen-Bonded Charge-Transfer Complexes
Néron, Sébastien; Morency, Mathieu; Malveau, Cédric; Maris, Thierry; Iftimie, Radu; Wuest, James D.; The Journal of organic chemistry 87 (2022) 15796–15805; doi:10.1021/acs.joc.2c01805

data_4039012
_publ_section_title
;
 Diphenoquinhydrones and Related Hydrogen-Bonded Charge-Transfer Complexes
;
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15796
_journal_page_last               15805
_journal_paper_doi               10.1021/acs.joc.2c01805
_journal_volume                  87
_journal_year                    2022
_chemical_formula_moiety         'C6 H3 Br2 O, C8 H8 O'
_chemical_formula_sum            'C14 H11 Br2 O2'
_chemical_formula_weight         371.05
_chemical_name_systematic
;
 3,3',5,5'-tetramethyl[1,1'-bi(cyclohexa-2,5-dien-1-ylidene)]-
4,4'-dione 3,3',5,5'-tetrabromo[1,1'-biphenyl]-4,4'-diol
;
_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
_audit_creation_date             2021-02-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                75.078(3)
_cell_angle_beta                 76.037(2)
_cell_angle_gamma                85.769(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8307(3)
_cell_length_b                   8.1915(3)
_cell_length_c                   10.2693(6)
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.645
_cell_measurement_theta_min      5.590
_cell_volume                     617.66(5)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12456
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.022
_diffrn_reflns_theta_min         4.579
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.81
_exptl_absorpt_coefficient_mu    8.249
_exptl_absorpt_correction_T_max  0.1370
_exptl_absorpt_correction_T_min  0.0334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1724 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.2438.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_description       Plate
_exptl_crystal_F_000             362
_exptl_crystal_recrystallization_method 'crystallised from Toluene/Et2O'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.641
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.279
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.1336P)^2^+0.0450P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.1938
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1966
_reflns_number_total             2349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3-3c_4e.cif
_cod_data_source_block           jw2379
_cod_database_code               4039012
_cod_database_fobs_code 4039012