Diastereoselective synthesis of a bicyclic beta-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene
Tim Schulz; Christian Farber; Michael Leibold; Clemens Bruhn; Pascal Prochnow; Julia E. Bandow; Tanja Schneider; Timo Porsch; Max C. Holthausen; Ulrich Siemeling; Chem.Commun. 50 (2014) 2341–; doi:10.1039/c3cc48538b

data_7112003
_publ_section_title
;
 Diastereoselective synthesis of a bicyclic beta-lactam with penicillin
 G-like spectrum of activity by carbonylation of an acyclic diaminocarbene
;
_journal_name_full               Chem.Commun.
_journal_page_first              2341
_journal_paper_doi               10.1039/c3cc48538b
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C16 H30 Cl4 N2 O'
_chemical_formula_weight         408.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                90.854(7)
_cell_angle_beta                 99.683(7)
_cell_angle_gamma                105.453(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0484(6)
_cell_length_b                   10.8646(9)
_cell_length_c                   14.7271(14)
_cell_measurement_reflns_used    11192
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.33
_cell_volume                     1069.40(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      ' 212 frames, detector distance = 135 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8101
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.18
_diffrn_reflns_theta_min         1.41
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.7787
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0522
_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^)+(0.1139P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                3262
_reflns_number_total             3779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48538b.txt
_cod_data_source_block           i1009
_cod_original_cell_volume        1069.40(16)
_cod_database_code               7112003