(Z)-1-[(3-Cyano-phen-yl)iminiometh-yl]-2-naphtholate.

The title compound, C(18)H(12)N(2)O, crystallizes in a zwitterionic form. The dihedral angle between the planes of the benzene ring and naphthalene ring system is 13.95 (5)°. An intra-molecular N-H⋯O inter-action results in the formation of a planar six-membered ring, which is oriented at dihedral angles of 13.50 (4) and 4.49 (4)° with respect to the benzene ring and naphthalene ring system, respectively. In the crystal structure, inter-molecular C-H⋯O and C-H⋯N inter-actions link the mol-ecules into a two-dimensional network. π-π contacts between the naphthalene systems [centroid-centroid distance = 3.974 (1) Å] may further stabilize the structure.

Related literature

For the pharmacological activity of Schiff base compounds, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶). For the role played by Schiff base compounds in coordination chemistry related to magnetism, see: Chen et al. (2008 ▶); Weber et al. (2007 ▶). For related structures, see: Elmali et al. (2001 ▶); Yüce et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H12N2O

M = 272.30

Triclinic,

a = 7.8943 (16) Å

b = 9.1356 (18) Å

c = 9.4933 (19) Å

α = 83.97 (3)°

β = 84.41 (3)°

γ = 82.50 (3)°

V = 672.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.976, T max = 0.983

6177 measured reflections

2628 independent reflections

1146 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.195

S = 0.94

2628 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020224/hk2700sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020224/hk2700Isup2.hkl

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

C18H12N2O	Z = 2
Mr = 272.30	F(000) = 284
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8943 (16) Å	Cell parameters from 4320 reflections
b = 9.1356 (18) Å	θ = 3.2–27.5°
c = 9.4933 (19) Å	µ = 0.09 mm−1
α = 83.97 (3)°	T = 294 K
β = 84.41 (3)°	Prism, yellow
γ = 82.50 (3)°	0.20 × 0.20 × 0.20 mm
V = 672.6 (2) Å3

Rigaku SCXmini diffractometer	2628 independent reflections
Radiation source: fine-focus sealed tube	1146 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.976, Tmax = 0.983	l = −11→11
6177 measured reflections

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3
2628 reflections	(Δ/σ)max = 0.016
190 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 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	0.9002 (3)	0.6505 (3)	0.2062 (2)	0.0608 (8)
N1	0.7833 (3)	0.3998 (3)	0.2569 (3)	0.0439 (7)
H1A	0.8270	0.4652	0.1974	0.053*
N2	0.4237 (5)	−0.1364 (4)	0.3557 (4)	0.0852 (12)
C1	0.7515 (4)	0.2689 (4)	0.2031 (3)	0.0421 (8)
C2	0.6494 (4)	0.1697 (3)	0.2774 (3)	0.0452 (9)
H2A	0.5984	0.1876	0.3675	0.054*
C3	0.6234 (4)	0.0444 (4)	0.2177 (4)	0.0482 (9)
C4	0.6973 (5)	0.0157 (4)	0.0832 (4)	0.0609 (11)
H4A	0.6799	−0.0695	0.0437	0.073*
C5	0.7971 (5)	0.1160 (4)	0.0093 (4)	0.0654 (11)
H5A	0.8467	0.0985	−0.0812	0.079*
C6	0.8240 (4)	0.2410 (4)	0.0675 (3)	0.0514 (10)
H6A	0.8914	0.3077	0.0160	0.062*
C7	0.5115 (5)	−0.0569 (4)	0.2954 (4)	0.0611 (11)
C8	0.7525 (4)	0.4310 (3)	0.3886 (3)	0.0408 (8)
H8A	0.7016	0.3630	0.4536	0.049*
C9	0.7916 (4)	0.5615 (3)	0.4381 (3)	0.0405 (8)
C10	0.8725 (4)	0.6662 (3)	0.3400 (4)	0.0433 (9)
C11	0.9241 (5)	0.7903 (4)	0.3945 (4)	0.0576 (11)
H11A	0.9789	0.8582	0.3323	0.069*
C12	0.8969 (5)	0.8139 (4)	0.5334 (4)	0.0577 (10)
H12A	0.9334	0.8968	0.5645	0.069*
C13	0.8122 (4)	0.7125 (3)	0.6335 (4)	0.0424 (9)
C14	0.7876 (4)	0.7374 (4)	0.7790 (4)	0.0533 (10)
H14A	0.8261	0.8199	0.8091	0.064*
C15	0.7077 (4)	0.6415 (4)	0.8761 (4)	0.0554 (10)
H15A	0.6908	0.6590	0.9715	0.067*
C16	0.6524 (4)	0.5185 (4)	0.8304 (4)	0.0509 (9)
H16A	0.5981	0.4529	0.8957	0.061*
C17	0.6766 (4)	0.4920 (4)	0.6902 (3)	0.0483 (9)
H17A	0.6374	0.4087	0.6623	0.058*
C18	0.7585 (4)	0.5863 (3)	0.5875 (3)	0.0367 (8)

