Acta Cryst. (2009). E65, o1194 [ doi:10.1107/S1600536809015797 ]
In the molecule of the title compound, C10H10N2O5, intramolecular C-H
O interactions result in the formation of a five- and a six-membered ring. The five-membered ring is planar and is oriented at a dihedral angle of 0.34 (3)° with respect to the plane of the aromatic ring, while the six-membered ring has a twist conformation. In the crystal structure, intermolecular C-HO interactions link the molecules into chains.
The title compound was prepared by the reaction of 4-aminophenol, fuming nitric acid and acetic anhydride (Gu, 2007). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.2 g) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 2 d.
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./hk2677fig1thm.gif)
| Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines. |
| C10H10N2O5 | F000 = 992 |
| Mr = 238.20 | Dx = 1.444 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 25 reflections |
| a = 24.859 (5) Å | θ = 9–13º |
| b = 4.7060 (9) Å | µ = 0.12 mm−1 |
| c = 19.773 (4) Å | T = 298 K |
| β = 108.67 (3)º | Needle, colorless |
| V = 2191.4 (8) Å3 | 0.30 × 0.10 × 0.10 mm |
| Z = 8 |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.021 |
| Radiation source: fine-focus sealed tube | θmax = 25.3º |
| Monochromator: graphite | θmin = 1.7º |
| T = 298 K | h = 0→29 |
| ω/2θ scans | k = 0→5 |
| Absorption correction: ψ scan (North et al., 1968) | l = −23→22 |
| Tmin = 0.966, Tmax = 0.988 | 3 standard reflections |
| 2039 measured reflections | every 120 min |
| 1992 independent reflections | intensity decay: 1% |
| 1310 reflections with I > 2σ(I) |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.1P)2 + 1.4P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.187 | (Δ/σ)max < 0.001 |
| S = 1.00 | Δρmax = 0.51 e Å−3 |
| 1992 reflections | Δρmin = −0.56 e Å−3 |
| 136 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008) |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.091 (8) |
| Secondary atom site location: difference Fourier map |
| C10H10N2O5 | V = 2191.4 (8) Å3 |
| Mr = 238.20 | Z = 8 |
| Monoclinic, C2/c | Mo Kα |
| a = 24.859 (5) Å | µ = 0.12 mm−1 |
| b = 4.7060 (9) Å | T = 298 K |
| c = 19.773 (4) Å | 0.30 × 0.10 × 0.10 mm |
| β = 108.67 (3)º |
| Enraf–Nonius CAD-4 diffractometer | 1310 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.021 |
| Tmin = 0.966, Tmax = 0.988 | 3 standard reflections |
| 2039 measured reflections | every 120 min |
| 1992 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.064 | 136 parameters |
| wR(F2) = 0.187 | H-atom parameters constrained |
| S = 1.00 | Δρmax = 0.51 e Å−3 |
| 1992 reflections | Δρmin = −0.56 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 | ||
| N1 | 0.07647 (10) | 0.5724 (5) | 0.10146 (12) | 0.0515 (4) | |
| H1A | 0.0516 | 0.7061 | 0.0897 | 0.062* | |
| N2 | 0.06554 (11) | −0.0326 (5) | −0.09742 (14) | 0.0514 (7) | |
| O1 | 0.12640 (12) | 0.2734 (6) | 0.18301 (13) | 0.0844 (9) | |
| O2 | 0.02074 (10) | −0.1112 (6) | −0.09213 (14) | 0.0857 (9) | |
| O3 | 0.08434 (11) | −0.1300 (6) | −0.14164 (15) | 0.0872 (9) | |
| O4 | 0.17417 (10) | 0.2065 (5) | −0.10210 (12) | 0.0688 (7) | |
| O5 | 0.21944 (11) | 0.6153 (5) | −0.11162 (14) | 0.0770 (8) | |
| C1 | 0.06037 (13) | 0.5863 (7) | 0.21107 (15) | 0.0515 (4) | |
| H1B | 0.0723 | 0.5004 | 0.2576 | 0.077* | |
| H1C | 0.0204 | 0.5560 | 0.1888 | 0.077* | |
| H1D | 0.0680 | 0.7866 | 0.2156 | 0.077* | |
| C2 | 0.09173 (14) | 0.4575 (7) | 0.16704 (16) | 0.0515 (4) | |
| C3 | 0.10194 (13) | 0.4694 (7) | 0.05257 (16) | 0.0515 (4) | |
| C4 | 0.07426 (12) | 0.2714 (6) | 0.00398 (15) | 0.0457 (7) | |
| H4A | 0.0399 | 0.1961 | 0.0048 | 0.055* | |
| C5 | 0.09830 (12) | 0.1834 (6) | −0.04697 (15) | 0.0441 (7) | |
| C6 | 0.14971 (11) | 0.2930 (6) | −0.05065 (15) | 0.0427 (7) | |
| C7 | 0.17661 (12) | 0.4918 (6) | 0.00190 (17) | 0.0512 (8) | |
| H7A | 0.2116 | 0.5645 | 0.0029 | 0.061* | |
| C8 | 0.15321 (13) | 0.5825 (6) | 0.05171 (16) | 0.0514 (8) | |
| H8A | 0.1716 | 0.7196 | 0.0850 | 0.062* | |
| C9 | 0.20627 (12) | 0.3744 (6) | −0.13076 (16) | 0.0484 (7) | |
| C10 | 0.22342 (15) | 0.2336 (7) | −0.18863 (18) | 0.0607 (9) | |
| H10A | 0.2458 | 0.3629 | −0.2061 | 0.091* | |
| H10B | 0.1901 | 0.1808 | −0.2270 | 0.091* | |
| H10C | 0.2454 | 0.0667 | −0.1699 | 0.091* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0594 (9) | 0.0497 (9) | 0.0486 (8) | 0.0021 (7) | 0.0217 (7) | 0.0021 (7) |
| N2 | 0.0494 (14) | 0.0471 (15) | 0.0587 (16) | −0.0106 (12) | 0.0185 (12) | −0.0027 (13) |
| O1 | 0.0895 (18) | 0.093 (2) | 0.0743 (17) | 0.0254 (16) | 0.0320 (14) | 0.0246 (15) |
| O2 | 0.0725 (16) | 0.093 (2) | 0.100 (2) | −0.0430 (15) | 0.0402 (15) | −0.0344 (16) |
| O3 | 0.0887 (18) | 0.095 (2) | 0.0935 (19) | −0.0414 (16) | 0.0506 (16) | −0.0460 (16) |
| O4 | 0.0795 (16) | 0.0577 (14) | 0.0814 (17) | −0.0073 (12) | 0.0426 (14) | −0.0024 (12) |
| O5 | 0.109 (2) | 0.0442 (14) | 0.0964 (19) | −0.0279 (13) | 0.0595 (16) | −0.0069 (13) |
| C1 | 0.0594 (9) | 0.0497 (9) | 0.0486 (8) | 0.0021 (7) | 0.0217 (7) | 0.0021 (7) |
| C2 | 0.0594 (9) | 0.0497 (9) | 0.0486 (8) | 0.0021 (7) | 0.0217 (7) | 0.0021 (7) |
| C3 | 0.0594 (9) | 0.0497 (9) | 0.0486 (8) | 0.0021 (7) | 0.0217 (7) | 0.0021 (7) |
| C4 | 0.0444 (15) | 0.0400 (16) | 0.0561 (17) | −0.0079 (13) | 0.0207 (13) | −0.0007 (14) |
| C5 | 0.0483 (15) | 0.0337 (14) | 0.0490 (16) | −0.0059 (13) | 0.0139 (13) | −0.0002 (13) |
| C6 | 0.0463 (15) | 0.0332 (14) | 0.0508 (16) | −0.0008 (13) | 0.0184 (13) | 0.0066 (13) |
| C7 | 0.0479 (16) | 0.0421 (16) | 0.0637 (19) | −0.0107 (13) | 0.0181 (15) | −0.0017 (15) |
| C8 | 0.0601 (18) | 0.0422 (17) | 0.0498 (17) | −0.0059 (15) | 0.0146 (14) | −0.0020 (14) |
| C9 | 0.0521 (17) | 0.0392 (17) | 0.0585 (18) | −0.0001 (14) | 0.0239 (14) | 0.0058 (14) |
| C10 | 0.076 (2) | 0.0516 (19) | 0.068 (2) | −0.0007 (17) | 0.0421 (18) | 0.0031 (17) |
| O1—C2 | 1.191 (4) | C3—C4 | 1.357 (4) |
| O4—C9 | 1.368 (3) | C3—C8 | 1.386 (4) |
| O4—C6 | 1.402 (3) | C4—C5 | 1.389 (4) |
| O5—C9 | 1.207 (3) | C4—H4A | 0.9300 |
| N1—C2 | 1.343 (4) | C5—C6 | 1.402 (4) |
| N1—C3 | 1.401 (4) | C6—C7 | 1.399 (4) |
| N1—H1A | 0.8600 | C7—C8 | 1.363 (4) |
| N2—O3 | 1.206 (3) | C7—H7A | 0.9300 |
| N2—O2 | 1.209 (3) | C8—H8A | 0.9300 |
| N2—C5 | 1.474 (4) | C9—C10 | 1.497 (4) |
| C1—C2 | 1.473 (4) | C10—H10A | 0.9600 |
| C1—H1B | 0.9600 | C10—H10B | 0.9600 |
