Versicoamides F-H, Prenylated Indole Alkaloids from Aspergillus tennesseensis.
Liu, Li; Wang, Long; Bao, Li; Ren, Jinwei; Bahadur Basnet, Buddha; Liu, Ruixing; He, Luwei; Han, Junjie; Yin, Wen-Bing; Liu, Hongwei; Organic letters 19 (2017) 942–945; doi:10.1021/acs.orglett.7b00145

data_1545473
_publ_section_title
;
 Versicoamides F-H, Prenylated Indole Alkaloids from Aspergillus
 tennesseensis.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              942
_journal_page_last               945
_journal_paper_doi               10.1021/acs.orglett.7b00145
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H37 N3 O8, C H4 O, 0.5(C0.4 H2.1999 O)'
_chemical_formula_sum            'C34.2 H42.09 N3 O9.5'
_chemical_formula_weight         647.18
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.197(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7527(6)
_cell_length_b                   8.9786(3)
_cell_length_c                   24.0362(9)
_cell_measurement_reflns_used    11528
_cell_measurement_temperature    104.7
_cell_measurement_theta_max      71.0593
_cell_measurement_theta_min      2.9501
_cell_volume                     3229.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      104.7
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -32.00   -3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -44.0000  161.0000 29

  2 omega  -20.00   22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000 -120.0000 42

  3 omega  -61.00  -34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -44.0000  161.0000 27

  4 omega   33.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000 -120.0000 27

  5 omega  -48.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -180.0000 29

  6 omega   44.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000 -180.0000 27

  7 omega   -9.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -37.0000 -180.0000 64

  8 omega   34.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000 -120.0000 27

  9 omega   61.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000  -90.0000 41

 10 omega   53.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000  -60.0000 28

 11 omega   38.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000 -180.0000 67

 12 omega   17.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000  -90.0000 37

 13 omega   75.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000 -120.0000 25

 14 omega  -26.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -77.0000   90.0000 88

 15 omega   10.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -97.0000   59.0000 40

 16 omega  -30.00   47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -77.0000 -180.0000 77

 17 omega   29.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000 -150.0000 26

 18 omega   25.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000   60.0000 70

 19 omega   15.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000  -90.0000 71

 20 omega  138.00  165.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 27

 21 omega   73.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 25

 22 omega   81.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 23 omega   38.00  110.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -97.0000   12.0000 72

 24 omega  118.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 56

 25 omega   72.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 31

 26 omega   40.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 57

 27 omega   91.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   44.0000 -161.0000 26

 28 omega   92.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 25

 29 omega  127.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 43

 30 omega  119.00  164.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 45

 31 omega   53.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 44

 32 omega   71.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 25

 33 omega   71.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 25

 34 omega   81.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 35 omega   70.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 106

 36 omega   42.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 39

 37 omega  124.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 48

 38 omega   81.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 39 omega   92.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 25

 40 omega   92.00  118.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 26

 41 omega   93.00  119.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 26

 42 omega  129.00  154.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 25

 43 omega   92.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   44.0000  -47.0000 25

 44 omega  152.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   44.0000  -47.0000 25

 45 omega   81.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 25

 46 omega  117.00  169.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 52

 47 omega   81.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 48 omega   51.00  110.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 59
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0978005000
_diffrn_orient_matrix_UB_12      -0.0513749000
_diffrn_orient_matrix_UB_13      -0.0252391000
_diffrn_orient_matrix_UB_21      0.0070755000
_diffrn_orient_matrix_UB_22      -0.0788590000
_diffrn_orient_matrix_UB_23      0.0582053000
_diffrn_orient_matrix_UB_31      -0.0310922000
_diffrn_orient_matrix_UB_32      0.1436897000
_diffrn_orient_matrix_UB_33      0.0228901000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27590
_diffrn_reflns_theta_full        71.21
_diffrn_reflns_theta_max         71.21
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1377
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     878
_refine_ls_number_reflns         11774
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.4830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                10885
_reflns_number_total             11774
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00145_si_001.cif
_cod_data_source_block           compound_2
_cod_original_formula_sum        'C34.20 H42.09 N3 O9.50'
_cod_database_code               1545473
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97