Novel liquid crystalline organogelators based on terephthalic acid and terephthalaldehyde derivatives: properties and promotion through the formation of halogen bonding
Huang, Yaodong; Zhang, Xiaojie; Cui, Wei; Wang, Xin; Li, Bin; Zhang, Yongxin; Yang, Junjiao; New Journal of Chemistry 44 (2020) 614–625; doi:10.1039/C9NJ05811G

data_7059189
_publ_section_title
;
 Novel liquid crystalline organogelators based on terephthalic acid and
 terephthalaldehyde derivatives: properties and promotion through the
 formation of halogen bonding
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              614
_journal_page_last               625
_journal_paper_doi               10.1039/C9NJ05811G
_journal_volume                  44
_journal_year                    2020
_chemical_compound_source        chemical
_chemical_formula_moiety         'C6 F4 I2, C20 H18 N4 O4'
_chemical_formula_sum            'C26 H18 F4 I2 N4 O4'
_chemical_formula_weight         780.24
_chemical_name_common            A2-OMe
_chemical_name_systematic        'A2-OMe and DIB'
_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     dual
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-08 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                82.895(2)
_cell_angle_beta                 73.539(2)
_cell_angle_gamma                84.883(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3364(3)
_cell_length_b                   8.9922(2)
_cell_length_c                   9.09840(10)
_cell_measurement_reflns_used    8908
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      76.8480
_cell_measurement_theta_min      4.9500
_cell_volume                     648.01(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -74.00  27.00   0.50    0.05    --  -45.87  86.00  25.00  202
  2  \w    -26.00  74.00   0.50    0.05    --   45.87 -86.00 -93.00  200
  3  \w   -173.00 -81.00   0.50    0.05    -- -100.00 -86.00 -93.00  184
  4  \w   -128.00 -27.00   0.50    0.05    -- -100.00  86.00  25.00  202
  5  \w     80.00 178.00   0.50    0.05    --  107.75  86.00  25.00  196
  6  \w     73.00 119.00   0.50    0.05    --   45.87 125.00 -30.00   92
  7  \w     73.00 119.00   0.50    0.05    --   45.87 125.00-150.00   92
  8  \w    -28.00  61.00   0.50    0.05    --   45.87 -37.00 -60.00  178
  9  \w     73.00 119.00   0.50    0.05    --   45.87 125.00 -60.00   92
 10  \w    -28.00  61.00   0.50    0.05    --   45.87 -37.00-180.00  178
 11  \w   -173.00 -27.00   0.50    0.05    -- -100.00   0.00 -90.00  292
 12  \w   -117.00 -27.00   0.50    0.05    -- -100.00 125.00 120.00  180
 13  \w   -117.00 -27.00   0.50    0.05    -- -100.00  61.00  30.00  180
 14  \w   -173.00 -84.00   0.50    0.05    -- -100.00 -94.00 -60.00  178
 15  \w   -115.00 -25.00   0.50    0.05    -- -100.00  30.00-120.00  180
 16  \w     35.00 109.00   0.50    0.05    --  107.75 -94.00-150.00  148
 17  \w     93.00 178.00   0.50    0.05    --  107.75  45.00-180.00  170
 18  \w     35.00 109.00   0.50    0.05    --  107.75 -94.00 -90.00  148
 19  \w     35.00 117.00   0.50    0.05    --  107.75-125.00 150.00  164
 20  \w     35.00 109.00   0.50    0.05    --  107.75 -94.00   0.00  148
 21  \w     35.00 109.00   0.50    0.05    --  107.75 -94.00-120.00  148
 22  \w     35.00 109.00   0.50    0.05    --  107.75 -94.00  60.00  148
 23  \w     90.00 178.00   0.50    0.05    --  107.75  15.00 -30.00  176
 24  \w     35.00 136.00   0.50    0.05    --  107.75 -86.00 -93.00  202
 25  \w     30.00 119.00   0.50    0.05    --   45.87  57.00  90.00  178
 26  \w     30.00 119.00   0.50    0.05    --   45.87  57.00  30.00  178
 27  \w     22.00 119.00   0.50    0.05    --   45.87  77.00 -60.00  194
 28  \w     22.00 119.00   0.50    0.05    --   45.87  77.00-120.00  194
 29  \w     22.00 119.00   0.50    0.05    --   45.87  77.00 120.00  194
 30  \w     22.00 119.00   0.50    0.05    --   45.87  77.00-180.00  194
 31  \w     90.00 178.00   0.50    0.05    --  107.75  15.00 120.00  176
 32  \w     92.00 135.00   0.50    0.05    --  107.75  30.00 150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1218631000
_diffrn_orient_matrix_UB_12      0.1271649000
_diffrn_orient_matrix_UB_13      -0.0357725000
_diffrn_orient_matrix_UB_21      0.0961647000
_diffrn_orient_matrix_UB_22      -0.0861720000
_diffrn_orient_matrix_UB_23      0.1088575000
_diffrn_orient_matrix_UB_31      0.1146945000
_diffrn_orient_matrix_UB_32      -0.0794203000
_diffrn_orient_matrix_UB_33      -0.1355662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10921
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.085
_diffrn_reflns_theta_min         4.964
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.766
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0248
_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^)+(0.0371P)^2^+1.2025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2578
_reflns_number_total             2624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj05811g2.cif
_cod_data_source_block           A2-OMe
_cod_depositor_comments          'Adding full bibliography for 7059189.cif.'
_cod_database_code               7059189
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.302
_shelx_estimated_absorpt_t_min   0.201
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C6(H6), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_res_checksum              53522
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.667
_oxdiff_exptl_absorpt_empirical_full_min 0.628