Iterative direct C(sp(3))-H functionalization of amines: diastereoselective divergent syntheses of α,α'-disubstituted alicyclic amines.
Mahato, Sujit; Jana, Chandan K.; Organic & biomolecular chemistry 15 (2017) 1655–1660; doi:10.1039/c6ob02257j

data_7155466
_publ_section_title
;
 Iterative direct C(sp(3))-H functionalization of amines:
 diastereoselective divergent syntheses of \a,\a'-disubstituted alicyclic
 amines.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1655
_journal_page_last               1660
_journal_paper_doi               10.1039/c6ob02257j
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C29 H27 N O'
_chemical_formula_sum            'C29 H27 N O'
_chemical_formula_weight         405.52
_chemical_name_systematic
(7aS,11R,13R)-11-benzyl-13-phenyl-7a,8,9,10,11,13-hexahydronaphtho[1,2-e]pyrido[2,1-b][1,3]oxazine
_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
_audit_update_record
;
2016-09-28 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.624(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9410(4)
_cell_length_b                   32.3062(15)
_cell_length_c                   17.2176(8)
_cell_measurement_reflns_used    3905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3120
_cell_measurement_theta_min      3.5580
_cell_volume                     4395.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17711
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0532P)^2^+1.2716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                4906
_reflns_number_total             7750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02257j3.cif
_cod_data_source_block           ckj_3_07_ab
_cod_depositor_comments
'Adding full bibliography for 7155463--7155466.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7155466