1-(4-{[(E)-4-Methyl­benzyl­idene]amino}­phen­yl)ethanone oxime

Zhao, L.; Ng, S.W.

doi:10.1107/S1600536810034598

organic compounds

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Volume 66| Part 10| October 2010| Page o2473

doi:10.1107/S1600536810034598

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1-(4-{[(E)-4-Methylbenzylidene]amino}phenyl)ethanone oxime

Li Zhao ^a ^* and Seik Weng Ng ^b

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: zhaoli_72@163.com

(Received 21 August 2010; accepted 27 August 2010; online 4 September 2010)

In the title compound, C₁₆H₁₆N₂O, the dihedral angle formed by the two benzene rings is 50.3 (1)°. In the crystal structure, molecules are linked into an infinite one-dimensional supramolecular structure by intermolecular O—H⋯N hydrogen-bond interactions.

Related literature

For background to oxime-type compounds, see: Dong et al. (2009a ,b ). For the synthesis, see: Rafiq et al. (2008 ); Dong et al. (2009c ).

Experimental

Crystal data

C₁₆H₁₆N₂O
M_r = 252.31
Monoclinic, P 2₁ /n
a = 5.7785 (6) Å
b = 14.581 (2) Å
c = 16.226 (2) Å
β = 94.285 (1)°
V = 1363.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.45 × 0.15 × 0.10 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.966, T_max = 0.992
6860 measured reflections
2396 independent reflections
1480 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.136
S = 0.95
2396 reflections
178 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 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
O1—H1⋯N2ⁱ	0.86 (1)	2.06 (1)	2.919 (2)	175 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034598/hg2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034598/hg2705Isup2.hkl

checkCIF report

Comment top

Oxime-type compounds are a great important ligands in modern coordination chemistry (Dong et al., 2009a; Dong et al., 2009b). Structures of oxime-type compounds derived from substituted benzaldehydes and 1-(4-aminophenyl)ethanone haven't been reported so far (Rafiq et al., 2008). Here we report the synthesis and crystal structure of (E)-4-[1-(Hydroxyimino)ethyl]-N-(4-methylbenzylidene)aniline (I), (Fig. 1).

The single-crystal structure of the title compound is built up by discrete C₁₆H₁₆N₂O molecules, in which all bond lengths are in normal ranges. Within the molecule, the dihedral angle formed by the two benzene rings is 50.3 (1)°. In the crystal structure, the molecules are linked into infinite one-dimensional supramolecular structure by intermolecular O—H···N hydrogen bond interaction (Table 1 and Fig. 2).

Related literature top

For background to oxime-type compounds, see: Dong et al. (2009a,b). For the synthesis, see: Rafiq et al. (2008); Dong et al. (2009c).

Experimental top

4-Aminophenylethanone oxime was prepared by 1-(4-aminophenyl)ethanone, hydroxylamine sulfate and sodium acetate (Rafiq et al., 2008; Dong et al., 2009c). To an ethanol solution (7 ml) of 4-aminophenylethanone oxime (151.0 mg, 1.00 mmol) was added dropwise an ethanol solution (8 ml) of 4-methylbenzaldehyde (121.6 mg, 1.00 mmol). The mixture solution was stirred at 330 K for 4 h. After cooling to room temperature, the precipitate was filtered off, and washed successively three times with ethanol. The product was dried in vacuo and purified by recrystallization from ethanol to yield 220.3 mg (Yield, 80.8%) of solid; m.p. 471–472 K. Pale-yellow block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of acetone of (I) at room temperature for about two weeks. Anal. Calcd. for C₁₆H₁₆N₂O: C, 76.16; H, 6.39; N, 11.10; Found: C, 76.08; H, 6.45; N, 11.02.

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₆H₁₆N₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Part of one-dimensional supramolecular structure is formed by O—H···N intermolecular interaction with H bonds drawn as dotted lines.

