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

Allen

Blaschke

Hai-Jun Ma

Hong-Jun Zhu

Li-Qin Guo

North

Sheldrick

Wei Chen

Yi-Li Tong

English

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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&#8212;H...O hydrogen bonds, forming infinite chains

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Acta Crystallographica Section E Structure Reports Online

N-(4-Cyanobenzyl)benzamide

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N-(4-Cyanobenzyl)benzamide
Yi-Li Tong,a Li-Qin Guo,b Hai-Jun Ma,b Wei Chena and
Hong-Jun Zhua*
aDepartment of Applied Chemistry, College of Science, Nanjing University of
Technology, Nanjing 210009, People’s Republic of China, and bJiangsu Pesticide
Research Institute Co. Ltd, Nanjing 210009, People’s Republic of China
Correspondence e-mail: zhuhj@njut.edu.cn
Received 9 October 2008; accepted 28 October 2008
Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.005 A˚;
R factor = 0.075; wR factor = 0.186; data-to-parameter ratio = 13.7.
The title compound, C15H12N2O, is a derivative of 4-(amino-
methyl)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); Gesing
(1989). For the synthetic procedure, see: Guo et al. (2008). For
bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
C15H12N2O
Mr = 236.27
Monoclinic, P21=n
a = 5.864 (1) A˚
b = 27.164 (5) A˚
c = 7.839 (2) A˚
 = 91.09 (3)
V = 1248.4 (4) A˚3
Z = 4
Mo K radiation
 = 0.08 mm1
T = 298 (2) K
0.30  0.20  0.10 mm
Data collection
Enraf–Nonius CAD-4
diffractometer
Absorption correction:  scan
(North et al., 1968)
Tmin = 0.976, Tmax = 0.992
2450 measured reflections
2233 independent reflections
1461 reflections with I > 2(I)
Rint = 0.041
3 standard reflections
every 200 reflections
intensity decay: none
Refinement
R[F 2 > 2(F 2)] = 0.075
wR(F 2) = 0.186
S = 1.00
2233 reflections
163 parameters
H-atom parameters constrained
max = 0.26 e A˚
3
min = 0.24 e A˚3
Table 1
Hydrogen-bond geometry (A˚, ).
D—H  A D—H H  A D  A D—H  A
N2—H2A  Oi 0.86 1.99 2.830 (4) 166
Symmetry code: (i) x 12;yþ 12; zþ 12.
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
refinement: CAD-4 Software; 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.
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 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.
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Nether-
lands.
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.
organic compounds
Acta Cryst. (2008). E64, o2271 doi:10.1107/S1600536808035137 Tong et al. o2271
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
supporting information
sup-1Acta Cryst. (2008). E64, o2271    
supporting information
Acta Cryst. (2008). E64, o2271    [doi:10.1107/S1600536808035137]
N-(4-Cyanobenzyl)benzamide
Yi-Li Tong, Li-Qin Guo, Hai-Jun Ma, Wei Chen and Hong-Jun Zhu
S1. 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).
S2. 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.
S3. 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.
Figure 1
Molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 
50% probability level. 
supporting information
sup-2Acta Cryst. (2008). E64, o2271    
Figure 2
Packing diagram of (I). Hydrogen bonds are shown as dashed lines. 
N-(4-Cyanobenzyl)benzamide 
Crystal data 
C15H12N2O
Mr = 236.27
Monoclinic, P21/n
Hall symbol: -P 2yn
