organic compounds Acta Crystallographica Section E
Data collection
Structure Reports Online
Rigaku Saturn CCD area-detector diffractometer Absorption correction: multi-scan (Jacobson, 1998) Tmin = 0.937, Tmax = 0.995
ISSN 1600-5368
3-(Acetylamino)benzoic acid
Refinement
Lars Kr. Hansen,a* German L. Perlovichb,c and Annette Bauer-Brandlb
R[F 2 > 2(F 2)] = 0.052 wR(F 2) = 0.037 S = 1.50 1168 reflections 152 parameters
9339 measured reflections 2325 independent reflections 1168 reflections with F 2 > 2(F 2) Rint = 0.031
H atoms treated by a mixture of independent and constrained refinement ˚ 3 max = 0.22 e A ˚ 3 min = 0.17 e A
a
Department of Chemistry, University of Tromsø, 9037 Tromsø, Norway, Department of Pharmaceutics and Biopharmaceutics, University of Tromsø, 9037 Tromsø, Norway, and cInstitute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo, Russian Federation Correspondence e-mail:
[email protected] b
Table 1 ˚ , ). Hydrogen-bond geometry (A D—H A
D—H
H A
D A
D—H A
O3—H7 O1i N1—H1 O2ii
1.02 (3) 1.02 (2)
1.71 (3) 2.01 (2)
2.714 (2) 3.022 (2)
164 (2) 173.3 (18)
Received 3 April 2007; accepted 10 April 2007 ˚; Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.003 A R factor = 0.052; wR factor = 0.037; data-to-parameter ratio = 7.8.
Symmetry codes: (i) x þ 12; y þ 12; z 12; (ii) x þ 2; y; z.
The title compound, C9H9NO3, was crystallized from methanol. The monoclinic structure features one molecule in the asymmetric unit. The topology of the O—H O and N— H O hydrogen-bond network can be characterized by the graph-set assignments C(9) and R22(14).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.
This study was supported by the Russian Foundation of Basic Research (No. 06-03-96304).
Related literature For the crystal structures of the ortho- and para-isomers of the title compound, see: Feeder & Jones (1992); Kashino et al. (1986); Kovalevsky (1999); Mascarenhas et al. (1980); Rajnikant & Deshmukh (2004). For related literature, see: Etter (1990).
Experimental Crystal data C9H9NO3 Mr = 179.17 Monoclinic, P21 =n ˚ a = 3.9522 (15) A ˚ b = 10.699 (4) A ˚ c = 19.831 (7) A = 93.393 (8)
Acta Cryst. (2007). E63, o2361
˚3 V = 837.1 (5) A Z=4 Mo K radiation = 0.11 mm1 T = 293.1 K 0.60 0.10 0.05 mm
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2363).
References Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P. W., Carruthers, J. R., Cooper, R. L., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. Feeder, N. & Jones, W. (1992). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 211, 111–124. Jacobson, R. (1998). Private communication to the Rigaku Corporation. Kashino, S., Matsushita, T., Iwamoto, T., Yamaguchi, K. & Haisa, M. (1986). Acta Cryst. C42, 457–462. Kovalevsky, A. Yu. (1999). Acta Cryst. C55, IUC9900093. Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Mascarenhas, Y. P., de Almeida, V. N., Lechat, J. R. & Barelli, N. (1980). Acta Cryst. B36, 502–504. Rajnikant, D. K. & Deshmukh, M. B. (2004). J. Chem. Crystallogr. 34, 471–475. Rigaku (2005). CrystalStructure (Version 3.7.0) and CrystalClear . Rigaku Corporation, Tokyo, Japan.
