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_7237597
_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         'C33 H23 N3 O S'
_chemical_formula_sum            'C33 H23 N3 O S'
_chemical_formula_weight         509.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_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            4
_cell_length_a                   9.3757(5)
_cell_length_b                   9.5330(6)
_cell_length_c                   28.1021(18)
_cell_measurement_reflns_used    4462
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.3422
_cell_measurement_theta_min      3.0413
_cell_volume                     2511.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      150
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -73.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000   30.0000 93

  2 omega  -13.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000  -30.0000 94

  3 omega  -59.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -38.0000  150.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0277242000
_diffrn_orient_matrix_UB_12      -0.0189803000
_diffrn_orient_matrix_UB_13      0.0225865000
_diffrn_orient_matrix_UB_21      0.0682744000
_diffrn_orient_matrix_UB_22      0.0248009000
_diffrn_orient_matrix_UB_23      -0.0069102000
_diffrn_orient_matrix_UB_31      -0.0173378000
_diffrn_orient_matrix_UB_32      0.0674748000
_diffrn_orient_matrix_UB_33      0.0088994000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         3.047
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_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     344
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0426P)^2^+0.4016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4005
_reflns_number_total             4606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc06176a2.cif
_cod_data_source_block           171019_pzx_4_6237
_cod_database_code               7237597
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o s'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C28(H28), C29(H29), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              44118
_shelx_hkl_checksum              49666
_olex2_submission_special_instructions 'No special instructions were received'