(E)-1-(4-Methyl­phenyl)-2-(4-nitro­phenyl)­ethene

The title compound, C₁₅H₁₃NO₂, is a stilbene derivative with a push-pull conjugated system. The mol­ecules form sheets with a head-to-tail arrangement both within and between the sheets.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.184
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H24A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H24B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H24C

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: DREAR (Blessing, 1987); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003).

(I)

Crystal data

C15H13NO2	Z = 2
Mr = 239.26	F(000) = 252
Triclinic, P1	Dx = 1.313 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.339 (1) Å	Cell parameters from 25 reflections
b = 7.521 (1) Å	θ = 6.1–17.6°
c = 12.230 (4) Å	µ = 0.09 mm^−1
α = 98.66 (2)°	T = 291 K
β = 99.26 (2)°	Prism, yellow
γ = 111.13 (1)°	0.26 × 0.13 × 0.13 mm
V = 605.3 (2) Å^3

Data collection

Enraf–Nonius MACH3 diffractometer	θmax = 25.3°, θmin = 1.7°
profiled ω/2θ scans	h = 0→8
2520 measured reflections	k = −9→8
2200 independent reflections	l = −14→14
1055 reflections with I > 2σ(I)	3 standard reflections every 60 min
Rint = 0.012	intensity decay: 2%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0901P)^2 + 0.1262P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.184	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.16 e Å^−3
2200 reflections	Δρmin = −0.21 e Å^−3
205 parameters

