##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_4
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,3-dicyanotetrabenzo-pentacyclo[8.2.2.2^4,7^.0^2,9^.0^3,8^]hexadeca-
5,11,13,15-tetraene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C34 H22 N2, C H Cl3'
_chemical_formula_sum     'C35 H23 Cl3 N2'
_chemical_formula_iupac     'C34 H22 N2, C H Cl3'
_chemical_formula_weight     577.90
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     10.626(4)
_cell_length_b     16.048(5)
_cell_length_c     16.580(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2827.3(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     50
_cell_measurement_theta_min     10
_cell_measurement_theta_max     11
_cell_measurement_temperature     178(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.7
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1192
_exptl_absorpt_coefficient_mu     0.352
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     178(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nicolet R3'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3618
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0630
_diffrn_reflns_theta_min     3.12
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     147
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3618
_reflns_number_gt     2199
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1352
_refine_ls_R_factor_gt     0.0735
_refine_ls_wR_factor_gt     0.1765
_refine_ls_wR_factor_ref     0.2223
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     3618
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
      'calc w = 1/[σ²(Fo²)+(0.087P)²+5.5143P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.079
_refine_diff_density_min     -0.972
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     0.4(2)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'P3 (Nicolet, 1987)'
_computing_cell_refinement     'P3'
_computing_data_reduction     'XDISK (Nicolet, 1987)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP (Siemens, 1994)'
_computing_publication_material     SHELXL97
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 0.2559(6) 0.4075(4) 0.5363(4) 0.0381(15) Uani d . 1 . . C
    H1 0.2043 0.4558 0.5343 0.046 Uiso calc R 1 . . H
    C1A 0.3474(6) 0.3986(4) 0.5965(4) 0.0330(14) Uani d . 1 . . C
    C2 0.2421(6) 0.3441(4) 0.4793(4) 0.0403(16) Uani d . 1 . . C
    H2 0.1819 0.3502 0.4374 0.048 Uiso calc R 1 . . H
    C3 0.3147(7) 0.2724(4) 0.4829(4) 0.0381(15) Uani d . 1 . . C
    H3 0.3027 0.2291 0.4447 0.046 Uiso calc R 1 . . H
    C4 0.4050(7) 0.2645(4) 0.5429(4) 0.0357(15) Uani d . 1 . . C
    H4 0.4557 0.2158 0.5452 0.043 Uiso calc R 1 . . H
    C4A 0.4220(6) 0.3271(4) 0.5995(4) 0.0338(14) Uani d . 1 . . C
    C5 0.4595(7) 0.3002(4) 0.8146(4) 0.0431(17) Uani d . 1 . . C
    H5 0.5150 0.2540 0.8177 0.052 Uiso calc R 1 . . H
    C5A 0.4495(6) 0.3467(4) 0.7438(4) 0.0370(15) Uani d . 1 . . C
