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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o432.
Published online 2010 January 23. doi:  10.1107/S1600536810001972
PMCID: PMC2979806

(E)-N-(3,4-Dimethoxy­pheneth­yl)-3-methoxy­but-2-enamide

Abstract

In the crystal of the title compound, C15H21NO4, inter­molecular N—H(...)O hydrogen bonds link mol­ecules related by translation along the c axis into hydrogen-bonded chains. C—H(...)O links are also present. The dihedral angle between benzene ring and enamide group is 50.08 (3)°

Related literature

For the applications of the title compound, see: Bernhard & Snieckus (1971 [triangle]); Ma et al. (2006 [triangle]). For bond-length data, see Allen et al. (1987 [triangle]).

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Object name is e-66-0o432-scheme1.jpg

Experimental

Crystal data

  • C15H21NO4
  • M r = 279.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o432-efi1.jpg
  • a = 12.509 (3) Å
  • b = 14.930 (3) Å
  • c = 8.2998 (17) Å
  • β = 107.59 (3)°
  • V = 1477.5 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 173 K
  • 0.30 × 0.20 × 0.15 mm

Data collection

  • Rigaku Mercury CCD/AFC diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 [triangle]) T min = 0.973, T max = 0.987
  • 10754 measured reflections
  • 2591 independent reflections
  • 2435 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.133
  • S = 1.18
  • 2591 reflections
  • 181 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2007 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001972/hg2630sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001972/hg2630Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound (E)—N-(3,4-dimethoxyphenethyl)-3-methoxybut-2-enamide was an important intermediate to the 3, 4-dihydroisoquinoline and some other heterocyclic compounds (Bernhard & Snieckus, 1971; Ma et al., 2006). In this paper, we use 3,4-dimethoxyphenethylamine and 3-methoxy-2-butenoyl chloride to synthesize the title compound and report its crystal structure here.

The title compound C15H21NO4(Fig. 1), all bond lengths in the molecular are normal (Allen et al., 1987). The intermolecular N—H···O hydrogen bonds [N···O 2.842 (2) Å] link the molecules related by translation along c axis into hydrogen-bonded chains.

Experimental

3,4-dimethoxyphenethylamine (20 mmol) was solved in CH2Cl2, Et3N (30 mmol) was added, then 3-methoxy-2-butenoyl chloride (20 mmol) was added during 30 min at 273 K, after react 2 h at room temperature, the solution was washed with water, the organic layer was separated, dried with Na2SO4, evaporated to obtain the primary product, the pure product was isolated by recrystallization from ethyl acetate. (4.74 g, 84.9%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and N—H = 0.86 Å; with Uiso(H) = 1.2 times Ueq(C, N) and 1.5 times Ueq(C)for methyl H atoms.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

Crystal data

C15H21NO4F(000) = 600
Mr = 279.33Dx = 1.256 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4588 reflections
a = 12.509 (3) Åθ = 1.4–27.5°
b = 14.930 (3) ŵ = 0.09 mm1
c = 8.2998 (17) ÅT = 173 K
β = 107.59 (3)°Rod, colorless
V = 1477.5 (5) Å30.30 × 0.20 × 0.15 mm
Z = 4

Data collection

Rigaku Mercury CCD/AFC diffractometer2591 independent reflections
Radiation source: Sealed Tube2435 reflections with I > 2σ(I)
Graphite MonochromatorRint = 0.049
[var phi] and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)h = −14→14
Tmin = 0.973, Tmax = 0.987k = −17→17
10754 measured reflectionsl = −9→8

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.18w = 1/[σ2(Fo2) + (0.045P)2 + 0.6856P] where P = (Fo2 + 2Fc2)/3
2591 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.18 e Å3

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 (Å2)

