[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_1563744
_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 H32 N2 O4'
_chemical_formula_sum            'C29 H32 N2 O4'
_chemical_formula_weight         472.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1710(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5395(3)
_cell_length_b                   5.87746(9)
_cell_length_c                   24.8986(4)
_cell_measurement_reflns_used    15191
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.4160
_cell_measurement_theta_min      3.0290
_cell_volume                     2975.25(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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     58.00  88.00   0.50    0.50    --    0.00  38.00 -90.00   60
  2  \w    -16.00  38.00   0.50    0.50    --    0.00  38.00  90.00  108
  3  \w    -13.00  17.00   0.50    0.50    --    0.00 -38.00 -30.00   60
  4  \w    -20.00  20.00   0.50    0.50    --    0.00  57.00  30.00   80
  5  \w     49.00  86.00   0.50    0.50    --    0.00  38.00  90.00   74
  6  \w     53.00  89.00   0.50    0.50    --    0.00  38.00   0.00   72
  7  \w     -8.00  17.00   0.50    0.50    --    0.00 -38.00 150.00   50
  8  \w    -17.00  40.00   0.50    0.50    --    0.00  38.00   0.00  114
  9  \w    -26.00  13.00   0.50    0.50    --    0.00 -57.00  30.00   78
 10  \w     63.00  89.00   0.50    0.50    --    0.00  57.00-180.00   52
 11  \w    -17.00  22.00   0.50    0.50    --    0.00  38.00 -90.00   78
 12  \w    -74.00 -45.00   0.50    0.50    --    0.00 -38.00 150.00   58
 13  \w    -84.00 -59.00   0.50    0.50    --    0.00 -57.00  30.00   50
 14  \w    -88.00 -41.00   0.50    0.50    --    0.00 -38.00 -30.00   94
 15  \w     51.00  85.00   0.50    0.50    --    0.00  57.00  30.00   68
 16  \w    -20.00  33.00   0.50    0.50    --    0.00  57.00-180.00  106
 17  \w    110.00 175.00   0.50    2.00    --   94.60  63.00-102.76  130
 18  \w     70.00 101.00   0.50    2.00    --   94.60  63.00-102.76   62
 19  \w     67.00  93.00   0.50    2.00    --   94.60  72.00  -0.05   52
 20  \w    146.00 172.00   0.50    2.00    --   94.60  60.00 -39.49   52
 21  \w     66.00  92.00   0.50    2.00    --   94.60  75.00-103.76   52
 22  \w     71.00  97.00   0.50    2.00    --   94.60  60.00 -39.49   52
 23  \w    145.00 184.00   0.50    2.00    --   94.60  72.00 157.19   78
 24  \w     66.00  92.00   0.50    2.00    --   94.60  74.00 -28.98   52
 25  \w     69.00 129.00   0.50    2.00    --   94.60  72.00  86.96  120
 26  \w    135.00 180.00   0.50    2.00    --   94.60  72.00  86.96   90
 27  \w     68.00  99.00   0.50    2.00    --   94.60  69.00-146.61   62
 28  \w    114.00 183.00   0.50    2.00    --   94.60  69.00-146.61  138
 29  \w     47.00 118.00   0.50    2.00    --   94.60 -61.00 150.00  142
 30  \w      6.00 123.00   0.50    2.00    --   94.60 -82.00 -60.00  234
 31  \w    148.00 174.00   0.50    2.00    --   94.60  73.00  23.30   52
 32  \w    159.00 184.00   0.50    2.00    --   94.60  68.00-160.90   50
 33  \w     69.00  95.00   0.50    2.00    --   94.60  68.00-160.90   52
 34  \w    126.00 183.00   0.50    2.00    --   94.60  60.00 -14.28  114
 35  \w    115.00 184.00   0.50    2.00    --   94.60  65.00-168.72  138
 36  \w     70.00  96.00   0.50    2.00    --   94.60  65.00-168.72   52
 37  \w     71.00 118.00   0.50    2.00    --   94.60  60.00 -14.28   94
 38  \w     67.00 119.00   0.50    2.00    --   94.60  72.00 157.19  104
 39  \w     71.00  96.00   0.50    2.00    --   94.60  61.00  60.00   50
