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_7249132
_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         'C30 H20 Br2 N2'
_chemical_formula_sum            'C30 H20 Br2 N2'
_chemical_formula_weight         568.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5732(3)
_cell_length_b                   11.1891(3)
_cell_length_c                   28.3670(6)
_cell_measurement_reflns_used    24405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.4940
_cell_measurement_theta_min      3.0970
_cell_volume                     4942.95(19)
_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      air
_diffrn_ambient_temperature      293(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 0.992
_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    -29.00  24.00   0.50    0.77    --  -48.57  32.00 -30.00  106
  2  \w    -24.00  43.00   0.50    0.77    --   48.57 -32.00 169.00  134
  3  \w   -158.00 -80.00   0.50    3.09    --  -90.00-115.00 -43.00  156
  4  \w     67.00 152.00   0.50    3.09    --  111.50 169.00-169.00  170
  5  \w    101.00 178.00   0.50    3.09    --  111.50  32.00 -30.00  154
  6  \w    104.00 178.00   0.50    3.09    --  111.50  93.00 151.00  148
  7  \w    -16.00  26.00   0.50    0.77    --  -48.57  19.00 120.00   84
  8  \w    -16.00  26.00   0.50    0.77    --  -48.57  19.00  90.00   84
  9  \w   -118.00 -73.00   0.50    0.77    --  -48.57-125.00 -90.00   90
 10  \w    -16.00  26.00   0.50    0.77    --  -48.57  19.00  60.00   84
 11  \w    -65.00 -18.00   0.50    3.09    --  -90.00  61.00-120.00   94
 12  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00 -90.00   78
 13  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00  30.00   78
 14  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00-150.00   78
 15  \w     42.00 111.00   0.50    3.09    --  111.50-125.00 150.00  138
 16  \w     40.00 105.00   0.50    3.09    --  111.50 -94.00-150.00  130
 17  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00 -30.00   78
 18  \w     90.00 178.00   0.50    3.09    --  111.50  77.00 -60.00  176
 19  \w     40.00 105.00   0.50    3.09    --  111.50 -94.00 150.00  130
 20  \w     42.00 111.00   0.50    3.09    --  111.50-125.00 -60.00  138
 21  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00  60.00   78
 22  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00-120.00   78
 23  \w     40.00 105.00   0.50    3.09    --  111.50 -94.00-180.00  130
 24  \w     40.00 133.00   0.50    3.09    --  111.50 -77.00 -30.00  186
 25  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00-180.00   78
 26  \w     40.00  79.00   0.50    3.09    --  111.50 -61.00 -60.00   78
 27  \w   -121.00 -35.00   0.50    0.77    --  -48.57 -57.00 -30.00  172
 28  \w   -121.00 -27.00   0.50    0.77    --  -48.57 -77.00-150.00  188
 29  \w   -121.00 -27.00   0.50    0.77    --  -48.57 -77.00 120.00  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      -0.0139229000
_diffrn_orient_matrix_UB_12      0.1357436000
_diffrn_orient_matrix_UB_13      0.0048479000
_diffrn_orient_matrix_UB_21      -0.0377848000
_diffrn_orient_matrix_UB_22      0.0039885000
_diffrn_orient_matrix_UB_23      -0.0501813000
_diffrn_orient_matrix_UB_31      -0.0903668000
_diffrn_orient_matrix_UB_32      -0.0225170000
_diffrn_orient_matrix_UB_33      0.0202190000
_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  0.0328
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            57548
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.574
_diffrn_reflns_theta_min         3.116
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75256
_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    1.527
_exptl_crystal_description       prism
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         10338
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+3.4199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                9022
_reflns_number_total             10338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra03735a2.cif
_cod_data_source_block           am-bam
_cod_database_code               7249132
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.506
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.63(3)
 0.37(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C35(H35), C36(H36), C38(H38), C39(H39), C41(H41), C42(H42),
 C44(H44), C45(H45), C49(H49), C50(H50), C51(H51), C52(H52), C54(H54), C56(H56),
  C57(H57), C58(H58), C59(H59)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              35503
_shelx_hkl_checksum              39612
_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 2.480
_oxdiff_exptl_absorpt_empirical_full_min 0.790