    C6 0.3866(8) 0.3230(5) 0.8805(4) 0.0490(19) Uani d . 1 . . C
    H6 0.3924 0.2917 0.9290 0.059 Uiso calc R 1 . . H
    C7 0.3049(8) 0.3911(5) 0.8768(5) 0.053(2) Uani d . 1 . . C
    H7 0.2538 0.4047 0.9220 0.064 Uiso calc R 1 . . H
    C8 0.2983(7) 0.4388(5) 0.8070(4) 0.0451(17) Uani d . 1 . . C
    H8 0.2437 0.4856 0.8042 0.054 Uiso calc R 1 . . H
    C8A 0.3725(6) 0.4170(4) 0.7416(4) 0.0354(14) Uani d . 1 . . C
    C9 0.3745(6) 0.4625(4) 0.6610(4) 0.0360(15) Uani d . 1 . . C
    H9 0.3151 0.5108 0.6594 0.043 Uiso calc R 1 . . H
    C10 0.5194(6) 0.3310(4) 0.6657(4) 0.0317(14) Uani d . 1 . . C
    H10 0.5712 0.2791 0.6682 0.038 Uiso calc R 1 . . H
    C11 0.5158(6) 0.4881(4) 0.6384(4) 0.0310(14) Uani d . 1 . . C
    C12 0.6008(6) 0.4091(4) 0.6464(4) 0.0298(13) Uani d . 1 . . C
    H12 0.6563 0.4007 0.5984 0.036 Uiso calc R 1 . . H
    C13 0.5063(6) 0.5329(4) 0.5598(4) 0.0322(14) Uani d . 1 . . C
    N 0.4878(6) 0.5696(4) 0.5024(4) 0.0473(16) Uani d . 1 . . N
    C1' 0.9221(7) 0.5354(4) 0.8344(4) 0.0401(16) Uani d . 1 . . C
    H1' 0.9620 0.4853 0.8511 0.048 Uiso calc R 1 . . H
    C1A' 0.8479(6) 0.5361(4) 0.7666(4) 0.0358(15) Uani d . 1 . . C
    C2' 0.9389(8) 0.6080(5) 0.8784(5) 0.0498(19) Uani d . 1 . . C
    H2' 0.9920 0.6073 0.9245 0.060 Uiso calc R 1 . . H
    C3' 0.8804(7) 0.6810(5) 0.8569(5) 0.0472(18) Uani d . 1 . . C
    H3' 0.8927 0.7303 0.8877 0.057 Uiso calc R 1 . . H
    C4' 0.8023(7) 0.6818(4) 0.7891(4) 0.0409(16) Uani d . 1 . . C
    H4' 0.7601 0.7316 0.7742 0.049 Uiso calc R 1 . . H
    C4A' 0.7862(6) 0.6109(4) 0.7438(4) 0.0324(14) Uani d . 1 . . C
    C5' 0.9220(6) 0.4494(5) 0.5717(4) 0.0436(17) Uani d . 1 . . C
    H5' 0.9668 0.4007 0.5868 0.052 Uiso calc R 1 . . H
    C5A' 0.8439(6) 0.4895(4) 0.6268(4) 0.0351(15) Uani d . 1 . . C
    C6' 0.9336(7) 0.4816(5) 0.4940(4) 0.0488(19) Uani d . 1 . . C
    H6' 0.9852 0.4538 0.4558 0.059 Uiso calc R 1 . . H
    C7' 0.8710(7) 0.5536(5) 0.4717(5) 0.052(2) Uani d . 1 . . C
    H7' 0.8810 0.5753 0.4188 0.063 Uiso calc R 1 . . H
    C8' 0.7925(7) 0.5946(5) 0.5272(4) 0.0446(17) Uani d . 1 . . C
    H8' 0.7487 0.6439 0.5123 0.053 Uiso calc R 1 . . H
    C8A' 0.7803(6) 0.5620(4) 0.6039(4) 0.0342(14) Uani d . 1 . . C
    C9' 0.7016(6) 0.6003(4) 0.6705(3) 0.0307(13) Uani d . 1 . . C
    H9' 0.6616 0.6539 0.6536 0.037 Uiso calc R 1 . . H
    C10' 0.8162(6) 0.4633(4) 0.7121(4) 0.0321(14) Uani d . 1 . . C
    H10' 0.8642 0.4121 0.7275 0.039 Uiso calc R 1 . . H
    C11' 0.6014(6) 0.5342(4) 0.7015(4) 0.0298(13) Uani d . 1 . . C
    C12' 0.6723(6) 0.4497(4) 0.7187(4) 0.0294(13) Uani d . 1 . . C
    H12' 0.6475 0.4246 0.7716 0.035 Uiso calc R 1 . . H
    C13' 0.5296(6) 0.5743(4) 0.7671(4) 0.0323(14) Uani d . 1 . . C
    N' 0.4742(6) 0.6100(3) 0.8149(3) 0.0373(13) Uani d . 1 . . N
    C99 1.0913(8) 0.6952(5) 0.6732(5) 0.061(2) Uani d . 1 . . C
    H99 1.0194 0.6636 0.6973 0.073 Uiso calc R 1 . . H
