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The crystal structure of the (E)-isomer of the title compound, C10H17NO3, is reported. The mol­ecules are linked along the c axis by intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201615X/cv6140sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201615X/cv6140Isup2.hkl
Contains datablock I

CCDC reference: 198953

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.058
  • wR factor = 0.166
  • Data-to-parameter ratio = 20.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(9) - C(10) = 1.38 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound (E)-ethyl 3-acetamido-2-hexenoate, (I), is one of the isomers of ethyl 3-acetamido-2-hexenoate – a prochiral olefinic substrate for producing beta-amino acids and derivatives by asymmetric hydrogenation (Lubell et al., 1991; Yasutake et al., 2001). The enantiomeric excess of the hydrogenation product of the (Z) and (E) isomers is significantly different. The crystal structure of (I) (Fig. 1) exhibits bond lengths and angles within normal ranges (Table 1). In the packing, the molecules are interconnected by N—H···O hydrogen bonding (Table 2). The hydrogen bonds link the molecules along the c axis (Fig. 2).

Experimental top

(E)-Ethyl 3-acetamido-2-hexenoate was synthesized according to literature methods (Zhu, et al. 1999) A crystal suitable for X-ray analysis was grown slowly in mixed solvent (ethyl acetate and hexane) at room temperature. 1H NMR (500 MHz, acetone-d6, Varian): δ 0.92(t, J = 7.36 Hz, 3H), 1.21(t, J = 7.11 Hz, 3H), 1.56(m, 2H), 2.04(s, 3H), 2.72(m, 2H), 4.06(q, J = 7.11 Hz, 2H), 6.91(s, 1H), 8.72(br, 1H).

Refinement top

Hydrogen atoms were included in the riding model approximation with Uiso equal to Ueq of the atom to which they were bound.

Computing details top

Data collection: SMART (Bruker, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Bruker, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram for (I). The hydrogen bonds are indicated by dashed lines.
(E)-Ethyl 3-acetamido-2-hexenoate top
Crystal data top
C10H17NO3F(000) = 432
Mr = 199.25Dx = 1.117 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.036 (2) ÅCell parameters from 2265 reflections
b = 12.260 (2) Åθ = 1–27.5°
c = 9.5764 (18) ŵ = 0.08 mm1
β = 113.851 (4)°T = 294 K
V = 1185.0 (4) Å3Block, colorless
Z = 40.40 × 0.32 × 0.30 mm
Data collection top
Siemens CCD area-detector
diffractometer
2709 independent reflections
Radiation source: fine-focus sealed tube1073 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scansθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.968, Tmax = 0.976k = 1513
7877 measured reflectionsl = 1212
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.060P)2]
where P = (Fo2 + 2Fc2)/3
2709 reflections(Δ/σ)max < 0.001
130 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C10H17NO3V = 1185.0 (4) Å3
Mr = 199.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.036 (2) ŵ = 0.08 mm1
b = 12.260 (2) ÅT = 294 K
c = 9.5764 (18) Å0.40 × 0.32 × 0.30 mm
β = 113.851 (4)°
Data collection top
Siemens CCD area-detector
diffractometer
2709 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1073 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.976Rint = 0.048
7877 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.23 e Å3
2709 reflectionsΔρmin = 0.17 e Å3
130 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
O10.8072 (2)0.11649 (17)0.6456 (3)0.1179 (8)
O20.53400 (18)0.22252 (13)0.34207 (18)0.0805 (6)
O30.7764 (2)0.08943 (15)0.4052 (2)0.1037 (7)
N10.56818 (17)0.17617 (14)0.58445 (19)0.0580 (5)
H1A0.55090.19710.66010.070*
C10.7598 (3)0.0632 (2)0.5318 (3)0.0727 (7)
C20.6801 (2)0.03531 (18)0.5059 (3)0.0613 (6)
H2A0.65350.06930.41140.074*
C30.6428 (2)0.07996 (18)0.6096 (2)0.0553 (6)
C40.6766 (2)0.03670 (19)0.7686 (3)0.0671 (7)
H4A0.69120.04140.76970.080*
H4B0.60230.04910.79630.080*
C50.7997 (3)0.0911 (2)0.8862 (3)0.0933 (9)
H5A0.87410.07840.85890.112*
H5B0.78530.16920.88490.112*
C60.8331 (4)0.0482 (3)1.0452 (3)0.1336 (13)
H6A0.76620.07091.07910.200*
H6B0.91750.07651.11330.200*
H6C0.83680.03001.04440.200*
C70.5190 (2)0.24139 (18)0.4594 (3)0.0615 (6)
C80.4443 (3)0.3393 (2)0.4759 (3)0.0862 (8)
H8A0.41830.38340.38560.129*
H8B0.50000.38120.56290.129*
H8C0.36690.31590.48970.129*
C90.8583 (4)0.1847 (3)0.4111 (4)0.1267 (13)
H9A0.87540.22530.50420.152*
H9B0.81090.23210.32520.152*
C100.9775 (4)0.1537 (3)0.4070 (6)0.166 (2)
H10A0.96070.10750.32020.250*
H10B1.02500.21740.39920.250*
H10C1.02950.11470.49870.250*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.161 (2)0.0953 (15)0.1147 (18)0.0534 (14)0.0735 (16)0.0409 (13)
O20.1295 (15)0.0687 (11)0.0547 (10)0.0140 (9)0.0490 (11)0.0092 (8)
O30.1421 (18)0.0850 (14)0.0983 (15)0.0324 (12)0.0632 (14)0.0072 (11)
N10.0805 (13)0.0552 (12)0.0431 (11)0.0037 (9)0.0301 (10)0.0008 (9)
C10.0885 (19)0.0612 (17)0.0772 (19)0.0004 (14)0.0426 (17)0.0029 (15)
C20.0746 (16)0.0571 (14)0.0524 (14)0.0008 (12)0.0260 (13)0.0015 (11)
C30.0659 (15)0.0514 (14)0.0464 (13)0.0058 (11)0.0205 (12)0.0005 (10)
C40.0834 (17)0.0617 (14)0.0544 (15)0.0034 (12)0.0261 (14)0.0084 (12)
C50.095 (2)0.102 (2)0.0618 (18)0.0104 (16)0.0101 (16)0.0094 (15)
C60.139 (3)0.165 (3)0.060 (2)0.020 (2)0.002 (2)0.022 (2)
C70.0860 (17)0.0538 (14)0.0483 (14)0.0018 (12)0.0310 (13)0.0009 (11)
C80.125 (2)0.0651 (17)0.0802 (19)0.0231 (15)0.0541 (18)0.0117 (14)
C90.170 (4)0.088 (2)0.146 (3)0.042 (2)0.089 (3)0.009 (2)
C100.116 (3)0.112 (3)0.281 (7)0.034 (2)0.091 (4)0.018 (3)
Geometric parameters (Å, º) top
O1—C11.195 (3)C5—H5A0.9700
O2—C71.223 (2)C5—H5B0.9700
O3—C11.336 (3)C6—H6A0.9600
O3—C91.464 (3)C6—H6B0.9600
N1—C71.357 (3)C6—H6C0.9600
N1—C31.402 (3)C7—C81.499 (3)
N1—H1A0.8600C8—H8A0.9600
C1—C21.455 (3)C8—H8B0.9600
C2—C31.336 (3)C8—H8C0.9600
C2—H2A0.9300C9—C101.386 (4)
C3—C41.510 (3)C9—H9A0.9700
C4—C51.524 (3)C9—H9B0.9700
C4—H4A0.9700C10—H10A0.9600
C4—H4B0.9700C10—H10B0.9600
C5—C61.508 (4)C10—H10C0.9600
C1—O3—C9117.8 (2)C5—C6—H6B109.5
C7—N1—C3130.14 (17)H6A—C6—H6B109.5
C7—N1—H1A114.9C5—C6—H6C109.5
C3—N1—H1A114.9H6A—C6—H6C109.5
O1—C1—O3121.8 (2)H6B—C6—H6C109.5
O1—C1—C2128.3 (2)O2—C7—N1123.0 (2)
O3—C1—C2109.9 (2)O2—C7—C8122.2 (2)
C3—C2—C1124.1 (2)N1—C7—C8114.80 (19)
C3—C2—H2A118.0C7—C8—H8A109.5
C1—C2—H2A118.0C7—C8—H8B109.5
C2—C3—N1123.6 (2)H8A—C8—H8B109.5
C2—C3—C4125.5 (2)C7—C8—H8C109.5
N1—C3—C4110.92 (18)H8A—C8—H8C109.5
C3—C4—C5111.99 (19)H8B—C8—H8C109.5
C3—C4—H4A109.2C10—C9—O3111.0 (3)
C5—C4—H4A109.2C10—C9—H9A109.4
C3—C4—H4B109.2O3—C9—H9A109.4
C5—C4—H4B109.2C10—C9—H9B109.4
H4A—C4—H4B107.9O3—C9—H9B109.4
C6—C5—C4112.0 (2)H9A—C9—H9B108.0
C6—C5—H5A109.2C9—C10—H10A109.5
C4—C5—H5A109.2C9—C10—H10B109.5
C6—C5—H5B109.2H10A—C10—H10B109.5
C4—C5—H5B109.2C9—C10—H10C109.5
H5A—C5—H5B107.9H10A—C10—H10C109.5
C5—C6—H6A109.5H10B—C10—H10C109.5
C9—O3—C1—O11.7 (4)C7—N1—C3—C4179.3 (2)
C9—O3—C1—C2177.9 (3)C2—C3—C4—C594.6 (3)
O1—C1—C2—C32.7 (4)N1—C3—C4—C584.1 (2)
O3—C1—C2—C3177.7 (2)C3—C4—C5—C6179.7 (2)
C1—C2—C3—N1178.6 (2)C3—N1—C7—O20.6 (4)
C1—C2—C3—C40.1 (4)C3—N1—C7—C8179.4 (2)
C7—N1—C3—C20.5 (4)C1—O3—C9—C10109.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.072.920 (2)167
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H17NO3
Mr199.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)11.036 (2), 12.260 (2), 9.5764 (18)
β (°) 113.851 (4)
V3)1185.0 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.32 × 0.30
Data collection
DiffractometerSiemens CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.968, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
7877, 2709, 1073
Rint0.048
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.166, 1.09
No. of reflections2709
No. of parameters130
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.17

Computer programs: SMART (Bruker, 1995), SMART, SHELXTL-NT (Bruker, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C11.195 (3)N1—C71.357 (3)
O2—C71.223 (2)C2—C31.336 (3)
C1—O3—C9117.8 (2)O1—C1—C2128.3 (2)
C7—N1—C3130.14 (17)
O1—C1—C2—C32.7 (4)C1—C2—C3—C40.1 (4)
C1—C2—C3—N1178.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.072.920 (2)167.3
Symmetry code: (i) x, y+1/2, z+1/2.
 

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