‘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_7226473
_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(C10 H7 F6 N2 O4 S), 2(C16 H36 N)'
_chemical_formula_sum            'C26 H43 F6 N3 O4 S'
_chemical_formula_weight         607.69
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-01
_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                 92.086(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3272(4)
_cell_length_b                   20.7771(6)
_cell_length_c                   22.3152(6)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      72.6420
_cell_measurement_theta_min      2.9020
_cell_volume                     6175.0(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      air
_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 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -69.00  33.00   1.00    7.50    --  -40.37  57.00 120.00  102
  2  \w    -95.00 -19.00   1.00    7.50    --  -40.37 -38.00 -60.00   76
  3  \w   -112.00 -74.00   1.00    7.50    --  -40.37 -57.00  60.00   38
  4  \w    100.00 154.00   1.00   30.00    --  105.19 111.00 -60.00   54
  5  \w    111.00 171.00   1.00   30.00    --  105.19  45.00 -90.00   60
  6  \w     81.00 108.00   1.00   30.00    --  105.19  45.00 -90.00   27
  7  \w     80.00 129.00   1.00   30.00    --  105.19 -30.00-150.00   49
  8  \w     52.00 109.00   1.00   30.00    --  105.19 -45.00-150.00   57
  9  \w     26.00  81.00   1.00   30.00    --  105.19 -94.00  30.00   55
 10  \w     49.00 138.00   1.00   30.00    --  105.19 -77.00 120.00   89
 11  \w     76.00 102.00   1.00   30.00    --  105.19  61.00  90.00   26
 12  \w     28.00 101.00   1.00   30.00    --  105.19 -94.00  60.00   73
;
_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      -0.0153185000
_diffrn_orient_matrix_UB_12      0.0227519000
_diffrn_orient_matrix_UB_13      0.0646984000
_diffrn_orient_matrix_UB_21      -0.0297273000
_diffrn_orient_matrix_UB_22      0.0671992000
_diffrn_orient_matrix_UB_23      -0.0236311000
_diffrn_orient_matrix_UB_31      -0.1107908000
_diffrn_orient_matrix_UB_32      -0.0214419000
_diffrn_orient_matrix_UB_33      -0.0052606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25495
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.062
_diffrn_reflns_theta_min         2.907
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.734
_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    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         12024
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0465P)^2^+1.7581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9632
_reflns_number_total             12024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01493c2.cif
_cod_data_source_block           Compound_6
_cod_depositor_comments
'Adding full bibliography for 7226468--7226476.cif.'
_cod_database_code               7226473
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.96
_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 C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C52A-C51A \\sim C51B-C52B \\sim C40-C39 \\sim C48A-C47A \\sim C48B-C47B \\sim
C32-C31 \\sim C28-C27 ~
 C24-C23 \\sim C36-C35 \\sim C44-C43
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C46A) = Uanis(C46B)
Uanis(C47A) = Uanis(C47B)
Uanis(C48A) = Uanis(C48B)
Uanis(C51A) = Uanis(C51B)
Uanis(C52A) = Uanis(C52B)
4. Others
 Sof(H45C)=Sof(H45D)=Sof(C46B)=Sof(H46C)=Sof(H46D)=Sof(C47B)=Sof(H47C)=
 Sof(H47D)=Sof(C48B)=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(1)
 Sof(H45A)=Sof(H45B)=Sof(C47A)=Sof(H47A)=Sof(H47B)=Sof(C46A)=Sof(H46A)=
 Sof(H46B)=Sof(C48A)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(1)
 Sof(C51B)=Sof(H51C)=Sof(H51D)=Sof(C52B)=Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(2)
 Sof(C51A)=Sof(H51A)=Sof(H51B)=Sof(C52A)=Sof(H52A)=Sof(H52B)=Sof(H52C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C33(H33A,H33B), C21(H21A,H21B), C29(H29A,H29B), C20(H20A,
 H20B), C10(H10A,H10B), C26(H26A,H26B), C42(H42A,H42B), C35(H35A,H35B),
 C22(H22A,H22B), C30(H30A,H30B), C34(H34A,H34B), C37(H37A,H37B), C41(H41A,H41B),
  C23(H23A,H23B), C27(H27A,H27B), C39(H39A,H39B), C43(H43A,H43B), C38(H38A,
 H38B), C31(H31A,H31B), C45(H45A,H45B), C45(H45C,H45D), C49(H49A,H49B),
 C50(H50A,H50B), C47A(H47A,H47B), C51A(H51A,H51B), C46A(H46A,H46B), C46B(H46C,
 H46D), C47B(H47C,H47D), C51B(H51C,H51D)
5.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), N3(H3), N2(H2), C6(H6), C7(H7), C17(H17), C1(H1A), C16(H16),
 C11(H11)
5.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C44(H44A,H44B,H44C), C36(H36A,H36B,H36C), C40(H40A,H40B,
 H40C), C32(H32A,H32B,H32C), C28(H28A,H28B,H28C), C48A(H48A,H48B,H48C),
 C52A(H52A,H52B,H52C), C48B(H48D,H48E,H48F), C52B(H52D,H52E,H52F)
;
_shelx_res_checksum              54575
_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 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.820