Four (E,Z,E)-1-(4-alkoxy­phen­yl)-6-(4-nitro­phen­yl)hexa-1,3,5-trienes

The crystal structures of the four E,Z,E isomers of 1-(4-alk­oxy­phen­yl)-6-(4-nitro­phen­yl)hexa-1,3,5-triene, namely (E,Z,E)-1-(4-methoxy­phen­yl)-6-(4-nitro­phen­yl)hexa-1,3,5-triene, C₁₉H₁₇NO₃, (E,Z,E)-1-(4-ethoxy­phen­yl)-6-(4-nitro­phen­yl)hexa-1,3,5-triene, C₂₀H₁₉NO₃, (E,Z,E)-1-(4-nitro­phen­yl)-6-(4-n-propoxyphen­yl)hexa-1,3,5-triene, C₂₁H₂₁NO₃, and (E,Z,E)-1-(4-n-butoxy­phen­yl)-6-(4-nitro­phen­yl)hexa-1,3,5-triene, C₂₂H₂₃NO₃, have been determined. Inter­molecular N...O dipole inter­actions between the nitro groups are observed for the meth­oxy derivative, while for the eth­oxy derivative, two adjacent mol­ecules are linked at both ends through N...O dipole–dipole inter­actions between the N atom of the nitro group and the O atom of the eth­oxy group to form a supra­molecular ring-like structure. In the crystal structures of the n-prop­oxy and n-but­oxy derivatives, the shortest inter­molecular distances are those between the two O atoms of the alk­oxy groups. Thus, the nearest two mol­ecules form an S-shaped supra­molecular dimer in these crystal structures.

S1. Comment

π-Conjugated bent molecules are attracting increased attention at the current time (Yamaguchi et al., 2005; Ros et al., 2005). We have recently reported the crystal structure and photophysical properties of a series of (E,E,E)-1-(4-alkoxyphenyl)-6-(4-nitrophenyl)hexa-1,3,5-trienes, namely the methoxy, ethoxy, n-propoxy and n-butoxy compounds (Sonoda et al., 2006). In the course of our study, we obtained single crystals of their E,Z,E isomers [(I)–(IV)], whose crystal structures we describe here. To the best of our knowledge, the crystal structure of 1,6-diphenylhexa-1,3,5-triene (DPH) having the E,Z,E configuration at the triene double bonds has not been reported so far. Our data can be compared with those for dibenzo[18]annulene incorporating two (E,Z,E)-DPH units (Michels et al., 1994).

For compounds (I), (III) and (IV), only one independent molecule is present in the asymmetric unit, while for compound (II), two crystallographically independent molecules, A and B, are contained in the unit cell (Figs. 1–4). Selected geometric parameters for (I)–(IV) are given in Table 1.

Bond-length alternation is one of the most important structural parameters that correlate tightly with the electronic and optical properties of one-dimensional conjugated compounds, such as polyene and polyyne, since it strongly affects the band gaps of these molecules (Yang & Kertesz, 2006). In the present compounds, the averaged values of bond-length alternation (δr, the difference between C—C single- and C═C double-bond lengths) in the hexatriene chain are 0.107 Å for (I), 0.103 and 0.091 Å for molecules A and B of (II), respectively, 0.101 Å for (III), and 0.104 Å for (IV). The value of δr for (E)-polyacetylene, the polyene with an infinite chain length, has been determined spectroscopically to be 0.08 Å (Yannoni & Clarke, 1983). The bond alternation is thus more distinctly observed in trienes (I)–(IV) than in polyacetylene, as expected. Interestingly, the single- and double-bond lengths and the resulting δr values of (I)–(IV) are not greatly different from those of their E,E,E counterparts. In the crystal of the E,E,E isomer of (I), for example, the single-bond lengths are 1.434 (5)–1.460 (5) Å, the double-bond lengths are 1.333 (5)–1.345 (5) Å, and the values of δr are 0.101 and 0.114 Å for the two crystallographically independent molecules (Sonoda et al., 2006).

The geometries of the isolated molecule of (I) were optimized by ab initio calculations. The GAUSSIAN03 program was used for ab initio calculations (Frisch et al., 2004). The lengths of single bonds in the MP2/6–31G* (Møller & Plesset, 1934) level geometries (C4—C7 = 1.460 Å, C8—C9 = C10—C11 = 1.441 Å and C12—C13 = 1.459 Å) agree well with the values determined from the crystal structure, although the calculated lengths of the double bonds (C7—C8 = C11—C12 = 1.358 Å and C9—C10 = 1.364 Å) are slightly longer than those found in the crystal. The value of δr = 0.090 Å obtained from the calculation is in reasonable agreement with that from the crystal structure determination. It should be noted that the calculation at the HF/6–31G* level yields a considerably large value of δr (0.133 Å). A similar trend has been reported for polyacetylene oligomers (Choi et al., 1997; Jacquemin et al., 2005).

The C—C—C internal bond angles in the hexatriene chain are all somewhat wider than 120° for all structures, which minimizes the steric hindrance between the C5—H and C8—H atoms, between the C8—H and C11—H atoms, and between the C11—H and C18—H atoms.

The torsion angle of the single bond between the aromatic ring and the triene chain is different for each molecule. The angles C5—C4—C7—C8 [-0.7 (2)°] in (I) and C25—C24—C27—C28 [20.9 (11)°] in (II) display the minimum and the maximum deviations from values of 0 or 180° in these molecules, respectively. The optimized geometry of an isolated molecule of (I) is such that the C5—C4—C7—C8 and C11—C12—C13—C18 torsion angles are -22.65 and -18.93°. Ab initio calculations of 4,4'-disubstituted DPHs show that the torsional potential is very shallow when the torsion angle is -30–30° (Tsuzuki, 2003). It is therefore very probable that the torsion angle will have a different value depending on the packing force in each crystal. Other torsion angles in the triene chains are almost 0 or 180° for all four compounds, indicating that the triene planes are nearly planar for conjugation.

Figs. 5–8 show the crystal structures of (I)–(IV). For all compounds, the neighboring molecules have head-to-tail orientation. This results from donor–acceptor substitution on the rings, as the calculated dipole moment of (I) is 6.38 D (MP2/6–311G**//MP2/6–31G* level).

In the crystal structure of (I), attractive N···O interactions between the nitro groups are observed. The nearest two nitro groups are in a parallel arrangement, which allows the overlap of the N—O dipoles (Szezesna & Urbańczyk-Lipkowska, 2002; Zeller & Hunter, 2004). The parallel arrangement is also observed in the E,E,E isomer of (I); however, the shortest intermolecular distance between the N and O atoms in (I) [O1···N1ⁱⁱⁱ = 3.417 (2) Å; symmetry code: (iii) -x + 2, -y + 1, -z + 2] is considerably larger than the N···O distance of 2.938 (4) Å in its E,E,E isomer (Sonoda et al., 2006).

In the crystal structure of (II), two adjacent molecules are linked at both ends through N···O dipole interactions between the N atom of the nitro group and the O atom of the ethoxy group to form a supramolecular ring-like structure. The intermolecular distances between the N and O atoms are 3.392 (9) Å [O6···N1ⁱⁱⁱ: symmetry code: (iii) x, y, z + 1] and 3.427 (9) Å [O3···N2ⁱⁱⁱ; symmetry code: (iii) x, y, z + 1]. These supramolecular rings are piled up along the c axis. The least-squares plane defined by the molecule (x, y, z) makes an angle of 56.47 (3)° with the least-squares plane defined by the molecule with symmetry code (x + 1/2, -y, z).

In the crystal structures of (III) and (IV), the shortest intermolecular distances are those between the two O atoms of the alkoxy groups: O3···O3ⁱⁱ = 4.284 (2) Å [symmetry code: (ii) -x + 1, -y + 1, -z + 2] for (III), and O3···O3ⁱⁱ = 3.832 (2) Å [symmetry code: (ii) -x, -y + 2, -z] for (IV). Thus, the nearest two molecules form an S-shaped supramolecular dimer in these crystal structures.

Related literature

For related literature, see: Choi et al. (1997); Frisch et al. (2004); Jacquemin et al. (2005); Møller & Plesset (1934); Michels et al. (1994); Ros et al. (2005); Sonoda et al. (2006); Szezesna & Urbańczyk-Lipkowska (2002); Tsuzuki (2003); Yamaguchi et al. (2005); Yang & Kertesz (2006); Yannoni & Clarke (1983); Zeller & Hunter (2004).

S2. Experimental

Compounds (I)–(IV) were prepared by the Wittig reactions of the triphenylphosphonium salt of (E)-4-nitrocinnamyl bromide and (E)-4-alkoxycinnamaldehydes (Sonoda et al., 2006). The reaction gave a mixture of E,Z,E and E,E,E isomers as a crude product, from which the E,E,E isomer was removed by recrystallization from toluene. Toluene was evaporated from the mother liquor under reduced pressure, and the resulting isomeric mixture (predominantly E,Z,E) was dissolved in an appropriate solvent [acetonitrile for (I) and dichloromethane–toluene for (II)–(IV)]. Crystals suitable for X-ray diffraction were obtained from these solutions by slow evaporation at room temperature in the dark. The melting points of (I)–(IV) could not be determined, probably because of thermal conversion to the E,E,E isomers in the solid state. ¹H NMR (CDCl₃, 300 MHz): for (I), δ 8.20 (2H, d, J = 8.9 Hz, arom.), 7.58 (2H, d, J = 8.6 Hz, arom.), 7.44 (2H, d, J = 8.6 Hz, arom.), 7.24 (1H, dd, J = 15.8 and 11.6 Hz, triene), 6.90 (2H, d, J = 8.9 Hz, arom.), 6.56–6.68 (3H, m, triene), 6.36 (1H, apparently (app.) t, J = 11.1 Hz, triene), 6.21 (1H, app. t, J = 11.4 Hz, triene), 3.84 (3H, s, OCH₃); for (II), δ 8.19 (2H, d, J = 8.8 Hz, arom.), 7.58 (2H, d, J = 8.8 Hz, arom.), 7.43 (2H, d, J = 8.9 Hz, arom.), 7.23 (1H, dd, J = 15.4 and 11.5 Hz, triene), 6.89 (2H, d, J = 8.8 Hz, arom.), 6.56–6.67 (3H, m, triene), 6.36 (1H, app. t, J = 11.3 Hz, triene), 6.20 (1H, app. t, J = 11.4 Hz, triene), 4.07 (2H, q, J = 7.0 Hz, OCH₂), 1.43 (3H, t, J = 7.0 Hz, CH₃); for (III), δ 8.20 (2H, d, J = 8.7 Hz, arom.), 7.58 (2H, d, J = 8.8 Hz, arom.), 7.43 (2H, d, J = 8.7 Hz, arom.), 7.23 (1H, dd, J = 15.4 and 10.9 Hz, triene), 6.89 (2H, d, J = 8.8 Hz, arom.), 6.56–6.67 (3H, m, triene), 6.36 (1H, app. t, J = 11.1 Hz, triene), 6.20 (1H, app. t, J = 11.0 Hz, triene), 3.94 (2H, t, J = 6.6 Hz, OCH₂), 1.76–1.87 (2H, m, CH₂Me), 1.04 (3H, t, J = 7.4 Hz, CH₃); for (IV), δ 8.20 (2H, d, J = 8.5 Hz, arom.), 7.58 (2H, d, J = 8.9 Hz, arom.), 7.42 (2H, d, J = 8.7 Hz, arom.), 7.23 (1H, dd, J = 15.5 and 11.3 Hz, triene), 6.89 (2H, d, J = 8.6 Hz, arom.), 6.56–6.67 (3H, m, triene), 6.36 (1H, app. t, J = 11.0 Hz, triene), 6.20 (1H, app. t, J = 11.0 Hz, triene), 3.99 (2H, t, J = 6.4 Hz, OCH₂), 1.73–1.83 (2H, m, CH₂Et), 1.44–1.57 (2H, m, CH₂Me), 0.99 (3H, t, J = 7.4 Hz, CH₃).