xyzUiso*/Ueq
O11.17428 (12)0.48028 (10)0.66017 (19)0.0356 (4)
O21.16017 (13)0.30958 (10)0.6857 (2)0.0446 (4)
O30.57963 (13)0.16546 (10)0.56367 (18)0.0352 (4)
O40.36035 (13)0.06101 (10)0.8340 (2)0.0417 (4)
N10.62813 (14)0.26957 (12)0.7715 (2)0.0308 (4)
H1A0.61280.29200.86010.037*
C10.91080 (17)0.37551 (15)0.8108 (3)0.0303 (5)
C20.99168 (17)0.32078 (14)0.7740 (3)0.0320 (5)
H2A0.98710.25760.78380.038*
C31.07767 (17)0.35758 (14)0.7239 (3)0.0307 (5)
C41.08529 (16)0.45083 (14)0.7088 (2)0.0285 (5)
C51.00533 (18)0.50451 (14)0.7431 (3)0.0321 (5)
H5A1.00930.56770.73220.038*
C60.91870 (18)0.46703 (15)0.7936 (3)0.0331 (5)
H6A0.86420.50500.81670.040*
C71.1604 (2)0.21485 (16)0.7102 (3)0.0484 (6)
H7A1.22310.18810.67930.073*
H7B1.08960.18950.63900.073*
H7C1.16880.20190.82920.073*
C81.1861 (2)0.57474 (15)0.6482 (3)0.0379 (5)
H8A1.25240.58780.61260.057*
H8B1.19480.60220.75870.057*
H8C1.11920.59920.56500.057*
C90.81715 (17)0.33412 (16)0.8642 (3)0.0342 (5)
H9A0.79540.37570.94180.041*
H9B0.84450.27810.92710.041*
C100.71449 (17)0.31312 (15)0.7155 (3)0.0316 (5)
H10A0.68430.36930.65570.038*
H10B0.73640.27350.63510.038*
C110.57000 (16)0.19712 (14)0.6969 (3)0.0283 (5)
C120.49832 (17)0.15920 (14)0.7913 (3)0.0304 (5)
H12A0.50820.18200.90170.036*
C130.42041 (17)0.09551 (14)0.7360 (3)0.0321 (5)
C140.3818 (2)0.05392 (18)0.5650 (3)0.0500 (7)
H14A0.42480.07880.49440.075*
H14B0.30190.06670.51290.075*
H14C0.3933−0.01100.57510.075*
C150.3837 (2)0.09322 (19)1.0043 (3)0.0500 (7)
H15A0.33490.06271.05940.075*
H15B0.37000.15791.00260.075*
H15C0.46230.08111.06690.075*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0300 (8)0.0331 (8)0.0494 (9)−0.0036 (6)0.0206 (7)0.0028 (7)
O20.0372 (9)0.0326 (9)0.0727 (12)0.0074 (7)0.0298 (8)0.0031 (8)
O30.0398 (9)0.0370 (9)0.0334 (9)−0.0040 (7)0.0180 (7)−0.0029 (7)
O40.0338 (9)0.0372 (9)0.0607 (11)−0.0059 (7)0.0242 (8)0.0051 (8)
N10.0318 (10)0.0340 (10)0.0330 (9)−0.0074 (8)0.0193 (8)−0.0034 (8)
C10.0255 (11)0.0361 (12)0.0296 (11)−0.0041 (9)0.0087 (8)−0.0002 (9)
C20.0300 (11)0.0301 (12)0.0365 (12)0.0005 (9)0.0109 (9)0.0042 (9)
C30.0244 (10)0.0324 (12)0.0369 (12)0.0027 (9)0.0116 (9)0.0016 (9)
C40.0230 (10)0.0332 (11)0.0301 (11)−0.0028 (8)0.0092 (8)0.0003 (9)
C50.0319 (11)0.0270 (11)0.0399 (12)−0.0020 (9)0.0147 (9)−0.0024 (9)
C60.0291 (11)0.0347 (12)0.0401 (12)0.0000 (9)0.0173 (9)−0.0043 (9)
C70.0537 (16)0.0342 (13)0.0615 (16)0.0135 (11)0.0237 (13)0.0057 (12)
C80.0401 (13)0.0358 (13)0.0407 (13)−0.0122 (10)0.0165 (10)−0.0027 (10)
C90.0303 (12)0.0414 (13)0.0341 (12)−0.0049 (10)0.0144 (9)0.0021 (10)
C100.0304 (11)0.0358 (12)0.0320 (12)−0.0059 (9)0.0147 (9)0.0019 (9)
C110.0240 (10)0.0298 (11)0.0331 (12)0.0011 (9)0.0115 (9)0.0029 (9)
C120.0294 (11)0.0322 (12)0.0318 (11)−0.0025 (9)0.0125 (9)0.0018 (9)
C130.0244 (10)0.0278 (11)0.0476 (13)0.0024 (9)0.0164 (9)0.0042 (9)
C140.0434 (14)0.0491 (15)0.0623 (17)−0.0151 (12)0.0235 (12)−0.0199 (13)
C150.0445 (15)0.0637 (17)0.0492 (15)−0.0082 (12)0.0252 (12)0.0135 (13)

Geometric parameters (Å, °)

