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_1547367
_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         'C12 H11 N2 O4 S, C16 H36 N, H2 O'
_chemical_formula_sum            'C28 H49 N3 O5 S'
_chemical_formula_weight         539.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.027(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1121(18)
_cell_length_b                   16.3159(14)
_cell_length_c                   13.6871(16)
_cell_measurement_reflns_used    5572
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      72.3010
_cell_measurement_theta_min      4.1150
_cell_volume                     2928.2(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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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    -71.00  25.00   1.00   10.00    --  -41.47  77.00  30.00   96
  2  \w   -115.00 -17.00   1.00   10.00    --  -41.47 -38.00 120.00   98
  3  \w    -66.00  28.00   1.00   10.00    --  -41.47  38.00 -60.00   94
  4  \w     60.00  94.00   1.00   10.00    --   41.47-125.00-120.00   34
  5  \w     41.00  68.00   1.00   10.00    --   41.47-125.00-180.00   27
  6  \w     47.00 106.00   1.00   30.00    --  104.59 -94.00-180.00   59
  7  \w     30.00 137.00   1.00   30.00    --  104.59 -77.00 -30.00  107
  8  \w     53.00  84.00   1.00   30.00    --  104.59 -61.00-180.00   31
  9  \w     63.00 111.00   1.00   30.00    --  104.59 178.00 -60.00   48
 10  \w     30.00 103.00   1.00   30.00    --  104.59-111.00 -60.00   73
 11  \w    116.00 178.00   1.00   30.00    --  104.59  30.00  90.00   62
 12  \w    140.00 169.00   1.00   30.00    --  104.59  61.00  30.00   29
 13  \w     68.00 115.00   1.00   30.00    --  104.59-111.00   0.00   47
 14  \w     30.00 122.00   1.00   30.00    --  104.59 -30.00  60.00   92
 15  \w    109.00 134.00   1.00   30.00    --  104.59 -61.00-180.00   25
 16  \w     41.00 118.00   1.00   30.00    --  104.59 -45.00 -30.00   77
 17  \w     23.00 145.00   1.00   30.00    --  104.59 -15.00 -90.00  122
 18  \w     52.00 110.00   1.00   30.00    --  104.59-111.00 150.00   58
;
_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      -0.0800307000
_diffrn_orient_matrix_UB_12      -0.0184960000
_diffrn_orient_matrix_UB_13      0.0793759000
_diffrn_orient_matrix_UB_21      -0.0458840000
_diffrn_orient_matrix_UB_22      0.0861509000
_diffrn_orient_matrix_UB_23      -0.0140782000
_diffrn_orient_matrix_UB_31      -0.0727354000
_diffrn_orient_matrix_UB_32      -0.0340025000
_diffrn_orient_matrix_UB_33      -0.0785274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20834
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.195
_diffrn_reflns_theta_min         4.216
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81639
_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    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0760P)^2^+0.7220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4527
_reflns_number_total             5754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03888g2.cif
_cod_data_source_block           2017jrh0018_res
_cod_database_code               1547367
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N4O4S2
_chemical_oxdiff_usercomment     naphalene
_reflns_odcompleteness_completeness 99.94
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1-C10A \\sim N1-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
Uanis(C6) = Uanis(C6A)
Uanis(C5) = Uanis(C5A)
Uanis(C4) = Uanis(C4A)
Uanis(C3) = Uanis(C3A)
4. Others
 Sof(H1B)=Sof(C2A)=Sof(H2AA)=Sof(C1A)=Sof(C10A)=Sof(C9A)=Sof(H9A)=Sof(C8A)=
 Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=
 Sof(C3A)=Sof(H3A)=1-FVAR(1)
 Sof(H1A)=Sof(C1)=Sof(C10)=Sof(C2)=Sof(H2A)=Sof(C3)=Sof(H3)=Sof(C6)=Sof(C9)=
 Sof(H9)=Sof(C4)=Sof(H4)=Sof(C7)=Sof(H7)=Sof(C5)=Sof(H5)=Sof(C8)=Sof(H8)=FVAR(1)
5.a Free rotating group:
 O5(H5B,H5C)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C24(H24A,H24B), C20(H20A,H20B), C18(H18A,H18B), C23(H23A,
 H23B), C28(H28A,H28B), C19(H19A,H19B), C15(H15A,H15B), C27(H27A,H27B),
 C26(H26A,H26B), C14(H14A,H14B), C22(H22A,H22B), C12(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1A), N1(H1B), C2(H2A), C3(H3), C9(H9), C4(H4), C7(H7), C5(H5),
 C8(H8), C2A(H2AA), C9A(H9A), C8A(H8A), C7A(H7A), C5A(H5A), C4A(H4A), C3A(H3A)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C17(H17A,H17B,
 H17C)
;
_shelx_res_checksum              10563
_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 2.198
_oxdiff_exptl_absorpt_empirical_full_min 0.756