#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2013025.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_2013025
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o645
_journal_page_last  o648
_publ_section_title
;
Structural motifs in acetoacetanilides: the effect of a fluorine substituent
;
loop_
_publ_author_name
  'Chisholm, Greig'
  'Kennedy, Alan R.'
  'Beaton, Laura'
  'Brook, Eve'
_chemical_formula_moiety  'C10 H10 F N O2'
_chemical_formula_sum  'C10 H10 F N O2'
_chemical_formula_weight  195.19
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  '-x-1/2, y-1/2, z'
  'x, -y-1/2, z-1/2'
_cell_length_a  9.4933(3)
_cell_length_b  9.7792(3)
_cell_length_c  20.2345(7)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1878.51(11)
_cell_formula_units_Z  8
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.380
_diffrn_ambient_temperature  150(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 -0.03629(9) 0.39731(10) 0.08777(4) 0.0366(3) Uani d . 1 . . F
  O1 0.25883(13) 0.13894(13) 0.37141(6) 0.0402(3) Uani d . 1 . . O
  O2 0.06376(10) 0.05021(13) 0.24909(5) 0.0363(3) Uani d . 1 . . O
  N1 0.27845(14) 0.09721(14) 0.20457(6) 0.0259(3) Uani d . 1 . . N
  H1N 0.370(2) 0.0787(17) 0.2078(8) 0.035(5) Uiso d . 1 . . H
  C1 0.3917(2) -0.0507(2) 0.40981(10) 0.0386(5) Uani d . 1 . . C
  H1A 0.366(2) -0.146(3) 0.4141(10) 0.062(7) Uiso d . 1 . . H
  H1B 0.482(3) -0.056(3) 0.3952(11) 0.075(8) Uiso d . 1 . . H
  H1C 0.394(2) -0.005(2) 0.4517(12) 0.064(7) Uiso d . 1 . . H
  C2 0.30144(16) 0.02397(18) 0.36163(8) 0.0273(4) Uani d . 1 . . C
  C3 0.26651(17) -0.05238(18) 0.29890(8) 0.0253(4) Uani d . 1 . . C
  H3A 0.3500(18) -0.0902(17) 0.2826(8) 0.029(4) Uiso d . 1 . . H
  H3B 0.2102(17) -0.1299(17) 0.3103(8) 0.031(5) Uiso d . 1 . . H
  C4 0.19230(15) 0.03588(17) 0.24888(7) 0.0250(4) Uani d . 1 . . C
  C5 0.23996(14) 0.17868(16) 0.14999(7) 0.0232(4) Uani d . 1 . . C
  C6 0.11316(16) 0.24979(17) 0.14672(8) 0.0252(4) Uani d . 1 . . C
  H6 0.0467(16) 0.2441(15) 0.1802(7) 0.026(4) Uiso d . 1 . . H
  C7 0.08714(15) 0.32580(17) 0.09095(8) 0.0262(4) Uani d . 1 . . C
  C8 0.17729(17) 0.33549(17) 0.03824(8) 0.0292(4) Uani d . 1 . . C
  H8 0.1454(16) 0.3909(17) -0.0017(9) 0.029(4) Uiso d . 1 . . H
  C9 0.30320(18) 0.26480(19) 0.04270(8) 0.0333(4) Uani d . 1 . . C
  H9 0.3750(16) 0.2711(17) 0.0060(8) 0.037(5) Uiso d . 1 . . H
  C10 0.33527(17) 0.18840(18) 0.09780(8) 0.0294(4) Uani d . 1 . . C
  H10 0.4221(19) 0.1432(18) 0.1014(8) 0.035(5) 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
  F1 0.0276(5) 0.0418(6) 0.0404(6) 0.0074(5) -0.0022(4) 0.0064(5)
  O1 0.0564(8) 0.0268(7) 0.0372(7) 0.0071(6) -0.0023(6) -0.0027(6)
  O2 0.0176(6) 0.0546(8) 0.0368(7) 0.0003(6) 0.0021(5) 0.0094(6)
  N1 0.0163(7) 0.0342(9) 0.0271(7) 0.0017(6) 0.0008(5) 0.0046(6)
  C1 0.0468(12) 0.0337(12) 0.0353(11) 0.0021(10) -0.0108(9) 0.0007(10)
  C2 0.0275(8) 0.0253(10) 0.0292(8) -0.0023(8) 0.0023(7) 0.0015(7)
  C3 0.0215(8) 0.0245(9) 0.0299(9) 0.0012(8) 0.0024(7) -0.0001(7)
  C4 0.0202(8) 0.0279(9) 0.0270(8) -0.0010(7) 0.0013(7) -0.0020(7)
  C5 0.0211(8) 0.0232(9) 0.0252(8) -0.0028(7) -0.0011(6) -0.0021(7)
  C6 0.0214(8) 0.0299(10) 0.0244(8) -0.0006(7) 0.0007(7) -0.0033(8)
  C7 0.0215(8) 0.0261(9) 0.0312(9) 0.0007(7) -0.0048(7) -0.0042(8)
  C8 0.0361(9) 0.0277(9) 0.0239(8) -0.0005(8) -0.0011(7) -0.0002(8)
  C9 0.0365(9) 0.0334(10) 0.0299(9) 0.0004(8) 0.0094(8) -0.0006(8)
  C10 0.0244(8) 0.0276(10) 0.0361(10) 0.0030(8) 0.0056(7) -0.0001(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 C7 . 1.3661(17) y
  O1 C2 . 1.211(2) y
  O2 C4 . 1.2283(16) y
  N1 C4 . 1.3536(19) y
  N1 C5 . 1.4101(19) y
  N1 H1N . 0.892(19) ?
  C1 C2 . 1.489(3) ?
  C1 H1A . 0.96(2) ?
  C1 H1B . 0.90(2) ?
  C1 H1C . 0.96(2) ?
  C2 C3 . 1.509(2) ?
  C3 C4 . 1.505(2) ?
  C3 H3A . 0.934(17) ?
  C3 H3B . 0.956(17) ?
  C5 C6 . 1.392(2) ?
  C5 C10 . 1.394(2) ?
  C6 C7 . 1.374(2) ?
  C6 H6 . 0.927(15) ?
  C7 C8 . 1.371(2) ?
  C8 C9 . 1.384(2) ?
  C8 H8 . 1.018(17) ?
  C9 C10 . 1.376(2) ?
  C9 H9 . 1.010(16) ?
  C10 H10 . 0.938(18) ?
_cod_database_code 2013025