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

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

doi:10.1107/S1600536813008131

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o653

https://doi.org/10.1107/S1600536813008131

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

Mohan Kumar,^a B. S. Madhukar,^b M. A. Sridhar,^a ^* D. G. Bhadregowda,^b Kamini Kapoor,^c Vivek K. Gupta ^c and Rajni Kant ^c

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Chemistry, Yuvarajas College, University of Mysore, Mysore 570005, India, and ^cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 4 March 2013; accepted 25 March 2013; online 5 April 2013)

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.

Related literature

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

Experimental

Crystal data

C₁₁H₁₂N₂O
M_r = 188.23
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.7573 (1) Å
b = 11.1432 (3) Å
c = 19.3311 (5) Å
V = 1024.77 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.965, T_max = 1.000
21018 measured reflections
1201 independent reflections
1097 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.079
S = 1.04
1201 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	2.04	2.878 (2)	165
C2—H2A⋯O1ⁱ	0.97	2.42	3.215 (2)	138
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813008131/gk2561sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008131/gk2561Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008131/gk2561Isup3.cml

checkCIF report

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.

Structure description top

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

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

	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.
	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.
	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

C₁₁H₁₂N₂O	F(000) = 400
M_r = 188.23	D_x = 1.220 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9923 reflections
a = 4.7573 (1) Å	θ = 3.6–29.1°
b = 11.1432 (3) Å	µ = 0.08 mm⁻¹
c = 19.3311 (5) Å	T = 293 K
V = 1024.77 (4) Å³	Block, white
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Oxford diffraction Xcalibur Sapphire3 diffractometer	1201 independent reflections
Radiation source: fine-focus sealed tube	1097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.7°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.965, T_max = 1.000	l = −23→23
21018 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0368P)² + 0.1643P] where P = (F_o² + 2F_c²)/3
1201 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₁H₁₂N₂O	V = 1024.77 (4) Å³
M_r = 188.23	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.7573 (1) Å	µ = 0.08 mm⁻¹
b = 11.1432 (3) Å	T = 293 K
c = 19.3311 (5) Å	0.3 × 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)
T_min = 0.965, T_max = 1.000	R_int = 0.039
21018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	Δρ_max = 0.10 e Å⁻³
1201 reflections	Δρ_min = −0.13 e Å⁻³
128 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.4540 (3)	0.94357 (13)	0.07761 (7)	0.0500 (4)
N1	0.3390 (6)	1.1444 (2)	−0.05721 (12)	0.0971 (8)
N2	0.0251 (3)	0.87304 (13)	0.10524 (7)	0.0381 (4)
H2	−0.1530	0.8858	0.1031	0.046*
C1	0.2139 (5)	1.10928 (18)	−0.01186 (11)	0.0532 (5)
C2	0.0562 (4)	1.06274 (17)	0.04640 (10)	0.0438 (4)
H2A	−0.1319	1.0416	0.0313	0.053*
H2B	0.0398	1.1246	0.0815	0.053*
C3	0.1970 (4)	0.95288 (16)	0.07756 (8)	0.0350 (4)
C4	0.1256 (4)	0.76346 (15)	0.13946 (9)	0.0392 (4)
H4	0.3068	0.7823	0.1610	0.047*
C5	0.1777 (6)	0.66621 (19)	0.08589 (11)	0.0667 (7)
H5A	0.0050	0.6479	0.0625	0.100*
H5B	0.2471	0.5954	0.1084	0.100*
H5C	0.3139	0.6939	0.0529	0.100*
C6	−0.0760 (4)	0.73086 (16)	0.19678 (8)	0.0371 (4)
C7	−0.2066 (5)	0.62085 (18)	0.20201 (11)	0.0527 (5)
H7	−0.1722	0.5620	0.1689	0.063*
C8	−0.3899 (5)	0.5972 (2)	0.25659 (13)	0.0670 (7)
H8	−0.4768	0.5226	0.2595	0.080*
C9	−0.4434 (5)	0.6819 (2)	0.30565 (12)	0.0675 (7)
H9	−0.5676	0.6657	0.3416	0.081*
C10	−0.3132 (6)	0.7905 (2)	0.30156 (11)	0.0640 (6)
H10	−0.3473	0.8486	0.3351	0.077*
C11	−0.1309 (4)	0.81478 (19)	0.24787 (10)	0.0514 (5)
H11	−0.0427	0.8892	0.2459	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0258 (6)	0.0575 (8)	0.0667 (8)	0.0020 (6)	0.0029 (6)	0.0128 (7)
N1	0.1117 (19)	0.0878 (16)	0.0917 (15)	0.0037 (16)	0.0391 (15)	0.0382 (14)
N2	0.0253 (7)	0.0399 (8)	0.0492 (8)	0.0027 (7)	−0.0020 (6)	0.0118 (7)
C1	0.0553 (12)	0.0439 (11)	0.0603 (12)	−0.0003 (10)	0.0039 (11)	0.0130 (9)
C2	0.0344 (9)	0.0414 (10)	0.0557 (10)	0.0029 (9)	0.0038 (9)	0.0109 (9)
C3	0.0289 (9)	0.0391 (10)	0.0370 (8)	0.0009 (8)	0.0001 (7)	0.0019 (8)
C4	0.0362 (10)	0.0374 (9)	0.0440 (9)	0.0049 (8)	−0.0020 (8)	0.0059 (8)
C5	0.0910 (18)	0.0519 (13)	0.0571 (12)	0.0138 (14)	0.0136 (13)	−0.0012 (10)
C6	0.0342 (9)	0.0363 (9)	0.0407 (9)	0.0025 (8)	−0.0075 (8)	0.0088 (7)
C7	0.0565 (12)	0.0385 (11)	0.0631 (12)	−0.0027 (11)	−0.0049 (11)	0.0081 (9)
C8	0.0604 (15)	0.0514 (13)	0.0892 (16)	−0.0123 (11)	0.0018 (14)	0.0289 (13)
C9	0.0589 (14)	0.0799 (17)	0.0636 (13)	0.0067 (14)	0.0136 (13)	0.0301 (13)
C10	0.0711 (15)	0.0698 (15)	0.0512 (11)	0.0076 (14)	0.0112 (12)	0.0047 (10)
C11	0.0567 (12)	0.0470 (10)	0.0504 (10)	−0.0064 (10)	0.0015 (10)	−0.0007 (9)

