2-Hydr-oxy-N'-[(E)-(3-hydr-oxy-2-naphth-yl)methyl-ene]benzohydrazide.

In the title mol-ecule, C(18)H(14)N(2)O(3), O-H⋯N and N-H⋯O hydrogen bonds influence the mol-ecular conformation; the benzene and naphthalene planes are inclined at a dihedral angle of 11.54 (5)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains running in the [01] direction.

Related literature

For useful applications of salicyloyl hydrazide derivatives, see: Sumita et al. (1999 ▶). For the crystal structure of (E)-2-hydr­oxy-N′-(3-hydr­oxy-4-methoxy­benzyl­idene)benzohydrazide, see: Luo (2007 ▶).

Experimental

Crystal data

C18H14N2O3

M = 306.31

Orthorhombic,

a = 21.124 (2) Å

b = 11.6212 (13) Å

c = 5.9826 (8) Å

V = 1468.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.32 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.986

6099 measured reflections

1422 independent reflections

896 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.076

S = 1.04

1422 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 I, global. DOI: 10.1107/S1600536808044073/cv2501sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044073/cv2501Isup2.hkl

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

C18H14N2O3	Dx = 1.385 Mg m−3
Mr = 306.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 1119 reflections
a = 21.124 (2) Å	θ = 2.6–25.4°
b = 11.6212 (13) Å	µ = 0.10 mm−1
c = 5.9826 (8) Å	T = 298 K
V = 1468.6 (3) Å3	Block, yellow
Z = 4	0.32 × 0.18 × 0.15 mm
F(000) = 640

Bruker SMART CCD area-detector diffractometer	1422 independent reflections
Radiation source: fine-focus sealed tube	896 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.970, Tmax = 0.986	k = −13→8
6099 measured reflections	l = −7→6

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0012P)2 + 0.7621P] where P = (Fo2 + 2Fc2)/3
1422 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.16 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 > 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
N1	0.22373 (16)	0.9395 (3)	0.7320 (6)	0.0514 (10)
H1	0.2172	0.8713	0.7828	0.062*
N2	0.19138 (18)	0.9753 (3)	0.5434 (6)	0.0536 (11)
O1	0.27673 (14)	1.1075 (2)	0.7748 (6)	0.0703 (10)
O2	0.25278 (12)	0.7725 (2)	1.0077 (6)	0.0574 (9)
H2	0.2526	0.7107	1.0739	0.086*
O3	0.16012 (13)	1.1067 (3)	0.2045 (6)	0.0664 (10)
H3	0.1787	1.0892	0.3199	0.100*
C1	0.2649 (2)	1.0079 (4)	0.8375 (8)	0.0504 (12)
C2	0.2955 (2)	0.9611 (3)	1.0404 (8)	0.0447 (11)
C3	0.2891 (2)	0.8497 (3)	1.1229 (7)	0.0441 (12)
C4	0.3185 (2)	0.8179 (4)	1.3196 (8)	0.0544 (13)
H4	0.3135	0.7435	1.3740	0.065*
C5	0.3548 (2)	0.8948 (5)	1.4348 (9)	0.0672 (15)
H5	0.3750	0.8718	1.5655	0.081*
C6	0.3618 (2)	1.0054 (5)	1.3596 (10)	0.0718 (16)
H6	0.3863	1.0578	1.4392	0.086*
C7	0.3321 (2)	1.0378 (4)	1.1646 (10)	0.0614 (14)
H7	0.3366	1.1130	1.1142	0.074*
C8	0.1536 (2)	0.8994 (4)	0.4641 (8)	0.0546 (13)
H8	0.1507	0.8288	0.5363	0.066*
C9	0.1152 (2)	0.9189 (4)	0.2659 (8)	0.0493 (12)
C10	0.1211 (2)	1.0193 (4)	0.1429 (8)	0.0495 (12)
C11	0.0868 (2)	1.0370 (4)	−0.0549 (8)	0.0560 (13)
H11	0.0914	1.1054	−0.1339	0.067*
C12	0.0468 (2)	0.9542 (4)	−0.1312 (9)	0.0607 (14)
H12	0.0255	0.9653	−0.2656	0.073*
C13	0.0369 (2)	0.8510 (4)	−0.0089 (9)	0.0548 (13)
C14	0.07102 (19)	0.8331 (4)	0.1920 (8)	0.0511 (12)
C15	0.0568 (2)	0.7320 (4)	0.3138 (9)	0.0656 (15)
H15	0.0780	0.7173	0.4470	0.079*
C16	0.0128 (2)	0.6564 (5)	0.2396 (11)	0.0790 (19)
H16	0.0044	0.5909	0.3239	0.095*
C17	−0.0202 (2)	0.6734 (5)	0.0415 (12)	0.0771 (17)
H17	−0.0500	0.6199	−0.0067	0.093*
C18	−0.0082 (2)	0.7700 (4)	−0.0809 (9)	0.0686 (16)
H18	−0.0301	0.7825	−0.2136	0.082*

