‘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_7226472
_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(C9 H8 F3 N2 O3 S2), C2 H6 O S, H2 O, 2(C16 H36 N)'
_chemical_formula_sum            'C26 H48 F3 N3 O4 S2.5'
_chemical_formula_weight         603.82
_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             2016-05-31
_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                78.866(5)
_cell_angle_beta                 76.851(4)
_cell_angle_gamma                82.631(5)
_cell_formula_units_Z            2
_cell_length_a                   12.3465(7)
_cell_length_b                   13.2148(9)
_cell_length_c                   20.8662(10)
_cell_measurement_reflns_used    7738
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      72.7640
_cell_measurement_theta_min      3.4110
_cell_volume                     3240.1(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 0.978
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -64.00  32.00   1.00    7.50    --  -40.37  38.00   0.00   96
  2  \w     13.00  72.00   1.00    7.50    --   40.37 -99.00  30.00   59
  3  \w     46.00 116.00   1.00   30.00    --  105.19-111.00 -30.00   70
  4  \w     83.00 126.00   1.00   30.00    --  105.19 -30.00-180.00   43
  5  \w     67.00 134.00   1.00   30.00    --  105.19  15.00 -60.00   67
  6  \w    149.00 176.00   1.00   30.00    --  105.19  15.00 -60.00   27
  7  \w    105.00 162.00   1.00   30.00    --  105.19 111.00 -60.00   57
  8  \w     88.00 173.00   1.00   30.00    --  105.19  45.00   0.00   85
  9  \w    103.00 130.00   1.00   30.00    --  105.19 -61.00 150.00   27
 10  \w     59.00  86.00   1.00   30.00    --  105.19 -61.00 150.00   27
 11  \w     46.00 104.00   1.00   30.00    --  105.19 -94.00  60.00   58
 12  \w     37.00 117.00   1.00   30.00    --  105.19 -30.00 -30.00   80
 13  \w     32.00  86.00   1.00    7.50    --   40.37-125.00-120.00   54
 14  \w     32.00 110.00   1.00   30.00    --  105.19-111.00-180.00   78
 15  \w     34.00  98.00   1.00   30.00    --  105.19 -61.00 -60.00   64
 16  \w     30.00  97.00   1.00   30.00    --  105.19 -94.00-120.00   67
 17  \w     57.00 124.00   1.00   30.00    --  105.19 178.00-150.00   67
 18  \w   -111.00 -23.00   1.00    7.50    --  -40.37 -57.00  90.00   88
 19  \w   -109.00 -16.00   1.00    7.50    --  -40.37 -38.00-180.00   93
;
_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      0.0151256000
_diffrn_orient_matrix_UB_12      -0.1187699000
_diffrn_orient_matrix_UB_13      0.0189463000
_diffrn_orient_matrix_UB_21      0.1168213000
_diffrn_orient_matrix_UB_22      -0.0010676000
_diffrn_orient_matrix_UB_23      -0.0460511000
_diffrn_orient_matrix_UB_31      0.0516899000
_diffrn_orient_matrix_UB_32      0.0109695000
_diffrn_orient_matrix_UB_33      0.0586458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0942
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21922
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         2.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.225
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.940
_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    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.063
_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     717
_refine_ls_number_reflns         11448
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0338P)^2^+0.6218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8101
_reflns_number_total             11448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01493c2.cif
_cod_data_source_block           Compound_5
_cod_depositor_comments
'Adding full bibliography for 7226468--7226476.cif.'
