Crystal structure of N-(2-hy-droxy-eth-yl)-5-nitro-isophthalamic acid monohydrate.

In the title compound, C10H10N2O6·H2O, the carb-oxy-lic acid group and the nitro group are essentially coplanar with the benzene ring [maximum deviation = 0.0264 (9) Å], while the amide group is oriented at a dihedral angle of 9.22 (5)° with respect to the benzene ring. In the crystal, classical O-H⋯O and N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions link the organic mol-ecules and water mol-ecules of crystallization into a three-dimensional supra-molecular architecture.

Related literature

The title compound is an inter­mediate for the preparation of iodinated X-ray contrast media, such as ioxitalamic acid and ioxilan, see: Prous et al. (1995 ▶); Sovak (1988 ▶); Stacul (2001 ▶). For a related structure, see: Liu et al. (2009 ▶).

Experimental

Crystal data

C10H10N2O6·H2O

M = 272.22

Triclinic,

a = 6.449 (3) Å

b = 8.670 (5) Å

c = 11.051 (6) Å

α = 106.581 (8)°

β = 101.466 (9)°

γ = 93.692 (4)°

V = 575.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 173 K

0.44 × 0.31 × 0.06 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008 ▶) T min = 0.93, T max = 0.98

8661 measured reflections

3775 independent reflections

2826 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.110

S = 1.00

3775 reflections

192 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681402337X/xu5826sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402337X/xu5826Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681402337X/xu5826Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S160053681402337X/xu5826fig1.tif

A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

CCDC reference: 1030629

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H10N2O6·H2O	Z = 2
Mr = 272.22	F(000) = 284
Triclinic, P1	Dx = 1.571 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.449 (3) Å	Cell parameters from 2242 reflections
b = 8.670 (5) Å	θ = 2.5–31.5°
c = 11.051 (6) Å	µ = 0.14 mm−1
α = 106.581 (8)°	T = 173 K
β = 101.466 (9)°	Platelet, colorless
γ = 93.692 (4)°	0.44 × 0.31 × 0.06 mm
V = 575.6 (5) Å3

