Diethyl 5-amino-2,4,6-triiodo­isophthalate

Wu, J.; Xie, M.-H.; Zou, P.; Liu, Y.-L.; He, Y.-J.

doi:10.1107/S1600536809051149

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o10-o11

doi:10.1107/S1600536809051149

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access

Diethyl 5-amino-2,4,6-triiodoisophthalate

Jun Wu,^a Min-Hao Xie,^a ^* Pei Zou,^a Ya-Ling Liu ^a and Yong-Jun He ^a

^aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: wujunnju@hotmail.com

(Received 26 October 2009; accepted 27 November 2009; online 4 December 2009)

The title compound, C₁₂H₁₂I₃NO₄, crystallizes with two molecules in an asymmetric unit. In one of the molecules, the conformation of the O—C—O—C in one ester group is cis and trans in the other. The corresponding conformations for both the ester groups in the other molecule are trans. The I atoms and the benzene rings in the two molecules are approximately coplanar, the I atoms deviating by 0.219 (14), 0.056 (15) and −0.143 (14) Å from the mean plane of the benzene ring in one molecule and 0.189 (14), −0.162 (15) and −0.068 (14) Å in the other. The planes of the ester groups are almost orthogonal to those of the benzene rings in both molecules, forming dihedral angles of 88.1 (4), 72.2 (4), 73.0 (4) and 86.6 (4)°. The mean planes of the benzene rings in the two molecules are inclined at 74.6 (4)° with respect to each other. In the crystal, intermolecular I⋯O interactions [3.138 (7) and 3.144 (7) Å] link the molecules into infinite chains along the a axis. In addition, non-classical C—H⋯O hydrogen bonds are observed.

Related literature

For iodine-based compounds as contrast agents for X-ray imaging, see: Stacul, (2001 ); Yu & Watson (1999 ); Tonnessen et al. (1996 ). For a related structure, see: Beck & Sheldrick (2008 ).

Experimental

Crystal data

C₁₂H₁₂I₃NO₄
M_r = 614.93
Monoclinic, P 2₁ /n
a = 9.7410 (8) Å
b = 9.6870 (7) Å
c = 37.7290 (15) Å
β = 94.430 (3)°
V = 3549.5 (4) Å³
Z = 8
Mo Kα radiation
μ = 5.29 mm⁻¹
T = 296 K
0.26 × 0.18 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989 ) T_min = 0.362, T_max = 0.528
6676 measured reflections
6281 independent reflections
4259 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.162
S = 1.06
6222 reflections
365 parameters
84 restraints
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2A2⋯O2Aⁱ	0.97	2.54	3.411 (8)	150
C12A—H12A⋯O2Bⁱⁱ	0.96	2.60	3.545 (11)	169
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051149/pv2229sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051149/pv2229Isup2.hkl

checkCIF report

Comment top

Iodine-based compounds have been in the focus as contrast agents for X-ray imaging (Stacul, 2001). The 1,3,5-triiodobenzene core has been the basis of many contrast agents (Yu & Watson, 1999). The ionic monomer, diatrizoate was one of the first X-ray contrast agents in clinical use based on triiodinated benzene (Tonnessen et al., 1996). In this paper, we present the crystal structure of the title compound, (I).

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules (A, B) in an asymmetric unit. The three I atoms deviate from the mean-planes of the the phenyl rings, respectively, by 0.219 (14), 0.056 (15) and -0.143 (14) Å for molecule A and 0.189 (14), -0.162 (15) and -0.068 (14) Å for molecule B. Bond lengths and angles are comparable to those observed in a related structure (Beck & Sheldrick, 2008). In molecule A, the conformation of the O–C–O–C is cis with respect to the O1A—C3A bond (torsion angle, -90.6 (8)°) and trans with respect to the O3A—C11A bond (torsion angle, 158.0 (8)°). On the other hand, the corresponding bonds exhibit trans conformations for both the ester groups with torsion angles about O1B—C3B and O3B—C11B bonds being 157.5 (8) and 177.5 (6) °, respectively. The planes of the ester groups in both molecule are almost orthogonal to the benzene rings, as indicated by the dihedral angles of 88.1 (4)° (O1A/O2A/C3A/C4A; C4A—C9A), 72.2 (4)° (O3A/O4A/C8A/C10A; C4A—C9A), 73.0 (4)° (O1B/O2B/C3B/C4B; C4B—C9B) and 86.6 (4)° (O3B/O4B/C8B/C10B/C11B/C12B; C4B—C9B). The dihedral angle between the ring (C4A—C9A) and the ring (C4B—C9B) is 74.6 (4)°.

