HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived <i>Aspergillus versicolor</i>.
Li, Huaqiang; Xu, Dan; Sun, Weiguang; Yang, Beiye; Li, Fengli; Liu, Mengting; Wang, Jianping; Xue, Yongbo; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 82 (2019) 2181–2188; doi:10.1021/acs.jnatprod.9b00183

data_1552623
_publ_section_title
;
 HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids
 from a Soil-Derived <i>Aspergillus versicolor</i>.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2181
_journal_page_last               2188
_journal_paper_doi               10.1021/acs.jnatprod.9b00183
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H31 N3 O5, C H4 O'
_chemical_formula_sum            'C27 H35 N3 O6'
_chemical_formula_weight         497.58
_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             2019-01-19
_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                   6.28231(2)
_cell_length_b                   18.57951(6)
_cell_length_c                   21.81012(8)
_cell_measurement_reflns_used    47753
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5870
_cell_measurement_theta_min      3.1240
_cell_volume                     2545.726(15)
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     27.00  54.00   0.50    0.50    --    0.00  38.00-150.00   54
  2  \w     32.00  74.00   0.50    0.50    --    0.00  57.00-120.00   84
  3  \w     -3.00  22.00   0.50    0.50    --    0.00 -57.00 120.00   50
  4  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00   0.00  212
  5  \w    -87.00 -23.00   0.50    0.50    --    0.00 -57.00 120.00  128
  6  \w     60.00  88.00   0.50    0.50    --    0.00  70.00  45.86   56
  7  \w    -22.00   9.00   0.50    0.50    --    0.00  57.00-120.00   62
  8  \w    -89.00 -49.00   0.50    0.50    --    0.00 -38.00  30.00   80
  9  \w    -17.00   9.00   0.50    0.50    --    0.00  38.00-150.00   52
 10  \w    -26.00  44.00   0.50    0.50    --    0.00  70.00  45.86  140
 11  \w    -22.00  58.00   0.50    0.50    --    0.00  57.00 -60.00  160
 12  \w     57.00  89.00   0.50    0.50    --    0.00  38.00 120.00   64
 13  \w    -16.00  17.00   0.50    0.50    --    0.00  38.00 120.00   66
 14  \w     70.00 119.00   0.50    0.50    --   94.60  65.00  68.86   98
 15  \w    138.00 164.00   0.50    0.50    --   94.60  59.00  88.05   52
 16  \w     69.00  94.00   0.50    0.50    --   94.60  66.00-139.02   50
 17  \w     71.00 114.00   0.50    0.50    --   94.60  59.00  88.05   86
 18  \w     67.00  93.00   0.50    0.50    --   94.60  72.00-172.84   52
 19  \w     69.00 131.00   0.50    0.50    --   94.60  66.00 -19.10  124
 20  \w     73.00 184.00   0.50    0.50    --   94.60  54.00 106.10  222
 21  \w     68.00  94.00   0.50    0.50    --   94.60  69.00 161.84   52
 22  \w     69.00 116.00   0.50    0.50    --   94.60  66.00 -79.08   94
 23  \w    132.00 181.00   0.50    0.50    --   94.60  69.00 161.84   98
 24  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 -81.53   50
 25  \w     67.00  93.00   0.50    0.50    --   94.60  71.00  35.85   52
 26  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 139.47   50
 27  \w     66.00  92.00   0.50    0.50    --   94.60  75.00  -9.31   52
 28  \w     71.00 105.00   0.50    0.50    --   94.60  60.00 109.76   68
 29  \w     69.00 149.00   0.50    0.50    --   94.60  68.00-108.30  160
 30  \w    155.00 181.00   0.50    0.50    --   94.60  68.00-108.30   52
 31  \w    138.00 164.00   0.50    0.50    --   94.60  75.00 -98.42   52
 32  \w    154.00 180.00   0.50    0.50    --   94.60  70.00 -39.91   52
 33  \w     68.00  98.00   0.50    0.50    --   94.60  70.00 -39.91   60
 34  \w     66.00  91.00   0.50    0.50    --   94.60  75.00 -98.42   50
 35  \w     72.00 184.00   0.50    0.50    --   94.60  55.00  53.54  224
 36  \w     19.00  93.00   0.50    0.50    --   94.60 -77.00 -30.00  148
 37  \w     66.00  92.00   0.50    0.50    --   94.60  75.00-107.38   52
 38  \w      6.00 126.00   0.50    0.50    --   94.60 -82.00-180.00  240
