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_1557523
_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_formula_moiety         'C17 H16 O9'
_chemical_formula_sum            'C17 H16 O9'
_chemical_formula_weight         364.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.165(11)
_cell_angle_beta                 79.443(10)
_cell_angle_gamma                80.100(11)
_cell_formula_units_Z            2
_cell_length_a                   8.1135(10)
_cell_length_b                   9.1532(13)
_cell_length_c                   11.5337(14)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6750
_cell_measurement_theta_min      3.9210
_cell_volume                     818.61(19)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.957
_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    -52.00  34.00   1.00    1.00    --  -40.73  38.00  90.00   86
  2  \w    -44.00 -17.00   1.00    1.00    --  -40.73 125.00  90.00   27
  3  \w    -95.00 -47.00   1.00    1.00    --  -40.73 125.00  90.00   48
  4  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00  100
  5  \w    -20.00  72.00   1.00    1.00    --   40.73 -77.00-180.00   92
  6  \w     32.00 120.00   1.00    1.00    --  106.95 -30.00 -60.00   88
  7  \w     81.00 108.00   1.00    1.00    --  106.95  45.00 -60.00   27
  8  \w    153.00 178.00   1.00    1.00    --  106.95  45.00 -60.00   25
  9  \w    131.00 165.00   1.00    1.00    --  106.95 125.00   0.00   34
 10  \w     97.00 122.00   1.00    1.00    --  106.95 125.00 -30.00   25
 11  \w     97.00 153.00   1.00    1.00    --  106.95 125.00-150.00   56
 12  \w     83.00 177.00   1.00    1.00    --  106.95  30.00 120.00   94
 13  \w     74.00 109.00   1.00    1.00    --  106.95 -94.00  90.00   35
 14  \w     50.00 109.00   1.00    1.00    --  106.95 -94.00  30.00   59
 15  \w     73.00 121.00   1.00    1.00    --  106.95-125.00 -30.00   48
 16  \w     47.00 104.00   1.00    1.00    --  106.95 -61.00 -90.00   57
 17  \w     47.00 105.00   1.00    1.00    --  106.95 -94.00-180.00   58
 18  \w     36.00  69.00   1.00    1.00    --  106.95-125.00 -30.00   33
 19  \w     37.00  79.00   1.00    1.00    --  106.95 -61.00  90.00   42
 20  \w     31.00 132.00   1.00    1.00    --  106.95 -30.00 120.00  101
;
_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      -0.1378011000
_diffrn_orient_matrix_UB_12      0.0369268000
_diffrn_orient_matrix_UB_13      0.1055922000
_diffrn_orient_matrix_UB_21      -0.0353332000
_diffrn_orient_matrix_UB_22      -0.1640218000
_diffrn_orient_matrix_UB_23      0.0259871000
_diffrn_orient_matrix_UB_31      0.1335673000
_diffrn_orient_matrix_UB_32      -0.0413085000
_diffrn_orient_matrix_UB_33      0.0844430000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5231
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.296
_diffrn_reflns_theta_min         3.951
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82508
_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    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0472P)^2^+3.6416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.1886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2651
_reflns_number_total             3143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00877_si_005.cif
_cod_data_source_block           ehl-63
_cod_original_cell_volume        818.60(19)
_cod_database_code               1557523
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.876
_reflns_odcompleteness_completeness 99.28
_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 Secondary CH2 refined with riding coordinates:
 C3'(H3'A,H3'B), C1'(H1'A,H1'B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.c Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C2'(H2'A,H2'B,H2'C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O3(H3), O4(H4)
;
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.727