#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/75/1557523.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1557523
loop_
_publ_author_name
'Yang, Zi-Ni'
'Su, Bao-Jun'
'Wang, Ya-Qi'
'Liao, Hai-Bing'
'Chen, Zhen-Feng'
'Liang, Dong'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -52.00  34.00   1.00    1.00    --  -40.73  38.00  90.00   86
  2  ω    -44.00 -17.00   1.00    1.00    --  -40.73 125.00  90.00   27
  3  ω    -95.00 -47.00   1.00    1.00    --  -40.73 125.00  90.00   48
  4  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00  100
  5  ω    -20.00  72.00   1.00    1.00    --   40.73 -77.00-180.00   92
  6  ω     32.00 120.00   1.00    1.00    --  106.95 -30.00 -60.00   88
  7  ω     81.00 108.00   1.00    1.00    --  106.95  45.00 -60.00   27
  8  ω    153.00 178.00   1.00    1.00    --  106.95  45.00 -60.00   25
  9  ω    131.00 165.00   1.00    1.00    --  106.95 125.00   0.00   34
 10  ω     97.00 122.00   1.00    1.00    --  106.95 125.00 -30.00   25
 11  ω     97.00 153.00   1.00    1.00    --  106.95 125.00-150.00   56
 12  ω     83.00 177.00   1.00    1.00    --  106.95  30.00 120.00   94
 13  ω     74.00 109.00   1.00    1.00    --  106.95 -94.00  90.00   35
 14  ω     50.00 109.00   1.00    1.00    --  106.95 -94.00  30.00   59
 15  ω     73.00 121.00   1.00    1.00    --  106.95-125.00 -30.00   48
 16  ω     47.00 104.00   1.00    1.00    --  106.95 -61.00 -90.00   57
 17  ω     47.00 105.00   1.00    1.00    --  106.95 -94.00-180.00   58
 18  ω     36.00  69.00   1.00    1.00    --  106.95-125.00 -30.00   33
 19  ω     37.00  79.00   1.00    1.00    --  106.95 -61.00  90.00   42
 20  ω     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       'ω 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/[σ²(Fo²)+(0.0472P)²+3.6416P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.4249(3) 0.7966(3) 0.5470(2) 0.0194(5) Uani 1 1 d . . . . .
O5 O 0.9596(3) 0.2506(3) 0.5244(2) 0.0268(6) Uani 1 1 d . . . . .
H5 H 1.037520 0.223019 0.473519 0.040 Uiso 1 1 calc GR . . . .
O6 O 0.2509(3) 1.0718(3) 0.4304(2) 0.0247(6) Uani 1 1 d . . . . .
O9 O 0.7587(3) 0.9328(3) 0.1852(2) 0.0245(6) Uani 1 1 d . . . . .
O005 O 0.4874(3) 0.6213(3) 0.6984(2) 0.0265(6) Uani 1 1 d . . . . .
O3 O 0.8763(3) 0.6393(3) 0.1960(2) 0.0290(6) Uani 1 1 d . . . . .
H3 H 0.850016 0.730887 0.184300 0.043 Uiso 1 1 calc GR . . . .
O4 O 1.0402(4) 0.3685(3) 0.2924(2) 0.0320(7) Uani 1 1 d . . . . .
H4 H 1.047010 0.408809 0.222228 0.048 Uiso 1 1 calc GR . . . .
O8 O 0.4335(4) 0.7353(3) 0.1727(2) 0.0349(7) Uani 1 1 d . . . . .
O7 O 0.6264(4) 0.8376(3) 0.0288(2) 0.0357(7) Uani 1 1 d . . . . .
C3 C 0.4617(4) 0.8536(4) 0.4299(3) 0.0190(7) Uani 1 1 d . . . . .
C10 C 0.6912(4) 0.6565(4) 0.3880(3) 0.0202(7) Uani 1 1 d . . . . .
C4 C 0.5848(4) 0.7940(4) 0.3501(3) 0.0210(7) Uani 1 1 d . . . . .
