Bis(2-amino-pyrimidin-1-ium) sulfate.

In the title compound, 2C(4)H(6)N(3) (+)·SO(4) (2-), the cations are each essentially planar with r.m.s. deviations of the fitted atoms of 0.008 and 0.002 Å. In the crystal, adjacent ions are linked by N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the crystal structures of 2-amino­pyrimidinium salts with other anions, see: Cheng et al. (2010 ▶); Eshtiagh-Hosseini et al. (2010 ▶).

Experimental

Crystal data

2C4H6N3 +·SO4 2−

M = 288.30

Monoclinic,

a = 8.1215 (8) Å

b = 11.4853 (12) Å

c = 13.0407 (14) Å

β = 97.206 (2)°

V = 1206.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.45 × 0.29 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.880, T max = 0.955

6656 measured reflections

2377 independent reflections

1976 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.093

S = 1.05

2377 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037725/pv2583sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037725/pv2583Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037725/pv2583Isup3.cml

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

2C4H6N3+·SO42−	F(000) = 600
Mr = 288.30	Dx = 1.587 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3511 reflections
a = 8.1215 (8) Å	θ = 2.5–26.0°
b = 11.4853 (12) Å	µ = 0.29 mm−1
c = 13.0407 (14) Å	T = 293 K
β = 97.206 (2)°	Plate, colourless
V = 1206.8 (2) Å3	0.45 × 0.29 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2377 independent reflections
Radiation source: fine-focus sealed tube	1976 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ & ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.880, Tmax = 0.955	k = −14→8
6656 measured reflections	l = −16→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1486P] where P = (Fo2 + 2Fc2)/3
2377 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
S	0.01967 (5)	0.48062 (3)	0.75579 (3)	0.03308 (15)
C1	0.4028 (2)	0.33089 (14)	0.95900 (13)	0.0353 (4)
C2	0.3254 (2)	0.46070 (16)	1.08388 (13)	0.0422 (4)
H2A	0.2577	0.5207	1.1019	0.051*
C3	0.4431 (2)	0.41520 (16)	1.15527 (15)	0.0498 (5)
H3A	0.4602	0.4431	1.2227	0.060*
C4	0.5372 (2)	0.32455 (17)	1.12244 (15)	0.0507 (5)
H4A	0.6183	0.2919	1.1706	0.061*
C5	0.32224 (19)	0.58057 (14)	0.50457 (12)	0.0328 (4)
C6	0.4389 (2)	0.72057 (15)	0.40373 (14)	0.0435 (4)
H6A	0.4403	0.7583	0.3408	0.052*
C7	0.5485 (2)	0.75007 (17)	0.48542 (16)	0.0514 (5)
H7A	0.6271	0.8081	0.4808	0.062*
C8	0.5392 (2)	0.69007 (16)	0.57723 (15)	0.0483 (5)
H8A	0.6150	0.7092	0.6342	0.058*
N1	0.3820 (2)	0.29315 (15)	0.86293 (12)	0.0455 (4)
H1NA	0.312 (2)	0.3295 (18)	0.8188 (16)	0.050 (6)*
H1NB	0.435 (3)	0.227 (2)	0.8471 (16)	0.065 (6)*
N2	0.30658 (17)	0.41906 (12)	0.98686 (11)	0.0362 (3)
H2N	0.230 (2)	0.4489 (17)	0.9436 (15)	0.042 (5)*
N3	0.51952 (18)	0.28162 (13)	1.02800 (12)	0.0458 (4)
N4	0.2118 (2)	0.49912 (14)	0.51195 (14)	0.0425 (4)
H4NA	0.207 (2)	0.4694 (18)	0.5680 (17)	0.047 (6)*
H4NB	0.157 (2)	0.4774 (17)	0.4623 (17)	0.044 (6)*
N5	0.32700 (18)	0.63601 (13)	0.41351 (11)	0.0365 (3)
H5N	0.258 (3)	0.6232 (18)	0.3654 (17)	0.055 (6)*
N6	0.43008 (17)	0.60804 (13)	0.58842 (11)	0.0407 (4)
O1	0.16275 (15)	0.42397 (11)	0.71839 (9)	0.0458 (3)
O2	0.06654 (16)	0.51991 (11)	0.86283 (9)	0.0481 (3)
O3	−0.03729 (15)	0.57920 (10)	0.68927 (9)	0.0455 (3)
O4	−0.11722 (15)	0.39661 (11)	0.75484 (9)	0.0470 (3)

	U11	U22	U33	U12	U13	U23
S	0.0389 (2)	0.0320 (2)	0.0269 (2)	−0.00002 (16)	−0.00122 (16)	0.00050 (15)
C1	0.0331 (8)	0.0321 (8)	0.0402 (9)	−0.0035 (6)	0.0027 (7)	0.0042 (7)
C2	0.0478 (10)	0.0425 (10)	0.0379 (10)	−0.0031 (8)	0.0115 (8)	0.0015 (7)
C3	0.0645 (12)	0.0507 (12)	0.0324 (9)	−0.0060 (9)	−0.0003 (8)	0.0056 (8)
C4	0.0527 (11)	0.0497 (11)	0.0454 (11)	−0.0019 (9)	−0.0103 (9)	0.0149 (8)
C5	0.0334 (8)	0.0348 (9)	0.0300 (8)	0.0057 (7)	0.0039 (6)	−0.0010 (6)
C6	0.0446 (10)	0.0397 (10)	0.0475 (10)	0.0027 (8)	0.0106 (8)	0.0083 (8)
C7	0.0492 (11)	0.0425 (11)	0.0611 (12)	−0.0085 (9)	0.0010 (9)	0.0039 (9)
C8	0.0470 (10)	0.0452 (11)	0.0496 (11)	−0.0040 (9)	−0.0064 (8)	−0.0052 (9)
N1	0.0529 (10)	0.0413 (9)	0.0402 (9)	0.0099 (7)	−0.0023 (7)	−0.0033 (7)
N2	0.0327 (7)	0.0390 (8)	0.0359 (8)	0.0016 (6)	0.0011 (6)	0.0042 (6)
N3	0.0454 (8)	0.0429 (9)	0.0468 (9)	0.0057 (7)	−0.0030 (7)	0.0083 (7)
N4	0.0437 (9)	0.0510 (10)	0.0318 (8)	−0.0089 (7)	0.0005 (7)	0.0033 (7)
N5	0.0367 (8)	0.0414 (8)	0.0306 (8)	0.0012 (6)	0.0013 (6)	0.0015 (6)
N6	0.0427 (8)	0.0446 (9)	0.0334 (7)	−0.0002 (6)	−0.0012 (6)	−0.0012 (6)
O1	0.0516 (7)	0.0509 (8)	0.0354 (7)	0.0103 (6)	0.0074 (5)	0.0021 (5)
O2	0.0541 (8)	0.0532 (8)	0.0334 (7)	0.0134 (6)	−0.0093 (5)	−0.0125 (5)
O3	0.0528 (7)	0.0358 (7)	0.0451 (7)	−0.0001 (5)	−0.0055 (6)	0.0084 (5)
O4	0.0518 (8)	0.0488 (8)	0.0387 (7)	−0.0128 (6)	−0.0012 (5)	0.0086 (5)

S—O3	1.4656 (12)	C5—N6	1.350 (2)
S—O1	1.4675 (13)	C5—N5	1.352 (2)
S—O4	1.4709 (12)	C6—C7	1.343 (3)
S—O2	1.4710 (12)	C6—N5	1.347 (2)
C1—N1	1.316 (2)	C6—H6A	0.9300
C1—N3	1.347 (2)	C7—C8	1.392 (3)
C1—N2	1.356 (2)	C7—H7A	0.9300
C2—N2	1.343 (2)	C8—N6	1.314 (2)
C2—C3	1.353 (3)	C8—H8A	0.9300
C2—H2A	0.9300	N1—H1NA	0.86 (2)
C3—C4	1.390 (3)	N1—H1NB	0.91 (2)
C3—H3A	0.9300	N2—H2N	0.86 (2)
C4—N3	1.318 (2)	N4—H4NA	0.81 (2)
C4—H4A	0.9300	N4—H4NB	0.78 (2)
C5—N4	1.308 (2)	N5—H5N	0.80 (2)
O3—S—O1	110.49 (8)	C7—C6—H6A	120.2
O3—S—O4	108.64 (7)	N5—C6—H6A	120.2
O1—S—O4	109.60 (8)	C6—C7—C8	117.11 (17)
O3—S—O2	110.46 (7)	C6—C7—H7A	121.4
O1—S—O2	109.27 (7)	C8—C7—H7A	121.4
O4—S—O2	108.34 (8)	N6—C8—C7	124.08 (17)
N1—C1—N3	119.53 (16)	N6—C8—H8A	118.0
N1—C1—N2	119.43 (16)	C7—C8—H8A	118.0
N3—C1—N2	121.03 (16)	C1—N1—H1NA	118.1 (14)
N2—C2—C3	119.86 (17)	C1—N1—H1NB	119.0 (14)
N2—C2—H2A	120.1	H1NA—N1—H1NB	122.7 (19)
C3—C2—H2A	120.1	C2—N2—C1	121.12 (15)
C2—C3—C4	116.45 (18)	C2—N2—H2N	117.7 (13)
C2—C3—H3A	121.8	C1—N2—H2N	121.2 (13)
C4—C3—H3A	121.8	C4—N3—C1	116.88 (16)
N3—C4—C3	124.65 (16)	C5—N4—H4NA	118.6 (14)
N3—C4—H4A	117.7	C5—N4—H4NB	119.6 (15)
C3—C4—H4A	117.7	H4NA—N4—H4NB	122 (2)
N4—C5—N6	119.26 (15)	C6—N5—C5	121.10 (16)
N4—C5—N5	119.79 (15)	C6—N5—H5N	118.3 (15)
N6—C5—N5	120.95 (15)	C5—N5—H5N	120.4 (15)
C7—C6—N5	119.64 (17)	C8—N6—C5	117.11 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O1	0.86 (2)	1.99 (2)	2.853 (2)	175.5 (17)
N1—H1NB···O3i	0.91 (2)	1.97 (2)	2.882 (2)	176.9 (2)
N2—H2N···O2	0.86 (2)	1.79 (2)	2.640 (2)	174.7 (18)
N4—H4NA···O1	0.81 (2)	2.10 (2)	2.902 (2)	167.6 (19)
N4—H4NB···O3ii	0.78 (2)	2.19 (2)	2.962 (2)	171.0 (2)
N5—H5N···O4ii	0.80 (2)	1.84 (2)	2.631 (2)	172.6 (2)
C2—H2A···O4iii	0.93	2.50	3.295 (2)	144
C3—H3A···N6iv	0.93	2.58	3.382 (2)	145
C4—H4A···O1v	0.93	2.57	3.231 (2)	128
C7—H7A···O2vi	0.93	2.51	3.101 (2)	121
C8—H8A···O4vii	0.93	2.59	3.237 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O1	0.86 (2)	1.99 (2)	2.853 (2)	175.5 (17)
N1—H1NB⋯O3i	0.91 (2)	1.97 (2)	2.882 (2)	176.9 (2)
N2—H2N⋯O2	0.86 (2)	1.79 (2)	2.640 (2)	174.7 (18)
N4—H4NA⋯O1	0.81 (2)	2.10 (2)	2.902 (2)	167.6 (19)
N4—H4NB⋯O3ii	0.78 (2)	2.19 (2)	2.962 (2)	171.0 (2)
N5—H5N⋯O4ii	0.80 (2)	1.84 (2)	2.631 (2)	172.6 (2)
C2—H2A⋯O4iii	0.93	2.50	3.295 (2)	144
C3—H3A⋯N6iv	0.93	2.58	3.382 (2)	145
C4—H4A⋯O1v	0.93	2.57	3.231 (2)	128
C7—H7A⋯O2vi	0.93	2.51	3.101 (2)	121
C8—H8A⋯O4vii	0.93	2.59	3.237 (2)	127

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