5 Ethyl L glutamate

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organic papers

o4028

Wuet al. _C

7H13NO4 doi:10.1107/S1600536805035919 Acta Cryst.(2005). E61, o4028–o4029

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

5-Ethyl

L

-glutamate

Yong-Fei Wu,aFeng-Ping Xiao,a Long-Fei Jin,a* Fen-Fang Liaand Xu-Ya Daib

a_{College of Chemistry, Central China Normal} Univesity, Wuhan 430079, People’s Republic of China, andb_{Department of Chemistry, Central} China Normal University, Wuhan, Hubei 430079, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 273 K

Mean(C–C) = 0.008 A˚ Rfactor = 0.060 wRfactor = 0.178 Data-to-parameter ratio = 8.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In the title compound, C7H13NO4, there are two independent

molecules in the asymmetric unit. All bond lengths and angles in the molecules are in normal ranges. The 1and 2torsion angles are 159.9 (4) and 23.4 (5)_{, respectively, in the first}

molecule, and the 3 and 4 torsion angles 157.7 (4) and 26.7 (5)_{, respectively, in the second. Each of the}

indepen-dent molecules has a different comformation. The transla-tionally and screw-related molecules are connected by N— H O hydrogen bonds, forming a two-dimensional network parallel to theacplane.

Comment

It has been reported that many esters of amino acids display a broad range of biological activities, e.g. as anti-oxidants, bactericides, food additives and cosmetics (Wang & Li, 1995); furthermore, these esters are useful ligands. As part of an ongoing study (Wu et al., 2005), we report here the crystal structure of the title compound, (I).

In the crystal structure, (I) exists as a zwitterion (Fig. 1). All bond lengths and angles in the two independent molecules of (I) (Fig. 1) are normal. The N1—C2—C1—O1 ( 1_{), N1—C2—}

C1—O2 ( 2), N2—C9—C8—O5 ( 3) and N2—C9—C8—O6 ( 4) torsion angles are 159.9 (4), 23.4 (5), 157.7 (4) and 26.7 (5)_{, respectively. In one independent molecule, atom}

[image:1.610.265.400.393.455.2] [image:1.610.209.459.569.723.2]

Received 31 October 2005 Accepted 2 November 2005 Online 10 November 2005

Figure 1

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Cis intermediate betweentransandgaucheto N [N1—C2— C3—C4 (1

) =159.8 (4)_{], while atom C}

istransto C[C2— C3—C4—C5 (2

) = 170.5 (4)_{]. In the second molecule, atom}

Cisgaucheto N [N2—C9—C10—C11 (3

) =57.3 (5)_{] and}

atom C is trans to C [C9—C10—C11—C12 (4

) = 175.8 (5)_{]. The C—O lengths of the ionized carboxylate}

group are almost equal (Table 1). In l-glutamic acid

(Lehmann & Nunes, 1980), the 1and 2torsion angles are 35 and 145_{(no s.u. values available), and the bond lengths}

and angles are similar to those in the title compound. In the crystal structure, translationally and screw-related molecules are connected by N—H O hydrogen bonds to form a two-dimensional network parallel to the ac plane (Table 2 and Fig. 2).

Experimental

Compound (I) was synthesized according to the literature procedure of Li & Wang (1999). Colourless plate-like crystals were grown by slow evaporation of an aqueous solution at room temperature.

Crystal data

C7H13NO4 Mr= 175.18 Monoclinic,P2₁ a= 9.691 (3) A˚ b= 5.2631 (17) A˚ c= 17.297 (6) A˚

= 90.752 (5)

V= 882.2 (5) A˚3 Z= 4

Dx= 1.319 Mg m

3 MoKradiation Cell parameters from 1376

reflections

= 3.1–21.6 = 0.11 mm1 T= 273 (2) K Plate, colourless 0.500.490.02 mm

Data collection

Bruker SMART-APEX CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin= 0.948,Tmax= 0.998 5098 measured reflections

1927 independent reflections 1546 reflections withI> 2(I) Rint= 0.027

max= 26.0

h=8!11 k=6!5 l=21!20

Refinement

Refinement onF2 R[F2> 2(F2)] = 0.060 wR(F2_{) = 0.178} S= 1.04 1927 reflections 221 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0984P)2 + 0.2865P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.50 e A˚

3 min=0.24 e A˚

[image:2.610.316.566.72.241.2]

3

Table 1

Selected geometric parameters (A˚ ,_).

