(E)-N'-[(2-Hydroxy-1-naphthyl)methyl-ene]benzohydrazide monohydrate.

In the title compound, C(18)H(14)N(2)O(2)·H(2)O, the dihedral angle between the benzene ring and the naphthalene system is 5.18 (10)°. Intra-molecular N-H⋯O hydrogen bonds influence the molecular conformation. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds are observed as well as π-π inter-actions between the phenyl ring and the substituted ring of the naphthalene [centroid-centroid distance = 3.676 (11) Å].

Related literature

For background to Schiff bases in coordination chemistry, see: Chakraborty & Patel (1996 ▶); Jeewoth et al. (1999 ▶). For their biological activity, see: Das et al. (1999 ▶). For related structures, see: Fun et al.(2008 ▶); Nie (2008 ▶).

Experimental

Crystal data

C18H14N2O2·H2O

M = 308.33

Monoclinic,

a = 16.346 (6) Å

b = 7.192 (3) Å

c = 13.880 (5) Å

β = 111.949 (4)°

V = 1513.5 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.48 × 0.43 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.961

7296 measured reflections

2669 independent reflections

1648 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.148

S = 1.07

2669 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 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/S160053680905212X/bq2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905212X/bq2175Isup2.hkl

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

C18H14N2O2·H2O	F(000) = 648
Mr = 308.33	Dx = 1.353 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2137 reflections
a = 16.346 (6) Å	θ = 2.7–26.8°
b = 7.192 (3) Å	µ = 0.09 mm−1
c = 13.880 (5) Å	T = 298 K
β = 111.949 (4)°	Block, colourless
V = 1513.5 (10) Å3	0.50 × 0.48 × 0.43 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2669 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
graphite	Rint = 0.027
phi and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→19
Tmin = 0.955, Tmax = 0.961	k = −8→8
7296 measured reflections	l = −16→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.5603P] where P = (Fo2 + 2Fc2)/3
2669 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 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	0.03568 (12)	0.2307 (3)	0.50343 (16)	0.0462 (5)
H1	0.0334	0.2363	0.5643	0.055*
N2	0.11241 (12)	0.1782 (3)	0.49103 (16)	0.0482 (5)
O1	−0.03364 (11)	0.2630 (3)	0.33109 (14)	0.0679 (6)
O2	0.21163 (12)	0.1127 (3)	0.38534 (13)	0.0711 (6)
H2	0.1675	0.1496	0.3941	0.107*
O3	0.06076 (12)	0.1282 (3)	0.71458 (14)	0.0790 (6)
H3C	0.0524	0.0128	0.7015	0.095*
H3D	0.0312	0.1610	0.7507	0.095*
C1	−0.03525 (15)	0.2726 (3)	0.41878 (19)	0.0437 (6)
C2	−0.11669 (14)	0.3308 (3)	0.43458 (18)	0.0407 (6)
C3	−0.12564 (16)	0.3358 (4)	0.5298 (2)	0.0513 (6)
H3	−0.0784	0.3025	0.5897	0.062*
C4	−0.20439 (17)	0.3902 (4)	0.5361 (2)	0.0602 (7)
H4	−0.2100	0.3933	0.6003	0.072*
