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_4035545
_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 H28 N3 O4'
_chemical_formula_sum            'C26 H31 N3 O4'
_chemical_formula_weight         449.54
_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   geom
_atom_sites_solution_primary     dual
_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                   8.14900(10)
_cell_length_b                   9.85930(10)
_cell_length_c                   28.6560(2)
_cell_measurement_reflns_used    8440
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6210
_cell_measurement_theta_min      4.5860
_cell_volume                     2302.32(4)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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    -65.00  34.00   1.00    1.00    --  -40.92  37.00   0.00   99
  2  \w    -65.00  34.00   1.00    1.00    --  -40.92  37.00 -90.00   99
  3  \w     23.00  97.00   1.00    1.00    --   40.92-125.00-180.00   74
  4  \w     34.00 122.00   1.00    1.00    --  107.58-125.00  90.00   88
  5  \w     82.00 178.00   1.00    1.00    --  107.58  45.00  30.00   96
  6  \w     31.00 136.00   1.00    1.00    --  107.58 -30.00  60.00  105
  7  \w     35.00 133.00   1.00    1.00    --  107.58 -45.00  30.00   98
  8  \w     34.00 122.00   1.00    1.00    --  107.58-125.00 -60.00   88
;
_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      0.0076645000
_diffrn_orient_matrix_UB_12      -0.1544112000
_diffrn_orient_matrix_UB_13      -0.0079858000
_diffrn_orient_matrix_UB_21      0.1855830000
_diffrn_orient_matrix_UB_22      0.0018327000
_diffrn_orient_matrix_UB_23      0.0102082000
_diffrn_orient_matrix_UB_31      -0.0351009000
_diffrn_orient_matrix_UB_32      -0.0239556000
_diffrn_orient_matrix_UB_33      0.0521758000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.745
_diffrn_reflns_theta_min         4.743
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70359
_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    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_coef       0.0088(9)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4507
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0738
_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^)+(0.0660P)^2^+3.4829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1731
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4401
_reflns_number_total             4507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01087_si_004.cif
_cod_data_source_block           4-20-8
_cod_database_code               4035545
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.889
_reflns_odcompleteness_completeness 99.83
_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. Rigid bond restraints
 C22, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C20A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C21, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C22, C23
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C22 \\sim C24: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
C23 \\sim C20A: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
C21 \\sim C20: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
C22 \\sim C23: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4. Others
 Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(2)
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(2)
 Fixed Sof: C20(0.5) H20A(0.5) H20B(0.5) C20A(0.5)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C17(H17)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N19(H19), C7(H7), C4(H4), C26(H26), C25(H25), C23(H23), C21(H21)
5.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
5.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C29A(H29D,H29E,
 H29F), C28A(H28D,H28E,H28F)
;
_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.769