supplementary materials


gk2561 scheme

Acta Cryst. (2013). E69, o653    [ doi:10.1107/S1600536813008131 ]

(R)-2-Cyano-N-(1-phenylethyl)acetamide

M. Kumar, B. S. Madhukar, M. A. Sridhar, D. G. Bhadregowda, K. Kapoor, V. K. Gupta and R. Kant

Abstract top

In the title compound, C11H12N2O, the dihedral angle between the acetamide group and the benzene ring is 68.7 (1)°. In the crystal, N-H...O and weak C-H...O hydrogen bonds link the molecules into chains along the a-axis direction.

Comment top

As part of our investigations on acetamide derivatives, the title compound has been prepared and its crystal structure is presented here.Bond lengths and angles in the title compound (Fig. 1) are comparable with the similar crystal structures (Resende et al., 2003; Gálvez et al., 2010). The dihedral angle between the acetamide group (C2/C3/O1/N2) and the benzene ring (C6—C11) is 68.7 (1)°. N—H···O and weak C—H···O hydrogen bonds link the molecules into chains along the a axis (Fig.2, Table 1). In the crystal, molecules are packed into layers parallel to the bc-plane (Fig.3).

Related literature top

For related structures, see: Resende et al. (2003); Gálvez et al. (2010).

Experimental top

The reaction of methyl 2-cyanoacetate (0.1 g, 0.01 mol) and (R)-1-phenylethanamine (0.1 g, 0.01 mol) were carried out in the presence of dilute acetic acid and the reaction mixture was allowed to stir at room temperature for 6-7 h in dry dichloromethane (25 ml). The progress of the reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure and residue was extracted with ethyl acetate. The compound was purified by successive recrystallization from methanol (yield 83%). The melting range was found to be 393-395 K.

