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_4033049
_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         'C15 H14 Br Cl O4'
_chemical_formula_sum            'C15 H14 Br Cl O4'
_chemical_formula_weight         373.61
_chemical_melting_point          118
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.101(2)
_cell_angle_beta                 90.003(2)
_cell_angle_gamma                102.300(2)
_cell_formula_units_Z            4
_cell_length_a                   8.7526(4)
_cell_length_b                   9.0170(4)
_cell_length_c                   19.8984(7)
_cell_measurement_reflns_used    7622
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.300
_cell_measurement_theta_min      2.31
_cell_volume                     1534.37(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18716
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    2.865
_exptl_absorpt_correction_T_max  0.564
_exptl_absorpt_correction_T_min  0.569
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square prizm'
_exptl_crystal_F_000             1139
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         7125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                3594
_reflns_number_total             7125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00684_si_002.cif
_cod_data_source_block           ups1590san_0ma_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4033049