3-Hydr-oxy-N'-(2-methoxy-benzyl-idene)-2-naphthohydrazide.

In the title Schiff base compound, C(19)H(16)N(2)O(3), the dihedral angle between the mean planes of the benzene ring and the naphthyl ring system is 0.8 (2)°. The mean plane of the hydrazide group forms dihedral angles of 2.0 (2) and 2.2 (2)°, respectively, with the mean planes of the benzene ring and the naphthyl ring system. A strong intra-molecular N-H⋯O hydrogen bond is present. In the crystal, inter-molecular O-H⋯O hydrogen bonds form chains along the c axis and help to provide stability in the crystal packing.

Related literature

For the pharmaceutical and medicinal activities of Schiff bases, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For the crystal structures of Schiff base compounds, see: Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶); Hao (2009a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H16N2O3

M = 320.34

Monoclinic,

a = 7.4990 (6) Å

b = 15.4256 (13) Å

c = 13.3903 (12) Å

β = 96.709 (4)°

V = 1538.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.984

9323 measured reflections

3349 independent reflections

2520 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.04

3349 reflections

223 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536809043086/jj2010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043086/jj2010Isup2.hkl

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

C19H16N2O3	F(000) = 672
Mr = 320.34	Dx = 1.383 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3028 reflections
a = 7.4990 (6) Å	θ = 2.6–30.0°
b = 15.4256 (13) Å	µ = 0.10 mm−1
c = 13.3903 (12) Å	T = 298 K
β = 96.709 (4)°	Block, yellow
V = 1538.3 (2) Å3	0.18 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3349 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.983, Tmax = 0.984	k = −19→19
9323 measured reflections	l = −17→14

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.2454P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3349 reflections	Δρmax = 0.20 e Å−3
223 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (13)

