N'-(3-Eth-oxy-2-hydroxy-benzyl-idene)-3-hydroxy-naphthalene-2-carbohydrazide.

In the mol-ecule of the title compound, C(20)H(18)N(2)O(4), the dihedral angle between the benzene ring and the naphthyl ring system is 8.5 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background on Schiff base compounds and their biological applications, see: Schiff (1864 ▶); Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For related structures, see: Diao (2007 ▶); Diao et al. (2007 ▶, 2008 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H18N2O4

M = 350.36

Monoclinic,

a = 28.420 (15) Å

b = 6.456 (5) Å

c = 18.800 (14) Å

β = 100.658 (10)°

V = 3390 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.972, T max = 0.974

13100 measured reflections

3503 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.178

S = 1.06

3503 reflections

242 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 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 (Sheldrick, 2008 ▶); 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/S1600536808010933/pv2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010933/pv2080Isup2.hkl

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

C20H18N2O4	F000 = 1472
Mr = 350.36	Dx = 1.373 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1359 reflections
a = 28.420 (15) Å	θ = 2.2–24.3º
b = 6.456 (5) Å	µ = 0.10 mm−1
c = 18.800 (14) Å	T = 298 (2) K
β = 100.658 (10)º	Block, colorless
V = 3390 (4) Å3	0.30 × 0.27 × 0.27 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −35→35
Tmin = 0.972, Tmax = 0.974	k = −8→8
13100 measured reflections	l = −23→22

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.178	w = 1/[σ2(Fo2) + 0.1909P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3503 reflections	Δρmax = 0.24 e Å−3
242 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (6)

