Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021396/ww6052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021396/ww6052Isup2.hkl |
CCDC reference: 202349
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.155
- Data-to-parameter ratio = 19.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was synthesized according to the literature (Zhu et al., 1999). A crystal suitable for X-ray analysis was slowly grown in a mixed solvent of ethyl acetate and hexane at room temperature. 1H NMR (400 MHz, acetone-d6, Bruker): δ 1.09–1.12 (t, J = 7.5 Hz, 3H), 2.06 (s, 3H), 2.71–2.77 (q, J = 7.5 Hz, 2H), 3.59 (s, 3H), 6.87 (s, 1H), 8.75 (br, 1H).
H atoms were included in the riding-model approximation, with Uiso values equal to Ueq of the atom to which they were bound.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level (Siemens, 1995). | |
Fig. 2. Packing diagram for (I). Hydrogen bonds are indicated by dashed lines. |
C8H13NO3 | F(000) = 736 |
Mr = 171.19 | Dx = 1.220 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2920 reflections |
a = 9.718 (7) Å | θ = 1–27.5° |
b = 12.673 (9) Å | µ = 0.09 mm−1 |
c = 15.653 (7) Å | T = 294 K |
β = 104.825 (15)° | Needle, colorless |
V = 1864 (2) Å3 | 0.38 × 0.12 × 0.10 mm |
Z = 8 |
Siemens CCD area-detector diffractometer | 4308 independent reflections |
Radiation source: fine-focus sealed tube | 1544 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ϕ and ω scans | θmax = 27.6°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.965, Tmax = 0.991 | k = −15→16 |
12544 measured reflections | l = −16→20 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
4308 reflections | (Δ/σ)max < 0.001 |
223 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C8H13NO3 | V = 1864 (2) Å3 |
Mr = 171.19 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.718 (7) Å | µ = 0.09 mm−1 |
b = 12.673 (9) Å | T = 294 K |
c = 15.653 (7) Å | 0.38 × 0.12 × 0.10 mm |
β = 104.825 (15)° |
Siemens CCD area-detector diffractometer | 4308 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1544 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.991 | Rint = 0.057 |
12544 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.17 e Å−3 |
4308 reflections | Δρmin = −0.19 e Å−3 |
223 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 | 0.9833 (2) | 0.69319 (16) | 0.09679 (19) | 0.1094 (9) | |
O2 | 1.18911 (19) | 0.62579 (15) | 0.08953 (14) | 0.0753 (6) | |
O3 | 1.10959 (18) | 0.30060 (14) | 0.17560 (15) | 0.0760 (7) | |
N1 | 0.8894 (2) | 0.36964 (16) | 0.15820 (14) | 0.0540 (6) | |
H1A | 0.8036 | 0.3530 | 0.1580 | 0.065* | |
C1 | 0.9105 (2) | 0.4745 (2) | 0.13860 (18) | 0.0507 (7) | |
