(E)-4-Phenyl-butan-2-one oxime.

In the title compound, C(10)H(13)NO, 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, inter-molecular O-H⋯N hydrogen bonds link pairs of mol-ecules into dimers, forming R(2) (2)(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 = 163.21

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.183

S = 1.04

2808 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031928/tk2777sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811031928/tk2777Isup3.cml

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

C10H13NO	F(000) = 352
Mr = 163.21	Dx = 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

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

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(Fo2) + (0.0833P)2 + 0.063P] where P = (Fo2 + 2Fc2)/3
2808 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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
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*

	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)

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)

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

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) .