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_7110188
_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         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
_chemical_name_systematic
rac-(7aS,12R)-12-(3-Nitro-phenyl)-8,9,10,11-tetrahydro-7aH,12H-7-oxa-11a-aza-benzo[a]anthracene
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8679(18)
_cell_length_b                   15.764(3)
_cell_length_c                   13.088(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1829.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19032
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method ethylacetate
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0492P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2632
_reflns_number_total             3926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46191b.txt
_cod_data_source_block           sh
_cod_original_cell_volume        1829.7(7)
_cod_database_code               7110188