Rigaku AFC10/Saturn724+ diffractometer	3775 independent reflections
Radiation source: Rotating Anode	2826 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 28.5714 pixels mm-1	θmax = 31.5°, θmin = 2.5°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −12→12
Tmin = 0.93, Tmax = 0.98	l = −16→16
8661 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.0635P] where P = (Fo2 + 2Fc2)/3
3775 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.13495 (17)	0.98481 (9)	0.27386 (8)	0.0329 (2)
O2	−0.24748 (15)	0.59705 (10)	−0.05062 (8)	0.0295 (2)
O3	0.18120 (14)	0.29530 (9)	0.34122 (8)	0.02551 (19)
O4	0.26622 (14)	0.33382 (9)	0.55509 (8)	0.02415 (19)
O5	0.39066 (19)	0.91355 (11)	0.83077 (8)	0.0419 (3)
O6	0.36654 (17)	1.10655 (10)	0.74248 (9)	0.0336 (2)
O7	0.33213 (16)	0.48483 (11)	0.83119 (10)	0.0321 (2)
N1	0.13279 (17)	0.73307 (11)	0.14290 (9)	0.0232 (2)
N2	0.35598 (17)	0.96255 (11)	0.73593 (9)	0.0246 (2)
C1	0.23184 (17)	0.38719 (12)	0.46364 (10)	0.0183 (2)
C2	0.24161 (17)	0.56423 (12)	0.47566 (10)	0.0175 (2)
C3	0.29369 (17)	0.67808 (12)	0.59893 (10)	0.0190 (2)
H3	0.3237	0.6453	0.6750	0.023*
C4	0.30003 (17)	0.84077 (12)	0.60621 (10)	0.0192 (2)
C5	0.25634 (17)	0.89481 (12)	0.49861 (10)	0.0197 (2)
H5	0.2607	1.0074	0.5079	0.024*
C6	0.20567 (17)	0.77954 (12)	0.37580 (10)	0.0183 (2)
C7	0.19851 (17)	0.61473 (12)	0.36545 (10)	0.0184 (2)
H7	0.1638	0.5361	0.2821	0.022*
C8	0.15561 (19)	0.83987 (12)	0.25990 (10)	0.0208 (2)
C9	0.0792 (2)	0.77886 (14)	0.02391 (11)	0.0269 (3)
H9A	0.1418	0.7084	−0.0433	0.032*
H9B	0.1419	0.8924	0.0411	0.032*
C10	−0.1591 (2)	0.76327 (13)	−0.02582 (11)	0.0278 (3)
H10A	−0.2227	0.8365	0.0393	0.033*
H10B	−0.1913	0.7940	−0.1066	0.033*
H1N	0.157 (2)	0.6305 (19)	0.1355 (14)	0.036 (4)*
H2O	−0.397 (5)	0.569 (3)	−0.096 (3)	0.120 (10)*
H3O	0.168 (3)	0.188 (2)	0.3314 (17)	0.053 (5)*
H7A	0.317 (3)	0.421 (2)	0.759 (2)	0.060 (6)*
H7B	0.302 (4)	0.440 (3)	0.888 (2)	0.089 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0600 (6)	0.0125 (4)	0.0251 (4)	0.0069 (4)	0.0059 (4)	0.0062 (3)
O2	0.0387 (5)	0.0219 (4)	0.0256 (4)	0.0048 (4)	0.0028 (4)	0.0064 (3)
O3	0.0422 (5)	0.0126 (3)	0.0208 (4)	0.0033 (3)	0.0063 (4)	0.0041 (3)
O4	0.0321 (5)	0.0200 (4)	0.0231 (4)	0.0051 (3)	0.0064 (3)	0.0104 (3)
O5	0.0755 (8)	0.0291 (5)	0.0179 (4)	0.0106 (5)	0.0042 (5)	0.0055 (3)
O6	0.0525 (6)	0.0160 (4)	0.0277 (5)	0.0007 (4)	0.0083 (4)	0.0010 (3)
O7	0.0448 (6)	0.0260 (5)	0.0239 (5)	0.0035 (4)	0.0052 (4)	0.0069 (4)
N1	0.0369 (6)	0.0134 (4)	0.0193 (4)	0.0037 (4)	0.0051 (4)	0.0055 (3)
N2	0.0317 (5)	0.0196 (4)	0.0195 (4)	0.0028 (4)	0.0048 (4)	0.0021 (3)
C1	0.0204 (5)	0.0153 (4)	0.0207 (5)	0.0035 (4)	0.0066 (4)	0.0063 (4)
C2	0.0187 (5)	0.0134 (4)	0.0211 (5)	0.0026 (4)	0.0058 (4)	0.0053 (4)
C3	0.0218 (5)	0.0172 (5)	0.0188 (5)	0.0035 (4)	0.0050 (4)	0.0060 (4)
C4	0.0221 (5)	0.0160 (5)	0.0171 (5)	0.0018 (4)	0.0039 (4)	0.0020 (4)
C5	0.0236 (5)	0.0133 (4)	0.0210 (5)	0.0014 (4)	0.0050 (4)	0.0036 (4)
C6	0.0220 (5)	0.0140 (4)	0.0188 (5)	0.0021 (4)	0.0043 (4)	0.0049 (4)
C7	0.0222 (5)	0.0139 (4)	0.0184 (5)	0.0022 (4)	0.0045 (4)	0.0041 (3)
C8	0.0273 (6)	0.0129 (4)	0.0207 (5)	0.0005 (4)	0.0039 (4)	0.0044 (4)
C9	0.0449 (7)	0.0175 (5)	0.0202 (5)	0.0030 (5)	0.0092 (5)	0.0077 (4)
C10	0.0466 (8)	0.0183 (5)	0.0189 (5)	0.0098 (5)	0.0064 (5)	0.0056 (4)

