#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:57:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178452 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/73/4027313.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4027313
loop_
_publ_author_name
'Sonja Geib'
'Susanne C. Martens'
'Ute Zschieschang'
'Florian Lombeck'
'Hubert Wadepohl'
'Hagen Klauk'
'Lutz H. Gade'
_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       'φ- and ω-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/[σ²(Fo²)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/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
#BEGIN Tags that were not found in dictionaries:
_audit_block_refno               1407
_audit_block_usercomment         SH222c
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.83989(4) 0.70815(3) 0.60435(3) 0.02274(11) Uani 1 1 d .
Br2 Br 0.30932(4) 0.27912(3) 0.66103(3) 0.02055(11) Uani 1 1 d .
F1 F 0.5581(2) 0.56831(19) 0.9285(2) 0.0280(6) Uani 1 1 d .
F2 F 0.6847(3) 0.5477(2) 1.1415(2) 0.0344(6) Uani 1 1 d .
F3 F 0.9123(3) 0.4378(2) 1.20769(19) 0.0335(6) Uani 1 1 d .
F4 F 1.0195(2) 0.35555(19) 1.06107(19) 0.0276(6) Uani 1 1 d .
F5 F 0.8983(2) 0.38044(18) 0.84930(18) 0.0247(5) Uani 1 1 d .
N1 N 0.7069(3) 0.5492(2) 0.7102(3) 0.0174(7) Uani 1 1 d .
N2 N 0.5447(3) 0.4257(2) 0.7282(3) 0.0164(7) Uani 1 1 d .
C1 C 0.6454(4) 0.5556(3) 0.6040(3) 0.0169(8) Uani 1 1 d .
C2 C 0.6938(4) 0.6245(3) 0.5366(3) 0.0174(8) Uani 1 1 d .
C3 C 0.3674(4) 0.3694(3) 0.5726(3) 0.0156(7) Uani 1 1 d .
C4 C 0.4833(4) 0.4324(3) 0.6219(3) 0.0168(8) Uani 1 1 d .
C5 C 0.5321(4) 0.4968(3) 0.5560(3) 0.0152(7) Uani 1 1 d .
C11 C 0.6536(4) 0.4844(3) 0.7652(3) 0.0175(8) Uani 1 1 d .
C14 C 0.7243(4) 0.4751(3) 0.8832(3) 0.0166(8) Uani 1 1 d .
C15 C 0.6730(4) 0.5167(3) 0.9601(3) 0.0208(8) Uani 1 1 d .
C16 C 0.7366(4) 0.5067(3) 1.0689(3) 0.0225(9) Uani 1 1 d .
C17 C 0.8535(4) 0.4524(3) 1.1024(3) 0.0235(9) Uani 1 1 d .
C18 C 0.9070(4) 0.4092(3) 1.0286(3) 0.0209(8) Uani 1 1 d .
C19 C 0.8431(4) 0.4214(3) 0.9199(3) 0.0175(8) Uani 1 1 d .
C21 C 0.1706(4) 0.6469(3) 0.4618(4) 0.0257(9) Uani 1 1 d .
C22 C 0.2228(5) 0.6396(4) 0.5723(4) 0.0330(11) Uani 1 1 d .
H22 H 0.1770 0.6006 0.6119 0.040 Uiso 1 1 calc R
C23 C 0.3395(5) 0.6875(4) 0.6265(4) 0.0346(11) Uani 1 1 d .
H23 H 0.3732 0.6814 0.7027 0.042 Uiso 1 1 calc R
C24 C 0.4086(5) 0.7450(3) 0.5704(4) 0.0300(10) Uani 1 1 d .
H24 H 0.4887 0.7790 0.6077 0.036 Uiso 1 1 calc R
C25 C 0.3589(5) 0.7516(3) 0.4599(4) 0.0281(10) Uani 1 1 d .
