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_4027314
_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 Cl4 F6 N4'
_chemical_formula_weight         479.98
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_sm33
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.425(11)
_cell_angle_beta                 82.339(7)
_cell_angle_gamma                76.700(13)
_cell_formula_units_Z            1
_cell_length_a                   5.101(3)
_cell_length_b                   7.908(4)
_cell_length_c                   9.882(5)
_cell_measurement_reflns_used    2991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.62
_cell_measurement_theta_min      3.16
_cell_volume                     380.7(4)
_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); SADABS (Bruker AXS, 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 0.990
_diffrn_measured_fraction_theta_max 0.939
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9329
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6560
_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            colourless
_exptl_crystal_density_diffrn    2.094
_exptl_crystal_description       irregular
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.090
_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   1.024
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0420P)^2^+0.3017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1924
_reflns_number_total             2489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300894p_si_002_11.cif
_cod_data_source_block           ga_sm33
_cod_original_cell_volume        380.7(3)
_cod_database_code               4027314
_audit_block_refno               1236