In the crystal structure, intermolecular I···O interactions of the order 3.138 (7) and 3.144 (7) Å link the molecules into infinite one-dimensional chains along the a axis (Fig. 2). In addition, non-classical C—H···O hydrogen bonds are observed (Table 1).

Related literature top

For iodine-based compounds as contrast agents for X-ray imaging, see: Stacul, (2001); Yu & Watson (1999); Tonnessen et al. (1996). For a related structure, see: Beck & Sheldrick (2008).

Experimental top

A mixture of 5-amino-2,4,6-triiodoisophthaloyl dichloride (5.95 g, 10 mmol) and ethanol (30 ml) was heated under reflux for four hours to produce diethyl 5-amino-2,4,6-triiodoisophthalate. It was recrystallized from an ethanol solution by slowly evaporating the solvent to obtain crystals suitable for X-ray single-crystal diffraction.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the two molecules of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 50% probability level.
	Fig. 2. A view of the molecular structure of the title compound showing infinite one dimensional chains formed by I···O interactions (dashed lines).

Diethyl 5-amino-2,4,6-triiodoisophthalate top

Crystal data top

C₁₂H₁₂I₃NO₄	F(000) = 2256
M_r = 614.93	D_x = 2.301 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5986 reflections
a = 9.7410 (8) Å	θ = 3.2–25.2°
b = 9.6870 (7) Å	µ = 5.29 mm⁻¹
c = 37.7290 (15) Å	T = 296 K
β = 94.430 (3)°	Chunk, colorless
V = 3549.5 (4) Å³	0.26 × 0.18 × 0.12 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	4259 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.0°, θ_min = 1.1°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989)	k = 0→11
T_min = 0.362, T_max = 0.528	l = 0→43
6676 measured reflections	3 standard reflections every 200 reflections
6281 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.085P)² + 12.P] where P = (F_o² + 2F_c²)/3
6222 reflections	(Δ/σ)_max = 0.004
365 parameters	Δρ_max = 0.84 e Å⁻³
84 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

