2-[(E)-(Naphthalen-2-yl)imino-meth-yl]phenol.

In the title compound, C(17)H(13)NO, the azomethine double bond adopts an E conformation. The naphthyl ring system and the benzene ring form a dihedral angle of 8.09 (10)°. The near-planar conformation of the molecule is consolidated by an intra-molecular O-H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, mol-ecules are arranged in a zigzag fashion parallel to the c axis.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ▶). For the crystal structure of a closely related Schiff base, see: Aslam et al. (2012 ▶).

Experimental

Crystal data

C17H13NO

M = 247.28

Orthorhombic,

a = 13.6348 (17) Å

b = 5.8768 (7) Å

c = 15.869 (2) Å

V = 1271.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.988, T max = 0.992

6852 measured reflections

2300 independent reflections

1655 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.089

S = 1.00

2300 reflections

176 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.08 e Å−3

Δρmin = −0.09 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033843/pv2571sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033843/pv2571Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033843/pv2571Isup3.cml

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

C17H13NO	F(000) = 520
Mr = 247.28	Dx = 1.292 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1294 reflections
a = 13.6348 (17) Å	θ = 2.6–27.8°
b = 5.8768 (7) Å	µ = 0.08 mm−1
c = 15.869 (2) Å	T = 273 K
V = 1271.5 (3) Å3	Block, yellow
Z = 4	0.15 × 0.13 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	2300 independent reflections
Radiation source: fine-focus sealed tube	1655 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scan	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.988, Tmax = 0.992	k = −7→6
6852 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0383P)2] where P = (Fo2 + 2Fc2)/3
2300 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.08 e Å−3
2 restraints	Δρmin = −0.09 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
O1	0.51540 (13)	1.1177 (3)	0.40612 (13)	0.0846 (6)
N1	0.58509 (13)	0.7914 (3)	0.50171 (12)	0.0592 (5)
C1	0.73882 (15)	0.8452 (4)	0.56875 (14)	0.0542 (5)
H1B	0.7413	0.9851	0.5415	0.065*
C2	0.81650 (15)	0.7835 (4)	0.62265 (13)	0.0519 (5)
C3	0.89755 (15)	0.9265 (4)	0.63756 (14)	0.0626 (6)
H3A	0.9012	1.0662	0.6103	0.075*
C4	0.97028 (19)	0.8641 (4)	0.69100 (17)	0.0718 (7)
H4A	1.0229	0.9616	0.7001	0.086*
C5	0.96686 (19)	0.6547 (5)	0.73249 (15)	0.0707 (7)
