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 ▶); 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,

• a = 5.864 (1) Å

• b = 27.164 (5) Å

• c = 7.839 (2) Å

• β = 91.09 (3)°

• V = 1248.4 (4) ų

• 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[F ² > 2σ(F ²)] = 0.075

• wR(F ²) = 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

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.

Supplementary Material

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

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) .

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 U_iso(H) = xU_eq(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

C15H12N2O	F000 = 496
Mr = 236.27	Dx = 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 = 10–13º
b = 27.164 (5) Å	µ = 0.08 mm−1
c = 7.839 (2) Å	T = 298 (2) K
β = 91.09 (3)º	Block, colorless
V = 1248.4 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.041
Radiation source: fine-focus sealed tube	θmax = 25.3º
Monochromator: graphite	θmin = 1.5º
T = 298(2) K	h = −7→7
ω/2θ scans	k = 0→32
Absorption correction: ψ scan(North et al., 1968)	l = 0→9
Tmin = 0.976, Tmax = 0.992	3 standard reflections
2450 measured reflections	every 200 reflections
2233 independent reflections	intensity decay: none
1461 reflections with I > 2σ(I)

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075	H-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 reflections	Δρmax = 0.26 e Å−3
163 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction 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 (Ų)

	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 (Ų)

	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—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, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Oi	0.86	1.99	2.830 (4)	166

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