Discotic Triphenylene Twins Linked through Thiophene Bridges: Controlling Nematic Behavior in an Intriguing Class of Functional Organic Materials
Liang Zhang; David L. Hughes; Andrew N. Cammidge; Journal of Organic Chemistry 77 (2012) 4288–4297; doi:10.1021/jo3002886

data_4027174
_publ_section_title
;
 Discotic Triphenylene Twins Linked through Thiophene Bridges: Controlling
 Nematic Behavior in an Intriguing Class of Functional Organic Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4288
_journal_page_last               4297
_journal_paper_doi               10.1021/jo3002886
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C58 H66 I2 O4'
_chemical_formula_structural     C18H6(OC6H13)4(CCC6H4I)2
_chemical_formula_sum            'C58 H66 I2 O4'
_chemical_formula_weight         1080.91
_chemical_name_common            'Compound 5'
_chemical_name_systematic
;
 2,11-bis-(CC-C6H4-I-3),-3,6,7,10-tetra-OC6H13-triphenylene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and CrysAlisPro RED'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.182(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.7085(18)
_cell_length_b                   9.4740(5)
_cell_length_c                   32.0035(16)
_cell_measurement_temperature    140(1)
_cell_volume                     10397.9(9)
_computing_cell_refinement
;
 CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 
;
_computing_data_collection
;
 CrysAlisPro CCD, Oxford Diffraction Ltd., Version 1.171.32.24 
;
_computing_data_reduction
;
 CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24
;
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(1)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/CCD'
_diffrn_measurement_method       'Thin slice \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2149
_diffrn_reflns_av_sigmaI/netI    0.1082
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            48371
_diffrn_reflns_theta_full        20.00
_diffrn_reflns_theta_max         20.00
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    1.254
_exptl_absorpt_correction_T_max  1.097
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 
 empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       'thin prism'
_exptl_crystal_F_000             4416
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.348
_refine_ls_R_factor_all          0.1808
_refine_ls_R_factor_gt           0.1477
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+482.7183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2219
_reflns_number_gt                3923
_reflns_number_total             4836
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo3002886_si_001.cif
_cod_data_source_block           zhangl2c
_cod_database_code               4027174