Conformationally-restricted bicarbazoles with phenylene bridges displaying deep-blue emission and high triplet energies: systematic structure-property relationships.
Wright, Iain A.; Al-Attar, Hameed A; Batsanov, Andrei S.; Monkman, Andrew P.; Bryce, Martin R.; Physical chemistry chemical physics : PCCP 20 (2018) 11867–11875; doi:10.1039/c8cp01636d

data_7230484
_publ_section_title
;
 Conformationally-restricted bicarbazoles with phenylene bridges
 displaying deep-blue emission and high triplet energies: systematic
 structure-property relationships.
;
_journal_issue                   17
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              11867
_journal_page_last               11875
_journal_paper_doi               10.1039/c8cp01636d
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C36 H26 N4'
_chemical_formula_sum            'C36 H26 N4'
_chemical_formula_weight         514.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-01 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                92.853(5)
_cell_angle_beta                 102.427(5)
_cell_angle_gamma                111.744(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3712(5)
_cell_length_b                   12.2475(7)
_cell_length_c                   12.7385(7)
_cell_measurement_reflns_used    3285
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.9150
_cell_measurement_theta_min      1.8260
_cell_volume                     1312.62(14)
_computing_cell_refinement
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -88.00   -1.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469  -57.0000  150.0000 174

  2 omega  -24.00   21.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -100.0000  -30.0000 90

  3 omega  -24.00   21.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -100.0000 -180.0000 90

  4 omega  -38.00   49.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469   57.0000  -60.0000 174

  5 omega  -94.00  -35.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -178.0000 -120.0000 118

  6 omega   -8.00   89.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -       20.1719   77.0000 -180.0000 194

  7 omega  -49.00   49.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -       20.1719  -77.0000   60.0000 196

  8 omega  -88.00  -45.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469  -57.0000   30.0000 86

  9 omega  -38.00   49.00   0.5000   20.6050
omega____ theta____ kappa____ phi______ frames
    -      -19.5469   57.0000 -180.0000 174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies, Gemini S Ultra kappa-diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0465518000
_diffrn_orient_matrix_UB_12      0.0178476000
_diffrn_orient_matrix_UB_13      0.0544429000
_diffrn_orient_matrix_UB_21      -0.0689927000
_diffrn_orient_matrix_UB_22      -0.0279133000
_diffrn_orient_matrix_UB_23      0.0187842000
_diffrn_orient_matrix_UB_31      0.0127612000
_diffrn_orient_matrix_UB_32      -0.0535791000
_diffrn_orient_matrix_UB_33      -0.0013200000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15132
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.809
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       tablet
_exptl_crystal_F_000             540
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol, chloroform, deuterochloroform'
_exptl_crystal_size_max          0.2495
_exptl_crystal_size_mid          0.1749
_exptl_crystal_size_min          0.0572
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0590P)^2^+0.4060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3317
_reflns_number_total             4626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cp01636d2.cif
_cod_data_source_block           1c
_cod_depositor_comments
'Adding full bibliography for 7230483--7230484.cif.'
_cod_original_cell_volume        1312.61(14)
_cod_database_code               7230484
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C36 H26 N4'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(1)
 Uiso(H36A)=Uiso(H36B)=Uiso(H36C)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C35(H35A,H35B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C14(H14),
 C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C28(H28), C29(H29), C32(H32)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              45015
_olex2_submission_special_instructions 'No special instructions were received'