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	1.00934 (6)	−0.1963 (2)	0.34159 (8)	0.0489 (5)
H1	1.0059	−0.3211	0.3470	0.073*
O2	0.98937 (6)	0.4267 (2)	0.38501 (9)	0.0528 (5)
O3	0.88269 (7)	0.6149 (3)	0.24267 (9)	0.0611 (6)
H3	0.9039	0.5398	0.2644	0.092*
O4	0.81068 (6)	0.8088 (3)	0.16639 (10)	0.0592 (5)
N1	0.96591 (7)	0.1590 (3)	0.31039 (10)	0.0396 (5)
N2	0.93488 (7)	0.2841 (3)	0.26466 (10)	0.0394 (5)
C1	1.02434 (7)	0.1001 (3)	0.41996 (11)	0.0336 (5)
C2	1.03361 (8)	−0.1122 (3)	0.40475 (11)	0.0363 (5)
C3	1.06657 (8)	−0.2231 (3)	0.45120 (13)	0.0405 (6)
H3A	1.0734	−0.3580	0.4390	0.049*
C4	1.09062 (8)	−0.1396 (3)	0.51714 (12)	0.0377 (5)
C5	1.12406 (8)	−0.2534 (4)	0.56714 (14)	0.0467 (6)
H5	1.1314	−0.3888	0.5563	0.056*
C6	1.14561 (9)	−0.1678 (4)	0.63087 (14)	0.0502 (6)
H6	1.1670	−0.2465	0.6635	0.060*
C7	1.13609 (8)	0.0384 (4)	0.64834 (13)	0.0498 (7)
H7	1.1516	0.0960	0.6917	0.060*
C8	1.10409 (8)	0.1528 (4)	0.60139 (12)	0.0431 (6)
H8	1.0976	0.2882	0.6133	0.052*
C9	1.08064 (8)	0.0685 (3)	0.53476 (11)	0.0364 (5)
C10	1.04759 (8)	0.1814 (3)	0.48433 (12)	0.0372 (5)
H10	1.0412	0.3179	0.4952	0.045*
C11	0.99190 (8)	0.2416 (3)	0.37086 (12)	0.0365 (5)
C12	0.91016 (8)	0.2028 (4)	0.20827 (12)	0.0402 (6)
H12	0.9147	0.0643	0.1977	0.048*
C13	0.87471 (8)	0.3253 (4)	0.16007 (12)	0.0392 (6)
C14	0.86145 (8)	0.5211 (4)	0.18082 (12)	0.0426 (6)
C15	0.82336 (9)	0.6255 (4)	0.13816 (13)	0.0471 (6)
C16	0.80210 (9)	0.5426 (4)	0.07255 (13)	0.0562 (7)
H16	0.7776	0.6148	0.0431	0.067*
C17	0.81680 (9)	0.3529 (4)	0.04985 (14)	0.0566 (7)
H17	0.8027	0.3001	0.0049	0.068*
C18	0.85201 (8)	0.2431 (4)	0.09359 (13)	0.0465 (6)
H18	0.8609	0.1134	0.0791	0.056*
C19	0.76647 (9)	0.9005 (4)	0.13279 (16)	0.0612 (8)
H19A	0.7413	0.7971	0.1251	0.073*
H19B	0.7694	0.9590	0.0863	0.073*
C20	0.75477 (11)	1.0676 (4)	0.18230 (17)	0.0764 (9)
H20A	0.7498	1.0067	0.2269	0.115*
H20B	0.7262	1.1384	0.1597	0.115*
H20C	0.7808	1.1643	0.1920	0.115*
H1A	0.9661 (10)	0.0234 (18)	0.2992 (15)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0656 (11)	0.0304 (9)	0.0453 (10)	0.0015 (8)	−0.0038 (8)	−0.0026 (7)
O2	0.0653 (12)	0.0272 (9)	0.0598 (11)	0.0042 (8)	−0.0043 (9)	0.0031 (8)
O3	0.0697 (13)	0.0505 (11)	0.0525 (11)	0.0209 (9)	−0.0165 (9)	−0.0120 (9)
O4	0.0558 (11)	0.0509 (11)	0.0628 (12)	0.0186 (8)	−0.0098 (9)	−0.0038 (9)
N1	0.0435 (11)	0.0338 (10)	0.0395 (11)	0.0055 (9)	0.0022 (9)	0.0036 (9)
N2	0.0412 (11)	0.0362 (11)	0.0388 (11)	0.0058 (8)	0.0020 (9)	0.0052 (9)
C1	0.0351 (12)	0.0299 (12)	0.0364 (12)	−0.0008 (9)	0.0082 (10)	0.0037 (9)
C2	0.0409 (13)	0.0313 (12)	0.0365 (12)	−0.0030 (10)	0.0066 (10)	0.0005 (10)
C3	0.0442 (14)	0.0308 (12)	0.0473 (14)	0.0021 (10)	0.0105 (11)	0.0017 (10)
C4	0.0351 (12)	0.0369 (13)	0.0422 (13)	0.0013 (10)	0.0099 (10)	0.0020 (10)
C5	0.0451 (14)	0.0446 (14)	0.0514 (15)	0.0114 (11)	0.0114 (12)	0.0047 (12)
C6	0.0422 (14)	0.0616 (17)	0.0448 (15)	0.0093 (12)	0.0029 (12)	0.0051 (12)
C7	0.0435 (15)	0.0634 (18)	0.0410 (14)	−0.0001 (12)	0.0041 (12)	−0.0010 (12)
C8	0.0463 (14)	0.0407 (13)	0.0430 (14)	−0.0013 (11)	0.0098 (11)	−0.0030 (11)
C9	0.0369 (12)	0.0394 (13)	0.0342 (12)	−0.0012 (10)	0.0099 (10)	0.0025 (10)
C10	0.0442 (13)	0.0275 (11)	0.0413 (13)	−0.0002 (10)	0.0113 (11)	0.0009 (10)
C11	0.0379 (12)	0.0312 (13)	0.0407 (13)	−0.0006 (10)	0.0077 (10)	0.0045 (10)
C12	0.0438 (14)	0.0388 (13)	0.0395 (13)	0.0073 (10)	0.0118 (11)	−0.0009 (10)
C13	0.0394 (13)	0.0432 (13)	0.0357 (13)	0.0042 (10)	0.0086 (10)	0.0016 (10)
C14	0.0427 (14)	0.0478 (15)	0.0349 (12)	0.0048 (11)	0.0009 (11)	0.0013 (11)
C15	0.0449 (14)	0.0476 (15)	0.0469 (14)	0.0064 (12)	0.0032 (12)	0.0020 (12)
C16	0.0531 (17)	0.0645 (18)	0.0455 (15)	0.0097 (13)	−0.0052 (12)	0.0103 (13)
C17	0.0573 (17)	0.0694 (19)	0.0389 (14)	0.0010 (14)	−0.0023 (12)	−0.0065 (13)
C18	0.0496 (15)	0.0490 (15)	0.0418 (14)	0.0010 (12)	0.0106 (12)	−0.0036 (11)
C19	0.0419 (15)	0.0561 (17)	0.081 (2)	0.0104 (12)	−0.0009 (14)	0.0025 (15)
C20	0.0619 (19)	0.066 (2)	0.101 (2)	0.0174 (15)	0.0127 (18)	−0.0019 (18)

