(E)-N'-[4-(Dimethyl-amino)-benzyl-idene]-2-meth-oxy-benzohydrazide.

In the title compound, C(17)H(19)N(3)O(2), the two benzene rings form a dihedral angle of 89.2 (2)°. In the crystal structure, mol-ecules are linked through N-H⋯O hydrogen bonds, forming C(4) chains running along the c axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ▶); Zhu et al. (2009 ▶); Jimenez-Pulido et al. (2008 ▶); Raj et al. (2007 ▶); Zhong et al. (2007 ▶). For hydrazones we have reported previously, see: Liu & You (2010a ▶,b ▶,c ▶). For the crystal structures of similar hydrazone compounds, see: Khaledi et al. (2009 ▶); Warad et al. (2009 ▶); Back et al. (2009 ▶); Vijayakumar et al. (2009 ▶). For other related structures, see: Cao (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C17H19N3O2

M = 297.35

Orthorhombic,

a = 24.726 (4) Å

b = 15.385 (3) Å

c = 8.2700 (15) Å

V = 3146.0 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.17 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.983, T max = 0.989

12277 measured reflections

2096 independent reflections

1545 reflections with I > 2σ(I)

R int = 0.045

θmax = 22.7°

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.04

2096 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023937/sj5024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023937/sj5024Isup2.hkl

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

C17H19N3O2	Dx = 1.256 Mg m−3
Mr = 297.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1881 reflections
a = 24.726 (4) Å	θ = 2.5–24.0°
b = 15.385 (3) Å	µ = 0.08 mm−1
c = 8.2700 (15) Å	T = 298 K
V = 3146.0 (10) Å3	Block, colourless
Z = 8	0.20 × 0.17 × 0.13 mm
F(000) = 1264

Bruker SMART CCD area-detector diffractometer	2096 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 22.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −26→26
Tmin = 0.983, Tmax = 0.989	k = −13→16
12277 measured reflections	l = −8→8

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.2933P] where P = (Fo2 + 2Fc2)/3
2096 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.15 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.

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	0.22678 (6)	0.40089 (10)	−0.07729 (18)	0.0681 (5)
O2	0.22007 (6)	0.33552 (10)	0.36694 (18)	0.0635 (5)
N1	0.18746 (6)	0.26778 (11)	0.1458 (2)	0.0497 (5)
H1	0.1951	0.2438	0.0491	0.060*
N2	0.14034 (6)	0.24198 (11)	0.2235 (2)	0.0485 (5)
N3	−0.07797 (7)	0.02776 (13)	0.3833 (2)	0.0649 (5)
C1	0.27573 (9)	0.37736 (13)	−0.0152 (3)	0.0529 (6)
C2	0.27502 (8)	0.33335 (12)	0.1323 (2)	0.0456 (5)
C3	0.32355 (9)	0.30874 (14)	0.2011 (3)	0.0611 (6)
H3	0.3234	0.2808	0.3009	0.073*
C4	0.37239 (10)	0.32468 (17)	0.1251 (4)	0.0754 (8)
H4	0.4047	0.3059	0.1707	0.090*
C5	0.37218 (11)	0.36868 (17)	−0.0186 (4)	0.0784 (8)
H5	0.4048	0.3805	−0.0699	0.094*
C6	0.32491 (11)	0.39565 (17)	−0.0884 (3)	0.0700 (7)
H6	0.3258	0.4264	−0.1852	0.084*
C7	0.22616 (11)	0.44770 (17)	−0.2266 (3)	0.0836 (8)
H7A	0.2432	0.4134	−0.3092	0.125*
H7B	0.2454	0.5014	−0.2138	0.125*
H7C	0.1894	0.4597	−0.2570	0.125*
C8	0.22464 (8)	0.31366 (12)	0.2249 (3)	0.0454 (5)
C9	0.11475 (8)	0.18206 (15)	0.1511 (3)	0.0511 (6)
H9	0.1286	0.1607	0.0545	0.061*
C10	0.06471 (8)	0.14545 (13)	0.2125 (2)	0.0477 (5)
C11	0.04784 (8)	0.06446 (15)	0.1597 (3)	0.0575 (6)
H11	0.0683	0.0359	0.0817	0.069*
C12	0.00212 (8)	0.02449 (15)	0.2177 (3)	0.0595 (6)
H12	−0.0070	−0.0307	0.1808	0.071*
C13	−0.03087 (8)	0.06541 (14)	0.3311 (2)	0.0505 (6)
C14	−0.01414 (8)	0.14694 (15)	0.3850 (3)	0.0578 (6)
H14	−0.0349	0.1759	0.4618	0.069*
C15	0.03229 (8)	0.18573 (14)	0.3275 (3)	0.0559 (6)
H15	0.0421	0.2402	0.3666	0.067*
C16	−0.09234 (10)	−0.05974 (17)	0.3378 (3)	0.0803 (8)
H16A	−0.0627	−0.0981	0.3608	0.120*
H16B	−0.1004	−0.0616	0.2243	0.120*
H16C	−0.1235	−0.0778	0.3981	0.120*
C17	−0.11115 (9)	0.07019 (18)	0.5026 (3)	0.0823 (8)
H17A	−0.1181	0.1290	0.4696	0.124*
H17B	−0.0927	0.0703	0.6048	0.124*
H17C	−0.1448	0.0396	0.5131	0.124*

