Open-Shell Effects on Optoelectronic Properties: Antiambipolar Charge Transport and Anti-Kasha Doublet Emission from a <i>N</i>-substituted Bisphenalenyl.
Imran, Muhammad; Wehrmann, Caleb M.; Chen, Mark S.; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b10677

data_4133858
_publ_section_title
;
 Open-Shell Effects on Optoelectronic Properties: Antiambipolar Charge
 Transport and Anti-Kasha Doublet Emission from a <i>N</i>-substituted
 Bisphenalenyl.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10677
_journal_year                    2019
_chemical_formula_moiety         'C F3 O3 S, C6 H5 Cl, C46 H30 N2'
_chemical_formula_sum            'C53 H35 Cl F3 N2 O3 S'
_chemical_formula_weight         872.4
_chemical_name_systematic        Ph2-Me2-PQPL+
_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
_audit_creation_date             2019-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                98.088(2)
_cell_angle_beta                 107.590(2)
_cell_angle_gamma                101.597(2)
_cell_formula_units_Z            2
_cell_length_a                   11.1341(8)
_cell_length_b                   11.4202(8)
_cell_length_c                   17.6484(13)
_cell_measurement_reflns_used    253
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.7
_cell_measurement_theta_min      2.38
_cell_volume                     2046.1(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30448
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.455
_diffrn_reflns_theta_min         2.863
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       parellepiped
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method chlorobenzene
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.191
_refine_diff_density_min         -1.263
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         7354
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0794
_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^)+(0.1195P)^2^+4.0399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5366
_reflns_number_total             7354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10677_si_002.cif
_cod_data_source_block           imran9_0m_a
_cod_database_code               4133858
_shelx_shelxl_version_number     2018/3
_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
2. Restrained distances
 S01-C01K \\sim S01-C0AA
 with sigma of 0.02
 F006-C01K \\sim F0-C0AA
 with sigma of 0.02
 F014-C01K \\sim F1-C0AA
 with sigma of 0.02
 F01F-C01K \\sim F01G-C0AA
 with sigma of 0.02
 S01-F006 \\sim S01-F0
 with sigma of 0.04
 S01-F014 \\sim S01-F1
 with sigma of 0.04
 S01-F01F \\sim S01-F01G
 with sigma of 0.04
 F006-F014 \\sim F0-F1
 with sigma of 0.04
 F006-F01F \\sim F0-F01G
 with sigma of 0.04
 F014-F01F \\sim F1-F01G
 with sigma of 0.04
3. Others
 Sof(C0AA)=Sof(F0)=Sof(F01G)=Sof(F1)=1-FVAR(1)
 Sof(F006)=Sof(F014)=Sof(F01F)=Sof(C01K)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C015(H015), C016(H016), C017(H017),
 C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D),
 C01E(H01E), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C01L(H01L),
 C01M(H01M), C01O(H01O), C01P(H01P), C01Q(H01Q), C01R(H01R)
4.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C), C00R(H00D,H00E,H00F)
;
_shelx_res_checksum              42523
_shelx_hkl_checksum              78156
_shelx_fab_checksum              30117
_olex2_submission_special_instructions 'No special instructions were received'