N'-[4-(Dimethyl-amino)benzyl-idene]-3-hydr-oxy-2-naphthohydrazide.

The title compound, C(20)H(19)N(3)O(2), was obtained by the condensation of 4-(dimethyl-amino)benzaldehyde with 3-hydr-oxy-2-naphthohydrazide. The mol-ecule is approximately planar, with an intra-molecular N-H⋯O hydrogen bond involving the imino H atom and the hydr-oxy O atom. The dihedral angle between the benzene ring and the naphthyl mean plane is 2.72 (13)°. In the crystal structure, symmetry-related mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds, forming chains propagating in the c-axis direction.

Related literature

For background on compounds obtained by the condensation of aldehydes with benzohydrazides, see: Qiu & Zhao (2008 ▶); Yathirajan et al. (2007 ▶); Salhin et al. (2007 ▶). For informtaion concerning their biological properties, see: Küçükgüzel et al. (2003 ▶); Charkoudian et al. (2007 ▶). For similar structures, see: Fun et al. (2008 ▶); Liu & Li (2004 ▶); Lei et al. (2008 ▶). For bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H19N3O2

M = 333.38

Monoclinic,

a = 8.090 (2) Å

b = 15.798 (3) Å

c = 13.428 (3) Å

β = 98.978 (3)°

V = 1695.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.27 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.981

13922 measured reflections

3670 independent reflections

1629 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.190

S = 1.03

3670 reflections

232 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (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 datablocks global, I. DOI: 10.1107/S160053680900960X/su2102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900960X/su2102Isup2.hkl

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

C20H19N3O2	F(000) = 704
Mr = 333.38	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 762 reflections
a = 8.090 (2) Å	θ = 2.5–24.3°
b = 15.798 (3) Å	µ = 0.09 mm−1
c = 13.428 (3) Å	T = 298 K
β = 98.978 (3)°	Block, colorless
V = 1695.2 (7) Å3	0.27 × 0.23 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3670 independent reflections
Radiation source: fine-focus sealed tube	1629 reflections with I > 2σ(I)
graphite	Rint = 0.075
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.977, Tmax = 0.981	k = −20→20
13922 measured reflections	l = −17→17

