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_7115464
_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            'C13 H10 Br N O3'
_chemical_formula_weight         308.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9842(14)
_cell_length_b                   8.9505(15)
_cell_length_c                   17.463(3)
_cell_measurement_temperature    305(2)
_cell_volume                     1248.0(4)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      305(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.586
_diffrn_reflns_point_group_measured_fraction_max 0.570
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.100
_diffrn_reflns_theta_min         2.557
_exptl_absorpt_coefficient_mu    3.292
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             612
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.415(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0430
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1538
_reflns_number_total             2091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc03090g3.cif
_cod_data_source_block
mo_5-bromo-4'-methyl-2'-nitro-[1,1'-biphenyl]-2-ol
_cod_database_code               7115464
_shelxl_version_number           2014-1
_shelx_res_checksum              50822