# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2467225'
loop_
_audit_author_name
_audit_author_address
'Tomoko Takashita'
;Kagawa University
Japan
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2026-05-04 downloaded from the CCDC.
;
_audit_creation_date             2023-07-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        D,L-tagatose
_chemical_formula_moiety         'C6 H12 O6'
_chemical_formula_sum            'C6 H12 O6'
_chemical_formula_weight         180.16
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.11340(10)
_cell_length_b                   9.4936(2)
_cell_length_c                   10.4731(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.067(7)
_cell_angle_gamma                90
_cell_volume                     785.81(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8307
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.34
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384.0
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8575
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         5.598
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1313
_reflns_number_total             1433
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.119
_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)+(0.0449P)²+0.2689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00D,H00E)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O004(H004), O005(H005), O006(H006)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.54464(13) 0.59950(10) 0.81973(9) 0.0251(3) Uani 1 1 d . . . . .
H001 H 0.514634 0.521525 0.839413 0.038 Uiso 1 1 calc R U . . .
O002 O 0.57669(13) 0.68612(11) 0.49343(9) 0.0277(3) Uani 1 1 d . . . . .
H002 H 0.547217 0.752758 0.443691 0.042 Uiso 1 1 calc R U . . .
O003 O 0.58602(12) 0.84128(9) 0.66812(10) 0.0243(3) Uani 1 1 d . . . . .
O004 O 0.86735(13) 0.49428(11) 0.82647(10) 0.0294(3) Uani 1 1 d . . . . .
H004 H 0.898988 0.426781 0.789401 0.044 Uiso 1 1 calc R U . . .
O005 O 0.26366(13) 0.82648(12) 0.50237(10) 0.0319(3) Uani 1 1 d . . . . .
H005 H 0.229623 0.889250 0.543665 0.048 Uiso 1 1 calc R U . . .
O006 O 1.03173(12) 0.76202(12) 0.78936(11) 0.0337(3) Uani 1 1 d . . . . .
H006 H 1.087858 0.721878 0.854070 0.051 Uiso 1 1 calc R U . . .
C007 C 0.79591(17) 0.59832(14) 0.73177(14) 0.0214(3) Uani 1 1 d . . . . .
H007 H 0.834616 0.581086 0.651033 0.026 Uiso 1 1 calc R U . . .
C008 C 0.60290(17) 0.58939(14) 0.70153(13) 0.0197(3) Uani 1 1 d . . . . .
H008 H 0.566912 0.498972 0.659173 0.024 Uiso 1 1 calc R U . . .
C009 C 0.52502(17) 0.70910(14) 0.61003(13) 0.0208(3) Uani 1 1 d . . . . .
C00A C 0.76629(18) 0.85644(15) 0.69237(16) 0.0272(4) Uani 1 1 d . . . . .
H00A H 0.798363 0.948315 0.730492 0.033 Uiso 1 1 calc R U . . .
H00B H 0.801544 0.850971 0.609972 0.033 Uiso 1 1 calc R U . . .
C00B C 0.85628(17) 0.74279(15) 0.78456(14) 0.0236(3) Uani 1 1 d . . . . .
H00C H 0.834342 0.755742 0.872067 0.028 Uiso 1 1 calc R U . . .
C00C C 0.33385(18) 0.71518(16) 0.58961(15) 0.0286(4) Uani 1 1 d . . . . .
H00D H 0.285648 0.626117 0.554012 0.034 Uiso 1 1 calc R U . . .
H00E H 0.304323 0.729430 0.673401 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O001 H001 0.8200 . ?
O001 C008 1.4247(17) . ?
O002 H002 0.8200 . ?
O002 C009 1.3950(17) . ?
O003 C009 1.4330(15) . ?
O003 C00A 1.4340(16) . ?
O004 H004 0.8200 . ?
O004 C007 1.4266(16) . ?
O005 H005 0.8200 . ?
O005 C00C 1.4284(18) . ?
O006 H006 0.8200 . ?
O006 C00B 1.4247(16) . ?
C007 H007 0.9800 . ?
C007 C008 1.5282(19) . ?
C007 C00B 1.5179(19) . ?
C008 H008 0.9800 . ?
C008 C009 1.5281(18) . ?
C009 C00C 1.5182(19) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00B 1.520(2) . ?
C00B H00C 0.9800 . ?
C00C H00D 0.9700 . ?
C00C H00E 0.9700 . ?

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
C008 O001 H001 109.5 . . ?
C009 O002 H002 109.5 . . ?
C009 O003 C00A 113.80(10) . . ?
C007 O004 H004 109.5 . . ?
C00C O005 H005 109.5 . . ?
C00B O006 H006 109.5 . . ?
O004 C007 H007 109.0 . . ?
O004 C007 C008 109.99(11) . . ?
O004 C007 C00B 108.99(11) . . ?
C008 C007 H007 109.0 . . ?
C00B C007 H007 109.0 . . ?
C00B C007 C008 110.90(11) . . ?
O001 C008 C007 110.00(11) . . ?
O001 C008 H008 109.2 . . ?
O001 C008 C009 108.87(11) . . ?
C007 C008 H008 109.2 . . ?
C009 C008 C007 110.35(11) . . ?
C009 C008 H008 109.2 . . ?
O002 C009 O003 111.42(11) . . ?
O002 C009 C008 105.62(11) . . ?
O002 C009 C00C 112.47(11) . . ?
O003 C009 C008 109.32(10) . . ?
O003 C009 C00C 105.68(11) . . ?
C00C C009 C008 112.40(11) . . ?
O003 C00A H00A 109.3 . . ?
O003 C00A H00B 109.3 . . ?
O003 C00A C00B 111.43(11) . . ?
H00A C00A H00B 108.0 . . ?
C00B C00A H00A 109.3 . . ?
C00B C00A H00B 109.3 . . ?
O006 C00B C007 111.48(12) . . ?
O006 C00B C00A 105.31(11) . . ?
O006 C00B H00C 110.0 . . ?
C007 C00B C00A 109.93(11) . . ?
C007 C00B H00C 110.0 . . ?
C00A C00B H00C 110.0 . . ?
O005 C00C C009 111.42(12) . . ?
O005 C00C H00D 109.3 . . ?
O005 C00C H00E 109.3 . . ?
C009 C00C H00D 109.3 . . ?
C009 C00C H00E 109.3 . . ?
H00D C00C H00E 108.0 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C008 C009 O002 -175.50(10) . . . . ?
O001 C008 C009 O003 64.51(13) . . . . ?
O001 C008 C009 C00C -52.50(14) . . . . ?
O002 C009 C00C O005 -60.12(15) . . . . ?
O003 C009 C00C O005 61.66(14) . . . . ?
O003 C00A C00B O006 174.40(11) . . . . ?
O003 C00A C00B C007 54.19(16) . . . . ?
O004 C007 C008 O001 54.57(14) . . . . ?
O004 C007 C008 C009 174.71(11) . . . . ?
O004 C007 C00B O006 70.03(14) . . . . ?
O004 C007 C00B C00A -173.58(11) . . . . ?
C007 C008 C009 O002 63.69(13) . . . . ?
C007 C008 C009 O003 -56.30(14) . . . . ?
C007 C008 C009 C00C -173.32(11) . . . . ?
C008 C007 C00B O006 -168.75(11) . . . . ?
C008 C007 C00B C00A -52.36(15) . . . . ?
C008 C009 C00C O005 -179.17(11) . . . . ?
C009 O003 C00A C00B -59.74(15) . . . . ?
C00A O003 C009 O002 -56.27(14) . . . . ?
C00A O003 C009 C008 60.09(14) . . . . ?
C00A O003 C009 C00C -178.72(11) . . . . ?
C00B C007 C008 O001 -66.06(14) . . . . ?
C00B C007 C008 C009 54.08(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