S3. Refinement

All H atoms were located by geometric considerations and refined as riding on their carrier atoms.

Computing details

For all compounds, data collection: SMART (Bruker, 2001). Cell refinement: SMART [or SAINT?] for (I), (III), (IV); SMART for (II). For all compounds, data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of the molecular structure and the atom-numbering scheme of the independent molecule in (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the molecular structure and the atom-numbering scheme of the independent molecules in (II). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. A view of the molecular structure and the atom-numbering scheme of the independent molecule in (III). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. A view of the molecular structure and the atom-numbering scheme of the independent molecule in (IV). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 5. A partial view of the molecular packing in (I). Dotted lines indicate the shortest O···N intermolecular distance [O1^i···N1^ii = 3.417 (2) Å; symmetry codes: (i) -x + 3/2, -y + 3/2, z - 1/2; (ii) x - 1/2, y + 1/2, -z + 3/2].
	Fig. 6. A partial view of the molecular packing in (II). Dotted lines indicate the intermolecular distances between the N atom of the nitro group and the O atom of the ethoxy group [O6^i···N1^ii = 3.392 (9) Å and N2^i··· O3^ii = 3.427 (9) Å; symmetry codes: (i) -x + 1, -y + 1, z + 1/2; (ii) -x + 1, -y + 1, z - 1/2].
	Fig. 7. A partial view of the molecular packing in (III). Dotted lines indicate the shortest O···O intermolecular distances [O3^i···O3^ii = O3^iii···O3^iv = O3^v···O3^vi = 4.284 (2) Å; symmetry codes: (i) x, y, z; (ii) -x + 1, -y + 1, -z + 2; (iii) -x + 1, y - 1/2, -z + 3/2; (iv) x, -y + 1/2, z - 1/2; (v) x, y, z - 1; (vi) -x + 1, -y + 1, -z + 1].
	Fig. 8. A partial view of the molecular packing in (IV). Dashed lines indicate the shortest O···O intermolecular distances [O3^i···O3^ii = O3^iii···O3^iv = O3^v···O3^vi = O3^vii···O3^viii = 3.832 (2) Å; symmetry codes: (i) x, y, z; (ii) -x, -y + 2, -z; (iii) -x + 1, y - 1/2, -z + 1/2; (iv) x + 1, -y + 3/2, z + 1/2; (v) x + 1, y, z + 1; (vi) -x + 1, -y + 2, -z + 1; (vii) x, -y + 3/2, z + 1/2; (viii) -x, y - 1/2, -z + 1/2].

(I) (E,Z,E)-1-(4-methoxyphenyl)-6-(4-nitrophenyl)hexa-1,3,5-triene

Crystal data

C19H17NO3	F(000) = 1296
Mr = 307.34	Dx = 1.297 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5293 reflections
a = 13.0541 (11) Å	θ = 2.4–27.6°
b = 6.9672 (6) Å	µ = 0.09 mm^−1
c = 34.604 (3) Å	T = 183 K
V = 3147.2 (5) Å^3	Rectangular, orange
Z = 8	0.30 × 0.10 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3715 independent reflections
Radiation source: rotating anode	2905 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.366 pixels mm^-1	θmax = 28.3°, θmin = 1.2°
ϕ and ω scans	h = −16→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→9
Tmin = 0.914, Tmax = 0.997	l = −34→45
18236 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0827P)^2 + 0.2636P] where P = (Fo^2 + 2Fc^2)/3
3715 reflections	(Δ/σ)max = 0.005
209 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. Sheldrick, G. M. (1996). SADABS, program for scaling and correction of area detector data. University of Göttingen, Germany.

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.

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

	x	y	z	Uiso*/Ueq
C1	0.88041 (10)	0.5098 (2)	0.95611 (4)	0.0397 (3)
C2	0.86381 (11)	0.7040 (2)	0.96131 (4)	0.0456 (4)
H2	0.8572	0.7568	0.9865	0.055*
C3	0.85708 (11)	0.8192 (2)	0.92906 (4)	0.0433 (3)
H3	0.8454	0.9529	0.9323	0.052*
C4	0.86695 (9)	0.7449 (2)	0.89172 (4)	0.0377 (3)
C5	0.88609 (11)	0.54830 (19)	0.88796 (4)	0.0400 (3)
H5	0.8947	0.4949	0.8629	0.048*
C6	0.89277 (10)	0.4309 (2)	0.91968 (4)	0.0409 (3)
H6	0.9057	0.2976	0.9167	0.049*
C7	0.85465 (10)	0.87210 (19)	0.85869 (4)	0.0413 (3)
H7	0.8410	1.0030	0.8644	0.050*
C8	0.86025 (10)	0.8263 (2)	0.82117 (4)	0.0397 (3)
H8	0.8775	0.6980	0.8145	0.048*
C9	0.84162 (10)	0.96038 (19)	0.79042 (4)	0.0422 (3)
H9	0.8265	1.0886	0.7978	0.051*
C10	0.84339 (10)	0.92345 (19)	0.75229 (4)	0.0416 (3)
H10	0.8270	1.0277	0.7357	0.050*
C11	0.86719 (9)	0.74411 (19)	0.73368 (4)	0.0376 (3)
H11	0.8898	0.6398	0.7492	0.045*
C12	0.85890 (10)	0.71789 (19)	0.69554 (4)	0.0381 (3)
H12	0.8378	0.8264	0.6810	0.046*
C13	0.87831 (9)	0.54296 (18)	0.67359 (4)	0.0350 (3)
C14	0.85294 (10)	0.53563 (19)	0.63447 (4)	0.0390 (3)
H14	0.8261	0.6475	0.6225	0.047*
C15	0.86538 (10)	0.3715 (2)	0.61254 (4)	0.0402 (3)
H15	0.8465	0.3709	0.5860	0.048*
C16	0.90548 (9)	0.20826 (18)	0.62948 (4)	0.0374 (3)
C17	0.93447 (10)	0.21290 (18)	0.66831 (4)	0.0383 (3)
H17	0.9642	0.1025	0.6799	0.046*
C18	0.92020 (10)	0.37636 (18)	0.68995 (4)	0.0369 (3)
H18	0.9391	0.3764	0.7165	0.044*
C19	0.89107 (13)	0.0236 (3)	0.57142 (4)	0.0530 (4)
H19A	0.8182	0.0556	0.5690	0.079*
H19B	0.9026	−0.1077	0.5622	0.079*
H19C	0.9317	0.1132	0.5559	0.079*
N1	0.88338 (10)	0.3837 (2)	0.98965 (3)	0.0478 (3)
O1	0.87144 (11)	0.45429 (19)	1.02176 (3)	0.0714 (4)
O2	0.89724 (11)	0.21154 (17)	0.98479 (3)	0.0650 (4)
O3	0.92112 (8)	0.03779 (15)	0.61096 (3)	0.0490 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0354 (6)	0.0482 (8)	0.0355 (7)	−0.0007 (6)	−0.0010 (5)	−0.0042 (5)
C2	0.0469 (8)	0.0523 (9)	0.0375 (8)	0.0003 (6)	−0.0011 (6)	−0.0146 (6)
C3	0.0459 (7)	0.0402 (7)	0.0438 (8)	0.0005 (6)	−0.0005 (6)	−0.0107 (6)
C4	0.0312 (6)	0.0415 (7)	0.0403 (7)	−0.0024 (5)	0.0019 (5)	−0.0050 (6)
C5	0.0439 (7)	0.0415 (7)	0.0347 (7)	0.0018 (6)	0.0059 (5)	−0.0075 (5)
C6	0.0439 (7)	0.0407 (7)	0.0380 (7)	0.0025 (6)	0.0036 (5)	−0.0066 (5)
C7	0.0399 (7)	0.0365 (7)	0.0474 (8)	0.0010 (5)	0.0036 (6)	−0.0047 (6)
C8	0.0379 (7)	0.0358 (7)	0.0454 (8)	0.0019 (5)	0.0027 (5)	−0.0037 (5)
C9	0.0438 (7)	0.0340 (7)	0.0489 (8)	0.0039 (5)	0.0032 (6)	−0.0002 (6)
C10	0.0424 (7)	0.0364 (6)	0.0461 (8)	0.0033 (5)	0.0021 (6)	0.0057 (6)
C11	0.0379 (6)	0.0336 (6)	0.0413 (7)	0.0012 (5)	0.0009 (5)	0.0061 (5)
C12	0.0382 (7)	0.0352 (7)	0.0408 (7)	0.0002 (5)	0.0006 (5)	0.0073 (5)
C13	0.0329 (6)	0.0367 (7)	0.0356 (7)	−0.0026 (5)	0.0005 (5)	0.0073 (5)
C14	0.0382 (7)	0.0410 (7)	0.0378 (7)	0.0018 (5)	−0.0020 (5)	0.0114 (6)
C15	0.0396 (7)	0.0511 (8)	0.0300 (7)	−0.0027 (6)	−0.0024 (5)	0.0063 (6)
C16	0.0363 (6)	0.0398 (7)	0.0360 (7)	−0.0029 (5)	0.0025 (5)	0.0002 (5)
C17	0.0421 (7)	0.0364 (7)	0.0365 (7)	0.0020 (5)	−0.0014 (5)	0.0076 (5)
C18	0.0409 (7)	0.0387 (7)	0.0310 (6)	−0.0009 (5)	−0.0031 (5)	0.0061 (5)
C19	0.0554 (9)	0.0641 (10)	0.0395 (8)	−0.0074 (7)	0.0014 (7)	−0.0100 (7)
N1	0.0505 (7)	0.0578 (8)	0.0352 (6)	0.0031 (6)	−0.0021 (5)	−0.0044 (5)
O1	0.1087 (11)	0.0737 (9)	0.0317 (6)	0.0128 (7)	0.0002 (6)	−0.0076 (5)
O2	0.0999 (10)	0.0511 (7)	0.0442 (7)	0.0088 (6)	0.0002 (6)	−0.0003 (5)
O3	0.0607 (6)	0.0471 (6)	0.0393 (6)	0.0035 (5)	−0.0029 (4)	−0.0075 (4)