	U11	U22	U33	U12	U13	U23
O1	0.083 (2)	0.0657 (17)	0.0347 (15)	−0.0255 (14)	0.0047 (13)	0.0010 (12)
N1	0.0520 (19)	0.0430 (17)	0.0370 (17)	−0.0146 (13)	0.0051 (13)	−0.0025 (14)
N2	0.120 (3)	0.064 (2)	0.076 (3)	−0.043 (2)	0.011 (2)	−0.010 (2)
C1	0.043 (2)	0.044 (2)	0.040 (2)	−0.0072 (16)	−0.0024 (16)	−0.0059 (17)
C2	0.057 (2)	0.044 (2)	0.035 (2)	−0.0102 (18)	0.0011 (16)	−0.0075 (16)
C3	0.057 (2)	0.042 (2)	0.048 (2)	−0.0068 (18)	−0.0062 (18)	−0.0107 (17)
C4	0.079 (3)	0.055 (2)	0.051 (3)	−0.008 (2)	−0.004 (2)	−0.018 (2)
C5	0.083 (3)	0.069 (3)	0.047 (2)	−0.018 (2)	0.010 (2)	−0.020 (2)
C6	0.053 (2)	0.061 (2)	0.040 (2)	−0.0129 (19)	0.0046 (17)	−0.0033 (18)
C7	0.080 (3)	0.051 (2)	0.054 (3)	−0.014 (2)	−0.001 (2)	−0.011 (2)
C8	0.040 (2)	0.044 (2)	0.038 (2)	−0.0066 (16)	0.0015 (15)	−0.0029 (16)
C9	0.039 (2)	0.041 (2)	0.041 (2)	−0.0065 (16)	−0.0007 (15)	0.0003 (16)
C10	0.052 (2)	0.0366 (19)	0.042 (2)	−0.0093 (16)	−0.0054 (17)	−0.0010 (16)
C11	0.070 (3)	0.047 (2)	0.058 (3)	−0.0253 (19)	−0.001 (2)	0.003 (2)
C12	0.068 (3)	0.050 (2)	0.060 (3)	−0.022 (2)	−0.003 (2)	−0.007 (2)
C13	0.041 (2)	0.042 (2)	0.046 (2)	−0.0029 (16)	−0.0066 (16)	−0.0074 (17)
C14	0.053 (2)	0.055 (2)	0.056 (3)	−0.0066 (19)	−0.0103 (19)	−0.020 (2)
C15	0.058 (2)	0.064 (3)	0.043 (2)	−0.003 (2)	0.0004 (18)	−0.009 (2)
C16	0.057 (2)	0.051 (2)	0.043 (2)	−0.0085 (18)	0.0046 (17)	−0.0013 (18)
C17	0.052 (2)	0.045 (2)	0.048 (2)	−0.0097 (18)	0.0029 (17)	−0.0074 (18)
C18	0.0366 (19)	0.0372 (19)	0.0377 (19)	−0.0076 (15)	−0.0012 (14)	−0.0074 (15)

