Crystal structure of N,N'-bis-[(pyridin-4-yl)meth-yl]naphthalene di-imide.

In the centrosymmetric title compound, C26H16N4O4 {systematic name: 6,13-bis-[(pyridin-4-yl)meth-yl]-6,13-di-aza-tetra-cyclo-[6.6.2.0(4,16)0(11,15)]hexa-deca-1,3,8,10,15-pantaene-5,7,12,14-tetrone}, the central ring system is essentially planar [maximum deviation = 0.0234 (8) Å] and approximately perpendicular to the terminal pyridine ring [dihedral angle = 84.38 (3)°]. The mol-ecules displays a trans conformation with the (pyridin-4-yl)methyl groups on both sides of the central naphthalene di-imide plane. In the crystal, mol-ecules are linked by π-π stacking between parallel pyridine rings [centroid-centroid distances = 3.7014 (8) and 3.8553 (8) Å] and weak C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular architecture.

Related literature

For crystal structures of related compounds, see: Xu et al. (2011 ▶); Reczek et al. (2006 ▶); Li et al. (2009 ▶). For colorimetric applications and nanoscale properties, see: Pandeeswar et al. (2014 ▶); Trivedi et al. (2009 ▶); Matsunaga et al. (2014 ▶); Pantoş et al. (2007 ▶). For the design of transistors, see: Jung et al. (2009 ▶); Oh et al. (2010 ▶). For organic supra­molecular solids, see: Cheney et al. (2007 ▶). For the design and synthesis of one-dimensional coordination polymers, see: Li et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C26H16N4O4

M = 448.43

Triclinic,

a = 5.5891 (4) Å

b = 7.5232 (5) Å

c = 11.9525 (8) Å

α = 77.093 (3)°

β = 88.445 (4)°

γ = 87.590 (4)°

V = 489.37 (6) Å3

Z = 1

Cu Kα radiation

μ = 0.87 mm−1

T = 296 K

0.34 × 0.13 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.555, T max = 0.753

14032 measured reflections

1748 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.05

1748 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814017917/xu5806sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017917/xu5806Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814017917/xu5806fig1.tif

The structure with displacement ellipsoids drawn at the 30% probability level and H atoms as small sphere of arbitrary radii.

Click here for additional data file.

p . DOI: 10.1107/S1600536814017917/xu5806fig2.tif

View p-stacking inter­actions in the crystal.

CCDC reference: 1017799

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H16N4O4	Z = 1
Mr = 448.43	F(000) = 232
Triclinic, P1	Dx = 1.522 Mg m−3
a = 5.5891 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.5232 (5) Å	Cell parameters from 9981 reflections
c = 11.9525 (8) Å	θ = 3.8–68.3°
α = 77.093 (3)°	µ = 0.87 mm−1
β = 88.445 (4)°	T = 296 K
γ = 87.590 (4)°	Plate, colourless
V = 489.37 (6) Å3	0.34 × 0.13 × 0.08 mm

Bruker APEXII CCD diffractometer	1748 independent reflections
Radiation source: Incoatec ImuS	1643 reflections with I > 2σ(I)
Mirrors monochromator	Rint = 0.045
ω scans	θmax = 68.3°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→6
Tmin = 0.555, Tmax = 0.753	k = −9→9
14032 measured reflections	l = −14→14

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0617P)2 + 0.0799P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1748 reflections	Δρmax = 0.19 e Å−3
154 parameters	Δρmin = −0.19 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.

	x	y	z	Uiso*/Ueq
O1	0.43898 (16)	0.61174 (13)	0.75255 (7)	0.0471 (3)
N1	−0.0333 (2)	0.68325 (18)	1.12186 (9)	0.0587 (3)
C1	0.1698 (3)	0.7665 (2)	1.09030 (12)	0.0600 (4)
H1	0.2727	0.7785	1.1478	0.072*
O2	−0.21818 (18)	0.96340 (12)	0.62202 (8)	0.0540 (3)
N2	0.10767 (18)	0.78494 (13)	0.68880 (8)	0.0375 (3)
C2	0.2394 (2)	0.83681 (19)	0.97785 (11)	0.0482 (3)
H2	0.3847	0.8938	0.9613	0.058*
C6	0.1602 (2)	0.90343 (17)	0.76740 (10)	0.0425 (3)
H6A	0.0742	1.0198	0.7428	0.051*
H6B	0.3301	0.9262	0.7628	0.051*
C3	0.0913 (2)	0.82151 (15)	0.89059 (9)	0.0372 (3)
C5	−0.1744 (3)	0.66899 (19)	1.03678 (12)	0.0511 (3)
H5	−0.3183	0.6110	1.0560	0.061*
C4	−0.1216 (2)	0.73457 (17)	0.92155 (10)	0.0435 (3)
H4	−0.2276	0.7204	0.8658	0.052*
C7	0.2667 (2)	0.63581 (16)	0.69075 (9)	0.0360 (3)
C8	0.2169 (2)	0.51409 (15)	0.61294 (9)	0.0337 (3)
C9	0.02134 (19)	0.55699 (14)	0.53820 (8)	0.0315 (3)
C10	−0.1324 (2)	0.71073 (15)	0.53795 (9)	0.0340 (3)
C11	−0.0899 (2)	0.83074 (15)	0.61813 (9)	0.0376 (3)
C12	0.3627 (2)	0.36316 (16)	0.61186 (9)	0.0383 (3)
H12	0.4906	0.3354	0.6618	0.046*
C13	−0.3204 (2)	0.74975 (16)	0.46403 (10)	0.0384 (3)
H13	−0.4206	0.8516	0.4641	0.046*

	U11	U22	U33	U12	U13	U23
O1	0.0449 (5)	0.0592 (6)	0.0403 (5)	−0.0028 (4)	−0.0085 (4)	−0.0169 (4)
N1	0.0686 (8)	0.0691 (8)	0.0368 (6)	0.0111 (6)	0.0030 (5)	−0.0118 (5)
C1	0.0676 (10)	0.0771 (10)	0.0401 (7)	0.0099 (7)	−0.0136 (6)	−0.0243 (7)
O2	0.0626 (6)	0.0463 (5)	0.0580 (6)	0.0133 (4)	−0.0097 (4)	−0.0237 (4)
N2	0.0465 (6)	0.0387 (5)	0.0292 (5)	−0.0039 (4)	0.0003 (4)	−0.0113 (4)
C2	0.0479 (8)	0.0572 (8)	0.0454 (7)	0.0002 (5)	−0.0060 (5)	−0.0234 (6)
C6	0.0530 (7)	0.0405 (6)	0.0372 (6)	−0.0087 (5)	0.0007 (5)	−0.0143 (5)
C3	0.0436 (6)	0.0356 (6)	0.0358 (6)	0.0031 (4)	−0.0018 (4)	−0.0156 (4)
C5	0.0508 (8)	0.0541 (7)	0.0456 (7)	0.0033 (6)	0.0064 (6)	−0.0074 (6)
C4	0.0454 (7)	0.0467 (7)	0.0391 (6)	−0.0006 (5)	−0.0036 (5)	−0.0108 (5)
C7	0.0376 (6)	0.0437 (6)	0.0264 (5)	−0.0056 (4)	0.0017 (4)	−0.0069 (4)
C8	0.0368 (6)	0.0388 (6)	0.0249 (5)	−0.0027 (4)	0.0023 (4)	−0.0060 (4)
C9	0.0349 (6)	0.0351 (6)	0.0235 (5)	−0.0026 (4)	0.0032 (4)	−0.0044 (4)
C10	0.0384 (6)	0.0356 (6)	0.0272 (5)	−0.0012 (4)	0.0026 (4)	−0.0055 (4)
C11	0.0436 (7)	0.0364 (6)	0.0325 (6)	−0.0003 (5)	0.0021 (4)	−0.0077 (4)
C12	0.0376 (6)	0.0453 (6)	0.0304 (6)	0.0027 (5)	−0.0051 (4)	−0.0055 (5)
C13	0.0420 (6)	0.0376 (6)	0.0346 (6)	0.0061 (5)	−0.0002 (4)	−0.0071 (4)

