1,3,6,8-Tetraazapyrenes: Synthesis, Solid-State Structures, and Properties as Redox-Active Materials
Sonja Geib; Susanne C. Martens; Ute Zschieschang; Florian Lombeck; Hubert Wadepohl; Hagen Klauk; Lutz H. Gade; Journal of Organic Chemistry 77 (2012) 6107–6116; doi:10.1021/jo300894p

data_4027306
_publ_section_title
;
 1,3,6,8-Tetraazapyrenes: Synthesis, Solid-State Structures, and
 Properties as Redox-Active Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6107
_journal_page_last               6116
_journal_paper_doi               10.1021/jo300894p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C14 H4 F6 N4'
_chemical_formula_weight         342.21
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_sh17
_audit_creation_date
;
'Mon Nov 07 11:56:38 2011'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_audit_update_record             'Mon Nov  7 11:55:41 CET 2011'
_cell_angle_alpha                90.00
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_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.24403(16)
_cell_length_b                   9.39943(9)
_cell_length_c                   19.2102(2)
_cell_measurement_reflns_used    20108
_cell_measurement_temperature    99.94(19)
_cell_measurement_theta_max      29.0204
_cell_measurement_theta_min      3.3477
_cell_volume                     2439.35(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
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_diffrn_ambient_temperature      99.94(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9241
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega  -46.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -75.0000  101.0000 92

  2 omega    0.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000   90.0000 86

  3 omega  -52.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -77.0000  -30.0000 98

  4 omega   40.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000 -120.0000 45

  5 omega  -31.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -77.0000  150.0000 79

  6 omega   -1.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000  -30.0000 32

  7 omega   -7.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   77.0000 -180.0000 84

  8 omega    6.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000    0.0000 72

  9 omega  -49.00    7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   77.0000  -90.0000 56

 10 omega   12.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   77.0000 -180.0000 34

 11 omega  -49.00  -24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   77.0000 -180.0000 25

 12 omega  -49.00  -22.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   77.0000 -120.0000 27

 13 omega   10.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   57.0000  -60.0000 30

 14 omega  -51.00   20.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   80.0000   17.0000 71

 15 omega  -55.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817    0.0000 -180.0000 146

 16 omega  -52.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -77.0000  150.0000 100

 17 omega   -3.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000 -150.0000 90

 18 omega   -3.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000  -90.0000 90

 19 omega  -50.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -57.0000  -60.0000 90

 20 omega  -50.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -57.0000 -150.0000 90

 21 omega  -52.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817  -77.0000  -90.0000 100

 22 omega   -3.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3817   57.0000    0.0000 90

 23 omega  -49.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286   77.0000  150.0000 100

 24 omega  -89.00  -25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9286  -75.0000  131.0000 64

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0080942000
_diffrn_orient_matrix_UB_12      0.0446511000
_diffrn_orient_matrix_UB_13      -0.0311181000
_diffrn_orient_matrix_UB_21      0.0518589000
_diffrn_orient_matrix_UB_22      0.0085127000
_diffrn_orient_matrix_UB_23      0.0082217000
_diffrn_orient_matrix_UB_31      0.0013706000
_diffrn_orient_matrix_UB_32      -0.0602306000
_diffrn_orient_matrix_UB_33      -0.0219065000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44685
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         29.0204
_diffrn_reflns_theta_min         3.3477
_diffrn_source                   'Agilent SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+3.2462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2810
_reflns_number_total             3166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300894p_si_002_03.cif
_cod_data_source_block           ga_sh17a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4027306
_audit_block_refno               1354
_cell_oxdiff_length_a            14.2444(4)
_cell_oxdiff_length_b            9.3999(2)
_cell_oxdiff_length_c            19.2096(4)
_cell_oxdiff_angle_alpha         90.0116(19)
_cell_oxdiff_angle_beta          108.488(2)
_cell_oxdiff_angle_gamma         89.962(2)
_cell_oxdiff_volume              2439.35(10)
_cell_oxdiff_measurement_reflns_used 20108
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_theta     26.32
_reflns_odcompleteness_iscentric 1