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_7246309
_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         'C15 H17 Br I N O'
_chemical_formula_sum            'C15 H17 Br I N O'
_chemical_formula_weight         434.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                106.418(3)
_cell_angle_beta                 94.206(3)
_cell_angle_gamma                113.861(4)
_cell_formula_units_Z            4
_cell_length_a                   10.0323(4)
_cell_length_b                   11.3017(4)
_cell_length_c                   15.5236(5)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      28.0000
_cell_measurement_theta_min      3.4300
_cell_volume                     1508.28(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details
;
  1 omega  -16.00   24.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000   60.0000 40

  2 omega  -25.00   38.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000  -90.0000 63

  3 omega    1.00   89.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000   60.0000 88

  4 omega  -28.00   85.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   19.0000 -180.0000 113

  5 omega  -19.00   57.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -99.0000 -150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0263250000
_diffrn_orient_matrix_UB_12      -0.0479414000
_diffrn_orient_matrix_UB_13      -0.0218054000
_diffrn_orient_matrix_UB_21      -0.0682988000
_diffrn_orient_matrix_UB_22      -0.0550552000
_diffrn_orient_matrix_UB_23      -0.0012831000
_diffrn_orient_matrix_UB_31      -0.0300954000
_diffrn_orient_matrix_UB_32      -0.0023768000
_diffrn_orient_matrix_UB_33      -0.0435972000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11341
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.065
_diffrn_reflns_theta_min         2.801
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.764
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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    1.912
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1594
_exptl_crystal_size_mid          0.0847
_exptl_crystal_size_min          0.0145
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0119P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5105
_reflns_number_total             6069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01555b2.cif
_cod_data_source_block           dwb1416
_cod_depositor_comments
'Adding full bibliography for 7246304--7246312.cif.'
_cod_original_cell_volume        1508.27(11)
_cod_database_code               7246309
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H17 Br1 N1 O1 I1'
_chemical_oxdiff_usercomment     'Linda E404D'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C27(H27a,H27b), C28(H28a,
 H28b), C29(H29a,H29b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C30(H30a,H30b,H30c)
;
_shelx_res_checksum              99601
_olex2_date_sample_data_collection 1389983177.66
_olex2_date_sample_submission    1389225600
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_olex2_submission_special_instructions 'No special instructions were received'