<i>Seco</i> and Nor-<i>seco</i> Isodhilarane-Type Meroterpenoids from <i>Penicillium purpurogenum</i> and the Configuration Revisions of Related Compounds.
Wu, Yu-Zhuo; Xia, Gui-Yang; Xia, Huan; Wang, Ling-Yan; Wang, Ya-Nan; Li, Li; Shang, Hong-Cai; Lin, Sheng; Journal of natural products 85 (2022) 248–255; doi:10.1021/acs.jnatprod.1c01025

data_1566295
_publ_section_title
;
 <i>Seco</i> and Nor-<i>seco</i> Isodhilarane-Type Meroterpenoids from
 <i>Penicillium purpurogenum</i> and the Configuration Revisions of
 Related Compounds.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              248
_journal_page_last               255
_journal_paper_doi               10.1021/acs.jnatprod.1c01025
_journal_volume                  85
_journal_year                    2022
_chemical_formula_moiety         'C24 H26 O9'
_chemical_formula_sum            'C24 H26 O9'
_chemical_formula_weight         458.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-14
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2389(7)
_cell_length_b                   12.4074(5)
_cell_length_c                   15.3250(7)
_cell_measurement_reflns_used    4407
_cell_measurement_temperature    103.4
_cell_measurement_theta_max      71.1249
_cell_measurement_theta_min      3.5605
_cell_volume                     2137.00(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      103.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega    3.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000  -60.0000 43

  2 omega   30.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000   60.0000 64

  3 omega   60.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -141.0000 -173.0000 35

  4 omega  -33.00    3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000    0.0000 36

  5 omega  -32.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000  -60.0000 32

  6 omega    8.00  100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000 -180.0000 92

  7 omega   51.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 42

  8 omega   46.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -123.0000 -166.0000 65

  9 omega   42.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 54

 10 omega   65.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 65

 11 omega   42.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 52

 12 omega   92.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 81

 13 omega  146.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 28

 14 omega   77.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 68
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0794623000
_diffrn_orient_matrix_UB_12      -0.0018796000
_diffrn_orient_matrix_UB_13      -0.0817196000
_diffrn_orient_matrix_UB_21      0.1110761000
_diffrn_orient_matrix_UB_22      -0.0130540000
_diffrn_orient_matrix_UB_23      0.0581020000
_diffrn_orient_matrix_UB_31      -0.0130428000
_diffrn_orient_matrix_UB_32      -0.1233937000
_diffrn_orient_matrix_UB_33      -0.0048359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.321
_diffrn_reflns_theta_min         4.585
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.3927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3899
_reflns_number_total             4047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c01025_si_004.cif
_cod_data_source_block           exp_4895
_cod_database_code               1566295
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.890
_shelx_hkl_checksum              70840
_shelx_res_checksum              50384
_shelx_shelxl_version_number     2014/7