#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227499.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_2227499
loop_
_publ_author_name
'Li, Wei'
'Bhadbhade, Mohan'
'Hook, James'
'Zhao, Jian'
_publ_section_title
;
 Dihydromyricetin hexaacetate
;
_journal_coeditor_code           HB5603
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2627
_journal_paper_doi               10.1107/S1600536810037578
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C27 H24 O14'
_chemical_formula_moiety         'C27 H24 O14'
_chemical_formula_sum            'C27 H24 O14'
_chemical_formula_weight         572.46
_chemical_melting_point_gt       436
_chemical_melting_point_lt       440
_chemical_name_common
;
(2RS,3RS)-3,5,7-triacetoxy-2-(3,4,5-
triacetoxyphenyl)-4H-1-benzopyran-4-one or
dihydromyricetin hexaacetate
;
_chemical_name_systematic
;
2,3-diacetoxy-5-[(2RS,3RS)-3,5,7-triacetoxy-
4-oxochromen-2-yl]phenyl acetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.8890(10)
_cell_angle_beta                 97.6000(10)
_cell_angle_gamma                109.0850(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7979(2)
_cell_length_b                   11.6652(3)
_cell_length_c                   16.2083(4)
_cell_measurement_reflns_used    7407
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.441
_cell_measurement_theta_min      2.454
_cell_volume                     1359.97(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT  (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD diffractometer'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16120
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.320
_refine_ls_extinction_coef       0.0070(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    90
_refine_ls_number_parameters     377
_refine_ls_number_reflns         5856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.5506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                4761
_reflns_number_total             5856
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5603.cif
_cod_data_source_block           I
_cod_database_code               2227499
_cod_database_fobs_code          2227499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.72782(15) 0.50439(9) 0.17597(6) 0.0248(2) Uani d . 1 . .
O O2 0.82930(16) 0.23522(10) 0.02789(7) 0.0285(3) Uani d . 1 . .
O O3 0.69164(15) 0.73102(9) -0.04552(6) 0.0249(2) Uani d . 1 . .
O O4 0.88884(16) 0.87775(10) 0.06016(7) 0.0332(3) Uani d . 1 . .
O O5 0.81318(15) 0.36393(9) -0.10513(6) 0.0243(2) Uani d . 1 . .
O O6 0.53693(17) 0.21507(11) -0.11517(8) 0.0395(3) Uani d . 1 . .
O O7 0.77402(16) 0.20741(10) 0.18599(7) 0.0276(3) Uani d . 1 . .
O O8 1.0734(2) 0.22913(14) 0.20952(9) 0.0503(4) Uani d . 1 . .
O O9 0.86595(16) 0.57686(10) 0.49672(6) 0.0275(3) Uani d . 1 . .
O O10 0.84901(17) 0.73527(11) 0.43165(7) 0.0320(3) Uani d . 1 . .
O O11 0.57423(16) 0.40577(11) 0.53218(6) 0.0275(3) Uani d . 1 . .
O O12 0.7581(2) 0.30683(15) 0.57861(8) 0.0540(4) Uani d . 1 . .
O O13 0.36896(15) 0.19986(10) 0.41469(7) 0.0294(3) Uani d . 1 . .
O O14 0.50639(19) 0.06354(12) 0.37879(10) 0.0475(4) Uani d . 1 . .
C C1 0.7183(2) 0.61969(13) 0.06911(9) 0.0220(3) Uani d . 1 . .
H H1 0.6996 0.6799 0.1083 0.026 Uiso calc R 1 . .
C C2 0.7256(2) 0.63424(13) -0.01355(9) 0.0206(3) Uani d . 1 . .
C C3 0.7503(2) 0.54634(13) -0.07242(9) 0.0213(3) Uani d . 1 . .
H H3 0.7523 0.5575 -0.1294 0.026 Uiso calc R 1 . .
C C4 0.77163(19) 0.44346(13) -0.04645(9) 0.0200(3) Uani d . 1 . .
C C5 0.76921(19) 0.42384(13) 0.03763(9) 0.0193(3) Uani d . 1 . .
C C6 0.8072(2) 0.32072(13) 0.07019(9) 0.0210(3) Uani d . 1 . .
C C7 0.8197(2) 0.32839(14) 0.16601(9) 0.0240(3) Uani d . 1 . .
H H7 0.9469 0.3811 0.1961 0.029 Uiso calc R 1 . .
C C8 0.6793(2) 0.38156(13) 0.19367(9) 0.0226(3) Uani d . 1 . .
H H8 0.5555 0.3313 0.1589 0.027 Uiso calc R 1 . .
C C9 0.7390(2) 0.51454(13) 0.09333(9) 0.0203(3) Uani d . 1 . .
C C10 0.7732(2) 0.84986(14) -0.00181(10) 0.0256(3) Uani d . 1 . .
C C11 0.6960(3) 0.93267(16) -0.04461(13) 0.0430(5) Uani d . 1 . .
H H11A 0.7555 1.0174 -0.0139 0.064 Uiso calc R 1 . .
H H11B 0.5628 0.9064 -0.0454 0.064 Uiso calc R 1 . .
H H11C 0.7187 0.9288 -0.1027 0.064 Uiso calc R 1 . .
C C12 0.6877(2) 0.24719(15) -0.13283(10) 0.0281(3) Uani d . 1 . .
C C13 0.7670(3) 0.17287(17) -0.18755(11) 0.0388(4) Uani d . 1 . .
H H13A 0.8635 0.1541 -0.1526 0.058 Uiso calc R 1 . .
H H13B 0.8201 0.2199 -0.2299 0.058 Uiso calc R 1 . .
H H13C 0.6693 0.0959 -0.2161 0.058 Uiso calc R 1 . .
C C14 0.9157(3) 0.16750(17) 0.20681(10) 0.0327(4) Uani d . 1 . .
C C15 0.8447(3) 0.04084(18) 0.22644(12) 0.0477(5) Uani d . 1 . .
H H15A 0.9488 0.0144 0.2444 0.072 Uiso calc R 1 . .
H H15B 0.7653 -0.0158 0.1759 0.072 Uiso calc R 1 . .
H H15C 0.7735 0.0405 0.2719 0.072 Uiso calc R 1 . .
C C16 0.6647(2) 0.38600(14) 0.28534(9) 0.0216(3) Uani d . 1 . .
C C17 0.7826(2) 0.48387(14) 0.34725(9) 0.0227(3) Uani d . 1 . .
H H17 0.8803 0.5474 0.3329 0.027 Uiso calc R 1 . .
C C18 0.7543(2) 0.48648(14) 0.42975(9) 0.0226(3) Uani d . 1 . .
C C19 0.6149(2) 0.39279(14) 0.45148(9) 0.0221(3) Uani d . 1 . .
C C20 0.5068(2) 0.29293(14) 0.39022(10) 0.0231(3) Uani d . 1 . .
C C21 0.5276(2) 0.29052(14) 0.30684(9) 0.0235(3) Uani d . 1 . .
H H21 0.4484 0.2239 0.2645 0.028 Uiso calc R 1 . .
C C22 0.9069(2) 0.69928(14) 0.49122(10) 0.0253(3) Uani d . 1 . .
C C23 1.0292(2) 0.77456(15) 0.57159(10) 0.0307(4) Uani d . 1 . .
H H23A 1.0586 0.8623 0.5690 0.046 Uiso calc R 1 . .
H H23B 1.1436 0.7560 0.5794 0.046 Uiso calc R 1 . .
H H23C 0.9659 0.7549 0.6192 0.046 Uiso calc R 1 . .
C C24 0.6593(2) 0.36239(15) 0.59285(10) 0.0282(3) Uani d . 1 . .
C C25 0.6109(3) 0.3970(2) 0.67600(11) 0.0462(5) Uani d . 1 . .
H H25A 0.4802 0.3516 0.6751 0.069 Uiso calc R 1 . .
H H25B 0.6337 0.4857 0.6866 0.069 Uiso calc R 1 . .
H H25C 0.6870 0.3765 0.7209 0.069 Uiso calc R 1 . .
C C26 0.3857(2) 0.08583(15) 0.40763(11) 0.0316(4) Uani d . 1 . .
C C27 0.2336(3) -0.00180(19) 0.43981(16) 0.0515(5) Uani d . 1 . .
H H27A 0.1167 -0.0205 0.4009 0.077 Uiso calc R 1 . .
H H27B 0.2249 0.0355 0.4959 0.077 Uiso calc R 1 . .
H H27C 0.2592 -0.0780 0.4438 0.077 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C8 . . 115.21(11) ?
C10 O3 C2 . . 120.74(12) ?
C12 O5 C4 . . 118.54(12) ?
C14 O7 C7 . . 116.89(13) ?
C22 O9 C18 . . 120.25(12) ?
C24 O11 C19 . . 118.70(12) ?
C26 O13 C20 . . 116.82(12) ?
C2 C1 C9 . . 117.87(13) ?
C2 C1 H1 . . 121.1 ?
C9 C1 H1 . . 121.1 ?
C1 C2 O3 . . 122.15(13) ?
C1 C2 C3 . . 122.11(13) ?
O3 C2 C3 . . 115.47(13) ?
C4 C3 C2 . . 118.70(13) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 O5 . . 116.72(13) ?
C3 C4 C5 . . 122.16(13) ?
O5 C4 C5 . . 120.86(13) ?
C9 C5 C4 . . 116.26(13) ?
C9 C5 C6 . . 119.47(13) ?
C4 C5 C6 . . 124.15(12) ?
O2 C6 C5 . . 125.38(13) ?
O2 C6 C7 . . 120.45(13) ?
C5 C6 C7 . . 114.16(12) ?
O7 C7 C8 . . 107.60(12) ?
O7 C7 C6 . . 109.39(12) ?
C8 C7 C6 . . 108.99(12) ?
O7 C7 H7 . . 110.3 ?
C8 C7 H7 . . 110.3 ?
C6 C7 H7 . . 110.3 ?
O1 C8 C16 . . 108.45(11) ?
O1 C8 C7 . . 107.80(12) ?
C16 C8 C7 . . 115.37(12) ?
O1 C8 H8 . . 108.3 ?
C16 C8 H8 . . 108.3 ?
C7 C8 H8 . . 108.3 ?
O1 C9 C1 . . 115.19(12) ?
O1 C9 C5 . . 121.95(13) ?
C1 C9 C5 . . 122.86(13) ?
O4 C10 O3 . . 123.10(14) ?
O4 C10 C11 . . 127.33(15) ?
O3 C10 C11 . . 109.57(13) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O6 C12 O5 . . 122.57(14) ?
O6 C12 C13 . . 127.38(16) ?
O5 C12 C13 . . 110.04(15) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O8 C14 O7 . . 122.91(17) ?
O8 C14 C15 . . 127.04(17) ?
O7 C14 C15 . . 110.04(17) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 C16 C17 . . 120.62(13) ?
C21 C16 C8 . . 117.82(13) ?
C17 C16 C8 . . 121.54(14) ?
C18 C17 C16 . . 118.70(14) ?
C18 C17 H17 . . 120.7 ?
C16 C17 H17 . . 120.7 ?
C17 C18 C19 . . 121.01(14) ?
C17 C18 O9 . . 123.72(14) ?
C19 C18 O9 . . 115.19(13) ?
C20 C19 C18 . . 119.42(13) ?
C20 C19 O11 . . 120.74(14) ?
C18 C19 O11 . . 119.56(13) ?
C21 C20 C19 . . 120.55(14) ?
C21 C20 O13 . . 121.56(14) ?
C19 C20 O13 . . 117.75(13) ?
C20 C21 C16 . . 119.51(14) ?
C20 C21 H21 . . 120.2 ?
C16 C21 H21 . . 120.2 ?
O10 C22 O9 . . 123.93(14) ?
O10 C22 C23 . . 127.63(15) ?
O9 C22 C23 . . 108.43(13) ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
O12 C24 O11 . . 122.55(15) ?
O12 C24 C25 . . 127.56(16) ?
O11 C24 C25 . . 109.88(14) ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O14 C26 O13 . . 122.89(16) ?
O14 C26 C27 . . 126.64(17) ?
O13 C26 C27 . . 110.47(15) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.3704(17) ?
O1 C8 . 1.4322(18) ?
O2 C6 . 1.2143(17) ?
O3 C10 . 1.3773(18) ?
O3 C2 . 1.3830(17) ?
O4 C10 . 1.1911(19) ?
O5 C12 . 1.3709(19) ?
O5 C4 . 1.3916(16) ?
O6 C12 . 1.196(2) ?
O7 C14 . 1.351(2) ?
O7 C7 . 1.4265(18) ?
O8 C14 . 1.197(2) ?
O9 C22 . 1.3743(19) ?
O9 C18 . 1.3867(18) ?
O10 C22 . 1.1910(19) ?
O11 C24 . 1.3525(19) ?
O11 C19 . 1.3886(17) ?
O12 C24 . 1.185(2) ?
O13 C26 . 1.371(2) ?
O13 C20 . 1.3941(18) ?
O14 C26 . 1.191(2) ?
C1 C2 . 1.377(2) ?
C1 C9 . 1.383(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.394(2) ?
C3 C4 . 1.370(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.410(2) ?
C5 C9 . 1.4072(19) ?
C5 C6 . 1.469(2) ?
C6 C7 . 1.533(2) ?
C7 C8 . 1.514(2) ?
C7 H7 . 1.0000 ?
C8 C16 . 1.5013(19) ?
C8 H8 . 1.0000 ?
C10 C11 . 1.486(2) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.494(2) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 C15 . 1.488(3) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C21 . 1.385(2) ?
C16 C17 . 1.397(2) ?
C17 C18 . 1.382(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.385(2) ?
C19 C20 . 1.383(2) ?
C20 C21 . 1.380(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.492(2) ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 C25 . 1.492(2) ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 C27 . 1.491(2) ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 O6 2_665 0.95 2.53 3.2847(19) 136
C8 H8 O3 2_665 1.00 2.33 3.2833(18) 158
C11 H11A O2 1_565 0.98 2.40 3.347(2) 161
C13 H13A O4 2_765 0.98 2.44 3.417(2) 176
C15 H15B O4 1_545 0.98 2.59 3.232(2) 124
C23 H23B Cg3 2_766 0.98 2.86 3.7598(18) 153
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10793198
