Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes.
Sharma, Shivangi; Parumala, Santosh Kumar Reddy; Peddinti, Rama Krishna; The Journal of organic chemistry 82 (2017) 9367–9383; doi:10.1021/acs.joc.7b00684

data_4033050
_publ_section_title
;
 Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from
 Methoxyphenols and Electron-Rich Arenes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9367
_journal_page_last               9383
_journal_paper_doi               10.1021/acs.joc.7b00684
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H28 O8'
_chemical_formula_sum            'C25 H28 O8'
_chemical_formula_weight         456.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                92.799(5)
_cell_angle_beta                 102.322(5)
_cell_angle_gamma                90.028(5)
_cell_formula_units_Z            2
_cell_length_a                   7.704(5)
_cell_length_b                   9.207(5)
_cell_length_c                   16.462(5)
_cell_measurement_reflns_used    5689
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.361
_cell_measurement_theta_min      1.268
_cell_volume                     1139.3(10)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17561
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_min         1.268
_exptl_absorpt_coefficient_mu    0.099
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      1.44
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3958
_reflns_number_total             5586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00684_si_004.cif
_cod_data_source_block           shelx
_cod_database_code               4033050
_shelxl_version_number           2014/6
_shelx_res_checksum              82943
_shelx_hkl_checksum              18699