Redetermination of 4-nitro-stilbene.

In the title compound, C(14)H(11)NO(2), the benzene rings are inclined to each other with a dihedral angle between their mean planes of 8.42 (6)°. The nitro group is almost coplanar with the attached benzene ring but is rotated about the C-N bond by 5.84 (12)°. This redetermination results in a crystal structure with significantly higher precision than the original determination [Hertel & Romer (1931 ▶). Z. Kristallogr.76, 467-469], and the intermolecular interactions have been established. In the crystal structure, mol-ecules are linked by C-H⋯O hydrogen bonds to generate C(5), C(13) and edge-fused R(3) (3)(28) rings.

Related literature

For a previous study of the title compound, see: Hertel & Romer (1931 ▶). For background information on photonic materials, see: Luo et al. (2003 ▶); Vidal et al. (2008 ▶); Park et al. (2004 ▶). For general background, see: Allen et al. (1987 ▶); Etter (1990 ▶); Nardelli (1995 ▶).

Experimental

Crystal data

C14H11NO2

M = 225.24

Orthorhombic,

a = 10.0839 (3) Å

b = 7.6849 (2) Å

c = 28.1176 (8) Å

V = 2178.94 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 123 (2) K

0.40 × 0.40 × 0.18 mm

Data collection

Oxford Xcalibur-S diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.965, T max = 0.985

13263 measured reflections

3173 independent reflections

2202 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.09

3173 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035459/hg2430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035459/hg2430Isup2.hkl

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

C14H11NO2	Dx = 1.373 Mg m−3
Mr = 225.24	Melting point: 421(1) K
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5152 reflections
a = 10.0839 (3) Å	θ = 2.7–30.7º
b = 7.6849 (2) Å	µ = 0.09 mm−1
c = 28.1176 (8) Å	T = 123 (2) K
V = 2178.94 (11) Å3	Cut lathe, light yellow
Z = 8	0.40 × 0.40 × 0.18 mm
F000 = 944

