N′-[4-(Dimethyl­amino)benzyl­idene]-3-hydr­oxy-2-naphthohydrazide

Huang, H.-T.

doi:10.1107/S160053680900960X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o892

doi:10.1107/S160053680900960X

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N′-[4-(Dimethylamino)benzylidene]-3-hydroxy-2-naphthohydrazide

Hai-Tao Huang ^a ^*

^aPharmacy School, Qiqihar Medical University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: huanghaitao09@163.com

(Received 10 March 2009; accepted 16 March 2009; online 28 March 2009)

The title compound, C₂₀H₁₉N₃O₂, was obtained by the condensation of 4-(dimethylamino)benzaldehyde with 3-hydroxy-2-naphthohydrazide. The molecule is approximately planar, with an intramolecular N—H⋯O hydrogen bond involving the imino H atom and the hydroxy O atom. The dihedral angle between the benzene ring and the naphthyl mean plane is 2.72 (13)°. In the crystal structure, symmetry-related molecules are linked by intermolecular 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_r = 333.38
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.190
S = 1.03
3670 reflections
232 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900960X/su2102sup1.cif

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

checkCIF report

Comment top

In recent years compounds derived from the condensation of aldehydes with benzohydrazides have been widely investigated, either for their structures (Qiu & Zhao, 2008; Yathirajan et al., 2007; Salhin et al., 2007) or for their biological properties (Küçükgüzel et al., 2003); Charkoudian et al., 2007). The author reports herein the crystal structure of the title compound, obtained by the condensation of 4-dimethylaminobenzaldehyde with 3-hydroxy-2-naphthohydrazide.

The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths are within normal values (Allen et al., 1987), and are comparable to the values in similar compounds (Fun et al., 2008; Liu & Li, 2004; Lei et al., 2008). The molecule is approximately coplanar, with the dihedral angle between the benzene ring and the naphthyl mean-plane being 2.72 (13)°. There is an intramolecular N-H···O hydrogen bond, involving the imino H-atom and the hydroxyl O-atom (Table 1).

In the crystal structure symmetry related molecules are linked via intermolecular O–H···O hydrogen bonds to form one-dimensional chains propagating in the c direction (Fig. 2 and Table 1).

Related literature top

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 top

The title compound was prepared by the condensation of 4-dimethylaminobenzaldehyde (0.1 mol) and 3-hydroxy-2-naphthohydrazide (0.1 mmol) in ethanol (20 ml). The excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals, suitable for X-ray diffraction, were obtained on slow evaporation of a solution of the title compound in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. The intramolecular N2-H2B···O2 hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The intermolecular O-H···O hydrogen bonds are shown as dashed lines - see Table 1 for details (H-atoms not involved in hydrogen bonding have been omitted for clarity).

N'-[4-(Dimethylamino)benzylidene]-3-hydroxy-2-naphthohydrazide top

Crystal data top

C₂₀H₁₉N₃O₂	F(000) = 704
M_r = 333.38	D_x = 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

Data collection top

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

Refinement top

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(F_o²)]
3670 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₀H₁₉N₃O₂	V = 1695.2 (7) Å³
M_r = 333.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.090 (2) Å	µ = 0.09 mm⁻¹
b = 15.798 (3) Å	T = 298 K
c = 13.428 (3) Å	0.27 × 0.23 × 0.22 mm
β = 98.978 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3670 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1629 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.075
13922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	1 restraint
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
3670 reflections	Δρ_min = −0.17 e Å⁻³
232 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₂
M_r	333.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.090 (2), 15.798 (3), 13.428 (3)
β (°)	98.978 (3)
V (Å³)	1695.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.23 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	13922, 3670, 1629
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.190, 1.03
No. of reflections	3670
No. of parameters	232
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	164.9

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

This work was supported by Qiqihar Medical University, China.

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