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organic compounds
N-(4-Cyanobenzyl)benzamide
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
The title compound, C15H12N2O, is a derivative of 4-(aminomethyl)benzonitrile, an important pestcide intermediate. In the 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
|
Refinement
|
|
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell 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
10.1107/S1600536808035137/im2085sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808035137/im2085Isup2.hkl
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.
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.
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
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).C15H12N2O | F(000) = 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 = 10–13° |
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 |
Enraf–Nonius CAD-4 diffractometer | 1461 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.3°, θmin = 1.5° |
ω/2θ scans | h = −7→7 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→32 |
Tmin = 0.976, Tmax = 0.992 | l = 0→9 |
2450 measured reflections | 3 standard reflections every 200 reflections |
2233 independent reflections | intensity decay: none |
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(Fo2) + (0.06P)2 + 2P] where P = (Fo2 + 2Fc2)/3 |
2233 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C15H12N2O | V = 1248.4 (4) Å3 |
Mr = 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)° |
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 = 0.992 | 3 standard reflections every 200 reflections |
2450 measured reflections | intensity decay: none |
2233 independent reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.26 e Å−3 |
2233 reflections | Δρmin = −0.24 e Å−3 |
163 parameters |
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. |
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.976, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2450, 2233, 1461 |
Rint | 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 |
Δρmax, Δρmin (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).
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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Blaschke, G., Joergens, R. & Claassen, G. (1976). Arch. Pharm. 309, 258–65. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gesing, E. (1989). Bayer AG, Germany. DE Patent No. 3 727 126. Google Scholar
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. Google Scholar
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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).