(E)-3,5-Dimeth­oxy­benzaldehyde oxime

Dong, B.; Zhang, Y.; Chen, J.-Z.

doi:10.1107/S1600536810038766

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2719

https://doi.org/10.1107/S1600536810038766

Open

access

(E)-3,5-Dimethoxybenzaldehyde oxime

Bin Dong,^a ^* Yu Zhang ^b and Jin-Zhe Chen ^a

^aAffliated Hospital of Hebei University, Baoding 071000, People's Republic of China, and ^bHebei Xushui County Health Bureau, Baoding 071000, People's Republic of China
^*Correspondence e-mail: dbin2000@hotmail.com

(Received 27 September 2010; accepted 28 September 2010; online 2 October 2010)

In the title compound, C₉H₁₁NO₃, the oxime grouping is twisted by 12.68 (6)° with respect to the dimethoxylbenzene ring. In the crystal, molecules 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 R₂²(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_r = 181.19
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.08
1239 reflections
124 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038766/hb5656Isup2.hkl

checkCIF report

Comment top

Oximes are an therapeutic agent in organophosphorus poisoning (Marrs et al., 2006; Jokanovic et al., 2009). As part of our interest in the study of oxime derivatives, we herein report the crystal structure of the title compound (I).

In the crystal structure of the title compound, Fig. 1, the oxime moiety has an E configuration [C5—C9—N1—O3= 178.22 (11)°] and is twisted with respect to the dimethoxylbenzene ring by 12.68 (6)°. Molecules are linked to form an infinite chain down the a axis via O—H···N hydrogen bonds (Fig. 2 and Table 1), which differates from the reported R₂²(6) graph-set motif (Etter et al., 1990; Bernstein et al., 1995; Bao, 2008; Abbas et al., 2010).

Related literature top

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 top

To a solution of 3,4-dimethoxylbenzaldehyde (0.95 g, 5 mmol) in 25 ml e thanol, hydroxylamine hydrochloride (0.42 g, 6 mmol) and aqueous sodium hydroxide (0.24 g, 6 mmol) were added and the mixture was heated under reflux until completion of the reaction. The reaction mixture was concentrated and water added. The precipitate was collected by filtration, washed with water and dried under vaccu. Colourless blocks of (I) were grown out via recrystallization from ethanol.

Structure description top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule of (I) showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The infinite chain formed via O—H···N down the a axis.

(E)-3,5-Dimethoxybenzaldehyde oxime top

Crystal data top

C₉H₁₁NO₃	F(000) = 384
M_r = 181.19	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0566P)² + 0.0067P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
1239 reflections	Δρ_max = 0.22 e Å⁻³
124 parameters	Δρ_min = −0.17 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)

Crystal data top

C₉H₁₁NO₃	V = 868.9 (3) Å³
M_r = 181.19	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.4027 (9) Å	µ = 0.11 mm⁻¹
b = 13.800 (3) Å	T = 113 K
c = 14.300 (3) Å	0.20 × 0.18 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1239 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1115 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.990	R_int = 0.036
7173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.22 e Å⁻³
1239 reflections	Δρ_min = −0.17 e Å⁻³
124 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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₉H₁₁NO₃
M_r	181.19
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	4.4027 (9), 13.800 (3), 14.300 (3)
V (Å³)	868.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.979, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	7173, 1239, 1115
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.08
No. of reflections	1239
No. of parameters	124
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+2.

Acknowledgements

This work was supported by a Hebei Province Heath Bureau grant (No. 20090176), the Ministry of Science and Technology of the People's Republic of China International Cooperation Project (No. 2008DFR10530) and the Science and Technology Support Program of Hebei Province Science and Technology Department (No. 08243531D).

References

Abbas, A., Hussain, S., Hafeez, N., Badshah, A., Hasan, A. & Lo, K. M. (2010). Acta Cryst. E66, o1130. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bao, F.-Y. (2008). Acta Cryst. E64, o2134. Web of Science CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jokanovic, M. & Prostran, M. (2009). Curr. Med. Chem. 16, 2177–2188. Web of Science CrossRef PubMed CAS Google Scholar
Marrs, T. C., Rice, P. & Vale, J. A. (2006). Toxicol. Rev. 25, 297–323. CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar