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_1558505
_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         'C11 H13 N O3'
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.22
_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             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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.42071(10)
_cell_length_b                   12.6801(3)
_cell_length_c                   14.9194(3)
_cell_measurement_reflns_used    6434
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3410
_cell_measurement_theta_min      2.9110
_cell_volume                     1025.49(4)
_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 0.995
_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   -115.00 -16.00   1.00    1.00    --  -40.48 -37.00 -90.00   99
  2  \w    -34.00  65.00   1.00    1.00    --   40.48 -37.00  30.00   99
  3  \w     27.00  99.00   1.00    1.00    --   40.48-129.00 -68.00   72
  4  \w     79.00 178.00   1.00    1.00    --  107.58  30.00   0.00   99
  5  \w     35.00 133.00   1.00    1.00    --  107.58 -45.00 150.00   98
  6  \w     94.00 178.00   1.00    1.00    --  107.58 125.00-180.00   84
  7  \w     29.00 113.00   1.00    1.00    --  107.58-104.00   8.00   84
  8  \w     94.00 178.00   1.00    1.00    --  107.58 125.00 -60.00   84
  9  \w     35.00 133.00   1.00    1.00    --  107.58 -45.00   0.00   98
 10  \w   -113.00 -12.00   1.00    1.00    --  -40.48 -57.00  30.00  101
 11  \w   -113.00 -12.00   1.00    1.00    --  -40.48 -57.00 150.00  101
 12  \w    -32.00  69.00   1.00    1.00    --   40.48 -57.00 -90.00  101
 13  \w     75.00 100.00   1.00    1.00    --  107.58  77.00  60.00   25
 14  \w     55.00 178.00   1.00    1.00    --  107.58  15.00 -90.00  123
 15  \w     79.00 178.00   1.00    1.00    --  107.58  30.00 150.00   99
 16  \w   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00 120.00  109
 17  \w   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00-120.00  109
 18  \w   -116.00 -17.00   1.00    1.00    --  -41.48 -37.00  30.00   99
 19  \w   -118.00  -9.00   1.00    1.00    --  -41.48 -77.00   0.00  109
 20  \w      4.00  85.00   1.00    1.00    --   41.48-104.00   8.00   81
 21  \w     23.00  98.00   1.00    1.00    --   41.48-125.00-150.00   75
 22  \w     79.00 178.00   1.00    3.00    --  106.95  30.00  90.00   99
 23  \w     30.00 116.00   1.00    3.00    --  106.95-111.00 150.00   86
 24  \w     81.00  97.00   1.00    3.00    --  106.95  45.00  30.00   16
;
_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      0.0486999000
_diffrn_orient_matrix_UB_12      -0.1030837000
_diffrn_orient_matrix_UB_13      -0.0517265000
_diffrn_orient_matrix_UB_21      0.0584990000
_diffrn_orient_matrix_UB_22      0.0641202000
_diffrn_orient_matrix_UB_23      -0.0850537000
_diffrn_orient_matrix_UB_31      0.2737813000
_diffrn_orient_matrix_UB_32      0.0046817000
_diffrn_orient_matrix_UB_33      0.0274893000
_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  0.0396
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12007
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.932
_diffrn_reflns_theta_min         4.576
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64647
_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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 760 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0518P)^2^+0.5620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2006
_reflns_number_total             2064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00298_si_003.cif
_cod_data_source_block           4-16-3-11
_cod_depositor_comments
'Adding full bibliography for 1558504--1558506.cif.'
_cod_database_code               1558505
_shelx_shelxl_version_number     2018/3
_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, All N(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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C9(H9), C8(H8), C6(H6), C7(H7), C5(H5)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              51234
_shelx_hkl_checksum              30230
_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 1.794
_oxdiff_exptl_absorpt_empirical_full_min 0.447