3,5-Dihydr-oxy-N'-[(2-hydr-oxy-1-naph-thyl)methyl-ene]benzohydrazide.

In the title compound, C(18)H(14)N(2)O(4), the dihedral angle between the benzene ring and the naphthyl ring system is 10.1 (2)°. The mol-ecule is nearly planar, with a mean deviation from the plane of 0.141 (2) Å for 24 non-H atoms. An intra-molecular O-H⋯N hydrogen bond forms a pseudo-6-membered ring and the mol-ecules are linked into sheets by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Brückner et al. (2000 ▶); Diao (2007 ▶); Diao et al. (2007 ▶); Harrop et al. (2003 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C18H14N2O4

M = 322.31

Orthorhombic,

a = 13.354 (3) Å

b = 14.133 (3) Å

c = 15.077 (3) Å

V = 2845.5 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.968, T max = 0.971

15775 measured reflections

2949 independent reflections

2433 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.03

2949 reflections

223 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062861/bi2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062861/bi2266Isup2.hkl

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

C18H14N2O4	F000 = 1344
Mr = 322.31	Dx = 1.505 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5426 reflections
a = 13.354 (3) Å	θ = 2.4–27.8º
b = 14.133 (3) Å	µ = 0.11 mm−1
c = 15.077 (3) Å	T = 298 (2) K
V = 2845.5 (10) Å3	Block, yellow
Z = 8	0.30 × 0.28 × 0.27 mm

Bruker SMART CCD diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	2433 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −16→15
Tmin = 0.968, Tmax = 0.971	k = −17→11
15775 measured reflections	l = −18→15

