Alkyne aminohalogenation enabled by DBU-activated N-haloimides: direct synthesis of halogenated enamines
Mengru Li; Haiyan Yuan; Baozhong Zhao; Fushun Liang; Jingping Zhang; Chem.Commun. 50 (2014) 2360–; doi:10.1039/c3cc49572h

data_7112013
_publ_section_title
;
 Alkyne aminohalogenation enabled by DBU-activated N-haloimides: direct
 synthesis of halogenated enamines
;
_journal_name_full               Chem.Commun.
_journal_page_first              2360
_journal_paper_doi               10.1039/c3cc49572h
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C16 H10 N O2 Br'
_chemical_formula_sum            'C16 H10 Br N O2'
_chemical_formula_weight         328.17
_chemical_name_common            'C16 H10 N O2 Br'
_space_group_IT_number           1
_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
_cell_angle_alpha                107.363(2)
_cell_angle_beta                 94.428(2)
_cell_angle_gamma                103.078(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5646(10)
_cell_length_b                   8.0027(11)
_cell_length_c                   12.4858(16)
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      1.73
_cell_volume                     694.13(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3742
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  0.411
_exptl_absorpt_correction_T_min  0.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0612P)^2^+0.7251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                2487
_reflns_number_total             3164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc49572h.txt
_cod_data_source_block           tan135
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7112013