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
F(000) = 496
Dx = 1.257 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 25 reflections
θ = 10–13°
µ = 0.08 mm−1
T = 298 K
Block, colorless
0.30 × 0.20 × 0.10 mm
Data collection 
Enraf–Nonius CAD-4 
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
ω/2θ scans
Absorption correction: ψ scan 
(North et al., 1968)
Tmin = 0.976, Tmax = 0.992
2450 measured reflections
2233 independent reflections
1461 reflections with I > 2σ(I)
Rint = 0.041
θmax = 25.3°, θmin = 1.5°
h = −7→7
k = 0→32
l = 0→9
3 standard reflections every 200 reflections
intensity decay: none
Refinement 
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.075
wR(F2) = 0.186
S = 1.00
2233 reflections
163 parameters
0 restraints
Primary atom site location: structure-invariant 
direct methods
Secondary atom site location: difference Fourier 
map
Hydrogen site location: inferred from 
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.06P)2 + 2P] 
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.26 e Å−3
Δρmin = −0.24 e Å−3
supporting information
sup-3Acta Cryst. (2008). E64, o2271    
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) 
x y z Uiso*/Ueq
O 0.3309 (5) 0.24546 (11) 0.3711 (3) 0.0728 (9)
C1 0.5980 (7) 0.02472 (18) 0.7639 (6) 0.0648 (11)
N1 0.7125 (8) −0.00565 (17) 0.8071 (6) 0.0976 (15)
N2 0.0883 (4) 0.23194 (10) 0.5795 (3) 0.0396 (7)
H2A 0.0269 0.2426 0.6711 0.048*
C2 0.4555 (6) 0.06509 (14) 0.7054 (4) 0.0465 (9)
C3 0.5228 (6) 0.11328 (14) 0.7289 (4) 0.0473 (9)
H3A 0.6602 0.1201 0.7852 0.057*
C4 0.3894 (5) 0.15128 (13) 0.6701 (4) 0.0422 (8)
H4A 0.4383 0.1836 0.6850 0.051*
C5 0.1830 (5) 0.14198 (12) 0.5889 (4) 0.0354 (8)
C6 0.1169 (6) 0.09393 (14) 0.5685 (5) 0.0514 (9)
H6A −0.0224 0.0873 0.5146 0.062*
C7 0.2468 (7) 0.05557 (15) 0.6239 (5) 0.0571 (10)
H7A 0.1971 0.0234 0.6077 0.069*
C8 0.0315 (5) 0.18301 (13) 0.5198 (4) 0.0431 (8)
H8A 0.0384 0.1828 0.3963 0.052*
H8B −0.1247 0.1759 0.5501 0.052*
C9 0.2321 (5) 0.26091 (13) 0.4974 (4) 0.0385 (8)
C10 0.2683 (5) 0.31165 (12) 0.5607 (3) 0.0332 (7)
C11 0.1042 (5) 0.33738 (13) 0.6512 (4) 0.0407 (8)
H11A −0.0302 0.3217 0.6809 0.049*
C12 0.1384 (6) 0.38530 (14) 0.6968 (5) 0.0528 (10)
H12A 0.0297 0.4020 0.7596 0.063*
C13 0.3361 (7) 0.40892 (15) 0.6489 (5) 0.0550 (10)
H13A 0.3575 0.4420 0.6745 0.066*
C14 0.5014 (6) 0.38324 (16) 0.5631 (5) 0.0542 (10)
H14A 0.6378 0.3986 0.5362 0.065*
C15 0.4657 (5) 0.33607 (14) 0.5182 (4) 0.0447 (9)
H15A 0.5765 0.3195 0.4572 0.054*
Atomic displacement parameters (Å2) 
U11 U22 U33 U12 U13 U23
O 0.094 (2) 0.0745 (19) 0.0522 (15) −0.0141 (16) 0.0520 (15) −0.0124 (14)
C1 0.052 (3) 0.075 (3) 0.067 (3) 0.006 (2) −0.011 (2) −0.005 (2)
supporting information
sup-4Acta Cryst. (2008). E64, o2271    
N1 0.087 (3) 0.079 (3) 0.125 (4) 0.026 (2) −0.026 (3) 0.003 (3)
N2 0.0334 (15) 0.0591 (18) 0.0267 (13) 0.0019 (13) 0.0090 (11) −0.0020 (12)
C2 0.044 (2) 0.055 (2) 0.0412 (19) 0.0021 (17) 0.0006 (16) −0.0035 (16)
C3 0.0340 (19) 0.067 (2) 0.0407 (19) −0.0052 (17) −0.0050 (15) −0.0033 (17)
C4 0.0356 (18) 0.053 (2) 0.0385 (18) −0.0108 (16) 0.0028 (14) −0.0059 (15)
C5 0.0255 (16) 0.055 (2) 0.0256 (15) 0.0002 (14) 0.0042 (12) −0.0041 (13)
C6 0.038 (2) 0.063 (2) 0.053 (2) −0.0110 (18) −0.0145 (17) −0.0085 (18)
C7 0.056 (2) 0.050 (2) 0.064 (2) −0.0027 (19) −0.013 (2) −0.0099 (19)
C8 0.0338 (18) 0.060 (2) 0.0356 (17) −0.0021 (16) −0.0016 (14) 0.0004 (15)
