1,4-Bis(4-nitro-styr-yl)benzene.

The complete molecule of the title compound, C(22)H(16)N(2)O(4), is generated by a crystallographic centre of inversion. The plane of the central aromatic ring is tilted by 11.85 (4)° with respect to the outer aromatic ring. The crystal packing is determined by van der Waals inter-actions, with stair-like stacking between adjacent aromatic rings. The stacks are staggered and each layer is approximately 3.8 Å from the next. The closest inter-molecular contact (approximately 2.42 Å) is between an O atom and a vinyl H atom.

Related literature

For background information on photonic materials, see: He et al. (2008 ▶). For stilbenes, see: Moreno-Fuquen et al. (2008 ▶, 2009 ▶). For the synthesis, see: Borsche (1912 ▶); Nakatsuji et al. (1991 ▶). For a related structure, see: Bazan et al. (2000 ▶).

Experimental

Crystal data

C22H16N2O4

M = 372.37

Monoclinic,

a = 7.4689 (12) Å

b = 16.615 (3) Å

c = 7.3917 (12) Å

β = 108.824 (3)°

V = 868.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.40 × 0.18 × 0.12 mm

Data collection

Bruker SMART Platform CCD diffractometer

Absorption correction: none

10088 measured reflections

2001 independent reflections

1486 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.116

S = 1.02

2001 reflections

159 parameters

All H-atom parameters refined

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024751/ng2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024751/ng2592Isup2.hkl

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

C22H16N2O4	F(000) = 388
Mr = 372.37	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 851 reflections
a = 7.4689 (12) Å	θ = 2.5–27.5°
b = 16.615 (3) Å	µ = 0.10 mm−1
c = 7.3917 (12) Å	T = 173 K
β = 108.824 (3)°	Needle, yellow
V = 868.2 (2) Å3	0.40 × 0.18 × 0.12 mm
Z = 2

Bruker SMART Platform CCD diffractometer	1486 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.041
graphite	θmax = 27.5°, θmin = 2.5°
ω scans	h = −9→9
10088 measured reflections	k = −21→21
2001 independent reflections	l = −9→9

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.1981P] where P = (Fo2 + 2Fc2)/3
2001 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.18 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	−0.18351 (16)	0.18081 (7)	−0.31257 (17)	0.0314 (3)
O1	−0.31485 (14)	0.14204 (7)	−0.29133 (16)	0.0424 (3)
O2	−0.20374 (14)	0.23244 (7)	−0.43745 (15)	0.0415 (3)
C1	0.00888 (18)	0.16483 (8)	−0.18509 (19)	0.0268 (3)
C2	0.03516 (19)	0.10424 (8)	−0.0511 (2)	0.0293 (3)
H2	−0.068 (2)	0.0758 (9)	−0.037 (2)	0.034 (4)*
C3	0.2169 (2)	0.08605 (8)	0.0623 (2)	0.0299 (3)
H3	0.234 (2)	0.0439 (10)	0.154 (2)	0.036 (4)*
C4	0.37281 (19)	0.12795 (8)	0.04412 (18)	0.0274 (3)
C5	0.3394 (2)	0.19080 (9)	−0.0888 (2)	0.0309 (3)
H5	0.440 (2)	0.2209 (9)	−0.102 (2)	0.032 (4)*
C6	0.1573 (2)	0.20926 (9)	−0.2043 (2)	0.0302 (3)
H6	0.137 (2)	0.2519 (10)	−0.294 (2)	0.037 (4)*
C7	0.56766 (19)	0.10807 (9)	0.1593 (2)	0.0304 (3)
H7	0.659 (2)	0.1468 (9)	0.145 (2)	0.036 (4)*
C8	0.62118 (19)	0.04369 (9)	0.27155 (19)	0.0296 (3)
H8	0.530 (2)	0.0058 (9)	0.282 (2)	0.027 (4)*
C9	0.81506 (18)	0.02312 (8)	0.38677 (18)	0.0270 (3)
C10	0.9717 (2)	0.07130 (9)	0.39725 (19)	0.0291 (3)
H10	0.959 (2)	0.1202 (10)	0.333 (2)	0.040 (4)*
C11	0.8479 (2)	−0.04871 (9)	0.49188 (19)	0.0295 (3)
H11	0.740 (2)	−0.0827 (10)	0.482 (2)	0.039 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0255 (6)	0.0340 (7)	0.0330 (6)	0.0040 (5)	0.0072 (5)	−0.0046 (5)
O1	0.0245 (5)	0.0545 (7)	0.0467 (7)	−0.0036 (5)	0.0091 (5)	−0.0009 (5)
O2	0.0348 (6)	0.0417 (6)	0.0426 (6)	0.0100 (5)	0.0050 (5)	0.0105 (5)
C1	0.0224 (6)	0.0296 (7)	0.0267 (7)	0.0041 (5)	0.0054 (5)	−0.0038 (5)
C2	0.0261 (7)	0.0292 (7)	0.0330 (7)	−0.0030 (5)	0.0103 (6)	−0.0011 (6)
C3	0.0309 (7)	0.0280 (7)	0.0299 (7)	−0.0001 (5)	0.0087 (6)	0.0026 (6)
C4	0.0267 (7)	0.0279 (7)	0.0260 (7)	0.0015 (5)	0.0064 (5)	−0.0017 (5)
C5	0.0246 (7)	0.0322 (7)	0.0355 (8)	−0.0021 (5)	0.0093 (6)	0.0031 (6)
C6	0.0295 (7)	0.0293 (7)	0.0312 (7)	0.0027 (5)	0.0089 (6)	0.0056 (6)
C7	0.0244 (7)	0.0331 (8)	0.0314 (7)	−0.0010 (6)	0.0059 (6)	−0.0005 (6)
C8	0.0260 (7)	0.0312 (7)	0.0300 (7)	0.0002 (6)	0.0071 (5)	−0.0017 (6)
C9	0.0278 (7)	0.0301 (7)	0.0221 (6)	0.0037 (5)	0.0066 (5)	−0.0032 (5)
C10	0.0313 (7)	0.0283 (7)	0.0268 (7)	0.0034 (5)	0.0082 (5)	0.0026 (5)
C11	0.0270 (7)	0.0313 (7)	0.0294 (7)	−0.0008 (5)	0.0082 (5)	−0.0011 (6)

