3-{(E)-[(4-Formyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

The title Schiff base compound, C(18)H(13)NO(2), is a zwitterion, with the naphthol hy-droxy group deprotonated and the imine N atom protonated. It adopts an E configuration about the central C=N double bond. The dihedral angle between the naphthyl ring system and the benzene ring is 1.73 (11)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, adjacent mol-ecules are connected by inter-molecular C-H⋯O hydrogen bonds, forming a supra-molecular ribbon along the b axis.

Related literature

For details and applications of condensation reactions, see: Alsalim et al. (2010 ▶); Wadher et al. (2009 ▶); Abou-Melha & Faruk (2008 ▶); Sondhi et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H13NO2

M = 275.29

Monoclinic,

a = 7.3685 (8) Å

b = 12.7437 (13) Å

c = 14.4586 (15) Å

β = 91.979 (7)°

V = 1356.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.86 × 0.08 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.928, T max = 0.994

11574 measured reflections

2394 independent reflections

1416 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.171

S = 1.04

2394 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051822/is2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051822/is2641Isup2.hkl

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

C18H13NO2	F(000) = 576
Mr = 275.29	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2561 reflections
a = 7.3685 (8) Å	θ = 3.2–30.0°
b = 12.7437 (13) Å	µ = 0.09 mm−1
c = 14.4586 (15) Å	T = 296 K
β = 91.979 (7)°	Needle, orange
V = 1356.9 (2) Å3	0.86 × 0.08 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2394 independent reflections
Radiation source: fine-focus sealed tube	1416 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.928, Tmax = 0.994	k = −15→14
11574 measured reflections	l = −16→17

