(E)-3,5-Dimeth-oxy-benzaldehyde oxime.

In the title compound, C(9)H(11)NO(3), the oxime grouping is twisted by 12.68 (6)° with respect to the dimethoxyl-benzene ring. In the crystal, mol-ecules are linked into an infinite [100] chain via O-H⋯N hydrogen bonds, instead of the more common oxime packing motif of dimers with an R(2) (2)(6) graph-set motif.

Related literature

For backgroud to oximes as therapeutic agents, see: Marrs et al. (2006 ▶); Jokanovic et al. (2009 ▶). For related structures, see: Bao (2008 ▶); Abbas et al. (2010 ▶). For graph-set theory, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H11NO3

M = 181.19

Orthorhombic,

a = 4.4027 (9) Å

b = 13.800 (3) Å

c = 14.300 (3) Å

V = 868.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.979, T max = 0.990

7173 measured reflections

1239 independent reflections

1115 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.08

1239 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038766/hb5656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038766/hb5656Isup2.hkl

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

C9H11NO3	F(000) = 384
Mr = 181.19	Dx = 1.385 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3117 reflections
a = 4.4027 (9) Å	θ = 2.1–27.9°
b = 13.800 (3) Å	µ = 0.11 mm−1
c = 14.300 (3) Å	T = 113 K
V = 868.9 (3) Å3	Block, colorless
Z = 4	0.20 × 0.18 × 0.10 mm

Rigaku Saturn CCD area-detector diffractometer	1239 independent reflections
Radiation source: rotating anode	1115 reflections with I > 2σ(I)
multilayer	Rint = 0.036
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω and φ scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→12
Tmin = 0.979, Tmax = 0.990	l = −18→18
7173 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.0067P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1239 reflections	Δρmax = 0.22 e Å−3
124 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.135 (12)

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	1.1440 (3)	0.57833 (8)	1.13939 (7)	0.0215 (3)
O2	1.2719 (3)	0.66671 (7)	0.81997 (7)	0.0212 (3)
O3	0.2763 (3)	0.27744 (7)	0.90865 (7)	0.0195 (3)
H3	0.211 (5)	0.2351 (13)	0.9537 (13)	0.029*
N1	0.4898 (3)	0.33604 (8)	0.95540 (9)	0.0159 (3)
C1	1.0843 (4)	0.56661 (10)	1.04608 (10)	0.0170 (3)
C2	1.2075 (4)	0.62501 (10)	0.97646 (10)	0.0179 (3)
H2	1.3404	0.6767	0.9923	0.021*
C3	1.1337 (4)	0.60688 (10)	0.88299 (10)	0.0169 (3)
C4	0.9316 (4)	0.53398 (10)	0.85910 (10)	0.0168 (3)
H4	0.8775	0.5233	0.7956	0.020*
C5	0.8078 (4)	0.47596 (10)	0.93064 (10)	0.0156 (3)
C6	0.8833 (4)	0.49179 (10)	1.02358 (10)	0.0167 (3)
H6	0.7994	0.4522	1.0714	0.020*
C7	1.3439 (4)	0.65620 (10)	1.16453 (11)	0.0221 (4)
H7A	1.5396	0.6476	1.1329	0.033*
H7B	1.3752	0.6561	1.2324	0.033*
H7C	1.2536	0.7180	1.1455	0.033*
C8	1.2008 (4)	0.65223 (11)	0.72320 (10)	0.0255 (4)
H8A	1.2574	0.5862	0.7048	0.038*
H8B	1.3140	0.6990	0.6852	0.038*
H8C	0.9824	0.6616	0.7135	0.038*
C9	0.5886 (3)	0.40214 (10)	0.90072 (10)	0.0161 (3)
H9	0.5170	0.4035	0.8381	0.019*

