Halogen-bonded liquid-crystalline complexes formed from 4-alkoxyphenylpyridines with iodine and with interhalogens
McAllister, Linda J.; Taylor, James; Pridmore, Natalie E.; McEllin, Alice J.; Whitwood, Adrian C.; Karadakov, Peter B.; Bruce, Duncan W.; CrystEngComm 25 (2023) 1683–1692; doi:10.1039/D2CE01555B

data_7246311
_publ_section_title
;
 Halogen-bonded liquid-crystalline complexes formed from
 4-alkoxyphenylpyridines with iodine and with interhalogens
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1683
_journal_page_last               1692
_journal_paper_doi               10.1039/D2CE01555B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'Br3, 2(C23 H33.465 N O)'
_chemical_formula_sum            'C46 H67 Br3 N2 O2'
_chemical_formula_weight         919.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-11-10
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.313(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.1904(12)
_cell_length_b                   9.1296(2)
_cell_length_c                   17.0705(6)
_cell_measurement_reflns_used    5037
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.0770
_cell_measurement_theta_min      3.2170
_cell_volume                     4347.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -17.00   12.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9304  -99.0000  -90.0000 29

  2 omega   -9.00   87.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       16.3366   37.0000  -90.0000 96

  3 omega  -20.00   56.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       16.3366  -99.0000   90.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0022988000
_diffrn_orient_matrix_UB_12      -0.0748572000
_diffrn_orient_matrix_UB_13      -0.0109140000
_diffrn_orient_matrix_UB_21      0.0253366000
_diffrn_orient_matrix_UB_22      -0.0063380000
_diffrn_orient_matrix_UB_23      0.0040613000
_diffrn_orient_matrix_UB_31      0.0006167000
_diffrn_orient_matrix_UB_32      -0.0197101000
_diffrn_orient_matrix_UB_33      0.0403166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15250
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.091
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.822
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.2274
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         7698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0333P)^2^+1.2128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5341
_reflns_number_total             7698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01555b2.cif
_cod_data_source_block           dwb1330
_cod_depositor_comments
'Adding full bibliography for 7246304--7246312.cif.'
_cod_database_code               7246311
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C46 H67 Br3 N2 O2'
_chemical_oxdiff_usercomment     'James Jat33'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H1A)=1-FVAR(1)
 Sof(H2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
  C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
 C34(H34), N2(H2), C1(H1), C2(H2A), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10),
 C11(H11), N1(H1A)
3.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              97775
_olex2_date_sample_data_collection 1369138142.16
_olex2_submission_special_instructions 'No special instructions were received'