N1—O1	1.2253 (16)	C5—H5	0.932 (16)
N1—O2	1.2332 (15)	C6—H6	0.950 (16)
N1—C1	1.4661 (17)	C7—C8	1.334 (2)
C1—C6	1.3765 (19)	C7—H7	0.969 (16)
C1—C2	1.381 (2)	C8—C9	1.4640 (19)
C2—C3	1.379 (2)	C8—H8	0.951 (15)
C2—H2	0.940 (16)	C9—C10	1.399 (2)
C3—C4	1.4001 (19)	C9—C11	1.4020 (19)
C3—H3	0.953 (16)	C10—C11i	1.384 (2)
C4—C5	1.3999 (19)	C10—H10	0.930 (17)
C4—C7	1.4670 (19)	C11—C10i	1.384 (2)
C5—C6	1.3868 (19)	C11—H11	0.968 (17)
O1—N1—O2	123.49 (12)	C1—C6—C5	118.71 (13)
O1—N1—C1	118.79 (12)	C1—C6—H6	121.2 (10)
O2—N1—C1	117.71 (11)	C5—C6—H6	120.1 (10)
C6—C1—C2	122.13 (12)	C8—C7—C4	125.71 (13)
C6—C1—N1	119.44 (12)	C8—C7—H7	121.2 (9)
C2—C1—N1	118.42 (12)	C4—C7—H7	113.1 (9)
C3—C2—C1	118.68 (13)	C7—C8—C9	126.21 (14)
C3—C2—H2	120.4 (9)	C7—C8—H8	120.2 (9)
C1—C2—H2	120.9 (9)	C9—C8—H8	113.6 (9)
C2—C3—C4	121.26 (13)	C10—C9—C11	117.57 (12)
C2—C3—H3	118.2 (9)	C10—C9—C8	123.46 (13)
C4—C3—H3	120.6 (9)	C11—C9—C8	118.97 (13)
C5—C4—C3	118.20 (12)	C11i—C10—C9	120.98 (13)
C5—C4—C7	119.61 (13)	C11i—C10—H10	117.5 (10)
C3—C4—C7	122.18 (13)	C9—C10—H10	121.5 (10)
C6—C5—C4	120.96 (13)	C10i—C11—C9	121.45 (13)
C6—C5—H5	118.6 (9)	C10i—C11—H11	121.0 (9)
C4—C5—H5	120.5 (9)	C9—C11—H11	117.6 (9)
O1—N1—C1—C6	−178.44 (12)	N1—C1—C6—C5	−176.92 (12)
O2—N1—C1—C6	2.28 (19)	C4—C5—C6—C1	0.4 (2)
O1—N1—C1—C2	2.67 (19)	C5—C4—C7—C8	−170.57 (14)
O2—N1—C1—C2	−176.61 (12)	C3—C4—C7—C8	9.5 (2)
C6—C1—C2—C3	−2.3 (2)	C4—C7—C8—C9	179.87 (13)
N1—C1—C2—C3	176.57 (12)	C7—C8—C9—C10	1.9 (2)
C1—C2—C3—C4	0.3 (2)	C7—C8—C9—C11	−177.62 (13)
C2—C3—C4—C5	1.9 (2)	C11—C9—C10—C11i	−0.2 (2)
C2—C3—C4—C7	−178.18 (13)	C8—C9—C10—C11i	−179.77 (13)
C3—C4—C5—C6	−2.3 (2)	C10—C9—C11—C10i	0.2 (2)
C7—C4—C5—C6	177.80 (13)	C8—C9—C11—C10i	179.80 (13)
C2—C1—C6—C5	1.9 (2)