Monomeric and Dimeric Cytotoxic Guaianolide-Type Sesquiterpenoids from the Aerial Parts of Chrysanthemum indicum.
Luo, Pan; Cheng, Yanfang; Yin, Zhiyong; Li, Chanjuan; Xu, Jun; Gu, Qiong; Journal of natural products 82 (2019) 349–357; doi:10.1021/acs.jnatprod.8b00863

data_1552648
_publ_section_title
;
 Monomeric and Dimeric Cytotoxic Guaianolide-Type Sesquiterpenoids from
 the Aerial Parts of Chrysanthemum indicum.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              349
_journal_page_last               357
_journal_paper_doi               10.1021/acs.jnatprod.8b00863
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         'C30 H38 O7'
_chemical_formula_sum            'C30 H38 O7'
_chemical_formula_weight         510.60
_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             2018-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3224(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.74469(7)
_cell_length_b                   11.28356(7)
_cell_length_c                   11.95583(9)
_cell_measurement_reflns_used    20353
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.8310
_cell_measurement_theta_min      3.7610
_cell_volume                     1284.315(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     18.00 114.00   1.00    3.00    --   44.06  57.00  90.00   96
  2  \w     18.00 114.00   1.00    3.00    --   44.06  57.00-180.00   96
  3  \w     18.00 114.00   1.00    3.00    --   44.06  57.00   0.00   96
  4  \w      4.00  99.00   1.00    3.00    --   44.06-128.00 -54.00   95
  5  \w     37.00 132.00   1.00   10.00    --  108.00 -45.00 150.00   95
  6  \w     34.00 121.00   1.00   10.00    --  108.00-125.00 -30.00   87
  7  \w     34.00 140.00   1.00   10.00    --  108.00 -77.00 120.00  106
  8  \w     35.00 135.00   1.00   10.00    --  108.00 -30.00  60.00  100
  9  \w     69.00 178.00   1.00   10.00    --  108.00  15.00 -60.00  109
 10  \w     34.00 121.00   1.00   10.00    --  108.00-125.00 120.00   87
 11  \w     81.00 178.00   1.00   10.00    --  108.00  61.00 120.00   97
 12  \w     25.00 109.00   1.00   10.00    --  108.00 -94.00 -30.00   84
 13  \w     25.00 109.00   1.00   10.00    --  108.00 -94.00  30.00   84
 14  \w     34.00 121.00   1.00   10.00    --  108.00-125.00 150.00   87
 15  \w     38.00 135.00   1.00   10.00    --  108.00 -61.00 -30.00   97
 16  \w     25.00 109.00   1.00   10.00    --  108.00 -94.00-180.00   84
 17  \w     25.00 109.00   1.00   10.00    --  108.00 -94.00-120.00   84
 18  \w     76.00 178.00   1.00   10.00    --  108.00  77.00  90.00  102
 19  \w   -118.00 -73.00   1.00    3.00    --  -44.06-125.00   0.00   45
 20  \w    -26.00  70.00   1.00    3.00    --   44.06 -57.00  30.00   96
 21  \w     18.00 114.00   1.00    3.00    --   44.06  57.00 -90.00   96
 22  \w     73.00 118.00   1.00    3.00    --   44.06 125.00-180.00   45
 23  \w     76.00 178.00   1.00   10.00    --  108.00  77.00  60.00  102
 24  \w     84.00 178.00   1.00   10.00    --  108.00  45.00  60.00   94
 25  \w     81.00 178.00   1.00   10.00    --  108.00  30.00  30.00   97
 26  \w     76.00 178.00   1.00   10.00    --  108.00  77.00 -90.00  102
 27  \w     81.00 178.00   1.00   10.00    --  108.00  30.00-150.00   97
 28  \w     81.00 178.00   1.00   10.00    --  108.00  61.00-150.00   97
 29  \w     81.00 178.00   1.00   10.00    --  108.00  61.00 150.00   97
 30  \w     76.00 174.00   1.00   10.00    --  108.00  77.00   0.00   98
 31  \w     80.00 178.00   1.00   10.00    --  108.00  66.00 -41.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0326186000
_diffrn_orient_matrix_UB_12      -0.1305893000
_diffrn_orient_matrix_UB_13      -0.0330526000
_diffrn_orient_matrix_UB_21      -0.1250476000
_diffrn_orient_matrix_UB_22      0.0393611000
_diffrn_orient_matrix_UB_23      -0.0946244000
_diffrn_orient_matrix_UB_31      0.0973761000
_diffrn_orient_matrix_UB_32      0.0068533000
_diffrn_orient_matrix_UB_33      -0.0857131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24724
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.113
_diffrn_reflns_theta_min         3.784
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (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    1.320
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2293 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0516P)^2^+0.2083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4946
_reflns_number_total             5045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00863_si_002.cif
_cod_data_source_block           lp_180115
_cod_original_cell_volume        1284.314(16)
_cod_database_code               1552648
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.864
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C14(H14), C19(H19), C21(H21), C24(H24), C30(H30), C31(H31), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C22(H22A,H22B), C27(H27A,H27B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C26(H26), C34(H34)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C28(H28A,H28B,H28C), C32(H32A,H32B,
 H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O8(H8)
;
_shelx_res_checksum              9749
_shelx_hkl_checksum              44535
_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 5.525
_oxdiff_exptl_absorpt_empirical_full_min 0.582