Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021554/ww6055sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021554/ww6055Isup2.hkl |
CCDC reference: 202351
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.064
- wR factor = 0.198
- Data-to-parameter ratio = 19.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.116
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was synthesized according to Zhu et al. (1999). A crystal suitable for X-ray analysis was grown slowly in a mixture of ethyl acetate and hexane at room temperature. 1H NMR (400 MHz, acetone-d6, Bruker): δ 1.13 (d, J = 7.1 Hz, 6H), 2.09 (s, 3H), 3.59 (s, 3H), 4.34 (sep, J = 7.1 Hz, 1H), 6.99 (s, 1H), 8.18 (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. |
C9H15NO3 | Dx = 1.182 Mg m−3 |
Mr = 185.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2463 reflections |
a = 9.806 (2) Å | θ = 1–27.5° |
b = 12.435 (3) Å | µ = 0.09 mm−1 |
c = 17.067 (4) Å | T = 294 K |
V = 2081.1 (9) Å3 | Needle, colorless |
Z = 8 | 0.28 × 0.10 × 0.10 mm |
F(000) = 800 |
Siemens CCD area-detector diffractometer | 2384 independent reflections |
Radiation source: fine-focus sealed tube | 888 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.116 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.976, Tmax = 0.991 | k = −14→16 |
13157 measured reflections | l = −18→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.198 | w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2384 reflections | Δρmax = 0.18 e Å−3 |
123 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.024 (5) |
C9H15NO3 | V = 2081.1 (9) Å3 |
Mr = 185.22 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.806 (2) Å | µ = 0.09 mm−1 |
b = 12.435 (3) Å | T = 294 K |
c = 17.067 (4) Å | 0.28 × 0.10 × 0.10 mm |
Siemens CCD area-detector diffractometer | 2384 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 888 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.991 | Rint = 0.116 |
13157 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.18 e Å−3 |
2384 reflections | Δρmin = −0.32 e Å−3 |
123 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 | 0.5932 (3) | 0.4260 (2) | 0.69203 (16) | 0.0987 (10) | |
O2 | 0.7795 (2) | 0.45268 (18) | 0.62146 (13) | 0.0695 (8) | |
O3 | 0.6352 (2) | 0.73287 (18) | 0.48475 (12) | 0.0641 (8) | |
N1 | 0.4320 (2) | 0.6810 (2) | 0.53746 (14) | 0.0537 (7) | |
H1 | 0.3459 | 0.6938 | 0.5354 | 0.064* | |
C1 | 0.6501 (3) | 0.4738 (3) | 0.63972 (19) | 0.0557 (9) | |
C2 | 0.5949 (3) | 0.5557 (2) | 0.58826 (17) | 0.0543 (9) | |
H2 | 0.6514 | 0.5782 | 0.5477 | 0.065* | |
C3 | 0.4732 (3) | 0.6023 (2) | 0.59198 (17) | 0.0487 (8) | |
C4 | 0.3648 (3) | 0.5779 (3) | 0.65281 (18) | 0.0574 (9) | |
H4 | 0.4073 | 0.5331 | 0.6932 | 0.069* | |
C5 | 0.2491 (3) | 0.5130 (3) | 0.6172 (2) | 0.0769 (12) | |
H5A | 0.2122 | 0.5511 | 0.5731 | 0.115* | |
H5B | 0.1789 | 0.5026 | 0.6557 | 0.115* | |