C₁₂H₁₂I₃NO₄	V = 3549.5 (4) Å³
M_r = 614.93	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7410 (8) Å	µ = 5.29 mm⁻¹
b = 9.6870 (7) Å	T = 296 K
c = 37.7290 (15) Å	0.26 × 0.18 × 0.12 mm
β = 94.430 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	4259 reflections with I > 2σ(I)
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989)	R_int = 0.045
T_min = 0.362, T_max = 0.528	3 standard reflections every 200 reflections
6676 measured reflections	intensity decay: 1%
6281 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	84 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.085P)² + 12.P] where P = (F_o² + 2F_c²)/3
6222 reflections	Δρ_max = 0.84 e Å⁻³
365 parameters	Δρ_min = −1.05 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1B	0.91907 (6)	0.24382 (7)	0.092312 (16)	0.04395 (16)
I1A	0.42314 (6)	0.32088 (7)	0.091767 (17)	0.04606 (17)
I3A	0.32374 (7)	0.63629 (7)	0.228910 (16)	0.04879 (18)
I2B	0.81984 (6)	−0.08251 (7)	0.227645 (16)	0.04797 (18)
I3B	0.50611 (7)	−0.22049 (8)	0.08379 (2)	0.0610 (2)
I2A	0.00810 (7)	0.78328 (8)	0.08607 (2)	0.0644 (2)
C7A	0.2827 (8)	0.6055 (9)	0.1725 (2)	0.031 (2)
O1A	0.2558 (6)	0.5972 (7)	0.03825 (7)	0.0469 (17)
O3B	0.7559 (6)	−0.0349 (7)	0.03756 (7)	0.0504 (18)
O1B	0.8887 (4)	0.2728 (4)	0.18292 (16)	0.0426 (17)
O4A	0.5601 (6)	0.4411 (6)	0.18705 (18)	0.0473 (18)
O3A	0.3932 (4)	0.2852 (4)	0.18200 (16)	0.0433 (17)
C3A	0.1782 (9)	0.5254 (10)	0.0593 (2)	0.042 (2)
O2B	1.0594 (6)	0.1144 (7)	0.18664 (19)	0.0493 (18)
O4B	0.5915 (7)	0.1160 (8)	0.04744 (18)	0.056 (2)
C5B	0.7797 (8)	−0.0506 (9)	0.1708 (2)	0.033 (2)
C10B	0.6797 (8)	0.0387 (9)	0.0585 (2)	0.031 (2)
O2A	0.0891 (6)	0.4496 (7)	0.04842 (18)	0.0550 (19)
C6A	0.1885 (8)	0.6946 (9)	0.1533 (2)	0.036 (2)
C5A	0.1544 (9)	0.6638 (9)	0.1165 (2)	0.036 (2)
C9B	0.8118 (7)	0.0883 (8)	0.11840 (19)	0.0262 (18)
N1B	0.6258 (8)	−0.2450 (8)	0.1678 (2)	0.050 (2)
H1B1	0.6454	−0.2589	0.1902	0.060*
H1B2	0.5685	−0.2985	0.1560	0.060*
C9A	0.3143 (8)	0.4725 (8)	0.1186 (2)	0.033 (2)
N1A	0.1263 (9)	0.8035 (8)	0.1696 (2)	0.056 (2)
H1A1	0.1446	0.8184	0.1919	0.068*
H1A2	0.0695	0.8562	0.1574	0.068*
