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In the title compound, 4-(
E)-but-1-enyl-2,6-dimethoxyphenyl pyridine-3-carboxylate, C
18H
19NO
4, the butenyl substituent is in the
trans configuration. The molecules are linked by weak intermolecular C—H
O hydrogen bonds, leading to the formation of a chain extending through the whole crystal structure.
Supporting information
CCDC reference: 214846
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.101
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Details of the synthesis will be published elsewere (Grabowski et al., 2003). Crystals were obtained by slow evaporation of an ethanol/hexane solution at room temperature.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å. For methoxy H atoms, Uiso = 1.5Ueq(C); for all other H atoms, Uiso = 1.2Ueq(C).
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1996).
4-(
E)-But-1-enyl-2,6-dimethoxyphenyl pyridine-3-carboxylate
top
Crystal data top
C18H19NO4 | F(000) = 664 |
Mr = 313.34 | Dx = 1.247 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 20 reflections |
a = 9.105 (2) Å | θ = 9.9–13.2° |
b = 22.729 (3) Å | µ = 0.72 mm−1 |
c = 8.157 (3) Å | T = 293 K |
β = 98.47 (2)° | Needle, colourless |
V = 1669.7 (8) Å3 | 0.43 × 0.15 × 0.08 mm |
Z = 4 | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 67.5°, θmin = 3.9° |
Graphite monochromator | h = −10→10 |
ω scans | k = 0→27 |
2927 measured reflections | l = 0→9 |
2927 independent reflections | 3 standard reflections every 150 reflections |
1259 reflections with I > 2σ(I) | intensity decay: <2% |
Refinement top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | [exp(4(sinθ/λ)2)]/
[σ2(Fo2) + (0.0485P)2]
where P = 0.33333Fo2 + 0.66667Fc2 |
2927 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Crystal data top
C18H19NO4 | V = 1669.7 (8) Å3 |
Mr = 313.34 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.105 (2) Å | µ = 0.72 mm−1 |
b = 22.729 (3) Å | T = 293 K |
c = 8.157 (3) Å | 0.43 × 0.15 × 0.08 mm |
β = 98.47 (2)° | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.000 |
2927 measured reflections | 3 standard reflections every 150 reflections |
2927 independent reflections | intensity decay: <2% |
1259 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.26 e Å−3 |
2927 reflections | Δρmin = −0.14 e Å−3 |
208 parameters | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O31 | 0.20148 (16) | 0.10903 (7) | 0.47890 (14) | 0.0668 (4) | |
O32 | 0.40686 (16) | 0.04210 (7) | 0.65119 (16) | 0.0737 (4) | |
O30 | −0.00077 (17) | 0.07045 (7) | 0.56448 (16) | 0.0771 (5) | |
C35 | 0.2795 (3) | 0.19614 (10) | 0.8588 (2) | 0.0692 (6) | |
H35 | 0.2478 | 0.2307 | 0.9034 | 0.083* | |
C3 | 0.0136 (2) | 0.07544 (8) | 0.2751 (2) | 0.0523 (5) | |
O36 | 0.10011 (19) | 0.20604 (7) | 0.60749 (17) | 0.0815 (5) | |
C36 | 0.2110 (2) | 0.17725 (10) | 0.7044 (2) | 0.0618 (6) | |