O1—C41.366 (2)C7—H7B0.9800
O1—C81.425 (3)C7—H7C0.9800
O2—C31.370 (2)C8—H8A0.9800
O2—C71.429 (3)C8—H8B0.9800
O3—C111.241 (2)C8—H8C0.9800
O4—C131.364 (2)C9—C101.521 (3)
O4—C151.436 (3)C9—H9A0.9900
N1—C111.345 (3)C9—H9B0.9900
N1—C101.453 (2)C10—H10A0.9900
N1—H1A0.8800C10—H10B0.9900
C1—C61.380 (3)C11—C121.471 (3)
C1—C21.404 (3)C12—C131.339 (3)
C1—C91.505 (3)C12—H12A0.9500
C2—C31.379 (3)C13—C141.490 (3)
C2—H2A0.9500C14—H14A0.9800
C3—C41.404 (3)C14—H14B0.9800
C4—C51.377 (3)C14—H14C0.9800
C5—C61.392 (3)C15—H15A0.9800
C5—H5A0.9500C15—H15B0.9800
C6—H6A0.9500C15—H15C0.9800
C7—H7A0.9800
C4—O1—C8116.74 (16)H8B—C8—H8C109.5
C3—O2—C7117.00 (18)C1—C9—C10112.77 (17)
C13—O4—C15118.37 (18)C1—C9—H9A109.0
C11—N1—C10124.27 (17)C10—C9—H9A109.0
C11—N1—H1A117.9C1—C9—H9B109.0
C10—N1—H1A117.9C10—C9—H9B109.0
C6—C1—C2118.36 (19)H9A—C9—H9B107.8
C6—C1—C9121.55 (19)N1—C10—C9111.08 (17)
C2—C1—C9120.1 (2)N1—C10—H10A109.4
C3—C2—C1120.8 (2)C9—C10—H10A109.4
C3—C2—H2A119.6N1—C10—H10B109.4
C1—C2—H2A119.6C9—C10—H10B109.4
O2—C3—C2124.9 (2)H10A—C10—H10B108.0
O2—C3—C4114.96 (18)O3—C11—N1122.13 (18)
C2—C3—C4120.15 (19)O3—C11—C12124.53 (19)
O1—C4—C5125.55 (19)N1—C11—C12113.31 (18)
O1—C4—C3115.39 (18)C13—C12—C11126.0 (2)
C5—C4—C3119.06 (19)C13—C12—H12A117.0
C4—C5—C6120.6 (2)C11—C12—H12A117.0
C4—C5—H5A119.7C12—C13—O4122.6 (2)
C6—C5—H5A119.7C12—C13—C14128.0 (2)
C1—C6—C5121.0 (2)O4—C13—C14109.43 (19)
C1—C6—H6A119.5C13—C14—H14A109.5
C5—C6—H6A119.5C13—C14—H14B109.5
O2—C7—H7A109.5H14A—C14—H14B109.5
O2—C7—H7B109.5C13—C14—H14C109.5
H7A—C7—H7B109.5H14A—C14—H14C109.5
O2—C7—H7C109.5H14B—C14—H14C109.5
H7A—C7—H7C109.5O4—C15—H15A109.5
H7B—C7—H7C109.5O4—C15—H15B109.5
O1—C8—H8A109.5H15A—C15—H15B109.5
O1—C8—H8B109.5O4—C15—H15C109.5
H8A—C8—H8B109.5H15A—C15—H15C109.5
O1—C8—H8C109.5H15B—C15—H15C109.5
H8A—C8—H8C109.5
C6—C1—C2—C30.7 (3)C9—C1—C6—C5−179.60 (19)
C9—C1—C2—C3179.61 (19)C4—C5—C6—C10.1 (3)
C7—O2—C3—C2−4.2 (3)C6—C1—C9—C1089.1 (3)
C7—O2—C3—C4175.8 (2)C2—C1—C9—C10−89.8 (2)
C1—C2—C3—O2179.9 (2)C11—N1—C10—C9−134.8 (2)
C1—C2—C3—C4−0.1 (3)C1—C9—C10—N1177.36 (18)
C8—O1—C4—C51.6 (3)C10—N1—C11—O3−5.9 (3)
C8—O1—C4—C3−178.34 (18)C10—N1—C11—C12172.39 (18)
O2—C3—C4—O1−0.7 (3)O3—C11—C12—C13−11.6 (3)
C2—C3—C4—O1179.31 (18)N1—C11—C12—C13170.1 (2)
O2—C3—C4—C5179.38 (19)C11—C12—C13—O4177.17 (19)
C2—C3—C4—C5−0.6 (3)C11—C12—C13—C14−5.3 (4)
O1—C4—C5—C6−179.30 (19)C15—O4—C13—C12−1.4 (3)
C3—C4—C5—C60.6 (3)C15—O4—C13—C14−179.3 (2)
C2—C1—C6—C5−0.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.881.962.842 (2)176
C15—H15A···O1ii0.982.483.434 (3)164

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2630).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bernhard, H. O. & Snieckus, V. (1971). Tetrahedron, 27, 2091–2100.
  • Ma, C., Liu, S., Xin, L., Zhang, Q., Ding, K., Falck, J. R. & Shin, D. (2006). Chem. Lett.35, 1010–1011.
  • Rigaku (2007). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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