C4A	0.2167 (7)	0.5527 (8)	0.0986 (2)	0.0280 (19)
C10A	0.4476 (8)	0.4076 (9)	0.1766 (2)	0.033 (2)
C4B	0.8418 (8)	0.0606 (8)	0.1547 (2)	0.030 (2)
C7B	0.6511 (8)	−0.1024 (9)	0.1146 (2)	0.037 (2)
C6B	0.6866 (8)	−0.1361 (8)	0.1508 (3)	0.038 (2)
C8A	0.3445 (7)	0.4994 (9)	0.1557 (2)	0.031 (2)
C12A	0.4169 (10)	0.0442 (10)	0.1878 (3)	0.055 (3)
H12A	0.3197	0.0535	0.1898	0.066*
H12B	0.4525	−0.0283	0.2032	0.066*
H12C	0.4331	0.0219	0.1637	0.066*
C3B	0.9446 (9)	0.1487 (9)	0.1769 (2)	0.036 (2)
C8B	0.7160 (8)	0.0048 (9)	0.0982 (2)	0.034 (2)
C2A	0.2210 (5)	0.5890 (6)	−0.00099 (8)	0.066 (3)
H2A1	0.2434	0.6767	−0.0115	0.079*
H2A2	0.1224	0.5756	−0.0053	0.079*
C11A	0.4865 (7)	0.1753 (7)	0.1980 (3)	0.059 (3)
H11A	0.5762	0.1802	0.1885	0.071*
H11B	0.4980	0.1847	0.2236	0.071*
C1A	0.2940 (11)	0.4747 (10)	−0.0198 (3)	0.079 (6)
H1A3	0.3820	0.5074	−0.0261	0.095*
H1A4	0.2392	0.4482	−0.0410	0.095*
H1A5	0.3068	0.3964	−0.0043	0.095*
C11B	0.7246 (4)	−0.0172 (6)	−0.00162 (7)	0.075 (4)
H11C	0.7324	0.0796	−0.0077	0.090*
H11D	0.6306	−0.0460	−0.0081	0.090*
C2B	0.9858 (5)	0.3800 (3)	0.1986 (2)	0.055 (3)
H2B1	1.0744	0.3733	0.1886	0.066*
H2B2	0.9993	0.3697	0.2242	0.066*
C12B	0.82239 (15)	−0.1014 (4)	−0.02254 (14)	0.091 (4)
H12D	0.9144	−0.0669	−0.0180	0.109*
H12E	0.7952	−0.0942	−0.0475	0.109*
H12F	0.8192	−0.1964	−0.0154	0.109*
C1B	0.9166 (8)	0.5171 (5)	0.1888 (3)	0.065 (3)
H1B3	0.9270	0.5371	0.1642	0.078*
H1B4	0.9587	0.5891	0.2034	0.078*
H1B5	0.8205	0.5115	0.1926	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1B	0.0448 (3)	0.0435 (4)	0.0429 (3)	−0.0117 (3)	−0.0009 (3)	0.0084 (3)
I1A	0.0493 (4)	0.0430 (4)	0.0450 (3)	0.0190 (3)	−0.0021 (3)	−0.0076 (3)
I3A	0.0498 (4)	0.0544 (4)	0.0417 (3)	−0.0005 (3)	0.0010 (3)	−0.0106 (3)
I2B	0.0499 (4)	0.0517 (4)	0.0420 (3)	0.0022 (3)	0.0012 (3)	0.0126 (3)
I3B	0.0494 (4)	0.0581 (5)	0.0734 (5)	−0.0217 (3)	−0.0083 (3)	−0.0128 (4)
I2A	0.0537 (4)	0.0603 (5)	0.0769 (5)	0.0315 (3)	−0.0088 (4)	0.0136 (4)
C7A	0.025 (4)	0.036 (5)	0.033 (4)	−0.012 (4)	−0.002 (3)	−0.003 (4)
O1A	0.042 (3)	0.059 (4)	0.038 (3)	−0.001 (3)	−0.003 (3)	0.011 (3)
