(E)-4-Phenyl­butan-2-one oxime

Fun, H.-K.; Loh, W.-S.; Kayarmar, R.; Dinesha; Nagaraja, G.K.

doi:10.1107/S1600536811031928

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2332

doi:10.1107/S1600536811031928

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(E)-4-Phenylbutan-2-one oxime

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § Reshma Kayarmar,^b Dinesha ^c and G. K. Nagaraja ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSequent Scientific Limited, Baikampady, New Mangalore, India, and ^cDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 6 August 2011; accepted 7 August 2011; online 11 August 2011)

In the title compound, C₁₀H₁₃NO, the C—C—C—C torsion angle formed between the benzene ring and the butan-2-one oxime unit is 73.7 (2)°, with the latter lying above the plane through the benzene ring. In the crystal, intermolecular O—H⋯N hydrogen bonds link pairs of molecules into dimers, forming R₂²(6) ring motifs which are stacked along the a axis.

Related literature

For background to oximes and their microbial activity, see: El-Sabbagh et al. (1990 ); El-Sayed et al. (1996 ); Althuis et al. (1979 ); Nargund et al. (1992 ); Srivastava et al. (2004 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₁₃NO
M_r = 163.21
Monoclinic, P 2₁ /c
a = 5.450 (3) Å
b = 9.698 (6) Å
c = 18.455 (12) Å
β = 93.888 (13)°
V = 973.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 297 K
0.67 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.953, T_max = 0.992
10336 measured reflections
2808 independent reflections
1448 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.183
S = 1.04
2808 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1ⁱ	0.85	1.97	2.785 (3)	160
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031928/tk2777sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031928/tk2777Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031928/tk2777Isup3.cml

checkCIF report

Comment top

Oximes are important intermediates for the preparation of primary amines by reduction. The primary amine generated can be used for the preparation of many heterocycles like quinoline, azetidinone, 1,2,4-triazole and 1,3,4-thiadiazole, benzothiazipines and thiazolidinone. These heterocycles show various biological activities such as anti-cancer (El-Sabbagh et al., 1990), anti-inflammatory (El-Sayed et al., 1996), anti-allergics (Althuis et al., 1979) anti-microbial (Nargund et al., 1992) and anthelmintic activities (Srivastava et al., 2004). The above motivated us to synthesize the title compound, (E)-4-phenylbutan-2-one oxime.

In the title compound (Fig. 1), the torsion angle, C5–C6–C7–C8, formed between the benzene ring (C1–C6) and the butan-2-one oxime (C7–C10/N1/O1) unit is 73.7 (2)°.

In the crystal packing (Fig. 2), pairs of intermolecular O1—H1O1···N1 hydrogen bonds (Table 1) link the molecules into dimers forming R₂²(6) ring motifs (Bernstein et al., 1995) which are stacked along the a axis.

Related literature top

For background to oximes and their microbial activity, see: El-Sabbagh et al. (1990); El-Sayed et al. (1996); Althuis et al. (1979); Nargund et al. (1992); Srivastava et al. (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 5-phenylpentan-2-one (2 g, 0.012 mole) and hydroxylamine HCl (1.25 g 0.0184 mole) in ethanol was refluxed for 4 h, during which white crystals separated out. After cooling to room temperature, the resulting (E)-4-phenylbutan-2-one oxime was filtered-off, dried and recrystallized from ethanol. Yield, 1.8 g (90%). Crystals suitable for X-ray analysis were obtained from its acetone solution by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis.

