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_4028366
_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            'C16 H23 N O5'
_chemical_formula_weight         309.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.123(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.235(16)
_cell_length_b                   7.700(8)
_cell_length_c                   14.339(15)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.81
_cell_volume                     1599(3)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7156
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0587P)^2^+0.0976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                1734
_reflns_number_total             2951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4007943_si_005.cif
_cod_data_source_block           p21c
_cod_database_code               4028366