H5C | 0.2830 | 0.4444 | 0.6002 | 0.115* | |
C6 | 0.3103 (4) | 0.6779 (3) | 0.6930 (2) | 0.0887 (13) | |
H6A | 0.3847 | 0.7176 | 0.7153 | 0.133* | |
H6B | 0.2479 | 0.6573 | 0.7337 | 0.133* | |
H6C | 0.2637 | 0.7219 | 0.6553 | 0.133* | |
C7 | 0.5116 (3) | 0.7396 (3) | 0.48738 (18) | 0.0523 (9) | |
C8 | 0.4351 (3) | 0.8151 (3) | 0.4358 (2) | 0.0782 (12) | |
H8A | 0.4556 | 0.8879 | 0.4505 | 0.117* | |
H8B | 0.3390 | 0.8025 | 0.4412 | 0.117* | |
H8C | 0.4615 | 0.8037 | 0.3822 | 0.117* | |
C9 | 0.8506 (4) | 0.3734 (3) | 0.6671 (2) | 0.0751 (12) | |
H9A | 0.8407 | 0.3897 | 0.7218 | 0.113* | |
H9B | 0.9455 | 0.3739 | 0.6534 | 0.113* | |
H9C | 0.8130 | 0.3036 | 0.6566 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.088 (2) | 0.115 (2) | 0.093 (2) | 0.0283 (16) | 0.0236 (16) | 0.0547 (18) |
O2 | 0.0538 (15) | 0.0714 (17) | 0.0832 (17) | 0.0097 (12) | −0.0024 (12) | 0.0256 (13) |
O3 | 0.0457 (15) | 0.0780 (18) | 0.0686 (16) | 0.0003 (12) | 0.0031 (10) | 0.0238 (12) |
N1 | 0.0388 (14) | 0.0616 (18) | 0.0608 (17) | 0.0021 (13) | 0.0032 (12) | 0.0173 (14) |
C1 | 0.052 (2) | 0.058 (2) | 0.057 (2) | 0.0023 (17) | −0.0023 (15) | 0.0062 (18) |
C2 | 0.055 (2) | 0.055 (2) | 0.053 (2) | 0.0014 (17) | 0.0041 (14) | 0.0097 (17) |
C3 | 0.0517 (19) | 0.052 (2) | 0.0428 (18) | −0.0036 (16) | 0.0002 (13) | 0.0051 (15) |
C4 | 0.058 (2) | 0.063 (2) | 0.051 (2) | 0.0009 (18) | 0.0082 (15) | 0.0157 (17) |
C5 | 0.069 (2) | 0.078 (3) | 0.083 (3) | −0.016 (2) | 0.0214 (19) | 0.004 (2) |
C6 | 0.114 (3) | 0.090 (3) | 0.062 (3) | 0.000 (3) | 0.024 (2) | −0.010 (2) |
C7 | 0.046 (2) | 0.060 (2) | 0.051 (2) | −0.0016 (18) | 0.0011 (14) | 0.0089 (16) |
C8 | 0.057 (2) | 0.089 (3) | 0.088 (3) | 0.002 (2) | 0.0022 (18) | 0.042 (2) |
C9 | 0.068 (2) | 0.078 (3) | 0.080 (3) | 0.017 (2) | −0.0131 (19) | 0.009 (2) |
O1—C1 | 1.209 (4) | C5—H5A | 0.9600 |
O2—C1 | 1.333 (4) | C5—H5B | 0.9600 |
O2—C9 | 1.437 (4) | C5—H5C | 0.9600 |
O3—C7 | 1.216 (3) | C6—H6A | 0.9600 |
N1—C7 | 1.368 (4) | C6—H6B | 0.9600 |
N1—C3 | 1.410 (4) | C6—H6C | 0.9600 |
N1—H1 | 0.8600 | C7—C8 | 1.491 (4) |
C1—C2 | 1.449 (4) | C8—H8A | 0.9600 |
C2—C3 | 1.328 (4) | C8—H8B | 0.9600 |
C2—H2 | 0.9300 | C8—H8C | 0.9600 |
C3—C4 | 1.516 (4) | C9—H9A | 0.9600 |
C4—C6 | 1.517 (5) | C9—H9B | 0.9600 |
C4—C5 | 1.520 (4) | C9—H9C | 0.9600 |
C4—H4 | 0.9800 | ||
C1—O2—C9 | 118.0 (3) | H5A—C5—H5C | 109.5 |
C7—N1—C3 | 128.2 (3) | H5B—C5—H5C | 109.5 |
C7—N1—H1 | 115.9 | C4—C6—H6A | 109.5 |
C3—N1—H1 | 115.9 | C4—C6—H6B | 109.5 |
O1—C1—O2 | 121.0 (3) | H6A—C6—H6B | 109.5 |
O1—C1—C2 | 128.4 (3) | C4—C6—H6C | 109.5 |
O2—C1—C2 | 110.6 (3) | H6A—C6—H6C | 109.5 |
C3—C2—C1 | 127.8 (3) | H6B—C6—H6C | 109.5 |
C3—C2—H2 | 116.1 | O3—C7—N1 | 123.8 (3) |
C1—C2—H2 | 116.1 | O3—C7—C8 | 121.5 (3) |
C2—C3—N1 | 122.0 (3) | N1—C7—C8 | 114.7 (3) |
C2—C3—C4 | 125.1 (3) | C7—C8—H8A | 109.5 |
N1—C3—C4 | 112.9 (3) | C7—C8—H8B | 109.5 |
C3—C4—C6 | 113.1 (3) | H8A—C8—H8B | 109.5 |
C3—C4—C5 | 110.8 (3) | C7—C8—H8C | 109.5 |
C6—C4—C5 | 110.6 (3) | H8A—C8—H8C | 109.5 |
C3—C4—H4 | 107.3 | H8B—C8—H8C | 109.5 |
C6—C4—H4 | 107.3 | O2—C9—H9A | 109.5 |
C5—C4—H4 | 107.3 | O2—C9—H9B | 109.5 |
C4—C5—H5A | 109.5 | H9A—C9—H9B | 109.5 |
C4—C5—H5B | 109.5 | O2—C9—H9C | 109.5 |
H5A—C5—H5B | 109.5 | H9A—C9—H9C | 109.5 |
C4—C5—H5C | 109.5 | H9B—C9—H9C | 109.5 |
C9—O2—C1—O1 | −1.6 (5) | C7—N1—C3—C4 | 163.4 (3) |
C9—O2—C1—C2 | 179.7 (3) | C2—C3—C4—C6 | 128.7 (3) |
O1—C1—C2—C3 | 6.4 (6) | N1—C3—C4—C6 | −51.7 (4) |
O2—C1—C2—C3 | −175.0 (3) | C2—C3—C4—C5 | −106.4 (4) |
C1—C2—C3—N1 | −179.7 (3) | N1—C3—C4—C5 | 73.2 (3) |
C1—C2—C3—C4 | −0.1 (5) | C3—N1—C7—O3 | −2.1 (5) |
C7—N1—C3—C2 | −17.0 (5) | C3—N1—C7—C8 | 178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.28 | 3.124 (3) | 166 |
Symmetry code: (i) x−1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C9H15NO3 |
Mr | 185.22 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 294 |
a, b, c (Å) | 9.806 (2), 12.435 (3), 17.067 (4) |
V (Å3) | 2081.1 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.28 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.976, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13157, 2384, 888 |
Rint | 0.116 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.198, 1.02 |
No. of reflections | 2384 |
No. of parameters | 123 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.32 |
Computer programs: SMART (Siemens, 1995), SMART, SHELXTL (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
O1—C1 | 1.209 (4) | N1—C7 | 1.368 (4) |
O2—C1 | 1.333 (4) | N1—C3 | 1.410 (4) |
O2—C9 | 1.437 (4) | C1—C2 | 1.449 (4) |
O3—C7 | 1.216 (3) | C4—C6 | 1.517 (5) |
C1—O2—C9 | 118.0 (3) | O1—C1—O2 | 121.0 (3) |
C7—N1—C3 | 128.2 (3) | O1—C1—C2 | 128.4 (3) |
C9—O2—C1—O1 | −1.6 (5) | C7—N1—C3—C4 | 163.4 (3) |
C9—O2—C1—C2 | 179.7 (3) | N1—C3—C4—C5 | 73.2 (3) |
C1—C2—C3—N1 | −179.7 (3) | C3—N1—C7—C8 | 178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.28 | 3.124 (3) | 166 |
Symmetry code: (i) x−1/2, −y+3/2, −z+1. |
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The title compound, (I), is one of the prochiral olefin widely investigated in the asymmetric hydrogenation reaction (Hackler et al., 1985; Lubell et al., 1991) for producing β-amino acids and their derivatives. The enantiomeric excess of the hydrogenation product is significantly influenced by the structure of the substrate. The structure determination of (I) was conducted in order to obtain more stereochemical information about β-amino acids and their derivatives.
In the structure of (I) (Fig. 1), the bond lengths and angles are in the expected ranges (Table 1). As shown in the packing diagram (Fig. 2), the crystal structure contains intermolecular hydrogen bonds, and infinite molecular chains stretch along the a axis.