Geometric parameters (Å, º) top

O1—C3	1.227 (2)	C5—H5B	0.9600
N1—C1	1.130 (3)	C5—H5C	0.9600
N2—C3	1.322 (2)	C6—C7	1.378 (3)
N2—C4	1.469 (2)	C6—C11	1.385 (3)
N2—H2	0.8600	C7—C8	1.394 (3)
C1—C2	1.449 (3)	C7—H7	0.9300
C2—C3	1.520 (2)	C8—C9	1.362 (3)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.362 (4)
C4—C6	1.510 (2)	C9—H9	0.9300
C4—C5	1.519 (3)	C10—C11	1.379 (3)
C4—H4	0.9800	C10—H10	0.9300
C5—H5A	0.9600	C11—H11	0.9300

C3—N2—C4	122.72 (14)	C4—C5—H5C	109.5
C3—N2—H2	118.6	H5A—C5—H5C	109.5
C4—N2—H2	118.6	H5B—C5—H5C	109.5
N1—C1—C2	179.1 (3)	C7—C6—C11	117.61 (18)
C1—C2—C3	111.60 (16)	C7—C6—C4	123.66 (17)
C1—C2—H2A	109.3	C11—C6—C4	118.72 (16)
C3—C2—H2A	109.3	C6—C7—C8	120.4 (2)
C1—C2—H2B	109.3	C6—C7—H7	119.8
C3—C2—H2B	109.3	C8—C7—H7	119.8
H2A—C2—H2B	108.0	C9—C8—C7	120.9 (2)
O1—C3—N2	124.01 (18)	C9—C8—H8	119.6
O1—C3—C2	120.49 (17)	C7—C8—H8	119.6
N2—C3—C2	115.47 (15)	C8—C9—C10	119.4 (2)
N2—C4—C6	108.88 (14)	C8—C9—H9	120.3
N2—C4—C5	109.82 (15)	C10—C9—H9	120.3
C6—C4—C5	115.61 (16)	C9—C10—C11	120.2 (2)
N2—C4—H4	107.4	C9—C10—H10	119.9
C6—C4—H4	107.4	C11—C10—H10	119.9
C5—C4—H4	107.4	C10—C11—C6	121.52 (19)
C4—C5—H5A	109.5	C10—C11—H11	119.2
C4—C5—H5B	109.5	C6—C11—H11	119.2
H5A—C5—H5B	109.5

C4—N2—C3—O1	0.1 (3)	C5—C4—C6—C11	179.27 (18)
C4—N2—C3—C2	−178.11 (15)	C11—C6—C7—C8	0.9 (3)
C1—C2—C3—O1	33.0 (3)	C4—C6—C7—C8	179.84 (18)
C1—C2—C3—N2	−148.74 (17)	C6—C7—C8—C9	0.0 (3)
C3—N2—C4—C6	148.29 (16)	C7—C8—C9—C10	−0.7 (4)
C3—N2—C4—C5	−84.2 (2)	C8—C9—C10—C11	0.6 (4)
N2—C4—C6—C7	124.55 (18)	C9—C10—C11—C6	0.4 (3)
C5—C4—C6—C7	0.4 (3)	C7—C6—C11—C10	−1.1 (3)
N2—C4—C6—C11	−56.6 (2)	C4—C6—C11—C10	179.93 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.04	2.878 (2)	165
C2—H2A···O1ⁱ	0.97	2.42	3.215 (2)	138

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂O
M_r	188.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	4.7573 (1), 11.1432 (3), 19.3311 (5)
V (Å³)	1024.77 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.965, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21018, 1201, 1097
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.079, 1.04
No. of reflections	1201
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Widows (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.04	2.878 (2)	165
C2—H2A···O1ⁱ	0.97	2.42	3.215 (2)	138

Symmetry code: (i) x−1, y, z.

Acknowledgements

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

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Resende, J. A. L. C., Santos Jr, S., Ellena, J. & Guilardi, S. (2003). Acta Cryst. E59, o723–o725. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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