Halogen-bonded liquid crystals of 4-alkoxystilbazoles with molecular iodine: a very short halogen bond and unusual mesophase stability
Linda J. McAllister; Carsten Prasang; Joanna P.-W. Wong; Robert J. Thatcher; Adrian C. Whitwood; Bertrand Donnio; Peter O'Brien; Peter B. Karadakov; Duncan W. Bruce; Chem.Commun. 49 (2013) 3946–; doi:10.1039/c3cc41227j

data_7109169
_publ_section_title
;
 Halogen-bonded liquid crystals of 4-alkoxystilbazoles with molecular
 iodine: a very short halogen bond and unusual mesophase stability
;
_journal_name_full               Chem.Commun.
_journal_page_first              3946
_journal_paper_doi               10.1039/c3cc41227j
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 Br2 N'
_chemical_formula_sum            'C17 H19 Br2 N'
_chemical_formula_weight         397.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-11
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.103(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.40904(18)
_cell_length_b                   12.6594(4)
_cell_length_c                   23.2463(8)
_cell_measurement_reflns_used    4587
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      32.1320
_cell_measurement_theta_min      3.2119
_cell_volume                     1591.50(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_details
;
1 omega -89.00 -61.00 1.0000 15.6800
omega____ theta____ kappa____ phi______ frames
- -25.0110 -178.0000 -60.0000 28
2 omega -98.00 26.00 1.0000 15.6800
omega____ theta____ kappa____ phi______ frames
- -25.0110 0.0000 150.0000 124
3 omega 54.00 89.00 1.0000 15.6800
omega____ theta____ kappa____ phi______ frames
- 26.5735 57.0000 0.0000 35
4 omega 39.00 83.00 1.0000 15.6800
omega____ theta____ kappa____ phi______ frames
- 26.5735 178.0000 -120.0000 44
5 omega 8.00 93.00 1.0000 15.6800
omega____ theta____ kappa____ phi______ frames
- 26.5735 57.0000 -30.0000 85
6 omega -43.00 50.00 1.0000 15.6800
omega____ theta____ kappa____ phi______ frames
- 26.5735 -37.0000 -90.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0724896000
_diffrn_orient_matrix_UB_12      0.0184429000
_diffrn_orient_matrix_UB_13      0.0230594000
_diffrn_orient_matrix_UB_21      0.0861292000
_diffrn_orient_matrix_UB_22      -0.0220262000
_diffrn_orient_matrix_UB_23      0.0200020000
_diffrn_orient_matrix_UB_31      0.0673333000
_diffrn_orient_matrix_UB_32      0.0480776000
_diffrn_orient_matrix_UB_33      0.0003696000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7949
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.20
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.084
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.1289
_exptl_crystal_size_min          0.1149
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.045(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4415
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+2.8003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                4268
_reflns_number_total             4415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41227j.txt
_cod_data_source_block           dwb1161
_cod_original_cell_volume        1591.51(9)
_cod_database_code               7109169
_chemical_oxdiff_formula         'C17 H19 Br2 N1'
_chemical_oxdiff_usercomment     'Linda's LJM186'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H6 of C6, {H14A,H14B} of C14, H7 of C7, H6A of C6A, H7B of C7B, H7A of C7A,
{H15A,H15B} of C15, H9 of C9, {H16A,H16B} of C16, H6B of C6B, H6C of C6C, H7C
of C7C, H5 of C5, H1 of C1, H4 of C4, H2 of C2, H10 of C10, H12 of C12, H13
of C13
At 1.5 times of:
{H17A,H17B,H17C} of C17
2. Uiso/Uaniso restraints and constraints
Uanis(C6C) ~ Ueq, Uanis(C7C) ~ Ueq, Uanis(C6B) ~ Ueq, Uanis(C7B) ~ Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1
Uanis(C6) = Uanis(C7)
Uanis(C6A) = Uanis(C7A)
Uanis(C6B) = Uanis(C7B)
Uanis(C6C) = Uanis(C7C)
3. Others
1*[Sof(C7A)+Sof(H7A)+Sof(C6A)+Sof(H6A)]+1*[Sof(C6)+Sof(H6)+Sof(C7)+Sof(H7)]+1*
[Sof(C6C)+Sof(H6C)+Sof(C7C)+Sof(H7C)]+1*[Sof(C7B)+Sof(H7B)+Sof(C6B)+Sof(H6B)]=
1 with esd of 0.0001
Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)
Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)
Sof(C6C)=Sof(H6C)=Sof(C7C)=Sof(H7C)
Sof(C7B)=Sof(H7B)=Sof(C6B)=Sof(H6B)
4.a Ternary CH refined with riding coordinates:
C6(H6), C7(H7), C7A(H7A), C6A(H6A), C7B(H7B), C6C(H6C), C7C(H7C), C6B(H6B)
4.b Secondary CH2 refined with riding coordinates:
C15(H15A,H15B), C16(H16A,H16B), C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
C1(H1), C4(H4), C2(H2), C5(H5), C10(H10), C12(H12), C13(H13), C9(H9)
4.d Idealised Me refined as rotating group:
C17(H17A,H17B,H17C)
;