O3B	0.047 (3)	0.066 (4)	0.036 (3)	0.023 (3)	−0.006 (3)	−0.013 (3)
O1B	0.028 (3)	0.027 (3)	0.072 (4)	−0.001 (3)	−0.003 (3)	−0.007 (3)
O4A	0.030 (3)	0.044 (4)	0.065 (4)	−0.007 (3)	−0.010 (3)	0.003 (3)
O3A	0.033 (3)	0.036 (4)	0.060 (4)	0.007 (3)	−0.002 (3)	0.018 (3)
C3A	0.037 (5)	0.036 (5)	0.050 (6)	0.012 (4)	−0.012 (4)	0.004 (4)
O2B	0.024 (3)	0.044 (4)	0.078 (5)	0.002 (3)	−0.014 (3)	0.007 (4)
O4B	0.057 (4)	0.060 (4)	0.048 (4)	0.012 (4)	−0.018 (3)	−0.004 (4)
C5B	0.031 (4)	0.036 (5)	0.030 (4)	−0.001 (4)	−0.005 (3)	0.010 (4)
C10B	0.027 (4)	0.033 (5)	0.034 (4)	0.007 (4)	−0.002 (3)	−0.002 (4)
O2A	0.046 (4)	0.054 (4)	0.061 (4)	−0.018 (3)	−0.014 (3)	0.002 (4)
C6A	0.022 (4)	0.030 (5)	0.056 (6)	0.006 (4)	0.004 (4)	−0.013 (4)
C5A	0.037 (5)	0.028 (4)	0.042 (5)	0.014 (4)	−0.001 (4)	0.012 (4)
C9B	0.020 (4)	0.035 (5)	0.024 (4)	−0.002 (3)	0.004 (3)	−0.004 (3)
N1B	0.046 (5)	0.037 (4)	0.069 (5)	−0.018 (4)	0.011 (4)	0.006 (4)
C9A	0.026 (4)	0.018 (4)	0.056 (5)	0.008 (3)	0.000 (4)	0.000 (4)
N1A	0.057 (5)	0.041 (5)	0.071 (6)	0.011 (4)	0.003 (4)	−0.014 (4)
C4A	0.018 (4)	0.029 (4)	0.037 (4)	−0.001 (3)	−0.001 (3)	0.004 (4)
C10A	0.029 (4)	0.027 (5)	0.040 (5)	0.006 (4)	−0.004 (4)	−0.001 (4)
C4B	0.023 (4)	0.021 (4)	0.047 (5)	0.005 (3)	−0.002 (3)	0.004 (4)
C7B	0.018 (4)	0.043 (5)	0.049 (5)	0.002 (4)	−0.005 (4)	−0.013 (4)
C6B	0.026 (4)	0.022 (5)	0.066 (6)	0.003 (3)	0.006 (4)	0.001 (4)
C8A	0.022 (4)	0.036 (5)	0.033 (4)	0.002 (3)	−0.001 (3)	0.009 (4)
C12A	0.051 (5)	0.041 (5)	0.074 (6)	0.014 (4)	0.018 (5)	−0.003 (5)
C3B	0.036 (5)	0.031 (5)	0.041 (5)	−0.003 (4)	0.002 (4)	0.002 (4)
C8B	0.035 (4)	0.030 (5)	0.035 (5)	0.004 (4)	−0.007 (4)	0.005 (4)
C2A	0.077 (7)	0.085 (7)	0.031 (5)	−0.010 (6)	−0.016 (5)	0.022 (5)
C11A	0.047 (5)	0.040 (5)	0.086 (7)	0.014 (4)	−0.014 (5)	0.003 (5)
C1A	0.059 (11)	0.052 (11)	0.110 (10)	0.007 (9)	0.001 (9)	−0.008 (9)
C11B	0.078 (7)	0.081 (8)	0.064 (7)	0.022 (6)	−0.005 (5)	−0.003 (6)
C2B	0.040 (5)	0.035 (5)	0.086 (7)	−0.008 (4)	−0.011 (5)	−0.021 (5)
C12B	0.105 (9)	0.102 (9)	0.068 (7)	0.002 (7)	0.030 (6)	−0.015 (7)
C1B	0.058 (6)	0.048 (6)	0.090 (7)	−0.001 (5)	0.021 (5)	0.001 (6)

