Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor.
Li, Huaqiang; Sun, Weiguang; Deng, Mengyi; Zhou, Qun; Wang, Jianping; Liu, Junjun; Chen, Chunmei; Qi, Changxing; Luo, Zengwei; Xue, Yongbo; Zhu, Hucheng; Zhang, Yonghui; The Journal of organic chemistry 83 (2018) 8483–8492; doi:10.1021/acs.joc.8b01087

data_4035543
_publ_section_title
;
 Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the
 Marine-Derived Fungus Aspergillus versicolor.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8483
_journal_page_last               8492
_journal_paper_doi               10.1021/acs.joc.8b01087
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H29 N3 O4, C H4 O'
_chemical_formula_sum            'C27 H33 N3 O5'
_chemical_formula_weight         479.56
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                93.959(2)
_cell_angle_beta                 106.285(2)
_cell_angle_gamma                95.686(2)
_cell_formula_units_Z            1
_cell_length_a                   7.01728(18)
_cell_length_b                   8.2752(2)
_cell_length_c                   10.7566(3)
_cell_measurement_reflns_used    10511
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3290
_cell_measurement_theta_min      4.2850
_cell_volume                     593.54(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_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   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00-150.00   99
  2  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00  60.00  100
  3  \w     13.00 113.00   1.00    1.00    --   41.11  57.00 -60.00  100
  4  \w     23.00  97.00   1.00    1.00    --   41.11-125.00 120.00   74
  5  \w     23.00  97.00   1.00    1.00    --   41.11-125.00 -90.00   74
  6  \w      6.00  33.00   1.00    1.00    --   42.00  88.00  87.84   27
  7  \w     17.00  47.00   1.00    1.00    --   50.00  79.00  85.62   30
  8  \w     16.00  45.00   1.00    1.00    --   50.00  82.00 -72.67   29
  9  \w     21.00  47.00   1.00    1.00    --   54.00  79.00-141.50   26
 10  \w     21.00  49.00   1.00    1.00    --   54.00  78.00  25.22   28
 11  \w     20.00  46.00   1.00    1.00    --   54.00  81.00 -52.03   26
 12  \w     26.00 133.00   1.00    1.00    --   58.00  75.00 -12.83  107
 13  \w     25.00 134.00   1.00    1.00    --   58.00  77.00-173.95  109
 14  \w     29.00 138.00   1.00    1.00    --   62.00  77.00-111.04  109
 15  \w     30.00 137.00   1.00    1.00    --   62.00  75.00 138.23  107
 16  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 152.10  108
 17  \w     33.00 142.00   1.00    1.00    --   66.00  77.00  42.51  109
 18  \w     33.00 142.00   1.00    1.00    --   66.00  77.00  75.18  109
 19  \w     33.00 142.00   1.00    1.00    --   66.00  77.00-160.92  109
 20  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 -58.47  108
 21  \w     37.00 146.00   1.00    1.00    --   70.00  77.00  99.86  109
 22  \w     74.00 178.00   1.00    1.00    --  106.95  77.00   0.00  104
 23  \w     81.00 171.00   1.00    1.00    --  106.95  61.00 150.00   90
 24  \w    145.00 172.00   1.00    1.00    --  106.95  77.00 -30.00   27
 25  \w    113.00 139.00   1.00    1.00    --  106.95  77.00 -30.00   26
 26  \w     75.00 101.00   1.00    1.00    --  106.95  77.00 -30.00   26
 27  \w     74.00  99.00   1.00    1.00    --  106.95  77.00 150.00   25
 28  \w     76.00 102.00   1.00    1.00    --  106.95  77.00 -60.00   26
 29  \w     79.00 114.00   1.00    1.00    --  106.95  61.00  90.00   35
 30  \w     77.00 158.00   1.00    1.00    --  106.95  77.00-180.00   81
 31  \w    105.00 155.00   1.00    1.00    --  106.95  77.00-120.00   50
 32  \w     74.00 101.00   1.00    1.00    --  106.95  77.00-120.00   27
 33  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
 34  \w     79.00 111.00   1.00    1.00    --  106.95  77.00 120.00   32
 35  \w     79.00 104.00   1.00    1.00    --  106.95  61.00   0.00   25
 36  \w     78.00 105.00   1.00    1.00    --  106.95  61.00-180.00   27
 37  \w     36.00 110.00   1.00    1.00    --  106.95 -61.00  30.00   74
 38  \w     68.00 121.00   1.00    1.00    --  106.95-125.00  90.00   53
 39  \w    116.00 143.00   1.00    1.00    --  106.95  77.00 120.00   27
 40  \w     76.00 178.00   1.00    1.00    --  106.95  77.00  30.00  102
 41  \w     56.00 137.00   1.00    1.00    --  106.95 -77.00 120.00   81
 42  \w     78.00 111.00   1.00    1.00    --  106.95  77.00 -90.00   33
 43  \w    115.00 162.00   1.00    1.00    --  106.95  77.00 -90.00   47
 44  \w     78.00 111.00   1.00    1.00    --  106.95  61.00 120.00   33
 45  \w    112.00 177.00   1.00    1.00    --  106.95  77.00 -60.00   65
 46  \w     24.00  82.00   1.00    1.00    --  106.95 -94.00   0.00   58
 47  \w     88.00 113.00   1.00    1.00    --  106.95-125.00-120.00   25
 48  \w    113.00 139.00   1.00    1.00    --  106.95  77.00  60.00   26
 49  \w     75.00 101.00   1.00    1.00    --  106.95  77.00  60.00   26
 50  \w     75.00 150.00   1.00    1.00    --  106.95  77.00-150.00   75
 51  \w     79.00 106.00   1.00    1.00    --  106.95  61.00 -30.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1659651000
_diffrn_orient_matrix_UB_12      0.0912580000
_diffrn_orient_matrix_UB_13      -0.0460704000
_diffrn_orient_matrix_UB_21      -0.1577152000
_diffrn_orient_matrix_UB_22      0.0350028000
_diffrn_orient_matrix_UB_23      -0.1238447000
_diffrn_orient_matrix_UB_31      -0.0265442000
_diffrn_orient_matrix_UB_32      0.1606587000
_diffrn_orient_matrix_UB_33      0.0709480000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11144
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.507
_diffrn_reflns_theta_min         4.304
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_coef       0.037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0443P)^2^+0.1184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                4389
_reflns_number_total             4395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01087_si_002.cif
_cod_data_source_block           420_6
_cod_original_cell_volume        593.55(3)
_cod_database_code               4035543
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.62
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N19(H19), N1(H1), C4(H4), C7(H7), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), C00Z(HA,HB,HC)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.594