#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/75/1557525.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_1557525
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         'C18 H16 O10, H2 O'
_chemical_formula_sum            'C18 H18 O11'
_chemical_formula_weight         410.32
_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             2019-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                107.857(6)
_cell_angle_beta                 90.985(5)
_cell_angle_gamma                111.419(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1273(5)
_cell_length_b                   9.5041(6)
_cell_length_c                   12.0575(9)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.1650
_cell_measurement_theta_min      2.4370
_cell_volume                     916.90(12)
_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      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -35.00  62.00   1.00    3.50    --  -11.59  57.00 -90.00   97
  2  ω    -75.00  14.00   1.00    3.50    --  -11.59 -57.00 120.00   89
  3  ω    -16.00  74.00   1.00    3.50    --   11.74  57.00  60.00   90
;
_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      0.0746090000
_diffrn_orient_matrix_UB_12      0.0314759000
_diffrn_orient_matrix_UB_13      0.0360055000
_diffrn_orient_matrix_UB_21      0.0392307000
_diffrn_orient_matrix_UB_22      0.0038376000
_diffrn_orient_matrix_UB_23      -0.0499154000
_diffrn_orient_matrix_UB_31      0.0037585000
_diffrn_orient_matrix_UB_32      0.0789951000
_diffrn_orient_matrix_UB_33      0.0107085000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5859
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.423
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72402
_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    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0467
_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)+(0.0445P)²+0.4355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2544
_reflns_number_total             3223
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b00877_si_004.cif
_cod_data_source_block           6t-5
_cod_original_cell_volume        916.91(11)
_cod_database_code               1557525
_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   0.990
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C13(H13A,H13B), 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), O4(H4), O2(H2)
;
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.567
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
O3 O 0.74847(15) 0.43471(16) 0.79304(13) 0.0246(4) Uani 1 1 d . . . . .
O5 O 0.97235(16) 0.99288(16) 0.86166(15) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.955343 1.074923 0.888547 0.046 Uiso 1 1 calc GR . . . .
O4 O 1.00367(16) 0.70926(17) 0.80124(15) 0.0306(4) Uani 1 1 d . . . . .
H4 H 1.059942 0.789766 0.787286 0.046 Uiso 1 1 calc GR . . . .
O1W O 0.93089(19) 1.26703(19) 0.93707(19) 0.0313(4) Uani 1 1 d . . . . .
O10 O 0.26977(17) 0.50841(19) 0.66908(14) 0.0363(4) Uani 1 1 d . . . . .
O6 O 0.64916(18) 0.18202(17) 0.78246(16) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.24027(17) 0.4695(2) 0.95155(14) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.145336 0.415818 0.927701 0.055 Uiso 1 1 calc GR . . . .
O1 O 0.33799(18) 0.78700(19) 0.93212(16) 0.0399(4) Uani 1 1 d . . . . .
O7 O 0.1907(2) -0.10822(18) 0.67969(15) 0.0421(5) Uani 1 1 d . . . . .
O8 O 0.3090(2) 0.08987(19) 0.60902(15) 0.0446(5) Uani 1 1 d . . . . .
O9 O 0.06788(18) 0.3472(2) 0.73140(16) 0.0453(5) Uani 1 1 d . . . . .
C10 C 0.5903(2) 0.5889(2) 0.84092(18) 0.0208(5) Uani 1 1 d . . . . .
C4 C 0.4543(2) 0.4520(2) 0.83757(18) 0.0214(5) Uani 1 1 d . . . . .
C5 C 0.7340(2) 0.5803(2) 0.81883(18) 0.0206(5) Uani 1 1 d . . . . .
C9 C 0.5678(2) 0.7319(2) 0.87090(19) 0.0215(5) Uani 1 1 d . . . . .
C7 C 0.8401(2) 0.8643(2) 0.85576(19) 0.0225(5) Uani 1 1 d . . . . .
C6 C 0.8617(2) 0.7172(2) 0.82334(19) 0.0224(5) Uani 1 1 d . . . . .
