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

In the title mol-ecule, C(17)H(19)N(3)O(2), the dihedral angle between the two benzene rings is 14.05 (15)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along b.

Related literature

For the biological properties of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For similar structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Su et al. (2011 ▶).

Experimental

Crystal data

C17H19N3O2

M = 297.35

Orthorhombic,

a = 16.065 (3) Å

b = 7.946 (2) Å

c = 24.534 (3) Å

V = 3131.8 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.989, T max = 0.993

13733 measured reflections

2800 independent reflections

1570 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.140

S = 0.99

2800 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025220/su2286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025220/su2286Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025220/su2286Isup3.cml

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

C17H19N3O2	F(000) = 1264
Mr = 297.35	Dx = 1.261 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1584 reflections
a = 16.065 (3) Å	θ = 2.5–24.5°
b = 7.946 (2) Å	µ = 0.09 mm−1
c = 24.534 (3) Å	T = 298 K
V = 3131.8 (11) Å3	Block, colourless
Z = 8	0.13 × 0.10 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	2800 independent reflections
Radiation source: fine-focus sealed tube	1570 reflections with I > 2σ(I)
graphite	Rint = 0.094
ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→14
Tmin = 0.989, Tmax = 0.993	k = −9→9
13733 measured reflections	l = −29→28

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)] = 0.064	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0579P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2800 reflections	Δρmax = 0.20 e Å−3
203 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (7)

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 > 2sigma(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	0.48383 (13)	0.6587 (3)	0.24567 (9)	0.0662 (7)
O2	0.14952 (11)	0.4522 (2)	0.11421 (8)	0.0472 (6)
N1	0.26607 (14)	0.5707 (3)	0.17978 (9)	0.0416 (6)
N2	0.24365 (13)	0.6531 (3)	0.13259 (8)	0.0416 (6)
H2	0.2698	0.7527	0.1273	0.050*
N3	0.05256 (15)	0.9526 (3)	−0.07705 (10)	0.0528 (7)
C1	0.34787 (17)	0.5653 (4)	0.25970 (11)	0.0411 (7)
C2	0.42874 (18)	0.5812 (4)	0.27952 (11)	0.0436 (7)
C3	0.4498 (2)	0.5152 (4)	0.32985 (13)	0.0559 (9)
H3	0.5038	0.5257	0.3431	0.067*
C4	0.3908 (2)	0.4350 (5)	0.35968 (13)	0.0665 (10)
H4	0.4047	0.3937	0.3940	0.080*
C5	0.3123 (2)	0.4135 (5)	0.34093 (14)	0.0695 (11)
H5	0.2736	0.3542	0.3615	0.083*
C6	0.29024 (19)	0.4800 (4)	0.29113 (13)	0.0588 (9)
H6	0.2360	0.4674	0.2785	0.071*
C7	0.5688 (2)	0.6547 (5)	0.26050 (16)	0.0847 (12)
H7A	0.5767	0.7171	0.2936	0.127*
H7B	0.6016	0.7041	0.2320	0.127*
H7C	0.5858	0.5401	0.2660	0.127*
C8	0.32433 (17)	0.6371 (3)	0.20687 (11)	0.0411 (7)
H8	0.3521	0.7310	0.1934	0.049*
C9	0.18162 (16)	0.5881 (4)	0.10239 (11)	0.0364 (7)
C10	0.15273 (16)	0.6857 (3)	0.05514 (10)	0.0353 (7)
C11	0.20007 (16)	0.8036 (4)	0.02693 (10)	0.0410 (8)
H11	0.2546	0.8242	0.0378	0.049*
C12	0.16804 (18)	0.8897 (4)	−0.01651 (11)	0.0460 (8)
H12	0.2016	0.9663	−0.0349	0.055*
C13	0.08536 (17)	0.8651 (4)	−0.03401 (11)	0.0387 (7)
C14	0.03883 (17)	0.7460 (4)	−0.00569 (11)	0.0428 (8)
H14	−0.0160	0.7254	−0.0160	0.051*
C15	0.07247 (17)	0.6587 (3)	0.03703 (11)	0.0405 (7)
H15	0.0401	0.5781	0.0545	0.049*
C16	−0.03085 (19)	0.9181 (4)	−0.09651 (12)	0.0630 (10)
H16A	−0.0354	0.8013	−0.1060	0.095*
H16B	−0.0421	0.9861	−0.1280	0.095*
H16C	−0.0703	0.9442	−0.0684	0.095*
C17	0.1000 (2)	1.0754 (5)	−0.10564 (15)	0.0850 (12)
H17A	0.1213	1.1568	−0.0803	0.128*
H17B	0.0653	1.1308	−0.1319	0.128*
H17C	0.1456	1.0215	−0.1240	0.128*

