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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2396.
Published online 2009 September 9. doi:  10.1107/S1600536809034941
PMCID: PMC2970234

3-Cyano­anilinium bromide

Abstract

In the cation of the title compound, C7H7N2 +·Br, all non-H atoms are essentially coplanar [r.m.s. deviation = 0.010 (5) Å]. The compound is isomorphous with the chloride analogue. In the crystal, the cations and anions are connected by N—H(...)Br hydrogen bonds.

Related literature

For applications of metal-organic coordination compounds, see: Fu et al. (2007 [triangle]); Chen et al. (2001 [triangle]); Fu & Xiong (2008 [triangle]); Xiong et al. (1999 [triangle]); Xie et al. (2003 [triangle]); Zhao et al. (2004 [triangle]). For nitrile derivatives, see: Fu et al. (2008 [triangle]); Wang et al. 2002 [triangle]. For the chloride analogue, see: Wen (2008 [triangle]).

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Object name is e-65-o2396-scheme1.jpg

Experimental

Crystal data

  • C7H7N2 +·Br
  • M r = 199.06
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2396-efi1.jpg
  • a = 4.6396 (9) Å
  • b = 6.1757 (12) Å
  • c = 13.542 (3) Å
  • α = 93.07 (3)°
  • β = 96.22 (3)°
  • γ = 97.33 (3)°
  • V = 381.68 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 5.31 mm−1
  • T = 298 K
  • 0.40 × 0.05 × 0.05 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.90, T max = 1.00
  • 3777 measured reflections
  • 1716 independent reflections
  • 1378 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.134
  • S = 1.10
  • 1716 reflections
  • 92 parameters
  • H-atom parameters constrained
  • Δρmax = 0.71 e Å−3
  • Δρmin = −0.75 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034941/bx2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034941/bx2236Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

The construction of metal-organic coordination compounds has attracted much attention owing to potential functions, such as permittivity, fluorescence, magnetism and optical properties (Fu et al., 2007; Chen et al., 2001; Fu & Xiong (2008); Xie et al., 2003; Zhao et al.,2004; Xiong et al., 1999). Nitrile derivatives are a class of excellent ligands for the construction of novel metal-organic frameworks. (Wang et al. 2002; Fu et al., 2008). We report here the crystal structure of the title compound, which is isomorphous with the chloride analogue (Wen, 2008). In the cation all non-H atoms are essentially coplanar [r.m.s. deviation 0.010 (5) Å]. In the crystal structure, the organic cations and bromide ions are connected by N—H···Br hydrogen bonds along b axis, (Table 1), (Fig. 2).

Experimental

The commercial 3-aminobenzonitrile (3 mmol, 0.55 g) and HBr (0.5 ml) were dissolved in ethanol (20 ml). Colourless block-shaped crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation at room temperature.

Refinement

All H atoms attached to C and N atoms were positioned geometrically and treated as riding, with C-H = 0.93 Å, N-H = 0.89 Å and Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(N). A rotating-group model was used for the -NH3 group.

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis showing the N—H···Br interactions (dotted line) in the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity. ...

Crystal data

C7H7N2+·BrZ = 2
Mr = 199.06F(000) = 196
Triclinic, P1Dx = 1.732 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.6396 (9) ÅCell parameters from 1378 reflections
b = 6.1757 (12) Åθ = 3.0–27.5°
c = 13.542 (3) ŵ = 5.31 mm1
α = 93.07 (3)°T = 298 K
β = 96.22 (3)°Block, colourless
γ = 97.33 (3)°0.40 × 0.05 × 0.05 mm
V = 381.68 (13) Å3

Data collection

Rigaku Mercury2 diffractometer1716 independent reflections
Radiation source: fine-focus sealed tube1378 reflections with I > 2σ(I)
graphiteRint = 0.063
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD profile fitting scansh = −6→5
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −8→8
Tmin = 0.90, Tmax = 1.00l = −17→17
3777 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.053P)2 + 0.0394P] where P = (Fo2 + 2Fc2)/3
1716 reflections(Δ/σ)max < 0.001
92 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = −0.75 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

xyzUiso*/Ueq
N20.6256 (9)0.2461 (6)0.6051 (3)0.0419 (10)
H2A0.74370.14460.59900.063*
H2B0.71750.37550.59270.063*
H2C0.46530.21180.56190.063*
N1−0.0113 (11)0.7158 (8)0.8871 (4)0.0575 (13)
C40.5438 (10)0.2565 (7)0.7064 (4)0.0339 (10)
C30.3783 (10)0.4177 (7)0.7330 (3)0.0349 (10)
H30.32150.51660.68770.042*
C20.3001 (10)0.4273 (7)0.8286 (4)0.0350 (10)
C50.6331 (11)0.1113 (7)0.7719 (4)0.0389 (11)
H50.74460.00480.75270.047*
C70.3878 (12)0.2814 (8)0.8962 (4)0.0429 (12)
H70.33450.28890.96040.051*
C60.5540 (12)0.1259 (8)0.8677 (4)0.0473 (13)
H60.61460.02870.91320.057*
C10.1216 (11)0.5910 (8)0.8593 (4)0.0422 (12)
Br10.09268 (11)0.23870 (7)0.42210 (4)0.0448 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N20.053 (3)0.044 (2)0.032 (2)0.0176 (19)0.0038 (19)0.0003 (18)
N10.058 (3)0.052 (3)0.067 (3)0.020 (2)0.016 (3)−0.004 (2)
C40.040 (3)0.028 (2)0.033 (3)0.0073 (18)0.004 (2)−0.0017 (18)
C30.039 (3)0.033 (2)0.032 (3)0.010 (2)0.000 (2)0.0010 (19)
C20.030 (2)0.034 (2)0.041 (3)0.0057 (18)0.005 (2)−0.002 (2)
C50.049 (3)0.034 (2)0.037 (3)0.018 (2)0.007 (2)−0.001 (2)
C70.056 (3)0.039 (3)0.035 (3)0.011 (2)0.010 (2)0.000 (2)
C60.062 (4)0.040 (3)0.045 (3)0.015 (2)0.010 (3)0.014 (2)
C10.045 (3)0.040 (3)0.044 (3)0.012 (2)0.011 (2)0.000 (2)
Br10.0573 (4)0.0399 (3)0.0423 (4)0.0214 (2)0.0112 (3)0.0037 (2)

Geometric parameters (Å, °)

N2—C41.463 (6)C3—H30.9300
N2—H2A0.8900C2—C71.384 (7)
N2—H2B0.8900C2—C11.457 (6)
N2—H2C0.8900C5—C61.388 (7)
N1—C11.121 (6)C5—H50.9300
C4—C51.365 (6)C7—C61.371 (7)
C4—C31.388 (6)C7—H70.9300
C3—C21.383 (7)C6—H60.9300
C4—N2—H2A109.5C3—C2—C1120.2 (4)
C4—N2—H2B109.5C7—C2—C1119.1 (5)
H2A—N2—H2B109.5C4—C5—C6118.6 (4)
C4—N2—H2C109.5C4—C5—H5120.7
H2A—N2—H2C109.5C6—C5—H5120.7
H2B—N2—H2C109.5C6—C7—C2119.4 (5)
C5—C4—C3122.0 (4)C6—C7—H7120.3
C5—C4—N2119.8 (4)C2—C7—H7120.3
C3—C4—N2118.2 (4)C7—C6—C5121.0 (5)
C2—C3—C4118.2 (4)C7—C6—H6119.5
C2—C3—H3120.9C5—C6—H6119.5
C4—C3—H3120.9N1—C1—C2177.0 (6)
C3—C2—C7120.7 (4)
C5—C4—C3—C2−0.9 (7)N2—C4—C5—C6179.6 (5)
N2—C4—C3—C2179.8 (4)C3—C2—C7—C60.0 (7)
C4—C3—C2—C70.7 (7)C1—C2—C7—C6179.5 (5)
C4—C3—C2—C1−178.8 (4)C2—C7—C6—C5−0.6 (8)
C3—C4—C5—C60.3 (7)C4—C5—C6—C70.5 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···Br1i0.892.593.434 (4)159
N2—H2B···Br1ii0.892.463.337 (4)169
N2—H2C···Br10.892.453.299 (4)160

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2236).

References

  • Chen, Z.-F., Li, B.-Q., Xie, Y.-R., Xiong, R.-G., You, X.-Z. & Feng, X.-L. (2001). Inorg. Chem. Commun.4, 346–349.
  • Fu, D.-W., Song, Y.-M., Wang, G.-X., Ye, Q., Xiong, R.-G., Akutagawa, T., Nakamura, T., Chan, P. W. H., Huang, S.-P. & -, D. (2007). J. Am. Chem. Soc.129, 5346–5347. [PubMed]
  • Fu, D.-W. & Xiong, R.-G. (2008). Dalton Trans. pp. 3946–3948. [PubMed]
  • Fu, D.-W., Zhang, W. & Xiong, R.-G. (2008). Cryst. Growth Des.8, 3461–3464.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, L.-Z., Wang, X.-S., Li, Y.-H., Bai, Z.-P., Xiong, R.-G., Xiong, M. & Li, G.-W. (2002). Chin. J. Inorg. Chem.18, 1191–1194.
  • Wen, X.-C. (2008). Acta Cryst. E64, o1462. [PMC free article] [PubMed]
  • Xie, Y.-R., Zhao, H., Wang, X.-S., Qu, Z.-R., Xiong, R.-G., Xue, X.-A., Xue, Z.-L. & You, X.-Z. (2003). Eur. J. Inorg. Chem.20, 3712–3715.
  • Xiong, R.-G., Zuo, J.-L., You, X.-Z., Fun, H.-K. & Raj, S. S. S. (1999). New J. Chem.23, 1051–1052.
  • Zhao, H., Ye, Q., Wu, Q., Song, Y.-M., Liu, Y.-J. & Xiong, R.-G. (2004). Z. Anorg. Allg. Chem.630, 1367–1370.

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