Aphidicolin Chemistry of the Deep-Sea-Derived Fungus <i>Botryotinia fuckeliana</i> MCCC 3A00494.
Niu, Siwen; Xia, Jin-Mei; Li, Zengpeng; Yang, Long-He; Yi, Zhi-Wei; Xie, Chun-Lan; Peng, Guizhen; Luo, Zhu-Hua; Shao, Zongze; Yang, Xian-Wen; Journal of natural products 82 (2019) 2307–2331; doi:10.1021/acs.jnatprod.9b00705

data_1552615
_publ_section_title
;
 Aphidicolin Chemistry of the Deep-Sea-Derived Fungus <i>Botryotinia
 fuckeliana</i> MCCC 3A00494.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2307
_journal_page_last               2331
_journal_paper_doi               10.1021/acs.jnatprod.9b00705
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         'C22 H36 O6, H2 O'
_chemical_formula_sum            'C22 H38 O7'
_chemical_formula_weight         414.52
_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             2017-06-26
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2255(2)
_cell_length_b                   11.9121(3)
_cell_length_c                   17.5037(4)
_cell_measurement_reflns_used    9225
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      62.1440
_cell_measurement_theta_min      4.4670
_cell_volume                     2132.08(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9953
_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    -47.00  -2.00   1.00    1.00    --  -32.31 -38.00 120.00   45
  2  \w     12.00  51.00   1.00    1.00    --   32.31 -57.00 150.00   39
  3  \w     22.00  84.00   1.00    1.38    --   94.50-112.00 150.00   62
  4  \w     82.00 136.00   1.00    1.38    --   94.50 -92.00  90.00   54
  5  \w     72.00 130.00   1.00    1.38    --   94.50 -92.00 -30.00   58
  6  \w     85.00 134.00   1.00    1.38    --   94.50 -92.00-180.00   49
  7  \w     23.00 120.00   1.00    1.38    --   94.50 -50.00 -30.00   97
  8  \w     68.00 139.00   1.00    1.38    --   94.50  64.00 -30.00   71
  9  \w    105.00 166.00   1.00    1.38    --   94.50  77.00 -30.00   61
 10  \w    121.00 167.00   1.00    1.38    --   94.50  77.00  30.00   46
 11  \w    105.00 161.00   1.00    1.38    --   94.50  64.00  90.00   56
 12  \w    101.00 141.00   1.00    1.38    --   94.50  77.00   0.00   40
 13  \w     94.00 141.00   1.00    1.38    --   94.50  77.00 -60.00   47
 14  \w     68.00 157.00   1.00    1.38    --   94.50  64.00-180.00   89
 15  \w     68.00 105.00   1.00    1.38    --   94.50  64.00 -90.00   37
 16  \w     68.00 154.00   1.00    1.38    --   94.50  64.00-150.00   86
 17  \w     68.00  96.00   1.00    1.38    --   94.50  64.00   0.00   28
 18  \w     68.00 142.00   1.00    1.38    --   94.50  64.00  30.00   74
 19  \w     69.00  95.00   1.00    1.38    --   94.50  64.00  90.00   26
 20  \w     68.00 160.00   1.00    1.38    --   94.50  64.00 120.00   92
 21  \w     68.00 145.00   1.00    1.38    --   94.50  64.00 150.00   77
 22  \w     61.00  87.00   1.00    1.38    --   94.50  77.00  90.00   26
 23  \w     61.00 164.00   1.00    1.38    --   94.50  77.00  60.00  103
 24  \w     68.00  94.00   1.00    1.38    --   94.50  64.00 -69.18   26
 25  \w     61.00 139.00   1.00    1.38    --   94.50  77.00-120.00   78
 26  \w     61.00  87.00   1.00    1.38    --   94.50  77.00  30.00   26
 27  \w     62.00  88.00   1.00    1.38    --   94.50  77.00   0.00   26
 28  \w     61.00  87.00   1.00    1.38    --   94.50  77.00 -30.00   26
 29  \w     61.00  87.00   1.00    1.38    --   94.50  77.00 -60.00   26
 30  \w     61.00 167.00   1.00    1.38    --   94.50  77.00 -90.00  106