C11 C 0.4673(2) 0.3097(2) 0.81789(19) 0.0242(5) Uani 1 1 d . . . . .
C12 C 0.6225(2) 0.3020(2) 0.7978(2) 0.0256(5) Uani 1 1 d . . . . .
C8 C 0.6942(2) 0.8729(2) 0.87938(19) 0.0246(5) Uani 1 1 d . . . . .
H8 H 0.682069 0.970224 0.900218 0.030 Uiso 1 1 calc R . . . .
C14 C 0.2719(2) 0.0303(3) 0.6954(2) 0.0282(5) Uani 1 1 d . . . . .
C3 C 0.3166(2) 0.5064(3) 0.8597(2) 0.0258(5) Uani 1 1 d . . . . .
C15 C 0.2008(2) 0.4412(3) 0.7455(2) 0.0273(5) Uani 1 1 d . . . . .
C1 C 0.4025(2) 0.6964(3) 0.8929(2) 0.0264(5) Uani 1 1 d . . . . .
C13 C 0.3368(3) 0.1558(2) 0.8151(2) 0.0286(5) Uani 1 1 d . . . . .
H13A H 0.249975 0.180607 0.849144 0.034 Uiso 1 1 calc R . . . .
H13B H 0.376698 0.110706 0.864841 0.034 Uiso 1 1 calc R . . . .
C3' C 0.1697(3) 0.4786(3) 0.5629(2) 0.0434(6) Uani 1 1 d . . . . .
H3'A H 0.088132 0.521173 0.582441 0.052 Uiso 1 1 calc R . . . .
H3'B H 0.118280 0.364235 0.520647 0.052 Uiso 1 1 calc R . . . .
C1' C 0.2470(4) -0.0194(3) 0.4887(2) 0.0597(9) Uani 1 1 d . . . . .
H1'A H 0.317066 -0.074440 0.460685 0.072 Uiso 1 1 calc R . . . .
H1'B H 0.142815 -0.099331 0.486518 0.072 Uiso 1 1 calc R . . . .
C4' C 0.2742(4) 0.5598(4) 0.4899(3) 0.0605(8) Uani 1 1 d . . . . .
H4'A H 0.210825 0.550135 0.421495 0.091 Uiso 1 1 calc GR . . . .
H4'B H 0.348807 0.510646 0.465812 0.091 Uiso 1 1 calc GR . . . .
H4'C H 0.330837 0.671200 0.534940 0.091 Uiso 1 1 calc GR . . . .
C2' C 0.2353(5) 0.0691(4) 0.4141(3) 0.0861(12) Uani 1 1 d . . . . .
H2'A H 0.194713 -0.003135 0.334849 0.129 Uiso 1 1 calc GR . . . .
H2'B H 0.338686 0.147515 0.416070 0.129 Uiso 1 1 calc GR . . . .
H2'C H 0.164643 0.122137 0.441466 0.129 Uiso 1 1 calc GR . . . .
H1WA H 0.882(4) 1.277(4) 0.998(3) 0.078(12) Uiso 1 1 d . . . . .
H1WB H 0.876(4) 1.266(4) 0.884(3) 0.067(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 0.0033 0.0016 '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 0.0106 0.0060 '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
C5 O3 C12 120.08(16) . . ?
C7 O5 H5 109.5 . . ?
C6 O4 H4 109.5 . . ?
H1WA O1W H1WB 108(3) . . ?
C15 O10 C3' 117.13(18) . . ?
C3 O2 H2 109.5 . . ?
C14 O8 C1' 117.67(19) . . ?
C5 C10 C4 122.19(19) . . ?
C5 C10 C9 122.59(18) . . ?
C9 C10 C4 115.20(18) . . ?
C10 C4 C3 106.96(17) . . ?
C11 C4 C10 119.65(18) . . ?
C11 C4 C3 133.39(18) . . ?
O3 C5 C6 121.19(17) . . ?