C1—O1 1.243 (5)

C1—O2 1.258 (5)

C8—O5 1.244 (6)

C8—O6 1.257 (5)

O1—C1—C2—N1 159.9 (4)

O2—C1—C2—N1 23.4 (5)

N1—C2—C3—C4 159.6 (4)

C2—C3—C4—C5 170.8 (4)

O5—C8—C9—N2 157.7 (4)

O6—C8—C9—N2 26.7 (5)

N2—C9—C10—C11 57.5 (5)

[image:2.610.313.567.303.384.2]

C9—C10—C11—C12 175.5 (5)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N2—H2A O5i

0.89 1.96 2.840 (5) 170

N2—H2B O2ii

0.89 1.99 2.828 (4) 157

N2—H2C O2iii

0.89 1.93 2.807 (4) 170

N1—H1A O1i 0.89 1.98 2.813 (5) 155

N1—H1B O6i

0.89 1.88 2.741 (4) 161

N1—H1C O6iv

0.89 2.18 2.950 (4) 144

N1—H1C O5iv 0.89 2.35 3.178 (4) 154

Symmetry codes: (i) x;y1;z; (ii) x;yþ1;z; (iii) xþ2;yþ1

2;zþ1; (iv)

xþ1;y3 2;zþ1.

All H atoms were placed in calculated positions, with N—H distances of 0.89 A˚ and C—H distances of 0.96 (CH3), 0.97 (CH2) and

0.98 A˚ (CH). They were included in the refinement in the riding-model approximation, with isotropic displacement parameters set to 1.2Ueqof the carrier atom (1.5Ueqfor CH3and NH3H atoms). In the

absence of significant anomalous scattering, Friedel pairs were merged prior to the final refinement; the absolute configuration is known from the synthesis (Carey & Sundberg, 1984).

Data collection:APEX(Bruker, 2001); cell refinement: SAINT-Plus(Bruker, 2001); data reduction:SAINT-Plus; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:

SHELXTL-NT(Bruker, 2001); software used to prepare material for publication:SHELXTL-NT.

References

Bruker (2001). APEX (Version 5.628), SAINT-Plus (Version 6.45) and SHELXTL-NT(Version 6.12). Bruker AXS Inc., Madison, Wisconsin,USA. Carey, F. A. & Sundberg, R. J. (1984).Advanced Organic Chemistry, pp. 64–66.

New York, London: Plenum Press.

Lehmann, M. S. & Nunes, A. C. (1980).Acta Cryst.B36, 1621–1625. Li, W.-M. & Wang, X.-M. (1999).Adv. Sci. Tech.9, 16–19.

Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

Go¨ttingen, Germany.

Wang, B.-Q. & Li, Z.-C. (1995).Amino Acids Biotic Resources,17, 40-45. Wu, Y.-F., Li, F.-F. & Jin, L.-F. (2005).Acta Cryst.E61, o3752–o3753.

Figure 2

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supporting information

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Acta Cryst. (2005). E61, o4028–o4029

supporting information

Acta Cryst. (2005). E61, o4028–o4029 [https://doi.org/10.1107/S1600536805035919]

5-Ethyl

L

-glutamate

Yong-Fei Wu, Feng-Ping Xiao, Long-Fei Jin, Fen-Fang Li and Xu-Ya Dai

5-Ethyl L-glutamate

Crystal data

C7H13NO4

Mr = 175.18 Monoclinic, P21

Hall symbol: P 2yb

a = 9.691 (3) Å

b = 5.2631 (17) Å

c = 17.297 (6) Å

β = 90.752 (5)°

V = 882.2 (5) Å3

Z = 4

F(000) = 376

Dx = 1.319 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1376 reflections

θ = 3.1–21.6°

µ = 0.11 mm−1

T = 273 K Plate, colorless 0.50 × 0.49 × 0.02 mm

Data collection

Bruker SMART-APEX CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996)

Tmin = 0.948, Tmax = 0.998

5098 measured reflections 1927 independent reflections 1546 reflections with I > 2σ(I)

Rint = 0.027

θmax = 26.0°, θmin = 2.4°

h = −8→11

k = −6→5

l = −21→20

Refinement

Refinement on F2

Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.060}

wR(F2_{) = 0.178}

S = 1.04 1927 reflections 221 parameters 2 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2₍_F

o2) + (0.0984P)2 + 0.2865P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.50 e Å−3

Δρmin = −0.24 e Å−3

Special details

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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₎

x y z Uiso*/Ueq

C1 0.7724 (4) −0.0270 (8) 0.5897 (2) 0.0336 (9) C2 0.6316 (4) −0.1298 (8) 0.6153 (2) 0.0355 (9)

