Phosphine-mediated sequential annulations of allenyl ketone and isocyanide: a bicyclization strategy to access furan-fused eight-membered ring and spirocycle
Li, Jian; Xue, Bingxiang; Su, Shikuan; Cui, Yongmei; Fei, Youwen; Jia, Xueshun; Fang, Jianhui; Chemical Communications  (2019) –; doi:10.1039/C9CC06267J

data_7124167
_publ_section_title
;
 Phosphine-mediated sequential annulations of allenyl ketone and
 isocyanide: a bicyclization strategy to access furan-fused eight-membered
 ring and spirocycle
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06267J
_journal_year                    2019
_chemical_formula_sum            'C33 H33 N O2'
_chemical_formula_weight         475.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc22zj4r
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-23 deposited with the CCDC.    2019-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.410(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1969(12)
_cell_length_b                   15.4461(17)
_cell_length_c                   10.9974(11)
_cell_measurement_reflns_used    1134
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.90
_cell_measurement_theta_min      3.56
_cell_volume                     2570.0(4)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18384
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.998
_diffrn_reflns_theta_min         4.306
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0927P)^2^+0.6281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4364
_reflns_number_total             5424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06267j2.cif
_cod_data_source_block           ga_80928aa_a
_cod_database_code               7124167
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.883
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              24557