(2Z,N'E)-N'-[(2-Hy-droxy-1-naphth-yl)methyl-idene]furan-2-carbohydrazonic acid.

In the title compound, C(16)H(12)N(2)O(3), the dihedral angle between the mean planes of the naphthalene ring system and the furan ring is 21.3 (6)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) graph-set motif.

Related literature

For historical background to aroylhydrazones, see: Arapov et al. (1987 ▶); Pickart et al. (1983 ▶); Offe et al. (1952 ▶); Nagaraju et al. (2009 ▶); Ghosh et al. (2007 ▶). For related structures, see: Monfared et al. (2010 ▶); Ali et al. (2005 ▶); Qian et al. (2006 ▶); Tarafder et al. (2002 ▶); Prathapachandra Kurup & Bessy Raj (2007 ▶). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12N2O3

M = 280.28

Orthorhombic,

a = 9.7427 (8) Å

b = 21.4182 (8) Å

c = 6.445 (2) Å

V = 1344.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.31 × 0.27 × 0.15 mm

Data collection

STOE IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.970, T max = 0.985

7278 measured reflections

1440 independent reflections

944 reflections with I > 2σ(I)

R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.095

S = 1.02

1440 reflections

191 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027935/jj2034sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027935/jj2034Isup2.hkl

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

C16H12N2O3	Dx = 1.384 Mg m−3
Mr = 280.28	Melting point = 470–471 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8863 reflections
a = 9.7427 (8) Å	θ = 1.9–27.1°
b = 21.4182 (8) Å	µ = 0.10 mm−1
c = 6.445 (2) Å	T = 293 K
V = 1344.8 (4) Å3	Prism, colourless
Z = 4	0.31 × 0.27 × 0.15 mm
F(000) = 584

STOE IPDS 2 diffractometer	1440 independent reflections
Radiation source: fine-focus sealed tube	944 reflections with I > 2σ(I)
plane graphite	Rint = 0.097
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.9°
rotation method scans	h = −12→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −26→24
Tmin = 0.970, Tmax = 0.985	l = −7→7
7278 measured reflections

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.031P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1440 reflections	Δρmax = 0.18 e Å−3
191 parameters	Δρmin = −0.13 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: 0.0063 (17)

Experimental. 12912 Friedel pairs have been merged

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C1	0.2976 (5)	0.54675 (18)	0.6316 (7)	0.0451 (11)
C2	0.2057 (5)	0.5256 (2)	0.4789 (8)	0.0522 (12)
H2	0.1969	0.5479	0.3559	0.063*
C3	0.1290 (6)	0.4730 (2)	0.5070 (8)	0.0706 (16)
H3	0.0688	0.4601	0.4036	0.085*
C4	0.1400 (7)	0.4384 (2)	0.6892 (10)	0.0786 (18)
H4	0.0883	0.4022	0.7065	0.094*
C5	0.2262 (6)	0.4574 (2)	0.8410 (10)	0.0714 (16)
H5	0.2320	0.4347	0.9636	0.086*
C6	0.3079 (5)	0.51178 (19)	0.8155 (7)	0.0499 (12)
C7	0.4022 (6)	0.5297 (2)	0.9729 (7)	0.0591 (14)
H7	0.4051	0.5078	1.0974	0.071*
C8	0.4882 (5)	0.5788 (2)	0.9420 (8)	0.0552 (13)
H8	0.5516	0.5897	1.0436	0.066*
C9	0.4814 (5)	0.61298 (19)	0.7575 (7)	0.0474 (11)
C10	0.3861 (5)	0.6002 (2)	0.6042 (6)	0.0406 (10)
C11	0.3758 (5)	0.63934 (18)	0.4226 (6)	0.0440 (11)
H11	0.3027	0.6340	0.3314	0.053*
C12	0.5461 (5)	0.7550 (2)	0.1419 (7)	0.0488 (11)
C13	0.5167 (5)	0.78815 (19)	−0.0481 (7)	0.0513 (12)
C14	0.5895 (6)	0.8270 (2)	−0.1646 (8)	0.0631 (14)
H14	0.6764	0.8425	−0.1343	0.076*
C15	0.5117 (7)	0.8404 (3)	−0.3412 (9)	0.0810 (19)
H15	0.5371	0.8661	−0.4511	0.097*
C16	0.3952 (7)	0.8095 (3)	−0.3215 (9)	0.0783 (18)
H16	0.3240	0.8102	−0.4178	0.094*
N1	0.4666 (4)	0.68174 (16)	0.3852 (6)	0.0488 (10)
N2	0.4425 (4)	0.71739 (15)	0.2109 (6)	0.0495 (10)
O1	0.5751 (3)	0.65972 (14)	0.7404 (5)	0.0632 (10)
H1	0.5641	0.6779	0.6296	0.095*
O2	0.6585 (3)	0.76014 (14)	0.2278 (5)	0.0658 (10)
H22	0.6598	0.7385	0.3328	0.099*
O3	0.3934 (3)	0.77680 (15)	−0.1422 (6)	0.0675 (10)

	U11	U22	U33	U12	U13	U23
C1	0.050 (3)	0.037 (2)	0.048 (3)	0.008 (2)	0.011 (2)	0.001 (2)
C2	0.052 (3)	0.048 (3)	0.056 (3)	0.002 (2)	0.008 (3)	−0.001 (2)
C3	0.075 (4)	0.056 (3)	0.081 (4)	−0.017 (3)	0.005 (3)	−0.006 (3)
C4	0.084 (5)	0.052 (3)	0.100 (5)	−0.015 (3)	0.023 (4)	0.005 (4)
C5	0.076 (4)	0.058 (3)	0.080 (4)	0.001 (3)	0.015 (4)	0.009 (3)
C6	0.052 (3)	0.040 (2)	0.057 (3)	0.010 (2)	0.011 (2)	0.002 (2)
C7	0.073 (4)	0.057 (3)	0.047 (3)	0.023 (3)	0.002 (3)	0.013 (2)
C8	0.055 (3)	0.060 (3)	0.050 (3)	0.016 (3)	−0.007 (2)	−0.011 (3)
C9	0.046 (3)	0.042 (2)	0.054 (3)	0.008 (2)	−0.001 (2)	−0.003 (2)
C10	0.036 (3)	0.043 (2)	0.043 (2)	0.011 (2)	0.003 (2)	0.001 (2)
C11	0.037 (3)	0.047 (2)	0.049 (3)	0.001 (2)	0.000 (2)	−0.002 (2)
C12	0.036 (3)	0.054 (3)	0.056 (3)	−0.002 (2)	0.005 (2)	−0.008 (2)
C13	0.044 (3)	0.047 (2)	0.063 (3)	0.000 (2)	0.007 (3)	0.005 (2)
C14	0.059 (3)	0.060 (3)	0.070 (3)	−0.018 (3)	0.012 (3)	0.009 (3)
C15	0.087 (5)	0.075 (4)	0.081 (4)	0.011 (4)	0.027 (4)	0.034 (3)
C16	0.060 (4)	0.087 (4)	0.088 (5)	0.022 (3)	0.011 (3)	0.033 (4)
N1	0.038 (2)	0.050 (2)	0.058 (3)	−0.002 (2)	0.0096 (18)	0.0013 (19)
N2	0.043 (2)	0.0485 (19)	0.057 (2)	−0.0082 (18)	0.0117 (19)	0.0134 (19)
O1	0.056 (2)	0.060 (2)	0.074 (2)	−0.0063 (18)	−0.0109 (19)	−0.0017 (18)
O2	0.056 (2)	0.078 (2)	0.064 (2)	−0.0186 (18)	0.001 (2)	0.0063 (19)
O3	0.040 (2)	0.078 (2)	0.085 (3)	0.0037 (18)	0.0047 (19)	0.0323 (19)

