A symbiotic supramolecular approach to the design of novel amphiphiles with antibacterial properties against MSRA
Tyuleva, Stilyana N.; Allen, Nyasha; White, Lisa J.; Pépés, Antigoni; Shepherd, Helena J.; Saines, Paul J.; Ellaby, Rebecca J.; Mulvihill, Daniel P.; Hiscock, Jennifer R.; Chemical Communications  (2018) –; doi:10.1039/C8CC08485H

data_7122693
_publ_section_title
;
 A symbiotic supramolecular approach to the design of novel amphiphiles
 with antibacterial properties against MSRA
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08485H
_journal_year                    2018
_chemical_formula_moiety
'C16 H12.69 N2 O4.31 S, 2(H2 O), C16 H11 N2 O6 S, C16 H36 N, C16 H35.41 N, 1(C2 H6 O S)'
_chemical_formula_sum            'C65.99 H105.09 N6 O13.31 S3'
_chemical_formula_weight         1291.64
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-06 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.236(5)
_cell_angle_beta                 90.694(6)
_cell_angle_gamma                105.370(7)
_cell_formula_units_Z            2
_cell_length_a                   11.4872(10)
_cell_length_b                   12.4679(9)
_cell_length_c                   25.0105(13)
_cell_measurement_reflns_used    7743
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      72.8830
_cell_measurement_theta_min      4.6450
_cell_volume                     3437.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_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     87.00 137.00   1.00   19.34    --  105.22 -77.00 150.00   50
  2  \w     77.00 178.00   1.00   19.34    --  105.22  30.00 120.00  101
  3  \w    103.00 140.00   1.00   19.34    --  105.22 111.00 -60.00   37
  4  \w    144.00 175.00   1.00   19.34    --  105.22  61.00 -90.00   31
  5  \w    103.00 156.00   1.00   19.34    --  105.22 111.00-180.00   53
  6  \w    101.00 146.00   1.00   19.34    --  105.22 178.00-180.00   45
  7  \w     87.00 141.00   1.00   19.34    --  105.22  61.00   0.00   54
  8  \w     93.00 119.00   1.00   19.34    --  105.22  61.00 -90.00   26
  9  \w     34.00 117.00   1.00   19.34    --  105.22 -61.00 -60.00   83
 10  \w     73.00 108.00   1.00   19.34    --  105.22 -94.00-180.00   35
 11  \w     60.00  86.00   1.00    4.84    --   41.47-125.00 -90.00   26
 12  \w     29.00 116.00   1.00   19.34    --  105.22-111.00 -30.00   87
 13  \w     52.00 133.00   1.00   19.34    --  105.22 -30.00 120.00   81
 14  \w     43.00 116.00   1.00   19.34    --  105.22-119.00 153.00   73
 15  \w     32.00  81.00   1.00   19.34    --  105.22 -77.00 150.00   49
 16  \w     15.00  42.00   1.00    4.84    --   41.47  57.00 150.00   27
 17  \w    -71.00  31.00   1.00    4.84    --  -41.47  77.00  30.00  102
 18  \w    -65.00  30.00   1.00    4.84    --  -41.47  38.00 -60.00   95
 19  \w   -110.00 -17.00   1.00    4.84    --  -41.47 -38.00 120.00   93
 20  \w     61.00  87.00   1.00   19.34    --  105.22 178.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289119000
_diffrn_orient_matrix_UB_12      0.0177723000
_diffrn_orient_matrix_UB_13      -0.0590523000
_diffrn_orient_matrix_UB_21      -0.0651162000
_diffrn_orient_matrix_UB_22      -0.1235734000
_diffrn_orient_matrix_UB_23      -0.0168146000
_diffrn_orient_matrix_UB_31      -0.1195675000
_diffrn_orient_matrix_UB_32      0.0315303000
_diffrn_orient_matrix_UB_33      -0.0078464000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22986
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.694
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       plate
_exptl_crystal_F_000             1395
_exptl_crystal_recrystallization_method
'a single crystal was obtained from a deuterated DMSO solution.'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.098
_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     865
_refine_ls_number_reflns         12134
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0981
_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^)+(0.1971P)^2^+0.7414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2610
_refine_ls_wR_factor_ref         0.2846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9438
_reflns_number_total             12134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08485h2.cif
_cod_data_source_block           2017jrh0045_res
_cod_database_code               7122693
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H10 N3 O2'
_chemical_oxdiff_usercomment     100K
_reflns_odcompleteness_completeness 99.89
_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
 O00J-C017 \\sim O00H-C018
 with sigma of 0.02
 O00H-C018 \\sim O00J-C017
 with sigma of 0.02
 S1-C5 \\sim S1A-C4A \\sim S1A-C5A \\sim S1-C4
 with sigma of 0.002
 S1-O3 \\sim S1A-O3A
 with sigma of 0.002
 S0AA-O2AA \\sim S1A-O3A \\sim S1-O3
 with sigma of 0.001
 S1-C5 \\sim S1A-C4A \\sim S1A-C5A \\sim S0AA-C4AA \\sim S0AA-C5AA \\sim S1-C4
 with sigma of 0.001
 O00H-C018 \\sim O24-C012 \\sim O3AA-C01C \\sim O00J-C017
 with sigma of 0.002
3. Restrained planarity
 C013, C01A, C00N, C00Q, C012, C01C
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O24 \\sim C012 \\sim C01C \\sim O3AA: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.01
Uanis(C01S) = Uanis(C0AA)
Uanis(C02B) = Uanis(C2AA)
Uanis(C02F) = Uanis(C02G)
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(C3AA) = Uanis(C3AB)
Uanis(C1AA) = Uanis(C1AB)
Uanis(C026) = Uanis(C0)
Uanis(S1) = Uanis(O3) = Uanis(C4) = Uanis(C5)
Uanis(C5) = Uanis(C5A)
Uanis(C4) = Uanis(C4A)
Uanis(S1) = Uanis(S1A)
Uanis(O3) = Uanis(O3A)
Uanis(S1) = Uanis(O3) = Uanis(C4) = Uanis(C5) = Uanis(C5A) = Uanis(S1A) =
Uanis(O3A) = Uanis(C4A)
Uanis(C5A) = Uanis(S1A) = Uanis(C4A) = Uanis(O3A) = Uanis(S1) = Uanis(O3) =
Uanis(C4) = Uanis(C5) = Uanis(S0AA) = Uanis(C4AA) = Uanis(O2AA) = Uanis(C5AA)
Uanis(O24) = Uanis(O3AA)
5. Others
 1*[Sof(C5A)+Sof(H5AB)+Sof(H5AC)+Sof(H5AD)+Sof(C4A)+Sof(H4AB)+Sof(H4AC)+
 Sof(H4AD)+Sof(S1A)+Sof(O3A)]+1*[Sof(C4AA)+Sof(H4AE)+Sof(H4AF)+Sof(H4AG)+
 Sof(S0AA)+Sof(O2AA)+Sof(C5AA)+Sof(H5AE)+Sof(H5AF)+Sof(H5AG)]+1*[Sof(S1)+
 Sof(O3)+Sof(C4)+Sof(H4A)+Sof(H4B)+Sof(H4C)+Sof(C5)+Sof(H5A)+Sof(H5B)+Sof(H5C)]=
 1 with esd of 0.001
 Sof(H01I)=Sof(H01J)=Sof(C2AA)=Sof(H2AC)=Sof(H2AD)=Sof(C0AA)=Sof(H0AA)=
 Sof(H0AB)=Sof(C02G)=Sof(H02N)=Sof(H02O)=Sof(H02P)=1-FVAR(1)
 Sof(H01G)=Sof(H01H)=Sof(C02B)=Sof(H02I)=Sof(H02J)=Sof(C02F)=Sof(H02K)=
 Sof(H02L)=Sof(H02M)=Sof(C01S)=Sof(H01Q)=Sof(H01R)=FVAR(1)
 Sof(H01C)=Sof(H01D)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(C3AB)=Sof(H3AD)=Sof(H3AE)=Sof(H3AF)=1-FVAR(2)
 Sof(H01A)=Sof(H01B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C1)=Sof(H1A)=Sof(H1B)=
 Sof(C3AA)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=FVAR(2)
 Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(C1AB)=Sof(H1AF)=Sof(H1AG)=Sof(H1AH)=1-FVAR(3)
 Sof(H02V)=Sof(H02W)=Sof(C026)=Sof(H5AA)=Sof(HI)=Sof(C1AA)=Sof(H1AC)=Sof(H1AD)=
 Sof(H1AE)=FVAR(3)
 Sof(C5A)=Sof(H5AB)=Sof(H5AC)=Sof(H5AD)=Sof(C4A)=Sof(H4AB)=Sof(H4AC)=Sof(H4AD)=
 Sof(S1A)=Sof(O3A)=FVAR(4)
 Sof(C4AA)=Sof(H4AE)=Sof(H4AF)=Sof(H4AG)=Sof(S0AA)=Sof(O2AA)=Sof(C5AA)=
 Sof(H5AE)=Sof(H5AF)=Sof(H5AG)=FVAR(5)
 Sof(S1)=Sof(O3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(H5A)=Sof(H5B)=
 Sof(H5C)=FVAR(6)
 Sof(H012)=Sof(H0BA)=1-FVAR(7)
 Sof(O3AA)=Sof(O24)=FVAR(7)
6.a Free rotating group:
 O11(H11A,H11B), O1(H1C,H1D)
6.b Secondary CH2 refined with riding coordinates:
 C010(H01S,H01T), C024(H02T,H02U), C021(H02V,H02W), C022(H02X,H02Y), C023(H02A,
 H02B), C025(H02Z,H), C016(H01A,H01B), C016(H01C,H01D), C01E(H01E,H01F),
 C01F(H01G,H01H), C01F(H01I,H01J), C01H(H01U,H01V), C01I(H01K,H01L), C01J(H01M,
 H01N), C01K(H1BA,HC), C01L(H01W,H01X), C01N(H01Y,HD), C01P(H01O,H01P),
 C00T(H00E,H00F), C01U(H01Z,HE), C01V(H01,HF), C00X(H00C,H00D), C00Z(H00A,H00B),
  C026(H5AA,HI), C2(H2A,H2B), C1(H1A,H1B), C02B(H02I,H02J), C01S(H01Q,H01R),
 C0(H0A,H0B), C2A(H2AA,H2AB), C1A(H1AA,H1AB), C2AA(H2AC,H2AD), C0AA(H0AA,H0AB)
6.c Aromatic/amide H refined with riding coordinates:
 N9(H9), N11(H11), N10(H10), N00G(H00G), C015(H015), C014(H014), C019(H019),
 C01M(H2BA), C01O(H3BA), C01Q(H6AA), C00R(H00R), C01R(H7AA), C00S(H00S),
 C01T(H4BA), C01X(H5BA), C01Y(H8AA), C00Y(H00Y), C01Z(H9AA), C012(H012),
 C01C(H0BA)
6.d Idealised Me refined as rotating group:
 C029(H02Q,H02R,H02S), C020(H02C,H02D,H02E), C02A(H02F,H02G,H02H), C02C(H02,HA,
 HB), C01W(H4AA,HG,HH), C3AA(H3AA,H3AB,H3AC), C1AA(H1AC,H1AD,H1AE), C02F(H02K,
 H02L,H02M), C3AB(H3AD,H3AE,H3AF), C1AB(H1AF,H1AG,H1AH), C02G(H02N,H02O,H02P),
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C5A(H5AB,H5AC,H5AD), C4A(H4AB,H4AC,H4AD),
 C4AA(H4AE,H4AF,H4AG), C5AA(H5AE,H5AF,H5AG)
;
_shelx_res_checksum              92128
_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 1.848
_oxdiff_exptl_absorpt_empirical_full_min 0.579