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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o432
https://doi.org/10.1107/S1600536810001972

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

Xiang Lia*

aChemistry and Chemical Engineering Department, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China
*Correspondence e-mail: lixiang_acta@yahoo.com.cn

(Received 10 January 2010; accepted 15 January 2010; online 23 January 2010)

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[Bernhard, H. O. & Snieckus, V. (1971). Tetrahedron, 27, 2091-2100.]); Ma et al. (2006[Ma, C., Liu, S., Xin, L., Zhang, Q., Ding, K., Falck, J. R. & Shin, D. (2006). Chem. Lett. 35, 1010-1011.]). For bond-length data, see Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data

  • C15H21NO4

  • Mr = 279.33

  • Monoclinic, P 21 /c

  • 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[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.973, Tmax = 0.987

  • 10754 measured reflections

  • 2591 independent reflections

  • 2435 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O3i 0.88 1.96 2.842 (2) 176
C15—H15A⋯O1ii 0.98 2.48 3.434 (3) 164
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001972/hg2630Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
(E)-N-(3,4-Dimethoxyphenethyl)-3-methoxybut-2-enamide top
Crystal data top
C15H21NO4F(000) = 600
Mr = 279.33Dx = 1.256 Mg m−3
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 mm−1
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 top
Rigaku Mercury CCD/AFC
diffractometer		2591 independent reflections
Radiation source: Sealed Tube2435 reflections with I > 2σ(I)
Graphite Monochromator monochromatorRint = 0.049
φ 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 top
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 = 1.18 w = 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 Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C15H21NO4V = 1477.5 (5) Å3
Mr = 279.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.509 (3) ŵ = 0.09 mm−1
b = 14.930 (3) ÅT = 173 K
c = 8.2998 (17) Å0.30 × 0.20 × 0.15 mm
β = 107.59 (3)°
Data collection top
Rigaku Mercury CCD/AFC
diffractometer		2591 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)		2435 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.987Rint = 0.049
10754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.18Δρmax = 0.16 e Å−3
2591 reflectionsΔρmin = −0.18 e Å−3
181 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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC15H21NO4
Mr279.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)12.509 (3), 14.930 (3), 8.2998 (17)
β (°) 107.59 (3)
V (Å3)1477.5 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.30 × 0.20 × 0.15
Data collection
DiffractometerRigaku Mercury CCD/AFC
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.973, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		10754, 2591, 2435
Rint0.049
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.133, 1.18
No. of reflections2591
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.16, −0.18

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.881.962.842 (2)176.4
C15—H15A···O1ii0.982.483.434 (3)163.8
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z+1/2.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBernhard, H. O. & Snieckus, V. (1971). Tetrahedron, 27, 2091–2100.  CrossRef CAS Web of Science Google Scholar
 First citationMa, C., Liu, S., Xin, L., Zhang, Q., Ding, K., Falck, J. R. & Shin, D. (2006). Chem. Lett. 35, 1010–1011.  Web of Science CrossRef CAS Google Scholar
 First citationRigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o432
https://doi.org/10.1107/S1600536810001972
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