#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014676.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_2014676
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o127
_journal_page_last  o130
_publ_section_title
;
Form III of 2,2',4,4',6,6'-hexanitroazobenzene (HNAB-III)
;
loop_
_publ_author_name
  'Mark A. Rodriguez'
  'Charles F. Campana'
  'A. David Rae'
  'Edward Graeber'
  'Bruno Morosin'
_chemical_name_common
;
2,2',4,4',6,6'-Hexanitroazobenzene (HNAB-III)
;
_chemical_formula_moiety  'C12 H4 N8 O12'
_chemical_formula_sum  'C12 H4 N8 O12'
_chemical_formula_iupac  'C12 H4 N8 O12'
_chemical_formula_weight  452.23
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  15.4015(8)
_cell_length_b  5.5240(3)
_cell_length_c  22.1182(11)
_cell_angle_alpha  90.00
_cell_angle_beta  110.367(2)
_cell_angle_gamma  90.00
_cell_volume  1764.13(16)
_cell_formula_units_Z  4
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.703
_diffrn_ambient_temperature  305(2)
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
  N1B 0.2686(3) 0.0000 0.52485(19) 0.0418(11) Uani d . 1 . . N
  C1B 0.3580(3) 0.9303(13) 0.5717(2) 0.0358(13) Uani d . 1 . . C
  C2B 0.3681(4) 0.7414(15) 0.6169(3) 0.0427(14) Uani d . 1 . . C
  C3B 0.4520(4) 0.6759(15) 0.6594(3) 0.0492(16) Uani d . 1 . . C
  H3BA 0.4572 0.5455 0.6870 0.059 Uiso calc R 1 . . H
  C4B 0.5291(4) 0.8045(15) 0.6611(3) 0.0528(16) Uani d . 1 . . C
  C5B 0.5239(4) 0.9946(14) 0.6198(3) 0.0498(15) Uani d . 1 . . C
  H5BA 0.5764 1.0818 0.6216 0.060 Uiso calc R 1 . . H
  C6B 0.4386(4) 1.0505(14) 0.5758(2) 0.0422(14) Uani d . 1 . . C
  N2B 0.2862(4) 0.6146(15) 0.6215(2) 0.0536(15) Uani d . 1 . . N
  O1B 0.2195(3) 0.7344(13) 0.6168(2) 0.0712(15) Uani d . 1 . . O
  O2B 0.2949(4) 0.3970(12) 0.6324(3) 0.0857(17) Uani d . 1 . . O
  N3B 0.6199(4) 0.7253(19) 0.7067(3) 0.097(2) Uani d . 1 . . N
  O3B 0.6234(4) 0.5239(19) 0.7319(3) 0.162(3) Uani d . 1 . . O
  O4B 0.6835(3) 0.8712(16) 0.7183(2) 0.116(2) Uani d . 1 . . O
  N4B 0.4333(3) 1.2488(13) 0.5282(2) 0.0529(12) Uani d . 1 . . N
  O5B 0.4958(3) 1.3981(13) 0.5452(2) 0.0857(15) Uani d . 1 . . O
  O6B 0.3726(3) 1.2481(13) 0.4775(2) 0.0893(18) Uani d . 1 . . O
  N5B 0.2336(3) 0.8231(14) 0.48988(18) 0.0427(11) Uani d . 1 . . N
  C7B 0.1455(3) 0.8825(14) 0.4411(2) 0.0364(13) Uani d . 1 . . C
  C8B 0.0798(4) 1.0445(14) 0.4445(2) 0.0383(13) Uani d . 1 . . C
  C9B -0.0026(4) 1.0777(14) 0.3948(2) 0.0433(15) Uani d . 1 . . C
