One-Pot Synthesis of Highly Functionalized Pyridines via a Rhodium Carbenoid Induced Ring Expansion of Isoxazoles
James R. Manning; Huw M. L. Davies; Journal of the American Chemical Society 130 (2008) 8602–8603; doi:10.1021/ja803139k

data_4107996
_publ_contact_author_address
;
Department of Chemistry
State University of New York at Buffalo
Buffalo, NY
14260-3000, USA
;
_publ_contact_author_email       mpitak@buffalo.edu
_publ_contact_author_name        'Mateusz Pitak'
_publ_contact_author_phone       (716)645-6800x2233
_publ_section_title
;
 One-Pot Synthesis of Highly Functionalized Pyridines via a Rhodium
 Carbenoid Induced Ring Expansion of Isoxazoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8602
_journal_page_last               8603
_journal_paper_doi               10.1021/ja803139k
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C16 H14 Br N O3'
_chemical_formula_sum            'C16 H14 Br N O3'
_chemical_formula_weight         348.19
_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                 94.616(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2150(8)
_cell_length_b                   10.9179(12)
_cell_length_c                   19.254(2)
_cell_measurement_reflns_used    8763
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.83
_cell_volume                     1511.8(3)
_computing_cell_refinement       'Bruker Saint v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'Bruker Saint v7.23A (Bruker, 2005)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(1)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21965
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.12
_diffrn_source_type              'RIGAKU RU-2000BEH'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.728
_exptl_absorpt_correction_T_max  0.341
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2004/1 Bruker 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0376(19)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0530P)^2^+0.3528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                3375
_reflns_number_total             3792
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803139k-file003.cif
_cod_data_source_block           Davies122007
_cod_original_cell_volume        1511.7(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4107996