Phosphine-catalyzed asymmetric synthesis of beta-lactones from arylketoketenes and aromatic aldehydes.
Mondal, Mukulesh; Ibrahim, Ahmad A.; Wheeler, Kraig A.; Kerrigan, Nessan J.; Organic letters 12 (2010) 1664–1667; doi:10.1021/ol100075m

data_1502846
_publ_section_title
;
 Phosphine-catalyzed asymmetric synthesis of beta-lactones from
 arylketoketenes and aromatic aldehydes.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1664
_journal_page_last               1667
_journal_paper_doi               10.1021/ol100075m
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration R
_chemical_formula_moiety         'C21 H15 N O4'
_chemical_formula_sum            'C21 H15 N O4'
_chemical_formula_weight         345.34
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5125(1)
_cell_length_b                   10.8526(1)
_cell_length_c                   16.4229(2)
_cell_measurement_reflns_used    8120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      4.62
_cell_measurement_theta_min      71.06
_cell_volume                     1695.42(3)
_computing_cell_refinement       'APEXII (Bruker, 2009)'
_computing_data_collection       'ApexII (Bruker, 2009)'
_computing_data_reduction
;
'SAINT (Bruker, 2009) and XPREP (Bruker, 2009)'  
;
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II 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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24408
_diffrn_reflns_theta_full        71.71
_diffrn_reflns_theta_max         71.71
_diffrn_reflns_theta_min         4.88
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.8127
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.05(Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent rod'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.2177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                3213
_reflns_number_total             3296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100075m_si_004.cif
_cod_data_source_block           nker02
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               1502846