C2 | 1.0278 (3) | 0.5087 (2) | 0.11740 (17) | 0.0516 (7) | |
H2 | 1.0956 | 0.4587 | 0.1130 | 0.062* | |
C3 | 1.0572 (3) | 0.6175 (2) | 0.10079 (19) | 0.0593 (8) | |
C4 | 1.2351 (4) | 0.7300 (3) | 0.0731 (2) | 0.0991 (12) | |
H4A | 1.1591 | 0.7658 | 0.0321 | 0.149* | |
H4B | 1.3160 | 0.7250 | 0.0487 | 0.149* | |
H4C | 1.2608 | 0.7687 | 0.1276 | 0.149* | |
C5 | 0.7856 (3) | 0.5444 (2) | 0.1451 (2) | 0.0661 (9) | |
H5A | 0.7403 | 0.5150 | 0.1883 | 0.079* | |
H5B | 0.8202 | 0.6143 | 0.1649 | 0.079* | |
C6 | 0.6797 (3) | 0.5522 (3) | 0.0579 (2) | 0.1045 (13) | |
H6A | 0.7240 | 0.5828 | 0.0156 | 0.157* | |
H6B | 0.6016 | 0.5958 | 0.0634 | 0.157* | |
H6C | 0.6451 | 0.4830 | 0.0385 | 0.157* | |
C7 | 0.9857 (3) | 0.2902 (2) | 0.17752 (19) | 0.0571 (8) | |
C8 | 0.9303 (3) | 0.1880 (2) | 0.2023 (2) | 0.0834 (11) | |
H8A | 0.8976 | 0.1452 | 0.1505 | 0.125* | |
H8B | 0.8528 | 0.2013 | 0.2285 | 0.125* | |
H8C | 1.0049 | 0.1516 | 0.2440 | 0.125* | |
O4 | 0.4679 (2) | −0.10593 (16) | 0.11316 (17) | 0.0964 (8) | |
O5 | 0.68342 (19) | −0.04784 (14) | 0.11396 (13) | 0.0686 (6) | |
O6 | 0.60226 (18) | 0.29268 (14) | 0.16089 (14) | 0.0742 (7) | |
N2 | 0.3890 (2) | 0.22289 (16) | 0.16423 (14) | 0.0524 (6) | |
H2A | 0.3053 | 0.2408 | 0.1677 | 0.063* | |
C9 | 0.4066 (2) | 0.1162 (2) | 0.14978 (17) | 0.0459 (7) | |
C10 | 0.5211 (3) | 0.07784 (19) | 0.12828 (17) | 0.0485 (7) | |
H10 | 0.5885 | 0.1258 | 0.1194 | 0.058* | |
C11 | 0.5477 (3) | −0.0328 (2) | 0.11787 (18) | 0.0555 (8) | |
C12 | 0.7239 (3) | −0.1552 (2) | 0.1038 (2) | 0.0859 (11) | |
H12A | 0.7171 | −0.1954 | 0.1546 | 0.129* | |
H12B | 0.8202 | −0.1570 | 0.0986 | 0.129* | |
H12C | 0.6616 | −0.1848 | 0.0517 | 0.129* | |
C13 | 0.2837 (3) | 0.0516 (2) | 0.16213 (18) | 0.0543 (8) | |
H13A | 0.2458 | 0.0842 | 0.2074 | 0.065* | |
H13B | 0.3178 | −0.0181 | 0.1828 | 0.065* | |
C14 | 0.1658 (3) | 0.0409 (2) | 0.0786 (2) | 0.0779 (10) | |
H14A | 0.1314 | 0.1096 | 0.0578 | 0.117* | |
H14B | 0.0895 | 0.0002 | 0.0906 | 0.117* | |
H14C | 0.2015 | 0.0059 | 0.0343 | 0.117* | |
C15 | 0.4841 (3) | 0.3031 (2) | 0.17365 (19) | 0.0549 (8) | |
C16 | 0.4349 (3) | 0.4060 (2) | 0.2011 (2) | 0.0767 (10) | |
H16A | 0.5118 | 0.4394 | 0.2433 | 0.115* | |
H16B | 0.3571 | 0.3942 | 0.2274 | 0.115* | |
H16C | 0.4039 | 0.4507 | 0.1502 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0791 (16) | 0.0514 (15) | 0.214 (3) | 0.0174 (13) | 0.0671 (18) | 0.0217 (15) |
O2 | 0.0552 (13) | 0.0565 (13) | 0.1210 (18) | −0.0154 (10) | 0.0349 (12) | 0.0012 (12) |
O3 | 0.0336 (11) | 0.0586 (13) | 0.144 (2) | 0.0072 (9) | 0.0368 (12) | 0.0141 (12) |
N1 | 0.0251 (11) | 0.0437 (14) | 0.0964 (18) | 0.0005 (10) | 0.0211 (12) | 0.0040 (12) |