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.1412 (4)	1.1714 (3)	0.9362 (2)	0.0863 (8)
O2	1.1132 (4)	1.3153 (3)	0.7991 (2)	0.0876 (9)
N1	1.0923 (4)	1.1693 (3)	0.8361 (2)	0.0599 (7)
C1	0.8366 (4)	0.6235 (4)	0.5986 (2)	0.0438 (7)
C2	0.8388 (5)	0.7936 (4)	0.5658 (3)	0.0514 (8)
C3	0.9218 (4)	0.9713 (4)	0.6428 (2)	0.0508 (8)
C4	1.0007 (4)	0.9790 (4)	0.7541 (2)	0.0458 (7)
C5	0.9998 (5)	0.8140 (4)	0.7907 (2)	0.0526 (8)
C6	0.9166 (5)	0.6373 (4)	0.7120 (2)	0.0515 (8)
C7	0.7511 (4)	0.4317 (4)	0.5182 (2)	0.0506 (7)
C8	0.6696 (4)	0.3935 (4)	0.4092 (3)	0.0504 (8)
C11	0.5835 (4)	0.2046 (4)	0.3269 (2)	0.0459 (7)
C12	0.5023 (4)	0.1957 (4)	0.2144 (3)	0.0530 (8)
C13	0.4173 (5)	0.0187 (5)	0.1347 (3)	0.0586 (8)
C14	0.4142 (4)	−0.1523 (4)	0.1632 (2)	0.0537 (8)
C15	0.4948 (4)	−0.1441 (4)	0.2749 (3)	0.0557 (8)
C16	0.5780 (4)	0.0308 (4)	0.3553 (3)	0.0516 (8)
C24	0.3235 (5)	−0.3437 (5)	0.0744 (3)	0.0796 (12)
H2	0.779 (4)	0.787 (4)	0.491 (2)	0.057 (9)*
H3	0.916 (5)	1.087 (5)	0.619 (3)	0.088 (11)*
H5	1.046 (5)	0.816 (5)	0.870 (3)	0.079 (10)*
H6	0.922 (4)	0.521 (4)	0.740 (2)	0.061 (8)*
H7	0.753 (4)	0.324 (5)	0.553 (3)	0.071 (9)*
H8	0.666 (4)	0.499 (4)	0.370 (2)	0.060 (8)*
H12	0.507 (4)	0.315 (5)	0.192 (2)	0.069 (9)*
H13	0.367 (5)	0.017 (4)	0.058 (3)	0.069 (9)*
H15	0.496 (4)	−0.261 (4)	0.301 (2)	0.056 (8)*
H16	0.631 (4)	0.026 (4)	0.433 (3)	0.067 (9)*
H24A	0.301 (3)	−0.3193 (7)	0.0048 (15)	0.119*
H24B	0.207 (3)	−0.421 (2)	0.0874 (13)	0.119*
H24C	0.409 (2)	−0.405 (2)	0.0784 (14)	0.119*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.124 (2)	0.0570 (14)	0.0543 (15)	0.0253 (14)	−0.0012 (14)	−0.0061 (12)
O2	0.118 (2)	0.0353 (12)	0.0887 (19)	0.0207 (12)	−0.0007 (15)	0.0035 (12)
N1	0.0666 (18)	0.0414 (15)	0.0598 (17)	0.0170 (12)	0.0054 (14)	−0.0017 (13)
C1	0.0433 (16)	0.0382 (13)	0.0452 (17)	0.0132 (12)	0.0101 (13)	0.0037 (12)
C2	0.0591 (19)	0.0472 (17)	0.0424 (17)	0.0192 (14)	0.0031 (14)	0.0082 (14)
C3	0.0559 (18)	0.0414 (15)	0.0518 (18)	0.0193 (14)	0.0060 (14)	0.0079 (13)
C4	0.0467 (16)	0.0350 (14)	0.0488 (16)	0.0121 (12)	0.0102 (13)	0.0006 (12)
C5	0.062 (2)	0.0473 (17)	0.0437 (17)	0.0200 (14)	0.0074 (14)	0.0046 (13)
C6	0.067 (2)	0.0378 (15)	0.0482 (17)	0.0222 (14)	0.0083 (14)	0.0060 (13)
C7	0.0541 (18)	0.0428 (16)	0.0516 (19)	0.0185 (14)	0.0107 (14)	0.0041 (14)
C8	0.0534 (18)	0.0432 (16)	0.0508 (18)	0.0194 (14)	0.0073 (14)	0.0042 (13)
C11	0.0433 (16)	0.0453 (15)	0.0451 (17)	0.0173 (13)	0.0084 (13)	0.0015 (13)
C12	0.0588 (19)	0.0452 (16)	0.0505 (18)	0.0187 (14)	0.0079 (14)	0.0071 (14)
C13	0.062 (2)	0.0595 (19)	0.0439 (18)	0.0178 (15)	0.0049 (15)	0.0044 (15)
C14	0.0546 (19)	0.0465 (17)	0.0489 (18)	0.0126 (14)	0.0105 (15)	−0.0011 (13)
C15	0.062 (2)	0.0460 (16)	0.0528 (18)	0.0194 (15)	0.0085 (15)	0.0033 (15)
C16	0.0570 (19)	0.0463 (16)	0.0445 (17)	0.0192 (14)	0.0035 (14)	0.0021 (13)
C24	0.092 (3)	0.0526 (19)	0.064 (2)	0.0093 (18)	0.0090 (18)	−0.0167 (16)

Geometric parameters (Å, º)

N1—O1	1.215 (3)	C8—H8	0.99 (3)
N1—O2	1.219 (3)	C11—C12	1.391 (4)
N1—C4	1.470 (3)	C11—C8	1.465 (4)
C1—C6	1.389 (4)	C12—C13	1.388 (4)
C1—C2	1.392 (4)	C12—H12	0.96 (3)
C1—C7	1.471 (4)	C13—H13	0.95 (3)
C2—H2	0.94 (3)	C14—C13	1.376 (4)
C3—C4	1.375 (4)	C14—C24	1.516 (4)
C3—C2	1.376 (4)	C15—C14	1.381 (4)
C3—H3	0.97 (3)	C15—H15	0.98 (3)
C5—C4	1.379 (4)	C16—C15	1.381 (4)
C5—C6	1.381 (4)	C16—C11	1.390 (4)
C5—H5	0.97 (3)	C16—H16	0.98 (3)
C6—H6	0.99 (3)	C24—H24A	0.8997
C7—H7	0.98 (3)	C24—H24B	0.8997
C8—C7	1.312 (4)	C24—H24C	0.8997
O1—N1—O2	124.1 (3)	C11—C8—H8	110.1 (17)
O1—N1—C4	118.3 (3)	C11—C12—H12	118.9 (18)
O2—N1—C4	117.7 (3)	C11—C16—H16	121.8 (17)
C1—C2—H2	120.0 (17)	C12—C11—C8	119.2 (3)
C1—C6—H6	121.6 (17)	C12—C13—H13	119.1 (18)
C1—C7—H7	113.7 (18)	C13—C12—C11	120.7 (3)
C2—C1—C7	122.4 (3)	C13—C12—H12	120.4 (18)
C3—C2—C1	121.1 (3)	C13—C14—C15	118.0 (3)
C3—C2—H2	118.9 (17)	C13—C14—C24	120.7 (3)
C2—C3—H3	119 (2)	C14—C13—C12	121.5 (3)
C3—C4—C5	121.9 (3)	C14—C13—H13	119.2 (18)
C3—C4—N1	119.0 (3)	C14—C15—C16	121.0 (3)
C4—C3—C2	119.0 (3)	C14—C15—H15	121.8 (17)
C4—C3—H3	121 (2)	C14—C24—H24A	109.5
C4—C5—C6	118.2 (3)	C14—C24—H24B	109.5
C4—C5—H5	123 (2)	C14—C24—H24C	109.5
C5—C4—N1	119.0 (3)	C15—C14—C24	121.3 (3)
C5—C6—C1	121.6 (3)	C15—C16—C11	121.4 (3)
C5—C6—H6	116.7 (17)	C15—C16—H16	116.8 (17)
C6—C1—C2	118.1 (3)	C16—C11—C12	117.4 (3)
C6—C1—C7	119.4 (3)	C16—C11—C8	123.4 (3)
C6—C5—H5	119 (2)	C16—C15—H15	117.1 (17)
C7—C8—C11	128.4 (3)	H24A—C24—H24B	109.5
C7—C8—H8	121.4 (17)	H24A—C24—H24C	109.5
C8—C7—C1	127.1 (3)	H24B—C24—H24C	109.5
C8—C7—H7	119.1 (18)
O1—N1—C4—C3	172.0 (3)	C7—C1—C6—C5	179.5 (3)
O1—N1—C4—C5	−9.3 (4)	C8—C11—C12—C13	−179.2 (3)
O2—N1—C4—C3	−7.5 (4)	C11—C8—C7—C1	179.9 (3)
O2—N1—C4—C5	171.3 (3)	C11—C12—C13—C14	−1.4 (5)
C2—C1—C7—C8	0.4 (5)	C11—C16—C15—C14	0.0 (4)
C2—C1—C6—C5	−1.2 (4)	C12—C11—C8—C7	179.4 (3)
C2—C3—C4—C5	0.3 (5)	C15—C14—C13—C12	1.3 (5)
C2—C3—C4—N1	179.0 (3)	C15—C16—C11—C12	−0.1 (4)
C4—C3—C2—C1	−1.0 (4)	C15—C16—C11—C8	179.8 (3)
C4—C5—C6—C1	0.5 (4)	C16—C11—C8—C7	−0.5 (5)
C6—C1—C2—C3	1.4 (4)	C16—C11—C12—C13	0.8 (4)
C6—C5—C4—C3	0.0 (5)	C16—C15—C14—C13	−0.7 (4)
C6—C5—C4—N1	−178.8 (2)	C16—C15—C14—C24	179.7 (3)
C6—C1—C7—C8	179.7 (3)	C24—C14—C13—C12	−179.1 (3)
C7—C1—C2—C3	−179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	1.00 (3)	2.54 (3)	3.447 (5)	151 (2)

Symmetry code: (i) x, y−1, z.