Oxford Xcalibur-S diffractometer	2202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Monochromator: graphite	θmax = 30.0º
ω scans	θmin = 2.9º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)	h = −14→12
Tmin = 0.965, Tmax = 0.985	k = −10→10
13263 measured reflections	l = −37→39
3173 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.491P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3173 reflections	Δρmax = 0.32 e Å−3
154 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.69853 (10)	0.14689 (14)	1.05469 (3)	0.0360 (3)
O2	0.51679 (11)	0.28695 (16)	1.04197 (4)	0.0453 (3)
N1	0.60967 (11)	0.19752 (15)	1.02843 (4)	0.0267 (3)
C1	0.61582 (12)	0.15108 (16)	0.97771 (4)	0.0209 (3)
C2	0.51199 (13)	0.19912 (17)	0.94826 (5)	0.0232 (3)
H2	0.4364	0.2572	0.9607	0.028*
C3	0.52059 (13)	0.16074 (16)	0.90021 (5)	0.0239 (3)
H3	0.4496	0.1910	0.8796	0.029*
C4	0.63344 (13)	0.07749 (15)	0.88166 (4)	0.0227 (3)
C5	0.73329 (13)	0.02692 (17)	0.91315 (5)	0.0247 (3)
H5	0.8083	−0.0340	0.9013	0.030*
C6	0.72573 (13)	0.06320 (16)	0.96111 (5)	0.0244 (3)
H6	0.7945	0.0285	0.9822	0.029*
C7	0.65267 (13)	0.04480 (16)	0.83078 (5)	0.0245 (3)
H7	0.7231	−0.0309	0.8221	0.029*
C8	0.58014 (13)	0.11181 (16)	0.79561 (4)	0.0236 (3)
H8	0.5084	0.1851	0.8044	0.028*
C9	0.60077 (12)	0.08280 (15)	0.74429 (4)	0.0218 (3)
C10	0.50863 (13)	0.15248 (16)	0.71267 (4)	0.0229 (3)
H10	0.4342	0.2142	0.7247	0.027*
C11	0.52360 (13)	0.13330 (17)	0.66384 (5)	0.0253 (3)
H11	0.4599	0.1819	0.6428	0.030*
C12	0.63151 (13)	0.04317 (16)	0.64595 (5)	0.0261 (3)
H12	0.6422	0.0302	0.6126	0.031*
C13	0.72366 (13)	−0.02793 (17)	0.67678 (5)	0.0263 (3)
H13	0.7973	−0.0904	0.6645	0.032*
C14	0.70911 (13)	−0.00852 (16)	0.72570 (5)	0.0246 (3)
H14	0.7730	−0.0575	0.7466	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0325 (6)	0.0503 (6)	0.0254 (5)	−0.0005 (5)	−0.0072 (5)	0.0044 (5)
O2	0.0382 (6)	0.0687 (8)	0.0291 (5)	0.0153 (6)	−0.0009 (5)	−0.0153 (5)
N1	0.0250 (6)	0.0335 (6)	0.0217 (5)	−0.0050 (5)	−0.0026 (5)	0.0008 (5)
C1	0.0213 (6)	0.0227 (6)	0.0188 (6)	−0.0036 (5)	−0.0003 (5)	0.0011 (5)
C2	0.0191 (6)	0.0269 (6)	0.0236 (6)	0.0000 (5)	−0.0005 (5)	−0.0002 (5)
C3	0.0225 (6)	0.0264 (6)	0.0226 (6)	−0.0018 (5)	−0.0041 (5)	0.0024 (5)
C4	0.0263 (6)	0.0196 (5)	0.0220 (6)	−0.0040 (5)	0.0010 (5)	0.0004 (5)
C5	0.0232 (6)	0.0242 (6)	0.0267 (7)	0.0028 (5)	0.0023 (5)	0.0001 (5)
C6	0.0231 (6)	0.0231 (6)	0.0271 (7)	0.0013 (5)	−0.0022 (5)	0.0039 (5)
C7	0.0244 (6)	0.0237 (6)	0.0253 (6)	0.0008 (5)	0.0014 (5)	−0.0023 (5)
C8	0.0243 (6)	0.0223 (6)	0.0242 (6)	−0.0003 (5)	0.0012 (5)	−0.0004 (5)
C9	0.0254 (6)	0.0177 (5)	0.0222 (6)	−0.0030 (5)	0.0010 (5)	−0.0002 (5)
C10	0.0222 (6)	0.0218 (6)	0.0247 (6)	0.0007 (5)	0.0017 (5)	−0.0005 (5)
C11	0.0282 (7)	0.0238 (6)	0.0240 (6)	−0.0002 (5)	−0.0028 (5)	0.0013 (5)
C12	0.0343 (7)	0.0225 (6)	0.0215 (6)	−0.0026 (6)	0.0027 (6)	−0.0023 (5)
C13	0.0257 (7)	0.0222 (6)	0.0309 (7)	0.0017 (5)	0.0057 (6)	−0.0039 (5)
C14	0.0240 (7)	0.0213 (6)	0.0285 (7)	0.0000 (5)	−0.0038 (5)	0.0012 (5)

