Cytotoxic and Anti-Inflammatory Sesquiterpenes from the Whole Plants of <i>Centipeda minima</i>.
Xue, Peng-Hui; Zhang, Nan; Liu, Da; Zhang, Qing-Ran; Duan, Jing-Shi; Yu, Ya-Qin; Li, Jin-Yan; Cao, Shi-Jie; Zhao, Feng; Kang, Ning; Qiu, Feng; Journal of natural products 84 (2021) 247–258; doi:10.1021/acs.jnatprod.0c00884

data_1560805
_publ_section_title
;
 Cytotoxic and Anti-Inflammatory Sesquiterpenes from the Whole Plants of
 <i>Centipeda minima</i>.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              247
_journal_page_last               258
_journal_paper_doi               10.1021/acs.jnatprod.0c00884
_journal_volume                  84
_journal_year                    2021
_chemical_formula_moiety         'C20 H26 O5'
_chemical_formula_sum            'C20 H26 O5'
_chemical_formula_weight         346.41
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.05.22 svn.r1d9e7f8d for OlexSys, GUI svn.r6115)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.962(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1415(6)
_cell_length_b                   8.1158(4)
_cell_length_c                   20.8793(12)
_cell_measurement_reflns_used    4112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0320
_cell_measurement_theta_min      3.9340
_cell_volume                     1877.74(18)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_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 0.972
_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     46.00  95.00   1.00    1.00    --   40.98-129.00  16.00   49
  2  \w     46.00  82.00   1.00    3.00    --  106.95 -77.00  90.00   36
  3  \w     42.00  99.00   1.00    3.00    --  106.95 -30.00  90.00   57
  4  \w     80.00 173.00   1.00    3.00    --  106.95  30.00   0.00   93
  5  \w    109.00 175.00   1.00    3.00    --  106.95 126.00  30.00   66
  6  \w     97.00 174.00   1.00    3.00    --  106.95  45.00-120.00   77
  7  \w    142.00 178.00   1.00    3.00    --  106.95 126.00-180.00   36
  8  \w     40.00  95.00   1.00    3.00    --  106.95 -77.00 -30.00   55
  9  \w   -112.00 -16.00   1.00    2.00    --  -40.98 -38.00   0.00   96
 10  \w   -111.00 -13.00   1.00    2.00    --  -40.98 -57.00 120.00   98
 11  \w    -93.00 -67.00   1.00    2.00    --  -40.98 -57.00 -30.00   26
 12  \w    -51.00 -17.00   1.00    2.00    --  -40.98 -38.00-120.00   34
 13  \w    -62.00 -21.00   1.00    1.93    --  -40.98 -57.00 -60.00   41
 14  \w    -81.00 -55.00   1.00    1.93    --  -40.98 -38.00-120.00   26
 15  \w     14.00  46.00   1.00    1.93    --   40.98-100.00  60.00   32
 16  \w      5.00  58.00   1.00    1.93    --   40.98-100.00-120.00   53
 17  \w     78.00 104.00   1.00    4.00    --  107.58  61.00   0.00   26
 18  \w     78.00 104.00   1.00    4.00    --  107.58  61.00 -60.00   26
 19  \w     89.00 117.00   1.00    4.00    --  107.58-127.00 -90.00   28
 20  \w     75.00 101.00   1.00    4.00    --  107.58  77.00 -30.00   26
 21  \w     76.00  86.00   1.00    4.00    --  107.58  77.00   0.00   10
;
_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      -0.0986676000
_diffrn_orient_matrix_UB_12      -0.0885121000
_diffrn_orient_matrix_UB_13      -0.0444041000
_diffrn_orient_matrix_UB_21      0.0592413000
_diffrn_orient_matrix_UB_22      0.0592901000
_diffrn_orient_matrix_UB_23      -0.0593363000
_diffrn_orient_matrix_UB_31      0.0781248000
_diffrn_orient_matrix_UB_32      -0.1570789000
_diffrn_orient_matrix_UB_33      0.0027049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10499
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.921
_diffrn_reflns_theta_min         2.128
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65115
_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    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0753P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.574
_reflns_Friedel_fraction_full    0.700
_reflns_Friedel_fraction_max     0.647
_reflns_number_gt                4458
_reflns_number_total             6239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00884_si_003.cif
_cod_data_source_block           1635de-26
_cod_original_cell_volume        1877.73(17)
_cod_database_code               1560805
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 99.97
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C17B, C18B, C19B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C17B \\sim C18B \\sim C19B: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C7(H7), C6(H6), C11B(H11B), C6B(H6B), C8(H8), C10B(H10B), C11(H11), C10(H10),
 C8B(H8B), C7B(H7B)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9B(H9BA,H9BB)
4.c Aromatic/amide H refined with riding coordinates:
 C3'(H3'), C2(H2), C2B(H2B), C18B(H18B)
4.d Idealised Me refined as rotating group:
 C15B(H15D,H15E,H15F), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C13B(H13D,
 H13E,H13F), C5'(H5'A,H5'B,H5'C), C14B(H14D,H14E,H14F), C14(H14A,H14B,H14C),
 C4'(H4'A,H4'B,H4'C), C19B(H19A,H19B,H19C), C20B(H20A,H20B,H20C)
;
_shelx_res_checksum              22959
_shelx_hkl_checksum              61332
_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 1.621
_oxdiff_exptl_absorpt_empirical_full_min 0.431