#------------------------------------------------------------------------------
#$Date: 2008-11-20 21:58:43 +0200 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008093.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_2008093
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  106
_journal_page_last  108
_publ_section_title
;
Interaction between an oxygen and an alkynyl carbon atom in
1-(2-nitrophenyl)-4-phenylbutadiyne
;
loop_
_publ_author_name
  'Hanne Skov Bengaard'
  'Sine Larsen'
  'Henning Osholm S\/orensen'
  'Kathryn J. Robinson'
  'John D. Wallis'
_chemical_formula_moiety  'C16 H9 N O2'
_chemical_formula_sum  'C16 H9 N O2'
_chemical_formula_structural  '(C6H5)CCCC(C6H4NO2)'
_chemical_formula_weight  247.24
_chemical_melting_point  433
_symmetry_cell_setting  'orthorhombic'
_symmetry_space_group_name_H-M  'P b c a'
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'
  '-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  7.532(5)
_cell_length_b  13.278(2)
_cell_length_c  23.7103(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2371.3(16)
_cell_formula_units_Z  8
_cell_measurement_temperature  122.0(5)
_exptl_crystal_density_diffrn  '1.385 (measured at 122 K)'
_exptl_crystal_density_meas  '1.305 (measured at 295 K)'
_diffrn_ambient_temperature  122(2)
_refine_ls_R_factor_obs  0.0364
_refine_ls_wR_factor_obs  0.0885
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.1311(2) 0.01525(7) 0.32021(4) 0.0347(3) Uani d . 1 . O
  O2 0.2143(2) 0.07953(8) 0.24093(4) 0.0369(3) Uani d . 1 . O
  N 0.14290(15) 0.08618(8) 0.28768(5) 0.0229(2) Uani d . 1 . N
  C1 -0.0859(2) 0.11124(10) 0.38890(5) 0.0212(3) Uani d . 1 . C
  C2 -0.1383(2) 0.05055(10) 0.42271(5) 0.0219(3) Uani d . 1 . C
  C3 -0.1971(2) -0.01961(10) 0.46083(5) 0.0221(3) Uani d . 1 . C
  C4 -0.2476(2) -0.08086(9) 0.49459(5) 0.0222(3) Uani d . 1 . C
  C11 0.0692(2) 0.18398(9) 0.30442(5) 0.0188(3) Uani d . 1 . C
  C12 -0.0365(2) 0.19249(9) 0.35274(5) 0.0191(3) Uani d . 1 . C
  C13 -0.1018(2) 0.28933(10) 0.36545(5) 0.0233(3) Uani d . 1 . C
  C14 -0.0632(2) 0.37115(10) 0.33167(6) 0.0262(3) Uani d . 1 . C
  C15 0.0436(2) 0.35999(10) 0.28436(6) 0.0249(3) Uani d . 1 . C
  C16 0.1098(2) 0.26606(10) 0.27052(6) 0.0226(3) Uani d . 1 . C
  C21 -0.3068(2) -0.15196(9) 0.53581(5) 0.0207(3) Uani d . 1 . C
  C22 -0.2646(2) -0.25486(10) 0.53059(6) 0.0250(3) Uani d . 1 . C
  C23 -0.3230(2) -0.32206(10) 0.57131(6) 0.0273(3) Uani d . 1 . C
  C24 -0.4208(2) -0.28904(10) 0.61699(6) 0.0270(3) Uani d . 1 . C
  C25 -0.4628(2) -0.18703(11) 0.62241(6) 0.0261(3) Uani d . 1 . C
  C26 -0.4063(2) -0.11905(10) 0.58189(6) 0.0229(3) Uani d . 1 . C
