#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014658.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_2014658
_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  '369(1)'
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  22.712(15)
_cell_length_b  7.474(5)
_cell_length_c  18.655(12)
_cell_angle_alpha  90.00
_cell_angle_beta  99.061(11)
_cell_angle_gamma  90.00
_cell_volume  3127(4)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.418
_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 0.38216(4) 0.94181(12) 0.03497(5) 0.0711(3) Uani d . 1 A . Cl
  F1 0.18203(8) 0.8311(3) 0.10933(11) 0.0697(6) Uani d . 1 . . F
  O1 0.20485(12) 0.6548(4) 0.25578(13) 0.0871(9) Uani d . 1 . . O
  O2 0.20038(11) 0.2630(3) 0.06959(13) 0.0688(6) Uani d . 1 . . O
  O3 0.40032(9) 0.5794(3) 0.07586(14) 0.0696(7) Uani d D 1 . . O
  N2 0.20966(10) 0.4858(3) 0.15471(13) 0.0497(6) Uani d . 1 . . N
  C1 0.19011(14) 0.5228(5) 0.21999(17) 0.0621(9) Uani d . 1 . . C
  C3 0.18841(13) 0.3225(4) 0.12499(17) 0.0533(8) Uani d . 1 . . C
  C3A 0.14951(16) 0.2418(6) 0.17440(19) 0.0718(10) Uani d . 1 . . C
  H3 0.1680 0.1298 0.1938 0.086 Uiso calc R 1 . . H
  C4 0.0892(2) 0.1989(10) 0.1331(3) 0.128(2) Uani d . 1 . . C
  H4A 0.0933 0.1511 0.0858 0.153 Uiso calc R 1 . . H
  H4B 0.0702 0.1087 0.1589 0.153 Uiso calc R 1 . . H
  C5 0.0519(2) 0.3607(13) 0.1240(3) 0.151(3) Uani d . 1 . . C
  H5 0.0276 0.3822 0.0800 0.181 Uiso calc R 1 . . H
  C6 0.0527(2) 0.4783(11) 0.1791(4) 0.145(3) Uani d . 1 . . C
  H6 0.0298 0.5819 0.1730 0.174 Uiso calc R 1 . . H
  C7 0.09085(19) 0.4390(8) 0.2494(2) 0.1023(16) Uani d . 1 . . C
  H7A 0.0717 0.3496 0.2756 0.123 Uiso calc R 1 . . H
  H7B 0.0962 0.5467 0.2787 0.123 Uiso calc R 1 . . H
  C7A 0.15069(15) 0.3709(6) 0.23609(17) 0.0689(10) Uani d . 1 . . C
  H7 0.1700 0.3116 0.2805 0.083 Uiso calc R 1 . . H
  C11 0.25059(13) 0.5954(4) 0.12441(15) 0.0476(7) Uani d . 1 A . C
  C12 0.23645(13) 0.7686(4) 0.10352(15) 0.0490(7) Uani d . 1 . . C
  C13 0.27591(13) 0.8775(4) 0.07586(15) 0.0511(7) Uani d . 1 A . C
  H13 0.2659 0.9949 0.0626 0.061 Uiso calc R 1 . . H
  C14 0.33070(13) 0.8087(4) 0.06832(15) 0.0476(7) Uani d . 1 . . C
  C15 0.34536(12) 0.6340(4) 0.08740(16) 0.0483(7) Uani d D 1 A . C
  C16 0.30554(13) 0.5278(4) 0.11614(16) 0.0513(7) Uani d . 1 . . C
  H16 0.3156 0.4108 0.1300 0.062 Uiso calc R 1 A . H
  C17 0.4128(2) 0.3914(5) 0.0823(6) 0.0705(18) Uani d PD 0.549(5) A 1 C
  H17A 0.4077 0.3516 0.1304 0.085 Uiso calc PR 0.549(5) A 1 H
  H17B 0.3843 0.3272 0.0473 0.085 Uiso calc PR 0.549(5) A 1 H
  C18 0.47157(19) 0.3489(6) 0.0703(3) 0.0623(17) Uani d PD 0.549(5) A 1 C
  C19 0.5184(2) 0.3206(10) 0.0571(4) 0.076(2) Uani d PD 0.549(5) A 1 C
  H19 0.5563 0.2977 0.0464 0.091 Uiso calc PR 0.549(5) A 1 H
  C17A 0.4220(4) 0.4110(12) 0.1013(4) 0.0705(18) Uani d PD 0.451(5) A 2 C
  H17C 0.4545 0.3773 0.0759 0.085 Uiso calc PR 0.451(5) A 2 H
  H17D 0.3905 0.3234 0.0893 0.085 Uiso calc PR 0.451(5) A 2 H
