Acta Cryst. (2008). E64, o1736 [ doi:10.1107/S1600536808024938 ]
The nitro group in the title compound, C10H9NO6, is rotated by 10.9 (5)° out of the plane of the benzene ring.
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%).
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.
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).
![[Figure 1]](./cs2086fig1thm.gif)
| Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. |
| C10H9NO6 | Z = 2 |
| Mr = 239.18 | F000 = 248 |
| Triclinic, P1 | Dx = 1.534 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 4.0130 (8) Å | Cell parameters from 25 reflections |
| b = 10.660 (2) Å | θ = 8–12º |
| c = 12.643 (3) Å | µ = 0.13 mm−1 |
| α = 106.11 (3)º | T = 293 (2) K |
| β = 93.74 (3)º | Needle, colourless |
| γ = 91.46 (3)º | 0.40 × 0.05 × 0.05 mm |
| V = 517.97 (18) Å3 |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.041 |
| Radiation source: fine-focus sealed tube | θmax = 25.3º |
| Monochromator: graphite | θmin = 1.7º |
| T = 293(2) K | h = −4→4 |
| ω/2θ scans | k = −12→12 |
| Absorption correction: ψ scan (North et al., 1968)) | l = 0→15 |
| Tmin = 0.950, Tmax = 0.994 | 3 standard reflections |
| 2178 measured reflections | every 200 reflections |
| 1885 independent reflections | intensity decay: none |
| 1144 reflections with I > 2σ(I) |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.073 | H-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 reflections | Δρmax = 0.28 e Å−3 |
| 154 parameters | Δρmin = −0.18 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C10H9NO6 | γ = 91.46 (3)º |
| Mr = 239.18 | V = 517.97 (18) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 4.0130 (8) Å | Mo Kα |
| b = 10.660 (2) Å | µ = 0.13 mm−1 |
| c = 12.643 (3) Å | T = 293 (2) K |
| α = 106.11 (3)º | 0.40 × 0.05 × 0.05 mm |
| β = 93.74 (3)º |
| 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 = 0.994 | 3 standard reflections |
| 2178 measured reflections | every 200 reflections |
| 1885 independent reflections | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.073 | 154 parameters |
| wR(F2) = 0.172 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 0.28 e Å−3 |
| 1885 reflections | Δρmin = −0.18 e Å−3 |
| x | y | z | Uiso*/Ueq | ||
| N | 0.5209 (9) | 0.7040 (3) | 0.8012 (3) | 0.0572 (8) | |
| O1 | 0.7307 (7) | 0.1642 (2) | 0.5059 (2) | 0.0642 (8) | |
| C1 | 0.8443 (12) | 0.0907 (4) | 0.4027 (3) | 0.0717 (13) | |
| H1A | 0.8215 | −0.0010 | 0.3965 | 0.108* | |
| H1B | 1.0748 | 0.1145 | 0.3992 | 0.108* | |
