#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/7/7051213.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_7051213
_journal_name_full  'New Journal of Chemistry'
_journal_year      2001
_journal_volume  25
_journal_page_first  1553
_publ_section_title
;
Design and synthesis of 4,4'-p-conjugated-[2,2']-bipyridines : a
versatile class of tuneable chromophores and fluorophores
;
loop_
_publ_author_name
'Olivier Maury'
'Jean-Paul Guegan'
'Thierry Renouard'
'Adam Hilton'
'Philippe Dupau'
'Nicolas Sandon'
'L. Toupet'
'H.Le Bozec'
_chemical_formula_sum  'C16 H18 N3'
_chemical_formula_weight  252.33
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a  7.309(3)
_cell_length_b  7.698(5)
_cell_length_c  25.101(7)
_cell_angle_alpha  90.00
_cell_angle_beta  92.13(2)
_cell_angle_gamma  90.00
_cell_volume  1411.3(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.188
_diffrn_ambient_temperature  293(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
N1 N 0.2672(5) 0.0634(5) 0.98447(12) 0.0874(11) Uani 1 1 d . . .
N8 N 0.6453(5) 0.0455(4) 0.82162(11) 0.0739(9) Uani 1 1 d . . .
N15 N 0.9763(5) 0.0493(5) 0.62386(14) 0.0964(11) Uani 1 1 d . . .
C2 C 0.4436(5) 0.0267(5) 0.97628(12) 0.0685(11) Uani 1 1 d . . .
C3 C 0.5184(5) 0.0371(5) 0.92661(13) 0.0704(11) Uani 1 1 d . . .
H3 H 0.6413 0.0107 0.9226 0.084 Uiso 1 1 calc R . .
C4 C 0.4104(6) 0.0867(5) 0.88292(14) 0.0711(11) Uani 1 1 d . . .
C5 C 0.2293(6) 0.1250(5) 0.89186(15) 0.0845(13) Uani 1 1 d . . .
H5 H 0.1515 0.1604 0.8638 0.101 Uiso 1 1 calc R . .
C6 C 0.1648(6) 0.1105(6) 0.94240(18) 0.1013(15) Uani 1 1 d . . .
H6 H 0.0420 0.1353 0.9473 0.122 Uiso 1 1 calc R . .
C7 C 0.4838(7) 0.0965(5) 0.82947(14) 0.0761(12) Uani 1 1 d . . .
H7 H 0.4117 0.1403 0.8013 0.091 Uiso 1 1 calc R . .
C9 C 0.7195(5) 0.0553(5) 0.77048(14) 0.0659(10) Uani 1 1 d . . .
C10 C 0.8741(6) -0.0447(5) 0.76292(15) 0.0774(11) Uani 1 1 d . . .
H10 H 0.9209 -0.1121 0.7910 0.093 Uiso 1 1 calc R . .
C11 C 0.9599(5) -0.0474(5) 0.71557(15) 0.0789(12) Uani 1 1 d . . .
H11 H 1.0636 -0.1158 0.7121 0.095 Uiso 1 1 calc R . .
C12 C 0.8945(5) 0.0509(5) 0.67219(15) 0.0720(11) Uani 1 1 d . . .
C13 C 0.7421(5) 0.1533(5) 0.68049(14) 0.0767(12) Uani 1 1 d . . .
H13 H 0.6968 0.2233 0.6528 0.092 Uiso 1 1 calc R . .
C14 C 0.6561(5) 0.1549(5) 0.72804(14) 0.0718(11) Uani 1 1 d . . .
H14 H 0.5532 0.2243 0.7318 0.086 Uiso 1 1 calc R . .
C16 C 1.1429(6) -0.0538(6) 0.61490(17) 0.1022(14) Uani 1 1 d . . .
H16A H 1.1366 -0.1624 0.6343 0.123 Uiso 1 1 calc R . .
