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_7117359
_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            'C19 H22 Cl N'
_chemical_formula_weight         299.82
_chemical_name_systematic
'Rac-2-methyl-1-phenyl-2,3,4,5,6,10b-hexahydro-1H-pyrrolo[2,1-a]isoquinolin-4-ium chloride'
_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'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4474(3)
_cell_length_b                   16.4971(8)
_cell_length_c                   12.9089(6)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1585.99(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 0.999
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15505
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.163
_diffrn_reflns_theta_min         2.003
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       lathe
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 2354 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         5870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                5410
_reflns_number_total             5870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03390j2.cif
_cod_data_source_block           majr_Pna21
_cod_database_code               7117359
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.948
_shelxl_version_number           2013-4
_shelx_res_checksum              11575