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_7249131
_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, 2(C H4 O)'
_chemical_formula_sum            'C47 H36 N2 O2 S2'
_chemical_formula_weight         724.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2k0pbm
_audit_creation_date             2023-05-15
_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                90
_cell_angle_beta                 105.1980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.62220(10)
_cell_length_b                   11.89850(10)
_cell_length_c                   19.71010(10)
_cell_measurement_reflns_used    30383
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.6580
_cell_measurement_theta_min      4.2300
_cell_volume                     3535.59(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -34.00  24.00   0.50    0.13    --  -48.37  37.00  90.00  116
  2  \w    -34.00  24.00   0.50    0.13    --  -48.37  37.00   0.00  116
  3  \w    -16.00  26.00   0.50    0.13    --  -48.37  19.00 -30.00   84
  4  \w    -34.00  24.00   0.50    0.13    --  -48.37  37.00-120.00  116
  5  \w    -16.00  26.00   0.50    0.13    --  -48.37  19.00-150.00   84
  6  \w     95.00 178.00   0.50    0.51    --  111.50 125.00 -60.00  166
  7  \w     95.00 178.00   0.50    0.51    --  111.50 125.00   0.00  166
  8  \w    101.00 178.00   0.50    0.51    --  111.50  88.00 -35.00  154
  9  \w     90.00 178.00   0.50    0.51    --  111.50  77.00 -90.00  176
 10  \w     90.00 178.00   0.50    0.51    --  111.50  77.00-120.00  176
 11  \w    101.00 178.00   0.50    0.51    --  111.50  45.00-180.00  154
 12  \w     96.00 178.00   0.50    0.51    --  111.50  61.00 -90.00  164
 13  \w    101.00 178.00   0.50    0.51    --  111.50  45.00 -60.00  154
 14  \w    101.00 178.00   0.50    0.51    --  111.50  45.00   0.00  154
 15  \w    101.00 178.00   0.50    0.51    --  111.50  45.00  30.00  154
 16  \w    101.00 178.00   0.50    0.51    --  111.50  30.00  90.00  154
 17  \w    101.00 178.00   0.50    0.51    --  111.50  15.00 120.00  154
 18  \w    101.00 178.00   0.50    0.51    --  111.50  45.00 120.00  154
 19  \w    101.00 178.00   0.50    0.51    --  111.50  30.00  60.00  154
 20  \w    101.00 178.00   0.50    0.51    --  111.50  15.00 -90.00  154
 21  \w    101.00 178.00   0.50    0.51    --  111.50  15.00-180.00  154
 22  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00-120.00   78
 23  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00 -90.00   78
 24  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00 -60.00   78
 25  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00   0.00   78
 26  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00  60.00   78
 27  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00 120.00   78
 28  \w     40.00  79.00   0.50    0.51    --  111.50 -61.00 150.00   78
 29  \w    -25.00  30.00   0.50    0.13    --   48.37 -19.00 120.00  110
 30  \w     34.00  93.00   0.50    0.13    --   48.37-125.00  60.00  118
 31  \w     42.00 111.00   0.50    0.51    --  111.50-125.00   0.00  138
 32  \w     42.00 111.00   0.50    0.51    --  111.50-125.00 -30.00  138
 33  \w     40.00 105.00   0.50    0.51    --  111.50 -94.00 -30.00  130
 34  \w     42.00 111.00   0.50    0.51    --  111.50-125.00 -60.00  138
 35  \w     40.00 105.00   0.50    0.51    --  111.50 -94.00   0.00  130
 36  \w     42.00 111.00   0.50    0.51    --  111.50-125.00 -90.00  138
 37  \w     40.00 105.00   0.50    0.51    --  111.50 -94.00 -90.00  130
 38  \w     42.00 111.00   0.50    0.51    --  111.50-125.00-180.00  138
 39  \w     40.00 105.00   0.50    0.51    --  111.50 -94.00-180.00  130
 40  \w     40.00 138.00   0.50    0.51    --  111.50 -88.00-151.00  196
 41  \w    -21.00  75.00   0.50    0.13    --   48.37 -88.00-151.00  192
 42  \w   -163.00 -79.00   0.50    0.51    --  -90.00 -30.00 120.00  168
 43  \w   -120.00 -71.00   0.50    0.13    --  -48.37 -57.00  60.00   98
 44  \w   -161.00 -76.00   0.50    0.51    --  -90.00 -58.00-106.16  170
 45  \w   -120.00 -27.00   0.50    0.13    --  -48.37 -77.00-150.00  186
 46  \w   -120.00 -34.00   0.50    0.13    --  -48.37 -57.00 -60.00  172
 47  \w    -75.00  24.00   0.50    0.13    --  -48.37  88.00 -35.00  198
 48  \w   -117.00 -18.00   0.50    0.51    --  -90.00  88.00 -35.00  198
 49  \w   -161.00 -83.00   0.50    0.51    --  -90.00 -94.00 150.00  156
 50  \w   -161.00 -79.00   0.50    0.51    --  -90.00 -88.00-151.00  164
;
_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      -0.0367083000
_diffrn_orient_matrix_UB_12      -0.0069021000
_diffrn_orient_matrix_UB_13      0.0652257000
_diffrn_orient_matrix_UB_21      -0.0390285000
_diffrn_orient_matrix_UB_22      -0.1168542000
_diffrn_orient_matrix_UB_23      -0.0236462000
_diffrn_orient_matrix_UB_31      0.0870048000
_diffrn_orient_matrix_UB_32      -0.0553039000
_diffrn_orient_matrix_UB_33      0.0417903000
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            43504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.344
_diffrn_reflns_theta_min         4.383
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (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    1.362
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0412P)^2^+5.5040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3713
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra03735a2.cif
_cod_data_source_block           tba
_cod_database_code               7249131
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.762
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1B
 0.84 with sigma of 0.02
 O1-H1A
 0.84 with sigma of 0.02
3. Others
 Fixed Sof: H1(0.5) H1A(0.5) H1B(0.5)
4.a Riding coordinates:
 O1(H1A)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24)
4.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              18459
_shelx_hkl_checksum              8769
_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 1.284
_oxdiff_exptl_absorpt_empirical_full_min 0.841