Geometric parameters (Å, º) top

I1B—C9B	2.119 (8)	C9A—C4A	1.403 (10)
I1A—C9A	2.115 (8)	C9A—C8A	1.433 (11)
I3A—C7A	2.156 (8)	N1A—H1A1	0.8600
I2B—C5B	2.171 (8)	N1A—H1A2	0.8600
I3B—C7B	2.098 (8)	C10A—C8A	1.515 (11)
I2A—C5A	2.107 (8)	C4B—C3B	1.517 (11)
C7A—C8A	1.370 (12)	C7B—C8B	1.386 (12)
C7A—C6A	1.418 (11)	C7B—C6B	1.421 (13)
O1A—C3A	1.334 (11)	C12A—C11A	1.477 (12)
O1A—C2A	1.495 (4)	C12A—H12A	0.9600
O3B—C10B	1.333 (9)	C12A—H12B	0.9600
O3B—C11B	1.496 (4)	C12A—H12C	0.9600
O1B—C3B	1.347 (9)	C2A—C1A	1.521 (12)
O1B—C2B	1.496 (6)	C2A—H2A1	0.9700
O4A—C10A	1.182 (9)	C2A—H2A2	0.9700
O3A—C10A	1.321 (9)	C11A—H11A	0.9700
O3A—C11A	1.495 (9)	C11A—H11B	0.9700
C3A—O2A	1.186 (10)	C1A—H1A3	0.9600
C3A—C4A	1.521 (12)	C1A—H1A4	0.9600
O2B—C3B	1.197 (10)	C1A—H1A5	0.9600
O4B—C10B	1.191 (10)	C11B—C12B	1.521 (6)
C5B—C4B	1.397 (11)	C11B—H11C	0.9700
C5B—C6B	1.405 (12)	C11B—H11D	0.9700
C10B—C8B	1.547 (11)	C2B—C1B	1.522 (7)
C6A—N1A	1.384 (11)	C2B—H2B1	0.9700
C6A—C5A	1.432 (12)	C2B—H2B2	0.9700
C5A—C4A	1.431 (11)	C12B—H12D	0.9600
C9B—C4B	1.405 (11)	C12B—H12E	0.9600
C9B—C8B	1.412 (11)	C12B—H12F	0.9600
N1B—C6B	1.390 (11)	C1B—H1B3	0.9600
N1B—H1B1	0.8600	C1B—H1B4	0.9600
N1B—H1B2	0.8600	C1B—H1B5	0.9600