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2)]
3670 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.17 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
O1	−0.0121 (3)	0.25089 (12)	0.13318 (14)	0.0832 (7)
O2	0.0653 (3)	0.25424 (12)	−0.16764 (12)	0.0674 (6)
H2	0.0589	0.2496	−0.2289	0.101*
N1	0.1356 (3)	0.39358 (17)	0.07447 (17)	0.0672 (7)
N2	0.0872 (3)	0.32477 (18)	0.01253 (17)	0.0675 (7)
N3	0.4476 (3)	0.76089 (17)	0.2113 (2)	0.0763 (8)
C1	0.2663 (4)	0.5303 (2)	0.0807 (2)	0.0619 (8)
C2	0.2427 (4)	0.5531 (2)	0.1772 (2)	0.0701 (9)
H2A	0.1870	0.5161	0.2144	0.084*
C3	0.2992 (4)	0.6282 (2)	0.2186 (2)	0.0726 (9)
H3	0.2785	0.6415	0.2830	0.087*
C4	0.3873 (4)	0.6862 (2)	0.1683 (2)	0.0615 (8)
C5	0.4095 (4)	0.6637 (2)	0.0710 (2)	0.0756 (10)
H5	0.4645	0.7006	0.0333	0.091*
C6	0.3512 (5)	0.5876 (2)	0.0302 (2)	0.0825 (10)
H6	0.3699	0.5741	−0.0345	0.099*
C7	0.4285 (4)	0.7842 (2)	0.3128 (2)	0.0881 (11)
H7A	0.3154	0.7738	0.3228	0.132*
H7B	0.4540	0.8432	0.3232	0.132*
H7C	0.5036	0.7512	0.3599	0.132*
C8	0.5351 (4)	0.8210 (2)	0.1573 (3)	0.0897 (11)
H8A	0.6426	0.7985	0.1496	0.134*
H8B	0.5496	0.8731	0.1944	0.134*
H8C	0.4711	0.8312	0.0920	0.134*
C9	0.2072 (4)	0.4523 (2)	0.0329 (2)	0.0716 (9)
H9	0.2226	0.4443	−0.0336	0.086*
C10	0.0123 (4)	0.25726 (19)	0.0455 (2)	0.0588 (8)
C11	−0.0405 (3)	0.18921 (19)	−0.02859 (18)	0.0542 (7)
C12	−0.0109 (3)	0.18591 (18)	−0.13032 (18)	0.0524 (7)
C13	−0.0562 (4)	0.11700 (19)	−0.18837 (19)	0.0589 (8)
H13	−0.0304	0.1152	−0.2535	0.071*
C14	−0.1407 (3)	0.0483 (2)	−0.1533 (2)	0.0580 (8)
C15	−0.1911 (4)	−0.0237 (2)	−0.2123 (2)	0.0721 (9)
H15	−0.1660	−0.0273	−0.2774	0.087*
C16	−0.2753 (4)	−0.0874 (2)	−0.1759 (3)	0.0830 (10)
H16	−0.3073	−0.1344	−0.2161	0.100*
C17	−0.3150 (4)	−0.0836 (2)	−0.0779 (3)	0.0845 (10)
H17	−0.3747	−0.1274	−0.0540	0.101*
C18	−0.2665 (4)	−0.0159 (2)	−0.0181 (2)	0.0736 (9)
H18	−0.2927	−0.0138	0.0469	0.088*
C19	−0.1767 (3)	0.0512 (2)	−0.0534 (2)	0.0567 (8)
C20	−0.1228 (4)	0.12143 (19)	0.00589 (19)	0.0598 (8)
H20	−0.1434	0.1226	0.0721	0.072*
H2B	0.104 (3)	0.3251 (17)	−0.0520 (10)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.134 (2)	0.0852 (15)	0.0327 (11)	0.0087 (13)	0.0201 (11)	−0.0037 (10)
O2	0.0922 (15)	0.0803 (15)	0.0320 (10)	0.0019 (12)	0.0165 (10)	0.0003 (10)
N1	0.0862 (19)	0.0724 (18)	0.0434 (14)	0.0093 (15)	0.0117 (13)	−0.0071 (13)
N2	0.0881 (19)	0.0812 (19)	0.0343 (13)	0.0019 (16)	0.0136 (13)	−0.0079 (14)
N3	0.090 (2)	0.079 (2)	0.0635 (16)	−0.0053 (16)	0.0226 (15)	−0.0080 (15)
C1	0.074 (2)	0.072 (2)	0.0400 (16)	0.0084 (17)	0.0105 (15)	0.0017 (16)
C2	0.077 (2)	0.087 (2)	0.0491 (18)	−0.0074 (19)	0.0202 (16)	−0.0056 (17)
C3	0.081 (2)	0.096 (3)	0.0452 (17)	−0.007 (2)	0.0232 (16)	−0.0104 (18)
C4	0.0603 (19)	0.076 (2)	0.0488 (17)	0.0130 (18)	0.0099 (15)	0.0022 (17)
C5	0.104 (3)	0.079 (2)	0.0494 (18)	0.003 (2)	0.0292 (17)	0.0065 (17)
C6	0.122 (3)	0.084 (2)	0.0449 (17)	−0.001 (2)	0.0248 (19)	−0.0022 (18)
C7	0.101 (3)	0.097 (3)	0.065 (2)	0.007 (2)	0.0097 (19)	−0.0166 (19)
C8	0.093 (3)	0.087 (3)	0.093 (3)	0.001 (2)	0.024 (2)	0.003 (2)
C9	0.092 (3)	0.082 (2)	0.0416 (17)	0.008 (2)	0.0126 (17)	−0.0021 (18)
C10	0.072 (2)	0.072 (2)	0.0328 (15)	0.0138 (18)	0.0078 (14)	0.0016 (15)
C11	0.0633 (19)	0.0687 (19)	0.0309 (14)	0.0171 (16)	0.0082 (13)	0.0025 (14)
C12	0.0582 (18)	0.065 (2)	0.0344 (14)	0.0108 (16)	0.0090 (13)	0.0047 (14)
C13	0.0668 (19)	0.078 (2)	0.0325 (14)	0.0126 (17)	0.0083 (13)	−0.0040 (15)
C14	0.0569 (19)	0.072 (2)	0.0437 (16)	0.0118 (16)	0.0039 (14)	0.0003 (16)
C15	0.073 (2)	0.091 (3)	0.0513 (18)	0.005 (2)	0.0053 (16)	−0.0084 (18)
C16	0.079 (2)	0.088 (3)	0.078 (2)	−0.010 (2)	0.001 (2)	−0.010 (2)
C17	0.071 (2)	0.097 (3)	0.087 (3)	−0.008 (2)	0.015 (2)	0.002 (2)
C18	0.069 (2)	0.092 (3)	0.063 (2)	0.006 (2)	0.0202 (17)	0.0032 (19)
C19	0.0537 (18)	0.072 (2)	0.0448 (16)	0.0105 (16)	0.0099 (14)	0.0046 (16)
C20	0.069 (2)	0.078 (2)	0.0344 (15)	0.0190 (18)	0.0154 (14)	0.0037 (15)

