[11]-Chaetoglobosins from Pseudeurotium bakeri Induce G2/M Cell Cycle Arrest and Apoptosis in Human Cancer Cells
Duan, Fang-Fang; Liu, Lin; Gao, Ying; Peng, Xiao-Gang; Meng, Xiang-Gao; Ruan, Han-Li; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.0c01335

data_1563742
_publ_section_title
;
 [11]-Chaetoglobosins from Pseudeurotium bakeri Induce G2/M Cell Cycle
 Arrest and Apoptosis in Human Cancer Cells
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01335
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H36 N2 O4'
_chemical_formula_sum            'C30 H36 N2 O4'
_chemical_formula_weight         488.61
_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     direct
_audit_creation_date             2020-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.221(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8479(2)
_cell_length_b                   21.3426(2)
_cell_length_c                   13.0062(2)
_cell_measurement_reflns_used    42963
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6530
_cell_measurement_theta_min      3.6330
_cell_volume                     2825.63(8)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_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     -9.00  17.00   0.50    0.50    --    0.00 -35.00 125.00   52
  2  \w    -17.00  66.00   0.50    0.50    --    0.00  35.00 -78.00  166
  3  \w     24.00  59.00   0.50    1.00    --   94.60 -35.00 125.00   70
  4  \w     78.00 119.00   0.50    1.00    --   94.60  35.00 -78.00   82
  5  \w    -13.00  82.00   0.50    0.50    --    0.00  57.00  90.00  190
  6  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00   0.00  212
  7  \w    -15.00  10.00   0.50    0.50    --    0.00  38.00-150.00   50
  8  \w    -43.00 -11.00   0.50    0.50    --    0.00 -77.00 120.00   64
  9  \w    -17.00  87.00   0.50    0.50    --    0.00  38.00 150.00  208
 10  \w    -30.00  24.00   0.50    0.50    --    0.00 -82.00   0.00  108
 11  \w     -8.00  27.00   0.50    0.50    --    0.00 -77.00 120.00   70
 12  \w     23.00  72.00   0.50    0.50    --    0.00  38.00-150.00   98
 13  \w    -21.00  29.00   0.50    0.50    --    0.00 -77.00  60.00  100
 14  \w     66.00  91.00   0.50    1.00    --   94.60  74.00  23.65   50
 15  \w    113.00 184.00   0.50    1.00    --   94.60  72.00-105.41  142
 16  \w     67.00  97.00   0.50    1.00    --   94.60  72.00-105.41   60
 17  \w     69.00  95.00   0.50    1.00    --   94.60  69.00   6.40   52
 18  \w     66.00  91.00   0.50    1.00    --   94.60  75.00 145.59   50
 19  \w     80.00 126.00   0.50    1.00    --   94.60 -82.00 150.00   92
 20  \w     66.00 183.00   0.50    1.00    --   94.60  74.00  53.75  234
 21  \w    145.00 171.00   0.50    1.00    --   94.60  69.00 -78.02   52
 22  \w     73.00 124.00   0.50    1.00    --   94.60  54.00 -37.13  102
 23  \w     67.00  93.00   0.50    1.00    --   94.60  71.00-178.55   52
 24  \w     68.00  93.00   0.50    1.00    --   94.60  69.00 -78.02   50
 25  \w     67.00  92.00   0.50    1.00    --   94.60  73.00 122.42   50
 26  \w     69.00 114.00   0.50    1.00    --   94.60  67.00  46.77   90
 27  \w     67.00  93.00   0.50    1.00    --   94.60  71.00-129.38   52
 28  \w    148.00 174.00   0.50    1.00    --   94.60  71.00-129.38   52
 29  \w      5.00 125.00   0.50    1.00    --   94.60 -82.00 120.00  240
 30  \w     69.00  95.00   0.50    1.00    --   94.60  67.00 140.03   52
 31  \w     71.00 129.00   0.50    1.00    --   94.60  59.00  29.25  116
 32  \w     70.00  96.00   0.50    1.00    --   94.60  65.00  90.45   52
 33  \w     67.00  93.00   0.50    1.00    --   94.60  72.00 -31.54   52
 34  \w      5.00 125.00   0.50    1.00    --   94.60 -82.00-120.00  240
 35  \w      9.00  74.00   0.50    1.00    --   94.60 -82.00 150.00  130
 36  \w     96.00 125.00   0.50    1.00    --   94.60 -82.00 -30.00   58
 37  \w     75.00 113.00   0.50    1.00    --   94.60  45.00 -60.00   76
