1-[(E)-(2-Methyl-3-nitro-phen-yl)imino-meth-yl]-2-naphthol.

The title Schiff base compound, C(18)H(14)N(2)O(3), has an inter-mediate state between NH and OH tautomers. The mol-ecular structure is stabilized by an O-H⋯N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 37.44 (5)°.

Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For Schiff base tautomerism, see: Hökelek et al. (2000 ▶); Karabıyık et al. (2007 ▶); Odabaşoğlu et al. (2005 ▶); Kılıç et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H14N2O3

M = 306.31

Monoclinic,

a = 12.5520 (9) Å

b = 7.4731 (4) Å

c = 15.8610 (13) Å

β = 90.806 (6)°

V = 1487.65 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.7 × 0.47 × 0.12 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.989, T max = 0.997

9684 measured reflections

3088 independent reflections

1969 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.153

S = 0.94

3088 reflections

213 parameters

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: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043461/bt5391sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043461/bt5391Isup2.hkl

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

C18H14N2O3	F(000) = 640
Mr = 306.31	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8237 reflections
a = 12.5520 (9) Å	θ = 1.3–27.3°
b = 7.4731 (4) Å	µ = 0.10 mm−1
c = 15.8610 (13) Å	T = 296 K
β = 90.806 (6)°	PRISM., yellow
V = 1487.65 (18) Å3	0.7 × 0.47 × 0.12 mm
Z = 4

Stoe IPDS II diffractometer	3088 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.6°
ω scans	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.989, Tmax = 0.997	l = −19→17
9684 measured reflections

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
3088 reflections	Δρmax = 0.24 e Å−3
213 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

