#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200652.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_2200652
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o1240
_journal_page_last  o1241
_publ_section_title
;
5-(4-Chlorophenyl)-3-oxa-4-azatricyclo[5.2.1.0^2,6^]dec-4-ene
;
loop_
_publ_author_name
  'A. Thiruvalluvar'
  'V. Parthasarathi'
  'V. Kabaleeswaran'
  'S. S. Rajan'
  'A. Nagarajan'
  'M. Krishna Pillay'
_chemical_formula_moiety  'C14 H14 Cl N O'
_chemical_formula_sum  'C14 H14 Cl N O'
_chemical_formula_iupac  'C14 H14 Cl N O'
_chemical_formula_weight  247.73
_chemical_melting_point  361
_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  11.782(4)
_cell_length_b  10.288(3)
_cell_length_c  20.461(3)
_cell_angle_alpha  90
_cell_angle_beta  100.20(2)
_cell_angle_gamma  90
_cell_volume  2440.9(11)
_cell_formula_units_Z  8
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.348
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
  Cl1  .87573(6)  .18028(7)  .06041(3)  .0799(2) Uani d ' ' 1 ' ' ' ' Cl
  C1A 1.15819(17)  .6428(2)  .42491(9)  .0535(5) Uani d ' ' 1 ' ' ' ' C
  H1A 1.2312  .686  .4428  .064 Uiso calc R 1 ' ' ' ' H
  C2A 1.16427(16)  .4950(2)  .42390(9)  .0524(5) Uani d ' ' 1 ' ' ' ' C
  H2A 1.1612  .4574  .4676  .063 Uiso calc R 1 ' ' ' ' H
  O3A 1.26383(11)  .44902(18)  .39747(7)  .0682(4) Uani d ' ' 1 ' ' ' ' O
  N4A 1.22713(14)  .38859(19)  .33543(9)  .0613(4) Uani d ' ' 1 ' ' ' ' N
  C5A 1.11702(15)  .39068(18)  .32094(9)  .0476(4) Uani d ' ' 1 ' ' ' ' C
  C6A 1.05861(15)  .45587(17)  .37161(8)  .0446(4) Uani d ' ' 1 ' ' ' ' C
  H6A 1.0058  .3978  .3896  .054 Uiso calc R 1 ' ' ' ' H
  C7A 1.00338(15)  .58780(17)  .34935(9)  .0459(4) Uani d ' ' 1 ' ' ' ' C
  H7A  .9515  .5865  .3062  .055 Uiso calc R 1 ' ' ' ' H
  C8A  .95014(17)  .6434(2)  .40661(10)  .0574(5) Uani d ' ' 1 ' ' ' ' C
  H8A1  .903  .5791  .4239  .069 Uiso calc R 1 ' ' ' ' H
  H8A2  .9034  .7194  .3925  .069 Uiso calc R 1 ' ' ' ' H
  C9A 1.05741(18)  .6798(2)  .45907(10)  .0609(5) Uani d ' ' 1 ' ' ' ' C
  H9A1 1.0584  .772  .4692  .073 Uiso calc R 1 ' ' ' ' H
  H9A2 1.0594  .6308  .4997  .073 Uiso calc R 1 ' ' ' ' H
  C10A 1.11013(17)  .67396(19)  .35214(9)  .0523(4) Uani d ' ' 1 ' ' ' ' C
  H10A 1.1603  .6452  .3222  .063 Uiso calc R 1 ' ' ' ' H
  H10B 1.0911  .7652  .3448  .063 Uiso calc R 1 ' ' ' ' H
  C51A 1.05794(16)  .33754(17)  .25742(9)  .0469(4) Uani d ' ' 1 ' ' ' ' C
  C52A 1.11838(17)  .3077(2)  .20646(10)  .0585(5) Uani d ' ' 1 ' ' ' ' C
