N'-[4-(Dimethyl-amino)-benzyl-idene]-4-meth-oxybenzohydrazide.

The title Schiff base compound, C(17)H(19)N(3)O(2), was obtained from the condensation of 4-dimethyl-amino-benzaldehyde with 4-methoxy-benzohydrazide in an ethanol solution. The mol-ecule is twisted with respect to the N-N single bond [C-N-N-C = -159.27 (14)°] and the dihedral angle between the two aromatic rings is 67.1 (2)°. In the crystal structure, the mol-ecules are linked into chains along the c axis by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H19N3O2

M = 297.35

Monoclinic,

a = 11.922 (4) Å

b = 13.224 (5) Å

c = 9.756 (4) Å

β = 91.469 (6)°

V = 1537.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.23 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.981, T max = 0.983

8744 measured reflections

3296 independent reflections

2507 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.03

3296 reflections

205 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808031012/ci2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031012/ci2684Isup2.hkl

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

C17H19N3O2	F(000) = 632
Mr = 297.35	Dx = 1.284 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3161 reflections
a = 11.922 (4) Å	θ = 2.5–27.2°
b = 13.224 (5) Å	µ = 0.09 mm−1
c = 9.756 (4) Å	T = 298 K
β = 91.469 (6)°	Block, colourless
V = 1537.6 (10) Å3	0.23 × 0.23 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3296 independent reflections
Radiation source: fine-focus sealed tube	2507 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.981, Tmax = 0.983	k = −16→14
8744 measured reflections	l = −12→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2298P] where P = (Fo2 + 2Fc2)/3
3296 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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
N1	0.23023 (11)	0.86331 (9)	0.18617 (12)	0.0451 (3)
N2	0.27424 (11)	0.77478 (9)	0.24111 (11)	0.0441 (3)
N3	0.06781 (13)	1.32361 (10)	0.12512 (17)	0.0665 (4)
O1	0.29961 (10)	0.70488 (7)	0.03342 (9)	0.0520 (3)
O2	0.46299 (11)	0.33676 (8)	0.39093 (12)	0.0612 (3)
C1	0.10930 (12)	1.23056 (11)	0.15842 (16)	0.0473 (4)
C2	0.07206 (14)	1.14376 (12)	0.09023 (18)	0.0552 (4)
H2	0.0181	1.1495	0.0201	0.066*
C3	0.11325 (14)	1.05048 (11)	0.12429 (17)	0.0517 (4)
H3	0.0874	0.9943	0.0757	0.062*
C4	0.19240 (12)	1.03716 (10)	0.22919 (14)	0.0428 (3)
C5	0.22870 (14)	1.12314 (11)	0.29766 (16)	0.0523 (4)
H5	0.2809	1.1166	0.3696	0.063*
C6	0.19031 (14)	1.21761 (12)	0.26300 (17)	0.0545 (4)
H6	0.2185	1.2738	0.3096	0.065*
C7	0.23746 (12)	0.93903 (11)	0.26614 (15)	0.0440 (3)
H7	0.2730	0.9311	0.3514	0.053*
