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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2271.
Published online 2008 November 8. doi:  10.1107/S1600536808035137
PMCID: PMC2959981

N-(4-Cyano­benz­yl)benzamide

Abstract

The title compound, C15H12N2O, is a derivative of 4-(amino­meth­yl)benzonitrile, an important pestcide inter­mediate. In the crystal structure, mol­ecules are linked via inter­molecular N—H(...)O hydrogen bonds, forming infinite chains.

Related literature

For general background, see: Blaschke et al. (1976 [triangle]); Gesing (1989 [triangle]). For the synthetic procedure, see: Guo et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o2271-scheme1.jpg

Experimental

Crystal data

  • C15H12N2O
  • M r = 236.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2271-efi1.jpg
  • a = 5.864 (1) Å
  • b = 27.164 (5) Å
  • c = 7.839 (2) Å
  • β = 91.09 (3)°
  • V = 1248.4 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.976, T max = 0.992
  • 2450 measured reflections
  • 2233 independent reflections
  • 1461 reflections with I > 2σ(I)
  • R int = 0.041
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.075
  • wR(F 2) = 0.186
  • S = 1.00
  • 2233 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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/S1600536808035137/im2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035137/im2085Isup2.hkl

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

Acknowledgments

The authors thank Dr Shan Liu, Nanjing University of Technology, for his useful suggestions and guidance, and thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

N-(4-Cyanobenzyl)benzamide is a derivative of 4-(aminomethyl)benzontrile (Gesing, 1989), which is an important in the synthesis of pestcides as well as of some drugs (Blaschke et al., 1976).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

In the crystal structure, molecules are linked together to form infinite chains via intermolecular N—H···O hydrogen bonds (Fig. 2).

Experimental

The title compound, (I) was prepared by a method reported by Guo et al. (2008).

Crystals were obtained by dissolving (I) (0.8 g, 3.4 mmol) in dichloromethane (20 ml) and slowly evaporating the solvent slowly at room temperature for about 5 d.

Refinement

H atoms were positioned geometrically, with N—H = 0.86 and C—H = 0.93Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C/N), where x = 1.2 for aromatic H and x = 1.5 for other H.

Figures

Fig. 1.
Molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C15H12N2OF000 = 496
Mr = 236.27Dx = 1.257 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 5.864 (1) Åθ = 10–13º
b = 27.164 (5) ŵ = 0.08 mm1
c = 7.839 (2) ÅT = 298 (2) K
β = 91.09 (3)ºBlock, colorless
V = 1248.4 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.041
Radiation source: fine-focus sealed tubeθmax = 25.3º
Monochromator: graphiteθmin = 1.5º
T = 298(2) Kh = −7→7
ω/2θ scansk = 0→32
Absorption correction: ψ scan(North et al., 1968)l = 0→9
Tmin = 0.976, Tmax = 0.9923 standard reflections
2450 measured reflections every 200 reflections
2233 independent reflections intensity decay: none
1461 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.186  w = 1/[σ2(Fo2) + (0.06P)2 + 2P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2233 reflectionsΔρmax = 0.26 e Å3
163 parametersΔρmin = −0.24 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

