Talaromynoids A-I, Highly Oxygenated Meroterpenoids from the Marine-Derived Fungus <i>Talaromyces purpureogenus</i> SCSIO 41517 and Their Lipid Accumulation Inhibitory Activities.
Huang, Zhong-Hui; Liang, Xiao; Li, Chan-Juan; Gu, Qiong; Ma, Xuan; Qi, Shu-Hua; Journal of natural products 84 (2021) 2727–2737; doi:10.1021/acs.jnatprod.1c00681

data_1565111
_publ_section_title
;
 Talaromynoids A-I, Highly Oxygenated Meroterpenoids from the
 Marine-Derived Fungus <i>Talaromyces purpureogenus</i> SCSIO 41517 and
 Their Lipid Accumulation Inhibitory Activities.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2727
_journal_page_last               2737
_journal_paper_doi               10.1021/acs.jnatprod.1c00681
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H32 O10'
_chemical_formula_sum            'C26 H32 O10'
_chemical_formula_weight         504.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                112.706(3)
_cell_angle_beta                 95.017(2)
_cell_angle_gamma                110.165(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2185(2)
_cell_length_b                   8.4465(2)
_cell_length_c                   10.2022(3)
_cell_measurement_reflns_used    9675
_cell_measurement_temperature    106(9)
_cell_measurement_theta_max      74.1200
_cell_measurement_theta_min      4.8510
_cell_volume                     593.06(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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      106(9)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.975
_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    -13.00  16.00   0.50    0.58    --    0.00 -38.00 120.00   58
  2  \w    -29.00  31.00   0.50    0.58    --    0.00 -82.00   0.00  120
  3  \w     27.00  71.00   0.50    0.58    --    0.00  38.00  60.00   88
  4  \w    -89.00 -41.00   0.50    0.58    --    0.00 -38.00 120.00   96
  5  \w    -37.00  15.00   0.50    0.58    --    0.00 -38.00-180.00  104
  6  \w    -13.00  22.00   0.50    0.58    --    0.00  38.00  60.00   70
  7  \w    -89.00 -56.00   0.50    0.58    --    0.00 -38.00-180.00   66
  8  \w    -10.00  16.00   0.50    0.58    --    0.00 -38.00 -60.00   52
  9  \w     -9.00  21.00   0.50    0.58    --    0.00 -77.00 -60.00   60
 10  \w    -43.00 -17.00   0.50    0.58    --    0.00 -77.00 -60.00   52
 11  \w    -87.00 -47.00   0.50    0.58    --    0.00 -38.00 -60.00   80
 12  \w    -44.00 -11.00   0.50    0.58    --    0.00 -77.00-120.00   66
 13  \w     72.00 111.00   0.50    1.50    --   95.80  61.00-180.00   78
 14  \w     71.00 105.00   0.50    1.50    --   95.80  66.00-109.78   68
 15  \w     18.00 109.00   0.50    1.50    --   95.80 -82.00   0.00  182
 16  \w     95.00 121.00   0.50    1.50    --   95.80 -77.00-180.00   52
 17  \w     68.00 109.00   0.50    1.50    --   95.80  75.00  -9.46   82
 18  \w     73.00 110.00   0.50    1.50    --   95.80  58.00 -35.72   74
 19  \w     72.00  98.00   0.50    1.50    --   95.80  61.00 -60.00   52
 20  \w      6.00  81.00   0.50    1.50    --   95.80 -77.00-180.00  150
 21  \w    150.00 176.00   0.50    1.50    --   95.80  61.00  30.00   52
 22  \w    107.00 133.00   0.50    1.50    --   95.80  61.00 -60.00   52
 23  \w     72.00 101.00   0.50    1.50    --   95.80  62.00  79.09   58
 24  \w      7.00  82.00   0.50    1.50    --   95.80 -77.00  30.00  150
 25  \w     49.00 119.00   0.50    1.50    --   95.80 -82.00 -90.00  140
 26  \w     82.00 108.00   0.50    1.50    --   95.80  45.00 150.00   52
 27  \w     72.00 128.00   0.50    1.50    --   95.80  61.00  30.00  112
 28  \w    129.00 185.00   0.50    1.50    --   95.80  70.00-102.80  112
 29  \w     77.00 107.00   0.50    1.50    --   95.80  44.00-140.32   60
 30  \w     77.00 179.00   0.50    1.50    --   95.80  45.00   0.00  204
 31  \w     72.00  97.00   0.50    1.50    --   95.80  61.00-120.00   50
 32  \w     56.00 127.00   0.50    1.50    --   95.80 -82.00 120.00  142
 33  \w    132.00 185.00   0.50    1.50    --   95.80  61.00  90.00  106
 34  \w     69.00  99.00   0.50    1.50    --   95.80  70.00-102.80   60
 35  \w      8.00  41.00   0.50    1.50    --   95.80 -82.00 120.00   66
 36  \w     79.00 118.00   0.50    1.50    --   95.80  45.00 -60.00   78
 37  \w     72.00 104.00   0.50    1.50    --   95.80  61.00 150.00   64
 38  \w     72.00 125.00   0.50    1.50    --   95.80  61.00  90.00  106
 39  \w    110.00 185.00   0.50    1.50    --   95.80  61.00-150.00  150
 40  \w     76.00 148.00   0.50    1.50    --   95.80  45.00-120.00  144
 41  \w      9.00 117.00   0.50    1.50    --   95.80 -61.00-150.00  216
 42  \w     72.00  97.00   0.50    1.50    --   95.80  61.00-150.00   50
 43  \w     74.00 181.00   0.50    1.50    --   95.80  53.00  60.06  214
 44  \w     72.00  98.00   0.50    1.50    --   95.80  61.00 -30.00   52
 45  \w     72.00  98.00   0.50    1.50    --   95.80  61.00   0.00   52
 46  \w     75.00 100.00   0.50    1.50    --   95.80  61.00 120.00   50
 47  \w    116.00 157.00   0.50    1.50    --   95.80  58.00 -35.72   82
 48  \w     77.00 103.00   0.50    1.50    --   95.80  61.00  60.00   52
 49  \w    152.00 184.00   0.50    1.50    --   95.80  38.00 140.72   64
 50  \w     88.00 122.00   0.50    1.50    --   95.80 -77.00  30.00   68
 51  \w     81.00 125.00   0.50    1.50    --   95.80  30.00-180.00   88
 52  \w     78.00 109.00   0.50    1.50    --   95.80  38.00 140.72   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1977863000
_diffrn_orient_matrix_UB_12      0.0890998000
_diffrn_orient_matrix_UB_13      0.0857244000
_diffrn_orient_matrix_UB_21      0.0438989000
_diffrn_orient_matrix_UB_22      0.1431481000
_diffrn_orient_matrix_UB_23      -0.0642128000
_diffrn_orient_matrix_UB_31      -0.0399387000
_diffrn_orient_matrix_UB_32      0.1365526000
_diffrn_orient_matrix_UB_33      0.1310749000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10725
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.352
_diffrn_reflns_theta_min         4.859
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                4220
_reflns_number_total             4256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00681_si_003.cif
_cod_data_source_block           liangxiao_lx-t-30_collect
_cod_database_code               1565111
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C26 H29 O10 '
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.914
_reflns_odcompleteness_completeness 99.48
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C23(H23), C22(H22), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C25(H25A,H25B,H25C), C18(H18A,H18B,
 H18C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O19(H19), O33(H33)
;
_shelx_res_checksum              38350
_shelx_hkl_checksum              34076
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.876