	U11	U22	U33	U12	U13	U23
O1	0.0796 (12)	0.0712 (11)	0.0536 (10)	−0.0085 (9)	0.0061 (8)	0.0234 (8)
O2	0.0784 (11)	0.0708 (10)	0.0414 (9)	−0.0189 (8)	0.0174 (8)	−0.0065 (8)
N1	0.0541 (10)	0.0541 (11)	0.0409 (10)	−0.0082 (9)	0.0165 (8)	−0.0036 (9)
N2	0.0496 (10)	0.0499 (11)	0.0459 (11)	−0.0043 (9)	0.0139 (8)	0.0023 (9)
N3	0.0521 (12)	0.0772 (14)	0.0653 (13)	−0.0155 (10)	0.0051 (10)	0.0058 (11)
C1	0.0655 (15)	0.0453 (13)	0.0479 (14)	−0.0098 (11)	0.0155 (12)	−0.0028 (11)
C2	0.0550 (14)	0.0359 (11)	0.0458 (13)	−0.0035 (10)	0.0138 (10)	−0.0035 (10)
C3	0.0631 (16)	0.0563 (14)	0.0639 (15)	−0.0020 (12)	0.0095 (13)	−0.0019 (12)
C4	0.0549 (15)	0.0767 (18)	0.095 (2)	−0.0044 (13)	0.0095 (14)	−0.0162 (17)
C5	0.0687 (18)	0.0812 (19)	0.085 (2)	−0.0273 (15)	0.0342 (16)	−0.0231 (17)
C6	0.0837 (19)	0.0681 (16)	0.0581 (16)	−0.0265 (14)	0.0266 (15)	−0.0032 (13)
C7	0.125 (2)	0.0708 (17)	0.0551 (16)	−0.0141 (16)	0.0011 (15)	0.0205 (14)
C8	0.0575 (13)	0.0362 (11)	0.0423 (13)	−0.0011 (10)	0.0121 (11)	0.0031 (10)
C9	0.0520 (13)	0.0587 (14)	0.0425 (13)	−0.0002 (11)	0.0080 (10)	−0.0007 (11)
C10	0.0466 (12)	0.0553 (14)	0.0413 (12)	0.0003 (10)	0.0009 (10)	−0.0011 (11)
C11	0.0540 (14)	0.0641 (15)	0.0545 (14)	−0.0009 (12)	0.0057 (11)	−0.0100 (12)
C12	0.0548 (14)	0.0567 (14)	0.0671 (16)	−0.0072 (12)	−0.0045 (12)	−0.0058 (12)
C13	0.0440 (12)	0.0620 (15)	0.0455 (13)	−0.0029 (11)	−0.0064 (10)	0.0062 (12)
C14	0.0497 (13)	0.0691 (16)	0.0545 (14)	−0.0016 (12)	0.0086 (11)	−0.0074 (12)
C15	0.0547 (13)	0.0534 (13)	0.0597 (14)	−0.0066 (11)	0.0042 (11)	−0.0074 (12)
C16	0.0687 (16)	0.0782 (19)	0.0941 (19)	−0.0233 (14)	−0.0054 (14)	0.0165 (16)
C17	0.0606 (15)	0.114 (2)	0.0728 (17)	−0.0136 (15)	0.0145 (14)	0.0077 (17)

O1—C1	1.363 (2)	C7—H7A	0.9600
O1—C7	1.429 (3)	C7—H7B	0.9600
O2—C8	1.227 (2)	C7—H7C	0.9600
N1—C8	1.331 (2)	C9—C10	1.451 (3)
N1—N2	1.389 (2)	C9—H9	0.9300
N1—H1	0.9002	C10—C11	1.385 (3)
N2—C9	1.269 (2)	C10—C15	1.390 (3)
N3—C13	1.370 (3)	C11—C12	1.373 (3)
N3—C17	1.440 (3)	C11—H11	0.9300
N3—C16	1.442 (3)	C12—C13	1.393 (3)
C1—C6	1.387 (3)	C12—H12	0.9300
C1—C2	1.396 (3)	C13—C14	1.394 (3)
C2—C3	1.381 (3)	C14—C15	1.379 (3)
C2—C8	1.493 (3)	C14—H14	0.9300
C3—C4	1.384 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.367 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.368 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C1—O1—C7	117.94 (17)	N1—C8—C2	115.55 (18)
C8—N1—N2	120.22 (16)	N2—C9—C10	122.83 (19)
C8—N1—H1	120.6	N2—C9—H9	118.6
N2—N1—H1	118.0	C10—C9—H9	118.6
C9—N2—N1	114.06 (16)	C11—C10—C15	116.31 (19)
C13—N3—C17	120.6 (2)	C11—C10—C9	119.73 (19)
C13—N3—C16	121.5 (2)	C15—C10—C9	123.93 (19)
C17—N3—C16	117.47 (19)	C12—C11—C10	122.7 (2)
O1—C1—C6	124.1 (2)	C12—C11—H11	118.6
O1—C1—C2	116.54 (18)	C10—C11—H11	118.6
C6—C1—C2	119.4 (2)	C11—C12—C13	121.0 (2)
C3—C2—C1	118.84 (19)	C11—C12—H12	119.5
C3—C2—C8	117.25 (19)	C13—C12—H12	119.5
C1—C2—C8	123.87 (19)	N3—C13—C12	121.2 (2)
C2—C3—C4	121.5 (2)	N3—C13—C14	122.1 (2)
C2—C3—H3	119.2	C12—C13—C14	116.62 (19)
C4—C3—H3	119.2	C15—C14—C13	121.8 (2)
C5—C4—C3	118.6 (2)	C15—C14—H14	119.1
C5—C4—H4	120.7	C13—C14—H14	119.1
C3—C4—H4	120.7	C14—C15—C10	121.6 (2)
C4—C5—C6	121.3 (2)	C14—C15—H15	119.2
C4—C5—H5	119.3	C10—C15—H15	119.2
C6—C5—H5	119.3	N3—C16—H16A	109.5
C5—C6—C1	120.2 (2)	N3—C16—H16B	109.5
C5—C6—H6	119.9	H16A—C16—H16B	109.5
C1—C6—H6	119.9	N3—C16—H16C	109.5
O1—C7—H7A	109.5	H16A—C16—H16C	109.5
O1—C7—H7B	109.5	H16B—C16—H16C	109.5
H7A—C7—H7B	109.5	N3—C17—H17A	109.5
O1—C7—H7C	109.5	N3—C17—H17B	109.5
H7A—C7—H7C	109.5	H17A—C17—H17B	109.5
H7B—C7—H7C	109.5	N3—C17—H17C	109.5
O2—C8—N1	123.55 (18)	H17A—C17—H17C	109.5
O2—C8—C2	120.81 (19)	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.90	2.03	2.914 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.90	2.03	2.914 (2)	165

Symmetry code: (i) .