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.7945P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2949 reflections	Δρmax = 0.20 e Å−3
223 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	0.70957 (9)	−0.44067 (6)	0.65672 (7)	0.0446 (3)
H1	0.6882	−0.4716	0.6987	0.067*
O2	0.64726 (9)	−0.17869 (7)	0.84818 (6)	0.0425 (3)
H2	0.6418	−0.2214	0.8847	0.064*
O3	0.61626 (10)	−0.17124 (7)	0.45805 (7)	0.0468 (3)
O4	0.61263 (10)	0.02287 (7)	0.29946 (7)	0.0486 (3)
H4	0.6170	−0.0031	0.3480	0.073*
N1	0.64522 (10)	−0.04149 (8)	0.53870 (8)	0.0359 (3)
N2	0.62939 (10)	0.01212 (8)	0.46461 (8)	0.0363 (3)
C1	0.65842 (10)	−0.19422 (9)	0.60952 (9)	0.0308 (3)
C2	0.67691 (11)	−0.28981 (9)	0.59712 (9)	0.0336 (3)
H2A	0.6811	−0.3150	0.5402	0.040*
C3	0.68890 (11)	−0.34676 (9)	0.67002 (9)	0.0320 (3)
C4	0.68089 (11)	−0.31096 (9)	0.75469 (9)	0.0317 (3)
H4A	0.6893	−0.3504	0.8035	0.038*
C5	0.66031 (10)	−0.21629 (9)	0.76661 (9)	0.0308 (3)
C6	0.65109 (10)	−0.15717 (9)	0.69414 (9)	0.0317 (3)
H6	0.6400	−0.0928	0.7022	0.038*
C7	0.63939 (11)	−0.13645 (9)	0.52904 (9)	0.0330 (3)
C8	0.62525 (11)	0.10148 (9)	0.47179 (9)	0.0329 (3)
H8	0.6324	0.1299	0.5271	0.040*
C9	0.60931 (10)	0.15896 (9)	0.39384 (9)	0.0306 (3)
C10	0.60344 (11)	0.11717 (10)	0.31095 (9)	0.0350 (3)
C11	0.58622 (12)	0.17008 (11)	0.23410 (10)	0.0423 (4)
H11	0.5823	0.1401	0.1793	0.051*
C12	0.57537 (12)	0.26432 (11)	0.23968 (10)	0.0428 (4)
H12	0.5621	0.2988	0.1885	0.051*
C13	0.58356 (11)	0.31214 (10)	0.32116 (10)	0.0373 (3)
C14	0.57676 (13)	0.41122 (11)	0.32600 (12)	0.0503 (4)
H14	0.5644	0.4457	0.2746	0.060*
C15	0.58771 (15)	0.45740 (11)	0.40359 (14)	0.0577 (5)
H15	0.5848	0.5231	0.4053	0.069*
C16	0.60341 (14)	0.40619 (11)	0.48111 (13)	0.0540 (5)
H16	0.6103	0.4380	0.5347	0.065*
C17	0.60877 (12)	0.30993 (10)	0.47952 (11)	0.0433 (4)
H17	0.6182	0.2770	0.5323	0.052*
C18	0.60030 (10)	0.25964 (9)	0.39969 (10)	0.0325 (3)
H1A	0.6770 (14)	−0.0170 (14)	0.5862 (10)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0747 (8)	0.0223 (5)	0.0367 (6)	0.0096 (5)	0.0150 (5)	0.0020 (4)
O2	0.0740 (8)	0.0276 (5)	0.0261 (5)	0.0017 (5)	0.0004 (5)	−0.0018 (4)
O3	0.0836 (9)	0.0298 (5)	0.0271 (5)	−0.0008 (5)	−0.0043 (5)	−0.0024 (4)
O4	0.0827 (9)	0.0315 (6)	0.0316 (6)	0.0044 (5)	−0.0025 (6)	−0.0048 (4)
N1	0.0559 (8)	0.0243 (6)	0.0275 (6)	0.0007 (5)	−0.0070 (5)	0.0027 (5)
N2	0.0542 (8)	0.0258 (6)	0.0290 (6)	0.0012 (5)	−0.0034 (5)	0.0028 (5)
C1	0.0384 (7)	0.0249 (6)	0.0291 (7)	0.0001 (5)	0.0015 (5)	0.0017 (5)
C2	0.0453 (8)	0.0275 (7)	0.0280 (7)	0.0016 (6)	0.0047 (6)	−0.0022 (5)
C3	0.0388 (7)	0.0219 (6)	0.0352 (7)	0.0032 (5)	0.0054 (6)	−0.0003 (5)
C4	0.0396 (7)	0.0267 (6)	0.0288 (7)	0.0019 (5)	0.0017 (6)	0.0042 (5)
C5	0.0380 (7)	0.0269 (6)	0.0275 (7)	−0.0019 (5)	0.0007 (5)	−0.0027 (5)
C6	0.0413 (8)	0.0224 (6)	0.0315 (7)	0.0010 (5)	0.0006 (6)	−0.0010 (5)
C7	0.0445 (8)	0.0257 (6)	0.0288 (7)	0.0014 (6)	0.0020 (6)	−0.0011 (5)
C8	0.0434 (8)	0.0262 (6)	0.0292 (7)	0.0011 (5)	−0.0024 (6)	−0.0012 (5)
C9	0.0348 (7)	0.0255 (6)	0.0315 (7)	0.0011 (5)	−0.0005 (5)	0.0021 (5)
C10	0.0408 (8)	0.0318 (7)	0.0324 (7)	0.0021 (6)	0.0004 (6)	0.0007 (6)
C11	0.0500 (9)	0.0474 (9)	0.0296 (8)	0.0016 (7)	−0.0006 (6)	0.0010 (6)
C12	0.0463 (8)	0.0475 (9)	0.0346 (8)	0.0041 (7)	0.0014 (7)	0.0164 (7)
C13	0.0350 (7)	0.0335 (7)	0.0435 (8)	0.0025 (6)	0.0041 (6)	0.0101 (6)
C14	0.0563 (10)	0.0338 (8)	0.0607 (11)	0.0060 (7)	0.0075 (8)	0.0189 (7)
C15	0.0718 (12)	0.0246 (7)	0.0767 (13)	0.0041 (7)	0.0076 (10)	0.0062 (8)
C16	0.0724 (12)	0.0295 (8)	0.0602 (11)	0.0032 (7)	−0.0002 (9)	−0.0059 (7)
C17	0.0588 (10)	0.0289 (7)	0.0422 (9)	0.0034 (6)	−0.0019 (7)	−0.0004 (6)
C18	0.0337 (7)	0.0261 (7)	0.0378 (8)	0.0016 (5)	0.0015 (6)	0.0040 (6)

