Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201615X/cv6140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680201615X/cv6140Isup2.hkl |
CCDC reference: 198953
(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).
Hydrogen atoms were included in the riding model approximation with Uiso equal to Ueq of the atom to which they were bound.
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.
Fig. 1. Molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level. | |
Fig. 2. Packing diagram for (I). The hydrogen bonds are indicated by dashed lines. |
C10H17NO3 | F(000) = 432 |
Mr = 199.25 | Dx = 1.117 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.036 (2) Å | Cell parameters from 2265 reflections |
b = 12.260 (2) Å | θ = 1–27.5° |
c = 9.5764 (18) Å | µ = 0.08 mm−1 |
β = 113.851 (4)° | T = 294 K |
V = 1185.0 (4) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.32 × 0.30 mm |
Siemens CCD area-detector diffractometer | 2709 independent reflections |
Radiation source: fine-focus sealed tube | 1073 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.968, Tmax = 0.976 | k = −15→13 |
7877 measured reflections | l = −12→12 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H 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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C10H17NO3 | V = 1185.0 (4) Å3 |
Mr = 199.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.036 (2) Å | µ = 0.08 mm−1 |
b = 12.260 (2) Å | T = 294 K |
c = 9.5764 (18) Å | 0.40 × 0.32 × 0.30 mm |
β = 113.851 (4)° |
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 = 0.976 | Rint = 0.048 |
7877 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.23 e Å−3 |
2709 reflections | Δρmin = −0.17 e Å−3 |
130 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8072 (2) | −0.11649 (17) | 0.6456 (3) | 0.1179 (8) | |
O2 | 0.53400 (18) | 0.22252 (13) | 0.34207 (18) | 0.0805 (6) | |
O3 | 0.7764 (2) | −0.08943 (15) | 0.4052 (2) | 0.1037 (7) | |
N1 | 0.56818 (17) | 0.17617 (14) | 0.58445 (19) | 0.0580 (5) | |
H1A | 0.5509 | 0.1971 | 0.6601 | 0.070* | |
C1 | 0.7598 (3) | −0.0632 (2) | 0.5318 (3) | 0.0727 (7) | |
C2 | 0.6801 (2) | 0.03531 (18) | 0.5059 (3) | 0.0613 (6) | |
H2A | 0.6535 | 0.0693 | 0.4114 | 0.074* | |
C3 | 0.6428 (2) | 0.07996 (18) | 0.6096 (2) | 0.0553 (6) | |
C4 | 0.6766 (2) | 0.03670 (19) | 0.7686 (3) | 0.0671 (7) | |
H4A | 0.6912 | −0.0414 | 0.7697 | 0.080* | |
H4B | 0.6023 | 0.0491 | 0.7963 | 0.080* | |
C5 | 0.7997 (3) | 0.0911 (2) | 0.8862 (3) | 0.0933 (9) | |
H5A | 0.8741 | 0.0784 | 0.8589 | 0.112* | |
H5B | 0.7853 | 0.1692 | 0.8849 | 0.112* | |
C6 | 0.8331 (4) | 0.0482 (3) | 1.0452 (3) | 0.1336 (13) | |
H6A | 0.7662 | 0.0709 | 1.0791 | 0.200* | |
H6B | 0.9175 | 0.0765 | 1.1133 | 0.200* | |
H6C | 0.8368 | −0.0300 | 1.0444 | 0.200* | |
C7 | 0.5190 (2) | 0.24139 (18) | 0.4594 (3) | 0.0615 (6) | |
C8 | 0.4443 (3) | 0.3393 (2) | 0.4759 (3) | 0.0862 (8) | |
H8A | 0.4183 | 0.3834 | 0.3856 | 0.129* | |
H8B | 0.5000 | 0.3812 | 0.5629 | 0.129* | |
H8C | 0.3669 | 0.3159 | 0.4897 | 0.129* | |
C9 | 0.8583 (4) | −0.1847 (3) | 0.4111 (4) | 0.1267 (13) | |
H9A | 0.8754 | −0.2253 | 0.5042 | 0.152* | |
H9B | 0.8109 | −0.2321 | 0.3252 | 0.152* | |
C10 | 0.9775 (4) | −0.1537 (3) | 0.4070 (6) | 0.166 (2) | |
H10A | 0.9607 | −0.1075 | 0.3202 | 0.250* | |
H10B | 1.0250 | −0.2174 | 0.3992 | 0.250* | |
H10C | 1.0295 | −0.1147 | 0.4987 | 0.250* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.161 (2) | 0.0953 (15) | 0.1147 (18) | 0.0534 (14) | 0.0735 (16) | 0.0409 (13) |
O2 | 0.1295 (15) | 0.0687 (11) | 0.0547 (10) | 0.0140 (9) | 0.0490 (11) | 0.0092 (8) |
O3 | 0.1421 (18) | 0.0850 (14) | 0.0983 (15) | 0.0324 (12) | 0.0632 (14) | −0.0072 (11) |
N1 | 0.0805 (13) | 0.0552 (12) | 0.0431 (11) | 0.0037 (9) | 0.0301 (10) | 0.0008 (9) |
C1 | 0.0885 (19) | 0.0612 (17) | 0.0772 (19) | 0.0004 (14) | 0.0426 (17) | −0.0029 (15) |
C2 | 0.0746 (16) | 0.0571 (14) | 0.0524 (14) | 0.0008 (12) | 0.0260 (13) | 0.0015 (11) |
C3 | 0.0659 (15) | 0.0514 (14) | 0.0464 (13) | −0.0058 (11) | 0.0205 (12) | −0.0005 (10) |
C4 | 0.0834 (17) | 0.0617 (14) | 0.0544 (15) | −0.0034 (12) | 0.0261 (14) | 0.0084 (12) |
C5 | 0.095 (2) | 0.102 (2) | 0.0618 (18) | −0.0104 (16) | 0.0101 (16) | 0.0094 (15) |
C6 | 0.139 (3) | 0.165 (3) | 0.060 (2) | −0.020 (2) | 0.002 (2) | 0.022 (2) |
C7 | 0.0860 (17) | 0.0538 (14) | 0.0483 (14) | −0.0018 (12) | 0.0310 (13) | −0.0009 (11) |
C8 | 0.125 (2) | 0.0651 (17) | 0.0802 (19) | 0.0231 (15) | 0.0541 (18) | 0.0117 (14) |
C9 | 0.170 (4) | 0.088 (2) | 0.146 (3) | 0.042 (2) | 0.089 (3) | −0.009 (2) |
C10 | 0.116 (3) | 0.112 (3) | 0.281 (7) | 0.034 (2) | 0.091 (4) | 0.018 (3) |
O1—C1 | 1.195 (3) | C5—H5A | 0.9700 |
O2—C7 | 1.223 (2) | C5—H5B | 0.9700 |
O3—C1 | 1.336 (3) | C6—H6A | 0.9600 |
O3—C9 | 1.464 (3) | C6—H6B | 0.9600 |
N1—C7 | 1.357 (3) | C6—H6C | 0.9600 |
N1—C3 | 1.402 (3) | C7—C8 | 1.499 (3) |
N1—H1A | 0.8600 | C8—H8A | 0.9600 |
C1—C2 | 1.455 (3) | C8—H8B | 0.9600 |
C2—C3 | 1.336 (3) | C8—H8C | 0.9600 |
C2—H2A | 0.9300 | C9—C10 | 1.386 (4) |
C3—C4 | 1.510 (3) | C9—H9A | 0.9700 |
C4—C5 | 1.524 (3) | C9—H9B | 0.9700 |
C4—H4A | 0.9700 | C10—H10A | 0.9600 |
C4—H4B | 0.9700 | C10—H10B | 0.9600 |
C5—C6 | 1.508 (4) | C10—H10C | 0.9600 |
C1—O3—C9 | 117.8 (2) | C5—C6—H6B | 109.5 |
C7—N1—C3 | 130.14 (17) | H6A—C6—H6B | 109.5 |
C7—N1—H1A | 114.9 | C5—C6—H6C | 109.5 |
C3—N1—H1A | 114.9 | H6A—C6—H6C | 109.5 |
O1—C1—O3 | 121.8 (2) | H6B—C6—H6C | 109.5 |
O1—C1—C2 | 128.3 (2) | O2—C7—N1 | 123.0 (2) |
O3—C1—C2 | 109.9 (2) | O2—C7—C8 | 122.2 (2) |
C3—C2—C1 | 124.1 (2) | N1—C7—C8 | 114.80 (19) |
C3—C2—H2A | 118.0 | C7—C8—H8A | 109.5 |
C1—C2—H2A | 118.0 | C7—C8—H8B | 109.5 |
C2—C3—N1 | 123.6 (2) | H8A—C8—H8B | 109.5 |
C2—C3—C4 | 125.5 (2) | C7—C8—H8C | 109.5 |
N1—C3—C4 | 110.92 (18) | H8A—C8—H8C | 109.5 |
C3—C4—C5 | 111.99 (19) | H8B—C8—H8C | 109.5 |
C3—C4—H4A | 109.2 | C10—C9—O3 | 111.0 (3) |
C5—C4—H4A | 109.2 | C10—C9—H9A | 109.4 |
C3—C4—H4B | 109.2 | O3—C9—H9A | 109.4 |
C5—C4—H4B | 109.2 | C10—C9—H9B | 109.4 |
H4A—C4—H4B | 107.9 | O3—C9—H9B | 109.4 |
C6—C5—C4 | 112.0 (2) | H9A—C9—H9B | 108.0 |
C6—C5—H5A | 109.2 | C9—C10—H10A | 109.5 |
C4—C5—H5A | 109.2 | C9—C10—H10B | 109.5 |
C6—C5—H5B | 109.2 | H10A—C10—H10B | 109.5 |
C4—C5—H5B | 109.2 | C9—C10—H10C | 109.5 |
H5A—C5—H5B | 107.9 | H10A—C10—H10C | 109.5 |
C5—C6—H6A | 109.5 | H10B—C10—H10C | 109.5 |
C9—O3—C1—O1 | −1.7 (4) | C7—N1—C3—C4 | 179.3 (2) |
C9—O3—C1—C2 | 177.9 (3) | C2—C3—C4—C5 | 94.6 (3) |
O1—C1—C2—C3 | −2.7 (4) | N1—C3—C4—C5 | −84.1 (2) |
O3—C1—C2—C3 | 177.7 (2) | C3—C4—C5—C6 | 179.7 (2) |
C1—C2—C3—N1 | 178.6 (2) | C3—N1—C7—O2 | 0.6 (4) |
C1—C2—C3—C4 | 0.1 (4) | C3—N1—C7—C8 | −179.4 (2) |
C7—N1—C3—C2 | 0.5 (4) | C1—O3—C9—C10 | −109.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.07 | 2.920 (2) | 167 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H17NO3 |
Mr | 199.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 11.036 (2), 12.260 (2), 9.5764 (18) |
β (°) | 113.851 (4) |
V (Å3) | 1185.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.32 × 0.30 |
Data collection | |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.968, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7877, 2709, 1073 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.166, 1.09 |
No. of reflections | 2709 |
No. of parameters | 130 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.17 |
Computer programs: SMART (Bruker, 1995), SMART, SHELXTL-NT (Bruker, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.
O1—C1 | 1.195 (3) | N1—C7 | 1.357 (3) |
O2—C7 | 1.223 (2) | C2—C3 | 1.336 (3) |
C1—O3—C9 | 117.8 (2) | O1—C1—C2 | 128.3 (2) |
C7—N1—C3 | 130.14 (17) | ||
O1—C1—C2—C3 | −2.7 (4) | C1—C2—C3—C4 | 0.1 (4) |
C1—C2—C3—N1 | 178.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.07 | 2.920 (2) | 167.3 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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).