Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] Pathways
Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A. Goddard; Hongchao Guo; Ohyun Kwon; Journal of the American Chemical Society 133 (2011) 13337–13348; doi:10.1021/ja200231v

data_4106649
_publ_section_title
;
 Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3
 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] Pathways
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13337
_journal_page_last               13348
_journal_paper_doi               10.1021/ja200231v
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C16 H17 N3 O5'
_chemical_formula_sum            'C16 H17 N3 O5'
_chemical_formula_weight         331.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.337(1)
_cell_angle_beta                 84.962(1)
_cell_angle_gamma                81.670(2)
_cell_formula_units_Z            4
_cell_length_a                   7.5943(7)
_cell_length_b                   14.3844(14)
_cell_length_c                   14.7836(14)
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      3.73
_cell_volume                     1556.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21996
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.83
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         8862
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.4154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                7500
_reflns_number_total             8862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200231v_si_003.cif
_cod_data_source_block           kw410s
_cod_original_sg_symbol_H-M      ' P -1'
_cod_database_code               4106649