Chiral Bisguanidine-Catalyzed Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Chalcones with Azlactones
Shunxi Dong; Xiaohua Liu; Xiaohong Chen; Fang Mei; Yulong Zhang; Bo Gao; Lili Lin; Xiaoming Feng; Journal of the American Chemical Society 133 (2011) 13761–13761; doi:10.1021/ja205501q

data_4106673
_publ_section_title
;
 Chiral Bisguanidine-Catalyzed Inverse-Electron-Demand Hetero-Diels-Alder
 Reaction of Chalcones with Azlactones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13761
_journal_page_last               13761
_journal_paper_doi               10.1021/ja205501q
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C52 H78 N8 O2'
_chemical_formula_sum            'C52 H78 N8 O2'
_chemical_formula_weight         847.22
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   10.7895(5)
_cell_length_b                   10.7895(5)
_cell_length_c                   72.850(7)
_cell_measurement_reflns_used    7975
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      9.04
_cell_volume                     7344.5(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       86
_diffrn_reflns_limit_l_min       -78
_diffrn_reflns_number            42033
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             2772
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.240
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0830
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+4.5084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2018
_refine_ls_wR_factor_ref         0.2034
_reflns_number_gt                4185
_reflns_number_total             4327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja205501q_si_002.cif
_cod_data_source_block           sa544
_cod_original_cell_volume        7344.5(8)
_cod_database_code               4106673