Catalytic Intramolecular Crossed Aldehyde-Ketone Benzoin Reactions: A Novel Synthesis of Functionalized Preanthraquinones
Yoshifumi Hachisu; Jeffrey W. Bode; Keisuke Suzuki; Journal of the American Chemical Society 125 (2003) 8432–8433; doi:10.1021/ja035308f

data_4113908
_publ_section_title
;
 Catalytic Intramolecular Crossed Aldehyde-Ketone Benzoin Reactions: A
 Novel Synthesis of Functionalized Preanthraquinones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8432
_journal_page_last               8433
_journal_paper_doi               10.1021/ja035308f
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C19 H19 N O6'
_chemical_formula_weight         357.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.588(6)
_cell_angle_beta                 105.928(7)
_cell_angle_gamma                89.890(5)
_cell_formula_units_Z            2
_cell_length_a                   7.565(2)
_cell_length_b                   10.303(3)
_cell_length_c                   11.618(4)
_cell_measurement_temperature    293(2)
_cell_volume                     848.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 12
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'AFC7 Mercury CCD'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'RIGAKU UX-18 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3651
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.7945
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0563
_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^)+(0.1189P)^2^+0.0270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                2709
_reflns_number_total             3651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja035308fsi20030407_113649.cif
_cod_data_source_block           C19H19NO6
_cod_database_code               4113908