Amino-guanidinium hydrogen succinate.

The title compound, CH(7)N(4) (+)·C(4)H(5)O(4) (-), is a molecular salt containing discrete amino-guanidinium and succinate ions. The amino-guanidinium cation is nearly planar, with a maximum deviation of 0.035 (1) Å. The dihedral angle between the amino-guanidinium cation and the succinate anion is 3.35 (6)°. The crystal packing exhibits inter-molecular N-H⋯O and O-H⋯·O hydrogen bonds.

Related literature

For related structures, see: Adams (1977 ▶); Mullen & Hellner (1978 ▶); Akella & Keszler (1994 ▶). For biological applications of amino­guanadine, see: Makita et al. (1995 ▶); Brownlee et al. (1986 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

CH7N4 +·C4H5O4 −

M = 192.19

Monoclinic,

a = 15.071 (5) Å

b = 6.565 (2) Å

c = 18.152 (5) Å

β = 109.733 (5)°

V = 1690.5 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 293 (2) K

0.25 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.980

11302 measured reflections

2773 independent reflections

2107 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.135

S = 1.05

2773 reflections

146 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003626/lx2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003626/lx2087Isup2.hkl

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

CH7N4+·C4H5O4−	F(000) = 816
Mr = 192.19	Dx = 1.510 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 2773 reflections
a = 15.071 (5) Å	θ = 2.4–31.4°
b = 6.565 (2) Å	µ = 0.13 mm−1
c = 18.152 (5) Å	T = 293 K
β = 109.733 (5)°	Block, colourless
V = 1690.5 (9) Å3	0.25 × 0.16 × 0.16 mm
Z = 8

Bruker APEXII CCD diffractometer	2773 independent reflections
Radiation source: fine-focus sealed tube	2107 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.0 pixels mm-1	θmax = 31.4°, θmin = 2.4°
ω scans	h = −22→21
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.968, Tmax = 0.980	l = −25→26
11302 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0746P)2 + 0.4733P] where P = (Fo2 + 2Fc2)/3
2773 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
H12A	0.1707 (12)	1.015 (3)	0.2850 (10)	0.053 (5)*
H12B	0.1337 (11)	0.802 (3)	0.2512 (9)	0.043 (4)*
H13A	0.3357 (16)	1.149 (3)	0.4112 (13)	0.090 (7)*
H13B	0.2620 (13)	1.136 (3)	0.4466 (12)	0.073 (6)*
H10A	0.1961 (13)	0.509 (3)	0.3165 (11)	0.055 (5)*
H10B	0.2701 (11)	0.531 (2)	0.3943 (10)	0.050 (4)*
H11	0.3229 (11)	0.826 (2)	0.4490 (9)	0.047 (4)*
C1	0.54873 (7)	0.08831 (15)	0.67511 (6)	0.0289 (2)
C2	0.47896 (7)	0.20438 (15)	0.61002 (6)	0.0306 (2)
H2A	0.4158	0.1689	0.6083	0.037*
H2B	0.4853	0.1628	0.5607	0.037*
C3	0.49064 (7)	0.43218 (15)	0.61797 (6)	0.0281 (2)
H3A	0.5542	0.4676	0.6209	0.034*
H3B	0.4826	0.4744	0.6666	0.034*
C4	0.42163 (7)	0.54741 (15)	0.55112 (6)	0.0291 (2)
C5	0.22849 (7)	0.78408 (16)	0.34760 (6)	0.0282 (2)
N10	0.23172 (8)	0.58414 (15)	0.35140 (6)	0.0381 (3)
N11	0.28683 (7)	0.88965 (14)	0.40661 (6)	0.0368 (2)
N12	0.16935 (7)	0.87957 (16)	0.28669 (6)	0.0379 (3)
N13	0.27963 (9)	1.10237 (16)	0.40542 (7)	0.0446 (3)
O6	0.54679 (6)	−0.10939 (12)	0.66765 (5)	0.0436 (2)
H6	0.5057	−0.1414	0.6265	0.065*
O7	0.60494 (6)	0.17027 (12)	0.73220 (5)	0.0386 (2)
O8	0.42768 (6)	0.74200 (11)	0.55212 (5)	0.0395 (2)
O9	0.36190 (7)	0.45581 (13)	0.49819 (5)	0.0489 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0314 (5)	0.0199 (4)	0.0270 (5)	−0.0002 (4)	−0.0011 (4)	0.0023 (3)
C2	0.0343 (5)	0.0190 (4)	0.0269 (5)	0.0002 (4)	−0.0052 (4)	0.0028 (3)
C3	0.0326 (5)	0.0185 (4)	0.0239 (4)	0.0009 (3)	−0.0028 (4)	0.0012 (3)
C4	0.0355 (5)	0.0195 (4)	0.0239 (4)	0.0026 (4)	−0.0012 (4)	0.0013 (3)
C5	0.0296 (5)	0.0241 (4)	0.0242 (4)	0.0005 (4)	0.0005 (4)	−0.0018 (3)
N10	0.0454 (6)	0.0221 (4)	0.0325 (5)	0.0001 (4)	−0.0058 (4)	−0.0020 (4)
N11	0.0443 (5)	0.0223 (4)	0.0285 (4)	0.0002 (4)	−0.0076 (4)	−0.0024 (3)
N12	0.0426 (5)	0.0261 (5)	0.0294 (5)	0.0009 (4)	−0.0082 (4)	0.0004 (4)
N13	0.0525 (7)	0.0224 (4)	0.0443 (6)	−0.0012 (4)	−0.0030 (5)	−0.0061 (4)
O6	0.0503 (5)	0.0181 (3)	0.0396 (5)	0.0004 (3)	−0.0147 (4)	0.0026 (3)
O7	0.0420 (5)	0.0250 (4)	0.0317 (4)	−0.0003 (3)	−0.0097 (3)	0.0007 (3)
O8	0.0485 (5)	0.0181 (3)	0.0347 (4)	0.0009 (3)	−0.0085 (3)	0.0027 (3)
O9	0.0592 (6)	0.0258 (4)	0.0348 (4)	0.0000 (4)	−0.0195 (4)	−0.0018 (3)

