Dicarboxylate and dicarboxylic acid appended supramolecular self-associating amphiphiles as antimicrobial agents against high priority bacterial pathogens.
White, Lisa J.; Streather, Bree; Sutton, J. Mark; Rankin, Jennifer; Baker, Jennifer; Bennett, Charlotte; Wilson, Hollie B.; Hind, Charlotte K.; Hiscock, Jennifer R.; Organic & biomolecular chemistry  (2025) –; doi:10.1039/d5ob01615k

data_7160871
_publ_section_title
;
 Dicarboxylate and dicarboxylic acid appended supramolecular
 self-associating amphiphiles as antimicrobial agents against high
 priority bacterial pathogens.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d5ob01615k
_journal_year                    2025
_chemical_formula_moiety         'C13 H16 N2 O6'
_chemical_formula_sum            'C13 H16 N2 O6'
_chemical_formula_weight         296.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.642(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.123(3)
_cell_length_b                   6.2205(5)
_cell_length_c                   7.7852(7)
_cell_measurement_reflns_used    1603
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      71.5080
_cell_measurement_theta_min      6.5010
_cell_volume                     1313.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_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   -111.00 -20.00   1.00   12.50    --  -41.91 -57.00-150.00   91
  2  \w    -68.00  30.00   1.00   12.50    --  -41.91  57.00   0.00   98
  3  \w    -62.00  31.00   1.00   12.50    --  -41.91  57.00 120.00   93
  4  \w     47.00  73.00   1.00   12.50    --   41.91 -77.00  90.00   26
  5  \w     97.00 147.00   1.00   22.50    --  103.72 125.00 -60.00   50
  6  \w    103.00 159.00   1.00   22.50    --  103.72  77.00  60.00   56
  7  \w     39.00 122.00   1.00   22.50    --  103.72 -45.00   0.00   83
  8  \w    136.00 177.00   1.00   22.50    --  103.72  45.00   0.00   41
  9  \w     44.00 105.00   1.00   22.50    --  103.72 -94.00   0.00   61
 10  \w     81.00 106.00   1.00   22.50    --  103.72 -94.00  60.00   25
 11  \w     32.00 126.00   1.00   22.50    --  103.72 -61.00-150.00   94
 12  \w     86.00 164.00   1.00   22.50    --  103.72  45.00  30.00   78
 13  \w    113.00 173.00   1.00   22.50    --  103.72 125.00 -90.00   60
 14  \w     50.00 108.00   1.00   22.50    --  103.72-125.00-120.00   58
 15  \w    108.00 158.00   1.00   22.50    --  103.72  45.00 -60.00   50
 16  \w     82.00 121.00   1.00   22.50    --  103.72  45.00   0.00   39
 17  \w    148.00 173.00   1.00   22.50    --  103.72 125.00-150.00   25
 18  \w     78.00 108.00   1.00   22.50    --  103.72-103.00 -89.58   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0529600000
_diffrn_orient_matrix_UB_12      -0.0174444000
_diffrn_orient_matrix_UB_13      -0.0682082000
_diffrn_orient_matrix_UB_21      -0.0087151000
_diffrn_orient_matrix_UB_22      0.2008040000
_diffrn_orient_matrix_UB_23      -0.1122296000
_diffrn_orient_matrix_UB_31      0.0185675000
_diffrn_orient_matrix_UB_32      0.1438163000
_diffrn_orient_matrix_UB_33      0.1480991000
_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  0.0941
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.953
_diffrn_reflns_theta_min         4.892
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.1379
_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/[\s^2^(Fo^2^)+(0.1819P)^2^+13.2416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3935
_refine_ls_wR_factor_ref         0.4113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1800
_reflns_number_total             2539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01615k2.cif
_cod_data_source_block           2024jrh0015_mono
_cod_database_code               7160871
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2F2
_chemical_oxdiff_usercomment     '150K 34-2'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.851
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C7(H7), C4(H4), C3(H3A), C6(H6A)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_shelx_res_checksum              39393
_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 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.790