Penispidins A-C, Aromatic Sesquiterpenoids from <i>Penicillium virgatum</i> and Their Inhibitory Effects on Hepatic Lipid Accumulation.
Yin, Guo-Ping; Gong, Man; Xue, Gui-Min; Gong, Tian; Cao, Xue; Wang, Weiyi; Hu, Chang-Hua; Journal of natural products 84 (2021) 2623–2629; doi:10.1021/acs.jnatprod.1c00185

data_1565109
_publ_section_title
;
 Penispidins A-C, Aromatic Sesquiterpenoids from <i>Penicillium
 virgatum</i> and Their Inhibitory Effects on Hepatic Lipid Accumulation.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2623
_journal_page_last               2629
_journal_paper_doi               10.1021/acs.jnatprod.1c00185
_journal_volume                  84
_journal_year                    2021
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5611(19)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   22.9072(4)
_cell_length_b                   7.95806(17)
_cell_length_c                   23.4273(4)
_cell_measurement_reflns_used    10659
_cell_measurement_temperature    291.27(19)
_cell_measurement_theta_max      70.4510
_cell_measurement_theta_min      4.0140
_cell_volume                     4093.56(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.27(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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   -105.00 -17.00   1.00    3.69    --  -35.97 -38.00-180.00   88
  2  \w   -105.00 -17.00   1.00    3.69    --  -35.97 -38.00  90.00   88
  3  \w    -97.00 -10.00   1.00    3.69    --  -35.97 139.00  65.00   87
  4  \w     17.00 105.00   1.00    3.69    --   35.97  38.00 -90.00   88
  5  \w     24.00  90.00   1.00    3.69    --   35.97-126.00-120.00   66
  6  \w     90.00 175.00   1.00   14.77    --  107.97  61.00-150.00   85
  7  \w     39.00 110.00   1.00   14.77    --  107.97 -95.00 -30.00   71
  8  \w     39.00 110.00   1.00   14.77    --  107.97 -95.00 -90.00   71
  9  \w     37.00 146.00   1.00   14.77    --  107.97 -15.00-180.00  109
 10  \w     91.00 176.00   1.00   14.77    --  107.97  45.00-180.00   85
 11  \w    101.00 178.00   1.00   14.77    --  107.97 112.00  60.00   77
 12  \w     41.00 126.00   1.00   14.77    --  107.97 -61.00-150.00   85
 13  \w     40.00 125.00   1.00   14.77    --  107.97 -45.00 120.00   85
 14  \w   -103.00 -19.00   1.00    3.69    --  -35.97 -57.00   0.00   84
 15  \w    -55.00  33.00   1.00    3.69    --  -35.97  38.00 -90.00   88
 16  \w    -53.00  31.00   1.00    3.69    --  -35.97  57.00  60.00   84
 17  \w   -104.00  -9.00   1.00    3.69    --  -35.97 -77.00  90.00   95
 18  \w   -103.00 -19.00   1.00    3.69    --  -35.97 -57.00 -60.00   84
 19  \w      1.00  75.00   1.00    3.69    --   35.97 -99.00 -30.00   74
 20  \w     87.00 178.00   1.00   14.77    --  107.97  30.00 -60.00   91
 21  \w     87.00 178.00   1.00   14.77    --  107.97  30.00  90.00   91
 22  \w     81.00 176.00   1.00   14.77    --  107.97  77.00-120.00   95
 23  \w     81.00 176.00   1.00   14.77    --  107.97  77.00 120.00   95
 24  \w     70.00 178.00   1.00   14.77    --  107.97  15.00  30.00  108
 25  \w     39.00 110.00   1.00   14.77    --  107.97 -95.00 120.00   71
 26  \w   -104.00 -35.00   1.00    3.69    --  -35.97 -77.00-180.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0547866000
_diffrn_orient_matrix_UB_12      -0.0052109000
_diffrn_orient_matrix_UB_13      0.0562360000
_diffrn_orient_matrix_UB_21      -0.0434655000
_diffrn_orient_matrix_UB_22      0.0169155000
_diffrn_orient_matrix_UB_23      0.0391959000
_diffrn_orient_matrix_UB_31      -0.0052322000
_diffrn_orient_matrix_UB_32      -0.1929051000
_diffrn_orient_matrix_UB_33      0.0019418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38674
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.854
_diffrn_reflns_theta_min         3.937
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.796
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7918
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.795
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.1217
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4237
_refine_ls_wR_factor_ref         0.4419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6004
_reflns_number_total             7918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00185_si_001.cif
_cod_data_source_block           ygp-1
_cod_depositor_comments
;

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C45 H54 O9'
_cod_original_formula_weight         738.88
_cod_original_formula_moiety         '3(C15 H18 O3)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4093.55(14)
_cod_database_code               1565109
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1'
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.740
_reflns_odcompleteness_completeness 99.94
_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. Restrained distances
 O5-H5
 0.9 with sigma of 0.02
 O7-H7A
 0.9 with sigma of 0.02
 O1-H1
 0.9 with sigma of 0.02
 C16-H5
 1.88 with sigma of 0.02
 H7A-C31
 1.88 with sigma of 0.02
 H1-C1
 1.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C24(H24A,H24B), C26(H26A,H26B), C28(H28A,H28B), C9(H9A,H9B),
 C11(H11A,H11B), C43(H43A,H43B), C27(H27A,H27B), C12(H12A,H12B), C41(H41A,H41B),
  C13(H13A,H13B), C42(H42A,H42B)
3.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C3(H3), C34(H34), C18(H18), C37(H37), C19(H19), C7(H7), C33(H33),
 C6(H6)
3.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C45(H45A,H45B,H45C), C15(H15A,H15B,
 H15C), C44(H44A,H44B,H44C), C14(H14A,H14B,H14C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.608