1-(4-{[(E)-3-Eth­oxy-2-hy­droxy­benzyl­idene]amino}­phen­yl)ethanone oxime

Zhao, L.; Dong, X.-T.; Xing, S.-J.; Cheng, Q.; Zhao, J.-X.

doi:10.1107/S1600536812001213

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o429

doi:10.1107/S1600536812001213

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1-(4-{[(E)-3-Ethoxy-2-hydroxybenzylidene]amino}phenyl)ethanone oxime

Li Zhao,^a ^* Xu-Tao Dong,^a Si-Jia Xing,^a Qian Cheng ^a and Ji-Xing Zhao ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: zhaoli_72@163.com

(Received 19 December 2011; accepted 10 January 2012; online 18 January 2012)

In the title compound, C₁₇H₁₈N₂O₃, the benzene rings form a dihedral angle of 3.34 (2)°. There is a strong intramolecular O—H⋯N hydrogen bonds (which induces planarity of the structure). In the crystal, molecules are linked by pairs of O—H⋯N hydrogen bonds, forming inversion dimers.

Related literature

For background to oxime-type compounds, see: Dong et al., (2009 ); Narasaka & Kitamura (2005 ). For their syntheses and structures, see: Dong et al. (2008 ); Akine et al. (2002 ); Wu et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₃
M_r = 298.33
Triclinic, $[P \overline 1]$
a = 7.0556 (7) Å
b = 7.4852 (9) Å
c = 14.7821 (16) Å
α = 96.890 (1)°
β = 98.762 (1)°
γ = 102.105 (2)°
V = 745.03 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.32 × 0.21 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.971, T_max = 0.988
3664 measured reflections
2561 independent reflections
1376 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.168
S = 1.02
2561 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	2.07	2.817 (4)	152
O2—H2⋯N2	0.82	1.84	2.567 (3)	147
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001213/hg5155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001213/hg5155Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001213/hg5155Isup3.cml

checkCIF report

Comment top

Oxime-type compounds are a traditional class of chelating ligands widely used in coordination and analytical chemistry and extraction metallurgy (Dong et al., 2009; Narasaka et al., 2005). In the last few years, a large number of oxime-type compounds and their complexes have been reported (Dong et al., 2008; Akine et al., 2002). However, the oxime-type compounds derived the 4-aminophenylethanone have never been reported. In this paper, the crystal structure of new oxime-type compound, 1-(4-{[(E)-3-ethoxy-2-hydroxybenzylidene] amino}phenyl)ethanone oxime, derived from the reaction of 4-amino-phenylethanone oxime and 3-ethoxysalicylaldehyde (I), (Fig. 1) is reported.

The single-crystal structure of the title compound was determined by X-ray crystallography. The crystal structure of the title compound is only built up by the C₁₇H₁₈N₂O₃ molecules, in which all bond lengths are in normal ranges. The two benzene rings form a dihedral angle of 3.34 (2) °. There is a strong intramolecular O2–H2···N2 hydrogen bonds (which induces planarity on the structure). In the crystal structure, the molecules form dimers disposed about two pairs of inter-molecular O—H..N hydrogen bonds. (Table 1)(Wu et al., 2010).

Related literature top

For background to oxime-type compounds, see: Dong et al., (2009); Narasaka et al. (2005). For their syntheses and structures, see: Dong et al. (2008); Akine et al. (2002); Wu et al. (2010).

Experimental top

To an ethanol solution (5 ml) of 3-ethoxysalicylaldehyde(166.2 mg, 1.00 mmol) was added an ethanol solution (5 ml) of 4-aminophenylethanone oxime (151.7 mg, 1.00 mmol). After the solution had been stirred at 328 K for 5 h, the mixture was filtered. The residue was washed successively with ethanol and n-hexane, respectively. The isolated compound was dried under reduced pressure to yield 281.1 mg of yellow solid (yield 80%, m.p. 436–437 K). Elemental analysis also supports composition of the title compound. Anal. calcd. for C₁₇H₁₈N₂O₃: C 68.44; H 6.08; N 9.39; Found: C, 68.30; H, 6.02; N, 9.52. The single crystals were obtained by slow evaporation from an acetonitrile solution at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule structure of the title compound with atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Digram showing the intramolecular O—H···N and intermolecular O—H···N hydrogen bonding interactions. Hydrogen atoms not involved have been deleted for clarity.