Geometric parameters (Å, º)

C1—C2	1.382 (2)	C11—H11	0.9500
C1—C6	1.3845 (18)	C12—C13	1.4582 (19)
C1—N1	1.4564 (19)	C12—H12	0.9500
C2—C3	1.377 (2)	C13—C14	1.3948 (19)
C2—H2	0.9500	C13—C18	1.4024 (17)
C3—C4	1.3978 (18)	C14—C15	1.382 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.3985 (19)	C15—C16	1.3825 (18)
C4—C7	1.455 (2)	C15—H15	0.9500
C5—C6	1.372 (2)	C16—O3	1.3648 (16)
C5—H5	0.9500	C16—C17	1.3964 (19)
C6—H6	0.9500	C17—C18	1.3757 (19)
C7—C8	1.339 (2)	C17—H17	0.9500
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.4369 (19)	C19—O3	1.4270 (18)
C8—H8	0.9500	C19—H19A	0.9800
C9—C10	1.345 (2)	C19—H19B	0.9800
C9—H9	0.9500	C19—H19C	0.9800
C10—C11	1.4397 (19)	N1—O2	1.2246 (18)
C10—H10	0.9500	N1—O1	1.2250 (16)
C11—C12	1.3367 (18)
C2—C1—C6	121.69 (14)	C10—C11—H11	118.6
C2—C1—N1	119.41 (13)	C11—C12—C13	127.90 (12)
C6—C1—N1	118.88 (14)	C11—C12—H12	116.0
C3—C2—C1	118.36 (13)	C13—C12—H12	116.0
C3—C2—H2	120.8	C14—C13—C18	117.01 (12)
C1—C2—H2	120.8	C14—C13—C12	119.66 (11)
C2—C3—C4	121.81 (13)	C18—C13—C12	123.32 (12)
C2—C3—H3	119.1	C15—C14—C13	122.37 (12)
C4—C3—H3	119.1	C15—C14—H14	118.8
C3—C4—C5	117.74 (13)	C13—C14—H14	118.8
C3—C4—C7	119.35 (13)	C14—C15—C16	119.50 (12)
C5—C4—C7	122.89 (12)	C14—C15—H15	120.3
C6—C5—C4	121.38 (13)	C16—C15—H15	120.3
C6—C5—H5	119.3	O3—C16—C15	124.99 (12)
C4—C5—H5	119.3	O3—C16—C17	115.56 (11)
C5—C6—C1	118.98 (13)	C15—C16—C17	119.45 (12)
C5—C6—H6	120.5	C18—C17—C16	120.42 (12)
C1—C6—H6	120.5	C18—C17—H17	119.8
C8—C7—C4	127.61 (13)	C16—C17—H17	119.8
C8—C7—H7	116.2	C17—C18—C13	121.21 (12)
C4—C7—H7	116.2	C17—C18—H18	119.4
C7—C8—C9	123.62 (13)	C13—C18—H18	119.4
C7—C8—H8	118.2	O3—C19—H19A	109.5
C9—C8—H8	118.2	O3—C19—H19B	109.5
C10—C9—C8	126.83 (13)	H19A—C19—H19B	109.5
C10—C9—H9	116.6	O3—C19—H19C	109.5
C8—C9—H9	116.6	H19A—C19—H19C	109.5
C9—C10—C11	127.50 (13)	H19B—C19—H19C	109.5
C9—C10—H10	116.2	O2—N1—O1	122.46 (14)
C11—C10—H10	116.2	O2—N1—C1	119.03 (12)
C12—C11—C10	122.88 (12)	O1—N1—C1	118.51 (14)
C12—C11—H11	118.6	C16—O3—C19	117.99 (11)
C6—C1—C2—C3	1.6 (2)	C11—C12—C13—C18	−7.0 (2)
N1—C1—C2—C3	−177.35 (12)	C18—C13—C14—C15	1.67 (19)
C1—C2—C3—C4	−0.2 (2)	C12—C13—C14—C15	−177.17 (12)
C2—C3—C4—C5	−1.2 (2)	C13—C14—C15—C16	−0.8 (2)
C2—C3—C4—C7	177.31 (13)	C14—C15—C16—O3	179.79 (12)
C3—C4—C5—C6	1.4 (2)	C14—C15—C16—C17	−1.14 (19)
C7—C4—C5—C6	−177.06 (13)	O3—C16—C17—C18	−178.69 (12)
C4—C5—C6—C1	−0.1 (2)	C15—C16—C17—C18	2.15 (19)
C2—C1—C6—C5	−1.4 (2)	C16—C17—C18—C13	−1.2 (2)
N1—C1—C6—C5	177.53 (12)	C14—C13—C18—C17	−0.64 (19)
C3—C4—C7—C8	−179.20 (13)	C12—C13—C18—C17	178.15 (12)
C5—C4—C7—C8	−0.7 (2)	C2—C1—N1—O2	179.37 (14)
C4—C7—C8—C9	176.58 (12)	C6—C1—N1—O2	0.4 (2)
C7—C8—C9—C10	−178.23 (14)	C2—C1—N1—O1	−0.3 (2)
C8—C9—C10—C11	−2.0 (2)	C6—C1—N1—O1	−179.33 (14)
C9—C10—C11—C12	174.50 (14)	C15—C16—O3—C19	−2.08 (19)
C10—C11—C12—C13	−178.43 (12)	C17—C16—O3—C19	178.81 (12)
C11—C12—C13—C14	171.77 (13)

(II) (E,Z,E)-1-(4-ethoxyphenyl)-6-(4-nitrophenyl)hexa-1,3,5-triene

Crystal data

C20H19NO3	F(000) = 1360
Mr = 321.36	Dx = 1.265 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 946 reflections
a = 18.914 (9) Å	θ = 2.3–24.4°
b = 6.880 (3) Å	µ = 0.09 mm^−1
c = 25.927 (11) Å	T = 183 K
V = 3374 (3) Å^3	Rectangular, orange
Z = 8	0.30 × 0.10 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2972 independent reflections
Radiation source: rotating unit	1583 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.135
Detector resolution: 8.366 pixels mm^-1	θmax = 25.0°, θmin = 1.6°
ϕ and ω scans	h = −22→19
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	k = −7→8
Tmin = 0.933, Tmax = 0.998	l = −30→30
11787 measured reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0531P)^2] where P = (Fo^2 + 2Fc^2)/3
2972 reflections	(Δ/σ)max = 0.003
435 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.20 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.

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.

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

	x	y	z	Uiso*/Ueq
C1	0.3896 (4)	1.1009 (12)	1.0080 (3)	0.0429 (19)
C2	0.3283 (4)	1.1630 (12)	0.9856 (3)	0.046 (2)
H2	0.3109	1.2911	0.9906	0.055*
C3	0.2923 (4)	1.0269 (12)	0.9548 (3)	0.046 (2)
H3	0.2495	1.0657	0.9386	0.055*
C4	0.3161 (3)	0.8406 (11)	0.9469 (3)	0.0397 (18)
C5	0.3782 (3)	0.7860 (12)	0.9713 (3)	0.050 (2)
H5	0.3950	0.6566	0.9676	0.060*
C6	0.4159 (3)	0.9148 (12)	1.0009 (3)	0.0468 (19)
H6	0.4594	0.8770	1.0162	0.056*
C7	0.2765 (3)	0.7124 (11)	0.9126 (3)	0.0407 (19)
H7	0.2300	0.7522	0.9037	0.049*
C8	0.2991 (3)	0.5434 (11)	0.8921 (3)	0.0407 (19)
H8	0.3456	0.4990	0.8994	0.049*
C9	0.2535 (4)	0.4287 (11)	0.8592 (3)	0.0453 (19)
H9	0.2069	0.4761	0.8539	0.054*
C10	0.2707 (4)	0.2612 (12)	0.8353 (3)	0.050 (2)
H10	0.2354	0.2064	0.8137	0.060*
C11	0.3366 (4)	0.1552 (12)	0.8385 (3)	0.0442 (19)
H11	0.3749	0.2103	0.8572	0.053*
C12	0.3453 (4)	−0.0193 (12)	0.8159 (3)	0.0460 (19)
H12	0.3061	−0.0648	0.7964	0.055*
C13	0.4061 (4)	−0.1473 (11)	0.8171 (3)	0.0421 (19)
C14	0.4035 (4)	−0.3243 (11)	0.7903 (3)	0.0438 (19)
H14	0.3614	−0.3571	0.7723	0.053*
C15	0.4590 (4)	−0.4516 (11)	0.7890 (3)	0.0439 (19)
H15	0.4551	−0.5701	0.7704	0.053*
C16	0.5207 (4)	−0.4067 (11)	0.8150 (3)	0.0424 (19)
C17	0.5253 (4)	−0.2315 (12)	0.8424 (3)	0.048 (2)
H17	0.5673	−0.1997	0.8608	0.057*
C18	0.4692 (4)	−0.1068 (12)	0.8426 (3)	0.045 (2)
H18	0.4733	0.0125	0.8609	0.054*
C19	0.5769 (4)	−0.6955 (11)	0.7850 (3)	0.050 (2)
H19A	0.5675	−0.6614	0.7486	0.060*
H19B	0.5380	−0.7799	0.7973	0.060*
C20	0.6463 (5)	−0.8012 (13)	0.7893 (4)	0.079 (3)
H20A	0.6840	−0.7205	0.7748	0.119*
H20B	0.6435	−0.9240	0.7703	0.119*
H20C	0.6564	−0.8280	0.8257	0.119*
C21	0.5910 (3)	−0.5610 (12)	−0.0304 (3)	0.0410 (19)
C22	0.6498 (4)	−0.6266 (11)	−0.0036 (3)	0.0411 (19)
H22	0.6657	−0.7569	−0.0071	0.049*
C23	0.6848 (3)	−0.4960 (12)	0.0287 (3)	0.0409 (18)
H23	0.7262	−0.5370	0.0463	0.049*
C24	0.6610 (3)	−0.3121 (12)	0.0354 (3)	0.0397 (19)
C25	0.6027 (3)	−0.2474 (11)	0.0067 (3)	0.0444 (19)
H25	0.5876	−0.1161	0.0094	0.053*
C26	0.5670 (4)	−0.3746 (12)	−0.0256 (3)	0.049 (2)
H26	0.5264	−0.3328	−0.0442	0.059*
C27	0.6992 (4)	−0.1802 (12)	0.0704 (3)	0.0423 (19)
H27	0.7460	−0.2176	0.0791	0.051*
C28	0.6761 (3)	−0.0134 (12)	0.0917 (3)	0.044 (2)
H28	0.6309	0.0340	0.0818	0.053*
C29	0.7158 (4)	0.0955 (12)	0.1282 (3)	0.0467 (19)
H29	0.7609	0.0446	0.1368	0.056*
C30	0.6973 (4)	0.2619 (13)	0.1520 (3)	0.053 (2)
H30	0.7300	0.3094	0.1768	0.063*
C31	0.6346 (3)	0.3771 (11)	0.1449 (3)	0.0406 (18)
H31	0.5979	0.3303	0.1232	0.049*
C32	0.6268 (4)	0.5532 (12)	0.1689 (3)	0.0432 (19)
H32	0.6645	0.5934	0.1906	0.052*
C33	0.5674 (3)	0.6846 (10)	0.1647 (2)	0.0346 (17)
C34	0.5695 (4)	0.8555 (12)	0.1930 (3)	0.0440 (19)
H34	0.6100	0.8803	0.2137	0.053*
C35	0.5154 (4)	0.9927 (12)	0.1925 (3)	0.0455 (19)
H35	0.5193	1.1099	0.2116	0.055*
C36	0.4558 (4)	0.9536 (12)	0.1633 (3)	0.0450 (19)
C37	0.4520 (4)	0.7843 (12)	0.1341 (3)	0.046 (2)
H37	0.4109	0.7583	0.1142	0.055*
C38	0.5066 (4)	0.6556 (12)	0.1336 (3)	0.0466 (19)
H38	0.5039	0.5441	0.1121	0.056*
C39	0.3993 (4)	1.2473 (11)	0.1912 (4)	0.056 (2)
H39A	0.4384	1.3328	0.1798	0.067*
H39B	0.4073	1.2131	0.2279	0.067*
C40	0.3306 (4)	1.3494 (14)	0.1854 (4)	0.084 (3)
H40A	0.3322	1.4332	0.1548	0.126*
H40B	0.3216	1.4289	0.2161	0.126*
H40C	0.2927	1.2536	0.1814	0.126*
N1	0.4304 (4)	1.2402 (11)	1.0395 (3)	0.0567 (18)
N2	0.5519 (4)	−0.7003 (11)	−0.0627 (3)	0.0541 (19)
O1	0.4013 (3)	1.3938 (10)	1.0511 (2)	0.0761 (19)
O2	0.4899 (3)	1.1938 (9)	1.0535 (2)	0.0694 (19)
O3	0.5800 (2)	−0.5236 (7)	0.8155 (2)	0.0479 (13)
O4	0.5801 (3)	−0.8518 (9)	−0.0741 (2)	0.0740 (18)
O5	0.4919 (3)	−0.6508 (8)	−0.0770 (2)	0.0673 (16)
O6	0.3976 (2)	1.0752 (8)	0.1604 (2)	0.0538 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.044 (4)	0.053 (6)	0.031 (4)	−0.003 (4)	−0.002 (3)	0.005 (4)
C2	0.053 (5)	0.044 (5)	0.041 (5)	0.007 (4)	0.008 (3)	0.009 (4)
C3	0.038 (4)	0.061 (6)	0.039 (5)	0.007 (4)	−0.002 (3)	0.005 (4)
C4	0.040 (4)	0.037 (5)	0.042 (5)	0.005 (3)	0.009 (3)	0.001 (4)
C5	0.038 (4)	0.047 (6)	0.065 (6)	0.009 (3)	−0.008 (4)	0.002 (4)
C6	0.035 (4)	0.056 (6)	0.049 (5)	0.008 (4)	−0.003 (3)	−0.006 (4)
C7	0.036 (4)	0.043 (5)	0.043 (5)	−0.002 (3)	0.005 (3)	0.008 (4)
C8	0.036 (4)	0.045 (5)	0.041 (5)	−0.004 (3)	0.002 (3)	0.005 (4)
C9	0.048 (4)	0.042 (5)	0.046 (5)	−0.005 (4)	−0.012 (4)	0.006 (4)
C10	0.062 (5)	0.048 (6)	0.039 (5)	−0.009 (4)	−0.009 (4)	0.006 (4)
C11	0.056 (5)	0.048 (6)	0.028 (4)	−0.008 (4)	0.000 (3)	0.003 (4)
C12	0.050 (4)	0.055 (6)	0.034 (4)	−0.012 (4)	−0.003 (3)	−0.005 (4)
C13	0.058 (5)	0.043 (5)	0.026 (4)	−0.011 (4)	0.006 (3)	0.002 (4)
C14	0.043 (4)	0.053 (6)	0.036 (4)	−0.011 (4)	−0.001 (3)	−0.004 (4)
C15	0.049 (5)	0.048 (5)	0.035 (4)	−0.011 (4)	0.000 (4)	−0.005 (4)
C16	0.049 (5)	0.051 (6)	0.028 (4)	−0.011 (4)	0.004 (3)	−0.003 (4)
C17	0.049 (4)	0.056 (6)	0.037 (5)	−0.018 (4)	−0.002 (3)	−0.014 (4)
C18	0.049 (4)	0.052 (6)	0.035 (4)	−0.008 (4)	−0.003 (3)	−0.013 (4)
C19	0.055 (5)	0.041 (5)	0.053 (5)	−0.006 (4)	−0.005 (4)	−0.003 (4)
C20	0.088 (7)	0.057 (7)	0.092 (8)	0.011 (5)	−0.019 (5)	−0.029 (6)
C21	0.034 (4)	0.051 (6)	0.038 (5)	0.001 (3)	0.001 (3)	−0.003 (4)
C22	0.052 (4)	0.033 (5)	0.039 (5)	0.009 (3)	0.009 (3)	0.010 (4)
C23	0.033 (4)	0.057 (6)	0.032 (4)	0.005 (4)	0.001 (3)	0.007 (4)
C24	0.027 (4)	0.057 (6)	0.035 (4)	0.009 (3)	0.004 (3)	0.004 (4)
C25	0.054 (4)	0.047 (5)	0.033 (4)	0.001 (4)	0.005 (4)	−0.004 (4)
C26	0.046 (4)	0.058 (6)	0.043 (5)	0.009 (4)	−0.001 (3)	0.006 (4)
C27	0.037 (4)	0.046 (6)	0.044 (5)	0.000 (4)	−0.003 (3)	0.011 (4)
C28	0.037 (4)	0.056 (6)	0.040 (5)	−0.001 (4)	0.008 (3)	0.013 (4)
C29	0.044 (4)	0.045 (6)	0.050 (5)	0.002 (4)	−0.002 (4)	0.005 (4)
C30	0.059 (5)	0.059 (7)	0.040 (5)	−0.001 (4)	−0.001 (4)	0.016 (4)
C31	0.046 (4)	0.047 (5)	0.029 (4)	−0.003 (3)	0.004 (3)	0.007 (4)
C32	0.058 (5)	0.049 (6)	0.023 (4)	−0.004 (4)	0.000 (3)	0.002 (4)
C33	0.057 (4)	0.026 (5)	0.020 (4)	−0.009 (3)	0.004 (3)	0.002 (3)
C34	0.046 (4)	0.047 (5)	0.039 (5)	−0.020 (4)	−0.003 (3)	0.004 (4)
C35	0.043 (4)	0.043 (5)	0.051 (5)	−0.008 (4)	0.002 (4)	0.001 (4)
C36	0.049 (5)	0.048 (6)	0.038 (5)	0.001 (4)	−0.006 (4)	−0.005 (4)
C37	0.044 (4)	0.055 (6)	0.040 (4)	−0.014 (4)	−0.011 (3)	−0.002 (4)
C38	0.062 (5)	0.045 (5)	0.033 (5)	−0.005 (4)	−0.005 (4)	−0.004 (4)
C39	0.079 (6)	0.030 (5)	0.058 (6)	0.003 (4)	−0.013 (4)	−0.006 (4)
C40	0.065 (6)	0.083 (8)	0.104 (8)	0.026 (5)	−0.024 (5)	−0.022 (6)
N1	0.065 (5)	0.060 (6)	0.046 (4)	−0.002 (4)	0.006 (4)	−0.003 (4)
N2	0.057 (5)	0.062 (6)	0.042 (4)	−0.005 (4)	0.001 (3)	0.003 (4)
O1	0.097 (5)	0.062 (5)	0.069 (4)	0.012 (4)	−0.007 (3)	−0.015 (4)
O2	0.059 (4)	0.083 (5)	0.067 (5)	−0.006 (3)	−0.019 (3)	0.001 (3)
O3	0.055 (3)	0.037 (3)	0.052 (4)	−0.004 (2)	−0.008 (2)	−0.006 (3)
O4	0.082 (4)	0.067 (5)	0.073 (5)	0.013 (3)	−0.013 (3)	−0.020 (4)
O5	0.058 (4)	0.077 (4)	0.067 (4)	−0.009 (3)	−0.008 (3)	−0.010 (4)
O6	0.051 (3)	0.049 (4)	0.061 (4)	−0.003 (2)	−0.012 (2)	−0.013 (3)

Geometric parameters (Å, º)

C1—C2	1.366 (10)	C21—N2	1.470 (10)
C1—C6	1.386 (10)	C22—C23	1.395 (10)
C1—N1	1.476 (10)	C22—H22	0.9500
C2—C3	1.407 (11)	C23—C24	1.354 (10)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.374 (10)	C24—C25	1.405 (10)
C3—H3	0.9500	C24—C27	1.472 (10)
C4—C5	1.387 (9)	C25—C26	1.387 (10)
C4—C7	1.459 (10)	C25—H25	0.9500
C5—C6	1.371 (11)	C26—H26	0.9500
C5—H5	0.9500	C27—C28	1.345 (10)
C6—H6	0.9500	C27—H27	0.9500
C7—C8	1.347 (10)	C28—C29	1.421 (11)
C7—H7	0.9500	C28—H28	0.9500
C8—C9	1.447 (10)	C29—C30	1.347 (11)
C8—H8	0.9500	C29—H29	0.9500
C9—C10	1.348 (10)	C30—C31	1.439 (10)
C9—H9	0.9500	C30—H30	0.9500
C10—C11	1.446 (10)	C31—C32	1.370 (10)
C10—H10	0.9500	C31—H31	0.9500
C11—C12	1.347 (10)	C32—C33	1.446 (10)
C11—H11	0.9500	C32—H32	0.9500
C12—C13	1.449 (10)	C33—C34	1.386 (10)
C12—H12	0.9500	C33—C38	1.418 (9)
C13—C18	1.392 (9)	C34—C35	1.392 (10)
C13—C14	1.403 (10)	C34—H34	0.9500
C14—C15	1.367 (10)	C35—C36	1.384 (10)
C14—H14	0.9500	C35—H35	0.9500
C15—C16	1.383 (9)	C36—O6	1.385 (9)
C15—H15	0.9500	C36—C37	1.390 (10)
C16—O3	1.380 (8)	C37—C38	1.359 (10)
C16—C17	1.402 (10)	C37—H37	0.9500
C17—C18	1.366 (10)	C38—H38	0.9500
C17—H17	0.9500	C39—O6	1.428 (9)
C18—H18	0.9500	C39—C40	1.486 (10)
C19—O3	1.423 (9)	C39—H39A	0.9900
C19—C20	1.505 (10)	C39—H39B	0.9900
C19—H19A	0.9900	C40—H40A	0.9800
C19—H19B	0.9900	C40—H40B	0.9800
C20—H20A	0.9800	C40—H40C	0.9800
C20—H20B	0.9800	N1—O2	1.224 (8)
C20—H20C	0.9800	N1—O1	1.230 (8)
C21—C26	1.366 (10)	N2—O4	1.209 (8)
C21—C22	1.387 (10)	N2—O5	1.241 (8)
C2—C1—C6	122.4 (7)	C21—C22—H22	120.9
C2—C1—N1	118.4 (7)	C23—C22—H22	120.9
C6—C1—N1	119.1 (7)	C24—C23—C22	121.5 (7)
C1—C2—C3	116.4 (7)	C24—C23—H23	119.3
C1—C2—H2	121.8	C22—C23—H23	119.3
C3—C2—H2	121.8	C23—C24—C25	119.2 (7)
C4—C3—C2	123.2 (7)	C23—C24—C27	119.6 (6)
C4—C3—H3	118.4	C25—C24—C27	121.1 (7)
C2—C3—H3	118.4	C26—C25—C24	120.2 (7)
C3—C4—C5	117.5 (7)	C26—C25—H25	119.9
C3—C4—C7	119.1 (7)	C24—C25—H25	119.9
C5—C4—C7	123.3 (7)	C21—C26—C25	119.1 (7)
C6—C5—C4	121.4 (7)	C21—C26—H26	120.5
C6—C5—H5	119.3	C25—C26—H26	120.5
C4—C5—H5	119.3	C28—C27—C24	128.3 (7)
C5—C6—C1	119.1 (7)	C28—C27—H27	115.9
C5—C6—H6	120.5	C24—C27—H27	115.9
C1—C6—H6	120.5	C27—C28—C29	123.5 (7)
C8—C7—C4	126.8 (7)	C27—C28—H28	118.3
C8—C7—H7	116.6	C29—C28—H28	118.3
C4—C7—H7	116.6	C30—C29—C28	128.1 (7)
C7—C8—C9	120.9 (7)	C30—C29—H29	116.0
C7—C8—H8	119.6	C28—C29—H29	116.0
C9—C8—H8	119.6	C29—C30—C31	128.6 (8)
C10—C9—C8	126.4 (7)	C29—C30—H30	115.7
C10—C9—H9	116.8	C31—C30—H30	115.7
C8—C9—H9	116.8	C32—C31—C30	121.2 (7)
C9—C10—C11	127.7 (7)	C32—C31—H31	119.4
C9—C10—H10	116.1	C30—C31—H31	119.4
C11—C10—H10	116.1	C31—C32—C33	127.0 (7)
C12—C11—C10	122.0 (7)	C31—C32—H32	116.5
C12—C11—H11	119.0	C33—C32—H32	116.5
C10—C11—H11	119.0	C34—C33—C38	116.4 (7)
C11—C12—C13	129.0 (7)	C34—C33—C32	117.8 (6)
C11—C12—H12	115.5	C38—C33—C32	125.8 (7)
C13—C12—H12	115.5	C33—C34—C35	123.2 (7)
C18—C13—C14	116.0 (7)	C33—C34—H34	118.4
C18—C13—C12	124.7 (7)	C35—C34—H34	118.4
C14—C13—C12	119.3 (6)	C36—C35—C34	118.2 (7)
C15—C14—C13	122.8 (7)	C36—C35—H35	120.9
C15—C14—H14	118.6	C34—C35—H35	120.9
C13—C14—H14	118.6	C35—C36—O6	124.0 (7)
C14—C15—C16	119.5 (7)	C35—C36—C37	120.2 (7)
C14—C15—H15	120.2	O6—C36—C37	115.9 (6)
C16—C15—H15	120.2	C38—C37—C36	120.7 (6)
O3—C16—C15	124.1 (7)	C38—C37—H37	119.6
O3—C16—C17	116.5 (6)	C36—C37—H37	119.6
C15—C16—C17	119.4 (7)	C37—C38—C33	121.3 (7)
C18—C17—C16	119.6 (7)	C37—C38—H38	119.4
C18—C17—H17	120.2	C33—C38—H38	119.4
C16—C17—H17	120.2	O6—C39—C40	108.4 (7)
C17—C18—C13	122.6 (8)	O6—C39—H39A	110.0
C17—C18—H18	118.7	C40—C39—H39A	110.0
C13—C18—H18	118.7	O6—C39—H39B	110.0
O3—C19—C20	108.9 (6)	C40—C39—H39B	110.0
O3—C19—H19A	109.9	H39A—C39—H39B	108.4
C20—C19—H19A	109.9	C39—C40—H40A	109.5
O3—C19—H19B	109.9	C39—C40—H40B	109.5
C20—C19—H19B	109.9	H40A—C40—H40B	109.5
H19A—C19—H19B	108.3	C39—C40—H40C	109.5
C19—C20—H20A	109.5	H40A—C40—H40C	109.5
C19—C20—H20B	109.5	H40B—C40—H40C	109.5
H20A—C20—H20B	109.5	O2—N1—O1	124.3 (7)
C19—C20—H20C	109.5	O2—N1—C1	118.4 (7)
H20A—C20—H20C	109.5	O1—N1—C1	117.3 (7)
H20B—C20—H20C	109.5	O4—N2—O5	124.5 (7)
C26—C21—C22	121.7 (7)	O4—N2—C21	118.7 (7)
C26—C21—N2	119.8 (7)	O5—N2—C21	116.8 (7)
C22—C21—N2	118.4 (7)	C16—O3—C19	116.5 (5)
C21—C22—C23	118.1 (7)	C36—O6—C39	116.9 (6)
C6—C1—C2—C3	0.4 (10)	C22—C21—C26—C25	0.5 (11)
N1—C1—C2—C3	178.2 (6)	N2—C21—C26—C25	177.2 (7)
C1—C2—C3—C4	0.1 (11)	C24—C25—C26—C21	−2.4 (11)
C2—C3—C4—C5	0.8 (11)	C23—C24—C27—C28	−162.7 (7)
C2—C3—C4—C7	−177.6 (6)	C25—C24—C27—C28	20.9 (11)
C3—C4—C5—C6	−2.2 (11)	C24—C27—C28—C29	175.1 (7)
C7—C4—C5—C6	176.1 (7)	C27—C28—C29—C30	−179.2 (7)
C4—C5—C6—C1	2.7 (12)	C28—C29—C30—C31	−3.4 (14)
C2—C1—C6—C5	−1.8 (11)	C29—C30—C31—C32	−173.8 (7)
N1—C1—C6—C5	−179.5 (7)	C30—C31—C32—C33	179.1 (7)
C3—C4—C7—C8	165.1 (7)	C31—C32—C33—C34	179.1 (6)
C5—C4—C7—C8	−13.2 (12)	C31—C32—C33—C38	−1.6 (11)
C4—C7—C8—C9	178.9 (7)	C38—C33—C34—C35	1.1 (10)
C7—C8—C9—C10	177.8 (7)	C32—C33—C34—C35	−179.5 (7)
C8—C9—C10—C11	2.7 (13)	C33—C34—C35—C36	1.7 (11)
C9—C10—C11—C12	174.6 (7)	C34—C35—C36—O6	178.3 (7)
C10—C11—C12—C13	−177.1 (7)	C34—C35—C36—C37	−2.1 (11)
C11—C12—C13—C18	−1.3 (12)	C35—C36—C37—C38	−0.2 (11)
C11—C12—C13—C14	−179.9 (7)	O6—C36—C37—C38	179.3 (7)
C18—C13—C14—C15	0.3 (10)	C36—C37—C38—C33	3.1 (11)
C12—C13—C14—C15	179.0 (7)	C34—C33—C38—C37	−3.5 (10)
C13—C14—C15—C16	0.0 (11)	C32—C33—C38—C37	177.1 (7)
C14—C15—C16—O3	−179.0 (6)	C2—C1—N1—O2	−169.9 (7)
C14—C15—C16—C17	0.3 (10)	C6—C1—N1—O2	8.0 (10)
O3—C16—C17—C18	178.5 (7)	C2—C1—N1—O1	12.1 (10)
C15—C16—C17—C18	−0.8 (11)	C6—C1—N1—O1	−170.1 (7)
C16—C17—C18—C13	1.1 (11)	C26—C21—N2—O4	166.6 (7)
C14—C13—C18—C17	−0.8 (10)	C22—C21—N2—O4	−16.5 (10)
C12—C13—C18—C17	−179.5 (7)	C26—C21—N2—O5	−12.0 (10)
C26—C21—C22—C23	−0.5 (10)	C22—C21—N2—O5	164.8 (6)
N2—C21—C22—C23	−177.2 (6)	C15—C16—O3—C19	3.0 (10)
C21—C22—C23—C24	2.5 (10)	C17—C16—O3—C19	−176.2 (6)
C22—C23—C24—C25	−4.4 (10)	C20—C19—O3—C16	178.7 (7)
C22—C23—C24—C27	179.1 (6)	C35—C36—O6—C39	−2.2 (10)
C23—C24—C25—C26	4.3 (10)	C37—C36—O6—C39	178.3 (7)
C27—C24—C25—C26	−179.3 (6)	C40—C39—O6—C36	−176.2 (8)