1-(4-{[(E)-4-Methylbenzylidene]amino}phenyl)ethanone oxime top

Crystal data top

C₁₆H₁₆N₂O	F(000) = 536
M_r = 252.31	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1735 reflections
a = 5.7785 (6) Å	θ = 2.5–25.3°
b = 14.581 (2) Å	µ = 0.08 mm⁻¹
c = 16.226 (2) Å	T = 293 K
β = 94.285 (1)°	Block, yellow
V = 1363.4 (2) Å³	0.45 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART diffractometer	2396 independent reflections
Radiation source: fine-focus sealed tube	1480 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.966, T_max = 0.992	k = −17→14
6860 measured reflections	l = −18→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0748P)²] where P = (F_o² + 2F_c²)/3
2396 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O	V = 1363.4 (2) Å³
M_r = 252.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.7785 (6) Å	µ = 0.08 mm⁻¹
b = 14.581 (2) Å	T = 293 K
c = 16.226 (2) Å	0.45 × 0.15 × 0.10 mm
β = 94.285 (1)°

Data collection top

Bruker SMART diffractometer	2396 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1480 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.992	R_int = 0.054
6860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.15 e Å⁻³
2396 reflections	Δρ_min = −0.17 e Å⁻³
178 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7517 (3)	0.26556 (12)	0.05236 (8)	0.0674 (5)
H1	0.861 (4)	0.2274 (16)	0.0445 (16)	0.107 (11)*
N1	0.7670 (3)	0.27459 (12)	0.13916 (9)	0.0529 (5)
N2	0.6350 (3)	0.35564 (11)	0.51824 (10)	0.0512 (5)
C1	0.4032 (4)	0.36066 (17)	0.11219 (13)	0.0710 (7)
H1A	0.4313	0.3513	0.0552	0.106*
H1B	0.3934	0.4252	0.1231	0.106*
H1C	0.2599	0.3316	0.1236	0.106*
C2	0.5974 (4)	0.32006 (13)	0.16606 (11)	0.0457 (5)
C3	0.6050 (3)	0.32942 (12)	0.25745 (11)	0.0419 (5)
C4	0.4248 (4)	0.36780 (14)	0.29717 (12)	0.0515 (5)
H4	0.2943	0.3890	0.2659	0.062*
C5	0.4343 (4)	0.37537 (14)	0.38259 (12)	0.0531 (6)
H5	0.3091	0.4001	0.4078	0.064*
C6	0.6290 (4)	0.34636 (13)	0.43064 (11)	0.0451 (5)
C7	0.8106 (4)	0.30705 (14)	0.39156 (11)	0.0508 (5)
H7	0.9415	0.2861	0.4228	0.061*
C8	0.7974 (4)	0.29896 (13)	0.30692 (12)	0.0506 (5)
H8	0.9206	0.2724	0.2819	0.061*
C9	0.8175 (4)	0.39055 (13)	0.55448 (12)	0.0502 (5)
H9	0.9316	0.4104	0.5211	0.060*
C10	0.8639 (4)	0.40224 (12)	0.64333 (12)	0.0470 (5)
C11	0.7108 (4)	0.37421 (14)	0.70052 (12)	0.0554 (6)
H11	0.5694	0.3481	0.6823	0.066*
C12	0.7675 (4)	0.38494 (14)	0.78433 (12)	0.0605 (6)
H12	0.6630	0.3658	0.8217	0.073*
C13	0.9766 (4)	0.42353 (14)	0.81375 (13)	0.0555 (6)
C14	1.1268 (4)	0.45209 (14)	0.75684 (13)	0.0624 (6)
H14	1.2677	0.4786	0.7752	0.075*
C15	1.0720 (4)	0.44209 (14)	0.67304 (13)	0.0593 (6)
H15	1.1759	0.4623	0.6359	0.071*
C16	1.0399 (5)	0.43398 (18)	0.90515 (13)	0.0821 (8)
H16A	1.1710	0.3958	0.9210	0.123*
H16B	0.9106	0.4160	0.9354	0.123*
H16C	1.0783	0.4968	0.9173	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0689 (12)	0.0968 (13)	0.0364 (9)	0.0112 (10)	0.0044 (7)	−0.0072 (8)
N1	0.0546 (12)	0.0723 (12)	0.0319 (9)	0.0032 (9)	0.0043 (8)	−0.0032 (8)
N2	0.0532 (11)	0.0621 (11)	0.0388 (10)	−0.0012 (9)	0.0078 (8)	−0.0002 (8)
C1	0.0772 (18)	0.0874 (17)	0.0466 (13)	0.0216 (14)	−0.0075 (12)	−0.0056 (11)
C2	0.0468 (13)	0.0492 (12)	0.0411 (11)	−0.0013 (10)	0.0027 (9)	0.0008 (9)
C3	0.0436 (12)	0.0441 (11)	0.0383 (10)	−0.0009 (9)	0.0034 (9)	0.0033 (8)
C4	0.0461 (13)	0.0631 (13)	0.0449 (12)	0.0082 (10)	0.0015 (10)	0.0029 (9)
C5	0.0472 (13)	0.0670 (14)	0.0462 (12)	0.0069 (11)	0.0110 (10)	−0.0012 (9)
C6	0.0503 (13)	0.0503 (11)	0.0356 (11)	−0.0028 (9)	0.0078 (9)	0.0025 (8)
C7	0.0469 (13)	0.0632 (13)	0.0422 (12)	0.0074 (10)	0.0016 (10)	0.0018 (9)
C8	0.0481 (13)	0.0610 (13)	0.0430 (12)	0.0088 (10)	0.0065 (10)	−0.0019 (9)
C9	0.0543 (14)	0.0529 (12)	0.0447 (12)	−0.0008 (10)	0.0122 (10)	0.0012 (9)
C10	0.0556 (14)	0.0451 (11)	0.0406 (11)	0.0013 (10)	0.0050 (10)	−0.0027 (8)
C11	0.0566 (14)	0.0648 (13)	0.0448 (12)	−0.0067 (11)	0.0048 (10)	−0.0059 (10)
C12	0.0717 (16)	0.0685 (15)	0.0419 (12)	−0.0052 (12)	0.0078 (11)	−0.0055 (10)
C13	0.0699 (16)	0.0499 (12)	0.0459 (12)	0.0042 (11)	−0.0017 (11)	−0.0061 (9)
C14	0.0628 (16)	0.0594 (13)	0.0629 (15)	−0.0095 (11)	−0.0096 (12)	−0.0083 (11)
C15	0.0609 (15)	0.0594 (14)	0.0582 (14)	−0.0098 (11)	0.0084 (12)	−0.0013 (10)
C16	0.101 (2)	0.0889 (18)	0.0538 (15)	0.0072 (15)	−0.0125 (14)	−0.0117 (12)