N1—C1	1.325 (2)	C5—H5	0.9300
N1—C5	1.3293 (19)	C6—H6A	0.9700
N2—C11	1.3931 (16)	C6—H6B	0.9700
N2—C7	1.3982 (16)	C7—C8	1.4823 (16)
N2—C6	1.4746 (14)	C8—C12	1.3718 (16)
O1—C7	1.2123 (14)	C8—C9	1.4110 (16)
O2—C11	1.2127 (15)	C9—C10	1.4113 (16)
C1—C2	1.382 (2)	C9—C9i	1.416 (2)
C1—H1	0.9300	C10—C13	1.3708 (17)
C2—C3	1.3766 (17)	C10—C11	1.4855 (16)
C2—H2	0.9300	C12—C13i	1.4046 (17)
C3—C4	1.3836 (18)	C12—H12	0.9300
C3—C6	1.5100 (16)	C13—C12i	1.4046 (17)
C4—C5	1.3834 (18)	C13—H13	0.9300
C4—H4	0.9300
C1—N1—C5	115.61 (12)	C3—C6—H6B	109.0
C11—N2—C7	125.48 (10)	H6A—C6—H6B	107.8
C11—N2—C6	118.44 (10)	O1—C7—N2	120.35 (10)
C7—N2—C6	116.06 (10)	O1—C7—C8	122.58 (11)
N1—C1—C2	124.53 (13)	N2—C7—C8	117.06 (10)
N1—C1—H1	117.7	C12—C8—C9	120.29 (11)
C2—C1—H1	117.7	C12—C8—C7	120.26 (11)
C3—C2—C1	119.25 (13)	C9—C8—C7	119.44 (10)
C3—C2—H2	120.4	C8—C9—C10	121.50 (11)
C1—C2—H2	120.4	C8—C9—C9i	119.18 (13)
C2—C3—C4	117.23 (11)	C10—C9—C9i	119.32 (13)
C2—C3—C6	120.00 (11)	C13—C10—C9	120.29 (11)
C4—C3—C6	122.74 (11)	C13—C10—C11	119.95 (10)
C5—C4—C3	118.95 (12)	C9—C10—C11	119.77 (11)
C5—C4—H4	120.5	O2—C11—N2	120.98 (11)
C3—C4—H4	120.5	O2—C11—C10	122.31 (11)
N1—C5—C4	124.44 (13)	N2—C11—C10	116.70 (10)
N1—C5—H5	117.8	C8—C12—C13i	120.51 (11)
C4—C5—H5	117.8	C8—C12—H12	119.7
N2—C6—C3	112.85 (9)	C13i—C12—H12	119.7
N2—C6—H6A	109.0	C10—C13—C12i	120.41 (10)
C3—C6—H6A	109.0	C10—C13—H13	119.8
N2—C6—H6B	109.0	C12i—C13—H13	119.8
C5—N1—C1—C2	0.1 (2)	C12—C8—C9—C10	179.61 (9)
N1—C1—C2—C3	0.0 (2)	C7—C8—C9—C10	−1.78 (16)
C11—N2—C6—C3	104.43 (12)	C12—C8—C9—C9i	−0.36 (19)
C7—N2—C6—C3	−76.70 (13)	C7—C8—C9—C9i	178.25 (10)
C1—C2—C3—C4	−0.20 (18)	C8—C9—C10—C13	179.67 (9)
C1—C2—C3—C6	177.80 (12)	C9i—C9—C10—C13	−0.36 (19)
N2—C6—C3—C2	139.13 (11)	C8—C9—C10—C11	−0.25 (17)
N2—C6—C3—C4	−42.99 (16)	C9i—C9—C10—C11	179.72 (10)
C1—N1—C5—C4	−0.1 (2)	C7—N2—C11—O2	−179.77 (10)
N1—C5—C4—C3	0.0 (2)	C6—N2—C11—O2	−1.01 (17)
C2—C3—C4—C5	0.19 (17)	C7—N2—C11—C10	−0.43 (17)
C6—C3—C4—C5	−177.75 (11)	C6—N2—C11—C10	178.33 (9)
C11—N2—C7—O1	177.16 (10)	C13—C10—C11—O2	0.79 (18)
C6—N2—C7—O1	−1.63 (16)	C9—C10—C11—O2	−179.29 (10)
C11—N2—C7—C8	−1.55 (16)	C13—C10—C11—N2	−178.55 (9)
C6—N2—C7—C8	179.67 (8)	C9—C10—C11—N2	1.38 (16)
O1—C7—C8—C12	2.58 (17)	C9—C8—C12—C13i	0.44 (17)
N2—C7—C8—C12	−178.75 (9)	C7—C8—C12—C13i	−178.16 (9)
O1—C7—C8—C9	−176.03 (10)	C9—C10—C13—C12i	0.29 (18)
N2—C7—C8—C9	2.64 (15)	C11—C10—C13—C12i	−179.78 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ii	0.93	2.59	3.5014 (15)	165
C13—H13···O2iii	0.93	2.51	3.3242 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.59	3.5014 (15)	165
C13—H13⋯O2ii	0.93	2.51	3.3242 (15)	146

Symmetry codes: (i) ; (ii) .