(III) (E,Z,E)-1-(4-nitrophenyl)-6-(4-n-propoxyphenyl)hexa-1,3,5-triene

Crystal data

C21H21NO3	F(000) = 712
Mr = 335.39	Dx = 1.251 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5309 reflections
a = 15.3615 (11) Å	θ = 2.4–28.3°
b = 6.8341 (5) Å	µ = 0.08 mm^−1
c = 17.6625 (12) Å	T = 223 K
β = 106.215 (1)°	Rectangular, red
V = 1780.5 (2) Å^3	0.45 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4007 independent reflections
Radiation source: rotating unit	3307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.366 pixels mm^-1	θmax = 28.3°, θmin = 1.4°
ϕ and ω scans	h = −19→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→8
Tmin = 0.873, Tmax = 0.984	l = −19→23
10440 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 0.288P] where P = (Fo^2 + 2Fc^2)/3
4007 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. Sheldrick, G. M. (1996). SADABS, program for scaling and correction of area detector data. University of Göttingen, Germany.

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.

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

	x	y	z	Uiso*/Ueq
C1	−0.17887 (8)	0.68308 (18)	0.40969 (7)	0.0405 (3)
C2	−0.20386 (8)	0.87765 (19)	0.40620 (7)	0.0429 (3)
H2	−0.2493	0.9265	0.3630	0.052*
C3	−0.16058 (7)	0.99830 (18)	0.46754 (7)	0.0402 (3)
H3	−0.1768	1.1312	0.4655	0.048*
C4	−0.09321 (7)	0.92933 (16)	0.53273 (6)	0.0345 (2)
C5	−0.07023 (8)	0.73096 (17)	0.53382 (7)	0.0409 (3)
H5	−0.0254	0.6804	0.5771	0.049*
C6	−0.11210 (9)	0.60887 (18)	0.47269 (7)	0.0438 (3)
H6	−0.0955	0.4763	0.4737	0.053*
C7	−0.05072 (7)	1.06399 (17)	0.59595 (6)	0.0364 (2)
H7	−0.0745	1.1916	0.5919	0.044*
C8	0.01881 (7)	1.02554 (17)	0.65954 (6)	0.0361 (2)
H8	0.0441	0.8993	0.6650	0.043*
C9	0.05648 (7)	1.16771 (17)	0.71968 (6)	0.0378 (2)
H9	0.0322	1.2948	0.7115	0.045*
C10	0.12334 (7)	1.13672 (17)	0.78683 (7)	0.0386 (3)
H10	0.1406	1.2448	0.8206	0.046*
C11	0.17121 (7)	0.95658 (17)	0.81245 (7)	0.0385 (3)
H11	0.1610	0.8493	0.7778	0.046*
C12	0.23005 (7)	0.93722 (17)	0.88440 (7)	0.0385 (3)
H12	0.2393	1.0496	0.9163	0.046*
C13	0.28125 (7)	0.76450 (16)	0.91922 (7)	0.0366 (2)
C14	0.33490 (8)	0.77312 (18)	0.99706 (7)	0.0430 (3)
H14	0.3386	0.8918	1.0247	0.052*
C15	0.38306 (8)	0.61317 (18)	1.03520 (7)	0.0431 (3)
H15	0.4186	0.6237	1.0878	0.052*
C16	0.37845 (7)	0.43777 (17)	0.99523 (7)	0.0381 (3)
C17	0.32796 (8)	0.42800 (17)	0.91590 (7)	0.0393 (3)
H17	0.3269	0.3112	0.8875	0.047*
C18	0.28010 (8)	0.58754 (17)	0.87928 (7)	0.0389 (3)
H18	0.2458	0.5777	0.8263	0.047*
C19	0.47326 (8)	0.27455 (18)	1.10809 (7)	0.0431 (3)
H19A	0.4354	0.3147	1.1417	0.052*
H19B	0.5223	0.3702	1.1143	0.052*
C20	0.51229 (9)	0.0758 (2)	1.13229 (8)	0.0511 (3)
H20A	0.5467	0.0327	1.0962	0.061*
H20B	0.4630	−0.0178	1.1287	0.061*
C21	0.57402 (10)	0.0784 (2)	1.21601 (9)	0.0634 (4)
H21A	0.6227	0.1716	1.2197	0.095*
H21B	0.5994	−0.0510	1.2299	0.095*
H21C	0.5394	0.1163	1.2519	0.095*
N1	−0.22321 (8)	0.55365 (18)	0.34488 (6)	0.0530 (3)
O1	−0.29183 (7)	0.61106 (19)	0.29632 (7)	0.0761 (4)
O2	−0.18905 (9)	0.39308 (17)	0.34138 (6)	0.0775 (4)
O3	0.41971 (6)	0.26844 (12)	1.02721 (5)	0.0447 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0431 (6)	0.0442 (6)	0.0348 (6)	−0.0008 (5)	0.0120 (5)	−0.0042 (5)
C2	0.0394 (6)	0.0495 (7)	0.0370 (6)	0.0090 (5)	0.0059 (5)	−0.0002 (5)
C3	0.0402 (6)	0.0390 (6)	0.0399 (6)	0.0098 (5)	0.0088 (5)	0.0005 (5)
C4	0.0347 (5)	0.0379 (6)	0.0325 (5)	0.0032 (4)	0.0121 (4)	0.0010 (4)
C5	0.0483 (6)	0.0385 (6)	0.0340 (6)	0.0070 (5)	0.0081 (5)	0.0034 (5)
C6	0.0562 (7)	0.0354 (6)	0.0392 (6)	0.0053 (5)	0.0121 (5)	0.0008 (5)
C7	0.0390 (5)	0.0355 (6)	0.0360 (6)	0.0043 (4)	0.0127 (4)	0.0007 (4)
C8	0.0399 (5)	0.0347 (6)	0.0347 (5)	0.0029 (4)	0.0122 (4)	0.0018 (4)
C9	0.0424 (6)	0.0338 (6)	0.0377 (6)	0.0021 (4)	0.0122 (5)	0.0007 (4)
C10	0.0433 (6)	0.0362 (6)	0.0362 (6)	−0.0031 (5)	0.0107 (5)	−0.0033 (4)
C11	0.0410 (6)	0.0366 (6)	0.0363 (6)	−0.0029 (5)	0.0082 (5)	−0.0011 (4)
C12	0.0399 (6)	0.0363 (6)	0.0376 (6)	−0.0070 (4)	0.0082 (5)	−0.0013 (4)
C13	0.0348 (5)	0.0371 (6)	0.0356 (6)	−0.0073 (4)	0.0058 (4)	0.0023 (4)
C14	0.0470 (6)	0.0370 (6)	0.0386 (6)	−0.0076 (5)	0.0017 (5)	−0.0034 (5)
C15	0.0449 (6)	0.0418 (6)	0.0343 (6)	−0.0071 (5)	−0.0027 (5)	0.0002 (5)
C16	0.0358 (5)	0.0394 (6)	0.0366 (6)	−0.0051 (4)	0.0061 (4)	0.0033 (5)
C17	0.0426 (6)	0.0389 (6)	0.0343 (6)	−0.0052 (5)	0.0071 (5)	−0.0019 (4)
C18	0.0404 (6)	0.0427 (6)	0.0303 (5)	−0.0063 (5)	0.0044 (4)	−0.0001 (4)
C19	0.0421 (6)	0.0460 (7)	0.0356 (6)	−0.0059 (5)	0.0015 (5)	0.0038 (5)
C20	0.0507 (7)	0.0500 (8)	0.0459 (7)	0.0010 (6)	0.0024 (6)	0.0076 (6)
C21	0.0630 (8)	0.0682 (10)	0.0487 (8)	0.0002 (7)	−0.0014 (7)	0.0179 (7)
N1	0.0642 (7)	0.0516 (7)	0.0402 (6)	−0.0015 (5)	0.0099 (5)	−0.0085 (5)
O1	0.0662 (7)	0.0855 (8)	0.0591 (7)	0.0083 (6)	−0.0112 (5)	−0.0247 (6)
O2	0.1151 (9)	0.0488 (6)	0.0550 (6)	0.0114 (6)	0.0010 (6)	−0.0145 (5)
O3	0.0494 (5)	0.0407 (5)	0.0370 (4)	0.0009 (4)	0.0005 (4)	0.0028 (3)

Geometric parameters (Å, º)