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
C1	0.41741 (13)	0.0570 (2)	0.21696 (11)	0.0439 (4)
C2	0.35899 (13)	0.0014 (2)	0.28723 (11)	0.0489 (4)
C3	0.24646 (15)	−0.0112 (3)	0.28256 (13)	0.0605 (5)
H3	0.2085	−0.0498	0.3291	0.073*
C4	0.19459 (14)	0.0329 (3)	0.21045 (13)	0.0627 (5)
H4	0.1206	0.0258	0.2086	0.075*
C5	0.24883 (13)	0.0898 (3)	0.13724 (12)	0.0510 (4)
C6	0.19243 (15)	0.1360 (3)	0.06252 (14)	0.0618 (5)
H6	0.1184	0.1309	0.0616	0.074*
C7	0.24441 (16)	0.1873 (3)	−0.00749 (14)	0.0648 (5)
H7	0.2062	0.2181	−0.0560	0.078*
C8	0.35511 (16)	0.1941 (3)	−0.00694 (13)	0.0606 (5)
H8	0.3907	0.2270	−0.0556	0.073*
C9	0.41227 (14)	0.1526 (3)	0.06482 (11)	0.0515 (5)
H9	0.4862	0.1594	0.0642	0.062*
C10	0.36138 (12)	0.1001 (2)	0.13924 (11)	0.0441 (4)
C11	0.53047 (13)	0.0720 (2)	0.22409 (12)	0.0471 (4)
H11	0.5686	0.1078	0.1772	0.057*
C12	0.69421 (13)	0.0479 (2)	0.29892 (11)	0.0487 (4)
C13	0.74005 (13)	0.1057 (2)	0.37579 (11)	0.0461 (4)
C14	0.85070 (14)	0.1110 (3)	0.37726 (12)	0.0557 (5)
C15	0.91392 (15)	0.0627 (4)	0.31127 (15)	0.0757 (7)
H15	0.9877	0.0702	0.3159	0.091*
C16	0.86568 (16)	0.0027 (4)	0.23779 (15)	0.0813 (7)
H16	0.9068	−0.0323	0.1924	0.098*
C17	0.75641 (15)	−0.0048 (3)	0.23229 (13)	0.0655 (6)
H17	0.7239	−0.0461	0.1830	0.079*
C18	0.67164 (14)	0.1657 (3)	0.44710 (12)	0.0562 (5)
H18A	0.7161	0.2005	0.4940	0.084*
H18B	0.6260	0.0692	0.4637	0.084*
H18C	0.6290	0.2657	0.4292	0.084*
N1	0.58208 (11)	0.0375 (2)	0.29377 (9)	0.0481 (4)
N2	0.90826 (13)	0.1746 (3)	0.45348 (12)	0.0695 (5)
O1	0.40602 (11)	−0.0411 (2)	0.36024 (8)	0.0609 (4)
O2	0.88124 (15)	0.1224 (3)	0.52187 (11)	0.1036 (7)
O3	0.98286 (12)	0.2763 (3)	0.44235 (12)	0.0997 (6)
H1	0.489 (3)	−0.023 (4)	0.343 (2)	0.128 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0467 (8)	0.0410 (9)	0.0437 (9)	0.0020 (7)	−0.0038 (7)	−0.0022 (8)
C2	0.0532 (9)	0.0499 (10)	0.0435 (10)	0.0026 (7)	0.0003 (7)	−0.0048 (8)
C3	0.0548 (10)	0.0759 (14)	0.0510 (11)	−0.0020 (9)	0.0092 (8)	−0.0036 (10)
C4	0.0419 (9)	0.0810 (14)	0.0652 (13)	0.0029 (9)	0.0014 (9)	−0.0089 (11)
C5	0.0472 (9)	0.0541 (11)	0.0515 (11)	0.0041 (7)	−0.0059 (8)	−0.0083 (9)
C6	0.0506 (10)	0.0709 (13)	0.0634 (13)	0.0104 (9)	−0.0158 (9)	−0.0083 (11)
C7	0.0716 (12)	0.0672 (13)	0.0552 (12)	0.0102 (10)	−0.0218 (10)	−0.0007 (10)
C8	0.0738 (12)	0.0603 (12)	0.0474 (11)	−0.0026 (9)	−0.0073 (9)	0.0052 (9)
C9	0.0531 (9)	0.0517 (10)	0.0496 (11)	−0.0050 (8)	−0.0061 (8)	0.0033 (9)
C10	0.0478 (9)	0.0391 (9)	0.0453 (9)	0.0011 (7)	−0.0044 (7)	−0.0029 (7)
C11	0.0493 (9)	0.0461 (10)	0.0459 (10)	−0.0011 (7)	−0.0026 (7)	0.0003 (8)
C12	0.0470 (9)	0.0509 (10)	0.0480 (10)	0.0015 (7)	−0.0048 (7)	−0.0003 (8)
C13	0.0473 (8)	0.0476 (10)	0.0434 (9)	−0.0002 (7)	−0.0050 (7)	0.0031 (8)
C14	0.0487 (9)	0.0655 (12)	0.0526 (11)	0.0008 (8)	−0.0113 (8)	−0.0018 (9)
C15	0.0443 (10)	0.1099 (19)	0.0727 (15)	0.0034 (10)	−0.0026 (9)	−0.0122 (14)
C16	0.0546 (11)	0.122 (2)	0.0674 (14)	0.0087 (12)	0.0058 (10)	−0.0223 (15)
C17	0.0570 (10)	0.0860 (15)	0.0533 (12)	0.0069 (10)	−0.0049 (9)	−0.0168 (11)
C18	0.0567 (10)	0.0636 (12)	0.0481 (10)	−0.0007 (8)	−0.0018 (8)	0.0019 (9)
N1	0.0471 (8)	0.0497 (8)	0.0473 (8)	0.0010 (6)	−0.0083 (6)	−0.0003 (7)
N2	0.0517 (9)	0.0915 (14)	0.0646 (12)	0.0002 (9)	−0.0173 (8)	−0.0044 (11)
O1	0.0635 (8)	0.0769 (10)	0.0422 (7)	0.0031 (7)	−0.0009 (6)	0.0051 (7)
O2	0.1009 (13)	0.154 (2)	0.0552 (10)	−0.0192 (12)	−0.0220 (9)	0.0058 (11)
O3	0.0650 (9)	0.1341 (17)	0.0991 (13)	−0.0299 (10)	−0.0239 (9)	−0.0091 (12)

C1—C2	1.406 (2)	C11—H11	0.9300
C1—C11	1.426 (2)	C12—C17	1.380 (3)
C1—C10	1.447 (2)	C12—C13	1.409 (2)
C2—O1	1.331 (2)	C12—N1	1.411 (2)
C2—C3	1.417 (3)	C13—C14	1.389 (2)
C3—C4	1.349 (3)	C13—C18	1.498 (3)
C3—H3	0.9300	C14—C15	1.371 (3)
C4—C5	1.420 (3)	C14—N2	1.478 (3)
C4—H4	0.9300	C15—C16	1.381 (3)
C5—C6	1.415 (3)	C15—H15	0.9300
C5—C10	1.415 (2)	C16—C17	1.374 (3)
C6—C7	1.351 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.390 (3)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.372 (3)	C18—H18C	0.9600
C8—H8	0.9300	N2—O2	1.206 (2)
C9—C10	1.406 (2)	N2—O3	1.221 (2)
C9—H9	0.9300	O1—H1	1.10 (3)
C11—N1	1.299 (2)
C2—C1—C11	119.33 (16)	C1—C11—H11	118.8
C2—C1—C10	119.26 (15)	C17—C12—C13	121.45 (16)
C11—C1—C10	121.41 (15)	C17—C12—N1	120.96 (16)
O1—C2—C1	122.05 (15)	C13—C12—N1	117.52 (15)
O1—C2—C3	117.35 (16)	C14—C13—C12	114.78 (16)
C1—C2—C3	120.60 (16)	C14—C13—C18	124.22 (16)
C4—C3—C2	119.81 (18)	C12—C13—C18	120.91 (15)
C4—C3—H3	120.1	C15—C14—C13	124.69 (17)
C2—C3—H3	120.1	C15—C14—N2	115.32 (16)
C3—C4—C5	122.38 (17)	C13—C14—N2	119.98 (17)
C3—C4—H4	118.8	C14—C15—C16	118.58 (18)
C5—C4—H4	118.8	C14—C15—H15	120.7
C6—C5—C10	119.57 (18)	C16—C15—H15	120.7
C6—C5—C4	121.22 (16)	C17—C16—C15	119.5 (2)
C10—C5—C4	119.21 (16)	C17—C16—H16	120.3
C7—C6—C5	121.06 (17)	C15—C16—H16	120.3
C7—C6—H6	119.5	C16—C17—C12	120.96 (19)
C5—C6—H6	119.5	C16—C17—H17	119.5
C6—C7—C8	119.95 (17)	C12—C17—H17	119.5
C6—C7—H7	120.0	C13—C18—H18A	109.5
C8—C7—H7	120.0	C13—C18—H18B	109.5
C9—C8—C7	120.52 (19)	H18A—C18—H18B	109.5
C9—C8—H8	119.7	C13—C18—H18C	109.5
C7—C8—H8	119.7	H18A—C18—H18C	109.5
C8—C9—C10	121.39 (17)	H18B—C18—H18C	109.5
C8—C9—H9	119.3	C11—N1—C12	121.57 (15)
C10—C9—H9	119.3	C11—N1—H1	97.0 (12)
C9—C10—C5	117.49 (16)	C12—N1—H1	141.0 (12)
C9—C10—C1	123.80 (15)	O2—N2—O3	123.89 (19)
C5—C10—C1	118.71 (16)	O2—N2—C14	119.41 (19)
N1—C11—C1	122.38 (17)	O3—N2—C14	116.68 (19)
N1—C11—H11	118.8	C2—O1—H1	99.5 (17)
C11—C1—C2—O1	−1.2 (3)	C2—C1—C11—N1	−0.6 (3)
C10—C1—C2—O1	179.59 (16)	C10—C1—C11—N1	178.56 (17)
C11—C1—C2—C3	178.70 (17)	C17—C12—C13—C14	2.2 (3)
C10—C1—C2—C3	−0.5 (3)	N1—C12—C13—C14	179.22 (16)
O1—C2—C3—C4	178.99 (19)	C17—C12—C13—C18	178.92 (19)
C1—C2—C3—C4	−0.9 (3)	N1—C12—C13—C18	−4.1 (3)
C2—C3—C4—C5	1.0 (3)	C12—C13—C14—C15	−0.9 (3)
C3—C4—C5—C6	−179.8 (2)	C18—C13—C14—C15	−177.5 (2)
C3—C4—C5—C10	0.4 (3)	C12—C13—C14—N2	178.16 (18)
C10—C5—C6—C7	1.0 (3)	C18—C13—C14—N2	1.6 (3)
C4—C5—C6—C7	−178.9 (2)	C13—C14—C15—C16	−0.6 (4)
C5—C6—C7—C8	0.5 (3)	N2—C14—C15—C16	−179.7 (2)
C6—C7—C8—C9	−1.4 (3)	C14—C15—C16—C17	0.8 (4)
C7—C8—C9—C10	0.8 (3)	C15—C16—C17—C12	0.5 (4)
C8—C9—C10—C5	0.6 (3)	C13—C12—C17—C16	−2.1 (3)
C8—C9—C10—C1	−179.21 (17)	N1—C12—C17—C16	−179.0 (2)
C6—C5—C10—C9	−1.5 (3)	C1—C11—N1—C12	178.07 (15)
C4—C5—C10—C9	178.39 (18)	C17—C12—N1—C11	−37.0 (3)
C6—C5—C10—C1	178.35 (17)	C13—C12—N1—C11	145.97 (18)
C4—C5—C10—C1	−1.8 (3)	C15—C14—N2—O2	−135.8 (2)
C2—C1—C10—C9	−178.35 (16)	C13—C14—N2—O2	45.0 (3)
C11—C1—C10—C9	2.5 (3)	C15—C14—N2—O3	42.8 (3)
C2—C1—C10—C5	1.8 (2)	C13—C14—N2—O3	−136.3 (2)
C11—C1—C10—C5	−177.34 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.10 (3)	1.48 (3)	2.5310 (19)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.10 (3)	1.48 (3)	2.5310 (19)	159 (3)