1-(4-{[(E)-3-Ethoxy-2-hydroxybenzylidene]amino}phenyl)ethanone oxime top

Crystal data top

C₁₇H₁₈N₂O₃	Z = 2
M_r = 298.33	F(000) = 316
Triclinic, P1	D_x = 1.330 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0556 (7) Å	Cell parameters from 818 reflections
b = 7.4852 (9) Å	θ = 2.8–27.5°
c = 14.7821 (16) Å	µ = 0.09 mm⁻¹
α = 96.890 (1)°	T = 298 K
β = 98.762 (1)°	Prismatical, yellow
γ = 102.105 (2)°	0.32 × 0.21 × 0.13 mm
V = 745.03 (14) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2561 independent reflections
Radiation source: fine-focus sealed tube	1376 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
phi and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.971, T_max = 0.988	k = −8→8
3664 measured reflections	l = −17→9

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0613P)² + 0.2977P] where P = (F_o² + 2F_c²)/3
2561 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₃	γ = 102.105 (2)°
M_r = 298.33	V = 745.03 (14) Å³
Triclinic, P1	Z = 2
a = 7.0556 (7) Å	Mo Kα radiation
b = 7.4852 (9) Å	µ = 0.09 mm⁻¹
c = 14.7821 (16) Å	T = 298 K
α = 96.890 (1)°	0.32 × 0.21 × 0.13 mm
β = 98.762 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2561 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1376 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.988	R_int = 0.037
3664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
2561 reflections	Δρ_min = −0.27 e Å⁻³
201 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
N1	0.3517 (4)	0.5142 (4)	0.91196 (19)	0.0451 (8)
N2	0.4699 (4)	0.7402 (4)	0.51348 (18)	0.0399 (7)
O1	0.2676 (4)	0.4614 (4)	0.98854 (17)	0.0644 (8)
H1	0.3548	0.4525	1.0301	0.097*
O2	0.3342 (3)	0.8040 (3)	0.35234 (16)	0.0518 (7)
H2	0.3308	0.7783	0.4046	0.078*
O3	0.3898 (3)	0.8888 (4)	0.19161 (16)	0.0522 (7)
C1	0.0075 (5)	0.5044 (6)	0.8478 (3)	0.0667 (13)
H1A	−0.0132	0.4861	0.9090	0.100*
H1B	−0.0658	0.3980	0.8041	0.100*
H1C	−0.0362	0.6120	0.8325	0.100*
C2	0.2226 (5)	0.5310 (5)	0.8443 (2)	0.0396 (9)
C3	0.2949 (5)	0.5820 (4)	0.7593 (2)	0.0332 (8)
C4	0.4926 (5)	0.6169 (5)	0.7524 (2)	0.0443 (10)
H4	0.5844	0.6042	0.8020	0.053*
C5	0.5573 (5)	0.6699 (5)	0.6740 (2)	0.0465 (10)
H5	0.6913	0.6937	0.6720	0.056*
C6	0.4246 (5)	0.6879 (4)	0.5984 (2)	0.0351 (8)
C7	0.2268 (5)	0.6483 (5)	0.6030 (2)	0.0446 (10)
H7	0.1352	0.6561	0.5522	0.053*
C8	0.1624 (5)	0.5971 (5)	0.6820 (2)	0.0449 (10)
