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_4028169
_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         'C16 H14 Br N O2'
_chemical_formula_sum            'C16 H14 Br N O2'
_chemical_formula_weight         332.20
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.65(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.954(17)
_cell_length_b                   8.03(3)
_cell_length_c                   15.54(4)
_cell_measurement_reflns_used    1257
_cell_measurement_temperature    125
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.64
_cell_volume                     738(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r6'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r6 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r6'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Schneider, et al., 2002)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6505
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       prism
_exptl_crystal_F_000             336.00
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.350
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1221 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.068(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                1690
_reflns_number_total             2652
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo4003079_si_004.cif
_cod_data_source_block           25
_cod_database_code               4028169