C8	0.30424 (12)	0.69893 (10)	0.15876 (13)	0.0389 (3)
C9	0.34473 (11)	0.60594 (10)	0.22874 (13)	0.0371 (3)
C10	0.41496 (13)	0.54231 (11)	0.15756 (14)	0.0468 (4)
H10	0.4359	0.5597	0.0695	0.056*
C11	0.45393 (14)	0.45430 (11)	0.21489 (16)	0.0506 (4)
H11	0.5018	0.4129	0.1661	0.061*
C12	0.42254 (13)	0.42666 (10)	0.34493 (15)	0.0442 (3)
C13	0.35380 (13)	0.48939 (11)	0.41792 (14)	0.0452 (3)
H13	0.3334	0.4719	0.5062	0.054*
C14	0.31545 (12)	0.57821 (10)	0.35951 (14)	0.0421 (3)
H14	0.2689	0.6203	0.4091	0.051*
C15	0.43137 (17)	0.30433 (13)	0.52240 (19)	0.0676 (5)
H15A	0.4527	0.3546	0.5891	0.101*
H15B	0.4683	0.2417	0.5444	0.101*
H15C	0.3516	0.2947	0.5230	0.101*
C16	−0.02077 (16)	1.33522 (15)	0.0240 (2)	0.0727 (6)
H16A	0.0088	1.3263	−0.0658	0.109*
H16B	−0.0526	1.4016	0.0311	0.109*
H16C	−0.0778	1.2855	0.0391	0.109*
C17	0.1166 (2)	1.41355 (13)	0.1829 (2)	0.0810 (6)
H17A	0.1116	1.4115	0.2809	0.121*
H17B	0.0768	1.4716	0.1481	0.121*
H17C	0.1939	1.4178	0.1584	0.121*
H2A	0.2875 (17)	0.7721 (14)	0.3316 (10)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0607 (8)	0.0397 (6)	0.0349 (6)	0.0055 (5)	−0.0015 (5)	0.0055 (5)
N2	0.0648 (8)	0.0385 (6)	0.0289 (6)	0.0075 (6)	−0.0026 (5)	0.0025 (5)
N3	0.0689 (10)	0.0429 (7)	0.0867 (11)	0.0069 (7)	−0.0189 (8)	0.0055 (7)
O1	0.0804 (8)	0.0482 (6)	0.0272 (5)	−0.0012 (5)	−0.0051 (5)	0.0000 (4)
O2	0.0753 (8)	0.0472 (6)	0.0613 (7)	0.0160 (5)	0.0055 (6)	0.0097 (5)
C1	0.0475 (8)	0.0404 (8)	0.0539 (9)	0.0031 (6)	0.0005 (7)	0.0035 (7)
C2	0.0551 (9)	0.0500 (9)	0.0595 (10)	−0.0008 (7)	−0.0172 (8)	0.0033 (7)
C3	0.0562 (9)	0.0421 (8)	0.0562 (10)	−0.0031 (7)	−0.0117 (7)	−0.0015 (7)
C4	0.0487 (8)	0.0404 (7)	0.0393 (7)	0.0024 (6)	0.0020 (6)	0.0027 (6)
C5	0.0606 (10)	0.0483 (9)	0.0473 (9)	0.0059 (7)	−0.0118 (7)	−0.0031 (7)
C6	0.0633 (10)	0.0424 (8)	0.0570 (10)	0.0023 (7)	−0.0099 (8)	−0.0065 (7)
C7	0.0525 (8)	0.0438 (8)	0.0357 (7)	0.0028 (6)	−0.0004 (6)	0.0037 (6)
C8	0.0482 (8)	0.0403 (7)	0.0279 (7)	−0.0055 (6)	−0.0018 (5)	−0.0009 (5)
C9	0.0462 (7)	0.0360 (7)	0.0291 (6)	−0.0029 (6)	−0.0012 (5)	−0.0028 (5)
C10	0.0597 (9)	0.0479 (8)	0.0332 (7)	0.0016 (7)	0.0091 (6)	−0.0009 (6)
C11	0.0598 (9)	0.0469 (8)	0.0457 (8)	0.0093 (7)	0.0110 (7)	−0.0053 (7)
C12	0.0491 (8)	0.0379 (7)	0.0453 (8)	0.0026 (6)	−0.0012 (6)	0.0003 (6)
C13	0.0572 (9)	0.0453 (8)	0.0334 (7)	0.0016 (7)	0.0048 (6)	0.0045 (6)
C14	0.0537 (8)	0.0393 (7)	0.0337 (7)	0.0057 (6)	0.0061 (6)	−0.0019 (6)
C15	0.0793 (12)	0.0550 (10)	0.0684 (12)	0.0059 (9)	−0.0023 (9)	0.0231 (9)
C16	0.0609 (11)	0.0672 (11)	0.0896 (15)	0.0183 (9)	−0.0083 (10)	0.0133 (10)
C17	0.1003 (16)	0.0422 (9)	0.0996 (16)	0.0101 (10)	−0.0138 (13)	−0.0015 (10)

