5-Amino-2,4,6-triiodo-isophthalic acid monohydrate.

The title compound, C(8)H(4)I(3)NO(4)·H(2)O, shows an extensive hydrogen-bond network; in the crystal structure, mol-ecules are linked by O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds involving all possible donors and also the water mol-ecule.

Related literature

For the synthetic procedure, see Larsen et al. (1956 ▶). For related crystal structure determinations: 1,3,5-triiodo­benzene, see: Margraf & Bats (2006 ▶); sodium diatrizoate, see: Tonnessen et al. (1996 ▶). For the 1,3,5-triiodo­benzene core as the basis of contrast agents, see: Yu & Watson (1999 ▶).

Experimental

Crystal data

C8H4I3NO4·H2O

M = 576.84

Orthorhombic,

a = 9.214 (1) Å

b = 15.735 (2) Å

c = 18.816 (2) Å

V = 2728.0 (5) Å3

Z = 8

Cu Kα radiation

μ = 54.11 mm−1

T = 100 (2) K

0.08 × 0.05 × 0.03 mm

Data collection

Bruker SMART 6000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.106, T max = 0.345 (expected range = 0.061–0.197)

49139 measured reflections

2716 independent reflections

2545 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.061

S = 1.03

2716 reflections

173 parameters

14 restraints

Only H-atom coordinates refined

Δρmax = 0.71 e Å−3

Δρmin = −1.71 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXL97 and SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017741/pk2102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017741/pk2102Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H4I3NO4·H2O	F000 = 2080
Mr = 576.84	Dx = 2.809 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9945 reflections
a = 9.214 (1) Å	θ = 4.7–60.8º
b = 15.735 (2) Å	µ = 54.11 mm−1
c = 18.816 (2) Å	T = 100 (2) K
V = 2728.0 (5) Å3	Block, yellow
Z = 8	0.08 × 0.05 × 0.03 mm

Bruker SMART 6000 diffractometer	2716 independent reflections
Radiation source: rotating anode	2545 reflections with I > 2σ(I)
Monochromator: INCOATEC multilayer optics	Rint = 0.043
Detector resolution: 5.602 pixels mm-1	θmax = 74.3º
T = 100(2) K	θmin = 4.7º
ω scans	h = −10→10
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −17→19
Tmin = 0.106, Tmax = 0.345	l = −23→23
49139 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	Only H-atom coordinates refined
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0277P)2 + 17.3624P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
2716 reflections	Δρmax = 0.72 e Å−3
173 parameters	Δρmin = −1.71 e Å−3
14 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.000058 (8)

Experimental. Intensities were measured with a Bruker SMART 6000 area-detector

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 > 2 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. Hydrogen atoms were located via the difference Fourier map and their geometrical positions were refined with restraints. The U values were set to 1.5 Ueq of their parent atom.

	x	y	z	Uiso*/Ueq
I1	1.18424 (3)	0.630616 (18)	0.012748 (16)	0.02419 (10)
I2	0.71499 (3)	0.674286 (18)	0.234093 (15)	0.02375 (10)
I3	1.04238 (3)	0.979824 (17)	0.124476 (17)	0.02693 (10)
C1	1.0827 (5)	0.7970 (3)	0.0781 (2)	0.0161 (8)
C2	1.0606 (5)	0.7094 (3)	0.0789 (2)	0.0161 (9)
C3	0.9544 (5)	0.6745 (3)	0.1231 (2)	0.0153 (9)
C4	0.8655 (5)	0.7276 (3)	0.1631 (2)	0.0163 (9)
C5	0.8803 (5)	0.8172 (3)	0.1604 (2)	0.0165 (9)
C6	0.9945 (5)	0.8492 (3)	0.1199 (2)	0.0180 (9)
C7	1.1981 (5)	0.8362 (3)	0.0320 (3)	0.0202 (10)
O8	1.1458 (4)	0.8648 (2)	−0.02803 (18)	0.0256 (7)
H8	1.205 (6)	0.883 (4)	−0.055 (3)	0.038*
O9	1.3242 (4)	0.8414 (2)	0.05017 (19)	0.0290 (8)
C10	0.9364 (5)	0.5794 (3)	0.1285 (2)	0.0173 (9)
O11	1.0376 (4)	0.5445 (2)	0.16663 (17)	0.0224 (7)
H11	1.031 (7)	0.494 (3)	0.170 (3)	0.034*
O12	0.8358 (4)	0.54161 (19)	0.10032 (17)	0.0213 (7)
N13	0.7889 (5)	0.8702 (2)	0.1997 (2)	0.0210 (8)
H13A	0.698 (5)	0.855 (4)	0.204 (3)	0.031*
H13B	0.785 (6)	0.922 (3)	0.183 (3)	0.031*
O14	1.0395 (4)	0.3834 (2)	0.17540 (18)	0.0235 (7)
H14A	1.074 (7)	0.366 (4)	0.139 (3)	0.035*
H14B	1.099 (6)	0.376 (4)	0.206 (3)	0.035*

