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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1736.
Published online 2008 August 9. doi:  10.1107/S1600536808024938
PMCID: PMC2960638

Dimethyl 5-nitro­isophthalate

Abstract

The nitro group in the title compound, C10H9NO6, is rotated by 10.9 (5)° out of the plane of the benzene ring.

Related literature

For related literature, see: Bjorsvik et al. (2001 [triangle]); Cutroneo et al. (2007 [triangle]); Enzweiler et al. (2006 [triangle]).

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Object name is e-64-o1736-scheme1.jpg

Experimental

Crystal data

  • C10H9NO6
  • M r = 239.18
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1736-efi1.jpg
  • a = 4.0130 (8) Å
  • b = 10.660 (2) Å
  • c = 12.643 (3) Å
  • α = 106.11 (3)°
  • β = 93.74 (3)°
  • γ = 91.46 (3)°
  • V = 517.97 (18) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 293 (2) K
  • 0.40 × 0.05 × 0.05 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle])) T min = 0.950, T max = 0.994
  • 2178 measured reflections
  • 1885 independent reflections
  • 1144 reflections with I > 2σ(I)
  • R int = 0.041
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.172
  • S = 1.01
  • 1885 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.18 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024938/cs2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024938/cs2086Isup2.hkl

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

Acknowledgments

The Key Laboratory of Nuclear Medicine of the Ministry Health of China is thanked for supporting this work.

supplementary crystallographic information

Comment

The title molecule (Fig.1), is useful as an important intermediate for the preparation of iodinated X-ray contrast media, in particular non-ionic ones such as Iopamidol, Iohexol and Ioversol, being used clinically all over the world (Cutroneo et al., 2007; Bjorsvik et al., 2001; Enzweiler et al., 2006). This crystal structure shows that the benzene ring and the nitro group are only slightly inclined, as shown by the torsion angles of O5—N—C7—C6 -10.6 (5)° and of O6—N—C7—C8 -11.2 (5)°.

Experimental

5-nitroisophthalic acid (0.5 mmol,100.6 mg) was dissolved in hot methanol (5 ml), then a drop of concentrated sulfuric acid was added and refluxed for 4 h. The precipitate was filtered off, washed with water and dissolved in 95% ethanol(20 mL). The solution was evaporated in air affording colourless needle crystals suitable for X-ray analysis (yield: 85.2%).

Refinement

Positional parameters of all the H atoms bonded to C atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with C—H = 0.93 (aromatic) and with Uiso(H) = 1.2Ueq(C) or 0.96 (methyl) and Uiso(H) = 1.5Ueq(C), respectively.

