1-[(4-{[(2-Oxo-1,2-dihydro-naphthalen-1-yl-idene)meth-yl]amino}-anilino)methyl-idene]naphthalen-2(1H)-one dihydrate.

The title compound, C(28)H(20)N(2)O(2)·2H(2)O, comprises a Schiff base mol-ecule with an imposed inversion centre in the middle of p-phenyl-enediamine unit and water mol-ecules of crystallization. In the structure, the Schiff base mol-ecule is present as the keto-amino tautomer with a strong intra-molecular N-H⋯O hydrogen bond. The Schiff base mol-ecules and water mol-ecules of crystallization create infinite [010] columns through O-H⋯O hydrogen bonds. Inter-molecular attractions within columns are through additional π-π inter-actions [centroid-centroid distance = 3.352 (1) Å] between parallel Schiff base mol-ecules. The columns are joined into infinite (011) layers through weak C-H⋯O hydrogen bonds. The layers pack in an assembly by van der Waals attractions, only being effective between bordering non-polar naphthalene ring systems.

Related literature

For general background to Schiff bases, see: Blagus et al. (2010 ▶). The stereochemistry of intrinsic Schiff bases differs significantly, see: Inabe et al. (1994 ▶). For the quinoid effect in 2-oxy-naphthaldimine Schiff base derivatives, see: Gavranić et al. (1996 ▶); Friščić et al. (1998 ▶). For the herringbone packing motif in fused aromatic systems, see: Desiraju & Gavezzotti (1989 ▶).

Experimental

Crystal data

C28H20N2O2·n class="Chemical">2H2O

M = 452.49

Monoclinic,

a = 17.4222 (11) Å

b = 4.4686 (5) Å

c = 15.9374 (10) Å

β = 116.30 (1)°

V = 1112.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.5 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

14006 measured reflections

2423 independent reflections

1351 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.190

S = 1.05

2423 reflections

160 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041870/kp2357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041870/kp2357Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041870/kp2357Isup3.cml

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

C28H20N2O2·2H2O	F(000) = 476
Mr = 452.49	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2423 reflections
a = 17.4222 (11) Å	θ = 4–27°
b = 4.4686 (5) Å	µ = 0.09 mm−1
c = 15.9374 (10) Å	T = 298 K
β = 116.30 (1)°	Prism, green
V = 1112.3 (2) Å3	0.5 × 0.2 × 0.1 mm
Z = 2

Oxford Diffraction Xcalibur CCD diffractometer	1351 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 27.0°, θmin = 3.9°
ω scans	h = −22→21
14006 measured reflections	k = −5→5
2423 independent reflections	l = −20→20