| H1C | 0.7126 | 0.1094 | 0.3431 | 0.108* | |
| O2 | 0.8638 (9) | 0.3487 (3) | 0.4668 (2) | 0.0825 (10) | |
| C2 | 0.7532 (9) | 0.2943 (3) | 0.5284 (3) | 0.0480 (9) | |
| O3 | 0.2103 (7) | 0.1601 (2) | 0.8322 (2) | 0.0608 (8) | |
| C3 | 0.0691 (12) | 0.0824 (4) | 0.8961 (4) | 0.0703 (12) | |
| H3A | 0.0833 | −0.0086 | 0.8583 | 0.105* | |
| H3B | −0.1610 | 0.1022 | 0.9054 | 0.105* | |
| H3C | 0.1906 | 0.1016 | 0.9671 | 0.105* | |
| O4 | 0.1018 (8) | 0.3426 (3) | 0.9595 (2) | 0.0739 (9) | |
| C4 | 0.2108 (9) | 0.2883 (3) | 0.8735 (3) | 0.0482 (9) | |
| C5 | 0.3639 (8) | 0.3588 (3) | 0.8013 (3) | 0.0424 (8) | |
| O5 | 0.3683 (10) | 0.7593 (3) | 0.8783 (3) | 0.0957 (12) | |
| C6 | 0.3703 (9) | 0.4947 (3) | 0.8341 (3) | 0.0465 (9) | |
| H6A | 0.2839 | 0.5401 | 0.8996 | 0.056* | |
| O6 | 0.6840 (9) | 0.7614 (3) | 0.7524 (3) | 0.0910 (11) | |
| C7 | 0.5090 (8) | 0.5598 (3) | 0.7663 (3) | 0.0445 (8) | |
| C8 | 0.6352 (8) | 0.4972 (3) | 0.6687 (3) | 0.0457 (8) | |
| H8A | 0.7276 | 0.5447 | 0.6254 | 0.055* | |
| C9 | 0.6236 (9) | 0.3612 (3) | 0.6351 (3) | 0.0448 (8) | |
| C10 | 0.4871 (8) | 0.2942 (3) | 0.7022 (3) | 0.0450 (8) | |
| H10A | 0.4781 | 0.2033 | 0.6802 | 0.054* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N | 0.065 (2) | 0.0474 (18) | 0.061 (2) | 0.0053 (16) | 0.0112 (17) | 0.0155 (16) |
| O1 | 0.091 (2) | 0.0508 (15) | 0.0511 (15) | 0.0022 (14) | 0.0238 (14) | 0.0100 (12) |
| C1 | 0.099 (4) | 0.062 (2) | 0.054 (2) | 0.013 (2) | 0.027 (2) | 0.009 (2) |
| O2 | 0.124 (3) | 0.0604 (17) | 0.0677 (19) | −0.0108 (17) | 0.0448 (18) | 0.0181 (15) |
| C2 | 0.049 (2) | 0.0464 (19) | 0.050 (2) | −0.0043 (16) | 0.0047 (17) | 0.0156 (17) |
| O3 | 0.085 (2) | 0.0465 (14) | 0.0549 (16) | 0.0031 (13) | 0.0257 (14) | 0.0166 (12) |
| C3 | 0.089 (3) | 0.057 (2) | 0.072 (3) | −0.002 (2) | 0.027 (2) | 0.025 (2) |
| O4 | 0.105 (2) | 0.0593 (17) | 0.0644 (18) | 0.0145 (16) | 0.0411 (17) | 0.0209 (14) |
| C4 | 0.049 (2) | 0.049 (2) | 0.048 (2) | 0.0061 (16) | 0.0103 (17) | 0.0131 (17) |
| C5 | 0.0417 (19) | 0.0443 (18) | 0.0420 (19) | 0.0034 (15) | 0.0021 (15) | 0.0139 (15) |
| O5 | 0.134 (3) | 0.0523 (17) | 0.107 (3) | 0.0219 (18) | 0.057 (2) | 0.0198 (17) |
| C6 | 0.050 (2) | 0.0473 (19) | 0.0437 (19) | 0.0042 (16) | 0.0029 (16) | 0.0145 (16) |
| O6 | 0.131 (3) | 0.0527 (17) | 0.089 (2) | −0.0210 (18) | 0.036 (2) | 0.0148 (16) |
| C7 | 0.0388 (19) | 0.0405 (17) | 0.054 (2) | 0.0001 (15) | −0.0011 (16) | 0.0137 (16) |
| C8 | 0.045 (2) | 0.0507 (19) | 0.0432 (19) | −0.0005 (16) | 0.0012 (16) | 0.0174 (16) |
