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_4035544
_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_formula_moiety         'C26 H29 N3 O3'
_chemical_formula_sum            'C26 H29 N3 O3'
_chemical_formula_weight         431.52
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-26
_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            8
_cell_length_a                   11.02750(10)
_cell_length_b                   11.02750(10)
_cell_length_c                   38.1512(5)
_cell_measurement_reflns_used    16794
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6330
_cell_measurement_theta_min      4.1060
_cell_volume                     4639.41(9)
_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 (Sheldrick, 2015)'
_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 0.996
_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    -66.00  33.00   1.00    1.00    --  -40.98  38.00 -60.00   99
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 -30.00  100
  3  \w     16.00 115.00   1.00    1.00    --   40.98  38.00 -90.00   99
  4  \w     23.00  97.00   1.00    1.00    --   40.98-125.00   0.00   74
  5  \w     35.00 133.00   1.00    2.89    --  107.58 -45.00 -90.00   98
  6  \w     78.00 178.00   1.00    2.89    --  107.58  61.00 -60.00  100
  7  \w     78.00 178.00   1.00    2.89    --  107.58  61.00 -90.00  100
  8  \w     35.00 133.00   1.00    2.89    --  107.58 -45.00 150.00   98
  9  \w     94.00 178.00   1.00    2.89    --  107.58 125.00-180.00   84
 10  \w     82.00 178.00   1.00    2.89    --  107.58  45.00   0.00   96
 11  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  60.00  100
 12  \w     13.00 108.00   1.00    1.00    --   40.98  57.00 150.00   95
;
_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      0.1086196000
_diffrn_orient_matrix_UB_12      -0.0878865000
_diffrn_orient_matrix_UB_13      0.0001657000
_diffrn_orient_matrix_UB_21      -0.0343985000
_diffrn_orient_matrix_UB_22      -0.0416353000
_diffrn_orient_matrix_UB_23      0.0372421000
_diffrn_orient_matrix_UB_31      -0.0808270000
_diffrn_orient_matrix_UB_32      -0.1002842000
_diffrn_orient_matrix_UB_33      -0.0156261000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            29747
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.001
_diffrn_reflns_theta_min         4.173
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13518
_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_density_diffrn    1.236
_exptl_crystal_F_000             1840
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1760 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0551P)^2^+2.1974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4534
_reflns_number_total             4674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01087_si_003.cif
_cod_data_source_block           30_3_2_2
_cod_original_cell_volume        4639.41(10)
_cod_database_code               4035544
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.96
_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:
 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:
 N1(H1), N19(H19), C4(H4), C7(H7), C26(H26), C25(H25)
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_date_sample_data_collection 2017-12-25
_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 5.570
_oxdiff_exptl_absorpt_empirical_full_min 0.514