<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_1566294
_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 O8'
_chemical_formula_sum            'C26 H30 O8'
_chemical_formula_weight         470.50
_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   mixed
_audit_creation_date             2017-11-16
_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                   9.14014(9)
_cell_length_b                   13.23545(16)
_cell_length_c                   19.4513(2)
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3530
_cell_measurement_theta_min      2.2570
_cell_volume                     2353.10(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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 -16.00   1.00    1.00    --  -40.73 -37.00-180.00   99
  2  \w     23.00  97.00   1.00    1.00    --   40.73-125.00 -90.00   74
  3  \w     23.00  97.00   1.00    1.00    --   40.73-125.00-120.00   74
  4  \w     34.00 121.00   1.00    1.00    --  106.95-125.00 -90.00   87
  5  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  90.00   84
  6  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00-150.00   99
  7  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00  60.00   85
  8  \w     25.00 160.00   1.00    1.00    --  106.95 -15.00  60.00  135
  9  \w   -117.00 -36.00   1.00    1.00    --  -40.73 -77.00 -30.00   81
;
_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      0.0424325000
_diffrn_orient_matrix_UB_12      0.0682977000
_diffrn_orient_matrix_UB_13      -0.0609636000
_diffrn_orient_matrix_UB_21      -0.0705170000
_diffrn_orient_matrix_UB_22      0.0912427000
_diffrn_orient_matrix_UB_23      0.0364208000
_diffrn_orient_matrix_UB_31      0.1469401000
_diffrn_orient_matrix_UB_32      0.0238319000
_diffrn_orient_matrix_UB_33      0.0351440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11097
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.480
_diffrn_reflns_theta_min         4.040
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38101
_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    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0743P)^2^+0.6769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                4541
_reflns_number_total             4612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c01025_si_002.cif
_cod_data_source_block           xgy_7
_cod_original_cell_volume        2353.10(5)
_cod_database_code               1566294
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 99.88
_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), C9(H9), C22(H22), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C21(H21A,H21B,H21C), C18(H18A,H18B,
 H18C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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 2.615
_oxdiff_exptl_absorpt_empirical_full_min 0.744