Emissions from a triphenylamine‒benzothiadiazole‒monocarbaborane triad and its applications as a fluorescent chemosensor and a white OLED component
Peng, Zhixing; Zhang, Kang; Huang, Zongwei; Wang, Zaibin; Duttwyler, Simon; Wang, Yanguang; Lu, Ping; Journal of Materials Chemistry C 7 (2019) 2430–; doi:10.1039/C8TC06176A

data_7237598
_publ_section_title
;
 Emissions from a triphenylamine--benzothiadiazole--monocarbaborane triad
 and its applications as a fluorescent chemosensor and a white OLED
 component
;
_journal_issue                   8
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2430
_journal_paper_doi               10.1039/C8TC06176A
_journal_volume                  7
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H27 B11 N3 S, C8 H20 N'
_chemical_formula_sum            'C35 H47 B11 N4 S'
_chemical_formula_weight         674.73
_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             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-06-20 deposited with the CCDC.
2019-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   38.0550(16)
_cell_length_b                   8.6859(4)
_cell_length_c                   48.844(2)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.80
_cell_measurement_theta_min      3.74
_cell_volume                     16145.0(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            126298
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.986
_diffrn_reflns_theta_min         3.108
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1919 before and 0.0929 after correction. The Ratio of minimum to maximum transmission is 0.7175. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       block
_exptl_crystal_F_000             5696
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.704
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 7865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.419(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1841
_refine_ls_number_reflns         26836
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0997
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1820P)^2^+17.8584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2594
_refine_ls_wR_factor_ref         0.2723
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.765
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                22602
_reflns_number_total             26836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc06176a2.cif
_cod_data_source_block           wmj18077
_cod_original_cell_volume        16144.9(12)
_cod_database_code               7237598
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C43-C42
 1.58 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C43) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(B1C) \\sim Ueq, Uanis(B1)
\\sim Ueq, Uanis(C17A) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C20) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C30(H30A,H30B), C32(H32A,H32B), C34(H34A,H34B), C36(H36A,
 H36B), C38(H38A,H38B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,H44B),
 C46(H46A,H46B), C48(H48A,H48B), C50(H50A,H50B), C58(H58A,H58B), C52(H52A,H52B),
  C54(H54A,H54B), C56(H56A,H56B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C5A(H5AA), C6A(H6AA), C11A(H11B), C12A(H12A), C14A(H14A), C15A(H15A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C23A(H23A),
 C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C5B(H5B), C6B(H6B), C11B(H11D),
  C12B(H12B), C14B(H14B), C15B(H15B), C17B(H17B), C18B(H18B), C19B(H19B),
 C20B(H20B), C21B(H21B), C23B(H23B), C24B(H24B), C25B(H25B), C26B(H26B),
 C27B(H27B), C5C(H5C), C6C(H6C), C11C(H11F), C12C(H12C), C14C(H14C), C15C(H15C),
  C17C(H17C), C18C(H18C), C19C(H19C), C20C(H20C), C21C(H21C), C23C(H23C),
 C24C(H24C), C25C(H25C), C26C(H26C), C27C(H27C)
4.c Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C21)
4.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C43(H43A,
 H43B,H43C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C),
 C51(H51A,H51B,H51C), C59(H59A,H59B,H59C), C53(H53A,H53B,H53C), C55(H55A,H55B,
 H55C), C57(H57A,H57B,H57C)
4.e Boron cage BH refined with riding coordinates:
 C1(H1), B2(H2), B3(H3), B4(H4), B5(H5A), B6(H6A), B7(H7), B8(H8), B9(H9),
 B10(H10), B11(H11A), C1A(H1A), B2A(H2A), B3A(H3A), B4A(H4A), B5A(H5AB),
 B6A(H6AB), B7A(H7A), B8A(H8A), B9A(H9A), B10A(H10A), B11A(H11C), C1B(H1B),
 B2B(H2B), B3B(H3B), B4B(H4B), B5B(H5BA), B6B(H6BA), B7B(H7B), B8B(H8B),
 B9B(H9B), B10B(H10B), B11B(H11E), C1C(H1C), B2C(H2C), B3C(H3C), B4C(H4C),
 B5C(H5CA), B6C(H6CA), B7C(H7C), B8C(H8C), B9C(H9C), B10C(H10C), B11C(H11G)
;
_shelx_res_checksum              94087
_shelx_hkl_checksum              39242
_shelx_fab_checksum              80698
_olex2_submission_special_instructions 'No special instructions were received'