BINAPHANE-Catalyzed Asymmetric Synthesis of trans-β-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines.
Chen, Shi; Salo, Eric C.; Wheeler, Kraig A.; Kerrigan, Nessan J.; Organic letters 14 (2012) 1784–1787; doi:10.1021/ol3003783

data_1507573
_publ_section_title
;
 BINAPHANE-Catalyzed Asymmetric Synthesis of trans-\b-Lactams from
 Disubstituted Ketenes and N-Tosyl Arylimines.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1784
_journal_page_last               1787
_journal_paper_doi               10.1021/ol3003783
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H29 N O3 S'
_chemical_formula_weight         411.54
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.321(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2199(7)
_cell_length_b                   13.2515(6)
_cell_length_c                   26.9912(14)
_cell_measurement_reflns_used    8084
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.482
_cell_measurement_theta_min      3.274
_cell_volume                     4728.3(4)
_computing_cell_refinement       APEX2
_computing_data_reduction
;
SAINT (Bruker, 2009) and XPREP (Bruker, 2009)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37323
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'tranparent rod'
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_platon_squeeze_details
;
 Refinement with this model resulted in a final R value of 7-8%.  Significant
 unidentifiable residual electron density was observed at 1.5 e/A3 suggesting
 the possible presence of disorded solvent.  Processing the data with
 Platon/Squeeze produced a solventless data set that gave satisfactory
 convergence.  The number of electrons (51 e's) determined for this
 void space (193 A3) corresponds to both recrystallization solvents
 used (hexanes, 51 e's;  EtOAc, 48 e's).  
;
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.032(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.009
_refine_ls_goodness_of_fit_obs   1.071
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1229
_refine_ls_number_reflns         13817
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.010
_refine_ls_restrained_S_obs      1.072
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_obs          0.0499
_refine_ls_shift/esd_max         0.069
_refine_ls_shift/esd_mean        0.044
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.3341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1232
_refine_ls_wR_factor_obs         0.1164
_reflns_number_gt                11176
_reflns_number_total             13817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3003783_si_004.cif
_cod_data_source_block           NKER05squeezed
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.3341P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.3341P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1507573