O1—C2	1.370 (3)	C7—C8	1.362 (3)
O1—H1	0.8200	C7—H7	0.9300
O2—C11	1.230 (3)	C8—C9	1.414 (3)
O3—C14	1.350 (3)	C8—H8	0.9300
O3—H3	0.8200	C9—C10	1.408 (3)
O4—C15	1.372 (3)	C10—H10	0.9300
O4—C19	1.426 (3)	C12—C13	1.457 (3)
N1—C11	1.346 (3)	C12—H12	0.9300
N1—N2	1.374 (2)	C13—C14	1.395 (3)
N1—H1A	0.900 (10)	C13—C18	1.401 (3)
N2—C12	1.272 (3)	C14—C15	1.396 (3)
C1—C10	1.371 (3)	C15—C16	1.377 (3)
C1—C2	1.434 (3)	C16—C17	1.387 (4)
C1—C11	1.490 (3)	C16—H16	0.9300
C2—C3	1.360 (3)	C17—C18	1.369 (3)
C3—C4	1.407 (3)	C17—H17	0.9300
C3—H3A	0.9300	C18—H18	0.9300
C4—C5	1.413 (3)	C19—C20	1.501 (4)
C4—C9	1.425 (3)	C19—H19A	0.9700
C5—C6	1.358 (3)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—C7	1.409 (4)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600
C2—O1—H1	109.5	O2—C11—N1	121.5 (2)
C14—O3—H3	109.5	O2—C11—C1	121.1 (2)
C15—O4—C19	117.36 (19)	N1—C11—C1	117.43 (19)
C11—N1—N2	118.96 (19)	N2—C12—C13	120.4 (2)
C11—N1—H1A	123.8 (18)	N2—C12—H12	119.8
N2—N1—H1A	117.1 (18)	C13—C12—H12	119.8
C12—N2—N1	118.05 (19)	C14—C13—C18	119.3 (2)
C10—C1—C2	117.73 (19)	C14—C13—C12	120.6 (2)
C10—C1—C11	117.0 (2)	C18—C13—C12	120.0 (2)
C2—C1—C11	125.3 (2)	O3—C14—C13	123.1 (2)
C3—C2—O1	121.6 (2)	O3—C14—C15	117.0 (2)
C3—C2—C1	120.3 (2)	C13—C14—C15	119.8 (2)
O1—C2—C1	118.02 (19)	O4—C15—C16	125.3 (2)
C2—C3—C4	121.9 (2)	O4—C15—C14	115.2 (2)
C2—C3—H3A	119.0	C16—C15—C14	119.5 (2)
C4—C3—H3A	119.0	C15—C16—C17	120.8 (2)
C3—C4—C5	123.0 (2)	C15—C16—H16	119.6
C3—C4—C9	118.7 (2)	C17—C16—H16	119.6
C5—C4—C9	118.3 (2)	C18—C17—C16	120.0 (2)
C6—C5—C4	120.9 (2)	C18—C17—H17	120.0
C6—C5—H5	119.6	C16—C17—H17	120.0
C4—C5—H5	119.6	C17—C18—C13	120.3 (2)
C5—C6—C7	121.0 (2)	C17—C18—H18	119.8
C5—C6—H6	119.5	C13—C18—H18	119.8
C7—C6—H6	119.5	O4—C19—C20	107.5 (2)
C8—C7—C6	119.7 (2)	O4—C19—H19A	110.2
C8—C7—H7	120.2	C20—C19—H19A	110.2
C6—C7—H7	120.2	O4—C19—H19B	110.2
C7—C8—C9	120.9 (2)	C20—C19—H19B	110.2
C7—C8—H8	119.5	H19A—C19—H19B	108.5
C9—C8—H8	119.5	C19—C20—H20A	109.5
C10—C9—C8	122.9 (2)	C19—C20—H20B	109.5
C10—C9—C4	117.9 (2)	H20A—C20—H20B	109.5
C8—C9—C4	119.2 (2)	C19—C20—H20C	109.5
C1—C10—C9	123.3 (2)	H20A—C20—H20C	109.5
C1—C10—H10	118.4	H20B—C20—H20C	109.5
C9—C10—H10	118.4

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.87	2.661 (3)	161
O3—H3···N2	0.82	1.87	2.589 (3)	146
N1—H1A···O1	0.900 (10)	1.95 (2)	2.619 (3)	130 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.87	2.661 (3)	161
O3—H3⋯N2	0.82	1.87	2.589 (3)	146
N1—H1A⋯O1	0.900 (10)	1.95 (2)	2.619 (3)	130 (2)

Symmetry code: (i) .