Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from <i>Isodon amethystoides</i> bearing a six/five/seven-membered carbon-ring system
Zhao, Chen-Liang; Sarwar, Md. Shahid; Ye, Jiang-Hai; Ku, Chuen Fai; Li, Wan-Fei; Luo, Guo-Yong; Zhang, Jing-Jie; Xu, Jun; Huang, Zhao-Feng; Tsang, Siu Wai; Pan, Lu-Tai; Zhang, Hong-Jie; Acta Crystallographica Section C 74 (2018) 635–640; doi:10.1107/S2053229618005740

data_2021093
_publ_section_title
;
 Isolation, evaluation of bioactivity and structure determination of
 amethinol A, a prototypic amethane diterpene from <i>Isodon
 amethystoides</i> bearing a six/five/seven-membered carbon-ring system
;
_journal_coeditor_code           LG3224
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              635
_journal_page_last               640
_journal_paper_doi               10.1107/S2053229618005740
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C20 H32 O5'
_chemical_formula_moiety         'C20 H32 O5'
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.45
_chemical_name_systematic
;(4a<i>R</i>,4 b<i>R</i>,7<i>R</i>,10<i>aS</i>)-4
b,7-Dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[<i>a</i>]azulene-4a(2<i>H</i>)-carboxylic acid
;
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4641(2)
_cell_length_b                   11.6518(4)
_cell_length_c                   25.4249(9)
_cell_measurement_reflns_used    3751
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      48.57
_cell_measurement_theta_min      5.62
_cell_volume                     1914.96(11)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24714
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.846
_diffrn_reflns_theta_min         4.174
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  0.7856
_exptl_absorpt_correction_T_min  0.7215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.142
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al</i>., 2013)
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0418P)^2^+0.3285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                3630
_reflns_number_total             3648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lg3224sup1.cif
_cod_data_source_block           I
_cod_database_code               2021093
_cod_database_fobs_code          2021093
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.921
_shelx_hkl_checksum              6060
_shelx_res_checksum              46470