#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013977.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_2013977
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o303
_journal_page_last  o304
_publ_section_title
;
3-(4-Acetylphenyl)-1-(4-nitrophenyl)triazene
;
loop_
_publ_author_name
  'H\"orner, Manfredo'
  'Brancher, Almir Luis'
  'Silva, Angela'
  'Bordinhao, Jairo'
  'M\"ossmer, C\"acilia M.'
_chemical_formula_moiety  'C14 H12 N4 O3'
_chemical_formula_sum  'C14 H12 N4 O3'
_chemical_formula_iupac  'C14 H12 N4 O3'
_chemical_formula_weight  284.28
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  14.357(6)
_cell_length_b  7.1964(13)
_cell_length_c  26.779(5)
_cell_angle_alpha  90
_cell_angle_beta  100.35(4)
_cell_angle_gamma  90
_cell_volume  2721.7(13)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.388
_diffrn_ambient_temperature  293(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
  O1 0.01964(11) 0.6804(2) 0.39769(6) 0.0771(5) Uani d . 1 . . O
  O11 0.76728(14) 0.2796(3) 0.75888(7) 0.1064(7) Uani d . 1 . . O
  O12 0.63806(14) 0.3986(3) 0.77367(6) 0.0976(7) Uani d . 1 . . O
  N1 0.68538(16) 0.3291(3) 0.74482(8) 0.0761(6) Uani d . 1 . . N
  N11 0.52677(12) 0.2366(3) 0.53903(6) 0.0566(5) Uani d . 1 . . N
  N12 0.44704(11) 0.3132(2) 0.52462(6) 0.0532(4) Uani d . 1 . . N
  N13 0.41564(12) 0.2878(3) 0.47558(7) 0.0567(5) Uani d . 1 . . N
  C2 0.07135(14) 0.5958(3) 0.37417(8) 0.0530(5) Uani d . 1 . . C
  C3 0.04492(16) 0.5816(4) 0.31830(8) 0.0720(7) Uani d . 1 . . C
  H3A -0.0176 0.6309 0.3076 0.108 Uiso calc R 1 . . H
  H3B 0.0459 0.4535 0.3084 0.108 Uiso calc R 1 . . H
  H3C 0.0891 0.6508 0.3027 0.108 Uiso calc R 1 . . H
  C11 0.56121(14) 0.2645(3) 0.59145(7) 0.0515(5) Uani d . 1 . . C
  C12 0.51637(15) 0.3705(3) 0.62349(8) 0.0607(6) Uani d . 1 . . C
  H12 0.4589 0.4281 0.611 0.073 Uiso calc R 1 . . H
  C13 0.55709(16) 0.3898(3) 0.67364(8) 0.0643(6) Uani d . 1 . . C
  H13 0.5273 0.4598 0.6954 0.077 Uiso calc R 1 . . H
  C14 0.64239(15) 0.3047(3) 0.69143(8) 0.0586(6) Uani d . 1 . . C
  C15 0.68790(16) 0.1988(3) 0.66067(8) 0.0626(6) Uani d . 1 . . C
  H15 0.7453 0.1416 0.6735 0.075 Uiso calc R 1 . . H
  C16 0.64685(14) 0.1788(3) 0.61037(8) 0.0578(6) Uani d . 1 . . C
  H16 0.6767 0.1075 0.589 0.069 Uiso calc R 1 . . H
  C21 0.32960(13) 0.3626(3) 0.45181(7) 0.0468(5) Uani d . 1 . . C
  C22 0.30022(14) 0.3275(3) 0.40068(7) 0.0510(5) Uani d . 1 . . C
  H22 0.3369 0.254 0.3832 0.061 Uiso calc R 1 . . H
  C23 0.21645(13) 0.4016(3) 0.37578(7) 0.0506(5) Uani d . 1 . . C
  H23 0.1972 0.378 0.3413 0.061 Uiso calc R 1 . . H
  C24 0.15986(12) 0.5111(3) 0.40088(7) 0.0463(5) Uani d . 1 . . C