  H52A 1.1977  .3209  .2132  .07 Uiso calc R 1 ' ' ' ' H
  C53A 1.06363(19)  .2594(2)  .14688(10)  .0643(5) Uani d ' ' 1 ' ' ' ' C
  H53A 1.1052  .2404  .1134  .077 Uiso calc R 1 ' ' ' ' H
  C54A  .94515(18)  .2391(2)  .13680(10)  .0555(5) Uani d ' ' 1 ' ' ' ' C
  C55A  .88366(17)  .26549(19)  .18622(11)  .0569(5) Uani d ' ' 1 ' ' ' ' C
  H55A  .8046  .2505  .1794  .068 Uiso calc R 1 ' ' ' ' H
  C56A  .93989(16)  .31461(18)  .24636(10)  .0525(4) Uani d ' ' 1 ' ' ' ' C
  H56A  .898  .3325  .2798  .063 Uiso calc R 1 ' ' ' ' H
  Cl2 1.15826(6) 1.11364(7)  .45644(3)  .0858(2) Uani d ' ' 1 ' ' ' ' Cl
  C1B  .83131(17)  .6838(2)  .08491(11)  .0594(5) Uani d ' ' 1 ' ' ' ' C
  H1B  .7548  .6503  .0656  .071 Uiso calc R 1 ' ' ' ' H
  C2B  .83813(16)  .8308(2)  .09176(10)  .0554(5) Uani d ' ' 1 ' ' ' ' C
  H2B  .8438  .8728  .0495  .066 Uiso calc R 1 ' ' ' ' H
  O3B  .74377(12)  .88295(17)  .12025(9)  .0735(5) Uani d ' ' 1 ' ' ' ' O
  N4B  .78645(14)  .93644(19)  .18343(10)  .0669(5) Uani d ' ' 1 ' ' ' ' N
  C5B  .89632(15)  .92208(17)  .19698(10)  .0485(4) Uani d ' ' 1 ' ' ' ' C
  C6B  .94730(14)  .85366(18)  .14431(8)  .0457(4) Uani d ' ' 1 ' ' ' ' C
  H6B 1.005  .9066  .1274  .055 Uiso calc R 1 ' ' ' ' H
  C7B  .98968(16)  .71445(19)  .16209(9)  .0504(4) Uani d ' ' 1 ' ' ' ' C
  H7B 1.041  .7061  .2051  .06 Uiso calc R 1 ' ' ' ' H
  C8B 1.03821(19)  .6589(2)  .10317(11)  .0660(6) Uani d ' ' 1 ' ' ' ' C
  H8B1 1.0776  .5771  .1147  .079 Uiso calc R 1 ' ' ' ' H
  H8B2 1.0913  .7194  .0881  .079 Uiso calc R 1 ' ' ' ' H
  C9B  .92884(19)  .6392(3)  .04953(11)  .0704(6) Uani d ' ' 1 ' ' ' ' C
  H9B1  .9319  .692  .0106  .084 Uiso calc R 1 ' ' ' ' H
  H9B2  .9195  .5488  .0363  .084 Uiso calc R 1 ' ' ' ' H
  C10B  .87574(19)  .6409(2)  .15656(11)  .0617(5) Uani d ' ' 1 ' ' ' ' C
  H10C  .8282  .6721  .1874  .074 Uiso calc R 1 ' ' ' ' H
  H10D  .8861  .5475  .1609  .074 Uiso calc R 1 ' ' ' ' H
  C51B  .95988(15)  .96878(17)  .26066(9)  .0468(4) Uani d ' ' 1 ' ' ' ' C
  C52B  .90520(17)  .9903(2)  .31505(11)  .0598(5) Uani d ' ' 1 ' ' ' ' C
  H52B  .8264  .975  .3106  .072 Uiso calc R 1 ' ' ' ' H
  C53B  .9650(2) 1.0333(2)  .37471(11)  .0655(5) Uani d ' ' 1 ' ' ' ' C
  H53B  .9276 1.0456  .4106  .079 Uiso calc R 1 ' ' ' ' H
  C54B 1.08210(18) 1.05827(19)  .38092(10)  .0560(5) Uani d ' ' 1 ' ' ' ' C
  C55B 1.13855(17) 1.03884(19)  .32838(10)  .0536(4) Uani d ' ' 1 ' ' ' ' C
  H55B 1.217 1.0562  .333  .064 Uiso calc R 1 ' ' ' ' H
  C56B 1.07809(15)  .99349(17)  .26885(9)  .0469(4) Uani d ' ' 1 ' ' ' ' C