C33 | 0.4404 (2) | 0.11191 (10) | 0.8818 (2) | 0.0647 (6) | |
H33 | 0.5169 | 0.0901 | 0.9410 | 0.078* | |
C34 | 0.3942 (2) | 0.16426 (10) | 0.9475 (2) | 0.0647 (6) | |
C2 | −0.1282 (2) | 0.05528 (10) | 0.2252 (2) | 0.0654 (6) | |
H2 | −0.1840 | 0.0445 | 0.3070 | 0.079* | |
N1 | −0.1910 (2) | 0.05014 (9) | 0.0680 (2) | 0.0763 (6) | |
C31 | 0.2591 (2) | 0.12577 (10) | 0.6407 (2) | 0.0594 (6) | |
C32 | 0.3720 (2) | 0.09236 (10) | 0.7276 (2) | 0.0595 (6) | |
C30 | 0.0663 (2) | 0.08356 (9) | 0.4539 (2) | 0.0553 (5) | |
C4 | 0.0996 (2) | 0.08932 (9) | 0.1534 (2) | 0.0637 (6) | |
H4 | 0.1969 | 0.1024 | 0.1815 | 0.076* | |
C5 | 0.0366 (3) | 0.08318 (10) | −0.0106 (2) | 0.0705 (6) | |
H5 | 0.0915 | 0.0915 | −0.0954 | 0.085* | |
C40 | 0.4667 (3) | 0.18770 (11) | 1.1075 (3) | 0.0824 (7) | |
H40 | 0.4261 | 0.2222 | 1.1429 | 0.099* | |
C6 | −0.1064 (3) | 0.06485 (10) | −0.0462 (3) | 0.0737 (7) | |
H6 | −0.1482 | 0.0624 | −0.1571 | 0.088* | |
C50 | 0.5790 (3) | 0.16676 (12) | 1.2051 (3) | 0.0940 (8) | |
H50 | 0.6169 | 0.1310 | 1.1751 | 0.113* | |
C320 | 0.5181 (3) | 0.00505 (10) | 0.7347 (3) | 0.0907 (8) | |
H321 | 0.5313 | −0.0284 | 0.6663 | 0.136* | |
H322 | 0.4888 | −0.0081 | 0.8370 | 0.136* | |
H323 | 0.6098 | 0.0264 | 0.7576 | 0.136* | |
C60 | 0.6556 (4) | 0.19491 (14) | 1.3645 (3) | 0.1125 (10) | |
H61 | 0.7597 | 0.2010 | 1.3564 | 0.135* | |
H62 | 0.6112 | 0.2330 | 1.3787 | 0.135* | |
C360 | 0.0277 (4) | 0.25154 (13) | 0.6809 (3) | 0.1189 (11) | |
H361 | −0.0492 | 0.2678 | 0.6005 | 0.178* | |
H362 | 0.0981 | 0.2817 | 0.7197 | 0.178* | |
H363 | −0.0153 | 0.2361 | 0.7726 | 0.178* | |
C70 | 0.6432 (4) | 0.15872 (15) | 1.5069 (4) | 0.1374 (12) | |
H71 | 0.6926 | 0.1776 | 1.6050 | 0.206* | |
H72 | 0.6884 | 0.1212 | 1.4940 | 0.206* | |
H73 | 0.5403 | 0.1532 | 1.5166 | 0.206* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O31 | 0.0654 (9) | 0.0930 (11) | 0.0419 (8) | −0.0160 (8) | 0.0071 (7) | −0.0082 (7) |
O32 | 0.0762 (10) | 0.0849 (12) | 0.0582 (9) | 0.0032 (9) | 0.0044 (7) | −0.0165 (8) |
O30 | 0.0826 (11) | 0.1025 (12) | 0.0486 (8) | −0.0225 (9) | 0.0173 (8) | −0.0002 (8) |
C35 | 0.0794 (16) | 0.0680 (16) | 0.0594 (13) | −0.0046 (13) | 0.0073 (12) | −0.0046 (12) |
C3 | 0.0557 (12) | 0.0590 (13) | 0.0415 (11) | 0.0010 (10) | 0.0042 (9) | −0.0005 (9) |
O36 | 0.0979 (12) | 0.0818 (12) | 0.0614 (9) | 0.0092 (10) | 0.0011 (9) | 0.0045 (8) |
C36 | 0.0680 (14) | 0.0708 (17) | 0.0451 (12) | −0.0064 (12) | 0.0037 (11) | 0.0020 (11) |
C33 | 0.0633 (14) | 0.0780 (16) | 0.0513 (12) | −0.0075 (12) | 0.0032 (11) | −0.0030 (11) |
C34 | 0.0731 (15) | 0.0707 (16) | 0.0500 (12) | −0.0121 (13) | 0.0082 (11) | −0.0090 (11) |
C2 | 0.0617 (15) | 0.0865 (18) | 0.0483 (12) | −0.0023 (12) | 0.0087 (10) | −0.0025 (11) |
N1 | 0.0656 (12) | 0.1054 (16) | 0.0561 (11) | −0.0040 (11) | 0.0031 (10) | −0.0069 (10) |
C31 | 0.0637 (14) | 0.0765 (16) | 0.0376 (11) | −0.0133 (12) | 0.0065 (10) | −0.0035 (11) |
