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_7249134
_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
'C29 H18 Br2 N2, 0.098(C H2 Cl2), 0.402(C2 H3 N)'
_chemical_formula_sum            'C29.9 H19.4 Br2 Cl0.2 N2.4'
_chemical_formula_weight         579.12
_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             2023-05-05
_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                84.7150(10)
_cell_angle_beta                 78.8930(10)
_cell_angle_gamma                72.8160(10)
_cell_formula_units_Z            8
_cell_length_a                   14.37750(10)
_cell_length_b                   15.7779(2)
_cell_length_c                   23.0024(2)
_cell_measurement_reflns_used    49273
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1390
_cell_measurement_theta_min      2.9300
_cell_volume                     4888.27(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (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 0.988
_diffrn_measured_fraction_theta_max 0.961
_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   -120.00 -27.00   0.50    3.90    --  -48.37 -75.00-109.00  186
  2  \w    -23.00  69.00   0.50    3.90    --   48.37 -75.00-109.00  184
  3  \w     28.00 121.00   0.50    3.90    --   48.37  75.00  18.00  186
  4  \w    -96.00 -18.00   0.50   15.58    --  -90.00  75.00  18.00  156
  5  \w   -161.00 -69.00   0.50   15.58    --  -90.00 -75.00-109.00  184
  6  \w     91.00 178.00   0.50   15.58    --  111.50  75.00  18.00  174
  7  \w     40.00 110.00   0.50   15.58    --  111.50 -75.00-109.00  140
  8  \w    -16.00  26.00   0.50    3.90    --  -48.37  19.00-180.00   84
  9  \w    -69.00  24.00   0.50    3.90    --  -48.37  75.00  18.00  186
 10  \w    -16.00  26.00   0.50    3.90    --  -48.37  19.00 150.00   84
 11  \w    -16.00  26.00   0.50    3.90    --  -48.37  19.00 120.00   84
 12  \w    -24.00  48.00   0.50    3.90    --   48.37 -37.00 -90.00  144
 13  \w     -1.00  80.00   0.50    3.90    --   48.37 -99.00  90.00  162
 14  \w    -65.00 -18.00   0.50   15.58    --  -90.00  61.00-150.00   94
 15  \w    101.00 178.00   0.50   15.58    --  111.50  15.00  90.00  154
 16  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00   0.00  130
 17  \w    101.00 178.00   0.50   15.58    --  111.50  30.00 -60.00  154
 18  \w     41.00 105.00   0.50   15.58    --  111.50 -96.00 102.92  128
 19  \w     42.00 111.00   0.50   15.58    --  111.50-125.00 -60.00  138
 20  \w     96.00 178.00   0.50   15.58    --  111.50  61.00 150.00  164
 21  \w     40.00  79.00   0.50   15.58    --  111.50 -61.00 -90.00   78
 22  \w    101.00 178.00   0.50   15.58    --  111.50  15.00 120.00  154
 23  \w    101.00 178.00   0.50   15.58    --  111.50  45.00 -30.00  154
 24  \w    101.00 178.00   0.50   15.58    --  111.50  30.00-120.00  154
 25  \w     43.00 124.00   0.50   15.58    --  111.50-141.00  90.93  162
 26  \w     40.00  79.00   0.50   15.58    --  111.50 -61.00 150.00   78
 27  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00 -30.00  130
 28  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00 150.00  130
 29  \w     96.00 178.00   0.50   15.58    --  111.50  61.00 -18.44  164
 30  \w    101.00 178.00   0.50   15.58    --  111.50  15.00-120.00  154
 31  \w     40.00  79.00   0.50   15.58    --  111.50 -61.00  90.00   78
 32  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00 -60.00  130
 33  \w     41.00 106.00   0.50   15.58    --  111.50 -99.00-158.58  130
 34  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00  30.00  130
 35  \w    101.00 178.00   0.50   15.58    --  111.50  30.00 150.00  154
 36  \w    101.00 178.00   0.50   15.58    --  111.50  45.00  30.00  154
 37  \w     40.00  79.00   0.50   15.58    --  111.50 -61.00-150.00   78
 38  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00-120.00  130
 39  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00 -90.00  130
 40  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00  60.00  130
