Combination of enzyme- and Lewis acid-catalyzed reactions: a new method for the synthesis of 6,7-dihydrobenzofuran-4(5H)-ones starting from 2,5-dimethylfuran and 1,3-cyclohexanediones.
Asta, Chimène; Schmidt, Dietmar; Conrad, Jürgen; Frey, Wolfgang; Beifuss, Uwe; Organic & biomolecular chemistry 11 (2013) 5692–5701; doi:10.1039/c3ob40926k

data_7153031
_publ_section_title
;
 Combination of enzyme- and Lewis acid-catalyzed reactions: a new method
 for the synthesis of 6,7-dihydrobenzofuran-4(5H)-ones starting from
 2,5-dimethylfuran and 1,3-cyclohexanediones.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5692
_journal_page_last               5701
_journal_paper_doi               10.1039/c3ob40926k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C14 H18 O3'
_chemical_formula_sum            'C14 H18 O3'
_chemical_formula_weight         234.28
_chemical_name_systematic        'compound 5d'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.603(4)
_cell_length_b                   11.0296(19)
_cell_length_c                   10.1777(17)
_cell_measurement_reflns_used    2839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      1.80
_cell_volume                     2537.3(8)
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14805
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0539P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2839
_reflns_number_total             4435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40926k.txt
_cod_data_source_block           bei04a
_cod_database_code               7153031