C5	−0.27411 (17)	0.4393 (4)	0.4486 (2)	0.0594 (7)
H5	−0.3271	0.4755	0.4534	0.071*
C6	−0.26626 (17)	0.4356 (4)	0.3545 (2)	0.0615 (7)
H6	−0.3140	0.4691	0.2951	0.074*
C7	−0.18785 (16)	0.3825 (3)	0.34665 (19)	0.0531 (6)
H7	−0.1827	0.3814	0.2821	0.064*
C8	0.17844 (15)	0.1408 (3)	0.5745 (2)	0.0466 (6)
H8	0.1727	0.1529	0.6384	0.056*
C9	0.26175 (14)	0.0802 (3)	0.57090 (18)	0.0412 (6)
C10	0.27378 (16)	0.0654 (3)	0.47759 (19)	0.0496 (6)
C11	0.35283 (17)	−0.0052 (4)	0.4732 (2)	0.0592 (7)
H11	0.3601	−0.0117	0.4100	0.071*
C12	0.41789 (17)	−0.0633 (4)	0.5610 (2)	0.0559 (7)
H12	0.4690	−0.1131	0.5568	0.067*
C13	0.41064 (15)	−0.0507 (3)	0.65878 (19)	0.0475 (6)
C14	0.33263 (14)	0.0262 (3)	0.66492 (18)	0.0422 (6)
C15	0.32900 (18)	0.0419 (4)	0.7644 (2)	0.0587 (7)
H15	0.2797	0.0953	0.7715	0.070*
C16	0.3967 (2)	−0.0201 (5)	0.8507 (2)	0.0741 (9)
H16	0.3927	−0.0077	0.9155	0.089*
C17	0.47164 (19)	−0.1017 (4)	0.8435 (2)	0.0724 (8)
H17	0.5164	−0.1468	0.9026	0.087*
C18	0.47854 (16)	−0.1145 (4)	0.7497 (2)	0.0603 (7)
H18	0.5290	−0.1665	0.7450	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0417 (11)	0.0484 (12)	0.0551 (12)	0.0012 (9)	0.0258 (10)	−0.0028 (10)
N2	0.0418 (12)	0.0468 (12)	0.0622 (14)	0.0010 (9)	0.0266 (10)	−0.0019 (10)
O1	0.0670 (12)	0.0933 (15)	0.0546 (11)	0.0107 (10)	0.0355 (10)	0.0084 (10)
O2	0.0629 (12)	0.0993 (16)	0.0516 (11)	0.0146 (11)	0.0218 (9)	0.0020 (11)
O3	0.0876 (15)	0.1016 (16)	0.0615 (12)	0.0114 (12)	0.0435 (11)	−0.0008 (12)
C1	0.0469 (14)	0.0405 (13)	0.0506 (15)	−0.0026 (11)	0.0261 (12)	0.0028 (11)
C2	0.0388 (13)	0.0358 (12)	0.0495 (14)	−0.0043 (10)	0.0189 (11)	−0.0012 (10)
C3	0.0439 (14)	0.0600 (16)	0.0530 (15)	0.0013 (12)	0.0215 (12)	0.0023 (13)
C4	0.0588 (17)	0.0674 (18)	0.0662 (17)	0.0024 (14)	0.0371 (14)	−0.0011 (15)
C5	0.0441 (15)	0.0564 (17)	0.083 (2)	0.0031 (12)	0.0301 (15)	−0.0041 (15)
C6	0.0449 (15)	0.0650 (18)	0.0677 (19)	0.0042 (13)	0.0131 (13)	0.0003 (15)
C7	0.0535 (15)	0.0539 (16)	0.0523 (15)	−0.0019 (12)	0.0203 (12)	−0.0010 (12)
C8	0.0460 (14)	0.0426 (14)	0.0575 (15)	−0.0036 (11)	0.0266 (12)	−0.0042 (12)
C9	0.0388 (13)	0.0376 (13)	0.0516 (14)	−0.0026 (10)	0.0219 (11)	−0.0042 (11)
C10	0.0451 (14)	0.0538 (15)	0.0523 (16)	−0.0010 (11)	0.0209 (12)	−0.0023 (12)
C11	0.0546 (16)	0.0729 (18)	0.0605 (17)	0.0019 (14)	0.0334 (14)	−0.0056 (14)
C12	0.0446 (15)	0.0598 (17)	0.0730 (19)	0.0016 (12)	0.0329 (14)	−0.0046 (14)
C13	0.0403 (13)	0.0417 (13)	0.0618 (16)	−0.0052 (11)	0.0206 (12)	−0.0011 (12)
C14	0.0409 (13)	0.0392 (13)	0.0513 (15)	−0.0075 (10)	0.0227 (11)	−0.0040 (11)
C15	0.0541 (16)	0.0702 (19)	0.0572 (17)	−0.0040 (13)	0.0271 (14)	−0.0011 (14)
C16	0.074 (2)	0.097 (2)	0.0544 (18)	−0.0059 (18)	0.0268 (16)	0.0034 (16)
C17	0.0600 (19)	0.081 (2)	0.0658 (19)	−0.0025 (16)	0.0115 (15)	0.0121 (17)
C18	0.0438 (15)	0.0566 (17)	0.0778 (19)	−0.0005 (13)	0.0197 (14)	0.0037 (15)

