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_4022892
_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_sum            'C19.5 H15 Cl3 N2 O2'
_chemical_formula_weight         415.68
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.499(4)
_cell_angle_beta                 73.807(5)
_cell_angle_gamma                64.670(5)
_cell_formula_units_Z            2
_cell_length_a                   9.378(3)
_cell_length_b                   9.474(3)
_cell_length_c                   12.814(4)
_cell_measurement_temperature    294(2)
_cell_volume                     973.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6196
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  0.9349
_exptl_absorpt_correction_T_min  0.9089
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.26(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         5173
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          1.407
_refine_ls_shift/su_mean         0.333
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.2845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                3099
_reflns_number_total             5173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0700631si20070205_041417.cif
_cod_data_source_block           60416a
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C39 H30 Cl6 N4 O4'
_cod_original_formula_weight         831.37
_cod_original_formula_units_Z            1
_cod_database_code               4022892