Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions
Noah Z. Burns; Michael R. Witten; Eric N. Jacobsen; Journal of the American Chemical Society 133 (2011) 14578–14581; doi:10.1021/ja206997e

data_4106789
_publ_section_title
;
 Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2]
 Cycloadditions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14578
_journal_page_last               14581
_journal_paper_doi               10.1021/ja206997e
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H21 F6 N O2'
_chemical_formula_weight         433.39
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.381(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.9461(7)
_cell_length_b                   5.07330(10)
_cell_length_c                   15.3388(4)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.8
_cell_measurement_theta_min      2.881
_cell_volume                     2330.30(9)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3818
_diffrn_reflns_theta_full        66.18
_diffrn_reflns_theta_max         66.18
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_T_max  0.9262
_exptl_absorpt_correction_T_min  0.8144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
;
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.9710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                3728
_reflns_number_total             3818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206997e_si_004.cif
_cod_data_source_block           diallylaniline
_cod_database_code               4106789