#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202472.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_2202472
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1066
_journal_page_last  o1067
_publ_section_title
;
4,5,6,7-Tetrachloro-2-(naphthalen-1-yl)isoindole-1,3-dione acetone solvate
;
loop_
_publ_author_name
  'Zhou, Li-shan'
  'Feng, Ya-Qing'
  'Bo Gao'
  'Da-xin Shi'
  'Li, Xiao-Fang'
_chemical_formula_moiety  'C18 H7 Cl4 N O2, C3 H6 O'
_chemical_formula_sum  'C21 H13 Cl4 N O3'
_chemical_formula_iupac  'C18 H7 Cl4 N O2, C3 H6 O'
_chemical_formula_weight  469.12
_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  7.706(3)
_cell_length_b  9.007(3)
_cell_length_c  16.213(6)
_cell_angle_alpha  94.985(6)
_cell_angle_beta  91.165(6)
_cell_angle_gamma  114.879(5)
_cell_volume  1015.0(6)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.535
_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 0.49679(10) 0.76588(8) 0.48951(4) 0.0536(2) Uani d . 1 . . Cl
  Cl2 0.31412(11) 0.50661(9) 0.61486(4) 0.0544(2) Uani d . 1 . . Cl
  Cl3 -0.03320(11) 0.17536(9) 0.55758(4) 0.0573(2) Uani d . 1 . . Cl
  Cl4 -0.19612(10) 0.09529(8) 0.37237(4) 0.0558(2) Uani d . 1 . . Cl
  O1 0.4191(3) 0.7739(2) 0.30108(11) 0.0549(5) Uani d . 1 . . O
  O2 -0.0896(3) 0.2890(3) 0.21518(12) 0.0712(6) Uani d . 1 . . O
  N1 0.1592(3) 0.5473(2) 0.23976(12) 0.0462(5) Uani d . 1 . . N
  C1 0.2910(4) 0.6421(3) 0.30486(14) 0.0409(6) Uani d . 1 . . C
  C2 0.2325(3) 0.5428(3) 0.37693(14) 0.0372(5) Uani d . 1 . . C
  C3 0.3078(3) 0.5805(3) 0.45807(14) 0.0385(6) Uani d . 1 . . C
  C4 0.2238(4) 0.4645(3) 0.51372(14) 0.0398(6) Uani d . 1 . . C
  C5 0.0683(4) 0.3147(3) 0.48757(14) 0.0402(6) Uani d . 1 . . C
  C6 -0.0059(4) 0.2789(3) 0.40504(15) 0.0403(6) Uani d . 1 . . C
  C7 0.0789(3) 0.3952(3) 0.35112(14) 0.0384(6) Uani d . 1 . . C
  C8 0.0309(4) 0.3942(3) 0.26106(16) 0.0467(6) Uani d . 1 . . C
  C9 0.1645(4) 0.6001(3) 0.15810(15) 0.0466(7) Uani d . 1 . . C
  C10 0.2875(4) 0.5795(4) 0.10489(17) 0.0568(7) Uani d . 1 . . C
  H10 0.3666 0.5311 0.1208 0.068 Uiso calc R 1 . . H
  C11 0.2946(5) 0.6322(4) 0.02529(18) 0.0657(9) Uani d . 1 . . C
  H11 0.3786 0.6183 -0.0117 0.079 Uiso calc R 1 . . H
  C12 0.1798(5) 0.7029(4) 0.00234(18) 0.0641(9) Uani d . 1 . . C
  H12 0.1863 0.7371 -0.0505 0.077 Uiso calc R 1 . . H
  C13 0.0511(4) 0.7259(3) 0.05631(17) 0.0544(7) Uani d . 1 . . C
  C14 -0.0696(5) 0.8000(4) 0.0337(2) 0.0744(10) Uani d . 1 . . C
  H14 -0.0657 0.8338 -0.0190 0.089 Uiso calc R 1 . . H
  C15 -0.1906(6) 0.8227(5) 0.0873(3) 0.0851(11) Uani d . 1 . . C
  H15 -0.2673 0.8733 0.0713 0.102 Uiso calc R 1 . . H
  C16 -0.2012(5) 0.7703(5) 0.1665(2) 0.0798(10) Uani d . 1 . . C
  H16 -0.2851 0.7858 0.2029 0.096 Uiso calc R 1 . . H
  C17 -0.0882(4) 0.6962(4) 0.19053(19) 0.0626(8) Uani d . 1 . . C
  H17 -0.0970 0.6613 0.2432 0.075 Uiso calc R 1 . . H
  C18 0.0402(4) 0.6720(3) 0.13719(16) 0.0474(7) Uani d . 1 . . C
  O3 0.5994(5) 0.6625(4) 0.7731(2) 0.1259(12) Uani d . 1 . . O
  C19 0.7113(6) 0.9027(4) 0.7079(2) 0.0831(11) Uani d . 1 . . C
  H19A 0.7192 0.8318 0.6618 0.125 Uiso calc R 1 . . H
  H19B 0.8375 0.9845 0.7258 0.125 Uiso calc R 1 . . H
  H19C 0.6331 0.9557 0.6913 0.125 Uiso calc R 1 . . H
