#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014600.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_2014600
_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
;
loop_
_publ_author_name
  'Youssif Ebead'
  'Artur Sikorski'
  'Karol Krzymi\'nski'
  'Lis, Tadeusz'
  'Jerzy B\/la\.zejowski'
_chemical_formula_moiety  'C19 H13 N O'
_chemical_formula_sum  'C19 H13 N O'
_chemical_formula_iupac  'C19 H13 N O'
_chemical_formula_weight  271.30
_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, -y, -z'
  '-x+1/2, y+1/2, -z+1/2'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  9.400(3)
_cell_length_b  10.301(3)
_cell_length_c  14.955(4)
_cell_angle_alpha  90
_cell_angle_beta  106.89(3)
_cell_angle_gamma  90
_cell_volume  1385.6(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.301
_diffrn_ambient_temperature  100(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 0.40970(12) 0.32673(10) 0.45547(7) 0.0199(2) Uani d . 1 . . C
  H1 0.4607(16) 0.3973(15) 0.4322(10) 0.030(4) Uiso d . 1 . . H
  C2 0.25823(12) 0.31650(11) 0.42525(7) 0.0228(2) Uani d . 1 . . C
  H2 0.1995(18) 0.3785(16) 0.3778(11) 0.036(4) Uiso d . 1 . . H
  C3 0.18362(11) 0.21753(10) 0.46085(7) 0.0220(2) Uani d . 1 . . C
  H3 0.0744(16) 0.2134(14) 0.4382(10) 0.027(3) Uiso d . 1 . . H
  C4 0.26163(11) 0.12980(10) 0.52465(7) 0.0193(2) Uani d . 1 . . C
  H4 0.2114(16) 0.0595(15) 0.5508(10) 0.030(4) Uiso d . 1 . . H
  C5 0.71990(12) -0.04360(10) 0.71688(7) 0.0209(2) Uani d . 1 . . C
  H5 0.6574(16) -0.1125(15) 0.7363(10) 0.029(4) Uiso d . 1 . . H
  C6 0.87133(12) -0.04110(11) 0.75046(7) 0.0244(2) Uani d . 1 . . C
  H6 0.9243(17) -0.1088(15) 0.7969(11) 0.032(4) Uiso d . 1 . . H
  C7 0.95607(12) 0.05573(11) 0.72090(8) 0.0245(2) Uani d . 1 . . C
  H7 1.0661(18) 0.0557(15) 0.7467(11) 0.034(4) Uiso d . 1 . . H
  C8 0.88709(11) 0.14837(10) 0.65785(7) 0.0212(2) Uani d . 1 . . C
  H8 0.9454(17) 0.2154(15) 0.6364(10) 0.031(4) Uiso d . 1 . . H
  C9 0.64990(11) 0.24061(9) 0.55635(6) 0.01609(19) Uani d . 1 . . C
  N10 0.49290(9) 0.04515(8) 0.61944(6) 0.01696(18) Uani d . 1 . . N
  C11 0.49501(10) 0.23634(9) 0.52209(6) 0.01595(19) Uani d . 1 . . C
  C12 0.42091(10) 0.13481(9) 0.55682(6) 0.01575(19) Uani d . 1 . . C
  C13 0.72841(11) 0.14904(9) 0.62084(6) 0.01678(19) Uani d . 1 . . C
  C14 0.64269(11) 0.05166(9) 0.65066(6) 0.01667(19) Uani d . 1 . . C
  O15 0.72711(8) 0.34171(7) 0.53074(5) 0.01975(17) Uani d . 1 . . O
  C16 0.76284(10) 0.33091(9) 0.44710(7) 0.01637(19) Uani d . 1 . . C
  C17 0.72803(10) 0.22247(9) 0.38962(7) 0.0181(2) Uani d . 1 . . C
  H17 0.6705(16) 0.1500(14) 0.4045(10) 0.026(3) Uiso d . 1 . . H
  C18 0.77383(11) 0.21988(11) 0.30876(7) 0.0232(2) Uani d . 1 . . C
  H18 0.7512(17) 0.1427(16) 0.2698(11) 0.033(4) Uiso d . 1 . . H
