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_1552616
_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_absolute_configuration unk
_chemical_formula_moiety         'C25 H40 O6'
_chemical_formula_sum            'C25 H40 O6'
_chemical_formula_weight         436.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_Int_Tables_number      5
_audit_creation_date             2017-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0090(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1097(4)
_cell_length_b                   7.25531(13)
_cell_length_c                   15.5015(3)
_cell_measurement_reflns_used    7818
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      62.2630
_cell_measurement_theta_min      5.0470
_cell_volume                     2253.06(7)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_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 0.9927
_diffrn_measured_fraction_theta_max 0.9927
_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    -18.00  43.00   1.00    1.73    --   32.31 -57.00  60.00   61
  2  \w     69.00 103.00   1.00    6.91    --   94.50 -64.00  90.00   34
  3  \w     51.00 135.00   1.00    6.91    --   94.50 -92.00  90.00   84
  4  \w     26.00  64.00   1.00    6.91    --   94.50 -64.00  90.00   38
  5  \w     29.00 120.00   1.00    6.91    --   94.50 -50.00 -30.00   91
  6  \w     70.00 114.00   1.00    6.91    --   94.50 -92.00-150.00   44
  7  \w     23.00  77.00   1.00    6.91    --   94.50-112.00 -60.00   54
  8  \w     22.00 118.00   1.00    6.91    --   94.50 -92.00 -30.00   96
  9  \w     21.00  64.00   1.00    6.91    --   94.50-112.00 -90.00   43
 10  \w    -15.00  74.00   1.00    1.73    --   32.31 -99.00-180.00   89
 11  \w    -35.00  -4.00   1.00    1.73    --  -32.31 -77.00-180.00   31
 12  \w    -40.00  -2.00   1.00    1.73    --  -32.31 -77.00-120.00   38
 13  \w    -42.00  -9.00   1.00    1.73    --  -32.31 -57.00 -90.00   33
 14  \w    -39.00   1.00   1.00    1.73    --  -32.31 -77.00 -30.00   40
 15  \w    -59.00  -6.00   1.00    1.73    --  -32.31 -77.00  30.00   53
 16  \w    -39.00  58.00   1.00    1.73    --   32.31 -77.00   0.00   97
 17  \w    -36.00  64.00   1.00    1.73    --   32.31 -38.00-150.00  100
 18  \w     68.00 108.00   1.00    6.91    --   94.50  64.00 -90.00   40
 19  \w    100.00 161.00   1.00    6.91    --   94.50  77.00 -90.00   61
 20  \w    137.00 166.00   1.00    6.91    --   94.50  77.00 -60.00   29
 21  \w    115.00 147.00   1.00    6.91    --   94.50  64.00   0.00   32
 22  \w    106.00 163.00   1.00    6.91    --   94.50  77.00  60.00   57
 23  \w    101.00 151.00   1.00    6.91    --   94.50  64.00  90.00   50
 24  \w     96.00 122.00   1.00    6.91    --   94.50  64.00 -60.00   26
 25  \w     68.00 107.00   1.00    6.91    --   94.50  64.00   0.00   39
 26  \w     68.00 149.00   1.00    6.91    --   94.50  64.00  30.00   81
 27  \w     68.00 163.00   1.00    6.91    --   94.50  64.00 150.00   95
 28  \w     68.00 113.00   1.00    6.91    --   94.50  64.00  60.00   45
 29  \w     68.00  99.00   1.00    6.91    --   94.50  64.00  90.00   31
 30  \w     68.00 165.00   1.00    6.91    --   94.50  64.00 120.00   97
 31  \w     68.00  94.00   1.00    6.91    --   94.50  64.00 -60.00   26
 32  \w     61.00  87.00   1.00    6.91    --   94.50  77.00-120.00   26
 33  \w     68.00 152.00   1.00    6.91    --   94.50  64.00-120.00   84
 34  \w    129.00 155.00   1.00    6.91    --   94.50  77.00-180.00   26
 35  \w     69.00 154.00   1.00    6.91    --   94.50  64.00-150.00   85
 36  \w     69.00 127.00   1.00    6.91    --   94.50  64.00-180.00   58
 37  \w     61.00  87.00   1.00    6.91    --   94.50  77.00-150.00   26
