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_4027313
_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            'C38 H16 Br4 F10 N4'
_chemical_formula_weight         1038.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_sh19
_audit_creation_method           SHELXL-97
_audit_update_record             'Tue Jan 10 13:41:14 CET 2012'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.308(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.572(2)
_cell_length_b                   12.965(4)
_cell_length_c                   12.987(3)
_cell_measurement_reflns_used    4319
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      2.56
_cell_volume                     1699.5(7)
_computing_cell_refinement
;
SAINT (Bruker AXS, 1997-2008). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT (Bruker AXS, 1997-2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            65782
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'fine-focus sealed tube (Mo)'
_exptl_absorpt_coefficient_mu    4.830
_exptl_absorpt_correction_T_max  0.746074
_exptl_absorpt_correction_T_min  0.485314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_recrystallization_method toluene
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.126
_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   1.190
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                3596
_reflns_number_total             5183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300894p_si_002_10.cif
_cod_data_source_block           ga_sh19_4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027313
_audit_block_refno               1407
_audit_block_usercomment         SH222c