Guanidinium l-glutamate

Peng, B.; Peng, Q.; Zhou, W.; Zhou, Z.

doi:10.1107/S1600536810036354

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2679

doi:10.1107/S1600536810036354

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Guanidinium L-glutamate

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

^aDepartment of Applied Chemistry, China Agricultural University, Yuanmingyuan, West Road 2, Haidian District, Beijing 100194, People's Republic of China
^*Correspondence e-mail: wenfengzhou@cau.edu.cn

(Received 31 August 2010; accepted 10 September 2010; online 30 September 2010)

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, P 2₁
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[F² > 2σ(F²)] = 0.031
wR(F²) = 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

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
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) x, y, z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (v) x+1, y, z+1; (vi) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of the title compound with hydrogen bonds shown as dashed lines.

bis(carbamimidoylazanium) (2R)-2-aminopentanedioate top

Crystal data top

CH₆N₃⁺·C₅H₈NO₄⁻	F(000) = 440
M_r = 206.21	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2748 reflections
a = 8.7793 (7) Å	θ = 2.4–27.5°
b = 10.8729 (10) Å	µ = 0.12 mm⁻¹
c = 10.0801 (9) Å	T = 150 K
β = 104.552 (1)°	Prism, colourless
V = 931.34 (14) Å³	0.42 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2220 independent reflections
Radiation source: fine-focus sealed tube	2087 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.950, T_max = 0.976	k = −14→9
5501 measured reflections	l = −8→13

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.044P)² + 0.2149P] where P = (F_o² + 2F_c²)/3
2220 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

CH₆N₃⁺·C₅H₈NO₄⁻	V = 931.34 (14) Å³
M_r = 206.21	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.7793 (7) Å	µ = 0.12 mm⁻¹
b = 10.8729 (10) Å	T = 150 K
c = 10.0801 (9) Å	0.42 × 0.26 × 0.20 mm
β = 104.552 (1)°

Data collection top

Bruker SMART APEX diffractometer	2220 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2087 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.976	R_int = 0.021
5501 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	1 restraint
wR(F²) = 0.081	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2220 reflections	Δρ_min = −0.23 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.3633 (2)	0.4498 (2)	−0.1328 (2)	0.0157 (4)
C2	0.4808 (2)	0.5516 (2)	−0.06507 (19)	0.0152 (4)
H2	0.5234	0.5892	−0.1389	0.018*
C3	0.6207 (2)	0.5030 (2)	0.0442 (2)	0.0175 (4)
H3C	0.6924	0.5723	0.0803	0.021*
H3D	0.6793	0.4434	0.0016	0.021*
C4	0.5727 (2)	0.4405 (2)	0.1632 (2)	0.0185 (4)
H4C	0.4937	0.3761	0.1264	0.022*
H4D	0.5227	0.5020	0.2111	0.022*
C5	0.7121 (2)	0.3823 (2)	0.2661 (2)	0.0161 (4)
C6	0.6284 (3)	0.5883 (2)	0.6253 (2)	0.0170 (4)
C7	0.5001 (2)	0.5088 (2)	0.5315 (2)	0.0142 (4)
H7	0.5153	0.5159	0.4368	0.017*
C8	0.3304 (2)	0.5466 (2)	0.52340 (19)	0.0164 (4)
H8C	0.3259	0.6367	0.5357	0.020*
H8D	0.2954	0.5067	0.5990	0.020*
C9	0.2181 (2)	0.5106 (2)	0.3863 (2)	0.0171 (4)
H9A	0.2379	0.4240	0.3655	0.020*
H9B	0.1083	0.5165	0.3946	0.020*
C10	0.2368 (2)	0.5920 (2)	0.2679 (2)	0.0156 (4)
C11	0.9131 (2)	0.7443 (2)	0.4492 (2)	0.0176 (4)
C12	0.9193 (3)	0.7368 (2)	0.9641 (2)	0.0179 (4)
N1	0.3944 (2)	0.65067 (18)	−0.01100 (17)	0.0155 (4)
H1A	0.3351	0.6164	0.0415	0.023*
H1B	0.3307	0.6918	−0.0823	0.023*
H1C	0.4648	0.7040	0.0407	0.023*
N2	0.5301 (2)	0.37747 (18)	0.57395 (19)	0.0183 (4)
H2A	0.4960	0.3633	0.6507	0.027*
H2B	0.6351	0.3617	0.5918	0.027*
H2C	0.4774	0.3275	0.5052	0.027*
N3	0.7857 (2)	0.6972 (2)	0.3634 (2)	0.0240 (4)
H3A	0.7411	0.7361	0.2870	0.029*
H3B	0.7461	0.6272	0.3832	0.029*
N4	0.9733 (2)	0.84922 (19)	0.42024 (19)	0.0204 (4)
H4A	1.0578	0.8797	0.4770	0.024*
H4B	0.9288	0.8887	0.3441	0.024*
N5	0.9797 (2)	0.68433 (19)	0.5639 (2)	0.0215 (4)
H5A	1.0643	0.7145	0.6209	0.026*
H5B	0.9394	0.6144	0.5829	0.026*
N6	0.9603 (2)	0.62410 (19)	0.9389 (2)	0.0242 (4)
H6A	0.9036	0.5832	0.8682	0.029*
H6B	1.0442	0.5899	0.9926	0.029*
N7	0.7924 (2)	0.78798 (19)	0.88260 (19)	0.0222 (4)
H7A	0.7361	0.7467	0.8121	0.027*
H7B	0.7648	0.8631	0.8991	0.027*
N8	1.0012 (2)	0.8000 (2)	1.0716 (2)	0.0248 (5)
H8A	1.0844	0.7668	1.1274	0.030*
H8B	0.9721	0.8751	1.0868	0.030*
O1	0.22034 (18)	0.47085 (14)	−0.15334 (15)	0.0197 (3)
O2	0.42560 (19)	0.35290 (15)	−0.16612 (15)	0.0206 (3)
O3	0.76473 (19)	0.43703 (16)	0.37806 (16)	0.0221 (4)
O4	0.76678 (19)	0.28334 (16)	0.23297 (16)	0.0236 (4)
O5	0.6030 (2)	0.70163 (15)	0.62702 (17)	0.0234 (4)
O6	0.75073 (18)	0.53379 (16)	0.68837 (16)	0.0225 (4)
O7	0.2657 (2)	0.70271 (16)	0.28796 (17)	0.0277 (4)
O8	0.21550 (17)	0.54149 (15)	0.15054 (14)	0.0184 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0218 (10)	0.0148 (10)	0.0098 (9)	−0.0013 (8)	0.0027 (8)	0.0026 (8)
C2	0.0177 (9)	0.0146 (10)	0.0126 (8)	−0.0017 (8)	0.0025 (7)	−0.0002 (8)
C3	0.0153 (9)	0.0193 (10)	0.0165 (10)	0.0003 (9)	0.0013 (8)	−0.0003 (8)
C4	0.0159 (10)	0.0222 (12)	0.0161 (10)	0.0029 (9)	0.0017 (8)	−0.0005 (9)
C5	0.0153 (9)	0.0163 (10)	0.0158 (10)	0.0001 (8)	0.0024 (8)	0.0010 (8)
C6	0.0180 (10)	0.0187 (11)	0.0135 (9)	−0.0030 (9)	0.0024 (8)	0.0002 (8)
C7	0.0177 (9)	0.0134 (10)	0.0110 (9)	0.0014 (8)	0.0023 (7)	0.0009 (8)
C8	0.0167 (9)	0.0203 (10)	0.0115 (9)	0.0013 (8)	0.0024 (7)	0.0006 (8)
C9	0.0166 (9)	0.0184 (10)	0.0151 (9)	−0.0024 (8)	0.0021 (7)	0.0000 (8)
C10	0.0126 (9)	0.0167 (10)	0.0155 (10)	0.0014 (8)	−0.0005 (7)	0.0014 (8)
C11	0.0169 (10)	0.0180 (11)	0.0182 (10)	0.0029 (8)	0.0048 (8)	−0.0029 (8)
C12	0.0186 (10)	0.0176 (11)	0.0169 (10)	0.0009 (8)	0.0035 (8)	0.0015 (8)
N1	0.0186 (8)	0.0142 (8)	0.0122 (8)	−0.0007 (7)	0.0008 (6)	0.0010 (7)
N2	0.0202 (9)	0.0136 (9)	0.0184 (9)	0.0008 (7)	−0.0003 (7)	−0.0010 (7)
N3	0.0246 (10)	0.0203 (10)	0.0214 (9)	−0.0026 (8)	−0.0052 (8)	0.0023 (8)
N4	0.0205 (9)	0.0211 (10)	0.0172 (9)	−0.0025 (8)	0.0001 (7)	0.0001 (8)
N5	0.0189 (9)	0.0211 (10)	0.0206 (9)	−0.0030 (8)	−0.0024 (7)	0.0020 (8)
N6	0.0237 (10)	0.0209 (11)	0.0233 (10)	0.0065 (8)	−0.0028 (8)	−0.0031 (8)
N7	0.0240 (10)	0.0171 (9)	0.0209 (9)	0.0043 (8)	−0.0032 (8)	−0.0035 (8)
N8	0.0284 (10)	0.0203 (11)	0.0195 (9)	0.0056 (8)	−0.0057 (8)	−0.0024 (8)
O1	0.0183 (7)	0.0212 (9)	0.0175 (7)	−0.0006 (6)	0.0010 (6)	−0.0013 (6)
O2	0.0253 (8)	0.0183 (8)	0.0167 (8)	0.0026 (7)	0.0024 (6)	−0.0035 (6)
O3	0.0235 (8)	0.0218 (9)	0.0171 (8)	0.0053 (7)	−0.0020 (6)	−0.0046 (7)
O4	0.0253 (8)	0.0208 (8)	0.0199 (8)	0.0068 (7)	−0.0032 (6)	−0.0048 (7)
O5	0.0280 (9)	0.0137 (8)	0.0232 (8)	−0.0024 (7)	−0.0033 (7)	0.0003 (6)
O6	0.0191 (8)	0.0201 (9)	0.0234 (8)	0.0000 (7)	−0.0035 (6)	−0.0009 (7)
O7	0.0405 (10)	0.0178 (8)	0.0195 (8)	−0.0069 (8)	−0.0025 (7)	0.0026 (7)
O8	0.0220 (7)	0.0185 (8)	0.0143 (7)	0.0015 (6)	0.0039 (6)	0.0016 (6)

