(E)-1-(4-Amino-phen-yl)ethanone oxime.

In the mol-ecule of the title compound, C(8)H(10)N(2)O, the oxime group is oriented at a dihedral angle of 5.58 (3)° with respect to the benzene ring. In the crystal structure, inter-molecular O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network.

Related literature

For general background, see: Bertolasi et al. (1982 ▶); Degorre et al. (1998 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H10N2O

M = 150.18

Monoclinic,

a = 4.8641 (2) Å

b = 9.2016 (3) Å

c = 17.1447 (7) Å

β = 95.535 (2)°

V = 763.78 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.34 × 0.28 × 0.26 mm

Data collection

Enraf–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997 ▶) T min = 0.972, T max = 0.979

6132 measured reflections

1761 independent reflections

1483 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.04

1761 reflections

113 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2007 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034120/hk2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034120/hk2552Isup2.hkl

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

C8H10N2O	F(000) = 320
Mr = 150.18	Dx = 1.306 Mg m−3
Monoclinic, P21/n	Melting point: 401(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8641 (2) Å	Cell parameters from 3781 reflections
b = 9.2016 (3) Å	θ = 1.0–30.0°
c = 17.1447 (7) Å	µ = 0.09 mm−1
β = 95.535 (2)°	T = 100 K
V = 763.78 (5) Å3	Block, pale yellow
Z = 4	0.34 × 0.28 × 0.26 mm

Enraf–Nonius KappaCCD diffractometer	1761 independent reflections
Radiation source: fine-focus sealed tube	1483 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.026
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 4.2°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.972, Tmax = 0.979	l = −22→22
6132 measured reflections

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)] = 0.040	Hydrogen site location: mixed
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2855P] where P = (Fo2 + 2Fc2)/3
1761 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.28 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	0.42570 (18)	0.21270 (10)	0.47528 (5)	0.0203 (2)
H1O	0.273 (4)	0.158 (2)	0.4589 (11)	0.049 (5)*
N1	0.38949 (19)	0.23108 (10)	0.55574 (5)	0.0168 (2)
N2	0.4407 (2)	0.42572 (11)	0.91465 (6)	0.0186 (2)
H2N	0.288 (4)	0.3807 (18)	0.9308 (10)	0.035 (4)*
H2M	0.440 (4)	0.525 (2)	0.9257 (10)	0.039 (4)*
C1	0.5281 (2)	0.34967 (12)	0.67458 (6)	0.0147 (2)
C2	0.3462 (2)	0.26638 (12)	0.71490 (7)	0.0179 (3)
H2	0.2421	0.1914	0.6878	0.021*
C3	0.3148 (2)	0.29074 (13)	0.79324 (7)	0.0177 (3)
H3	0.1903	0.2327	0.8192	0.021*
C4	0.4655 (2)	0.40050 (12)	0.83408 (6)	0.0156 (2)
C5	0.6512 (2)	0.48187 (13)	0.79535 (7)	0.0187 (3)
H5	0.7588	0.5550	0.8230	0.022*
C6	0.6810 (2)	0.45726 (13)	0.71660 (7)	0.0178 (3)
H6	0.8075	0.5146	0.6910	0.021*
C7	0.5571 (2)	0.32441 (12)	0.59009 (6)	0.0149 (2)
C8	0.7713 (2)	0.40782 (13)	0.55104 (7)	0.0195 (3)
H8A	0.7606	0.3815	0.4954	0.029*
H8B	0.9553	0.3841	0.5762	0.029*
H8C	0.7377	0.5123	0.5560	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (5)	0.0272 (5)	0.0121 (4)	−0.0020 (4)	0.0043 (3)	−0.0033 (3)
N1	0.0190 (5)	0.0200 (5)	0.0118 (5)	0.0020 (4)	0.0038 (4)	−0.0010 (4)
N2	0.0230 (5)	0.0190 (5)	0.0141 (5)	0.0005 (4)	0.0032 (4)	−0.0012 (4)
C1	0.0144 (5)	0.0144 (5)	0.0156 (5)	0.0029 (4)	0.0024 (4)	0.0005 (4)
C2	0.0191 (6)	0.0168 (5)	0.0178 (5)	−0.0026 (4)	0.0018 (4)	−0.0015 (4)
C3	0.0172 (5)	0.0182 (6)	0.0181 (6)	−0.0017 (4)	0.0042 (4)	0.0018 (4)
C4	0.0168 (5)	0.0160 (5)	0.0138 (5)	0.0042 (4)	0.0012 (4)	0.0003 (4)
C5	0.0200 (6)	0.0173 (6)	0.0187 (6)	−0.0025 (4)	0.0017 (4)	−0.0036 (4)
C6	0.0179 (5)	0.0176 (5)	0.0185 (6)	−0.0017 (4)	0.0041 (4)	0.0006 (4)
C7	0.0139 (5)	0.0158 (5)	0.0153 (5)	0.0039 (4)	0.0027 (4)	0.0019 (4)
C8	0.0177 (5)	0.0231 (6)	0.0182 (5)	−0.0019 (4)	0.0045 (4)	0.0010 (4)

