Cytotoxic Germacranolides from the Whole Plant of Carpesium minus
Zhu, Li; Liu, Xiao-Qin; Lin, Yao-Lan; Wang, Wen-Li; Luo, Jian-Guang; Kong, Ling-Yi; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00428

data_1559313
_publ_section_title
;
 Cytotoxic Germacranolides from the Whole Plant of Carpesium minus
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00428
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H28 O7'
_chemical_formula_sum            'C20 H28 O7'
_chemical_formula_weight         380.42
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2716(2)
_cell_length_b                   12.1391(2)
_cell_length_c                   17.1059(3)
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.406
_cell_measurement_theta_min      5.022
_cell_volume                     2132.90(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21475
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.406
_diffrn_reflns_theta_min         5.022
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1661 before and 0.0954 after correction. The Ratio of minimum to maximum transmission is 0.6108. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
TITL 22019709_0m_a.res in P2(1)2(1)2(1)
CELL   10.2716   12.1391   17.1059     90.00     90.00     90.00
SPGR P212121
Q101 0.488 0.487 0.764 !       8.23 eA-3
C102 0.790 0.373 0.282 !       4.92 eA-3
C103 0.226 0.984 0.247 !       3.03 eA-3
Q104 0.087 0.589 0.245 !       1.28 eA-3
Q105 0.138 0.234 0.331 !       1.04 eA-3
Q106 0.883 0.468 0.529 !       0.67 eA-3
Q107 0.977 0.896 0.512 !       0.66 eA-3
Q108 0.805 0.503 0.017 !       0.64 eA-3
Q109 0.298 0.513 0.153 !       0.62 eA-3
Q110 0.234 0.730 0.111 !       0.62 eA-3
Q111 0.943 0.580 0.263 !       0.61 eA-3
Q112 0.649 0.547 0.094 !       0.61 eA-3
Q113 0.790 0.095 0.001 !       0.60 eA-3
Q114 0.701 0.379 0.785 !       0.55 eA-3
Q115 0.929 0.643 0.066 !       0.55 eA-3
Q116 0.548 0.246 0.579 !       0.54 eA-3
Q117 0.379 0.824 0.083 !       0.54 eA-3
Q118 0.190 0.816 0.609 !       0.53 eA-3
Q119 0.981 0.385 0.297 !       0.53 eA-3
Q120 0.447 0.728 0.579 !       0.53 eA-3
Q121 0.101 0.484 0.263 !       0.53 eA-3
Q122 0.059 0.460 0.157 !       0.52 eA-3
Q123 0.162 0.822 0.357 !       0.50 eA-3
;
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0784P)^2^+0.9588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4020
_reflns_number_total             4170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00428_si_007.cif
_cod_data_source_block           22019709_0m_sq
_cod_database_code               1559313
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.878
_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. Restrained distances
 O7-H7
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7A), C8(H8), C2(H2A), C9(H9), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C1(H1A,H1B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C3'(H3')
3.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C5'(H5'A,H5'B,H5'C), C4'(H4'A,H4'B,
 H4'C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'