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0914P)2 + 0.2128P] where P = (Fo2 + 2Fc2)/3
2423 reflections	(Δ/σ)max = 0.009
160 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.27 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	0.19806 (12)	0.2820 (4)	0.25053 (12)	0.0537 (6)
N1	0.12888 (13)	0.5855 (4)	0.09888 (14)	0.0420 (5)
H1	0.1321	0.5349	0.1524	0.050*
C1	0.24546 (15)	0.2518 (5)	0.13184 (17)	0.0383 (6)
C2	0.25000 (16)	0.1743 (5)	0.22164 (17)	0.0416 (6)
C3	0.31492 (17)	−0.0329 (6)	0.27967 (18)	0.0486 (7)
H3	0.3186	−0.0853	0.3378	0.058*
C4	0.37040 (18)	−0.1525 (6)	0.25139 (19)	0.0495 (7)
H4	0.4116	−0.2855	0.2910	0.059*
C5	0.36876 (15)	−0.0839 (5)	0.16289 (18)	0.0427 (6)
C6	0.42800 (18)	−0.2111 (6)	0.1358 (2)	0.0527 (7)
H6	0.4696	−0.3410	0.1764	0.063*
C7	0.42563 (19)	−0.1479 (7)	0.0517 (2)	0.0583 (8)
H7	0.4654	−0.2326	0.0345	0.070*
C8	0.36356 (19)	0.0436 (6)	−0.0084 (2)	0.0568 (8)
H8	0.3616	0.0850	−0.0665	0.068*
C9	0.30524 (18)	0.1733 (6)	0.01493 (19)	0.0498 (7)
H9	0.2643	0.3014	−0.0274	0.060*
C10	0.30542 (15)	0.1174 (5)	0.10235 (17)	0.0387 (6)
C11	0.18466 (15)	0.4573 (5)	0.07490 (17)	0.0399 (6)
H11	0.1832	0.5066	0.0175	0.048*
C12	0.06465 (15)	0.7953 (5)	0.04716 (18)	0.0396 (6)
C13	0.05037 (17)	0.8940 (6)	−0.04079 (19)	0.0466 (7)
H13	0.0838	0.8227	−0.0685	0.056*
C14	−0.01402 (16)	1.0993 (6)	−0.08723 (18)	0.0450 (6)
H14	−0.0233	1.1673	−0.1461	0.054*
O1W	0.1500 (2)	0.8211 (6)	0.3392 (2)	0.0919 (9)
H1A	0.160 (3)	0.978 (4)	0.317 (3)	0.110*
H1B	0.170 (3)	0.687 (5)	0.318 (3)	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0561 (12)	0.0580 (12)	0.0539 (12)	0.0074 (10)	0.0306 (10)	0.0081 (9)
N1	0.0396 (12)	0.0385 (11)	0.0463 (12)	0.0040 (10)	0.0177 (10)	0.0037 (10)
C1	0.0330 (13)	0.0333 (12)	0.0435 (14)	−0.0026 (11)	0.0122 (11)	−0.0004 (11)
C2	0.0396 (14)	0.0392 (14)	0.0462 (15)	−0.0029 (12)	0.0193 (13)	0.0003 (12)
C3	0.0490 (16)	0.0481 (15)	0.0434 (15)	0.0008 (13)	0.0156 (13)	0.0080 (12)
C4	0.0414 (15)	0.0442 (15)	0.0511 (16)	0.0031 (13)	0.0097 (13)	0.0079 (13)
C5	0.0323 (13)	0.0402 (13)	0.0495 (15)	−0.0007 (11)	0.0124 (12)	−0.0009 (12)
C6	0.0394 (15)	0.0461 (16)	0.0653 (19)	0.0066 (12)	0.0166 (14)	0.0016 (14)
C7	0.0535 (18)	0.0555 (17)	0.074 (2)	0.0034 (15)	0.0361 (17)	−0.0068 (16)
C8	0.0609 (19)	0.0574 (18)	0.0573 (18)	0.0021 (15)	0.0309 (16)	−0.0027 (14)
C9	0.0511 (17)	0.0498 (16)	0.0480 (16)	0.0090 (13)	0.0214 (14)	0.0045 (12)
C10	0.0345 (13)	0.0333 (12)	0.0442 (14)	−0.0025 (11)	0.0138 (11)	−0.0025 (11)
C11	0.0373 (14)	0.0352 (13)	0.0449 (14)	−0.0005 (11)	0.0162 (12)	−0.0029 (11)
C12	0.0365 (14)	0.0328 (13)	0.0451 (14)	0.0008 (11)	0.0142 (12)	−0.0017 (11)
C13	0.0433 (15)	0.0454 (14)	0.0536 (16)	0.0058 (13)	0.0238 (13)	0.0002 (13)
C14	0.0454 (15)	0.0457 (14)	0.0427 (14)	0.0052 (13)	0.0185 (13)	0.0039 (12)
O1W	0.113 (2)	0.0952 (18)	0.0958 (19)	0.0004 (18)	0.0719 (17)	0.0129 (17)