 41  \w    101.00 178.00   0.50   15.58    --  111.50  45.00 -60.00  154
 42  \w     41.00 107.00   0.50   15.58    --  111.50-103.00-138.23  132
 43  \w     40.00 133.00   0.50   15.58    --  111.50 -77.00  90.00  186
 44  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00-180.00  130
 45  \w     40.00 105.00   0.50   15.58    --  111.50 -94.00 120.00  130
 46  \w     40.00  79.00   0.50   15.58    --  111.50 -61.00  30.00   78
 47  \w   -120.00 -27.00   0.50    3.90    --  -48.37 -77.00  60.00  186
 48  \w   -120.00 -27.00   0.50    3.90    --  -48.37 -77.00 -30.00  186
 49  \w   -120.00 -53.00   0.50    3.90    --  -48.37 -77.00-150.00  134
 50  \w   -120.00 -27.00   0.50    3.90    --  -48.37 -77.00 150.00  186
;
_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      -0.0324453000
_diffrn_orient_matrix_UB_12      -0.0564129000
_diffrn_orient_matrix_UB_13      -0.0391025000
_diffrn_orient_matrix_UB_21      0.0347126000
_diffrn_orient_matrix_UB_22      -0.0824169000
_diffrn_orient_matrix_UB_23      0.0403301000
_diffrn_orient_matrix_UB_31      -0.1035085000
_diffrn_orient_matrix_UB_32      0.0220280000
_diffrn_orient_matrix_UB_33      0.0388516000
_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  0.0539
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            111890
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.375
_diffrn_reflns_theta_min         2.934
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.573
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.574
_exptl_crystal_description       plate
_exptl_crystal_F_000             2312
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.579
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1289
_refine_ls_number_reflns         20384
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0437P)^2^+13.0148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17953
_reflns_number_total             20384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra03735a2.cif
_cod_data_source_block           am-ba
_cod_original_formula_sum        'C29.90 H19.40 Br2 Cl0.20 N2.40'
_cod_database_code               7249134
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.758
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-C119
 1.78 with sigma of 0.02
 Cl1-C119
 1.77 with sigma of 0.02
 Cl2-C119 = Cl1-C119
 1.771 with sigma of 0.01
 Cl2-Cl1
 2.916 with sigma of 0.03
 N10-C120
 1.14 with sigma of 0.02
 C120-N10
 1.137 with sigma of 0.01
 C121-N10
 2.593 with sigma of 0.02
 C120-C121
 1.456 with sigma of 0.01
 Cl2-Cl1
 2.92 with sigma of 0.04
 N10-C121
 2.59 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl2 \\sim C119: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
N10 \\sim C120 \\sim C121: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 Cl1, Cl2, C119
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N10, C120, C121
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N10)=Sof(C120)=Sof(C121)=Sof(H12A)=Sof(H12B)=Sof(H12C)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(C119)=Sof(H11D)=Sof(H11E)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C119(H11D,H11E)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8A), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41),
 C43(H43), C44(H44), C47(H47), C48(H48), C49(H49), C50(H50), C52(H52), C54(H54),
  C55(H55), C56(H56), C57(H57), C63(H63), C64(H64), C66(H66), C67(H67),
 C69(H69), C70(H70), C72(H72), C73(H73), C76(H76), C77(H77), C78(H78), C79(H79),
  C81(H81), C83(H83), C84(H84), C85(H85), C86(H86), C92(H92), C93(H93),
 C95(H95), C96(H96), C98(H98), C99(H99), C101(H101), C102(H102), C105(H105),
 C106(H106), C107(H107), C108(H108), C110(H110), C112(H112), C113(H113),
 C114(H114), C115(H115)
6.c Idealised Me refined as rotating group:
 C118(H11A,H11B,H11C), C121(H12A,H12B,H12C)
;
_shelx_res_checksum              27603
_shelx_hkl_checksum              42204
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.587