doi:10.1107/S1600536807017783
# 2007 International Union of Crystallography
o2361
supplementary materials
supplementary materials Acta Cryst. (2007). E63, o2361
[ doi:10.1107/S1600536807017783 ]
3-(Acetylamino)benzoic acid L. K. Hansen, G. L. Perlovich and A. Bauer-Brandl Comment The crystal structures of 2-acetylaminobenzoic acid, (I) (Kovalevsky, 1999; Mascarenhas et al., 1980; Rajnikant & Deshmukh, 2004), and 4-acetylaminobenzoic acid, (III) (Kashino et al., 1986; Feeder & Jones, 1992), have been described in the literature. The crystal structure of the title compound (II) has not been solved to date. Therefore, in the present work, we have attempted to fill this gap (Fig. 1, Table 1). The dihedral angle in (II) between the mean plane of the aromatic ring and the plane of atoms C7/O3/O1 is 6.5 (3)°. The corresponding angle between the ring and the acetyl group C2/C1/N1/C8 is 6.3 (3)°. The unit-cell packing of (II) is shown in Figs. 2 and 3. The molecules form layers held together by N—H···O and O—H···O hydrogen bonds. The layers interact with each other by van der Waals forces. The topology of the hydrogen-bond network of (II) can be described by the graph-set assignments introduced by Etter (1990) as a C(9) chain along the c axis and an R22(14) intermolecular ring. The hydrogen-bond networks in (I) and (III) can be characterized as S(6) and C(8), and C(4) and R22(8), respectively. Experimental A commercial sample of 3-acetylaminobenzoic acid was used. Single crystals of (II) were grown from a water–methanol solution by vapour diffusion of water. Refinement The crystals of (II) were of poor quality and weakly diffracting, which accounts for the low fraction of measured reflections. All H atoms, except for those attached to the C9 methyl group, were located in difference maps and their positions and Uiso values were refined freely. The C9 H atoms were positioned geometrically over two orientations of equal occupancy and refined as riding, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C9).
Figures
Fig. 1. A view of (II), showing displacement ellipsoids drawn at the 40% probability level (arbitrary spheres for the H atoms).
sup-1
supplementary materials
Fig. 2. A projection of the molecular packing of (II) along the a axis.
Fig. 3. A projection of the molecular packing of (II) along the b axis.
Fig. 4. Compounds (I), (II) and (III).
3-(Acetylamino)benzoic acid Crystal data C9H9NO3
F000 = 376.00
Mr = 179.17
Dx = 1.422 Mg m−3
Monoclinic, P21/n Hall symbol: -P 2yn a = 3.9522 (15) Å b = 10.699 (4) Å c = 19.831 (7) Å β = 93.393 (8)º V = 837.1 (5) Å3 Z=4
Mo Kα radiation λ = 0.71070 Å Cell parameters from 1899 reflections θ = 2.8–30.5º µ = 0.11 mm−1 T = 293.1 K Prism, colourless 0.60 × 0.10 × 0.05 mm
Data collection Rigaku Saturn CCD area-detector diffractometer
1168 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1
Rint = 0.031
ω scans
θmax = 32.0º
Absorption correction: multi-scan (Jacobson, 1998) Tmin = 0.937, Tmax = 0.995 9339 measured reflections 2325 independent reflections
h = −5→4 k = −15→14 l = −27→26
Refinement Refinement on F
sup-2
(Δ/σ)max = 0.012
supplementary materials R[F2 > 2σ(F2)] = 0.052
Δρmax = 0.22 e Å−3
wR(F2) = 0.037
Δρmin = −0.17 e Å−3
S = 1.50 1187 reflections 152 parameters H atoms treated by a mixture of independent and constrained refinement Weighting scheme based on measured s.u.'s w = 1/ σ2(Fo)
Extinction correction: Larson (1970), equation 22 Extinction coefficient: 50 (6)
Special details Refinement. Refinement using reflections with F2 > 2.0 sigma(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) O1 O2 O3 N1 C1 C2 C3 C4 C5 C6 C7 C8 C9 H1 H2 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13
x
y
z
Uiso*/Ueq
Occ. (