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 > 2σ(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	0.12815 (15)	1.07729 (7)	0.87156 (7)	0.0541 (3)
O2	0.53258 (17)	0.75013 (6)	1.13388 (7)	0.0558 (3)
O3	0.43652 (16)	0.74188 (7)	0.81939 (7)	0.0526 (3)
H3	0.4525	0.7391	0.7599	0.079*
N1	0.36704 (15)	0.89208 (7)	1.04707 (8)	0.0409 (3)
N2	0.41657 (16)	0.82106 (7)	0.99432 (8)	0.0408 (3)
C1	0.23017 (18)	1.03244 (9)	1.03531 (10)	0.0394 (3)
C2	0.14420 (18)	1.09540 (9)	0.97151 (10)	0.0399 (3)
C3	0.0791 (2)	1.17049 (10)	1.01086 (12)	0.0502 (4)
H3A	0.0221	1.2122	0.9682	0.060*
C4	0.0989 (3)	1.18316 (11)	1.11277 (13)	0.0663 (5)
H4	0.0542	1.2334	1.1391	0.080*
C5	0.1840 (3)	1.12260 (12)	1.17626 (12)	0.0731 (6)
H5	0.1976	1.1321	1.2453	0.088*
C6	0.2491 (2)	1.04788 (10)	1.13819 (11)	0.0553 (4)
H6	0.3067	1.0071	1.1818	0.066*
C7	0.0339 (3)	1.13737 (12)	0.80462 (11)	0.0631 (5)
H7A	−0.0867	1.1436	0.8210	0.095*
H7B	0.0313	1.1166	0.7369	0.095*
H7C	0.0934	1.1925	0.8107	0.095*
C8	0.29350 (19)	0.95271 (9)	0.99292 (10)	0.0422 (3)
H8	0.2795	0.9460	0.9234	0.051*
C9	0.49987 (18)	0.75329 (8)	1.04213 (9)	0.0371 (3)
C10	0.55517 (17)	0.68060 (8)	0.97827 (9)	0.0348 (3)
C11	0.52607 (18)	0.67543 (9)	0.87108 (9)	0.0381 (3)
C12	0.5848 (2)	0.60516 (9)	0.82249 (10)	0.0439 (3)
H12	0.5655	0.6030	0.7526	0.053*
C13	0.67397 (19)	0.53573 (9)	0.87531 (10)	0.0410 (3)
C14	0.7369 (2)	0.46152 (10)	0.82747 (12)	0.0561 (4)
H14	0.7206	0.4577	0.7577	0.067*
C15	0.8204 (2)	0.39614 (10)	0.88198 (14)	0.0615 (5)
H15	0.8599	0.3480	0.8490	0.074*
C16	0.8481 (2)	0.39985 (10)	0.98705 (13)	0.0558 (4)
H16	0.9060	0.3546	1.0235	0.067*
C17	0.79016 (19)	0.46984 (9)	1.03570 (11)	0.0459 (3)
H17	0.8084	0.4720	1.1056	0.055*
C18	0.70267 (17)	0.53921 (8)	0.98165 (10)	0.0370 (3)
C19	0.64040 (17)	0.61253 (9)	1.02959 (9)	0.0376 (3)
H19	0.6579	0.6150	1.0994	0.045*
H2	0.398 (2)	0.8200 (12)	0.9273 (7)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0763 (8)	0.0503 (6)	0.0362 (5)	0.0137 (5)	0.0089 (5)	0.0025 (4)
O2	0.0943 (9)	0.0461 (6)	0.0267 (5)	0.0082 (5)	0.0067 (5)	−0.0025 (4)
O3	0.0792 (8)	0.0541 (6)	0.0249 (5)	0.0150 (5)	0.0074 (5)	0.0044 (4)
N1	0.0482 (7)	0.0378 (6)	0.0375 (6)	−0.0002 (5)	0.0085 (5)	−0.0037 (5)
N2	0.0546 (7)	0.0381 (6)	0.0302 (6)	0.0043 (5)	0.0072 (5)	−0.0025 (5)
C1	0.0418 (7)	0.0381 (7)	0.0388 (7)	−0.0053 (6)	0.0063 (6)	−0.0028 (6)
C2	0.0435 (8)	0.0392 (7)	0.0375 (7)	−0.0052 (6)	0.0059 (6)	−0.0016 (6)
C3	0.0600 (9)	0.0390 (8)	0.0502 (8)	0.0048 (7)	0.0007 (7)	−0.0027 (6)
C4	0.0891 (13)	0.0515 (10)	0.0554 (10)	0.0164 (9)	−0.0042 (9)	−0.0200 (8)
C5	0.1083 (15)	0.0666 (12)	0.0402 (9)	0.0207 (11)	−0.0087 (9)	−0.0189 (8)
C6	0.0726 (11)	0.0507 (9)	0.0398 (8)	0.0091 (8)	−0.0047 (7)	−0.0034 (7)
C7	0.0817 (12)	0.0653 (11)	0.0412 (8)	0.0150 (9)	0.0030 (8)	0.0094 (8)
C8	0.0514 (8)	0.0423 (8)	0.0338 (7)	0.0004 (6)	0.0087 (6)	0.0007 (6)
C9	0.0471 (8)	0.0370 (7)	0.0279 (6)	−0.0065 (6)	0.0071 (5)	−0.0007 (5)
C10	0.0398 (7)	0.0376 (7)	0.0274 (6)	−0.0055 (5)	0.0060 (5)	−0.0005 (5)
C11	0.0457 (8)	0.0412 (7)	0.0279 (6)	−0.0021 (6)	0.0063 (5)	0.0036 (5)
C12	0.0595 (9)	0.0474 (8)	0.0261 (6)	−0.0037 (7)	0.0102 (6)	−0.0022 (6)
C13	0.0468 (8)	0.0398 (7)	0.0385 (7)	−0.0054 (6)	0.0137 (6)	−0.0024 (6)
C14	0.0767 (11)	0.0485 (9)	0.0469 (9)	−0.0011 (8)	0.0237 (8)	−0.0075 (7)
C15	0.0700 (11)	0.0409 (9)	0.0788 (12)	0.0036 (8)	0.0303 (9)	−0.0059 (8)
C16	0.0529 (9)	0.0421 (9)	0.0737 (11)	0.0035 (7)	0.0128 (8)	0.0066 (8)
C17	0.0446 (8)	0.0430 (8)	0.0498 (8)	−0.0024 (6)	0.0039 (6)	0.0051 (6)
C18	0.0362 (7)	0.0372 (7)	0.0381 (7)	−0.0056 (5)	0.0068 (5)	0.0009 (5)
C19	0.0427 (7)	0.0415 (7)	0.0280 (6)	−0.0058 (6)	0.0023 (5)	0.0003 (5)

O1—C2	1.3587 (16)	C7—H7B	0.9600
O1—C7	1.4190 (18)	C7—H7C	0.9600
O2—C9	1.2253 (15)	C8—H8	0.9300
O3—C11	1.3683 (16)	C9—C10	1.4978 (18)
O3—H3	0.8200	C10—C19	1.3713 (18)
N1—C8	1.2693 (17)	C10—C11	1.4287 (17)
N1—N2	1.3778 (15)	C11—C12	1.3635 (19)
N2—C9	1.3415 (17)	C12—C13	1.409 (2)
N2—H2	0.892 (9)	C12—H12	0.9300
C1—C6	1.3889 (19)	C13—C18	1.4160 (18)
C1—C2	1.4000 (19)	C13—C14	1.419 (2)
C1—C8	1.4571 (19)	C14—C15	1.355 (2)
C2—C3	1.385 (2)	C14—H14	0.9300
C3—C4	1.369 (2)	C15—C16	1.399 (2)
C3—H3A	0.9300	C15—H15	0.9300
C4—C5	1.369 (2)	C16—C17	1.358 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.373 (2)	C17—C18	1.4101 (19)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.4069 (19)
C7—H7A	0.9600	C19—H19	0.9300
C2—O1—C7	117.92 (11)	O2—C9—N2	122.48 (12)
C11—O3—H3	109.5	O2—C9—C10	120.42 (12)
C8—N1—N2	114.72 (11)	N2—C9—C10	117.10 (11)
C9—N2—N1	120.89 (11)	C19—C10—C11	117.92 (12)
C9—N2—H2	118.3 (12)	C19—C10—C9	115.53 (11)
N1—N2—H2	120.7 (12)	C11—C10—C9	126.54 (12)
C6—C1—C2	118.21 (13)	C12—C11—O3	121.40 (11)
C6—C1—C8	122.06 (13)	C12—C11—C10	120.25 (12)
C2—C1—C8	119.71 (12)	O3—C11—C10	118.34 (11)
O1—C2—C3	123.52 (13)	C11—C12—C13	121.71 (12)
O1—C2—C1	116.10 (12)	C11—C12—H12	119.1
C3—C2—C1	120.38 (13)	C13—C12—H12	119.1
C4—C3—C2	119.77 (14)	C12—C13—C18	118.92 (12)
C4—C3—H3A	120.1	C12—C13—C14	123.37 (13)
C2—C3—H3A	120.1	C18—C13—C14	117.71 (13)
C3—C4—C5	120.65 (15)	C15—C14—C13	120.96 (15)
C3—C4—H4	119.7	C15—C14—H14	119.5
C5—C4—H4	119.7	C13—C14—H14	119.5
C4—C5—C6	120.15 (15)	C14—C15—C16	121.09 (15)
C4—C5—H5	119.9	C14—C15—H15	119.5
C6—C5—H5	119.9	C16—C15—H15	119.5
C5—C6—C1	120.84 (15)	C17—C16—C15	119.77 (15)
C5—C6—H6	119.6	C17—C16—H16	120.1
C1—C6—H6	119.6	C15—C16—H16	120.1
O1—C7—H7A	109.5	C16—C17—C18	120.85 (14)
O1—C7—H7B	109.5	C16—C17—H17	119.6
H7A—C7—H7B	109.5	C18—C17—H17	119.6
O1—C7—H7C	109.5	C19—C18—C17	122.36 (12)
H7A—C7—H7C	109.5	C19—C18—C13	118.02 (12)
H7B—C7—H7C	109.5	C17—C18—C13	119.62 (12)
N1—C8—C1	122.61 (12)	C10—C19—C18	123.16 (12)
N1—C8—H8	118.7	C10—C19—H19	118.4
C1—C8—H8	118.7	C18—C19—H19	118.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.89 (1)	1.93 (1)	2.6613 (14)	138 (2)
O3—H3···O2i	0.82	1.86	2.6689 (13)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.892 (9)	1.929 (14)	2.6613 (14)	138.3 (16)
O3—H3⋯O2i	0.82	1.86	2.6689 (13)	167

Symmetry code: (i) .