Magnesium Coordination-Directed N-Selective Stereospecific Alkylation of 2-Pyridones, Carbamates, and Amides Using α-Halocarboxylic Acids
Yuan-Qing Fang; Matthew M. Bio; Karl B. Hansen; Matthew S. Potter; Andrew Clausen; Journal of the American Chemical Society 132 (2010) 15525–15527; doi:10.1021/ja107709w

data_4103462
_publ_section_title
;
 Magnesium Coordination-Directed N-Selective Stereospecific Alkylation of
 2-Pyridones, Carbamates, and Amides Using \a-Halocarboxylic Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15525
_journal_page_last               15527
_journal_paper_doi               10.1021/ja107709w
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H8 Br N O3'
_chemical_formula_sum            'C8 H8 Br N O3'
_chemical_formula_weight         246.06
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4414(2)
_cell_length_b                   9.7195(5)
_cell_length_c                   16.8074(6)
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.26
_cell_measurement_theta_min      5.26
_cell_volume                     888.90(6)
_computing_cell_refinement       'APEX2 (BRUKER, V5-0, 2008)'
_computing_data_collection       'COSMO (BRUKER, V1.58, 2007)'
_computing_data_reduction        'SAINT (BRUKER, V7.56A, 2008)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6055
_diffrn_reflns_theta_full        68.14
_diffrn_reflns_theta_max         68.14
_diffrn_reflns_theta_min         5.26
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.124
_exptl_absorpt_correction_T_max  0.5269
_exptl_absorpt_correction_T_min  0.2386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                1596
_reflns_number_total             1609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja107709w_si_002.cif
_cod_data_source_block           amg2609_0m
_cod_database_code               4103462