#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009137.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_2009137
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1888
_journal_page_last  1889
_publ_section_title
;
An o-xylyl cross-bridged 5,12-dioxocyclam
;
loop_
_publ_author_name
  'Hubin, Timothy J.'
  'Tyryshkin, Nickolay '
  'Alcock, Nathaniel W.'
  'Busch, Daryle H.'
_chemical_formula_sum  'C18 H28 N4 O3'
_chemical_formula_weight  348.44
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
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'
_cell_length_a  9.9190(10)
_cell_length_b  12.898(2)
_cell_length_c  14.045(2)
_cell_angle_alpha  90.00
_cell_angle_beta  101.983(5)
_cell_angle_gamma  90.00
_cell_volume  1757.7(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  220(2)
_exptl_crystal_density_diffrn  1.317
_diffrn_ambient_temperature  220(2)
_refine_ls_wR_factor_obs  .124
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
  N1  .86843(15)  .48592(11)  .85920(10)  .0338(3) Uani d . 1 . N
  H1A  .922(2)  .4684(15)  .8209(15)  .040(5) Uiso d . 1 . H
  C2  .90147(17)  .57015(13)  .91285(11)  .0301(4) Uani d . 1 . C
  O3  .83270(14)  .60317(10)  .97098(8)  .0412(3) Uani d . 1 . O
  C4 1.03040(18)  .62455(13)  .89868(12)  .0338(4) Uani d . 1 . C
  H4A 1.1092  .5939  .9436  .041 Uiso calc R 1 . H
  H4B 1.0246  .6974  .9174  .041 Uiso calc R 1 . H
  C5 1.06006(17)  .62131(12)  .79568(12)  .0295(4) Uani d . 1 . C
  H5A  .9799  .6484  .7495  .035 Uiso calc R 1 . H
  H5B 1.1386  .6666  .7932  .035 Uiso calc R 1 . H
  N6 1.09084(13)  .51606(10)  .76535(9)  .0260(3) Uani d . 1 . N
  C7 1.23491(16)  .48933(13)  .81010(12)  .0317(4) Uani d . 1 . C
  H7A 1.2526  .5086  .8791  .038 Uiso calc R 1 . H
  H7B 1.2965  .5307  .7789  .038 Uiso calc R 1 . H
  C8 1.27019(16)  .37535(13)  .80229(12)  .0325(4) Uani d . 1 . C
  H8A 1.2689  .3580  .7342  .039 Uiso calc R 1 . H
  H8B 1.3632  .3621  .8402  .039 Uiso calc R 1 . H
  N9 1.17206(15)  .31054(11)  .83823(10)  .0316(3) Uani d . 1 . N
  H9A 1.155(2)  .3282(16)  .8935(15)  .039(5) Uiso d . 1 . H
  C10 1.08598(17)  .24684(12)  .78037(12)  .0308(4) Uani d . 1 . C
  O11 1.10119(13)  .22170(10)  .69823(9)  .0383(3) Uani d . 1 . O
  C12  .96406(18)  .20810(14)  .81961(13)  .0364(4) Uani d . 1 . C
  H12A  .9612  .2433  .8810  .044 Uiso calc R 1 . H
  H12B  .9733  .1335  .8323  .044 Uiso calc R 1 . H
  C13  .83121(18)  .22976(14)  .74520(13)  .0349(4) Uani d . 1 . C
  H13A  .8299  .1869  .6874  .042 Uiso calc R 1 . H
  H13B  .7523  .2094  .7730  .042 Uiso calc R 1 . H
  N14  .81576(13)  .33959(11)  .71550(9)  .0286(3) Uani d . 1 . N
  C15  .70018(17)  .39080(14)  .74598(12)  .0337(4) Uani d . 1 . C
  H15A  .6222  .3428  .7391  .040 Uiso calc R 1 . H
  H15B  .6708  .4510  .7042  .040 Uiso calc R 1 . H
  C16  .74287(18)  .42565(15)  .85151(12)  .0366(4) Uani d . 1 . C
  H16A  .6702  .4681  .8697  .044 Uiso calc R 1 . H
  H16B  .7595  .3654  .8949  .044 Uiso calc R 1 . H
  C17  .81887(18)  .35328(14)  .61152(11)  .0330(4) Uani d . 1 . C
  H17A  .7400  .3166  .5723  .040 Uiso calc R 1 . H
  H17B  .9029  .3210  .5989  .040 Uiso calc R 1 . H
  C18  .81464(16)  .46544(13)  .57850(11)  .0291(4) Uani d . 1 . C
  C19  .69335(17)  .50007(15)  .51754(12)  .0351(4) Uani d . 1 . C
  H19A  .6178  .4546  .5026  .042 Uiso calc R 1 . H
  C20  .68053(19)  .59877(15)  .47846(12)  .0391(4) Uani d . 1 . C
  H20A  .5974  .6197  .4377  .047 Uiso calc R 1 . H
  C21  .79075(19)  .66661(14)  .49961(12)  .0374(4) Uani d . 1 . C
  H21A  .7834  .7340  .4737  .045 Uiso calc R 1 . H
  C22  .91217(18)  .63363(14)  .55967(12)  .0335(4) Uani d . 1 . C
  H22A  .9872  .6797  .5735  .040 Uiso calc R 1 . H
  C23  .92711(16)  .53425(13)  .60041(11)  .0282(3) Uani d . 1 . C
  C24 1.06821(17)  .50405(14)  .65832(11)  .0318(4) Uani d . 1 . C
  H24A 1.0849  .4314  .6440  .038 Uiso calc R 1 . H
  H24B 1.1374  .5458  .6351  .038 Uiso calc R 1 . H
  O001  .9949(3)  .11321(16)  .52164(14)  .1081(9) 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
  N1  .0373(8)  .0352(8)  .0322(7)  -.0038(6)  .0151(6)  -.0085(6)
  C2  .0400(9)  .0290(8)  .0206(7)  .0068(7)  .0045(6)  .0009(6)
  O3  .0552(8)  .0433(8)  .0272(6)  .0075(6)  .0131(6)  -.0049(5)
  C4  .0424(9)  .0275(9)  .0294(8)  -.0009(7)  .0030(7)  -.0068(7)
  C5  .0331(8)  .0237(8)  .0309(8)  -.0014(6)  .0050(6)  -.0004(6)
  N6  .0260(6)  .0259(7)  .0248(6)  .0006(5)  .0024(5)  -.0019(5)
  C7  .0259(8)  .0322(9)  .0349(9)  -.0030(7)  .0012(7)  -.0010(7)
  C8  .0276(8)  .0349(9)  .0340(9)  .0036(7)  .0039(7)  -.0002(7)
  N9  .0390(8)  .0291(7)  .0262(7)  .0008(6)  .0057(6)  -.0023(6)
  C10  .0361(9)  .0246(8)  .0299(8)  .0080(7)  .0029(7)  .0006(6)
  O11  .0422(7)  .0403(7)  .0323(6)  .0036(6)  .0079(5)  -.0105(5)
  C12  .0443(10)  .0293(9)  .0344(9)  -.0022(7)  .0057(8)  .0050(7)
  C13  .0368(9)  .0305(9)  .0371(9)  -.0073(7)  .0070(7)  .0012(7)
  N14  .0301(7)  .0287(7)  .0269(7)  -.0017(6)  .0055(5)  .0007(5)
  C15  .0282(8)  .0406(10)  .0329(8)  -.0028(7)  .0076(7)  -.0014(7)
  C16  .0388(9)  .0421(10)  .0318(9)  -.0059(8)  .0142(7)  -.0033(7)
  C17  .0390(9)  .0334(9)  .0261(8)  .0001(7)  .0060(7)  -.0036(7)
  C18  .0331(8)  .0343(9)  .0208(7)  .0039(7)  .0076(6)  -.0016(6)
  C19  .0312(9)  .0459(11)  .0280(8)  .0026(7)  .0058(7)  -.0014(7)
  C20  .0372(9)  .0499(11)  .0296(9)  .0142(8)  .0055(7)  .0050(8)
  C21  .0502(10)  .0360(10)  .0283(8)  .0127(8)  .0134(8)  .0063(7)
  C22  .0414(9)  .0357(9)  .0252(8)  .0010(7)  .0110(7)  -.0010(7)
  C23  .0314(8)  .0349(9)  .0195(7)  .0051(7)  .0080(6)  -.0012(6)
  C24  .0305(8)  .0405(10)  .0256(8)  .0028(7)  .0085(6)  -.0014(7)
  O001  .159(2)  .0668(13)  .0692(12)  .0377(13)  -.0435(13)  -.0263(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
  N1 C2 . 1.324(2) ?
  N1 C16 . 1.453(2) ?
  C2 O3 . 1.2428(19) ?
  C2 C4 . 1.508(2) ?
  C4 C5 . 1.535(2) ?
  C5 N6 . 1.474(2) ?
  N6 C7 . 1.477(2) ?
  N6 C24 . 1.4812(19) ?
  C7 C8 . 1.520(2) ?
  C8 N9 . 1.451(2) ?
  N9 C10 . 1.333(2) ?
  C10 O11 . 1.2372(19) ?
  C10 C12 . 1.514(2) ?
  C12 C13 . 1.528(2) ?
  C13 N14 . 1.476(2) ?
  N14 C15 . 1.462(2) ?
  N14 C17 . 1.478(2) ?
  C15 C16 . 1.522(2) ?
  C17 C18 . 1.517(2) ?
  C18 C19 . 1.397(2) ?
  C18 C23 . 1.409(2) ?
  C19 C20 . 1.382(3) ?
  C20 C21 . 1.384(3) ?
  C21 C22 . 1.386(2) ?
  C22 C23 . 1.399(2) ?
  C23 C24 . 1.516(2) ?