2,2'-[1,1'-(Propane-1,3-diyldioxy-dinitrilo)diethyl-idyne]di-1-naphthol.

The mol-ecule of the title compound, C(27)H(26)N(2)O(4), lies across a crystallographic inversion centre and adopts an l-shaped configuration. Within the mol-ecule, the two naphthalene units are approximately perpendicular, making a dihedral angle of 80.24 (5)°. The two intramolecular O-H⋯N hydrogen bonds, generate S(6) ring motifs. In the crystal structure, every mol-ecule links five other mol-ecules into an infinite cross-linked layered supra-molecular structure via inter-molecular C-H⋯O hydrogen bonds, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distance = 3.956 (4) Å].

Related literature

For the steric and electronic properties of Schiff bases, see: Yamada (1999 ▶). For background to this study, see: Dong et al. (2006 ▶). For related structures, see: Dong & Duan (2008 ▶); Dong et al. (2008a ▶,b ▶,c ▶,d ▶); Duan et al. (2007 ▶); He et al. (2008 ▶).

Experimental

Crystal data

C27H26N2O4

M = 442.50

Triclinic,

a = 7.4411 (10) Å

b = 8.8911 (16) Å

c = 18.106 (2) Å

α = 100.645 (1)°

β = 94.331 (1)°

γ = 106.329 (2)°

V = 1119.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.42 × 0.37 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.968

5800 measured reflections

3876 independent reflections

2325 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.145

S = 1.04

3876 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023241/hg2527sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023241/hg2527Isup2.hkl

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

C27H26N2O4	Z = 2
Mr = 442.50	F(000) = 468
Triclinic, P1	Dx = 1.313 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4411 (10) Å	Cell parameters from 1962 reflections
b = 8.8911 (16) Å	θ = 2.3–26.3°
c = 18.106 (2) Å	µ = 0.09 mm−1
α = 100.645 (1)°	T = 298 K
β = 94.331 (1)°	Block-like, colorless
γ = 106.329 (2)°	0.50 × 0.42 × 0.37 mm
V = 1119.4 (3) Å3

Siemens SMART 1000 CCD area-detector diffractometer	3876 independent reflections
Radiation source: fine-focus sealed tube	2325 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
Tmin = 0.957, Tmax = 0.968	k = −10→10
5800 measured reflections	l = −20→21