C1 | 0.0295 (14) | 0.0463 (18) | 0.074 (2) | 0.0026 (13) | 0.0094 (14) | 0.0000 (14) |
C2 | 0.0353 (15) | 0.0428 (17) | 0.078 (2) | 0.0040 (13) | 0.0174 (15) | 0.0014 (14) |
C3 | 0.0494 (18) | 0.049 (2) | 0.081 (2) | −0.0011 (15) | 0.0205 (17) | −0.0001 (16) |
C4 | 0.093 (3) | 0.067 (2) | 0.144 (3) | −0.039 (2) | 0.044 (2) | 0.000 (2) |
C5 | 0.0452 (17) | 0.056 (2) | 0.097 (3) | 0.0040 (14) | 0.0190 (18) | 0.0010 (16) |
C6 | 0.058 (2) | 0.104 (3) | 0.132 (4) | 0.023 (2) | −0.011 (2) | −0.009 (2) |
C7 | 0.0365 (16) | 0.0494 (19) | 0.091 (2) | 0.0052 (14) | 0.0263 (17) | 0.0047 (15) |
C8 | 0.057 (2) | 0.058 (2) | 0.146 (3) | 0.0071 (16) | 0.046 (2) | 0.019 (2) |
O4 | 0.0780 (16) | 0.0512 (14) | 0.172 (2) | −0.0170 (12) | 0.0546 (16) | −0.0154 (14) |
O5 | 0.0581 (13) | 0.0486 (13) | 0.1061 (17) | 0.0146 (10) | 0.0337 (12) | −0.0038 (11) |
O6 | 0.0350 (11) | 0.0538 (13) | 0.144 (2) | −0.0060 (9) | 0.0408 (12) | −0.0171 (12) |
N2 | 0.0267 (11) | 0.0465 (15) | 0.0864 (18) | 0.0005 (10) | 0.0189 (12) | −0.0055 (12) |
C9 | 0.0323 (14) | 0.0467 (18) | 0.0577 (18) | −0.0035 (13) | 0.0099 (13) | −0.0001 (14) |
C10 | 0.0366 (15) | 0.0399 (17) | 0.072 (2) | −0.0009 (13) | 0.0185 (14) | −0.0043 (14) |
C11 | 0.0519 (18) | 0.049 (2) | 0.070 (2) | 0.0029 (16) | 0.0225 (16) | 0.0013 (16) |
C12 | 0.104 (3) | 0.054 (2) | 0.110 (3) | 0.0340 (19) | 0.046 (2) | 0.0111 (18) |
C13 | 0.0395 (16) | 0.0590 (19) | 0.066 (2) | −0.0068 (13) | 0.0170 (15) | 0.0015 (14) |
C14 | 0.0469 (18) | 0.094 (3) | 0.089 (3) | −0.0220 (16) | 0.0105 (18) | −0.0117 (19) |
C15 | 0.0360 (16) | 0.0464 (18) | 0.085 (2) | −0.0009 (13) | 0.0204 (16) | −0.0071 (15) |
C16 | 0.0472 (18) | 0.057 (2) | 0.129 (3) | 0.0012 (15) | 0.0281 (19) | −0.0221 (19) |
O1—C3 | 1.190 (3) | O4—C11 | 1.198 (3) |
O2—C3 | 1.342 (3) | O5—C11 | 1.349 (3) |
O2—C4 | 1.438 (3) | O5—C12 | 1.436 (3) |
O3—C7 | 1.219 (3) | O6—C15 | 1.222 (3) |
N1—C7 | 1.355 (3) | N2—C15 | 1.356 (3) |
N1—C1 | 1.391 (3) | N2—C9 | 1.388 (3) |
N1—H1A | 0.8600 | N2—H2A | 0.8600 |
C1—C2 | 1.338 (3) | C9—C10 | 1.334 (3) |
C1—C5 | 1.527 (3) | C9—C13 | 1.500 (3) |
C2—C3 | 1.445 (4) | C10—C11 | 1.443 (3) |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C4—H4A | 0.9600 | C12—H12A | 0.9600 |
C4—H4B | 0.9600 | C12—H12B | 0.9600 |
C4—H4C | 0.9600 | C12—H12C | 0.9600 |
C5—C6 | 1.488 (4) | C13—C14 | 1.508 (4) |
C5—H5A | 0.9700 | C13—H13A | 0.9700 |
C5—H5B | 0.9700 | C13—H13B | 0.9700 |
C6—H6A | 0.9600 | C14—H14A | 0.9600 |
C6—H6B | 0.9600 | C14—H14B | 0.9600 |
C6—H6C | 0.9600 | C14—H14C | 0.9600 |
C7—C8 | 1.492 (4) | C15—C16 | 1.489 (3) |
C8—H8A | 0.9600 | C16—H16A | 0.9600 |