xyzUiso*/Ueq
O0.3309 (5)0.24546 (11)0.3711 (3)0.0728 (9)
C10.5980 (7)0.02472 (18)0.7639 (6)0.0648 (11)
N10.7125 (8)−0.00565 (17)0.8071 (6)0.0976 (15)
N20.0883 (4)0.23194 (10)0.5795 (3)0.0396 (7)
H2A0.02690.24260.67110.048*
C20.4555 (6)0.06509 (14)0.7054 (4)0.0465 (9)
C30.5228 (6)0.11328 (14)0.7289 (4)0.0473 (9)
H3A0.66020.12010.78520.057*
C40.3894 (5)0.15128 (13)0.6701 (4)0.0422 (8)
H4A0.43830.18360.68500.051*
C50.1830 (5)0.14198 (12)0.5889 (4)0.0354 (8)
C60.1169 (6)0.09393 (14)0.5685 (5)0.0514 (9)
H6A−0.02240.08730.51460.062*
C70.2468 (7)0.05557 (15)0.6239 (5)0.0571 (10)
H7A0.19710.02340.60770.069*
C80.0315 (5)0.18301 (13)0.5198 (4)0.0431 (8)
H8A0.03840.18280.39630.052*
H8B−0.12470.17590.55010.052*
C90.2321 (5)0.26091 (13)0.4974 (4)0.0385 (8)
C100.2683 (5)0.31165 (12)0.5607 (3)0.0332 (7)
C110.1042 (5)0.33738 (13)0.6512 (4)0.0407 (8)
H11A−0.03020.32170.68090.049*
C120.1384 (6)0.38530 (14)0.6968 (5)0.0528 (10)
H12A0.02970.40200.75960.063*
C130.3361 (7)0.40892 (15)0.6489 (5)0.0550 (10)
H13A0.35750.44200.67450.066*
C140.5014 (6)0.38324 (16)0.5631 (5)0.0542 (10)
H14A0.63780.39860.53620.065*
C150.4657 (5)0.33607 (14)0.5182 (4)0.0447 (9)
H15A0.57650.31950.45720.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O0.094 (2)0.0745 (19)0.0522 (15)−0.0141 (16)0.0520 (15)−0.0124 (14)
C10.052 (3)0.075 (3)0.067 (3)0.006 (2)−0.011 (2)−0.005 (2)
N10.087 (3)0.079 (3)0.125 (4)0.026 (2)−0.026 (3)0.003 (3)
N20.0334 (15)0.0591 (18)0.0267 (13)0.0019 (13)0.0090 (11)−0.0020 (12)
C20.044 (2)0.055 (2)0.0412 (19)0.0021 (17)0.0006 (16)−0.0035 (16)
C30.0340 (19)0.067 (2)0.0407 (19)−0.0052 (17)−0.0050 (15)−0.0033 (17)
C40.0356 (18)0.053 (2)0.0385 (18)−0.0108 (16)0.0028 (14)−0.0059 (15)
C50.0255 (16)0.055 (2)0.0256 (15)0.0002 (14)0.0042 (12)−0.0041 (13)
C60.038 (2)0.063 (2)0.053 (2)−0.0110 (18)−0.0145 (17)−0.0085 (18)
C70.056 (2)0.050 (2)0.064 (2)−0.0027 (19)−0.013 (2)−0.0099 (19)
C80.0338 (18)0.060 (2)0.0356 (17)−0.0021 (16)−0.0016 (14)0.0004 (15)
C90.0300 (17)0.061 (2)0.0250 (15)0.0000 (15)0.0120 (13)0.0029 (14)
C100.0218 (15)0.057 (2)0.0206 (14)0.0046 (14)−0.0001 (12)0.0082 (13)
C110.0242 (16)0.061 (2)0.0365 (17)0.0016 (15)0.0004 (13)0.0025 (15)
C120.052 (2)0.057 (2)0.049 (2)0.0076 (19)−0.0028 (17)−0.0064 (18)
C130.057 (2)0.058 (2)0.049 (2)−0.011 (2)−0.0165 (19)0.0015 (18)
C140.037 (2)0.076 (3)0.049 (2)−0.0154 (19)−0.0079 (17)0.0077 (19)
C150.0305 (18)0.070 (3)0.0343 (17)0.0034 (17)0.0040 (14)0.0054 (16)

Geometric parameters (Å, °)

