N-(4-Cyano­benz­yl)benzamide

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

doi:10.1107/S1600536808035137

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2271

doi:10.1107/S1600536808035137

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N-(4-Cyanobenzyl)benzamide

Yi-Li Tong,^a Li-Qin Guo,^b Hai-Jun Ma,^b Wei Chen ^a and Hong-Jun Zhu ^a ^*

^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; online 8 November 2008)

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

Experimental

Crystal data

C₁₅H₁₂N₂O
M_r = 236.27
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.075
wR(F²) = 0.186
S = 1.00
2233 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035137/im2085sup1.cif

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

checkCIF report

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.

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

	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.

N-(4-Cyanobenzyl)benzamide top

Crystal data top

C₁₅H₁₂N₂O	F(000) = 496
M_r = 236.27	D_x = 1.257 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 5.864 (1) Å	θ = 10–13°
b = 27.164 (5) Å	µ = 0.08 mm⁻¹
c = 7.839 (2) Å	T = 298 K
β = 91.09 (3)°	Block, colorless
V = 1248.4 (4) Å³	0.30 × 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 tube	R_int = 0.041
Graphite monochromator	θ_max = 25.3°, θ_min = 1.5°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→32
T_min = 0.976, T_max = 0.992	l = 0→9
2450 measured reflections	3 standard reflections every 200 reflections
2233 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.06P)² + 2P] where P = (F_o² + 2F_c²)/3
2233 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O	V = 1248.4 (4) Å³
M_r = 236.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.864 (1) Å	µ = 0.08 mm⁻¹
b = 27.164 (5) Å	T = 298 K
c = 7.839 (2) Å	0.30 × 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)	R_int = 0.041
T_min = 0.976, T_max = 0.992	3 standard reflections every 200 reflections
2450 measured reflections	intensity decay: none
2233 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
2233 reflections	Δρ_min = −0.24 e Å⁻³
163 parameters

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

	x	y	z	U_iso*/U_eq
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) top

	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)
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) top

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
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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O
M_r	236.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.864 (1), 27.164 (5), 7.839 (2)
β (°)	91.09 (3)
V (Å³)	1248.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.976, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	2450, 2233, 1461
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.186, 1.00
No. of reflections	2233
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Oⁱ	0.8600	1.9900	2.830 (4)	166.00

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

Acknowledgements

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

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