Amino-guanidinium hydrogen fumarate.

The title compound, CH(7)N(4) (+)·C(4)H(3)O(4) (-), is a molecular salt in which the amino-guanidinium cations and fumarate monoanions are close to planar, with maximum deviations of 0.011 (1) and 0.177 (1) Å, respectively. The crystal packing is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

CH7N4 +·C4H3O4 −

M = 190.17

Monoclinic,

a = 6.3869 (3) Å

b = 19.8731 (10) Å

c = 7.0482 (4) Å

β = 114.688 (3)°

V = 812.84 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.26 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.976

10713 measured reflections

2340 independent reflections

1824 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.132

S = 1.04

2340 reflections

146 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004553/wm2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004553/wm2220Isup2.hkl

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

CH7N4+·C4H3O4−	F(000) = 400
Mr = 190.17	Dx = 1.554 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1824 reflections
a = 6.3869 (3) Å	θ = 2–29.9°
b = 19.8731 (10) Å	µ = 0.13 mm−1
c = 7.0482 (4) Å	T = 293 K
β = 114.688 (3)°	Block, colourless
V = 812.84 (8) Å3	0.26 × 0.15 × 0.15 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2340 independent reflections
Radiation source: fine-focus sealed tube	1824 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 29.9°, θmin = 2.1°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −24→27
Tmin = 0.966, Tmax = 0.976	l = −9→9
10713 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0756P)2 + 0.1408P] where P = (Fo2 + 2Fc2)/3
2340 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 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
H11B	0.243 (3)	0.4484 (12)	0.254 (3)	0.057 (5)*
H12	0.573 (3)	0.3932 (11)	0.302 (3)	0.056 (5)*
H13A	0.861 (4)	0.3941 (12)	0.204 (3)	0.072 (6)*
C1	1.12336 (19)	0.84396 (5)	0.68336 (19)	0.0281 (3)
C2	0.9984 (2)	0.78049 (5)	0.68320 (19)	0.0274 (2)
H2	1.0738	0.7396	0.6953	0.033*
C3	0.7863 (2)	0.78034 (6)	0.6666 (2)	0.0292 (3)
H3	0.7125	0.8212	0.6595	0.035*
C4	0.6603 (2)	0.71704 (5)	0.65888 (19)	0.0279 (3)
O6	1.04931 (17)	0.89803 (5)	0.71551 (19)	0.0466 (3)
O7	1.30209 (15)	0.83829 (4)	0.64654 (17)	0.0362 (2)
O8	0.45191 (15)	0.72255 (4)	0.64769 (17)	0.0374 (2)
H8	0.4189	0.7625	0.6465	0.056*
O9	0.74557 (17)	0.66199 (4)	0.66416 (19)	0.0434 (3)
H10A	0.521 (3)	0.5783 (9)	0.214 (3)	0.046 (5)*
H10B	0.747 (4)	0.5370 (10)	0.245 (3)	0.057 (5)*
H11A	0.221 (3)	0.5225 (10)	0.224 (3)	0.053 (5)*
C5	0.5133 (2)	0.48405 (6)	0.25398 (18)	0.0277 (3)
N10	0.6094 (2)	0.54110 (5)	0.23653 (19)	0.0350 (3)
N11	0.3028 (2)	0.48299 (6)	0.2428 (2)	0.0412 (3)
N12	0.6265 (2)	0.42625 (5)	0.2812 (2)	0.0361 (3)
N13	0.8519 (2)	0.42556 (6)	0.2974 (2)	0.0431 (3)
H13B	0.935 (4)	0.4125 (10)	0.424 (3)	0.061 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0233 (5)	0.0217 (5)	0.0413 (6)	−0.0015 (4)	0.0153 (5)	0.0003 (4)
C2	0.0253 (5)	0.0198 (5)	0.0400 (6)	−0.0004 (4)	0.0166 (5)	0.0010 (4)
C3	0.0270 (6)	0.0179 (5)	0.0477 (7)	−0.0010 (4)	0.0206 (5)	−0.0004 (4)
C4	0.0264 (5)	0.0200 (5)	0.0412 (6)	−0.0018 (4)	0.0180 (5)	0.0000 (4)
O6	0.0395 (5)	0.0226 (4)	0.0891 (8)	−0.0035 (4)	0.0382 (6)	−0.0077 (5)
O7	0.0291 (4)	0.0264 (4)	0.0620 (6)	−0.0027 (3)	0.0279 (4)	0.0003 (4)
O8	0.0280 (4)	0.0228 (4)	0.0683 (7)	−0.0027 (3)	0.0272 (4)	−0.0004 (4)
O9	0.0390 (5)	0.0196 (4)	0.0796 (7)	0.0023 (3)	0.0328 (5)	0.0019 (4)
C5	0.0301 (6)	0.0208 (5)	0.0345 (6)	0.0007 (4)	0.0158 (5)	0.0002 (4)
N10	0.0341 (6)	0.0206 (5)	0.0553 (7)	−0.0007 (4)	0.0238 (5)	0.0025 (4)
N11	0.0350 (6)	0.0254 (5)	0.0713 (9)	0.0000 (5)	0.0304 (6)	0.0024 (5)
N12	0.0353 (6)	0.0193 (5)	0.0599 (7)	0.0021 (4)	0.0260 (5)	0.0052 (4)
N13	0.0345 (6)	0.0348 (6)	0.0638 (9)	0.0076 (5)	0.0244 (6)	0.0025 (6)

C1—O6	1.2325 (14)	C5—N10	1.3190 (15)
C1—O7	1.2770 (14)	C5—N12	1.3278 (15)
C1—C2	1.4922 (15)	N10—H10A	0.905 (18)
C2—C3	1.3105 (16)	N10—H10B	0.86 (2)
C2—H2	0.9300	N11—H11B	0.80 (2)
C3—C4	1.4820 (15)	N11—H11A	0.92 (2)
C3—H3	0.9300	N12—N13	1.3960 (16)
C4—O9	1.2159 (14)	N12—H12	0.78 (2)
C4—O8	1.3044 (14)	N13—H13A	0.93 (2)
O8—H8	0.8200	N13—H13B	0.87 (2)
C5—N11	1.3136 (17)
O6—C1—O7	123.96 (10)	N11—C5—N12	118.46 (11)
O6—C1—C2	119.40 (10)	N10—C5—N12	120.71 (11)
O7—C1—C2	116.64 (10)	C5—N10—H10A	115.9 (12)
C3—C2—C1	122.32 (10)	C5—N10—H10B	114.5 (14)
C3—C2—H2	118.8	H10A—N10—H10B	129.6 (19)
C1—C2—H2	118.8	C5—N11—H11B	121.4 (15)
C2—C3—C4	122.04 (10)	C5—N11—H11A	120.0 (12)
C2—C3—H3	119.0	H11B—N11—H11A	119 (2)
C4—C3—H3	119.0	C5—N12—N13	120.06 (11)
O9—C4—O8	120.67 (10)	C5—N12—H12	120.1 (15)
O9—C4—C3	122.22 (10)	N13—N12—H12	119.5 (15)
O8—C4—C3	117.11 (10)	N12—N13—H13A	108.3 (15)
C4—O8—H8	109.5	N12—N13—H13B	104.9 (14)
N11—C5—N10	120.83 (11)	H13A—N13—H13B	109.7 (19)
O6—C1—C2—C3	16.50 (19)	C2—C3—C4—O8	178.28 (11)
O7—C1—C2—C3	−162.59 (12)	N11—C5—N12—N13	−178.90 (13)
C1—C2—C3—C4	177.74 (11)	N10—C5—N12—N13	1.8 (2)
C2—C3—C4—O9	−1.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O7i	0.82	1.68	2.489 (1)	168
N10—H10A···O7ii	0.91 (2)	2.09 (2)	2.993 (1)	177 (2)
N11—H11A···O6ii	0.92 (2)	1.91 (2)	2.827 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O7i	0.82	1.68	2.489 (1)	168
N10—H10A⋯O7ii	0.91 (2)	2.09 (2)	2.993 (1)	177 (2)
N11—H11A⋯O6ii	0.92 (2)	1.91 (2)	2.827 (2)	173 (2)

Symmetry codes: (i) ; (ii) .