  H13 -0.179(2)  0.2986(11) 0.3976(6) 0.025(4) Uiso d . 1 . H
  H14 -0.109(2)  0.4407(12) 0.3420(6) 0.035(4) Uiso d . 1 . H
  H15 0.068(2)  0.4183(12) 0.2603(6) 0.038(5) Uiso d . 1 . H
  H16 0.184(2)  0.2568(11) 0.2380(6) 0.021(4) Uiso d . 1 . H
  H22 -0.187(2)  -0.2762(11) 0.4987(6) 0.028(4) Uiso d . 1 . H
  H23 -0.295(2)  -0.3935(12) 0.5666(6) 0.036(4) Uiso d . 1 . H
  H24 -0.460(2)  -0.3356(13) 0.6462(6) 0.038(5) Uiso d . 1 . H
  H25 -0.538(2)  -0.1639(11) 0.6548(6) 0.030(4) Uiso d . 1 . H
  H26 -0.433(2)  -0.0481(11) 0.5838(6) 0.026(4) 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 0.0515(7) 0.0209(5) 0.0315(5) 0.0066(5) 0.0115(5) 0.0073(4)
  O2 0.0493(7) 0.0322(5) 0.0291(5) 0.0054(5) 0.0179(5) 0.0001(4)
  N 0.0244(5) 0.0215(5) 0.0228(6) -0.0005(4) 0.0023(4) 0.0003(4)
  C1 0.0215(6) 0.0231(6) 0.0190(6) -0.0009(5) -0.0004(5) -0.0005(5)
  C2 0.0221(6) 0.0231(6) 0.0204(6) -0.0005(5) 0.0001(5) -0.0005(5)
  C3 0.0228(6) 0.0235(6) 0.0200(6) -0.0010(5) 0.0004(5) -0.0008(5)
  C4 0.0219(6) 0.0230(6) 0.0217(6) -0.0011(5) -0.0005(5) -0.0009(5)
  C11 0.0194(6) 0.0169(6) 0.0203(6) -0.0011(5) -0.0030(5) -0.0010(5)
  C12 0.0196(6) 0.0196(6) 0.0182(6) -0.0029(5) -0.0032(5) 0.0009(5)
  C13 0.0247(6) 0.0237(7) 0.0216(6) -0.0009(5) -0.0013(5) -0.0029(5)
  C14 0.0294(7) 0.0197(6) 0.0295(7) 0.0000(5) -0.0065(6) -0.0032(5)
  C15 0.0291(7) 0.0197(6) 0.0260(7) -0.0062(5) -0.0062(5) 0.0055(5)
  C16 0.0219(6) 0.0249(7) 0.0209(6) -0.0046(5) -0.0014(5) 0.0026(5)
  C21 0.0200(6) 0.0213(6) 0.0207(6) -0.0025(5) -0.0021(5) 0.0021(5)
  C22 0.0260(6) 0.0231(6) 0.0258(6) 0.0007(5) -0.0015(6) -0.0014(5)
  C23 0.0295(7) 0.0196(6) 0.0327(7) -0.0006(6) -0.0052(6) 0.0027(5)
  C24 0.0263(7) 0.0265(7) 0.0283(7) -0.0058(6) -0.0039(5) 0.0096(6)
  C25 0.0249(7) 0.0305(7) 0.0230(7) -0.0014(6) 0.0028(5) 0.0041(5)
  C26 0.0228(6) 0.0206(6) 0.0251(7) 0.0005(5) 0.0001(5) 0.0014(5)
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 N . 1.2207(14) yes
  O2 N . 1.2352(14) yes
  N C11 . 1.467(2) yes
  C1 C2 . 1.203(2) yes
  C1 C12 . 1.428(2) yes
  C2 C3 . 1.371(2) yes
  C3 C4 . 1.203(2) yes
  C4 C21 . 1.430(2) yes
  C11 C16 . 1.388(2) yes
  C11 C12 . 1.399(2) yes
  C12 C13 . 1.409(2) yes
  C13 C14 . 1.381(2) yes
  C13 H13 . 0.964(14) ?
  C14 C15 . 1.388(2) yes
  C14 H14 . 1.02(2) ?
  C15 C16 . 1.383(2) yes
  C15 H15 . 0.98(2) ?
  C16 H16 . 0.960(14) ?
  C21 C26 . 1.395(2) ?
  C21 C22 . 1.408(2) ?
  C22 C23 . 1.387(2) ?
  C22 H22 . 1.00(2) ?
  C23 C24 . 1.381(2) ?
  C23 H23 . 0.98(2) ?
  C24 C25 . 1.397(2) ?
  C24 H24 . 0.97(2) ?
  C25 C26 . 1.385(2) ?
  C25 H25 . 1.00(2) ?
  C26 H26 . 0.964(15) ?