Crystal structure of N-(2-hy­droxy­eth­yl)-5-nitro­isophthalamic acid monohydrate

Zou, P.; Wang, H.-Y.; Luo, S.-N.; Liu, Y.-L.; Shen, Y.-J.

doi:10.1107/S160053681402337X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1205-o1206

doi:10.1107/S160053681402337X

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Crystal structure of N-(2-hydroxyethyl)-5-nitroisophthalamic acid monohydrate

Pei Zou,^a ‡ Hong-Yong Wang,^b Shi-Neng Luo,^b Ya-Ling Liu ^b and Yong-Jia Shen ^a ^*

^aInstitute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, People's Republic of China, and ^bJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: zou-pei@163.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 21 October 2014; accepted 23 October 2014; online 29 October 2014)

In the title compound, C₁₀H₁₀N₂O₆·H₂O, the carboxylic 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 interactions link the organic molecules and water molecules of crystallization into a three-dimensional supramolecular architecture.

Keywords: crystal structure; isophthalamic acid; hydrogen bonding; C—H⋯O interactions; X-ray contrast media.

CCDC reference: 1030629

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₀H₁₀N₂O₆·H₂O
M_r = 272.22
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.110
S = 1.00
3775 reflections
192 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O2^iv	0.87 (2)	2.01 (2)	2.853 (2)	164 (2)
C3—H3⋯O7	0.95	2.50	3.422 (2)	163
C9—H9A⋯O7^v	0.99	2.58	3.537 (3)	164
C10—H10B⋯O3ⁱ	0.99	2.50	3.348 (2)	143
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z-1; (iii) x, y-1, z; (iv) -x, -y+1, -z+1; (v) x, y, z-1.

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.

Supporting information

CCDC reference: 1030629

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681402337X/xu5826sup1.cif

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

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

checkCIF report

Comment top

The title compound has been used as an important intermediate for the preparation of iodinated X-ray contrast media, such as ioxitalamic acid and ioxilan, which are used clinically all over the world (Prous et al., 1995; Sovak et al., 1988; Stacul et al., 2001). We report here the crystal structure of title compound.

The structure of the title compound is shown in Fig. 1 and hydrogen bond geometry is given in Table 1. The crystal data show that the bond lengths and angles are within expected ranges and agree well with the corresponding molecular dimensions reported for a similar compound (Liu et al., 2009) . In the title compound, the carboxylic acid group and nitro group are approximately co-planar with the benzene ring [maximum deviation = 0.0264 (9) Å], while the amide moiety is oriented with respect to the benzene ring at 9.22 (5)°. In the crystal, classic O—H···O, N—H···O hydrogen bonds and weak C—H···O hydrogen interactions link organic molecules and crystalline water molecules into the three dimensional supramolecular architecture.

Exprimental top

Monomethyl 5-nitrobenzene-1,3-dihydrogencarboxylate (900 mg, 4 mmol) was dissolved in methanol (5 ml), then ethanolamine (610 mg, 10 mmol) was added and the mixture was refluxed for 16 h. Methanol was distilled off. The residue was dissolved in water and methanol (v/v 1:1), then acidified with 1 M hydrochloric acid to pH = 3. The precipitate was filtered and washed with water. The crude product was recrystallized from ethanol/water. Single crystals were obtained by slow evaporation of an ethanol/water (v/v 7:1) solution.

Refinement top

Hydroxyl H, water H and amino H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed in calculated positions with C—H = 0.95–0.99 Å, and refined in riding mode, U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for the others.

Related literature top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

N-(2-Hydroxyethyl)-5-nitroisophthalamic acid monohydrate top

Crystal data top

C₁₀H₁₀N₂O₆·H₂O	Z = 2
M_r = 272.22	F(000) = 284
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.042	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(F_o²) + (0.0516P)² + 0.0635P] where P = (F_o² + 2F_c²)/3
3775 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₁₀N₂O₆·H₂O	γ = 93.692 (4)°
M_r = 272.22	V = 575.6 (5) Å³
Triclinic, P1	Z = 2
a = 6.449 (3) Å	Mo Kα radiation
b = 8.670 (5) Å	µ = 0.14 mm⁻¹
c = 11.051 (6) Å	T = 173 K
α = 106.581 (8)°	0.44 × 0.31 × 0.06 mm
β = 101.466 (9)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	3775 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	2826 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.98	R_int = 0.028
8661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.41 e Å⁻³
3775 reflections	Δρ_min = −0.21 e Å⁻³
192 parameters

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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.87 (2)	2.01 (2)	2.853 (2)	164 (2)
C3—H3···O7	0.95	2.50	3.422 (2)	163
C9—H9A···O7^v	0.99	2.58	3.537 (3)	164
C10—H10B···O3ⁱ	0.99	2.50	3.348 (2)	143

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

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.87 (2)	2.01 (2)	2.853 (2)	164 (2)
C3—H3···O7	0.95	2.50	3.422 (2)	163
C9—H9A···O7^v	0.99	2.58	3.537 (3)	164
C10—H10B···O3ⁱ	0.99	2.50	3.348 (2)	143

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

Footnotes

‡Permanent address: Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China.

Acknowledgements

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

References

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1205-o1206

doi:10.1107/S160053681402337X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of N-(2-hy­dr­oxy­eth­yl)-5-nitro­isophthalamic acid monohydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Crystal structure of N-(2-hydroxyethyl)-5-nitroisophthalamic acid monohydrate