Regioselective Arene Homologation through Rhenium-Catalyzed Deoxygenative Aromatization of 7-Oxabicyclo[2.2.1]hepta-2,5-dienes
Murai, Masahito; Ogita, Takuya; Takai, Kazuhiko; Chemical Communications  (2019) –; doi:10.1039/C9CC00270G

data_7122922
_publ_section_title
;
 Regioselective Arene Homologation through Rhenium-Catalyzed Deoxygenative
 Aromatization of 7-Oxabicyclo[2.2.1]hepta-2,5-dienes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00270G
_journal_year                    2019
_chemical_formula_moiety         'C26 H20 O5'
_chemical_formula_sum            'C26 H20 O5'
_chemical_formula_weight         412.44
_chemical_melting_point          474
_chemical_name_common            '1,2-Ph shift'
_chemical_name_systematic
'Dimethyl 1-oxo-2,4-diphenyl-1,2-dihydronaphthalene-2,3-dicarboxylate'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-10-15 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.731(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   15.7487(10)
_cell_length_b                   7.427(5)
_cell_length_c                   17.812(11)
_cell_measurement_reflns_used    5871
_cell_measurement_temperature    110
_cell_measurement_theta_max      31.20
_cell_measurement_theta_min      2.30
_cell_volume                     2069.0(19)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32142
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.036
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0994
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0826P)^2^+2.2072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2221
_reflns_number_gt                4236
_reflns_number_total             4746
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9cc00270g2.cif
_cod_data_source_block           6729-HoriS-deO3
_cod_database_code               7122922