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0799P)2 + 0.244P] where P = (Fo2 + 2Fc2)/3
2394 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6211 (3)	−0.00216 (15)	0.67024 (13)	0.0694 (7)
O2	0.9842 (4)	−0.31405 (18)	0.16917 (18)	0.0913 (8)
N1	0.7418 (3)	−0.02531 (16)	0.50829 (17)	0.0496 (6)
C1	0.6323 (4)	0.0967 (2)	0.65940 (19)	0.0527 (7)
C2	0.5864 (4)	0.1658 (2)	0.73351 (19)	0.0578 (8)
H2	0.5496	0.1373	0.7890	0.069*
C3	0.5952 (4)	0.2702 (2)	0.72465 (19)	0.0563 (8)
H3	0.5634	0.3119	0.7743	0.068*
C4	0.6515 (4)	0.3201 (2)	0.64209 (19)	0.0503 (7)
C5	0.6622 (4)	0.4289 (2)	0.6367 (2)	0.0673 (9)
H4	0.6302	0.4692	0.6872	0.081*
C6	0.7185 (5)	0.4774 (2)	0.5590 (2)	0.0804 (11)
H5	0.7255	0.5502	0.5564	0.096*
C7	0.7654 (5)	0.4169 (2)	0.4837 (2)	0.0752 (10)
H6	0.8034	0.4496	0.4302	0.090*
C8	0.7564 (4)	0.3100 (2)	0.4871 (2)	0.0587 (8)
H7	0.7884	0.2712	0.4356	0.070*
C9	0.7000 (3)	0.25724 (19)	0.56633 (17)	0.0450 (7)
C10	0.6907 (3)	0.14332 (19)	0.57427 (17)	0.0448 (7)
C11	0.7430 (3)	0.07881 (19)	0.50285 (18)	0.0463 (7)
H11A	0.7807	0.1098	0.4485	0.056*
C12	0.7929 (3)	−0.09668 (18)	0.44023 (18)	0.0440 (7)
C13	0.7754 (4)	−0.20274 (19)	0.46048 (19)	0.0524 (7)
H13A	0.7329	−0.2236	0.5175	0.063*
C14	0.8209 (4)	−0.2768 (2)	0.39614 (19)	0.0537 (7)
H14A	0.8092	−0.3476	0.4104	0.064*
C15	0.8834 (3)	−0.24824 (19)	0.31103 (18)	0.0455 (7)
C16	0.9013 (4)	−0.1417 (2)	0.29133 (19)	0.0534 (7)
H16A	0.9443	−0.1212	0.2344	0.064*
C17	0.8566 (4)	−0.0671 (2)	0.35455 (18)	0.0513 (7)
H17A	0.8688	0.0037	0.3403	0.062*
C18	0.9279 (4)	−0.3289 (2)	0.2450 (2)	0.0625 (8)
H18A	0.9115	−0.3982	0.2629	0.075*
H1N1	0.698 (4)	−0.048 (2)	0.570 (2)	0.086 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0902 (17)	0.0565 (13)	0.0634 (14)	0.0048 (11)	0.0285 (12)	0.0080 (10)
O2	0.116 (2)	0.0838 (16)	0.0757 (17)	−0.0014 (13)	0.0242 (15)	−0.0122 (12)
N1	0.0528 (15)	0.0482 (14)	0.0486 (15)	0.0021 (10)	0.0130 (12)	−0.0011 (11)
C1	0.0472 (18)	0.0561 (18)	0.0552 (18)	0.0041 (13)	0.0085 (14)	0.0025 (14)
C2	0.0542 (19)	0.074 (2)	0.0461 (17)	−0.0002 (15)	0.0125 (14)	−0.0011 (14)
C3	0.053 (2)	0.065 (2)	0.0511 (18)	0.0029 (14)	0.0072 (15)	−0.0126 (14)
C4	0.0432 (17)	0.0557 (17)	0.0520 (17)	0.0027 (12)	0.0037 (14)	−0.0088 (13)
C5	0.080 (2)	0.0574 (19)	0.065 (2)	0.0052 (15)	0.0082 (18)	−0.0145 (15)
C6	0.115 (3)	0.0487 (18)	0.078 (2)	0.0010 (17)	0.016 (2)	−0.0039 (17)
C7	0.104 (3)	0.055 (2)	0.068 (2)	0.0024 (17)	0.0191 (19)	0.0091 (16)
C8	0.072 (2)	0.0506 (18)	0.0543 (18)	0.0065 (14)	0.0099 (16)	−0.0014 (13)
C9	0.0373 (16)	0.0488 (15)	0.0487 (16)	0.0020 (11)	0.0018 (13)	−0.0020 (12)
C10	0.0379 (16)	0.0494 (16)	0.0475 (16)	0.0032 (11)	0.0058 (13)	−0.0001 (12)
C11	0.0440 (16)	0.0482 (16)	0.0470 (16)	0.0035 (12)	0.0053 (13)	0.0025 (12)
C12	0.0374 (16)	0.0447 (15)	0.0500 (17)	0.0019 (11)	0.0053 (13)	−0.0008 (12)
C13	0.0563 (19)	0.0534 (17)	0.0479 (16)	0.0013 (13)	0.0088 (14)	0.0058 (13)
C14	0.0603 (19)	0.0427 (15)	0.0581 (18)	0.0008 (12)	0.0048 (15)	−0.0005 (13)
C15	0.0385 (16)	0.0478 (15)	0.0501 (17)	0.0002 (12)	0.0022 (13)	−0.0032 (12)
C16	0.0525 (19)	0.0583 (18)	0.0500 (17)	−0.0030 (13)	0.0124 (14)	−0.0004 (13)
C17	0.0570 (18)	0.0440 (15)	0.0539 (17)	−0.0007 (12)	0.0152 (14)	0.0032 (12)
C18	0.071 (2)	0.0581 (18)	0.059 (2)	−0.0023 (15)	0.0134 (17)	−0.0067 (14)

