The Laccase-Catalyzed Domino Reaction between Catechols and Heterocyclic 1,3-Dicarbonyls and the Unambiguous Structure Elucidation of the Products by NMR Spectroscopy and X-ray Crystal Structure Analysis
Szilvia Hajdok; Jürgen Conrad; Heiko Leutbecher; Sabine Strobel; Thomas Schleid; Uwe Beifuss; Journal of Organic Chemistry 74 (2009) 7230–7237; doi:10.1021/jo9011915

data_4024871
_publ_section_title
;
The Laccase-Catalyzed Domino Reaction between Catechols and Heterocyclic
1,3-Dicarbonyls and the Unambiguous Structure Elucidation of the Products
by NMR Spectroscopy and X-ray Crystal Structure Analysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7230
_journal_page_last               7237
_journal_paper_doi               10.1021/jo9011915
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H17 N O7'
_chemical_formula_sum            'C18 H17 N O7'
_chemical_formula_weight         359.33
_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                90.973(3)
_cell_angle_beta                 99.975(3)
_cell_angle_gamma                100.225(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6700(4)
_cell_length_b                   10.6575(5)
_cell_length_c                   10.9645(6)
_cell_measurement_reflns_used    4855
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.82
_cell_measurement_theta_min      0.41
_cell_volume                     867.65(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1692
_diffrn_reflns_av_sigmaI/netI    0.0936
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14236
_diffrn_reflns_theta_full        23.80
_diffrn_reflns_theta_max         23.80
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SCALEPACK (W. Minor & Z. Otwinowski)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0353P)^2^+0.3851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                1640
_reflns_number_total             2654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011915_si_001.cif
_cod_data_source_block           c:\crystal\x-red\ihapr08
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024871