Geometric parameters (Å, º) top

C1—O1	1.241 (3)	C10—O7	1.237 (3)
C1—O2	1.271 (3)	C10—O8	1.275 (3)
C1—C2	1.549 (3)	C11—N4	1.321 (3)
C2—N1	1.497 (3)	C11—N5	1.328 (3)
C2—C3	1.524 (3)	C11—N3	1.332 (3)
C2—H2	1.0000	C12—N6	1.319 (3)
C3—C4	1.527 (3)	C12—N7	1.329 (3)
C3—H3C	0.9900	C12—N8	1.331 (3)
C3—H3D	0.9900	N1—H1A	0.9100
C4—C5	1.529 (3)	N1—H1B	0.9100
C4—H4C	0.9900	N1—H1C	0.9100
C4—H4D	0.9900	N2—H2A	0.9100
C5—O4	1.257 (3)	N2—H2B	0.9100
C5—O3	1.257 (3)	N2—H2C	0.9100
C6—O6	1.251 (3)	N3—H3A	0.8800
C6—O5	1.253 (3)	N3—H3B	0.8800
C6—C7	1.541 (3)	N4—H4A	0.8800
C7—N2	1.495 (3)	N4—H4B	0.8800
C7—C8	1.528 (3)	N5—H5A	0.8800
C7—H7	1.0000	N5—H5B	0.8800
C8—C9	1.533 (3)	N6—H6A	0.8800
C8—H8C	0.9900	N6—H6B	0.8800
C8—H8D	0.9900	N7—H7A	0.8800
C9—C10	1.527 (3)	N7—H7B	0.8800
C9—H9A	0.9900	N8—H8A	0.8800
C9—H9B	0.9900	N8—H8B	0.8800

O1—C1—O2	126.4 (2)	C10—C9—H9B	109.1
O1—C1—C2	118.4 (2)	C8—C9—H9B	109.1
O2—C1—C2	115.21 (18)	H9A—C9—H9B	107.8
N1—C2—C3	112.11 (16)	O7—C10—O8	123.2 (2)
N1—C2—C1	109.42 (16)	O7—C10—C9	119.6 (2)
C3—C2—C1	113.44 (18)	O8—C10—C9	117.14 (19)
N1—C2—H2	107.2	N4—C11—N5	120.2 (2)
C3—C2—H2	107.2	N4—C11—N3	120.4 (2)
C1—C2—H2	107.2	N5—C11—N3	119.4 (2)
C2—C3—C4	112.99 (17)	N6—C12—N7	119.7 (2)
C2—C3—H3C	109.0	N6—C12—N8	121.3 (2)
C4—C3—H3C	109.0	N7—C12—N8	119.0 (2)
C2—C3—H3D	109.0	C2—N1—H1A	109.5
C4—C3—H3D	109.0	C2—N1—H1B	109.5
H3C—C3—H3D	107.8	H1A—N1—H1B	109.5
C3—C4—C5	112.67 (17)	C2—N1—H1C	109.5
C3—C4—H4C	109.1	H1A—N1—H1C	109.5
C5—C4—H4C	109.1	H1B—N1—H1C	109.5
C3—C4—H4D	109.1	C7—N2—H2A	109.5
C5—C4—H4D	109.1	C7—N2—H2B	109.5
H4C—C4—H4D	107.8	H2A—N2—H2B	109.5
O4—C5—O3	124.40 (19)	C7—N2—H2C	109.5
O4—C5—C4	117.95 (18)	H2A—N2—H2C	109.5
O3—C5—C4	117.6 (2)	H2B—N2—H2C	109.5
O6—C6—O5	126.2 (2)	C11—N3—H3A	120.0
O6—C6—C7	116.6 (2)	C11—N3—H3B	120.0
O5—C6—C7	117.06 (19)	H3A—N3—H3B	120.0
N2—C7—C8	111.79 (18)	C11—N4—H4A	120.0
N2—C7—C6	108.12 (16)	C11—N4—H4B	120.0
C8—C7—C6	115.78 (18)	H4A—N4—H4B	120.0
N2—C7—H7	106.9	C11—N5—H5A	120.0
C8—C7—H7	106.9	C11—N5—H5B	120.0
C6—C7—H7	106.9	H5A—N5—H5B	120.0
C7—C8—C9	112.17 (17)	C12—N6—H6A	120.0
C7—C8—H8C	109.2	C12—N6—H6B	120.0
C9—C8—H8C	109.2	H6A—N6—H6B	120.0
C7—C8—H8D	109.2	C12—N7—H7A	120.0
C9—C8—H8D	109.2	C12—N7—H7B	120.0
H8C—C8—H8D	107.9	H7A—N7—H7B	120.0
C10—C9—C8	112.69 (17)	C12—N8—H8A	120.0
C10—C9—H9A	109.1	C12—N8—H8B	120.0
C8—C9—H9A	109.1	H8A—N8—H8B	120.0