(E)-4-Phenylbutan-2-one oxime top

Crystal data top

C₁₀H₁₃NO	F(000) = 352
M_r = 163.21	D_x = 1.114 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1653 reflections
a = 5.450 (3) Å	θ = 3.8–22.7°
b = 9.698 (6) Å	µ = 0.07 mm⁻¹
c = 18.455 (12) Å	T = 297 K
β = 93.888 (13)°	Needle, colourless
V = 973.1 (11) Å³	0.67 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	1448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.953, T_max = 0.992	k = −13→13
10336 measured reflections	l = −18→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0833P)² + 0.063P] where P = (F_o² + 2F_c²)/3
2808 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₀H₁₃NO	V = 973.1 (11) Å³
M_r = 163.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.450 (3) Å	µ = 0.07 mm⁻¹
b = 9.698 (6) Å	T = 297 K
c = 18.455 (12) Å	0.67 × 0.15 × 0.12 mm
β = 93.888 (13)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	2808 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1448 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.992	R_int = 0.033
10336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	Δρ_max = 0.18 e Å⁻³
2808 reflections	Δρ_min = −0.14 e Å⁻³
110 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
O1	0.0482 (2)	0.64909 (13)	0.46391 (6)	0.0829 (4)
H1O1	−0.0382	0.5764	0.4564	0.124*
N1	0.1886 (2)	0.60421 (14)	0.52725 (7)	0.0663 (4)
C1	0.8076 (3)	0.3977 (2)	0.72018 (9)	0.0761 (5)
H1A	0.8150	0.3423	0.6793	0.091*
C2	0.9742 (4)	0.3766 (3)	0.77902 (11)	0.0949 (6)
H2A	1.0896	0.3062	0.7775	0.114*
C3	0.9709 (4)	0.4577 (3)	0.83903 (11)	0.0972 (7)
H3A	1.0844	0.4433	0.8783	0.117*
C4	0.8004 (4)	0.5602 (3)	0.84143 (10)	0.0977 (7)
H4A	0.7989	0.6169	0.8821	0.117*
C5	0.6284 (4)	0.5800 (2)	0.78301 (10)	0.0871 (6)
H5A	0.5100	0.6486	0.7856	0.104*
C6	0.6307 (3)	0.49911 (17)	0.72088 (8)	0.0644 (4)
C7	0.4539 (3)	0.52421 (19)	0.65522 (9)	0.0771 (5)
H7A	0.2888	0.5351	0.6710	0.093*
H7B	0.4542	0.4447	0.6233	0.093*
C8	0.5231 (3)	0.65179 (17)	0.61365 (9)	0.0691 (5)
H8A	0.5223	0.7300	0.6464	0.083*
H8B	0.6904	0.6404	0.5997	0.083*
C9	0.3630 (3)	0.68632 (15)	0.54665 (8)	0.0621 (4)
C10	0.4212 (4)	0.8158 (2)	0.50706 (11)	0.0922 (6)
H10D	0.4040	0.7993	0.4557	0.138*
H10A	0.5870	0.8435	0.5207	0.138*
H10B	0.3098	0.8874	0.5194	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0914 (9)	0.0805 (8)	0.0714 (7)	−0.0160 (6)	−0.0336 (6)	0.0219 (6)
N1	0.0682 (8)	0.0669 (8)	0.0603 (7)	−0.0095 (6)	−0.0206 (6)	0.0125 (6)
C1	0.0762 (11)	0.0854 (11)	0.0650 (10)	0.0016 (10)	−0.0076 (8)	0.0009 (8)
C2	0.0778 (12)	0.1242 (17)	0.0802 (12)	0.0272 (12)	−0.0129 (10)	0.0050 (11)
C3	0.0823 (13)	0.1379 (18)	0.0681 (11)	0.0064 (13)	−0.0184 (9)	0.0096 (12)
C4	0.1167 (17)	0.1168 (16)	0.0582 (10)	0.0051 (14)	−0.0042 (10)	−0.0083 (10)
C5	0.0883 (13)	0.0952 (13)	0.0767 (11)	0.0192 (11)	−0.0007 (10)	0.0041 (10)
C6	0.0567 (9)	0.0725 (10)	0.0622 (9)	−0.0149 (8)	−0.0088 (7)	0.0149 (7)
C7	0.0691 (10)	0.0795 (11)	0.0787 (11)	−0.0199 (9)	−0.0238 (8)	0.0216 (8)
C8	0.0655 (9)	0.0738 (10)	0.0654 (9)	−0.0189 (8)	−0.0160 (8)	0.0101 (7)
C9	0.0658 (9)	0.0599 (8)	0.0591 (8)	−0.0107 (7)	−0.0068 (7)	0.0047 (6)
C10	0.1152 (16)	0.0778 (12)	0.0808 (12)	−0.0301 (11)	−0.0151 (11)	0.0204 (9)