C1—O7	1.2200 (13)	C5—N12	1.3207 (13)
C1—O6	1.3043 (13)	C5—N11	1.3285 (13)
C1—C2	1.4978 (13)	N10—H10A	0.840 (19)
C2—C3	1.5071 (15)	N10—H10B	0.871 (17)
C2—H2A	0.9700	N11—N13	1.4003 (15)
C2—H2B	0.9700	N11—H11	0.884 (17)
C3—C4	1.5080 (13)	N12—H12A	0.891 (19)
C3—H3A	0.9700	N12—H12B	0.852 (16)
C3—H3B	0.9700	N13—H13A	0.87 (2)
C4—O9	1.2293 (13)	N13—H13B	0.90 (2)
C4—O8	1.2804 (12)	O6—H6	0.8200
C5—N10	1.3144 (15)
O7—C1—O6	120.79 (9)	O8—C4—C3	117.56 (9)
O7—C1—C2	123.16 (9)	N10—C5—N12	121.37 (10)
O6—C1—C2	116.06 (8)	N10—C5—N11	118.42 (10)
C1—C2—C3	113.65 (8)	N12—C5—N11	120.21 (10)
C1—C2—H2A	108.8	C5—N10—H10A	123.2 (12)
C3—C2—H2A	108.8	C5—N10—H10B	116.7 (11)
C1—C2—H2B	108.8	H10A—N10—H10B	119.9 (16)
C3—C2—H2B	108.8	C5—N11—N13	118.76 (9)
H2A—C2—H2B	107.7	C5—N11—H11	120.0 (10)
C2—C3—C4	113.22 (8)	N13—N11—H11	120.6 (10)
C2—C3—H3A	108.9	C5—N12—H12A	119.1 (11)
C4—C3—H3A	108.9	C5—N12—H12B	115.2 (11)
C2—C3—H3B	108.9	H12A—N12—H12B	125.7 (16)
C4—C3—H3B	108.9	N11—N13—H13A	106.3 (15)
H3A—C3—H3B	107.7	N11—N13—H13B	106.1 (13)
O9—C4—O8	121.94 (9)	H13A—N13—H13B	111 (2)
O9—C4—C3	120.50 (9)	C1—O6—H6	109.5
O7—C1—C2—C3	5.34 (16)	C2—C3—C4—O8	−178.55 (10)
O6—C1—C2—C3	−174.44 (10)	N10—C5—N11—N13	−175.87 (12)
C1—C2—C3—C4	178.57 (9)	N12—C5—N11—N13	4.49 (17)
C2—C3—C4—O9	1.74 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10B···O9	0.87 (2)	1.99 (2)	2.851 (1)	171 (2)
N11—H11···O8	0.88 (2)	2.07 (2)	2.939 (1)	166 (1)
N12—H12B···O6i	0.85 (2)	2.07 (2)	2.921 (1)	178 (2)
N10—H10A···O7i	0.84 (2)	2.05 (2)	2.886 (1)	178 (2)
O6—H6···O8ii	0.82	1.65	2.456 (1)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10B⋯O9	0.87 (2)	1.99 (2)	2.851 (1)	171 (2)
N11—H11⋯O8	0.88 (2)	2.07 (2)	2.939 (1)	166 (1)
N12—H12B⋯O6i	0.85 (2)	2.07 (2)	2.921 (1)	178 (2)
N10—H10A⋯O7i	0.84 (2)	2.05 (2)	2.886 (1)	178 (2)
O6—H6⋯O8ii	0.82	1.65	2.456 (1)	167

Symmetry codes: (i) ; (ii) .