#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202627.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_2202627
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1962
_journal_page_last  o1963
_publ_section_title
;
8-Chloro-5-(4-methylpiperazin-1-yl)-11H-pyrido[2,3-b][1,5]benzoxazepine
;
loop_
_publ_author_name
  'Dupont, L\'eon'
  'Li\'egeois, Jean-Fran\,cois'
_chemical_formula_moiety  'C17 H17 Cl N4 O'
_chemical_formula_sum  'C17 H17 Cl N4 O'
_chemical_formula_iupac  'C17 H17 Cl N4 O'
_chemical_formula_weight  328.80
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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  8.5531(8)
_cell_length_b  10.6765(8)
_cell_length_c  17.2457(12)
_cell_angle_alpha  90.00
_cell_angle_beta  93.347(10)
_cell_angle_gamma  90.00
_cell_volume  1572.1(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.389
_diffrn_ambient_temperature  293(2)
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
  C1 0.00422(19) 0.20631(17) 0.61519(9) 0.0517(4) Uani d . 1 . . C
  H1 -0.0708 0.2069 0.6521 0.062 Uiso calc R 1 . . H
  C2 0.0628(2) 0.09517(16) 0.58895(10) 0.0560(4) Uani d . 1 . . C
  H2 0.0271 0.0211 0.6101 0.067 Uiso calc R 1 . . H
  N3 0.16793(16) 0.08744(12) 0.53487(8) 0.0495(3) Uani d . 1 . . N
  C4 0.21674(16) 0.19443(13) 0.50722(8) 0.0382(3) Uani d . 1 . . C
  O5 0.32398(12) 0.18517(10) 0.45021(6) 0.0431(2) Uani d . 1 . . O
  C6 0.25296(16) 0.22125(13) 0.37867(8) 0.0379(3) Uani d . 1 . . C
  C7 0.23291(18) 0.13148(14) 0.32117(9) 0.0455(3) Uani d . 1 . . C
  H7 0.2657 0.0496 0.3309 0.055 Uiso calc R 1 . . H
  C8 0.16402(19) 0.16301(14) 0.24891(9) 0.0467(4) Uani d . 1 . . C
  H8 0.1512 0.1034 0.2097 0.056 Uiso calc R 1 . . H
  C9 0.11504(17) 0.28485(14) 0.23672(8) 0.0412(3) Uani d . 1 . . C
  C10 0.13608(16) 0.37598(13) 0.29367(7) 0.0381(3) Uani d . 1 . . C
  H10 0.1033 0.4577 0.2834 0.046 Uiso calc R 1 . . H
  C11 0.20663(15) 0.34544(12) 0.36672(7) 0.0350(3) Uani d . 1 . . C
  N12 0.23932(14) 0.44283(11) 0.41931(6) 0.0372(3) Uani d . 1 . . N
  C13 0.23326(15) 0.42733(12) 0.49376(7) 0.0343(3) Uani d . 1 . . C
  C14 0.17071(16) 0.31289(13) 0.53038(7) 0.0358(3) Uani d . 1 . . C
  C15 0.05923(17) 0.31736(15) 0.58556(8) 0.0430(3) Uani d . 1 . . C
  H15 0.0219 0.3939 0.6024 0.052 Uiso calc R 1 . . H
  N16 0.27086(14) 0.52564(11) 0.54208(6) 0.0378(3) Uani d . 1 . . N
  C17 0.32023(18) 0.64462(13) 0.50907(8) 0.0400(3) Uani d . 1 . . C
  H171 0.2682 0.6565 0.4581 0.048 Uiso calc . 1 . . H
  H172 0.4324 0.6435 0.5033 0.048 Uiso calc . 1 . . H
  C18 0.27903(19) 0.75092(13) 0.56199(8) 0.0440(3) Uani d . 1 . . C
  H181 0.3146 0.8294 0.5408 0.053 Uiso calc . 1 . . H
  H182 0.1662 0.7554 0.5645 0.053 Uiso calc . 1 . . H
  N19 0.35089(15) 0.73371(11) 0.63995(7) 0.0439(3) Uani d . 1 . . N
  C20 0.29896(19) 0.61611(15) 0.67175(8) 0.0459(3) Uani d . 1 . . C
  H201 0.1863 0.6183 0.6758 0.055 Uiso calc . 1 . . H
  H202 0.3474 0.6047 0.7235 0.055 Uiso calc . 1 . . H
  C21 0.34137(17) 0.50731(13) 0.62094(8) 0.0406(3) Uani d . 1 . . C
  H211 0.4543 0.5016 0.6193 0.049 Uiso calc . 1 . . H
