#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013902.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_2013902
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o232
_journal_page_last  o234
_publ_section_title
;
3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
and
3-[4-(2-fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
;
loop_
_publ_author_name
  'Yavuz K\"oysal'
  '\,Samil I\,s\?ik'
  'Meri\,c K\"oksal'
  'Hakk\?i Erdo\~gan'
  'Nesrin Gokhan'
_chemical_formula_moiety  'C19 H20 F N3 O2'
_chemical_formula_sum  'C19 H20 F N3 O2'
_chemical_formula_iupac  'C19 H20 F N3 O2'
_chemical_formula_weight  341.22
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  15.7467(10)
_cell_length_b  9.5470(4)
_cell_length_c  11.4779(6)
_cell_angle_alpha  90.00
_cell_angle_beta  91.422(5)
_cell_angle_gamma  90.00
_cell_volume  1724.98(16)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.314
_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
  F1 -0.02623(7) 0.84447(13) 0.02487(12) 0.1032(4) Uani d . 1 . . F
  O1 0.41098(7) 0.76653(12) -0.10543(10) 0.0726(3) Uani d . 1 . . O
  O2 0.44069(6) 0.54729(11) -0.16695(8) 0.0625(3) Uani d . 1 . . O
  N1 0.07924(7) 0.67022(13) 0.15050(9) 0.0566(3) Uani d . 1 . . N
  N2 0.25221(6) 0.60123(11) 0.11386(8) 0.0514(3) Uani d . 1 . . N
  N3 0.37578(6) 0.56932(12) 0.00110(9) 0.0525(3) Uani d . 1 . . N
  C1 -0.06219(10) 0.75215(18) 0.09803(15) 0.0711(4) Uani d . 1 . . C
  C2 -0.14883(11) 0.7532(2) 0.10515(19) 0.0895(6) Uani d . 1 . . C
  H2 -0.1814 0.8125 0.0580 0.123(8) Uiso d R 1 . . H
  C3 -0.18693(11) 0.6660(3) 0.18300(19) 0.0957(7) Uani d . 1 . . C
  H3 -0.2456 0.6656 0.1895 0.100(6) Uiso d R 1 . . H
  C4 -0.13785(12) 0.5789(3) 0.24992(18) 0.0979(7) Uani d . 1 . . C
  H4 -0.1633 0.5208 0.3039 0.117(7) Uiso d R 1 . . H
  C5 -0.05018(10) 0.5767(2) 0.23999(15) 0.0797(5) Uani d . 1 . . C
  H5 -0.0182 0.5151 0.2860 0.102(7) Uiso d R 1 . . H
  C6 -0.00974(9) 0.66396(16) 0.16311(12) 0.0586(3) Uani d . 1 . . C
  C7 0.13017(9) 0.5996(2) 0.23995(12) 0.0679(4) Uani d . 1 . . C
  H7A 0.1108 0.6258 0.3164 0.075(5) Uiso d R 1 . . H
  H7B 0.1239 0.4991 0.2315 0.085(6) Uiso d R 1 . . H
  C8 0.22230(9) 0.63949(19) 0.22851(11) 0.0644(4) Uani d . 1 . . C
  H8A 0.2562 0.5918 0.2880 0.080(5) Uiso d R 1 . . H
  H8B 0.2288 0.7396 0.2401 0.083(5) Uiso d R 1 . . H
  C9 0.20062(8) 0.66981(17) 0.02394(12) 0.0608(4) Uani d . 1 . . C
  H9A 0.2201 0.6424 -0.0523 0.077(5) Uiso d R 1 . . H
  H9B 0.2067 0.7706 0.0310 0.071(5) Uiso d R 1 . . H
  C10 0.10865(9) 0.63019(18) 0.03537(11) 0.0615(4) Uani d . 1 . . C
  H10A 0.0747 0.6774 -0.0244 0.081(5) Uiso d R 1 . . H
  H10B 0.1020 0.5300 0.0246 0.077(5) Uiso d R 1 . . H
  C11 0.34135(8) 0.63315(15) 0.10457(11) 0.0547(3) Uani d . 1 . . C
  H11A 0.3491 0.7339 0.1013 0.063(4) Uiso d R 1 . . H
  H11B 0.3719 0.5984 0.1731 0.061(4) Uiso d R 1 . . H
  C12 0.40852(8) 0.64277(16) -0.08915(11) 0.0567(3) Uani d . 1 . . C
  C13 0.42527(8) 0.41439(15) -0.12344(11) 0.0547(3) Uani d . 1 . . C
  C14 0.44493(8) 0.28826(17) -0.17164(13) 0.0637(4) Uani d . 1 . . C
  H14 0.4730 0.2815 -0.2418 0.081(5) Uiso d R 1 . . H
  C15 0.42038(9) 0.17060(17) -0.11008(14) 0.0651(4) Uani d . 1 . . C
  H15 0.4328 0.0827 -0.1401 0.073(5) Uiso d R 1 . . H
  C16 0.37814(9) 0.17879(15) -0.00525(13) 0.0596(3) Uani d . 1 . . C
  C17 0.35979(8) 0.30978(15) 0.04181(11) 0.0550(3) Uani d . 1 . . C
  H17 0.3317 0.3178 0.1118 0.054(4) Uiso d R 1 . . H
  C18 0.38446(7) 0.42639(14) -0.01861(11) 0.0495(3) Uani d . 1 . . C
  C19 0.35196(13) 0.04793(18) 0.05641(16) 0.0813(5) Uani d . 1 . . C
  H19A 0.3211 0.0723 0.1246 0.122 Uiso calc R 1 . . H
  H19B 0.4016 -0.0049 0.0789 0.122 Uiso calc R 1 . . H
  H19C 0.3164 -0.0075 0.0053 0.122 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
  F1 0.0863(7) 0.0943(8) 0.1281(10) 0.0026(5) -0.0140(6) 0.0365(7)
  O1 0.0836(7) 0.0659(7) 0.0688(6) -0.0086(5) 0.0142(5) 0.0060(5)
  O2 0.0627(5) 0.0744(6) 0.0510(5) -0.0081(5) 0.0152(4) -0.0044(4)
  N1 0.0525(6) 0.0705(7) 0.0470(6) 0.0032(5) 0.0021(4) -0.0039(5)
  N2 0.0538(6) 0.0595(6) 0.0413(5) 0.0023(5) 0.0057(4) -0.0025(4)
  N3 0.0531(6) 0.0580(6) 0.0469(6) -0.0002(5) 0.0096(4) -0.0035(5)
  C1 0.0651(8) 0.0691(9) 0.0785(10) 0.0010(7) -0.0075(7) -0.0073(8)
  C2 0.0625(9) 0.1030(14) 0.1022(14) 0.0110(9) -0.0153(9) -0.0196(12)
  C3 0.0548(9) 0.1387(19) 0.0936(13) -0.0036(10) 0.0030(9) -0.0254(13)
  C4 0.0688(10) 0.145(2) 0.0809(12) -0.0152(11) 0.0165(9) -0.0046(12)
  C5 0.0659(9) 0.1091(14) 0.0644(9) -0.0007(9) 0.0112(7) 0.0058(9)
  C6 0.0540(7) 0.0681(8) 0.0539(7) 0.0014(6) 0.0018(6) -0.0129(6)
  C7 0.0609(8) 0.0990(12) 0.0440(7) 0.0111(7) 0.0081(6) 0.0060(7)
  C8 0.0593(7) 0.0932(12) 0.0409(7) 0.0121(7) 0.0018(6) -0.0065(7)
  C9 0.0597(8) 0.0784(10) 0.0445(7) -0.0013(6) 0.0034(6) 0.0056(6)
  C10 0.0601(7) 0.0810(10) 0.0435(7) -0.0025(7) 0.0021(6) -0.0033(6)
  C11 0.0547(7) 0.0603(8) 0.0494(7) 0.0009(6) 0.0056(5) -0.0089(6)
  C12 0.0521(7) 0.0659(9) 0.0524(7) -0.0060(6) 0.0064(5) -0.0011(6)
  C13 0.0460(6) 0.0691(8) 0.0491(7) -0.0021(6) 0.0052(5) -0.0058(6)
  C14 0.0541(7) 0.0811(10) 0.0563(8) 0.0031(6) 0.0091(6) -0.0174(7)
  C15 0.0602(8) 0.0678(9) 0.0674(9) 0.0105(7) -0.0001(6) -0.0175(7)
  C16 0.0587(7) 0.0606(8) 0.0591(8) 0.0069(6) -0.0041(6) -0.0037(6)
  C17 0.0554(7) 0.0617(8) 0.0479(7) 0.0056(6) 0.0034(5) -0.0025(6)
  C18 0.0440(6) 0.0586(7) 0.0458(6) 0.0032(5) 0.0025(5) -0.0054(5)
  C19 0.1041(13) 0.0597(9) 0.0802(11) 0.0072(8) 0.0023(9) 0.0005(8)
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
  F1 C1 . 1.351(2) yes
  O1 C12 . 1.1970(18) yes
  O2 C12 . 1.3810(17) yes
  O2 C13 . 1.3872(17) yes
  N1 C6 . 1.4134(17) yes
  N1 C7 . 1.4530(18) yes
  N1 C10 . 1.4620(17) yes
  N2 C11 . 1.4429(16) yes
  N2 C9 . 1.4535(17) yes
  N2 C8 . 1.4553(16) yes
  N3 C12 . 1.3628(17) yes
  N3 C18 . 1.3905(17) yes
  N3 C11 . 1.4518(15) yes
  C1 C2 . 1.369(2) ?
  C1 C6 . 1.385(2) ?
  C2 C3 . 1.371(3) ?
  C2 H2 . 0.9289 ?
  C3 C4 . 1.359(3) ?
  C3 H3 . 0.9293 ?
  C4 C5 . 1.388(2) ?
  C4 H4 . 0.9297 ?
  C5 C6 . 1.381(2) ?
  C5 H5 . 0.9299 ?
  C7 C8 . 1.509(2) ?
  C7 H7A . 0.9691 ?
  C7 H7B . 0.9691 ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9699 ?
  C9 C10 . 1.5056(19) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9699 ?
  C10 H10A . 0.9699 ?
  C10 H10B . 0.9697 ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9699 ?
  C13 C14 . 1.364(2) ?
  C13 C18 . 1.3828(17) ?
  C14 C15 . 1.387(2) ?
  C14 H14 . 0.9297 ?
  C15 C16 . 1.391(2) ?
  C15 H15 . 0.9298 ?
  C16 C17 . 1.3953(19) ?
  C16 C19 . 1.499(2) ?
  C17 C18 . 1.3728(19) ?
  C17 H17 . 0.9298 ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?