O—C91.230 (4)C7—H7A0.9300
C1—N11.113 (5)C8—H8A0.9700
C1—C21.448 (6)C8—H8B0.9700
N2—C91.329 (4)C9—C101.479 (5)
N2—C81.446 (4)C10—C151.380 (4)
N2—H2A0.8600C10—C111.394 (4)
C2—C31.379 (5)C11—C121.364 (5)
C2—C71.394 (5)C11—H11A0.9300
C3—C41.370 (5)C12—C131.383 (5)
C3—H3A0.9300C12—H12A0.9300
C4—C51.380 (4)C13—C141.380 (5)
C4—H4A0.9300C13—H13A0.9300
C5—C61.370 (5)C14—C151.344 (5)
C5—C81.519 (5)C14—H14A0.9300
C6—C71.357 (5)C15—H15A0.9300
C6—H6A0.9300
N1—C1—C2178.1 (5)N2—C8—H8B108.4
C9—N2—C8122.1 (3)C5—C8—H8B108.4
C9—N2—H2A118.9H8A—C8—H8B107.5
C8—N2—H2A118.9O—C9—N2120.0 (3)
C3—C2—C7118.9 (3)O—C9—C10121.4 (3)
C3—C2—C1121.0 (3)N2—C9—C10118.5 (3)
C7—C2—C1120.1 (3)C15—C10—C11118.2 (3)
C4—C3—C2120.7 (3)C15—C10—C9118.9 (3)
C4—C3—H3A119.7C11—C10—C9122.8 (3)
C2—C3—H3A119.7C12—C11—C10120.8 (3)
C3—C4—C5120.5 (3)C12—C11—H11A119.6
C3—C4—H4A119.8C10—C11—H11A119.6
C5—C4—H4A119.8C11—C12—C13119.4 (4)
C6—C5—C4118.2 (3)C11—C12—H12A120.3
C6—C5—C8119.7 (3)C13—C12—H12A120.3
C4—C5—C8122.1 (3)C14—C13—C12119.9 (4)
C7—C6—C5122.6 (3)C14—C13—H13A120.1
C7—C6—H6A118.7C12—C13—H13A120.1
C5—C6—H6A118.7C15—C14—C13120.1 (3)
C6—C7—C2119.1 (4)C15—C14—H14A119.9
C6—C7—H7A120.4C13—C14—H14A119.9
C2—C7—H7A120.4C14—C15—C10121.5 (3)
N2—C8—C5115.5 (3)C14—C15—H15A119.3
N2—C8—H8A108.4C10—C15—H15A119.3
C5—C8—H8A108.4
C7—C2—C3—C4−1.3 (5)C8—N2—C9—C10175.9 (3)
C1—C2—C3—C4178.7 (3)O—C9—C10—C15−22.3 (5)
C2—C3—C4—C51.2 (5)N2—C9—C10—C15158.1 (3)
C3—C4—C5—C6−0.3 (5)O—C9—C10—C11152.8 (3)
C3—C4—C5—C8−179.2 (3)N2—C9—C10—C11−26.8 (4)
C4—C5—C6—C7−0.4 (5)C15—C10—C11—C12−0.2 (5)
C8—C5—C6—C7178.5 (3)C9—C10—C11—C12−175.4 (3)
C5—C6—C7—C20.2 (6)C10—C11—C12—C131.6 (5)
C3—C2—C7—C60.7 (6)C11—C12—C13—C14−3.2 (5)
C1—C2—C7—C6−179.3 (4)C12—C13—C14—C153.4 (5)
C9—N2—C8—C590.5 (4)C13—C14—C15—C10−2.1 (5)
C6—C5—C8—N2166.8 (3)C11—C10—C15—C140.4 (5)
C4—C5—C8—N2−14.4 (4)C9—C10—C15—C14175.8 (3)
C8—N2—C9—O−3.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···Oi0.861.992.830 (4)166

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2085).

References

  • 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.
  • Blaschke, G., Joergens, R. & Claassen, G. (1976). Arch. Pharm.309, 258–65. [PubMed]
  • Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Gesing, E. (1989). Bayer AG, Germany. DE Patent No. 3 727 126.
  • Guo, L. Q., Ma, H. J., Ni, J. P., Xu, S. C., Liu, L., Wan, Q. & Wang, X. J. (2008). Agrochem. Res. Appl 12, 15–18.
  • 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. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography