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_1552696
_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         '2(C20 H30 O4), C H4 O'
_chemical_formula_sum            'C41 H64 O9'
_chemical_formula_weight         700.92
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-14
_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                   11.05762(2)
_cell_length_b                   11.05762(2)
_cell_length_c                   32.17474(13)
_cell_measurement_reflns_used    91331
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6910
_cell_measurement_theta_min      2.8080
_cell_volume                     3934.036(19)
_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 0.998
_diffrn_measured_fraction_theta_max 0.992
_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     12.00  38.00   0.50    0.50    --    0.00  -7.00 142.00   52
  2  \w    -35.00  24.00   0.50    0.50    --    0.00   7.00 -42.00  118
  3  \w     94.00 119.00   0.50    0.50    --   94.60   7.00 -42.00   50
  4  \w     28.00  93.00   0.50    0.50    --   94.60  -7.00 142.00  130
  5  \w    -20.00  47.00   0.50    0.50    --    0.00  57.00   0.00  134
  6  \w    -39.00  22.00   0.50    0.50    --    0.00 -57.00  90.00  122
  7  \w    -16.00  86.00   0.50    0.50    --    0.00  38.00  30.00  204
  8  \w    -16.00  24.00   0.50    0.50    --    0.00  38.00 150.00   80
  9  \w     48.00  77.00   0.50    0.50    --    0.00  38.00 150.00   58
 10  \w     17.00  84.00   0.50    0.50    --    0.00  57.00  90.00  134
 11  \w    -22.00  13.00   0.50    0.50    --    0.00  57.00  90.00   70
 12  \w    -89.00 -63.00   0.50    0.50    --    0.00 -57.00  90.00   52
 13  \w    -17.00  80.00   0.50    0.50    --    0.00  38.00-150.00  194
 14  \w    -16.00  31.00   0.50    0.50    --    0.00 -82.00  30.00   94
 15  \w    128.00 165.00   0.50    0.50    --   94.60  72.00  37.46   74
 16  \w     66.00  91.00   0.50    0.50    --   94.60  75.00 -31.63   50
 17  \w     67.00 101.00   0.50    0.50    --   94.60  71.00  92.20   68
 18  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00-150.00  242
 19  \w     66.00  91.00   0.50    0.50    --   94.60  75.00  62.26   50
 20  \w     67.00  92.00   0.50    0.50    --   94.60  72.00  37.46   50
 21  \w     94.00 120.00   0.50    0.50    --   94.60  74.00 115.53   52
 22  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 -99.05   50
 23  \w     73.00 184.00   0.50    0.50    --   94.60  61.00 150.00  222
 24  \w     71.00 107.00   0.50    0.50    --   94.60  61.00  30.00   72
 25  \w     69.00 120.00   0.50    0.50    --   94.60  66.00-149.27  102
 26  \w    146.00 172.00   0.50    0.50    --   94.60  66.00-149.27   52
 27  \w      5.00 125.00   0.50    0.50    --   94.60 -82.00  30.00  240
 28  \w     71.00 162.00   0.50    0.50    --   94.60  61.00-180.00  182
 29  \w     69.00 105.00   0.50    0.50    --   94.60  66.00 116.15   72
 30  \w    144.00 169.00   0.50    0.50    --   94.60  66.00 116.15   50
 31  \w     68.00  94.00   0.50    0.50    --   94.60  69.00 -40.38   52
 32  \w    157.00 183.00   0.50    0.50    --   94.60  69.00 -40.38   52
 33  \w     67.00  92.00   0.50    0.50    --   94.60  71.00-107.38   50
 34  \w     71.00 183.00   0.50    0.50    --   94.60  61.00  70.18  224
 35  \w    138.00 174.00   0.50    0.50    --   94.60  74.00  -3.95   72
 36  \w    103.00 128.00   0.50    0.50    --   94.60  74.00-177.61   50
 37  \w     72.00  98.00   0.50    0.50    --   94.60  58.00 -67.26   52
 38  \w     11.00 125.00   0.50    0.50    --   94.60 -82.00 -60.00  228
 39  \w     66.00  91.00   0.50    0.50    --   94.60  74.00  -3.95   50
 40  \w     69.00  95.00   0.50    0.50    --   94.60  66.00  35.46   52
 41  \w     71.00 184.00   0.50    0.50    --   94.60  61.00   0.00  226
 42  \w     67.00 100.00   0.50    0.50    --   94.60  73.00-173.01   66
 43  \w    147.00 172.00   0.50    0.50    --   94.60  73.00-173.01   50
 44  \w     67.00 182.00   0.50    0.50    --   94.60  72.00 100.95  230
 45  \w     68.00  93.00   0.50    0.50    --   94.60  69.00 130.69   50
 46  \w    144.00 182.00   0.50    0.50    --   94.60  69.00 130.69   76
 47  \w     72.00 153.00   0.50    0.50    --   94.60  61.00  60.00  162
 48  \w     67.00  92.00   0.50    0.50    --   94.60  72.00  82.81   50
 49  \w     73.00 133.00   0.50    0.50    --   94.60  53.00 -13.19  120
 50  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 151.81   50
 51  \w     71.00  97.00   0.50    0.50    --   94.60  60.00  24.72   52
 52  \w     67.00  93.00   0.50    0.50    --   94.60  73.00 175.01   52
 53  \w     71.00 184.00   0.50    0.50    --   94.60  62.00-106.93  226
 54  \w     67.00  93.00   0.50    0.50    --   94.60  73.00  17.12   52
 55  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -16.63   50
 56  \w     67.00  92.00   0.50    0.50    --   94.60  73.00-126.86   50
 57  \w    146.00 172.00   0.50    0.50    --   94.60  69.00  81.61   52
 58  \w     72.00 142.00   0.50    0.50    --   94.60  56.00 145.80  140
 59  \w     71.00  97.00   0.50    0.50    --   94.60  59.00 -75.44   52
 60  \w    134.00 182.00   0.50    0.50    --   94.60  59.00 -75.44   96
 61  \w     68.00  94.00   0.50    0.50    --   94.60  70.00 -56.00   52
 62  \w     70.00  96.00   0.50    0.50    --   94.60  64.00-133.94   52
 63  \w     68.00  93.00   0.50    0.50    --   94.60  69.00  81.61   50
 64  \w     66.00  91.00   0.50    0.50    --   94.60  75.00 -80.00   50
 65  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 151.39   52
 66  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 -57.40   50
 67  \w     66.00  92.00   0.50    0.50    --   94.60  74.00-177.61   52
 68  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 158.59   52
 69  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 115.53   50
 70  \w     72.00 184.00   0.50    0.50    --   94.60  56.00 -55.27  224
 71  \w     70.00 182.00   0.50    0.50    --   94.60  64.00-128.32  224
 72  \w     41.00 126.00   0.50    0.50    --   94.60 -82.00-120.00  170
 73  \w     17.00  84.00   0.50    0.50    --   94.60 -82.00  60.00  134
 74  \w     91.00 126.00   0.50    0.50    --   94.60 -82.00  60.00   70
 75  \w     38.00 108.00   0.50    0.50    --   94.60 -82.00 120.00  140
;
_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      0.1199921000
_diffrn_orient_matrix_UB_12      0.0703099000
_diffrn_orient_matrix_UB_13      -0.0030187000
_diffrn_orient_matrix_UB_21      0.0696188000
_diffrn_orient_matrix_UB_22      -0.1201598000
_diffrn_orient_matrix_UB_23      -0.0035737000
_diffrn_orient_matrix_UB_31      -0.0128624000
_diffrn_orient_matrix_UB_32      0.0045831000
_diffrn_orient_matrix_UB_33      -0.0476613000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            114202
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.963
_diffrn_reflns_theta_min         4.228
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62891
_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    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(13)
_refine_ls_extinction_coef       0.00173(16)
_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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0364P)^2^+0.9726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3967
_reflns_number_total             3974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00305_si_004.cif
_cod_data_source_block           20181115_2_16_2
_cod_original_cell_volume        3934.04(2)
_cod_database_code               1552696
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 99.63
_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. Restrained distances
 O1S-C1S
 1.42 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O1S(0.5) H1S(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C13(H13)
5.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), C1S(H1SA,H1SB,H1SC)
5.e Idealised tetrahedral OH refined as rotating group:
 O5'(H5'), O6'(H6'), 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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.554