	U11	U22	U33	U12	U13	U23
I1	0.02850 (18)	0.02100 (16)	0.02307 (16)	0.00785 (12)	0.00724 (12)	0.00027 (11)
I2	0.02603 (18)	0.02156 (16)	0.02364 (16)	−0.00544 (11)	0.00910 (12)	−0.00016 (11)
I3	0.02852 (19)	0.01260 (15)	0.03966 (19)	−0.00146 (11)	0.00662 (13)	0.00096 (11)
C1	0.018 (2)	0.0143 (19)	0.0162 (19)	0.0012 (17)	0.0007 (17)	0.0000 (16)
C2	0.019 (2)	0.014 (2)	0.0150 (19)	0.0033 (17)	−0.0002 (17)	−0.0002 (16)
C3	0.020 (2)	0.013 (2)	0.0135 (19)	0.0006 (17)	−0.0052 (17)	0.0019 (15)
C4	0.018 (2)	0.016 (2)	0.0150 (19)	−0.0072 (16)	0.0005 (17)	0.0017 (16)
C5	0.018 (2)	0.015 (2)	0.016 (2)	0.0003 (17)	−0.0023 (17)	−0.0006 (16)
C6	0.023 (2)	0.013 (2)	0.017 (2)	−0.0022 (18)	−0.0013 (18)	0.0009 (16)
C7	0.023 (3)	0.014 (2)	0.023 (2)	−0.0007 (17)	0.0010 (19)	−0.0016 (17)
O8	0.0251 (19)	0.0276 (18)	0.0241 (17)	−0.0019 (14)	0.0036 (15)	0.0093 (14)
O9	0.0216 (19)	0.038 (2)	0.0276 (18)	−0.0045 (15)	0.0035 (15)	0.0013 (15)
C10	0.023 (2)	0.014 (2)	0.015 (2)	−0.0007 (18)	0.0048 (18)	0.0001 (16)
O11	0.0274 (18)	0.0132 (15)	0.0265 (17)	−0.0007 (13)	−0.0074 (14)	0.0043 (13)
O12	0.0279 (18)	0.0121 (14)	0.0239 (16)	−0.0039 (13)	−0.0064 (14)	0.0014 (12)
N13	0.021 (2)	0.0148 (18)	0.027 (2)	0.0019 (15)	0.0035 (17)	−0.0026 (15)
O14	0.0255 (19)	0.0217 (16)	0.0233 (17)	0.0028 (14)	−0.0003 (14)	0.0027 (14)