  C18A 0.4428(4) 0.4036(11) 0.1777(3) 0.088(3) Uani d PD 0.451(5) A 2 C
  C19A 0.4564(7) 0.409(2) 0.2399(4) 0.155(7) Uani d PD 0.451(5) A 2 C
  H19A 0.4674 0.4127 0.2901 0.186 Uiso calc PR 0.451(5) A 2 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 0.0766(6) 0.0556(5) 0.0844(6) -0.0070(4) 0.0231(5) 0.0078(5)
  F1 0.0558(11) 0.0611(12) 0.0929(14) 0.0188(9) 0.0138(10) -0.0071(11)
  O1 0.0920(18) 0.111(2) 0.0621(15) -0.0254(18) 0.0229(13) -0.0300(16)
  O2 0.0893(17) 0.0551(14) 0.0661(14) 0.0038(13) 0.0248(13) -0.0057(12)
  O3 0.0542(13) 0.0522(14) 0.1066(19) 0.0089(11) 0.0260(12) 0.0020(13)
  N2 0.0489(13) 0.0555(15) 0.0455(13) 0.0029(12) 0.0103(11) -0.0009(12)
  C1 0.0551(18) 0.085(3) 0.0453(17) -0.0038(18) 0.0043(14) -0.0042(18)
  C3 0.0514(17) 0.0535(19) 0.0543(18) 0.0060(15) 0.0059(14) 0.0101(16)
  C3A 0.071(2) 0.079(2) 0.066(2) -0.014(2) 0.0143(18) 0.007(2)
  C4 0.080(3) 0.203(7) 0.102(4) -0.062(4) 0.022(3) -0.037(4)
  C5 0.047(2) 0.317(11) 0.086(3) 0.002(4) 0.000(2) 0.007(5)
  C6 0.074(3) 0.234(8) 0.136(5) 0.059(4) 0.043(3) 0.042(5)
  C7 0.081(3) 0.141(5) 0.093(3) -0.006(3) 0.037(3) -0.013(3)
  C7A 0.062(2) 0.099(3) 0.0481(18) -0.009(2) 0.0132(15) 0.0073(19)
  C11 0.0500(17) 0.0490(17) 0.0442(15) 0.0053(14) 0.0089(13) -0.0022(13)
  C12 0.0473(16) 0.0489(17) 0.0498(16) 0.0111(14) 0.0041(13) -0.0090(14)
  C13 0.0616(19) 0.0382(15) 0.0513(17) 0.0098(15) 0.0020(14) -0.0023(14)
  C14 0.0582(18) 0.0429(16) 0.0418(15) -0.0001(14) 0.0082(13) -0.0008(13)
  C15 0.0457(16) 0.0464(17) 0.0541(17) 0.0058(14) 0.0119(13) -0.0002(14)
  C16 0.0537(17) 0.0418(16) 0.0592(18) 0.0087(14) 0.0111(14) 0.0023(14)
  C17 0.076(3) 0.061(3) 0.078(5) 0.021(3) 0.024(3) -0.005(3)
  C18 0.060(4) 0.052(4) 0.078(4) -0.003(3) 0.018(3) -0.005(3)
  C19 0.052(4) 0.083(5) 0.098(5) 0.010(3) 0.029(3) -0.009(4)
  C17A 0.076(3) 0.061(3) 0.078(5) 0.021(3) 0.024(3) -0.005(3)
  C18A 0.077(6) 0.068(6) 0.127(9) 0.024(5) 0.037(6) 0.003(6)
  C19A 0.202(14) 0.162(14) 0.097(8) 0.085(11) 0.012(10) 0.005(9)
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 . 1.724(3) ?
  F1 C12 . 1.342(3) ?
  O1 C1 . 1.208(4) ?
  O2 C3 . 1.195(4) ?
  O3 C15 . 1.362(3) ?
  O3 C17A . 1.407(7) ?
  O3 C17 . 1.435(3) ?
  N2 C1 . 1.388(4) ?
  N2 C3 . 1.395(4) ?
  N2 C11 . 1.421(4) ?
  C1 C7A . 1.505(5) ?
  C3 C3A . 1.500(4) ?
  C3A C4 . 1.497(6) ?
  C3A C7A . 1.499(5) ?
  C3A H3 . 0.98 ?
  C4 C5 . 1.470(10) ?
  C4 H4A . 0.97 ?
  C4 H4B . 0.97 ?
  C5 C6 . 1.349(9) ?
  C5 H5 . 0.93 ?
  C6 C7 . 1.483(7) ?
  C6 H6 . 0.93 ?
  C7 C7A . 1.508(5) ?
  C7 H7A . 0.97 ?
  C7 H7B . 0.97 ?
  C7A H7 . 0.98 ?
  C11 C12 . 1.375(4) ?
  C11 C16 . 1.378(4) ?
  C12 C13 . 1.370(4) ?
  C13 C14 . 1.374(4) ?
  C13 H13 . 0.93 ?
  C14 C15 . 1.380(4) ?
  C15 C16 . 1.374(4) ?
  C16 H16 . 0.93 ?
  C17 C18 . 1.424(3) ?
  C17 H17A . 0.97 ?
  C17 H17B . 0.97 ?
  C18 C19 . 1.148(3) ?
  C19 H19 . 0.93 ?
  C17A C18A . 1.429(3) ?
  C17A H17C . 0.97 ?
  C17A H17D . 0.97 ?
  C18A C19A . 1.155(3) ?
  C19A H19A . 0.93 ?