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.1652P] where P = (Fo2 + 2Fc2)/3
3876 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 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	0.4304 (3)	0.3291 (2)	0.39356 (10)	0.0472 (5)
N2	0.5352 (3)	0.4359 (2)	0.09736 (10)	0.0490 (5)
O1	0.3227 (2)	0.35088 (19)	0.33130 (9)	0.0531 (5)
O2	0.6102 (2)	0.55995 (19)	0.16190 (9)	0.0568 (5)
O3	0.7381 (2)	0.38979 (19)	0.48069 (9)	0.0567 (5)
H3	0.6693	0.3990	0.4453	0.085*
O4	0.2690 (2)	0.2606 (2)	−0.00541 (9)	0.0589 (5)
H4	0.3176	0.3292	0.0332	0.088*
C1	0.4460 (3)	0.4646 (3)	0.29743 (12)	0.0444 (6)
H1A	0.5504	0.4264	0.2822	0.053*
H1B	0.4971	0.5663	0.3336	0.053*
C2	0.3361 (3)	0.4864 (3)	0.22958 (12)	0.0494 (6)
H2A	0.2300	0.5216	0.2451	0.059*
H2B	0.2864	0.3843	0.1936	0.059*
C3	0.4578 (4)	0.6083 (3)	0.19140 (13)	0.0557 (7)
H3A	0.3795	0.6253	0.1503	0.067*
H3B	0.5088	0.7097	0.2278	0.067*
C4	0.1200 (3)	0.1930 (3)	0.42415 (14)	0.0608 (7)
H4A	0.0746	0.2444	0.3878	0.091*
H4B	0.0718	0.2184	0.4710	0.091*
H4C	0.0779	0.0789	0.4052	0.091*
C5	0.3322 (3)	0.2511 (2)	0.43736 (12)	0.0421 (5)
C6	0.6336 (3)	0.2932 (2)	0.52118 (12)	0.0409 (5)
C7	0.4391 (3)	0.2236 (2)	0.50250 (11)	0.0385 (5)
C8	0.3456 (3)	0.1201 (3)	0.54803 (13)	0.0488 (6)
H8	0.2156	0.0725	0.5366	0.059*
C9	0.4393 (4)	0.0885 (3)	0.60760 (13)	0.0510 (6)
H9	0.3730	0.0189	0.6356	0.061*
C10	0.6365 (3)	0.1598 (3)	0.62776 (12)	0.0445 (6)
C11	0.7339 (3)	0.2654 (2)	0.58449 (12)	0.0413 (5)
C12	0.9311 (3)	0.3417 (3)	0.60585 (14)	0.0552 (7)
H12	0.9972	0.4118	0.5781	0.066*
C13	1.0230 (4)	0.3126 (3)	0.66666 (16)	0.0673 (8)
H13	1.1520	0.3636	0.6803	0.081*
C14	0.9279 (4)	0.2076 (3)	0.70901 (16)	0.0667 (8)
H14	0.9933	0.1888	0.7504	0.080*
C15	0.7397 (4)	0.1326 (3)	0.69001 (14)	0.0585 (7)
H15	0.6777	0.0621	0.7185	0.070*
C16	0.8658 (4)	0.4430 (3)	0.09754 (15)	0.0681 (8)
H16A	0.8829	0.5187	0.1447	0.102*
H16B	0.9350	0.4952	0.0620	0.102*
H16C	0.9112	0.3557	0.1058	0.102*
C17	0.6600 (3)	0.3798 (3)	0.06659 (12)	0.0449 (6)
C18	0.4008 (3)	0.1992 (3)	−0.03454 (12)	0.0419 (5)
C19	0.5894 (3)	0.2506 (3)	−0.00192 (12)	0.0419 (5)
C20	0.7126 (3)	0.1727 (3)	−0.03704 (14)	0.0518 (6)
H20	0.8390	0.2047	−0.0161	0.062*
C21	0.6529 (3)	0.0533 (3)	−0.10000 (14)	0.0552 (6)
H21	0.7382	0.0044	−0.1209	0.066*
C22	0.4635 (3)	0.0022 (3)	−0.13423 (13)	0.0460 (6)
C23	0.3358 (3)	0.0756 (3)	−0.10137 (12)	0.0422 (5)
C24	0.1464 (4)	0.0254 (3)	−0.13600 (14)	0.0582 (7)
H24	0.0612	0.0739	−0.1147	0.070*
C25	0.0862 (4)	−0.0921 (3)	−0.19974 (16)	0.0677 (8)
H25	−0.0393	−0.1237	−0.2217	0.081*
C26	0.2131 (4)	−0.1659 (3)	−0.23247 (15)	0.0669 (8)
H26	0.1715	−0.2467	−0.2761	0.080*
C27	0.3962 (4)	−0.1200 (3)	−0.20072 (14)	0.0604 (7)
H27	0.4792	−0.1697	−0.2231	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0453 (12)	0.0502 (11)	0.0435 (11)	0.0087 (9)	0.0039 (9)	0.0134 (9)
N2	0.0551 (13)	0.0511 (12)	0.0396 (11)	0.0148 (10)	0.0066 (10)	0.0086 (9)
O1	0.0478 (10)	0.0605 (10)	0.0468 (9)	0.0058 (8)	0.0015 (8)	0.0198 (8)
O2	0.0626 (11)	0.0590 (11)	0.0434 (10)	0.0119 (9)	0.0087 (8)	0.0069 (8)
O3	0.0413 (9)	0.0685 (11)	0.0573 (10)	0.0017 (8)	0.0116 (8)	0.0277 (9)
O4	0.0453 (10)	0.0706 (12)	0.0605 (11)	0.0237 (9)	0.0085 (8)	0.0031 (9)
C1	0.0471 (14)	0.0396 (12)	0.0447 (13)	0.0090 (11)	0.0113 (11)	0.0087 (10)
C2	0.0585 (16)	0.0495 (14)	0.0412 (13)	0.0188 (12)	0.0078 (11)	0.0081 (11)
C3	0.0747 (19)	0.0512 (15)	0.0442 (14)	0.0223 (13)	0.0116 (13)	0.0113 (11)
C4	0.0441 (15)	0.0763 (18)	0.0544 (16)	0.0052 (13)	0.0058 (12)	0.0158 (14)
C5	0.0420 (13)	0.0375 (12)	0.0426 (13)	0.0075 (10)	0.0103 (11)	0.0034 (10)
C6	0.0445 (13)	0.0351 (12)	0.0408 (13)	0.0067 (10)	0.0145 (11)	0.0071 (10)
C7	0.0403 (13)	0.0343 (11)	0.0376 (12)	0.0070 (10)	0.0084 (10)	0.0053 (9)
C8	0.0430 (13)	0.0431 (13)	0.0539 (15)	0.0020 (11)	0.0112 (12)	0.0102 (11)
C9	0.0600 (16)	0.0413 (13)	0.0504 (15)	0.0067 (12)	0.0157 (13)	0.0164 (11)
C10	0.0529 (15)	0.0363 (12)	0.0448 (14)	0.0150 (11)	0.0103 (12)	0.0054 (10)
C11	0.0424 (13)	0.0393 (12)	0.0417 (13)	0.0127 (10)	0.0088 (10)	0.0052 (10)
C12	0.0428 (14)	0.0619 (16)	0.0589 (16)	0.0134 (12)	0.0089 (12)	0.0107 (13)
C13	0.0509 (16)	0.0782 (19)	0.0696 (19)	0.0214 (14)	−0.0028 (14)	0.0092 (16)
C14	0.076 (2)	0.0709 (18)	0.0596 (17)	0.0337 (16)	−0.0010 (15)	0.0152 (14)
C15	0.0749 (19)	0.0511 (15)	0.0553 (16)	0.0245 (14)	0.0129 (14)	0.0161 (12)
C16	0.0544 (17)	0.083 (2)	0.0582 (17)	0.0127 (14)	0.0003 (13)	0.0089 (14)
C17	0.0450 (14)	0.0517 (14)	0.0406 (13)	0.0115 (11)	0.0052 (11)	0.0213 (11)
C18	0.0390 (13)	0.0483 (13)	0.0447 (13)	0.0163 (11)	0.0123 (11)	0.0180 (11)
C19	0.0415 (13)	0.0496 (13)	0.0389 (13)	0.0142 (11)	0.0081 (10)	0.0187 (10)
C20	0.0400 (14)	0.0594 (16)	0.0589 (16)	0.0165 (12)	0.0073 (12)	0.0170 (13)
C21	0.0497 (16)	0.0591 (16)	0.0639 (17)	0.0251 (13)	0.0170 (13)	0.0137 (13)
C22	0.0502 (15)	0.0424 (13)	0.0500 (14)	0.0145 (11)	0.0118 (12)	0.0182 (11)
C23	0.0428 (13)	0.0426 (13)	0.0447 (13)	0.0129 (10)	0.0072 (11)	0.0175 (10)
C24	0.0511 (16)	0.0580 (16)	0.0629 (17)	0.0149 (13)	0.0031 (13)	0.0110 (13)
C25	0.0582 (17)	0.0597 (17)	0.074 (2)	0.0070 (14)	−0.0095 (15)	0.0113 (15)
C26	0.083 (2)	0.0475 (15)	0.0576 (17)	0.0083 (15)	−0.0031 (16)	0.0039 (13)
C27	0.074 (2)	0.0469 (15)	0.0600 (17)	0.0194 (14)	0.0116 (15)	0.0090 (12)

