Dhilirolides E-N, Meroterpenoids Produced in Culture by the Fungus Penicillium purpurogenum Collected in Sri Lanka: Structure Elucidation, Stable Isotope Feeding Studies, and Insecticidal Activity.
Centko, Ryan M; Williams, David E; Patrick, Brian O; Akhtar, Yasmin; Garcia Chavez, Miguel Angel; Wang, Yan Alexander; Isman, Murray B; de Silva, E Dilip; Andersen, Raymond J; The Journal of organic chemistry 79 (2014) 3327–3335; doi:10.1021/jo4024039

data_4029233
_publ_section_title
;
 Dhilirolides E-N, Meroterpenoids Produced in Culture by the Fungus
 Penicillium purpurogenum Collected in Sri Lanka: Structure Elucidation,
 Stable Isotope Feeding Studies, and Insecticidal Activity.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3327
_journal_page_last               3335
_journal_paper_doi               10.1021/jo4024039
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C25 H28 O7'
_chemical_formula_weight         440.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   11.4640(7)
_cell_length_b                   13.4589(8)
_cell_length_c                   14.0080(8)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      67.2
_cell_measurement_theta_min      4.56
_cell_volume                     2161.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19561
_diffrn_reflns_theta_full        67.61
_diffrn_reflns_theta_max         67.61
_diffrn_reflns_theta_min         4.56
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0016(2)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0409P)^2^+0.5097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0698
_reflns_number_gt                3796
_reflns_number_total             3836
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo4024039_si_001.cif
_cod_data_source_block           cu_ra056_0m
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029233.cif.
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4029233