Towards quantifying the role of hydrogen bonding within amphiphile self-association and resultant aggregate formation
White, L. J.; Wells, N. J.; Blackholly, L. R.; Shepherd, H. J.; Wilson, B.; Bustone, G. P.; Runacres, T. J.; Hiscock, J. R.; Chem. Sci.  (2017) –; doi:10.1039/C7SC03888G

data_1547368
_publ_section_title
;
 Towards quantifying the role of hydrogen bonding within amphiphile
 self-association and resultant aggregate formation
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03888G
_journal_year                    2017
_chemical_formula_moiety         'C16 H14 N3 O4 S2, 2(C8 H18 N0.5), 0.5(O)'
_chemical_formula_sum            'C32 H50 N4 O4.5 S2'
_chemical_formula_weight         626.88
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-04 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.706(3)
_cell_length_b                   13.689(4)
_cell_length_c                   19.969(4)
_cell_measurement_reflns_used    1635
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      72.8630
_cell_measurement_theta_min      3.9180
_cell_volume                     3319.4(15)
_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_temperature      100.0(4)
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_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    -62.00  33.00   1.00   10.00    --  -41.59  38.00 -60.00   95
  2  \w    -66.00  32.00   1.00   10.00    --  -41.59  38.00-150.00   98
  3  \w     29.00  60.00   1.00   10.00    --   41.59-125.00-180.00   31
  4  \w     64.00  90.00   1.00   10.00    --   41.59-125.00-180.00   26
  5  \w     35.00 109.00   1.00   30.00    --  104.59 -94.00 -90.00   74
  6  \w     86.00 115.00   1.00   30.00    --  104.59-111.00-180.00   29
  7  \w     56.00 129.00   1.00   30.00    --  104.59 -45.00-120.00   73
  8  \w     97.00 177.00   1.00   30.00    --  104.59  45.00  30.00   80
  9  \w    100.00 175.00   1.00   30.00    --  104.59 111.00-150.00   75
 10  \w     88.00 123.00   1.00   30.00    --  104.59 178.00 -90.00   35
 11  \w     82.00 121.00   1.00   30.00    --  104.59 178.00 150.00   39
 12  \w     74.00 109.00   1.00   30.00    --  104.59 -94.00  30.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1197
_diffrn_reflns_av_unetI/netI     0.1660
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12807
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.695
_exptl_absorpt_coefficient_mu    1.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0673
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3279
_reflns_number_total             5872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03888g2.cif
_cod_data_source_block           2017jrh0006_res
_cod_original_cell_volume        3319.3(16)
_cod_original_formula_sum        'C32 H50 N4 O4.50 S2'
_cod_database_code               1547368
_shelxl_version_number           2013-4
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C31B) = Uanis(C31A)
Uanis(C29B) = Uanis(C29A)
Uanis(C28B) = Uanis(C28A)
Uanis(C27B) = Uanis(C27A)
Uanis(C30B) = Uanis(C30A)
Uanis(C32B) = Uanis(C32A)
3. Others
 Fixed Sof: C28B(0.5) H28A(0.5) H28B(0.5) C27B(0.5) H27A(0.5) H27B(0.5)
 C28A(0.5) H28C(0.5) H28D(0.5) C27A(0.5) H27C(0.5) H27D(0.5) C29B(0.5)
 H29A(0.5) H29B(0.5) C29A(0.5) H29C(0.5) H29D(0.5) H26C(0.5) H26D(0.5)
 H26A(0.5) H26B(0.5) C30B(0.5) H30A(0.5) H30B(0.5) C31B(0.5) H31A(0.5)
 H31B(0.5) C31A(0.5) H31C(0.5) H31D(0.5) C32B(0.5) H32A(0.5) H32B(0.5)
 H32C(0.5) C30A(0.5) H30C(0.5) H30D(0.5) C32A(0.5) H32D(0.5) H32E(0.5) H32F(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C16(H16A,H16B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C28B(H28A,H28B), C27B(H27A,H27B),
 C28A(H28C,H28D), C27A(H27C,H27D), C29B(H29A,H29B), C29A(H29C,H29D), C26(H26C,
 H26D), C26(H26A,H26B), C30B(H30A,H30B), C31B(H31A,H31B), C31A(H31C,H31D),
 C30A(H30C,H30D)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C11(H11), C10(H10), C13(H13), C3(H3A), C14(H14), C6(H6),
 C2(H2A)
4.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C32B(H32A,H32B,H32C), C32A(H32D,H32E,H32F)
;
_shelx_res_checksum              11774
_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
;