Absolute Configurations and Bioactivities of Guaiane-Type Sesquiterpenoids Isolated from Pogostemon cablin.
Zhou, Qin-Mei; Chen, Ming-Hua; Li, Xiao-Hong; Peng, Cheng; Lin, Da-Sheng; Li, Xiao-Nian; He, Yang; Xiong, Liang; Journal of natural products 81 (2018) 1919–1927; doi:10.1021/acs.jnatprod.7b00690

data_1553316
_publ_section_title
;
 Absolute Configurations and Bioactivities of Guaiane-Type
 Sesquiterpenoids Isolated from Pogostemon cablin.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              1919
_journal_page_last               1927
_journal_paper_doi               10.1021/acs.jnatprod.7b00690
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.0400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5078(3)
_cell_length_b                   10.0306(3)
_cell_length_c                   12.1928(3)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.31
_cell_measurement_theta_min      3.69
_cell_volume                     1381.37(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14185
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.630
_diffrn_reflns_theta_min         3.693
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          1.030
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.7532
_exptl_transmission_factor_min   0.6524
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.609
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.609
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0430P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.631
_reflns_Friedel_fraction_full    0.707
_reflns_Friedel_fraction_max     0.683
_reflns_number_gt                4197
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00690_si_002.cif
_cod_data_source_block           cu_ghx50_0m_Compound_6
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1553316
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.591
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              23479
_shelx_hkl_checksum              50658