Isolation, Structure Elucidation, and Absolute Configuration of Highly Oxygenated Germacranolides from Carpesium cernuum.
Liu, Qing-Xin; Yang, Yong-Xun; Zhang, Jian-Ping; Chen, Li-Ping; Shen, Yun-Heng; Li, Hui-Liang; Zhang, Wei-Dong; Journal of natural products 79 (2016) 2479–2486; doi:10.1021/acs.jnatprod.6b00315

data_1544493
_publ_section_title
;
 Isolation, Structure Elucidation, and Absolute Configuration of Highly
 Oxygenated Germacranolides from Carpesium cernuum.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2479
_journal_page_last               2486
_journal_paper_doi               10.1021/acs.jnatprod.6b00315
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H40 O10'
_chemical_formula_sum            'C26 H40 O10'
_chemical_formula_weight         512.58
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   22.8955(3)
_cell_length_b                   22.8955(3)
_cell_length_c                   9.7127(2)
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      66.431
_cell_measurement_theta_min      3.861
_cell_volume                     4409.31(12)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.973
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24657
_diffrn_reflns_point_group_measured_fraction_full 0.833
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.053
_diffrn_reflns_theta_min         2.228
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1504 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.8092.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       prism
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1020P)^2^+0.5296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.599
_reflns_Friedel_fraction_full    0.669
_reflns_Friedel_fraction_max     0.661
_reflns_number_gt                4156
_reflns_number_total             4615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00315_si_002.cif
_cod_data_source_block           cu_dm15690_0m
_cod_original_cell_volume        4409.31(15)
_cod_database_code               1544493
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.879
_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. Uiso/Uaniso restraints and constraints
C1" \\sim C2" \\sim C3" \\sim C4" \\sim C5": within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01
C1' \\sim C2' \\sim C3' \\sim C4' \\sim C5': within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(C2") \\sim Ueq, Uanis(C5") \\sim Ueq, Uanis(C3") \\sim Ueq, Uanis(C4")
\\sim Ueq, Uanis(C3') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C5') \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7A), C8(H8), C9(H9), C10(H10), C11(H11), C3'(H3')
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C13(H13A,H13B), C2'(H2'A,H2'B)
3.c Aromatic/amide H refined with riding coordinates:
 C3"(H3")
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C4"(H4"A,H4"B,
 H4"C), C5"(H5"A,H5"B,H5"C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7)
;
_shelx_res_checksum              37535
_shelx_hkl_checksum              98242
_olex2_submission_special_instructions 'No special instructions were received'