H2 0.5601 −0.0151 0.5951 0.043*

C3 0.6165 (5) −0.1438 (10) 0.7029 (3) 0.0539 (12)

H3A 0.7005 −0.2124 0.7258 0.065*

H3B 0.5411 −0.2571 0.7154 0.065*

C4 0.5885 (6) 0.1205 (12) 0.7366 (3) 0.0652 (14)

H4A 0.6702 0.2248 0.7308 0.078*

H4B 0.5141 0.1996 0.7073 0.078*

C5 0.5520 (6) 0.1137 (13) 0.8168 (4) 0.0680 (15) C6 0.4263 (7) 0.3222 (14) 0.9150 (3) 0.088 (2)

H6A 0.5059 0.3626 0.9473 0.106*

H6B 0.3865 0.1646 0.9333 0.106*

C7 0.3237 (7) 0.5285 (15) 0.9193 (5) 0.114 (3)

H7A 0.2434 0.4833 0.8892 0.171*

H7B 0.3627 0.6823 0.8992 0.171*

H7C 0.2981 0.5540 0.9721 0.171*

C8 0.7212 (4) 0.8910 (8) 0.3978 (2) 0.0354 (9) C9 0.8542 (4) 0.7526 (8) 0.3775 (2) 0.0372 (9)

H9 0.9323 0.8696 0.3836 0.045*

C10 0.8450 (4) 0.6629 (10) 0.2931 (2) 0.0487 (11)

H10A 0.7639 0.5565 0.2867 0.058*

H10B 0.8333 0.8099 0.2598 0.058*

C11 0.9692 (5) 0.5170 (13) 0.2678 (3) 0.0631 (15)

H11A 0.9766 0.3629 0.2984 0.076*

H11B 1.0510 0.6182 0.2781 0.076*

C12 0.9650 (5) 0.4466 (13) 0.1833 (3) 0.0615 (14) C13 1.0697 (6) 0.1975 (16) 0.0882 (3) 0.0791 (19)

H13A 1.0952 0.3434 0.0572 0.095*

H13B 0.9827 0.1315 0.0684 0.095*

C14 1.1764 (7) 0.0022 (17) 0.0839 (4) 0.095 (2)

H14A 1.1447 −0.1498 0.1087 0.143*

H14B 1.2588 0.0615 0.1096 0.143*

H14C 1.1959 −0.0333 0.0307 0.143*

N1 0.6080 (3) −0.3841 (7) 0.5805 (2) 0.0414 (9)

H1A 0.6709 −0.4926 0.5988 0.062*

H1B 0.6149 −0.3736 0.5293 0.062*

H1C 0.5240 −0.4388 0.5925 0.062*

N2 0.8749 (3) 0.5308 (7) 0.43012 (19) 0.0352 (8)

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Acta Cryst. (2005). E61, o4028–o4029

H2B 0.8605 0.5786 0.4787 0.053*

H2C 0.9609 0.4734 0.4258 0.053*

O1 0.7927 (3) 0.2056 (6) 0.5943 (2) 0.0522 (9) O2 0.8608 (2) −0.1875 (6) 0.56902 (16) 0.0397 (7) O3 0.5922 (6) −0.0364 (12) 0.8655 (3) 0.113 (2) O4 0.4675 (4) 0.2946 (10) 0.8362 (2) 0.0795 (13) O5 0.7104 (3) 1.1172 (6) 0.3778 (2) 0.0554 (9) O6 0.6278 (2) 0.7623 (6) 0.42901 (17) 0.0426 (8) O7 0.8926 (5) 0.5428 (12) 0.1356 (2) 0.112 (2) O8 1.0561 (4) 0.2709 (9) 0.16801 (19) 0.0755 (13)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

