Chiral NHC-catalyzed oxodiene Diels-Alder reactions with alpha-chloroaldehyde bisulfite salts.
He, Ming; Beahm, Brendan J.; Bode, Jeffrey W.; Organic letters 10 (2008) 3817–3820; doi:10.1021/ol801502h

data_1504847
_publ_section_title
;
 Chiral NHC-catalyzed oxodiene Diels-Alder reactions with
 alpha-chloroaldehyde bisulfite salts.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3817
_journal_page_last               3820
_journal_paper_doi               10.1021/ol801502h
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H13 Br O4'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
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_diffrn_measurement_device_type  'CCD area detector'
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_diffrn_radiation_monochromator  graphite
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_exptl_absorpt_correction_T_min  0.190
_exptl_absorpt_correction_type   empirical
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.745
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_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.2382
_refine_ls_R_factor_gt           0.0544
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_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                805
_reflns_number_total             2752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801502h_si_003.cif
_cod_data_source_block
(R)-Ethyl_6-(4-bromophenyl)-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthrohmbic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_original_cell_volume        1412.7(9)
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_cod_database_code               1504847