#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/8/8101646.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_8101646
_journal_name_full  'Zeitschrift fur Kristallographie - NCS'
_journal_year       1998
_publ_section_title
;
Crystal structure of 5-(iodomethyl)-3-(5-iodo-7oxabicyclo[4.3.0]non-
8-ylidene)oxolan-2-one, C~13~ H~16~ I~2~ O~2~
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
loop_
_publ_author_name
  'Zukerman-Schpector, J.'
  'Stefani, A. Helio'
  'Valduga, Claud\'ete I.'
  'Brandt, Carlos A.'
  'Caracelli, I.'
_chemical_formula_moiety  'C13 H16 I2 O3'
_chemical_formula_sum  'C13 H16 I2 O3'
_chemical_formula_weight  474.06
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z'
_cell_length_a  9.246(1)
_cell_length_b  12.879(1)
_cell_length_c  13.404(3)
_cell_angle_alpha  90.00
_cell_angle_beta  106.66(1)
_cell_angle_gamma  90.00
_cell_volume  1529.1(4)
_cell_formula_units_Z  4
_exptl_crystal_density_diffrn  2.059
_diffrn_ambient_temperature  191(1)
_refine_ls_R_factor_obs  0.0565
_refine_ls_wR_factor_obs  0.1274
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
I1 I 0.67855(11) 0.37626(8) 0.12600(8) 0.0677(4) Uani 1 d . .
I2 I 1.40964(12) 0.33204(8) 0.82155(7) 0.0747(4) Uani 1 d . .
O1 O 0.8140(8) 0.2361(6) 0.3412(6) 0.048(2) Uani 1 d . .
O2 O 1.2603(9) 0.1968(7) 0.5995(7) 0.065(3) Uani 1 d . .
O3 O 1.2171(9) 0.0607(8) 0.4943(7) 0.060(2) Uani 1 d . .
C1 C 0.7359(13) 0.2139(10) 0.1566(9) 0.046(3) Uani 1 d . .
H1 H 0.8437(13) 0.2048(10) 0.1640(9) 0.055 Uiso 1 calc R .
C2 C 0.6459(15) 0.1461(11) 0.0664(9) 0.058(4) Uani 1 d . .
H2A H 0.6609(15) 0.1699(11) 0.0014(9) 0.069 Uiso 1 calc R .
H2B H 0.5390(15) 0.1500(11) 0.0607(9) 0.069 Uiso 1 calc R .
C3 C 0.7027(15) 0.0334(13) 0.0891(11) 0.074(5) Uani 1 d . .
H3A H 0.6478(15) -0.0117(13) 0.0330(11) 0.089 Uiso 1 calc R .
H3B H 0.8090(15) 0.0298(13) 0.0933(11) 0.089 Uiso 1 calc R .
C4 C 0.6790(14) -0.0023(12) 0.1913(12) 0.068(4) Uani 1 d . .
H4A H 0.5716(14) -0.0114(12) 0.1808(12) 0.082 Uiso 1 calc R .
H4B H 0.7262(14) -0.0697(12) 0.2083(12) 0.082 Uiso 1 calc R .
C5 C 0.7390(12) 0.0684(9) 0.2835(9) 0.046(3) Uani 1 d . .
H5 H 0.6913(12) 0.0492(9) 0.3374(9) 0.055 Uiso 1 calc R .
C6 C 0.7065(13) 0.1839(9) 0.2567(8) 0.042(3) Uani 1 d . .
H6 H 0.6029(13) 0.2016(9) 0.2556(8) 0.051 Uiso 1 calc R .
C7 C 0.9097(13) 0.0691(10) 0.3322(9) 0.052(3) Uani 1 d . .
H7A H 0.9415(13) 0.0133(10) 0.3824(9) 0.062 Uiso 1 calc R .
H7B H 0.9624(13) 0.0629(10) 0.2795(9) 0.062 Uiso 1 calc R .
C8 C 0.9362(12) 0.1727(10) 0.3840(9) 0.043(3) Uani 1 d . .
