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_1547365
_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 H13 N2 O4 S, C16 H11 N2 O6 S, 2(C16 H36 N)'
_chemical_formula_sum            'C64 H96 N6 O10 S2'
_chemical_formula_weight         1173.58
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-01
_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                88.359(8)
_cell_angle_beta                 86.588(8)
_cell_angle_gamma                76.689(10)
_cell_formula_units_Z            2
_cell_length_a                   11.2916(13)
_cell_length_b                   12.5010(13)
_cell_length_c                   23.9203(16)
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      66.1440
_cell_measurement_theta_min      3.6090
_cell_volume                     3279.6(6)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.578
_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     -9.00  16.00   1.00   10.00    --   34.00 102.00  98.42   25
  2  \w      0.00  25.00   1.00   10.00    --   38.00  93.00 -31.67   25
  3  \w   -113.00 -13.00   1.00   10.00    --  -40.62 -57.00  90.00  100
  4  \w   -115.00 -30.00   1.00   10.00    --  -40.62 -38.00   0.00   85
  5  \w    -94.00 -18.00   1.00   10.00    --  -40.62 -38.00-180.00   76
  6  \w    -68.00  29.00   1.00   10.00    --  -40.62  57.00  60.00   97
  7  \w   -112.00 -25.00   1.00   10.00    --  -40.62 -38.00 -90.00   87
  8  \w     23.00  86.00   1.00   10.00    --   40.62-125.00-180.00   63
  9  \w     23.00  83.00   1.00   10.00    --   40.62-125.00 -60.00   60
 10  \w     12.00  37.00   1.00   10.00    --   46.00  83.00-123.06   25
 11  \w     16.00  41.00   1.00   10.00    --   50.00  82.00 157.87   25
 12  \w     16.00  41.00   1.00   10.00    --   50.00  82.00  63.22   25
 13  \w     21.00  46.00   1.00   10.00    --   54.00  79.00 -23.57   25
 14  \w     20.00  45.00   1.00   10.00    --   54.00  81.00 -77.67   25
 15  \w     20.00  45.00   1.00   10.00    --   54.00  81.00  -0.17   25
 16  \w     21.00  46.00   1.00   10.00    --   54.00  79.00 176.49   25
 17  \w     20.00  46.00   1.00   10.00    --   54.00  81.00  91.90   26
 18  \w     33.00  79.00   1.00   10.00    --   66.00  77.00-153.30   46
 19  \w     35.00  60.00   1.00   10.00    --   66.00  76.00-110.99   25
 20  \w     33.00  59.00   1.00   10.00    --   66.00  77.00 -69.87   26
 21  \w    100.00 126.00   1.00   10.00    --   66.00  77.00 -69.87   26
 22  \w     34.00  61.00   1.00   10.00    --   66.00  76.00 124.95   27
 23  \w    100.00 137.00   1.00   10.00    --   70.00  76.00  95.68   37
 24  \w     38.00  71.00   1.00   10.00    --   70.00  76.00  95.68   33
 25  \w     39.00  69.00   1.00   10.00    --   70.00  76.00 -47.88   30
 26  \w     38.00  96.00   1.00   10.00    --   70.00  76.00 162.48   58
 27  \w    110.00 143.00   1.00   10.00    --   70.00  77.00   1.68   33
 28  \w     37.00  64.00   1.00   10.00    --   70.00  77.00   1.68   27
 29  \w     41.00  73.00   1.00   20.00    --   74.00  77.00  34.15   32
 30  \w    102.00 128.00   1.00   20.00    --   74.00  77.00  34.15   26
 31  \w     73.00 148.00   1.00   20.00    --  105.19  77.00 -90.00   75
 32  \w     32.00 116.00   1.00   20.00    --  105.19-111.00-120.00   84
 33  \w     53.00 112.00   1.00   20.00    --  105.19-111.00  60.00   59
 34  \w     76.00 107.00   1.00   20.00    --  105.19  61.00-120.00   31
 35  \w     55.00  98.00   1.00   20.00    --  105.19 -94.00 -30.00   43
 36  \w     77.00 111.00   1.00   20.00    --  105.19  61.00 120.00   34
 37  \w     76.00 103.00   1.00   20.00    --  105.19  61.00 -60.00   27
 38  \w     29.00 100.00   1.00   20.00    --  105.19 -94.00 150.00   71
 39  \w     73.00 143.00   1.00   20.00    --  105.19  77.00  30.00   70
 40  \w    109.00 178.00   1.00   20.00    --  105.19  77.00 -60.00   69
 41  \w     73.00 100.00   1.00   20.00    --  105.19  77.00 -60.00   27
 42  \w     73.00 177.00   1.00   20.00    --  105.19  77.00   0.00  104
 43  \w     76.00 103.00   1.00   20.00    --  105.19  61.00 -30.00   27
 44  \w     73.00 176.00   1.00   20.00    --  105.19  77.00 120.00  103
 45  \w     73.00 147.00   1.00   20.00    --  105.19  77.00 -30.00   74
