Stereoisomerism-dependent gelation and crystal structures of glycosylated <i>N</i>-methylbromomaleimide-based supramolecular hydrogels.
Yamashita, Kotoyo; Ito, Akitaka; Ishida, Masashi; Shintani, Yuki; Ikeda, Masato; Hadano, Shingo; Izumi, Masayuki; Ochi, Rika; Soft matter 21 (2025) 2124–2132; doi:10.1039/d4sm01325e

data_1573898
_publ_section_title
;
 Stereoisomerism-dependent gelation and crystal structures of glycosylated
 <i>N</i>-methylbromomaleimide-based supramolecular hydrogels.
;
_journal_issue                   11
_journal_name_full               'Soft matter'
_journal_page_first              2124
_journal_page_last               2132
_journal_paper_doi               10.1039/d4sm01325e
_journal_volume                  21
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H19 Br N2 O8, 3(H2 O)'
_chemical_formula_sum            'C17 H25 Br N2 O11'
_chemical_formula_weight         513.30
_chemical_name_systematic        alphaGal-AAB-Me
_chemical_properties_physical    Heat-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2025-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.231(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8648(7)
_cell_length_b                   4.7385(2)
_cell_length_c                   18.1370(10)
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      29.5480
_cell_measurement_theta_min      2.2210
_cell_volume                     1071.70(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -43.00  -9.00   0.50   34.27    --   12.72 -19.00 -60.00   68
  2  \w    -28.00   4.00   0.50   34.27    --   12.72 -97.00  19.00   64
  3  \w    -27.00  20.00   0.50   34.27    --  -13.34 -97.00  19.00   94
  4  \w    -20.00  25.00   0.50   34.27    --   12.72 -99.00 -90.00   90
  5  \w    -54.00  17.00   0.50   34.27    --  -13.34  97.00 127.00  142
  6  \w     56.00  92.00   0.50   34.27    --   12.72 178.00  60.00   72
  7  \w     45.00  85.00   0.50   34.27    --   12.72 178.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0211645000
_diffrn_orient_matrix_UB_12      -0.0409621000
_diffrn_orient_matrix_UB_13      -0.0383649000
_diffrn_orient_matrix_UB_21      -0.0129054000
_diffrn_orient_matrix_UB_22      -0.1346915000
_diffrn_orient_matrix_UB_23      0.0123285000
_diffrn_orient_matrix_UB_31      -0.0512027000
_diffrn_orient_matrix_UB_32      0.0509119000
_diffrn_orient_matrix_UB_33      0.0017405000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7763
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.980
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.639
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.3207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_full    0.746
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                3262
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sm01325e2.cif
_cod_data_source_block           alphagal-aab_nh-me_ph67_1
_cod_depositor_comments          'Adding full bibliography for 1573898.cif.'
_cod_database_code               1573898
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H19 Br N2 O8'
_diffrn_oxdiff_digest_frames
;
017d8e0f603cde739e7064f99b8f49a8b600610ef51
;
_diffrn_oxdiff_digest_hkl
;
01e046c2f2551db10a274839cc6e8ba43d0c58
;
_reflns_odcompleteness_completeness 99.84
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O002(H00O,H00Q), O007(H00S,H00T)
2.b Ternary CH refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00M(H00M), C00N(H00N), C00R(H00R)
2.c Secondary CH2 refined with riding coordinates:
 C00S(H00B,H00C)
2.d Aromatic/amide H refined with riding coordinates:
 N00D(H00D), C00E(H00E), C00I(H00I), C00K(H00K), C00P(H00P)
2.e Idealised Me refined as rotating group:
 C00V(H00G,H00H,H00L)
2.f Idealised tetrahedral OH refined as rotating group:
 O005(H005), O00A(H00A)
;
_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 1.077
_oxdiff_exptl_absorpt_empirical_full_min 0.930