Highly meta-selective halogenation of 2-phenylpyridine with a ruthenium(i) catalyst
Reddy, Ganapam Manohar; Rao, Naidu Sambasiva; Maheswaran, H.; Organic Chemistry Frontiers 5 (2018) 1118–; doi:10.1039/C7QO01133D

data_1553973
_publ_section_title
;
 Highly meta-selective halogenation of 2-phenylpyridine with a
 ruthenium(i) catalyst
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1118
_journal_paper_doi               10.1039/C7QO01133D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 Br N O'
_chemical_formula_sum            'C12 H10 Br N O'
_chemical_formula_weight         264.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-16 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.062(3)
_cell_length_b                   4.0452(9)
_cell_length_c                   21.707(5)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.77
_cell_measurement_theta_min      2.52
_cell_volume                     1059.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.800
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 0.800
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8904
_diffrn_reflns_point_group_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_min         1.688
_exptl_absorpt_coefficient_mu    3.851
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.776
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.776
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0296P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1118
_reflns_number_total             2179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo01133d2.cif
_cod_data_source_block           AY61
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553973
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.561
_shelx_estimated_absorpt_t_max   0.748
_shelx_res_checksum              60305
_shelx_hkl_checksum              77172