#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:17:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180070 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/16/7051609.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_7051609
loop_
_publ_author_name
'Rosokha, Sergiy V.'
'Lu, Jianjiang'
'Han, Bing'
'Kochi, Jay K.'
_publ_section_title
;
 Unusual structural effects of intermolecular π-bonding in the
 tetracyanopyrazine (ion-radical) dimer
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              545
_journal_paper_doi               10.1039/b812829d
_journal_volume                  33
_journal_year                    2009
_chemical_formula_moiety         'C12 H8, C8 N6'
_chemical_formula_sum            'C20 H8 N6'
_chemical_formula_weight         332.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.2680(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6134(4)
_cell_length_b                   6.9065(3)
_cell_length_c                   13.2991(6)
_cell_measurement_temperature    173(2)
_cell_volume                     791.13(6)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT & SADABS (Bruker, 2003)'
_computing_molecular_graphics    'XP (Bruker, 1999)'
_computing_publication_material  'SHELXL, XCIF (Bruker, 1999)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_method       'omega-scan, full sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3439
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         35.77
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0423
_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)+(0.0820P)²+0.0544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2926
_reflns_number_total             3439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812829d.txt
_cod_data_source_block           kimusx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7051609
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.85974(7) 0.44449(9) 0.03031(5) 0.01761(12) Uani 1 1 d . . .
C2A C 0.90211(7) 0.44270(10) -0.07187(5) 0.01784(12) Uani 1 1 d . . .
N3A N 1.04218(7) 0.49851(9) -0.10227(4) 0.01852(12) Uani 1 1 d . . .
C3A C 0.70606(8) 0.38902(10) 0.06156(5) 0.02107(14) Uani 1 1 d . . .
C4A C 0.79463(8) 0.37646(11) -0.14805(5) 0.02246(14) Uani 1 1 d . . .
N1 N 0.58248(8) 0.34886(11) 0.08631(5) 0.02753(15) Uani 1 1 d . . .
N2 N 0.70770(9) 0.31922(13) -0.20691(5) 0.03278(17) Uani 1 1 d . . .
C1 C 0.03470(7) 0.00622(9) -0.07442(5) 0.01661(12) Uani 1 1 d . . .
C2 C 0.10652(8) 0.02708(11) -0.16558(5) 0.02019(13) Uani 1 1 d . . .
C3 C 0.26272(8) 0.09169(11) -0.16091(5) 0.02216(14) Uani 1 1 d . . .
C4 C 0.33728(8) 0.13020(11) -0.07055(5) 0.02142(14) Uani 1 1 d . . .
C5 C 0.26220(7) 0.10836(10) 0.02359(5) 0.01951(13) Uani 1 1 d . . .
C6 C 0.11105(7) 0.04687(9) 0.01841(5) 0.01627(12) Uani 1 1 d . . .
H2 H 0.0619(15) 0.0008(18) -0.2273(9) 0.034(3) Uiso 1 1 d . . .
H3 H 0.3254(13) 0.1025(19) -0.2272(9) 0.035(3) Uiso 1 1 d . . .
H4 H 0.4480(13) 0.1759(19) -0.0712(8) 0.032(3) Uiso 1 1 d . . .
H5 H 0.3173(13) 0.1380(18) 0.0844(9) 0.035(3) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1A 0.0176(2) 0.0159(3) 0.0193(3) 0.0004(2) 0.00281(19) -0.00045(19)
C2A 0.0186(3) 0.0167(3) 0.0182(2) 0.00016(19) 0.00094(19) -0.00011(19)
N3A 0.0190(2) 0.0176(3) 0.0190(2) 0.00039(18) 0.00205(18) -0.00046(18)
C3A 0.0205(3) 0.0213(3) 0.0214(3) -0.0013(2) 0.0026(2) -0.0024(2)
C4A 0.0214(3) 0.0247(3) 0.0212(3) 0.0008(2) 0.0004(2) -0.0003(2)
N1 0.0221(3) 0.0323(3) 0.0281(3) -0.0037(2) 0.0038(2) -0.0061(2)
N2 0.0287(3) 0.0394(4) 0.0301(3) -0.0017(3) -0.0066(3) -0.0018(3)
C1 0.0170(2) 0.0162(3) 0.0167(2) 0.00043(19) 0.00141(18) -0.00083(19)
C2 0.0213(3) 0.0223(3) 0.0170(2) -0.0004(2) 0.0025(2) -0.0020(2)
C3 0.0216(3) 0.0239(3) 0.0211(3) 0.0003(2) 0.0064(2) -0.0025(2)
C4 0.0176(3) 0.0217(3) 0.0250(3) -0.0005(2) 0.0038(2) -0.0026(2)
C5 0.0163(3) 0.0209(3) 0.0213(3) -0.0008(2) 0.0005(2) -0.0023(2)
C6 0.0160(2) 0.0161(3) 0.0167(2) 0.00010(19) 0.00138(18) -0.00109(18)
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'
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
_geom_angle_publ_flag
N3A C1A C2A 121.93(6) 3_765 . ?
N3A C1A C3A 116.83(6) 3_765 . ?
C2A C1A C3A 121.22(6) . . ?
N3A C2A C1A 121.98(6) . . ?
N3A C2A C4A 117.24(6) . . ?
C1A C2A C4A 120.77(6) . . ?
C2A N3A C1A 116.09(6) . 3_765 ?
N1 C3A C1A 178.53(8) . . ?
N2 C4A C2A 177.96(8) . . ?
C2 C1 C6 122.51(6) . . ?
C2 C1 C6 147.38(6) . 3 ?
C6 C1 C6 90.10(5) . 3 ?
C1 C2 C3 115.22(6) . . ?
C1 C2 H2 125.3(8) . . ?
C3 C2 H2 119.5(8) . . ?
C4 C3 C2 122.27(6) . . ?
C4 C3 H3 118.8(7) . . ?
C2 C3 H3 118.9(7) . . ?
C3 C4 C5 122.22(6) . . ?
C3 C4 H4 119.3(6) . . ?
C5 C4 H4 118.5(6) . . ?
C6 C5 C4 115.15(6) . . ?
C6 C5 H5 125.1(7) . . ?
C4 C5 H5 119.7(7) . . ?
C5 C6 C1 122.63(6) . . ?
C5 C6 C1 147.48(6) . 3 ?
C1 C6 C1 89.90(5) . 3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N3A 1.3330(9) 3_765 ?
C1A C2A 1.4087(9) . ?
C1A C3A 1.4412(9) . ?
C2A N3A 1.3312(8) . ?
C2A C4A 1.4436(10) . ?
N3A C1A 1.3330(9) 3_765 ?
C3A N1 1.1496(9) . ?
C4A N2 1.1507(10) . ?
C1 C2 1.3711(9) . ?
C1 C6 1.4240(9) . ?
C1 C6 1.5080(8) 3 ?
C2 C3 1.4186(10) . ?
C2 H2 0.923(12) . ?
C3 C4 1.3856(10) . ?
C3 H3 1.038(12) . ?
C4 C5 1.4198(9) . ?
C4 H4 1.005(11) . ?
C5 C6 1.3709(9) . ?
C5 H5 0.958(12) . ?
C6 C1 1.5080(8) 3 ?