I1—C2	2.094 (4)	C5—N13	1.396 (6)
I2—C4	2.100 (4)	C7—O9	1.214 (6)
I3—C6	2.103 (4)	C7—O8	1.308 (6)
C1—C2	1.394 (6)	O8—H8	0.80 (5)
C1—C6	1.398 (6)	C10—O12	1.223 (6)
C1—C7	1.504 (6)	C10—O11	1.299 (6)
C2—C3	1.396 (6)	O11—H11	0.79 (5)
C3—C4	1.391 (6)	N13—H13A	0.88 (4)
C3—C10	1.509 (6)	N13—H13B	0.88 (4)
C4—C5	1.418 (6)	O14—H14A	0.81 (4)
C5—C6	1.393 (6)	O14—H14B	0.81 (4)
C2—C1—C6	119.4 (4)	C5—C6—C1	122.3 (4)
C2—C1—C7	121.0 (4)	C5—C6—I3	119.3 (3)
C6—C1—C7	119.6 (4)	C1—C6—I3	118.4 (3)
C1—C2—C3	119.8 (4)	O9—C7—O8	125.0 (4)
C1—C2—I1	120.0 (3)	O9—C7—C1	122.7 (4)
C3—C2—I1	120.2 (3)	O8—C7—C1	112.3 (4)
C4—C3—C2	120.0 (4)	C7—O8—H8	115 (5)
C4—C3—C10	119.6 (4)	O12—C10—O11	125.3 (4)
C2—C3—C10	120.4 (4)	O12—C10—C3	122.5 (4)
C3—C4—C5	121.3 (4)	O11—C10—C3	112.3 (4)
C3—C4—I2	119.6 (3)	C10—O11—H11	114 (5)
C5—C4—I2	119.0 (3)	C5—N13—H13A	117 (4)
C6—C5—N13	122.0 (4)	C5—N13—H13B	113 (4)
C6—C5—C4	116.9 (4)	H13A—N13—H13B	105 (6)
N13—C5—C4	121.0 (4)	H14A—O14—H14B	108 (6)
C6—C1—C2—C3	−2.2 (6)	N13—C5—C6—C1	−177.4 (4)
C7—C1—C2—C3	179.0 (4)	C4—C5—C6—C1	6.0 (6)
C6—C1—C2—I1	176.7 (3)	N13—C5—C6—I3	5.2 (5)
C7—C1—C2—I1	−2.0 (5)	C4—C5—C6—I3	−171.4 (3)
C1—C2—C3—C4	3.5 (6)	C2—C1—C6—C5	−2.8 (6)
I1—C2—C3—C4	−175.4 (3)	C7—C1—C6—C5	176.0 (4)
C1—C2—C3—C10	−175.6 (4)	C2—C1—C6—I3	174.7 (3)
I1—C2—C3—C10	5.5 (5)	C7—C1—C6—I3	−6.5 (5)
C2—C3—C4—C5	−0.1 (6)	C2—C1—C7—O9	−84.0 (6)
C10—C3—C4—C5	179.1 (4)	C6—C1—C7—O9	97.2 (5)
C2—C3—C4—I2	−176.2 (3)	C2—C1—C7—O8	97.3 (5)
C10—C3—C4—I2	3.0 (5)	C6—C1—C7—O8	−81.5 (5)
C3—C4—C5—C6	−4.6 (6)	C4—C3—C10—O12	75.4 (5)
I2—C4—C5—C6	171.5 (3)	C2—C3—C10—O12	−105.5 (5)
C3—C4—C5—N13	178.8 (4)	C4—C3—C10—O11	−103.6 (4)
I2—C4—C5—N13	−5.1 (5)	C2—C3—C10—O11	75.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O14	0.79 (5)	1.75 (5)	2.540 (5)	173 (7)
O8—H8···O12i	0.80 (5)	1.90 (5)	2.662 (5)	161 (7)
O14—H14A···O9ii	0.81 (4)	1.95 (4)	2.751 (5)	170 (6)
O14—H14B···N13iii	0.81 (4)	2.05 (4)	2.841 (5)	166 (6)
N13—H13A···O14iv	0.88 (4)	2.30 (5)	3.067 (6)	147 (5)
N13—H13B···O12iv	0.88 (4)	2.68 (5)	3.478 (5)	152 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O14	0.79 (5)	1.75 (5)	2.540 (5)	173 (7)
O8—H8⋯O12i	0.80 (5)	1.90 (5)	2.662 (5)	161 (7)
O14—H14A⋯O9ii	0.81 (4)	1.95 (4)	2.751 (5)	170 (6)
O14—H14B⋯N13iii	0.81 (4)	2.05 (4)	2.841 (5)	166 (6)
N13—H13A⋯O14iv	0.88 (4)	2.30 (5)	3.067 (6)	147 (5)
N13—H13B⋯O12iv	0.88 (4)	2.68 (5)	3.478 (5)	152 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .