‘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_7226468
_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 H11 N2 O5 S, C16 H36 N'
_chemical_formula_sum            'C25 H47 N3 O5 S'
_chemical_formula_weight         501.71
_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   geom
_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                96.202(3)
_cell_angle_beta                 103.112(3)
_cell_angle_gamma                94.223(3)
_cell_formula_units_Z            4
_cell_length_a                   10.8520(3)
_cell_length_b                   14.2506(6)
_cell_length_c                   19.6911(8)
_cell_measurement_reflns_used    5898
_cell_measurement_temperature    300(1)
_cell_measurement_theta_max      72.2120
_cell_measurement_theta_min      3.1250
_cell_volume                     2933.2(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w     50.00 115.00   1.00   35.00    --  105.19-111.00  90.00   65
  2  \w     62.00  96.00   1.00    5.00    --   40.62-125.00 120.00   34
  3  \w     35.00 117.00   1.00   35.00    --  105.19 -61.00  90.00   82
  4  \w     59.00 116.00   1.00   35.00    --  105.19-111.00 -60.00   57
  5  \w     90.00 124.00   1.00   35.00    --  105.19 -45.00 -90.00   34
  6  \w     73.00 100.00   1.00   35.00    --  105.19 -94.00-180.00   27
  7  \w     36.00  71.00   1.00   35.00    --  105.19 -45.00 -90.00   35
  8  \w     23.00  83.00   1.00   35.00    --  105.19 -94.00   0.00   60
  9  \w     24.00 152.00   1.00   35.00    --  105.19 -15.00   0.00  128
 10  \w    114.00 178.00   1.00   35.00    --  105.19 111.00  60.00   64
 11  \w    150.00 175.00   1.00   35.00    --  105.19 111.00   0.00   25
 12  \w    100.00 178.00   1.00   35.00    --  105.19  30.00-180.00   78
 13  \w     34.00 118.00   1.00   35.00    --  105.19 -30.00 150.00   84
 14  \w     22.00  58.00   1.00    5.00    --   40.62 -57.00  30.00   36
 15  \w     27.00  86.00   1.00   35.00    --  105.19 -94.00  90.00   59
 16  \w    -64.00  24.00   1.00    5.00    --  -40.62  38.00 -60.00   88
 17  \w    -40.00 -14.00   1.00    5.00    --  -40.62 -77.00 -90.00   26
 18  \w    -57.00  33.00   1.00    5.00    --  -40.62  57.00  30.00   90
 19  \w   -114.00 -17.00   1.00    5.00    --  -40.62 -38.00 120.00   97
;
_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  0.0179
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20872
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.536
_diffrn_reflns_theta_min         2.323
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.762
_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    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         11353
_refine_ls_number_restraints     549
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1075P)^2^+0.1544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7615
_reflns_number_total             11353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01493c2.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
'Adding full bibliography for 7226468--7226476.cif.'
_cod_original_cell_volume        2933.22(19)
_cod_database_code               7226468
_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
2. Restrained distances
 O1A-C1A
 1.4 with sigma of 0.02
 O1B-C1B
 1.4 with sigma of 0.02
 N1-C5A
 1.4 with sigma of 0.02
 N1-C5B
 1.4 with sigma of 0.02
 C49B-C50B
 1.5 with sigma of 0.02
 C49A-C50A
 1.5 with sigma of 0.02
 C48-C49B
 1.5 with sigma of 0.02
 C48-C49A
 1.5 with sigma of 0.02
 C32-C33A
 1.5 with sigma of 0.02
 C33A-C34A
 1.5 with sigma of 0.02
 C32-C33B
 1.5 with sigma of 0.02
 C33B-C34B
 1.5 with sigma of 0.02
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(H48C)=Sof(H48D)=Sof(C49B)=Sof(H49C)=Sof(H49D)=Sof(C50B)=Sof(H50D)=
 Sof(H50E)=Sof(H50F)=1-FVAR(1)
 Sof(H48A)=Sof(H48B)=Sof(C49A)=Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50A)=
 Sof(H50B)=Sof(H50C)=FVAR(1)
 Sof(H32C)=Sof(H32D)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C34B)=Sof(H34D)=
 Sof(H34E)=Sof(H34F)=1-FVAR(2)
 Sof(H32A)=Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C34A)=Sof(H34A)=
 Sof(H34B)=Sof(H34C)=FVAR(2)
 Sof(H29C)=Sof(H29D)=Sof(C30B)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(3)
 Sof(H29A)=Sof(H29B)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(3)
 Sof(O1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=1-FVAR(4)
 Sof(O1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C5A)=Sof(C4A)=Sof(H4A)=
 Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)=FVAR(4)
 Fixed Sof: H1A(0.5) H1B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B),
 C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B), C29(H29C,H29D),
  C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C32(H32C,H32D), C33A(H33A,
 H33B), C33B(H33C,H33D), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B),
 C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C43(H43A,H43B), C44(H44A,H44B),
  C45(H45A,H45B), C47(H47A,H47B), C48(H48A,H48B), C48(H48C,H48D), C49A(H49A,
 H49B), C49B(H49C,H49D), C18(H18A,H18B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), N1(H1B), N2(H2), C4A(H4A), C3A(H3A), C7A(H7A), C6A(H6A), C6B(H6B),
 C7B(H7B), C3B(H3B), C4B(H4B), N3(H3), N4(H4), C12(H12), C13(H13), C15(H15),
 C16(H16)
5.c Fitted hexagon refined as free rotating group:
 C5A(C4A,C3A,C2A,C7A,C6A), C5B(C6B,C7B,C2B,C3B,C4B)
5.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C), C30A(H30A,H30B,H30C), C34A(H34A,H34B,H34C), C30B(H30D,H30E,H30F),
 C34B(H34D,H34E,H34F), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C46(H46A,H46B,
 H46C), C50A(H50A,H50B,H50C), C50B(H50D,H50E,H50F), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              43552
_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
;