 39  \w     71.00  98.00   0.50    0.50    --   94.60  61.00-150.00   54
 40  \w     71.00 110.00   0.50    0.50    --   94.60  61.00  30.00   78
 41  \w     71.00 184.00   0.50    0.50    --   94.60  61.00   0.00  226
 42  \w      6.00 126.00   0.50    0.50    --   94.60 -82.00 -90.00  240
 43  \w     70.00  95.00   0.50    0.50    --   94.60  68.00 -43.96   50
 44  \w     70.00  95.00   0.50    0.50    --   94.60  65.00 -47.02   50
 45  \w    144.00 169.00   0.50    0.50    --   94.60  71.00-121.91   50
 46  \w     67.00  93.00   0.50    0.50    --   94.60  71.00-121.91   52
 47  \w     72.00 176.00   0.50    0.50    --   94.60  55.00-114.57  208
 48  \w     72.00 155.00   0.50    0.50    --   94.60  61.00-180.00  166
 49  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  60.00   50
 50  \w     77.00 162.00   0.50    0.50    --   94.60  45.00 -30.00  170
 51  \w    142.00 179.00   0.50    0.50    --   94.60  69.00 123.65   74
 52  \w    134.00 159.00   0.50    0.50    --   94.60  60.00  21.22   50
 53  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  90.00   52
 54  \w     67.00  92.00   0.50    0.50    --   94.60  71.00 103.69   50
 55  \w    159.00 184.00   0.50    0.50    --   94.60  71.00 103.69   50
 56  \w     74.00 101.00   0.50    0.50    --   94.60 -82.00   0.00   54
 57  \w     11.00 105.00   0.50    0.50    --   94.60 -82.00-150.00  188
 58  \w     71.00  97.00   0.50    0.50    --   94.60  60.00  21.22   52
 59  \w     74.00 100.00   0.50    0.50    --   94.60  61.00 -60.00   52
 60  \w    119.00 145.00   0.50    0.50    --   94.60  61.00 -60.00   52
 61  \w     71.00 183.00   0.50    0.50    --   94.60  61.00 150.00  224
 62  \w     10.00 119.00   0.50    0.50    --   94.60 -82.00  60.00  218
 63  \w     68.00 133.00   0.50    0.50    --   94.60  69.00 123.65  130
 64  \w     70.00  95.00   0.50    0.50    --   94.60  64.00-119.21   50
 65  \w     16.00 105.00   0.50    0.50    --   94.60 -61.00  60.00  178
 66  \w     67.00  93.00   0.50    0.50    --   94.60  72.00-179.41   52
;
_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      -0.0200371000
_diffrn_orient_matrix_UB_12      0.0594441000
_diffrn_orient_matrix_UB_13      0.0489020000
_diffrn_orient_matrix_UB_21      -0.1052546000
_diffrn_orient_matrix_UB_22      -0.0540940000
_diffrn_orient_matrix_UB_23      0.0441263000
_diffrn_orient_matrix_UB_31      0.2206147000
_diffrn_orient_matrix_UB_32      -0.0203759000
_diffrn_orient_matrix_UB_33      0.0254878000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            64259
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.936
_diffrn_reflns_theta_min         3.125
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72598
_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    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0415P)^2^+0.6482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5057
_reflns_number_total             5138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00183_si_002.cif
_cod_data_source_block           20181219_lhq6-4-8
_cod_original_cell_volume        2545.726(16)
_cod_database_code               1552623
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.753
_reflns_odcompleteness_completeness 100.00
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups, All O(H) groups
2. Others
 Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(H25)=Sof(C24')=Sof(H24A)=Sof(H24B)=1-FVAR(1)
 Sof(H23)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C24)=Sof(H24C)=Sof(H24D)=FVAR(1)
3.a Riding coordinates:
 C23(H23,H23A,H23B,H23C)
3.b Ternary CH refined with riding coordinates:
 C15(H15)
3.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C25(H25), N1(H1), N2(H2A)
3.e X=CH2 refined with riding coordinates:
 C24'(H24A,H24B), C24(H24C,H24D)
3.f Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
3.g Idealised tetrahedral OH refined as rotating group:
 O2(H2B), O6(H6A)
;
_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 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.629