Synthesis of zwitterionic asymmetric and symmetric carboxy-imidazolium derivatives and their use in molecular interactions with bovine serum albumin.
Sultanova, Elza D.; Bogdanov, Ilshat M.; Gromova, Nadezhda I.; Astrakhantseva, Anna V.; Kapralov, Mikhail A.; Nizamutdinov, Alexey S.; Mukhametzyanov, Timur A.; Islamov, Daut R.; Usachev, Konstantin S.; Serov, Nikita Y.; Burilov, Vladimir A.; Solovieva, Svetlana E.; Antipin, Igor S.; Organic & biomolecular chemistry 23 (2025) 1981–1994; doi:10.1039/d4ob01685h

data_7160341
_publ_section_title
;
 Synthesis of zwitterionic asymmetric and symmetric carboxy-imidazolium
 derivatives and their use in molecular interactions with bovine serum
 albumin.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1981
_journal_page_last               1994
_journal_paper_doi               10.1039/d4ob01685h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H26 N10 O8, 4(H2 O)'
_chemical_formula_sum            'C23 H34 N10 O12'
_chemical_formula_weight         642.60
_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     dual
_audit_creation_date             2024-10-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2025-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                64.644(2)
_cell_angle_beta                 82.453(2)
_cell_angle_gamma                80.303(2)
_cell_formula_units_Z            4
_cell_length_a                   13.9306(3)
_cell_length_b                   15.1094(3)
_cell_length_c                   15.4146(3)
_cell_measurement_reflns_used    23329
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9140
_cell_measurement_theta_min      3.2170
_cell_volume                     2883.67(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_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     82.00 176.00   0.50    0.27    --  103.80  77.00 -90.00  188
  2  \w    150.00 176.00   0.50    0.27    --  103.80  45.00  60.00   52
  3  \w     93.00 119.00   0.50    0.27    --  103.80  45.00  60.00   52
  4  \w    -26.00  22.00   0.50    0.07    --   46.19 -19.00-120.00   96
  5  \w     40.00  68.00   0.50    0.27    --  103.80 -61.00 -60.00   56
  6  \w    -14.00  17.00   0.50    0.07    --   46.19 -19.00 120.00   62
  7  \w     33.00  71.00   0.50    0.27    --  103.80 -61.00  90.00   76
  8  \w     71.00 102.00   0.50    0.27    --  103.80 -77.00  30.00   62
  9  \w     31.00  56.00   0.50    0.27    --  103.80 -77.00  30.00   50
 10  \w     44.00  69.00   0.50    0.27    --  103.80 -90.00  29.00   50
 11  \w     35.00  72.00   0.50    0.27    --  103.80 -94.00  90.00   74
 12  \w     52.00  79.00   0.50    0.27    --  103.80 -94.00 150.00   54
 13  \w     44.00  93.00   0.50    0.07    --   46.19-125.00-150.00   98
 14  \w     81.00 106.00   0.50    0.27    --  103.80 -94.00-150.00   50
 15  \w    -25.00  73.00   0.50    0.07    --   46.19 -90.00  29.00  196
 16  \w     79.00 106.00   0.50    0.27    --  103.80 -94.00  90.00   54
 17  \w     81.00 107.00   0.50    0.07    --   46.19 125.00 -90.00   52
 18  \w     79.00 157.00   0.50    0.27    --  103.80  90.00 144.00  156
 19  \w     74.00 100.00   0.50    0.07    --   46.19 125.00  60.00   52
 20  \w     81.00 109.00   0.50    0.07    --   46.19 125.00  30.00   56
 21  \w    -26.00  23.00   0.50    0.07    --  -47.44  19.00  60.00   98
 22  \w   -102.00 -77.00   0.50    0.27    -- -105.05  77.00  60.00   50
 23  \w    -73.00 -33.00   0.50    0.27    -- -105.05  77.00  60.00   80
 24  \w    -71.00 -41.00   0.50    0.27    -- -105.05  61.00  30.00   60