C7 C 0.8737(4) 0.3835(4) 0.4786(3) 0.0217(7) Uani 1 1 d . . . . .
C1 C 0.5216(4) 0.6643(4) 0.5935(3) 0.0203(7) Uani 1 1 d . . . . .
C9 C 0.6559(4) 0.5920(4) 0.5092(3) 0.0198(7) Uani 1 1 d . . . . .
C11 C 0.5926(5) 0.8945(4) 0.2291(3) 0.0223(8) Uani 1 1 d . . . . .
C5 C 0.8254(5) 0.5843(4) 0.3138(3) 0.0225(8) Uani 1 1 d . . . . .
C6 C 0.9119(4) 0.4461(4) 0.3591(3) 0.0233(8) Uani 1 1 d . . . . .
C8 C 0.7465(4) 0.4563(4) 0.5551(3) 0.0206(7) Uani 1 1 d . . . . .
H8 H 0.722455 0.415126 0.635324 0.025 Uiso 1 1 calc R . . . .
C13 C 0.3692(4) 0.9954(4) 0.3785(3) 0.0211(7) Uani 1 1 d . . . . .
C14 C 0.5538(5) 0.8183(4) 0.1302(3) 0.0255(8) Uani 1 1 d . . . . .
C12 C 0.4513(5) 1.0302(4) 0.2491(3) 0.0233(8) Uani 1 1 d . . . . .
C3' C 0.8237(5) 1.0185(4) 0.2563(3) 0.0282(8) Uani 1 1 d . . . . .
H3'A H 0.804040 0.974724 0.340129 0.034 Uiso 1 1 calc R . . . .
H3'B H 0.767150 1.121440 0.247276 0.034 Uiso 1 1 calc R . . . .
C4' C 1.0095(5) 1.0147(5) 0.2129(4) 0.0353(9) Uani 1 1 d . . . . .
H4'A H 1.027978 1.049423 0.128316 0.053 Uiso 1 1 calc GR . . . .
H4'B H 1.065694 0.913588 0.229572 0.053 Uiso 1 1 calc GR . . . .
H4'C H 1.053981 1.078602 0.252965 0.053 Uiso 1 1 calc GR . . . .
C2' C 0.2697(6) 0.7396(5) 0.0141(4) 0.0428(11) Uani 1 1 d . . . . .
H2'A H 0.258142 0.685619 -0.047088 0.064 Uiso 1 1 calc GR . . . .
H2'B H 0.310522 0.832586 -0.022305 0.064 Uiso 1 1 calc GR . . . .
H2'C H 0.161582 0.760111 0.062634 0.064 Uiso 1 1 calc GR . . . .
C1' C 0.3912(7) 0.6480(5) 0.0894(4) 0.0440(11) Uani 1 1 d . . . . .
H1'A H 0.342644 0.560804 0.134664 0.053 Uiso 1 1 calc R . . . .
H1'B H 0.493898 0.612740 0.038658 0.053 Uiso 1 1 calc R . . . .
H12A H 0.369(6) 1.039(5) 0.199(4) 0.031(11) Uiso 1 1 d . . . . .
H12B H 0.507(6) 1.125(5) 0.235(4) 0.032(12) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C1 119.1(3) . . ?
C7 O5 H5 109.5 . . ?
C11 O9 C3' 116.2(3) . . ?
C5 O3 H3 109.5 . . ?
C6 O4 H4 109.5 . . ?
C14 O8 C1' 116.3(3) . . ?
O2 C3 C13 121.0(3) . . ?
C4 C3 O2 126.1(3) . . ?
C4 C3 C13 112.9(3) . . ?
C9 C10 C4 116.3(3) . . ?
C5 C10 C4 125.0(3) . . ?
C5 C10 C9 118.7(3) . . ?
C3 C4 C10 119.6(3) . . ?
C3 C4 C11 110.6(3) . . ?
C10 C4 C11 129.8(3) . . ?
O5 C7 C6 121.2(3) . . ?
O5 C7 C8 118.1(3) . . ?