C8—H8B | 0.9600 | C16—H16B | 0.9600 |
C8—H8C | 0.9600 | C16—H16C | 0.9600 |
C3—O2—C4 | 116.5 (2) | C11—O5—C12 | 115.9 (2) |
C7—N1—C1 | 128.8 (2) | C15—N2—C9 | 129.7 (2) |
C7—N1—H1A | 115.6 | C15—N2—H2A | 115.1 |
C1—N1—H1A | 115.6 | C9—N2—H2A | 115.1 |
C2—C1—N1 | 123.2 (2) | C10—C9—N2 | 122.8 (2) |
C2—C1—C5 | 124.8 (2) | C10—C9—C13 | 125.2 (2) |
N1—C1—C5 | 112.0 (2) | N2—C9—C13 | 112.0 (2) |
C1—C2—C3 | 125.1 (2) | C9—C10—C11 | 124.6 (2) |
C1—C2—H2 | 117.5 | C9—C10—H10 | 117.7 |
C3—C2—H2 | 117.5 | C11—C10—H10 | 117.7 |
O1—C3—O2 | 120.9 (3) | O4—C11—O5 | 120.9 (3) |
O1—C3—C2 | 129.4 (3) | O4—C11—C10 | 128.8 (3) |
O2—C3—C2 | 109.7 (2) | O5—C11—C10 | 110.3 (2) |
O2—C4—H4A | 109.5 | O5—C12—H12A | 109.5 |
O2—C4—H4B | 109.5 | O5—C12—H12B | 109.5 |
H4A—C4—H4B | 109.5 | H12A—C12—H12B | 109.5 |
O2—C4—H4C | 109.5 | O5—C12—H12C | 109.5 |
H4A—C4—H4C | 109.5 | H12A—C12—H12C | 109.5 |
H4B—C4—H4C | 109.5 | H12B—C12—H12C | 109.5 |
C6—C5—C1 | 110.6 (2) | C9—C13—C14 | 113.0 (2) |
C6—C5—H5A | 109.5 | C9—C13—H13A | 109.0 |
C1—C5—H5A | 109.5 | C14—C13—H13A | 109.0 |
C6—C5—H5B | 109.5 | C9—C13—H13B | 109.0 |
C1—C5—H5B | 109.5 | C14—C13—H13B | 109.0 |
H5A—C5—H5B | 108.1 | H13A—C13—H13B | 107.8 |
C5—C6—H6A | 109.5 | C13—C14—H14A | 109.5 |
C5—C6—H6B | 109.5 | C13—C14—H14B | 109.5 |
H6A—C6—H6B | 109.5 | H14A—C14—H14B | 109.5 |
C5—C6—H6C | 109.5 | C13—C14—H14C | 109.5 |
H6A—C6—H6C | 109.5 | H14A—C14—H14C | 109.5 |
H6B—C6—H6C | 109.5 | H14B—C14—H14C | 109.5 |
O3—C7—N1 | 123.0 (2) | O6—C15—N2 | 123.0 (2) |
O3—C7—C8 | 121.7 (2) | O6—C15—C16 | 121.7 (2) |
N1—C7—C8 | 115.4 (2) | N2—C15—C16 | 115.3 (2) |
C7—C8—H8A | 109.5 | C15—C16—H16A | 109.5 |
C7—C8—H8B | 109.5 | C15—C16—H16B | 109.5 |
H8A—C8—H8B | 109.5 | H16A—C16—H16B | 109.5 |
C7—C8—H8C | 109.5 | C15—C16—H16C | 109.5 |
H8A—C8—H8C | 109.5 | H16A—C16—H16C | 109.5 |
H8B—C8—H8C | 109.5 | H16B—C16—H16C | 109.5 |
C7—N1—C1—C2 | 14.8 (4) | C15—N2—C9—C10 | −11.3 (4) |
C7—N1—C1—C5 | −164.6 (3) | C15—N2—C9—C13 | 168.1 (3) |
N1—C1—C2—C3 | −176.8 (3) | N2—C9—C10—C11 | 176.1 (2) |
C5—C1—C2—C3 | 2.6 (4) | C13—C9—C10—C11 | −3.2 (4) |
C4—O2—C3—O1 | 0.3 (4) | C12—O5—C11—O4 | 0.1 (4) |
C4—O2—C3—C2 | −179.4 (2) | C12—O5—C11—C10 | 179.8 (2) |
C1—C2—C3—O1 | −5.5 (5) | C9—C10—C11—O4 | 12.2 (5) |
C1—C2—C3—O2 | 174.2 (3) | C9—C10—C11—O5 | −167.5 (3) |
C2—C1—C5—C6 | 88.7 (3) | C10—C9—C13—C14 | −91.6 (3) |
N1—C1—C5—C6 | −91.8 (3) | N2—C9—C13—C14 | 89.0 (3) |
C1—N1—C7—O3 | −4.0 (5) | C9—N2—C15—O6 | 8.2 (5) |
C1—N1—C7—C8 | 175.5 (3) | C9—N2—C15—C16 | −171.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O6 | 0.86 | 2.11 | 2.967 (3) | 173 |
N2—H2A···O3i | 0.86 | 2.08 | 2.936 (3) | 174 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H13NO3 |