H5A	1.0167	0.6140	0.7695	0.085*
C6	0.89085 (18)	0.5111 (4)	0.71880 (14)	0.0664 (7)
H6A	0.8901	0.3702	0.7455	0.080*
C7	0.81231 (16)	0.5715 (4)	0.66451 (13)	0.0552 (6)
C8	0.73097 (17)	0.4295 (4)	0.64880 (16)	0.0662 (7)
H8A	0.7274	0.2883	0.6750	0.079*
C9	0.65784 (16)	0.4950 (4)	0.59615 (17)	0.0694 (7)
H9A	0.6051	0.3977	0.5869	0.083*
C10	0.66026 (15)	0.7071 (3)	0.55524 (14)	0.0527 (5)
C11	0.50538 (16)	0.6824 (4)	0.49001 (14)	0.0591 (6)
H11A	0.4976	0.5400	0.5147	0.071*
C12	0.42625 (15)	0.7755 (4)	0.43905 (13)	0.0538 (6)
C13	0.33980 (16)	0.6545 (4)	0.43146 (16)	0.0676 (6)
H13A	0.3340	0.5137	0.4577	0.081*
C14	0.26177 (19)	0.7392 (5)	0.38553 (15)	0.0753 (7)
H14A	0.2040	0.6559	0.3808	0.090*
C15	0.27038 (18)	0.9489 (5)	0.34667 (16)	0.0738 (7)
H15A	0.2179	1.0067	0.3159	0.089*
C16	0.35529 (17)	1.0725 (5)	0.35294 (16)	0.0709 (7)
H16A	0.3606	1.2121	0.3257	0.085*
C17	0.43405 (15)	0.9890 (4)	0.40022 (15)	0.0596 (6)
H1C	0.5580 (15)	1.045 (4)	0.4354 (15)	0.085 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0667 (11)	0.0733 (12)	0.1138 (16)	−0.0103 (10)	−0.0150 (11)	0.0200 (12)
N1	0.0481 (10)	0.0643 (12)	0.0652 (12)	0.0001 (9)	−0.0006 (9)	0.0003 (10)
C1	0.0549 (12)	0.0528 (13)	0.0549 (13)	0.0019 (10)	0.0028 (11)	0.0091 (11)
C2	0.0526 (12)	0.0541 (13)	0.0490 (13)	0.0030 (10)	0.0050 (10)	0.0028 (12)
C3	0.0625 (14)	0.0623 (15)	0.0628 (15)	−0.0067 (12)	−0.0046 (12)	0.0083 (13)
C4	0.0656 (16)	0.080 (2)	0.0693 (15)	−0.0074 (13)	−0.0103 (14)	−0.0022 (15)
C5	0.0682 (16)	0.0849 (19)	0.0589 (14)	0.0102 (14)	−0.0107 (12)	0.0035 (15)
C6	0.0729 (17)	0.0688 (15)	0.0576 (16)	0.0126 (14)	0.0048 (14)	0.0094 (13)
C7	0.0581 (13)	0.0592 (14)	0.0484 (13)	0.0059 (11)	0.0069 (11)	0.0063 (12)
C8	0.0656 (16)	0.0570 (14)	0.0759 (17)	−0.0038 (12)	0.0015 (14)	0.0200 (13)
C9	0.0588 (14)	0.0648 (16)	0.0847 (17)	−0.0092 (12)	0.0021 (14)	0.0113 (15)
C10	0.0483 (12)	0.0548 (14)	0.0551 (13)	0.0041 (10)	0.0036 (12)	0.0051 (12)
C11	0.0591 (14)	0.0567 (13)	0.0616 (15)	0.0047 (11)	0.0037 (12)	−0.0055 (12)
C12	0.0506 (12)	0.0585 (14)	0.0523 (13)	0.0013 (11)	0.0029 (10)	−0.0084 (12)
C13	0.0669 (14)	0.0712 (16)	0.0649 (15)	−0.0051 (13)	−0.0020 (13)	−0.0112 (14)
C14	0.0649 (15)	0.095 (2)	0.0659 (17)	−0.0086 (14)	−0.0118 (13)	−0.0116 (16)
C15	0.0617 (15)	0.096 (2)	0.0642 (16)	0.0132 (14)	−0.0109 (13)	−0.0180 (16)
C16	0.0726 (16)	0.0752 (18)	0.0649 (16)	0.0103 (14)	−0.0071 (15)	−0.0064 (14)
C17	0.0521 (13)	0.0641 (15)	0.0627 (15)	0.0007 (11)	0.0031 (12)	−0.0067 (13)

