Palladium-Catalyzed Synthesis of 5-Iminopyrrolones through Isocyanide Double Insertion Reaction with Terminal Alkynes and Water.
He, Yan; Wang, Ying-Chun; Hu, Kun; Xu, Xiao-Ling; Wang, Heng-Shan; Pan, Ying-Ming; The Journal of organic chemistry 81 (2016) 11813–11818; doi:10.1021/acs.joc.6b02288

data_4037419
_publ_section_title
;
 Palladium-Catalyzed Synthesis of 5-Iminopyrrolones through Isocyanide
 Double Insertion Reaction with Terminal Alkynes and Water.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11813
_journal_page_last               11818
_journal_paper_doi               10.1021/acs.joc.6b02288
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C18 H23 F N2 O'
_chemical_formula_sum            'C18 H23 F N2 O'
_chemical_formula_weight         302.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-17
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.368(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.518(3)
_cell_length_b                   11.375(4)
_cell_length_c                   16.123(5)
_cell_measurement_reflns_used    6523
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.19
_cell_volume                     1745.1(10)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15340
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.14
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     594
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0697
_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^)+(0.1160P)^2^+0.2271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                2712
_reflns_number_total             3558
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02288_si_001.cif
_cod_data_source_block           aaaa
_cod_original_cell_volume        1745.0(10)
_cod_database_code               4037419