    Cl1 1.1543(6) 0.6361(3) 0.6002(2) 0.202(3) Uani d . 1 . . Cl
    Cl2 1.1987(3) 0.7139(2) 0.74848(17) 0.1070(11) Uani d . 1 . . Cl
    Cl3 1.0313(3) 0.78576(15) 0.6302(2) 0.1018(11) Uani d . 1 . . Cl
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
  Non-bonded distances:
      2.2180 (0.0085)  C11 - C12'
      2.2052 (0.0084)  C12 - C11'
 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
 - 7.0350 (0.0319) x - 4.9508 (0.0592) y + 11.3244 (0.0484) z = 1.1259 (0.0590)
 *    0.0577 (0.0031)  C11
 *   -0.0581 (0.0031)  C12
 *   -0.0571 (0.0031)  C11'
 *    0.0575 (0.0031)  C12'
 Rms deviation of fitted atoms =   0.0576
 - 7.0350 (0.0319) x - 4.9508 (0.0592) y + 11.3244 (0.0484) z = 1.1259 (0.0590)
 *    0.0577 (0.0031)  C11
 *   -0.0581 (0.0031)  C12
 *   -0.0571 (0.0031)  C11'
 *    0.0575 (0.0031)  C12'
 Rms deviation of fitted atoms =   0.0576
  7.0010 (0.0320) x + 6.4591 (0.0976) y - 10.5374 (0.0670) z = 0.0375 (0.0847)
 Angle to previous plane (with approximate esd) =  6.04 ( 0.68 )
 *    0.0000 (0.0001)  C11
 *    0.0000 (0.0000)  C12
 *    0.0000 (0.0000)  C12'
 Rms deviation of fitted atoms =   0.0000
 - 6.9920 (0.0323) x - 3.4276 (0.1013) y + 11.9722 (0.0563) z = 2.3628 (0.0887)
 Angle to previous plane (with approximate esd) = 11.93 ( 0.69 )
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.397(9) ?
    C1 C1A . 1.401(9) ?
    C1 H1 . 0.9500 ?
    C1A C4A . 1.396(9) ?
    C1A C9 . 1.509(9) ?
    C2 C3 . 1.387(10) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.388(9) ?
    C3 H3 . 0.9500 ?
    C4 C4A . 1.386(9) ?
    C4 H4 . 0.9500 ?
    C4A C10 . 1.510(9) ?
    C5 C6 . 1.388(10) ?
    C5 C5A . 1.394(9) ?
    C5 H5 . 0.9500 ?
    C5A C8A . 1.395(9) ?
    C5A C10 . 1.514(9) ?
    C6 C7 . 1.397(11) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.390(10) ?
    C7 H7 . 0.9500 ?
    C8 C8A . 1.386(9) ?
    C8 H8 . 0.9500 ?
    C8A C9 . 1.522(9) ?
    C9 C11 . 1.602(9) y
    C9 H9 . 1.0000 ?
    C10 C12 . 1.557(8) ?
    C10 H10 . 1.0000 ?
    C11 C13 . 1.491(9) ?
    C11 C12 . 1.563(8) y
    C11 C11' . 1.571(9) y
    C12 C12' . 1.560(8) y
    C12 H12 . 1.0000 ?
    C13 N . 1.136(8) ?
    C1' C1A' . 1.373(9) ?
    C1' C2' . 1.386(9) ?
    C1' H1' . 0.9500 ?
    C1A' C4A' . 1.419(9) ?
    C1A' C10' . 1.515(9) ?
    C2' C3' . 1.374(10) ?
    C2' H2' . 0.9500 ?
    C3' C4' . 1.397(10) ?
    C3' H3' . 0.9500 ?
    C4' C4A' . 1.373(9) ?
    C4' H4' . 0.9500 ?
    C4A' C9' . 1.522(8) ?
    C5' C5A' . 1.392(9) ?
    C5' C6' . 1.393(10) ?
    C5' H5' . 0.9500 ?
    C5A' C8A' . 1.397(9) ?
    C5A' C10' . 1.506(9) ?
    C6' C7' . 1.383(11) ?
    C6' H6' . 0.9500 ?
    C7' C8' . 1.406(10) ?
    C7' H7' . 0.9500 ?
    C8' C8A' . 1.381(9) ?
    C8' H8' . 0.9500 ?
    C8A' C9' . 1.516(8) ?
    C9' C11' . 1.589(9) y
    C9' H9' . 1.0000 ?
    C10' C12' . 1.549(9) ?
    C10' H10' . 1.0000 ?
    C11' C13' . 1.476(9) ?
