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_1552695
_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         'C23 H34 O5, H2 O'
_chemical_formula_sum            'C23 H36 O6'
_chemical_formula_weight         408.52
_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   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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.76810(10)
_cell_length_b                   10.5647(2)
_cell_length_c                   23.8071(2)
_cell_measurement_reflns_used    34957
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6940
_cell_measurement_theta_min      3.7020
_cell_volume                     2205.31(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 0.996
_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     34.00  65.00   0.50    0.50    --    0.00  38.00 -60.00   62
  2  \w    -17.00  27.00   0.50    0.50    --    0.00  38.00 -60.00   88
  3  \w    -18.00  28.00   0.50    0.50    --    0.00 -82.00 -30.00   92
  4  \w     30.00  78.00   0.50    0.50    --    0.00  38.00  90.00   96
  5  \w    -17.00  87.00   0.50    0.50    --    0.00  38.00 150.00  208
  6  \w     24.00  82.00   0.50    0.50    --    0.00  57.00  30.00  116
  7  \w    -21.00   9.00   0.50    0.50    --    0.00  57.00  30.00   60
  8  \w     -5.00  26.00   0.50    0.50    --    0.00 -77.00-120.00   62
  9  \w    -16.00  74.00   0.50    0.50    --    0.00  38.00   0.00  180
 10  \w     -1.00  28.00   0.50    0.50    --    0.00  38.00  90.00   58
 11  \w     66.00  92.00   0.50    1.50    --   94.60  75.00 -72.47   52
 12  \w     71.00 176.00   0.50    1.50    --   94.60  63.00-178.03  210
 13  \w     67.00 183.00   0.50    1.50    --   94.60  72.00-159.94  232
 14  \w     71.00 181.00   0.50    1.50    --   94.60  60.00 -13.44  220
 15  \w     66.00  92.00   0.50    1.50    --   94.60  74.00 131.78   52
 16  \w     68.00 184.00   0.50    1.50    --   94.60  72.00   0.84  232
 17  \w    141.00 167.00   0.50    1.50    --   94.60  73.00  86.30   52
 18  \w     68.00  93.00   0.50    1.50    --   94.60  69.00-114.67   50
 19  \w     67.00  95.00   0.50    1.50    --   94.60  72.00 152.43   56
 20  \w    120.00 161.00   0.50    1.50    --   94.60  73.00 -99.79   82
 21  \w     67.00  93.00   0.50    1.50    --   94.60  71.00 124.78   52
 22  \w     69.00 146.00   0.50    1.50    --   94.60  67.00 124.96  154
 23  \w     68.00  95.00   0.50    1.50    --   94.60  73.00  57.31   54
 24  \w     66.00  93.00   0.50    1.50    --   94.60  75.00 137.89   54
 25  \w     68.00  93.00   0.50    1.50    --   94.60  73.00-148.33   50
 26  \w     67.00  92.00   0.50    1.50    --   94.60  72.00-151.39   50
 27  \w     69.00  94.00   0.50    1.50    --   94.60  68.00 -14.84   50
 28  \w     67.00 168.00   0.50    1.50    --   94.60  72.00 -57.09  202
 29  \w     28.00 126.00   0.50    1.50    --   94.60 -82.00-150.00  196
 30  \w     32.00  59.00   0.50    1.50    --   94.60 -82.00  30.00   54
 31  \w     67.00 127.00   0.50    1.50    --   94.60  74.00-112.70  120
 32  \w    113.00 139.00   0.50    1.50    --   94.60  70.00  24.50   52
 33  \w     67.00 112.00   0.50    1.50    --   94.60  73.00 -99.79   90
 34  \w     40.00 113.00   0.50    1.50    --   94.60 -82.00 150.00  146
 35  \w     68.00 163.00   0.50    1.50    --   94.60  70.00 -87.53  190
 36  \w     68.00  94.00   0.50    1.50    --   94.60  69.00  82.93   52
 37  \w      6.00 123.00   0.50    1.50    --   94.60 -77.00   0.00  234
 38  \w     71.00  97.00   0.50    1.50    --   94.60  61.00 -30.00   52
 39  \w     68.00  93.00   0.50    1.50    --   94.60  69.00  -3.84   50
 40  \w     71.00 105.00   0.50    1.50    --   94.60  61.00 -60.00   68
 41  \w     68.00  95.00   0.50    1.50    --   94.60  69.00 163.74   54
 42  \w     71.00 144.00   0.50    1.50    --   94.60  61.00-120.00  146
 43  \w    152.00 178.00   0.50    1.50    --   94.60  61.00-120.00   52
 44  \w     71.00  97.00   0.50    1.50    --   94.60  61.00  30.00   52
 45  \w     71.00 152.00   0.50    1.50    --   94.60  61.00  60.00  162
 46  \w     66.00  92.00   0.50    1.50    --   94.60  74.00-172.33   52
 47  \w    146.00 183.00   0.50    1.50    --   94.60  72.00  37.92   74
 48  \w      7.00  79.00   0.50    1.50    --   94.60 -82.00 -90.00  144
 49  \w     93.00 125.00   0.50    1.50    --   94.60 -82.00 -90.00   64
 50  \w     80.00 126.00   0.50    1.50    --   94.60 -82.00  30.00   92
 51  \w     67.00  92.00   0.50    1.50    --   94.60  72.00  37.92   50
 52  \w     70.00 184.00   0.50    1.50    --   94.60  63.00 108.28  228
 53  \w    128.00 182.00   0.50    1.50    --   94.60  75.00 -72.47  108
 54  \w     68.00  94.00   0.50    1.50    --   94.60  70.00  24.50   52
 55  \w     71.00  97.00   0.50    1.50    --   94.60  61.00 120.00   52
 56  \w     72.00 116.00   0.50    1.50    --   94.60 -82.00-120.00   88
 57  \w     68.00  93.00   0.50    1.50    --   94.60  73.00  86.30   50
 58  \w     41.00  66.00   0.50    1.50    --   94.60 -82.00  60.00   50
 59  \w     97.00 126.00   0.50    1.50    --   94.60 -82.00  60.00   58
 60  \w     75.00 183.00   0.50    1.50    --   94.60  54.00  90.70  216
;
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            51631
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.926
_diffrn_reflns_theta_min         3.713
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48088
_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    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.4749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4346
_reflns_number_total             4443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00305_si_005.cif
_cod_data_source_block           20180912_2-16-1
_cod_database_code               1552695
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.718
_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, All O(H,H) groups
2. Restrained distances
 C18-C19 \\sim C18-C19A
 with sigma of 0.02
 C18-C20 \\sim C18-C20A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C19A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=
 Sof(H20F)=1-FVAR(1)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 FVAR(1)
5.a Free rotating group:
 O1W(H1WA,H1WB)
5.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C9(H9), C11(H11)
5.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C21(H21A,H21B)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13)
5.e 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), C19A(H19D,H19E,H19F),
 C20A(H20D,H20E,H20F)
5.f Idealised tetrahedral OH refined as rotating group:
 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
;