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

The title compound, C(18)H(14)N(2)O(3), is an aroylhydrazone with an approximately planar structure [dihedral angle of 15.27 (13)° between the benzene ring and the naphthyl ring system], stabilized by intra-molecular N-H⋯O and O-H⋯N hydrogen bonds. Inter-molecular O-H⋯O hydrogen bonds with the keto group as acceptor lead to strands along [100]. In terms of graph-set analysis, the descriptor on the unitary level is C(1) (1)(6)S(6)S(6).

Related literature

For historical background to aroylhydrazones, see: Savanini et al. (2002 ▶); Craliz et al. (1955 ▶); Pickart et al. (1983 ▶); Offe et al. (1952 ▶); Arapov et al. (1987 ▶); Ranford et al. (1998 ▶). For related structures, see: Liu et al. (2004 ▶); Lei et al. (2008 ▶). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C18H14N2O3

M = 306.32

Orthorhombic,

a = 12.6749 (4) Å

b = 4.9666 (1) Å

c = 22.7299 (6) Å

V = 1430.87 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.50 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer

10328 measured reflections

1676 independent reflections

1416 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.09

1676 reflections

220 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053793/bg2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053793/bg2308Isup2.hkl

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

C18H14N2O3	F(000) = 640
Mr = 306.32	Dx = 1.422 (1) Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5508 reflections
a = 12.6749 (4) Å	θ = 3.1–27.5°
b = 4.9666 (1) Å	µ = 0.10 mm−1
c = 22.7299 (6) Å	T = 200 K
V = 1430.87 (7) Å3	Rod, yellow
Z = 4	0.50 × 0.10 × 0.09 mm