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C10H9NO6Z = 2
Mr = 239.18F000 = 248
Triclinic, P1Dx = 1.534 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 4.0130 (8) ÅCell parameters from 25 reflections
b = 10.660 (2) Åθ = 8–12º
c = 12.643 (3) ŵ = 0.13 mm1
α = 106.11 (3)ºT = 293 (2) K
β = 93.74 (3)ºNeedle, colourless
γ = 91.46 (3)º0.40 × 0.05 × 0.05 mm
V = 517.97 (18) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.041
Radiation source: fine-focus sealed tubeθmax = 25.3º
Monochromator: graphiteθmin = 1.7º
T = 293(2) Kh = −4→4
ω/2θ scansk = −12→12
Absorption correction: ψ scan(North et al., 1968))l = 0→15
Tmin = 0.950, Tmax = 0.9943 standard reflections
2178 measured reflections every 200 reflections
1885 independent reflections intensity decay: none
1144 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073H-atom parameters constrained
wR(F2) = 0.172  w = 1/[σ2(Fo2) + (0.05P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1885 reflectionsΔρmax = 0.28 e Å3
154 parametersΔρmin = −0.18 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
N0.5209 (9)0.7040 (3)0.8012 (3)0.0572 (8)
O10.7307 (7)0.1642 (2)0.5059 (2)0.0642 (8)
C10.8443 (12)0.0907 (4)0.4027 (3)0.0717 (13)
H1A0.8215−0.00100.39650.108*
H1B1.07480.11450.39920.108*
H1C0.71260.10940.34310.108*
O20.8638 (9)0.3487 (3)0.4668 (2)0.0825 (10)
C20.7532 (9)0.2943 (3)0.5284 (3)0.0480 (9)
O30.2103 (7)0.1601 (2)0.8322 (2)0.0608 (8)
C30.0691 (12)0.0824 (4)0.8961 (4)0.0703 (12)
H3A0.0833−0.00860.85830.105*
H3B−0.16100.10220.90540.105*
H3C0.19060.10160.96710.105*
O40.1018 (8)0.3426 (3)0.9595 (2)0.0739 (9)
C40.2108 (9)0.2883 (3)0.8735 (3)0.0482 (9)
C50.3639 (8)0.3588 (3)0.8013 (3)0.0424 (8)
O50.3683 (10)0.7593 (3)0.8783 (3)0.0957 (12)
C60.3703 (9)0.4947 (3)0.8341 (3)0.0465 (9)
H6A0.28390.54010.89960.056*
O60.6840 (9)0.7614 (3)0.7524 (3)0.0910 (11)
C70.5090 (8)0.5598 (3)0.7663 (3)0.0445 (8)
C80.6352 (8)0.4972 (3)0.6687 (3)0.0457 (8)
H8A0.72760.54470.62540.055*
C90.6236 (9)0.3612 (3)0.6351 (3)0.0448 (8)
C100.4871 (8)0.2942 (3)0.7022 (3)0.0450 (8)
H10A0.47810.20330.68020.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N0.065 (2)0.0474 (18)0.061 (2)0.0053 (16)0.0112 (17)0.0155 (16)
O10.091 (2)0.0508 (15)0.0511 (15)0.0022 (14)0.0238 (14)0.0100 (12)
C10.099 (4)0.062 (2)0.054 (2)0.013 (2)0.027 (2)0.009 (2)
O20.124 (3)0.0604 (17)0.0677 (19)−0.0108 (17)0.0448 (18)0.0181 (15)
C20.049 (2)0.0464 (19)0.050 (2)−0.0043 (16)0.0047 (17)0.0156 (17)
O30.085 (2)0.0465 (14)0.0549 (16)0.0031 (13)0.0257 (14)0.0166 (12)
C30.089 (3)0.057 (2)0.072 (3)−0.002 (2)0.027 (2)0.025 (2)
O40.105 (2)0.0593 (17)0.0644 (18)0.0145 (16)0.0411 (17)0.0209 (14)
C40.049 (2)0.049 (2)0.048 (2)0.0061 (16)0.0103 (17)0.0131 (17)
C50.0417 (19)0.0443 (18)0.0420 (19)0.0034 (15)0.0021 (15)0.0139 (15)
O50.134 (3)0.0523 (17)0.107 (3)0.0219 (18)0.057 (2)0.0198 (17)
C60.050 (2)0.0473 (19)0.0437 (19)0.0042 (16)0.0029 (16)0.0145 (16)
O60.131 (3)0.0527 (17)0.089 (2)−0.0210 (18)0.036 (2)0.0148 (16)
C70.0388 (19)0.0405 (17)0.054 (2)0.0001 (15)−0.0011 (16)0.0137 (16)
C80.045 (2)0.0507 (19)0.0432 (19)−0.0005 (16)0.0012 (16)0.0174 (16)
C90.047 (2)0.0464 (19)0.0412 (18)0.0013 (16)0.0028 (16)0.0127 (15)
C100.044 (2)0.0449 (18)0.046 (2)−0.0032 (15)0.0042 (16)0.0130 (16)

Geometric parameters (Å, °)