    C11' C12' . 1.578(8) y
    C12' H12' . 1.0000 ?
    C13' N' . 1.141(8) ?
    C99 Cl1 . 1.676(9) ?
    C99 Cl2 . 1.717(9) ?
    C99 Cl3 . 1.740(8) ?
    C99 H99 . 1.0000 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C1A . . 118.8(6) ?
    C2 C1 H1 . . 120.6 ?
    C1A C1 H1 . . 120.6 ?
    C4A C1A C1 . . 120.2(6) ?
    C4A C1A C9 . . 115.1(6) ?
    C1 C1A C9 . . 124.7(6) ?
    C3 C2 C1 . . 121.1(6) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C2 C3 C4 . . 119.5(6) ?
    C2 C3 H3 . . 120.3 ?
    C4 C3 H3 . . 120.3 ?
    C4A C4 C3 . . 120.6(6) ?
    C4A C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C4A C1A . . 119.9(6) ?
    C4 C4A C10 . . 127.7(6) ?
    C1A C4A C10 . . 112.4(6) ?
    C6 C5 C5A . . 118.6(7) ?
    C6 C5 H5 . . 120.7 ?
    C5A C5 H5 . . 120.7 ?
    C5 C5A C8A . . 120.0(7) ?
    C5 C5A C10 . . 126.4(6) ?
    C8A C5A C10 . . 113.5(6) ?
    C5 C6 C7 . . 121.2(7) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C8 C7 C6 . . 119.9(7) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C8A C8 C7 . . 119.0(7) ?
    C8A C8 H8 . . 120.5 ?
    C7 C8 H8 . . 120.5 ?
    C8 C8A C5A . . 121.1(6) ?
    C8 C8A C9 . . 125.1(6) ?
    C5A C8A C9 . . 113.8(6) ?
    C1A C9 C8A . . 107.1(5) ?
    C1A C9 C11 . . 100.8(5) ?
    C8A C9 C11 . . 110.0(5) ?
    C1A C9 H9 . . 112.7 ?
    C8A C9 H9 . . 112.7 ?
    C11 C9 H9 . . 112.7 ?
    C4A C10 C5A . . 107.0(5) ?
    C4A C10 C12 . . 105.4(5) ?
    C5A C10 C12 . . 108.4(5) ?
    C4A C10 H10 . . 111.9 ?
    C5A C10 H10 . . 111.9 ?
    C12 C10 H10 . . 111.9 ?
    C13 C11 C12 . . 120.3(5) ?
    C13 C11 C11' . . 113.3(5) ?
    C12 C11 C11' . . 89.4(4) y
    C13 C11 C9 . . 105.4(5) ?
    C12 C11 C9 . . 108.3(5) ?
    C11' C11 C9 . . 120.5(5) ?
    C10 C12 C12' . . 116.6(5) ?
    C10 C12 C11 . . 110.4(5) ?
    C12' C12 C11 . . 90.5(4) y
    C10 C12 H12 . . 112.5 ?
    C12' C12 H12 . . 112.5 ?
    C11 C12 H12 . . 112.5 ?
    N C13 C11 . . 173.3(7) ?
    C1A' C1' C2' . . 119.9(7) ?
    C1A' C1' H1' . . 120.1 ?
    C2' C1' H1' . . 120.1 ?
    C1' C1A' C4A' . . 119.3(6) ?
    C1' C1A' C10' . . 127.6(6) ?
    C4A' C1A' C10' . . 113.0(5) ?
    C3' C2' C1' . . 121.4(7) ?
    C3' C2' H2' . . 119.3 ?
    C1' C2' H2' . . 119.3 ?
    C2' C3' C4' . . 119.0(7) ?
    C2' C3' H3' . . 120.5 ?
    C4' C3' H3' . . 120.5 ?
    C4A' C4' C3' . . 120.4(7) ?
    C4A' C4' H4' . . 119.8 ?
    C3' C4' H4' . . 119.8 ?
    C4' C4A' C1A' . . 119.8(6) ?
    C4' C4A' C9' . . 127.0(6) ?
    C1A' C4A' C9' . . 113.1(5) ?
    C5A' C5' C6' . . 119.2(7) ?
    C5A' C5' H5' . . 120.4 ?