C9 0.0300 (17) 0.061 (2) 0.0250 (15) 0.0000 (15) 0.0120 (13) 0.0029 (14)
C10 0.0218 (15) 0.057 (2) 0.0206 (14) 0.0046 (14) −0.0001 (12) 0.0082 (13)
C11 0.0242 (16) 0.061 (2) 0.0365 (17) 0.0016 (15) 0.0004 (13) 0.0025 (15)
C12 0.052 (2) 0.057 (2) 0.049 (2) 0.0076 (19) −0.0028 (17) −0.0064 (18)
C13 0.057 (2) 0.058 (2) 0.049 (2) −0.011 (2) −0.0165 (19) 0.0015 (18)
C14 0.037 (2) 0.076 (3) 0.049 (2) −0.0154 (19) −0.0079 (17) 0.0077 (19)
C15 0.0305 (18) 0.070 (3) 0.0343 (17) 0.0034 (17) 0.0040 (14) 0.0054 (16)
Geometric parameters (Å, º) 
O—C9 1.230 (4) C7—H7A 0.9300
C1—N1 1.113 (5) C8—H8A 0.9700
C1—C2 1.448 (6) C8—H8B 0.9700
N2—C9 1.329 (4) C9—C10 1.479 (5)
N2—C8 1.446 (4) C10—C15 1.380 (4)
N2—H2A 0.8600 C10—C11 1.394 (4)
C2—C3 1.379 (5) C11—C12 1.364 (5)
C2—C7 1.394 (5) C11—H11A 0.9300
C3—C4 1.370 (5) C12—C13 1.383 (5)
C3—H3A 0.9300 C12—H12A 0.9300
C4—C5 1.380 (4) C13—C14 1.380 (5)
C4—H4A 0.9300 C13—H13A 0.9300
C5—C6 1.370 (5) C14—C15 1.344 (5)
C5—C8 1.519 (5) C14—H14A 0.9300
C6—C7 1.357 (5) C15—H15A 0.9300
C6—H6A 0.9300
N1—C1—C2 178.1 (5) N2—C8—H8B 108.4
C9—N2—C8 122.1 (3) C5—C8—H8B 108.4
C9—N2—H2A 118.9 H8A—C8—H8B 107.5
C8—N2—H2A 118.9 O—C9—N2 120.0 (3)
C3—C2—C7 118.9 (3) O—C9—C10 121.4 (3)
C3—C2—C1 121.0 (3) N2—C9—C10 118.5 (3)
C7—C2—C1 120.1 (3) C15—C10—C11 118.2 (3)
C4—C3—C2 120.7 (3) C15—C10—C9 118.9 (3)
C4—C3—H3A 119.7 C11—C10—C9 122.8 (3)
C2—C3—H3A 119.7 C12—C11—C10 120.8 (3)
C3—C4—C5 120.5 (3) C12—C11—H11A 119.6
C3—C4—H4A 119.8 C10—C11—H11A 119.6
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sup-5Acta Cryst. (2008). E64, o2271    
C5—C4—H4A 119.8 C11—C12—C13 119.4 (4)
C6—C5—C4 118.2 (3) C11—C12—H12A 120.3
C6—C5—C8 119.7 (3) C13—C12—H12A 120.3
C4—C5—C8 122.1 (3) C14—C13—C12 119.9 (4)
C7—C6—C5 122.6 (3) C14—C13—H13A 120.1
C7—C6—H6A 118.7 C12—C13—H13A 120.1
C5—C6—H6A 118.7 C15—C14—C13 120.1 (3)
C6—C7—C2 119.1 (4) C15—C14—H14A 119.9
C6—C7—H7A 120.4 C13—C14—H14A 119.9
C2—C7—H7A 120.4 C14—C15—C10 121.5 (3)
N2—C8—C5 115.5 (3) C14—C15—H15A 119.3
N2—C8—H8A 108.4 C10—C15—H15A 119.3
C5—C8—H8A 108.4
C7—C2—C3—C4 −1.3 (5) C8—N2—C9—C10 175.9 (3)
C1—C2—C3—C4 178.7 (3) O—C9—C10—C15 −22.3 (5)
C2—C3—C4—C5 1.2 (5) N2—C9—C10—C15 158.1 (3)
C3—C4—C5—C6 −0.3 (5) O—C9—C10—C11 152.8 (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—C7 178.5 (3) C9—C10—C11—C12 −175.4 (3)
C5—C6—C7—C2 0.2 (6) C10—C11—C12—C13 1.6 (5)
C3—C2—C7—C6 0.7 (6) C11—C12—C13—C14 −3.2 (5)
C1—C2—C7—C6 −179.3 (4) C12—C13—C14—C15 3.4 (5)
C9—N2—C8—C5 90.5 (4) C13—C14—C15—C10 −2.1 (5)
C6—C5—C8—N2 166.8 (3) C11—C10—C15—C14 0.4 (5)
C4—C5—C8—N2 −14.4 (4) C9—C10—C15—C14 175.8 (3)
C8—N2—C9—O −3.7 (5)
Hydrogen-bond geometry (Å, º) 
D—H···A D—H H···A D···A D—H···A
N2—H2A···Oi 0.86 1.99 2.830 (4) 166
Symmetry code: (i) x−1/2, −y+1/2, z+1/2.


Acta Cryst. A64, 112–122. organic compounds Acta Cryst.

CAD-4 Software. Enraf–Nonius,

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq

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

Packing diagram of (I). Hydrogen bonds are shown as dashed lines. N-(4-Cyanobenzyl)benzamide Crystal data

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

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N-(4-Cyano­benz­yl)benzamide

N-(4-Cyanobenzyl)benzamide

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N-(4-Cyano­benz­yl)benzamide

Abstract

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N-(4-Cyanobenzyl)benzamide