‘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_7226474
_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         'C10 H7 F6 N2 O3 S2, C16 H36 N, H2 O'
_chemical_formula_sum            'C26 H43 F6 N3 O4 S2'
_chemical_formula_weight         639.75
_chemical_name_systematic
;
 ?
;
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-17 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                74.424(4)
_cell_angle_beta                 87.100(4)
_cell_angle_gamma                84.476(3)
_cell_formula_units_Z            4
_cell_length_a                   12.1225(5)
_cell_length_b                   13.1483(4)
_cell_length_c                   21.4144(11)
_cell_measurement_reflns_used    7166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4770
_cell_measurement_theta_min      3.4970
_cell_volume                     3271.5(2)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w   -114.00 -16.00   1.00    7.50    --  -40.37 -38.00  30.00   98
  2  \w    -72.00  19.00   1.00    7.50    --  -40.37  77.00-180.00   91
  3  \w   -114.00 -23.00   1.00    7.50    --  -40.37 -38.00 -60.00   91
  4  \w      2.00  80.00   1.00    7.50    --   40.37 -99.00 -90.00   78
  5  \w     23.00  77.00   1.00    7.50    --   40.37-125.00 120.00   54
  6  \w     84.00 120.00   1.00   30.00    --  105.19  45.00  90.00   36
  7  \w     90.00 174.00   1.00   30.00    --  105.19  45.00 -90.00   84
  8  \w     71.00 105.00   1.00   30.00    --  105.19 -94.00 -60.00   34
  9  \w     35.00 112.00   1.00   30.00    --  105.19 -61.00 -30.00   77
 10  \w     37.00 130.00   1.00   30.00    --  105.19 -61.00-150.00   93
 11  \w     33.00 130.00   1.00   30.00    --  105.19 -30.00  90.00   97
 12  \w     81.00 116.00   1.00   30.00    --  105.19-111.00-150.00   35
 13  \w    145.00 170.00   1.00   30.00    --  105.19  45.00  90.00   25
 14  \w     79.00 116.00   1.00   30.00    --  105.19-111.00  60.00   37
 15  \w     31.00 135.00   1.00   30.00    --  105.19 -77.00  90.00  104
 16  \w     36.00  63.00   1.00   30.00    --  105.19 -94.00 -60.00   27
 17  \w     26.00 141.00   1.00   30.00    --  105.19 -15.00 -90.00  115
;
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21742
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.503
_exptl_absorpt_coefficient_mu    2.082
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.636
_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    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.004
_refine_diff_density_max         1.772
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     896
_refine_ls_number_reflns         11568
_refine_ls_number_restraints     898
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.1110
_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^)+(0.1841P)^2^+9.5549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3006
_refine_ls_wR_factor_ref         0.3293
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8722
_reflns_number_total             11568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01493c2.cif
_cod_data_source_block           compound_7
_cod_depositor_comments
'Adding full bibliography for 7226468--7226476.cif.'
_cod_database_code               7226474
_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,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C14B-C12B
 1.54 with sigma of 0.02
 F12B-C12B
 1.3 with sigma of 0.02
 C12B-F11B
 1.3 with sigma of 0.02
 C12B-F10B
 1.3 with sigma of 0.02
 F12B-F11B
 2 with sigma of 0.02
 F12B-F10B
 2 with sigma of 0.02
 F10B-F11B
 2 with sigma of 0.02
 F7B-F8B
 2 with sigma of 0.02
 F8B-F9B
 2 with sigma of 0.02
 F9B-F7B
 2 with sigma of 0.02
 F12A-F10A \\sim F10A-F11A \\sim F11A-F12A \\sim F8A-F9A \\sim F9A-F7A \\sim
F7A-F8A
 with sigma of 0.002
 C17A-C13A \\sim C17A-C16A
 with sigma of 0.02
 F12A-C12A \\sim F11A-C12A \\sim F10A-C12A \\sim F8A-C11A \\sim F7A-C11A \\sim
F9A-C11A \\sim F3-C2 ~
 F1-C2 \\sim F2-C2 \\sim F6-C3 \\sim F5-C3 \\sim F4-C3
 with sigma of 0.02
 C12A-C14A \\sim C16A-C11A \\sim C3-C5 \\sim C2-C4
 with sigma of 0.02
 C32-C31 \\sim C24-C23 \\sim C48_$1-C47_$1 \\sim C44_$1-C43_$1 \\sim
C51_$1-C52_$1
 with sigma of 0.02
 C31-C30 \\sim C46_$1-C47_$1 \\sim C39_$1-C38_$1 \\sim C51_$1-C50_$1 \\sim
C43_$1-C42_$1
 with sigma of 0.02
 C36-C35 \\sim C36A-C35A
 with sigma of 0.02
 C35-C34 \\sim C35A-C34
 with sigma of 0.02
3. Restrained planarity
 C13A, C14A, C12A, C15A
 with sigma of 0.1
 C17A, C16A, C15A, C11A
 with sigma of 0.1
 C13B, C14B, C12B, C15B
 with sigma of 0.1
 C17B, C16B, C15B, C11B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C14B) \\sim Ueq, Uanis(C12B) \\sim Ueq, Uanis(F12B) \\sim Ueq,
Uanis(F11B) \\sim Ueq, Uanis(F10B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.1
Uanis(C14A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(F10A) \\sim Ueq,
Uanis(F12A) \\sim Ueq, Uanis(F11A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.1
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(H26C)=Sof(H26D)=Sof(C27B)=Sof(H27C)=Sof(H27D)=Sof(C28B)=Sof(H28D)=
 Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(H26A)=Sof(H26B)=Sof(C28A)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(H34C)=Sof(H34D)=Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36D)=
 Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=FVAR(2)
 Sof(H3B)=Sof(C14B)=Sof(C13B)=Sof(H13B)=Sof(C18B)=Sof(C17B)=Sof(H17B)=
 Sof(C16B)=Sof(C15B)=Sof(H15B)=Sof(C11B)=Sof(F7B)=Sof(F9B)=Sof(F8B)=Sof(F10B)=
 Sof(F12B)=Sof(F11B)=Sof(C12B)=1-FVAR(3)
 Sof(H3A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(C11A)=Sof(C18A)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(F11A)=
 Sof(F12A)=Sof(F10A)=Sof(C12A)=FVAR(3)
7.a Free rotating group:
 O8(H8A,H8B), O7(H7A,H7B)
7.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C45(H45A,H45B), C41(H41A,H41B), C49(H49A,H49B), C20(H20A,
 H20B), C42(H42A,H42B), C29(H29A,H29B), C50(H50A,H50B), C47(H47A,H47B),
 C37(H37A,H37B), C46(H46A,H46B), C30(H30A,H30B), C31(H31A,H31B), C21(H21A,H21B),
  C51(H51A,H51B), C43(H43A,H43B), C22(H22A,H22B), C38(H38A,H38B), C39(H39A,
 H39B), C23(H23A,H23B), C33(H33A,H33B), C34(H34A,H34B), C34(H34C,H34D),
 C35(H35A,H35B), C27A(H27A,H27B), C26(H26A,H26B), C26(H26C,H26D), C25(H25A,
 H25B), C27B(H27C,H27D), C35A(H35C,H35D)
7.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), N2(H2), N3(H3A), N3(H3B), C6(H6), C7(H7), C1(H1A), C13A(H13A),
  C15A(H15A), C17A(H17A), C13B(H13B), C17B(H17B), C15B(H15B)
7.d Fitted hexagon refined as free rotating group:
 C18A(C13A,C14A,C15A,C16A,C17A), C14B(C13B,C18B,C17B,C16B,C15B)
7.e Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C48(H48A,H48B,H48C), C32(H32A,H32B,H32C), C44(H44A,H44B,
 H44C), C24(H24A,H24B,H24C), C40(H40A,H40B,H40C), C36(H36A,H36B,H36C),
 C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F), C36A(H36D,H36E,H36F)
;
_shelx_res_checksum              69426
_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
;