Diels-Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives.
Blanc, Romain; Héran, Virginie; Rahmani, Raphaël; Commeiras, Laurent; Parrain, Jean-Luc; Organic & biomolecular chemistry 8 (2010) 5490–5494; doi:10.1039/c0ob00448k

data_7153503
_publ_section_title
;
 Diels-Alder cycloaddition of o-quinonedimethides and
 alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores
 and arthrinone derivatives.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5490
_journal_page_last               5494
_journal_paper_doi               10.1039/c0ob00448k
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H10 O4'
_chemical_formula_sum            'C14 H10 O4'
_chemical_formula_weight         242.22
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-05-19T10:48:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0794(3)
_cell_length_b                   5.2878(1)
_cell_length_c                   19.8876(6)
_cell_measurement_reflns_used    10207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.85
_cell_measurement_wavelength     0.71073
_cell_volume                     1165.13(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10207
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.85
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1457
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.1994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1273
_reflns_number_total             1457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00448k.txt
_cod_data_source_block           lcf265
_cod_database_code               7153503