 38  \w     61.00  87.00   1.00    6.91    --   94.50  77.00-180.00   26
 39  \w     61.00  87.00   1.00    6.91    --   94.50  77.00 -90.00   26
 40  \w     61.00 134.00   1.00    6.91    --   94.50  77.00 -60.00   73
 41  \w     61.00  87.00   1.00    6.91    --   94.50  77.00  30.00   26
 42  \w     62.00  88.00   1.00    6.91    --   94.50  77.00  60.00   26
 43  \w     61.00  87.00   1.00    6.91    --   94.50  77.00  90.00   26
 44  \w     61.00  87.00   1.00    6.91    --   94.50  77.00 120.00   26
 45  \w     61.00  87.00   1.00    6.91    --   94.50  77.00 150.00   26
 46  \w     63.00  89.00   1.00    6.91    --   94.50  77.00   0.00   26
 47  \w     61.00 166.00   1.00    6.91    --   94.50  77.00 -30.00  105
 48  \w    -78.00   0.00   1.00    1.73    --  -32.31 -77.00  90.00   78
 49  \w    -87.00  -9.00   1.00    1.73    --  -32.31 -57.00 120.00   78
 50  \w    -96.00 -63.00   1.00    1.73    --  -32.31 -77.00  30.00   33
 51  \w   -103.00 -54.00   1.00    1.73    --  -32.31 -77.00 -30.00   49
 52  \w    -95.00 -70.00   1.00    1.73    --  -32.31 -57.00 -90.00   25
 53  \w   -105.00 -46.00   1.00    1.73    --  -32.31 -77.00-120.00   59
 54  \w   -109.00 -76.00   1.00    1.73    --  -32.31-178.00-150.00   33
;
_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      -0.0352144000
_diffrn_orient_matrix_UB_12      -0.1673598000
_diffrn_orient_matrix_UB_13      0.0368449000
_diffrn_orient_matrix_UB_21      0.0146167000
_diffrn_orient_matrix_UB_22      -0.1142448000
_diffrn_orient_matrix_UB_23      -0.0799739000
_diffrn_orient_matrix_UB_31      0.0667812000
_diffrn_orient_matrix_UB_32      -0.0632615000
_diffrn_orient_matrix_UB_33      0.0469530000
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12412
_diffrn_reflns_theta_full        62.0782
_diffrn_reflns_theta_max         62.08
_diffrn_reflns_theta_min         4.41
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69480
_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_density_diffrn    1.2870
_exptl_crystal_description       block
_exptl_crystal_F_000             955.0775
_refine_diff_density_max         0.9753
_refine_diff_density_min         -0.1918
_refine_diff_density_rms         0.0396
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.16(16)
_refine_ls_d_res_high            0.8725
_refine_ls_d_res_low             10.0165
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0466
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    61
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0466
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+1.0232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.985
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                3471
_reflns_number_total             3537
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            np9b00705_si_002.cif
_cod_data_source_block           exp_16555
_cod_original_cell_volume        2253.07(8)
_cod_original_sg_symbol_Hall     ' C 2y'
_cod_database_code               1552616
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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:
 C007(H007), C009(H009), C00B(H00B), C00M(H00p), C00P(H00u)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00a,H00c), C00D(H00d,H00e), C00E(H00f,H00g), C00G(H00h,H00i), C00H(H00j,
 H00k), C00I(H00l,H00m), C00L(H00n,H00o), C00N(H00q,H00r), C00O(H00s,H00t)
2.c Idealised Me refined as rotating group:
 C00R(H00v,H00w,H00x), C00S(H00y,H,Ha), C00T(H00z,Hb,Hc), C00U(H00,Hd,He),
 C00V(H0aa,Hf,Hg)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002), 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 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.611