(E)-N'-[4-(Di-methyl-amino)-benzyl-idene]-2-(4-methyl-phen-oxy)acetohydrazide.

In the title compound, C18H21N3O2, the dihedral angle between the benzene rings is 68.85 (11)°. In the crystal, the mol-ecules are linked by C-H⋯O and N-H⋯O hydrogen bonds, as well as weak C-H⋯π contacts, forming a three-dimensional supra-molecular architecture.

Related literature

For biological background to hydrazone derivatives, see: Nithinchandra et al. (2012 ▶, 2013 ▶); Holla et al. (1992 ▶); Kalluraya et al. (1995 ▶). For related structures, see: Sarfraz et al. (2010 ▶); Fun et al. (2011 ▶).

Experimental

Crystal data

C18H21N3O2

M = 311.38

Monoclinic,

a = 11.2237 (6) Å

b = 9.4471 (5) Å

c = 15.8785 (9) Å

β = 100.868 (3)°

V = 1653.42 (16) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2013 ▶) T min = 0.862, T max = 0.873

13214 measured reflections

2725 independent reflections

2318 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.211

S = 1.05

2725 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813034879/xu5759sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034879/xu5759Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034879/xu5759Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H21N3O2	F(000) = 664
Mr = 311.38	Dx = 1.251 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2725 reflections
a = 11.2237 (6) Å	θ = 4.0–64.7°
b = 9.4471 (5) Å	µ = 0.67 mm−1
c = 15.8785 (9) Å	T = 296 K
β = 100.868 (3)°	Block, red
V = 1653.42 (16) Å3	0.23 × 0.22 × 0.21 mm
Z = 4

Bruker X8 Proteum diffractometer	2725 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2318 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.069
Detector resolution: 10.7 pixels mm-1	θmax = 64.7°, θmin = 4.0°
φ and ω scans	h = −12→13
Absorption correction: multi-scan SADABS (Bruker, 2013)	k = −11→5
Tmin = 0.862, Tmax = 0.873	l = −18→18
13214 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)] = 0.075	H-atom parameters constrained
wR(F2) = 0.211	w = 1/[σ2(Fo2) + (0.1529P)2 + 0.2569P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2725 reflections	Δρmax = 0.43 e Å−3
211 parameters	Δρmin = −0.43 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: 0.0102 (18)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.69278 (13)	0.22073 (19)	0.19031 (9)	0.0526 (6)
O2	0.53999 (16)	0.07569 (16)	0.28054 (9)	0.0536 (6)
N1	0.47999 (15)	0.29874 (18)	0.30708 (10)	0.0404 (5)
N2	0.43122 (16)	0.25856 (19)	0.37754 (10)	0.0411 (6)
N3	0.19247 (18)	0.2905 (2)	0.71623 (11)	0.0513 (7)
C1	0.9297 (3)	0.2897 (4)	−0.0930 (2)	0.0937 (14)
C2	0.8634 (2)	0.2746 (3)	−0.01891 (16)	0.0601 (9)
C3	0.9184 (2)	0.2062 (4)	0.05636 (18)	0.0714 (10)
C4	0.8604 (2)	0.1913 (3)	0.12481 (16)	0.0622 (9)
C5	0.74458 (19)	0.2438 (2)	0.11927 (12)	0.0438 (7)
C6	0.6868 (2)	0.3118 (2)	0.04553 (13)	0.0453 (7)
C7	0.7476 (2)	0.3253 (2)	−0.02276 (15)	0.0527 (8)
C8	0.56985 (18)	0.2615 (2)	0.18410 (12)	0.0414 (6)
C9	0.52905 (19)	0.2017 (2)	0.26216 (12)	0.0392 (6)
C10	0.39327 (18)	0.3609 (2)	0.41754 (12)	0.0399 (6)
C11	0.33822 (18)	0.3394 (2)	0.49233 (12)	0.0384 (6)
C12	0.3056 (2)	0.2065 (2)	0.51882 (14)	0.0456 (7)
C13	0.2569 (2)	0.1908 (2)	0.59149 (14)	0.0474 (7)
C14	0.23959 (18)	0.3070 (2)	0.64313 (13)	0.0409 (6)
C15	0.2715 (2)	0.4407 (2)	0.61621 (13)	0.0434 (6)
C16	0.31855 (19)	0.4555 (2)	0.54258 (13)	0.0428 (7)
C17	0.1550 (3)	0.1517 (3)	0.74088 (16)	0.0636 (9)
C18	0.1782 (2)	0.4102 (3)	0.76985 (15)	0.0612 (9)
H1	0.47880	0.38630	0.29210	0.0490*
H1A	1.00830	0.24650	−0.07820	0.1410*
H1B	0.93890	0.38830	−0.10510	0.1410*
H1C	0.88410	0.24400	−0.14280	0.1410*
H3	0.99620	0.16970	0.06030	0.0860*
H4	0.89910	0.14610	0.17450	0.0740*
H6	0.60880	0.34760	0.04170	0.0540*
H7	0.70870	0.37010	−0.07260	0.0630*
H8A	0.52070	0.22370	0.13210	0.0500*
H8B	0.56260	0.36380	0.18310	0.0500*
H10	0.40110	0.45270	0.39820	0.0480*
H12	0.31690	0.12710	0.48670	0.0550*
H13	0.23490	0.10090	0.60690	0.0570*
H15	0.26080	0.52040	0.64840	0.0520*
H16	0.33790	0.54560	0.52580	0.0510*
H17A	0.08590	0.12040	0.70000	0.0950*
H17B	0.13400	0.15720	0.79670	0.0950*
H17C	0.22040	0.08570	0.74230	0.0950*
H18A	0.25520	0.45570	0.78800	0.0920*
H18B	0.14790	0.37840	0.81920	0.0920*
H18C	0.12190	0.47610	0.73800	0.0920*

