2,2'-[(1E,1'E)-2,2'-(2,5-Dibut-oxy-1,4-phenyl-ene)bis-(ethene-2,1-di-yl)]dipyridine.

The centrosymmetric title mol-ecule, C(28)H(32)N(2)O(2), has a central benzene ring subsituted in the 1- and 4-positions by (ethene-2,1-di-yl)pyridine groups, and in the 2- and 5-positions by but-oxy groups. The whole mol-ecule is X-shaped and relatively flat, the dihedral angle between the pyridine and the central benzene ring being 11.29 (10)°. In the crystal, neighboring mol-ecules are linked by weak C-H⋯N inter-actions, forming a two-dimensional undulating network.

Related literature

For information on pyridine-based photo-refractive materials, see: Naumov et al. (2002 ▶); Liu et al. (2008 ▶).

Experimental

Crystal data

C28H32N2O2

M = 428.56

Monoclinic,

a = 8.882 (5) Å

b = 13.892 (5) Å

c = 10.387 (5) Å

β = 107.392 (5)°

V = 1223.0 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.986

8512 measured reflections

2162 independent reflections

1385 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.154

S = 1.03

2162 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013656/su2172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013656/su2172Isup2.hkl

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

C28H32N2O2	F(000) = 460
Mr = 428.56	Dx = 1.164 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 1446 reflections
a = 8.882 (5) Å	θ = 2.5–21.8°
b = 13.892 (5) Å	µ = 0.07 mm−1
c = 10.387 (5) Å	T = 298 K
β = 107.392 (5)°	Block, yellow
V = 1223.0 (10) Å3	0.50 × 0.30 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2162 independent reflections
Radiation source: fine-focus sealed tube	1385 reflections with I > 2σ(I)
graphite	Rint = 0.040
phi and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.964, Tmax = 0.986	k = −16→16
8512 measured reflections	l = −11→12

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0821P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3
2162 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.10160 (17)	0.50961 (9)	0.22161 (12)	0.0589 (4)
C2	0.0431 (2)	0.57863 (13)	0.43825 (17)	0.0477 (5)
H2	0.0725	0.6313	0.3960	0.057*
C1	−0.0472 (2)	0.50707 (13)	0.36022 (17)	0.0458 (5)
C5	0.2548 (2)	0.72369 (13)	0.61936 (18)	0.0491 (5)
H5	0.2324	0.7310	0.5265	0.059*
C4	0.1898 (2)	0.64922 (13)	0.66286 (18)	0.0487 (5)
H4	0.2083	0.6442	0.7556	0.058*
C6	0.3587 (2)	0.79507 (14)	0.70512 (19)	0.0500 (5)
C3	0.0919 (2)	0.57414 (13)	0.57915 (17)	0.0447 (5)
N1	0.3841 (2)	0.78919 (14)	0.83829 (17)	0.0781 (6)
C7	0.4305 (3)	0.86549 (15)	0.6486 (2)	0.0617 (6)
H7	0.4106	0.8689	0.5556	0.074*
C11	−0.0751 (3)	0.59382 (15)	0.15295 (19)	0.0620 (6)
H11A	0.0359	0.5996	0.1601	0.074*
H11B	−0.1069	0.6507	0.1922	0.074*
C12	−0.1717 (3)	0.58404 (16)	0.00746 (18)	0.0639 (6)
H12A	−0.1503	0.5217	−0.0253	0.077*
H12B	−0.2826	0.5857	0.0020	0.077*
C8	0.5312 (3)	0.93013 (17)	0.7318 (3)	0.0770 (7)
H8	0.5797	0.9780	0.6957	0.092*
C10	0.4832 (3)	0.8533 (2)	0.9145 (2)	0.0988 (10)
H10	0.5018	0.8498	1.0074	0.119*
C9	0.5588 (3)	0.9232 (2)	0.8671 (3)	0.0907 (9)
H9	0.6277	0.9652	0.9258	0.109*
C13	−0.1405 (4)	0.6606 (2)	−0.0831 (2)	0.0963 (9)
H13A	−0.0302	0.6582	−0.0795	0.116*
H13B	−0.1603	0.7231	−0.0499	0.116*
C14	−0.2407 (4)	0.6502 (2)	−0.2276 (2)	0.0996 (10)
H14A	−0.2273	0.5868	−0.2594	0.149*
H14B	−0.2092	0.6972	−0.2822	0.149*
H14C	−0.3496	0.6599	−0.2335	0.149*

	U11	U22	U33	U12	U13	U23
O1	0.0777 (10)	0.0571 (9)	0.0353 (8)	−0.0123 (7)	0.0069 (7)	−0.0006 (6)
C2	0.0541 (12)	0.0462 (10)	0.0408 (11)	−0.0014 (9)	0.0111 (9)	−0.0001 (8)
C1	0.0492 (11)	0.0514 (11)	0.0330 (10)	0.0032 (9)	0.0066 (9)	−0.0017 (8)
C5	0.0514 (12)	0.0543 (12)	0.0386 (11)	0.0007 (9)	0.0090 (9)	−0.0031 (9)
C4	0.0550 (12)	0.0529 (11)	0.0346 (11)	−0.0021 (9)	0.0081 (9)	−0.0050 (8)
C6	0.0510 (12)	0.0529 (12)	0.0467 (12)	−0.0029 (9)	0.0155 (10)	−0.0073 (9)
C3	0.0466 (11)	0.0463 (11)	0.0387 (10)	0.0006 (8)	0.0090 (9)	−0.0034 (8)
N1	0.0928 (15)	0.0965 (15)	0.0456 (11)	−0.0454 (12)	0.0215 (10)	−0.0188 (10)
C7	0.0672 (14)	0.0618 (13)	0.0568 (13)	−0.0111 (11)	0.0194 (11)	−0.0026 (10)
C11	0.0807 (16)	0.0550 (13)	0.0478 (12)	−0.0075 (11)	0.0154 (11)	0.0028 (10)
C12	0.0770 (16)	0.0679 (14)	0.0421 (12)	−0.0073 (11)	0.0107 (11)	0.0048 (10)
C8	0.0811 (17)	0.0685 (15)	0.0898 (19)	−0.0262 (13)	0.0385 (14)	−0.0114 (13)
C10	0.115 (2)	0.129 (2)	0.0536 (15)	−0.067 (2)	0.0270 (15)	−0.0310 (15)
C9	0.0903 (19)	0.105 (2)	0.0823 (19)	−0.0484 (16)	0.0338 (15)	−0.0386 (16)
C13	0.131 (2)	0.0873 (18)	0.0572 (16)	−0.0271 (17)	0.0078 (16)	0.0158 (13)
C14	0.125 (3)	0.108 (2)	0.0532 (15)	−0.0132 (18)	0.0064 (15)	0.0242 (14)

O1—C1	1.375 (2)	C11—C12	1.504 (3)
O1—C11	1.426 (2)	C11—H11A	0.9700
C2—C1	1.379 (3)	C11—H11B	0.9700
C2—C3	1.398 (2)	C12—C13	1.499 (3)
C2—H2	0.9300	C12—H12A	0.9700
C1—C3i	1.406 (3)	C12—H12B	0.9700
C5—C4	1.328 (3)	C8—C9	1.356 (3)
C5—C6	1.462 (3)	C8—H8	0.9300
C5—H5	0.9300	C10—C9	1.353 (3)
C4—C3	1.466 (3)	C10—H10	0.9300
C4—H4	0.9300	C9—H9	0.9300
C6—N1	1.336 (2)	C13—C14	1.506 (3)
C6—C7	1.390 (3)	C13—H13A	0.9700
C3—C1i	1.406 (3)	C13—H13B	0.9700
N1—C10	1.334 (3)	C14—H14A	0.9600
C7—C8	1.375 (3)	C14—H14B	0.9600
C7—H7	0.9300	C14—H14C	0.9600
C1—O1—C11	119.07 (14)	H11A—C11—H11B	108.5
C1—C2—C3	121.80 (18)	C13—C12—C11	114.19 (19)
C1—C2—H2	119.1	C13—C12—H12A	108.7
C3—C2—H2	119.1	C11—C12—H12A	108.7
O1—C1—C2	123.88 (17)	C13—C12—H12B	108.7
O1—C1—C3i	115.58 (15)	C11—C12—H12B	108.7
C2—C1—C3i	120.53 (17)	H12A—C12—H12B	107.6
C4—C5—C6	125.48 (18)	C9—C8—C7	119.1 (2)
C4—C5—H5	117.3	C9—C8—H8	120.4
C6—C5—H5	117.3	C7—C8—H8	120.4
C5—C4—C3	126.43 (18)	N1—C10—C9	125.0 (2)
C5—C4—H4	116.8	N1—C10—H10	117.5
C3—C4—H4	116.8	C9—C10—H10	117.5
N1—C6—C7	121.57 (18)	C10—C9—C8	118.2 (2)
N1—C6—C5	118.03 (18)	C10—C9—H9	120.9
C7—C6—C5	120.38 (18)	C8—C9—H9	120.9
C2—C3—C1i	117.66 (16)	C12—C13—C14	113.1 (2)
C2—C3—C4	122.17 (17)	C12—C13—H13A	109.0
C1i—C3—C4	120.15 (16)	C14—C13—H13A	109.0
C10—N1—C6	116.8 (2)	C12—C13—H13B	109.0
C8—C7—C6	119.3 (2)	C14—C13—H13B	109.0
C8—C7—H7	120.4	H13A—C13—H13B	107.8
C6—C7—H7	120.4	C13—C14—H14A	109.5
O1—C11—C12	107.37 (16)	C13—C14—H14B	109.5
O1—C11—H11A	110.2	H14A—C14—H14B	109.5
C12—C11—H11A	110.2	C13—C14—H14C	109.5
O1—C11—H11B	110.2	H14A—C14—H14C	109.5
C12—C11—H11B	110.2	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1ii	0.93	2.70	3.446 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1i	0.93	2.70	3.446 (3)	138

Symmetry code: (i) .