H25 H 0.4063 0.7892 0.4205 0.034 Uiso 1 1 calc R
C26 C 0.2416(4) 0.7044(3) 0.4059(4) 0.0259(9) Uani 1 1 d .
H26 H 0.2081 0.7108 0.3297 0.031 Uiso 1 1 calc R
C27 C 0.0421(5) 0.5962(4) 0.4001(4) 0.0367(12) Uani 1 1 d .
H27A H 0.0604 0.5277 0.3759 0.055 Uiso 1 1 calc R
H27B H -0.0026 0.6386 0.3373 0.055 Uiso 1 1 calc R
H27C H -0.0149 0.5893 0.4470 0.055 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 N1 C1 116.0(3) . .
C4 N2 C11 115.6(3) . .
N1 C1 C5 120.9(3) . .
N1 C1 C2 120.7(3) . .
C5 C1 C2 118.5(3) . .
C3 C2 C1 121.1(3) 3_666 .
C3 C2 Br1 121.3(3) 3_666 .
C1 C2 Br1 117.6(3) . .
C2 C3 C4 119.9(3) 3_666 .
C2 C3 Br2 122.0(3) 3_666 .
C4 C3 Br2 118.0(3) . .
N2 C4 C5 120.9(3) . .
N2 C4 C3 120.2(3) . .
C5 C4 C3 118.8(3) . .
C4 C5 C1 118.4(3) . .
C4 C5 C5 120.8(4) . 3_666
C1 C5 C5 120.8(4) . 3_666
N1 C11 N2 128.3(4) . .
N1 C11 C14 116.0(3) . .
N2 C11 C14 115.7(3) . .
C15 C14 C19 117.2(4) . .
C15 C14 C11 121.8(4) . .
C19 C14 C11 121.0(3) . .
F1 C15 C16 118.8(4) . .
F1 C15 C14 119.3(4) . .
C16 C15 C14 121.9(4) . .
F2 C16 C17 120.0(4) . .
F2 C16 C15 120.6(4) . .
C17 C16 C15 119.4(4) . .
F3 C17 C18 119.6(4) . .
F3 C17 C16 119.9(4) . .
C18 C17 C16 120.4(4) . .
F4 C18 C17 120.5(4) . .
F4 C18 C19 120.2(4) . .
C17 C18 C19 119.4(4) . .
F5 C19 C18 118.4(4) . .
F5 C19 C14 119.9(3) . .
C18 C19 C14 121.7(4) . .
C22 C21 C26 117.6(4) . .
C22 C21 C27 122.8(4) . .
C26 C21 C27 119.5(4) . .
C23 C22 C21 121.5(5) . .
C23 C22 H22 119.2 . .
C21 C22 H22 119.2 . .
C22 C23 C24 120.3(5) . .
C22 C23 H23 119.8 . .
C24 C23 H23 119.8 . .
C25 C24 C23 118.9(4) . .
C25 C24 H24 120.6 . .
C23 C24 H24 120.6 . .
C26 C25 C24 120.7(4) . .
C26 C25 H25 119.6 . .
C24 C25 H25 119.6 . .
C25 C26 C21 120.9(4) . .
C25 C26 H26 119.6 . .
C21 C26 H26 119.6 . .
C21 C27 H27A 109.5 . .
C21 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C21 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.878(4) .
Br2 C3 1.867(4) .
F1 C15 1.340(4) .
F2 C16 1.335(5) .
F3 C17 1.336(4) .
F4 C18 1.333(5) .
F5 C19 1.334(4) .
N1 C11 1.331(5) .
N1 C1 1.340(5) .
N2 C4 1.342(5) .
N2 C11 1.344(5) .
C1 C5 1.400(5) .
C1 C2 1.446(5) .
C2 C3 1.375(5) 3_666
C3 C2 1.375(5) 3_666
C3 C4 1.453(5) .
C4 C5 1.399(5) .
C5 C5 1.413(7) 3_666
C11 C14 1.497(5) .
C14 C15 1.379(6) .
C14 C19 1.391(5) .
C15 C16 1.378(6) .
C16 C17 1.375(6) .
C17 C18 1.370(6) .
C18 C19 1.381(5) .
C21 C22 1.379(7) .
C21 C26 1.404(6) .
C21 C27 1.507(6) .
C22 C23 1.374(7) .
C22 H22 0.9500 .
C23 C24 1.391(7) .
C23 H23 0.9500 .
C24 C25 1.377(7) .
C24 H24 0.9500 .
C25 C26 1.373(6) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C11 N1 C1 C5 0.0(5) . .
C11 N1 C1 C2 179.3(3) . .
N1 C1 C2 C3 179.0(4) . 3_666
C5 C1 C2 C3 -1.7(6) . 3_666
N1 C1 C2 Br1 -2.8(5) . .
C5 C1 C2 Br1 176.5(3) . .
C11 N2 C4 C5 0.1(5) . .
C11 N2 C4 C3 177.7(3) . .
C2 C3 C4 N2 -179.0(4) 3_666 .
Br2 C3 C4 N2 -0.7(5) . .
C2 C3 C4 C5 -1.4(5) 3_666 .
Br2 C3 C4 C5 177.0(3) . .
N2 C4 C5 C1 -1.1(6) . .
C3 C4 C5 C1 -178.7(3) . .
N2 C4 C5 C5 179.5(4) . 3_666
C3 C4 C5 C5 1.9(7) . 3_666
N1 C1 C5 C4 1.0(5) . .
C2 C1 C5 C4 -178.3(4) . .
N1 C1 C5 C5 -179.5(4) . 3_666
C2 C1 C5 C5 1.2(6) . 3_666
C1 N1 C11 N2 -1.2(6) . .
C1 N1 C11 C14 178.5(3) . .
C4 N2 C11 N1 1.1(6) . .
C4 N2 C11 C14 -178.6(3) . .
N1 C11 C14 C15 107.6(4) . .
N2 C11 C14 C15 -72.7(5) . .
N1 C11 C14 C19 -74.3(5) . .
N2 C11 C14 C19 105.5(4) . .
C19 C14 C15 F1 -179.4(3) . .
C11 C14 C15 F1 -1.2(6) . .
C19 C14 C15 C16 0.6(6) . .
C11 C14 C15 C16 178.8(4) . .
F1 C15 C16 F2 0.0(6) . .
C14 C15 C16 F2 180.0(4) . .
F1 C15 C16 C17 178.9(4) . .
C14 C15 C16 C17 -1.1(6) . .
F2 C16 C17 F3 2.4(6) . .
C15 C16 C17 F3 -176.5(4) . .
F2 C16 C17 C18 179.4(4) . .
C15 C16 C17 C18 0.5(6) . .
F3 C17 C18 F4 -2.2(6) . .
C16 C17 C18 F4 -179.2(4) . .
F3 C17 C18 C19 177.6(4) . .
C16 C17 C18 C19 0.6(6) . .
F4 C18 C19 F5 -1.5(6) . .
C17 C18 C19 F5 178.7(3) . .
F4 C18 C19 C14 178.7(3) . .
C17 C18 C19 C14 -1.1(6) . .
C15 C14 C19 F5 -179.3(3) . .
C11 C14 C19 F5 2.5(5) . .
C15 C14 C19 C18 0.5(6) . .
C11 C14 C19 C18 -177.7(4) . .
C26 C21 C22 C23 0.6(7) . .
C27 C21 C22 C23 -179.4(4) . .
C21 C22 C23 C24 -0.1(7) . .
C22 C23 C24 C25 -0.9(7) . .
C23 C24 C25 C26 1.5(6) . .
C24 C25 C26 C21 -1.1(6) . .
C22 C21 C26 C25 0.0(6) . .
C27 C21 C26 C25 179.9(4) . .
