Ionic N-phenylpyridinium tetracatenar mesogens: competing driving forces in mesophase formation and unprecedented difference in phase stabilisation within a homologous series.
Herod, Jordan D.; Bates, Martin A.; Whitwood, Adrian C.; Bruce, Duncan W.; Soft matter 15 (2019) 4432–4436; doi:10.1039/c9sm00846b

data_1551057
_publ_section_title
;
 Ionic N-phenylpyridinium tetracatenar mesogens: competing driving forces
 in mesophase formation and unprecedented difference in phase
 stabilisation within a homologous series.
;
_journal_issue                   22
_journal_name_full               'Soft matter'
_journal_page_first              4432
_journal_page_last               4436
_journal_paper_doi               10.1039/c9sm00846b
_journal_volume                  15
_journal_year                    2019
_chemical_formula_moiety         'C55 H82 N O4, C F3 O3 S, 0.96(H2 O)'
_chemical_formula_sum            'C56 H83.92 F3 N O7.96 S'
_chemical_formula_weight         987.58
_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     dual
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-25 deposited with the CCDC.    2019-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                92.279(2)
_cell_angle_beta                 97.130(2)
_cell_angle_gamma                113.899(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2146(3)
_cell_length_b                   10.5078(3)
_cell_length_c                   31.0190(7)
_cell_measurement_reflns_used    13214
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.9540
_cell_measurement_theta_min      4.3020
_cell_volume                     2711.22(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -30.00  70.00   1.00    3.00    --    0.00  77.00   0.00  100
  2  \w    -69.00  21.00   1.00    3.00    --    0.00 -57.00-120.00   90
  3  \w     33.00 123.00   1.00   12.00    --   54.00  57.00   0.00   90
  4  \w     24.00 124.00   1.00   12.00    --   54.00  77.00 -90.00  100
  5  \w     10.00 127.00   1.00   12.00    --   54.00  19.00-120.00  117
  6  \w    -15.00  75.00   1.00   12.00    --   54.00 -57.00  60.00   90
  7  \w     23.00 111.00   1.00   12.00    --   54.00-125.00  60.00   88
  8  \w     23.00 111.00   1.00   12.00    --   54.00-125.00 -30.00   88
  9  \w     23.00 111.00   1.00   12.00    --   54.00-125.00-120.00   88
 10  \w     36.00 113.00   1.00   12.00    --  108.00-111.00 -60.00   77
 11  \w    100.00 178.00   1.00   12.00    --  108.00 111.00-150.00   78
 12  \w     36.00 113.00   1.00   12.00    --  108.00-111.00-180.00   77
 13  \w     82.00 178.00   1.00   12.00    --  108.00  37.00  30.00   96
 14  \w     82.00 178.00   1.00   12.00    --  108.00  37.00 -90.00   96
 15  \w     35.00 142.00   1.00   12.00    --  108.00 -25.00  90.00  107
 16  \w     36.00 146.00   1.00   12.00    --  108.00 -91.00 120.00  110
 17  \w     36.00 113.00   1.00   12.00    --  108.00-111.00  60.00   77
 18  \w     35.00 134.00   1.00   12.00    --  108.00 -35.00-148.00   99
 19  \w     36.00 134.00   1.00   12.00    --  108.00 -37.00 -30.00   98
 20  \w     38.00 138.00   1.00   12.00    --  108.00 -77.00 -30.00  100
 21  \w     35.00 142.00   1.00   12.00    --  108.00 -25.00  30.00  107
 22  \w     40.00 130.00   1.00   12.00    --  108.00 -63.00-180.00   90
 23  \w     40.00 130.00   1.00   12.00    --  108.00 -63.00  90.00   90
 24  \w    100.00 178.00   1.00   12.00    --  108.00 111.00  90.00   78
 25  \w    -69.00  21.00   1.00    3.00    --    0.00 -57.00 -90.00   90
 26  \w    -72.00  26.00   1.00    3.00    --    0.00 -37.00 -60.00   98
 27  \w     33.00 123.00   1.00   12.00    --   54.00  57.00  90.00   90
 28  \w     24.00 124.00   1.00   12.00    --   54.00  77.00  30.00  100
 29  \w     24.00 124.00   1.00   12.00    --   54.00  77.00-150.00  100
 30  \w     24.00 124.00   1.00   12.00    --   54.00  77.00  90.00  100
 31  \w     24.00 124.00   1.00   12.00    --   54.00  77.00 150.00  100
 32  \w     24.00 124.00   1.00   12.00    --   54.00  77.00 -30.00  100
 33  \w     82.00 178.00   1.00   12.00    --  108.00  37.00-150.00   96
 34  \w     82.00 178.00   1.00   12.00    --  108.00  37.00 -30.00   96
 35  \w     36.00 178.00   1.00   12.00    --  108.00  12.00-180.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1721961000
_diffrn_orient_matrix_UB_12      -0.0084418000
_diffrn_orient_matrix_UB_13      -0.0079129000
_diffrn_orient_matrix_UB_21      -0.0606417000
_diffrn_orient_matrix_UB_22      -0.1383588000
_diffrn_orient_matrix_UB_23      0.0213220000
_diffrn_orient_matrix_UB_31      0.0302966000
_diffrn_orient_matrix_UB_32      0.0822003000
_diffrn_orient_matrix_UB_33      0.0448654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38061
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.331
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       needle
_exptl_crystal_F_000             1067
_exptl_crystal_size_max          0.623
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         9663
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0776P)^2^+2.0412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8161
_reflns_number_total             9663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sm00846b2.cif
_cod_data_source_block           dwb1804c
_cod_depositor_comments          'Adding full bibliography for 1551057.cif.'
_cod_original_cell_volume        2711.22(13)
_cod_database_code               1551057
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C56 H82 F3 N1 O7 S1'
_chemical_oxdiff_usercomment     'Jordan Herod JDH298_C8_OTf'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.563
_reflns_odcompleteness_completeness 99.98
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C26A-C25 = C27A-C26A = C28A-C27A = C29A-C28A = C30A-C29A = C26-C25 = C27-C26 =
  C27-C28 = C29-C28 = C30-C29
 1.54 with sigma of 0.01
 C30-C31 = C30A-C31A
 1.52 with sigma of 0.01
 F2A-C56A = F1A-C56A = F3A-C56A
 1.33 with sigma of 0.05
 S1A-O6A = S1A-O5A = S1A-O7A
 1.44 with sigma of 0.05
 S1A-C56A \\sim S1-C56
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O6A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A)
\\sim Ueq, Uanis(O7A) \\sim Ueq, Uanis(C56A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C26) = Uanis(C26A)
Uanis(C28) = Uanis(C28A)
Uanis(O5A) = Uanis(O5)
4. Others
 Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27C)=
 Sof(H27D)=Sof(C28A)=Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29C)=Sof(H29D)=
 Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(1)
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=
 Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(1)
 Sof(C56A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O5A)=Sof(O6A)=Sof(O7A)=Sof(S1A)=1-
 FVAR(2)
 Sof(C56)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(O5)=Sof(O6)=Sof(O7)=Sof(O8)=Sof(H8A)=
 Sof(H8B)=Sof(S1)=FVAR(2)
5.a Free rotating group:
 O8(H8A,H8B)
5.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C25(H25C,H25D), C26(H26A,H26B), C26A(H26C,
 H26D), C27(H27A,H27B), C27A(H27C,H27D), C28(H28A,H28B), C28A(H28C,H28D),
 C29(H29A,H29B), C29A(H29C,H29D), C30(H30A,H30B), C30A(H30C,H30D), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C37(H37A,H37B), C38(H38A,H38B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B),
  C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C48(H48A,
 H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B),
 C53(H53A,H53B), C54(H54A,H54B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C22(H22), C23(H23)
5.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C31A(H31D,H31E,H31F), C39(H39A,H39B,H39C), C47(H47A,H47B,
 H47C), C55(H55A,H55B,H55C)
;
_shelx_res_checksum              57472
_shelx_hkl_checksum              31542
_olex2_date_sample_data_collection 2018-06-19
_olex2_date_sample_submission    2018-06-19
_olex2_exptl_crystal_mounting_method
'oil on micromount. Whilst the crystal is longer than ideal, all attempts to cut the needles led to fragmentation.'
_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 1.816
_oxdiff_exptl_absorpt_empirical_full_min 0.639