New Synthetic Technologies for the Construction of Heterocycles and Tryptamines
K. C. Nicolaou; Arkady Krasovskiy; Utpal Majumder; Vincent É. Trépanier; David Y.-K. Chen; Journal of the American Chemical Society 131 (2009) 3690–3699; doi:10.1021/ja808692j

data_4104007
_publ_contact_author_email       arkady@scripps.edu
_publ_contact_author_name        'Arkady Krasovskiy'
_publ_section_title
;
 New Synthetic Technologies for the Construction of Heterocycles and
 Tryptamines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3690
_journal_page_last               3699
_journal_paper_doi               10.1021/ja808692j
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C16 H20 N2 O4'
_chemical_formula_sum            'C16 H20 N2 O4'
_chemical_formula_weight         304.34
_chemical_melting_point          450.15
_chemical_name_systematic
;
(RS)-tert-butyl 2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,3'-pyrrolidine]
-1'-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.79
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.423
_cell_length_b                   6.004
_cell_length_c                   20.005
_cell_measurement_temperature    293(2)
_cell_volume                     3099.246
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_radiation_monochromator  'Rigaku RAXIS-SPIDER'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1881
_diffrn_reflns_av_sigmaI/netI    0.1513
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8399
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.9814
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0005(12)
_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   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1604
_refine_ls_R_factor_gt           0.1128
_refine_ls_shift/su_max          2.494
_refine_ls_shift/su_mean         0.217
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2364
_refine_ls_wR_factor_ref         0.3274
_reflns_number_gt                1058
_reflns_number_total             1933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808692j_si_003.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        3099.3
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4104007