H8	0.0282	0.5724	0.6836	0.054*
C9	0.6452 (5)	0.7803 (4)	0.4955 (2)	0.0376 (9)
H9	0.7514	0.7766	0.5404	0.045*
C10	0.6814 (5)	0.8313 (4)	0.4067 (2)	0.0344 (8)
C11	0.5221 (5)	0.8398 (4)	0.3389 (2)	0.0355 (8)
C12	0.5558 (5)	0.8854 (5)	0.2518 (2)	0.0382 (9)
C13	0.7458 (5)	0.9199 (5)	0.2339 (2)	0.0412 (9)
H13	0.7682	0.9488	0.1764	0.049*
C14	0.9048 (5)	0.9119 (5)	0.3015 (2)	0.0427 (9)
H14	1.0321	0.9360	0.2890	0.051*
C15	0.8720 (5)	0.8682 (5)	0.3863 (2)	0.0384 (9)
H15	0.9781	0.8630	0.4309	0.046*
C16	0.4125 (5)	0.9423 (5)	0.1031 (2)	0.0506 (10)
H16A	0.4586	0.8501	0.0659	0.061*
H16B	0.5070	1.0601	0.1109	0.061*
C17	0.2127 (6)	0.9575 (7)	0.0572 (3)	0.0781 (15)
H17A	0.1228	0.8383	0.0466	0.117*
H17B	0.2220	1.0006	−0.0009	0.117*
H17C	0.1655	1.0433	0.0966	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0459 (19)	0.059 (2)	0.0336 (18)	0.0094 (15)	0.0162 (14)	0.0153 (14)
N2	0.0371 (18)	0.0485 (19)	0.0364 (18)	0.0112 (14)	0.0100 (13)	0.0084 (14)
O1	0.0549 (18)	0.103 (2)	0.0438 (17)	0.0163 (16)	0.0224 (13)	0.0324 (15)
O2	0.0305 (15)	0.085 (2)	0.0447 (16)	0.0123 (13)	0.0110 (11)	0.0243 (13)
O3	0.0358 (15)	0.085 (2)	0.0345 (15)	0.0073 (13)	0.0001 (11)	0.0229 (13)
C1	0.043 (3)	0.111 (4)	0.048 (3)	0.014 (2)	0.0157 (19)	0.018 (2)
C2	0.038 (2)	0.046 (2)	0.033 (2)	0.0060 (17)	0.0095 (16)	0.0061 (17)
C3	0.033 (2)	0.037 (2)	0.031 (2)	0.0085 (15)	0.0097 (14)	0.0051 (15)
C4	0.034 (2)	0.071 (3)	0.032 (2)	0.0155 (18)	0.0049 (15)	0.0166 (19)
C5	0.031 (2)	0.071 (3)	0.043 (2)	0.0136 (19)	0.0118 (17)	0.0162 (19)
C6	0.042 (2)	0.038 (2)	0.030 (2)	0.0128 (17)	0.0108 (15)	0.0097 (16)
C7	0.037 (2)	0.063 (3)	0.038 (2)	0.0144 (19)	0.0075 (16)	0.0171 (19)
C8	0.032 (2)	0.062 (3)	0.044 (2)	0.0126 (18)	0.0096 (16)	0.0113 (19)
C9	0.038 (2)	0.043 (2)	0.032 (2)	0.0111 (17)	0.0029 (15)	0.0089 (16)
C10	0.035 (2)	0.039 (2)	0.030 (2)	0.0110 (16)	0.0047 (14)	0.0077 (15)
C11	0.030 (2)	0.044 (2)	0.035 (2)	0.0091 (16)	0.0106 (15)	0.0081 (16)
C12	0.032 (2)	0.045 (2)	0.034 (2)	0.0044 (17)	0.0019 (15)	0.0063 (16)
C13	0.038 (2)	0.046 (2)	0.040 (2)	0.0087 (17)	0.0090 (16)	0.0100 (17)
C14	0.031 (2)	0.051 (2)	0.047 (2)	0.0067 (17)	0.0134 (16)	0.0093 (18)
C15	0.031 (2)	0.049 (2)	0.036 (2)	0.0109 (17)	0.0047 (15)	0.0102 (17)
C16	0.054 (3)	0.060 (3)	0.037 (2)	0.009 (2)	0.0047 (17)	0.0163 (19)
C17	0.064 (3)	0.110 (4)	0.059 (3)	0.013 (3)	−0.003 (2)	0.038 (3)

