#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008404.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_2008404
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_publ_section_title
;
6-Chloro-1H-2,3,4,5-tetrahydroazepino[3,2-c]quinoline
;
loop_
_publ_author_name
  'Bureau, Isabelle'
  'Chardon, Josiane'
  'Leclaire, Andre'
  'Hinschberger, Antoine'
  'Rault, Sylvain'
_chemical_name_common  azepinoquinoleine
_chemical_formula_sum  'C13 H13 Cl N2'
_chemical_formula_weight  232.5
_chemical_melting_point  449
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  -P_2ybc
loop_
_symmetry_equiv_pos_as_xyz
  +x,+y,+z
  -x,1/2+y,1/2-z
  -x,-y,-z
  +x,1/2-y,1/2+z
_cell_length_a  9.1581(5)
_cell_length_b  9.3318(7)
_cell_length_c  13.4647(8)
_cell_angle_alpha  90.
_cell_angle_beta  100.140(5)
_cell_angle_gamma  90.
_cell_volume  1132.70(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.365
_diffrn_ambient_temperature  294
_refine_ls_R_factor_obs  .044
_refine_ls_wR_factor_obs  .044
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_calc_attached_atom
  Cl1 .31680(8) .44013(5) .51036(3) .0759(3) Uani ? ?
  C1 .2798(2) .5737(2) .41780(10)
  .0424(8) Uani ? ?
  N1 .2275(2) .69160(10)
  .45046(9) .0401(6) Uani ? ?
  C2 .3084(2) .5422(2) .32080(10)
  .0383(7) Uani ? ?
  C3 .2785(2) .65320(10)
  .25030(10)
  .0305(6) Uani ? ?
  C4 .2074(2) .78110(10)
  .27810(10)
  .0294(6) Uani ? ?
  C5 .1590(2) .8936(2) .20980(10)
  .0391(7) Uani ? ?
  C6 .0986(2) 1.0158(2) .24160(10)
  .0463(9) Uani ? ?
  C7 .0841(2) 1.0321(2) .34240(10)
  .0465(9) Uani ? ?
  C8 .1265(2) .9245(2) .41020(10)
  .0412(8) Uani ? ?
  C9 .1876(2) .79620(10)
  .37940(10)
  .0318(6) Uani ? ?
  C10 .3608(3) .3929(2) .29660(10)
  .0570(10)
  Uani ? ?
  C11 .3078(3) .3428(2) .18950(10)
  .0520(10)
  Uani ? ?
  C12 .3958(2) .4014(2) .11360(10)
  .0453(9) Uani ? ?
  C13 .4356(2) .5574(2) .13350(10)
  .0471(9) Uani ? ?
  N2 .3129(2) .64380(10)
  .15608(9) .0394(6) Uani ? ?
  H2 .283(2) .707(2) .117(2) .058(6) Uiso ? ?
  H5 .167(2) .883(2) .1390(10)
  .045(5) Uiso ? ?
  H6 .065(2) 1.087(2) .195(2) .060(6) Uiso ? ?
  H7 .044(2) 1.118(2) .364(2) .064(6) Uiso ? ?
  H8 .115(2) .931(2) .4820(10)
  .052(5) Uiso ? ?
  H10a .480(3) .386(3) .310(2) .086(8) Uiso ? ?
  H10b .314(3) .334(3) .338(2) .095(9) Uiso ? ?
  H11a .311(2) .240(3) .190(2) .077(7) Uiso ? ?
  H11b .196(2) .376(2) .172(2) .067(6) Uiso ? ?
  H12a .338(2) .390(2) .046(2) .055(6) Uiso ? ?
  H12b .488(2) .348(2) .115(2) .061(6) Uiso ? ?
  H13a .518(2) .565(2) .1910(10)
  .048(5) Uiso ? ?
  H13b .469(2) .602(2) .074(2) .066(6) Uiso ? ?
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 .1446(6) .0511(3) .0381(2) .0380(3) .0330(3) .0200(2)
  C1 .0690(10)
  .0343(7) .0256(6) .0108(8) .0132(7) .0060(5)
  N1 .0589(9) .0360(6) .0266(5) .0103(6) .0107(6) .0017(5)
  C2 .0610(10)
  .0288(7) .0269(6) .0083(7) .0110(7) .0011(5)
  C3 .0409(8) .0271(6) .0234(5) -.0014(6) .0055(6) -.0013(5)
  C4 .0349(8) .0265(6) .0267(6) -.0011(6) .0052(5) .0008(5)
  C5 .0481(9) .0345(7) .0354(7) .0027(7) .0093(7) .0082(6)
  C6 .0510(10)
  .0359(8) .0520(10)
  .0104(7) .0101(8) .0134(7)
  C7 .0500(10)
  .0339(8) .0560(10)
  .0124(7) .0108(9) -.0011(7)
  C8 .0480(10)
  .0385(8) .0381(8) .0088(7) .0088(7) -.0050(6)
  C9 .0372(8) .0296(6) .0286(6) .0020(6) .0055(6) -.0011(5)
  C10 .102(2) .0335(8) .0393(9) .0200(10)
  .0210(10)
  .0023(7)
  C11 .0780(10)
  .0313(8) .0510(10)
  .0034(9) .0200(10)
  -.0073(7)
  C12 .0560(10)
  .0424(9) .0385(8) .0095(8) .0113(8) -.0088(7)
  C13 .0550(10)
  .0470(9) .0448(9) -.0014(8) .0222(9) -.0061(8)
  N2 .0610(9) .0329(6) .0268(6) .0041(6) .0141(6) .0014(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl1 C1 . . 1.753(2) yes
  C1 N1 . . 1.307(2) yes
  C1 C2 . . 1.408(2) yes
  N1 C9 . . 1.371(2) yes
  C2 C3 . . 1.398(2) yes
  C2 C10 . . 1.528(3) yes
  C3 C4 . . 1.440(2) yes
  C3 N2 . . 1.363(2) yes
  C4 C5 . . 1.414(2) yes
  C4 C9 . . 1.414(2) yes
  C5 C6 . . 1.369(2) yes
  C5 H5 . . .98(2) no
  C6 C7 . . 1.395(3) yes
  C6 H6 . . .93(2) no
  C7 C8 . . 1.366(2) yes
  C7 H7 . . .94(2) no
  C8 C9 . . 1.414(2) yes
  C8 H8 . . .99(2) no
  C10 C11 . . 1.513(3) yes
  C10 H10a . . 1.08(2) no
  C10 H10b . . .94(3) no
  C11 C12 . . 1.510(3) yes
  C11 H11a . . .96(2) no
  C11 H11b . . 1.05(2) no
  C12 C13 . . 1.514(3) yes
  C12 H12a . . .98(2) no
  C12 H12b . . .97(2) no
  C13 N2 . . 1.458(3) yes
  C13 H13a . . .98(2) no
  C13 H13b . . 1.00(2) no
  N2 H2 . . .81(2) no