#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:57:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178452 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/73/4027309.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_4027309
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            'C18 H4 F14 N4'
_chemical_formula_weight         542.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_sm12a
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.630(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.469(4)
_cell_length_b                   8.662(6)
_cell_length_c                   19.040(14)
_cell_measurement_reflns_used    5676
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      3.18
_cell_volume                     901.6(11)
_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 (Bruker AXS, 1997-2003)'
_computing_data_reduction        'SAINT (Bruker AXS, 1997-2008)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD-PXL-KAF2 (Bruker AXS Smart 1000)'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17408
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.14
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.99143
_exptl_absorpt_correction_T_min  0.94025
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.093
_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   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0692
_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/[σ²(Fo²)+(0.0000P)²+4.7642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                1718
_reflns_number_total             2245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300894p_si_002_06.cif
_cod_data_source_block           ga_sm12a
_cod_original_cell_volume        901.7(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027309
#BEGIN Tags that were not found in dictionaries:
_audit_block_refno               937
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.1347(7) 0.2311(4) 0.0380(2) 0.0266(8) Uani 1 1 d .
H1 H 0.1520 0.1230 0.0451 0.032 Uiso 1 1 calc R
C2 C 0.2923(7) 0.3297(4) 0.0709(2) 0.0257(8) Uani 1 1 d .
H2 H 0.4203 0.2900 0.1005 0.031 Uiso 1 1 calc R
C3 C 0.2681(7) 0.4943(4) 0.0616(2) 0.0246(8) Uani 1 1 d .
C4 C 0.0812(7) 0.5506(4) 0.01715(19) 0.0234(8) Uani 1 1 d .
C5 C 0.0584(7) 0.7113(4) 0.0074(2) 0.0232(8) Uani 1 1 d .
C6 C 0.3835(7) 0.7409(4) 0.0824(2) 0.0246(8) Uani 1 1 d .
C7 C 0.5494(7) 0.8517(4) 0.1231(2) 0.0264(8) Uani 1 1 d .
C8 C 0.4384(7) 0.9040(5) 0.1925(2) 0.0272(8) Uani 1 1 d .
C9 C 0.5966(8) 1.0079(5) 0.2401(2) 0.0295(9) Uani 1 1 d .
F1 F 0.7659(4) 0.7846(3) 0.13807(13) 0.0304(5) Uani 1 1 d .
F2 F 0.5912(5) 0.9790(3) 0.08441(13) 0.0326(6) Uani 1 1 d .
F3 F 0.3820(5) 0.7780(3) 0.22984(13) 0.0375(6) Uani 1 1 d .
F4 F 0.2317(5) 0.9819(3) 0.17718(14) 0.0407(7) Uani 1 1 d .
F5 F 0.8022(5) 0.9416(3) 0.25945(14) 0.0404(7) Uani 1 1 d .
F6 F 0.4740(5) 1.0418(3) 0.29736(14) 0.0445(7) Uani 1 1 d .
F7 F 0.6475(6) 1.1380(3) 0.20750(15) 0.0534(9) Uani 1 1 d .
N1 N 0.4242(6) 0.5918(4) 0.09456(17) 0.0253(7) Uani 1 1 d .
N2 N 0.2135(6) 0.8079(4) 0.04150(17) 0.0245(7) Uani 1 1 d .
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'
N N 0.0061 0.0033 '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'
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
C2 C1 C5 120.5(3) . 3_565
C2 C1 H1 119.7 . .
C5 C1 H1 119.7 3_565 .
C1 C2 C3 120.7(4) . .
C1 C2 H2 119.6 . .
C3 C2 H2 119.6 . .
N1 C3 C4 120.5(3) . .
N1 C3 C2 120.6(4) . .
C4 C3 C2 118.9(4) . .
C3 C4 C4 120.6(4) . 3_565
C3 C4 C5 119.0(3) . .
C4 C4 C5 120.4(5) 3_565 .
N2 C5 C4 119.9(4) . .
N2 C5 C1 121.2(3) . 3_565
C4 C5 C1 118.9(3) . 3_565
N2 C6 N1 129.6(4) . .
N2 C6 C7 114.9(3) . .
N1 C6 C7 115.5(3) . .
F1 C7 F2 107.9(3) . .
F1 C7 C6 110.2(3) . .
F2 C7 C6 110.2(3) . .
F1 C7 C8 108.2(3) . .
F2 C7 C8 107.8(3) . .
C6 C7 C8 112.3(3) . .
F4 C8 F3 108.6(3) . .
F4 C8 C9 107.0(3) . .
F3 C8 C9 107.3(3) . .
F4 C8 C7 108.2(3) . .
F3 C8 C7 108.5(3) . .
C9 C8 C7 116.9(3) . .
F5 C9 F7 108.4(4) . .
F5 C9 F6 108.5(3) . .
F7 C9 F6 108.4(3) . .
F5 C9 C8 112.1(3) . .
F7 C9 C8 110.2(3) . .
F6 C9 C8 109.1(3) . .
C6 N1 C3 115.3(3) . .
C6 N2 C5 115.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.354(5) .
C1 C5 1.435(5) 3_565
C1 H1 0.9500 .
C2 C3 1.442(5) .
C2 H2 0.9500 .
C3 N1 1.344(5) .
C3 C4 1.396(5) .
C4 C4 1.397(7) 3_565
C4 C5 1.409(5) .
C5 N2 1.345(5) .
C5 C1 1.435(5) 3_565
C6 N2 1.329(5) .
C6 N1 1.330(5) .
C6 C7 1.518(5) .
C7 F1 1.343(4) .
C7 F2 1.349(4) .
C7 C8 1.537(6) .
C8 F4 1.341(5) .
C8 F3 1.343(5) .
C8 C9 1.529(6) .
C9 F5 1.306(5) .
C9 F7 1.321(5) .
C9 F6 1.328(5) .
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
C5 C1 C2 C3 0.7(6) 3_565 .
C1 C2 C3 N1 179.7(4) . .
C1 C2 C3 C4 -1.0(6) . .
N1 C3 C4 C4 180.0(4) . 3_565
C2 C3 C4 C4 0.7(7) . 3_565
N1 C3 C4 C5 -0.1(6) . .
C2 C3 C4 C5 -179.4(4) . .
C3 C4 C5 N2 -0.9(6) . .
C4 C4 C5 N2 179.0(4) 3_565 .
C3 C4 C5 C1 -179.7(3) . 3_565
C4 C4 C5 C1 0.2(7) 3_565 3_565
N2 C6 C7 F1 -154.2(3) . .
N1 C6 C7 F1 27.9(5) . .
N2 C6 C7 F2 -35.2(5) . .
N1 C6 C7 F2 147.0(3) . .
N2 C6 C7 C8 85.0(4) . .
N1 C6 C7 C8 -92.8(4) . .
F1 C7 C8 F4 175.1(3) . .
F2 C7 C8 F4 58.7(4) . .
C6 C7 C8 F4 -63.0(4) . .
F1 C7 C8 F3 -67.2(4) . .
F2 C7 C8 F3 176.3(3) . .
C6 C7 C8 F3 54.7(4) . .
F1 C7 C8 C9 54.3(4) . .
F2 C7 C8 C9 -62.1(4) . .
C6 C7 C8 C9 176.2(3) . .
F4 C8 C9 F5 178.8(3) . .
F3 C8 C9 F5 62.4(4) . .
C7 C8 C9 F5 -59.7(5) . .
F4 C8 C9 F7 -60.3(4) . .
F3 C8 C9 F7 -176.7(3) . .
C7 C8 C9 F7 61.2(5) . .
F4 C8 C9 F6 58.6(4) . .
F3 C8 C9 F6 -57.8(4) . .
C7 C8 C9 F6 -179.9(3) . .
N2 C6 N1 C3 -1.2(6) . .
C7 C6 N1 C3 176.3(3) . .
C4 C3 N1 C6 1.0(5) . .
C2 C3 N1 C6 -179.6(4) . .
N1 C6 N2 C5 0.3(6) . .
C7 C6 N2 C5 -177.2(3) . .
C4 C5 N2 C6 0.8(5) . .
C1 C5 N2 C6 179.6(3) 3_565 .