| C9 | 0.047 (2) | 0.0464 (19) | 0.0412 (18) | 0.0013 (16) | 0.0028 (16) | 0.0127 (15) |
| C10 | 0.044 (2) | 0.0449 (18) | 0.046 (2) | −0.0032 (15) | 0.0042 (16) | 0.0130 (16) |
| N—O6 | 1.194 (4) | C3—H3B | 0.9600 |
| N—O5 | 1.204 (4) | C3—H3C | 0.9600 |
| N—C7 | 1.475 (4) | O4—C4 | 1.198 (4) |
| O1—C2 | 1.336 (4) | C4—C5 | 1.485 (5) |
| O1—C1 | 1.433 (4) | C5—C10 | 1.381 (4) |
| C1—H1A | 0.9600 | C5—C6 | 1.391 (5) |
| C1—H1B | 0.9600 | C6—C7 | 1.378 (5) |
| C1—H1C | 0.9600 | C6—H6A | 0.9300 |
| O2—C2 | 1.193 (4) | C7—C8 | 1.366 (5) |
| C2—C9 | 1.475 (5) | C8—C9 | 1.392 (5) |
| O3—C4 | 1.320 (4) | C8—H8A | 0.9300 |
| O3—C3 | 1.438 (4) | C9—C10 | 1.381 (5) |
| C3—H3A | 0.9600 | C10—H10A | 0.9300 |
| O6—N—O5 | 122.5 (3) | O4—C4—C5 | 123.3 (3) |
| O6—N—C7 | 118.6 (3) | O3—C4—C5 | 112.4 (3) |
| O5—N—C7 | 118.9 (3) | C10—C5—C6 | 119.7 (3) |
| C2—O1—C1 | 116.9 (3) | C10—C5—C4 | 122.3 (3) |
| O1—C1—H1A | 109.5 | C6—C5—C4 | 117.9 (3) |
| O1—C1—H1B | 109.5 | C7—C6—C5 | 117.8 (3) |
| H1A—C1—H1B | 109.5 | C7—C6—H6A | 121.1 |
| O1—C1—H1C | 109.5 | C5—C6—H6A | 121.1 |
| H1A—C1—H1C | 109.5 | C8—C7—C6 | 123.1 (3) |
| H1B—C1—H1C | 109.5 | C8—C7—N | 118.7 (3) |
| O2—C2—O1 | 122.5 (3) | C6—C7—N | 118.2 (3) |
| O2—C2—C9 | 124.5 (3) | C7—C8—C9 | 119.0 (3) |
| O1—C2—C9 | 112.9 (3) | C7—C8—H8A | 120.5 |
| C4—O3—C3 | 116.9 (3) | C9—C8—H8A | 120.5 |
| O3—C3—H3A | 109.5 | C10—C9—C8 | 118.7 (3) |
| O3—C3—H3B | 109.5 | C10—C9—C2 | 122.6 (3) |
| H3A—C3—H3B | 109.5 | C8—C9—C2 | 118.7 (3) |
| O3—C3—H3C | 109.5 | C5—C10—C9 | 121.6 (3) |
| H3A—C3—H3C | 109.5 | C5—C10—H10A | 119.2 |
| H3B—C3—H3C | 109.5 | C9—C10—H10A | 119.2 |
| O4—C4—O3 | 124.3 (3) | ||
| C1—O1—C2—O2 | −0.4 (6) | O6—N—C7—C6 | 168.8 (4) |
| C1—O1—C2—C9 | 178.7 (3) | O5—N—C7—C6 | −10.6 (5) |
| C3—O3—C4—O4 | −0.1 (6) | C6—C7—C8—C9 | 0.2 (5) |
| C3—O3—C4—C5 | 179.7 (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—C10 | 0.4 (5) | C7—C8—C9—C2 | 178.6 (3) |
| O4—C4—C5—C6 | −2.1 (5) | O2—C2—C9—C10 | 177.7 (4) |
| O3—C4—C5—C6 | 178.1 (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—C8 | 179.5 (3) |
| C5—C6—C7—C8 | 0.8 (5) | C6—C5—C10—C9 | 1.2 (5) |
| C5—C6—C7—N | −179.2 (3) | C4—C5—C10—C9 | 178.9 (3) |
| O6—N—C7—C8 | −11.2 (5) | C8—C9—C10—C5 | −0.1 (5) |
| O5—N—C7—C8 | 169.4 (4) | C2—C9—C10—C5 | −179.3 (3) |
The Key Laboratory of Nuclear Medicine of Ministry Health of China are thanked for supporting this work.
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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)°.