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_1558504
_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 4S,5R,10S
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_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     direct
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.77217(5)
_cell_length_b                   9.81597(5)
_cell_length_c                   13.76057(8)
_cell_measurement_reflns_used    25938
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7120
_cell_measurement_theta_min      4.5380
_cell_volume                     1319.960(12)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_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 0.992
_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    -70.00 -36.00   0.50    0.50    --    0.00 -51.00 -75.00   68
  2  \w    -11.00  67.00   0.50    0.50    --    0.00  51.00  70.00  156
  3  \w     77.00 152.00   0.50    0.50    --   94.60  51.00  70.00  150
  4  \w      5.00 115.00   0.50    0.50    --   94.60 -51.00 -75.00  220
  5  \w    -17.00  84.00   0.50    0.50    --    0.00  38.00 -90.00  202
  6  \w     -5.00  30.00   0.50    0.50    --    0.00 -82.00  30.00   70
  7  \w     34.00  60.00   0.50    0.50    --    0.00  38.00  60.00   52
  8  \w    -17.00  21.00   0.50    0.50    --    0.00  38.00  60.00   76
  9  \w    -17.00  88.00   0.50    0.50    --    0.00  38.00-180.00  210
 10  \w    -32.00  31.00   0.50    0.50    --    0.00 -82.00  90.00  126
 11  \w    123.00 161.00   0.50    0.50    --   94.60  65.00-174.05   76
 12  \w     70.00 109.00   0.50    0.50    --   94.60  65.00-174.05   78
 13  \w     66.00  93.00   0.50    0.50    --   94.60  74.00 -74.92   54
 14  \w     69.00 103.00   0.50    0.50    --   94.60  67.00 -83.94   68
 15  \w    132.00 158.00   0.50    0.50    --   94.60  67.00 -83.94   52
 16  \w     66.00  94.00   0.50    0.50    --   94.60  75.00 148.97   56
 17  \w    109.00 135.00   0.50    0.50    --   94.60  75.00 148.97   52
 18  \w      7.00  34.00   0.50    0.50    --   94.60 -82.00-180.00   54
 19  \w     99.00 184.00   0.50    0.50    --   94.60  73.00-123.83  170
 20  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  242
 21  \w     67.00  92.00   0.50    0.50    --   94.60  73.00-123.83   50
 22  \w    137.00 170.00   0.50    0.50    --   94.60  60.00 112.78   66
 23  \w    100.00 148.00   0.50    0.50    --   94.60  61.00 120.00   96
 24  \w     72.00  97.00   0.50    0.50    --   94.60  55.00 -55.66   50
 25  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -30.00   50
 26  \w     66.00  96.00   0.50    0.50    --   94.60  75.00 118.18   60
 27  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 -10.98   52
 28  \w     71.00 129.00   0.50    0.50    --   94.60  60.00  48.75  116
 29  \w     71.00 101.00   0.50    0.50    --   94.60  61.00  90.00   60
 30  \w     71.00  99.00   0.50    0.50    --   94.60  61.00-120.00   56
 31  \w     68.00  94.00   0.50    0.50    --   94.60  72.00  52.67   52
 32  \w    134.00 177.00   0.50    0.50    --   94.60  72.00  52.67   86
 33  \w     28.00 120.00   0.50    0.50    --   94.60 -82.00 -30.00  184
 34  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 -90.00   52
 35  \w    136.00 162.00   0.50    0.50    --   94.60  61.00  30.00   52
 36  \w     71.00 181.00   0.50    0.50    --   94.60  61.00 150.00  220
 37  \w     77.00 110.00   0.50    0.50    --   94.60  45.00 120.00   66
 38  \w     71.00  96.00   0.50    0.50    --   94.60  60.00 112.78   50
 39  \w      5.00 102.00   0.50    0.50    --   94.60 -82.00 -90.00  194
 40  \w     79.00 182.00   0.50    0.50    --   94.60  45.00 -30.00  206
 41  \w     71.00 139.00   0.50    0.50    --   94.60  61.00-180.00  136
 42  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 120.00   52
 43  \w     71.00 140.00   0.50    0.50    --   94.60  61.00-150.00  138
 44  \w    158.00 183.00   0.50    0.50    --   94.60  61.00 120.00   50
 45  \w     38.00 125.00   0.50    0.50    --   94.60 -82.00-180.00  174
 46  \w     72.00  98.00   0.50    0.50    --   94.60  59.00 -96.73   52
 47  \w     41.00  70.00   0.50    0.50    --   94.60 -82.00  30.00   58
 48  \w     96.00 122.00   0.50    0.50    --   94.60 -82.00  30.00   52
 49  \w     72.00  98.00   0.50    0.50    --   94.60  58.00-105.86   52
 50  \w     72.00  99.00   0.50    0.50    --   94.60  61.00  13.53   54
 51  \w     69.00  94.00   0.50    0.50    --   94.60  68.00  69.08   50
 52  \w     33.00  78.00   0.50    0.50    --   94.60 -82.00-150.00   90
 53  \w     92.00 118.00   0.50    0.50    --   94.60 -82.00-150.00   52
 54  \w     71.00 120.00   0.50    0.50    --   94.60  61.00  30.00   98
 55  \w    113.00 180.00   0.50    0.50    --   94.60  74.00 -74.92  134
 56  \w     70.00  96.00   0.50    0.50    --   94.60  65.00-150.96   52
 57  \w     72.00 178.00   0.50    0.50    --   94.60  55.00  -9.04  212
;
_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      -0.0380329000
_diffrn_orient_matrix_UB_12      0.1173489000
_diffrn_orient_matrix_UB_13      0.0692056000
_diffrn_orient_matrix_UB_21      0.1484932000
_diffrn_orient_matrix_UB_22      0.0522430000
_diffrn_orient_matrix_UB_23      -0.0040376000
_diffrn_orient_matrix_UB_31      -0.0365723000
_diffrn_orient_matrix_UB_32      0.0901187000
_diffrn_orient_matrix_UB_33      -0.0879926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0068
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28879
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.109
_diffrn_reflns_theta_min         5.536
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46350
_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_density_diffrn    1.260
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0129(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0343P)^2^+0.2790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2657
_reflns_number_total             2658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00298_si_002.cif
_cod_data_source_block           lhq6-4-22
_cod_depositor_comments
'Adding full bibliography for 1558504--1558506.cif.'
_cod_original_cell_volume        1319.959(12)
_cod_database_code               1558504
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.922
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C11(H11A,
 H11B), C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.801
_oxdiff_exptl_absorpt_empirical_full_min 0.752