Cu(II)-promoted Tandem Decarboxylative Halogenation and Oxidative Diamination Reaction of 2-Aminopyridines with Alkynoic Acids for the Synthesis of 2-Haloimidazo[1,2-a]pyridines
Liu, Yun; Wang, Wenhui; Han, Junwen; Sun, Jinwei Wei; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02014G

data_7155927
_publ_section_title
;
 Cu(II)-promoted Tandem Decarboxylative Halogenation and Oxidative
 Diamination Reaction of 2-Aminopyridines with Alkynoic Acids for the
 Synthesis of 2-Haloimidazo[1,2-a]pyridines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02014G
_journal_year                    2017
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-30 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                96.591(2)
_cell_angle_beta                 93.902(2)
_cell_angle_gamma                105.608(2)
_cell_formula_units_Z            4
_cell_length_a                   7.6418(4)
_cell_length_b                   9.2290(5)
_cell_length_c                   16.4366(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1103.14(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8120
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.696
_exptl_absorpt_correction_T_max  0.5252
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0375P)^2^+0.0246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0773
_reflns_number_gt                3103
_reflns_number_total             3860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02014g2.cif
_cod_data_source_block           a
_cod_database_code               7155927