(E)-N'-(4-Meth-oxy-benzyl-idene)-2-m-tolyl-acetohydrazide.

In the title mol-ecule, C17H18N2O2, the benzene rings form a dihedral angle of 83.0 (7)°. In the crystal, N-H⋯O hydrogen bonds, in an R(2)2(8) graph-set motif, link mol-ecules into centrocymmetric dimers, and weak C-H⋯π inter-actions further link these dimers into columns in [100].

Related literature

For the biological activity of Schiff bases, see: Desai et al. (2001 ▶); El-Masry et al. (2000 ▶); Hodnett & Dunn (1970 ▶); Pandey et al. (1999 ▶); Singh & Dash (1988 ▶). For Schiff bases employed as ligands for complexation of metal ions, see: Aydogan et al. (2001 ▶). For Schiff bases with applications in dyes and pigments, see: Taggi et al. (2002 ▶). For related structures, see: Akkurt et al. (2011 ▶); Lv et al. (2009a ▶,b ▶); Yu & Lv (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H18N2O2

M = 282.33

Triclinic,

a = 6.4961 (8) Å

b = 9.8047 (10) Å

c = 12.7464 (13) Å

α = 112.130 (9)°

β = 95.507 (10)°

γ = 96.601 (9)°

V = 738.45 (14) Å3

Z = 2

Cu Kα radiation

μ = 0.68 mm−1

T = 173 K

0.34 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.735, T max = 1.000

4418 measured reflections

2840 independent reflections

2032 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.158

S = 1.04

2840 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812047113/cv5364sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047113/cv5364Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047113/cv5364Isup3.cml

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

C17H18N2O2	Z = 2
Mr = 282.33	F(000) = 300
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.4961 (8) Å	Cell parameters from 1237 reflections
b = 9.8047 (10) Å	θ = 3.8–72.4°
c = 12.7464 (13) Å	µ = 0.68 mm−1
α = 112.130 (9)°	T = 173 K
β = 95.507 (10)°	Chunk, colorless
γ = 96.601 (9)°	0.34 × 0.14 × 0.06 mm
V = 738.45 (14) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2840 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2032 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 16.0416 pixels mm-1	θmax = 72.6°, θmin = 3.8°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→8
Tmin = 0.735, Tmax = 1.000	l = −11→15
4418 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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.064P)2 + 0.071P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2840 reflections	Δρmax = 0.21 e Å−3
193 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0097 (12)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4694 (2)	0.19694 (16)	0.05426 (13)	0.0429 (4)
O2	1.6491 (2)	−0.04156 (17)	−0.38486 (13)	0.0482 (4)
N1	0.7161 (2)	0.09164 (19)	−0.04553 (14)	0.0363 (4)
H1	0.6645	0.0052	−0.0486	0.044*
N2	0.8879 (2)	0.10557 (19)	−0.09800 (14)	0.0365 (4)
C1	0.6266 (3)	0.2111 (2)	0.01087 (17)	0.0376 (5)
C2	0.7332 (4)	0.3634 (2)	0.02237 (19)	0.0447 (5)
H2A	0.8138	0.3528	−0.0397	0.054*
H2B	0.6288	0.4255	0.0188	0.054*
C3	0.8763 (3)	0.4349 (2)	0.13628 (19)	0.0397 (5)
C4	1.0802 (4)	0.4059 (2)	0.1471 (2)	0.0488 (6)
H4	1.1354	0.3504	0.0826	0.059*
C5	1.2004 (4)	0.4600 (3)	0.2543 (3)	0.0584 (7)
H5	1.3365	0.4402	0.2617	0.070*
C6	1.1199 (4)	0.5432 (3)	0.3507 (3)	0.0596 (7)
H6	1.2023	0.5784	0.4222	0.071*
C7	0.9182 (4)	0.5748 (2)	0.3419 (2)	0.0487 (6)
C8	0.7994 (3)	0.5198 (2)	0.2336 (2)	0.0419 (5)
H8	0.6640	0.5408	0.2262	0.050*
C9	0.9579 (3)	−0.0161 (2)	−0.14981 (17)	0.0353 (5)
H9	0.8927	−0.1052	−0.1490	0.042*
C10	1.1381 (3)	−0.0163 (2)	−0.20977 (16)	0.0336 (4)
C11	1.2404 (3)	0.1120 (2)	−0.21651 (17)	0.0365 (5)
H11	1.1929	0.2020	−0.1818	0.044*
C12	1.4114 (3)	0.1087 (2)	−0.27377 (18)	0.0376 (5)
H12	1.4781	0.1958	−0.2771	0.045*
C13	1.4832 (3)	−0.0259 (2)	−0.32644 (17)	0.0362 (5)
C14	1.3827 (3)	−0.1543 (2)	−0.31983 (18)	0.0403 (5)
H14	1.4310	−0.2441	−0.3541	0.048*
C15	1.2124 (3)	−0.1503 (2)	−0.26320 (17)	0.0379 (5)
H15	1.1458	−0.2377	−0.2603	0.045*
C16	1.7630 (3)	0.0894 (3)	−0.3878 (2)	0.0523 (6)
H16A	1.6733	0.1318	−0.4272	0.078*
H16B	1.8807	0.0643	−0.4272	0.078*
H16C	1.8118	0.1605	−0.3109	0.078*
C17	0.8251 (5)	0.6648 (3)	0.4450 (2)	0.0709 (8)
H17A	0.7722	0.7457	0.4325	0.106*
H17B	0.9312	0.7039	0.5114	0.106*
H17C	0.7128	0.6020	0.4568	0.106*