Geometric parameters (Å, º) top

O1—N1	1.4212 (17)	C5—H5A	0.9300
O1—H1O1	0.8540	C6—C7	1.516 (2)
N1—C9	1.273 (2)	C7—C8	1.517 (2)
C1—C6	1.378 (3)	C7—H7A	0.9700
C1—C2	1.383 (3)	C7—H7B	0.9700
C1—H1A	0.9300	C8—C9	1.502 (2)
C2—C3	1.360 (3)	C8—H8A	0.9700
C2—H2A	0.9300	C8—H8B	0.9700
C3—C4	1.364 (3)	C9—C10	1.497 (2)
C3—H3A	0.9300	C10—H10D	0.9600
C4—C5	1.393 (3)	C10—H10A	0.9600
C4—H4A	0.9300	C10—H10B	0.9600
C5—C6	1.390 (3)

N1—O1—H1O1	98.1	C6—C7—H7A	109.3
C9—N1—O1	112.95 (12)	C8—C7—H7A	109.3
C6—C1—C2	121.40 (18)	C6—C7—H7B	109.3
C6—C1—H1A	119.3	C8—C7—H7B	109.3
C2—C1—H1A	119.3	H7A—C7—H7B	108.0
C3—C2—C1	120.6 (2)	C9—C8—C7	116.60 (13)
C3—C2—H2A	119.7	C9—C8—H8A	108.1
C1—C2—H2A	119.7	C7—C8—H8A	108.1
C2—C3—C4	119.67 (19)	C9—C8—H8B	108.1
C2—C3—H3A	120.2	C7—C8—H8B	108.1
C4—C3—H3A	120.2	H8A—C8—H8B	107.3
C3—C4—C5	119.97 (19)	N1—C9—C10	124.47 (15)
C3—C4—H4A	120.0	N1—C9—C8	118.24 (13)
C5—C4—H4A	120.0	C10—C9—C8	117.29 (14)
C6—C5—C4	121.15 (19)	C9—C10—H10D	109.5
C6—C5—H5A	119.4	C9—C10—H10A	109.5
C4—C5—H5A	119.4	H10D—C10—H10A	109.5
C1—C6—C5	117.14 (16)	C9—C10—H10B	109.5
C1—C6—C7	120.95 (16)	H10D—C10—H10B	109.5
C5—C6—C7	121.86 (17)	H10A—C10—H10B	109.5
C6—C7—C8	111.64 (13)

C6—C1—C2—C3	−1.3 (3)	C1—C6—C7—C8	−103.8 (2)
C1—C2—C3—C4	0.5 (3)	C5—C6—C7—C8	73.7 (2)
C2—C3—C4—C5	1.0 (3)	C6—C7—C8—C9	179.16 (15)
C3—C4—C5—C6	−1.7 (3)	O1—N1—C9—C10	−1.1 (2)
C2—C1—C6—C5	0.5 (3)	O1—N1—C9—C8	179.05 (13)
C2—C1—C6—C7	178.14 (17)	C7—C8—C9—N1	−3.1 (2)
C4—C5—C6—C1	0.9 (3)	C7—C8—C9—C10	177.02 (17)
C4—C5—C6—C7	−176.64 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.85	1.97	2.785 (3)	160

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO
M_r	163.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	5.450 (3), 9.698 (6), 18.455 (12)
β (°)	93.888 (13)
V (Å³)	973.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.67 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.953, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	10336, 2808, 1448
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.183, 1.04
No. of reflections	2808
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.85	1.97	2.785 (3)	160

Symmetry code: (i) −x, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for a Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship.

References

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