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_4028170
_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         'C15 H12 Br N O2'
_chemical_formula_sum            'C15 H12 Br N O2'
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_symmetry_cell_setting           orthorhombic
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_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.379(2)
_cell_length_b                   13.342(5)
_cell_length_c                   15.871(5)
_cell_measurement_reflns_used    4416
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.57
_cell_volume                     1350.8(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
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_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.048
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       platelet
_exptl_crystal_F_000             640.00
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
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_refine_diff_density_min         -0.530
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1008 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.007(17)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                2004
_reflns_number_total             2447
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo4003079_si_005.cif
_cod_data_source_block           27
_cod_original_cell_volume        1350.9(8)
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