C32 | 0.0594 (14) | 0.0707 (16) | 0.0495 (12) | −0.0122 (11) | 0.0118 (10) | −0.0076 (11) |
C30 | 0.0589 (14) | 0.0594 (14) | 0.0469 (12) | −0.0027 (11) | 0.0052 (10) | −0.0026 (10) |
C4 | 0.0676 (14) | 0.0746 (15) | 0.0491 (12) | −0.0101 (12) | 0.0095 (11) | −0.0025 (10) |
C5 | 0.0873 (18) | 0.0817 (17) | 0.0432 (12) | −0.0144 (14) | 0.0122 (11) | −0.0019 (11) |
C40 | 0.0931 (19) | 0.0897 (19) | 0.0610 (14) | 0.0007 (15) | −0.0003 (14) | −0.0165 (13) |
C6 | 0.0775 (17) | 0.0890 (18) | 0.0508 (13) | −0.0031 (14) | −0.0029 (12) | −0.0027 (12) |
C50 | 0.104 (2) | 0.101 (2) | 0.0690 (17) | 0.0065 (17) | −0.0133 (15) | −0.0206 (14) |
C320 | 0.0959 (19) | 0.0915 (19) | 0.0792 (17) | 0.0170 (16) | −0.0057 (15) | −0.0137 (14) |
C60 | 0.134 (3) | 0.127 (3) | 0.0714 (17) | −0.010 (2) | −0.0006 (17) | −0.0137 (18) |
C360 | 0.134 (3) | 0.119 (3) | 0.097 (2) | 0.049 (2) | −0.0041 (18) | −0.0084 (18) |
C70 | 0.177 (3) | 0.154 (3) | 0.083 (2) | −0.028 (3) | 0.028 (2) | −0.015 (2) |
Geometric parameters (Å, º) top
O31—C30 | 1.348 (2) | C4—C5 | 1.383 (3) |
O31—C31 | 1.399 (2) | C4—H4 | 0.9300 |
O32—C32 | 1.361 (2) | C5—C6 | 1.357 (3) |
O32—C320 | 1.413 (2) | C5—H5 | 0.9300 |
O30—C30 | 1.199 (2) | C40—C50 | 1.291 (3) |
C35—C34 | 1.384 (3) | C40—H40 | 0.9300 |
C35—C36 | 1.389 (3) | C6—H6 | 0.9300 |
C35—H35 | 0.9300 | C50—C60 | 1.523 (3) |
C3—C2 | 1.373 (3) | C50—H50 | 0.9300 |
C3—C4 | 1.388 (3) | C320—H321 | 0.9600 |
C3—C30 | 1.478 (3) | C320—H322 | 0.9600 |
O36—C36 | 1.356 (2) | C320—H323 | 0.9600 |
O36—C360 | 1.407 (3) | C60—C70 | 1.441 (4) |
C36—C31 | 1.378 (3) | C60—H61 | 0.9700 |
C33—C32 | 1.392 (3) | C60—H62 | 0.9700 |
C33—C34 | 1.395 (3) | C360—H361 | 0.9600 |
C33—H33 | 0.9300 | C360—H362 | 0.9600 |
C34—C40 | 1.473 (3) | C360—H363 | 0.9600 |
C2—N1 | 1.330 (2) | C70—H71 | 0.9600 |
C2—H2 | 0.9300 | C70—H72 | 0.9600 |
N1—C6 | 1.336 (3) | C70—H73 | 0.9600 |
C31—C32 | 1.386 (3) | | |
| | | |
C30—O31—C31 | 117.81 (15) | C6—C5—H5 | 120.5 |
C32—O32—C320 | 118.58 (16) | C4—C5—H5 | 120.5 |
C34—C35—C36 | 121.0 (2) | C50—C40—C34 | 128.6 (3) |
C34—C35—H35 | 119.5 | C50—C40—H40 | 115.7 |
C36—C35—H35 | 119.5 | C34—C40—H40 | 115.7 |
C2—C3—C4 | 117.95 (18) | N1—C6—C5 | 124.1 (2) |
C2—C3—C30 | 119.23 (19) | N1—C6—H6 | 117.9 |
C4—C3—C30 | 122.78 (19) | C5—C6—H6 | 117.9 |
C36—O36—C360 | 117.53 (18) | C40—C50—C60 | 126.4 (3) |
O36—C36—C31 | 116.13 (19) | C40—C50—H50 | 116.8 |
O36—C36—C35 | 125.2 (2) | C60—C50—H50 | 116.8 |
C31—C36—C35 | 118.7 (2) | O32—C320—H321 | 109.5 |
C32—C33—C34 | 120.0 (2) | O32—C320—H322 | 109.5 |
C32—C33—H33 | 120.0 | H321—C320—H322 | 109.5 |
C34—C33—H33 | 120.0 | O32—C320—H323 | 109.5 |
C35—C34—C33 | 119.51 (19) | H321—C320—H323 | 109.5 |
C35—C34—C40 | 118.6 (2) | H322—C320—H323 | 109.5 |
C33—C34—C40 | 121.9 (2) | C70—C60—C50 | 111.6 (3) |
N1—C2—C3 | 124.6 (2) | C70—C60—H61 | 109.3 |
N1—C2—H2 | 117.7 | C50—C60—H61 | 109.3 |
C3—C2—H2 | 117.7 | C70—C60—H62 | 109.3 |