 38  \w     72.00  98.00   0.50    1.00    --   94.60  61.00 -60.00   52
 39  \w      9.00  74.00   0.50    1.00    --   94.60 -82.00 -30.00  130
 40  \w     68.00 182.00   0.50    1.00    --   94.60  69.00  79.73  228
 41  \w     71.00 184.00   0.50    1.00    --   94.60  61.00 120.00  226
 42  \w     70.00 184.00   0.50    1.00    --   94.60  63.00 170.97  228
 43  \w     70.00 134.00   0.50    1.00    --   94.60  63.00   7.58  128
 44  \w     68.00 112.00   0.50    1.00    --   94.60  70.00 143.61   88
 45  \w    138.00 164.00   0.50    1.00    --   94.60  70.00 143.61   52
 46  \w     73.00 183.00   0.50    1.00    --   94.60  53.00 -23.84  220
 47  \w     70.00 129.00   0.50    1.00    --   94.60  64.00 102.53  118
 48  \w     69.00  95.00   0.50    1.00    --   94.60  67.00  74.32   52
 49  \w     68.00  94.00   0.50    1.00    --   94.60  70.00 173.35   52
 50  \w     67.00 184.00   0.50    1.00    --   94.60  71.00-172.30  234
 51  \w    157.00 182.00   0.50    1.00    --   94.60  72.00 -20.07   50
 52  \w     66.00  93.00   0.50    1.00    --   94.60  75.00-123.86   54
 53  \w     69.00  94.00   0.50    1.00    --   94.60  66.00-148.46   50
 54  \w     71.00 151.00   0.50    1.00    --   94.60  61.00   0.00  160
 55  \w     27.00 121.00   0.50    1.00    --   94.60 -82.00  30.00  188
 56  \w     67.00  93.00   0.50    1.00    --   94.60  72.00 -20.07   52
 57  \w    142.00 168.00   0.50    1.00    --   94.60  74.00  23.65   52
 58  \w     73.00 151.00   0.50    1.00    --   94.60  52.00-115.94  156
 59  \w     17.00  42.00   0.50    1.00    --   94.60 -82.00-180.00   50
 60  \w     52.00  77.00   0.50    1.00    --   94.60 -82.00-180.00   50
 61  \w     98.00 123.00   0.50    1.00    --   94.60 -82.00-180.00   50
 62  \w    156.00 181.00   0.50    1.00    --   94.60  67.00-155.39   50
 63  \w     68.00  94.00   0.50    1.00    --   94.60  73.00 -43.11   52
 64  \w     79.00 109.00   0.50    1.00    --   94.60 -82.00 -60.00   60
 65  \w     69.00  95.00   0.50    1.00    --   94.60  67.00-155.39   52
;
_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      0.1280998000
_diffrn_orient_matrix_UB_12      -0.0301557000
_diffrn_orient_matrix_UB_13      0.0759239000
_diffrn_orient_matrix_UB_21      -0.0655356000
_diffrn_orient_matrix_UB_22      -0.0129509000
_diffrn_orient_matrix_UB_23      0.0857174000
_diffrn_orient_matrix_UB_31      -0.0469511000
_diffrn_orient_matrix_UB_32      -0.0643164000
_diffrn_orient_matrix_UB_33      -0.0529607000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            72867
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.025
_diffrn_reflns_theta_min         3.622
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64338
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 5005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         11281
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.4642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                10887
_reflns_number_total             11281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01335_si_007.cif
_cod_data_source_block           20200110_pps-7
_cod_database_code               1563742
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.915
_reflns_odcompleteness_completeness 99.98
_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:
 C3(H3), C4(H4), C5(H5), C8(H8), C16(H16), C20(H20), C3A(H3A), C4A(H4A),
 C5A(H5A), C8A(H8A), C16A(H16A), C20A(H20A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C10A(H10C,
 H10D), C15A(H15C,H15D), C17A(H17C,H17D), C19A(H19C,H19D)
2.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C5'(H5'), C6'(H6'), C7(H7), C7'(H7'), C8'(H8'), C13(H13), C14(H14),
 N1'(H1'), N2(H2), C2"(H2"), C5"(H5"), C6"(H6"), C7"(H7"), C7A(H7A), C8"(H8"),
 C13A(H13A), C14A(H14A), N2"(H2"A), N2A(H2A)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F)
;
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.847