 40  \w      5.00 123.00   0.50    2.00    --   94.60 -82.00-180.00  236
 41  \w     71.00  97.00   0.50    2.00    --   94.60  61.00 -60.00   52
 42  \w     87.00 116.00   0.50    2.00    --   94.60 -82.00  30.00   58
 43  \w     68.00 104.00   0.50    2.00    --   94.60  70.00  63.47   72
 44  \w     88.00 118.00   0.50    2.00    --   94.60 -77.00 -30.00   60
 45  \w     71.00 104.00   0.50    2.00    --   94.60  61.00-180.00   66
 46  \w     70.00 104.00   0.50    2.00    --   94.60  63.00 113.54   68
 47  \w     77.00 145.00   0.50    2.00    --   94.60  44.00  64.91  136
 48  \w      6.00  75.00   0.50    2.00    --   94.60 -77.00 -30.00  138
 49  \w     70.00 107.00   0.50    2.00    --   94.60  64.00 123.13   74
 50  \w     71.00  97.00   0.50    2.00    --   94.60  61.00-120.00   52
 51  \w     71.00  97.00   0.50    2.00    --   94.60  61.00 -30.00   52
 52  \w     71.00  97.00   0.50    2.00    --   94.60  61.00  30.00   52
 53  \w    139.00 183.00   0.50    2.00    --   94.60  61.00  30.00   88
 54  \w     78.00 176.00   0.50    2.00    --   94.60  30.00-180.00  196
 55  \w     71.00 152.00   0.50    2.00    --   94.60  61.00   0.00  162
 56  \w     75.00 146.00   0.50    2.00    --   94.60  48.00 -32.75  142
 57  \w    135.00 161.00   0.50    2.00    --   94.60  61.00 150.00   52
 58  \w     71.00  97.00   0.50    2.00    --   94.60  61.00 150.00   52
 59  \w    118.00 164.00   0.50    2.00    --   94.60  74.00  75.03   92
 60  \w     52.00 106.00   0.50    2.00    --   94.60 -61.00  60.00  108
 61  \w     66.00  92.00   0.50    2.00    --   94.60  74.00  75.03   52
 62  \w     67.00 179.00   0.50    2.00    --   94.60  73.00 -91.20  224
 63  \w     71.00 112.00   0.50    2.00    --   94.60  61.00-168.91   82
 64  \w     67.00  92.00   0.50    2.00    --   94.60  73.00  23.30   50
 65  \w     76.00 102.00   0.50    2.00    --   94.60  42.00-107.77   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      0.0121580000
_diffrn_orient_matrix_UB_12      0.0135828000
_diffrn_orient_matrix_UB_13      -0.0595583000
_diffrn_orient_matrix_UB_21      0.0747319000
_diffrn_orient_matrix_UB_22      -0.0137523000
_diffrn_orient_matrix_UB_23      0.0185003000
_diffrn_orient_matrix_UB_31      -0.0033020000
_diffrn_orient_matrix_UB_32      -0.2613855000
_diffrn_orient_matrix_UB_33      -0.0040820000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29508
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        64.982
_diffrn_reflns_theta_max         64.982
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77778
_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    1.055
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.1868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                4405
_reflns_number_total             4731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01335_si_002.cif
_cod_data_source_block           20190918_pss-36
_cod_database_code               1563744
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.766
_reflns_odcompleteness_completeness 99.90
_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), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C5'(H5'), C6'(H6'), C7(H7), C7'(H7'), C8'(H8'), C13(H13), C14(H14),
 N2(H2), N1(H1)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              65483
_shelx_hkl_checksum              80844
_shelx_fab_checksum              10045
_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 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.570