Asymmetric Diels-Alder Reactions of 2-Pyrones with a Bifunctional Organic Catalyst
Yi Wang; Hongming Li; Yong-Qiang Wang; Yan Liu; Bruce M. Foxman; Li Deng; Journal of the American Chemical Society 129 (2007) 6364–6365; doi:10.1021/ja070859h

data_4109431
_publ_section_title
;
 Asymmetric Diels-Alder Reactions of 2-Pyrones with a Bifunctional Organic
 Catalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6364
_journal_page_last               6365
_journal_paper_doi               10.1021/ja070859h
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H6 Cl1 N1 O3'
_chemical_formula_sum            'C8 H6 Cl N O3'
_chemical_formula_weight         199.59
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-01-28
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1373(2)
_cell_length_b                   8.1373(2)
_cell_length_c                   13.0130(4)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    294
_cell_measurement_theta_max      32
_cell_measurement_theta_min      3
_cell_volume                     861.66(4)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'KappaCCD ApexII'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3304
_diffrn_reflns_theta_full        33.136
_diffrn_reflns_theta_max         33.136
_diffrn_reflns_theta_min         2.503
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.8536
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.007711
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0720
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0720
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -20
_reflns_number_gt                2975
_reflns_number_total             3304
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          1.319(5)
_oxford_structure_analysis_title 'wy_14_153 in P4(3)'
_cod_data_source_file            ja070859hrom20070206_025039.cif
_cod_data_source_block           wy_14_153
_cod_original_sg_symbol_H-M      'P 43 '
_cod_original_formula_sum        'C8 H6 Cl1 N1 O3'
_cod_database_code               4109431