Germacrane-Type Sesquiterpenoids with Antiproliferative Activities from Eupatorium chinense
Yu, Xiaoqin; Zhang, Qingqing; Tian, Li; Guo, Zhiyong; Liu, Chengxiong; Chen, Jianfeng; Ebrahim, Weaam; Liu, Zhen; Proksch, Peter; Zou, Kun; Journal of Natural Products  (2017) –; doi:10.1021/acs.jnatprod.7b00693

data_1548548
_publ_section_title
;
 Germacrane-Type Sesquiterpenoids with Antiproliferative Activities from
 Eupatorium chinense
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00693
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H28 O8'
_chemical_formula_sum            'C22 H28 O8'
_chemical_formula_weight         420.44
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6433(2)
_cell_length_b                   13.6676(3)
_cell_length_c                   14.8419(3)
_cell_measurement_reflns_used    7400
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      73.3420
_cell_measurement_theta_min      5.1010
_cell_volume                     2159.03(8)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00 -60.00   98
  2  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00  30.00   98
  3  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00-180.00   81
  4  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00 120.00   99
  5  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00   0.00   85
  6  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -90.00   85
  7  \w     35.00 136.00   1.00    1.00    --  106.95 -61.00 -60.00  101
  8  \w     25.00 140.00   1.00    1.00    --  106.95 -15.00  30.00  115
;
_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      0.0030578000
_diffrn_orient_matrix_UB_12      0.0180859000
_diffrn_orient_matrix_UB_13      -0.1024895000
_diffrn_orient_matrix_UB_21      -0.1426978000
_diffrn_orient_matrix_UB_22      0.0191661000
_diffrn_orient_matrix_UB_23      0.0006845000
_diffrn_orient_matrix_UB_31      0.0246831000
_diffrn_orient_matrix_UB_32      0.1094908000
_diffrn_orient_matrix_UB_33      0.0165246000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.707
_diffrn_reflns_theta_min         4.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68343
_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            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0440P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                4128
_reflns_number_total             4248
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00693_si_002.cif
_cod_data_source_block           exp_314
_cod_original_cell_volume        2159.04(8)
_cod_database_code               1548548
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.821
_reflns_odcompleteness_completeness 99.91
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C6(H6), C2(H2), C7(H7), C8(H8A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C4'(H4'A,H4'B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C2'(H2')
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C5'(H5'A,H5'B,
 H5'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O3(H3)
;
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.752