Aerobic Copper-Catalyzed Halocyclization of Methyl N-Heteroaromatics with Aliphatic Amines: Access to Functionalized Imidazo-Fused N-Heterocycles.
Tan, Zhenda; Zhao, He; Zhou, Changjian; Jiang, Huanfeng; Zhang, Min; The Journal of organic chemistry 81 (2016) 9939–9946; doi:10.1021/acs.joc.6b02117

data_4037389
_publ_section_title
;
 Aerobic Copper-Catalyzed Halocyclization of Methyl N-Heteroaromatics with
 Aliphatic Amines: Access to Functionalized Imidazo-Fused N-Heterocycles.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9939
_journal_page_last               9946
_journal_paper_doi               10.1021/acs.joc.6b02117
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H11 Br N2'
_chemical_formula_sum            'C17 H11 Br N2'
_chemical_formula_weight         323.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.523(5)
_cell_length_b                   14.642(4)
_cell_length_c                   5.1195(15)
_cell_measurement_reflns_used    1185
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.97
_cell_measurement_theta_min      2.60
_cell_volume                     1388.5(7)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0879
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8008
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.981
_diffrn_reflns_theta_min         1.773
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.950
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1015P)^2^+2.1551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                1544
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02117_si_002.cif
_cod_data_source_block           1
_cod_database_code               4037389
_shelxl_version_number           2014-3
_shelx_res_checksum              40160
_shelx_hkl_checksum              14867