Rearrangement of 4-Amino-3-halo-pyridines by Nucleophilic Aromatic Substitution
Matthäus Getlik; Brian J. Wilson; M. Monzur Morshed; Iain D. G. Watson; Doris Tang; Pandiaraju Subramanian; Rima Al-awar; Journal of Organic Chemistry 78 (2013) 5705–5710; doi:10.1021/jo4003773

data_4028271
_publ_section_title
;
 Rearrangement of 4-Amino-3-halo-pyridines by Nucleophilic Aromatic
 Substitution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5705
_journal_page_last               5710
_journal_paper_doi               10.1021/jo4003773
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H16 Br Cl N2 O3'
_chemical_formula_sum            'C16 H16 Br Cl N2 O3'
_chemical_formula_weight         399.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.096(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4067(6)
_cell_length_b                   4.7337(2)
_cell_length_c                   26.7972(13)
_cell_measurement_reflns_used    7496
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      65.82
_cell_measurement_theta_min      3.40
_cell_volume                     1649.43(13)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_source         'Bruker microsource'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10312
_diffrn_reflns_theta_full        66.24
_diffrn_reflns_theta_max         66.24
_diffrn_reflns_theta_min         3.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.031
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0794P)^2^+4.6311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                2591
_reflns_number_total             2780
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo4003773_si_002_2.cif
_cod_data_source_block           d1264
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028271