2,2'-[Naphthalene-1,5-diylbis(nitrilo-methanylyl-idene)]diphenol.

The title compound, C(24)H(18)N(2)O(2), lies about an inversion centre and the asymmetric unit contains one half-mol-ecule. An intra-molecular O-H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The crystal packing exhibits inter-molecular π-π stacking inter-actions between the aromatic rings with a centroid-centroid distance of 3.851 (2) Å.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For applications of Schiff base ligands, see: Pandeya et al. (1999 ▶, 2000 ▶); Singh & Dash (1988 ▶); Kelley et al. (1995 ▶); Turan-Zitouni et al. (2007 ▶); Tarafder et al. (2002 ▶); Sakyan et al. (2004 ▶); Gianneshi et al. (2005 ▶); Morris et al. (2001 ▶); Lu et al. (2007 ▶); Lau et al. (1999 ▶). For a related structure, see: Al-Douh et al. (2009 ▶).

Experimental

Crystal data

C24H18N2O2

M = 366.40

Monoclinic,

a = 3.8510 (9) Å

b = 19.395 (6) Å

c = 11.796 (2) Å

β = 95.85 (3)°

V = 876.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.23 × 0.15 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.980, T max = 0.990

4711 measured reflections

1544 independent reflections

1004 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.206

S = 1.18

1544 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023099/sj5163sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023099/sj5163Isup2.hkl

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

C24H18N2O2	F(000) = 384
Mr = 366.40	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4711 reflections
a = 3.8510 (9) Å	θ = 3.5–25.0°
b = 19.395 (6) Å	µ = 0.09 mm−1
c = 11.796 (2) Å	T = 293 K
β = 95.85 (3)°	Block, yellow
V = 876.4 (4) Å3	0.23 × 0.15 × 0.11 mm
Z = 2

Oxford Diffraction Xcalibur-S diffractometer	1544 independent reflections
Radiation source: fine-focus sealed tube	1004 reflections with I > 2σ(I)
graphite	Rint = 0.099
Detector resolution: 15.9948 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −4→3
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −22→23
Tmin = 0.980, Tmax = 0.990	l = −13→13
4711 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
1544 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.36 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
N1	0.3017 (6)	0.64602 (13)	−0.0063 (2)	0.0372 (7)
C1	0.5621 (8)	0.77817 (16)	0.0770 (3)	0.0380 (8)
C6	0.3700 (7)	0.76789 (15)	−0.0294 (3)	0.0355 (8)
C8	0.0499 (7)	0.53316 (14)	0.0215 (3)	0.0331 (8)
C7	0.2450 (8)	0.70066 (16)	−0.0666 (3)	0.0390 (8)
H7	0.1174	0.6968	−0.1376	0.047*
C9	0.1929 (7)	0.58080 (15)	−0.0513 (3)	0.0361 (8)
O1	0.6420 (7)	0.72510 (12)	0.1490 (2)	0.0531 (8)
H1	0.5617	0.6893	0.1202	0.080*
C11	−0.0030 (8)	0.54993 (16)	0.1351 (3)	0.0381 (8)
H11	0.0586	0.5934	0.1638	0.046*
C5	0.2987 (9)	0.82501 (16)	−0.1005 (3)	0.0428 (9)
H5	0.1709	0.8190	−0.1711	0.051*
C10	0.2399 (8)	0.56269 (17)	−0.1607 (3)	0.0384 (8)
H10	0.3368	0.5942	−0.2078	0.046*
C2	0.6767 (8)	0.84352 (17)	0.1085 (3)	0.0442 (9)
H2	0.8043	0.8504	0.1788	0.053*
C12	−0.1435 (8)	0.50288 (16)	0.2025 (3)	0.0398 (8)
H12	−0.1760	0.5143	0.2773	0.048*
C3	0.6030 (9)	0.89849 (18)	0.0363 (3)	0.0484 (10)
H3	0.6824	0.9422	0.0585	0.058*
C4	0.4136 (9)	0.88975 (18)	−0.0682 (3)	0.0471 (9)
H4	0.3641	0.9273	−0.1163	0.057*

	U11	U22	U33	U12	U13	U23
N1	0.0418 (13)	0.0354 (15)	0.0331 (17)	−0.0021 (11)	−0.0027 (12)	0.0029 (12)
C1	0.0390 (15)	0.0432 (19)	0.031 (2)	0.0014 (13)	0.0018 (15)	0.0017 (15)
C6	0.0381 (15)	0.0395 (18)	0.028 (2)	−0.0038 (13)	−0.0007 (14)	0.0010 (15)
C8	0.0324 (13)	0.0363 (16)	0.0288 (19)	0.0033 (12)	−0.0058 (13)	0.0026 (14)
C7	0.0399 (16)	0.0445 (19)	0.031 (2)	−0.0027 (13)	−0.0045 (14)	−0.0004 (15)
C9	0.0338 (14)	0.0405 (18)	0.032 (2)	−0.0013 (13)	−0.0065 (14)	−0.0012 (15)
O1	0.0687 (16)	0.0534 (15)	0.0332 (16)	−0.0045 (12)	−0.0141 (12)	0.0057 (12)
C11	0.0404 (16)	0.0384 (17)	0.034 (2)	0.0013 (13)	−0.0035 (14)	−0.0021 (16)
C5	0.0516 (18)	0.0440 (19)	0.031 (2)	−0.0015 (15)	−0.0023 (16)	0.0016 (16)
C10	0.0400 (16)	0.0456 (19)	0.029 (2)	−0.0017 (13)	0.0012 (14)	0.0067 (15)
C2	0.0442 (17)	0.052 (2)	0.034 (2)	−0.0037 (15)	−0.0051 (15)	−0.0082 (16)
C12	0.0443 (16)	0.051 (2)	0.0241 (19)	0.0029 (14)	0.0012 (15)	−0.0032 (15)
C3	0.0515 (19)	0.0410 (19)	0.052 (3)	−0.0047 (15)	0.0024 (18)	−0.0059 (18)
C4	0.056 (2)	0.043 (2)	0.042 (2)	0.0001 (15)	0.0030 (18)	0.0070 (17)

N1—C7	1.283 (4)	C11—C12	1.358 (5)
N1—C9	1.418 (4)	C11—H11	0.9300
C1—O1	1.350 (4)	C5—C4	1.372 (5)
C1—C2	1.381 (4)	C5—H5	0.9300
C1—C6	1.404 (4)	C10—C12i	1.400 (4)
C6—C5	1.400 (4)	C10—H10	0.9300
C6—C7	1.443 (4)	C2—C3	1.376 (5)
C8—C9	1.411 (5)	C2—H2	0.9300
C8—C11	1.414 (4)	C12—C10i	1.400 (4)
C8—C8i	1.421 (6)	C12—H12	0.9300
C7—H7	0.9300	C3—C4	1.378 (5)
C9—C10	1.367 (5)	C3—H3	0.9300
O1—H1	0.8200	C4—H4	0.9300
C7—N1—C9	120.2 (3)	C8—C11—H11	119.8
O1—C1—C2	119.0 (3)	C4—C5—C6	121.3 (3)
O1—C1—C6	121.3 (3)	C4—C5—H5	119.3
C2—C1—C6	119.7 (3)	C6—C5—H5	119.3
C1—C6—C5	118.4 (3)	C9—C10—C12i	120.7 (3)
C1—C6—C7	122.0 (3)	C9—C10—H10	119.7
C5—C6—C7	119.6 (3)	C12i—C10—H10	119.7
C9—C8—C11	121.9 (3)	C3—C2—C1	120.3 (3)
C9—C8—C8i	119.0 (4)	C3—C2—H2	119.8
C11—C8—C8i	119.1 (4)	C1—C2—H2	119.8
N1—C7—C6	123.0 (3)	C11—C12—C10i	120.7 (3)
N1—C7—H7	118.5	C11—C12—H12	119.6
C6—C7—H7	118.5	C10i—C12—H12	119.6
C10—C9—C8	120.2 (3)	C2—C3—C4	121.0 (3)
C10—C9—N1	121.3 (3)	C2—C3—H3	119.5
C8—C9—N1	118.4 (3)	C4—C3—H3	119.5
C1—O1—H1	109.5	C5—C4—C3	119.2 (3)
C12—C11—C8	120.3 (3)	C5—C4—H4	120.4
C12—C11—H11	119.8	C3—C4—H4	120.4
O1—C1—C6—C5	−179.4 (3)	C9—C8—C11—C12	179.6 (3)
C2—C1—C6—C5	−0.3 (5)	C8i—C8—C11—C12	0.8 (5)
O1—C1—C6—C7	0.7 (5)	C1—C6—C5—C4	0.3 (5)
C2—C1—C6—C7	179.8 (3)	C7—C6—C5—C4	−179.9 (3)
C9—N1—C7—C6	−175.5 (3)	C8—C9—C10—C12i	0.7 (4)
C1—C6—C7—N1	−0.5 (5)	N1—C9—C10—C12i	177.5 (3)
C5—C6—C7—N1	179.7 (3)	O1—C1—C2—C3	179.2 (3)
C11—C8—C9—C10	−180.0 (3)	C6—C1—C2—C3	0.1 (5)
C8i—C8—C9—C10	−1.2 (5)	C8—C11—C12—C10i	−0.4 (4)
C11—C8—C9—N1	3.2 (4)	C1—C2—C3—C4	0.2 (5)
C8i—C8—C9—N1	−178.0 (3)	C6—C5—C4—C3	0.1 (5)
C7—N1—C9—C10	43.0 (4)	C2—C3—C4—C5	−0.3 (5)
C7—N1—C9—C8	−140.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.634 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.634 (3)	148