C8A—C7A—C6A	120.7 (7)	C11A—C12A—H12B	109.5
C8A—C7A—I3A	120.3 (6)	H12A—C12A—H12B	109.5
C6A—C7A—I3A	119.0 (6)	C11A—C12A—H12C	109.5
C3A—O1A—C2A	117.8 (6)	H12A—C12A—H12C	109.5
C10B—O3B—C11B	116.3 (5)	H12B—C12A—H12C	109.5
C3B—O1B—C2B	115.8 (5)	O2B—C3B—O1B	125.2 (8)
C10A—O3A—C11A	117.6 (5)	O2B—C3B—C4B	125.1 (8)
O2A—C3A—O1A	123.3 (8)	O1B—C3B—C4B	109.7 (6)
O2A—C3A—C4A	124.3 (9)	C7B—C8B—C9B	119.5 (7)
O1A—C3A—C4A	112.4 (7)	C7B—C8B—C10B	120.9 (7)
C4B—C5B—C6B	120.3 (8)	C9B—C8B—C10B	119.5 (7)
C4B—C5B—I2B	119.2 (6)	O1A—C2A—C1A	115.0 (7)
C6B—C5B—I2B	120.4 (6)	O1A—C2A—H2A1	108.5
O4B—C10B—O3B	123.3 (7)	C1A—C2A—H2A1	108.5
O4B—C10B—C8B	125.3 (8)	O1A—C2A—H2A2	108.5
O3B—C10B—C8B	111.4 (6)	C1A—C2A—H2A2	108.5
N1A—C6A—C7A	121.6 (8)	H2A1—C2A—H2A2	107.5
N1A—C6A—C5A	120.9 (8)	C12A—C11A—O3A	104.8 (6)
C7A—C6A—C5A	117.4 (7)	C12A—C11A—H11A	110.8
C4A—C5A—C6A	122.7 (7)	O3A—C11A—H11A	110.8
C4A—C5A—I2A	116.6 (6)	C12A—C11A—H11B	110.8
C6A—C5A—I2A	120.7 (6)	O3A—C11A—H11B	110.8
C4B—C9B—C8B	119.7 (7)	H11A—C11A—H11B	108.9
C4B—C9B—I1B	121.0 (5)	C2A—C1A—H1A3	109.5
C8B—C9B—I1B	119.0 (6)	C2A—C1A—H1A4	109.5
C6B—N1B—H1B1	120.0	H1A3—C1A—H1A4	109.5
C6B—N1B—H1B2	120.0	C2A—C1A—H1A5	109.5
H1B1—N1B—H1B2	120.0	H1A3—C1A—H1A5	109.5
C4A—C9A—C8A	120.4 (7)	H1A4—C1A—H1A5	109.5
C4A—C9A—I1A	118.1 (6)	O3B—C11B—C12B	111.3 (4)
C8A—C9A—I1A	121.4 (5)	O3B—C11B—H11C	109.4
C6A—N1A—H1A1	120.0	C12B—C11B—H11C	109.4
C6A—N1A—H1A2	120.0	O3B—C11B—H11D	109.4
H1A1—N1A—H1A2	120.0	C12B—C11B—H11D	109.4
C9A—C4A—C5A	117.1 (7)	H11C—C11B—H11D	108.0
C9A—C4A—C3A	122.2 (7)	O1B—C2B—C1B	104.8 (4)
C5A—C4A—C3A	120.7 (7)	O1B—C2B—H2B1	110.8
O4A—C10A—O3A	124.5 (7)	C1B—C2B—H2B1	110.8
O4A—C10A—C8A	125.0 (8)	O1B—C2B—H2B2	110.8
O3A—C10A—C8A	110.5 (6)	C1B—C2B—H2B2	110.8
C5B—C4B—C9B	120.5 (7)	H2B1—C2B—H2B2	108.9
C5B—C4B—C3B	118.9 (7)	C11B—C12B—H12D	109.5
C9B—C4B—C3B	120.6 (7)	C11B—C12B—H12E	109.5
C8B—C7B—C6B	121.1 (7)	H12D—C12B—H12E	109.5
C8B—C7B—I3B	118.1 (6)	C11B—C12B—H12F	109.5
C6B—C7B—I3B	120.7 (6)	H12D—C12B—H12F	109.5
N1B—C6B—C5B	118.7 (8)	H12E—C12B—H12F	109.5
N1B—C6B—C7B	122.5 (8)	C2B—C1B—H1B3	109.5
C5B—C6B—C7B	118.7 (8)	C2B—C1B—H1B4	109.5
C7A—C8A—C9A	121.6 (7)	H1B3—C1B—H1B4	109.5
C7A—C8A—C10A	119.9 (7)	C2B—C1B—H1B5	109.5
C9A—C8A—C10A	118.6 (7)	H1B3—C1B—H1B5	109.5
C11A—C12A—H12A	109.5	H1B4—C1B—H1B5	109.5