O1—C2	1.277 (3)	C6—H6	0.9300
N1—C11	1.322 (3)	C7—C8	1.378 (4)
N1—C12	1.412 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.357 (4)
C1—C11	1.392 (3)	C8—H8	0.9300
C1—C2	1.440 (3)	C9—C10	1.414 (4)
C1—C10	1.452 (3)	C9—H9	0.9300
C2—C3	1.437 (3)	C11—H11	0.9300
C3—C4	1.345 (4)	C12—C13	1.383 (4)
C3—H3	0.9300	C13—C14	1.383 (4)
C4—C5	1.431 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.404 (4)	O1W—H1A	0.836 (10)
C5—C10	1.419 (3)	O1W—H1B	0.831 (10)
C6—C7	1.353 (4)
C11—N1—C12	127.8 (2)	C6—C7—C8	119.2 (3)
C11—N1—H1	116.1	C6—C7—H7	120.4
C12—N1—H1	116.1	C8—C7—H7	120.4
C11—C1—C2	119.8 (2)	C9—C8—C7	121.9 (3)
C11—C1—C10	120.7 (2)	C9—C8—H8	119.1
C2—C1—C10	119.5 (2)	C7—C8—H8	119.1
O1—C2—C3	119.5 (2)	C8—C9—C10	121.3 (3)
O1—C2—C1	122.1 (2)	C8—C9—H9	119.4
C3—C2—C1	118.4 (2)	C10—C9—H9	119.4
C4—C3—C2	121.2 (2)	C9—C10—C5	116.3 (2)
C4—C3—H3	119.4	C9—C10—C1	123.9 (2)
C2—C3—H3	119.4	C5—C10—C1	119.8 (2)
C3—C4—C5	122.8 (2)	N1—C11—C1	122.8 (2)
C3—C4—H4	118.6	N1—C11—H11	118.6
C5—C4—H4	118.6	C1—C11—H11	118.6
C6—C5—C10	120.3 (2)	C13—C12—N1	122.9 (2)
C6—C5—C4	121.3 (2)	C12—C13—C14	119.5 (2)
C10—C5—C4	118.4 (2)	C12—C13—H13	120.2
C7—C6—C5	121.1 (3)	C14—C13—H13	120.2
C7—C6—H6	119.4	C13—C14—H14	119.6
C5—C6—H6	119.4	H1A—O1W—H1B	103 (2)
C11—C1—C2—O1	2.0 (4)	C8—C9—C10—C1	179.3 (2)
C10—C1—C2—O1	−178.9 (2)	C6—C5—C10—C9	1.3 (4)
C11—C1—C2—C3	−178.5 (2)	C4—C5—C10—C9	−178.7 (2)
C10—C1—C2—C3	0.6 (3)	C6—C5—C10—C1	−178.9 (2)
O1—C2—C3—C4	179.6 (2)	C4—C5—C10—C1	1.1 (3)
C1—C2—C3—C4	0.0 (4)	C11—C1—C10—C9	−2.3 (4)
C2—C3—C4—C5	−0.1 (4)	C2—C1—C10—C9	178.6 (2)
C3—C4—C5—C6	179.6 (3)	C11—C1—C10—C5	177.9 (2)
C3—C4—C5—C10	−0.5 (4)	C2—C1—C10—C5	−1.2 (3)
C10—C5—C6—C7	−0.7 (4)	C12—N1—C11—C1	−179.9 (2)
C4—C5—C6—C7	179.3 (3)	C2—C1—C11—N1	−0.9 (3)
C5—C6—C7—C8	−0.3 (4)	C10—C1—C11—N1	−179.9 (2)
C6—C7—C8—C9	0.7 (4)	C11—N1—C12—C13	1.3 (4)
C7—C8—C9—C10	−0.1 (4)	N1—C12—C13—C14	179.8 (2)
C8—C9—C10—C5	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.86	2.560 (3)	138
O1W—H1B···O1	0.83	2.27	3.090 (4)	169
O1W—H1A···O1i	0.84	2.01	2.826 (4)	165
C13—H13···O1Wii	0.93	2.33	3.247 (5)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.86	2.560 (3)	138
O1W—H1B⋯O1	0.83	2.27	3.090 (4)	169
O1W—H1A⋯O1i	0.84	2.01	2.826 (4)	165
C13—H13⋯O1Wii	0.93	2.33	3.247 (5)	170

Symmetry codes: (i) ; (ii) .