NHC-Promoted Asymmetric β-Lactone Formation from Arylalkylketenes and Electron-Deficient Benzaldehydes or Pyridinecarboxaldehydes
James Douglas; James E. Taylor; Gwydion Churchill; Alexandra M. Z. Slawin; Andrew D. Smith; Journal of Organic Chemistry 78 (2013) 3925–3938; doi:10.1021/jo4003079

data_4028167
_publ_section_title
;
 NHC-Promoted Asymmetric \b-Lactone Formation from Arylalkylketenes and
 Electron-Deficient Benzaldehydes or Pyridinecarboxaldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3925
_journal_page_last               3938
_journal_paper_doi               10.1021/jo4003079
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_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                 98.455(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.679(6)
_cell_length_b                   9.166(5)
_cell_length_c                   16.543(10)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.7
_cell_measurement_theta_min      21.7
_cell_volume                     1451.7(15)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18752
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.11
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       Prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1694P)^2^+0.7304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1993
_refine_ls_wR_factor_ref         0.2300
_reflns_number_gt                4498
_reflns_number_total             4913
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4003079_si_002.cif
_cod_data_source_block           4
_cod_database_code               4028167