	U11	U22	U33	U12	U13	U23
O1	0.0382 (8)	0.0476 (9)	0.0442 (8)	0.0160 (7)	0.0149 (7)	0.0148 (7)
O2	0.0452 (9)	0.0510 (10)	0.0483 (9)	0.0128 (7)	0.0216 (7)	0.0144 (7)
N1	0.0370 (9)	0.0360 (9)	0.0391 (9)	0.0108 (7)	0.0137 (7)	0.0150 (7)
N2	0.0349 (9)	0.0411 (10)	0.0373 (9)	0.0126 (7)	0.0123 (7)	0.0163 (8)
C1	0.0375 (11)	0.0448 (12)	0.0347 (10)	0.0177 (9)	0.0081 (9)	0.0164 (9)
C2	0.0544 (13)	0.0416 (12)	0.0501 (13)	0.0228 (10)	0.0188 (10)	0.0245 (10)
C3	0.0438 (12)	0.0301 (10)	0.0523 (13)	0.0117 (9)	0.0164 (10)	0.0204 (9)
C4	0.0453 (13)	0.0380 (12)	0.0692 (16)	0.0117 (10)	0.0231 (12)	0.0232 (11)
C5	0.0348 (12)	0.0457 (14)	0.096 (2)	0.0049 (10)	0.0052 (13)	0.0307 (14)
C6	0.0587 (16)	0.0412 (13)	0.0705 (18)	−0.0021 (11)	−0.0082 (13)	0.0199 (12)
C7	0.0599 (14)	0.0317 (11)	0.0513 (14)	0.0062 (10)	0.0098 (11)	0.0127 (10)
C8	0.0418 (12)	0.0312 (10)	0.0584 (14)	0.0134 (9)	0.0173 (10)	0.0194 (10)
C9	0.0378 (11)	0.0337 (10)	0.0366 (10)	0.0095 (8)	0.0089 (8)	0.0144 (8)
C10	0.0347 (10)	0.0361 (10)	0.0310 (10)	0.0106 (8)	0.0071 (8)	0.0126 (8)
C11	0.0397 (11)	0.0330 (10)	0.0391 (11)	0.0134 (8)	0.0097 (9)	0.0135 (9)
C12	0.0389 (11)	0.0360 (11)	0.0403 (11)	0.0089 (8)	0.0086 (9)	0.0160 (9)
C13	0.0348 (10)	0.0428 (11)	0.0310 (10)	0.0098 (8)	0.0075 (8)	0.0130 (9)
C14	0.0429 (12)	0.0357 (11)	0.0405 (11)	0.0149 (9)	0.0126 (9)	0.0091 (9)
C15	0.0426 (11)	0.0320 (10)	0.0400 (11)	0.0095 (8)	0.0103 (9)	0.0132 (9)
C16	0.0429 (13)	0.0643 (16)	0.0530 (14)	0.0051 (11)	0.0186 (11)	0.0249 (12)
C17	0.096 (2)	0.0541 (16)	0.0542 (16)	0.0169 (15)	0.0162 (15)	0.0096 (13)