O1—N1	1.2246 (14)	C7—H7	0.9500
O2—N1	1.2225 (15)	C8—C9	1.4750 (17)
N1—C1	1.4712 (16)	C8—H8	0.9500
C1—C6	1.3793 (17)	C9—C10	1.3931 (17)
C1—C2	1.3851 (18)	C9—C14	1.3998 (17)
C2—C3	1.3855 (17)	C10—C11	1.3890 (18)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.4058 (18)	C11—C12	1.3845 (18)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.3960 (18)	C12—C13	1.3833 (19)
C4—C7	1.4653 (17)	C12—H12	0.9500
C5—C6	1.3789 (18)	C13—C14	1.3914 (18)
C5—H5	0.9500	C13—H13	0.9500
C6—H6	0.9500	C14—H14	0.9500
C7—C8	1.3334 (18)
O2—N1—O1	123.46 (11)	C4—C7—H7	117.1
O2—N1—C1	118.07 (11)	C7—C8—C9	126.15 (12)
O1—N1—C1	118.46 (12)	C7—C8—H8	116.9
C6—C1—C2	122.37 (12)	C9—C8—H8	116.9
C6—C1—N1	118.74 (11)	C10—C9—C14	118.36 (12)
C2—C1—N1	118.88 (11)	C10—C9—C8	118.19 (11)
C1—C2—C3	118.62 (12)	C14—C9—C8	123.45 (12)
C1—C2—H2	120.7	C11—C10—C9	121.17 (12)
C3—C2—H2	120.7	C11—C10—H10	119.4
C2—C3—C4	120.62 (12)	C9—C10—H10	119.4
C2—C3—H3	119.7	C12—C11—C10	119.85 (12)
C4—C3—H3	119.7	C12—C11—H11	120.1
C5—C4—C3	118.37 (11)	C10—C11—H11	120.1
C5—C4—C7	118.43 (12)	C13—C12—C11	119.86 (12)
C3—C4—C7	123.18 (11)	C13—C12—H12	120.1
C6—C5—C4	121.61 (12)	C11—C12—H12	120.1
C6—C5—H5	119.2	C12—C13—C14	120.42 (12)
C4—C5—H5	119.2	C12—C13—H13	119.8
C5—C6—C1	118.32 (12)	C14—C13—H13	119.8
C5—C6—H6	120.8	C13—C14—C9	120.34 (11)
C1—C6—H6	120.8	C13—C14—H14	119.8
C8—C7—C4	125.82 (12)	C9—C14—H14	119.8
C8—C7—H7	117.1
O2—N1—C1—C6	174.44 (12)	C5—C4—C7—C8	−167.03 (12)
O1—N1—C1—C6	−4.53 (17)	C3—C4—C7—C8	11.53 (19)
O2—N1—C1—C2	−4.71 (18)	C4—C7—C8—C9	178.48 (12)
O1—N1—C1—C2	176.32 (11)	C7—C8—C9—C10	174.99 (12)
C6—C1—C2—C3	−1.49 (19)	C7—C8—C9—C14	−6.1 (2)
N1—C1—C2—C3	177.63 (11)	C14—C9—C10—C11	−0.39 (18)
C1—C2—C3—C4	−1.10 (18)	C8—C9—C10—C11	178.59 (11)
C2—C3—C4—C5	3.13 (18)	C9—C10—C11—C12	0.17 (18)
C2—C3—C4—C7	−175.43 (12)	C10—C11—C12—C13	0.24 (19)
C3—C4—C5—C6	−2.73 (18)	C11—C12—C13—C14	−0.42 (19)
C7—C4—C5—C6	175.91 (11)	C12—C13—C14—C9	0.19 (18)
C4—C5—C6—C1	0.27 (19)	C10—C9—C14—C13	0.21 (17)
C2—C1—C6—C5	1.90 (19)	C8—C9—C14—C13	−178.71 (11)
N1—C1—C6—C5	−177.22 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.55	3.3762 (17)	146
C12—H12···O1ii	0.95	2.66	3.4139 (16)	137
C12—H12···O2iii	0.95	2.74	3.4046 (17)	128
C11—H11···O2iii	0.95	2.90	3.4820 (17)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.55	3.3762 (17)	146
C12—H12⋯O1ii	0.95	2.66	3.4139 (16)	137
C12—H12⋯O2iii	0.95	2.74	3.4046 (17)	128
C11—H11⋯O2iii	0.95	2.90	3.4820 (17)	121

Symmetry codes: (i) ; (ii) ; (iii) .