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_7124166
_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            'C31 H28 Br N O2'
_chemical_formula_weight         526.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc22zj3q
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-06-23 deposited with the CCDC.    2019-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                74.1180(10)
_cell_angle_beta                 87.1980(10)
_cell_angle_gamma                76.0350(10)
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_cell_length_c                   19.3114(6)
_cell_measurement_reflns_used    2222
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      3.74
_cell_volume                     2570.98(14)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31426
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.497
_diffrn_reflns_theta_min         3.736
_exptl_absorpt_coefficient_mu    1.575
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_refine_diff_density_max         0.650
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         10671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+1.1498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9116
_reflns_number_total             10671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06267j2.cif
_cod_data_source_block           ga_90304a_a
_cod_original_cell_volume        2570.98(13)
_cod_database_code               7124166
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.616
_shelx_estimated_absorpt_t_max   0.884
_shelx_res_checksum              81186