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_4035542
_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 H31 N3 O3'
_chemical_formula_sum            'C26 H31 N3 O3'
_chemical_formula_weight         433.54
_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
_audit_creation_date             2017-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9246(7)
_cell_length_b                   15.7608(5)
_cell_length_c                   6.6049(2)
_cell_measurement_reflns_used    8183
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6420
_cell_measurement_theta_min      4.8790
_cell_volume                     2282.32(12)
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -129.00  47.00   1.00    1.00    --  -40.98   0.00-120.00  176
  2  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 -60.00   74
  3  \w     79.00 178.00   1.00    1.89    --  106.95  30.00  30.00   99
  4  \w     31.00 135.00   1.00    1.89    --  106.95 -30.00  30.00  104
  5  \w     94.00 178.00   1.00    1.89    --  106.95 125.00 -30.00   84
  6  \w     94.00 178.00   1.00    1.89    --  106.95 125.00 120.00   84
  7  \w     24.00 109.00   1.00    1.89    --  106.95 -94.00 -90.00   85
  8  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 150.00  100
  9  \w     13.00 113.00   1.00    1.00    --   40.98  57.00  90.00  100
 10  \w     78.00 178.00   1.00    1.89    --  106.95  61.00-180.00  100
 11  \w     54.00 128.00   1.00    1.89    --  106.95  15.00 -60.00   74
;
_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      0.0644884000
_diffrn_orient_matrix_UB_12      0.0315467000
_diffrn_orient_matrix_UB_13      -0.0544168000
_diffrn_orient_matrix_UB_21      -0.0247512000
_diffrn_orient_matrix_UB_22      0.0909716000
_diffrn_orient_matrix_UB_23      -0.0226829000
_diffrn_orient_matrix_UB_31      0.0130054000
_diffrn_orient_matrix_UB_32      0.0167215000
_diffrn_orient_matrix_UB_33      0.2256437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14262
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.705
_diffrn_reflns_theta_min         3.454
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69661
_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    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0834P)^2^+3.0468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4276
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01087_si_005.cif
_cod_data_source_block           exp_914
_cod_original_cell_volume        2282.32(13)
_cod_database_code               4035542
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.92
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N19(H19), C4(H4), C7(H7), C21(H21), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.653