1-(4-{[(E)-4-Methyl-benzyl-idene]amino}-phen-yl)ethanone oxime.

In the title compound, C(16)H(16)N(2)O, the dihedral angle formed by the two benzene rings is 50.3 (1)°. In the crystal structure, mol-ecules are linked into an infinite one-dimensional supra-molecular structure by inter-molecular O-H⋯N hydrogen-bond inter-actions.

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 = 252.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 0.95

2396 reflections

178 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

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 ▶).

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

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

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

C16H16N2O	F(000) = 536
Mr = 252.31	Dx = 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

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

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(Fo2) + (0.0748P)2] where P = (Fo2 + 2Fc2)/3
2396 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.17 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .