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_1552700
_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         'C24 H34 O5, C H4 O'
_chemical_formula_sum            'C25 H38 O6'
_chemical_formula_weight         434.55
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.942(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6586(2)
_cell_length_b                   17.0782(3)
_cell_length_c                   10.2338(2)
_cell_measurement_reflns_used    20171
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5460
_cell_measurement_theta_min      4.3270
_cell_volume                     1157.50(5)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  18.00   0.50    0.50    --    0.00  60.00 -94.00   80
  2  \w     46.00  83.00   0.50    0.50    --    0.00  60.00 -94.00   74
  3  \w     72.00  98.00   0.50    1.00    --   94.60  60.00 -94.00   52
  4  \w      5.00 117.00   0.50    1.00    --   94.60 -60.00 126.00  224
  5  \w    -16.00  23.00   0.50    0.50    --    0.00 -60.00 126.00   78
  6  \w     52.00  89.00   0.50    0.50    --    0.00  57.00-150.00   74
  7  \w    -19.00  15.00   0.50    0.50    --    0.00 -38.00 150.00   68
  8  \w    -19.00  12.00   0.50    0.50    --    0.00  57.00 -30.00   62
  9  \w    -12.00  18.00   0.50    0.50    --    0.00  38.00-150.00   60
 10  \w    -22.00  11.00   0.50    0.50    --    0.00  57.00-180.00   66
 11  \w    -14.00  28.00   0.50    0.50    --    0.00  57.00-150.00   84
 12  \w    -88.00 -32.00   0.50    0.50    --    0.00 -38.00 150.00  112
 13  \w     19.00  81.00   0.50    0.50    --    0.00  57.00 -30.00  124
 14  \w    -33.00  30.00   0.50    0.50    --    0.00 -82.00  60.00  126
 15  \w     35.00  88.00   0.50    0.50    --    0.00  57.00-180.00  106
 16  \w     41.00  89.00   0.50    0.50    --    0.00  38.00-150.00   96
 17  \w     22.00  50.00   0.50    1.00    --   94.60 -82.00-150.00   56
 18  \w     67.00 183.00   0.50    1.00    --   94.60  71.00  69.54  232
 19  \w    112.00 182.00   0.50    1.00    --   94.60  67.00  46.84  140
 20  \w     68.00  93.00   0.50    1.00    --   94.60  70.00 -44.95   50
 21  \w     71.00 177.00   0.50    1.00    --   94.60  61.00-150.00  212
 22  \w     69.00  94.00   0.50    1.00    --   94.60  67.00  46.84   50
 23  \w     69.00 104.00   0.50    1.00    --   94.60  66.00  97.74   70
 24  \w     71.00 183.00   0.50    1.00    --   94.60  62.00 126.29  224
 25  \w     68.00 140.00   0.50    1.00    --   94.60  70.00 -93.01  144
 26  \w    112.00 163.00   0.50    1.00    --   94.60  68.00  21.20  102
 27  \w     76.00 114.00   0.50    1.00    --   94.60  45.00-180.00   76
 28  \w     72.00 105.00   0.50    1.00    --   94.60  61.00  60.00   66
 29  \w     66.00 101.00   0.50    1.00    --   94.60  74.00-141.12   70
 30  \w    109.00 145.00   0.50    1.00    --   94.60  74.00-141.12   72
 31  \w     77.00 120.00   0.50    1.00    --   94.60 -82.00   0.00   86
 32  \w     69.00 106.00   0.50    1.00    --   94.60  68.00  21.20   74
 33  \w     72.00 116.00   0.50    1.00    --   94.60  61.00 150.00   88
 34  \w     72.00 156.00   0.50    1.00    --   94.60  56.00 -38.58  168
 35  \w      5.00 126.00   0.50    1.00    --   94.60 -82.00 120.00  242
 36  \w    151.00 176.00   0.50    1.00    --   94.60  69.00 -72.54   50
 37  \w     75.00 118.00   0.50    1.00    --   94.60  45.00 -90.00   86
 38  \w     69.00  94.00   0.50    1.00    --   94.60  69.00  11.67   50
 39  \w     68.00 108.00   0.50    1.00    --   94.60  69.00 -72.54   80
 40  \w    148.00 174.00   0.50    1.00    --   94.60  75.00 166.20   52
 41  \w     73.00 106.00   0.50    1.00    --   94.60  55.00  54.88   66
 42  \w     48.00 118.00   0.50    1.00    --   94.60 -61.00-120.00  140
 43  \w     73.00  99.00   0.50    1.00    --   94.60  55.00 123.45   52
 44  \w    136.00 161.00   0.50    1.00    --   94.60  55.00 123.45   50
 45  \w      8.00  75.00   0.50    1.00    --   94.60 -61.00   0.00  134
 46  \w     82.00 108.00   0.50    1.00    --   94.60 -61.00   0.00   52
 47  \w     69.00  95.00   0.50    1.00    --   94.60  66.00-139.70   52
 48  \w     67.00  92.00   0.50    1.00    --   94.60  75.00 -10.04   50
 49  \w    122.00 148.00   0.50    1.00    --   94.60  45.00-150.00   52
 50  \w     71.00 115.00   0.50    1.00    --   94.60  61.00   0.00   88
 51  \w     80.00 118.00   0.50    1.00    --   94.60  45.00-150.00   76
 52  \w     59.00 126.00   0.50    1.00    --   94.60 -82.00-150.00  134
 53  \w     67.00 160.00   0.50    1.00    --   94.60  73.00 -33.87  186
 54  \w     66.00  92.00   0.50    1.00    --   94.60  75.00 166.20   52
 55  \w    155.00 180.00   0.50    1.00    --   94.60  66.00  97.74   50
 56  \w     80.00 120.00   0.50    1.00    --   94.60 -77.00 -60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.793
_diffrn_reflns_theta_min         4.343
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29839
_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    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0665P)^2^+0.4413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                4567
_reflns_number_total             4604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00305_si_007.cif
_cod_data_source_block           20180912_2-18-3
_cod_database_code               1552700
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.790
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H23A,H23B,H23C} of C23, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, {H17A,H17B,H17C} of C17, {H20A,H20B,H20C} of C20, {H1SA,
  H1SB,H1SC} of C1S, {H19A,H19B,H19C} of C19, {H16A,H16B,H16C} of C16
2.a Riding coordinates:
 C3(H3A,H3B), C11(H11)
2.b Ternary CH refined with riding coordinates:
 C6(H6), C18(H18), C21(H21), C22(H22)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C), C1S(H1SA,H1SB,H1SC)
2.f Idealised tetrahedral OH refined as rotating group:
 O15'(H15'), O22'(H22'), O1S(H1S)
;
_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
;