Discovery of two <i>ent</i>-atisane diterpenoid lactones with AChE inhibitory activity from the roots of <i>Euphorbia fischeriana</i>.
Wei, Jiangchun; Li, Zhiyue; Shan, Min; Wu, Fengzhi; Li, Limin; Ma, Yucui; Wu, Junhong; Li, Xinping; Liu, Yaqian; Hu, Zhengxi; Zhang, Yonghui; Wu, Zhengzhi; Organic & biomolecular chemistry 21 (2023) 6949–6955; doi:10.1039/d3ob01007d

data_7159522
_publ_section_title
;
 Discovery of two <i>ent</i>-atisane diterpenoid lactones with AChE
 inhibitory activity from the roots of <i>Euphorbia fischeriana</i>.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6949
_journal_page_last               6955
_journal_paper_doi               10.1039/d3ob01007d
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H26 O3'
_chemical_formula_sum            'C19 H26 O3'
_chemical_formula_weight         302.40
_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     dual
_audit_creation_date             2021-07-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-14 deposited with the CCDC.	2023-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.22994(11)
_cell_length_b                   10.47670(16)
_cell_length_c                   24.3448(4)
_cell_measurement_reflns_used    5498
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9940
_cell_measurement_theta_min      4.5790
_cell_volume                     1588.97(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    2.00    --  -41.80 -38.00  90.00   99
  2  \w    -96.00  -2.00   1.00    2.00    --  -41.80 125.00  30.00   94
  3  \w     17.00 116.00   1.00    2.00    --   41.80  38.00  30.00   99
  4  \w     25.00 110.00   1.00    6.00    --  107.51 -95.00 -30.00   85
  5  \w     94.00 178.00   1.00    6.00    --  107.51 125.00 -30.00   84
  6  \w     31.00 136.00   1.00    6.00    --  107.51 -30.00   0.00  105
  7  \w     31.00 136.00   1.00    6.00    --  107.51 -30.00 -90.00  105
  8  \w     25.00  52.00   1.00    6.00    --  107.51 -95.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0051281000
_diffrn_orient_matrix_UB_12      -0.1139955000
_diffrn_orient_matrix_UB_13      -0.0399676000
_diffrn_orient_matrix_UB_21      -0.0102060000
_diffrn_orient_matrix_UB_22      0.0928848000
_diffrn_orient_matrix_UB_23      -0.0489718000
_diffrn_orient_matrix_UB_31      0.2470254000
_diffrn_orient_matrix_UB_32      0.0014505000
_diffrn_orient_matrix_UB_33      -0.0028845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6671
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.802
_diffrn_reflns_theta_min         3.631
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0410P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                2952
_reflns_number_total             2997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01007d2.cif
_cod_data_source_block           18h3
_cod_depositor_comments          'Adding full bibliography for 7159522.cif.'
_cod_original_cell_volume        1588.96(4)
_cod_database_code               7159522
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N30 O30 '
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C13(H13A,H13B),
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              51202
_olex2_date_sample_data_collection 2021-07-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.464