O1—C10	1.228 (3)	C7—H7C	0.9600
O2—C12	1.376 (3)	C8—H8A	0.9600
O2—H2	0.8200	C8—H8B	0.9600
N1—C9	1.268 (3)	C8—H8C	0.9600
N1—N2	1.387 (3)	C9—H9	0.9300
N2—C10	1.336 (3)	C10—C11	1.481 (4)
N2—H2B	0.898 (10)	C11—C20	1.379 (4)
N3—C4	1.370 (4)	C11—C12	1.424 (3)
N3—C7	1.444 (4)	C12—C13	1.356 (4)
N3—C8	1.444 (4)	C13—C14	1.403 (4)
C1—C6	1.376 (4)	C13—H13	0.9300
C1—C2	1.386 (4)	C14—C15	1.410 (4)
C1—C9	1.436 (4)	C14—C19	1.417 (3)
C2—C3	1.359 (4)	C15—C16	1.349 (4)
C2—H2A	0.9300	C15—H15	0.9300
C3—C4	1.399 (4)	C16—C17	1.404 (5)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.392 (4)	C17—C18	1.359 (4)
C5—C6	1.375 (4)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.408 (4)
C6—H6	0.9300	C18—H18	0.9300
C7—H7A	0.9600	C19—C20	1.395 (4)
C7—H7B	0.9600	C20—H20	0.9300
C12—O2—H2	109.5	H8B—C8—H8C	109.5
C9—N1—N2	114.5 (2)	N1—C9—C1	125.1 (3)
C10—N2—N1	121.8 (2)	N1—C9—H9	117.5
C10—N2—H2B	117.9 (18)	C1—C9—H9	117.5
N1—N2—H2B	120.3 (18)	O1—C10—N2	122.1 (3)
C4—N3—C7	122.3 (3)	O1—C10—C11	120.8 (3)
C4—N3—C8	121.7 (3)	N2—C10—C11	117.1 (2)
C7—N3—C8	116.0 (3)	C20—C11—C12	117.1 (3)
C6—C1—C2	116.3 (3)	C20—C11—C10	116.2 (2)
C6—C1—C9	120.0 (3)	C12—C11—C10	126.6 (3)
C2—C1—C9	123.7 (3)	C13—C12—O2	121.1 (2)
C3—C2—C1	121.5 (3)	C13—C12—C11	120.7 (3)
C3—C2—H2A	119.2	O2—C12—C11	118.2 (3)
C1—C2—H2A	119.2	C12—C13—C14	122.0 (3)
C2—C3—C4	122.6 (3)	C12—C13—H13	119.0
C2—C3—H3	118.7	C14—C13—H13	119.0
C4—C3—H3	118.7	C13—C14—C15	123.3 (3)
N3—C4—C5	121.7 (3)	C13—C14—C19	118.4 (3)
N3—C4—C3	122.4 (3)	C15—C14—C19	118.3 (3)
C5—C4—C3	115.9 (3)	C16—C15—C14	121.1 (3)
C6—C5—C4	120.7 (3)	C16—C15—H15	119.5
C6—C5—H5	119.6	C14—C15—H15	119.5
C4—C5—H5	119.6	C15—C16—C17	120.6 (3)
C5—C6—C1	123.0 (3)	C15—C16—H16	119.7
C5—C6—H6	118.5	C17—C16—H16	119.7
C1—C6—H6	118.5	C18—C17—C16	120.1 (3)
N3—C7—H7A	109.5	C18—C17—H17	119.9
N3—C7—H7B	109.5	C16—C17—H17	119.9
H7A—C7—H7B	109.5	C17—C18—C19	120.7 (3)
N3—C7—H7C	109.5	C17—C18—H18	119.7
H7A—C7—H7C	109.5	C19—C18—H18	119.7
H7B—C7—H7C	109.5	C20—C19—C18	122.6 (3)
N3—C8—H8A	109.5	C20—C19—C14	118.3 (3)
N3—C8—H8B	109.5	C18—C19—C14	119.1 (3)
H8A—C8—H8B	109.5	C11—C20—C19	123.4 (2)
N3—C8—H8C	109.5	C11—C20—H20	118.3
H8A—C8—H8C	109.5	C19—C20—H20	118.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.90 (1)	1.90 (2)	2.644 (3)	139 (2)
O2—H2···O1i	0.82	1.85	2.651 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2	0.898 (10)	1.90 (2)	2.644 (3)	139 (2)
O2—H2⋯O1i	0.82	1.85	2.651 (3)	165

Symmetry code: (i) .