 31  \w     62.00  87.00   1.00    1.38    --   94.50  75.00-124.65   25
 32  \w     61.00  87.00   1.00    1.38    --   94.50  77.00-150.00   26
 33  \w     61.00  87.00   1.00    1.38    --   94.50  77.00-180.00   26
 34  \w     33.00  58.00   1.00    1.38    --   94.50 -92.00 -30.00   25
 35  \w     22.00 133.00   1.00    1.38    --   94.50 -92.00-120.00  111
 36  \w     32.00 114.00   1.00    1.00    --   32.31-178.00  90.00   82
 37  \w     21.00  59.00   1.00    1.38    --   94.50 -92.00-180.00   38
 38  \w    -37.00  53.00   1.00    1.00    --   32.31 -57.00-120.00   90
 39  \w    -69.00 -44.00   1.00    1.00    --  -32.31 105.00-124.00   25
 40  \w   -114.00 -88.00   1.00    1.00    --  -32.31 178.00  30.00   26
 41  \w    -39.00  38.00   1.00    1.00    --  -32.31  57.00 150.00   77
 42  \w    -30.00  -3.00   1.00    1.00    --   32.31 -57.00 150.00   27
 43  \w    -73.00  -2.00   1.00    1.00    --  -32.31 -77.00 -30.00   71
 44  \w    -99.00  -1.00   1.00    1.00    --  -32.31 -77.00 120.00   98
 45  \w   -105.00 -79.00   1.00    1.00    --  -32.31 -77.00 -30.00   26
 46  \w   -101.00 -58.00   1.00    1.00    --  -32.31 -38.00 120.00   43
 47  \w   -103.00   1.00   1.00    1.00    --  -32.31 -77.00  30.00  104
 48  \w   -104.00   1.00   1.00    1.00    --  -32.31 -77.00-150.00  105
 49  \w   -100.00 -12.00   1.00    1.00    --  -32.31 -77.00 -90.00   88
 50  \w     61.00  86.00   1.00    1.38    --   94.50  77.00 150.00   25
 51  \w     61.00  86.00   1.00    1.38    --   94.50  77.00 120.00   25
 52  \w     36.00  93.00   1.00    1.00    --   32.31 178.00 150.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0294680000
_diffrn_orient_matrix_UB_12      0.0260595000
_diffrn_orient_matrix_UB_13      -0.0844581000
_diffrn_orient_matrix_UB_21      0.1358411000
_diffrn_orient_matrix_UB_22      0.0547710000
_diffrn_orient_matrix_UB_23      -0.0083270000
_diffrn_orient_matrix_UB_31      0.0579453000
_diffrn_orient_matrix_UB_32      -0.1142884000
_diffrn_orient_matrix_UB_33      -0.0233107000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24196
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        62.222
_diffrn_reflns_theta_max         62.222
_diffrn_reflns_theta_min         4.490
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0442P)^2^+0.4026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3248
_reflns_number_total             3351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00705_si_005.cif
_cod_data_source_block           exp_16703
_cod_original_cell_volume        2132.09(8)
_cod_database_code               1552615
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_date_sample_data_collection 2017-06-06
_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.a Free rotating group:
 O007(H0AA,H)
2.b Ternary CH refined with riding coordinates:
 C008(H008), C00B(H00D), C00H(H00K), C00I(H00L), C00J(H00M)
2.c Secondary CH2 refined with riding coordinates:
 C00C(H00E,H00F), C00E(H00G,H00H), C00G(H00I,H00J), C00L(H00N,H00O), C00M(H00P,
 H00Q), C00N(H00R,H00S), C00P(H00T,H00U), C00Q(H00V,H00W), C00R(H00X,H00Y)
2.d Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00S(H00Z,HA,HB), C00T(H00,HC,HD)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O004(H004), O005(H005)
;
_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.476
_shelx_hkl_checksum              61823
_shelx_res_checksum              76737
_shelx_shelxl_version_number     2014/8