C9 C 1.0535(12) 0.2089(10) 0.4602(8) 0.040(3) Uani 1 d . .
C10 C 1.1774(13) 0.1450(11) 0.5138(10) 0.047(3) Uani 1 d . .
C11 C 1.1843(19) 0.2900(15) 0.6135(13) 0.107(7) Uani 1 d . .
H11 H 1.1217(19) 0.2669(15) 0.6572(13) 0.128 Uiso 1 calc R .
C12 C 1.0655(13) 0.3131(10) 0.5077(9) 0.052(3) Uani 1 d . .
H12A H 0.9702(13) 0.3360(10) 0.5168(9) 0.063 Uiso 1 calc R .
H12B H 1.1017(13) 0.3643(10) 0.4674(9) 0.063 Uiso 1 calc R .
C13 C 1.2667(29) 0.3633(13) 0.6699(14) 0.159(12) Uani 1 d . .
H13A H 1.1984(29) 0.4183(13) 0.6765(14) 0.190 Uiso 1 calc R .
H13B H 1.3298(29) 0.3914(13) 0.6298(14) 0.190 Uiso 1 calc R .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0650(6) 0.0646(7) 0.0715(7) 0.0176(5) 0.0163(5) 0.0051(5)
I2 0.0871(8) 0.0629(7) 0.0548(6) -0.0025(5) -0.0103(5) -0.0002(5)
O1 0.044(5) 0.054(5) 0.040(4) -0.009(4) 0.000(4) 0.003(4)
O2 0.047(5) 0.076(7) 0.060(6) -0.014(5) -0.005(5) 0.012(5)
O3 0.046(5) 0.064(7) 0.066(6) 0.005(5) 0.010(4) 0.004(5)
C1 0.038(7) 0.055(8) 0.039(7) -0.004(6) 0.003(5) -0.003(6)
C2 0.060(8) 0.076(10) 0.034(7) -0.013(7) 0.009(6) -0.007(7)
C3 0.045(8) 0.110(14) 0.062(9) -0.049(9) 0.007(7) 0.002(8)
C4 0.037(8) 0.069(10) 0.092(11) -0.024(9) 0.007(7) -0.002(7)
C5 0.037(7) 0.050(8) 0.052(7) -0.003(6) 0.015(6) -0.003(6)
C6 0.034(6) 0.056(8) 0.033(6) -0.008(6) 0.003(5) -0.005(6)
C7 0.061(8) 0.052(9) 0.047(7) 0.005(7) 0.024(6) 0.001(7)
C8 0.025(6) 0.057(8) 0.048(7) 0.014(6) 0.013(5) 0.012(6)
C9 0.034(7) 0.054(8) 0.032(6) 0.002(6) 0.010(5) 0.001(6)
C10 0.036(7) 0.058(10) 0.049(8) 0.005(7) 0.012(6) -0.002(6)
C11 0.085(12) 0.121(15) 0.082(12) -0.053(11) -0.029(9) 0.052(11)
C12 0.039(7) 0.066(10) 0.046(7) -0.007(7) 0.002(6) -0.003(6)
C13 0.227(26) 0.070(12) 0.090(14) -0.010(10) -0.097(16) 0.020(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C1 2.168(13)  no
I2 C13 2.122(15)  no
O1 C8 1.379(13)  no
O1 C6 1.442(12)  no
O2 C10 1.360(14)  no
O2 C11 1.43(2)  no
O3 C10 1.198(14)  no
C1 C6 1.49(2)  no
C1 C2 1.53(2)  no
C2 C3 1.54(2)  no
C3 C4 1.52(2)  no
C4 C5 1.51(2)  no
C5 C7 1.52(2)  no
C5 C6 1.54(2)  no
C7 C8 1.49(2)  no
C8 C9 1.34(2)  no
C9 C10 1.43(2)  no
C9 C12 1.48(2)  no
C11 C13 1.31(2)  no
C11 C12 1.55(2)  no
_cod_database_code 8101646