#------------------------------------------------------------------------------
#$Date: 2025-07-03 12:18:25 +0300 (Thu, 03 Jul 2025) $
#$Revision: 300305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573684.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_1573684
loop_
_publ_author_name
'Culver, Shawn'
'Rhoad, Jonathan S.'
_journal_coeditor_code           HB4504
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x250016
_journal_paper_doi               10.1107/S2414314625000161
_journal_volume                  10
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C13 H18 O9'
_chemical_formula_moiety         'C13 H18 O9'
_chemical_formula_sum            'C13 H18 O9'
_chemical_formula_weight         318.27
_chemical_name_systematic
;
Acetyl α-D-2,3,4-triacetyllyxopyranoside
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                90
_cell_angle_beta                 109.7341(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1174(3)
_cell_length_b                   9.5597(4)
_cell_length_c                   10.2580(4)
_cell_measurement_reflns_used    5073
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.98
_cell_measurement_theta_min      6.52
_cell_volume                     749.27(5)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick 2008)
;
_computing_structure_refinement
;
SHELXL2019/1 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5524
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         70.081
_diffrn_reflns_theta_min         6.516
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.245
_refine_ls_abs_structure_details
;
Flack x determined using 630 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019/1 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2107
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0317
_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)+(0.0444P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0757
_reflns_number_gt                2081
_reflns_number_total             2107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4504.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1573684
#BEGIN Tags that were not found in dictionaries:
_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_min   0.818
_shelx_estimated_absorpt_t_max   0.954
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.12797(18) 0.61079(17) 0.65441(14) 0.0265(4) Uani d 1 . .
O O2 0.18123(17) 0.40848(17) 0.55297(15) 0.0261(4) Uani d 1 . .
O O3 0.05956(18) 0.56065(17) 0.31122(15) 0.0278(4) Uani d 1 . .
O O4 -0.2996(2) 0.45517(19) 0.21466(16) 0.0335(4) Uani d 1 . .
O O5 -0.14941(18) 0.37458(16) 0.58585(15) 0.0267(4) Uani d 1 . .
O O6 -0.1547(2) 0.5135(2) 0.84634(17) 0.0396(4) Uani d 1 . .
O O7 0.4179(2) 0.5469(2) 0.5983(2) 0.0458(5) Uani d 1 . .
O O8 -0.1219(2) 0.7203(2) 0.17276(16) 0.0374(4) Uani d 1 . .
O O9 -0.2878(4) 0.2352(3) 0.1434(2) 0.0698(7) Uani d 1 . .
C C1 -0.0355(3) 0.4874(2) 0.6386(2) 0.0249(5) Uani d 1 . .
H H1 0.038(3) 0.457(3) 0.730(3) 0.025(6) Uiso d 1 . .
C C2 0.0676(2) 0.5270(2) 0.5439(2) 0.0237(4) Uani d 1 . .
H H2 0.138(3) 0.606(3) 0.571(3) 0.020(5) Uiso d 1 . .
C C3 -0.0509(3) 0.5479(2) 0.3942(2) 0.0244(4) Uani d 1 . .
H H3 -0.117(3) 0.631(3) 0.386(2) 0.018(5) Uiso d 1 . .
C C4 -0.1710(3) 0.4228(3) 0.3476(2) 0.0260(5) Uani d 1 . .
H H4 -0.103(3) 0.344(3) 0.343(2) 0.020(6) Uiso d 1 . .
C C5 -0.2688(3) 0.3961(3) 0.4481(2) 0.0273(5) Uani d 1 . .
H H5A -0.342(3) 0.470(3) 0.446(2) 0.017(6) Uiso d 1 . .
H H5B -0.336(3) 0.315(3) 0.427(3) 0.021(6) Uiso d 1 . .
C C6 -0.1753(3) 0.6122(3) 0.7703(2) 0.0285(5) Uani d 1 . .
C C7 -0.2522(4) 0.7496(3) 0.7883(3) 0.0381(6) Uani d 1 . .
H H7A -0.211(2) 0.7748(15) 0.880(5) 0.075(12) Uiso d 1 . .
H H7B -0.232(7) 0.826(6) 0.730(6) 0.093(15) Uiso d 1 . .
H H7C -0.369(8) 0.738(7) 0.761(6) 0.104(18) Uiso d 1 . .
C C8 0.3551(3) 0.4327(3) 0.5903(2) 0.0267(5) Uani d 1 . .
C C9 0.4529(3) 0.2978(3) 0.6181(2) 0.0305(5) Uani d 1 . .
H H9A 0.414(4) 0.237(4) 0.535(4) 0.050(9) Uiso d 1 . .
H H9B 0.428(4) 0.251(4) 0.691(3) 0.034(7) Uiso d 1 . .
H H9C 0.579(4) 0.312(4) 0.648(3) 0.045(8) Uiso d 1 . .
C C10 0.0097(3) 0.6518(3) 0.2030(2) 0.0301(5) Uani d 1 . .
C C11 0.1387(4) 0.6508(4) 0.1280(3) 0.0423(6) Uani d 1 . .
H H11A 0.246(5) 0.623(5) 0.185(4) 0.051(9) Uiso d 1 . .
H H11B 0.141(7) 0.742(7) 0.088(6) 0.092(15) Uiso d 1 . .
H H11C 0.090(5) 0.577(5) 0.045(4) 0.060(10) Uiso d 1 . .
C C12 -0.3453(3) 0.3515(3) 0.1204(2) 0.0394(6) Uani d 1 . .
C C13 -0.4761(4) 0.4017(5) -0.0120(3) 0.0540(9) Uani d 1 . .
H H13A -0.544(7) 0.482(7) 0.009(5) 0.092(16) Uiso d 1 . .
H H13B -0.546(6) 0.333(6) -0.055(5) 0.074(13) Uiso d 1 . .
H H13C -0.410(6) 0.421(6) -0.067(5) 0.074(12) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C1 . . 114.64(16) ?
C8 O2 C2 . . 117.83(18) ?
C10 O3 C3 . . 117.73(17) ?
C12 O4 C4 . . 117.2(2) ?
C1 O5 C5 . . 114.06(16) ?
O5 C1 O1 . . 111.88(15) ?
O5 C1 C2 . . 112.09(17) ?
O1 C1 C2 . . 106.69(17) ?
O5 C1 H1 . . 104.6(17) ?
O1 C1 H1 . . 108.5(16) ?
C2 C1 H1 . . 113.1(15) ?
O2 C2 C3 . . 109.81(16) ?
O2 C2 C1 . . 103.86(16) ?
C3 C2 C1 . . 112.22(16) ?
O2 C2 H2 . . 107.6(16) ?
C3 C2 H2 . . 108.1(15) ?
C1 C2 H2 . . 115.0(15) ?
O3 C3 C4 . . 110.17(17) ?
O3 C3 C2 . . 107.51(15) ?
C4 C3 C2 . . 109.53(17) ?
O3 C3 H3 . . 109.2(15) ?
C4 C3 H3 . . 110.3(15) ?
C2 C3 H3 . . 110.1(14) ?
O4 C4 C3 . . 108.18(18) ?
O4 C4 C5 . . 107.47(16) ?
C3 C4 C5 . . 110.29(17) ?
O4 C4 H4 . . 111.8(15) ?
C3 C4 H4 . . 108.6(15) ?
C5 C4 H4 . . 110.5(15) ?
O5 C5 C4 . . 111.03(16) ?
O5 C5 H5A . . 110.3(15) ?
C4 C5 H5A . . 109.7(15) ?
O5 C5 H5B . . 105.0(15) ?
C4 C5 H5B . . 112.4(15) ?
H5A C5 H5B . . 108(2) ?
O6 C6 O1 . . 122.7(2) ?
O6 C6 C7 . . 125.7(2) ?
O1 C6 C7 . . 111.6(2) ?
C6 C7 H7A . . 109.7 ?
C6 C7 H7B . . 114(3) ?
H7A C7 H7B . . 110.1 ?
C6 C7 H7C . . 107(4) ?
H7A C7 H7C . . 109.4 ?
H7B C7 H7C . . 106(5) ?
O7 C8 O2 . . 123.8(2) ?
O7 C8 C9 . . 126.10(19) ?
O2 C8 C9 . . 110.1(2) ?
C8 C9 H9A . . 110(2) ?
C8 C9 H9B . . 109(2) ?
H9A C9 H9B . . 108(3) ?
C8 C9 H9C . . 112(2) ?
H9A C9 H9C . . 110(3) ?
H9B C9 H9C . . 107(3) ?
O8 C10 O3 . . 123.6(2) ?
O8 C10 C11 . . 126.0(2) ?
O3 C10 C11 . . 110.4(2) ?
C10 C11 H11A . . 111(2) ?
C10 C11 H11B . . 109(3) ?
H11A C11 H11B . . 113(4) ?
C10 C11 H11C . . 106(2) ?
H11A C11 H11C . . 109(3) ?
H11B C11 H11C . . 108(4) ?
O9 C12 O4 . . 123.2(2) ?
O9 C12 C13 . . 126.0(3) ?
O4 C12 C13 . . 110.8(3) ?
C12 C13 H13A . . 109(3) ?