C1 0.0214 (16) 0.037 (2) 0.042 (2) −0.0026 (17) 0.0025 (14) 0.0027 (18) C2 0.0216 (16) 0.032 (2) 0.053 (2) 0.0031 (16) 0.0046 (15) 0.0030 (19) C3 0.060 (3) 0.048 (3) 0.054 (3) −0.006 (2) 0.012 (2) 0.004 (2) C4 0.074 (3) 0.060 (3) 0.062 (3) 0.001 (3) 0.006 (3) 0.001 (3) C5 0.061 (3) 0.058 (3) 0.085 (4) 0.009 (3) 0.011 (3) −0.007 (3) C6 0.089 (4) 0.095 (5) 0.083 (4) 0.002 (4) 0.026 (3) −0.019 (4) C7 0.099 (5) 0.114 (7) 0.130 (6) −0.011 (5) 0.047 (5) −0.044 (6) C8 0.0260 (18) 0.033 (2) 0.047 (2) 0.0059 (17) −0.0028 (16) −0.0060 (18) C9 0.0238 (17) 0.037 (2) 0.051 (2) 0.0047 (17) 0.0038 (16) −0.0004 (19) C10 0.037 (2) 0.059 (3) 0.049 (2) 0.013 (2) 0.0036 (17) −0.003 (2) C11 0.055 (3) 0.082 (4) 0.053 (3) 0.023 (3) 0.002 (2) −0.011 (3) C12 0.051 (3) 0.082 (4) 0.052 (3) 0.016 (3) 0.006 (2) −0.005 (3) C13 0.073 (4) 0.108 (5) 0.056 (3) 0.013 (4) 0.007 (3) −0.019 (4) C14 0.079 (4) 0.100 (5) 0.107 (5) 0.004 (4) 0.023 (4) −0.041 (5) N1 0.0219 (15) 0.046 (2) 0.057 (2) −0.0117 (16) 0.0005 (14) 0.0060 (18) N2 0.0219 (14) 0.0352 (18) 0.0486 (18) 0.0067 (13) 0.0026 (13) −0.0040 (15) O1 0.0417 (17) 0.0298 (17) 0.085 (2) −0.0054 (13) 0.0095 (15) −0.0027 (16) O2 0.0211 (12) 0.0390 (16) 0.0593 (17) −0.0041 (12) 0.0058 (11) −0.0111 (14) O3 0.159 (5) 0.109 (4) 0.072 (3) 0.063 (4) 0.019 (3) 0.016 (3) O4 0.079 (3) 0.097 (3) 0.062 (2) 0.029 (3) 0.0120 (19) −0.009 (2) O5 0.0422 (17) 0.0332 (18) 0.091 (2) 0.0096 (14) −0.0055 (16) 0.0040 (16) O6 0.0211 (12) 0.0472 (18) 0.0595 (17) 0.0039 (13) 0.0045 (12) −0.0009 (15) O7 0.122 (4) 0.155 (6) 0.060 (2) 0.080 (4) −0.018 (2) −0.018 (3) O8 0.068 (2) 0.103 (4) 0.056 (2) 0.033 (3) 0.0055 (17) −0.013 (2)

Geometric parameters (Å, º)

C1—O1 1.243 (5) C9—N2 1.492 (5)

C1—O2 1.258 (5) C9—C10 1.537 (6)

C1—C2 1.538 (5) C9—H9 0.9800

C2—N1 1.484 (6) C10—C11 1.498 (6)

C2—C3 1.526 (6) C10—H10A 0.9700

C2—H2 0.9800 C10—H10B 0.9700

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C3—H3A 0.9700 C11—H11A 0.9700

C3—H3B 0.9700 C11—H11B 0.9700

C4—C5 1.437 (8) C12—O7 1.190 (6)

C4—H4A 0.9700 C12—O8 1.308 (7)

C4—H4B 0.9700 C13—O8 1.442 (6)

C5—O3 1.215 (8) C13—C14 1.461 (10)

C5—O4 1.303 (7) C13—H13A 0.9700

C6—O4 1.432 (6) C13—H13B 0.9700

C6—C7 1.475 (5) C14—H14A 0.9600

C6—H6A 0.9700 C14—H14B 0.9600

C6—H6B 0.9700 C14—H14C 0.9600

C7—H7A 0.9600 N1—H1A 0.8900

C7—H7B 0.9600 N1—H1B 0.8900

C7—H7C 0.9600 N1—H1C 0.8900

C8—O5 1.244 (6) N2—H2A 0.8900

C8—O6 1.257 (5) N2—H2B 0.8900

C8—C9 1.526 (5) N2—H2C 0.8900

O1—C1—O2 124.9 (4) C8—C9—H9 109.2

O1—C1—C2 117.9 (4) C10—C9—H9 109.2

O2—C1—C2 117.1 (4) C11—C10—C9 113.4 (4)

N1—C2—C3 110.0 (3) C11—C10—H10A 108.9

N1—C2—C1 109.5 (3) C9—C10—H10A 108.9

C3—C2—C1 113.6 (3) C11—C10—H10B 108.9

N1—C2—H2 107.9 C9—C10—H10B 108.9

C3—C2—H2 107.9 H10A—C10—H10B 107.7

C1—C2—H2 107.9 C10—C11—C12 113.4 (4)

