Isolation, Absolute Configuration, and Biological Activities of Chebulic Acid and Brevifolincarboxylic Acid Derivatives from Euphorbia hirta
Yang, Zi-Ni; Su, Bao-Jun; Wang, Ya-Qi; Liao, Hai-Bing; Chen, Zhen-Feng; Liang, Dong; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b00877

data_1557524
_publ_section_title
;
 Isolation, Absolute Configuration, and Biological Activities of Chebulic
 Acid and Brevifolincarboxylic Acid Derivatives from Euphorbia hirta
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00877
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 O11'
_chemical_formula_sum            'C20 H24 O11'
_chemical_formula_weight         440.39
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-03
_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                   8.40725(14)
_cell_length_b                   9.73467(14)
_cell_length_c                   25.8797(4)
_cell_measurement_reflns_used    11045
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3490
_cell_measurement_theta_min      3.4190
_cell_volume                     2118.04(6)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -66.00  33.00   1.00    1.00    --  -41.11  38.00-150.00   99
  2  \w     23.00  97.00   1.00    1.00    --   41.11-125.00  30.00   74
  3  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00-180.00   81
  4  \w     23.00  97.00   1.00    1.00    --   41.11-125.00-180.00   74
  5  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00 120.00   84
  6  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00   0.00   99
  7  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00  30.00   84
  8  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00 -60.00   84
  9  \w     94.00 178.00   1.00    1.00    --  106.95 125.00   0.00   84
 10  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  60.00   97
 11  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00  60.00  100
 12  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 -90.00  100
 13  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 150.00  100
 14  \w     79.00 169.00   1.00    1.00    --  106.95  30.00 -90.00   90
;
_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      0.1060499000
_diffrn_orient_matrix_UB_12      0.0627275000
_diffrn_orient_matrix_UB_13      0.0424071000
_diffrn_orient_matrix_UB_21      -0.0199166000
_diffrn_orient_matrix_UB_22      -0.1310968000
_diffrn_orient_matrix_UB_23      0.0327258000
_diffrn_orient_matrix_UB_31      0.1480468000
_diffrn_orient_matrix_UB_32      -0.0625587000
_diffrn_orient_matrix_UB_33      -0.0260267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15020
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.740
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63905
_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    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0375P)^2^+0.5138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4034
_reflns_number_total             4202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00877_si_006.cif
_cod_data_source_block           ehl-33
_cod_database_code               1557524
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.95
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C11(H11), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C3'(H3'A,H3'B), C5'(H5'A,H5'B), C1'(H1'A,H1'B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d Idealised Me refined as rotating group:
 C6'(H6'A,H6'B,H6'C), C4'(H4'A,H4'B,H4'C), C2'(H2'A,H2'B,H2'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O5(H5)
;
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.599