  H9BA -0.0444 1.1957 0.3970 0.052 Uiso calc R 1 . . H
  C10B -0.0214(4) 0.9301(14) 0.3413(3) 0.0479(16) Uani d . 1 . . C
  C11B 0.0394(4) 0.7564(14) 0.3361(3) 0.0444(14) Uani d . 1 . . C
  H11B 0.0244 0.6555 0.3003 0.053 Uiso calc R 1 . . H
  C12B 0.1223(4) 0.7367(14) 0.3850(3) 0.0397(14) Uani d . 1 . . C
  N6B 0.0926(3) 1.1940(12) 0.5024(2) 0.0430(12) Uani d . 1 . . N
  O7B 0.0900(3) 1.0931(12) 0.55023(17) 0.0611(12) Uani d . 1 . . O
  O8B 0.1052(4) 1.4080(11) 0.4985(2) 0.0699(13) Uani d . 1 . . O
  N7B -0.1085(4) 0.9668(15) 0.2868(2) 0.0677(16) Uani d . 1 . . N
  O9B -0.1437(4) 1.1668(15) 0.2803(2) 0.107(2) Uani d . 1 . . O
  O10B -0.1388(4) 0.7941(15) 0.2508(2) 0.115(2) Uani d . 1 . . O
  N8B 0.1951(4) 0.5763(15) 0.3770(2) 0.0530(13) Uani d . 1 . . N
  O11B 0.1754(4) 0.3636(12) 0.3668(2) 0.0755(14) Uani d . 1 . . O
  O12B 0.2670(3) 0.6695(13) 0.3823(3) 0.0810(16) Uani d . 1 . . O
  N1A 0.2495(2) 0.2591(15) -0.0195(2) 0.0419(11) Uani d . 1 . . N
  C1A 0.2892(4) 0.2011(13) -0.0680(3) 0.0401(14) Uani d . 1 . . C
  C2A 0.2552(3) 0.0231(14) -0.1140(3) 0.0385(14) Uani d . 1 . . C
  C3A 0.2929(4) -0.0224(16) -0.1617(3) 0.0505(16) Uani d . 1 . . C
  H3A 0.2706 -0.1461 -0.1917 0.061 Uiso calc R 1 . . H
  C4A 0.3645(4) 0.1240(16) -0.1624(3) 0.0551(17) Uani d . 1 . . C
  C5A 0.4021(4) 0.3076(16) -0.1186(3) 0.0527(16) Uani d . 1 . . C
  H5A 0.4503 0.4040 -0.1209 0.063 Uiso calc R 1 . . H
  C6A 0.3633(4) 0.3404(14) -0.0704(3) 0.0448(15) Uani d . 1 . . C
  N2A 0.1727(4) -0.1217(14) -0.1189(2) 0.0517(14) Uani d . 1 . . N
  O1A 0.1043(3) -0.0072(13) -0.1177(2) 0.0700(14) Uani d . 1 . . O
  O2A 0.1777(4) -0.3374(12) -0.1246(3) 0.0878(17) Uani d . 1 . . O
  N3A 0.4041(4) 0.082(2) -0.2138(3) 0.094(2) Uani d . 1 . . N
  O3A 0.3888(5) -0.1144(19) -0.2394(3) 0.172(4) Uani d . 1 . . O
  O4A 0.4497(4) 0.2442(18) -0.2250(2) 0.131(3) Uani d . 1 . . O
  N4A 0.4048(3) 0.5248(14) -0.0218(3) 0.0644(15) Uani d . 1 . . N
  O5A 0.4383(4) 0.7029(11) -0.0378(2) 0.0990(17) Uani d . 1 . . O
  O6A 0.4036(4) 0.4898(14) 0.0317(2) 0.0880(17) Uani d . 1 . . O
  N5A 0.2418(3) 0.0763(12) 0.0111(2) 0.0419(11) Uani d . 1 . . N
  C7A 0.2020(4) 0.1295(13) 0.0597(3) 0.0355(13) Uani d . 1 . . C
  C8A 0.1337(4) 0.3007(14) 0.0548(2) 0.0374(13) Uani d . 1 . . C
  C9A 0.0979(4) 0.3385(14) 0.1039(3) 0.0479(16) Uani d . 1 . . C
  H9A 0.0555 0.4614 0.1012 0.058 Uiso calc R 1 . . H
  C10A 0.1275(4) 0.1881(15) 0.1559(3) 0.0473(15) Uani d . 1 . . C