  C20 0.6253(5) 0.8046(4) 0.7767(2) 0.0684(9) Uani d . 1 . . C
  C21 0.5669(7) 0.8878(6) 0.8460(3) 0.1204(18) Uani d . 1 . . C
  H21A 0.4947 0.9419 0.8243 0.181 Uiso calc R 1 . . H
  H21B 0.6789 0.9676 0.8777 0.181 Uiso calc R 1 . . H
  H21C 0.4892 0.8078 0.8810 0.181 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 0.0539(4) 0.0534(4) 0.0449(4) 0.0154(3) -0.0059(3) 0.0018(3)
  Cl2 0.0648(5) 0.0729(5) 0.0335(4) 0.0364(4) -0.0010(3) 0.0104(3)
  Cl3 0.0759(5) 0.0582(4) 0.0467(4) 0.0326(4) 0.0164(3) 0.0267(3)
  Cl4 0.0561(4) 0.0444(4) 0.0555(4) 0.0084(3) 0.0040(3) 0.0152(3)
  O1 0.0572(12) 0.0448(11) 0.0464(11) 0.0047(10) 0.0012(9) 0.0118(8)
  O2 0.0739(15) 0.0580(12) 0.0472(12) -0.0058(11) -0.0144(10) 0.0117(9)
  N1 0.0529(13) 0.0443(12) 0.0331(11) 0.0107(10) -0.0004(9) 0.0144(9)
  C1 0.0434(15) 0.0431(14) 0.0355(14) 0.0166(12) 0.0025(10) 0.0095(10)
  C2 0.0391(14) 0.0404(13) 0.0352(13) 0.0189(11) 0.0037(10) 0.0083(10)
  C3 0.0387(14) 0.0459(14) 0.0354(13) 0.0221(12) 0.0023(10) 0.0056(10)
  C4 0.0462(15) 0.0522(15) 0.0319(13) 0.0305(13) 0.0032(10) 0.0094(11)
  C5 0.0480(15) 0.0474(14) 0.0374(14) 0.0293(13) 0.0101(11) 0.0170(11)
  C6 0.0413(14) 0.0404(13) 0.0435(15) 0.0202(12) 0.0049(11) 0.0099(11)
  C7 0.0397(14) 0.0418(14) 0.0368(13) 0.0187(12) 0.0040(10) 0.0120(10)
  C8 0.0499(16) 0.0441(15) 0.0412(15) 0.0137(13) 0.0006(12) 0.0126(12)
  C9 0.0527(16) 0.0422(14) 0.0324(14) 0.0066(13) -0.0029(11) 0.0119(10)
  C10 0.0613(19) 0.0579(17) 0.0459(17) 0.0184(15) 0.0046(14) 0.0146(13)
  C11 0.073(2) 0.068(2) 0.0423(17) 0.0146(17) 0.0138(15) 0.0124(14)
  C12 0.074(2) 0.0605(18) 0.0366(16) 0.0059(16) -0.0028(14) 0.0185(13)
  C13 0.0586(18) 0.0445(15) 0.0438(16) 0.0044(13) -0.0084(13) 0.0157(12)
  C14 0.080(2) 0.064(2) 0.069(2) 0.0171(18) -0.0193(18) 0.0287(17)
  C15 0.074(3) 0.080(2) 0.104(3) 0.032(2) -0.013(2) 0.030(2)
  C16 0.066(2) 0.083(2) 0.093(3) 0.033(2) 0.0063(19) 0.017(2)
  C17 0.060(2) 0.0660(19) 0.0534(18) 0.0169(16) -0.0002(14) 0.0155(14)
  C18 0.0479(16) 0.0405(14) 0.0390(14) 0.0034(12) -0.0041(12) 0.0105(11)
  O3 0.171(3) 0.092(2) 0.128(3) 0.064(2) -0.003(2) 0.0416(18)
  C19 0.099(3) 0.074(2) 0.077(2) 0.036(2) 0.012(2) 0.0149(18)
  C20 0.067(2) 0.065(2) 0.065(2) 0.0207(17) -0.0143(16) 0.0112(16)
  C21 0.109(4) 0.122(4) 0.079(3) 0.000(3) 0.024(2) 0.005(3)
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 C3 . 1.716(3) y
  Cl2 C4 . 1.715(2) y
  Cl3 C5 . 1.713(2) y
  Cl4 C6 . 1.715(3) y
  O1 C1 . 1.190(3) y
  O2 C8 . 1.192(3) y
  N1 C1 . 1.394(3) y
  N1 C8 . 1.396(3) y
  N1 C9 . 1.441(3) y
  C1 C2 . 1.494(3) ?
  C2 C7 . 1.379(3) ?
  C2 C3 . 1.381(3) ?
  C3 C4 . 1.394(3) ?
  C4 C5 . 1.398(4) ?
  C5 C6 . 1.400(3) ?
  C6 C7 . 1.376(3) ?
  C7 C8 . 1.497(3) ?
  C9 C10 . 1.353(4) ?
  C9 C18 . 1.414(4) ?
  C10 C11 . 1.407(4) ?
  C10 H10 . 0.93 ?
  C11 C12 . 1.352(5) ?
  C11 H11 . 0.93 ?
  C12 C13 . 1.403(4) ?
  C12 H12 . 0.93 ?
  C13 C14 . 1.412(5) ?
  C13 C18 . 1.429(4) ?
  C14 C15 . 1.352(5) ?
  C14 H14 . 0.93 ?
  C15 C16 . 1.399(5) ?
  C15 H15 . 0.93 ?
  C16 C17 . 1.369(4) ?
  C16 H16 . 0.93 ?
  C17 C18 . 1.399(4) ?
  C17 H17 . 0.93 ?
  O3 C20 . 1.206(4) y
  C19 C20 . 1.474(5) y
  C19 H19A . 0.96 ?
  C19 H19B . 0.96 ?
  C19 H19C . 0.96 ?
  C20 C21 . 1.478(5) y
  C21 H21A . 0.96 ?
  C21 H21B . 0.96 ?
  C21 H21C . 0.96 ?