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_7160869
_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 H15 N2 O6, H2 O, C16 H36 N'
_chemical_formula_sum            'C29 H53 N3 O7'
_chemical_formula_weight         555.74
_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             2024-09-30
_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                93.880(3)
_cell_angle_beta                 95.670(3)
_cell_angle_gamma                100.995(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6519(3)
_cell_length_b                   9.5272(3)
_cell_length_c                   19.0975(7)
_cell_measurement_reflns_used    5988
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      71.7690
_cell_measurement_theta_min      4.6400
_cell_volume                     1531.68(9)
_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 0.975
_diffrn_measured_fraction_theta_max 1.000
_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    -63.00  25.00   1.00    4.00    --  -41.91  57.00-150.00   88
  2  \w    -86.00 -57.00   1.00    4.00    --  -41.91 125.00 -90.00   29
  3  \w    -65.00  31.00   1.00    4.00    --  -41.91  38.00   0.00   96
  4  \w   -114.00 -16.00   1.00    4.00    --  -41.91 -57.00  60.00   98
  5  \w     77.00 175.00   1.00   15.99    --  103.72  30.00   0.00   98
  6  \w     88.00 113.00   1.00   15.99    --  103.72-125.00 -30.00   25
  7  \w     79.00 173.00   1.00   15.99    --  103.72  30.00 -90.00   94
  8  \w     50.00 133.00   1.00   15.99    --  103.72 -61.00-180.00   83
  9  \w     71.00  97.00   1.00   15.99    --  103.72 -94.00-180.00   26
 10  \w     45.00 123.00   1.00   15.99    --  103.72 -30.00 -60.00   78
 11  \w     98.00 132.00   1.00   15.99    --  103.72 125.00 -90.00   34
 12  \w    134.00 175.00   1.00   15.99    --  103.72 125.00 -90.00   41
 13  \w     28.00  60.00   1.00   15.99    --  103.72 -94.00-150.00   32
 14  \w     88.00 113.00   1.00   15.99    --  103.72-125.00 120.00   25
 15  \w     40.00  72.00   1.00   15.99    --  103.72-125.00 120.00   32
 16  \w     41.00 110.00   1.00   15.99    --  103.72-125.00 150.00   69
 17  \w     28.00  54.00   1.00   15.99    --  103.72 -94.00-180.00   26
 18  \w     81.00 106.00   1.00   15.99    --  103.72 -94.00-150.00   25
 19  \w     28.00 133.00   1.00   15.99    --  103.72 -77.00 -60.00  105
;
_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      0.0199682000
_diffrn_orient_matrix_UB_12      -0.0145090000
_diffrn_orient_matrix_UB_13      -0.0792724000
_diffrn_orient_matrix_UB_21      -0.1736729000
_diffrn_orient_matrix_UB_22      -0.0799266000
_diffrn_orient_matrix_UB_23      -0.0162289000
_diffrn_orient_matrix_UB_31      -0.0526761000
_diffrn_orient_matrix_UB_32      0.1440489000
_diffrn_orient_matrix_UB_33      -0.0087151000
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10263
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.672
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_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    1.205
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0527P)^2^+0.3949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4603
_reflns_number_total             5412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01615k2.cif
_cod_data_source_block           2024jrh0012_auto_res
_cod_database_code               7160869
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2F3
_chemical_oxdiff_usercomment     '150 K lisa W 3-34-3'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 99.91
_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 C(H,H,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. Restrained distances
 C29A-C28 \\sim C29B-C28 \\sim C17-C16 \\sim C21-C20 \\sim C25-C24
 with sigma of 0.02
3. Others
 Sof(H28C)=Sof(H28D)=Sof(C29B)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H28A)=Sof(H28B)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
4.a Free rotating group:
 O7(H7A,H7B)
4.b Ternary CH refined with riding coordinates:
 C9(H9)
4.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B), C11(H11A,H11B), C18(H18A,H18B), C26(H26A,
 H26B), C12(H12A,H12B), C23(H23A,H23B), C15(H15A,H15B), C24(H24A,H24B),
 C19(H19A,H19B), C16(H16A,H16B), C27(H27A,H27B), C20(H20A,H20B), C28(H28A,H28B),
  C28(H28C,H28D)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6), C7(H7), C4(H4), C3(H3A)
4.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C17(H17A,H17B,
 H17C), C29A(H29A,H29B,H29C), C29B(H29D,H29E,H29F)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              23412
_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 1.968
_oxdiff_exptl_absorpt_empirical_full_min 0.723