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_4104009
_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         'C15 H20 N2 O2'
_chemical_formula_sum            'C15 H20 N2 O2'
_chemical_formula_weight         260.33
_chemical_melting_point          398.15
_chemical_name_systematic
'tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 97.237(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.331(2)
_cell_length_b                   16.104(3)
_cell_length_c                   10.041(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1496.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.1103
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            39662
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         2.53
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9847
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.014(5)
_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   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0969
_refine_ls_shift/su_max          4.379
_refine_ls_shift/su_mean         0.270
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1297P)^2^+0.2670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2114
_reflns_number_gt                1771
_reflns_number_total             1923
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808692j_si_005.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4104009