	U11	U22	U33	U12	U13	U23
O1	0.0498 (14)	0.0811 (17)	0.0678 (14)	−0.0141 (13)	−0.0137 (12)	0.0283 (13)
O2	0.0488 (12)	0.0363 (12)	0.0566 (13)	−0.0065 (10)	−0.0030 (10)	0.0106 (10)
N1	0.0426 (14)	0.0413 (15)	0.0410 (14)	0.0018 (13)	−0.0046 (12)	0.0138 (12)
N2	0.0451 (14)	0.0384 (15)	0.0413 (13)	−0.0043 (12)	−0.0076 (12)	0.0132 (11)
N3	0.0532 (16)	0.0579 (18)	0.0473 (15)	0.0045 (14)	−0.0077 (13)	0.0092 (14)
C1	0.0442 (18)	0.0409 (18)	0.0383 (16)	0.0080 (15)	0.0006 (14)	0.0076 (14)
C2	0.0500 (19)	0.0403 (18)	0.0404 (17)	0.0013 (15)	−0.0037 (15)	0.0065 (15)
C3	0.064 (2)	0.053 (2)	0.050 (2)	0.0052 (18)	−0.0167 (17)	0.0033 (17)
C4	0.082 (3)	0.077 (3)	0.0406 (19)	0.023 (2)	−0.0012 (19)	0.0167 (19)
C5	0.059 (2)	0.089 (3)	0.061 (2)	0.017 (2)	0.0184 (19)	0.033 (2)
C6	0.0423 (19)	0.075 (2)	0.059 (2)	0.0147 (17)	0.0046 (16)	0.0217 (19)
C7	0.052 (2)	0.089 (3)	0.113 (3)	−0.012 (2)	−0.017 (2)	0.027 (2)
C8	0.0428 (17)	0.0364 (17)	0.0442 (17)	0.0034 (15)	0.0008 (14)	0.0058 (15)
C9	0.0333 (16)	0.0327 (17)	0.0432 (17)	0.0046 (14)	0.0030 (13)	0.0020 (14)
C10	0.0389 (17)	0.0317 (16)	0.0352 (15)	0.0019 (13)	−0.0008 (13)	−0.0013 (13)
C11	0.0367 (16)	0.0471 (19)	0.0391 (17)	−0.0054 (14)	−0.0056 (14)	0.0044 (14)
C12	0.0526 (19)	0.0443 (19)	0.0412 (17)	−0.0085 (15)	0.0032 (15)	0.0094 (15)
C13	0.0444 (17)	0.0364 (18)	0.0353 (15)	0.0056 (15)	−0.0035 (14)	−0.0031 (14)
C14	0.0404 (16)	0.0459 (19)	0.0423 (17)	−0.0048 (15)	−0.0070 (14)	−0.0044 (15)
C15	0.0424 (18)	0.0375 (18)	0.0414 (17)	−0.0033 (14)	−0.0007 (14)	0.0001 (14)
C16	0.069 (2)	0.068 (2)	0.0512 (19)	0.0169 (19)	−0.0200 (17)	−0.0021 (18)
C17	0.077 (3)	0.099 (3)	0.079 (3)	−0.002 (2)	−0.007 (2)	0.050 (2)

