2-Amino-pyrimidin-1-ium 4-methyl-benzene-sulfonate.

In the crystal structure of the title compound, C(4)H(6)N(3) (+)·C(7)H(7)O(3)S(-), inter-molecular N-H⋯O hydrogen bonds link the cations and anions into chains along [100]. Additional stabilization is provided by weak C-H⋯O hydrogen bonds. An inter-molecular π-π stacking inter-action with a centroid-centroid distance of 3.6957 (7) Å is also observed. The H atoms of the methyl group were refined as disordered over two sets of sites with equal occupancies.

Related literature

For related structures, see: Tabatabaee et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C4H6N3 +·C7H7O3S−

M = 267.30

Monoclinic,

a = 6.2567 (3) Å

b = 13.3756 (6) Å

c = 15.2512 (7) Å

β = 101.335 (1)°

V = 1251.43 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.50 × 0.36 × 0.32 mm

Data collection

Bruker SMART APEXII diffractometer

12275 measured reflections

3617 independent reflections

3160 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.04

3617 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018198/lh5246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018198/lh5246Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018198/lh5246Isup3.cml

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

C4H6N3+·C7H7O3S−	F(000) = 560
Mr = 267.30	Dx = 1.419 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5926 reflections
a = 6.2567 (3) Å	θ = 2.7–34.6°
b = 13.3756 (6) Å	µ = 0.26 mm−1
c = 15.2512 (7) Å	T = 100 K
β = 101.335 (1)°	Prism, colourless
V = 1251.43 (10) Å3	0.50 × 0.36 × 0.32 mm
Z = 4

Bruker SMART APEXII diffractometer	3160 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 30.0°, θmin = 2.0°
ω scans	h = −8→8
12275 measured reflections	k = −18→18
3617 independent reflections	l = −21→21

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: difference Fourier map
wR(F2) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.3689P] where P = (Fo2 + 2Fc2)/3
3617 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.38 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	Occ. (<1)
S1	0.28924 (4)	0.172328 (19)	0.105904 (16)	0.01392 (8)
O1	0.28421 (13)	0.21695 (6)	0.19437 (5)	0.01877 (17)
O2	0.51293 (13)	0.15402 (6)	0.09590 (5)	0.01855 (16)
O3	0.14528 (13)	0.08711 (6)	0.08830 (5)	0.01966 (17)
C1	0.18525 (17)	0.26582 (8)	0.02687 (7)	0.01501 (19)
C2	−0.03778 (18)	0.27159 (8)	−0.00789 (7)	0.0183 (2)
H2A	−0.1349	0.2244	0.0096	0.022*
C3	−0.1167 (2)	0.34700 (9)	−0.06827 (8)	0.0220 (2)
H3A	−0.2687	0.3509	−0.0919	0.026*
C4	0.0232 (2)	0.41735 (9)	−0.09488 (8)	0.0236 (2)
C5	0.2456 (2)	0.41027 (9)	−0.05918 (8)	0.0254 (2)
H5A	0.3429	0.4576	−0.0764	0.031*
C6	0.3277 (2)	0.33500 (9)	0.00123 (8)	0.0213 (2)
H6A	0.4797	0.3309	0.0248	0.026*
C7	−0.0643 (3)	0.49831 (10)	−0.16093 (9)	0.0348 (3)
H7A	−0.1992	0.4752	−0.1997	0.052*	0.50
H7B	0.0438	0.5140	−0.1975	0.052*	0.50
H7C	−0.0944	0.5584	−0.1286	0.052*	0.50
H7D	0.0326	0.5565	−0.1508	0.052*	0.50
H7E	−0.2103	0.5178	−0.1530	0.052*	0.50
H7F	−0.0721	0.4734	−0.2219	0.052*	0.50
N1	0.61962 (15)	0.31572 (7)	0.29233 (6)	0.01640 (18)
H1A	0.5121	0.2804	0.2612	0.020*
N2	0.99877 (15)	0.33985 (7)	0.33945 (6)	0.01665 (18)
N3	0.86604 (16)	0.21369 (8)	0.23970 (7)	0.0210 (2)
H3B	1.0008	0.1961	0.2382	0.025*
H3C	0.7560	0.1808	0.2076	0.025*
C8	0.82865 (17)	0.29000 (8)	0.29050 (7)	0.0154 (2)
C9	0.57354 (18)	0.39454 (8)	0.34102 (7)	0.0177 (2)
H9A	0.4264	0.4116	0.3415	0.021*
C10	0.73953 (18)	0.44934 (8)	0.38933 (7)	0.0179 (2)
H10A	0.7132	0.5064	0.4228	0.022*
C11	0.95194 (17)	0.41679 (8)	0.38686 (7)	0.0170 (2)
H11A	1.0701	0.4525	0.4217	0.020*

	U11	U22	U33	U12	U13	U23
S1	0.01196 (12)	0.01471 (13)	0.01493 (13)	−0.00058 (8)	0.00229 (9)	−0.00101 (8)
O1	0.0151 (4)	0.0257 (4)	0.0156 (3)	−0.0016 (3)	0.0034 (3)	−0.0040 (3)
O2	0.0135 (4)	0.0209 (4)	0.0214 (4)	0.0022 (3)	0.0038 (3)	−0.0016 (3)
O3	0.0186 (4)	0.0161 (4)	0.0234 (4)	−0.0036 (3)	0.0017 (3)	0.0011 (3)
C1	0.0159 (5)	0.0137 (4)	0.0158 (4)	0.0009 (4)	0.0039 (4)	−0.0015 (4)
C2	0.0171 (5)	0.0189 (5)	0.0186 (5)	0.0003 (4)	0.0028 (4)	−0.0008 (4)
C3	0.0225 (5)	0.0222 (5)	0.0200 (5)	0.0044 (4)	0.0006 (4)	−0.0002 (4)
C4	0.0361 (7)	0.0172 (5)	0.0175 (5)	0.0044 (5)	0.0056 (4)	0.0002 (4)
C5	0.0324 (6)	0.0185 (5)	0.0274 (6)	−0.0025 (5)	0.0107 (5)	0.0029 (4)
C6	0.0191 (5)	0.0203 (5)	0.0252 (5)	−0.0023 (4)	0.0063 (4)	0.0008 (4)
C7	0.0563 (9)	0.0225 (6)	0.0245 (6)	0.0088 (6)	0.0054 (6)	0.0064 (5)
N1	0.0124 (4)	0.0201 (4)	0.0166 (4)	−0.0024 (3)	0.0026 (3)	−0.0015 (3)
N2	0.0138 (4)	0.0189 (4)	0.0169 (4)	−0.0014 (3)	0.0021 (3)	−0.0005 (3)
N3	0.0145 (4)	0.0258 (5)	0.0231 (5)	−0.0018 (4)	0.0043 (3)	−0.0087 (4)
C8	0.0138 (5)	0.0182 (5)	0.0145 (4)	−0.0008 (4)	0.0035 (3)	0.0012 (4)
C9	0.0163 (5)	0.0193 (5)	0.0180 (5)	0.0028 (4)	0.0048 (4)	0.0016 (4)
C10	0.0191 (5)	0.0164 (5)	0.0186 (5)	0.0010 (4)	0.0044 (4)	0.0000 (4)
C11	0.0165 (5)	0.0169 (5)	0.0168 (5)	−0.0029 (4)	0.0013 (4)	0.0003 (4)

S1—O3	1.4449 (8)	C7—H7C	0.9800
S1—O2	1.4580 (8)	C7—H7D	0.9800
S1—O1	1.4814 (8)	C7—H7E	0.9800
S1—C1	1.7697 (11)	C7—H7F	0.9800
C1—C6	1.3930 (15)	N1—C9	1.3529 (14)
C1—C2	1.3941 (15)	N1—C8	1.3579 (14)
C2—C3	1.3895 (16)	N1—H1A	0.8800
C2—H2A	0.9500	N2—C11	1.3233 (14)
C3—C4	1.3985 (18)	N2—C8	1.3500 (14)
C3—H3A	0.9500	N3—C8	1.3296 (14)
C4—C5	1.3946 (19)	N3—H3B	0.8800
C4—C7	1.5067 (17)	N3—H3C	0.8800
C5—C6	1.3929 (17)	C9—C10	1.3631 (15)
C5—H5A	0.9500	C9—H9A	0.9500
C6—H6A	0.9500	C10—C11	1.4060 (15)
C7—H7A	0.9800	C10—H10A	0.9500
C7—H7B	0.9800	C11—H11A	0.9500
O3—S1—O2	115.10 (5)	H7B—C7—H7D	56.3
O3—S1—O1	111.29 (5)	H7C—C7—H7D	56.3
O2—S1—O1	110.83 (5)	C4—C7—H7E	109.5
O3—S1—C1	107.38 (5)	H7A—C7—H7E	56.3
O2—S1—C1	106.22 (5)	H7B—C7—H7E	141.1
O1—S1—C1	105.36 (5)	H7C—C7—H7E	56.3
C6—C1—C2	120.29 (10)	H7D—C7—H7E	109.5
C6—C1—S1	119.39 (8)	C4—C7—H7F	109.5
C2—C1—S1	120.31 (8)	H7A—C7—H7F	56.3
C3—C2—C1	119.41 (11)	H7B—C7—H7F	56.3
C3—C2—H2A	120.3	H7C—C7—H7F	141.1
C1—C2—H2A	120.3	H7D—C7—H7F	109.5
C2—C3—C4	121.30 (11)	H7E—C7—H7F	109.5
C2—C3—H3A	119.4	C9—N1—C8	121.24 (9)
C4—C3—H3A	119.4	C9—N1—H1A	119.4
C5—C4—C3	118.33 (11)	C8—N1—H1A	119.4
C5—C4—C7	120.89 (12)	C11—N2—C8	116.81 (10)
C3—C4—C7	120.78 (12)	C8—N3—H3B	120.0
C6—C5—C4	121.14 (11)	C8—N3—H3C	120.0
C6—C5—H5A	119.4	H3B—N3—H3C	120.0
C4—C5—H5A	119.4	N3—C8—N2	119.44 (10)
C5—C6—C1	119.52 (11)	N3—C8—N1	119.13 (10)
C5—C6—H6A	120.2	N2—C8—N1	121.43 (10)
C1—C6—H6A	120.2	N1—C9—C10	119.59 (10)
C4—C7—H7A	109.5	N1—C9—H9A	120.2
C4—C7—H7B	109.5	C10—C9—H9A	120.2
H7A—C7—H7B	109.5	C9—C10—C11	116.28 (10)
C4—C7—H7C	109.5	C9—C10—H10A	121.9
H7A—C7—H7C	109.5	C11—C10—H10A	121.9
H7B—C7—H7C	109.5	N2—C11—C10	124.57 (10)
C4—C7—H7D	109.5	N2—C11—H11A	117.7
H7A—C7—H7D	141.1	C10—C11—H11A	117.7
O3—S1—C1—C6	−152.15 (9)	C7—C4—C5—C6	−179.36 (12)
O2—S1—C1—C6	−28.51 (10)	C4—C5—C6—C1	−0.34 (18)
O1—S1—C1—C6	89.14 (9)	C2—C1—C6—C5	0.24 (17)
O3—S1—C1—C2	29.29 (10)	S1—C1—C6—C5	−178.32 (9)
O2—S1—C1—C2	152.94 (9)	C11—N2—C8—N3	178.22 (10)
O1—S1—C1—C2	−89.42 (9)	C11—N2—C8—N1	−2.14 (15)
C6—C1—C2—C3	−0.06 (16)	C9—N1—C8—N3	−178.11 (10)
S1—C1—C2—C3	178.49 (9)	C9—N1—C8—N2	2.25 (16)
C1—C2—C3—C4	−0.03 (17)	C8—N1—C9—C10	−0.06 (16)
C2—C3—C4—C5	−0.07 (18)	N1—C9—C10—C11	−1.95 (15)
C2—C3—C4—C7	179.54 (11)	C8—N2—C11—C10	−0.04 (16)
C3—C4—C5—C6	0.25 (18)	C9—C10—C11—N2	2.07 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.79	2.674 (1)	176
N3—H3B···O1i	0.88	2.03	2.835 (1)	151
N3—H3C···O2	0.88	2.08	2.902 (1)	155
C10—H10A···O3ii	0.95	2.46	3.1035 (14)	124
C11—H11A···O3iii	0.95	2.56	3.3629 (14)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.88	1.79	2.674 (1)	176
N3—H3B⋯O1i	0.88	2.03	2.835 (1)	151
N3—H3C⋯O2	0.88	2.08	2.902 (1)	155
C10—H10A⋯O3ii	0.95	2.46	3.1035 (14)	124
C11—H11A⋯O3iii	0.95	2.56	3.3629 (14)	143

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