Antimicrobial Dolabellanes and Atranones from a Marine-Derived Strain of the Toxigenic Fungus <i>Stachybotrys chartarum</i>.
Yang, Beiye; He, Yan; Lin, Shuang; Zhang, Jinwen; Li, Huaqiang; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 82 (2019) 1923–1929; doi:10.1021/acs.jnatprod.9b00305

data_1552697
_publ_section_title
;
 Antimicrobial Dolabellanes and Atranones from a Marine-Derived Strain of
 the Toxigenic Fungus <i>Stachybotrys chartarum</i>.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              1923
_journal_page_last               1929
_journal_paper_doi               10.1021/acs.jnatprod.9b00305
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O3'
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_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             2019-06-13
_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                   8.03171(10)
_cell_length_b                   9.21545(10)
_cell_length_c                   24.1141(2)
_cell_measurement_reflns_used    35509
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.6110
_cell_measurement_theta_min      3.6680
_cell_volume                     1784.82(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -17.00  30.00   0.50    0.50    --    0.00  38.00 150.00   94
  2  \w    -45.00 -20.00   0.50    0.50    --    0.00 -77.00-120.00   50
  3  \w    -12.00  89.00   0.50    0.50    --    0.00  38.00  60.00  202
  4  \w     41.00  88.00   0.50    0.50    --    0.00  57.00 -30.00   94
  5  \w     -8.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00   78
  6  \w     34.00  85.00   0.50    0.50    --    0.00  38.00 -90.00  102
  7  \w     64.00  89.00   0.50    0.50    --    0.00  38.00   0.00   50
  8  \w     18.00  43.00   0.50    0.50    --    0.00  38.00   0.00   50
  9  \w    -21.00  38.00   0.50    0.50    --    0.00  57.00 -30.00  118
 10  \w    -17.00  27.00   0.50    0.50    --    0.00  38.00 -90.00   88
 11  \w    -13.00  29.00   0.50    0.50    --    0.00 -77.00-120.00   84
 12  \w     70.00  96.00   0.50    0.50    --   94.60  66.00  13.01   52
 13  \w    144.00 170.00   0.50    0.50    --   94.60  64.00  44.86   52
 14  \w    159.00 184.00   0.50    0.50    --   94.60  66.00  13.01   50
 15  \w     70.00  96.00   0.50    0.50    --   94.60  64.00-101.85   52
 16  \w    159.00 184.00   0.50    0.50    --   94.60  67.00 -26.15   50
 17  \w     70.00 131.00   0.50    0.50    --   94.60  64.00  44.86  122
 18  \w    113.00 183.00   0.50    0.50    --   94.60  73.00-174.32  140
 19  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 168.40   52
 20  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 -26.15   50
 21  \w    120.00 184.00   0.50    0.50    --   94.60  71.00 113.23  128
 22  \w     69.00  94.00   0.50    0.50    --   94.60  66.00 113.97   50
 23  \w      5.00  92.00   0.50    0.50    --   94.60 -77.00 -60.00  174
 24  \w     96.00 124.00   0.50    0.50    --   94.60 -77.00 -60.00   56
 25  \w     16.00  72.00   0.50    0.50    --   94.60 -82.00 120.00  112
 26  \w     80.00 126.00   0.50    0.50    --   94.60 -82.00 120.00   92
 27  \w     67.00  92.00   0.50    0.50    --   94.60  71.00 113.23   50
 28  \w     36.00 123.00   0.50    0.50    --   94.60 -82.00-180.00  174
 29  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 150.00   52
 30  \w     71.00 138.00   0.50    0.50    --   94.60  61.00  90.00  134
 31  \w     73.00 112.00   0.50    0.50    --   94.60  58.00 165.96   78
 32  \w     66.00  98.00   0.50    0.50    --   94.60  74.00 118.38   64
 33  \w     66.00  92.00   0.50    0.50    --   94.60  75.00  54.49   52
 34  \w     71.00 104.00   0.50    0.50    --   94.60  62.00  -8.80   66
 35  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -90.00   52
 36  \w     66.00  92.00   0.50    0.50    --   94.60  75.00 -62.12   52
 37  \w    108.00 184.00   0.50    0.50    --   94.60  62.00  -8.80  152
 38  \w     75.00 104.00   0.50    0.50    --   94.60  61.00  30.00   58
 39  \w     72.00  98.00   0.50    0.50    --   94.60  61.00-150.00   52
 40  \w     71.00 165.00   0.50    0.50    --   94.60  61.00  60.00  188
 41  \w     70.00 174.00   0.50    0.50    --   94.60  65.00 167.72  208
 42  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 -30.00   52
 43  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-120.00   50
 44  \w     23.00 126.00   0.50    0.50    --   94.60 -82.00   0.00  206
 45  \w     75.00 121.00   0.50    0.50    --   94.60  45.00-150.00   92
 46  \w     75.00 135.00   0.50    0.50    --   94.60  45.00 -60.00  120
 47  \w    143.00 175.00   0.50    0.50    --   94.60  45.00 -60.00   64
 48  \w     71.00 105.00   0.50    0.50    --   94.60  62.00  10.84   68
 49  \w     73.00 168.00   0.50    0.50    --   94.60  53.00 -24.91  190
 50  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -60.00   52
 51  \w    109.00 180.00   0.50    0.50    --   94.60  61.00 -60.00  142
 52  \w     11.00 121.00   0.50    0.50    --   94.60 -82.00 -90.00  220
 53  \w    129.00 181.00   0.50    0.50    --   94.60  59.00-129.83  104
 54  \w     71.00  98.00   0.50    0.50    --   94.60  59.00-129.83   54
 55  \w     71.00  96.00   0.50    0.50    --   94.60  62.00 -71.35   50
 56  \w     69.00 173.00   0.50    0.50    --   94.60  68.00  95.14  208
 57  \w     67.00  92.00   0.50    0.50    --   94.60  73.00-174.32   50
 58  \w      5.00 123.00   0.50    0.50    --   94.60 -82.00  90.00  236
 59  \w     76.00 113.00   0.50    0.50    --   94.60  49.00 -93.77   74
;
_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      -0.0485952000
_diffrn_orient_matrix_UB_12      -0.0486982000
_diffrn_orient_matrix_UB_13      -0.0588878000
_diffrn_orient_matrix_UB_21      -0.1804204000
_diffrn_orient_matrix_UB_22      -0.0247888000
_diffrn_orient_matrix_UB_23      0.0195422000
_diffrn_orient_matrix_UB_31      -0.0434078000
_diffrn_orient_matrix_UB_32      0.1580482000
_diffrn_orient_matrix_UB_33      -0.0151111000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0069
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            40013
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.036
_diffrn_reflns_theta_min         3.666
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45534
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0077(5)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0332P)^2^+0.3855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3577
_reflns_number_total             3581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00305_si_002.cif
_cod_data_source_block           20181115_2_15_3
_cod_database_code               1552697
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 99.95
_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:
 C3(H3), C6(H6), C11(H11), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6'(H6')
;
_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 1.847
_oxdiff_exptl_absorpt_empirical_full_min 0.765