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_7232595
_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         'C23 H34 O8'
_chemical_formula_sum            'C23 H34 O8'
_chemical_formula_weight         438.50
_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             2017-11-06
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2017-11-16 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            4
_cell_length_a                   5.61656(10)
_cell_length_b                   18.3134(3)
_cell_length_c                   22.9609(6)
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    104.4
_cell_measurement_theta_max      70.9135
_cell_measurement_theta_min      3.8479
_cell_volume                     2361.72(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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)/Bruker'
_diffrn_ambient_temperature      104.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -11.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000 -150.0000 26

  2 omega   28.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000 -150.0000 27

  3 omega  -33.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000 -150.0000 95

  4 omega    8.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000  -30.0000 33

  5 omega   34.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   37.0000  -60.0000 69

  6 omega   53.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000  -30.0000 34

  7 omega   18.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000 -150.0000 25

  8 omega   40.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 28

  9 omega   44.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 54

 10 omega  147.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 28

 11 omega   40.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 48

 12 omega   61.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 71

 13 omega   54.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 26

 14 omega   78.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -116.0000 -116.0000 39

 15 omega   73.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 103

 16 omega   52.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 41
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0407153000
_diffrn_orient_matrix_UB_12      -0.0253193000
_diffrn_orient_matrix_UB_13      -0.0632091000
_diffrn_orient_matrix_UB_21      -0.0301833000
_diffrn_orient_matrix_UB_22      0.0792396000
_diffrn_orient_matrix_UB_23      -0.0213299000
_diffrn_orient_matrix_UB_31      0.2694675000
_diffrn_orient_matrix_UB_32      0.0125678000
_diffrn_orient_matrix_UB_33      0.0071152000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.051
_diffrn_reflns_theta_min         3.850
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1678 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0585P)^2^+0.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                4244
_reflns_number_total             4456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00478e2.cif
_cod_data_source_block           exp_5183
_cod_original_cell_volume        2361.72(9)
_cod_database_code               7232595
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.832
_shelx_res_checksum              88261
_shelx_shelxl_version_number     2014/7