O1—C8	1.2408 (14)	C2—C7	1.3921 (16)
O2—C10	1.4435 (16)	C2—C3	1.3967 (15)
O2—H2O	0.98 (3)	C3—C4	1.3871 (16)
O3—C1	1.3219 (14)	C3—H3	0.9500
O3—H3O	0.904 (19)	C4—C5	1.3837 (16)
O4—C1	1.2147 (14)	C5—C6	1.3983 (15)
O5—N2	1.2257 (14)	C5—H5	0.9500
O6—N2	1.2264 (14)	C6—C7	1.3974 (15)
O7—H7A	0.81 (2)	C6—C8	1.5027 (16)
O7—H7B	0.88 (3)	C7—H7	0.9500
N1—C8	1.3321 (15)	C9—C10	1.509 (2)
N1—C9	1.4632 (16)	C9—H9A	0.9900
N1—H1N	0.897 (16)	C9—H9B	0.9900
N2—C4	1.4770 (15)	C10—H10A	0.9900
C1—C2	1.4984 (16)	C10—H10B	0.9900
C10—O2—H2O	115.2 (15)	C6—C5—H5	120.8
C1—O3—H3O	113.6 (11)	C7—C6—C5	119.40 (10)
H7A—O7—H7B	113 (2)	C7—C6—C8	122.83 (9)
C8—N1—C9	122.19 (10)	C5—C6—C8	117.75 (10)
C8—N1—H1N	119.9 (10)	C2—C7—C6	120.85 (10)
C9—N1—H1N	117.8 (10)	C2—C7—H7	119.6
O5—N2—O6	123.86 (10)	C6—C7—H7	119.6
O5—N2—C4	117.95 (10)	O1—C8—N1	121.55 (10)
O6—N2—C4	118.19 (10)	O1—C8—C6	120.47 (10)
O4—C1—O3	123.79 (10)	N1—C8—C6	117.98 (10)
O4—C1—C2	124.30 (10)	N1—C9—C10	111.50 (10)
O3—C1—C2	111.91 (9)	N1—C9—H9A	109.3
C7—C2—C3	120.36 (10)	C10—C9—H9A	109.3
C7—C2—C1	120.47 (9)	N1—C9—H9B	109.3
C3—C2—C1	119.16 (9)	C10—C9—H9B	109.3
C4—C3—C2	117.51 (10)	H9A—C9—H9B	108.0
C4—C3—H3	121.2	O2—C10—C9	108.51 (9)
C2—C3—H3	121.2	O2—C10—H10A	110.0
C5—C4—C3	123.53 (10)	C9—C10—H10A	110.0
C5—C4—N2	118.37 (10)	O2—C10—H10B	110.0
C3—C4—N2	118.10 (10)	C9—C10—H10B	110.0
C4—C5—C6	118.34 (10)	H10A—C10—H10B	108.4
C4—C5—H5	120.8
O4—C1—C2—C7	−179.61 (11)	C4—C5—C6—C7	0.66 (16)
O3—C1—C2—C7	0.41 (14)	C4—C5—C6—C8	179.17 (10)
O4—C1—C2—C3	0.13 (16)	C3—C2—C7—C6	−0.23 (16)
O3—C1—C2—C3	−179.85 (10)	C1—C2—C7—C6	179.51 (10)
C7—C2—C3—C4	0.08 (16)	C5—C6—C7—C2	−0.15 (16)
C1—C2—C3—C4	−179.66 (9)	C8—C6—C7—C2	−178.58 (10)
C2—C3—C4—C5	0.46 (17)	C9—N1—C8—O1	−0.92 (19)
C2—C3—C4—N2	−179.69 (10)	C9—N1—C8—C6	178.56 (10)
O5—N2—C4—C5	178.70 (11)	C7—C6—C8—O1	169.92 (11)
O6—N2—C4—C5	−1.81 (16)	C5—C6—C8—O1	−8.53 (17)
O5—N2—C4—C3	−1.16 (16)	C7—C6—C8—N1	−9.56 (17)
O6—N2—C4—C3	178.33 (10)	C5—C6—C8—N1	171.99 (11)
C3—C4—C5—C6	−0.84 (17)	C8—N1—C9—C10	−88.93 (13)
N2—C4—C5—C6	179.31 (10)	N1—C9—C10—O2	−59.16 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.896 (17)	2.103 (16)	2.947 (2)	156.6 (13)
O2—H2O···O7ii	0.97 (3)	1.78 (3)	2.744 (2)	169 (2)
O3—H3O···O1iii	0.902 (18)	1.677 (18)	2.5601 (19)	165.7 (17)
O7—H7A···O4	0.81 (2)	2.11 (2)	2.887 (2)	159.3 (18)
O7—H7B···O2iv	0.87 (2)	2.01 (2)	2.853 (2)	164 (2)
C3—H3···O7	0.95	2.50	3.422 (2)	163
C9—H9A···O7v	0.99	2.58	3.537 (3)	164
C10—H10B···O3i	0.99	2.50	3.348 (2)	143

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO2i	0.896(17)	2.103(16)	2.947(2)	156.6(13)
O2H2OO7ii	0.97(3)	1.78(3)	2.744(2)	169(2)
O3H3OO1iii	0.902(18)	1.677(18)	2.5601(19)	165.7(17)
O7H7AO4	0.81(2)	2.11(2)	2.887(2)	159.3(18)
O7H7BO2iv	0.87(2)	2.01(2)	2.853(2)	164(2)
C3H3O7	0.95	2.50	3.422(2)	163
C9H9AO7v	0.99	2.58	3.537(3)	164
C10H10BO3i	0.99	2.50	3.348(2)	143

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