An indole diketopiperazine alkaloid and a bisabolane sesquiterpenoid with unprecedented skeletons from <i>Aspergillus fumigatus</i>.
Jiang, Yaqin; Chen, Chunmei; Zhu, Hucheng; Li, Qin; Mao, Lina; Liao, Hong; Nan, Yiyang; Wang, Zhiping; Zhou, Hongjian; Zhou, Qun; Zhang, Yonghui; Organic & biomolecular chemistry 21 (2023) 2236–2242; doi:10.1039/d2ob02220f

data_7159181
_publ_section_title
;
 An indole diketopiperazine alkaloid and a bisabolane sesquiterpenoid with
 unprecedented skeletons from <i>Aspergillus fumigatus</i>.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2236
_journal_page_last               2242
_journal_paper_doi               10.1039/d2ob02220f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H33 N3 O5'
_chemical_formula_sum            'C27 H33 N3 O5'
_chemical_formula_weight         479.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9746(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.57868(7)
_cell_length_b                   5.12531(3)
_cell_length_c                   17.35284(9)
_cell_measurement_reflns_used    23365
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8700
_cell_measurement_theta_min      3.2830
_cell_volume                     1195.991(11)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (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_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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     90.00 117.00   0.50    0.50    --   32.00  72.00 122.12   54
  2  \w      6.00  41.00   0.50    0.50    --   32.00  72.00 122.12   70
  3  \w    -54.00  -3.00   0.50    0.50    --   32.00 -43.00-121.06  102
  4  \w      3.00  50.00   0.50    0.50    --   32.00 -43.00-121.06   94
  5  \w     15.00  42.00   0.50    0.50    --   40.00  72.00 -63.25   54
  6  \w     14.00  58.00   0.50    0.50    --   40.00  70.00-137.82   88
  7  \w     98.00 123.00   0.50    0.50    --   40.00  70.00-137.82   50
  8  \w     32.00  57.00   0.50    0.50    --   60.00  75.00 101.37   50
  9  \w     32.00  66.00   0.50    0.50    --   60.00  75.00  18.82   68
 10  \w     32.00  59.00   0.50    0.50    --   60.00  75.00 -19.23   54
 11  \w     32.00  58.00   0.50    0.50    --   60.00  74.00  56.13   52
 12  \w     39.00  83.00   0.50    0.50    --   60.00  73.00 -60.35   88
 13  \w     36.00  73.00   0.50    0.50    --   64.00  75.00 127.51   74
 14  \w     87.00 143.00   0.50    0.50    --   64.00  75.00 127.51  112
 15  \w     44.00  69.00   0.50    0.50    --   68.00  68.00  74.12   50
 16  \w     40.00  65.00   0.50    0.50    --   68.00  75.00 -92.86   50
 17  \w    112.00 156.00   0.50    0.50    --   68.00  75.00 -92.86   88
 18  \w    129.00 161.00   0.50    0.50    --   72.00  74.00 131.15   64
 19  \w     52.00  78.00   0.50    0.50    --   72.00  50.00  13.98   52
 20  \w     45.00  73.00   0.50    0.50    --   72.00  73.00-120.63   56
 21  \w     44.00  70.00   0.50    0.50    --   72.00  74.00 131.15   52
 22  \w    108.00 161.00   0.50    0.50    --   72.00  73.00-120.63  106
 23  \w     44.00  70.00   0.50    0.50    --   72.00  75.00-145.78   52
 24  \w     48.00  99.00   0.50    0.50    --   76.00  75.00 170.40  102
 25  \w    112.00 139.00   0.50    0.50    --   76.00  75.00 170.40   54
 26  \w     48.00  93.00   0.50    0.50    --   76.00  74.00 149.25   90
 27  \w    138.00 164.00   0.50    0.50    --   76.00  74.00 149.25   52
 28  \w    125.00 165.00   0.50    0.50    --   80.00  66.00 -67.43   80
 29  \w     55.00  81.00   0.50    0.50    --   80.00  66.00 -67.43   52
 30  \w     55.00  81.00   0.50    0.50    --   80.00  69.00  94.77   52
 31  \w     57.00  92.00   0.50    0.50    --   84.00  75.00-148.88   70
 32  \w     64.00 125.00   0.50    0.50    --   95.20 -82.00 -90.00  122
 33  \w      6.00  43.00   0.50    0.50    --   95.20 -82.00 -90.00   74
 34  \w     73.00 104.00   0.50    0.50    --   95.20  62.00  52.22   62
 35  \w     96.00 126.00   0.50    0.50    --   95.20 -82.00-150.00   60
 36  \w     76.00 180.00   0.50    0.50    --   95.20  61.00  90.00  208
 37  \w    120.00 153.00   0.50    0.50    --   95.20  61.00-180.00   66
 38  \w     62.00  93.00   0.50    0.50    --   95.20 -82.00-150.00   62
 39  \w     56.00 126.00   0.50    0.50    --   95.20 -82.00  60.00  140
 40  \w     27.00  63.00   0.50    0.50    --   95.20 -45.00 -30.00   72
 41  \w     11.00  52.00   0.50    0.50    --   95.20 -82.00  60.00   82
 42  \w     67.00 117.00   0.50    0.50    --   95.20 -61.00-180.00  100
 43  \w     29.00  55.00   0.50    0.50    --   95.20 -61.00-180.00   52
 44  \w     76.00 156.00   0.50    0.50    --   95.20  45.00-120.00  160
 45  \w     72.00 175.00   0.50    0.50    --   95.20  61.00   0.00  206
 46  \w     74.00 126.00   0.50    0.50    --   95.20  57.00 -71.69  104
 47  \w    140.00 185.00   0.50    0.50    --   95.20  61.00 -60.00   90
 48  \w     73.00 130.00   0.50    0.50    --   95.20  61.00 -60.00  114
 49  \w     68.00 180.00   0.50    0.50    --   95.20  71.00 104.20  224
 50  \w    123.00 184.00   0.50    0.50    --   95.20  68.00-114.62  122
 51  \w     72.00 108.00   0.50    0.50    --   95.20  68.00-114.62   72
 52  \w     73.00 112.00   0.50    0.50    --   95.20 -45.00 -30.00   78
 53  \w     69.00 145.00   0.50    0.50    --   95.20  70.00  19.03  152
 54  \w     76.00 113.00   0.50    0.50    --   95.20  61.00-180.00   74
 55  \w     72.00 116.00   0.50    0.50    --   95.20  61.00 -30.00   88
 56  \w     97.00 183.00   0.50    0.50    --   95.20  77.00 150.00  172
 57  \w     72.00 146.00   0.50    0.50    --   95.20  71.00  54.80  148
 58  \w     23.00 116.00   0.50    0.50    --   95.20 -61.00 120.00  186
 59  \w     75.00 105.00   0.50    0.50    --   95.20  58.00 144.90   60
;
_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      -0.0517297000
_diffrn_orient_matrix_UB_12      -0.0463820000
_diffrn_orient_matrix_UB_13      -0.0836458000
_diffrn_orient_matrix_UB_21      0.1012570000
_diffrn_orient_matrix_UB_22      0.0163885000
_diffrn_orient_matrix_UB_23      -0.0302170000
_diffrn_orient_matrix_UB_31      0.0137188000
_diffrn_orient_matrix_UB_32      -0.2965254000
_diffrn_orient_matrix_UB_33      0.0114505000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25692
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.171
_diffrn_reflns_theta_min         2.571
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62650
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0084(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0390P)^2^+0.3549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                4688
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02220f2.cif
_cod_data_source_block           20220628_jyq1-41-1
_cod_depositor_comments          'Adding full bibliography for 7159181.cif.'
_cod_original_cell_volume        1195.992(11)
_cod_database_code               7159181
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.729
_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:
 C00E(H00E), C00H(H00H), C00K(H00K), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00O(H00D,H00F), C00Q(H00G,H00I), C00U(H00L,H00M)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008), C00C(H00C), C00J(H00J), C00P(H00P), C00R(H00R)
2.d X=CH2 refined with riding coordinates:
 C00W(H00T,H00U)
2.e Idealised Me refined as rotating group:
 C00V(H00N,H00O,H00Q), C00X(H00V,H00W,H00X), C00Y(H00Y,H,HA), C00Z(H00Z,HB,HC)
2.f Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_shelx_res_checksum              53696
_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 1.829
_oxdiff_exptl_absorpt_empirical_full_min 0.486