Geometric parameters (Å, º) top

N1—C2	1.283 (4)	C7—C8	1.383 (5)
N1—O1	1.416 (3)	C7—H7	0.9300
N2—C9	1.286 (4)	C8—H8	0.9300
N2—C6	1.420 (4)	C9—C10	1.454 (4)
O1—H1	0.8200	C9—H9	0.9300
O2—C11	1.346 (4)	C10—C15	1.401 (4)
O2—H2	0.8200	C10—C11	1.406 (4)
O3—C12	1.366 (4)	C11—C12	1.411 (4)
O3—C16	1.435 (4)	C12—C13	1.384 (4)
C1—C2	1.498 (5)	C13—C14	1.400 (4)
C1—H1A	0.9600	C13—H13	0.9300
C1—H1B	0.9600	C14—C15	1.374 (4)
C1—H1C	0.9600	C14—H14	0.9300
C2—C3	1.488 (4)	C15—H15	0.9300
C3—C4	1.387 (4)	C16—C17	1.502 (5)
C3—C8	1.393 (4)	C16—H16A	0.9700
C4—C5	1.379 (5)	C16—H16B	0.9700
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.384 (4)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.378 (5)

C2—N1—O1	112.6 (3)	N2—C9—H9	119.2
C9—N2—C6	124.4 (3)	C10—C9—H9	119.2
N1—O1—H1	109.5	C15—C10—C11	119.0 (3)
C11—O2—H2	109.5	C15—C10—C9	121.4 (3)
C12—O3—C16	118.0 (3)	C11—C10—C9	119.6 (3)
C2—C1—H1A	109.5	O2—C11—C10	122.8 (3)
C2—C1—H1B	109.5	O2—C11—C12	117.3 (3)
H1A—C1—H1B	109.5	C10—C11—C12	119.9 (3)
C2—C1—H1C	109.5	O3—C12—C13	125.9 (3)
H1A—C1—H1C	109.5	O3—C12—C11	114.6 (3)
H1B—C1—H1C	109.5	C13—C12—C11	119.5 (3)
N1—C2—C3	117.0 (3)	C12—C13—C14	120.7 (3)
N1—C2—C1	123.4 (3)	C12—C13—H13	119.7
C3—C2—C1	119.5 (3)	C14—C13—H13	119.7
C4—C3—C8	116.9 (3)	C15—C14—C13	119.8 (3)
C4—C3—C2	122.9 (3)	C15—C14—H14	120.1
C8—C3—C2	120.2 (3)	C13—C14—H14	120.1
C5—C4—C3	122.0 (3)	C14—C15—C10	121.1 (3)
C5—C4—H4	119.0	C14—C15—H15	119.4
C3—C4—H4	119.0	C10—C15—H15	119.4
C4—C5—C6	120.6 (3)	O3—C16—C17	106.4 (3)
C4—C5—H5	119.7	O3—C16—H16A	110.5
C6—C5—H5	119.7	C17—C16—H16A	110.5
C7—C6—C5	118.2 (3)	O3—C16—H16B	110.5
C7—C6—N2	115.2 (3)	C17—C16—H16B	110.5
C5—C6—N2	126.6 (3)	H16A—C16—H16B	108.7
C6—C7—C8	121.1 (3)	C16—C17—H17A	109.5
C6—C7—H7	119.4	C16—C17—H17B	109.5
C8—C7—H7	119.4	H17A—C17—H17B	109.5
C7—C8—C3	121.2 (3)	C16—C17—H17C	109.5
C7—C8—H8	119.4	H17A—C17—H17C	109.5
C3—C8—H8	119.4	H17B—C17—H17C	109.5
N2—C9—C10	121.7 (3)

O1—N1—C2—C3	−178.6 (3)	N2—C9—C10—C15	−177.6 (3)
O1—N1—C2—C1	2.1 (5)	N2—C9—C10—C11	0.9 (5)
N1—C2—C3—C4	−2.2 (5)	C15—C10—C11—O2	179.1 (3)
C1—C2—C3—C4	177.1 (3)	C9—C10—C11—O2	0.6 (5)
N1—C2—C3—C8	178.0 (3)	C15—C10—C11—C12	−0.1 (5)
C1—C2—C3—C8	−2.7 (5)	C9—C10—C11—C12	−178.6 (3)
C8—C3—C4—C5	2.0 (5)	C16—O3—C12—C13	−3.5 (5)
C2—C3—C4—C5	−177.8 (3)	C16—O3—C12—C11	177.2 (3)
C3—C4—C5—C6	−0.8 (6)	O2—C11—C12—O3	0.6 (4)
C4—C5—C6—C7	−1.2 (5)	C10—C11—C12—O3	179.8 (3)
C4—C5—C6—N2	−179.7 (3)	O2—C11—C12—C13	−178.8 (3)
C9—N2—C6—C7	−179.2 (3)	C10—C11—C12—C13	0.5 (5)
C9—N2—C6—C5	−0.6 (5)	O3—C12—C13—C14	−179.9 (3)
C5—C6—C7—C8	1.9 (5)	C11—C12—C13—C14	−0.6 (5)
N2—C6—C7—C8	−179.4 (3)	C12—C13—C14—C15	0.4 (5)
C6—C7—C8—C3	−0.7 (5)	C13—C14—C15—C10	0.0 (5)
C4—C3—C8—C7	−1.3 (5)	C11—C10—C15—C14	−0.1 (5)
C2—C3—C8—C7	178.6 (3)	C9—C10—C15—C14	178.4 (3)
C6—N2—C9—C10	179.5 (3)	C12—O3—C16—C17	−172.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.07	2.817 (4)	152
O2—H2···N2	0.82	1.84	2.567 (3)	147

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₃
M_r	298.33
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.0556 (7), 7.4852 (9), 14.7821 (16)
α, β, γ (°)	96.890 (1), 98.762 (1), 102.105 (2)
V (Å³)	745.03 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.21 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.971, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	3664, 2561, 1376
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.168, 1.02
No. of reflections	2561
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.27

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
O1—H1···N1ⁱ	0.82	2.07	2.817 (4)	151.9
O2—H2···N2	0.82	1.84	2.567 (3)	147.1

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province, which is gratefully acknowledged. The authors are also thankful to Professor Da-Qi Wang of Liaocheng University for the data collection and structure solution.

References

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