Switchable foldamer ion channels with antibacterial activity
Peters, Anna D.; Borsley, Stefan; della Sala, Flavio; Cairns-Gibson, Dominic F.; Leonidou, Marios; Clayden, Jonathan; Whitehead, George F. S.; Vitorica-Yrzebal, Inigo; Takano, Eriko; Burthem, John; Cockroft, Scott Lee; Webb, Simon; Chemical Science  (2020) –; doi:10.1039/D0SC02393K

data_1558182
_publ_section_title
;
 Switchable foldamer ion channels with antibacterial activity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02393K
_journal_year                    2020
_chemical_formula_moiety         'C52 H83 N13 O9 Si, C1.81 H4.52 O0.45'
_chemical_formula_sum            'C53.81 H87.51 N13 O9.45 Si'
_chemical_formula_weight         1095.83
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-27 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                85.168(2)
_cell_angle_beta                 79.223(2)
_cell_angle_gamma                76.681(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2070(3)
_cell_length_b                   15.6088(3)
_cell_length_c                   23.6308(5)
_cell_measurement_reflns_used    26334
_cell_measurement_temperature    220.01(10)
_cell_measurement_theta_max      72.2980
_cell_measurement_theta_min      1.8700
_cell_volume                     3243.35(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.972
_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    -85.00  25.00   1.00    3.00    --    0.00  51.00  94.88  110
  2  \w     80.00 105.00   1.00    3.00    --   16.00  60.00 -92.03   25
  3  \w    -72.00 -32.00   1.00    3.00    --   16.00  60.00 -92.03   40
  4  \w     19.00  80.00   1.00    3.00    --   40.00  55.00-135.44   61
  5  \w    -49.00 -14.00   1.00    3.00    --   40.00  60.00  -5.94   35
  6  \w    -49.00   7.00   1.00    3.00    --   40.00  60.00 -70.79   56
  7  \w     11.00  82.00   1.00    3.00    --   40.00  58.00  67.87   71
  8  \w    -48.00 -12.00   1.00    3.00    --   40.00  59.00 132.74   36
  9  \w    -48.00 -14.00   1.00    3.00    --   40.00  58.00  67.87   34
 10  \w    -49.00 -13.00   1.00    3.00    --   40.00  55.00-135.44   36
 11  \w    -45.00 133.00   1.00    3.00    --   44.00  60.00 152.10  178
 12  \w    -45.00  -5.00   1.00    3.00    --   44.00  60.00  17.07   40
 13  \w    -37.00 -11.00   1.00    3.00    --   52.00  58.00 110.82   26
 14  \w    -37.00   2.00   1.00    3.00    --   52.00  58.00  71.04   39
 15  \w    -37.00 -11.00   1.00    3.00    --   52.00  60.00-122.05   26
 16  \w    -37.00  -2.00   1.00    3.00    --   52.00  56.00 -52.48   35
 17  \w    -33.00  -2.00   1.00    3.00    --   56.00  60.00 178.33   31
 18  \w    120.00 145.00   1.00    3.00    --   56.00  60.00 178.33   25
 19  \w    -33.00   5.00   1.00    3.00    --   56.00  56.00 -17.75   38
 20  \w    -33.00  -6.00   1.00    3.00    --   56.00  59.00-102.15   27
 21  \w    116.00 142.00   1.00    3.00    --   60.00  60.00  20.30   26
 22  \w    -29.00 100.00   1.00    3.00    --   60.00  60.00  20.30  129
 23  \w    -25.00  10.00   1.00    3.00    --   64.00  60.00 -14.18   35
 24  \w    -25.00   1.00   1.00    3.00    --   64.00  60.00 114.44   26
 25  \w    -25.00   2.00   1.00    3.00    --   64.00  59.00 132.18   27
 26  \w    -24.00  11.00   1.00    3.00    --   64.00  60.00-141.02   35
 27  \w    -25.00 151.00   1.00    3.00    --   64.00  60.00-179.74  176
 28  \w    -25.00   1.00   1.00    3.00    --   64.00  57.00 176.42   26
 29  \w    -21.00 157.00   1.00    3.00    --   68.00  58.00  -0.50  178
 30  \w    -20.00 156.00   1.00    3.00    --   68.00  59.00 -61.85  176
 31  \w    112.00 138.00   1.00    3.00    --   68.00  60.00  48.81   26
 32  \w    -21.00  23.00   1.00    3.00    --   68.00  57.00-129.14   44
 33  \w    -21.00  11.00   1.00    3.00    --   68.00  60.00  48.81   32
 34  \w     24.00  56.00   1.00    3.00    --   68.00  59.00 -72.31   32
 35  \w    -21.00  14.00   1.00    3.00    --   68.00  59.00 -72.31   35
 36  \w    -21.00  74.00   1.00    3.00    --   68.00  57.00  90.38   95
 37  \w    -17.00  39.00   1.00    3.00    --   72.00  60.00  56.87   56
 38  \w    -17.00  94.00   1.00    3.00    --   72.00  58.00 118.87  111
 39  \w     58.00 117.00   1.00    3.00    --   72.00  60.00-100.92   59
 40  \w    -17.00  52.00   1.00    3.00    --   72.00  60.00-100.92   69
 41  \w     21.00  47.00   1.00   10.00    --  110.00  60.00 150.00   26
 42  \w     21.00  47.00   1.00   10.00    --  110.00  46.00-120.00   26
 43  \w     21.00 159.00   1.00   10.00    --  110.00  34.00  30.00  138
 44  \w    173.00 199.00   1.00   10.00    --  110.00  60.00-180.00   26
 45  \w     57.00 114.00   1.00   10.00    --  110.00  46.00 -90.00   57
 46  \w    142.00 169.00   1.00   10.00    --  110.00  60.00-180.00   27
 47  \w    115.00 141.00   1.00   10.00    --  110.00  60.00-180.00   26
 48  \w     21.00  53.00   1.00   10.00    --  110.00  46.00-150.00   32
 49  \w     63.00  89.00   1.00   10.00    --  110.00  60.00-180.00   26
 50  \w     21.00  75.00   1.00   10.00    --  110.00  46.00   0.00   54
 51  \w     22.00 198.00   1.00   10.00    --  110.00  34.00  60.00  176
 52  \w     21.00  47.00   1.00   10.00    --  110.00  46.00 150.00   26
 53  \w     21.00  48.00   1.00   10.00    --  110.00  46.00  90.00   27
 54  \w     21.00  46.00   1.00   10.00    --  110.00  46.00 -90.00   25
 55  \w     21.00  47.00   1.00   10.00    --  110.00  60.00-180.00   26
 56  \w     21.00  46.00   1.00   10.00    --  110.00  46.00-180.00   25
 57  \w    136.00 187.00   1.00   10.00    --  110.00  60.00   0.00   51
 58  \w     21.00  57.00   1.00   10.00    --  110.00  46.00 -30.00   36
 59  \w    132.00 164.00   1.00   10.00    --  110.00  60.00  30.00   32
 60  \w     21.00  46.00   1.00   10.00    --  110.00  46.00 120.00   25
 61  \w     21.00  46.00   1.00   10.00    --  110.00  60.00   0.00   25
 62  \w     71.00  97.00   1.00   10.00    --  110.00  60.00  30.00   26
 63  \w     21.00  47.00   1.00   10.00    --  110.00  60.00  30.00   26
 64  \w     21.00 199.00   1.00   10.00    --  110.00  60.00-120.00  178
 65  \w     74.00 100.00   1.00   10.00    --  110.00  57.00 120.00   26
 66  \w     21.00  46.00   1.00   10.00    --  110.00  57.00 120.00   25
 67  \w     22.00 181.00   1.00   10.00    --  110.00  34.00 -60.00  159
 68  \w    133.00 159.00   1.00   10.00    --  110.00  60.00-150.00   26
 69  \w     21.00 198.00   1.00   10.00    --  110.00  34.00 120.00  177
 70  \w     22.00 121.00   1.00   10.00    --  110.00  34.00 -30.00   99
 71  \w     21.00  49.00   1.00   10.00    --  110.00  60.00-150.00   28
 72  \w    142.00 167.00   1.00   10.00    --  110.00  60.00 -30.00   25
 73  \w     22.00  67.00   1.00   10.00    --  110.00  34.00 150.00   45
 74  \w     21.00 115.00   1.00   10.00    --  110.00  34.00-180.00   94
 75  \w     21.00  47.00   1.00   10.00    --  110.00  60.00 -30.00   26
 76  \w     21.00  46.00   1.00   10.00    --  110.00  46.00  60.00   25
 77  \w    111.00 196.00   1.00   10.00    --  110.00  60.00  90.00   85
 78  \w     21.00  46.00   1.00   10.00    --  110.00  60.00  90.00   25
 79  \w     21.00  46.00   1.00   10.00    --  110.00  46.00  30.00   25
 80  \w    139.00 164.00   1.00   10.00    --  110.00  60.00 -60.00   25
 81  \w     22.00 112.00   1.00   10.00    --  110.00  34.00-150.00   90
 82  \w    143.00 193.00   1.00   10.00    --  110.00  60.00 -90.00   50
 83  \w     21.00  46.00   1.00   10.00    --  110.00  60.00 -60.00   25
 84  \w     21.00  46.00   1.00   10.00    --  110.00  46.00 -60.00   25
 85  \w     71.00 128.00   1.00   10.00    --  110.00  60.00 -90.00   57
 86  \w    130.00 155.00   1.00   10.00    --  110.00  60.00  60.00   25
 87  \w     21.00  47.00   1.00   10.00    --  110.00  60.00 -90.00   26
 88  \w     21.00  47.00   1.00   10.00    --  110.00  60.00  60.00   26
 89  \w    103.00 150.00   1.00   10.00    --  110.00  60.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0182066000
_diffrn_orient_matrix_UB_12      -0.0322645000
_diffrn_orient_matrix_UB_13      -0.0613008000
_diffrn_orient_matrix_UB_21      -0.0501870000
_diffrn_orient_matrix_UB_22      0.0958267000
_diffrn_orient_matrix_UB_23      -0.0225182000
_diffrn_orient_matrix_UB_31      0.1662150000
_diffrn_orient_matrix_UB_32      0.0090893000
_diffrn_orient_matrix_UB_33      -0.0121427000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            73644
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.882
_diffrn_reflns_theta_min         1.905
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
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    1.122
_exptl_crystal_description       needle
_exptl_crystal_F_000             1182
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.124
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     866
_refine_ls_number_reflns         12599
_refine_ls_number_restraints     832
_refine_ls_restrained_S_all      1.703
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0809
_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^)+(0.1642P)^2^+1.1611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2505
_refine_ls_wR_factor_ref         0.2641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9985
_reflns_number_total             12599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02393k2.cif
_cod_data_source_block           s4824l
_cod_database_code               1558182
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C20H20N2O2
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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
2. Restrained distances
 C3S-C2S
 1.54 with sigma of 0.02
 H27A_$1-H39B
 2.05 with sigma of 0.02
 C2S-C2S_$2
 2.4 with sigma of 0.002
 C3S-O1S
 2.4 with sigma of 0.02
 O1S-C2S = O1S-C2S_$2
 1.45 with sigma of 0.002
 C21A-C19A \\sim C21-C19
 with sigma of 0.002
 N8A-C18A \\sim N8-C18
 with sigma of 0.002
 C18A-C17 \\sim C18-C17
 with sigma of 0.002
 C35A-C18A \\sim C35-C18 \\sim C36-C18 \\sim C36A-C18A
 with sigma of 0.002
 N34A-C28A \\sim C28A-C30A
 with sigma of 0.02
 N11A-C21A \\sim N11-C21 \\sim N11A-C22A \\sim N11-C22 \\sim N11A-C28A \\sim
N11-C28
 with sigma of 0.002
 C23-C22 \\sim C29A-C28A \\sim C23A-C22A \\sim C29-C28
 with sigma of 0.002
 N12A-C22A \\sim C22A-C27A
 with sigma of 0.02
3. Restrained planarity
 C28A, C29A, C33A, N34A, C30A, C31A, C32A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N12 \\sim C26 \\sim C25 \\sim C29A \\sim C30A \\sim C31A \\sim N34A \\sim C24
\\sim C32A \\sim C33A \\sim C23 \\sim C27: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
N8 \\sim N9 \\sim N10 \\sim C19 \\sim C20 \\sim N8A \\sim N9A \\sim N10A \\sim
C19A \\sim C20A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C35A \\sim C35: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C18A \\sim C18: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C22A \\sim C22 \\sim N11A \\sim N11 \\sim C28 \\sim C21A \\sim C21 \\sim C28A:
within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C30 \\sim C31 \\sim C32 \\sim C33 \\sim N34 \\sim C29 \\sim N12A \\sim C24A
\\sim C25A \\sim C26A \\sim C27A \\sim C23A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C36) = Uanis(C36A)
Uanis(N34A) = Uanis(N12A)
Uanis(N12A) = Uanis(N34)
5. Rigid body (RIGU) restrains
 N12, N11, C23, C27, C26, C25, C24, C22, C28, C30, C31, C32, C33, N34, C29, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N8A, N9A, N10A, C19A, C20A, C21A, H21C, H21D, N11A, C28A, H28C, H28D, C29A,
 C30A, H30A, C31A, H31A, C32A, H32A, C33A, H33A, N34A, C22A, H22C, H22D, N12A,
 C24A, H24A, C25A, H25A, C26A, H26A, C27A, H27A, C23A, C18A, C35A, H35D, H35E,
 H35F, C36A, H36D, H36E, H36F
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O1S, C2S, C3S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Sof(N8A)=Sof(N9A)=Sof(N10A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21C)=
 Sof(H21D)=Sof(N11A)=Sof(C28A)=Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(C30A)=
 Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=
 Sof(N34A)=Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(N12A)=Sof(C24A)=Sof(H24A)=
 Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C23A)=
 Sof(C18A)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C36A)=Sof(H36D)=
 Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(O1S)=0.5*FVAR(2)
 Sof(N12)=Sof(N11)=Sof(N8)=Sof(N9)=Sof(N10)=Sof(C23)=Sof(C27)=Sof(H27)=
 Sof(C26)=Sof(H26)=Sof(C25)=Sof(H25)=Sof(C24)=Sof(H24)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(N34)=Sof(C29)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(C19)=Sof(C20)=Sof(H20)=Sof(C18)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(H35C)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=
 Sof(H3SC)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C28(H28A,H28B), C21(H21A,H21B), C2(H2A,H2B), C1(H1A,H1B),
 C21A(H21C,H21D), C28A(H28C,H28D), C22A(H22C,H22D), C2S(H2SA,H2SB)
7.b Me refined with riding coordinates:
 C3S(H3SA,H3SB,H3SC)
7.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N6(H6), N5(H5), N4(H4), N3(H3), N2(H2), N1(H1), C27(H27), C26(H26),
 C25(H25), C24(H24), C30(H30), C31(H31), C32(H32), C33(H33), C20(H20),
 C20A(H20A), C30A(H30A), C31A(H31A), C32A(H32A), C33A(H33A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A)
7.d Fitted pentagon refined as free rotating group:
 N8A(N9A,N10A,C19A,C20A)
7.e Fitted hexagon refined as free rotating group:
 C30(C31,C32,C33,N34,C29), C29A(C30A,C31A,C32A,C33A,N34A), N12A(C24A,C25A,C26A,
 C27A,C23A)
7.f Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C49(H49A,H49B,
 H49C), C50(H50A,H50B,H50C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C45(H45A,
 H45B,H45C), C46(H46A,H46B,H46C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C),
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C35A(H35D,H35E,H35F), C36A(H36D,H36E,H36F)
;
_shelx_res_checksum              1294
_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 39.387
_oxdiff_exptl_absorpt_empirical_full_min 0.362