	U11	U22	U33	U12	U13	U23
O1	0.0494 (9)	0.0749 (12)	0.0419 (8)	0.0043 (8)	0.0300 (7)	0.0077 (7)
O2	0.0804 (11)	0.0332 (9)	0.0576 (9)	0.0002 (7)	0.0400 (8)	−0.0008 (6)
N1	0.0560 (10)	0.0323 (9)	0.0426 (9)	−0.0035 (7)	0.0339 (8)	−0.0003 (7)
N2	0.0524 (10)	0.0392 (10)	0.0400 (9)	−0.0055 (8)	0.0303 (8)	0.0012 (7)
N3	0.0648 (12)	0.0524 (12)	0.0479 (10)	−0.0071 (9)	0.0394 (9)	−0.0023 (8)
C1	0.096 (2)	0.122 (3)	0.083 (2)	−0.018 (2)	0.0681 (18)	0.0022 (18)
C2	0.0650 (15)	0.0688 (17)	0.0579 (14)	−0.0183 (13)	0.0411 (12)	−0.0044 (12)
C3	0.0470 (13)	0.103 (2)	0.0736 (17)	−0.0075 (14)	0.0351 (12)	−0.0028 (15)
C4	0.0482 (13)	0.089 (2)	0.0539 (13)	−0.0008 (12)	0.0214 (10)	0.0062 (12)
C5	0.0489 (12)	0.0480 (13)	0.0423 (11)	−0.0087 (9)	0.0284 (9)	−0.0037 (9)
C6	0.0566 (12)	0.0370 (12)	0.0496 (12)	−0.0001 (9)	0.0287 (10)	−0.0008 (9)
C7	0.0727 (15)	0.0441 (13)	0.0498 (12)	−0.0088 (11)	0.0330 (11)	0.0017 (9)
C8	0.0499 (11)	0.0375 (11)	0.0446 (10)	0.0009 (9)	0.0289 (9)	−0.0020 (8)
C9	0.0489 (11)	0.0335 (11)	0.0416 (10)	−0.0040 (8)	0.0252 (9)	−0.0030 (8)
C10	0.0509 (11)	0.0345 (11)	0.0411 (10)	−0.0030 (9)	0.0261 (9)	0.0005 (8)
C11	0.0457 (10)	0.0365 (11)	0.0388 (10)	−0.0001 (8)	0.0230 (8)	0.0019 (8)
C12	0.0626 (13)	0.0343 (12)	0.0484 (11)	−0.0039 (10)	0.0324 (10)	−0.0052 (9)
C13	0.0646 (13)	0.0340 (12)	0.0532 (12)	−0.0086 (10)	0.0357 (10)	−0.0012 (9)
C14	0.0434 (10)	0.0454 (13)	0.0403 (10)	−0.0020 (9)	0.0245 (8)	0.0003 (8)
C15	0.0535 (11)	0.0364 (11)	0.0476 (11)	0.0019 (9)	0.0286 (9)	−0.0043 (9)
C16	0.0563 (12)	0.0314 (11)	0.0479 (11)	0.0008 (9)	0.0285 (9)	0.0024 (8)
C17	0.0766 (16)	0.0648 (17)	0.0608 (14)	−0.0097 (13)	0.0422 (12)	0.0107 (12)
C18	0.0734 (16)	0.0681 (17)	0.0530 (13)	0.0017 (13)	0.0397 (11)	−0.0070 (11)