    C6' C5' H5' . . 120.4 ?
    C5' C5A' C8A' . . 119.7(6) ?
    C5' C5A' C10' . . 127.2(6) ?
    C8A' C5A' C10' . . 113.2(6) ?
    C7' C6' C5' . . 121.0(7) ?
    C7' C6' H6' . . 119.5 ?
    C5' C6' H6' . . 119.5 ?
    C6' C7' C8' . . 120.1(7) ?
    C6' C7' H7' . . 120.0 ?
    C8' C7' H7' . . 120.0 ?
    C8A' C8' C7' . . 118.7(7) ?
    C8A' C8' H8' . . 120.6 ?
    C7' C8' H8' . . 120.6 ?
    C8' C8A' C5A' . . 121.4(6) ?
    C8' C8A' C9' . . 124.6(6) ?
    C5A' C8A' C9' . . 114.0(5) ?
    C8A' C9' C4A' . . 107.5(5) ?
    C8A' C9' C11' . . 109.5(5) ?
    C4A' C9' C11' . . 102.2(5) ?
    C8A' C9' H9' . . 112.3 ?
    C4A' C9' H9' . . 112.3 ?
    C11' C9' H9' . . 112.3 ?
    C5A' C10' C1A' . . 107.6(5) ?
    C5A' C10' C12' . . 107.3(5) ?
    C1A' C10' C12' . . 106.6(5) ?
    C5A' C10' H10' . . 111.7 ?
    C1A' C10' H10' . . 111.7 ?
    C12' C10' H10' . . 111.7 ?
    C13' C11' C11 . . 113.4(5) ?
    C13' C11' C12' . . 119.2(5) ?
    C11 C11' C12' . . 89.5(4) y
    C13' C11' C9' . . 107.1(5) ?
    C11 C11' C9' . . 119.1(5) ?
    C12' C11' C9' . . 108.2(5) ?
    C10' C12' C12 . . 119.0(5) ?
    C10' C12' C11' . . 109.7(5) ?
    C12 C12' C11' . . 89.3(4) y
    C10' C12' H12' . . 112.2 ?
    C12 C12' H12' . . 112.2 ?
    C11' C12' H12' . . 112.2 ?
    N' C13' C11' . . 175.5(7) ?
    Cl1 C99 Cl2 . . 111.0(5) ?
    Cl1 C99 Cl3 . . 108.8(5) ?
    Cl2 C99 Cl3 . . 113.3(5) ?
    Cl1 C99 H99 . . 107.9 ?
    Cl2 C99 H99 . . 107.9 ?
    Cl3 C99 H99 . . 107.9 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 C1 C1A C4A . . . . -0.6(9) ?
    C2 C1 C1A C9 . . . . 178.9(6) ?
    C1A C1 C2 C3 . . . . 1.7(10) ?
    C1 C2 C3 C4 . . . . -1.7(10) ?
    C2 C3 C4 C4A . . . . 0.8(10) ?
    C3 C4 C4A C1A . . . . 0.3(10) ?
    C3 C4 C4A C10 . . . . -176.6(6) ?
    C1 C1A C4A C4 . . . . -0.3(9) ?
    C9 C1A C4A C4 . . . . -179.9(6) ?
    C1 C1A C4A C10 . . . . 177.0(6) ?
    C9 C1A C4A C10 . . . . -2.5(8) ?
    C6 C5 C5A C8A . . . . 3.3(10) ?
    C6 C5 C5A C10 . . . . -179.1(6) ?
    C5A C5 C6 C7 . . . . -0.2(11) ?
    C5 C6 C7 C8 . . . . -1.9(11) ?
    C6 C7 C8 C8A . . . . 0.8(11) ?
    C7 C8 C8A C5A . . . . 2.4(10) ?
    C7 C8 C8A C9 . . . . 179.3(7) ?
    C5 C5A C8A C8 . . . . -4.5(10) ?
    C10 C5A C8A C8 . . . . 177.7(6) ?
    C5 C5A C8A C9 . . . . 178.3(6) ?
    C10 C5A C8A C9 . . . . 0.4(8) ?
    C4A C1A C9 C8A . . . . -51.2(7) ?
    C1 C1A C9 C8A . . . . 129.2(6) ?
