C-H functionalization of cyclic amines: redox-annulations with alpha,beta-unsaturated carbonyl compounds
YoungKu Kang; Matthew T. Richers; Conrad H. Sawicki; Daniel Seidel; Chem.Commun. 51 (2015) 10648–; doi:10.1039/C5cc03390J

data_7117360
_publ_section_title
;
 C-H functionalization of cyclic amines: redox-annulations with
 alpha,beta-unsaturated carbonyl compounds
;
_journal_name_full               Chem.Commun.
_journal_page_first              10648
_journal_paper_doi               10.1039/C5cc03390J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C20 H23 Br N'
_chemical_formula_weight         357.30
_chemical_name_systematic
Rac-1-(4-bromophenyl)-3-phenyloctahydropyrrolizin-4-ium-4-yl)trihydroborate
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-04-21 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3551(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9903(5)
_cell_length_b                   6.5457(3)
_cell_length_c                   19.1580(7)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.60
_cell_measurement_theta_min      2.35
_cell_volume                     1706.97(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23857
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.679
_diffrn_reflns_theta_min         1.496
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       plate
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         6256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                5107
_reflns_number_total             6256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03390j2.cif
_cod_data_source_block           yk944_P21c
_cod_database_code               7117360
_shelx_estimated_absorpt_t_min   0.523
_shelx_estimated_absorpt_t_max   0.778
_shelxl_version_number           2013-4
_shelx_res_checksum              45668