Geometric parameters (Å, º) top

O1—N1	1.4107 (19)	C7—H7	0.9300
O1—H1	0.860 (10)	C8—H8	0.9300
N1—C2	1.286 (2)	C9—C10	1.457 (3)
N2—C9	1.275 (2)	C9—H9	0.9300
N2—C6	1.426 (2)	C10—C15	1.389 (3)
C1—C2	1.492 (3)	C10—C11	1.390 (3)
C1—H1A	0.9600	C11—C12	1.384 (3)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C12—C13	1.385 (3)
C2—C3	1.487 (2)	C12—H12	0.9300
C3—C4	1.383 (3)	C13—C14	1.378 (3)
C3—C8	1.394 (3)	C13—C16	1.509 (3)
C4—C5	1.387 (3)	C14—C15	1.381 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.386 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.389 (3)	C16—H16B	0.9600
C7—C8	1.375 (3)	C16—H16C	0.9600

N1—O1—H1	102.5 (18)	C3—C8—H8	119.0
C2—N1—O1	113.22 (16)	N2—C9—C10	126.0 (2)
C9—N2—C6	117.10 (18)	N2—C9—H9	117.0
C2—C1—H1A	109.5	C10—C9—H9	117.0
C2—C1—H1B	109.5	C15—C10—C11	117.95 (19)
H1A—C1—H1B	109.5	C15—C10—C9	118.88 (19)
C2—C1—H1C	109.5	C11—C10—C9	123.16 (19)
H1A—C1—H1C	109.5	C12—C11—C10	120.5 (2)
H1B—C1—H1C	109.5	C12—C11—H11	119.8
N1—C2—C3	114.78 (17)	C10—C11—H11	119.8
N1—C2—C1	124.35 (18)	C11—C12—C13	121.4 (2)
C3—C2—C1	120.87 (19)	C11—C12—H12	119.3
C4—C3—C8	117.15 (17)	C13—C12—H12	119.3
C4—C3—C2	122.31 (17)	C14—C13—C12	118.0 (2)
C8—C3—C2	120.54 (18)	C14—C13—C16	120.6 (2)
C3—C4—C5	121.51 (18)	C12—C13—C16	121.4 (2)
C3—C4—H4	119.2	C13—C14—C15	121.2 (2)
C5—C4—H4	119.2	C13—C14—H14	119.4
C6—C5—C4	120.5 (2)	C15—C14—H14	119.4
C6—C5—H5	119.8	C14—C15—C10	121.0 (2)
C4—C5—H5	119.8	C14—C15—H15	119.5
C5—C6—C7	118.56 (18)	C10—C15—H15	119.5
C5—C6—N2	119.34 (18)	C13—C16—H16A	109.5
C7—C6—N2	122.08 (18)	C13—C16—H16B	109.5
C8—C7—C6	120.26 (19)	H16A—C16—H16B	109.5
C8—C7—H7	119.9	C13—C16—H16C	109.5
C6—C7—H7	119.9	H16A—C16—H16C	109.5
C7—C8—C3	122.00 (19)	H16B—C16—H16C	109.5
C7—C8—H8	119.0

O1—N1—C2—C3	178.84 (15)	C4—C3—C8—C7	−0.6 (3)
O1—N1—C2—C1	−0.6 (3)	C2—C3—C8—C7	179.64 (18)
N1—C2—C3—C4	−173.15 (18)	C6—N2—C9—C10	−176.97 (17)
C1—C2—C3—C4	6.3 (3)	N2—C9—C10—C15	−179.7 (2)
N1—C2—C3—C8	6.6 (3)	N2—C9—C10—C11	1.2 (3)
C1—C2—C3—C8	−173.93 (19)	C15—C10—C11—C12	−0.9 (3)
C8—C3—C4—C5	−0.3 (3)	C9—C10—C11—C12	178.23 (18)
C2—C3—C4—C5	179.52 (18)	C10—C11—C12—C13	0.0 (3)
C3—C4—C5—C6	1.6 (3)	C11—C12—C13—C14	0.7 (3)
C4—C5—C6—C7	−2.0 (3)	C11—C12—C13—C16	−179.1 (2)
C4—C5—C6—N2	179.47 (18)	C12—C13—C14—C15	−0.4 (3)
C9—N2—C6—C5	−132.4 (2)	C16—C13—C14—C15	179.4 (2)
C9—N2—C6—C7	49.1 (3)	C13—C14—C15—C10	−0.5 (3)
C5—C6—C7—C8	1.2 (3)	C11—C10—C15—C14	1.1 (3)
N2—C6—C7—C8	179.67 (18)	C9—C10—C15—C14	−178.03 (18)
C6—C7—C8—C3	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.86 (1)	2.06 (1)	2.919 (2)	175 (3)

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O
M_r	252.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.7785 (6), 14.581 (2), 16.226 (2)
β (°)	94.285 (1)
V (Å³)	1363.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	6860, 2396, 1480
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.136, 0.95
No. of reflections	2396
No. of parameters	178
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.86 (1)	2.06 (1)	2.919 (2)	175 (3)

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

We thank the Educational Department Foundation of Gansu Province (No. 20873) and the University of Malaya for supporting this study.

References

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