C2—N1—C6 | 116.1 (2) | C50—C60—H62 | 109.3 |
C36—C31—C32 | 121.66 (19) | H61—C60—H62 | 108.0 |
C36—C31—O31 | 119.4 (2) | O36—C360—H361 | 109.5 |
C32—C31—O31 | 118.7 (2) | O36—C360—H362 | 109.5 |
O32—C32—C31 | 115.52 (18) | H361—C360—H362 | 109.5 |
O32—C32—C33 | 125.3 (2) | O36—C360—H363 | 109.5 |
C31—C32—C33 | 119.1 (2) | H361—C360—H363 | 109.5 |
O30—C30—O31 | 123.18 (17) | H362—C360—H363 | 109.5 |
O30—C30—C3 | 125.7 (2) | C60—C70—H71 | 109.5 |
O31—C30—C3 | 111.08 (17) | C60—C70—H72 | 109.5 |
C5—C4—C3 | 118.1 (2) | H71—C70—H72 | 109.5 |
C5—C4—H4 | 120.9 | C60—C70—H73 | 109.5 |
C3—C4—H4 | 120.9 | H71—C70—H73 | 109.5 |
C6—C5—C4 | 119.1 (2) | H72—C70—H73 | 109.5 |
| | | |
C360—O36—C36—C31 | 167.2 (2) | O31—C31—C32—O32 | −6.2 (3) |
C360—O36—C36—C35 | −13.9 (3) | C36—C31—C32—C33 | −1.2 (3) |
C34—C35—C36—O36 | −178.69 (19) | O31—C31—C32—C33 | 173.48 (17) |
C34—C35—C36—C31 | 0.2 (3) | C34—C33—C32—O32 | −179.8 (2) |
C36—C35—C34—C33 | −0.9 (3) | C34—C33—C32—C31 | 0.5 (3) |
C36—C35—C34—C40 | 177.5 (2) | C31—O31—C30—O30 | −6.2 (3) |
C32—C33—C34—C35 | 0.5 (3) | C31—O31—C30—C3 | 172.84 (18) |
C32—C33—C34—C40 | −177.9 (2) | C2—C3—C30—O30 | 5.1 (3) |
C4—C3—C2—N1 | −2.6 (3) | C4—C3—C30—O30 | −177.2 (2) |
C30—C3—C2—N1 | 175.2 (2) | C2—C3—C30—O31 | −173.82 (18) |
C3—C2—N1—C6 | 1.4 (3) | C4—C3—C30—O31 | 3.8 (3) |
O36—C36—C31—C32 | 179.86 (18) | C2—C3—C4—C5 | 1.3 (3) |
C35—C36—C31—C32 | 0.8 (3) | C30—C3—C4—C5 | −176.39 (19) |
O36—C36—C31—O31 | 5.2 (3) | C3—C4—C5—C6 | 1.0 (3) |
C35—C36—C31—O31 | −173.83 (18) | C35—C34—C40—C50 | −176.4 (3) |
C30—O31—C31—C36 | −79.5 (2) | C33—C34—C40—C50 | 2.0 (4) |
C30—O31—C31—C32 | 105.7 (2) | C2—N1—C6—C5 | 1.2 (4) |
C320—O32—C32—C31 | −178.25 (19) | C4—C5—C6—N1 | −2.4 (4) |
C320—O32—C32—C33 | 2.1 (3) | C34—C40—C50—C60 | 176.0 (2) |
C36—C31—C32—O32 | 179.06 (18) | C40—C50—C60—C70 | 117.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C35—H35···O36i | 0.93 | 2.70 | 3.564 (3) | 154 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C18H19NO4 |
Mr | 313.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.105 (2), 22.729 (3), 8.157 (3) |
β (°) | 98.47 (2) |
V (Å3) | 1669.7 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.43 × 0.15 × 0.08 |
|
Data collection |
Diffractometer | Rigaku AFC-5S diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2927, 2927, 1259 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.599 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.101, 1.03 |
No. of reflections | 2927 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.14 |
Selected geometric parameters (Å, º) topO31—C30 | 1.348 (2) | O36—C36 | 1.356 (2) |
O31—C31 | 1.399 (2) | O36—C360 | 1.407 (3) |
O32—C32 | 1.361 (2) | C2—N1 | 1.330 (2) |
O32—C320 | 1.413 (2) | N1—C6 | 1.336 (3) |
O30—C30 | 1.199 (2) | | |
| | | |
C30—O31—C31 | 117.81 (15) | C36—C31—O31 | 119.4 (2) |
C32—O32—C320 | 118.58 (16) | C32—C31—O31 | 118.7 (2) |
C36—O36—C360 | 117.53 (18) | O32—C32—C31 | 115.52 (18) |
O36—C36—C31 | 116.13 (19) | O32—C32—C33 | 125.3 (2) |
O36—C36—C35 | 125.2 (2) | O30—C30—O31 | 123.18 (17) |
N1—C2—C3 | 124.6 (2) | O30—C30—C3 | 125.7 (2) |
C2—N1—C6 | 116.1 (2) | O31—C30—C3 | 111.08 (17) |
| | | |
C360—O36—C36—C31 | 167.2 (2) | C320—O32—C32—C33 | 2.1 (3) |
C360—O36—C36—C35 | −13.9 (3) | C36—C31—C32—O32 | 179.06 (18) |
C34—C35—C36—O36 | −178.69 (19) | O31—C31—C32—O32 | −6.2 (3) |
O36—C36—C31—C32 | 179.86 (18) | O31—C31—C32—C33 | 173.48 (17) |
O36—C36—C31—O31 | 5.2 (3) | C31—O31—C30—O30 | −6.2 (3) |
C35—C36—C31—O31 | −173.83 (18) | C31—O31—C30—C3 | 172.84 (18) |
C30—O31—C31—C36 | −79.5 (2) | C2—C3—C30—O30 | 5.1 (3) |
C30—O31—C31—C32 | 105.7 (2) | C4—C3—C30—O30 | −177.2 (2) |
C320—O32—C32—C31 | −178.25 (19) | C40—C50—C60—C70 | 117.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C35—H35···O36i | 0.93 | 2.70 | 3.564 (3) | 154 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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α-Asarone is a principal active ingredient of the bark extract of Guatteria gaumeri (Enriquez & Chàvez, 1980) and Acorus calamus (Gracza & Spaich, 1978). These extracts are used to prevent elevation of plasma lipids. It has been found, in earlier studies of α-asarone derivatives, that some of them could be effective hypolipidaemic agents (Popławski et al., 2000; Labarrios et al., 1999). α-Asarones have already been investigated by X-ray crystallography (Wolska et al., 1998). In those studies, the occurrence of weak intra- and intermolecular C—H···O hydrogen bonding was reported. In this paper, the crystal and molecular structure of a new α-asarone derivative, (I), is presented.
The molecule of (I) consists of two aromatic rings, viz. a pyridine ring present as a nicotinic acid fragment and a benzene ring forming the basic α-asarone moiety. The least-squares planes of these rings form a dihedral angle of 76.39 (6)°. The carboxylic acid group is almost coplanar with the pyridine ring; the plane through atoms C3/C30/O30/O31 forms an angle of 6.28 (7)° with the plane of the pyridine ring. The atoms of the methoxy groups do not deviate significantly from the benzene-ring plane, the maximum deviation being 0.274 (4) Å for atom C360. Such an arrangement of methoxy groups attached to the benzene ring is most advantageous energetically, as has been proved both experimentally and theoretically (Federsel et al., 2001). The butenyl group is in the trans configuration. The C34/C40/C50/C60 plane makes an angle of 3.9 (2)° with the plane of the benzene ring. Atom C70 deviates from the C34/C40/C50/C60 plane by 1.162 (4) Å.
Detailed geometrical analysis suggests the presence of a weak intermolecular C—H···O hydrogen bond (Table 2). Finally, the molecules link together, forming a chain whose topological motif corresponds to the first-order graph set descriptor C(4) (Bernstein et al., 1995).