O1—C2	1.361 (3)	C7—H7A	0.9600
O1—C7	1.413 (3)	C7—H7B	0.9600
O2—C9	1.231 (3)	C7—H7C	0.9600
N1—C8	1.263 (3)	C8—H8	0.9300
N1—N2	1.378 (3)	C9—C10	1.470 (4)
N2—C9	1.345 (3)	C10—C15	1.381 (3)
N2—H2	0.9056	C10—C11	1.391 (3)
N3—C13	1.369 (3)	C11—C12	1.367 (4)
N3—C17	1.424 (4)	C11—H11	0.9300
N3—C16	1.449 (4)	C12—C13	1.410 (4)
C1—C6	1.383 (4)	C12—H12	0.9300
C1—C2	1.393 (4)	C13—C14	1.392 (4)
C1—C8	1.466 (4)	C14—C15	1.368 (4)
C2—C3	1.383 (4)	C14—H14	0.9300
C3—C4	1.357 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.353 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.378 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C2—O1—C7	117.4 (2)	C1—C8—H8	120.2
C8—N1—N2	115.9 (2)	O2—C9—N2	121.1 (2)
C9—N2—N1	118.3 (2)	O2—C9—C10	121.1 (3)
C9—N2—H2	127.0	N2—C9—C10	117.8 (2)
N1—N2—H2	114.4	C15—C10—C11	117.1 (2)
C13—N3—C17	121.4 (3)	C15—C10—C9	117.8 (2)
C13—N3—C16	121.0 (3)	C11—C10—C9	125.1 (2)
C17—N3—C16	117.6 (3)	C12—C11—C10	121.3 (3)
C6—C1—C2	118.3 (3)	C12—C11—H11	119.4
C6—C1—C8	120.7 (3)	C10—C11—H11	119.4
C2—C1—C8	120.9 (3)	C11—C12—C13	121.5 (3)
O1—C2—C3	123.8 (3)	C11—C12—H12	119.2
O1—C2—C1	115.7 (2)	C13—C12—H12	119.2
C3—C2—C1	120.4 (3)	N3—C13—C14	121.6 (3)
C4—C3—C2	119.2 (3)	N3—C13—C12	121.8 (3)
C4—C3—H3	120.4	C14—C13—C12	116.6 (2)
C2—C3—H3	120.4	C15—C14—C13	121.0 (3)
C5—C4—C3	121.8 (3)	C15—C14—H14	119.5
C5—C4—H4	119.1	C13—C14—H14	119.5
C3—C4—H4	119.1	C14—C15—C10	122.5 (3)
C4—C5—C6	119.5 (3)	C14—C15—H15	118.8
C4—C5—H5	120.2	C10—C15—H15	118.8
C6—C5—H5	120.2	N3—C16—H16A	109.5
C5—C6—C1	120.7 (3)	N3—C16—H16B	109.5
C5—C6—H6	119.7	H16A—C16—H16B	109.5
C1—C6—H6	119.7	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
N1—C8—C1	119.6 (3)	H17A—C17—H17C	109.5
N1—C8—H8	120.2	H17B—C17—H17C	109.5
C8—N1—N2—C9	−179.6 (2)	O2—C9—C10—C15	23.9 (4)
C7—O1—C2—C3	7.1 (4)	N2—C9—C10—C15	−155.4 (2)
C7—O1—C2—C1	−170.6 (3)	O2—C9—C10—C11	−156.0 (3)
C6—C1—C2—O1	176.7 (3)	N2—C9—C10—C11	24.7 (4)
C8—C1—C2—O1	−3.2 (4)	C15—C10—C11—C12	0.6 (4)
C6—C1—C2—C3	−1.1 (4)	C9—C10—C11—C12	−179.6 (3)
C8—C1—C2—C3	179.0 (3)	C10—C11—C12—C13	1.1 (4)
O1—C2—C3—C4	−177.7 (3)	C17—N3—C13—C14	179.4 (3)
C1—C2—C3—C4	0.0 (5)	C16—N3—C13—C14	−3.1 (4)
C2—C3—C4—C5	1.9 (5)	C17—N3—C13—C12	−1.2 (4)
C3—C4—C5—C6	−2.6 (6)	C16—N3—C13—C12	176.2 (3)
C4—C5—C6—C1	1.4 (5)	C11—C12—C13—N3	179.1 (3)
C2—C1—C6—C5	0.4 (5)	C11—C12—C13—C14	−1.5 (4)
C8—C1—C6—C5	−179.6 (3)	N3—C13—C14—C15	179.6 (3)
N2—N1—C8—C1	175.3 (2)	C12—C13—C14—C15	0.2 (4)
C6—C1—C8—N1	−28.0 (4)	C13—C14—C15—C10	1.5 (4)
C2—C1—C8—N1	152.0 (3)	C11—C10—C15—C14	−1.8 (4)
N1—N2—C9—O2	−5.2 (4)	C9—C10—C15—C14	178.3 (2)
N1—N2—C9—C10	174.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.91	2.07	2.966 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.91	2.07	2.966 (3)	169

Symmetry code: (i) .