N1—C1	1.341 (3)	C7—H7	0.9300
N1—N2	1.381 (2)	C8—C9	1.448 (3)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.282 (3)	C9—C10	1.385 (3)
O1—C1	1.229 (3)	C9—C14	1.437 (3)
O2—C10	1.347 (3)	C10—C11	1.410 (3)
O2—H2	0.8200	C11—C12	1.349 (3)
O3—H3C	0.8500	C11—H11	0.9301
O3—H3D	0.8501	C12—C13	1.409 (3)
C1—C2	1.488 (3)	C12—H12	0.9300
C2—C3	1.383 (3)	C13—C18	1.410 (3)
C2—C7	1.385 (3)	C13—C14	1.421 (3)
C3—C4	1.379 (3)	C14—C15	1.408 (3)
C3—H3	0.9300	C15—C16	1.367 (4)
C4—C5	1.365 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.395 (4)
C5—C6	1.361 (4)	C16—H16	0.9300
C5—H5	0.9301	C17—C18	1.352 (4)
C6—C7	1.380 (3)	C17—H17	0.9300
C6—H6	0.9301	C18—H18	0.9300
C1—N1—N2	118.7 (2)	C10—C9—C14	118.7 (2)
C1—N1—H1	120.6	C10—C9—C8	121.3 (2)
N2—N1—H1	120.6	C14—C9—C8	120.0 (2)
C8—N2—N1	116.2 (2)	O2—C10—C9	123.3 (2)
C10—O2—H2	109.5	O2—C10—C11	115.3 (2)
H3C—O3—H3D	108.4	C9—C10—C11	121.4 (2)
O1—C1—N1	121.6 (2)	C12—C11—C10	119.9 (2)
O1—C1—C2	120.9 (2)	C12—C11—H11	120.1
N1—C1—C2	117.5 (2)	C10—C11—H11	120.1
C3—C2—C7	118.7 (2)	C11—C12—C13	121.9 (2)
C3—C2—C1	124.6 (2)	C11—C12—H12	119.1
C7—C2—C1	116.6 (2)	C13—C12—H12	119.1
C4—C3—C2	120.2 (2)	C12—C13—C18	121.3 (2)
C4—C3—H3	119.9	C12—C13—C14	118.9 (2)
C2—C3—H3	119.9	C18—C13—C14	119.8 (2)
C5—C4—C3	120.4 (3)	C15—C14—C13	117.2 (2)
C5—C4—H4	119.8	C15—C14—C9	123.6 (2)
C3—C4—H4	119.8	C13—C14—C9	119.2 (2)
C6—C5—C4	120.1 (3)	C16—C15—C14	121.1 (3)
C6—C5—H5	119.9	C16—C15—H15	119.5
C4—C5—H5	119.9	C14—C15—H15	119.5
C5—C6—C7	120.3 (2)	C15—C16—C17	121.3 (3)
C5—C6—H6	119.8	C15—C16—H16	119.4
C7—C6—H6	119.8	C17—C16—H16	119.4
C6—C7—C2	120.2 (2)	C18—C17—C16	119.3 (3)
C6—C7—H7	119.9	C18—C17—H17	120.3
C2—C7—H7	119.9	C16—C17—H17	120.3
N2—C8—C9	121.1 (2)	C17—C18—C13	121.2 (3)
N2—C8—H8	119.4	C17—C18—H18	119.4
C9—C8—H8	119.4	C13—C18—H18	119.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	2.11	2.899 (3)	152
O2—H2···N2	0.82	1.89	2.604 (3)	145
O3—H3C···O1i	0.85	2.03	2.882 (3)	179
O3—H3D···O1ii	0.85	1.88	2.734 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	2.11	2.899 (3)	152
O2—H2⋯N2	0.82	1.89	2.604 (3)	145
O3—H3C⋯O1i	0.85	2.03	2.882 (3)	179
O3—H3D⋯O1ii	0.85	1.88	2.734 (3)	179

Symmetry codes: (i) ; (ii) .