    C4A C1A C9 C11 . . . . 63.8(6) ?
    C1 C1A C9 C11 . . . . -115.7(6) ?
    C8 C8A C9 C1A . . . . -125.0(7) ?
    C5A C8A C9 C1A . . . . 52.1(7) ?
    C8 C8A C9 C11 . . . . 126.3(7) ?
    C5A C8A C9 C11 . . . . -56.6(7) ?
    C4 C4A C10 C5A . . . . -127.1(7) ?
    C1A C4A C10 C5A . . . . 55.8(7) ?
    C4 C4A C10 C12 . . . . 117.7(7) ?
    C1A C4A C10 C12 . . . . -59.4(6) ?
    C5 C5A C10 C4A . . . . 127.5(7) ?
    C8A C5A C10 C4A . . . . -54.9(7) ?
    C5 C5A C10 C12 . . . . -119.3(7) ?
    C8A C5A C10 C12 . . . . 58.3(7) ?
    C1A C9 C11 C13 . . . . 68.0(6) ?
    C8A C9 C11 C13 . . . . -179.2(5) ?
    C1A C9 C11 C12 . . . . -62.0(6) ?
    C8A C9 C11 C12 . . . . 50.9(7) ?
    C1A C9 C11 C11' . . . . -162.4(5) ?
    C8A C9 C11 C11' . . . . -49.6(7) ?
    C4A C10 C12 C12' . . . . 156.5(5) ?
    C5A C10 C12 C12' . . . . 42.2(7) ?
    C4A C10 C12 C11 . . . . 55.1(6) ?
    C5A C10 C12 C11 . . . . -59.2(6) ?
    C13 C11 C12 C10 . . . . -115.9(6) ?
    C11' C11 C12 C10 . . . . 127.2(5) ?
    C9 C11 C12 C10 . . . . 5.2(7) ?
    C13 C11 C12 C12' . . . . 125.3(6) ?
    C11' C11 C12 C12' . . . . 8.5(5) y
    C9 C11 C12 C12' . . . . -113.6(5) ?
    C2' C1' C1A' C4A' . . . . -1.7(10) ?
    C2' C1' C1A' C10' . . . . -178.6(7) ?
    C1A' C1' C2' C3' . . . . 1.4(12) ?
    C1' C2' C3' C4' . . . . 0.0(12) ?
    C2' C3' C4' C4A' . . . . -1.2(11) ?
    C3' C4' C4A' C1A' . . . . 0.9(10) ?
    C3' C4' C4A' C9' . . . . 177.7(6) ?
    C1' C1A' C4A' C4' . . . . 0.6(10) ?
    C10' C1A' C4A' C4' . . . . 177.9(6) ?
    C1' C1A' C4A' C9' . . . . -176.6(6) ?
    C10' C1A' C4A' C9' . . . . 0.6(8) ?
    C6' C5' C5A' C8A' . . . . -1.1(10) ?
    C6' C5' C5A' C10' . . . . 178.2(7) ?
    C5A' C5' C6' C7' . . . . 1.4(11) ?
    C5' C6' C7' C8' . . . . -1.1(11) ?
    C6' C7' C8' C8A' . . . . 0.4(11) ?
    C7' C8' C8A' C5A' . . . . -0.1(10) ?
    C7' C8' C8A' C9' . . . . 178.6(6) ?
    C5' C5A' C8A' C8' . . . . 0.5(10) ?
    C10' C5A' C8A' C8' . . . . -178.9(6) ?
    C5' C5A' C8A' C9' . . . . -178.4(6) ?
    C10' C5A' C8A' C9' . . . . 2.2(8) ?
    C8' C8A' C9' C4A' . . . . -126.5(7) ?
    C5A' C8A' C9' C4A' . . . . 52.3(7) ?
    C8' C8A' C9' C11' . . . . 123.2(7) ?
    C5A' C8A' C9' C11' . . . . -58.0(7) ?
    C4' C4A' C9' C8A' . . . . 129.5(7) ?
    C1A' C4A' C9' C8A' . . . . -53.5(7) ?
    C4' C4A' C9' C11' . . . . -115.2(7) ?
    C1A' C4A' C9' C11' . . . . 61.8(6) ?