N1—C5	1.284 (3)	C10—C11	1.413 (3)
N1—O1	1.408 (2)	C11—C12	1.422 (3)
N2—C17	1.287 (3)	C12—C13	1.356 (3)
N2—O2	1.404 (2)	C12—H12	0.9300
O1—C1	1.426 (2)	C13—C14	1.391 (4)
O2—C3	1.427 (3)	C13—H13	0.9300
O3—C6	1.350 (2)	C14—C15	1.357 (4)
O3—H3	0.8200	C14—H14	0.9300
O4—C18	1.345 (3)	C15—H15	0.9300
O4—H4	0.8200	C16—C17	1.498 (3)
C1—C2	1.497 (3)	C16—H16A	0.9600
C1—H1A	0.9700	C16—H16B	0.9600
C1—H1B	0.9700	C16—H16C	0.9600
C2—C3	1.514 (3)	C17—C19	1.473 (3)
C2—H2A	0.9700	C18—C19	1.393 (3)
C2—H2B	0.9700	C18—C23	1.424 (3)
C3—H3A	0.9700	C19—C20	1.417 (3)
C3—H3B	0.9700	C20—C21	1.355 (3)
C4—C5	1.502 (3)	C20—H20	0.9300
C4—H4A	0.9600	C21—C22	1.408 (3)
C4—H4B	0.9600	C21—H21	0.9300
C4—H4C	0.9600	C22—C23	1.405 (3)
C5—C7	1.469 (3)	C22—C27	1.414 (3)
C6—C7	1.392 (3)	C23—C24	1.410 (3)
C6—C11	1.418 (3)	C24—C25	1.356 (3)
C7—C8	1.420 (3)	C24—H24	0.9300
C8—C9	1.356 (3)	C25—C26	1.401 (4)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.414 (3)	C26—C27	1.355 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C15	1.412 (3)	C27—H27	0.9300
C5—N1—O1	114.40 (18)	C13—C12—C11	120.2 (2)
C17—N2—O2	113.84 (19)	C13—C12—H12	119.9
N1—O1—C1	107.51 (15)	C11—C12—H12	119.9
N2—O2—C3	108.21 (17)	C12—C13—C14	121.1 (3)
C6—O3—H3	109.5	C12—C13—H13	119.4
C18—O4—H4	109.5	C14—C13—H13	119.4
O1—C1—C2	108.60 (18)	C15—C14—C13	120.1 (3)
O1—C1—H1A	110.0	C15—C14—H14	119.9
C2—C1—H1A	110.0	C13—C14—H14	119.9
O1—C1—H1B	110.0	C14—C15—C10	121.1 (2)
C2—C1—H1B	110.0	C14—C15—H15	119.4
H1A—C1—H1B	108.4	C10—C15—H15	119.4
C1—C2—C3	111.5 (2)	C17—C16—H16A	109.5
C1—C2—H2A	109.3	C17—C16—H16B	109.5
C3—C2—H2A	109.3	H16A—C16—H16B	109.5
C1—C2—H2B	109.3	C17—C16—H16C	109.5
C3—C2—H2B	109.3	H16A—C16—H16C	109.5
H2A—C2—H2B	108.0	H16B—C16—H16C	109.5
O2—C3—C2	112.91 (19)	N2—C17—C19	116.1 (2)
O2—C3—H3A	109.0	N2—C17—C16	122.3 (2)
C2—C3—H3A	109.0	C19—C17—C16	121.5 (2)
O2—C3—H3B	109.0	O4—C18—C19	123.0 (2)
C2—C3—H3B	109.0	O4—C18—C23	115.8 (2)
H3A—C3—H3B	107.8	C19—C18—C23	121.2 (2)
C5—C4—H4A	109.5	C18—C19—C20	117.3 (2)
C5—C4—H4B	109.5	C18—C19—C17	122.1 (2)
H4A—C4—H4B	109.5	C20—C19—C17	120.6 (2)
C5—C4—H4C	109.5	C21—C20—C19	122.4 (2)
H4A—C4—H4C	109.5	C21—C20—H20	118.8
H4B—C4—H4C	109.5	C19—C20—H20	118.8
N1—C5—C7	116.2 (2)	C20—C21—C22	120.9 (2)
N1—C5—C4	122.4 (2)	C20—C21—H21	119.6
C7—C5—C4	121.34 (19)	C22—C21—H21	119.6
O3—C6—C7	122.7 (2)	C23—C22—C21	118.9 (2)
O3—C6—C11	116.03 (19)	C23—C22—C27	118.5 (2)
C7—C6—C11	121.28 (19)	C21—C22—C27	122.6 (2)
C6—C7—C8	117.5 (2)	C22—C23—C24	118.9 (2)
C6—C7—C5	122.24 (19)	C22—C23—C18	119.4 (2)
C8—C7—C5	120.3 (2)	C24—C23—C18	121.7 (2)
C9—C8—C7	122.2 (2)	C25—C24—C23	121.2 (3)
C9—C8—H8	118.9	C25—C24—H24	119.4
C7—C8—H8	118.9	C23—C24—H24	119.4
C8—C9—C10	120.9 (2)	C24—C25—C26	120.0 (3)
C8—C9—H9	119.5	C24—C25—H25	120.0
C10—C9—H9	119.5	C26—C25—H25	120.0
C15—C10—C11	118.6 (2)	C27—C26—C25	120.2 (2)
C15—C10—C9	123.0 (2)	C27—C26—H26	119.9
C11—C10—C9	118.4 (2)	C25—C26—H26	119.9
C10—C11—C6	119.6 (2)	C26—C27—C22	121.2 (3)
C10—C11—C12	118.8 (2)	C26—C27—H27	119.4
C6—C11—C12	121.6 (2)	C22—C27—H27	119.4
C5—N1—O1—C1	168.65 (19)	C13—C14—C15—C10	−0.5 (4)
C17—N2—O2—C3	−178.59 (18)	C11—C10—C15—C14	1.0 (4)
N1—O1—C1—C2	178.37 (17)	C9—C10—C15—C14	−177.7 (2)
O1—C1—C2—C3	178.99 (18)	O2—N2—C17—C19	−179.28 (16)
N2—O2—C3—C2	72.6 (2)	O2—N2—C17—C16	−0.2 (3)
C1—C2—C3—O2	63.2 (3)	O4—C18—C19—C20	178.18 (19)
O1—N1—C5—C7	179.14 (16)	C23—C18—C19—C20	−1.3 (3)
O1—N1—C5—C4	−1.8 (3)	O4—C18—C19—C17	−1.4 (3)
O3—C6—C7—C8	178.1 (2)	C23—C18—C19—C17	179.14 (19)
C11—C6—C7—C8	−1.7 (3)	N2—C17—C19—C18	4.1 (3)
O3—C6—C7—C5	−0.5 (3)	C16—C17—C19—C18	−175.1 (2)
C11—C6—C7—C5	179.8 (2)	N2—C17—C19—C20	−175.5 (2)
N1—C5—C7—C6	7.2 (3)	C16—C17—C19—C20	5.4 (3)
C4—C5—C7—C6	−171.8 (2)	C18—C19—C20—C21	0.3 (3)
N1—C5—C7—C8	−171.3 (2)	C17—C19—C20—C21	179.9 (2)
C4—C5—C7—C8	9.7 (3)	C19—C20—C21—C22	0.8 (4)
C6—C7—C8—C9	−0.1 (3)	C20—C21—C22—C23	−0.9 (3)
C5—C7—C8—C9	178.5 (2)	C20—C21—C22—C27	178.8 (2)
C7—C8—C9—C10	0.8 (4)	C21—C22—C23—C24	179.4 (2)
C8—C9—C10—C15	178.9 (2)	C27—C22—C23—C24	−0.3 (3)
C8—C9—C10—C11	0.2 (3)	C21—C22—C23—C18	−0.1 (3)
C15—C10—C11—C6	179.3 (2)	C27—C22—C23—C18	−179.8 (2)
C9—C10—C11—C6	−1.9 (3)	O4—C18—C23—C22	−178.33 (19)
C15—C10—C11—C12	−0.8 (3)	C19—C18—C23—C22	1.2 (3)
C9—C10—C11—C12	178.0 (2)	O4—C18—C23—C24	2.2 (3)
O3—C6—C11—C10	−177.05 (19)	C19—C18—C23—C24	−178.3 (2)
C7—C6—C11—C10	2.7 (3)	C22—C23—C24—C25	0.3 (3)
O3—C6—C11—C12	3.1 (3)	C18—C23—C24—C25	179.8 (2)
C7—C6—C11—C12	−177.2 (2)	C23—C24—C25—C26	−0.1 (4)
C10—C11—C12—C13	0.2 (3)	C24—C25—C26—C27	−0.1 (4)
C6—C11—C12—C13	−179.9 (2)	C25—C26—C27—C22	0.2 (4)
C11—C12—C13—C14	0.3 (4)	C23—C22—C27—C26	0.1 (3)
C12—C13—C14—C15	−0.2 (4)	C21—C22—C27—C26	−179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	1.83	2.543 (2)	145
O4—H4···N2	0.82	1.82	2.540 (2)	146
C12—H12···O3i	0.93	2.68	3.588 (3)	166
C1—H1B···Cg1ii	0.97	2.78	3.480 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	1.83	2.543 (2)	145
O4—H4⋯N2	0.82	1.82	2.540 (2)	146
C12—H12⋯O3i	0.93	2.68	3.588 (3)	166
C1—H1B⋯Cg1ii	0.97	2.78	3.480 (2)	129

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C6–C15 ring.