	U11	U22	U33	U12	U13	U23
N1	0.053 (2)	0.058 (2)	0.043 (3)	0.005 (2)	−0.001 (2)	0.022 (2)
N2	0.051 (2)	0.070 (3)	0.040 (2)	0.016 (2)	0.000 (2)	0.017 (2)
O1	0.086 (2)	0.0454 (18)	0.079 (3)	0.0026 (17)	0.004 (2)	0.0291 (19)
O2	0.076 (2)	0.0427 (16)	0.053 (2)	−0.0038 (16)	−0.012 (2)	0.0166 (17)
O3	0.063 (2)	0.081 (2)	0.056 (3)	−0.0053 (18)	−0.0055 (19)	0.029 (2)
C1	0.052 (3)	0.049 (3)	0.050 (3)	0.007 (2)	0.006 (3)	0.012 (2)
C2	0.046 (3)	0.043 (3)	0.044 (3)	0.005 (2)	0.001 (2)	0.009 (2)
C3	0.050 (3)	0.042 (3)	0.040 (3)	0.000 (2)	−0.001 (2)	0.005 (2)
C4	0.060 (3)	0.058 (3)	0.045 (3)	0.008 (3)	0.001 (3)	0.017 (3)
C5	0.062 (3)	0.087 (4)	0.053 (4)	0.012 (3)	−0.010 (3)	0.003 (3)
C6	0.065 (3)	0.073 (4)	0.077 (4)	−0.006 (3)	−0.012 (3)	−0.011 (3)
C7	0.066 (3)	0.050 (3)	0.068 (4)	−0.002 (3)	0.002 (3)	0.007 (3)
C8	0.055 (3)	0.062 (3)	0.047 (3)	0.013 (3)	0.007 (3)	0.018 (3)
C9	0.047 (3)	0.063 (3)	0.037 (3)	0.011 (2)	0.005 (2)	0.014 (3)
C10	0.044 (3)	0.068 (3)	0.037 (3)	0.007 (2)	0.007 (3)	0.016 (3)
C11	0.054 (3)	0.075 (3)	0.039 (3)	0.011 (3)	−0.001 (3)	0.020 (3)
C12	0.059 (3)	0.088 (4)	0.035 (3)	0.009 (3)	0.000 (3)	0.007 (3)
C13	0.049 (3)	0.064 (3)	0.051 (3)	0.009 (3)	0.009 (3)	0.001 (3)
C14	0.049 (3)	0.059 (3)	0.046 (3)	0.017 (2)	0.006 (3)	0.004 (3)
C15	0.056 (3)	0.071 (3)	0.070 (4)	0.008 (3)	0.000 (3)	0.017 (3)
C16	0.069 (4)	0.068 (4)	0.100 (6)	0.003 (3)	0.001 (4)	0.018 (4)
C17	0.068 (4)	0.067 (4)	0.096 (5)	−0.003 (3)	0.002 (4)	0.001 (4)
C18	0.060 (3)	0.079 (4)	0.066 (4)	0.007 (3)	0.008 (3)	−0.008 (4)