Nonius KappaCCD diffractometer	1416 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.054
MONTEL, graded multilayered X-ray optics	θmax = 27.4°, θmin = 3.3°
Detector resolution: 9 pixels mm-1	h = −16→16
CCD; rotation images; thick slices, phi/ω–scan	k = −6→6
10328 measured reflections	l = −29→29
1676 independent reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.052P)2 + 0.1709P] where P = (Fo2 + 2Fc2)/3
1676 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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 > 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	0.23226 (13)	0.2694 (4)	0.22862 (9)	0.0383 (4)
O2	0.31563 (16)	−0.3045 (5)	0.09755 (11)	0.0533 (6)
H2	0.280 (4)	−0.182 (9)	0.124 (2)	0.092 (14)*
O3	−0.08649 (14)	0.4024 (3)	0.18929 (8)	0.0325 (4)
H3	−0.151 (3)	0.377 (6)	0.1953 (15)	0.044 (8)*
N1	0.09013 (15)	0.1311 (4)	0.17680 (9)	0.0283 (4)
H1	0.019 (2)	0.157 (5)	0.1723 (13)	0.037 (7)*
N2	0.14658 (15)	−0.0532 (4)	0.14425 (8)	0.0290 (4)
C1	0.13752 (17)	0.2878 (5)	0.21681 (10)	0.0258 (5)
C2	0.06987 (17)	0.4915 (5)	0.24682 (10)	0.0250 (5)
C3	−0.03790 (17)	0.5489 (5)	0.23284 (10)	0.0255 (5)
C4	−0.09057 (18)	0.7497 (5)	0.26178 (11)	0.0283 (5)
H4	−0.1612	0.7897	0.2509	0.034*
C5	−0.04258 (17)	0.8986 (5)	0.30734 (10)	0.0272 (5)
C6	−0.0956 (2)	1.1070 (5)	0.33832 (11)	0.0332 (6)
H6	−0.1660	1.1524	0.3280	0.040*
C7	−0.0461 (2)	1.2432 (5)	0.38286 (11)	0.0353 (6)
H7	−0.0828	1.3807	0.4035	0.042*
C8	0.0589 (2)	1.1808 (6)	0.39843 (12)	0.0380 (6)
H8	0.0925	1.2761	0.4294	0.046*
C9	0.1119 (2)	0.9845 (5)	0.36906 (11)	0.0344 (6)
H9	0.1827	0.9443	0.3797	0.041*
C10	0.06327 (18)	0.8391 (5)	0.32300 (10)	0.0279 (5)
C11	0.11661 (18)	0.6368 (5)	0.29118 (11)	0.0282 (5)
H11	0.1880	0.5994	0.3008	0.034*
C12	0.0899 (2)	−0.1961 (5)	0.10947 (11)	0.0301 (5)
H12	0.0156	−0.1697	0.1093	0.036*
C13	0.1346 (2)	−0.3955 (5)	0.07051 (10)	0.0310 (5)
C14	0.2435 (2)	−0.4434 (6)	0.06574 (12)	0.0372 (6)
C15	0.2796 (2)	−0.6364 (7)	0.02599 (16)	0.0501 (7)
H15	0.3532	−0.6656	0.0216	0.060*
C16	0.2097 (3)	−0.7845 (6)	−0.00686 (14)	0.0488 (8)
H16	0.2356	−0.9187	−0.0329	0.059*
C17	0.1027 (3)	−0.7416 (5)	−0.00265 (13)	0.0450 (7)
H17	0.0548	−0.8429	−0.0259	0.054*
C18	0.0665 (2)	−0.5492 (5)	0.03591 (11)	0.0388 (6)
H18	−0.0073	−0.5201	0.0391	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0226 (8)	0.0433 (10)	0.0489 (10)	0.0037 (7)	−0.0027 (8)	−0.0084 (9)
O2	0.0286 (10)	0.0615 (14)	0.0697 (15)	0.0054 (9)	−0.0018 (10)	−0.0210 (12)
O3	0.0207 (8)	0.0394 (10)	0.0373 (10)	−0.0008 (7)	−0.0018 (7)	−0.0050 (8)
N1	0.0209 (9)	0.0316 (10)	0.0324 (10)	0.0024 (8)	0.0015 (8)	−0.0025 (8)
N2	0.0265 (9)	0.0297 (10)	0.0309 (10)	0.0024 (8)	0.0038 (8)	0.0004 (8)
C1	0.0216 (10)	0.0267 (11)	0.0290 (12)	0.0000 (9)	0.0025 (9)	0.0035 (10)
C2	0.0218 (11)	0.0243 (12)	0.0288 (11)	−0.0016 (9)	0.0026 (9)	0.0038 (9)
C3	0.0228 (11)	0.0268 (11)	0.0270 (11)	−0.0034 (9)	−0.0004 (9)	0.0021 (10)
C4	0.0213 (10)	0.0295 (12)	0.0340 (12)	0.0016 (9)	0.0003 (9)	0.0056 (10)
C5	0.0266 (11)	0.0260 (12)	0.0292 (11)	−0.0020 (9)	0.0012 (9)	0.0044 (9)
C6	0.0321 (12)	0.0314 (13)	0.0362 (14)	0.0010 (10)	0.0045 (10)	0.0029 (11)
C7	0.0439 (14)	0.0290 (13)	0.0330 (13)	0.0009 (11)	0.0056 (11)	−0.0026 (11)
C8	0.0447 (15)	0.0367 (14)	0.0326 (13)	−0.0053 (12)	−0.0032 (12)	−0.0016 (11)
C9	0.0341 (12)	0.0335 (13)	0.0357 (13)	−0.0029 (10)	−0.0065 (11)	0.0020 (11)
C10	0.0289 (12)	0.0263 (12)	0.0285 (12)	−0.0030 (10)	−0.0008 (10)	0.0036 (10)
C11	0.0238 (11)	0.0293 (12)	0.0315 (12)	−0.0007 (9)	−0.0016 (9)	0.0023 (10)
C12	0.0270 (11)	0.0311 (13)	0.0320 (11)	0.0009 (10)	0.0028 (10)	0.0020 (11)
C13	0.0338 (12)	0.0287 (13)	0.0305 (13)	0.0016 (9)	0.0028 (10)	0.0023 (10)
C14	0.0335 (12)	0.0361 (15)	0.0419 (14)	0.0007 (10)	0.0018 (11)	−0.0029 (12)
C15	0.0440 (16)	0.0484 (17)	0.0577 (17)	0.0120 (13)	0.0099 (15)	−0.0050 (15)
C16	0.072 (2)	0.0361 (15)	0.0389 (15)	0.0052 (14)	0.0104 (14)	−0.0061 (13)
C17	0.062 (2)	0.0370 (15)	0.0365 (15)	−0.0039 (14)	−0.0021 (13)	−0.0023 (13)
C18	0.0411 (14)	0.0380 (15)	0.0372 (13)	−0.0031 (11)	−0.0018 (12)	−0.0019 (12)

O1—C1	1.234 (3)	C7—H7	0.9500
O2—C14	1.354 (3)	C8—C9	1.360 (4)
O2—H2	0.96 (5)	C8—H8	0.9500
O3—C3	1.374 (3)	C9—C10	1.413 (3)
O3—H3	0.84 (4)	C9—H9	0.9500
N1—C1	1.339 (3)	C10—C11	1.411 (3)
N1—N2	1.378 (3)	C11—H11	0.9500
N1—H1	0.92 (3)	C12—C13	1.444 (3)
N2—C12	1.283 (3)	C12—H12	0.9500
C1—C2	1.491 (3)	C13—C18	1.395 (3)
C2—C11	1.374 (3)	C13—C14	1.405 (3)
C2—C3	1.431 (3)	C14—C15	1.394 (4)
C3—C4	1.368 (3)	C15—C16	1.372 (5)
C4—C5	1.410 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.377 (5)
C5—C10	1.419 (3)	C16—H16	0.9500
C5—C6	1.421 (3)	C17—C18	1.375 (4)
C6—C7	1.369 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.411 (4)
C14—O2—H2	110 (3)	C8—C9—C10	121.0 (2)
C3—O3—H3	114 (2)	C8—C9—H9	119.5
C1—N1—N2	121.20 (19)	C10—C9—H9	119.5
C1—N1—H1	115.9 (18)	C11—C10—C9	122.3 (2)
N2—N1—H1	122.9 (18)	C11—C10—C5	118.2 (2)
C12—N2—N1	114.05 (19)	C9—C10—C5	119.5 (2)
O1—C1—N1	122.8 (2)	C2—C11—C10	122.9 (2)
O1—C1—C2	120.7 (2)	C2—C11—H11	118.5
N1—C1—C2	116.55 (19)	C10—C11—H11	118.5
C11—C2—C3	118.0 (2)	N2—C12—C13	122.5 (2)
C11—C2—C1	116.35 (19)	N2—C12—H12	118.8
C3—C2—C1	125.6 (2)	C13—C12—H12	118.8
C4—C3—O3	120.88 (19)	C18—C13—C14	118.1 (2)
C4—C3—C2	120.3 (2)	C18—C13—C12	118.6 (2)
O3—C3—C2	118.84 (19)	C14—C13—C12	123.3 (2)
C3—C4—C5	121.6 (2)	O2—C14—C15	118.4 (2)
C3—C4—H4	119.2	O2—C14—C13	122.4 (2)
C5—C4—H4	119.2	C15—C14—C13	119.2 (3)
C4—C5—C10	118.9 (2)	C16—C15—C14	120.7 (3)
C4—C5—C6	122.8 (2)	C16—C15—H15	119.7
C10—C5—C6	118.3 (2)	C14—C15—H15	119.7
C7—C6—C5	120.7 (2)	C15—C16—C17	121.0 (3)
C7—C6—H6	119.7	C15—C16—H16	119.5
C5—C6—H6	119.7	C17—C16—H16	119.5
C6—C7—C8	120.6 (2)	C18—C17—C16	118.7 (3)
C6—C7—H7	119.7	C18—C17—H17	120.6
C8—C7—H7	119.7	C16—C17—H17	120.6
C9—C8—C7	120.0 (2)	C17—C18—C13	122.2 (3)
C9—C8—H8	120.0	C17—C18—H18	118.9
C7—C8—H8	120.0	C13—C18—H18	118.9
C1—N1—N2—C12	177.3 (2)	C4—C5—C10—C11	1.4 (3)
N2—N1—C1—O1	−3.1 (3)	C6—C5—C10—C11	−178.4 (2)
N2—N1—C1—C2	176.38 (18)	C4—C5—C10—C9	−179.2 (2)
O1—C1—C2—C11	−5.6 (3)	C6—C5—C10—C9	1.0 (3)
N1—C1—C2—C11	174.9 (2)	C3—C2—C11—C10	−0.3 (3)
O1—C1—C2—C3	173.6 (2)	C1—C2—C11—C10	179.0 (2)
N1—C1—C2—C3	−5.9 (3)	C9—C10—C11—C2	179.1 (2)
C11—C2—C3—C4	2.3 (3)	C5—C10—C11—C2	−1.5 (3)
C1—C2—C3—C4	−177.0 (2)	N1—N2—C12—C13	178.3 (2)
C11—C2—C3—O3	−178.9 (2)	N2—C12—C13—C18	177.4 (2)
C1—C2—C3—O3	1.8 (3)	N2—C12—C13—C14	−2.4 (4)
O3—C3—C4—C5	178.8 (2)	C18—C13—C14—O2	−179.9 (3)
C2—C3—C4—C5	−2.4 (4)	C12—C13—C14—O2	−0.1 (4)
C3—C4—C5—C10	0.5 (3)	C18—C13—C14—C15	1.5 (4)
C3—C4—C5—C6	−179.7 (2)	C12—C13—C14—C15	−178.7 (3)
C4—C5—C6—C7	179.0 (2)	O2—C14—C15—C16	179.3 (3)
C10—C5—C6—C7	−1.2 (3)	C13—C14—C15—C16	−2.1 (5)
C5—C6—C7—C8	0.7 (4)	C14—C15—C16—C17	1.8 (5)
C6—C7—C8—C9	0.1 (4)	C15—C16—C17—C18	−0.9 (4)
C7—C8—C9—C10	−0.3 (4)	C16—C17—C18—C13	0.4 (4)
C8—C9—C10—C11	179.1 (2)	C14—C13—C18—C17	−0.7 (4)
C8—C9—C10—C5	−0.2 (4)	C12—C13—C18—C17	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.96 (5)	1.87 (5)	2.697 (3)	142 (4)
O3—H3···O1i	0.84 (4)	1.81 (4)	2.609 (2)	157 (3)
N1—H1···O3	0.92 (3)	1.85 (3)	2.628 (3)	141 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.96 (5)	1.87 (5)	2.697 (3)	142 (4)
O3—H3⋯O1i	0.84 (4)	1.81 (4)	2.609 (2)	157 (3)
N1—H1⋯O3	0.92 (3)	1.85 (3)	2.628 (3)	141 (2)

Symmetry code: (i) .