O1—C17	1.346 (3)	C7—C8	1.410 (3)
O1—H1C	0.86 (2)	C8—C9	1.356 (3)
N1—C11	1.275 (2)	C8—H8A	0.9300
N1—C10	1.421 (2)	C9—C10	1.406 (3)
C1—C10	1.361 (3)	C9—H9A	0.9300
C1—C2	1.409 (3)	C11—C12	1.455 (3)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.408 (3)	C12—C13	1.382 (3)
C2—C7	1.413 (3)	C12—C17	1.402 (3)
C3—C4	1.355 (3)	C13—C14	1.382 (3)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.396 (3)	C14—C15	1.383 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.354 (3)	C15—C16	1.370 (3)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.419 (3)	C16—C17	1.399 (3)
C6—H6A	0.9300	C16—H16A	0.9300
C17—O1—H1C	108.4 (18)	C8—C9—H9A	119.4
C11—N1—C10	121.78 (19)	C10—C9—H9A	119.4
C10—C1—C2	122.3 (2)	C1—C10—C9	118.3 (2)
C10—C1—H1B	118.9	C1—C10—N1	116.99 (18)
C2—C1—H1B	118.9	C9—C10—N1	124.66 (19)
C3—C2—C1	122.6 (2)	N1—C11—C12	121.6 (2)
C3—C2—C7	118.60 (19)	N1—C11—H11A	119.2
C1—C2—C7	118.80 (19)	C12—C11—H11A	119.2
C4—C3—C2	121.2 (2)	C13—C12—C17	119.1 (2)
C4—C3—H3A	119.4	C13—C12—C11	119.2 (2)
C2—C3—H3A	119.4	C17—C12—C11	121.6 (2)
C3—C4—C5	120.6 (2)	C12—C13—C14	121.2 (2)
C3—C4—H4A	119.7	C12—C13—H13A	119.4
C5—C4—H4A	119.7	C14—C13—H13A	119.4
C6—C5—C4	119.9 (2)	C13—C14—C15	119.4 (2)
C6—C5—H5A	120.0	C13—C14—H14A	120.3
C4—C5—H5A	120.0	C15—C14—H14A	120.3
C5—C6—C7	121.3 (2)	C16—C15—C14	120.8 (2)
C5—C6—H6A	119.4	C16—C15—H15A	119.6
C7—C6—H6A	119.4	C14—C15—H15A	119.6
C8—C7—C2	118.1 (2)	C15—C16—C17	120.1 (3)
C8—C7—C6	123.5 (2)	C15—C16—H16A	120.0
C2—C7—C6	118.4 (2)	C17—C16—H16A	120.0
C9—C8—C7	121.3 (2)	O1—C17—C16	118.2 (2)
C9—C8—H8A	119.4	O1—C17—C12	122.3 (2)
C7—C8—H8A	119.4	C16—C17—C12	119.4 (2)
C8—C9—C10	121.2 (2)
C10—C1—C2—C3	−179.4 (2)	C8—C9—C10—C1	0.9 (3)
C10—C1—C2—C7	−0.4 (3)	C8—C9—C10—N1	−177.6 (2)
C1—C2—C3—C4	178.8 (2)	C11—N1—C10—C1	−174.8 (2)
C7—C2—C3—C4	−0.2 (3)	C11—N1—C10—C9	3.8 (3)
C2—C3—C4—C5	0.3 (4)	C10—N1—C11—C12	176.38 (18)
C3—C4—C5—C6	0.7 (4)	N1—C11—C12—C13	−177.2 (2)
C4—C5—C6—C7	−1.8 (4)	N1—C11—C12—C17	0.2 (3)
C3—C2—C7—C8	−179.76 (19)	C17—C12—C13—C14	0.8 (3)
C1—C2—C7—C8	1.2 (3)	C11—C12—C13—C14	178.27 (19)
C3—C2—C7—C6	−0.9 (3)	C12—C13—C14—C15	−0.1 (3)
C1—C2—C7—C6	−179.89 (19)	C13—C14—C15—C16	0.3 (4)
C5—C6—C7—C8	−179.3 (2)	C14—C15—C16—C17	−1.1 (4)
C5—C6—C7—C2	1.9 (3)	C15—C16—C17—O1	−178.7 (2)
C2—C7—C8—C9	−1.0 (3)	C15—C16—C17—C12	1.7 (3)
C6—C7—C8—C9	−179.8 (2)	C13—C12—C17—O1	178.9 (2)
C7—C8—C9—C10	−0.1 (4)	C11—C12—C17—O1	1.5 (3)
C2—C1—C10—C9	−0.7 (3)	C13—C12—C17—C16	−1.6 (3)
C2—C1—C10—N1	177.97 (18)	C11—C12—C17—C16	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N1	0.86 (2)	1.86 (2)	2.623 (3)	147 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯N1	0.86 (2)	1.86 (2)	2.623 (3)	147 (2)