  H56B 1.1167  .9791  .2336  .056 Uiso calc R 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
  Cl1  .0890(4)  .0842(4)  .0601(3)  -.0167(3)  -.0045(3)  .0004(3)
  C1A  .0493(10)  .0671(12)  .0410(9)  -.0107(9)  -.0002(7)  .0007(8)
  C2A  .0469(10)  .0706(12)  .0390(8)  .0064(9)  .0059(7)  .0127(8)
  O3A  .0430(7)  .1011(12)  .0568(8)  .0150(7)  -.0010(6)  -.0025(8)
  N4A  .0442(9)  .0828(12)  .0559(9)  .0102(8)  .0061(7)  .0009(8)
  C5A  .0422(9)  .0510(10)  .0507(10)  .0059(7)  .0110(7)  .0103(8)
  C6A  .0431(9)  .0471(9)  .0444(9)  -.0006(7)  .0097(7)  .0080(7)
  C7A  .0433(9)  .0477(9)  .0441(9)  .0022(7)  .0006(7)  .0051(7)
  C8A  .0515(11)  .0594(11)  .0611(11)  .0044(9)  .0094(9)  -.0055(9)
  C9A  .0671(13)  .0684(13)  .0460(10)  .0031(10)  .0066(9)  -.0037(9)
  C10A  .0583(11)  .0518(10)  .0448(9)  -.0096(8)  .0040(8)  .0085(8)
  C51A  .0468(9)  .0430(9)  .0517(10)  .0042(7)  .0113(8)  .0071(7)
  C52A  .0466(10)  .0738(13)  .0572(11)  -.0019(9)  .0150(8)  .0018(10)
  C53A  .0636(12)  .0794(14)  .0526(11)  -.0025(11)  .0179(9)  .0000(10)
  C54A  .0616(11)  .0498(10)  .0524(10)  -.0016(8)  .0025(9)  .0062(8)
  C55A  .0459(10)  .0496(10)  .0733(13)  -.0011(8)  .0058(9)  .0034(9)
  C56A  .0464(10)  .0494(10)  .0639(11)  .0016(8)  .0159(8)  .0007(8)
  Cl2  .0954(5)  .0990(5)  .0599(3)  -.0053(4)  .0049(3)  -.0191(3)
  C1B  .0476(10)  .0624(12)  .0637(12)  -.0105(9)  -.0023(9)  -.0021(9)
  C2B  .0450(10)  .0606(11)  .0552(10)  -.0016(8)  -.0055(8)  .0102(9)
  O3B  .0400(7)  .0825(10)  .0885(11)  .0098(7)  -.0142(7)  -.0068(8)
  N4B  .0401(8)  .0713(11)  .0855(13)  .0057(8)  .0006(8)  -.0054(10)
  C5B  .0381(8)  .0456(9)  .0605(11)  .0018(7)  .0054(8)  .0085(8)
  C6B  .0380(8)  .0518(10)  .0452(9)  -.0045(7)  .0015(7)  .0099(7)
  C7B  .0458(9)  .0545(10)  .0474(9)  .0069(8)  -.0009(7)  .0051(8)
  C8B  .0527(11)  .0785(14)  .0642(12)  .0074(10)  .0038(9)  -.0122(11)
  C9B  .0636(13)  .0854(16)  .0591(12)  -.0017(11)  .0026(10)  -.0119(11)
  C10B  .0676(13)  .0503(11)  .0668(12)  -.0079(9)  .0112(10)  .0092(9)
  C51B  .0420(9)  .0415(8)  .0570(10)  .0036(7)  .0090(7)  .0064(8)
  C52B  .0433(10)  .0668(12)  .0719(13)  .0027(9)  .0171(9)  -.0012(10)
  C53B  .0681(13)  .0705(13)  .0629(12)  .0057(11)  .0256(10)  -.0056(10)
  C54B  .0625(12)  .0505(10)  .0544(10)  .0039(9)  .0088(9)  -.0019(8)
  C55B  .0466(10)  .0539(10)  .0594(11)  -.0002(8)  .0070(8)  .0016(9)
  C56B  .0424(9)  .0475(9)  .0518(9)  .0009(7)  .0109(7)  .0034(7)
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
  Cl1 C54A ' ' 1.739(2) ?
  C1A C2A ' ' 1.523(3) ?
  C1A C9A ' ' 1.529(3) ?
  C1A C10A ' ' 1.530(2) ?
  C1A H1A ' '  .98 ?
  C2A O3A ' ' 1.455(2) ?
  C2A C6A ' ' 1.544(3) ?
  C2A H2A ' '  .98 ?
  O3A N4A ' ' 1.411(2) yes
  N4A C5A ' ' 1.279(2) yes
  C5A C51A ' ' 1.467(3) ?
  C5A C6A ' ' 1.500(3) ?
  C6A C7A ' ' 1.539(2) ?
  C6A H6A ' '  .98 ?
  C7A C10A ' ' 1.531(3) ?
  C7A C8A ' ' 1.534(3) ?
  C7A H7A ' '  .98 ?
  C8A C9A ' ' 1.552(3) ?
  C8A H8A1 ' '  .97 ?
  C8A H8A2 ' '  .97 ?
  C9A H9A1 ' '  .97 ?
  C9A H9A2 ' '  .97 ?
  C10A H10A ' '  .97 ?
  C10A H10B ' '  .97 ?
  C51A C56A ' ' 1.389(3) ?
  C51A C52A ' ' 1.397(3) ?
  C52A C53A ' ' 1.368(3) ?
  C52A H52A ' '  .93 ?
  C53A C54A ' ' 1.390(3) ?
  C53A H53A ' '  .93 ?
  C54A C55A ' ' 1.372(3) ?
  C55A C56A ' ' 1.386(3) ?
  C55A H55A ' '  .93 ?
  C56A H56A ' '  .93 ?
  Cl2 C54B ' ' 1.740(2) ?
  C1B C2B ' ' 1.519(3) ?
  C1B C10B ' ' 1.532(3) ?
  C1B C9B ' ' 1.533(3) ?
  C1B H1B ' '  .98 ?
  C2B O3B ' ' 1.447(3) ?
  C2B C6B ' ' 1.541(2) ?
  C2B H2B ' '  .98 ?
  O3B N4B ' ' 1.413(2) yes
  N4B C5B ' ' 1.283(2) yes
  C5B C51B ' ' 1.464(3) ?
  C5B C6B ' ' 1.499(3) ?
  C6B C7B ' ' 1.539(3) ?
  C6B H6B ' '  .98 ?
  C7B C10B ' ' 1.528(3) ?
  C7B C8B ' ' 1.533(3) ?
  C7B H7B ' '  .98 ?
  C8B C9B ' ' 1.551(3) ?
  C8B H8B1 ' '  .97 ?
  C8B H8B2 ' '  .97 ?
  C9B H9B1 ' '  .97 ?
  C9B H9B2 ' '  .97 ?
  C10B H10C ' '  .97 ?
  C10B H10D ' '  .97 ?
  C51B C56B ' ' 1.396(2) ?
  C51B C52B ' ' 1.399(3) ?
  C52B C53B ' ' 1.370(3) ?
  C52B H52B ' '  .93 ?
  C53B C54B ' ' 1.387(3) ?
  C53B H53B ' '  .93 ?
  C54B C55B ' ' 1.375(3) ?
  C55B C56B ' ' 1.379(3) ?
  C55B H55B ' '  .93 ?
  C56B H56B ' '  .93 ?