Refinement top

All H atoms were positioned geometrically and were treated as riding on their parent C/N atoms, with C—H distances of 0.93–0.98 Å and N—H distance of 0.86 with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The 799 Friedel equivalents were merged. The absolute configuration could not be established from the X-ray data, but was already known from the known configuration of the starting material.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Widows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Hydrogen bonded chains of molecules via N—H···O and weak C—H···O hydrogen bonds. Only H atoms involved in hydrogen bonds are shown. Hydrogen bonds are represented by dashed lines.
[Figure 3] Fig. 3. The packing arrangement of molecules viewed down the a axis. Hydrogen atoms have been omitted for clarity.
(R)-2-Cyano-N-(1-phenylethyl)acetamide top
Crystal data top
C11H12N2OF(000) = 400
Mr = 188.23Dx = 1.220 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9923 reflections
a = 4.7573 (1) Åθ = 3.6–29.1°
b = 11.1432 (3) ŵ = 0.08 mm1
c = 19.3311 (5) ÅT = 293 K
V = 1024.77 (4) Å3Block, white
Z = 40.3 × 0.2 × 0.2 mm
Data collection top
Oxford diffraction Xcalibur Sapphire3
diffractometer
1201 independent reflections
Radiation source: fine-focus sealed tube1097 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.7°
ω scansh = 55
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 1313
Tmin = 0.965, Tmax = 1.000l = 2323
21018 measured reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0368P)2 + 0.1643P]
where P = (Fo2 + 2Fc2)/3
1201 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.10 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C11H12N2OV = 1024.77 (4) Å3
Mr = 188.23Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.7573 (1) ŵ = 0.08 mm1
b = 11.1432 (3) ÅT = 293 K
c = 19.3311 (5) Å0.3 × 0.2 × 0.2 mm
Data collection top
Oxford diffraction Xcalibur Sapphire3
diffractometer
1201 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
1097 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 1.000Rint = 0.039
21018 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.079Δρmax = 0.10 e Å3
S = 1.04Δρmin = 0.13 e Å3
1201 reflectionsAbsolute structure: ?
128 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O10.4540 (3)0.94357 (13)0.07761 (7)0.0500 (4)
N10.3390 (6)1.1444 (2)0.05721 (12)0.0971 (8)
N20.0251 (3)0.87304 (13)0.10524 (7)0.0381 (4)
H20.15300.88580.10310.046*
C10.2139 (5)1.10928 (18)0.01186 (11)0.0532 (5)
C20.0562 (4)1.06274 (17)0.04640 (10)0.0438 (4)
H2A0.13191.04160.03130.053*
H2B0.03981.12460.08150.053*
C30.1970 (4)0.95288 (16)0.07756 (8)0.0350 (4)
C40.1256 (4)0.76346 (15)0.13946 (9)0.0392 (4)
H40.30680.78230.16100.047*
C50.1777 (6)0.66621 (19)0.08589 (11)0.0667 (7)
H5A0.00500.64790.06250.100*
H5B0.24710.59540.10840.100*
H5C0.31390.69390.05290.100*
C60.0760 (4)0.73086 (16)0.19678 (8)0.0371 (4)
C70.2066 (5)0.62085 (18)0.20201 (11)0.0527 (5)
H70.17220.56200.16890.063*
C80.3899 (5)0.5972 (2)0.25659 (13)0.0670 (7)
H80.47680.52260.25950.080*
C90.4434 (5)0.6819 (2)0.30565 (12)0.0675 (7)
H90.56760.66570.34160.081*
C100.3132 (6)0.7905 (2)0.30156 (11)0.0640 (6)
H100.34730.84860.33510.077*
C110.1309 (4)0.81478 (19)0.24787 (10)0.0514 (5)
H110.04270.88920.24590.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0258 (6)0.0575 (8)0.0667 (8)0.0020 (6)0.0029 (6)0.0128 (7)
N10.1117 (19)0.0878 (16)0.0917 (15)0.0037 (16)0.0391 (15)0.0382 (14)
N20.0253 (7)0.0399 (8)0.0492 (8)0.0027 (7)0.0020 (6)0.0118 (7)
C10.0553 (12)0.0439 (11)0.0603 (12)0.0003 (10)0.0039 (11)0.0130 (9)
C20.0344 (9)0.0414 (10)0.0557 (10)0.0029 (9)0.0038 (9)0.0109 (9)
C30.0289 (9)0.0391 (10)0.0370 (8)0.0009 (8)0.0001 (7)0.0019 (8)
C40.0362 (10)0.0374 (9)0.0440 (9)0.0049 (8)0.0020 (8)0.0059 (8)
C50.0910 (18)0.0519 (13)0.0571 (12)0.0138 (14)0.0136 (13)0.0012 (10)
C60.0342 (9)0.0363 (9)0.0407 (9)0.0025 (8)0.0075 (8)0.0088 (7)
C70.0565 (12)0.0385 (11)0.0631 (12)0.0027 (11)0.0049 (11)0.0081 (9)
C80.0604 (15)0.0514 (13)0.0892 (16)0.0123 (11)0.0018 (14)0.0289 (13)
C90.0589 (14)0.0799 (17)0.0636 (13)0.0067 (14)0.0136 (13)0.0301 (13)
C100.0711 (15)0.0698 (15)0.0512 (11)0.0076 (14)0.0112 (12)0.0047 (10)
C110.0567 (12)0.0470 (10)0.0504 (10)0.0064 (10)0.0015 (10)0.0007 (9)
Geometric parameters (Å, º) top
O1—C31.227 (2)C5—H5B0.9600
N1—C11.130 (3)C5—H5C0.9600
N2—C31.322 (2)C6—C71.378 (3)
N2—C41.469 (2)C6—C111.385 (3)
N2—H20.8600C7—C81.394 (3)
C1—C21.449 (3)C7—H70.9300
C2—C31.520 (2)C8—C91.362 (3)
C2—H2A0.9700C8—H80.9300
C2—H2B0.9700C9—C101.362 (4)
C4—C61.510 (2)C9—H90.9300
C4—C51.519 (3)C10—C111.379 (3)
C4—H40.9800C10—H100.9300
C5—H5A0.9600C11—H110.9300
C3—N2—C4122.72 (14)C4—C5—H5C109.5
C3—N2—H2118.6H5A—C5—H5C109.5
C4—N2—H2118.6H5B—C5—H5C109.5
N1—C1—C2179.1 (3)C7—C6—C11117.61 (18)
C1—C2—C3111.60 (16)C7—C6—C4123.66 (17)
C1—C2—H2A109.3C11—C6—C4118.72 (16)
C3—C2—H2A109.3C6—C7—C8120.4 (2)
C1—C2—H2B109.3C6—C7—H7119.8
C3—C2—H2B109.3C8—C7—H7119.8
H2A—C2—H2B108.0C9—C8—C7120.9 (2)
O1—C3—N2124.01 (18)C9—C8—H8119.6
O1—C3—C2120.49 (17)C7—C8—H8119.6
N2—C3—C2115.47 (15)C8—C9—C10119.4 (2)
N2—C4—C6108.88 (14)C8—C9—H9120.3
N2—C4—C5109.82 (15)C10—C9—H9120.3
C6—C4—C5115.61 (16)C9—C10—C11120.2 (2)
N2—C4—H4107.4C9—C10—H10119.9
C6—C4—H4107.4C11—C10—H10119.9
C5—C4—H4107.4C10—C11—C6121.52 (19)
C4—C5—H5A109.5C10—C11—H11119.2
C4—C5—H5B109.5C6—C11—H11119.2
H5A—C5—H5B109.5
C4—N2—C3—O10.1 (3)C5—C4—C6—C11179.27 (18)
C4—N2—C3—C2178.11 (15)C11—C6—C7—C80.9 (3)
C1—C2—C3—O133.0 (3)C4—C6—C7—C8179.84 (18)
C1—C2—C3—N2148.74 (17)C6—C7—C8—C90.0 (3)
C3—N2—C4—C6148.29 (16)C7—C8—C9—C100.7 (4)
C3—N2—C4—C584.2 (2)C8—C9—C10—C110.6 (4)
N2—C4—C6—C7124.55 (18)C9—C10—C11—C60.4 (3)
C5—C4—C6—C70.4 (3)C7—C6—C11—C101.1 (3)
N2—C4—C6—C1156.6 (2)C4—C6—C11—C10179.93 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.042.878 (2)165
C2—H2A···O1i0.972.423.215 (2)138
Symmetry code: (i) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.042.878 (2)165
C2—H2A···O1i0.972.423.215 (2)138
Symmetry code: (i) x1, y, z.
Acknowledgements top

MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola for his research work. RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

references
References top

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

Gálvez, J. A., Quiroga, J., Cobo, J. & Glidewell, C. (2010). Acta Cryst. C66, o521–o523.

Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.

Resende, J. A. L. C., Santos, S. Jr, Ellena, J. & Guilardi, S. (2003). Acta Cryst. E59, o723–o725.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.