Synthesis and characterization of 2-(anthracene-9-yl)-4,5-diphenyl-1H-imidazole derivatives as environmentally sensitive fluorophores
Younes, Eyad A.; AL-Snaid, Amneh M.; Abu-Safieh, Kayed A.; Salami, Fatemeh; Aljaar, Nayyef; Zhao, Yuming; RSC Advances 14 (2024) 23511–23519; doi:10.1039/D4RA03735A

data_7249133
_publ_section_title
;
 Synthesis and characterization of
 2-(anthracene-9-yl)-4,5-diphenyl-1H-imidazole derivatives as
 environmentally sensitive fluorophores
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              23511
_journal_page_last               23519
_journal_paper_doi               10.1039/D4RA03735A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C45 H28 N2 S2'
_chemical_formula_sum            'C45 H28 N2 S2'
_chemical_formula_weight         660.81
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                91.4770(10)
_cell_angle_beta                 94.0740(10)
_cell_angle_gamma                99.8870(10)
_cell_formula_units_Z            4
_cell_length_a                   11.57220(10)
_cell_length_b                   13.9231(2)
_cell_length_c                   24.5599(3)
_cell_measurement_reflns_used    48449
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.3120
_cell_measurement_theta_min      3.2080
_cell_volume                     3885.59(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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  24.00   0.50    1.01    --  -48.57  85.00 129.00  196
  2  \w    -21.00  74.00   0.50    1.01    --   48.57 -85.00  10.00  190
  3  \w   -161.00 -79.00   0.50    4.04    --  -90.00 -85.00  10.00  164
  4  \w   -115.00 -18.00   0.50    4.04    --  -90.00  85.00 129.00  194
  5  \w     40.00 137.00   0.50    4.04    --  111.50 -85.00  10.00  194
  6  \w    101.00 178.00   0.50    4.04    --  111.50  85.00 129.00  154
  7  \w    -34.00  24.00   0.50    1.01    --  -48.57  37.00 120.00  116
  8  \w   -118.00 -73.00   0.50    1.01    --  -48.57-125.00  90.00   90
  9  \w    -34.00  24.00   0.50    1.01    --  -48.57  37.00  60.00  116
 10  \w    -16.00  26.00   0.50    1.01    --  -48.57  19.00  30.00   84
 11  \w    -16.00  26.00   0.50    1.01    --  -48.57  19.00-180.00   84
 12  \w    -34.00  24.00   0.50    1.01    --  -48.57  37.00-150.00  116
 13  \w   -118.00 -73.00   0.50    1.01    --  -48.57-125.00 120.00   90
 14  \w     34.00  93.00   0.50    1.01    --   48.57-125.00   0.00  118
 15  \w   -161.00 -83.00   0.50    4.04    --  -90.00 -94.00 120.00  156
 16  \w    -65.00 -18.00   0.50    4.04    --  -90.00  61.00  90.00   94
 17  \w    101.00 178.00   0.50    4.04    --  111.50  30.00   0.00  154
 18  \w    101.00 178.00   0.50    4.04    --  111.50  15.00 120.00  154
 19  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00 150.00  130
 20  \w     42.00 111.00   0.50    4.04    --  111.50-125.00 -90.00  138
 21  \w     95.00 178.00   0.50    4.04    --  111.50 125.00  60.00  166
 22  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00 -30.00  130
 23  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00   0.00  130
 24  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00  30.00  130
 25  \w    101.00 178.00   0.50    4.04    --  111.50  30.00  60.00  154
 26  \w     42.00 111.00   0.50    4.04    --  111.50-125.00-120.00  138
 27  \w    101.00 178.00   0.50    4.04    --  111.50  30.00 -60.00  154
 28  \w     40.00  79.00   0.50    4.04    --  111.50 -61.00   0.00   78
 29  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00 120.00  130
 30  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00  90.00  130
 31  \w    101.00 178.00   0.50    4.04    --  111.50  45.00-180.00  154
 32  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00 -60.00  130
 33  \w     40.00 105.00   0.50    4.04    --  111.50 -95.00 -99.25  130
 34  \w     41.00 106.00   0.50    4.04    --  111.50-100.00-133.93  130
 35  \w    101.00 178.00   0.50    4.04    --  111.50  45.00-120.00  154
 36  \w     40.00  79.00   0.50    4.04    --  111.50 -61.00  60.00   78
 37  \w    101.00 178.00   0.50    4.04    --  111.50  45.00 150.00  154
 38  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00 -90.00  130
 39  \w     40.00  79.00   0.50    4.04    --  111.50 -61.00  30.00   78
 40  \w     40.00  79.00   0.50    4.04    --  111.50 -61.00 120.00   78
 41  \w     40.00  79.00   0.50    4.04    --  111.50 -61.00 -60.00   78
 42  \w     42.00 107.00   0.50    4.04    --  111.50-108.00 143.70  130
 43  \w    101.00 178.00   0.50    4.04    --  111.50  45.00 -60.00  154
 44  \w     40.00 105.00   0.50    4.04    --  111.50 -94.00-180.00  130
 45  \w     41.00 106.00   0.50    4.04    --  111.50 -99.00 -67.43  130
 46  \w    101.00 178.00   0.50    4.04    --  111.50  45.00  30.00  154
 47  \w    101.00 178.00   0.50    4.04    --  111.50  45.00-150.00  154
 48  \w   -121.00 -27.00   0.50    1.01    --  -48.57 -77.00 -90.00  188
 49  \w   -121.00 -27.00   0.50    1.01    --  -48.57 -77.00-180.00  188
 50  \w   -121.00 -27.00   0.50    1.01    --  -48.57 -77.00   0.00  188
 51  \w   -121.00 -27.00   0.50    1.01    --  -48.57 -77.00  90.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0681065000
_diffrn_orient_matrix_UB_12      0.0964913000
_diffrn_orient_matrix_UB_13      -0.0193117000
_diffrn_orient_matrix_UB_21      -0.0833056000
_diffrn_orient_matrix_UB_22      -0.0092282000
_diffrn_orient_matrix_UB_23      -0.0523767000
_diffrn_orient_matrix_UB_31      -0.0824052000
_diffrn_orient_matrix_UB_32      0.0569036000
_diffrn_orient_matrix_UB_33      0.0290563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            96398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.374
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.91a (Rigaku Oxford Diffraction, 2023)
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    1.130
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     891
_refine_ls_number_reflns         16607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0388P)^2^+2.9711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14725
_reflns_number_total             16607
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra03735a2.cif
_cod_data_source_block           am-tba
_cod_database_code               7249133
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.810
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39),
 C41(H41), C42(H42), C43(H43), C44(H44), C50(H50), C51(H51), C53(H53), C54(H54),
  C55(H55), C58(H58), C59(H59), C60(H60), C61(H61), C64(H64), C65(H65),
 C67(H67), C68(H68), C69(H69), C72(H72), C73(H73), C74(H74), C75(H75), C79(H79),
  C80(H80), C81(H81), C82(H82), C84(H84), C86(H86), C87(H87), C88(H88), C89(H89)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              27747
_shelx_hkl_checksum              18201
_shelx_fab_checksum              89637
_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 1.162
_oxdiff_exptl_absorpt_empirical_full_min 0.805