_cod_database_code               7226472
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H7A(0.059) H7B(0.059) H1(0.029) H2(0.031) H4(0.034) H3(0.037)
 H9A(0.03) H9B(0.03) H20A(0.03) H20B(0.03) H19A(0.027) H19B(0.027) H4A(0.033)
 H31A(0.029) H31B(0.029) H21A(0.034) H21B(0.034) H6(0.03) H27A(0.031)
 H27B(0.031) H25A(0.036) H25B(0.036) H3A(0.036) H15(0.035) H23A(0.028)
 H23B(0.028) H7(0.034) H18A(0.035) H18B(0.035) H48A(0.034) H48B(0.034)
 H32A(0.031) H32B(0.031) H24A(0.032) H24B(0.032) H33A(0.031) H33B(0.031)
 H43A(0.033) H43B(0.033) H16(0.036) H36A(0.039) H36B(0.039) H39A(0.035)
 H39B(0.035) H49A(0.036) H49B(0.036) H47A(0.032) H47B(0.032) H34A(0.048)
 H34B(0.048) H34C(0.048) H35A(0.034) H35B(0.034) H44A(0.037) H44B(0.037)
 H45A(0.045) H45B(0.045) H22A(0.051) H22B(0.051) H22C(0.051) H13(0.042)
 H28A(0.04) H28B(0.04) H12(0.044) H40A(0.046) H40B(0.046) H37A(0.041)
 H37B(0.041) H26A(0.065) H26B(0.065) H26C(0.065) H41A(0.05) H41B(0.05)
 H38A(0.07) H38B(0.07) H38C(0.07) H29A(0.056) H29B(0.056) H29C(0.056)
 H29D(0.056) H50A(0.065) H50B(0.065) H50C(0.065) H46A(0.074) H46B(0.074)
 H46C(0.074) H42A(0.081) H42B(0.081) H42C(0.081) H51A(0.101) H51B(0.101)
 H51C(0.101) H30A(0.077) H30B(0.077) H30C(0.077) H52A(0.091) H52B(0.091)
 H52C(0.091) H52D(0.091) H52E(0.091) H52F(0.091) H30D(0.077) H30E(0.077)
 H30F(0.077)
 Fixed X: H7A(0.3185) H7B(0.4318) H1(0.8915) H2(0.8297) H4(0.8291) H3(0.691)
 H9A(0.7101) H9B(0.6179) H20A(0.8961) H20B(0.9314) H19A(0.7322) H19B(0.7658)
 H4A(0.7161) H31A(0.7153) H31B(0.8297) H21A(0.91) H21B(0.9246) H6(1.0272)
 H27A(0.7648) H27B(0.6635) H25A(0.3671) H25B(0.427) H3A(0.772) H15(0.5346)
 H23A(0.6012) H23B(0.5516) H7(1.0806) H18A(1.0003) H18B(1.0325) H48A(0.3679)
 H48B(0.4057) H32A(0.735) H32B(0.8522) H24A(0.5538) H24B(0.4954) H33A(0.7982)
 H33B(0.9119) H43A(0.3856) H43B(0.3182) H16(0.4043) H36A(0.2465) H36B(0.3347)
 H39A(0.105) H39B(0.1203) H49A(0.2409) H49B(0.2871) H47A(0.2235) H47B(0.1842)
 H34A(0.847) H34B(0.9631) H34C(0.9323) H35A(0.4229) H35B(0.3623) H44A(0.2279)
 H44B(0.1715) H45A(0.3763) H45B(0.3272) H22A(1.1009) H22B(1.0978) H22C(1.0858)
 H13(0.7391) H28A(0.5377) H28B(0.6327) H12(0.6104) H40A(0.2002) H40B(0.1883)
 H37A(0.3874) H37B(0.476) H26A(0.2731) H26B(0.308) H26C(0.378) H41A(0.0079)
 H41B(0.0419) H38A(0.3857) H38B(0.4201) H38C(0.296) H29A(0.6139) H29B(0.7073)
 H29C(0.558) H29D(0.6642) H50A(0.3712) H50B(0.4121) H50C(0.463) H46A(0.2238)
 H46B(0.175) H46C(0.287) H42A(-0.0584) H42B(-0.0116) H42C(-0.1118) H51A(0.2204)
 H51B(0.2213) H51C(0.3305) H30A(0.5687) H30B(0.5773) H30C(0.4812) H52A(0.0675)
 H52B(0.0542) H52C(0.0497) H52D(0.3391) H52E(0.2295) H52F(0.2365) H30D(0.7774)
 H30E(0.6896) H30F(0.6819)
 Fixed Y: H7A(0.597) H7B(0.5987) H1(0.8814) H2(0.8134) H4(0.6374) H3(0.7067)