N1—C1	1.336 (5)	C8—C9	1.455 (6)
N1—N2	1.383 (5)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.386 (5)
N2—C8	1.280 (5)	C9—C14	1.435 (5)
O1—C1	1.242 (5)	C10—C11	1.403 (6)
O2—C3	1.366 (5)	C11—C12	1.360 (6)
O2—H2	0.8200	C11—H11	0.9300
O3—C10	1.359 (5)	C12—C13	1.420 (6)
O3—H3	0.8200	C12—H12	0.9300
C1—C2	1.479 (6)	C13—C18	1.407 (6)
C2—C3	1.392 (5)	C13—C14	1.417 (6)
C2—C7	1.395 (6)	C14—C15	1.415 (6)
C3—C4	1.381 (6)	C15—C16	1.354 (6)
C4—C5	1.364 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.389 (7)
C5—C6	1.370 (7)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.364 (6)
C6—C7	1.377 (7)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300
C1—N1—N2	121.8 (4)	C10—C9—C14	118.7 (4)
C1—N1—H1	119.1	C10—C9—C8	120.9 (4)
N2—N1—H1	119.1	C14—C9—C8	120.4 (4)
C8—N2—N1	113.8 (4)	O3—C10—C9	122.7 (4)
C3—O2—H2	109.5	O3—C10—C11	115.7 (4)
C10—O3—H3	109.5	C9—C10—C11	121.6 (5)
O1—C1—N1	122.9 (4)	C12—C11—C10	120.1 (5)
O1—C1—C2	120.2 (5)	C12—C11—H11	120.0
N1—C1—C2	116.9 (4)	C10—C11—H11	120.0
C3—C2—C7	117.3 (4)	C11—C12—C13	121.1 (5)
C3—C2—C1	126.2 (4)	C11—C12—H12	119.5
C7—C2—C1	116.4 (4)	C13—C12—H12	119.5
O2—C3—C4	120.5 (4)	C18—C13—C14	120.4 (5)
O2—C3—C2	119.1 (4)	C18—C13—C12	120.4 (5)
C4—C3—C2	120.5 (4)	C14—C13—C12	119.1 (5)
C5—C4—C3	120.6 (5)	C15—C14—C13	116.8 (5)
C5—C4—H4	119.7	C15—C14—C9	123.8 (5)
C3—C4—H4	119.7	C13—C14—C9	119.4 (4)
C4—C5—C6	120.6 (5)	C16—C15—C14	121.1 (5)
C4—C5—H5	119.7	C16—C15—H15	119.5
C6—C5—H5	119.7	C14—C15—H15	119.5
C5—C6—C7	119.0 (5)	C15—C16—C17	122.1 (6)
C5—C6—H6	120.5	C15—C16—H16	118.9
C7—C6—H6	120.5	C17—C16—H16	118.9
C6—C7—C2	122.0 (5)	C18—C17—C16	118.8 (6)
C6—C7—H7	119.0	C18—C17—H17	120.6
C2—C7—H7	119.0	C16—C17—H17	120.6
N2—C8—C9	122.9 (4)	C17—C18—C13	120.8 (6)
N2—C8—H8	118.6	C17—C18—H18	119.6
C9—C8—H8	118.6	C13—C18—H18	119.6

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.90	2.623 (5)	146
N1—H1···O2	0.86	1.92	2.620 (4)	137
O2—H2···O1i	0.82	1.81	2.573 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.90	2.623 (5)	146
N1—H1⋯O2	0.86	1.92	2.620 (4)	137
O2—H2⋯O1i	0.82	1.81	2.573 (4)	155

Symmetry code: (i) .