Delitschiapyrone A, a pyrone-naphthalenone adduct bearing a new pentacyclic ring system from the leaf-associated fungus Delitschia sp. FL1581.
Luo, Jian-Guang; Wang, Xiao-Bing; Xu, Ya-Ming; U'Ren, Jana M; Arnold, A. Elizabeth; Kong, Ling-Yi; Gunatilaka, A. A. Leslie; Organic letters 16 (2014) 5944–5947; doi:10.1021/ol502973c

data_1518184
_publ_section_title
;
 Delitschiapyrone A, a pyrone-naphthalenone adduct bearing a new
 pentacyclic ring system from the leaf-associated fungus Delitschia sp.
 FL1581.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5944
_journal_page_last               5947
_journal_paper_doi               10.1021/ol502973c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C24 H26 O9, H O0.5'
_chemical_formula_sum            'C24 H27 O9.5'
_chemical_formula_weight         467.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-04-30
_audit_creation_method
;

Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1928(13)
_cell_length_b                   17.7023(16)
_cell_length_c                   10.7282(10)
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      19.77
_cell_measurement_theta_min      2.22
_cell_volume                     2695.4(4)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      119.99
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7596
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        17.500
_diffrn_reflns_theta_max         20.813
_diffrn_reflns_theta_min         1.839
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0645 before and 0.0442 after correction. The Ratio of minimum to maximum transmission is 0.6810. The \l/2 correction factor is 0.0015.'
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0774
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+6.8724P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1894
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2288
_reflns_number_total             2828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502973c_si_002.cif
_cod_data_source_block           final
_cod_depositor_comments          'Adding full bibliography for 1518184.cif.'
_cod_original_formula_sum        'C24 H27 O9.50'
_cod_database_code               1518184
_shelxl_version_number           2012-9
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1W-H1W
 0.88 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C7(H7)
4.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2), O4(H4)
;
_shelx_res_checksum              29866
_shelx_hkl_checksum              8497