Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides: highly efficient construction of azaspiro[4.4]nonenes
Mei Yang; Tianyi Wang; Shixuan Cao; Zhengjie He; Chem.Commun. 50 (2014) 13506–; doi:10.1039/C4cc05624H

data_7115874
_publ_section_title
;
 Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides:
 highly efficient construction of azaspiro[4.4]nonenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              13506
_journal_paper_doi               10.1039/C4cc05624H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C25 H19 N3 O4'
_chemical_formula_weight         425.43
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 104.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.697(2)
_cell_length_b                   14.397(3)
_cell_length_c                   26.731(7)
_cell_measurement_reflns_used    10533
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.9064
_cell_measurement_theta_min      1.7950
_cell_volume                     4366.1(17)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            43094
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_coef       0.0203(6)
_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   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1173
_refine_ls_number_reflns         19506
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0568P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                13847
_reflns_number_total             19506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05624h2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        4366.1(16)
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               7115874