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_7160870
_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         'C14 H15 F3 N2 O5'
_chemical_formula_sum            'C14 H15 F3 N2 O5'
_chemical_formula_weight         348.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-03-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.477(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.781(3)
_cell_length_b                   10.9013(10)
_cell_length_c                   10.0416(7)
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      71.7980
_cell_measurement_theta_min      4.3140
_cell_volume                     3035.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.970
_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    -56.00 -10.00   1.00   10.00    --  -41.91 125.00 120.00   46
  2  \w   -114.00 -18.00   1.00   10.00    --  -41.91 -38.00 -30.00   96
  3  \w    -86.00 -11.00   1.00   10.00    --  -41.91 125.00-150.00   75
  4  \w   -109.00 -17.00   1.00   10.00    --  -41.91 -38.00  60.00   92
  5  \w     55.00  96.00   1.00   10.00    --   41.91-125.00-180.00   41
  6  \w     69.00 113.00   1.00   22.50    --  103.72-125.00 -30.00   44
  7  \w     21.00 106.00   1.00   22.50    --  103.72 -94.00 120.00   85
  8  \w     67.00  94.00   1.00   22.50    --  103.72 -77.00 120.00   27
  9  \w     32.00 126.00   1.00   22.50    --  103.72 -45.00-150.00   94
 10  \w     55.00 118.00   1.00   22.50    --  103.72 -61.00 -30.00   63
 11  \w     42.00 116.00   1.00   22.50    --  103.72 -45.00 120.00   74
 12  \w     34.00 129.00   1.00   22.50    --  103.72 -30.00 -60.00   95
 13  \w     77.00 113.00   1.00   22.50    --  103.72-125.00-120.00   36
 14  \w    106.00 176.00   1.00   22.50    --  103.72  77.00 -90.00   70
 15  \w     52.00 105.00   1.00   22.50    --  103.72 -94.00 -30.00   53
 16  \w     81.00 113.00   1.00   22.50    --  103.72-125.00 120.00   32
 17  \w    145.00 172.00   1.00   22.50    --  103.72 125.00   0.00   27
 18  \w     17.00 170.00   1.00   22.50    --  103.72   0.00 -90.00  153
;
_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      0.0024087000
_diffrn_orient_matrix_UB_12      0.1412438000
_diffrn_orient_matrix_UB_13      0.0035427000
_diffrn_orient_matrix_UB_21      -0.0554863000
_diffrn_orient_matrix_UB_22      0.0063425000
_diffrn_orient_matrix_UB_23      -0.0056452000
_diffrn_orient_matrix_UB_31      0.0013440000
_diffrn_orient_matrix_UB_32      -0.0030010000
_diffrn_orient_matrix_UB_33      0.1534653000
_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  0.0912
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11086
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.473
_diffrn_reflns_theta_min         4.358
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       plank
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.1299
_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^)+(0.1754P)^2^+31.1281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3830
_refine_ls_wR_factor_ref         0.4072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1938
_reflns_number_total             2932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01615k2.cif
_cod_data_source_block           2024jrh0013_notwin
_cod_database_code               7160870
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2F3
_chemical_oxdiff_usercomment     '150 k lisa w 3-31-2'
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.800
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C13(H13), C12(H12), C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              23524
_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 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.617