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The structure of the title compound, C8H13NO3, refined in space group Pna21, which was chosen over Pnam as the space group because of the lack of mirror or inversion symmetry. An N—H...O intermolecular hydrogen bond is observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005609/ac6031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005609/ac6031Isup2.hkl
Contains datablock I

CCDC reference: 209984

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.087
  • Data-to-parameter ratio = 18.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -0.500 From the CIF: _refine_ls_abs_structure_Flack_su 1.600 Alert C Flack parameter is too small General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.55 From the CIF: _reflns_number_total 2037 Count of symmetry unique reflns 1134 Completeness (_total/calc) 179.63% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 903 Fraction of Friedel pairs measured 0.796 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), is one of the by-products obtained during the synthesis of methyl 3-acetamido-2-pentenoate from the reaction of methyl 3-aminopent-2-enoate reflux with acetic anhydride in THF for 24 h (Hackler et al., 1985; Lubell et al., 1991; Yasutake et al., 2001). The structure determination of (I) was conducted in order to obtain more sterochemical imformation.

In the crystal structure of (I) (Fig. 1), the N1—C1—C2—C5, C1—C2—C5—O3 and C1—C2—C5—C6 torsion angles are −2.0 (4), −1.1 (4) and 179.4 (3)°, respectively. This show that atoms N1/C1/C2/C5/O3 are almost in the same plane and the C1C2 and C5O3 double bond form a conjugated system (Table 1). The molecules in the crystal structure are interconnected by N—H···O hydrogen bonding (Table 2). As shown in the packing diagram (Fig. 2), the hydrogen bond links the molecules along the c axis.

Experimental top

The title compound, (I), was synthesized according the literature (Zhu et al., 1999). A crystal suitable for X-ray analysis was grown slowly from mixed solution in ethyl acetate and hexane (1:5) at room temperature.