O1—N1	1.4175 (11)	C3—C4	1.3961 (16)
O1—H1O	0.92 (2)	C3—H3	0.9500
N1—C7	1.2869 (15)	C4—C5	1.3905 (16)
N2—C4	1.4173 (14)	C5—C6	1.3903 (15)
N2—H2N	0.916 (18)	C5—H5	0.9500
N2—H2M	0.929 (19)	C6—H6	0.9500
C1—C6	1.3961 (16)	C7—C8	1.5026 (15)
C1—C2	1.4020 (16)	C8—H8A	0.9800
C1—C7	1.4872 (14)	C8—H8B	0.9800
C2—C3	1.3846 (15)	C8—H8C	0.9800
C2—H2	0.9500
N1—O1—H1O	100.9 (11)	C3—C4—N2	121.15 (10)
C7—N1—O1	113.10 (9)	C6—C5—C4	120.63 (10)
C4—N2—H2N	111.6 (10)	C6—C5—H5	119.7
C4—N2—H2M	111.1 (11)	C4—C5—H5	119.7
H2N—N2—H2M	111.2 (15)	C5—C6—C1	121.09 (10)
C6—C1—C2	117.60 (10)	C5—C6—H6	119.5
C6—C1—C7	121.17 (10)	C1—C6—H6	119.5
C2—C1—C7	121.23 (10)	N1—C7—C1	115.76 (9)
C3—C2—C1	121.59 (11)	N1—C7—C8	124.95 (10)
C3—C2—H2	119.2	C1—C7—C8	119.29 (10)
C1—C2—H2	119.2	C7—C8—H8A	109.5
C2—C3—C4	120.12 (10)	C7—C8—H8B	109.5
C2—C3—H3	119.9	H8A—C8—H8B	109.5
C4—C3—H3	119.9	C7—C8—H8C	109.5
C5—C4—C3	118.94 (10)	H8A—C8—H8C	109.5
C5—C4—N2	119.85 (10)	H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2i	0.92 (2)	1.88 (2)	2.7919 (14)	169.8 (18)
N2—H2N···O1ii	0.916 (18)	2.165 (18)	3.0790 (13)	175.7 (15)
N2—H2M···N1iii	0.929 (19)	2.525 (19)	3.3000 (14)	141.0 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2i	0.92 (2)	1.88 (2)	2.7919 (14)	169.8 (18)
N2—H2N⋯O1ii	0.916 (18)	2.165 (18)	3.0790 (13)	175.7 (15)
N2—H2M⋯N1iii	0.929 (19)	2.525 (19)	3.3000 (14)	141.0 (14)

Symmetry codes: (i) ; (ii) ; (iii) .