 25  \w    -76.00 -33.00   0.50    0.27    -- -105.05  77.00 -90.00   86
 26  \w    -71.00 -33.00   0.50    0.27    -- -105.05  61.00 -90.00   76
 27  \w    -38.00  14.00   0.50    0.07    --  -47.44  37.00 120.00  104
 28  \w    -74.00  23.00   0.50    0.07    --  -47.44  90.00 144.00  194
 29  \w   -127.00 -54.00   0.50    0.27    -- -105.05 146.00 128.35  146
 30  \w   -123.00 -91.00   0.50    0.27    -- -105.05 141.00 -81.50   64
 31  \w    -83.00 -33.00   0.50    0.27    -- -105.05 141.00 -81.50  100
 32  \w   -110.00 -33.00   0.50    0.27    -- -105.05 125.00 -90.00  154
 33  \w   -107.00 -60.00   0.50    0.27    -- -105.05 107.00 -92.16   94
 34  \w   -106.00 -71.00   0.50    0.27    -- -105.05 104.00  54.67   70
 35  \w    -63.00 -38.00   0.50    0.27    -- -105.05 104.00  54.67   50
 36  \w    -93.00 -68.00   0.50    0.27    -- -105.05  90.00 144.00   50
 37  \w   -172.00 -93.00   0.50    0.27    -- -105.05 -61.00  90.00  158
 38  \w   -174.00 -96.00   0.50    0.27    -- -105.05 -61.00 120.00  156
 39  \w   -125.00 -93.00   0.50    0.27    -- -105.05 -15.00   0.00   64
 40  \w   -173.00-131.00   0.50    0.27    -- -105.05 -15.00   0.00   84
 41  \w   -157.00-110.00   0.50    0.27    -- -105.05 -90.00  29.00   94
 42  \w   -164.00 -74.00   0.50    0.27    -- -105.05-125.00  90.00  180
 43  \w   -100.00 -74.00   0.50    0.07    --  -47.44-125.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1028870000
_diffrn_orient_matrix_UB_12      0.0213469000
_diffrn_orient_matrix_UB_13      0.0052420000
_diffrn_orient_matrix_UB_21      0.0066834000
_diffrn_orient_matrix_UB_22      -0.0854646000
_diffrn_orient_matrix_UB_23      0.1009231000
_diffrn_orient_matrix_UB_31      0.0448587000
_diffrn_orient_matrix_UB_32      -0.0719277000
_diffrn_orient_matrix_UB_33      -0.0455270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38113
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.622
_diffrn_reflns_theta_min         3.180
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       prism
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     851
_refine_ls_number_reflns         11616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0634P)^2^+1.2692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10074
_reflns_number_total             11616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01685h2.cif
_cod_data_source_block           burv852_corr
_cod_depositor_comments          'Adding full bibliography for 7160341.cif.'
_cod_database_code               7160341
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C23H34N10O12
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.726
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H,H) groups
2.a Free rotating group:
 O11(H11A,H11B), O43(H43A,H43B), O87(H87A,H87B), O89(H89A,H89B)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C45(H45A,H45B), C49(H49A,H49B), C57(H57A,H57B), C61(H61A,
 H61B), C63(H63A,H63B), C76(H76A,H76B), C80(H80A,H80B), C82(H82A,H82B),
 C10(H10A,H10B), C18(H18A,H18B), C28(H28A,H28B), C38(H38A,H38B), C47(H47A,H47B),
  C53(H53A,H53B), C60(H60A,H60B), C78(H78A,H78B), C84(H84A,H84B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C36(H36), C44(H44), C56(H56), C70(H70), C72(H72), C12(H12),
 C20(H20), C42(H42), C51(H51), C65(H65), C66(H66)
2.d Idealised tetrahedral OH refined as rotating group:
 O67(H67), O69(H69), O33(H33), O83(H83)
;
_shelx_res_checksum              86507
_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 1.680
_oxdiff_exptl_absorpt_empirical_full_min 0.673