C12 C13 H13B . . 111(3) ?
H13A C13 H13B . . 112(4) ?
C12 C13 H13C . . 104(3) ?
H13A C13 H13C . . 117(5) ?
H13B C13 H13C . . 104(4) ?
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 C6 . 1.367(3) ?
O1 C1 . 1.437(3) ?
O2 C8 . 1.352(3) ?
O2 C2 . 1.444(2) ?
O3 C10 . 1.361(3) ?
O3 C3 . 1.435(2) ?
O4 C12 . 1.346(3) ?
O4 C4 . 1.443(2) ?
O5 C1 . 1.405(3) ?
O5 C5 . 1.433(2) ?
O6 C6 . 1.199(3) ?
O7 C8 . 1.196(3) ?
O8 C10 . 1.201(3) ?
O9 C12 . 1.198(4) ?
C1 C2 . 1.528(3) ?
C1 H1 . 0.97(3) ?
C2 C3 . 1.525(3) ?
C2 H2 . 0.94(3) ?
C3 C4 . 1.515(3) ?
C3 H3 . 0.94(3) ?
C4 C5 . 1.520(3) ?
C4 H4 . 0.95(3) ?
C5 H5A . 0.92(3) ?
C5 H5B . 0.94(3) ?
C6 C7 . 1.493(4) ?
C7 H7A . 0.91(5) ?
C7 H7B . 0.99(6) ?
C7 H7C . 0.90(6) ?
C8 C9 . 1.491(3) ?
C9 H9A . 0.99(4) ?
C9 H9B . 0.95(3) ?
C9 H9C . 0.97(3) ?
C10 C11 . 1.494(3) ?
C11 H11A . 0.91(4) ?
C11 H11B . 0.96(7) ?
C11 H11C . 1.07(4) ?
C12 C13 . 1.493(4) ?
C13 H13A . 1.01(6) ?
C13 H13B . 0.89(6) ?
C13 H13C . 0.92(5) ?
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
_geom_hbond_publ_flag
C1 H1 O8 2_546 0.97(3) 2.47(3) 3.198(3) 132(2) yes
C5 H5B O7 2_546 0.94(3) 2.63(3) 3.528(3) 160(2) yes
C9 H9C O5 1_655 0.97(3) 2.57(3) 3.434(3) 149(3) yes
C11 H11C O6 1_554 1.07(4) 2.39(4) 3.331(3) 145(3) yes
C13 H13C O6 1_554 0.92(5) 2.66(5) 3.554(4) 162(4) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O5 C1 O1 . . . . 64.6(2) ?
C5 O5 C1 C2 . . . . -55.2(2) ?
C6 O1 C1 O5 . . . . 79.4(2) ?
C6 O1 C1 C2 . . . . -157.64(16) ?
C8 O2 C2 C3 . . . . 114.69(18) ?
C8 O2 C2 C1 . . . . -125.12(17) ?
O5 C1 C2 O2 . . . . -67.48(19) ?
O1 C1 C2 O2 . . . . 169.73(14) ?
O5 C1 C2 C3 . . . . 51.1(2) ?
O1 C1 C2 C3 . . . . -71.7(2) ?
C10 O3 C3 C4 . . . . 97.3(2) ?
C10 O3 C3 C2 . . . . -143.44(18) ?
O2 C2 C3 O3 . . . . -55.3(2) ?
C1 C2 C3 O3 . . . . -170.28(18) ?
O2 C2 C3 C4 . . . . 64.4(2) ?
C1 C2 C3 C4 . . . . -50.6(2) ?
C12 O4 C4 C3 . . . . 141.0(2) ?
C12 O4 C4 C5 . . . . -99.9(2) ?
O3 C3 C4 O4 . . . . -71.1(2) ?
C2 C3 C4 O4 . . . . 170.86(16) ?
O3 C3 C4 C5 . . . . 171.64(17) ?
C2 C3 C4 C5 . . . . 53.6(2) ?
C1 O5 C5 C4 . . . . 58.9(2) ?
O4 C4 C5 O5 . . . . -175.16(18) ?
C3 C4 C5 O5 . . . . -57.5(2) ?
C1 O1 C6 O6 . . . . -6.1(3) ?
C1 O1 C6 C7 . . . . 173.50(18) ?
C2 O2 C8 O7 . . . . -10.3(3) ?
C2 O2 C8 C9 . . . . 170.07(16) ?
C3 O3 C10 O8 . . . . -0.8(3) ?
C3 O3 C10 C11 . . . . -179.63(19) ?
C4 O4 C12 O9 . . . . 1.9(4) ?
C4 O4 C12 C13 . . . . -178.94(19) ?
