Donor‒Acceptor Materials Exhibiting Thermally Activated Delayed Fluorescence Using a Planarized N-Phenylbenzimidazole Acceptor
Sauvé, Ethan R.; Paeng, Jaesuk; Yamaguchi, Shigehiro; Hudson, Zachary M.; The Journal of Organic Chemistry  (2019) –; doi:10.1021/acs.joc.9b02283

data_4036074
_publ_section_title
;
 Donor--Acceptor Materials Exhibiting Thermally Activated Delayed
 Fluorescence Using a Planarized N-Phenylbenzimidazole Acceptor
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02283
_journal_year                    2019
_chemical_formula_moiety         '1.64(C H2 Cl2), C34 H25 N3'
_chemical_formula_sum            'C35.64 H28.28 Cl3.28 N3'
_chemical_formula_weight         614.85
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                108.743(2)
_cell_angle_beta                 92.547(2)
_cell_angle_gamma                106.776(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8715(8)
_cell_length_b                   12.1969(9)
_cell_length_c                   12.8986(9)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.40
_cell_volume                     1532.85(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.387
_diffrn_reflns_theta_min         1.687
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction. wR2(int) was 0.0622 before and 0.0518 after correction. The ratio of minimum to maximum transmission is 0.8448. The \l/2 correction factor is not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       blade
_exptl_crystal_F_000             638
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         7648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0667P)^2^+0.6067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1407
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5374
_reflns_number_total             7648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02283_si_002.cif
_cod_data_source_block           zh023
_cod_database_code               4036074
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.907
_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. Others
 Sof(Cl1)=Sof(Cl2)=Sof(C35)=Sof(H35A)=Sof(H35B)=FVAR(1)
 Sof(Cl3)=Sof(Cl4)=Sof(C36)=Sof(H36A)=Sof(H36B)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30),
  C31(H31), C32(H32), C33(H33)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              36172
_shelx_hkl_checksum              9965
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_original_sample_id JP-4
_olex2_submission_special_instructions 'No special instructions were received'