C6 C7 C8 120.7(3) . . ?
O2 C1 C9 117.1(3) . . ?
O005 C1 O2 116.5(3) . . ?
O005 C1 C9 126.4(3) . . ?
C10 C9 C1 121.7(3) . . ?
C8 C9 C10 121.4(3) . . ?
C8 C9 C1 116.8(3) . . ?
O9 C11 C4 111.7(3) . . ?
O9 C11 C14 104.0(3) . . ?
O9 C11 C12 115.2(3) . . ?
C4 C11 C14 113.3(3) . . ?
C4 C11 C12 104.4(3) . . ?
C14 C11 C12 108.6(3) . . ?
O3 C5 C10 124.0(3) . . ?
O3 C5 C6 116.4(3) . . ?
C6 C5 C10 119.6(3) . . ?
O4 C6 C7 116.4(3) . . ?
O4 C6 C5 122.9(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C8 C9 118.8(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
O6 C13 C3 126.5(3) . . ?
O6 C13 C12 126.8(3) . . ?
C3 C13 C12 106.7(3) . . ?
O8 C14 C11 110.6(3) . . ?
O7 C14 O8 126.8(4) . . ?
O7 C14 C11 122.6(4) . . ?
C11 C12 H12A 111(3) . . ?
C11 C12 H12B 108(3) . . ?
C13 C12 C11 105.4(3) . . ?
C13 C12 H12A 109(3) . . ?
C13 C12 H12B 111(2) . . ?
H12A C12 H12B 112(4) . . ?
O9 C3' H3'A 110.2 . . ?
O9 C3' H3'B 110.2 . . ?
O9 C3' C4' 107.6(3) . . ?
H3'A C3' H3'B 108.5 . . ?
C4' C3' H3'A 110.2 . . ?
C4' C3' H3'B 110.2 . . ?
C3' C4' H4'A 109.5 . . ?
C3' C4' H4'B 109.5 . . ?
C3' C4' H4'C 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C1' C2' H2'A 109.5 . . ?
C1' C2' H2'B 109.5 . . ?
C1' C2' H2'C 109.5 . . ?
O8 C1' C2' 111.4(4) . . ?
O8 C1' H1'A 109.4 . . ?
O8 C1' H1'B 109.4 . . ?
C2' C1' H1'A 109.4 . . ?
C2' C1' H1'B 109.4 . . ?
H1'A C1' H1'B 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.352(4) . ?
O2 C1 1.397(4) . ?
O5 H5 0.8200 . ?
O5 C7 1.359(4) . ?
O6 C13 1.218(4) . ?
O9 C11 1.429(4) . ?
O9 C3' 1.452(5) . ?
O005 C1 1.196(4) . ?
O3 H3 0.8200 . ?
O3 C5 1.370(4) . ?
O4 H4 0.8200 . ?
O4 C6 1.355(4) . ?
O8 C14 1.307(5) . ?
O8 C1' 1.477(5) . ?
O7 C14 1.205(5) . ?
C3 C4 1.344(5) . ?
C3 C13 1.462(5) . ?
C10 C4 1.442(5) . ?
C10 C9 1.410(5) . ?
C10 C5 1.407(5) . ?
C4 C11 1.517(5) . ?
C7 C6 1.389(5) . ?
C7 C8 1.392(5) . ?
C1 C9 1.476(4) . ?
C9 C8 1.394(5) . ?
C11 C14 1.546(5) . ?
C11 C12 1.559(5) . ?
C5 C6 1.396(5) . ?
C8 H8 0.9300 . ?
C13 C12 1.518(5) . ?
C12 H12A 0.94(5) . ?
C12 H12B 1.02(5) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.495(6) . ?
C4' H4'A 0.9600 . ?
C4' H4'B 0.9600 . ?
C4' H4'C 0.9600 . ?
C2' H2'A 0.9600 . ?
C2' H2'B 0.9600 . ?
C2' H2'C 0.9600 . ?
C2' C1' 1.478(7) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306192
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 34.4 18.1 ?