N1—C7	1.2710 (18)	C7—H7	0.93
N1—N2	1.3851 (16)	C8—C9	1.4814 (19)
N2—C8	1.3395 (17)	C9—C14	1.3810 (19)
N2—H2A	0.893 (9)	C9—C10	1.386 (2)
N3—C1	1.3624 (19)	C10—C11	1.367 (2)
N3—C17	1.433 (2)	C10—H10	0.93
N3—C16	1.435 (2)	C11—C12	1.381 (2)
O1—C8	1.2252 (16)	C11—H11	0.93
O2—C12	1.3550 (17)	C12—C13	1.377 (2)
O2—C15	1.413 (2)	C13—C14	1.3784 (19)
C1—C2	1.394 (2)	C13—H13	0.93
C1—C6	1.397 (2)	C14—H14	0.93
C2—C3	1.366 (2)	C15—H15A	0.96
C2—H2	0.93	C15—H15B	0.96
C3—C4	1.385 (2)	C15—H15C	0.96
C3—H3	0.93	C16—H16A	0.96
C4—C5	1.383 (2)	C16—H16B	0.96
C4—C7	1.447 (2)	C16—H16C	0.96
C5—C6	1.370 (2)	C17—H17A	0.96
C5—H5	0.93	C17—H17B	0.96
C6—H6	0.93	C17—H17C	0.96
C7—N1—N2	114.15 (12)	C10—C9—C8	117.84 (12)
C8—N2—N1	120.33 (11)	C11—C10—C9	121.00 (13)
C8—N2—H2A	121.3 (13)	C11—C10—H10	119.5
N1—N2—H2A	118.2 (13)	C9—C10—H10	119.5
C1—N3—C17	120.98 (15)	C10—C11—C12	120.25 (14)
C1—N3—C16	121.12 (15)	C10—C11—H11	119.9
C17—N3—C16	117.75 (15)	C12—C11—H11	119.9
C12—O2—C15	117.78 (13)	O2—C12—C13	124.65 (14)
N3—C1—C2	121.39 (14)	O2—C12—C11	115.72 (13)
N3—C1—C6	121.65 (14)	C13—C12—C11	119.63 (13)
C2—C1—C6	116.96 (13)	C12—C13—C14	119.67 (13)
C3—C2—C1	121.31 (14)	C12—C13—H13	120.2
C3—C2—H2	119.3	C14—C13—H13	120.2
C1—C2—H2	119.3	C13—C14—C9	121.28 (13)
C2—C3—C4	121.90 (14)	C13—C14—H14	119.4
C2—C3—H3	119.0	C9—C14—H14	119.4
C4—C3—H3	119.0	O2—C15—H15A	109.5
C5—C4—C3	116.82 (13)	O2—C15—H15B	109.5
C5—C4—C7	120.51 (13)	H15A—C15—H15B	109.5
C3—C4—C7	122.66 (13)	O2—C15—H15C	109.5
C6—C5—C4	122.15 (15)	H15A—C15—H15C	109.5
C6—C5—H5	118.9	H15B—C15—H15C	109.5
C4—C5—H5	118.9	N3—C16—H16A	109.5
C5—C6—C1	120.82 (15)	N3—C16—H16B	109.5
C5—C6—H6	119.6	H16A—C16—H16B	109.5
C1—C6—H6	119.6	N3—C16—H16C	109.5
N1—C7—C4	122.33 (13)	H16A—C16—H16C	109.5
N1—C7—H7	118.8	H16B—C16—H16C	109.5
C4—C7—H7	118.8	N3—C17—H17A	109.5
O1—C8—N2	123.01 (13)	N3—C17—H17B	109.5
O1—C8—C9	121.27 (12)	H17A—C17—H17B	109.5
N2—C8—C9	115.72 (11)	N3—C17—H17C	109.5
C14—C9—C10	118.16 (13)	H17A—C17—H17C	109.5
C14—C9—C8	124.00 (12)	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.90 (1)	1.99 (1)	2.873 (2)	167 (2)
C7—H7···O1i	0.93	2.54	3.297 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.90 (1)	1.99 (1)	2.873 (2)	167 (2)
C7—H7⋯O1i	0.93	2.54	3.297 (2)	139

Symmetry code: (i) .