 46  \w     73.00 175.00   1.00   20.00    --  105.19  77.00 150.00  102
 47  \w     73.00 178.00   1.00   20.00    --  105.19  77.00  60.00  105
 48  \w     73.00 177.00   1.00   20.00    --  105.19  77.00-120.00  104
 49  \w     79.00 106.00   1.00   20.00    --  105.19  61.00-150.00   27
 50  \w    127.00 153.00   1.00   20.00    --  105.19  61.00-150.00   26
 51  \w    110.00 160.00   1.00   20.00    --  105.19  77.00-180.00   50
 52  \w     23.00  94.00   1.00   20.00    --  105.19 -94.00  90.00   71
 53  \w     73.00  98.00   1.00   20.00    --  105.19  77.00-180.00   25
 54  \w     31.00  95.00   1.00   20.00    --  105.19 -94.00 -90.00   64
 55  \w    115.00 175.00   1.00   20.00    --  105.19  77.00  90.00   60
 56  \w     73.00  99.00   1.00   20.00    --  105.19  77.00  90.00   26
;
_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  0.1754
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_Laue_measured_fraction_full 0.578
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37401
_diffrn_reflns_point_group_measured_fraction_full 0.578
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         50.435
_diffrn_reflns_theta_min         3.634
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92331
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.060
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.460
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         6864
_refine_ls_number_restraints     223
_refine_ls_restrained_S_all      1.476
_refine_ls_R_factor_all          0.2097
_refine_ls_R_factor_gt           0.1405
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3336
_refine_ls_wR_factor_ref         0.3767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3357
_reflns_number_total             6864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03888g2.cif
_cod_data_source_block           2016jrh0053_res
_cod_database_code               1547365
_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. Restrained distances
 N5-C33 \\sim N5-C45 \\sim N5-C37 \\sim N5-C41 \\sim N62_$1-C49_$1 \\sim
N62_$1-C53_$1 \\sim N62_$1-
 C57_$1 \\sim N62_$1-C61_$1
 with sigma of 0.002
 C58-C57 \\sim C59-C58 \\sim C49-C50 \\sim C51-C50 \\sim C53-C54 \\sim C55-C54
\\sim C63A-C62A \\sim C63B-
 C62B \\sim C61-C62B \\sim C61-C62A
 with sigma of 0.002
 C64A-C63A \\sim C55-C56 \\sim C44-C43 \\sim C36-C35 \\sim C60-C59 \\sim
C48-C47 \\sim C51-C52 \\sim C39-
 C40 \\sim C63B-C64B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C56 \\sim N62 \\sim C49 \\sim C53 \\sim C61 \\sim C57 \\sim C50 \\sim C54 \\sim
C62A \\sim C62B \\sim C58 \\sim C51 \\sim C55 \\sim C63A \\sim C63B \\sim C59
\\sim C52 \\sim C64A \\sim C64B \\sim C60: within 2A with sigma of 0.008 and
sigma for terminal atoms of 0.004
Uanis(C62A) = Uanis(C62B)
Uanis(C63A) = Uanis(C64B)
Uanis(C64A) = Uanis(C63B)
4. Others
 Sof(H61A)=Sof(H61B)=Sof(C62B)=Sof(H62C)=Sof(H62D)=Sof(C64B)=Sof(H64D)=
 Sof(H64E)=Sof(H64F)=Sof(C63B)=Sof(H63C)=Sof(H63D)=1-FVAR(1)
 Sof(H61C)=Sof(H61D)=Sof(C63A)=Sof(H63A)=Sof(H63B)=Sof(C64A)=Sof(H64A)=
 Sof(H64B)=Sof(H64C)=Sof(C62A)=Sof(H62A)=Sof(H62B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C17(H17A,H17B), C45(H45A,H45B), C34(H34A,H34B), C33(H33A,H33B),
 C37(H37A,H37B), C35(H35A,H35B), C41(H41A,H41B), C42(H42A,H42B), C47(H47A,H47B),
  C38(H38A,H38B), C46(H46A,H46B), C43(H43A,H43B), C39(H39A,H39B), C54(H54A,
 H54B), C50(H50A,H50B), C49(H49A,H49B), C55(H55A,H55B), C51(H51A,H51B),
 C53(H53A,H53B), C61(H61C,H61D), C61(H61A,H61B), C58(H58A,H58B), C59(H59A,H59B),
  C57(H57A,H57B), C63A(H63A,H63B), C62A(H62A,H62B), C62B(H62C,H62D), C63B(H63C,
 H63D)
5.b Me refined with riding coordinates:
 C52(H52A,H52B,H52C), C56(H56A,H56B,H56C), C64A(H64A,H64B,H64C), C64B(H64D,
 H64E,H64F), C60(H60A,H60B,H60C)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C4(H4), N4(H4A), C9(H9), N3(H3), C24(H24), C10(H10), C8(H8),
 C15(H15), C21(H21), C16(H16), C7(H7), C20(H20), C13(H13), C14(H14), C29(H29),
 C31(H31), C32(H32), C30(H30)
5.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C48(H48A,H48B,H48C), C40(H40A,H40B,
 H40C)
;
_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
;