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_4028168
_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_formula_moiety         'C16 H15 N O2'
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.30
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
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_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 122.001(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   28.023(13)
_cell_length_b                   5.984(3)
_cell_length_c                   18.353(9)
_cell_measurement_reflns_used    1259
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      41.14
_cell_volume                     2610(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b6'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b6'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
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_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.440
_refine_ls_extinction_coef       0.0155(12)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2366
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_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1050P)^2^+0.4908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1676
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_reflns_threshold_expression     F^2^>2.0\s(F^2^)
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_cod_data_source_block           20
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