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_1560806
_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         'C24 H36 O6'
_chemical_formula_sum            'C24 H36 O6'
_chemical_formula_weight         420.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6873(2)
_cell_length_b                   15.0723(4)
_cell_length_c                   24.1896(6)
_cell_measurement_reflns_used    7263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2980
_cell_measurement_theta_min      3.4080
_cell_volume                     2438.14(11)
_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 0.988
_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   -129.00  47.00   1.00    1.00    --  -40.98   0.00-120.00  176
  2  \w     24.00  98.00   1.00    1.00    --   40.98-126.00-180.00   74
  3  \w     94.00 178.00   1.00    2.50    --  106.95 126.00  60.00   84
  4  \w     25.00 109.00   1.00    2.50    --  106.95 -95.00-180.00   84
  5  \w     25.00 109.00   1.00    2.50    --  106.95 -95.00 -30.00   84
  6  \w     79.00 178.00   1.00    2.50    --  106.95  30.00  90.00   99
  7  \w     81.00 178.00   1.00    2.50    --  106.95  45.00-180.00   97
  8  \w     94.00 178.00   1.00    2.50    --  106.95 126.00-150.00   84
  9  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 150.00  100
 10  \w      8.00 117.00   1.00    1.00    --   40.98  77.00  60.00  109
 11  \w     79.00 137.00   1.00    2.50    --  106.95  30.00   0.00   58
;
_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      -0.1202221000
_diffrn_orient_matrix_UB_12      0.0695759000
_diffrn_orient_matrix_UB_13      0.0327532000
_diffrn_orient_matrix_UB_21      0.0765936000
_diffrn_orient_matrix_UB_22      -0.0400526000
_diffrn_orient_matrix_UB_23      0.0546327000
_diffrn_orient_matrix_UB_31      0.1808945000
_diffrn_orient_matrix_UB_32      0.0632371000
_diffrn_orient_matrix_UB_33      -0.0014117000
_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     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.738
_diffrn_reflns_theta_min         3.455
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45193
_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    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0689
_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^)+(0.1734P)^2^+0.1313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2259
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                4285
_reflns_number_total             4820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00884_si_004.cif
_cod_data_source_block           16552-1
_cod_database_code               1560806
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.919
_reflns_odcompleteness_completeness 99.96
_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
 C2", C4", C3"
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2" \\sim C4" \\sim C3": 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:
 C1(H1), C2(H2), C4(H4), C7(H7), C8(H8), C10(H10), C2"(H2"), C3'(H3')
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C9(H9A,H9B), C2'(H2'A,H2'B)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C4"(H4"A,H4"B,H4"C), C3"(H3"A,H3"B,
 H3"C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C)
;
_shelx_res_checksum              78604
_shelx_hkl_checksum              1483
_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.576