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

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Di­methyl 5-nitro­isophthalate

aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
*Correspondence e-mail: xiemh0704@sina.com

(Received 9 July 2008; accepted 3 August 2008; online 9 August 2008)

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[Bjorsvik, H.-R., Priebe, H., Cervenka, J., Aabye, A. W., Gulbrandsen, T. & Bryde, A. C. (2001). Org. Process Res. Dev. 5, 472-478.]); Cutroneo et al. (2007[Cutroneo, P., Polimeni, G., Curcuruto, R., Calapai, G. & Caputi, A. P. (2007). Pharmacol. Res. 56, 35-41.]); Enzweiler et al. (2006[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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NO6

  • Mr = 239.18

  • Triclinic, [P \overline 1]

  • 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.])) Tmin = 0.950, Tmax = 0.994

  • 2178 measured reflections

  • 1885 independent reflections

  • 1144 reflections with I > 2σ(I)

  • Rint = 0.041

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 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[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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)°.

Related literature top

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

Experimental top

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 top

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.

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: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
Dimethyl 5-nitrobenzene-1,3-dicarboxylate top
Crystal data top
C10H9NO6Z = 2
Mr = 239.18F(000) = 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 = 8–12°
c = 12.643 (3) ŵ = 0.13 mm1
α = 106.11 (3)°T = 293 K
β = 93.74 (3)°Needle, colourless
γ = 91.46 (3)°0.40 × 0.05 × 0.05 mm
V = 517.97 (18) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.3°, θmin = 1.7°
ω/2θ scansh = 44
Absorption correction: ψ scan
(North et al., 1968))
k = 1212
Tmin = 0.950, Tmax = 0.994l = 015
2178 measured reflections3 standard reflections every 200 reflections
1885 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.05P)2 + 0.6P]
where P = (Fo2 + 2Fc2)/3
1885 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C10H9NO6γ = 91.46 (3)°
Mr = 239.18V = 517.97 (18) Å3
Triclinic, P1Z = 2
a = 4.0130 (8) ÅMo Kα radiation
b = 10.660 (2) ŵ = 0.13 mm1
c = 12.643 (3) ÅT = 293 K
α = 106.11 (3)°0.40 × 0.05 × 0.05 mm
β = 93.74 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1144 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968))
Rint = 0.041
Tmin = 0.950, Tmax = 0.9943 standard reflections every 200 reflections
2178 measured reflections intensity decay: none
1885 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0730 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.01Δρmax = 0.28 e Å3
1885 reflectionsΔρmin = 0.18 e Å3
154 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H1A0.82150.00100.39650.108*
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)
H3A0.08330.00860.85830.105*
H3B0.16100.10220.90540.105*
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) top
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, º) top
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—O20.4 (6)O6—N—C7—C6168.8 (4)
C1—O1—C2—C9178.7 (3)O5—N—C7—C610.6 (5)
C3—O3—C4—O40.1 (6)C6—C7—C8—C90.2 (5)
C3—O3—C4—C5179.7 (3)N—C7—C8—C9179.7 (3)
O4—C4—C5—C10179.8 (4)C7—C8—C9—C100.6 (5)
O3—C4—C5—C100.4 (5)C7—C8—C9—C2178.6 (3)
O4—C4—C5—C62.1 (5)O2—C2—C9—C10177.7 (4)
O3—C4—C5—C6178.1 (3)O1—C2—C9—C101.4 (5)
C10—C5—C6—C71.5 (5)O2—C2—C9—C81.4 (6)
C4—C5—C6—C7179.3 (3)O1—C2—C9—C8179.5 (3)
C5—C6—C7—C80.8 (5)C6—C5—C10—C91.2 (5)
C5—C6—C7—N179.2 (3)C4—C5—C10—C9178.9 (3)
O6—N—C7—C811.2 (5)C8—C9—C10—C50.1 (5)
O5—N—C7—C8169.4 (4)C2—C9—C10—C5179.3 (3)

Experimental details

Crystal data
Chemical formulaC10H9NO6
Mr239.18
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)4.0130 (8), 10.660 (2), 12.643 (3)
α, β, γ (°)106.11 (3), 93.74 (3), 91.46 (3)
V3)517.97 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.40 × 0.05 × 0.05
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968))
Tmin, Tmax0.950, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
2178, 1885, 1144
Rint0.041
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.172, 1.01
No. of reflections1885
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.18

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

 

Acknowledgements

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

References

First citationBjorsvik, H.-R., Priebe, H., Cervenka, J., Aabye, A. W., Gulbrandsen, T. & Bryde, A. C. (2001). Org. Process Res. Dev. 5, 472–478.  Web of Science CrossRef CAS Google Scholar
First citationCutroneo, P., Polimeni, G., Curcuruto, R., Calapai, G. & Caputi, A. P. (2007). Pharmacol. Res. 56, 35–41.  Web of Science CrossRef PubMed CAS Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationEnzweiler, C. N. H., Höhn, S., Taupitz, M., Lembcke, A. E., Wiese, T. H., Hamm, B. & Kivelitz, D. E. (2006). Acad. Radiol. 13, 95–103.  Web of Science CrossRef PubMed Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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