#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/45/2014599.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_2014599
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o85
_journal_page_last  o87
_publ_section_title
;
9-(2-Chloroethylamino)acridine monohydrate and its precursor
9-phenoxyacridine
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_publ_author_name
  'Youssif Ebead'
  'Artur Sikorski'
  'Karol Krzymi\'nski'
  'Lis, Tadeusz'
  'Jerzy B\/la\.zejowski'
_chemical_formula_moiety  'C15 H13 Cl N2, H2 O'
_chemical_formula_sum  'C15 H15 Cl N2 O'
_chemical_formula_iupac  'C15 H13 Cl N2, H2 O'
_chemical_formula_weight  274.74
_symmetry_cell_setting  'monoclinic'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  '-x, -y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1/2, -z'
  '-x+1/2, y+1/2, -z+1/2'
  'x, -y, z-1/2'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  14.052(3)
_cell_length_b  11.330(2)
_cell_length_c  17.283(3)
_cell_angle_alpha  90
_cell_angle_beta  107.20(3)
_cell_angle_gamma  90
_cell_volume  2628.6(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.388
_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 0.3630(2) 0.1946(2) 0.43440(14) 0.0478(6) Uani d . 1 . . C
  H1 0.348(2) 0.193(2) 0.3781(18) 0.053(8) Uiso d . 1 . . H
  C2 0.3817(2) 0.0902(2) 0.47443(16) 0.0540(7) Uani d . 1 . . C
  H2 0.381(2) 0.020(3) 0.4454(19) 0.068(10) Uiso d . 1 . . H
  C3 0.4086(2) 0.0873(2) 0.55918(16) 0.0510(7) Uani d . 1 . . C
  H3 0.422(2) 0.012(3) 0.588(2) 0.070(10) Uiso d . 1 . . H
  C4 0.4179(2) 0.1889(2) 0.60156(14) 0.0455(6) Uani d . 1 . . C
  H4 0.438(2) 0.189(2) 0.6606(18) 0.050(7) Uiso d . 1 . . H
  C5 0.4175(2) 0.6046(2) 0.62351(15) 0.0482(6) Uani d . 1 . . C
  H5 0.439(2) 0.591(3) 0.681(2) 0.066(9) Uiso d . 1 . . H
  C6 0.4042(2) 0.7146(2) 0.59147(18) 0.0548(7) Uani d . 1 . . C
  H6 0.415(3) 0.779(3) 0.625(2) 0.081(11) Uiso d . 1 . . H
  C7 0.3730(2) 0.7301(3) 0.50762(18) 0.0544(7) Uani d . 1 . . C
  H7 0.358(3) 0.806(3) 0.484(2) 0.088(12) Uiso d . 1 . . H
  C8 0.3558(2) 0.6354(2) 0.45724(15) 0.0446(6) Uani d . 1 . . C
  H8 0.3310(19) 0.648(2) 0.3994(16) 0.044(7) Uiso d . 1 . . H
  C9 0.35264(17) 0.41649(19) 0.43715(12) 0.0343(5) Uani d . 1 . . C
  N10 0.41450(16) 0.39637(18) 0.60992(11) 0.0409(5) Uani d . 1 . . N
  C11 0.36840(17) 0.3039(2) 0.47552(12) 0.0341(5) Uani d . 1 . . C
  C12 0.39901(17) 0.3003(2) 0.56203(13) 0.0361(5) Uani d . 1 . . C
  C13 0.36966(16) 0.5183(2) 0.48793(13) 0.0338(5) Uani d . 1 . . C
  C14 0.40056(18) 0.5032(2) 0.57327(13) 0.0367(5) Uani d . 1 . . C
  N15 0.32497(17) 0.43216(19) 0.35597(11) 0.0422(5) Uani d . 1 . . N
  H15 0.333(2) 0.499(3) 0.3391(18) 0.051(8) Uiso d . 1 . . H
  C16 0.2696(2) 0.3541(2) 0.29262(14) 0.0465(6) Uani d . 1 . . C
  H16A 0.228(2) 0.304(2) 0.3142(17) 0.051(8) Uiso d . 1 . . H
  H16B 0.311(3) 0.307(3) 0.271(2) 0.071(10) Uiso d . 1 . . H
  C17 0.2099(2) 0.4234(3) 0.22029(15) 0.0522(7) Uani d . 1 . . C
  H17A 0.249(2) 0.475(3) 0.1963(19) 0.058(8) Uiso d . 1 . . H
  H17B 0.175(2) 0.372(3) 0.1778(19) 0.062(9) Uiso d . 1 . . H
  Cl18 0.12332(6) 0.51965(8) 0.24439(5) 0.0699(3) Uani d . 1 . . Cl
  O19 0.38779(12) 0.63302(15) 0.26947(9) 0.0491(4) Uani d . 1 . . O
  H19A 0.397(3) 0.609(4) 0.217(2) 0.096(12) Uiso d . 1 . . H
  H19B 0.451(3) 0.628(3) 0.301(2) 0.082(11) Uiso d . 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
  C1 0.0681(18) 0.0393(13) 0.0302(11) 0.0023(12) 0.0056(11) -0.0024(10)
  C2 0.078(2) 0.0357(13) 0.0420(13) 0.0035(13) 0.0081(13) -0.0025(11)
  C3 0.0686(19) 0.0376(14) 0.0427(13) 0.0021(12) 0.0099(12) 0.0074(11)
  C4 0.0592(17) 0.0444(14) 0.0314(11) 0.0010(12) 0.0112(11) 0.0060(10)
  C5 0.0595(17) 0.0446(14) 0.0368(12) -0.0021(12) 0.0088(11) -0.0073(11)
  C6 0.073(2) 0.0388(14) 0.0533(15) -0.0029(13) 0.0197(14) -0.0115(12)
  C7 0.073(2) 0.0375(14) 0.0551(16) 0.0009(13) 0.0222(14) 0.0014(12)
  C8 0.0569(16) 0.0380(13) 0.0392(12) 0.0025(11) 0.0148(11) 0.0056(10)
  C9 0.0340(12) 0.0381(12) 0.0290(10) -0.0015(9) 0.0066(8) 0.0010(9)
  N10 0.0530(13) 0.0397(11) 0.0270(8) -0.0004(9) 0.0073(8) 0.0000(8)
  C11 0.0369(12) 0.0353(11) 0.0277(10) -0.0001(9) 0.0059(8) 0.0007(8)
  C12 0.0399(13) 0.0374(12) 0.0301(10) 0.0003(10) 0.0089(9) 0.0020(9)
  C13 0.0334(12) 0.0341(11) 0.0331(10) -0.0001(9) 0.0086(9) 0.0007(9)
  C14 0.0387(13) 0.0391(13) 0.0308(10) -0.0007(10) 0.0079(9) -0.0022(9)
  N15 0.0548(13) 0.0392(11) 0.0268(9) -0.0072(9) 0.0028(8) 0.0051(8)
  C16 0.0611(18) 0.0442(14) 0.0289(11) -0.0038(13) 0.0053(11) -0.0001(10)
  C17 0.0627(19) 0.0578(17) 0.0284(11) -0.0055(14) 0.0019(11) 0.0038(11)
  Cl18 0.0613(5) 0.0852(6) 0.0608(4) 0.0124(4) 0.0142(3) 0.0270(4)
  O19 0.0484(10) 0.0600(10) 0.0384(8) 0.0005(8) 0.0122(7) 0.0057(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
  C9 C11 . 1.425(3) yes
  C9 C13 . 1.427(3) yes
  C9 N15 . 1.352(3) yes
  N10 C12 . 1.345(3) yes
  N10 C14 . 1.353(3) yes
  N15 H15 . 0.84(3) ?
  N15 C16 . 1.443(3) yes
  C16 C17 . 1.504(3) yes
  C17 Cl18 . 1.773(3) yes
  C1 C2 . 1.357(4) ?
  C1 C11 . 1.418(3) ?
  C1 H1 . 0.93(3) ?
  C2 C3 . 1.401(4) ?
  C2 H2 . 0.94(3) ?
  C3 C4 . 1.350(4) ?
  C3 H3 . 0.98(3) ?
  C4 C12 . 1.422(3) ?
  C4 H4 . 0.98(3) ?
  C5 C6 . 1.354(4) ?
  C5 C14 . 1.417(3) ?
  C5 H5 . 0.96(3) ?
  C6 C7 . 1.395(4) ?
  C6 H6 . 0.92(4) ?
  C7 C8 . 1.358(4) ?
  C7 H7 . 0.94(4) ?
  C8 C13 . 1.420(3) ?
  C8 H8 . 0.97(3) ?
  C11 C12 . 1.429(3) ?
  C13 C14 . 1.419(3) ?
  C16 H16A . 0.97(3) ?
  C16 H16B . 0.94(4) ?
  C17 H17A . 0.98(3) ?
  C17 H17B . 0.95(3) ?
  O19 H19A . 1.00(4) ?
  O19 H19B . 0.90(4) ?
_cod_database_code 2014599