Two new red emitting ternary europium(III) complexes with high photoluminescence quantum yields and exceptional performance in OLED devices
Ilmi, Rashid; Li, Xiaofang; Al Rasbi, Nawal K.; Zhou, Liang; Wong, Wai-Yeung Raymond; Raithby, Paul R.; Khan, Muhammad S.; Dalton Transactions  (2023) –; doi:10.1039/D3DT02147E

data_7713748
_publ_section_title
;
 Two new red emitting ternary europium(III) complexes with high
 photoluminescence quantum yields and exceptional performance in OLED
 devices
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02147E
_journal_year                    2023
_chemical_compound_source        'Chemical synthesis'
_chemical_formula_moiety         'C54 H34 Eu F9 N2 O6'
_chemical_formula_sum            'C54 H34 Eu F9 N2 O6'
_chemical_formula_weight         1129.79
_chemical_name_systematic        msk50
_chemical_properties_physical    Luminescent
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2g0fvs
_audit_creation_date             2023-05-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-21 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.441(10)
_cell_length_b                   13.850(3)
_cell_length_c                   34.650(10)
_cell_measurement_reflns_used    80534
_cell_measurement_temperature    297
_cell_measurement_theta_max      33.67
_cell_measurement_theta_min      2.07
_cell_volume                     11249(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'stoe ipds II'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_unetI/netI     0.1137
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            80534
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         33.672
_diffrn_reflns_theta_min         2.072
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Stoe IPSD II Diffractometer'
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-RED, Stoe & Cie (2002)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             4512
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Recrystallised from a water/ethanol mix'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   0.95
_exptl_transmission_factor_min   0.85
_refine_diff_density_max         0.700
_refine_diff_density_min         -1.300
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.00063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     835
_refine_ls_number_reflns         21988
_refine_ls_number_restraints     483
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1667
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0770P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8858
_reflns_number_total             21988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02147e2.cif
_cod_data_source_block           msk50fp
_cod_original_sg_symbol_H-M      'I 2/c'
_cod_database_code               7713748
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F7-C44 \\sim F7A-C44
 with sigma of 0.02
 F8-C44 \\sim F8A-C44
 with sigma of 0.02
 F9-C44 \\sim F9A-C44
 with sigma of 0.02
 F7-F8 \\sim F7-F9 \\sim F8-F9 \\sim F7A-F8A \\sim F7A-F9A \\sim F8A-F9A
 with sigma of 0.04
 F4-C34 \\sim F4A-C34
 with sigma of 0.02
 F5-C34 \\sim F5A-C34
 with sigma of 0.02
 F6-C34 \\sim F6A-C34
 with sigma of 0.02
 F4-F5 \\sim F4-F6 \\sim F5-F6 \\sim F4A-F5A \\sim F4A-F6A \\sim F5A-F6A
 with sigma of 0.04
 F1-F2 \\sim F1A-F2A \\sim F1-F3 \\sim F1A-F3A \\sim F2-F3 \\sim F2A-F3A
 with sigma of 0.04
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5
 with sigma of 0.02
 C8-C7 \\sim C8A-C7A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C54-C9 \\sim C54A-C9A
 with sigma of 0.02
 C54-C5 \\sim C54A-C5
 with sigma of 0.02
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C8-C54 \\sim C8A-C54A
 with sigma of 0.04
 C7-C9 \\sim C7A-C9A
 with sigma of 0.04
 C7-C5 \\sim C7A-C5
 with sigma of 0.04
 C9-C5 \\sim C9A-C5
 with sigma of 0.04
 C37-C38 \\sim C37-C38A
 with sigma of 0.02
 C38-C39 \\sim C38A-C39A
 with sigma of 0.02
 C38-C43 \\sim C38A-C43A
 with sigma of 0.02
 C39-C40 \\sim C39A-C40A
 with sigma of 0.02
 C40-C41 \\sim C40A-C41A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42A
 with sigma of 0.02
 C42-C43 \\sim C42A-C43A
 with sigma of 0.02
 C37-C39 \\sim C37-C39A
 with sigma of 0.04
 C37-C43 \\sim C37-C43A
 with sigma of 0.04
 C38-C40 \\sim C38A-C40A
 with sigma of 0.04
 C38-C42 \\sim C38A-C42A
 with sigma of 0.04
 C39-C41 \\sim C39A-C41A
 with sigma of 0.04
 C39-C43 \\sim C39A-C43A
 with sigma of 0.04
 C40-C42 \\sim C40A-C42A
 with sigma of 0.04
 C41-C43 \\sim C41A-C43A
 with sigma of 0.04
3. Restrained planarity
 C5, C6, C7, C8, C9, C54
 with sigma of 0.1
 C38, C39, C40, C41, C42, C43
 with sigma of 0.1
 C38A, C39A, C40A, C41A, C42A, C43A
 with sigma of 0.1
4. Rigid bond restraints
 F1, F2, F3, F4, F5, F6, F7, F8, F9, F7A, F8A, F9A, F6A, F4A, F5A, F3A, F2A, F1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C39, C40, C41, C42, C43, C38
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C6, C7, C8, C9, C54
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6A, C7A, C8A, C9A, C54A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C38A, C39A, C40A, C41A, C42A, C43A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9
\\sim F7A \\sim F8A \\sim F9A \\sim F6A \\sim F4A \\sim F5A \\sim F3A \\sim F2A
\\sim F1A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C38: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C54: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
C6A \\sim C7A \\sim C8A \\sim C9A \\sim C54A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
6. Rigid body (RIGU) restrains
 C44, F8, C44, F9, C44, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C44, F8A, C44, F9A, C44, F7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C34, F4, C34, F5, C34, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C34, F4A, C34, F5A, C34, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, F1, C1, F2, C1, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, F1A, C1, F2A, C1, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6, C8, C7, C54, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6A, C8A, C7A, C54A, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(F6A)=Sof(F4A)=Sof(F5A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(F3A)=Sof(F2A)=Sof(F1A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(3)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(3)
 Sof(C54A)=Sof(H54A)=Sof(C9A)=Sof(H9A)=Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=
 Sof(C6A)=Sof(H6A)=1-FVAR(4)
 Sof(C6)=Sof(H6)=Sof(C8)=Sof(H8)=Sof(C7)=Sof(H7)=Sof(C54)=Sof(H54)=Sof(C9)=
 Sof(H9)=FVAR(4)
 Sof(C38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(H41A)=
 Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=1-FVAR(5)
 Sof(C38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=
 Sof(H42)=Sof(C43)=Sof(H43)=FVAR(5)
8.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C36(H36), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43),
 C46(H46), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C6(H6), C8(H8),
 C7(H7), C54(H54), C9(H9), C54A(H54A), C9A(H9A), C8A(H8A), C7A(H7A), C6A(H6A),
 C39A(H39A), C40A(H40A), C41A(H41A), C42A(H42A), C43A(H43A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'on a glass fibre with glue'
_olex2_submission_original_sample_id msk50
_olex2_submission_special_instructions 'No special instructions were received'