O1—C10	1.287 (4)	C9—C10	1.431 (4)
N1—C1	1.409 (4)	C9—C18	1.453 (4)
N1—C8	1.304 (4)	C11—C10	1.416 (4)
N1—H1A	0.8600	C11—C12	1.350 (5)
N2—C7	1.142 (4)	C11—H11A	0.9300
C2—C1	1.384 (4)	C12—H12A	0.9300
C2—C3	1.376 (4)	C13—C12	1.435 (4)
C2—H2A	0.9300	C13—C14	1.414 (4)
C4—C3	1.387 (5)	C13—C18	1.403 (4)
C4—C5	1.377 (5)	C14—H14A	0.9300
C4—H4A	0.9300	C15—C14	1.370 (4)
C5—H5A	0.9300	C15—C16	1.382 (5)
C6—C1	1.392 (4)	C15—H15A	0.9300
C6—C5	1.369 (5)	C16—H16A	0.9300
C6—H6A	0.9300	C17—C16	1.369 (4)
C7—C3	1.458 (5)	C17—C18	1.399 (4)
C8—H8A	0.9300	C17—H17A	0.9300
C9—C8	1.406 (4)
C1—N1—H1A	117.0	O1—C10—C9	122.5 (3)
C8—N1—C1	126.0 (3)	O1—C10—C11	119.7 (3)
C8—N1—H1A	117.0	C11—C10—C9	117.8 (3)
C2—C1—N1	123.1 (3)	C10—C11—H11A	118.7
C2—C1—C6	119.0 (3)	C12—C11—C10	122.6 (3)
C6—C1—N1	117.9 (3)	C12—C11—H11A	118.7
C1—C2—H2A	120.1	C11—C12—C13	120.8 (3)
C3—C2—C1	119.8 (3)	C11—C12—H12A	119.6
C3—C2—H2A	120.1	C13—C12—H12A	119.6
C2—C3—C4	121.1 (3)	C14—C13—C12	120.0 (3)
C2—C3—C7	119.2 (3)	C18—C13—C12	119.9 (3)
C4—C3—C7	119.6 (3)	C18—C13—C14	120.0 (3)
C3—C4—H4A	120.7	C13—C14—H14A	119.6
C5—C4—C3	118.6 (4)	C15—C14—C13	120.8 (3)
C5—C4—H4A	120.7	C15—C14—H14A	119.6
C4—C5—H5A	119.6	C14—C15—C16	119.1 (3)
C6—C5—C4	120.9 (4)	C14—C15—H15A	120.5
C6—C5—H5A	119.6	C16—C15—H15A	120.5
C1—C6—H6A	119.7	C15—C16—H16A	119.6
C5—C6—C1	120.5 (3)	C17—C16—C15	120.8 (3)
C5—C6—H6A	119.7	C17—C16—H16A	119.6
N2—C7—C3	179.7 (4)	C16—C17—C18	122.1 (3)
N1—C8—C9	123.9 (3)	C16—C17—H17A	119.0
N1—C8—H8A	118.0	C18—C17—H17A	119.0
C9—C8—H8A	118.0	C13—C18—C9	118.5 (3)
C8—C9—C10	118.8 (3)	C17—C18—C13	117.1 (3)
C8—C9—C18	120.7 (3)	C17—C18—C9	124.4 (3)
C10—C9—C18	120.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.87	2.562 (3)	136
C2—H2A···N2i	0.93	2.61	3.463 (3)	152
C6—H6A···O1ii	0.93	2.57	3.376 (3)	145
C17—H17A···N2i	0.93	2.62	3.522 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.87	2.562 (3)	136
C2—H2A⋯N2i	0.93	2.61	3.463 (3)	152
C6—H6A⋯O1ii	0.93	2.57	3.376 (3)	145
C17—H17A⋯N2i	0.93	2.62	3.522 (3)	163

Symmetry codes: (i) ; (ii) .