‘Frustrated’ hydrogen bond mediated amphiphile self-assembly ‒ a solid state study
Blackholly, Laura R.; Shepherd, Helena J.; Hiscock, Jennifer R.; CrystEngComm 18 (2016) 7021–; doi:10.1039/C6CE01493C

data_7226470
_publ_section_title
;
 &#x2018;Frustrated&#x2019; hydrogen bond mediated amphiphile
 self-assembly -- a solid state study
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7021
_journal_paper_doi               10.1039/C6CE01493C
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C8 H8 N3 O6 S), 2(C16 H36 N), (H2 O)'
_chemical_formula_sum            'C48 H90 N8 O13 S2'
_chemical_formula_weight         1051.39
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-04 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.850(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1853(5)
_cell_length_b                   16.9662(4)
_cell_length_c                   19.0342(5)
_cell_measurement_reflns_used    6355
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      72.4900
_cell_measurement_theta_min      3.5810
_cell_volume                     5827.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w      4.00  34.00   1.00    1.00    --   40.37 -57.00-120.00   30
  2  \w     36.00  72.00   1.00    1.00    --   40.37-125.00 -90.00   36
  3  \w      2.00  80.00   1.00    1.00    --   40.37 -99.00   0.00   78
  4  \w     34.00 116.00   1.00   10.00    --  105.19-111.00   0.00   82
  5  \w     46.00 131.00   1.00   10.00    --  105.19 -45.00 150.00   85
  6  \w     91.00 177.00   1.00   10.00    --  105.19  61.00 -60.00   86
  7  \w    145.00 176.00   1.00   10.00    --  105.19 111.00 -60.00   31
  8  \w    112.00 172.00   1.00   10.00    --  105.19  45.00-180.00   60
  9  \w     39.00 109.00   1.00   10.00    --  105.19 -45.00   0.00   70
 10  \w      8.00 117.00   1.00    1.00    --   40.37  77.00 120.00  109
;
_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      0.0569647000
_diffrn_orient_matrix_UB_12      0.0580094000
_diffrn_orient_matrix_UB_13      0.0505942000
_diffrn_orient_matrix_UB_21      0.0040597000
_diffrn_orient_matrix_UB_22      0.0433486000
_diffrn_orient_matrix_UB_23      -0.0696805000
_diffrn_orient_matrix_UB_31      -0.0634252000
_diffrn_orient_matrix_UB_32      0.0546792000
_diffrn_orient_matrix_UB_33      0.0016632000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         73.098
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.349
_exptl_absorpt_correction_T_max  0.272
_exptl_absorpt_correction_T_min  0.027
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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 colourless'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     176
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0794
_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^)+(0.1517P)^2^+3.6060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2289
_refine_ls_wR_factor_ref         0.2406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4888
_reflns_number_total             5674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01493c2.cif
_cod_data_source_block           Compound_3a
_cod_depositor_comments
'Adding full bibliography for 7226468--7226476.cif.'
_cod_database_code               7226470
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.98
_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, All O(H,H) groups
2. Restrained distances
 N4-C13A \\sim N4-C13B \\sim N4-C17B \\sim N4-C17A \\sim N4-C9B \\sim N4-C9A
\\sim N4-C21B \\sim N4-C21A
 with sigma of 0.02
 C9A-C10A \\sim C10B-C9B \\sim C11B-C10B \\sim C11A-C10A \\sim C22B-C21B \\sim
C21A-C22A \\sim C23A-
 C22A \\sim C22B-C23B \\sim C13A-C14A \\sim C14B-C15B \\sim C15A-C14A \\sim
C14B-C13B \\sim C18B-C17B ~
 C17A-C18A \\sim C19A-C18A \\sim C19B-C18B
 with sigma of 0.02
 C19B-C20B \\sim C20A-C19A \\sim C11B-C12B \\sim C11A-C12A \\sim C15A-C16A
\\sim C16B-C15B \\sim C24B-
 C23B \\sim C23A-C24A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17A) = Uanis(C17B)
Uanis(C21A) = Uanis(C21B)
Uanis(C9A) = Uanis(C9B)
Uanis(C13A) = Uanis(C13B)
Uanis(C10A) = Uanis(C10B)
Uanis(C18A) = Uanis(C18B)
Uanis(C14A) = Uanis(C14B)
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
Uanis(C19A) = Uanis(C19B)
Uanis(C11A) = Uanis(C11B)
Uanis(C15A) = Uanis(C15B)
Uanis(C12A) = Uanis(C12B)
Uanis(C16A) = Uanis(C16B)
Uanis(C20A) = Uanis(C20B)
Uanis(C24A) = Uanis(C24B)
4. Others
 Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C9B)=
 Sof(H9BA)=Sof(H9BB)=Sof(C13B)=Sof(H13C)=Sof(H13D)=Sof(C10B)=Sof(H10C)=
 Sof(H10D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=Sof(C14B)=Sof(H14C)=Sof(H14D)=
 Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C19B)=
 Sof(H19C)=Sof(H19D)=Sof(C11B)=Sof(H11C)=Sof(H11D)=Sof(C15B)=Sof(H15C)=
 Sof(H15D)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C16B)=Sof(H16D)=
 Sof(H16E)=Sof(H16F)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C24B)=
 Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C18A)=
 Sof(H18A)=Sof(H18B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C22A)=Sof(H22A)=Sof(H22B)=
 Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(C20A)=
 Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C24A)=
 Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C23A)=
 Sof(H23A)=Sof(H23B)=FVAR(1)
 Fixed Sof: H7A(0.5) H7B(0.5)
5.a Free rotating group:
 O7(H7A,H7B)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14A(H14A,H14B), C10A(H10A,H10B), C18A(H18A,H18B), C13A(H13A,
 H13B), C9A(H9AA,H9AB), C22A(H22A,H22B), C17A(H17A,H17B), C21A(H21A,H21B),
 C19A(H19A,H19B), C11A(H11A,H11B), C15A(H15A,H15B), C23A(H23A,H23B), C17B(H17C,
 H17D), C21B(H21C,H21D), C9B(H9BA,H9BB), C13B(H13C,H13D), C10B(H10C,H10D),
 C18B(H18C,H18D), C14B(H14C,H14D), C22B(H22C,H22D), C23B(H23C,H23D), C19B(H19C,
 H19D), C11B(H11C,H11D), C15B(H15C,H15D)
5.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C5(H5), C2(H2A), C6(H6), C3(H3A)
5.d Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C12A(H12A,H12B,H12C), C20A(H20A,H20B,H20C), C24A(H24A,
 H24B,H24C), C12B(H12D,H12E,H12F), C16B(H16D,H16E,H16F), C20B(H20D,H20E,H20F),
 C24B(H24D,H24E,H24F)
;
_shelx_res_checksum              14157
_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 2.424
_oxdiff_exptl_absorpt_empirical_full_min 0.217