  C11A 0.1925(4) 0.0040(15) 0.1629(3) 0.0514(16) Uani d . 1 . . C
  H11A 0.2093 -0.1016 0.1978 0.062 Uiso calc R 1 . . H
  C12A 0.2309(4) -0.0120(14) 0.1142(3) 0.0404(14) Uani d . 1 . . C
  N6A 0.0927(3) 0.4484(12) -0.0033(2) 0.0456(13) Uani d . 1 . . N
  O7A 0.0443(3) 0.3469(11) -0.05259(16) 0.0642(12) Uani d . 1 . . O
  O8A 0.1045(3) 0.6679(11) 0.0026(2) 0.0707(13) Uani d . 1 . . O
  N7A 0.0909(4) 0.2207(18) 0.2093(2) 0.0786(18) Uani d . 1 . . N
  O9A 0.0708(4) 0.4297(15) 0.2175(2) 0.098(2) Uani d . 1 . . O
  O10A 0.0875(5) 0.0475(17) 0.2402(3) 0.134(3) Uani d . 1 . . O
  N8A 0.3082(4) -0.1806(14) 0.1253(2) 0.0563(14) Uani d . 1 . . N
  O11A 0.3024(4) -0.3852(13) 0.1448(3) 0.0892(17) Uani d . 1 . . O
  O12A 0.3773(4) -0.0999(14) 0.1156(2) 0.0851(18) Uani d . 1 . . O
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  N1B 0.038(2) 0.047(3) 0.041(2) 0.004(2) 0.014(2) 0.000(2)
  C1B 0.026(3) 0.044(3) 0.034(3) 0.001(2) 0.006(2) -0.008(2)
  C2B 0.040(3) 0.052(4) 0.036(3) -0.001(3) 0.014(3) -0.003(3)
  C3B 0.042(3) 0.071(4) 0.037(3) -0.001(3) 0.015(3) 0.002(3)
  C4B 0.033(3) 0.085(4) 0.036(3) -0.003(3) 0.006(2) 0.013(3)
  C5B 0.036(3) 0.070(4) 0.045(3) -0.003(3) 0.017(3) -0.002(3)
  C6B 0.036(3) 0.059(3) 0.034(3) 0.001(3) 0.016(2) 0.000(3)
  N2B 0.036(3) 0.074(4) 0.045(3) -0.005(3) 0.007(2) -0.008(3)
  O1B 0.044(2) 0.106(4) 0.070(3) -0.004(3) 0.028(2) 0.006(3)
  O2B 0.083(4) 0.060(3) 0.104(4) -0.010(3) 0.021(3) 0.018(3)
  N3B 0.038(3) 0.190(8) 0.051(3) 0.001(4) -0.001(3) 0.042(4)
  O3B 0.069(3) 0.214(7) 0.156(6) 0.008(4) -0.019(4) 0.112(6)
  O4B 0.036(2) 0.217(6) 0.076(3) -0.016(3) -0.003(2) 0.047(4)
  N4B 0.043(3) 0.061(3) 0.061(3) -0.002(3) 0.026(3) -0.001(3)
  O5B 0.093(3) 0.087(3) 0.078(3) -0.042(3) 0.032(3) -0.003(2)
  O6B 0.052(3) 0.118(5) 0.084(3) 0.008(3) 0.006(3) 0.060(3)
  N5B 0.030(2) 0.051(3) 0.040(2) -0.002(2) 0.0041(19) -0.002(2)
  C7B 0.026(3) 0.047(3) 0.036(3) -0.003(3) 0.010(2) 0.004(2)
  C8B 0.034(3) 0.047(3) 0.036(3) -0.003(3) 0.016(2) -0.002(3)
  C9B 0.036(3) 0.056(4) 0.041(3) 0.015(3) 0.017(3) 0.007(3)
  C10B 0.033(3) 0.076(4) 0.035(3) 0.006(3) 0.011(3) 0.010(3)
  C11B 0.048(3) 0.052(3) 0.034(3) 0.002(3) 0.016(3) 0.002(3)
  C12B 0.038(3) 0.049(3) 0.037(3) 0.010(3) 0.019(3) -0.002(3)
  N6B 0.031(2) 0.055(3) 0.044(3) -0.003(2) 0.016(2) -0.010(3)
  O7B 0.078(3) 0.069(3) 0.044(2) -0.001(2) 0.031(2) -0.011(2)
  O8B 0.098(4) 0.038(3) 0.073(3) -0.003(2) 0.029(3) -0.006(2)
  N7B 0.045(3) 0.109(5) 0.041(3) 0.014(3) 0.006(2) 0.002(3)
  O9B 0.091(4) 0.156(6) 0.056(3) 0.078(4) 0.001(3) 0.006(3)
  O10B 0.083(4) 0.126(4) 0.087(4) -0.003(4) -0.032(3) -0.015(4)
  N8B 0.052(3) 0.062(3) 0.042(3) 0.012(3) 0.012(2) 0.002(3)
  O11B 0.102(4) 0.049(3) 0.086(3) 0.010(3) 0.046(3) -0.012(2)
  O12B 0.048(3) 0.094(4) 0.109(4) 0.008(3) 0.037(3) -0.020(3)
  N1A 0.033(2) 0.054(3) 0.043(2) 0.000(2) 0.0186(18) 0.001(2)
  C1A 0.033(3) 0.050(4) 0.039(3) 0.001(3) 0.015(2) -0.008(3)
  C2A 0.032(3) 0.051(3) 0.035(3) 0.005(3) 0.016(2) 0.007(3)
  C3A 0.041(3) 0.076(4) 0.033(3) 0.003(3) 0.011(3) -0.003(3)
  C4A 0.038(3) 0.091(5) 0.040(3) 0.000(3) 0.018(3) -0.003(3)
  C5A 0.034(3) 0.078(4) 0.049(3) -0.002(3) 0.018(3) 0.019(3)
  C6A 0.029(3) 0.055(4) 0.049(3) -0.003(3) 0.011(3) -0.004(3)
  N2A 0.041(3) 0.069(4) 0.043(3) -0.014(3) 0.012(2) -0.009(3)
  O1A 0.046(2) 0.086(4) 0.077(3) -0.014(3) 0.021(2) -0.008(3)
  O2A 0.111(4) 0.052(3) 0.110(4) -0.011(3) 0.052(3) -0.001(3)
  N3A 0.065(4) 0.179(8) 0.053(4) -0.013(5) 0.039(3) -0.015(4)
  O3A 0.185(7) 0.246(9) 0.140(6) -0.064(6) 0.125(6) -0.110(6)
  O4A 0.084(4) 0.252(8) 0.074(3) -0.041(5) 0.049(3) 0.018(4)
  N4A 0.040(3) 0.059(4) 0.087(4) -0.001(3) 0.013(3) -0.011(3)
  O5A 0.087(3) 0.067(3) 0.114(4) -0.032(3) -0.003(3) 0.015(3)
  O6A 0.082(3) 0.110(4) 0.081(3) -0.040(3) 0.041(3) -0.052(3)
  N5A 0.039(2) 0.049(3) 0.038(2) 0.003(2) 0.015(2) -0.002(2)
  C7A 0.038(3) 0.038(3) 0.032(3) -0.003(3) 0.013(2) -0.008(2)
  C8A 0.038(3) 0.045(3) 0.030(3) -0.008(3) 0.013(2) -0.002(3)
  C9A 0.040(3) 0.057(4) 0.050(3) -0.003(3) 0.020(3) -0.005(3)
  C10A 0.041(3) 0.072(4) 0.033(3) 0.001(3) 0.018(2) -0.005(3)
  C11A 0.054(4) 0.069(4) 0.028(3) -0.016(3) 0.009(3) 0.000(3)
  C12A 0.038(3) 0.043(3) 0.035(3) -0.003(3) 0.006(3) -0.011(3)
  N6A 0.047(3) 0.042(3) 0.049(3) 0.004(2) 0.019(3) -0.003(3)
  O7A 0.060(2) 0.070(3) 0.049(2) 0.005(2) 0.001(2) -0.004(2)
  O8A 0.091(3) 0.046(3) 0.078(3) -0.002(2) 0.033(3) 0.007(2)
  N7A 0.071(4) 0.128(6) 0.040(3) -0.013(4) 0.023(3) -0.015(4)
  O9A 0.102(4) 0.140(6) 0.054(3) 0.046(4) 0.032(3) -0.012(3)
  O10A 0.191(7) 0.154(5) 0.100(4) -0.039(5) 0.107(5) 0.008(5)
  N8A 0.061(3) 0.061(4) 0.041(3) 0.012(3) 0.011(3) -0.003(3)
  O11A 0.103(4) 0.057(3) 0.091(3) 0.015(3) 0.013(3) 0.018(3)
  O12A 0.069(3) 0.112(5) 0.081(3) 0.033(3) 0.035(3) 0.014(3)
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
  N1B N5B 1_545 1.247(7) ?
  N1B C1B 1_545 1.457(7) ?
  C1B C6B . 1.382(8) ?
  C1B C2B . 1.415(8) ?
  C1B N1B 1_565 1.457(7) ?
  C2B C3B . 1.356(8) ?
  C2B N2B . 1.478(8) ?
  C3B C4B . 1.372(8) ?
  C3B H3BA . 0.9300 ?
  C4B C5B . 1.377(8) ?
  C4B N3B . 1.477(8) ?
  C5B C6B . 1.370(8) ?
  C5B H5BA . 0.9300 ?
  C6B N4B . 1.502(8) ?
  N2B O1B . 1.196(7) ?
  N2B O2B . 1.224(7) ?
  N3B O4B . 1.225(8) ?
  N3B O3B . 1.237(10) ?
  N4B O6B . 1.185(6) ?
  N4B O5B . 1.222(6) ?
  N5B N1B 1_565 1.247(7) ?
  N5B C7B . 1.447(6) ?
  C7B C8B . 1.373(8) ?
  C7B C12B . 1.416(8) ?
  C8B C9B . 1.372(7) ?
  C8B N6B . 1.478(7) ?
  C9B C10B . 1.381(8) ?
  C9B H9BA . 0.9300 ?
  C10B C11B . 1.373(7) ?
  C10B N7B . 1.473(7) ?
  C11B C12B . 1.360(8) ?
  C11B H11B . 0.9300 ?
  C12B N8B . 1.488(8) ?
  N6B O8B . 1.206(5) ?
  N6B O7B . 1.209(5) ?
  N7B O9B . 1.217(7) ?
  N7B O10B . 1.226(7) ?
  N8B O12B . 1.189(7) ?
  N8B O11B . 1.215(8) ?
  N1A N5A . 1.244(6) ?
  N1A C1A . 1.442(7) ?
  C1A C2A . 1.381(8) ?
  C1A C6A . 1.393(8) ?
  C2A C3A . 1.392(8) ?
  C2A N2A . 1.474(8) ?
  C3A C4A . 1.372(8) ?
  C3A H3A . 0.9300 ?
  C4A C5A . 1.384(9) ?
  C4A N3A . 1.482(8) ?
  C5A C6A . 1.403(8) ?
  C5A H5A . 0.9300 ?
  C6A N4A . 1.457(8) ?
  N2A O2A . 1.204(7) ?
  N2A O1A . 1.236(7) ?
  N3A O3A . 1.207(11) ?
  N3A O4A . 1.218(10) ?
  N4A O6A . 1.205(7) ?
  N4A O5A . 1.220(7) ?
  N5A C7A . 1.441(7) ?
  C7A C12A . 1.375(8) ?
  C7A C8A . 1.391(8) ?
  C8A C9A . 1.393(7) ?
  C8A N6A . 1.467(7) ?
  C9A C10A . 1.362(8) ?
  C9A H9A . 0.9300 ?
  C10A C11A . 1.397(8) ?
  C10A N7A . 1.487(7) ?
  C11A C12A . 1.400(8) ?
  C11A H11A . 0.9300 ?
  C12A N8A . 1.464(8) ?
  N6A O7A . 1.221(5) ?
  N6A O8A . 1.227(5) ?
  N7A O10A . 1.187(8) ?
  N7A O9A . 1.224(8) ?
  N8A O11A . 1.224(8) ?
  N8A O12A . 1.239(7) ?