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_7109058
_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_moiety         'C8 H4 Cl N O2'
_chemical_formula_sum            'C8 H4 Cl N O2'
_chemical_formula_weight         181.57
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.168(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.337(3)
_cell_length_b                   3.8023(10)
_cell_length_c                   15.603(4)
_cell_measurement_reflns_used    5115
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.35
_cell_volume                     722.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7021
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0262
_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^)+(0.0352P)^2^+0.3486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                1690
_reflns_number_total             1788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41124a.txt
_cod_data_source_block           tr1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7109058