#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014657.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_2014657
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o114
_journal_page_last  o117
_publ_section_title
;
Two isomeric
2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]hexahydroisoindole-1,3-dione
compounds
;
loop_
_publ_author_name
  'Bin Li'
  'Hai-Bin Song'
  'Chi-Tung Hsu'
  'Ke-Liang Zhang'
  'Chao Wu'
  'Hua-Zheng Yang'
_chemical_formula_moiety  'C17 H13 Cl F N O3'
_chemical_formula_sum  'C17 H13 Cl F N O3'
_chemical_formula_iupac  'C17 H13 Cl F N O3'
_chemical_formula_weight  333.73
_chemical_melting_point  '409(1)'
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.313(5)
_cell_length_b  9.380(5)
_cell_length_c  10.485(6)
_cell_angle_alpha  99.663(9)
_cell_angle_beta  104.263(9)
_cell_angle_gamma  112.778(8)
_cell_volume  782.1(7)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.417
_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
  Cl1 1.10934(8) 0.63339(8) 0.87631(7) 0.0561(2) Uani d . 1 . . Cl
  F1 0.88880(18) 0.69124(17) 0.40938(15) 0.0555(4) Uani d . 1 . . F
  O1 0.5461(2) 0.6103(2) 0.32370(19) 0.0545(5) Uani d . 1 . . O
  O2 0.5902(2) 0.13836(19) 0.24919(17) 0.0479(4) Uani d . 1 . . O
  O3 0.8209(2) 0.33054(19) 0.76829(16) 0.0470(4) Uani d . 1 . . O
  N2 0.6090(2) 0.3948(2) 0.32126(19) 0.0389(5) Uani d . 1 . . N
  C1 0.5233(3) 0.4773(3) 0.2666(2) 0.0390(5) Uani d . 1 . . C
  C3 0.5445(3) 0.2389(3) 0.2296(2) 0.0379(5) Uani d . 1 . . C
  C3A 0.4144(3) 0.2288(3) 0.1088(2) 0.0404(6) Uani d . 1 . . C
  C4 0.3108(4) 0.0863(3) -0.0159(3) 0.0578(7) Uani d . 1 . . C
  H4A 0.2350 -0.0012 0.0079 0.069 Uiso calc R 1 . . H
  H4B 0.3812 0.0490 -0.0509 0.069 Uiso calc R 1 . . H
  C5 0.2141(6) 0.1325(5) -0.1248(4) 0.1062(16) Uani d . 1 . . C
  H5A 0.2828 0.1767 -0.1780 0.127 Uiso calc R 1 . . H
  H5B 0.1182 0.0346 -0.1867 0.127 Uiso calc R 1 . . H
  C6 0.1578(5) 0.2458(5) -0.0785(4) 0.0925(13) Uani d . 1 . . C
  H6A 0.0691 0.1917 -0.0450 0.111 Uiso calc R 1 . . H
  H6B 0.1101 0.2744 -0.1575 0.111 Uiso calc R 1 . . H
  C7 0.2833(3) 0.4007(3) 0.0325(3) 0.0521(7) Uani d . 1 . . C
  H7A 0.3419 0.4794 -0.0087 0.063 Uiso calc R 1 . . H
  H7B 0.2273 0.4453 0.0816 0.063 Uiso calc R 1 . . H
  C7A 0.4029(3) 0.3668(3) 0.1298(2) 0.0395(5) Uani d . 1 . . C
  C11 0.7297(3) 0.4524(3) 0.4541(2) 0.0363(5) Uani d . 1 . . C
  C12 0.8663(3) 0.6014(3) 0.4975(2) 0.0392(5) Uani d . 1 . . C
  C13 0.9835(3) 0.6593(3) 0.6260(2) 0.0418(6) Uani d . 1 . . C
  H13 1.0744 0.7603 0.6537 0.050 Uiso calc R 1 . . H
  C14 0.9637(3) 0.5642(3) 0.7134(2) 0.0385(5) Uani d . 1 . . C
  C15 0.8289(3) 0.4130(3) 0.6725(2) 0.0368(5) Uani d . 1 . . C
  C16 0.7123(3) 0.3584(3) 0.5431(2) 0.0373(5) Uani d . 1 . . C
  H16 0.6210 0.2576 0.5153 0.045 Uiso calc R 1 . . H
  C17 0.6888(3) 0.1711(3) 0.7292(3) 0.0498(7) Uani d . 1 . . C
  H17A 0.5853 0.1721 0.6831 0.060 Uiso calc R 1 . . H
  H17B 0.6807 0.1389 0.8113 0.060 Uiso calc R 1 . . H
  C18 0.7120(3) 0.0534(3) 0.6384(3) 0.0556(7) Uani d . 1 . . C
  C19 0.7317(4) -0.0416(4) 0.5683(4) 0.0859(11) Uani d . 1 . . C
  H19 0.7475 -0.1179 0.5119 0.103 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
  Cl1 0.0504(4) 0.0462(4) 0.0451(4) 0.0108(3) -0.0030(3) 0.0041(3)
  F1 0.0557(9) 0.0493(9) 0.0580(9) 0.0168(7) 0.0178(8) 0.0262(7)
  O1 0.0559(11) 0.0441(11) 0.0579(11) 0.0287(9) 0.0089(9) 0.0020(9)
  O2 0.0539(11) 0.0374(9) 0.0513(10) 0.0235(8) 0.0118(9) 0.0117(8)
  O3 0.0540(10) 0.0342(9) 0.0377(9) 0.0107(8) 0.0069(8) 0.0099(7)
  N2 0.0414(11) 0.0339(10) 0.0372(11) 0.0178(9) 0.0072(9) 0.0072(8)
  C1 0.0417(13) 0.0361(13) 0.0421(13) 0.0202(11) 0.0151(11) 0.0105(10)
  C3 0.0379(13) 0.0339(12) 0.0393(13) 0.0137(10) 0.0140(10) 0.0095(10)
  C3A 0.0412(13) 0.0387(13) 0.0386(13) 0.0166(11) 0.0130(11) 0.0093(10)
  C4 0.0626(18) 0.0456(15) 0.0482(16) 0.0231(14) 0.0012(14) 0.0017(12)
  C5 0.124(3) 0.080(3) 0.070(2) 0.057(3) -0.033(2) -0.0150(19)
  C6 0.091(3) 0.086(3) 0.070(2) 0.053(2) -0.0247(19) -0.0073(19)
  C7 0.0520(16) 0.0560(16) 0.0493(15) 0.0303(13) 0.0094(13) 0.0150(13)
  C7A 0.0400(13) 0.0400(13) 0.0401(13) 0.0192(11) 0.0136(11) 0.0123(10)
  C11 0.0372(12) 0.0351(12) 0.0332(12) 0.0173(10) 0.0088(10) 0.0038(10)
  C12 0.0435(13) 0.0341(12) 0.0435(13) 0.0183(11) 0.0172(11) 0.0141(10)
  C13 0.0362(13) 0.0306(12) 0.0480(14) 0.0099(10) 0.0109(11) 0.0042(11)
  C14 0.0370(13) 0.0331(12) 0.0376(13) 0.0146(10) 0.0066(10) 0.0029(10)
  C15 0.0398(13) 0.0322(12) 0.0361(12) 0.0168(10) 0.0109(10) 0.0056(10)
  C16 0.0352(12) 0.0308(12) 0.0383(13) 0.0107(10) 0.0102(10) 0.0049(10)
  C17 0.0548(16) 0.0358(14) 0.0489(15) 0.0121(12) 0.0139(13) 0.0143(12)
  C18 0.0518(16) 0.0370(15) 0.0599(18) 0.0133(13) 0.0045(14) 0.0080(13)
  C19 0.076(2) 0.059(2) 0.098(3) 0.0294(18) 0.010(2) -0.0056(19)
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
  Cl1 C14 . 1.728(2) ?
  F1 C12 . 1.352(3) ?
  O1 C1 . 1.201(3) ?
  O2 C3 . 1.202(3) ?
  O3 C15 . 1.366(3) ?
  O3 C17 . 1.428(3) ?
  N2 C1 . 1.402(3) ?
  N2 C3 . 1.409(3) ?
  N2 C11 . 1.414(3) ?
  C1 C7A . 1.482(3) ?
  C3 C3A . 1.481(3) ?
  C3A C7A . 1.326(3) ?
  C3A C4 . 1.490(3) ?
  C4 C5 . 1.505(4) ?
  C4 H4A . 0.97 ?
  C4 H4B . 0.97 ?
  C5 C6 . 1.422(5) ?
  C5 H5A . 0.97 ?
  C5 H5B . 0.97 ?
  C6 C7 . 1.509(4) ?
  C6 H6A . 0.97 ?
  C6 H6B . 0.97 ?
  C7 C7A . 1.485(3) ?
  C7 H7A . 0.97 ?
  C7 H7B . 0.97 ?
  C11 C12 . 1.379(3) ?
  C11 C16 . 1.384(3) ?
  C12 C13 . 1.369(3) ?
  C13 C14 . 1.377(3) ?
  C13 H13 . 0.93 ?
  C14 C15 . 1.387(3) ?
  C15 C16 . 1.375(3) ?
  C16 H16 . 0.93 ?
  C17 C18 . 1.451(4) ?
  C17 H17A . 0.97 ?
  C17 H17B . 0.97 ?
  C18 C19 . 1.158(4) ?
  C19 H19 . 0.93 ?
_cod_database_code 2014657