Guanidinium l-glutamate

Bing Peng; Qingrong Peng; Wenfeng Zhou; Zhiqiang Zhou

doi:10.1107/S1600536810036354

. 2010 Sep 30;66(Pt 10):o2679. doi: 10.1107/S1600536810036354

Guanidinium l-glutamate

Bing Peng ^a, Qingrong Peng ^a, Wenfeng Zhou ^a,^*, Zhiqiang Zhou ^a,^‡

PMCID: PMC2983255 PMID: 21587647

Abstract

In the title compound, CH₆N₃ ⁺·C₅H₈NO₄ ⁻, there are two independent cations and two independent anions in the asymmetric unit. In the crystal structure, cations and anions are linked by intermolecular N—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For an early report of salts formed from amino acids and guanidines, see: Armstrong (1956 ▶).

Experimental

Crystal data

CH₆N₃ ⁺·C₅H₈NO₄ ⁻
M _r = 206.21
Monoclinic,
a = 8.7793 (7) Å
b = 10.8729 (10) Å
c = 10.0801 (9) Å
β = 104.552 (1)°
V = 931.34 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 K
0.42 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.950, T _max = 0.976
5501 measured reflections
2220 independent reflections
2087 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.081
S = 1.06
2220 reflections
255 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036354/lh5125sup1.cif

e-66-o2679-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036354/lh5125Isup2.hkl

e-66-o2679-Isup2.hkl^{(109.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O8	0.91	1.89	2.795 (2)	179
N1—H1B⋯O4ⁱ	0.91	1.84	2.738 (2)	170
N1—H1C⋯O2ⁱ	0.91	2.13	3.017 (2)	165
N2—H2A⋯O2ⁱⁱ	0.91	2.09	2.998 (2)	173
N2—H2B⋯O7ⁱⁱⁱ	0.91	2.16	2.740 (2)	120
N2—H2C⋯O5ⁱⁱⁱ	0.91	1.92	2.817 (3)	170
N3—H3A⋯O2ⁱ	0.88	2.08	2.900 (3)	154
N3—H3B⋯O3	0.88	2.08	2.841 (3)	145
N4—H4A⋯O3^iv	0.88	1.95	2.826 (2)	173
N4—H4B⋯O1ⁱ	0.88	2.22	3.095 (2)	170
N5—H5A⋯O4^iv	0.88	1.96	2.831 (2)	172
N5—H5B⋯O6	0.88	2.35	3.092 (3)	142
N6—H6A⋯O6	0.88	2.04	2.897 (2)	165
N6—H6B⋯O8^v	0.88	1.97	2.824 (2)	164
N7—H7A⋯O5	0.88	2.00	2.851 (2)	163
N7—H7B⋯O8^vi	0.88	2.02	2.775 (3)	143
N8—H8A⋯O7^v	0.88	2.08	2.954 (3)	170
N8—H8B⋯O1^vi	0.88	2.23	2.953 (3)	140

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

This work was supported by NSFC (project No. 20772210) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry. The authors acknowledge Dr Deng Xuebin for collecting the data at the Testing Center, College of Chemistry, Beijing Normal University.

supplementary crystallographic information

Comment

To better understand the formation of complex salts between a guanidine compounds and amino acids we carried out the crystal structure determination of the title compound. The asymmetric unit of the title compound is shown in Fig. 1. There are two independent cations and two indpendent anions in the asymmetric unit. In the crystal structure, cations and anions are linked by intramolecular N—H···O hydrogen bonds into a three-dimensional network (see Fig. 2).

Experimental

L-Glutamic acid (1.47 g.) and guanidine carbonate (0.90 g) were suspended in 10 ml of water. When the evolution of CO₂ had ceased the solution was diluted with 20 ml of acetone, and evaporated to a clear syrup. The syrup was dissolved in 30 ml of absolute methanol to yield a clear solution, and was allowed to stand overnight at room temperature. This solution was then placed in a fume hood for another day, whereupon the crystals of the title compound were collected and dried.