Dhilirolides A-D, meroterpenoids produced in culture by the fruit-infecting fungus Penicillium purpurogenum collected in Sri Lanka.
de Silva, E. Dilip; Williams, David E.; Jayanetti, Dinith R.; Centko, Ryan M.; Patrick, Brian O.; Wijesundera, Ravi L. C.; Andersen, Raymond J.; Organic letters 13 (2011) 1174–1177; doi:10.1021/ol200031t

data_1501997
_publ_section_title
;
 Dhilirolides A-D, meroterpenoids produced in culture by the
 fruit-infecting fungus Penicillium purpurogenum collected in Sri Lanka.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1174
_journal_page_last               1177
_journal_paper_doi               10.1021/ol200031t
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H28 O9'
_chemical_formula_weight         472.47
_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                65.339(2)
_cell_angle_beta                 65.488(2)
_cell_angle_gamma                64.504(2)
_cell_formula_units_Z            4
_cell_length_a                   13.5779(5)
_cell_length_b                   13.6410(5)
_cell_length_c                   15.0542(6)
_cell_measurement_reflns_used    9179
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      66.57
_cell_measurement_theta_min      3.37
_cell_volume                     2191.10(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34168
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         67.40
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1266
_refine_ls_number_reflns         13627
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0481P)^2^+1.8111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                13323
_reflns_number_total             13627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200031t_si_002.cif
_cod_data_source_block           ra047
_cod_original_cell_volume        2191.10(14)
_cod_database_code               1501997