Copper(II)-Catalyzed Indolizines Formation Followed by Dehydrogenative Functionalization Cascade to Synthesize 1-Bromoindolizines.
Wang, Fuyao; Shen, Yongmiao; Hu, Huayou; Wang, Xiangshan; Wu, Hui; Liu, Yun; The Journal of organic chemistry 79 (2014) 9556–9566; doi:10.1021/jo501626b

data_4029974
_publ_section_title
;
 Copper(II)-Catalyzed Indolizines Formation Followed by Dehydrogenative
 Functionalization Cascade to Synthesize 1-Bromoindolizines.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9556
_journal_page_last               9566
_journal_paper_doi               10.1021/jo501626b
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C19 H12 Br N O'
_chemical_formula_weight         350.21
_space_group_IT_number           14
_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                 93.276(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9141(2)
_cell_length_b                   11.5887(3)
_cell_length_c                   21.4526(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1467.89(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11448
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    2.801
_exptl_absorpt_correction_T_max  0.6043
_exptl_absorpt_correction_T_min  0.4871
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.4659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                2415
_reflns_number_total             2874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501626b_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 4029974.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4029974