Structurally Diverse Meroterpenoids from a Marine-Derived Aspergillus sp. Fungus
Wen, Huiling; Yang, Xiliang; Liu, Qian; Li, Shuangjun; Li, Qin; Zang, Yi; Chen, Chunmei; Wang, Jianping; Zhu, Hucheng; Zhang, Yonghui; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.9b00878

data_1556714
_publ_section_title
;
 Structurally Diverse Meroterpenoids from a Marine-Derived Aspergillus sp.
 Fungus
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00878
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H32 O8'
_chemical_formula_sum            'C27 H32 O8'
_chemical_formula_weight         484.52
_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     dual
_audit_creation_date             2018-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.27860(10)
_cell_length_b                   12.99470(10)
_cell_length_c                   15.25810(10)
_cell_measurement_reflns_used    46035
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6860
_cell_measurement_theta_min      4.4460
_cell_volume                     2434.53(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -22.00  27.00   0.50    0.50    --    0.00  57.00   0.00   98
  2  \w     30.00  82.00   0.50    0.50    --    0.00  57.00   0.00  104
  3  \w    -21.00  88.00   0.50    0.50    --    0.00  57.00 -60.00  218
  4  \w     22.00  48.00   0.50    0.50    --    0.00  57.00-120.00   52
  5  \w    -17.00  32.00   0.50    0.50    --    0.00  38.00  60.00   98
  6  \w     17.00  42.00   0.50    0.50    --    0.00  57.00  60.00   50
  7  \w     27.00  88.00   0.50    0.50    --    0.00  38.00-120.00  122
  8  \w    -17.00  44.00   0.50    0.50    --    0.00  38.00-180.00  122
  9  \w    -20.00   6.00   0.50    0.50    --    0.00 -77.00 -60.00   52
 10  \w    -15.00  11.00   0.50    0.50    --    0.00  57.00-120.00   52
 11  \w     50.00  89.00   0.50    0.50    --    0.00  57.00  60.00   78
 12  \w    -16.00  11.00   0.50    0.50    --    0.00  38.00-120.00   54
 13  \w     57.00  83.00   0.50    0.50    --    0.00  38.00-180.00   52
 14  \w     36.00  84.00   0.50    0.50    --    0.00  38.00  60.00   96
 15  \w     68.00 109.00   0.50    1.00    --   94.60  69.00  81.57   82
 16  \w     69.00 184.00   0.50    1.00    --   94.60  67.00  -5.37  230
 17  \w    105.00 131.00   0.50    1.00    --   94.60  56.00  55.15   52
 18  \w     70.00 144.00   0.50    1.00    --   94.60  64.00 133.71  148
 19  \w     67.00  93.00   0.50    1.00    --   94.60  73.00 124.23   52
 20  \w     72.00  99.00   0.50    1.00    --   94.60  56.00  55.15   54
 21  \w    156.00 182.00   0.50    1.00    --   94.60  66.00 -69.67   52
 22  \w     67.00  93.00   0.50    1.00    --   94.60  73.00   4.76   52
 23  \w     68.00 111.00   0.50    1.00    --   94.60  69.00 167.64   86
 24  \w     67.00  93.00   0.50    1.00    --   94.60  72.00  61.17   52
 25  \w     72.00  99.00   0.50    1.00    --   94.60  55.00  47.19   54
 26  \w     69.00  95.00   0.50    1.00    --   94.60  72.00 -26.14   52
 27  \w     67.00  93.00   0.50    1.00    --   94.60  72.00  51.55   52
 28  \w     67.00 183.00   0.50    1.00    --   94.60  71.00 139.86  232
 29  \w     74.00  99.00   0.50    1.00    --   94.60  53.00-126.61   50
 30  \w     66.00  92.00   0.50    1.00    --   94.60  75.00 -92.39   52
 31  \w     70.00  96.00   0.50    1.00    --   94.60  63.00-109.11   52
 32  \w     68.00  94.00   0.50    1.00    --   94.60  69.00 -64.32   52
 33  \w    132.00 178.00   0.50    1.00    --   94.60  72.00  14.45   92
 34  \w     67.00  92.00   0.50    1.00    --   94.60  72.00  14.45   50
 35  \w    157.00 184.00   0.50    1.00    --   94.60  63.00 162.28   54
 36  \w     74.00 184.00   0.50    1.00    --   94.60  51.00 116.22  220
 37  \w     93.00 118.00   0.50    1.00    --   94.60 -82.00-180.00   50
 38  \w    142.00 184.00   0.50    1.00    --   94.60  71.00 179.78   84
 39  \w     71.00 183.00   0.50    1.00    --   94.60  61.00-150.00  224
 40  \w     41.00  68.00   0.50    1.00    --   94.60 -82.00-180.00   54
 41  \w     67.00 138.00   0.50    1.00    --   94.60  71.00 179.78  142
 42  \w     24.00  73.00   0.50    1.00    --   94.60 -77.00 120.00   98
 43  \w     95.00 123.00   0.50    1.00    --   94.60 -77.00 120.00   56
 44  \w     71.00 107.00   0.50    1.00    --   94.60  61.00 -30.00   72
 45  \w     70.00  96.00   0.50    1.00    --   94.60  63.00 162.28   52
 46  \w     75.00 126.00   0.50    1.00    --   94.60 -82.00   0.00  102
 47  \w     71.00 134.00   0.50    1.00    --   94.60  61.00 -90.00  126
 48  \w     71.00  97.00   0.50    1.00    --   94.60  61.00 120.00   52
 49  \w     71.00 164.00   0.50    1.00    --   94.60  61.00  60.00  186
 50  \w     71.00  97.00   0.50    1.00    --   94.60  61.00-158.62   52
 51  \w     28.00  70.00   0.50    1.00    --   94.60 -82.00   0.00   84
 52  \w     67.00  92.00   0.50    1.00    --   94.60  71.00 113.28   50
 53  \w      9.00 125.00   0.50    1.00    --   94.60 -82.00 -90.00  232
 54  \w     68.00  94.00   0.50    1.00    --   94.60  73.00  -5.40   52
 55  \w     71.00  97.00   0.50    1.00    --   94.60  61.00-120.00   52
 56  \w      5.00 121.00   0.50    1.00    --   94.60 -82.00 150.00  232
 57  \w    148.00 182.00   0.50    1.00    --   94.60  69.00  81.57   68
 58  \w    150.00 175.00   0.50    1.00    --   94.60  56.00  55.15   50
 59  \w     71.00 183.00   0.50    1.00    --   94.60  61.00 -67.47  224
 60  \w     71.00 110.00   0.50    1.00    --   94.60  59.00 -38.29   78
 61  \w     69.00  95.00   0.50    1.00    --   94.60  66.00 -69.67   52
 62  \w     70.00  95.00   0.50    1.00    --   94.60  65.00-136.55   50
 63  \w    102.00 183.00   0.50    1.00    --   94.60  65.00-136.55  162
 64  \w     21.00 124.00   0.50    1.00    --   94.60 -82.00 -60.00  206
 65  \w     67.00 106.00   0.50    1.00    --   94.60 -82.00  60.00   78
 66  \w     70.00 161.00   0.50    1.00    --   94.60  64.00 -21.88  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1181853000
_diffrn_orient_matrix_UB_12      -0.0293279000
_diffrn_orient_matrix_UB_13      -0.0227377000
_diffrn_orient_matrix_UB_21      0.0267242000
_diffrn_orient_matrix_UB_22      0.0095710000
_diffrn_orient_matrix_UB_23      -0.0983424000
_diffrn_orient_matrix_UB_31      0.0325315000
_diffrn_orient_matrix_UB_32      -0.1144820000
_diffrn_orient_matrix_UB_33      -0.0022545000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            60107
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.138
_diffrn_reflns_theta_min         4.469
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0410P)^2^+0.6444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4791
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00878_si_003.cif
_cod_data_source_block           20180625_2_20_25
_cod_database_code               1556714
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.795
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C19(H19a,H19b)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C20(H20a,H20b)
2.e Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c), C25(H25a,H25b,H25c), C26(H26a,H26b,H26c), C27(H27a,H27b,H27c)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              46365
_shelx_hkl_checksum              70426
_shelx_shelxl_version_number     2018/3
_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 2.359
_oxdiff_exptl_absorpt_empirical_full_min 0.544