Diastereoselective alpha-C-H functionalization of aliphatic N-heterocycles: an efficient route to ring fused oxazines
Sujit Mahato; Surajit Haldar; Chandan K. Jana; Chem.Commun. 50 (2014) 332–; doi:10.1039/c3cc46191b

data_7110183
_publ_section_title
;
 Diastereoselective alpha-C-H functionalization of aliphatic
 N-heterocycles: an efficient route to ring fused oxazines
;
_journal_name_full               Chem.Commun.
_journal_page_first              332
_journal_paper_doi               10.1039/c3cc46191b
_journal_volume                  50
_journal_year                    2014
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_name_systematic
rac-(7aS,12R)-12-Phenyl-7a,8,10,11-tetrahydro-12H-7,9-dioxa-11a-aza-benzo[a]anthracene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 115.984(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6693(12)
_cell_length_b                   6.1313(3)
_cell_length_c                   17.7664(17)
_cell_measurement_temperature    293(2)
_cell_volume                     1632.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5126
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method ethylacetate
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0400P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                1946
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46191b.txt
_cod_data_source_block           ckj_132b
_cod_original_cell_volume        1632.3(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7110183