O1—C5	1.380 (2)	C14—C15	1.402 (3)
O1—C8	1.418 (3)	C15—C16	1.378 (3)
O2—C9	1.226 (2)	C1—H1A	0.9600
N1—N2	1.388 (2)	C1—H1B	0.9600
N1—C9	1.342 (3)	C1—H1C	0.9600
N2—C10	1.273 (3)	C3—H3	0.9300
N3—C14	1.372 (3)	C4—H4	0.9300
N3—C17	1.453 (3)	C6—H6	0.9300
N3—C18	1.443 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—H8A	0.9700
C1—C2	1.513 (4)	C8—H8B	0.9700
C2—C7	1.376 (3)	C10—H10	0.9300
C2—C3	1.396 (4)	C12—H12	0.9300
C3—C4	1.375 (4)	C13—H13	0.9300
C4—C5	1.379 (3)	C15—H15	0.9300
C5—C6	1.385 (3)	C16—H16	0.9300
C6—C7	1.392 (3)	C17—H17A	0.9600
C8—C9	1.510 (3)	C17—H17B	0.9600
C10—C11	1.453 (3)	C17—H17C	0.9600
C11—C16	1.398 (3)	C18—H18A	0.9600
C11—C12	1.395 (3)	C18—H18B	0.9600
C12—C13	1.375 (3)	C18—H18C	0.9600
C13—C14	1.405 (3)
C5—O1—C8	117.04 (15)	H1A—C1—H1C	109.00
N2—N1—C9	120.36 (17)	H1B—C1—H1C	109.00
N1—N2—C10	114.47 (17)	C2—C3—H3	119.00
C14—N3—C17	120.51 (19)	C4—C3—H3	119.00
C14—N3—C18	120.91 (19)	C3—C4—H4	120.00
C17—N3—C18	118.58 (19)	C5—C4—H4	120.00
N2—N1—H1	120.00	C5—C6—H6	121.00
C9—N1—H1	120.00	C7—C6—H6	121.00
C3—C2—C7	117.4 (2)	C2—C7—H7	119.00
C1—C2—C3	120.4 (2)	C6—C7—H7	119.00
C1—C2—C7	122.1 (2)	O1—C8—H8A	110.00
C2—C3—C4	121.7 (2)	O1—C8—H8B	110.00
C3—C4—C5	119.6 (2)	C9—C8—H8A	110.00
O1—C5—C6	124.19 (19)	C9—C8—H8B	110.00
O1—C5—C4	115.37 (18)	H8A—C8—H8B	109.00
C4—C5—C6	120.4 (2)	N2—C10—H10	119.00
C5—C6—C7	118.8 (2)	C11—C10—H10	119.00
C2—C7—C6	122.1 (2)	C11—C12—H12	119.00
O1—C8—C9	106.44 (16)	C13—C12—H12	119.00
N1—C9—C8	113.53 (16)	C12—C13—H13	119.00
O2—C9—C8	121.76 (18)	C14—C13—H13	119.00
O2—C9—N1	124.71 (18)	C14—C15—H15	120.00
N2—C10—C11	122.37 (18)	C16—C15—H15	120.00
C12—C11—C16	117.09 (18)	C11—C16—H16	119.00
C10—C11—C12	123.28 (18)	C15—C16—H16	119.00
C10—C11—C16	119.61 (17)	N3—C17—H17A	110.00
C11—C12—C13	121.25 (18)	N3—C17—H17B	109.00
C12—C13—C14	121.74 (18)	N3—C17—H17C	109.00
N3—C14—C15	121.45 (18)	H17A—C17—H17B	109.00
N3—C14—C13	121.50 (18)	H17A—C17—H17C	109.00
C13—C14—C15	117.04 (19)	H17B—C17—H17C	109.00
C14—C15—C16	120.74 (18)	N3—C18—H18A	110.00
C11—C16—C15	122.12 (18)	N3—C18—H18B	109.00
C2—C1—H1A	109.00	N3—C18—H18C	109.00
C2—C1—H1B	110.00	H18A—C18—H18B	109.00
C2—C1—H1C	110.00	H18A—C18—H18C	109.00
H1A—C1—H1B	109.00	H18B—C18—H18C	109.00
C8—O1—C5—C4	−174.36 (19)	O1—C5—C6—C7	−178.31 (18)
C8—O1—C5—C6	4.4 (3)	C4—C5—C6—C7	0.3 (3)
C5—O1—C8—C9	169.91 (16)	C5—C6—C7—C2	−0.7 (3)
C9—N1—N2—C10	176.45 (19)	O1—C8—C9—O2	−53.8 (2)
N2—N1—C9—O2	−3.4 (3)	O1—C8—C9—N1	126.83 (18)
N2—N1—C9—C8	175.95 (16)	N2—C10—C11—C12	−10.0 (3)
N1—N2—C10—C11	179.34 (17)	N2—C10—C11—C16	168.4 (2)
C17—N3—C14—C13	−2.1 (3)	C10—C11—C12—C13	178.1 (2)
C17—N3—C14—C15	177.3 (2)	C16—C11—C12—C13	−0.4 (3)
C18—N3—C14—C13	178.3 (2)	C10—C11—C16—C15	−177.2 (2)
C18—N3—C14—C15	−2.3 (3)	C12—C11—C16—C15	1.4 (3)
C1—C2—C3—C4	179.8 (3)	C11—C12—C13—C14	−1.1 (3)
C7—C2—C3—C4	−0.9 (5)	C12—C13—C14—N3	−179.1 (2)
C1—C2—C7—C6	−179.8 (2)	C12—C13—C14—C15	1.5 (3)
C3—C2—C7—C6	0.9 (4)	N3—C14—C15—C16	−179.9 (2)
C2—C3—C4—C5	0.6 (5)	C13—C14—C15—C16	−0.5 (3)
C3—C4—C5—O1	178.5 (2)	C14—C15—C16—C11	−0.9 (3)
C3—C4—C5—C6	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.12	2.952 (2)	163
C8—H8B···O2i	0.97	2.43	3.303 (2)	149
C8—H8A···Cg2ii	0.97	2.65	3.442 (2)	139
C16—H16···Cg1i	0.93	2.71	3.394 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.12	2.952 (2)	163
C8—H8B⋯O2i	0.97	2.43	3.303 (2)	149
C8—H8A⋯Cg2ii	0.97	2.65	3.442 (2)	139
C16—H16⋯Cg1i	0.93	2.71	3.394 (2)	131

Symmetry codes: (i) ; (ii) .