O1—C1—C2—N1	11.3 (3)	O6—C6—C7—N2	18.9 (3)
O2—C1—C2—N1	−170.89 (17)	O5—C6—C7—N2	−163.9 (2)
O1—C1—C2—C3	137.29 (19)	O6—C6—C7—C8	145.18 (19)
O2—C1—C2—C3	−44.9 (2)	O5—C6—C7—C8	−37.6 (3)
N1—C2—C3—C4	63.7 (2)	N2—C7—C8—C9	−83.4 (2)
C1—C2—C3—C4	−60.8 (2)	C6—C7—C8—C9	152.21 (18)
C2—C3—C4—C5	174.99 (19)	C7—C8—C9—C10	−73.5 (2)
C3—C4—C5—O4	−75.2 (3)	C8—C9—C10—O7	−36.4 (3)
C3—C4—C5—O3	104.4 (2)	C8—C9—C10—O8	146.12 (19)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x, y, z+1; (iii) −x+1, y−1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) x+1, y, z+1; (vi) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	CH₆N₃⁺·C₅H₈NO₄⁻
M_r	206.21
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	8.7793 (7), 10.8729 (10), 10.0801 (9)
β (°)	104.552 (1)
V (Å³)	931.34 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.42 × 0.26 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	5501, 2220, 2087
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.06
No. of reflections	2220
No. of parameters	255
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8	0.91	1.89	2.795 (2)	178.5
N1—H1B···O4ⁱ	0.91	1.84	2.738 (2)	170.3
N1—H1C···O2ⁱ	0.91	2.13	3.017 (2)	164.8
N2—H2A···O2ⁱⁱ	0.91	2.09	2.998 (2)	173.0
N2—H2B···O7ⁱⁱⁱ	0.91	2.16	2.740 (2)	120.4
N2—H2C···O5ⁱⁱⁱ	0.91	1.92	2.817 (3)	169.6
N3—H3A···O2ⁱ	0.88	2.08	2.900 (3)	153.8
N3—H3B···O3	0.88	2.08	2.841 (3)	144.8
N4—H4A···O3^iv	0.88	1.95	2.826 (2)	172.5
N4—H4B···O1ⁱ	0.88	2.22	3.095 (2)	170.2
N5—H5A···O4^iv	0.88	1.96	2.831 (2)	171.6
N5—H5B···O6	0.88	2.35	3.092 (3)	142.1
N6—H6A···O6	0.88	2.04	2.897 (2)	164.8
N6—H6B···O8^v	0.88	1.97	2.824 (2)	164.4
N7—H7A···O5	0.88	2.00	2.851 (2)	163.3
N7—H7B···O8^vi	0.88	2.02	2.775 (3)	143.0
N8—H8A···O7^v	0.88	2.08	2.954 (3)	169.5
N8—H8B···O1^vi	0.88	2.23	2.953 (3)	139.6

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x, y, z+1; (iii) −x+1, y−1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) x+1, y, z+1; (vi) −x+1, y+1/2, −z+1.

Footnotes

‡Additional corresponding author, e-mail: zqzhou@cau.edu.cn.

Acknowledgements

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.

References

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Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar