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_7122692
_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         '2(C16 H11 N2 O6 S), C16 H18 N, C16 H24 N'
_chemical_formula_sum            'C64 H64 N6 O12 S2'
_chemical_formula_weight         1173.33
_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   geom
_audit_creation_date             2018-09-06
_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                84.931(5)
_cell_angle_beta                 84.247(6)
_cell_angle_gamma                75.288(6)
_cell_formula_units_Z            2
_cell_length_a                   11.9182(9)
_cell_length_b                   12.8979(8)
_cell_length_c                   23.0180(13)
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    292.9(9)
_cell_measurement_theta_max      57.1950
_cell_measurement_theta_min      4.5150
_cell_volume                     3397.8(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)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.9(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_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    106.00 177.00   1.00   30.00    --  105.91  77.00 150.00   71
  2  \w     86.00 113.00   1.00   30.00    --  105.91 -45.00 -60.00   27
  3  \w     63.00 108.00   1.00   30.00    --  105.91 -94.00 -60.00   45
  4  \w     53.00 137.00   1.00   30.00    --  105.91 -77.00   0.00   84
  5  \w     87.00 121.00   1.00   30.00    --  105.91-125.00 150.00   34
  6  \w     39.00 132.00   1.00   30.00    --  105.91 -45.00  90.00   93
  7  \w     45.00  72.00   1.00   30.00    --  105.91 -45.00 -60.00   27
  8  \w     35.00  62.00   1.00   30.00    --  105.91 -61.00-150.00   27
  9  \w     43.00 131.00   1.00   30.00    --  105.91 -45.00-150.00   88
 10  \w     50.00 108.00   1.00   30.00    --  105.91 -94.00-150.00   58
 11  \w     38.00  99.00   1.00   15.00    --   41.91-126.00-147.00   61
 12  \w    -14.00  64.00   1.00   15.00    --   41.91 -38.00  60.00   78
 13  \w     23.00  55.00   1.00   30.00    --  105.91 -94.00  90.00   32
 14  \w     35.00  62.00   1.00   30.00    --  105.91-125.00 150.00   27
 15  \w     18.00 169.00   1.00   30.00    --  105.91   0.00 150.00  151
 16  \w    144.00 172.00   1.00   30.00    --  105.91 126.00 -71.00   28
 17  \w    -70.00  29.00   1.00   15.00    --  -41.91  57.00  30.00   99
 18  \w   -107.00 -61.00   1.00   15.00    --  -41.91-144.00  43.00   46
 19  \w   -112.00 -21.00   1.00   15.00    --  -41.91 -57.00-120.00   91
;
_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      -0.0171728000
_diffrn_orient_matrix_UB_12      -0.1030698000
_diffrn_orient_matrix_UB_13      -0.0229877000
_diffrn_orient_matrix_UB_21      0.0093619000
_diffrn_orient_matrix_UB_22      0.0491165000
_diffrn_orient_matrix_UB_23      -0.0632435000
_diffrn_orient_matrix_UB_31      0.1326471000
_diffrn_orient_matrix_UB_32      -0.0477487000
_diffrn_orient_matrix_UB_33      -0.0040151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23306
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.551
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.202
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.713
_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    1.147
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.027
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.400
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         12023
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.400
_refine_ls_R_factor_all          0.2031
_refine_ls_R_factor_gt           0.1495
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4104
_refine_ls_wR_factor_ref         0.4690
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5482
_reflns_number_total             12023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08485h2.cif
_cod_data_source_block           2018jrh0039_res_test
_cod_database_code               7122692
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O3
_chemical_oxdiff_usercomment     '294 K stell 1-4'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.726
_reflns_odcompleteness_completeness 99.95
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C64-C63 = C56-C55B = C56-C55A = C40-C39
 1.46 with sigma of 0.001
 C39-C38 = C38-C37 = C55B-C54 = C55A-C54 = C63-C62
 1.5 with sigma of 0.001
 C61-C63
 2.425 with sigma of 0.001
 C53-C55B
 2.425 with sigma of 0.001
 C53-C55A
 2.425 with sigma of 0.001
 C37-C39
 2.425 with sigma of 0.001
 C56-C54
 2.425 with sigma of 0.02
 C40-C38
 2.425 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uiso(C37) = Uiso(C38) = Uiso(C39) = Uiso(C40) = Uiso(C64) = Uiso(C63) =
Uiso(C62) = Uiso(C61) = Uiso(C53) = Uiso(C54) = Uiso(C55B) = Uiso(C55A) =
Uiso(C56)
4. Others
 Sof(C55A)=1-FVAR(1)
 Sof(C55B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C60(H60A,H60B), C52(H52A,H52B), C51(H51A,H51B), C1(H1A,H1B),
 C50(H50A,H50B), C59(H59A,H59B), C45(H45A,H45B), C36(H36A,H36B), C35(H35A,H35B),
  C44(H44A,H44B), C46(H46A,H46B), C47(H47A,H47B), C34(H34A,H34B), C58(H58A,
 H58B), C43(H43A,H43B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N4(H4), C16(H16), N1(H1), C4(H4A), C20(H20), C5(H5), C12(H12),
  C9(H9), C11(H11), C10(H10), C31(H31), C32(H32), C24(H24), C26(H26), C27(H27),
 C25(H25), C42(H42)
5.c Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C33(H33A,H33B,H33C), C48(H48A,H48B,H48C), C57(H57A,H57B,
 H57C)
5.d :
 C41(H41)
;
_shelx_res_checksum              791
_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 1.854
_oxdiff_exptl_absorpt_empirical_full_min 0.667