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_7160872
_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         'C12 H11 Br N2 O5, 7(H2 O), 2(C16 H36 N)'
_chemical_formula_sum            'C44 H97 Br N4 O12'
_chemical_formula_weight         954.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.3063(13)
_cell_length_b                   16.6092(12)
_cell_length_c                   33.619(2)
_cell_measurement_reflns_used    3647
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      56.2740
_cell_measurement_theta_min      3.7020
_cell_volume                     10780.3(12)
_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 0.974
_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   -110.00 -16.00   1.00   12.50    --  -42.16 -57.00  30.00   94
  2  \w    -54.00 -16.00   1.00   12.50    --  -42.16 125.00-180.00   38
  3  \w     14.00  50.00   1.00   12.50    --   42.16  19.00 150.00   36
  4  \w     80.00 177.00   1.00   20.00    --  103.72  30.00 120.00   97
  5  \w     44.00  70.00   1.00   20.00    --  103.72-125.00-180.00   26
  6  \w     83.00 111.00   1.00   20.00    --  103.72-125.00-180.00   28
  7  \w    104.00 172.00   1.00   20.00    --  103.72  77.00 -30.00   68
  8  \w     59.00 112.00   1.00   20.00    --  103.72-125.00 -30.00   53
  9  \w    138.00 168.00   1.00   20.00    --  103.72 125.00 -60.00   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      -0.0026241000
_diffrn_orient_matrix_UB_12      -0.0154660000
_diffrn_orient_matrix_UB_13      0.0451911000
_diffrn_orient_matrix_UB_21      0.0675112000
_diffrn_orient_matrix_UB_22      -0.0490791000
_diffrn_orient_matrix_UB_23      -0.0028458000
_diffrn_orient_matrix_UB_31      0.0424427000
_diffrn_orient_matrix_UB_32      0.0771189000
_diffrn_orient_matrix_UB_33      0.0072074000
_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  0.0575
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            28580
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.496
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.905
_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    1.176
_exptl_crystal_description       needle
_exptl_crystal_F_000             4160
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         9503
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0867
_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^)+(0.1405P)^2^+12.5390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2368
_refine_ls_wR_factor_ref         0.2843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5339
_reflns_number_total             9503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01615k2.cif
_cod_data_source_block           2024jrh0022a_auto_res
_cod_original_cell_volume        10780.2(13)
_cod_database_code               7160872
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20H20N2O2Br
_chemical_oxdiff_usercomment     '150 K lisa w 35-3 '
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.853
_reflns_odcompleteness_completeness 99.70
_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,H) groups
2. Restrained distances
 C43-C44A \\sim C43-C44B
 with sigma of 0.02
3. Others
 Sof(H43C)=Sof(H43D)=Sof(C44B)=Sof(H44D)=Sof(H44E)=Sof(H44F)=1-FVAR(1)
 Sof(H43A)=Sof(H43B)=Sof(C44A)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
 Fixed Sof: H8A(0.5) H8B(0.5) H9A(0.5) H9B(0.5)
4.a Free rotating group:
 O12(H12A,H12B), O7(H7A,H7B), O8(H8A,H8B), O6(H6A,H6B), O9(H9A,H9B), O13(H13C,
 H13D), O11(H11C,H11D), O10(H10C,H10D)
4.b Ternary CH refined with riding coordinates:
 C8(H8)
4.c Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C17(H17A,H17B), C33(H33A,H33B), C13(H13A,H13B), C37(H37A,
 H37B), C22(H22A,H22B), C41(H41A,H41B), C10(H10A,H10B), C29(H29A,H29B),
 C25(H25A,H25B), C34(H34A,H34B), C23(H23A,H23B), C18(H18A,H18B), C14(H14A,H14B),
  C11(H11A,H11B), C26(H26A,H26B), C38(H38A,H38B), C35(H35A,H35B), C42(H42A,
 H42B), C30(H30A,H30B), C15(H15A,H15B), C39(H39A,H39B), C19(H19A,H19B),
 C31(H31A,H31B), C43(H43A,H43B), C43(H43C,H43D), C27(H27A,H27B)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C2(H2A), C5(H5), C6(H6)
4.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C36(H36A,H36B,H36C), C16(H16A,H16B,
 H16C), C40(H40A,H40B,H40C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C),
 C44A(H44A,H44B,H44C), C44B(H44D,H44E,H44F)
;
_shelx_res_checksum              93584
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.838