(E,E)-1-[2-(4-Nitro­phenyl)­ethen­yl]-4-[2-(2,4,6-trimethoxy­phenyl)­ethen­yl]benzene

The crystal structure of the title compound, C₂₅H₂₃NO₅, is centrosymmetric; it crystallizes in ribbons inter­acting through C—H...π contacts and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 287 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.040
• wR factor = 0.121
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

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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: Mercury (Bruno et al., 2002) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

(E,E)-4-(4-Nitrophenylethenyl)-1-(2,4,6-trimethoxyphenylethenyl)benzene

Crystal data

C25H23NO5	F(000) = 880
Mr = 417.44	Dx = 1.306 Mg m^−3
Monoclinic, P21/c	Melting point: 451 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.785 (5) Å	Cell parameters from 25 reflections
b = 10.357 (2) Å	θ = 7.5–21.8°
c = 13.502 (1) Å	µ = 0.09 mm^−1
β = 105.96 (2)°	T = 287 K
V = 2122.2 (8) Å^3	Rhomboid, red-orange
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius MACH3 diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 25.3°, θmin = 1.3°
Graphite monochromator	h = −18→18
ω/2θ scans	k = −12→4
4890 measured reflections	l = −16→0
3880 independent reflections	3 standard reflections every 60 min
2320 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.121	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.3937P] where P = (Fo^2 + 2Fc^2)/3
3880 reflections	(Δ/σ)max < 0.001
372 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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
O46	0.31193 (9)	0.92938 (13)	0.77035 (10)	0.0556 (4)
O42	0.21210 (9)	0.57320 (14)	0.55387 (11)	0.0612 (4)
O44	0.47551 (10)	0.80455 (17)	0.54253 (12)	0.0739 (5)
C41	0.26307 (12)	0.74666 (18)	0.66547 (13)	0.0433 (4)
C4	−0.18582 (13)	0.6229 (2)	1.09063 (15)	0.0507 (5)
C42	0.27383 (12)	0.66837 (19)	0.58474 (14)	0.0471 (4)
C24	0.06833 (12)	0.63745 (18)	0.76996 (14)	0.0469 (5)
C44	0.40338 (13)	0.7806 (2)	0.57725 (15)	0.0531 (5)
C46	0.32509 (12)	0.84750 (19)	0.69592 (13)	0.0458 (5)
N1	−0.37402 (14)	0.5676 (2)	1.25683 (16)	0.0733 (6)
C21	−0.05229 (12)	0.60648 (19)	0.89040 (15)	0.0484 (5)
C1	−0.30872 (14)	0.5884 (2)	1.19953 (17)	0.0580 (6)
C27	0.12820 (13)	0.6498 (2)	0.70529 (15)	0.0498 (5)
C45	0.39434 (13)	0.8636 (2)	0.65373 (15)	0.0521 (5)
C26	0.01835 (14)	0.6922 (2)	0.91974 (16)	0.0547 (5)
O1	−0.42445 (12)	0.4753 (2)	1.23247 (16)	0.0883 (6)
C28	0.19698 (13)	0.7287 (2)	0.72155 (15)	0.0475 (5)
C8	−0.11775 (13)	0.5883 (2)	0.94735 (16)	0.0521 (5)
C43	0.34257 (13)	0.6847 (2)	0.54037 (15)	0.0518 (5)
C22	−0.06000 (13)	0.5351 (2)	0.80089 (16)	0.0536 (5)
C23	−0.00161 (14)	0.5501 (2)	0.74276 (16)	0.0527 (5)
C5	−0.17465 (15)	0.6787 (2)	1.18674 (17)	0.0591 (6)
C7	−0.11897 (14)	0.6430 (2)	1.03552 (16)	0.0523 (5)
C25	0.07664 (14)	0.7069 (2)	0.86104 (16)	0.0549 (5)
O2	−0.37513 (14)	0.6428 (2)	1.32600 (15)	0.1036 (7)
C2	−0.32233 (16)	0.5307 (3)	1.10489 (19)	0.0694 (7)
C6	−0.23589 (16)	0.6630 (2)	1.24115 (18)	0.0652 (6)
C3	−0.26102 (15)	0.5491 (3)	1.05150 (18)	0.0686 (7)
C56	0.3666 (2)	1.0413 (3)	0.7947 (2)	0.0675 (6)
C52	0.22186 (19)	0.4812 (3)	0.47907 (19)	0.0651 (6)
C54	0.4886 (2)	0.7279 (4)	0.4609 (2)	0.0815 (8)
H28	0.2061 (13)	0.780 (2)	0.7816 (16)	0.061 (6)*
H43	0.3493 (13)	0.631 (2)	0.4901 (16)	0.057 (6)*
H8	−0.1649 (13)	0.529 (2)	0.9156 (16)	0.057 (6)*
H45	0.4374 (14)	0.931 (2)	0.6744 (16)	0.062 (6)*
H23	−0.0094 (13)	0.496 (2)	0.6817 (16)	0.061 (6)*
H7	−0.0725 (15)	0.702 (2)	1.0698 (16)	0.065 (6)*
H6	−0.2269 (16)	0.699 (2)	1.3036 (19)	0.082 (8)*
H22	−0.1093 (14)	0.475 (2)	0.7784 (16)	0.064 (6)*
H561	0.3436 (14)	1.095 (2)	0.8414 (19)	0.077 (7)*
H27	0.1151 (13)	0.596 (2)	0.6478 (16)	0.060 (6)*
H562	0.4294 (17)	1.018 (2)	0.8249 (18)	0.078 (8)*
H541	0.4397 (17)	0.742 (2)	0.399 (2)	0.081 (8)*
H563	0.3602 (16)	1.097 (2)	0.733 (2)	0.088 (8)*
H25	0.1242 (15)	0.763 (2)	0.8854 (16)	0.066 (6)*
H26	0.0284 (14)	0.746 (2)	0.9807 (18)	0.076 (7)*
H3	−0.2716 (16)	0.511 (2)	0.986 (2)	0.090 (8)*
H521	0.2789 (16)	0.430 (2)	0.5044 (18)	0.075 (7)*
H5	−0.1220 (16)	0.728 (2)	1.2156 (18)	0.081 (8)*
H522	0.1716 (17)	0.418 (3)	0.4716 (19)	0.087 (8)*
H543	0.5401 (18)	0.761 (3)	0.4507 (19)	0.091 (8)*
H2	−0.3763 (18)	0.482 (3)	1.077 (2)	0.093 (8)*
H523	0.2184 (16)	0.524 (2)	0.417 (2)	0.081 (8)*
H542	0.4932 (18)	0.630 (3)	0.478 (2)	0.096 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O46	0.0598 (8)	0.0598 (9)	0.0539 (8)	−0.0076 (7)	0.0267 (7)	−0.0105 (7)
O42	0.0695 (9)	0.0630 (9)	0.0582 (8)	−0.0119 (8)	0.0294 (7)	−0.0153 (7)
O44	0.0606 (9)	0.1017 (13)	0.0721 (10)	−0.0155 (9)	0.0396 (8)	−0.0250 (9)
C41	0.0431 (10)	0.0493 (11)	0.0384 (9)	0.0056 (9)	0.0126 (8)	0.0037 (8)
C4	0.0484 (11)	0.0558 (12)	0.0491 (11)	0.0036 (9)	0.0156 (9)	0.0035 (9)
C42	0.0485 (10)	0.0499 (11)	0.0428 (10)	0.0007 (9)	0.0126 (8)	0.0016 (9)
C24	0.0476 (10)	0.0462 (11)	0.0478 (10)	0.0044 (9)	0.0145 (8)	0.0037 (9)
C44	0.0464 (11)	0.0698 (14)	0.0469 (11)	0.0001 (10)	0.0191 (9)	−0.0008 (10)
C46	0.0460 (10)	0.0533 (12)	0.0383 (9)	0.0062 (9)	0.0116 (8)	−0.0002 (9)
N1	0.0649 (13)	0.0932 (16)	0.0709 (13)	0.0313 (12)	0.0341 (11)	0.0292 (13)
C21	0.0443 (10)	0.0522 (11)	0.0498 (11)	0.0010 (9)	0.0149 (9)	0.0068 (9)
C1	0.0514 (12)	0.0682 (14)	0.0607 (13)	0.0164 (11)	0.0258 (10)	0.0147 (11)
C27	0.0496 (11)	0.0549 (12)	0.0466 (11)	0.0013 (10)	0.0160 (9)	0.0000 (10)
C45	0.0470 (11)	0.0630 (13)	0.0471 (11)	−0.0040 (10)	0.0143 (9)	−0.0028 (10)
C26	0.0578 (12)	0.0601 (13)	0.0496 (11)	−0.0056 (10)	0.0205 (10)	−0.0047 (10)
O1	0.0676 (11)	0.1025 (15)	0.1066 (14)	0.0156 (10)	0.0441 (11)	0.0390 (12)
C28	0.0498 (11)	0.0503 (11)	0.0459 (11)	0.0064 (9)	0.0187 (9)	0.0026 (9)
C8	0.0458 (11)	0.0578 (13)	0.0533 (12)	−0.0015 (10)	0.0148 (9)	0.0034 (10)
C43	0.0549 (12)	0.0612 (13)	0.0431 (10)	0.0026 (10)	0.0197 (9)	−0.0041 (10)
C22	0.0475 (11)	0.0592 (13)	0.0547 (12)	−0.0084 (10)	0.0150 (9)	−0.0027 (10)
C23	0.0523 (11)	0.0573 (13)	0.0492 (11)	−0.0043 (10)	0.0155 (9)	−0.0065 (10)
C5	0.0600 (13)	0.0626 (14)	0.0574 (12)	−0.0021 (11)	0.0209 (11)	−0.0087 (11)
C7	0.0504 (11)	0.0551 (13)	0.0533 (12)	−0.0002 (10)	0.0171 (10)	0.0023 (10)
C25	0.0533 (12)	0.0570 (13)	0.0575 (12)	−0.0119 (10)	0.0204 (10)	−0.0035 (11)
O2	0.1112 (15)	0.1366 (18)	0.0825 (12)	0.0399 (13)	0.0596 (12)	0.0072 (13)
C2	0.0543 (13)	0.0911 (19)	0.0663 (14)	−0.0115 (13)	0.0227 (12)	−0.0061 (13)
C6	0.0740 (15)	0.0709 (16)	0.0552 (13)	0.0093 (13)	0.0252 (12)	−0.0060 (12)
C3	0.0601 (14)	0.0951 (19)	0.0543 (13)	−0.0133 (13)	0.0221 (11)	−0.0149 (13)
C56	0.0804 (18)	0.0602 (15)	0.0699 (16)	−0.0110 (13)	0.0340 (14)	−0.0132 (13)
C52	0.0784 (17)	0.0646 (15)	0.0558 (14)	−0.0079 (14)	0.0244 (13)	−0.0136 (12)
C54	0.0761 (19)	0.106 (3)	0.0778 (18)	−0.0081 (18)	0.0461 (17)	−0.0240 (18)

Geometric parameters (Å, º)

C4—C7	1.464 (3)	C1—C6	1.371 (3)
C7—C8	1.324 (3)	C1—C2	1.373 (3)
C8—C21	1.460 (3)	C27—H27	0.93 (2)
C21—C22	1.393 (3)	C45—H45	0.96 (2)
C22—C23	1.374 (3)	C26—C25	1.378 (3)
C23—C24	1.396 (3)	C26—H26	0.97 (2)
C24—C27	1.458 (3)	C28—H28	0.95 (2)
C27—C28	1.328 (3)	C8—H8	0.97 (2)
C28—C41	1.460 (3)	C43—H43	0.91 (2)
O46—C46	1.374 (2)	C22—H22	0.98 (2)
O46—C56	1.428 (3)	C23—H23	0.98 (2)
O42—C42	1.368 (2)	C5—C6	1.375 (3)
O42—C52	1.428 (3)	C5—H5	0.96 (2)
O44—C44	1.368 (2)	C7—H7	0.97 (2)
O44—C54	1.419 (3)	C25—H25	0.93 (2)
C41—C42	1.406 (3)	C2—C3	1.370 (3)
C41—C46	1.413 (3)	C2—H2	0.98 (3)
C4—C5	1.387 (3)	C6—H6	0.90 (2)
C4—C3	1.388 (3)	C3—H3	0.94 (3)
C42—C43	1.387 (3)	C56—H561	0.98 (2)
C24—C25	1.399 (3)	C56—H562	0.99 (2)
C44—C43	1.375 (3)	C56—H563	1.00 (3)
C44—C45	1.381 (3)	C52—H521	1.02 (2)
C46—C45	1.375 (3)	C52—H522	1.01 (3)
N1—O2	1.220 (3)	C52—H523	0.94 (3)
N1—O1	1.230 (3)	C54—H541	0.98 (3)
N1—C1	1.465 (3)	C54—H543	0.93 (3)
C21—C26	1.395 (3)	C54—H542	1.04 (3)
C46—O46—C56	117.78 (16)	C44—C43—C42	118.88 (19)
C42—O42—C52	119.36 (17)	C44—C43—H43	120.1 (13)
C44—O44—C54	118.5 (2)	C42—C43—H43	120.9 (13)
C42—C41—C46	115.47 (16)	C23—C22—C21	121.6 (2)
C42—C41—C28	125.80 (18)	C23—C22—H22	119.8 (13)
C46—C41—C28	118.68 (17)	C21—C22—H22	118.7 (12)
C5—C4—C3	117.45 (19)	C22—C23—C24	122.0 (2)
C5—C4—C7	119.5 (2)	C22—C23—H23	117.9 (12)
C3—C4—C7	123.07 (19)	C24—C23—H23	120.1 (12)
O42—C42—C43	122.20 (18)	C6—C5—C4	121.6 (2)
O42—C42—C41	115.09 (16)	C6—C5—H5	120.2 (14)
C43—C42—C41	122.70 (19)	C4—C5—H5	118.3 (14)
C23—C24—C25	116.14 (18)	C8—C7—C4	125.9 (2)
C23—C24—C27	119.70 (18)	C8—C7—H7	120.3 (13)
C25—C24—C27	124.15 (18)	C4—C7—H7	113.8 (13)
O44—C44—C43	124.81 (18)	C26—C25—C24	122.2 (2)
O44—C44—C45	114.21 (19)	C26—C25—H25	117.7 (13)
C43—C44—C45	120.97 (18)	C24—C25—H25	120.1 (13)
O46—C46—C45	121.72 (18)	C3—C2—C1	118.5 (2)
O46—C46—C41	115.91 (15)	C3—C2—H2	122.3 (15)
C45—C46—C41	122.37 (18)	C1—C2—H2	119.2 (15)
O2—N1—O1	123.8 (2)	C1—C6—C5	118.8 (2)
O2—N1—C1	118.1 (3)	C1—C6—H6	121.3 (16)
O1—N1—C1	118.1 (2)	C5—C6—H6	119.9 (16)
C22—C21—C26	117.15 (18)	C2—C3—C4	122.0 (2)
C22—C21—C8	118.88 (19)	C2—C3—H3	117.8 (16)
C26—C21—C8	123.97 (19)	C4—C3—H3	120.2 (16)
C6—C1—C2	121.7 (2)	O46—C56—H561	107.7 (14)
C6—C1—N1	119.9 (2)	O46—C56—H562	111.6 (14)
C2—C1—N1	118.4 (2)	H561—C56—H562	112.3 (19)
C28—C27—C24	126.2 (2)	O46—C56—H563	111.1 (15)
C28—C27—H27	119.2 (13)	H561—C56—H563	104 (2)
C24—C27—H27	114.6 (13)	H562—C56—H563	110 (2)
C46—C45—C44	119.5 (2)	O42—C52—H521	111.6 (13)
C46—C45—H45	123.1 (12)	O42—C52—H522	105.5 (14)
C44—C45—H45	117.4 (12)	H521—C52—H522	106.9 (19)
C25—C26—C21	121.0 (2)	O42—C52—H523	109.1 (15)
C25—C26—H26	116.5 (14)	H521—C52—H523	112 (2)
C21—C26—H26	122.5 (13)	H522—C52—H523	111 (2)
C27—C28—C41	131.4 (2)	O44—C54—H541	109.3 (15)
C27—C28—H28	114.3 (12)	O44—C54—H543	103.1 (17)
C41—C28—H28	114.3 (12)	H541—C54—H543	109 (2)
C7—C8—C21	127.3 (2)	O44—C54—H542	113.3 (15)
C7—C8—H8	118.0 (12)	H541—C54—H542	109 (2)
C21—C8—H8	114.7 (12)	H543—C54—H542	113 (2)
C52—O42—C42—C43	4.9 (3)	C46—C41—C28—C27	174.4 (2)
C52—O42—C42—C41	−174.23 (19)	C22—C21—C8—C7	176.9 (2)
C46—C41—C42—O42	−178.30 (16)	C26—C21—C8—C7	−3.4 (3)
C28—C41—C42—O42	4.5 (3)	O44—C44—C43—C42	178.0 (2)
C46—C41—C42—C43	2.6 (3)	C45—C44—C43—C42	−3.1 (3)
C28—C41—C42—C43	−174.63 (19)	O42—C42—C43—C44	−178.39 (18)
C54—O44—C44—C43	1.5 (4)	C41—C42—C43—C44	0.6 (3)
C54—O44—C44—C45	−177.4 (2)	C26—C21—C22—C23	−1.2 (3)
C56—O46—C46—C45	7.0 (3)	C8—C21—C22—C23	178.51 (19)
C56—O46—C46—C41	−172.7 (2)	C21—C22—C23—C24	−0.1 (3)
C42—C41—C46—O46	176.13 (16)	C25—C24—C23—C22	1.3 (3)
C28—C41—C46—O46	−6.4 (2)	C27—C24—C23—C22	−179.79 (19)
C42—C41—C46—C45	−3.6 (3)	C3—C4—C5—C6	−0.6 (3)
C28—C41—C46—C45	173.82 (18)	C7—C4—C5—C6	179.7 (2)
O2—N1—C1—C6	19.3 (3)	C21—C8—C7—C4	179.88 (19)
O1—N1—C1—C6	−160.6 (2)	C5—C4—C7—C8	174.7 (2)
O2—N1—C1—C2	−161.2 (2)	C3—C4—C7—C8	−5.0 (4)
O1—N1—C1—C2	18.8 (3)	C21—C26—C25—C24	0.0 (3)
C23—C24—C27—C28	179.8 (2)	C23—C24—C25—C26	−1.2 (3)
C25—C24—C27—C28	−1.4 (3)	C27—C24—C25—C26	179.9 (2)
O46—C46—C45—C44	−178.37 (18)	C6—C1—C2—C3	0.0 (4)
C41—C46—C45—C44	1.4 (3)	N1—C1—C2—C3	−179.5 (2)
O44—C44—C45—C46	−178.88 (18)	C2—C1—C6—C5	−0.8 (3)
C43—C44—C45—C46	2.1 (3)	N1—C1—C6—C5	178.6 (2)
C22—C21—C26—C25	1.3 (3)	C4—C5—C6—C1	1.2 (3)
C8—C21—C26—C25	−178.4 (2)	C1—C2—C3—C4	0.6 (4)
C24—C27—C28—C41	177.42 (19)	C5—C4—C3—C2	−0.3 (4)
C42—C41—C28—C27	−8.5 (3)	C7—C4—C3—C2	179.4 (2)