N—O61.194 (4)C3—H3B0.9600
N—O51.204 (4)C3—H3C0.9600
N—C71.475 (4)O4—C41.198 (4)
O1—C21.336 (4)C4—C51.485 (5)
O1—C11.433 (4)C5—C101.381 (4)
C1—H1A0.9600C5—C61.391 (5)
C1—H1B0.9600C6—C71.378 (5)
C1—H1C0.9600C6—H6A0.9300
O2—C21.193 (4)C7—C81.366 (5)
C2—C91.475 (5)C8—C91.392 (5)
O3—C41.320 (4)C8—H8A0.9300
O3—C31.438 (4)C9—C101.381 (5)
C3—H3A0.9600C10—H10A0.9300
O6—N—O5122.5 (3)O4—C4—C5123.3 (3)
O6—N—C7118.6 (3)O3—C4—C5112.4 (3)
O5—N—C7118.9 (3)C10—C5—C6119.7 (3)
C2—O1—C1116.9 (3)C10—C5—C4122.3 (3)
O1—C1—H1A109.5C6—C5—C4117.9 (3)
O1—C1—H1B109.5C7—C6—C5117.8 (3)
H1A—C1—H1B109.5C7—C6—H6A121.1
O1—C1—H1C109.5C5—C6—H6A121.1
H1A—C1—H1C109.5C8—C7—C6123.1 (3)
H1B—C1—H1C109.5C8—C7—N118.7 (3)
O2—C2—O1122.5 (3)C6—C7—N118.2 (3)
O2—C2—C9124.5 (3)C7—C8—C9119.0 (3)
O1—C2—C9112.9 (3)C7—C8—H8A120.5
C4—O3—C3116.9 (3)C9—C8—H8A120.5
O3—C3—H3A109.5C10—C9—C8118.7 (3)
O3—C3—H3B109.5C10—C9—C2122.6 (3)
H3A—C3—H3B109.5C8—C9—C2118.7 (3)
O3—C3—H3C109.5C5—C10—C9121.6 (3)
H3A—C3—H3C109.5C5—C10—H10A119.2
H3B—C3—H3C109.5C9—C10—H10A119.2
O4—C4—O3124.3 (3)
C1—O1—C2—O2−0.4 (6)O6—N—C7—C6168.8 (4)
C1—O1—C2—C9178.7 (3)O5—N—C7—C6−10.6 (5)
C3—O3—C4—O4−0.1 (6)C6—C7—C8—C90.2 (5)
C3—O3—C4—C5179.7 (3)N—C7—C8—C9−179.7 (3)
O4—C4—C5—C10−179.8 (4)C7—C8—C9—C10−0.6 (5)
O3—C4—C5—C100.4 (5)C7—C8—C9—C2178.6 (3)
O4—C4—C5—C6−2.1 (5)O2—C2—C9—C10177.7 (4)
O3—C4—C5—C6178.1 (3)O1—C2—C9—C10−1.4 (5)
C10—C5—C6—C7−1.5 (5)O2—C2—C9—C8−1.4 (6)
C4—C5—C6—C7−179.3 (3)O1—C2—C9—C8179.5 (3)
C5—C6—C7—C80.8 (5)C6—C5—C10—C91.2 (5)
C5—C6—C7—N−179.2 (3)C4—C5—C10—C9178.9 (3)
O6—N—C7—C8−11.2 (5)C8—C9—C10—C5−0.1 (5)
O5—N—C7—C8169.4 (4)C2—C9—C10—C5−179.3 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2086).

References

  • Bjorsvik, H.-R., Priebe, H., Cervenka, J., Aabye, A. W., Gulbrandsen, T. & Bryde, A. C. (2001). Org. Process Res. Dev.5, 472–478.
  • Cutroneo, P., Polimeni, G., Curcuruto, R., Calapai, G. & Caputi, A. P. (2007). Pharmacol. Res.56, 35–41. [PubMed]
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Enzweiler, C. N. H., Höhn, S., Taupitz, M., Lembcke, A. E., Wiese, T. H., Hamm, B. & Kivelitz, D. E. (2006). Acad. Radiol.13, 95–103. [PubMed]
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography