Diacetamidinium sulfate.

In the crystal structure of the title compound, 2C(2)H(7)N(2) (+)·SO(4) (2-), which contains four cations and two anions in the asymmetric unit, the ions are inter-connected by an extensive hydrogen-bonding system whereby two of the O atoms of sulfate ion are hydrogen-bonded to the amidinium H atoms of two cations, leading to the formation of two eight-membered rings. The two remaining O atoms inter-connect two H atoms of acetamidinium cations, forming an infinite chain. The C⋯N separations within the H(2)N⋯C⋯NH(2) moieties are similar, with an average value of 1.305 (2) Å, which is in good agreement with a delocalization model.

Related literature

For preparation, reactivity and behaviour of similar compounds, see: Jalový et al. (2005 ▶); Latypov et al. (1998 ▶); Taylor & Ehrhart (1960 ▶). For related structures, see: Calov & Jost (1990 ▶); Cannon et al. (1976 ▶); Emirdag-Eanes & Ibers (2002) ▶; Ferretti et al. (2004 ▶); Jalový et al. (2009 ▶); Tominey et al. (2006 ▶).

Experimental

Crystal data

2C2H7N2 +·SO4 2−

M = 214.26

Triclinic,

a = 8.0961 (3) Å

b = 11.1668 (4) Å

c = 11.8821 (6) Å

α = 96.199 (4)°

β = 105.905 (3)°

γ = 105.615 (4)°

V = 975.63 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 150 K

0.44 × 0.23 × 0.21 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: Gaussian (Coppens, 1970 ▶) T min = 0.915, T max = 0.958

20866 measured reflections

4459 independent reflections

3623 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.10

4459 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.46 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwin­owski & Minor, 1997 ▶); cell refinement: COLLECT and DEn class="Chemical">NZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049160/rk2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049160/rk2242Isup2.hkl

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

2C2H7N2+·O4S2−	Z = 4
Mr = 214.26	F(000) = 456
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P 1	Melting point = 483–485 K
a = 8.0961 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1668 (4) Å	Cell parameters from 20921 reflections
c = 11.8821 (6) Å	θ = 1–27.5°
α = 96.199 (4)°	µ = 0.33 mm−1
β = 105.905 (3)°	T = 150 K
γ = 105.615 (4)°	Block, colourless
V = 975.63 (8) Å3	0.44 × 0.23 × 0.21 mm

Bruker–Nonius KappaCCD area-detector diffractometer	4459 independent reflections
Radiation source: fine–focus sealed tube	3623 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ– and ω–scans to fill the Ewald sphere	h = −10→10
Absorption correction: gaussian (Coppens, 1970)	k = −14→14
Tmin = 0.915, Tmax = 0.958	l = −15→15
20866 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) = 0.105	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.6492P] where P = (Fo2 + 2Fc2)/3
4459 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.79775 (6)	0.46840 (4)	0.72331 (4)	0.01727 (12)
S2	0.19510 (6)	0.03481 (4)	0.78098 (4)	0.01627 (12)
O6	0.16125 (19)	0.02135 (13)	0.89534 (12)	0.0213 (3)
O7	0.1162 (2)	−0.08915 (13)	0.69712 (12)	0.0239 (3)
O3	0.71625 (18)	0.37497 (12)	0.60982 (12)	0.0209 (3)
O2	0.71148 (19)	0.42348 (14)	0.81242 (12)	0.0235 (3)
O4	0.99312 (18)	0.48642 (13)	0.76995 (12)	0.0219 (3)
O5	0.11266 (18)	0.12598 (12)	0.72686 (12)	0.0208 (3)
N12	−0.0434 (2)	0.77755 (16)	0.91285 (15)	0.0216 (3)
H12A	−0.1251	0.7271	0.8509	0.026*
H12B	0.0103	0.8539	0.9086	0.026*
O8	0.39298 (18)	0.07972 (14)	0.80283 (12)	0.0240 (3)
N18	0.4617 (2)	0.13845 (16)	0.59125 (15)	0.0215 (3)
H18A	0.4545	0.1115	0.6554	0.026*
H18B	0.5520	0.2017	0.5939	0.026*
N15	0.3313 (2)	0.36087 (16)	0.70691 (15)	0.0215 (3)
H15A	0.4408	0.3939	0.7535	0.026*
H15B	0.2610	0.2951	0.7205	0.026*
O1	0.7676 (2)	0.59000 (13)	0.70173 (12)	0.0242 (3)
N16	0.3762 (2)	0.51104 (15)	0.59222 (15)	0.0213 (3)
H16A	0.4861	0.5455	0.6377	0.026*
H16B	0.3343	0.5421	0.5315	0.026*
N11	−0.0796 (2)	0.62260 (16)	1.02350 (15)	0.0215 (3)
H11A	−0.1618	0.5704	0.9628	0.026*
H11B	−0.0493	0.5990	1.0907	0.026*
N13	0.2530 (2)	0.72388 (16)	0.79442 (15)	0.0225 (4)
H13A	0.2178	0.7767	0.7537	0.027*
H13B	0.1849	0.6465	0.7801	0.027*
N14	0.5176 (2)	0.87828 (16)	0.90289 (15)	0.0227 (4)
H14A	0.4860	0.9332	0.8636	0.027*
H14B	0.6201	0.9001	0.9585	0.027*
C7	0.3355 (3)	0.08310 (17)	0.48927 (17)	0.0183 (4)
N17	0.1957 (2)	−0.01346 (15)	0.48128 (15)	0.0215 (3)
H17A	0.1850	−0.0424	0.5440	0.026*
H17B	0.1146	−0.0480	0.4132	0.026*
C3	0.4094 (3)	0.76088 (18)	0.87780 (17)	0.0195 (4)
C5	0.2718 (3)	0.41071 (17)	0.61547 (17)	0.0179 (4)
C1	−0.0009 (3)	0.73845 (18)	1.01366 (17)	0.0182 (4)
C6	0.0825 (3)	0.3512 (2)	0.53533 (19)	0.0242 (4)
H6A	0.0713	0.2708	0.4909	0.036*
H6B	0.0520	0.4056	0.4811	0.036*
H6C	0.0020	0.3390	0.5822	0.036*
C4	0.4675 (3)	0.6675 (2)	0.9475 (2)	0.0314 (5)
H4A	0.4360	0.6735	1.0197	0.047*
H4B	0.5960	0.6857	0.9670	0.047*
H4C	0.4079	0.5834	0.9007	0.047*
C2	0.1430 (3)	0.82735 (19)	1.11939 (18)	0.0235 (4)
H2A	0.2583	0.8190	1.1205	0.035*
H2B	0.1189	0.8074	1.1911	0.035*
H2C	0.1442	0.9128	1.1146	0.035*
C8	0.3526 (3)	0.1306 (2)	0.37894 (18)	0.0278 (5)
H8A	0.2818	0.1869	0.3620	0.042*
H8B	0.3099	0.0602	0.3131	0.042*
H8C	0.4771	0.1753	0.3907	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0150 (2)	0.0162 (2)	0.0149 (2)	−0.00007 (17)	0.00017 (17)	0.00432 (17)
S2	0.0153 (2)	0.0161 (2)	0.0141 (2)	0.00153 (17)	0.00173 (17)	0.00533 (16)
O6	0.0210 (7)	0.0234 (7)	0.0168 (7)	0.0018 (5)	0.0056 (5)	0.0072 (5)
O7	0.0275 (8)	0.0182 (7)	0.0197 (7)	0.0040 (6)	0.0012 (6)	0.0022 (5)
O3	0.0208 (7)	0.0179 (7)	0.0167 (6)	0.0004 (5)	0.0004 (5)	0.0026 (5)
O2	0.0189 (7)	0.0289 (8)	0.0194 (7)	0.0017 (6)	0.0048 (6)	0.0090 (6)
O4	0.0154 (7)	0.0233 (7)	0.0210 (7)	0.0006 (5)	0.0008 (5)	0.0072 (5)
O5	0.0201 (7)	0.0172 (7)	0.0211 (7)	0.0030 (5)	0.0015 (5)	0.0079 (5)
N12	0.0230 (9)	0.0174 (8)	0.0190 (8)	0.0015 (6)	0.0028 (7)	0.0034 (6)
O8	0.0158 (7)	0.0305 (8)	0.0223 (7)	0.0027 (6)	0.0035 (6)	0.0102 (6)
N18	0.0202 (8)	0.0201 (8)	0.0193 (8)	−0.0008 (6)	0.0059 (7)	0.0036 (6)
N15	0.0186 (8)	0.0202 (8)	0.0233 (8)	0.0024 (6)	0.0052 (7)	0.0083 (7)
O1	0.0267 (8)	0.0163 (7)	0.0222 (7)	0.0029 (6)	−0.0001 (6)	0.0041 (5)
N16	0.0206 (8)	0.0210 (8)	0.0187 (8)	0.0035 (7)	0.0020 (7)	0.0081 (6)
N11	0.0203 (8)	0.0217 (8)	0.0178 (8)	0.0029 (7)	0.0010 (7)	0.0063 (6)
N13	0.0194 (8)	0.0176 (8)	0.0252 (9)	0.0022 (6)	0.0026 (7)	0.0043 (7)
N14	0.0187 (8)	0.0224 (8)	0.0209 (8)	0.0021 (7)	0.0003 (7)	0.0049 (7)
C7	0.0184 (9)	0.0173 (9)	0.0202 (9)	0.0067 (7)	0.0068 (7)	0.0038 (7)
N17	0.0188 (8)	0.0229 (8)	0.0167 (8)	0.0003 (7)	0.0022 (6)	0.0036 (6)
C3	0.0198 (9)	0.0209 (9)	0.0186 (9)	0.0063 (7)	0.0076 (7)	0.0035 (7)
C5	0.0192 (9)	0.0161 (9)	0.0181 (9)	0.0058 (7)	0.0064 (7)	0.0009 (7)
C1	0.0158 (9)	0.0203 (9)	0.0197 (9)	0.0068 (7)	0.0064 (7)	0.0032 (7)
C6	0.0181 (10)	0.0256 (10)	0.0255 (10)	0.0040 (8)	0.0043 (8)	0.0049 (8)
C4	0.0303 (12)	0.0270 (11)	0.0352 (12)	0.0107 (9)	0.0045 (10)	0.0099 (9)
C2	0.0195 (10)	0.0243 (10)	0.0215 (10)	0.0044 (8)	0.0028 (8)	−0.0003 (8)
C8	0.0304 (12)	0.0301 (11)	0.0216 (10)	0.0045 (9)	0.0096 (9)	0.0083 (8)

S1—O4	1.4743 (14)	N13—H13A	0.8600
S1—O3	1.4766 (14)	N13—H13B	0.8600
S1—O1	1.4795 (14)	N14—C3	1.315 (3)
S1—O2	1.4806 (14)	N14—H14A	0.8600
S2—O5	1.4722 (14)	N14—H14B	0.8600
S2—O6	1.4732 (13)	C7—N17	1.309 (2)
S2—O7	1.4813 (14)	C7—C8	1.493 (3)
S2—O8	1.4822 (14)	N17—H17A	0.8600
N12—C1	1.308 (3)	N17—H17B	0.8600
N12—H12A	0.8600	C3—C4	1.494 (3)
N12—H12B	0.8600	C5—C6	1.487 (3)
N18—C7	1.309 (3)	C1—C2	1.492 (3)
N18—H18A	0.8600	C6—H6A	0.9600
N18—H18B	0.8600	C6—H6B	0.9600
N15—C5	1.308 (3)	C6—H6C	0.9600
N15—H15A	0.8600	C4—H4A	0.9600
N15—H15B	0.8600	C4—H4B	0.9600
N16—C5	1.316 (2)	C4—H4C	0.9600
N16—H16A	0.8600	C2—H2A	0.9600
N16—H16B	0.8600	C2—H2B	0.9600
N11—C1	1.313 (3)	C2—H2C	0.9600
N11—H11A	0.8600	C8—H8A	0.9600
N11—H11B	0.8600	C8—H8B	0.9600
N13—C3	1.303 (3)	C8—H8C	0.9600
O4—S1—O3	110.00 (8)	C7—N17—H17A	120.1
O4—S1—O1	110.05 (8)	C7—N17—H17B	119.9
O3—S1—O1	108.83 (8)	H17A—N17—H17B	120.0
O4—S1—O2	109.08 (8)	N13—C3—N14	121.98 (18)
O3—S1—O2	110.04 (8)	N13—C3—C4	119.16 (19)
O1—S1—O2	108.83 (9)	N14—C3—C4	118.87 (19)
O5—S2—O6	110.39 (8)	N15—C5—N16	121.47 (18)
O5—S2—O7	108.65 (8)	N15—C5—C6	119.04 (17)
O6—S2—O7	110.07 (8)	N16—C5—C6	119.49 (17)
O5—S2—O8	109.79 (8)	N12—C1—N11	121.67 (18)
O6—S2—O8	108.87 (8)	N12—C1—C2	119.00 (17)
O7—S2—O8	109.07 (9)	N11—C1—C2	119.31 (17)
C1—N12—H12A	120.1	C5—C6—H6A	109.5
C1—N12—H12B	119.9	C5—C6—H6B	109.5
H12A—N12—H12B	120.0	H6A—C6—H6B	109.5
C7—N18—H18A	120.1	C5—C6—H6C	109.5
C7—N18—H18B	119.8	H6A—C6—H6C	109.5
H18A—N18—H18B	120.1	H6B—C6—H6C	109.5
C5—N15—H15A	120.0	C3—C4—H4A	109.5
C5—N15—H15B	120.1	C3—C4—H4B	109.5
H15A—N15—H15B	119.9	H4A—C4—H4B	109.5
C5—N16—H16A	120.1	C3—C4—H4C	109.5
C5—N16—H16B	119.9	H4A—C4—H4C	109.5
H16A—N16—H16B	120.0	H4B—C4—H4C	109.5
C1—N11—H11A	120.0	C1—C2—H2A	109.5
C1—N11—H11B	120.0	C1—C2—H2B	109.5
H11A—N11—H11B	120.0	H2A—C2—H2B	109.5
C3—N13—H13A	120.1	C1—C2—H2C	109.5
C3—N13—H13B	119.9	H2A—C2—H2C	109.5
H13A—N13—H13B	120.0	H2B—C2—H2C	109.5
C3—N14—H14A	120.0	C7—C8—H8A	109.5
C3—N14—H14B	120.0	C7—C8—H8B	109.5
H14A—N14—H14B	120.0	H8A—C8—H8B	109.5
N18—C7—N17	121.79 (18)	C7—C8—H8C	109.5
N18—C7—C8	119.04 (18)	H8A—C8—H8C	109.5
N17—C7—C8	119.17 (18)	H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12A···O1i	0.86	2.02	2.838 (2)	158
N12—H12A···S1i	0.86	2.93	3.6038 (17)	136
N12—H12B···O6ii	0.86	1.99	2.843 (2)	172
N12—H12B···S2ii	0.86	2.98	3.7523 (17)	150
N18—H18A···O8	0.86	1.99	2.826 (2)	164
N18—H18A···S2	0.86	2.90	3.6006 (17)	140
N18—H18B···O3	0.86	1.99	2.823 (2)	164
N15—H15A···O2	0.86	2.03	2.841 (2)	157
N15—H15A···S1	0.86	2.92	3.5841 (17)	136
N15—H15B···S2	0.86	3.01	3.7829 (17)	150
N15—H15B···O5	0.86	1.97	2.817 (2)	169
N16—H16A···O1	0.86	2.09	2.915 (2)	160
N16—H16A···S1	0.86	2.85	3.5245 (18)	137
N16—H16B···O3iii	0.86	2.00	2.852 (2)	170
N16—H16B···S1iii	0.86	2.90	3.6821 (17)	152
N11—H11A···O2i	0.86	2.10	2.922 (2)	161
N11—H11A···S1i	0.86	2.84	3.5335 (17)	138
N11—H11B···O4iv	0.86	2.01	2.856 (2)	170
N11—H11B···S1iv	0.86	2.88	3.6657 (17)	152
N13—H13A···O7ii	0.86	1.99	2.826 (2)	165
N13—H13A···S2ii	0.86	2.93	3.6408 (18)	142
N13—H13B···O4i	0.86	1.99	2.835 (2)	165
N14—H14A···O8ii	0.86	2.09	2.938 (2)	167
N14—H14A···S2ii	0.86	2.87	3.5920 (18)	143
N14—H14B···O6iv	0.86	2.02	2.863 (2)	167
N14—H14B···S2iv	0.86	2.96	3.6973 (17)	145
N17—H17A···O7	0.86	2.12	2.964 (2)	167
N17—H17B···S2v	0.86	2.95	3.7158 (17)	149
N17—H17B···O5v	0.86	2.01	2.861 (2)	168
N17—H17B···S2v	0.86	2.95	3.7158 (17)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12A⋯O1i	0.86	2.02	2.838 (2)	158
N12—H12A⋯S1i	0.86	2.93	3.6038 (17)	136
N12—H12B⋯O6ii	0.86	1.99	2.843 (2)	172
N12—H12B⋯S2ii	0.86	2.98	3.7523 (17)	150
N18—H18A⋯O8	0.86	1.99	2.826 (2)	164
N18—H18A⋯S2	0.86	2.90	3.6006 (17)	140
N18—H18B⋯O3	0.86	1.99	2.823 (2)	164
N15—H15A⋯O2	0.86	2.03	2.841 (2)	157
N15—H15A⋯S1	0.86	2.92	3.5841 (17)	136
N15—H15B⋯S2	0.86	3.01	3.7829 (17)	150
N15—H15B⋯O5	0.86	1.97	2.817 (2)	169
N16—H16A⋯O1	0.86	2.09	2.915 (2)	160
N16—H16A⋯S1	0.86	2.85	3.5245 (18)	137
N16—H16B⋯O3iii	0.86	2.00	2.852 (2)	170
N16—H16B⋯S1iii	0.86	2.90	3.6821 (17)	152
N11—H11A⋯O2i	0.86	2.10	2.922 (2)	161
N11—H11A⋯S1i	0.86	2.84	3.5335 (17)	138
N11—H11B⋯O4iv	0.86	2.01	2.856 (2)	170
N11—H11B⋯S1iv	0.86	2.88	3.6657 (17)	152
N13—H13A⋯O7ii	0.86	1.99	2.826 (2)	165
N13—H13A⋯S2ii	0.86	2.93	3.6408 (18)	142
N13—H13B⋯O4i	0.86	1.99	2.835 (2)	165
N14—H14A⋯O8ii	0.86	2.09	2.938 (2)	167
N14—H14A⋯S2ii	0.86	2.87	3.5920 (18)	143
N14—H14B⋯O6iv	0.86	2.02	2.863 (2)	167
N14—H14B⋯S2iv	0.86	2.96	3.6973 (17)	145
N17—H17A⋯O7	0.86	2.12	2.964 (2)	167
N17—H17B⋯S2v	0.86	2.95	3.7158 (17)	149
N17—H17B⋯O5v	0.86	2.01	2.861 (2)	168
N17—H17B⋯S2v	0.86	2.95	3.7158 (17)	149

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