Refinement top

H atoms were included in the riding-model approximation, with Uiso values equal to Ueq of the atom to which they were bound.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level (Siemens, 1995).
[Figure 2] Fig. 2. Packing diagram for (I). The hydrogen bonds are indicated by dashed lines.
(I) top
Crystal data top
C8H13NO3Dx = 1.238 Mg m3
Mr = 171.19Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 1585 reflections
a = 23.998 (7) Åθ = 1–27.5°
b = 4.2785 (13) ŵ = 0.10 mm1
c = 8.944 (3) ÅT = 294 K
V = 918.3 (5) Å3Needle, colorless
Z = 40.50 × 0.40 × 0.38 mm
F(000) = 368
Data collection top
Siemens SMART CCD area-detector
diffractometer
2037 independent reflections
Radiation source: fine-focus sealed tube903 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ and ω scansθmax = 27.6°, θmin = 3.4°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 2731
Tmin = 0.954, Tmax = 0.965k = 55
5793 measured reflectionsl = 1110
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.015P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.15 e Å3
2037 reflectionsΔρmin = 0.14 e Å3
113 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0098 (18)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.5 (16)
Crystal data top
C8H13NO3V = 918.3 (5) Å3
Mr = 171.19Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 23.998 (7) ŵ = 0.10 mm1
b = 4.2785 (13) ÅT = 294 K
c = 8.944 (3) Å0.50 × 0.40 × 0.38 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2037 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
903 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.965Rint = 0.069
5793 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.088Δρmax = 0.15 e Å3
S = 1.03Δρmin = 0.14 e Å3
2037 reflectionsAbsolute structure: Flack (1983)
113 parametersAbsolute structure parameter: 0.5 (16)
1 restraint
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
O10.44379 (8)0.1383 (5)0.2634 (2)0.0754 (8)
O20.45293 (7)0.3468 (6)0.4878 (2)0.0698 (7)
O30.29467 (8)0.0214 (6)0.5840 (2)0.0787 (8)
N10.27088 (9)0.2708 (7)0.3271 (3)0.0679 (8)
H1A0.25780.18050.40550.081*
H1B0.24850.33910.25940.081*
C10.32485 (12)0.3042 (7)0.3106 (3)0.0447 (7)
C20.36303 (12)0.1983 (7)0.4164 (3)0.0405 (7)
C30.42254 (11)0.2214 (8)0.3776 (4)0.0489 (8)
C40.51181 (11)0.3632 (9)0.4619 (5)0.0940 (13)
H4A0.52810.16110.47810.141*
H4B0.52820.51140.52950.141*
H4C0.51860.42800.36080.141*
C50.34507 (13)0.0534 (7)0.5535 (3)0.0519 (8)
C60.38585 (12)0.0638 (7)0.6674 (4)0.0655 (9)
H6A0.40120.11000.72130.098*
H6B0.41530.17530.61790.098*
H6C0.36720.20110.73590.098*
C70.34162 (11)0.4897 (8)0.1762 (3)0.0498 (7)
H7A0.37840.57690.19280.060*
H7B0.31580.66240.16360.060*
C80.34246 (13)0.2961 (8)0.0336 (3)0.0672 (10)
H8A0.36990.13400.04240.101*
H8B0.35150.42820.04970.101*
H8C0.30650.20400.01800.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0569 (13)0.118 (2)0.0511 (15)0.0050 (12)0.0160 (13)0.0220 (15)
O20.0460 (12)0.105 (2)0.0586 (16)0.0033 (12)0.0041 (13)0.0246 (14)
O30.0556 (13)0.126 (2)0.0547 (15)0.0022 (15)0.0120 (11)0.0308 (15)
N10.0440 (15)0.114 (2)0.0456 (19)0.0007 (16)0.0024 (13)0.0214 (18)
C10.0500 (18)0.052 (2)0.0325 (17)0.0022 (15)0.0016 (15)0.0011 (17)
C20.0437 (16)0.050 (2)0.0279 (16)0.0013 (14)0.0019 (14)0.0012 (17)
C30.0469 (17)0.058 (2)0.0413 (19)0.0021 (18)0.0046 (18)0.0036 (16)
C40.045 (2)0.136 (4)0.101 (3)0.007 (2)0.0074 (19)0.027 (3)
C50.0592 (19)0.058 (2)0.039 (2)0.0067 (17)0.0050 (16)0.0019 (18)
C60.078 (2)0.077 (2)0.0412 (18)0.0095 (19)0.0014 (18)0.013 (2)
C70.0565 (17)0.0484 (17)0.045 (2)0.0012 (15)0.0023 (16)0.0079 (19)
C80.091 (2)0.070 (2)0.040 (2)0.001 (2)0.0037 (17)0.0063 (18)
Geometric parameters (Å, º) top
O1—C31.196 (4)C4—H4B0.9600
O2—C31.339 (3)C4—H4C0.9600
O2—C41.433 (3)C5—C61.499 (4)
O3—C51.247 (3)C6—H6A0.9600
N1—C11.311 (3)C6—H6B0.9600
N1—H1A0.8600C6—H6C0.9600
N1—H1B0.8600C7—C81.521 (4)
C1—C21.393 (4)C7—H7A0.9700
C1—C71.496 (4)C7—H7B0.9700
C2—C51.440 (4)C8—H8A0.9600
C2—C31.473 (3)C8—H8B0.9600
C4—H4A0.9600C8—H8C0.9600
C3—O2—C4115.9 (3)O3—C5—C6116.6 (3)
C1—N1—H1A120.0C2—C5—C6121.8 (3)
C1—N1—H1B120.0C5—C6—H6A109.5
H1A—N1—H1B120.0C5—C6—H6B109.5
N1—C1—C2122.5 (3)H6A—C6—H6B109.5
N1—C1—C7114.4 (3)C5—C6—H6C109.5
C2—C1—C7122.8 (2)H6A—C6—H6C109.5
C1—C2—C5121.4 (3)H6B—C6—H6C109.5
C1—C2—C3117.1 (2)C1—C7—C8112.9 (2)
C5—C2—C3121.3 (3)C1—C7—H7A109.0
O1—C3—O2121.1 (3)C8—C7—H7A109.0
O1—C3—C2126.5 (3)C1—C7—H7B109.0
O2—C3—C2112.4 (3)C8—C7—H7B109.0
O2—C4—H4A109.5H7A—C7—H7B107.8
O2—C4—H4B109.5C7—C8—H8A109.5
H4A—C4—H4B109.5C7—C8—H8B109.5
O2—C4—H4C109.5H8A—C8—H8B109.5
H4A—C4—H4C109.5C7—C8—H8C109.5
H4B—C4—H4C109.5H8A—C8—H8C109.5
O3—C5—C2121.6 (3)H8B—C8—H8C109.5
N1—C1—C2—C52.0 (4)C1—C2—C3—O2132.4 (3)
C7—C1—C2—C5172.4 (3)C5—C2—C3—O251.7 (4)
N1—C1—C2—C3173.9 (3)C1—C2—C5—O31.1 (4)
C7—C1—C2—C311.7 (4)C3—C2—C5—O3176.9 (3)
C4—O2—C3—O12.2 (5)C1—C2—C5—C6179.4 (3)
C4—O2—C3—C2177.0 (3)C3—C2—C5—C63.7 (5)
C1—C2—C3—O148.5 (5)N1—C1—C7—C882.2 (3)
C5—C2—C3—O1127.5 (4)C2—C1—C7—C8102.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.861.952.597 (3)131
N1—H1B···O3i0.862.042.890 (3)172
Symmetry code: (i) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC8H13NO3
Mr171.19
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)294
a, b, c (Å)23.998 (7), 4.2785 (13), 8.944 (3)
V3)918.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.40 × 0.38
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.954, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
5793, 2037, 903
Rint0.069
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.088, 1.03
No. of reflections2037
No. of parameters113
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.14
Absolute structureFlack (1983)
Absolute structure parameter0.5 (16)

Computer programs: SMART (Siemens, 1995), SMART, SHELXTL (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C31.196 (4)C1—C21.393 (4)
O2—C31.339 (3)C2—C51.440 (4)
O3—C51.247 (3)C5—C61.499 (4)
N1—C11.311 (3)C7—C81.521 (4)
N1—C1—C2122.5 (3)C1—C2—C5121.4 (3)
N1—C1—C7114.4 (3)C1—C2—C3117.1 (2)
N1—C1—C2—C52.0 (4)C7—C1—C2—C311.7 (4)
C7—C1—C2—C5172.4 (3)C1—C2—C5—O31.1 (4)
N1—C1—C2—C3173.9 (3)C1—C2—C5—C6179.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.861.952.597 (3)131
N1—H1B···O3i0.862.042.890 (3)172
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

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