Mr | 171.19 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 9.718 (7), 12.673 (9), 15.653 (7) |
β (°) | 104.825 (15) |
V (Å3) | 1864 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.38 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.965, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12544, 4308, 1544 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.156, 1.06 |
No. of reflections | 4308 |
No. of parameters | 223 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.19 |
Computer programs: SMART (Siemens, 1995), SMART, SHELXTL (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
O1—C3 | 1.190 (3) | O4—C11 | 1.198 (3) |
O3—C7 | 1.219 (3) | O6—C15 | 1.222 (3) |
N1—C7 | 1.355 (3) | N2—C15 | 1.356 (3) |
N1—C1 | 1.391 (3) | N2—C9 | 1.388 (3) |
C1—C2 | 1.338 (3) | C9—C10 | 1.334 (3) |
C2—C3 | 1.445 (4) | C10—C11 | 1.443 (3) |
C2—C1—C5 | 124.8 (2) | O1—C3—C2 | 129.4 (3) |
N1—C1—C5 | 112.0 (2) | O2—C3—C2 | 109.7 (2) |
C1—C2—C3 | 125.1 (2) | O3—C7—N1 | 123.0 (2) |
O1—C3—O2 | 120.9 (3) | O3—C7—C8 | 121.7 (2) |
N1—C1—C2—C3 | −176.8 (3) | C4—O2—C3—C2 | −179.4 (2) |
C5—C1—C2—C3 | 2.6 (4) | C1—N1—C7—O3 | −4.0 (5) |
C4—O2—C3—O1 | 0.3 (4) | C1—N1—C7—C8 | 175.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O6 | 0.86 | 2.11 | 2.967 (3) | 173 |
N2—H2A···O3i | 0.86 | 2.08 | 2.936 (3) | 174 |
Symmetry code: (i) x−1, y, z. |
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The title compound, (I), is one of the products obtained from reaction of methyl 3-amine-2-pentenoate with acetic anhydride at reflux for 24 h. This prochiral olefin is a model substrate studied in the asymmetric hydrogenation reaction (Hackler et al., 1985; Lubell et al., 1991). The structure determination of (I) was conducted in order to obtain more stereochemical information about the behaviours of these kinds of substrates in hydrogenation reaction. The crystal structure of (I) contains two independent molecules in the asymmetric unit (Fig. 1). A pairwise comparison between these two molecules shows no significant differences in their bond lengths or angles although the conformations of the two molecules are different (Table 1). The C1—C2 bond distance of 1.338 (3) Å is indicative of double-bond character. The angles of C1—C2—C3 [125.1 (2)°], C2—C1—C5 [124.8 (2)°] are larger and N1—C1—C5 [112.0 (2)°] smaller than 120°. This results in a close mutual repulsion between the ethyl group on C1 and carbonyl group on C3.
The molecules are interconnected by N—H···O hydrogen bonding in the crystal (Table 2). As illustrated in Fig. 2, the hydrogen bonding links the molecules along the a axis.