| C1—H1C | 0.9600 | C10—H10C | 0.9600 |
| C1—H1D | 0.9600 | ||
| C9—O4—C6 | 125.4 (2) | C4—C5—C6 | 122.6 (3) |
| C2—N1—C3 | 118.5 (3) | C4—C5—N2 | 115.1 (2) |
| C2—N1—H1A | 120.8 | C6—C5—N2 | 122.3 (3) |
| C3—N1—H1A | 120.8 | C7—C6—C5 | 115.7 (3) |
| O2—N2—C5 | 118.5 (3) | C7—C6—O4 | 121.2 (2) |
| O3—N2—O2 | 121.8 (3) | C5—C6—O4 | 123.0 (3) |
| O3—N2—C5 | 119.6 (2) | C8—C7—C6 | 122.2 (3) |
| C2—C1—H1B | 109.5 | C8—C7—H7A | 118.9 |
| C2—C1—H1C | 109.5 | C6—C7—H7A | 118.9 |
| H1B—C1—H1C | 109.5 | C7—C8—C3 | 119.7 (3) |
| C2—C1—H1D | 109.5 | C7—C8—H8A | 120.2 |
| H1B—C1—H1D | 109.5 | C3—C8—H8A | 120.2 |
| H1C—C1—H1D | 109.5 | O5—C9—O4 | 123.2 (3) |
| O1—C2—N1 | 120.4 (3) | O5—C9—C10 | 122.7 (3) |
| O1—C2—C1 | 128.2 (3) | O4—C9—C10 | 114.1 (3) |
| N1—C2—C1 | 111.5 (3) | C9—C10—H10A | 109.5 |
| C4—C3—C8 | 121.0 (3) | C9—C10—H10B | 109.5 |
| C4—C3—N1 | 119.2 (3) | H10A—C10—H10B | 109.5 |
| C8—C3—N1 | 119.7 (3) | C9—C10—H10C | 109.5 |
| C3—C4—C5 | 118.7 (3) | H10A—C10—H10C | 109.5 |
| C3—C4—H4A | 120.7 | H10B—C10—H10C | 109.5 |
| C5—C4—H4A | 120.7 | ||
| C3—N1—C2—O1 | 0.4 (5) | N2—C5—C6—C7 | −178.6 (3) |
| C3—N1—C2—C1 | −179.1 (3) | C4—C5—C6—O4 | −179.7 (3) |
| C2—N1—C3—C4 | 97.3 (4) | N2—C5—C6—O4 | −0.2 (4) |
| C2—N1—C3—C8 | −86.5 (4) | C9—O4—C6—C7 | −33.5 (4) |
| C8—C3—C4—C5 | 0.0 (5) | C9—O4—C6—C5 | 148.2 (3) |
| N1—C3—C4—C5 | 176.2 (3) | C5—C6—C7—C8 | −2.7 (4) |
| C3—C4—C5—C6 | −0.7 (5) | O4—C6—C7—C8 | 178.9 (3) |
| C3—C4—C5—N2 | 179.8 (3) | C6—C7—C8—C3 | 2.2 (5) |
| O3—N2—C5—C4 | −177.0 (3) | C4—C3—C8—C7 | −0.7 (5) |
| O2—N2—C5—C4 | 1.6 (4) | N1—C3—C8—C7 | −176.9 (3) |
| O3—N2—C5—C6 | 3.5 (4) | C6—O4—C9—O5 | 3.9 (5) |
| O2—N2—C5—C6 | −178.0 (3) | C6—O4—C9—C10 | −175.7 (3) |
| C4—C5—C6—C7 | 1.9 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4A···O2 | 0.93 | 2.33 | 2.647 (4) | 100 |
| C7—H7A···O5 | 0.93 | 2.35 | 2.836 (4) | 113 |
| C10—H10C···O5i | 0.96 | 2.59 | 3.300 (4) | 130 |
| Symmetry codes: (i) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4A···O2 | 0.93 | 2.33 | 2.647 (4) | 100 |
| C7—H7A···O5 | 0.93 | 2.35 | 2.836 (4) | 113 |
| C10—H10C···O5i | 0.96 | 2.59 | 3.300 (4) | 130 |
| Symmetry codes: (i) x, y−1, z. |
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gu, Z. (2007). Faming Zhuanli Shenqing Gongkai Shuomingshu, 101085741. [Please define this number. Page, deposition, reference number, patent application?]
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.
The title compound is an important medical intermediate used to synthesize 3,4-diaminophenol, which is the main raw material of luxabendazole (Gu, 2007). We report herein the crystal structure of the title compound, which is of interest to us in the field.
In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C3-C8) is, of course, planar. Intramolecular C-H···O interactions (Table 1) result in the formations of five- and six-membered rings: B (O2/N2/C4/C5/H4A) and C (O4/O5/C5-C7/C9/H7A). Ring B is planar and it is oriented with respect to ring A at a dihedral angle of 0.34 (3)°, while ring C has a twisted conformation.
In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules into chains, in which they may be effective in the stabilization of the structure.