C2—C3—C4 110.7 (4) C10—C11—H11A 108.9

C2—C3—H3A 109.5 C12—C11—H11A 108.9

C4—C3—H3A 109.5 C10—C11—H11B 108.9

C2—C3—H3B 109.5 C12—C11—H11B 108.9

C4—C3—H3B 109.5 H11A—C11—H11B 107.7

H3A—C3—H3B 108.1 O7—C12—O8 123.6 (5)

C5—C4—C3 113.1 (5) O7—C12—C11 125.2 (5)

C5—C4—H4A 109.0 O8—C12—C11 111.2 (4)

C3—C4—H4A 109.0 O8—C13—C14 108.1 (5)

C5—C4—H4B 109.0 O8—C13—H13A 110.1

C3—C4—H4B 109.0 C14—C13—H13A 110.1

H4A—C4—H4B 107.8 O8—C13—H13B 110.1

O3—C5—O4 119.6 (6) C14—C13—H13B 110.1

O3—C5—C4 127.2 (6) H13A—C13—H13B 108.4

O4—C5—C4 113.2 (6) C13—C14—H14A 109.5

O4—C6—C7 108.6 (6) C13—C14—H14B 109.5

O4—C6—H6A 110.0 H14A—C14—H14B 109.5

C7—C6—H6A 110.0 C13—C14—H14C 109.5

O4—C6—H6B 110.0 H14A—C14—H14C 109.5

C7—C6—H6B 110.0 H14B—C14—H14C 109.5

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Acta Cryst. (2005). E61, o4028–o4029

C6—C7—H7A 109.5 C2—N1—H1B 109.5

C6—C7—H7B 109.5 H1A—N1—H1B 109.5

H7A—C7—H7B 109.5 C2—N1—H1C 109.5

C6—C7—H7C 109.5 H1A—N1—H1C 109.5

H7A—C7—H7C 109.5 H1B—N1—H1C 109.5

H7B—C7—H7C 109.5 C9—N2—H2A 109.5

O5—C8—O6 125.3 (4) C9—N2—H2B 109.5

O5—C8—C9 117.4 (4) H2A—N2—H2B 109.5

O6—C8—C9 117.2 (4) C9—N2—H2C 109.5

N2—C9—C8 109.9 (3) H2A—N2—H2C 109.5

N2—C9—C10 110.2 (3) H2B—N2—H2C 109.5

C8—C9—C10 109.0 (3) C5—O4—C6 120.2 (5)

N2—C9—H9 109.2 C12—O8—C13 117.0 (5)

O1—C1—C2—N1 159.9 (4) O6—C8—C9—C10 94.1 (4) O2—C1—C2—N1 −23.4 (5) N2—C9—C10—C11 −57.5 (5) O1—C1—C2—C3 −76.8 (5) C8—C9—C10—C11 −178.2 (4) O2—C1—C2—C3 100.0 (4) C9—C10—C11—C12 −175.5 (5) N1—C2—C3—C4 −159.6 (4) C10—C11—C12—O7 17.9 (10) C1—C2—C3—C4 77.3 (5) C10—C11—C12—O8 −164.6 (5) C2—C3—C4—C5 170.8 (4) O3—C5—O4—C6 2.3 (10) C3—C4—C5—O3 32.3 (10) C4—C5—O4—C6 −176.9 (6) C3—C4—C5—O4 −148.6 (5) C7—C6—O4—C5 −176.0 (6) O5—C8—C9—N2 157.7 (4) O7—C12—O8—C13 1.5 (10) O6—C8—C9—N2 −26.7 (5) C11—C12—O8—C13 −176.0 (5) O5—C8—C9—C10 −81.5 (5) C14—C13—O8—C12 179.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N2—H2A···O5i _0.89 _1.96 _{2.840 (5)} ₁₇₀

N2—H2B···O2ii _0.89 _1.99 _{2.828 (4)} ₁₅₇

N2—H2C···O2iii _0.89 _1.93 _{2.807 (4)} ₁₇₀

N1—H1A···O1i _0.89 _1.98 _{2.813 (5)} ₁₅₅

N1—H1B···O6i _0.89 _1.88 _{2.741 (4)} ₁₆₁

N1—H1C···O6iv _0.89 _2.18 _{2.950 (4)} ₁₄₄

N1—H1C···O5iv _0.89 _2.35 _{3.178 (4)} ₁₅₄