[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_1563741
_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         'C29 H34 N2 O2'
_chemical_formula_sum            'C29 H34 N2 O2'
_chemical_formula_weight         442.58
_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             2019-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3759(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.91054(5)
_cell_length_b                   7.54833(5)
_cell_length_c                   18.54365(11)
_cell_measurement_reflns_used    19121
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      73.4920
_cell_measurement_theta_min      4.7890
_cell_volume                     1246.881(13)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -80.00  22.00   0.50    0.50    --    0.00 -57.00 150.00  204
  2  \w    -88.00  17.00   0.50    0.50    --    0.00 -38.00  30.00  210
  3  \w     21.00  57.00   0.50    0.50    --    0.00  38.00-120.00   72
  4  \w    -18.00  10.00   0.50    0.50    --    0.00  19.00-180.00   56
  5  \w    -82.00 -22.00   0.50    0.50    --    0.00 -57.00 -60.00  120
  6  \w    -85.00 -26.00   0.50    0.50    --    0.00 -38.00-150.00  118
  7  \w     36.00  89.00   0.50    0.50    --    0.00  19.00-180.00  106
  8  \w     -9.00  17.00   0.50    0.50    --    0.00 -38.00-150.00   52
  9  \w    -10.00  19.00   0.50    0.50    --    0.00 -57.00 -60.00   58
 10  \w    128.00 183.00   0.50    0.50    --   94.60  52.00-175.77  110
 11  \w     66.00  93.00   0.50    0.50    --   94.60  74.00 132.73   54
 12  \w     69.00 183.00   0.50    0.50    --   94.60  67.00  53.94  228
 13  \w    111.00 183.00   0.50    0.50    --   94.60  74.00 132.73  144
 14  \w     71.00  97.00   0.50    0.50    --   94.60  59.00 -32.79   52
 15  \w     73.00 110.00   0.50    0.50    --   94.60  52.00-175.77   74
 16  \w     73.00 177.00   0.50    0.50    --   94.60  52.00 -84.76  208
 17  \w    111.00 184.00   0.50    0.50    --   94.60  63.00-166.01  146
 18  \w     68.00  94.00   0.50    0.50    --   94.60  69.00 -11.92   52
 19  \w     66.00 148.00   0.50    0.50    --   94.60  74.00-150.32  164
 20  \w     70.00 106.00   0.50    0.50    --   94.60  63.00-166.01   72
 21  \w    123.00 174.00   0.50    0.50    --   94.60  69.00 -11.92  102
 22  \w     68.00  94.00   0.50    0.50    --   94.60  69.00 171.40   52
 23  \w     67.00 102.00   0.50    0.50    --   94.60  71.00 -79.64   70
 24  \w    108.00 135.00   0.50    0.50    --   94.60  71.00 -79.64   54
 25  \w    144.00 182.00   0.50    0.50    --   94.60  71.00 -79.64   76
 26  \w     17.00  42.00   0.50    0.50    --   94.60 -82.00  90.00   50
 27  \w     46.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  160
 28  \w      7.00 125.00   0.50    0.50    --   94.60 -82.00 -90.00  236
 29  \w     43.00  73.00   0.50    0.50    --   94.60 -82.00 150.00   60
 30  \w     96.00 125.00   0.50    0.50    --   94.60 -82.00 150.00   58
 31  \w     70.00 109.00   0.50    0.50    --   94.60  64.00  75.87   78
 32  \w     66.00  92.00   0.50    0.50    --   94.60  75.00  33.33   52
 33  \w     71.00 116.00   0.50    0.50    --   94.60  64.00 134.95   90
 34  \w     75.00 133.00   0.50    0.50    --   94.60  45.00   0.00  116
 35  \w    135.00 181.00   0.50    0.50    --   94.60  75.00   3.81   92
 36  \w    140.00 184.00   0.50    0.50    --   94.60  75.00-132.79   88
 37  \w      7.00  78.00   0.50    0.50    --   94.60 -77.00 -60.00  142
 38  \w     97.00 122.00   0.50    0.50    --   94.60 -77.00 -60.00   50
 39  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -90.00   50
 40  \w     71.00 107.00   0.50    0.50    --   94.60  61.00  90.00   72
 41  \w     74.00 181.00   0.50    0.50    --   94.60  61.00 120.00  214
 42  \w     77.00 103.00   0.50    0.50    --   94.60  45.00-180.00   52
 43  \w     71.00 101.00   0.50    0.50    --   94.60  61.00-150.00   60
 44  \w     75.00 122.00   0.50    0.50    --   94.60 -82.00 120.00   94
 45  \w     75.00 112.00   0.50    0.50    --   94.60  45.00  60.00   74
 46  \w     70.00 147.00   0.50    0.50    --   94.60  67.00 -58.82  154
 47  \w     66.00  92.00   0.50    0.50    --   94.60  75.00   3.81   52
 48  \w     75.00 102.00   0.50    0.50    --   94.60 -82.00   0.00   54
 49  \w    126.00 176.00   0.50    0.50    --   94.60  59.00 -32.79  100
 50  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 51  \w     66.00  97.00   0.50    0.50    --   94.60  75.00-132.79   62
 52  \w     73.00  99.00   0.50    0.50    --   94.60  55.00  19.93   52
 53  \w    148.00 173.00   0.50    0.50    --   94.60  60.00 109.27   50
 54  \w     71.00  96.00   0.50    0.50    --   94.60  60.00 109.27   50
;
_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      0.1666270000
_diffrn_orient_matrix_UB_12      -0.0294050000
_diffrn_orient_matrix_UB_13      -0.0167945000
_diffrn_orient_matrix_UB_21      0.0318746000
_diffrn_orient_matrix_UB_22      -0.0516503000
_diffrn_orient_matrix_UB_23      0.0792478000
_diffrn_orient_matrix_UB_31      -0.0335309000
_diffrn_orient_matrix_UB_32      -0.1953216000
_diffrn_orient_matrix_UB_33      -0.0184323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25442
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.883
_diffrn_reflns_theta_min         2.383
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86795
_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    1.179
_exptl_crystal_description       plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details
;
 Flack x determined using 2061 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       0.0118(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4835
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0407P)^2^+0.0853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0734
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                4758
_reflns_number_total             4835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01335_si_003.cif
_cod_data_source_block           20191029_pss-4
_cod_original_cell_volume        1246.880(13)
_cod_database_code               1563741
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 100.00
_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)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
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),
 C19(H19), C20(H20), N1'(H1'), N2(H2)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              31954
_shelx_hkl_checksum              31989
_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 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.589