<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_1566293
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H30 O9'
_chemical_formula_sum            'C26 H30 O9'
_chemical_formula_weight         486.50
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.20954(15)
_cell_length_b                   13.0261(2)
_cell_length_c                   22.2179(3)
_cell_measurement_reflns_used    11268
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6330
_cell_measurement_theta_min      3.9210
_cell_volume                     2375.94(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00  90.00   98
  2  \w    -65.00  33.00   1.00    1.00    --  -40.98  37.00 -90.00   98
  3  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 -60.00   74
  4  \w     24.00 109.00   1.00    1.01    --  106.95 -94.00-150.00   85
  5  \w     78.00 178.00   1.00    1.01    --  106.95  61.00  90.00  100
  6  \w     94.00 178.00   1.00    1.01    --  106.95 125.00 -60.00   84
  7  \w     34.00 121.00   1.00    1.01    --  106.95-125.00 150.00   87
  8  \w     24.00 109.00   1.00    1.01    --  106.95 -94.00   0.00   85
  9  \w     74.00 178.00   1.00    1.01    --  106.95  77.00  30.00  104
 10  \w   -121.00   0.00   1.00    1.00    --  -40.98 -19.00-150.00  121
 11  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00   0.00  109
 12  \w     81.00 178.00   1.00    1.01    --  106.95  45.00-180.00   97
 13  \w     79.00 178.00   1.00    1.01    --  106.95  30.00   0.00   99
 14  \w     76.00 178.00   1.00    1.01    --  106.95  70.00-170.00  102
 15  \w     79.00 178.00   1.00    1.01    --  106.95  30.00 -90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0824833000
_diffrn_orient_matrix_UB_12      -0.0181575000
_diffrn_orient_matrix_UB_13      -0.0613874000
_diffrn_orient_matrix_UB_21      0.1224542000
_diffrn_orient_matrix_UB_22      -0.0864779000
_diffrn_orient_matrix_UB_23      -0.0136751000
_diffrn_orient_matrix_UB_31      -0.1159017000
_diffrn_orient_matrix_UB_32      -0.0786329000
_diffrn_orient_matrix_UB_33      0.0291328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20105
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.634
_diffrn_reflns_theta_min         3.934
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0681P)^2^+0.2429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                4517
_reflns_number_total             4708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c01025_si_003.cif
_cod_data_source_block           xgy-3
_cod_original_cell_volume        2375.95(7)
_cod_database_code               1566293
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C22(H22), C23(H23), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C2(H2)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C26(H26A,H26B,H26C), C21(H21A,H21B,H21C)
;
_olex2_date_sample_data_collection 2017-11-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.020
_oxdiff_exptl_absorpt_empirical_full_min 0.651