O1—C1	1.272 (3)	C7—H6	0.9300
O2—C18	1.201 (3)	C8—C9	1.404 (4)
N1—C11	1.329 (3)	C8—H7	0.9300
N1—C12	1.401 (3)	C9—C10	1.458 (3)
N1—H1N1	1.00 (3)	C10—C11	1.385 (3)
C1—C2	1.437 (4)	C11—H11A	0.9300
C1—C10	1.446 (3)	C12—C13	1.390 (3)
C2—C3	1.338 (4)	C12—C17	1.392 (3)
C2—H2	0.9300	C13—C14	1.374 (4)
C3—C4	1.427 (4)	C13—H13A	0.9300
C3—H3	0.9300	C14—C15	1.378 (4)
C4—C5	1.390 (4)	C14—H14A	0.9300
C4—C9	1.413 (3)	C15—C16	1.394 (3)
C5—C6	1.359 (4)	C15—C18	1.448 (4)
C5—H4	0.9300	C16—C17	1.367 (3)
C6—C7	1.389 (4)	C16—H16A	0.9300
C6—H5	0.9300	C17—H17A	0.9300
C7—C8	1.364 (4)	C18—H18A	0.9300
C11—N1—C12	127.2 (2)	C4—C9—C10	119.3 (2)
C11—N1—H1N1	110.3 (17)	C11—C10—C1	119.3 (2)
C12—N1—H1N1	122.6 (17)	C11—C10—C9	121.2 (2)
O1—C1—C2	119.8 (2)	C1—C10—C9	119.5 (2)
O1—C1—C10	122.3 (2)	N1—C11—C10	123.1 (2)
C2—C1—C10	117.9 (2)	N1—C11—H11A	118.5
C3—C2—C1	121.7 (3)	C10—C11—H11A	118.5
C3—C2—H2	119.2	C13—C12—C17	119.2 (2)
C1—C2—H2	119.2	C13—C12—N1	117.0 (2)
C2—C3—C4	122.7 (3)	C17—C12—N1	123.8 (2)
C2—C3—H3	118.7	C14—C13—C12	119.9 (2)
C4—C3—H3	118.7	C14—C13—H13A	120.1
C5—C4—C9	120.3 (3)	C12—C13—H13A	120.1
C5—C4—C3	120.7 (3)	C13—C14—C15	121.4 (2)
C9—C4—C3	119.0 (2)	C13—C14—H14A	119.3
C6—C5—C4	121.3 (3)	C15—C14—H14A	119.3
C6—C5—H4	119.3	C14—C15—C16	118.4 (2)
C4—C5—H4	119.3	C14—C15—C18	119.5 (2)
C5—C6—C7	119.1 (3)	C16—C15—C18	122.1 (3)
C5—C6—H5	120.5	C17—C16—C15	120.9 (2)
C7—C6—H5	120.5	C17—C16—H16A	119.5
C8—C7—C6	120.9 (3)	C15—C16—H16A	119.5
C8—C7—H6	119.6	C16—C17—C12	120.2 (2)
C6—C7—H6	119.6	C16—C17—H17A	119.9
C7—C8—C9	121.6 (3)	C12—C17—H17A	119.9
C7—C8—H7	119.2	O2—C18—C15	125.7 (3)
C9—C8—H7	119.2	O2—C18—H18A	117.2
C8—C9—C4	116.8 (2)	C15—C18—H18A	117.2
C8—C9—C10	123.9 (2)
O1—C1—C2—C3	−179.6 (3)	C4—C9—C10—C11	−177.8 (2)
C10—C1—C2—C3	0.6 (4)	C8—C9—C10—C1	179.4 (3)
C1—C2—C3—C4	−0.4 (4)	C4—C9—C10—C1	−0.1 (3)
C2—C3—C4—C5	−178.7 (3)	C12—N1—C11—C10	−179.6 (2)
C2—C3—C4—C9	0.0 (4)	C1—C10—C11—N1	0.2 (4)
C9—C4—C5—C6	0.2 (5)	C9—C10—C11—N1	177.9 (2)
C3—C4—C5—C6	178.9 (3)	C11—N1—C12—C13	−178.2 (2)
C4—C5—C6—C7	0.3 (5)	C11—N1—C12—C17	0.8 (4)
C5—C6—C7—C8	−0.3 (5)	C17—C12—C13—C14	0.0 (4)
C6—C7—C8—C9	−0.1 (5)	N1—C12—C13—C14	179.1 (2)
C7—C8—C9—C4	0.6 (4)	C12—C13—C14—C15	−0.3 (4)
C7—C8—C9—C10	−179.0 (3)	C13—C14—C15—C16	0.5 (4)
C5—C4—C9—C8	−0.6 (4)	C13—C14—C15—C18	−179.4 (3)
C3—C4—C9—C8	−179.3 (2)	C14—C15—C16—C17	−0.5 (4)
C5—C4—C9—C10	178.9 (2)	C18—C15—C16—C17	179.3 (3)
C3—C4—C9—C10	0.2 (4)	C15—C16—C17—C12	0.3 (4)
O1—C1—C10—C11	−2.4 (4)	C13—C12—C17—C16	0.0 (4)
C2—C1—C10—C11	177.4 (2)	N1—C12—C17—C16	−179.1 (2)
O1—C1—C10—C9	179.8 (2)	C14—C15—C18—O2	−179.6 (3)
C2—C1—C10—C9	−0.3 (4)	C16—C15—C18—O2	0.5 (5)
C8—C9—C10—C11	1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	1.00 (3)	1.68 (3)	2.551 (3)	143 (2)
C8—H7···O2i	0.93	2.54	3.399 (4)	153
C17—H17A···O2i	0.93	2.57	3.453 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	1.00 (3)	1.68 (3)	2.551 (3)	143 (2)
C8—H7⋯O2i	0.93	2.54	3.399 (4)	153
C17—H17A⋯O2i	0.93	2.57	3.453 (4)	159

Symmetry code: (i) .