Structural, Spectroscopic, Electrochemical, and Electroluminescent Properties of Tetraalkoxydinaphthophenazines: New Solution-Processable Nonlinear Azaacenes
Kotwica, Kamil; Bujak, Piotr; Wamil, Damian; Pieczonka, Adam; Wiosna-Salyga, Gabriela; Gunka, Piotr A.; Jaroch, Tomasz; Nowakowski, Robert; Luszczynska, Beata; Witkowska, Ewelina; Glowacki, Ireneusz; Ulanski, Jacek; Zagorska, Malgorzata; Pron, Adam; The Journal of Physical Chemistry C 119 (2015) 10700–; doi:10.1021/acs.jpcc.5b01557

data_1554057
_publ_section_title
;
 Structural, Spectroscopic, Electrochemical, and Electroluminescent
 Properties of Tetraalkoxydinaphthophenazines: New Solution-Processable
 Nonlinear Azaacenes
;
_journal_issue                   19
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              10700
_journal_paper_doi               10.1021/acs.jpcc.5b01557
_journal_volume                  119
_journal_year                    2015
_chemical_formula_moiety         'C68 H96 N2 O4'
_chemical_formula_sum            'C68 H96 N2 O4'
_chemical_formula_weight         1005.46
_chemical_name_systematic
5,9,14,18-tetradecyloxy-dinaphto[2,3-a:2,3-h]phenazine
_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     direct
_audit_creation_date             2014-09-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                68.547(4)
_cell_angle_beta                 87.477(4)
_cell_angle_gamma                89.776(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8574(5)
_cell_length_b                   17.6322(7)
_cell_length_c                   17.7861(8)
_cell_measurement_reflns_used    6552
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      66.8330
_cell_measurement_theta_min      4.4430
_cell_volume                     2874.1(2)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -35.00   68.00   1.0000   26.5000
omega____ theta____ kappa____ phi______ frames
    -       41.1363  -38.0000 -120.0000 103

  2 omega  -33.00   71.00   1.0000   26.5000
omega____ theta____ kappa____ phi______ frames
    -       41.1363  -57.0000  120.0000 104

  3 omega   15.00  117.00   1.0000   26.5000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   38.0000   60.0000 102

  4 omega -121.00  -18.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000 -180.0000 103

  5 omega    9.00  133.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -89.0577 124

  6 omega    8.00  132.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  143.9435 124

  7 omega    8.00  132.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -119.5094 124

  8 omega   19.00  124.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -60.0000 105

  9 omega    8.00  132.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  152.8910 124

 10 omega   16.00   69.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 53

 11 omega   10.00  155.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  120.0000 145

 12 omega   73.00  168.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 95

 13 omega   10.00   84.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000   90.0000 74

 14 omega   19.00  124.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -180.0000 105

 15 omega   19.00  124.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -64.0000  115.6915 105

 16 omega   32.00  164.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000    0.0000 132

 17 omega   21.00   63.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   30.0000 42

 18 omega   92.00  119.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 27

 19 omega   63.00  114.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  150.0000 51

 20 omega  127.00  154.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  150.0000 27

 21 omega   64.00  168.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -150.0000 104

 22 omega   40.00   69.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -60.0000 29

 23 omega   30.00   57.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 27

 24 omega   84.00  118.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 34

 25 omega   69.00  101.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -180.0000 32

 26 omega   75.00  165.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -120.0000 90

 27 omega   71.00  109.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   90.0000 38

 28 omega   23.00   77.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 54

 29 omega   73.00  167.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  120.0000 94

 30 omega   88.00  127.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   30.0000 39

 31 omega   55.00   82.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000 -150.0000 27

 32 omega  137.00  168.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  120.0000 31

 33 omega   93.00  133.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 40

 34 omega   52.00  110.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -37.3562 58

 35 omega   32.00   59.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 27

 36 omega   81.00  119.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 38

 37 omega   91.00  125.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  120.0000 34

 38 omega   75.00  114.00   1.0000   68.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   46.0382 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0094181000
_diffrn_orient_matrix_UB_12      0.0537293000
_diffrn_orient_matrix_UB_13      -0.0905932000
_diffrn_orient_matrix_UB_21      -0.1421761000
_diffrn_orient_matrix_UB_22      0.0336683000
_diffrn_orient_matrix_UB_23      0.0078877000
_diffrn_orient_matrix_UB_31      0.0646082000
_diffrn_orient_matrix_UB_32      0.0692378000
_diffrn_orient_matrix_UB_33      0.0202412000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48313
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.110
_diffrn_reflns_theta_min         4.436
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59075
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       plate
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         10168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0686
_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^)+(0.1341P)^2^+0.7196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6217
_reflns_number_total             10168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jp5b01557_si_002.cif
_cod_data_source_block           DNP-C10
_cod_database_code               1554057
_shelxl_version_number           2014-3
_shelx_res_checksum              61548