Chemoselective arylation of phenols with bromo-nitroarenes: synthesis of nitro-biaryl-ols and their conversion into benzofurans and carbazoles
Amit Kumar; Abhimanyu Yadav; Ajay Verma; Sadhan Jana; Moh. Sattar; Shailesh Kumar; Ch. Durga Prasad; Sangit Kumar; Chem.Commun. 50 (2014) 9481–; doi:10.1039/C4cc03090G

data_7115465
_publ_section_title
;
 Chemoselective arylation of phenols with bromo-nitroarenes: synthesis of
 nitro-biaryl-ols and their conversion into benzofurans and carbazoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              9481
_journal_paper_doi               10.1039/C4cc03090G
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_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                82.195(3)
_cell_angle_beta                 79.847(3)
_cell_angle_gamma                85.040(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8419(3)
_cell_length_b                   8.4340(3)
_cell_length_c                   12.6395(5)
_cell_measurement_temperature    296(2)
_cell_volume                     709.82(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.740
_diffrn_measured_fraction_theta_max 0.740
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2208
_diffrn_reflns_theta_full        26.63
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+0.1709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1787
_reflns_number_total             2208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03090g3.cif
_cod_data_source_block
2,3,4',5-tetramethyl-2'-nitro-[1,1'-biphenyl]-4-ol
_cod_database_code               7115465