Ruthenium-catalyzed intramolecular selective halogenation of O-methylbenzohydroximoyl halides: a new route to halogenated aromatic nitriles
Ravi Kiran Chinnagolla; Sandeep Pimparkar; Masilamani Jeganmohan; Chem.Commun. 49 (2013) 3146–; doi:10.1039/c3cc41124a

data_7109059
_publ_section_title
;
 Ruthenium-catalyzed intramolecular selective halogenation of
 O-methylbenzohydroximoyl halides: a new route to halogenated aromatic
 nitriles
;
_journal_name_full               Chem.Commun.
_journal_page_first              3146
_journal_paper_doi               10.1039/c3cc41124a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C8 H6 Br N O2'
_chemical_formula_weight         228.05
_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                85.645(3)
_cell_angle_beta                 89.563(3)
_cell_angle_gamma                70.248(3)
_cell_formula_units_Z            4
_cell_length_a                   7.2030(10)
_cell_length_b                   9.5004(12)
_cell_length_c                   12.9717(16)
_cell_measurement_temperature    200(2)
_cell_volume                     832.88(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13496
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    4.889
_exptl_absorpt_correction_T_max  0.6153
_exptl_absorpt_correction_T_min  0.5084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0282P)^2^+0.4897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0613
_reflns_number_gt                3572
_reflns_number_total             4127
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3cc41124a.txt
_cod_data_source_block           4c
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7109059