	U11	U22	U33	U12	U13	U23
O1	0.0254 (6)	0.0209 (5)	0.0180 (5)	−0.0057 (5)	−0.0022 (5)	−0.0001 (4)
O2	0.0242 (6)	0.0191 (5)	0.0204 (5)	−0.0043 (4)	0.0028 (5)	0.0047 (4)
O3	0.0208 (6)	0.0195 (5)	0.0182 (5)	−0.0073 (5)	−0.0012 (5)	−0.0006 (4)
N1	0.0136 (6)	0.0151 (6)	0.0188 (6)	−0.0007 (5)	−0.0006 (6)	−0.0019 (4)
C1	0.0169 (7)	0.0151 (7)	0.0189 (7)	0.0014 (6)	−0.0015 (6)	−0.0009 (5)
C2	0.0161 (7)	0.0137 (6)	0.0238 (7)	−0.0007 (6)	−0.0006 (6)	−0.0007 (5)
C3	0.0156 (7)	0.0135 (7)	0.0218 (7)	0.0024 (6)	0.0032 (6)	0.0038 (5)
C4	0.0175 (7)	0.0163 (7)	0.0166 (7)	0.0015 (6)	0.0001 (6)	0.0009 (5)
C5	0.0132 (7)	0.0134 (6)	0.0203 (7)	0.0018 (6)	−0.0003 (6)	0.0002 (5)
C6	0.0162 (7)	0.0149 (7)	0.0188 (7)	−0.0005 (6)	0.0008 (6)	0.0020 (5)
C7	0.0230 (8)	0.0214 (8)	0.0218 (8)	−0.0030 (6)	−0.0016 (7)	−0.0046 (6)
C8	0.0334 (10)	0.0252 (8)	0.0179 (8)	−0.0010 (7)	0.0049 (7)	0.0048 (6)
C9	0.0157 (7)	0.0171 (7)	0.0156 (7)	0.0010 (6)	−0.0014 (6)	0.0000 (5)

O1—C1	1.3697 (18)	C4—C5	1.4089 (19)
O1—C7	1.4349 (19)	C4—H4	0.9500
O2—C3	1.3653 (17)	C5—C6	1.387 (2)
O2—C8	1.4328 (17)	C5—C9	1.467 (2)
O3—N1	1.4087 (15)	C6—H6	0.9500
O3—H3	0.916 (19)	C7—H7A	0.9800
N1—C9	1.2777 (18)	C7—H7B	0.9800
C1—C2	1.391 (2)	C7—H7C	0.9800
C1—C6	1.397 (2)	C8—H8A	0.9800
C2—C3	1.398 (2)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C3—C4	1.386 (2)	C9—H9	0.9500
C1—O1—C7	116.76 (12)	C5—C6—C1	119.26 (14)
C3—O2—C8	117.12 (12)	C5—C6—H6	120.4
N1—O3—H3	103.9 (12)	C1—C6—H6	120.4
C9—N1—O3	110.28 (12)	O1—C7—H7A	109.5
O1—C1—C2	123.64 (14)	O1—C7—H7B	109.5
O1—C1—C6	115.67 (13)	H7A—C7—H7B	109.5
C2—C1—C6	120.68 (14)	O1—C7—H7C	109.5
C1—C2—C3	119.34 (14)	H7A—C7—H7C	109.5
C1—C2—H2	120.3	H7B—C7—H7C	109.5
C3—C2—H2	120.3	O2—C8—H8A	109.5
O2—C3—C4	124.22 (13)	O2—C8—H8B	109.5
O2—C3—C2	114.79 (13)	H8A—C8—H8B	109.5
C4—C3—C2	120.98 (13)	O2—C8—H8C	109.5
C3—C4—C5	118.82 (14)	H8A—C8—H8C	109.5
C3—C4—H4	120.6	H8B—C8—H8C	109.5
C5—C4—H4	120.6	N1—C9—C5	122.77 (13)
C6—C5—C4	120.89 (14)	N1—C9—H9	118.6
C6—C5—C9	123.12 (13)	C5—C9—H9	118.6
C4—C5—C9	115.94 (13)
C7—O1—C1—C2	0.4 (2)	C3—C4—C5—C6	0.7 (2)
C7—O1—C1—C6	−178.53 (13)	C3—C4—C5—C9	178.22 (13)
O1—C1—C2—C3	179.67 (14)	C4—C5—C6—C1	0.2 (2)
C6—C1—C2—C3	−1.4 (2)	C9—C5—C6—C1	−177.15 (13)
C8—O2—C3—C4	0.0 (2)	O1—C1—C6—C5	179.15 (14)
C8—O2—C3—C2	−179.10 (14)	C2—C1—C6—C5	0.2 (2)
C1—C2—C3—O2	−178.50 (13)	O3—N1—C9—C5	178.28 (12)
C1—C2—C3—C4	2.3 (2)	C6—C5—C9—N1	−12.4 (2)
O2—C3—C4—C5	178.97 (14)	C4—C5—C9—N1	170.15 (14)
C2—C3—C4—C5	−2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1i	0.916 (19)	1.90 (2)	2.7970 (17)	166.5 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1i	0.916 (19)	1.90 (2)	2.7970 (17)	166.5 (19)

Symmetry code: (i) .