  H212 0.3034 0.4298 0.6424 0.049 Uiso calc . 1 . . H
  C22 0.3158(3) 0.83910(17) 0.68957(11) 0.0692(6) Uani d . 1 . . C
  H221 0.3499 0.9154 0.6664 0.104 Uiso calc R 1 . . H
  H222 0.3693 0.8285 0.7396 0.104 Uiso calc R 1 . . H
  H223 0.2049 0.8430 0.6954 0.104 Uiso calc R 1 . . H
  Cl1 0.02232(6) 0.32653(4) 0.14795(2) 0.06032(15) Uani d . 1 . . Cl
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
  C1 0.0484(9) 0.0614(10) 0.0455(8) -0.0104(8) 0.0047(7) 0.0060(7)
  C2 0.0652(10) 0.0480(9) 0.0542(9) -0.0158(8) -0.0027(8) 0.0113(7)
  N3 0.0610(8) 0.0373(6) 0.0493(7) -0.0045(6) -0.0037(6) 0.0046(5)
  C4 0.0401(7) 0.0375(7) 0.0360(6) 0.0001(6) -0.0058(5) 0.0009(5)
  O5 0.0435(5) 0.0442(6) 0.0412(5) 0.0093(4) -0.0007(4) 0.0001(4)
  C6 0.0374(7) 0.0397(7) 0.0365(6) 0.0024(6) 0.0004(5) -0.0031(5)
  C7 0.0508(8) 0.0373(7) 0.0481(8) 0.0056(6) 0.0017(6) -0.0072(6)
  C8 0.0510(8) 0.0440(8) 0.0446(8) -0.0006(7) -0.0004(6) -0.0135(6)
  C9 0.0426(7) 0.0453(8) 0.0354(6) -0.0030(6) -0.0004(5) -0.0048(6)
  C10 0.0410(7) 0.0379(7) 0.0354(6) -0.0021(6) 0.0020(5) -0.0019(5)
  C11 0.0360(6) 0.0358(7) 0.0333(6) -0.0031(5) 0.0030(5) -0.0030(5)
  N12 0.0434(6) 0.0336(6) 0.0342(5) -0.0022(5) -0.0008(5) -0.0029(4)
  C13 0.0342(6) 0.0327(6) 0.0357(6) 0.0022(5) -0.0017(5) -0.0010(5)
  C14 0.0379(7) 0.0354(7) 0.0335(6) -0.0013(5) -0.0036(5) 0.0006(5)
  C15 0.0424(7) 0.0462(8) 0.0403(7) 0.0000(6) 0.0007(6) -0.0004(6)
  N16 0.0494(7) 0.0330(6) 0.0304(5) -0.0026(5) -0.0033(5) 0.0002(4)
  C17 0.0508(8) 0.0347(7) 0.0342(6) -0.0043(6) -0.0008(6) 0.0005(5)
  C18 0.0539(9) 0.0353(7) 0.0418(7) -0.0006(6) -0.0051(6) -0.0013(6)
  N19 0.0544(7) 0.0382(6) 0.0381(6) -0.0027(5) -0.0045(5) -0.0063(5)
  C20 0.0565(9) 0.0470(8) 0.0340(6) -0.0038(7) 0.0009(6) -0.0021(6)
  C21 0.0474(8) 0.0391(7) 0.0341(6) -0.0021(6) -0.0065(5) 0.0015(5)
  C22 0.1069(16) 0.0492(10) 0.0503(9) 0.0018(10) -0.0046(10) -0.0163(8)
  Cl1 0.0780(3) 0.0590(3) 0.0415(2) 0.0023(2) -0.01722(18) -0.00837(17)
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
  C1 C2 . 1.375(3) no
  C1 C15 . 1.384(2) no
  C1 H1 . 0.9300 no
  C2 N3 . 1.335(2) yes
  C2 H2 . 0.9300 no
  N3 C4 . 1.3153(19) yes
  C4 O5 . 1.3867(17) yes
  C4 C14 . 1.3902(19) no
  O5 C6 . 1.3971(16) yes
  C6 C7 . 1.3826(19) no
  C6 C11 . 1.3958(19) no
  C7 C8 . 1.388(2) no
  C7 H7 . 0.9300 no
  C8 C9 . 1.379(2) no
  C8 H8 . 0.9300 no
  C9 C10 . 1.3867(19) no
  C9 Cl1 . 1.7403(15) yes
  C10 C11 . 1.4032(18) no
  C10 H10 . 0.9300 no
  C11 N12 . 1.3972(16) yes
  N12 C13 . 1.2986(16) yes
  C13 N16 . 1.3667(17) yes
  C13 C14 . 1.4890(19) no
  C14 C15 . 1.387(2) no
  C15 H15 . 0.9300 no
  N16 C17 . 1.4642(17) no
  N16 C21 . 1.4684(16) no
  C17 C18 . 1.511(2) no
  C17 H171 . 0.9700 no
  C17 H172 . 0.9700 no
  C18 N19 . 1.4570(18) no
  C18 H181 . 0.9700 no
  C18 H182 . 0.9700 no
  N19 C20 . 1.4502(19) no
  N19 C22 . 1.455(2) no
  C20 C21 . 1.512(2) no
  C20 H201 . 0.9700 no
  C20 H202 . 0.9700 no
  C21 H211 . 0.9700 no
  C21 H212 . 0.9700 no
  C22 H221 . 0.9600 no
  C22 H222 . 0.9600 no
  C22 H223 . 0.9600 no