C10 C5 O3 119.26(17) . . ?
C10 C5 C6 119.55(18) . . ?
C10 C9 C1 107.34(17) . . ?
C8 C9 C10 119.60(18) . . ?
C8 C9 C1 133.0(2) . . ?
O5 C7 C6 114.16(17) . . ?
O5 C7 C8 123.67(18) . . ?
C8 C7 C6 122.16(18) . . ?
O4 C6 C5 119.78(18) . . ?
O4 C6 C7 122.08(17) . . ?
C5 C6 C7 118.09(18) . . ?
C4 C11 C12 117.98(18) . . ?
C4 C11 C13 126.17(19) . . ?
C12 C11 C13 115.84(19) . . ?
O3 C12 C11 120.52(18) . . ?
O6 C12 O3 115.70(18) . . ?
O6 C12 C11 123.76(19) . . ?
C9 C8 C7 117.96(19) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
O7 C14 O8 123.6(2) . . ?
O7 C14 C13 123.8(2) . . ?
O8 C14 C13 112.60(18) . . ?
O2 C3 C4 113.46(18) . . ?
O2 C3 C15 112.10(17) . . ?
O2 C3 C1 110.00(18) . . ?
C4 C3 C15 110.02(18) . . ?
C4 C3 C1 102.56(15) . . ?
C15 C3 C1 108.17(17) . . ?
O10 C15 C3 109.95(17) . . ?
O9 C15 O10 126.3(2) . . ?
O9 C15 C3 123.8(2) . . ?
O1 C1 C9 129.3(2) . . ?
O1 C1 C3 123.36(18) . . ?
C9 C1 C3 107.25(18) . . ?
C11 C13 C14 115.64(19) . . ?
C11 C13 H13A 108.4 . . ?
C11 C13 H13B 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
O10 C3' H3'A 110.3 . . ?
O10 C3' H3'B 110.3 . . ?
O10 C3' C4' 107.0(2) . . ?
H3'A C3' H3'B 108.6 . . ?
C4' C3' H3'A 110.3 . . ?
C4' C3' H3'B 110.3 . . ?
O8 C1' H1'A 109.7 . . ?
O8 C1' H1'B 109.7 . . ?
H1'A C1' H1'B 108.2 . . ?
C2' C1' O8 109.6(2) . . ?
C2' C1' H1'A 109.7 . . ?
C2' C1' H1'B 109.7 . . ?
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 . . ?
C1' C2' H2'A 109.5 . . ?
C1' C2' H2'B 109.5 . . ?
C1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
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
O3 C5 1.378(2) . ?
O3 C12 1.380(2) . ?
O5 H5 0.8200 . ?
O5 C7 1.350(2) . ?
O4 H4 0.8200 . ?
O4 C6 1.351(2) . ?
O1W H1WA 0.86(4) . ?
O1W H1WB 0.80(3) . ?
O10 C15 1.319(3) . ?
O10 C3' 1.450(3) . ?
O6 C12 1.212(2) . ?
O2 H2 0.8200 . ?
O2 C3 1.386(3) . ?
O1 C1 1.201(3) . ?
O7 C14 1.203(3) . ?
O8 C14 1.325(3) . ?
O8 C1' 1.457(3) . ?
O9 C15 1.186(3) . ?
C10 C4 1.422(3) . ?
C10 C5 1.369(3) . ?
C10 C9 1.388(3) . ?
C4 C11 1.349(3) . ?
C4 C3 1.524(3) . ?
C5 C6 1.379(3) . ?
C9 C8 1.386(3) . ?
C9 C1 1.468(3) . ?
C7 C6 1.420(3) . ?
C7 C8 1.392(3) . ?
C11 C12 1.466(3) . ?
C11 C13 1.501(3) . ?
C8 H8 0.9300 . ?
C14 C13 1.501(3) . ?
C3 C15 1.531(3) . ?
C3 C1 1.595(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.479(4) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' C2' 1.433(4) . ?
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 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306193