    C5' C5A' C10' C1A' . . . . 124.8(7) ?
    C8A' C5A' C10' C1A' . . . . -55.9(7) ?
    C5' C5A' C10' C12' . . . . -120.8(7) ?
    C8A' C5A' C10' C12' . . . . 58.5(7) ?
    C1' C1A' C10' C5A' . . . . -129.0(7) ?
    C4A' C1A' C10' C5A' . . . . 54.0(7) ?
    C1' C1A' C10' C12' . . . . 116.1(7) ?
    C4A' C1A' C10' C12' . . . . -60.9(7) ?
    C13 C11 C11' C13' . . . . 106.7(6) ?
    C12 C11 C11' C13' . . . . -130.3(5) ?
    C9 C11 C11' C13' . . . . -19.3(8) ?
    C13 C11 C11' C12' . . . . -131.4(5) ?
    C12 C11 C11' C12' . . . . -8.4(4) ?
    C9 C11 C11' C12' . . . . 102.6(5) ?
    C13 C11 C11' C9' . . . . -20.7(7) ?
    C12 C11 C11' C9' . . . . 102.3(5) ?
    C9 C11 C11' C9' . . . . -146.7(5) ?
    C8A' C9' C11' C13' . . . . 178.8(5) ?
    C4A' C9' C11' C13' . . . . 65.0(6) ?
    C8A' C9' C11' C11 . . . . -50.9(7) ?
    C4A' C9' C11' C11 . . . . -164.7(5) ?
    C8A' C9' C11' C12' . . . . 49.1(6) ?
    C4A' C9' C11' C12' . . . . -64.7(6) ?
    C5A' C10' C12' C12 . . . . 38.3(7) ?
    C1A' C10' C12' C12 . . . . 153.3(5) ?
    C5A' C10' C12' C11' . . . . -62.3(6) ?
    C1A' C10' C12' C11' . . . . 52.8(6) ?
    C10 C12 C12' C10' . . . . 126.1(6) ?
    C11 C12 C12' C10' . . . . -120.7(6) ?
    C10 C12 C12' C11' . . . . -121.7(5) ?
    C11 C12 C12' C11' . . . . -8.4(5) ?
    C13' C11' C12' C10' . . . . -114.1(6) ?
    C11 C11' C12' C10' . . . . 129.1(5) ?
    C9' C11' C12' C10' . . . . 8.5(7) ?
    C13' C11' C12' C12 . . . . 125.2(6) ?
    C11 C11' C12' C12 . . . . 8.4(4) ?
    C9' C11' C12' C12 . . . . -112.2(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C2 H2 N' 2_564 0.95 2.70 3.641(9) 172
    C6' H6' N' 2_664 0.95 2.59 3.455(9) 152
    C9 H9 Cl1 1_455 1.00 2.82 3.776(7) 161
data_global
_journal_date_recd_electronic     2003-01-06
_journal_date_accepted     2003-01-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue      2
_journal_page_first     o167
_journal_page_last     o168
_journal_paper_category     EO
_publ_contact_author_name     'Peter G. Jones'
_publ_contact_author_address
;
Institut fur Anorganische und Analytische Chemie
Technische Universitat Braunschweig
Postfach 3329
38023 Braunschweig
Germany
;
_publ_contact_author_email     p.jones@tu-bs.de
_publ_contact_author_fax     '049 531 391-5387'
_publ_contact_author_phone     '049 531 391-5382'
_publ_section_title
;
A dimer of 7-cyanodibenzobarrelene
;
loop_
    _publ_author_name
    _publ_author_address
    'Jones, Peter G.'
;
Institut für Anorganische und Analytische Chemie
Technische Universität Braunschweig
Postfach 3329
38023 Braunschweig
Germany
;
    'Bubenitschek, Peter'
;
Institut für Organische Chemie
Technische Universität Braunschweig
Postfach 3329
38023 Braunschweig
Germany
;
    'Hopf, Henning'
;
Institut für Organische Chemie
Technische Universität Braunschweig
Postfach 3329
38023 Braunschweig
Germany
;
    'Witulkski, Bernhard'
;
Institut für Organische Chemie
Technische Universität Braunschweig
Postfach 3329
38023 Braunschweig
Germany
;
