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_1552699
_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         'C25 H38 O7'
_chemical_formula_sum            'C25 H38 O7'
_chemical_formula_weight         450.55
_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   geom
_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                 114.0450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5715(2)
_cell_length_b                   13.8018(3)
_cell_length_c                   9.9943(2)
_cell_measurement_reflns_used    22071
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7030
_cell_measurement_theta_min      3.1840
_cell_volume                     1205.72(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     23.00  88.00   0.50    0.50    --    0.00  38.00-180.00  130
  2  \w    -17.00  19.00   0.50    0.50    --    0.00  38.00-180.00   72
  3  \w     80.00 105.00   0.50    0.50    --   16.00  72.00-120.00   50
  4  \w    -10.00  32.00   0.50    0.50    --   16.00  72.00-120.00   84
  5  \w    -30.00  55.00   0.50    0.50    --   36.00 -46.00 -15.50  170
  6  \w     14.00  59.00   0.50    0.50    --   40.00  72.00  76.03   90
  7  \w     25.00  61.00   0.50    0.50    --   52.00  72.00-124.41   72
  8  \w     34.00  60.00   0.50    0.50    --   56.00  75.00 -42.50   52
  9  \w     30.00  61.00   0.50    0.50    --   56.00  73.00 -70.23   62
 10  \w     92.00 126.00   0.50    0.50    --   56.00  73.00 -70.23   68
 11  \w     85.00 113.00   0.50    0.50    --   60.00  70.00 179.13   56
 12  \w     32.00  62.00   0.50    0.50    --   60.00  75.00  -2.96   60
 13  \w     32.00  61.00   0.50    0.50    --   60.00  74.00 126.55   58
 14  \w     34.00  68.00   0.50    0.50    --   60.00  75.00  68.01   68
 15  \w     38.00  75.00   0.50    0.50    --   60.00  70.00 179.13   74
 16  \w     36.00  66.00   0.50    0.50    --   64.00  75.00 144.26   60
 17  \w     40.00  65.00   0.50    0.50    --   68.00  75.00-157.76   50
 18  \w    136.00 161.00   0.50    0.50    --   72.00  73.00 -48.97   50
 19  \w     46.00  77.00   0.50    0.50    --   72.00  75.00-133.69   62
 20  \w     44.00  86.00   0.50    0.50    --   72.00  75.00  89.20   84
 21  \w     45.00  71.00   0.50    0.50    --   72.00  73.00  46.49   52
 22  \w     45.00  98.00   0.50    0.50    --   72.00  73.00 -48.97  106
 23  \w    135.00 163.00   0.50    0.50    --   76.00  74.00  11.53   56
 24  \w     49.00  78.00   0.50    0.50    --   76.00  74.00  11.53   58
 25  \w     49.00  83.00   0.50    0.50    --   76.00  75.00 -91.67   68
 26  \w    141.00 177.00   0.50    0.50    --   94.60  72.00-143.47   72
 27  \w     67.00 117.00   0.50    0.50    --   94.60  72.00-143.47  100
 28  \w     37.00 113.00   0.50    0.50    --   94.60 -61.00-180.00  152
 29  \w     71.00 102.00   0.50    0.50    --   94.60  61.00 -90.00   62
 30  \w    106.00 134.00   0.50    0.50    --   94.60  61.00 -90.00   56
 31  \w     71.00 125.00   0.50    0.50    --   94.60  61.00  90.00  108
 32  \w     68.00 161.00   0.50    0.50    --   94.60  70.00  45.05  186
 33  \w     79.00 142.00   0.50    0.50    --   94.60  77.00 150.00  126
 34  \w     84.00 179.00   0.50    0.50    --   94.60  45.00 -90.00  190
 35  \w      7.00 117.00   0.50    0.50    --   94.60 -82.00 -60.00  220
 36  \w     49.00 113.00   0.50    0.50    --   94.60 -82.00-180.00  128
 37  \w     69.00 174.00   0.50    0.50    --   94.60  66.00-165.83  210
 38  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  60.00  242
 39  \w     73.00 161.00   0.50    0.50    --   94.60  61.00  30.00  176
 40  \w      5.00 104.00   0.50    0.50    --   94.60 -61.00 -60.00  198
 41  \w     67.00 171.00   0.50    0.50    --   94.60  72.00 -44.89  208
 42  \w     74.00 156.00   0.50    0.50    --   94.60  61.00 -60.00  164
 43  \w     73.00 167.00   0.50    0.50    --   94.60  63.00 141.52  188
 44  \w     71.00 148.00   0.50    0.50    --   94.60  61.00 120.00  154
 45  \w     35.00 113.00   0.50    0.50    --   94.60 -61.00  60.00  156
 46  \w     73.00 167.00   0.50    0.50    --   94.60  68.00 -21.80  188
;
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22452
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.992
_diffrn_reflns_theta_max         65.992
_diffrn_reflns_theta_min         4.845
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65508
_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    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       0.0226(10)
_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   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0235
_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^)+(0.0365P)^2^+0.2300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4200
_reflns_number_total             4203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00305_si_006.cif
_cod_data_source_block           20180912_2-22-3
_cod_database_code               1552699
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.759
_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:
 C4(H4), C6(H6), C9(H9), C11(H11), C18(H18), C21(H21), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), 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), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5'(H5'), O9'(H9')
;
_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
;