 H9A(0.8094) H9B(0.8696) H20A(0.2248) H20B(0.2899) H19A(0.1894) H19B(0.2657)
 H4A(1.038) H31A(0.4964) H31B(0.4309) H21A(0.0733) H21B(0.1348) H6(1.0028)
 H27A(0.306) H27B(0.2438) H25A(0.3584) H25B(0.3074) H3A(1.1614) H15(0.6497)
 H23A(0.3752) H23B(0.424) H7(1.129) H18A(0.5499) H18B(0.6153) H48A(0.7977)
 H48B(0.9071) H32A(0.4792) H32B(0.418) H24A(0.2095) H24B(0.2644) H33A(0.6288)
 H33B(0.5687) H43A(0.7311) H43B(0.7145) H16(0.7013) H36A(1.0403) H36B(1.0567)
 H39A(0.8165) H39B(0.934) H49A(0.8792) H49B(0.9857) H47A(0.9615) H47B(0.854)
 H34A(0.5996) H34B(0.5471) H34C(0.6654) H35A(0.8962) H35B(0.8823) H44A(0.6855)
 H44B(0.6575) H45A(0.5597) H45B(0.535) H22A(0.1756) H22B(0.0552) H22C(0.1221)
 H13(0.8545) H28A(0.381) H28B(0.4565) H12(0.9052) H40A(0.7854) H40B(0.9058)
 H37A(1.042) H37B(1.0575) H26A(0.2191) H26B(0.2014) H26C(0.1437) H41A(0.7811)
 H41B(0.8351) H38A(1.2209) H38B(1.2168) H38C(1.2053) H29A(0.2867) H29B(0.3632)
 H29C(0.3627) H29D(0.2879) H50A(0.9213) H50B(0.8175) H50C(0.9205) H46A(0.4913)
 H46B(0.4665) H46C(0.4074) H42A(0.9366) H42B(0.9973) H42C(0.9297) H51A(0.3992)
 H51B(0.347) H51C(0.3883) H30A(0.4959) H30B(0.4078) H30C(0.4132) H52A(0.6026)
 H52B(0.4839) H52C(0.5544) H52D(0.5133) H52E(0.4703) H52F(0.5901) H30D(0.4089)
 H30E(0.4327) H30F(0.4983)
 Fixed Z: H7A(0.6123) H7B(0.6091) H1(0.6918) H2(0.6292) H4(0.7188) H3(0.7757)
 H9A(0.5617) H9B(0.6091) H20A(0.6138) H20B(0.5421) H19A(0.582) H19B(0.5149)
 H4A(0.7883) H31A(0.5885) H31B(0.5901) H21A(0.5705) H21B(0.4972) H6(0.679)
 H27A(0.6799) H27B(0.6833) H25A(0.5892) H25B(0.5268) H3A(0.8362) H15(0.8659)
 H23A(0.5267) H23B(0.5911) H7(0.7252) H18A(0.7053) H18B(0.7524) H48A(0.6637)
 H48B(0.6631) H32A(0.4757) H32B(0.4779) H24A(0.5898) H24B(0.6507) H33A(0.4919)
 H33B(0.504) H43A(0.7689) H43B(0.8426) H16(0.9551) H36A(0.8169) H36B(0.7494)
 H39A(0.8279) H39B(0.8212) H49A(0.594) H49B(0.5905) H47A(0.7133) H47B(0.7127)
 H34A(0.3798) H34B(0.3927) H34C(0.3949) H35A(0.7724) H35B(0.8476) H44A(0.7352)
 H44B(0.8112) H45A(0.7494) H45B(0.8263) H22A(0.501) H22B(0.52) H22C(0.576)
 H13(0.8791) H28A(0.7089) H28B(0.6923) H12(0.9683) H40A(0.9206) H40B(0.9175)
 H37A(0.8765) H37B(0.8091) H26A(0.5781) H26B(0.6474) H26C(0.5904) H41A(0.9459)
 H41B(0.998) H38A(0.7773) H38B(0.8456) H38C(0.8441) H29A(0.8001) H29B(0.7838)
 H29C(0.8136) H29D(0.7915) H50A(0.4945) H50B(0.5363) H50C(0.5357) H46A(0.7284)
 H46B(0.8054) H46C(0.7741) H42A(0.8923) H42B(0.9361) H42C(0.9686) H51A(0.9378)
 H51B(1.0118) H51C(0.9649) H30A(0.81) H30B(0.8713) H30C(0.8325) H52A(1.0455)
 H52B(1.0552) H52C(0.9861) H52D(1.0543) H52E(1.0998) H52F(1.078) H30D(0.776)
 H30E(0.8397) H30F(0.7695)
;
_shelx_res_checksum              96265
_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 2.001
_oxdiff_exptl_absorpt_empirical_full_min 0.719