  C25 0.18991(14) 0.5430(3) 0.45256(7) 0.0518(5) Uani d . 1 . . C
  H25 0.1524 0.614 0.4702 0.062 Uiso calc R 1 . . H
  C26 0.27378(13) 0.4716(3) 0.47791(7) 0.0526(5) Uani d . 1 . . C
  H26 0.2933 0.4957 0.5123 0.063 Uiso calc R 1 . . H
  H3 0.4492(16) 0.231(3) 0.4581(8) 0.064(7) Uiso d . 1 . . H
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
  O1 0.0617(10) 0.0969(13) 0.0741(11) 0.0288(9) 0.0160(8) 0.0031(9)
  O11 0.0804(13) 0.154(2) 0.0741(12) 0.0106(14) -0.0147(10) 0.0004(13)
  O12 0.0881(13) 0.1498(19) 0.0564(10) -0.0121(13) 0.0170(10) -0.0025(11)
  N1 0.0706(14) 0.0978(17) 0.0571(12) -0.0151(12) 0.0042(11) 0.0136(12)
  N11 0.0468(10) 0.0631(11) 0.0567(10) 0.0047(9) 0.0012(8) 0.0034(9)
  N12 0.0477(10) 0.0593(11) 0.0518(10) -0.0020(8) 0.0070(8) 0.0054(8)
  N13 0.0461(10) 0.0718(13) 0.0516(11) 0.0092(9) 0.0071(8) -0.0003(9)
  C2 0.0424(11) 0.0556(13) 0.0613(13) 0.0007(10) 0.0102(10) 0.0024(10)
  C3 0.0576(14) 0.0901(18) 0.0636(14) 0.0080(13) -0.0015(11) 0.0056(13)
  C11 0.0476(11) 0.0535(12) 0.0526(11) -0.0052(10) 0.0066(9) 0.0063(10)
  C12 0.0500(12) 0.0704(15) 0.0608(14) 0.0056(11) 0.0075(10) 0.0061(11)
  C13 0.0630(14) 0.0727(16) 0.0585(13) -0.0013(12) 0.0144(11) 0.0033(12)
  C14 0.0553(13) 0.0689(15) 0.0496(12) -0.0117(11) 0.0042(10) 0.0110(11)
  C15 0.0500(12) 0.0703(15) 0.0641(14) 0.0007(11) 0.0013(10) 0.0142(12)
  C16 0.0496(12) 0.0609(14) 0.0613(13) 0.0022(11) 0.0056(10) 0.0049(11)
  C21 0.0412(10) 0.0496(12) 0.0500(11) -0.0010(9) 0.0087(8) 0.0030(9)
  C22 0.0467(11) 0.0556(12) 0.0516(11) 0.0043(10) 0.0109(9) -0.0058(10)
  C23 0.0455(11) 0.0593(13) 0.0460(11) -0.0018(10) 0.0054(9) -0.0056(10)
  C24 0.0393(10) 0.0499(12) 0.0505(11) -0.0012(9) 0.0103(8) 0.0004(9)
  C25 0.0470(11) 0.0601(13) 0.0508(11) 0.0040(10) 0.0152(9) -0.0027(10)
  C26 0.0491(12) 0.0641(14) 0.0444(11) 0.0010(10) 0.0076(9) -0.0023(10)
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
  O1 C2 . 1.219(2) yes
  O11 N1 . 1.222(3) yes
  O11 N1 4_646 3.317(3) no
  O12 N1 . 1.223(3) yes
  N1 C14 . 1.462(3) no
  N1 O11 4_656 3.317(3) no
  N11 N12 . 1.267(2) yes
  N11 C11 . 1.416(3) no
  N12 N13 . 1.322(2) yes
  N13 C21 . 1.392(3) no
  C2 C24 . 1.474(3) no
  C2 C3 . 1.479(3) no
  C3 H3A . 0.96 no
  C3 H3B . 0.96 no
  C3 H3C . 0.96 no
  C11 C16 . 1.387(3) no
  C11 C12 . 1.389(3) no
  C12 C13 . 1.372(3) no
  C12 H12 . 0.93 no
  C13 C14 . 1.375(3) no
  C13 H13 . 0.93 no
  C14 C15 . 1.371(3) no
  C15 C16 . 1.377(3) no
  C15 H15 . 0.93 no
  C16 H16 . 0.93 no
  C21 C22 . 1.382(3) no
  C21 C26 . 1.395(3) no
  C22 C23 . 1.374(3) no
  C22 H22 . 0.93 no
  C23 C24 . 1.389(3) no
  C23 H23 . 0.93 no
  C24 C25 . 1.393(3) no
  C25 C26 . 1.371(3) no
  C25 H25 . 0.93 no
  C26 H26 . 0.93 no