  C19 0.85183(12) 0.32302(12) 0.28585(7) 0.0259(2) Uani d . 1 . . C
  H19 0.8829(17) 0.3227(15) 0.2292(11) 0.033(4) Uiso d . 1 . . H
  C20 0.88308(11) 0.43128(11) 0.34377(8) 0.0238(2) Uani d . 1 . . C
  H20 0.9370(17) 0.5042(16) 0.3258(10) 0.034(4) Uiso d . 1 . . H
  C21 0.83817(10) 0.43659(10) 0.42441(7) 0.0200(2) Uani d . 1 . . C
  H21 0.8585(16) 0.5101(15) 0.4651(10) 0.027(3) 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 0.0240(5) 0.0169(4) 0.0197(4) 0.0015(4) 0.0078(4) 0.0013(3)
  C2 0.0234(5) 0.0221(5) 0.0223(5) 0.0052(4) 0.0057(4) 0.0026(4)
  C3 0.0181(4) 0.0245(5) 0.0232(5) 0.0018(4) 0.0055(4) -0.0019(4)
  C4 0.0183(4) 0.0194(4) 0.0216(4) -0.0012(3) 0.0081(4) -0.0021(3)
  C5 0.0254(5) 0.0196(5) 0.0187(4) 0.0026(4) 0.0081(4) 0.0010(4)
  C6 0.0269(5) 0.0244(5) 0.0199(5) 0.0057(4) 0.0036(4) 0.0007(4)
  C7 0.0202(5) 0.0264(5) 0.0241(5) 0.0014(4) 0.0018(4) -0.0039(4)
  C8 0.0186(5) 0.0214(5) 0.0232(5) -0.0024(4) 0.0051(4) -0.0045(4)
  C9 0.0202(4) 0.0138(4) 0.0161(4) -0.0025(3) 0.0082(3) -0.0029(3)
  N10 0.0194(4) 0.0166(4) 0.0166(4) 0.0003(3) 0.0079(3) -0.0009(3)
  C11 0.0194(4) 0.0147(4) 0.0150(4) 0.0002(3) 0.0069(3) -0.0018(3)
  C12 0.0178(4) 0.0158(4) 0.0150(4) 0.0001(3) 0.0069(3) -0.0024(3)
  C13 0.0181(4) 0.0166(4) 0.0160(4) -0.0010(3) 0.0056(3) -0.0036(3)
  C14 0.0205(4) 0.0160(4) 0.0148(4) 0.0004(3) 0.0071(3) -0.0022(3)
  O15 0.0246(4) 0.0159(3) 0.0208(3) -0.0060(3) 0.0099(3) -0.0029(3)
  C16 0.0137(4) 0.0166(4) 0.0186(4) 0.0004(3) 0.0045(3) 0.0017(3)
  C17 0.0170(4) 0.0176(4) 0.0198(4) -0.0016(3) 0.0056(3) 0.0000(3)
  C18 0.0214(5) 0.0293(5) 0.0190(5) 0.0001(4) 0.0059(4) -0.0018(4)
  C19 0.0202(5) 0.0379(6) 0.0206(5) 0.0027(4) 0.0077(4) 0.0078(4)
  C20 0.0156(4) 0.0254(5) 0.0302(5) 0.0010(4) 0.0065(4) 0.0126(4)
  C21 0.0149(4) 0.0166(4) 0.0270(5) -0.0010(3) 0.0038(4) 0.0033(4)
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 . 1.3671(15) ?
  C1 C11 . 1.4278(14) ?
  C1 H1 . 0.988(15) ?
  C2 C3 . 1.4252(15) ?
  C2 H2 . 0.994(16) ?
  C3 C4 . 1.3632(15) ?
  C3 H3 . 0.984(14) ?
  C4 C12 . 1.4343(14) ?
  C4 H4 . 1.004(15) ?
  C5 C6 . 1.3652(16) ?
  C5 C14 . 1.4327(14) ?
  C5 H5 . 1.016(15) ?
  C6 C7 . 1.4247(16) ?
  C6 H6 . 1.008(16) ?
  C7 C8 . 1.3657(15) ?
  C7 H7 . 0.993(16) ?
  C8 C13 . 1.4322(14) ?
  C8 H8 . 0.991(16) ?
  C9 C11 . 1.3966(14) yes
  C9 C13 . 1.3969(14) yes
  C9 O15 . 1.3854(11) yes
  N10 C12 . 1.3490(13) yes
  N10 C14 . 1.3502(13) yes
  O15 C16 . 1.3907(12) yes
  C11 C12 . 1.4349(13) ?
  C13 C14 . 1.4364(13) ?
  C16 C17 . 1.3893(14) ?
  C16 C21 . 1.3933(13) ?
  C17 C18 . 1.3967(14) ?
  C17 H17 . 0.984(14) ?
  C18 C19 . 1.3892(16) ?
  C18 H18 . 0.973(16) ?
  C19 C20 . 1.3901(17) ?
  C19 H19 . 0.974(16) ?
  C20 C21 . 1.3897(15) ?
  C20 H20 . 0.986(16) ?
  C21 H21 . 0.955(15) ?