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Acta Cryst. (2008). E64, o2271    [ doi:10.1107/S1600536808035137 ]

N-(4-Cyanobenzyl)benzamide

Y.-L. Tong, L.-Q. Guo, H.-J. Ma, W. Chen and H.-J. Zhu

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I). Hydrogen bonds are shown as dashed lines.
N-(4-Cyanobenzyl)benzamide top
Crystal data top
C15H12N2OF(000) = 496
Mr = 236.27Dx = 1.257 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 5.864 (1) Åθ = 10–13°
b = 27.164 (5) ŵ = 0.08 mm−1
c = 7.839 (2) ÅT = 298 K
β = 91.09 (3)°Block, colorless
V = 1248.4 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		1461 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
graphiteθmax = 25.3°, θmin = 1.5°
ω/2θ scansh = −7→7
Absorption correction: ψ scan
(North et al., 1968)		k = 0→32
Tmin = 0.976, Tmax = 0.992l = 0→9
2450 measured reflections3 standard reflections every 200 reflections
2233 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.06P)2 + 2P]
where P = (Fo2 + 2Fc2)/3
2233 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C15H12N2OV = 1248.4 (4) Å3
Mr = 236.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.864 (1) ŵ = 0.08 mm−1
b = 27.164 (5) ÅT = 298 K
c = 7.839 (2) Å0.30 × 0.20 × 0.10 mm
β = 91.09 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1461 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.041
Tmin = 0.976, Tmax = 0.992θmax = 25.3°
2450 measured reflections3 standard reflections every 200 reflections
2233 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.186Δρmax = 0.26 e Å−3
S = 1.00Δρmin = −0.24 e Å−3
2233 reflectionsAbsolute structure: ?
163 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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.

references
References top

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