C1—C2	1.406 (6)	C10—C11	1.443 (6)
C1—C6	1.406 (6)	C11—N1	1.291 (5)
C1—C10	1.444 (6)	C11—H11	0.9300
C2—C3	1.364 (7)	C12—O2	1.232 (5)
C2—H2	0.9300	C12—N2	1.366 (5)
C3—C4	1.393 (8)	C12—C13	1.444 (6)
C3—H3	0.9300	C13—C14	1.326 (6)
C4—C5	1.352 (8)	C13—O3	1.367 (5)
C4—H4	0.9300	C14—C15	1.398 (7)
C5—C6	1.420 (7)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.321 (8)
C6—C7	1.422 (7)	C15—H15	0.9300
C7—C8	1.359 (7)	C16—O3	1.352 (6)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.397 (6)	N1—N2	1.379 (5)
C8—H8	0.9300	O1—H1	0.8200
C9—O1	1.359 (5)	O2—H22	0.8200
C9—C10	1.384 (6)
C2—C1—C6	117.6 (4)	C9—C10—C11	120.7 (4)
C2—C1—C10	123.4 (4)	C9—C10—C1	118.1 (4)
C6—C1—C10	118.9 (4)	C11—C10—C1	121.2 (4)
C3—C2—C1	121.5 (5)	N1—C11—C10	120.8 (4)
C3—C2—H2	119.3	N1—C11—H11	119.6
C1—C2—H2	119.3	C10—C11—H11	119.6
C2—C3—C4	120.6 (5)	O2—C12—N2	124.3 (4)
C2—C3—H3	119.7	O2—C12—C13	120.9 (4)
C4—C3—H3	119.7	N2—C12—C13	114.8 (4)
C5—C4—C3	119.8 (5)	C14—C13—O3	109.3 (4)
C5—C4—H4	120.1	C14—C13—C12	133.0 (5)
C3—C4—H4	120.1	O3—C13—C12	117.6 (4)
C4—C5—C6	120.8 (6)	C13—C14—C15	107.5 (5)
C4—C5—H5	119.6	C13—C14—H14	126.3
C6—C5—H5	119.6	C15—C14—H14	126.3
C1—C6—C5	119.6 (5)	C16—C15—C14	106.5 (5)
C1—C6—C7	120.3 (4)	C16—C15—H15	126.7
C5—C6—C7	120.1 (5)	C14—C15—H15	126.7
C8—C7—C6	120.2 (5)	C15—C16—O3	110.7 (6)
C8—C7—H7	119.9	C15—C16—H16	124.7
C6—C7—H7	119.9	O3—C16—H16	124.7
C7—C8—C9	120.0 (5)	C11—N1—N2	115.1 (4)
C7—C8—H8	120.0	C12—N2—N1	117.7 (4)
C9—C8—H8	120.0	C9—O1—H1	109.5
O1—C9—C10	122.6 (4)	C12—O2—H22	109.5
O1—C9—C8	115.0 (5)	C16—O3—C13	106.0 (4)
C10—C9—C8	122.4 (5)
C6—C1—C2—C3	−0.1 (7)	C6—C1—C10—C9	2.6 (6)
C10—C1—C2—C3	176.6 (4)	C2—C1—C10—C11	6.2 (6)
C1—C2—C3—C4	−0.2 (8)	C6—C1—C10—C11	−177.3 (4)
C2—C3—C4—C5	0.9 (9)	C9—C10—C11—N1	9.5 (6)
C3—C4—C5—C6	−1.3 (8)	C1—C10—C11—N1	−170.6 (4)
C2—C1—C6—C5	−0.3 (6)	O2—C12—C13—C14	−0.1 (8)
C10—C1—C6—C5	−177.1 (4)	N2—C12—C13—C14	−178.3 (5)
C2—C1—C6—C7	178.0 (4)	O2—C12—C13—O3	175.5 (4)
C10—C1—C6—C7	1.2 (6)	N2—C12—C13—O3	−2.6 (6)
C4—C5—C6—C1	1.0 (7)	O3—C13—C14—C15	−0.9 (5)
C4—C5—C6—C7	−177.3 (5)	C12—C13—C14—C15	175.0 (5)
C1—C6—C7—C8	−3.5 (7)	C13—C14—C15—C16	0.7 (6)
C5—C6—C7—C8	174.8 (5)	C14—C15—C16—O3	−0.1 (7)
C6—C7—C8—C9	1.8 (7)	C10—C11—N1—N2	−177.8 (4)
C7—C8—C9—O1	−177.9 (4)	O2—C12—N2—N1	−1.6 (6)
C7—C8—C9—C10	2.2 (7)	C13—C12—N2—N1	176.5 (4)
O1—C9—C10—C11	−4.3 (6)	C11—N1—N2—C12	−168.4 (4)
C8—C9—C10—C11	175.5 (4)	C15—C16—O3—C13	−0.5 (6)
O1—C9—C10—C1	175.7 (4)	C14—C13—O3—C16	0.9 (5)
C8—C9—C10—C1	−4.5 (6)	C12—C13—O3—C16	−175.7 (4)
C2—C1—C10—C9	−173.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.565 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.565 (5)	146