Cytotoxic 2, 4-Linked Sesquiterpene Lactone Dimers from Carpesium faberi Exhibiting NF-κB Inhibitory Activity
Yang, Yong-xun; Gao, Shuang; Zhang, Shoude; Zu, Xian-peng; Shen, Yunheng; Shan, Lei; Li, Hui-Liang; Zhang, Weidong; RSC Adv.  (2015) –; doi:10.1039/C5RA09243D

data_7220790
_publ_section_title
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 Cytotoxic 2, 4-Linked Sesquiterpene Lactone Dimers from Carpesium faberi
 Exhibiting NF-\kB Inhibitory Activity
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_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA09243D
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H38 O6'
_chemical_formula_sum            'C30 H38 O6'
_chemical_formula_weight         494.60
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-05 deposited with the CCDC.
2015-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6885(2)
_cell_length_b                   19.3149(4)
_cell_length_c                   40.8677(9)
_cell_measurement_reflns_used    6697
_cell_measurement_temperature    296
_cell_measurement_theta_max      51.76
_cell_measurement_theta_min      3.15
_cell_volume                     6069.0(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            47051
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.718
_diffrn_reflns_theta_min         2.162
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1412 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.7928.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       plate
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 3034 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.761
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         11227
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.781
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1647P)^2^+0.8090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1882
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                8412
_reflns_number_total             11227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra09243d2.cif
_cod_data_source_block           cu_dm14653_0m
_cod_database_code               7220790
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.932
_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. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim O2: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(O2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C2"(H2"), C7"(H7"), C8"(H8"), C10"(H10"), C1A(H1A), C5A(H5A), C7A(H7A),
 C8A(H8A), C1(H1), C5(H5), C7(H7), C8(H8), C2'(H2'), C7'(H7'), C8'(H8'),
 C10'(H10')
3.b Secondary CH2 refined with riding coordinates:
 C3"(H3"A,H3"B), C6"(H6"A,H6"B), C9"(H9"A,H9"B), C2A(H2AA,H2AB), C3A(H3AA,
 H3AB), C6A(H6AA,H6AB), C9A(H9AA,H9AB), C13A(H13C,H13D), C2(H2A,H2B), C3(H3A,
 H3B), C6(H6A,H6B), C9(H9A,H9B), C13(H13E,H13F), C3'(H3'A,H3'B), C6'(H6'A,H6'B),
  C9'(H9'A,H9'B)
3.c X=CH2 refined with riding coordinates:
 C13"(H13A,H13B), C13'(H13G,H13H)
3.d Idealised Me refined as rotating group:
 C14"(H14A,H14B,H14C), C15"(H15A,H15B,H15C), C14A(H14D,H14E,H14F), C15A(H15D,
 H15E,H15F), C14(H14G,H14H,H14I), C15(H15G,H15H,H15I), C14'(H14J,H14K,H14L),
 C15'(H15J,H15K,H15L)
There are infinite channels containing disordered solvent(acetone), to which OLEX2 solvent-masking procedure was applied. F000, mu and f.w. are calculated without the solvent.
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_shelx_res_checksum              27161
_shelx_hkl_checksum              56919
_olex2_submission_special_instructions 'No special instructions were received'