Interaction of β-Lactam Carbenes with Aryl Isonitriles: An Unprecedented Rearrangement of 2-Azetidinonylidene Indoles to δ-Carbolinones
Ying Cheng; Lan-Qing Cheng; Journal of Organic Chemistry 72 (2007) 2625–2630; doi:10.1021/jo0700631

data_4022890
_publ_section_title
;
 Interaction of \b-Lactam Carbenes with Aryl Isonitriles:
 An Unprecedented Rearrangement of 2-Azetidinonylidene Indoles
 to \d-Carbolinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2625
_journal_page_last               2630
_journal_paper_doi               10.1021/jo0700631
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C39 H34 Br2 Cl2 N4 O3.50'
_chemical_formula_sum            'C39 H34 Br2 Cl2 N4 O3.5'
_chemical_formula_weight         845.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.109(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9918(14)
_cell_length_b                   16.947(3)
_cell_length_c                   24.121(4)
_cell_measurement_reflns_used    10413
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      1.5
_cell_volume                     3654.8(10)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            33571
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    2.410
_exptl_absorpt_correction_T_max  0.6991
_exptl_absorpt_correction_T_min  0.4946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.675
_refine_diff_density_min         -1.332
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.0074(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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         8679
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0806P)^2^+3.4078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                6774
_reflns_number_total             8679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0700631si20070205_041341.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C39 H34 Br2 Cl2 N4 O3.50'
_cod_database_code               4022890