#------------------------------------------------------------------------------
#$Date: 2012-01-03 17:39:29 +0000 (Tue, 03 Jan 2012) $
#$Revision: 31972 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006580.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_2006580
loop_
_publ_author_name
'Johannes, Hans-Hermann'
'Grahn, Walter'
'Dix, Ina'
'Jones, Peter G.'
_publ_section_title
;
5-Iodo-2-[iodo(5-iodo-1,3,3-trimethyl-2-indolinylidene)methyl]-
1,3,3-trimethyl-3H-indolium Perchlorate:
a Highly Overcrowded Cyanine Dye
;
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1432
_journal_page_last               1434
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C23 H24 I3 N2 1+, Cl O4 1-'
_chemical_formula_sum            'C23 H24 Cl I3 N2 O4'
_chemical_formula_weight         808.59
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.30(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.448(2)
_cell_length_b                   12.098(2)
_cell_length_c                   19.305(3)
_cell_measurement_temperature    143(2)
_cell_volume                     2566.4(7)
_diffrn_ambient_temperature      143(2)
_exptl_crystal_density_diffrn    2.093
_refine_ls_R_factor_obs          .0286
_refine_ls_wR_factor_obs         .0558
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2006580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
I1 .03118(18) .02225(17) .02336(17) .00419(14) .00768(13) -.00327(13)
I2 .02809(17) .02717(17) .01905(16) -.00093(14) .00772(13) .00364(13)
I3 .02666(17) .02723(17) .01974(16) .00133(14) .00873(13) -.00035(13)
N1 .020(2) .019(2) .0154(19) .0017(16) .0066(16) -.0012(16)
N1' .019(2) .018(2) .019(2) -.0028(16) .0059(16) .0000(16)
C2 .016(2) .016(2) .017(2) -.0045(18) .0040(19) -.0051(18)
C2' .015(2) .017(2) .025(2) .0024(18) .0087(19) .0013(19)
C3 .022(2) .026(3) .016(2) .001(2) .010(2) .003(2)
C3' .021(2) .016(2) .022(2) .0006(19) .005(2) .0020(19)
C4 .027(3) .025(3) .014(2) -.007(2) .009(2) -.002(2)
C4' .023(2) .011(2) .030(3) -.0005(19) .010(2) .001(2)
C5 .018(2) .024(2) .016(2) -.002(2) .0045(19) .0014(19)
C5' .021(2) .029(3) .017(2) .006(2) .004(2) .003(2)
C6 .019(2) .021(2) .025(3) -.004(2) .006(2) .000(2)
C6' .023(2) .016(2) .027(3) -.001(2) .006(2) -.007(2)
C7 .027(3) .022(3) .016(2) -.001(2) .006(2) -.0017(19)
C7' .021(2) .020(2) .028(3) .002(2) .007(2) .001(2)
C8 .020(2) .020(2) .016(2) -.004(2) .0035(19) -.0012(19)
C8' .014(2) .022(2) .017(2) .0010(19) .0044(18) .0033(19)
C9 .018(2) .023(3) .021(2) -.008(2) .0064(19) -.006(2)
C9' .016(2) .024(2) .018(2) .0031(19) .0054(19) -.0014(19)
C10 .021(2) .019(2) .024(2) -.001(2) .010(2) -.006(2)
C11 .026(3) .028(3) .023(2) .004(2) .014(2) .001(2)
C11' .028(3) .027(3) .023(3) -.013(2) .009(2) .000(2)
C12 .043(3) .027(3) .018(3) .002(2) .007(2) -.005(2)
C12' .032(3) .017(2) .026(3) .008(2) .009(2) -.001(2)
C13 .022(3) .040(3) .030(3) .003(2) .013(2) .006(2)
C13' .031(3) .025(3) .026(3) -.005(2) .011(2) -.003(2)
Cl .0467(8) .0270(7) .0270(7) .0055(6) .0141(6) .0027(5)
O1 .086(4) .071(3) .044(3) .025(3) .001(3) .024(2)
O2 .100(4) .092(4) .053(3) -.037(3) .037(3) .001(3)
O3 .118(5) .106(5) .069(4) .077(4) .043(3) .021(3)
O4 .109(5) .059(3) .099(4) -.033(3) .012(4) -.024(3)
loop_
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
I1 .70025(3) .71656(3) .366676(17) .02559(9) Uani d . 1 . I
I2 .99492(3) .10332(3) .638937(16) .02455(9) Uani d . 1 . I
I3 .68285(3) .48954(3) -.092631(16) .02409(9) Uani d . 1 . I
N1 .8497(3) .3937(3) .36337(19) .0180(8) Uani d . 1 . N
N1' .6535(3) .4459(3) .22268(19) .0186(8) Uani d . 1 . N
C2 .7798(4) .4760(4) .3787(2) .0164(9) Uani d . 1 . C
C2' .6966(4) .5433(4) .2537(2) .0182(10) Uani d . 1 . C
C3 .7693(4) .4563(4) .4560(2) .0203(10) Uani d . 1 . C
C3' .7074(4) .6234(4) .1932(2) .0196(10) Uani d . 1 . C
C4 .8705(4) .2906(4) .5398(2) .0214(10) Uani d . 1 . C
H4 .8430 .3129 .5797 .026 Uiso calc R 1 . H
C4' .6892(4) .5625(4) .0597(3) .0209(10) Uani d . 1 . C
H4' .7106 .6327 .0448 .025 Uiso calc R 1 . H
C5 .9429(4) .1969(4) .5438(2) .0193(10) Uani d . 1 . C
C5' .6623(4) .4738(4) .0117(2) .0223(10) Uani d . 1 . C
C6 .9835(4) .1628(4) .4860(2) .0217(10) Uani d . 1 . C
H6 1.0317 .0979 .4901 .026 Uiso calc R 1 . H
C6' .6281(4) .3717(4) .0322(3) .0222(10) Uani d . 1 . C
H6' .6090 .3129 -.0018 .027 Uiso calc R 1 . H
C7 .9543(4) .2228(4) .4226(2) .0218(10) Uani d . 1 . C
H7 .9817 .2007 .3826 .026 Uiso calc R 1 . H
C7' .6216(4) .3548(4) .1025(3) .0229(10) Uani d . 1 . C
H7' .5982 .2855 .1175 .027 Uiso calc R 1 . H
C8 .8840(4) .3156(4) .4196(2) .0193(10) Uani d . 1 . C
C8' .6505(4) .4429(4) .1488(2) .0178(10) Uani d . 1 . C
C9 .8399(4) .3498(4) .4764(2) .0208(10) Uani d . 1 . C
C9' .6837(4) .5455(4) .1291(2) .0189(10) Uani d . 1 . C
C10 .7283(4) .5575(4) .3286(2) .0205(10) Uani d . 1 . C
C11 .9043(4) .3911(4) .3040(2) .0245(11) Uani d . 1 . C
H11A .8573 .3415 .2662 .029 Uiso calc R 1 . H
H11B .9882 .3642 .3214 .029 Uiso calc R 1 . H
H11C .9042 .4657 .2842 .029 Uiso calc R 1 . H
C11' .6047(4) .3559(4) .2563(3) .0258(11) Uani d . 1 . C
H11D .6702 .3041 .2787 .031 Uiso calc R 1 . H
H11E .5413 .3172 .2196 .031 Uiso calc R 1 . H
H11F .5698 .3859 .2933 .031 Uiso calc R 1 . H
C12 .8311(5) .5465(4) .5115(2) .0297(12) Uani d . 1 . C
H12A .8446 .5176 .5605 .036 Uiso calc R 1 . H
H12B .7785 .6117 .5050 .036 Uiso calc R 1 . H
H12C .9094 .5669 .5038 .036 Uiso calc R 1 . H
C12' .6082(4) .7137(4) .1767(3) .0251(11) Uani d . 1 . C
H12D .6037 .7479 .1300 .030 Uiso calc R 1 . H
H12E .6285 .7702 .2146 .030 Uiso calc R 1 . H
H12F .5294 .6805 .1750 .030 Uiso calc R 1 . H
C13 .6359(4) .4427(4) .4543(3) .0296(12) Uani d . 1 . C
H13A .6001 .3814 .4221 .036 Uiso calc R 1 . H
H13B .5915 .5110 .4366 .036 Uiso calc R 1 . H
H13C .6304 .4269 .5031 .036 Uiso calc R 1 . H
C13' .8348(4) .6770(4) .2100(3) .0268(11) Uani d . 1 . C
H13D .8960 .6196 .2117 .032 Uiso calc R 1 . H
H13E .8530 .7147 .2567 .032 Uiso calc R 1 . H
H13F .8363 .7306 .1722 .032 Uiso calc R 1 . H
Cl .73957(13) .04994(11) .20830(7) .0328(3) Uani d . 1 . Cl
O1 .6689(5) .0891(4) .1404(2) .0702(15) Uani d . 1 . O
O2 .6659(5) -.0086(5) .2437(3) .0785(17) Uani d . 1 . O
O3 .8317(6) -.0219(5) .1992(3) .094(2) Uani d . 1 . O
O4 .7931(6) .1402(4) .2519(3) .0925(19) Uani d . 1 . O
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
I1 C10 . 2.116(4) y
I2 C5 . 2.097(4) y
I3 C5' . 2.101(5) y
N1 C2 . 1.360(6) y
N1 C8 . 1.409(6) ?
N1 C11 . 1.452(5) y
N1' C2' . 1.351(6) y
N1' C8' . 1.418(6) ?
N1' C11' . 1.457(6) y
C2 C10 . 1.392(6) y
C2 C3 . 1.550(6) ?
C2' C10 . 1.398(6) y
C2' C3' . 1.550(6) ?
C3 C9 . 1.514(6) ?
C3 C13 . 1.527(6) ?
C3 C12 . 1.553(6) ?
C3' C9' . 1.518(6) ?
C3' C12' . 1.544(6) ?
C3' C13' . 1.546(6) ?
C4 C9 . 1.376(6) ?
C4 C5 . 1.393(6) ?
C4' C9' . 1.375(6) ?
C4' C5' . 1.394(6) ?
C5 C6 . 1.386(6) ?
C5' C6' . 1.388(7) ?
C6 C7 . 1.382(6) ?
C6' C7' . 1.394(7) ?
C7 C8 . 1.374(6) ?
C7' C8' . 1.371(6) ?
C8 C9 . 1.392(6) ?
C8' C9' . 1.382(6) ?
Cl O4 . 1.410(5) ?
Cl O1 . 1.415(4) ?
Cl O2 . 1.415(5) ?
Cl O3 . 1.415(5) ?