O1—C1	1.225 (2)	C7—C17	1.508 (3)
O2—C13	1.358 (2)	C8—H8	0.9300
O2—C16	1.422 (3)	C9—C10	1.457 (3)
N1—C1	1.352 (2)	C9—H9	0.9300
N1—N2	1.374 (2)	C10—C11	1.390 (3)
N1—H1	0.8600	C10—C15	1.399 (3)
N2—C9	1.286 (2)	C11—C12	1.383 (3)
C1—C2	1.520 (3)	C11—H11	0.9300
C2—C3	1.513 (3)	C12—C13	1.394 (3)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.386 (3)
C3—C8	1.385 (3)	C14—C15	1.374 (3)
C3—C4	1.391 (3)	C14—H14	0.9300
C4—C5	1.383 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.383 (4)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.384 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C7—C8	1.389 (3)	C17—H17C	0.9600
C13—O2—C16	117.66 (17)	N2—C9—H9	119.5
C1—N1—N2	121.37 (17)	C10—C9—H9	119.5
C1—N1—H1	119.3	C11—C10—C15	118.04 (18)
N2—N1—H1	119.3	C11—C10—C9	122.64 (18)
C9—N2—N1	115.66 (17)	C15—C10—C9	119.32 (18)
O1—C1—N1	121.0 (2)	C12—C11—C10	121.44 (18)
O1—C1—C2	121.47 (18)	C12—C11—H11	119.3
N1—C1—C2	117.52 (18)	C10—C11—H11	119.3
C3—C2—C1	108.30 (17)	C11—C12—C13	119.67 (19)
C3—C2—H2A	110.0	C11—C12—H12	120.2
C1—C2—H2A	110.0	C13—C12—H12	120.2
C3—C2—H2B	110.0	O2—C13—C14	116.24 (18)
C1—C2—H2B	110.0	O2—C13—C12	124.44 (19)
H2A—C2—H2B	108.4	C14—C13—C12	119.32 (19)
C8—C3—C4	118.9 (2)	C15—C14—C13	120.69 (19)
C8—C3—C2	119.98 (19)	C15—C14—H14	119.7
C4—C3—C2	120.8 (2)	C13—C14—H14	119.7
C5—C4—C3	119.6 (2)	C14—C15—C10	120.84 (19)
C5—C4—H4	120.2	C14—C15—H15	119.6
C3—C4—H4	120.2	C10—C15—H15	119.6
C4—C5—C6	120.6 (2)	O2—C16—H16A	109.5
C4—C5—H5	119.7	O2—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C5—C6—C7	120.8 (3)	O2—C16—H16C	109.5
C5—C6—H6	119.6	H16A—C16—H16C	109.5
C7—C6—H6	119.6	H16B—C16—H16C	109.5
C6—C7—C8	117.9 (2)	C7—C17—H17A	109.5
C6—C7—C17	122.3 (3)	C7—C17—H17B	109.5
C8—C7—C17	119.8 (2)	H17A—C17—H17B	109.5
C3—C8—C7	122.1 (2)	C7—C17—H17C	109.5
C3—C8—H8	119.0	H17A—C17—H17C	109.5
C7—C8—H8	119.0	H17B—C17—H17C	109.5
N2—C9—C10	120.92 (18)
C1—N1—N2—C9	−179.39 (18)	C17—C7—C8—C3	−179.1 (2)
N2—N1—C1—O1	177.62 (17)	N1—N2—C9—C10	179.35 (16)
N2—N1—C1—C2	−4.8 (3)	N2—C9—C10—C11	−1.4 (3)
O1—C1—C2—C3	83.1 (2)	N2—C9—C10—C15	178.72 (18)
N1—C1—C2—C3	−94.5 (2)	C15—C10—C11—C12	−0.2 (3)
C1—C2—C3—C8	−88.4 (2)	C9—C10—C11—C12	179.85 (18)
C1—C2—C3—C4	85.9 (2)	C10—C11—C12—C13	0.2 (3)
C8—C3—C4—C5	1.0 (3)	C16—O2—C13—C14	−176.56 (19)
C2—C3—C4—C5	−173.3 (2)	C16—O2—C13—C12	3.1 (3)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—O2	179.91 (18)
C4—C5—C6—C7	−0.3 (4)	C11—C12—C13—C14	−0.5 (3)
C5—C6—C7—C8	0.3 (4)	O2—C13—C14—C15	−179.62 (18)
C5—C6—C7—C17	179.8 (2)	C12—C13—C14—C15	0.7 (3)
C4—C3—C8—C7	−1.2 (3)	C13—C14—C15—C10	−0.7 (3)
C2—C3—C8—C7	173.23 (19)	C11—C10—C15—C14	0.5 (3)
C6—C7—C8—C3	0.5 (3)	C9—C10—C15—C14	−179.58 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.04	2.902 (2)	178
C15—H15···Cgii	0.93	2.63	3.557 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.04	2.902 (2)	178
C15—H15⋯Cg ii	0.93	2.63	3.557 (2)	173

Symmetry codes: (i) ; (ii) .