O1—C3	1.3704 (15)	C6—H6	0.930
O1—H1	0.820	C8—C9	1.4445 (18)
O2—C5	1.3511 (15)	C8—H8	0.930
O2—H2	0.820	C9—C10	1.3845 (19)
O3—C7	1.2177 (17)	C9—C18	1.4307 (18)
O4—C10	1.3496 (17)	C10—C11	1.398 (2)
O4—H4	0.820	C11—C12	1.342 (2)
N1—C7	1.3521 (17)	C11—H11	0.930
N1—N2	1.3661 (16)	C12—C13	1.406 (2)
N1—H1A	0.903 (9)	C12—H12	0.930
N2—C8	1.2688 (17)	C13—C14	1.405 (2)
C1—C6	1.3826 (19)	C13—C18	1.4150 (19)
C1—C2	1.3859 (18)	C14—C15	1.348 (3)
C1—C7	1.4845 (18)	C14—H14	0.930
C2—C3	1.3716 (19)	C15—C16	1.391 (3)
C2—H2A	0.930	C15—H15	0.930
C3—C4	1.3774 (19)	C16—C17	1.363 (2)
C4—C5	1.3776 (17)	C16—H16	0.930
C4—H4A	0.930	C17—C18	1.402 (2)
C5—C6	1.3810 (18)	C17—H17	0.930
C3—O1—H1	109.5	C10—C9—C18	118.36 (12)
C5—O2—H2	109.5	C10—C9—C8	120.20 (12)
C10—O4—H4	109.5	C18—C9—C8	121.44 (12)
C7—N1—N2	116.97 (11)	O4—C10—C9	122.13 (12)
C7—N1—H1A	119.6 (14)	O4—C10—C11	115.90 (13)
N2—N1—H1A	120.6 (14)	C9—C10—C11	121.96 (13)
C8—N2—N1	119.28 (12)	C12—C11—C10	119.77 (14)
C6—C1—C2	120.41 (12)	C12—C11—H11	120.1
C6—C1—C7	122.26 (12)	C10—C11—H11	120.1
C2—C1—C7	117.16 (12)	C11—C12—C13	121.54 (13)
C3—C2—C1	118.99 (12)	C11—C12—H12	119.2
C3—C2—H2A	120.5	C13—C12—H12	119.2
C1—C2—H2A	120.5	C14—C13—C12	121.28 (14)
O1—C3—C2	118.34 (12)	C14—C13—C18	119.30 (15)
O1—C3—C4	120.46 (12)	C12—C13—C18	119.42 (13)
C2—C3—C4	121.20 (12)	C15—C14—C13	121.38 (15)
C3—C4—C5	119.55 (12)	C15—C14—H14	119.3
C3—C4—H4A	120.2	C13—C14—H14	119.3
C5—C4—H4A	120.2	C14—C15—C16	119.60 (15)
O2—C5—C4	121.77 (12)	C14—C15—H15	120.2
O2—C5—C6	118.08 (12)	C16—C15—H15	120.2
C4—C5—C6	120.15 (12)	C17—C16—C15	120.85 (17)
C5—C6—C1	119.64 (12)	C17—C16—H16	119.6
C5—C6—H6	120.2	C15—C16—H16	119.6
C1—C6—H6	120.2	C16—C17—C18	121.13 (15)
O3—C7—N1	120.67 (12)	C16—C17—H17	119.4
O3—C7—C1	122.67 (12)	C18—C17—H17	119.4
N1—C7—C1	116.62 (12)	C17—C18—C13	117.72 (13)
N2—C8—C9	119.79 (13)	C17—C18—C9	123.38 (13)
N2—C8—H8	120.1	C13—C18—C9	118.90 (13)
C9—C8—H8	120.1

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.96	2.7671 (15)	167
O2—H2···O3i	0.82	1.91	2.7227 (15)	172
O4—H4···N2	0.82	1.78	2.5046 (16)	147
N1—H1A···O1ii	0.903 (9)	2.141 (12)	2.9929 (16)	157.0 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.96	2.7671 (15)	167
O2—H2⋯O3i	0.82	1.91	2.7227 (15)	172
O4—H4⋯N2	0.82	1.78	2.5046 (16)	147
N1—H1A⋯O1ii	0.903 (9)	2.141 (12)	2.9929 (16)	157.0 (19)

Symmetry codes: (i) ; (ii) .