Metabolites of the higher fungi. Part 32. Rosnecatrone, a phytotoxic bicyclo[4.1.0]hept-3-en-2-one from the fungus Rosellinia necatrix Prill
Edwards, Raymond L.; Maitland, Derek J.; Scowen, Ian J.; De Sousa, Antonio J. T.; Whalley, Anthony J. S.; Journal of the Chemical Society, Perkin Transactions 1  (2001) 537–; doi:10.1039/b008195g

data_7213440
_publ_contact_author             'Dr Raymond L. Edwards'
_publ_section_title
;
 Metabolites of the higher fungi. Part 32. Rosnecatrone, a phytotoxic
 bicyclo[4.1.0]hept-3-en-2-one from the fungus Rosellinia necatrix Prill
;
_journal_issue                   5
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              537
_journal_paper_doi               10.1039/b008195g
_journal_year                    2001
_chemical_formula_sum            'C23 H30 O9'
_chemical_formula_weight         450.47
_chemical_name_common            'rosnecatrol tetraacetate'
_space_group_IT_number           1
_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                67.40(3)
_cell_angle_beta                 75.08(3)
_cell_angle_gamma                67.33(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3738(17)
_cell_length_b                   8.5966(17)
_cell_length_c                   10.291(2)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     625.9(3)
_computing_cell_refinement       'Stoe DIF4 6.2D'
_computing_data_collection       'Stoe DIF4 6.2D'
_computing_data_reduction        'XRED 1.05 (Stoe 1995)'
_computing_molecular_graphics    'ORTEP 3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WIN-GX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe STADI-4 four-circle'
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_radiation_detector       'NaI(Tl) Scintillation Counter'
_diffrn_radiation_monochromator  'Planar graphite'
_diffrn_radiation_polarisn_norm  90.0
_diffrn_radiation_polarisn_ratio 0.9560
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0096
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2112
_diffrn_reflns_theta_full        59.99
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         4.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0258(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.1002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2009
_reflns_number_total             2108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b008195gsup1.cif
_cod_data_source_block           py004_0
_cod_original_cell_volume        625.9(2)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7213440
_audit_contact_author            'Dr Ian J. Scowen'