H16B H 1.1488 -0.0810 0.5773 0.123 Uiso 1 1 calc R . .
C17 C 1.3082(6) 0.0400(7) 0.6322(2) 0.165(2) Uani 1 1 d . . .
H17A H 1.4136 -0.0310 0.6265 0.198 Uiso 1 1 calc R . .
H17B H 1.3026 0.0670 0.6695 0.198 Uiso 1 1 calc R . .
H17C H 1.3170 0.1456 0.6122 0.198 Uiso 1 1 calc R . .
C18 C 0.9200(8) 0.1656(7) 0.58070(19) 0.126(2) Uani 1 1 d . . .
H18A H 1.0256 0.1934 0.5600 0.151 Uiso 1 1 calc R . .
H18B H 0.8752 0.2729 0.5957 0.151 Uiso 1 1 calc R . .
C19 C 0.7745(8) 0.0898(8) 0.54465(19) 0.156(3) Uani 1 1 d . . .
H19A H 0.7417 0.1719 0.5171 0.187 Uiso 1 1 calc R . .
H19B H 0.6689 0.0634 0.5648 0.187 Uiso 1 1 calc R . .
H19C H 0.8193 -0.0147 0.5288 0.187 Uiso 1 1 calc R . .
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
N1 0.098(3) 0.101(3) 0.064(2) 0.006(2) 0.013(2) 0.024(2)
N8 0.098(3) 0.070(2) 0.0542(19) -0.0030(17) 0.0048(18) 0.006(2)
N15 0.084(3) 0.111(3) 0.096(3) 0.020(2) 0.030(2) 0.025(2)
C2 0.092(3) 0.062(3) 0.052(2) -0.0014(19) 0.011(2) 0.006(2)
C3 0.086(3) 0.067(3) 0.058(2) 0.001(2) 0.008(2) 0.002(2)
C4 0.089(3) 0.067(3) 0.058(2) 0.001(2) 0.006(2) 0.006(2)
C5 0.100(4) 0.089(3) 0.065(3) 0.006(2) 0.000(2) 0.028(3)
C6 0.109(4) 0.121(4) 0.075(3) 0.012(3) 0.013(3) 0.035(3)
C7 0.104(3) 0.070(3) 0.054(2) 0.004(2) 0.002(2) 0.004(3)
C9 0.073(3) 0.068(3) 0.057(2) -0.001(2) 0.001(2) -0.001(2)
C10 0.091(3) 0.080(3) 0.060(2) 0.006(2) -0.008(2) 0.007(3)
C11 0.076(3) 0.085(3) 0.076(3) 0.005(2) 0.001(2) 0.016(2)
C12 0.073(3) 0.078(3) 0.065(3) 0.001(2) 0.012(2) 0.002(3)
C13 0.088(3) 0.082(3) 0.061(3) 0.017(2) 0.008(2) 0.010(3)
C14 0.080(3) 0.074(3) 0.061(2) 0.008(2) 0.003(2) 0.013(2)
C16 0.101(3) 0.106(4) 0.101(3) 0.000(3) 0.026(3) -0.012(3)
C17 0.097(4) 0.146(5) 0.254(7) -0.021(5) 0.026(4) -0.038(4)
C18 0.159(5) 0.125(5) 0.099(4) 0.049(4) 0.060(4) 0.047(4)
C19 0.185(6) 0.197(7) 0.086(4) 0.032(4) 0.019(4) 0.089(5)
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
N1 C6 1.322(5) . ?
N1 C2 1.343(4) . ?
N8 C7 1.267(4) . ?
N8 C9 1.414(4) . ?
N15 C12 1.373(4) . ?
N15 C18 1.453(5) . ?
N15 C16 1.478(5) . ?
C2 C3 1.382(4) . ?
C2 C2 1.482(7) 3_657 ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C7 1.465(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C14 1.378(4) . ?
C9 C10 1.386(5) . ?
C10 C11 1.364(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(5) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.459(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.489(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?