C2A—O1A—C3A—O2A	4.7 (12)	C8B—C7B—C6B—N1B	−178.5 (8)
C2A—O1A—C3A—C4A	−175.0 (6)	I3B—C7B—C6B—N1B	−1.7 (11)
C11B—O3B—C10B—O4B	−0.5 (12)	C8B—C7B—C6B—C5B	6.0 (12)
C11B—O3B—C10B—C8B	176.6 (6)	I3B—C7B—C6B—C5B	−177.3 (6)
C8A—C7A—C6A—N1A	−179.1 (8)	C6A—C7A—C8A—C9A	−1.4 (12)
I3A—C7A—C6A—N1A	2.4 (11)	I3A—C7A—C8A—C9A	177.0 (6)
C8A—C7A—C6A—C5A	3.9 (12)	C6A—C7A—C8A—C10A	178.5 (7)
I3A—C7A—C6A—C5A	−174.6 (6)	I3A—C7A—C8A—C10A	−3.1 (10)
N1A—C6A—C5A—C4A	179.6 (8)	C4A—C9A—C8A—C7A	−1.8 (12)
C7A—C6A—C5A—C4A	−3.4 (12)	I1A—C9A—C8A—C7A	174.2 (6)
N1A—C6A—C5A—I2A	−0.1 (12)	C4A—C9A—C8A—C10A	178.3 (7)
C7A—C6A—C5A—I2A	176.9 (6)	I1A—C9A—C8A—C10A	−5.7 (10)
C8A—C9A—C4A—C5A	2.3 (11)	O4A—C10A—C8A—C7A	−72.2 (12)
I1A—C9A—C4A—C5A	−173.8 (6)	O3A—C10A—C8A—C7A	106.5 (9)
C8A—C9A—C4A—C3A	−178.2 (7)	O4A—C10A—C8A—C9A	107.7 (10)
I1A—C9A—C4A—C3A	5.6 (10)	O3A—C10A—C8A—C9A	−73.6 (9)
C6A—C5A—C4A—C9A	0.3 (12)	C2B—O1B—C3B—O2B	8.9 (12)
I2A—C5A—C4A—C9A	180.0 (6)	C2B—O1B—C3B—C4B	−169.2 (6)
C6A—C5A—C4A—C3A	−179.2 (8)	C5B—C4B—C3B—O2B	73.7 (12)
I2A—C5A—C4A—C3A	0.5 (10)	C9B—C4B—C3B—O2B	−104.8 (10)
O2A—C3A—C4A—C9A	89.2 (11)	C5B—C4B—C3B—O1B	−108.2 (8)
O1A—C3A—C4A—C9A	−91.1 (9)	C9B—C4B—C3B—O1B	73.3 (10)
O2A—C3A—C4A—C5A	−91.4 (11)	C6B—C7B—C8B—C9B	−4.6 (12)
O1A—C3A—C4A—C5A	88.3 (9)	I3B—C7B—C8B—C9B	178.6 (6)
C11A—O3A—C10A—O4A	−9.2 (13)	C6B—C7B—C8B—C10B	178.4 (7)
C11A—O3A—C10A—C8A	172.1 (7)	I3B—C7B—C8B—C10B	1.6 (10)
C6B—C5B—C4B—C9B	0.1 (12)	C4B—C9B—C8B—C7B	0.9 (12)
I2B—C5B—C4B—C9B	−176.5 (6)	I1B—C9B—C8B—C7B	176.3 (6)
C6B—C5B—C4B—C3B	−178.4 (7)	C4B—C9B—C8B—C10B	178.0 (7)
I2B—C5B—C4B—C3B	5.0 (10)	I1B—C9B—C8B—C10B	−6.7 (10)
C8B—C9B—C4B—C5B	1.4 (12)	O4B—C10B—C8B—C7B	89.1 (11)
I1B—C9B—C4B—C5B	−173.9 (6)	O3B—C10B—C8B—C7B	−87.9 (9)
C8B—C9B—C4B—C3B	179.8 (7)	O4B—C10B—C8B—C9B	−87.9 (11)
I1B—C9B—C4B—C3B	4.5 (10)	O3B—C10B—C8B—C9B	95.1 (9)
C4B—C5B—C6B—N1B	−179.4 (8)	C3A—O1A—C2A—C1A	−90.6 (9)
I2B—C5B—C6B—N1B	−2.9 (11)	C10A—O3A—C11A—C12A	−158.0 (8)
C4B—C5B—C6B—C7B	−3.6 (12)	C10B—O3B—C11B—C12B	177.5 (6)
I2B—C5B—C6B—C7B	172.9 (6)	C3B—O1B—C2B—C1B	157.5 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2A2···O2Aⁱ	0.97	2.54	3.411 (8)	150
C12A—H12A···O2Bⁱⁱ	0.96	2.60	3.545 (11)	169

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂I₃NO₄
M_r	614.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.7410 (8), 9.6870 (7), 37.7290 (15)
β (°)	94.430 (3)
V (Å³)	3549.5 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.29
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (CAD-4 Software; Enraf–Nonius, 1989)
T_min, T_max	0.362, 0.528
No. of measured, independent and observed [I > 2σ(I)] reflections	6676, 6281, 4259
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.162, 1.06
No. of reflections	6222
No. of parameters	365
No. of restraints	84
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.085P)² + 12.P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.84, −1.05

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2A2···O2Aⁱ	0.97	2.54	3.411 (8)	150
C12A—H12A···O2Bⁱⁱ	0.96	2.60	3.545 (11)	169

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z.

Acknowledgements

The authors acknowledge financial support from Jiangsu Institute of Nuclear Medicine.

References

Beck, T. & Sheldrick, G. M. (2008). Acta Cryst. E64, o1286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stacul, F. (2001). Eur. Radiol. 11, 690–697. Web of Science CrossRef PubMed CAS Google Scholar
Tonnessen, L. E., Pedersen, B. F. & Klaveness, J. (1996). Acta Chem. Scand. 50, 603–608. CrossRef Web of Science Google Scholar
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