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_7246305
_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 I2 N O'
_chemical_formula_sum            'C15 H17 I2 N O'
_chemical_formula_weight         481.09
_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                106.226(5)
_cell_angle_beta                 98.182(4)
_cell_angle_gamma                100.729(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7375(3)
_cell_length_b                   9.2799(4)
_cell_length_c                   10.6024(7)
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.7300
_cell_measurement_theta_min      3.4670
_cell_volume                     793.61(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details
;
  1 omega  -19.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000   90.0000 45

  2 omega   -7.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000  -60.0000 35

  3 omega   -9.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000   90.0000 90

  4 omega  -22.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784    0.0000   30.0000 99

  5 omega  -20.00   58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -99.0000 -120.0000 78

  6 omega  -20.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000 -150.0000 47

  7 omega   -9.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000 -180.0000 98

  8 omega  -56.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -37.0000    0.0000 98
;
_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      -0.0137097000
_diffrn_orient_matrix_UB_12      0.0245097000
_diffrn_orient_matrix_UB_13      0.0661667000
_diffrn_orient_matrix_UB_21      0.0790880000
_diffrn_orient_matrix_UB_22      -0.0008546000
_diffrn_orient_matrix_UB_23      0.0261279000
_diffrn_orient_matrix_UB_31      0.0261966000
_diffrn_orient_matrix_UB_32      0.0781985000
_diffrn_orient_matrix_UB_33      0.0030207000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71071
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9193
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_min         2.950
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.955
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.664
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2291
_exptl_crystal_size_mid          0.1083
_exptl_crystal_size_min          0.0148
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0130P)^2^+0.3111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2759
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01555b2.cif
_cod_data_source_block           dwb1368
_cod_depositor_comments
'Adding full bibliography for 7246304--7246312.cif.'
_cod_database_code               7246305
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H17 O1 N1 I2'
_chemical_oxdiff_usercomment     'Linda E380F'
_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. Restrained distances
 C14A-C15A
 1.55 with sigma of 0.02
 C12A-C13A = C13A-C14A
 1.51 with sigma of 0.02
 O1A-C12A
 1.41 with sigma of 0.02
 C9A-O1A
 1.36 with sigma of 0.02
 I1A-I2A
 2.8 with sigma of 0.02
 C3A-C6A
 1.45 with sigma of 0.02
 I1A-N1A
 2.45 with sigma of 0.02
 C13A-C15A
 2.54 with sigma of 0.04
 C12A-C14A
 2.52 with sigma of 0.04
 O1A-C13A
 2.37 with sigma of 0.04
 C9A-C12A
 2.38 with sigma of 0.04
3. Restrained planarity
 C6A, C7A, C8A, C9A, C10A, C11A, O1A, C12A, C13A, C14A, C15A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(I2) = Uanis(C15A)
Uanis(I1) = Uanis(C12A) = Uanis(C13A) = Uanis(C14A)
Uanis(C3) = Uanis(C6A)
Uanis(C2) = Uanis(C11A)
Uanis(C4) = Uanis(C7A)
Uanis(C5) = Uanis(C8A)
Uanis(C1) = Uanis(C10A)
Uanis(N1) = Uanis(C9A) = Uanis(O1A)
Uanis(C15) = Uanis(I2A)
Uanis(C13) = Uanis(I1A)
Uanis(C9) = Uanis(N1A)
Uanis(C8) = Uanis(C5A)
Uanis(C7) = Uanis(C4A)
Uanis(C10) = Uanis(C1A)
Uanis(C11) = Uanis(C2A)
Uanis(C6) = Uanis(C3A)
5. Others
 Sof(C6A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(C8A)=Sof(H8A)=
 Sof(C7A)=Sof(H7A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(I1A)=
 Sof(I2A)=Sof(N1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(O1A)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(I1)=Sof(I2)=
 Sof(N1)=Sof(O1)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C12A(H12C,H12D), C13A(H13C,
 H13D), C14A(H14C,H14D)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11),
 C11A(H11A), C10A(H10A), C8A(H8A), C7A(H7A), C1A(H1A), C2A(H2A), C4A(H4A),
 C5A(H5A)
6.c Fitted hexagon refined as free rotating group:
 C6A(C11A,C10A,C9A,C8A,C7A), N1A(C1A,C2A,C3A,C4A,C5A)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_shelx_res_checksum              40099
_olex2_date_sample_data_collection 1386321692.84
_olex2_date_sample_submission    1385424000
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_olex2_submission_special_instructions 'No special instructions were received'