C1—C2	1.3806 (18)	C13—C14	1.3928 (16)
C1—C6	1.3821 (17)	C13—C18	1.3977 (16)
C1—N1	1.4565 (16)	C14—C15	1.3848 (17)
C2—C3	1.3760 (17)	C14—H14	0.9400
C2—H2	0.9400	C15—C16	1.3829 (17)
C3—C4	1.3977 (15)	C15—H15	0.9400
C3—H3	0.9400	C16—O3	1.3638 (14)
C4—C5	1.3996 (16)	C16—C17	1.4009 (16)
C4—C7	1.4535 (15)	C17—C18	1.3719 (16)
C5—C6	1.3739 (17)	C17—H17	0.9400
C5—H5	0.9400	C18—H18	0.9400
C6—H6	0.9400	C19—O3	1.4362 (14)
C7—C8	1.3422 (15)	C19—C20	1.4980 (18)
C7—H7	0.9400	C19—H19A	0.9800
C8—C9	1.4366 (16)	C19—H19B	0.9800
C8—H8	0.9400	C20—C21	1.5176 (19)
C9—C10	1.3514 (16)	C20—H20A	0.9800
C9—H9	0.9400	C20—H20B	0.9800
C10—C11	1.4405 (16)	C21—H21A	0.9700
C10—H10	0.9400	C21—H21B	0.9700
C11—C12	1.3446 (15)	C21—H21C	0.9700
C11—H11	0.9400	N1—O1	1.2230 (15)
C12—C13	1.4560 (16)	N1—O2	1.2253 (16)
C12—H12	0.9400
C2—C1—C6	121.60 (11)	C18—C13—C12	123.99 (10)
C2—C1—N1	119.13 (11)	C15—C14—C13	122.36 (11)
C6—C1—N1	119.27 (11)	C15—C14—H14	118.8
C3—C2—C1	118.35 (11)	C13—C14—H14	118.8
C3—C2—H2	120.8	C16—C15—C14	119.45 (11)
C1—C2—H2	120.8	C16—C15—H15	120.3
C2—C3—C4	122.03 (11)	C14—C15—H15	120.3
C2—C3—H3	119.0	O3—C16—C15	124.92 (10)
C4—C3—H3	119.0	O3—C16—C17	115.93 (10)
C3—C4—C5	117.63 (10)	C15—C16—C17	119.15 (11)
C3—C4—C7	119.32 (10)	C18—C17—C16	120.51 (11)
C5—C4—C7	123.05 (10)	C18—C17—H17	119.7
C6—C5—C4	121.10 (11)	C16—C17—H17	119.7
C6—C5—H5	119.4	C17—C18—C13	121.34 (10)
C4—C5—H5	119.4	C17—C18—H18	119.3
C5—C6—C1	119.28 (11)	C13—C18—H18	119.3
C5—C6—H6	120.4	O3—C19—C20	109.26 (10)
C1—C6—H6	120.4	O3—C19—H19A	109.8
C8—C7—C4	126.91 (11)	C20—C19—H19A	109.8
C8—C7—H7	116.5	O3—C19—H19B	109.8
C4—C7—H7	116.5	C20—C19—H19B	109.8
C7—C8—C9	123.26 (11)	H19A—C19—H19B	108.3
C7—C8—H8	118.4	C19—C20—C21	111.03 (12)
C9—C8—H8	118.4	C19—C20—H20A	109.4
C10—C9—C8	126.40 (11)	C21—C20—H20A	109.4
C10—C9—H9	116.8	C19—C20—H20B	109.4
C8—C9—H9	116.8	C21—C20—H20B	109.4
C9—C10—C11	127.29 (11)	H20A—C20—H20B	108.0
C9—C10—H10	116.4	C20—C21—H21A	109.5
C11—C10—H10	116.4	C20—C21—H21B	109.5
C12—C11—C10	122.04 (11)	H21A—C21—H21B	109.5
C12—C11—H11	119.0	C20—C21—H21C	109.5
C10—C11—H11	119.0	H21A—C21—H21C	109.5
C11—C12—C13	128.34 (11)	H21B—C21—H21C	109.5
C11—C12—H12	115.8	O1—N1—O2	123.32 (12)
C13—C12—H12	115.8	O1—N1—C1	118.60 (12)
C14—C13—C18	117.09 (10)	O2—N1—C1	118.08 (11)
C14—C13—C12	118.92 (10)	C16—O3—C19	117.27 (9)
C6—C1—C2—C3	−0.11 (18)	C18—C13—C14—C15	−2.19 (18)
N1—C1—C2—C3	−179.30 (11)	C12—C13—C14—C15	177.69 (11)
C1—C2—C3—C4	−0.43 (18)	C13—C14—C15—C16	0.12 (19)
C2—C3—C4—C5	0.29 (17)	C14—C15—C16—O3	−177.26 (11)
C2—C3—C4—C7	−179.40 (10)	C14—C15—C16—C17	2.54 (18)
C3—C4—C5—C6	0.39 (17)	O3—C16—C17—C18	176.71 (10)
C7—C4—C5—C6	−179.92 (11)	C15—C16—C17—C18	−3.11 (17)
C4—C5—C6—C1	−0.91 (18)	C16—C17—C18—C13	0.99 (17)
C2—C1—C6—C5	0.78 (18)	C14—C13—C18—C17	1.61 (17)
N1—C1—C6—C5	179.96 (11)	C12—C13—C18—C17	−178.26 (10)
C3—C4—C7—C8	−175.01 (11)	O3—C19—C20—C21	176.62 (11)
C5—C4—C7—C8	5.31 (18)	C2—C1—N1—O1	−12.90 (18)
C4—C7—C8—C9	−179.65 (10)	C6—C1—N1—O1	167.89 (12)
C7—C8—C9—C10	176.68 (11)	C2—C1—N1—O2	166.30 (13)
C8—C9—C10—C11	0.23 (19)	C6—C1—N1—O2	−12.90 (18)
C9—C10—C11—C12	−172.82 (11)	C15—C16—O3—C19	−1.22 (17)
C10—C11—C12—C13	178.20 (10)	C17—C16—O3—C19	178.98 (9)
C11—C12—C13—C14	−176.22 (11)	C20—C19—O3—C16	179.74 (10)
C11—C12—C13—C18	3.65 (19)

(IV) (E,Z,E)-1-(4-n-butoxyphenyl)-6-(4-nitrophenyl)hexa-1,3,5-triene

Crystal data

C22H23NO3	F(000) = 744
Mr = 349.41	Dx = 1.222 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5402 reflections
a = 17.0571 (10) Å	θ = 2.4–28.1°
b = 6.7244 (4) Å	µ = 0.08 mm^−1
c = 17.2095 (10) Å	T = 183 K
β = 105.884 (1)°	Rectangular, orange
V = 1898.54 (19) Å^3	0.40 × 0.15 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4309 independent reflections
Radiation source: rotating unit	3596 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.366 pixels mm^-1	θmax = 28.2°, θmin = 2.4°
ϕ and ω scans	h = −21→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→4
Tmin = 0.888, Tmax = 0.997	l = −20→21
11363 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0687P)^2 + 0.3548P] where P = (Fo^2 + 2Fc^2)/3
4309 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. Sheldrick, G. M. (1996). SADABS, program for scaling and correction of area detector data. University of Göttingen, Germany.

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.

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

	x	y	z	Uiso*/Ueq
C1	0.66312 (7)	0.82779 (19)	0.58353 (7)	0.0379 (3)
C2	0.69457 (8)	0.6376 (2)	0.58700 (8)	0.0447 (3)
H2	0.7407	0.5999	0.6294	0.054*
C3	0.65767 (8)	0.50399 (19)	0.52772 (7)	0.0416 (3)
H3	0.6790	0.3730	0.5296	0.050*
C4	0.58955 (7)	0.55577 (17)	0.46470 (7)	0.0335 (2)
C5	0.56058 (7)	0.75163 (18)	0.46264 (7)	0.0360 (3)
H5	0.5152	0.7916	0.4198	0.043*
C6	0.59677 (7)	0.88668 (18)	0.52161 (7)	0.0373 (3)
H6	0.5765	1.0186	0.5198	0.045*
C7	0.55240 (7)	0.40636 (17)	0.40463 (7)	0.0360 (3)
H7	0.5786	0.2805	0.4095	0.043*
C8	0.48492 (7)	0.42851 (17)	0.34316 (7)	0.0355 (3)
H8	0.4576	0.5530	0.3371	0.043*
C9	0.45174 (7)	0.27339 (18)	0.28592 (7)	0.0376 (3)
H9	0.4769	0.1464	0.2961	0.045*
C10	0.38838 (7)	0.29124 (18)	0.21929 (7)	0.0379 (3)
H10	0.3730	0.1748	0.1875	0.045*
C11	0.34151 (7)	0.46822 (18)	0.19116 (7)	0.0378 (3)
H11	0.3496	0.5815	0.2254	0.045*
C12	0.28687 (7)	0.47921 (18)	0.11832 (7)	0.0370 (3)
H12	0.2796	0.3626	0.0859	0.044*
C13	0.23756 (7)	0.65117 (18)	0.08378 (7)	0.0356 (3)
C14	0.19030 (7)	0.64741 (19)	0.00360 (7)	0.0406 (3)
H14	0.1911	0.5319	−0.0280	0.049*
C15	0.14211 (8)	0.8074 (2)	−0.03142 (8)	0.0435 (3)
H15	0.1110	0.8014	−0.0864	0.052*
C16	0.13960 (8)	0.97538 (19)	0.01405 (8)	0.0426 (3)
C17	0.18606 (8)	0.9823 (2)	0.09453 (8)	0.0453 (3)
H17	0.1845	1.0973	0.1261	0.054*
C18	0.23406 (8)	0.82371 (19)	0.12820 (7)	0.0417 (3)
H18	0.2656	0.8312	0.1829	0.050*
C19	0.04326 (9)	1.1428 (2)	−0.09347 (8)	0.0521 (3)
H19A	0.0044	1.0302	−0.1026	0.063*
H19B	0.0772	1.1305	−0.1316	0.063*
C20	−0.00246 (9)	1.3378 (2)	−0.10661 (9)	0.0545 (4)
H20A	−0.0383	1.3442	−0.0701	0.065*
H20B	0.0372	1.4485	−0.0922	0.065*
C21	−0.05353 (11)	1.3651 (3)	−0.19259 (10)	0.0738 (5)
H21A	−0.0918	1.2519	−0.2080	0.089*
H21B	−0.0176	1.3652	−0.2291	0.089*
C22	−0.10171 (11)	1.5589 (3)	−0.20315 (12)	0.0838 (6)
H22A	−0.1367	1.5601	−0.1665	0.126*
H22B	−0.1355	1.5697	−0.2591	0.126*
H22C	−0.0639	1.6715	−0.1907	0.126*
N1	0.70014 (7)	0.97044 (18)	0.64688 (7)	0.0492 (3)
O1	0.76613 (8)	0.9295 (2)	0.69331 (7)	0.0785 (4)
O2	0.66309 (7)	1.12423 (15)	0.65132 (6)	0.0616 (3)
O3	0.09348 (6)	1.14076 (15)	−0.01225 (6)	0.0558 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0412 (6)	0.0404 (6)	0.0327 (6)	0.0011 (5)	0.0112 (5)	0.0004 (5)
C2	0.0418 (6)	0.0485 (7)	0.0392 (6)	0.0107 (5)	0.0035 (5)	0.0037 (5)
C3	0.0433 (6)	0.0389 (6)	0.0415 (6)	0.0118 (5)	0.0096 (5)	0.0042 (5)
C4	0.0361 (5)	0.0360 (6)	0.0315 (5)	0.0056 (5)	0.0145 (4)	0.0050 (4)
C5	0.0382 (6)	0.0371 (6)	0.0324 (6)	0.0079 (5)	0.0093 (4)	0.0039 (4)
C6	0.0431 (6)	0.0347 (6)	0.0354 (6)	0.0069 (5)	0.0127 (5)	0.0037 (5)
C7	0.0429 (6)	0.0318 (6)	0.0365 (6)	0.0064 (5)	0.0166 (5)	0.0045 (4)
C8	0.0416 (6)	0.0329 (6)	0.0353 (6)	0.0038 (5)	0.0162 (5)	0.0028 (4)
C9	0.0457 (6)	0.0321 (6)	0.0387 (6)	0.0042 (5)	0.0175 (5)	0.0014 (5)
C10	0.0450 (6)	0.0341 (6)	0.0378 (6)	−0.0004 (5)	0.0171 (5)	−0.0030 (5)
C11	0.0410 (6)	0.0349 (6)	0.0392 (6)	−0.0009 (5)	0.0141 (5)	−0.0033 (5)
C12	0.0378 (6)	0.0358 (6)	0.0395 (6)	−0.0033 (5)	0.0138 (5)	−0.0040 (5)
C13	0.0336 (6)	0.0363 (6)	0.0374 (6)	−0.0050 (5)	0.0108 (4)	−0.0012 (5)
C14	0.0371 (6)	0.0429 (7)	0.0409 (6)	−0.0038 (5)	0.0090 (5)	−0.0070 (5)
C15	0.0389 (6)	0.0500 (7)	0.0383 (6)	−0.0033 (5)	0.0052 (5)	−0.0016 (5)
C16	0.0414 (6)	0.0385 (6)	0.0453 (7)	−0.0019 (5)	0.0076 (5)	0.0040 (5)
C17	0.0522 (7)	0.0370 (6)	0.0431 (7)	−0.0016 (5)	0.0070 (6)	−0.0043 (5)
C18	0.0465 (7)	0.0392 (6)	0.0360 (6)	−0.0019 (5)	0.0059 (5)	−0.0023 (5)
C19	0.0496 (8)	0.0602 (9)	0.0433 (7)	0.0073 (6)	0.0072 (6)	0.0050 (6)
C20	0.0507 (8)	0.0525 (8)	0.0576 (8)	0.0036 (6)	0.0100 (6)	0.0116 (7)
C21	0.0629 (10)	0.1044 (15)	0.0563 (9)	0.0327 (10)	0.0202 (8)	0.0215 (9)
C22	0.0665 (11)	0.1091 (16)	0.0836 (12)	0.0365 (11)	0.0341 (9)	0.0475 (12)
N1	0.0572 (7)	0.0494 (7)	0.0377 (6)	−0.0008 (5)	0.0076 (5)	−0.0020 (5)
O1	0.0676 (7)	0.0828 (9)	0.0645 (7)	0.0102 (6)	−0.0167 (6)	−0.0209 (6)
O2	0.0853 (8)	0.0427 (6)	0.0500 (6)	0.0064 (5)	0.0068 (5)	−0.0070 (4)
O3	0.0639 (6)	0.0435 (5)	0.0494 (6)	0.0067 (4)	−0.0024 (5)	0.0027 (4)

Geometric parameters (Å, º)

C1—C2	1.3815 (18)	C13—C18	1.3997 (17)
C1—C6	1.3831 (16)	C14—C15	1.3875 (18)
C1—N1	1.4597 (16)	C14—H14	0.9500
C2—C3	1.3759 (18)	C15—C16	1.3815 (19)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.3991 (16)	C16—O3	1.3658 (16)
C3—H3	0.9500	C16—C17	1.3957 (17)
C4—C5	1.4038 (16)	C17—C18	1.3727 (18)
C4—C7	1.4564 (17)	C17—H17	0.9500
C5—C6	1.3759 (17)	C18—H18	0.9500
C5—H5	0.9500	C19—O3	1.4257 (16)
C6—H6	0.9500	C19—C20	1.511 (2)
C7—C8	1.3415 (16)	C19—H19A	0.9900
C7—H7	0.9500	C19—H19B	0.9900
C8—C9	1.4400 (17)	C20—C21	1.509 (2)
C8—H8	0.9500	C20—H20A	0.9900
C9—C10	1.3486 (17)	C20—H20B	0.9900
C9—H9	0.9500	C21—C22	1.525 (3)
C10—C11	1.4415 (17)	C21—H21A	0.9900
C10—H10	0.9500	C21—H21B	0.9900
C11—C12	1.3438 (17)	C22—H22A	0.9800
C11—H11	0.9500	C22—H22B	0.9800
C12—C13	1.4575 (17)	C22—H22C	0.9800
C12—H12	0.9500	N1—O1	1.2203 (15)
C13—C14	1.3948 (16)	N1—O2	1.2252 (16)
C2—C1—C6	121.63 (12)	C13—C14—H14	119.0
C2—C1—N1	119.50 (11)	C16—C15—C14	119.64 (11)
C6—C1—N1	118.86 (11)	C16—C15—H15	120.2
C3—C2—C1	118.63 (11)	C14—C15—H15	120.2
C3—C2—H2	120.7	O3—C16—C15	125.63 (12)
C1—C2—H2	120.7	O3—C16—C17	114.87 (12)
C2—C3—C4	121.77 (11)	C15—C16—C17	119.49 (12)
C2—C3—H3	119.1	C18—C17—C16	120.26 (12)
C4—C3—H3	119.1	C18—C17—H17	119.9
C3—C4—C5	117.71 (11)	C16—C17—H17	119.9
C3—C4—C7	119.09 (11)	C17—C18—C13	121.55 (11)
C5—C4—C7	123.19 (10)	C17—C18—H18	119.2
C6—C5—C4	121.12 (11)	C13—C18—H18	119.2
C6—C5—H5	119.4	O3—C19—C20	107.60 (12)
C4—C5—H5	119.4	O3—C19—H19A	110.2
C5—C6—C1	119.13 (11)	C20—C19—H19A	110.2
C5—C6—H6	120.4	O3—C19—H19B	110.2
C1—C6—H6	120.4	C20—C19—H19B	110.2
C8—C7—C4	126.58 (11)	H19A—C19—H19B	108.5
C8—C7—H7	116.7	C21—C20—C19	112.84 (14)
C4—C7—H7	116.7	C21—C20—H20A	109.0
C7—C8—C9	123.43 (11)	C19—C20—H20A	109.0
C7—C8—H8	118.3	C21—C20—H20B	109.0
C9—C8—H8	118.3	C19—C20—H20B	109.0
C10—C9—C8	126.20 (11)	H20A—C20—H20B	107.8
C10—C9—H9	116.9	C20—C21—C22	111.61 (16)
C8—C9—H9	116.9	C20—C21—H21A	109.3
C9—C10—C11	126.92 (11)	C22—C21—H21A	109.3
C9—C10—H10	116.5	C20—C21—H21B	109.3
C11—C10—H10	116.5	C22—C21—H21B	109.3
C12—C11—C10	122.55 (11)	H21A—C21—H21B	108.0
C12—C11—H11	118.7	C21—C22—H22A	109.5
C10—C11—H11	118.7	C21—C22—H22B	109.5
C11—C12—C13	126.84 (11)	H22A—C22—H22B	109.5
C11—C12—H12	116.6	C21—C22—H22C	109.5
C13—C12—H12	116.6	H22A—C22—H22C	109.5
C14—C13—C18	117.12 (11)	H22B—C22—H22C	109.5
C14—C13—C12	120.12 (11)	O1—N1—O2	123.29 (12)
C18—C13—C12	122.75 (11)	O1—N1—C1	118.27 (12)
C15—C14—C13	121.93 (12)	O2—N1—C1	118.44 (11)
C15—C14—H14	119.0	C16—O3—C19	118.02 (11)
C6—C1—C2—C3	−1.0 (2)	C18—C13—C14—C15	0.43 (18)
N1—C1—C2—C3	178.52 (11)	C12—C13—C14—C15	179.56 (11)
C1—C2—C3—C4	−0.1 (2)	C13—C14—C15—C16	−0.74 (19)
C2—C3—C4—C5	1.34 (18)	C14—C15—C16—O3	−178.39 (12)
C2—C3—C4—C7	−178.90 (11)	C14—C15—C16—C17	0.43 (19)
C3—C4—C5—C6	−1.47 (17)	O3—C16—C17—C18	179.11 (12)
C7—C4—C5—C6	178.77 (10)	C15—C16—C17—C18	0.2 (2)
C4—C5—C6—C1	0.41 (18)	C16—C17—C18—C13	−0.5 (2)
C2—C1—C6—C5	0.87 (18)	C14—C13—C18—C17	0.18 (18)
N1—C1—C6—C5	−178.66 (10)	C12—C13—C18—C17	−178.93 (12)
C3—C4—C7—C8	176.45 (11)	O3—C19—C20—C21	175.82 (13)
C5—C4—C7—C8	−3.80 (18)	C19—C20—C21—C22	177.56 (14)
C4—C7—C8—C9	179.96 (10)	C2—C1—N1—O1	12.57 (19)
C7—C8—C9—C10	−174.14 (11)	C6—C1—N1—O1	−167.89 (13)
C8—C9—C10—C11	0.7 (2)	C2—C1—N1—O2	−166.69 (13)
C9—C10—C11—C12	170.46 (12)	C6—C1—N1—O2	12.85 (18)
C10—C11—C12—C13	−178.94 (11)	C15—C16—O3—C19	0.0 (2)
C11—C12—C13—C14	172.53 (11)	C17—C16—O3—C19	−178.88 (12)
C11—C12—C13—C18	−8.39 (19)	C20—C19—O3—C16	178.64 (11)