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_1552698
_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 O4, 0.06(O)'
_chemical_formula_sum            'C20 H30 O4.06'
_chemical_formula_weight         335.44
_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     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                 95.7705(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.56330(10)
_cell_length_b                   8.37430(10)
_cell_length_c                   15.3907(2)
_cell_measurement_reflns_used    33976
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6890
_cell_measurement_theta_min      2.8920
_cell_volume                     1867.50(4)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_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    -32.00  31.00   0.50    0.50    --    0.00 -82.00-150.00  126
  2  \w    -46.00 -18.00   0.50    0.50    --    0.00 -77.00 -90.00   56
  3  \w    -32.00  17.00   0.50    0.50    --    0.00 -38.00-120.00   98
  4  \w     42.00  88.00   0.50    0.50    --    0.00  38.00-180.00   92
  5  \w     49.00  85.00   0.50    0.50    --    0.00  38.00   0.00   72
  6  \w    -78.00 -20.00   0.50    0.50    --    0.00 -57.00 -30.00  116
  7  \w    -22.00  45.00   0.50    0.50    --    0.00  57.00  60.00  134
  8  \w    -17.00  39.00   0.50    0.50    --    0.00  38.00   0.00  112
  9  \w     -3.00  22.00   0.50    0.50    --    0.00 -57.00 -30.00   50
 10  \w    -17.00  37.00   0.50    0.50    --    0.00  38.00-180.00  108
 11  \w     -9.00  16.00   0.50    0.50    --    0.00 -38.00 150.00   50
 12  \w    -87.00 -45.00   0.50    0.50    --    0.00 -38.00 150.00   84
 13  \w    -86.00 -36.00   0.50    0.50    --    0.00 -38.00-120.00  100
 14  \w     69.00 133.00   0.50    0.50    --   94.60  67.00-108.32  128
 15  \w     69.00 102.00   0.50    0.50    --   94.60  66.00 -13.64   66
 16  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 148.17   52
 17  \w     71.00 134.00   0.50    0.50    --   94.60  59.00  68.58  126
 18  \w     66.00  92.00   0.50    0.50    --   94.60  74.00  66.25   52
 19  \w     70.00  95.00   0.50    0.50    --   94.60  63.00  13.38   50
 20  \w    147.00 173.00   0.50    0.50    --   94.60  61.00 170.91   52
 21  \w      8.00 118.00   0.50    0.50    --   94.60 -61.00 120.00  220
 22  \w     67.00  92.00   0.50    0.50    --   94.60  72.00-157.28   50
 23  \w    135.00 160.00   0.50    0.50    --   94.60  61.00-180.00   50
 24  \w      7.00 124.00   0.50    0.50    --   94.60 -82.00 120.00  234
 25  \w      5.00 117.00   0.50    0.50    --   94.60 -61.00   0.00  224
 26  \w     71.00 102.00   0.50    0.50    --   94.60  61.00-120.00   62
 27  \w      5.00 119.00   0.50    0.50    --   94.60 -82.00   0.00  228
 28  \w     71.00  98.00   0.50    0.50    --   94.60  60.00 128.13   54
 29  \w     67.00  93.00   0.50    0.50    --   94.60  73.00 173.10   52
 30  \w     76.00 121.00   0.50    0.50    --   94.60  45.00 -60.00   90
 31  \w     72.00 181.00   0.50    0.50    --   94.60  57.00 -47.86  218
 32  \w     67.00  92.00   0.50    0.50    --   94.60  71.00 -34.47   50
 33  \w     72.00 165.00   0.50    0.50    --   94.60  55.00 113.52  186
 34  \w     68.00  94.00   0.50    0.50    --   94.60  69.00  27.66   52
 35  \w     71.00 183.00   0.50    0.50    --   94.60  62.00  19.93  224
 36  \w     69.00  94.00   0.50    0.50    --   94.60  68.00 -49.59   50
 37  \w     76.00 169.00   0.50    0.50    --   94.60  53.00-126.27  186
 38  \w     74.00 177.00   0.50    0.50    --   94.60  61.00   0.00  206
 39  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 120.00   52
 40  \w     71.00 141.00   0.50    0.50    --   94.60  61.00 150.00  140
 41  \w      8.00  74.00   0.50    0.50    --   94.60 -82.00 -60.00  132
 42  \w     78.00 104.00   0.50    0.50    --   94.60 -82.00 -60.00   52
 43  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  90.00   52
 44  \w    124.00 166.00   0.50    0.50    --   94.60  61.00-150.00   84
 45  \w     68.00  94.00   0.50    0.50    --   94.60  69.00 -99.98   52
 46  \w     71.00 131.00   0.50    0.50    --   94.60  61.00-180.00  120
 47  \w     71.00 118.00   0.50    0.50    --   94.60  61.00-150.00   94
 48  \w     71.00 159.00   0.50    0.50    --   94.60  61.00 -30.00  176
 49  \w     70.00 126.00   0.50    0.50    --   94.60  63.00-165.78  112
 50  \w     72.00  98.00   0.50    0.50    --   94.60  56.00 -59.10   52
 51  \w     72.00 114.00   0.50    0.50    --   94.60  55.00 146.44   84
 52  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 170.91   52
 53  \w     71.00  96.00   0.50    0.50    --   94.60  62.00 109.63   50
 54  \w     73.00 124.00   0.50    0.50    --   94.60 -82.00-150.00  102
 55  \w     35.00 125.00   0.50    0.50    --   94.60 -82.00-120.00  180
 56  \w     70.00 179.00   0.50    0.50    --   94.60  64.00  49.82  218
;
_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      0.0806331000
_diffrn_orient_matrix_UB_12      -0.0153610000
_diffrn_orient_matrix_UB_13      0.0722652000
_diffrn_orient_matrix_UB_21      0.0540904000
_diffrn_orient_matrix_UB_22      -0.0999653000
_diffrn_orient_matrix_UB_23      -0.0617672000
_diffrn_orient_matrix_UB_31      0.0432408000
_diffrn_orient_matrix_UB_32      0.1537839000
_diffrn_orient_matrix_UB_33      -0.0328361000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43133
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.941
_diffrn_reflns_theta_min         2.886
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43813
_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            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             730
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.0018(3)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7473
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0405P)^2^+0.4743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                7368
_reflns_number_total             7473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00305_si_003.cif
_cod_data_source_block           2
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H60 O8.12'
_cod_original_formula_weight         670.88
_cod_original_formula_moiety         '2(C20 H30 O4), 0.12(O)'
_cod_original_formula_units_Z            2
_cod_database_code               1552698
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.908
_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. Others
 Fixed Sof: O1W(0.12309)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C18(H18), C3B(H3B), C6B(H6B), C11B(H11B), C18B(H18B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B), C2B(H2BA,H2BB),
 C5B(H5BA,H5BB), C9B(H9BA,H9BB), C10B(H10C,H10D)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C7B(H7B), C13B(H13B)
3.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), C15B(H15D,H15E,H15F), C16B(H16D,H16E,H16F),
 C17B(H17D,H17E,H17F), C19B(H19D,H19E,H19F), C20B(H20D,H20E,H20F)
3.e Idealised tetrahedral OH refined as rotating group:
 O6'(H6'), O6B(H6BA)
;
_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 2.101
_oxdiff_exptl_absorpt_empirical_full_min 0.331