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_1557527
_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         'C15 H12 O8, 2(H2 O)'
_chemical_formula_sum            'C15 H16 O10'
_chemical_formula_weight         356.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.615(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5499(6)
_cell_length_b                   9.7031(4)
_cell_length_c                   8.6354(3)
_cell_measurement_reflns_used    3156
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5950
_cell_measurement_theta_min      5.0180
_cell_volume                     1463.45(9)
_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    'ShelXT (Sheldrick, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.970
_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    -26.00   5.00   1.00    1.00    --   40.98 -38.00  90.00   31
  2  \w     15.00  66.00   1.00    1.00    --   40.98 -38.00  90.00   51
  3  \w     20.00  47.00   1.00    1.00    --   40.98 -99.00 -30.00   27
  4  \w     49.00 132.00   1.00    3.00    --  107.58 -45.00-120.00   83
  5  \w     67.00 107.00   1.00    3.00    --  107.58 -95.00-120.00   40
  6  \w     66.00 135.00   1.00    3.00    --  107.58 -77.00 -60.00   69
  7  \w     79.00 177.00   1.00    3.00    --  107.58  30.00  60.00   98
  8  \w    109.00 135.00   1.00    3.00    --  107.58 125.00  60.00   26
  9  \w     96.00 143.00   1.00    3.00    --  107.58 125.00-120.00   47
 10  \w     45.00 120.00   1.00    3.00    --  107.58-125.00-180.00   75
 11  \w    -93.00 -59.00   1.00    1.00    --  -40.98 125.00 -30.00   34
 12  \w   -113.00 -16.00   1.00    1.00    --  -40.98 -38.00 -60.00   97
;
_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      0.0172867000
_diffrn_orient_matrix_UB_12      0.1535717000
_diffrn_orient_matrix_UB_13      -0.0251393000
_diffrn_orient_matrix_UB_21      -0.0775994000
_diffrn_orient_matrix_UB_22      0.0390450000
_diffrn_orient_matrix_UB_23      0.0571026000
_diffrn_orient_matrix_UB_31      0.0381597000
_diffrn_orient_matrix_UB_32      0.0096619000
_diffrn_orient_matrix_UB_33      0.1681281000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5622
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.864
_diffrn_reflns_theta_min         2.530
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76467
_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    1.617
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0295P)^2^+3.0393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2511
_reflns_number_total             2877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00877_si_001.cif
_cod_data_source_block           ehl-30
_cod_database_code               1557527
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.89
_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, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA), O2W(H2WA,H2WB)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C3(H3A,H3B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), 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 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.353