New antiproliferative germacranolides from Carpesium divaricatum
Zhang, Tao; Zhang, Qiu-Bo; Fu, Lu; Li, Ling-Yu; Ma, Li-Yan; Si, Jin-Guang; Zhang, Hong-Wu; Wei, Jian-He; Yu, Shi-Shan; Zou, Zhong-Mei; RSC Advances 9 (2019) 11493–; doi:10.1039/C9RA00478E

data_7232596
_publ_section_title
;
 New antiproliferative germacranolides from Carpesium divaricatum
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              11493
_journal_paper_doi               10.1039/C9RA00478E
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C24 H34 O9'
_chemical_formula_sum            'C24 H34 O9'
_chemical_formula_weight         466.51
_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   geom
_audit_creation_date             2018-04-27
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2018-05-03 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8307(12)
_cell_length_b                   17.7908(13)
_cell_length_c                   27.106(2)
_cell_measurement_reflns_used    7997
_cell_measurement_temperature    109.45(10)
_cell_measurement_theta_max      71.0130
_cell_measurement_theta_min      4.0950
_cell_volume                     4740.7(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.45(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9707
_diffrn_measurement_details
;
  1 omega   -1.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  120.0000 74

  2 omega   53.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000  120.0000 56

  3 omega   49.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 32

  4 omega   60.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 31

  5 omega   64.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 26

  6 omega   55.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 34

  7 omega   39.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 50

  8 omega   46.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 37

  9 omega   42.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 52

 10 omega   47.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 78

 11 omega  100.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 78

 12 omega   81.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 59

 13 omega   57.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000   60.0000 25

 14 omega   22.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -90.0000 79

 15 omega   41.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -150.0000 62

 16 omega  -27.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1467610000
_diffrn_orient_matrix_UB_12      -0.0298885000
_diffrn_orient_matrix_UB_13      -0.0027958000
_diffrn_orient_matrix_UB_21      0.0079882000
_diffrn_orient_matrix_UB_22      0.0245319000
_diffrn_orient_matrix_UB_23      -0.0545272000
_diffrn_orient_matrix_UB_31      0.0542227000
_diffrn_orient_matrix_UB_32      0.0774095000
_diffrn_orient_matrix_UB_33      0.0161756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18022
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.163
_diffrn_reflns_theta_min         4.785
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 3357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         8922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0631P)^2^+1.8430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                8334
_reflns_number_total             8922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00478e2.cif
_cod_data_source_block           exp_5446
_cod_original_cell_volume        4740.8(8)
_cod_database_code               7232596
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.733
_shelx_res_checksum              60658
_shelx_shelxl_version_number     2014/7