Proversilins A-E, Drimane-Type Sesquiterpenoids from the Endophytic <i>Aspergillus versicolor</i>.
Li, Huaqiang; Zhang, Runge; Cao, Fei; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 83 (2020) 2200–2206; doi:10.1021/acs.jnatprod.0c00298

data_1558506
_publ_section_title
;
 Proversilins A-E, Drimane-Type Sesquiterpenoids from the Endophytic
 <i>Aspergillus versicolor</i>.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2200
_journal_page_last               2206
_journal_paper_doi               10.1021/acs.jnatprod.0c00298
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 O4'
_chemical_formula_sum            'C15 H22 O4'
_chemical_formula_weight         266.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-16
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.05.07 svn.rd67b107b for OlexSys, GUI svn.r6105)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6003(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.34756(13)
_cell_length_b                   7.9249(2)
_cell_length_c                   13.5609(3)
_cell_measurement_reflns_used    6566
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7080
_cell_measurement_theta_min      3.2060
_cell_volume                     680.82(3)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (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 0.989
_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    -47.00 -11.00   1.00    1.00    --  -41.23 -19.00-180.00   36
  2  \w   -112.00 -55.00   1.00    1.00    --  -41.23-152.00   7.00   57
  3  \w    -90.00  -2.00   1.00    1.00    --  -41.23 125.00 -30.00   88
  4  \w     15.00  79.00   1.00    1.00    --   41.23  57.00 -30.00   64
  5  \w     64.00 104.00   1.00    1.00    --   41.23  57.00-150.00   40
  6  \w     10.00  86.00   1.00    1.00    --   41.23  77.00-120.00   76
  7  \w     14.00  62.00   1.00    1.00    --   41.23  57.00-150.00   48
  8  \w     75.00 100.00   1.00    1.00    --  106.95  77.00 150.00   25
  9  \w     79.00 104.00   1.00    1.00    --  106.95  61.00-120.00   25
 10  \w     35.00 119.00   1.00    1.00    --  106.95-125.00  60.00   84
 11  \w     83.00 151.00   1.00    1.00    --  106.95  45.00 -60.00   68
 12  \w     79.00 104.00   1.00    1.00    --  106.95  61.00 -90.00   25
 13  \w     82.00 109.00   1.00    1.00    --  106.95  45.00 -90.00   27
 14  \w    119.00 146.00   1.00    1.00    --  106.95  77.00 150.00   27
 15  \w     74.00 177.00   1.00    1.00    --  106.95  77.00-120.00  103
 16  \w    144.00 170.00   1.00    1.00    --  106.95  77.00-180.00   26
 17  \w     75.00 100.00   1.00    1.00    --  106.95  77.00-150.00   25
 18  \w     80.00 106.00   1.00    1.00    --  106.95  61.00-150.00   26
 19  \w     74.00 100.00   1.00    1.00    --  106.95  77.00 -60.00   26
 20  \w    113.00 175.00   1.00    1.00    --  106.95  77.00 -60.00   62
 21  \w     79.00 104.00   1.00    1.00    --  106.95  61.00-180.00   25
 22  \w    107.00 137.00   1.00    1.00    --  106.95  61.00-180.00   30
 23  \w     55.00  83.00   1.00    1.00    --  106.95 -94.00 -30.00   28
 24  \w     78.00 104.00   1.00    1.00    --  106.95  61.00 -60.00   26
 25  \w     74.00 100.00   1.00    1.00    --  106.95  77.00-180.00   26
 26  \w     83.00 176.00   1.00    1.00    --  106.95  45.00-150.00   93
 27  \w     26.00  52.00   1.00    1.00    --  106.95 -94.00 -30.00   26
 28  \w     82.00 109.00   1.00    1.00    --  106.95  45.00 -30.00   27
 29  \w     74.00 100.00   1.00    1.00    --  106.95  77.00 -90.00   26
 30  \w     79.00 106.00   1.00    1.00    --  106.95  61.00 150.00   27
 31  \w     24.00  97.00   1.00    1.00    --  106.95 -94.00 -90.00   73
 32  \w    -93.00 -67.00   1.00    1.00    --  -41.23 -37.00-150.00   26
 33  \w     81.00 107.00   1.00    1.00    --  106.95  45.00-180.00   26
 34  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00  90.00  108
 35  \w    -66.00  33.00   1.00    1.00    --  -41.23  37.00 -90.00   99
 36  \w     13.00 113.00   1.00    1.00    --   41.23  57.00  90.00  100
 37  \w      9.00 117.00   1.00    1.00    --   41.23  77.00 -60.00  108
 38  \w     23.00  97.00   1.00    1.00    --   41.23-125.00-150.00   74
 39  \w    -33.00  66.00   1.00    1.00    --   41.23 -37.00 -90.00   99
 40  \w     17.00 116.00   1.00    1.00    --   41.23  37.00  30.00   99
 41  \w     13.00 109.00   1.00    1.00    --   41.23  57.00  30.00   96
;
_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      -0.1325984000
_diffrn_orient_matrix_UB_12      0.0121991000
_diffrn_orient_matrix_UB_13      -0.0988774000
_diffrn_orient_matrix_UB_21      0.2032422000
_diffrn_orient_matrix_UB_22      0.0222545000
_diffrn_orient_matrix_UB_23      -0.0550375000
_diffrn_orient_matrix_UB_31      0.0152539000
_diffrn_orient_matrix_UB_32      -0.1926950000
_diffrn_orient_matrix_UB_33      -0.0125955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7784
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.824
_diffrn_reflns_theta_min         3.265
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79543
_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    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0737P)^2^+0.0976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                2512
_reflns_number_total             2533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00298_si_004.cif
_cod_data_source_block           4-16-3-6
_cod_depositor_comments
'Adding full bibliography for 1558504--1558506.cif.'
_cod_database_code               1558506
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_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:
 C2(H2A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C14(H14A,
 H14B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              55433
_shelx_hkl_checksum              48812
_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 2.240
_oxdiff_exptl_absorpt_empirical_full_min 0.551