Transannular Reductive Rearrangement of α-Amino Ketones: construction of Aza-tricyclic Frameworks of Several Alkaloids
Jian Zhang; Yong-Qiang Wang; Xin-Wei Wang; Wei-Dong Z. Li; Journal of Organic Chemistry 78 (2013) 6154–6162; doi:10.1021/jo4007943

data_4028367
_publ_section_title
;
 Transannular Reductive Rearrangement of \a-Amino Ketones: construction of
 Aza-tricyclic Frameworks of Several Alkaloids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6154
_journal_page_last               6162
_journal_paper_doi               10.1021/jo4007943
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C14 H23 N O4'
_chemical_formula_weight         269.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.767(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.978(6)
_cell_length_b                   8.194(5)
_cell_length_c                   17.056(10)
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      2.40
_cell_volume                     1387.4(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0617
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9956
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1042P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.2098
_reflns_number_gt                2687
_reflns_number_total             4978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4007943_si_006.cif
_cod_data_source_block           p21
_cod_database_code               4028367