‘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_7226471
_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         'C9 H8 F3 N2 O4 S, C16 H36 N, H O0.5'
_chemical_formula_sum            'C25 H45 F3 N3 O4.5 S'
_chemical_formula_weight         548.70
_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
_audit_creation_date             2016-08-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_audit_update_record
;
2016-08-16 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.145(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4863(8)
_cell_length_b                   16.9500(6)
_cell_length_c                   19.0704(5)
_cell_measurement_reflns_used    4100
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      72.4260
_cell_measurement_theta_min      3.5450
_cell_volume                     5913.5(4)
_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)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -65.00 -13.00   1.00    5.00    --  -40.62 -77.00  90.00   52
  2  \w   -112.00 -82.00   1.00    5.00    --  -40.62 -77.00  90.00   30
  3  \w     41.00  87.00   1.00    5.00    --   40.62-125.00   0.00   46
  4  \w      0.00  98.00   1.00    5.00    --   40.62  19.00   0.00   98
  5  \w     80.00 172.00   1.00   20.00    --  105.19  61.00 150.00   92
  6  \w     33.00 131.00   1.00   20.00    --  105.19 -61.00   0.00   98
  7  \w     60.00 159.00   1.00   20.00    --  105.19  15.00 120.00   99
  8  \w     32.00 108.00   1.00   20.00    --  105.19 -45.00-150.00   76
;
_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  0.0146
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9536
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.555
_exptl_absorpt_coefficient_mu    1.438
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.978
_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_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       needle
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         5202
_refine_ls_number_restraints     351
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0620P)^2^+10.9899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4441
_reflns_number_total             5202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01493c2.cif
_cod_data_source_block           compound_4
_cod_depositor_comments
'Adding full bibliography for 7226468--7226476.cif.'
_cod_original_formula_sum        'C25 H45 F3 N3 O4.50 S'
_cod_database_code               7226471
_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) groups
2. Uiso/Uaniso restraints and constraints
C21B \\sim C21A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(C14B)=Sof(H14C)=Sof(H14D)=Sof(C10B)=
 Sof(H10C)=Sof(H10D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=Sof(C15B)=Sof(H15C)=
 Sof(H15D)=Sof(C11B)=Sof(H11C)=Sof(H11D)=Sof(C19B)=Sof(H19C)=Sof(H19D)=
 Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C16B)=
 Sof(H16C)=Sof(H16D)=Sof(C20B)=Sof(H20C)=Sof(H20D)=Sof(C24B)=Sof(H24C)=
 Sof(H24D)=Sof(C13B)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C17B)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=Sof(C21B)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C25B)=
 Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C11A)=
 Sof(H11A)=Sof(H11B)=Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(C10A)=Sof(H10A)=
 Sof(H10B)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=
 Sof(H13C)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C24A)=Sof(H24A)=Sof(H24B)=
 Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 Sof(C20A)=Sof(H20A)=Sof(H20B)=FVAR(1)
5.a Free rotating group:
 O5(H5)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C15A(H15A,H15B), C23A(H23A,H23B), C11A(H11A,H11B), C22A(H22A,
 H22B), C10A(H10A,H10B), C14A(H14A,H14B), C19A(H19A,H19B), C18A(H18A,H18B),
 C16A(H16A,H16B), C24A(H24A,H24B), C12A(H12A,H12B), C20A(H20A,H20B), C22B(H22C,
 H22D), C14B(H14C,H14D), C10B(H10C,H10D), C18B(H18C,H18D), C15B(H15C,H15D),
 C11B(H11C,H11D), C19B(H19C,H19D), C23B(H23C,H23D), C12B(H12C,H12D), C16B(H16C,
 H16D), C20B(H20C,H20D), C24B(H24C,H24D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C7(H7), C4(H4), C3(H3)
5.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C17A(H17A,H17B,H17C), C25A(H25A,H25B,H25C), C21A(H21A,
 H21B,H21C), C13B(H13D,H13E,H13F), C17B(H17D,H17E,H17F), C21B(H21D,H21E,H21F),
 C25B(H25D,H25E,H25F)
;
_shelx_res_checksum              50082
_shelx_shelxl_version_number     2014/7
_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
;