Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction
Claire C. A. Cariou; Guy J. Clarkson; Michael Shipman; Journal of Organic Chemistry 73 (2008) 9762–9764; doi:10.1021/jo801664g

data_4023928
_publ_contact_author_address
;
Department of Chemistry
University of Warwick
Gibbethill Road
Coventry
CV4 7AL
UK
;
_publ_contact_author_email       m.shipman@warwick.ac.uk
_publ_contact_author_name        'Michael Shipman'
_publ_contact_author_phone       '024 765 23186'
_publ_section_title
;
 Rapid Synthesis of 1,3,4,4-Tetrasubstituted \b-Lactams from
 Methyleneaziridines Using a Four-Component Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9762
_journal_page_last               9764
_journal_paper_doi               10.1021/jo801664g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C34 H35 N O3'
_chemical_formula_weight         505.63
_space_group_IT_number           2
_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                106.709(2)
_cell_angle_beta                 99.009(2)
_cell_angle_gamma                112.083(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7661(3)
_cell_length_b                   11.6217(3)
_cell_length_c                   14.3084(4)
_cell_measurement_reflns_used    30507
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.91
_cell_volume                     1375.72(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29928
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0549P)^2^+0.3974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                4937
_reflns_number_total             6292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801664g_si_001.cif
_cod_data_source_block           cc3(2a)
_cod_database_code               4023928