2-Amino-4,6-di-methyl-pyrimidine-sorbic acid (1/1).

In the crystal of the title compound, C6H9N3·C6H8O2, the 2-amino-4,6-di-methyl-pyrimidine and sorbic acid mol-ecules are linked through N-H⋯O and O-H⋯N hydrogen bonds, which generate a cyclic bimolecular heterosynthon with an R 2 (2)(8) graph-set motif. Further, two inversion-related pyrimidine mol-ecules are base-paired via a pair of N-H⋯N hydrogen bonds, forming a cyclic bimolecular homosynthon with a graph-set of R 2 (2)(8). A discrete hetero tetra-meric supra-molecular unit along the b axis is formed by the fusion of two heterosynthons and one homosynthon. An aromatic π-π inter-action [centroid-centroid distance = 3.7945 (16) Å] is observed between these tetra-meric units.

Related literature

For amino­pyrimidine–carb­oxy­lic acid inter­actions, see: Hunt et al. (1980 ▶). For related structures, see: Thanigaimani et al. (2007 ▶); Ebenezer & Mu­thiah (2010 ▶, 2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C6H9N3·C6H8O2

M = 235.29

Triclinic,

a = 7.8441 (6) Å

b = 9.9413 (8) Å

c = 10.2846 (13) Å

α = 112.058 (7)°

β = 98.333 (8)°

γ = 111.306 (5)°

V = 654.69 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.12 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.990, T max = 0.993

9667 measured reflections

2280 independent reflections

1585 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.210

S = 1.03

2280 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2008 ▶) and POV-RAY (Cason, 2004 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018175/is5286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018175/is5286Isup2.hkl

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

C6H9N3·C6H8O2	Z = 2
Mr = 235.29	F(000) = 252
Triclinic, P1	Dx = 1.194 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8441 (6) Å	Cell parameters from 2280 reflections
b = 9.9413 (8) Å	θ = 2.3–25.1°
c = 10.2846 (13) Å	µ = 0.08 mm−1
α = 112.058 (7)°	T = 296 K
β = 98.333 (8)°	Prism, colourless
γ = 111.306 (5)°	0.12 × 0.11 × 0.09 mm
V = 654.69 (13) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2280 independent reflections
Radiation source: fine-focus sealed tube	1585 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.990, Tmax = 0.993	k = −11→11
9667 measured reflections	l = −12→12

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1185P)2 + 0.152P] where P = (Fo2 + 2Fc2)/3
2280 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N1	0.2301 (3)	0.2463 (2)	0.49425 (19)	0.0543 (7)
N2	0.0413 (4)	0.3650 (3)	0.5821 (3)	0.0802 (10)
N3	0.1624 (3)	0.4209 (2)	0.40922 (19)	0.0554 (7)
C2	0.1464 (3)	0.3438 (3)	0.4937 (2)	0.0539 (7)
C4	0.2658 (3)	0.3961 (3)	0.3191 (2)	0.0567 (8)
C5	0.3524 (4)	0.2964 (3)	0.3122 (3)	0.0652 (9)
C6	0.3326 (3)	0.2233 (3)	0.4030 (2)	0.0582 (8)
C7	0.2823 (4)	0.4809 (4)	0.2244 (3)	0.0739 (10)
C8	0.4239 (5)	0.1142 (4)	0.4044 (3)	0.0839 (11)
O1	0.0710 (4)	0.2287 (3)	0.7892 (2)	0.1067 (10)
O2	0.2211 (3)	0.1013 (2)	0.6675 (2)	0.0774 (8)
C9	0.1482 (4)	0.1403 (3)	0.7730 (3)	0.0673 (9)
C10	0.1635 (4)	0.0674 (3)	0.8719 (3)	0.0765 (10)
C11	0.2168 (3)	−0.0479 (3)	0.8489 (3)	0.0625 (8)
C12	0.2269 (4)	−0.1235 (3)	0.9435 (3)	0.0713 (9)
C13	0.2681 (4)	−0.2440 (4)	0.9157 (3)	0.0788 (11)
C14	0.2767 (5)	−0.3265 (4)	1.0101 (4)	0.0994 (14)
H2A	−0.017 (4)	0.428 (3)	0.589 (3)	0.072 (7)*
H2B	0.036 (4)	0.321 (4)	0.640 (4)	0.095 (10)*
H5	0.42270	0.27890	0.24760	0.0780*
H7A	0.17580	0.41340	0.13310	0.1110*
H7B	0.40180	0.50070	0.20330	0.1110*
H7C	0.27990	0.58280	0.27620	0.1110*
H8A	0.49650	0.14980	0.50460	0.1250*
H8B	0.50880	0.11920	0.34600	0.1250*
H8C	0.32460	0.00410	0.36340	0.1250*
H2	0.212 (5)	0.160 (4)	0.610 (4)	0.125 (12)*
H10	0.13270	0.10620	0.95800	0.0920*
H11	0.25130	−0.08420	0.76420	0.0750*
H12	0.20160	−0.08200	1.03180	0.0860*
H13	0.29520	−0.28350	0.82780	0.0940*
H14A	0.20900	−0.30130	1.07910	0.1480*
H14B	0.40940	−0.28880	1.06350	0.1480*
H14C	0.21730	−0.44230	0.94810	0.1480*

	U11	U22	U33	U12	U13	U23
N1	0.0710 (12)	0.0621 (12)	0.0571 (10)	0.0416 (10)	0.0276 (9)	0.0408 (9)
N2	0.129 (2)	0.1113 (19)	0.0869 (15)	0.0945 (18)	0.0700 (15)	0.0785 (15)
N3	0.0718 (12)	0.0614 (12)	0.0544 (10)	0.0374 (10)	0.0231 (9)	0.0399 (9)
C2	0.0704 (14)	0.0616 (13)	0.0540 (11)	0.0398 (12)	0.0244 (10)	0.0395 (10)
C4	0.0640 (13)	0.0602 (14)	0.0558 (12)	0.0265 (12)	0.0198 (10)	0.0382 (11)
C5	0.0774 (16)	0.0819 (17)	0.0676 (14)	0.0467 (14)	0.0384 (12)	0.0496 (13)
C6	0.0665 (14)	0.0676 (15)	0.0602 (13)	0.0393 (12)	0.0246 (11)	0.0387 (11)
C7	0.0909 (18)	0.0837 (18)	0.0752 (16)	0.0404 (15)	0.0363 (14)	0.0601 (15)
C8	0.109 (2)	0.106 (2)	0.0947 (19)	0.0792 (19)	0.0544 (17)	0.0657 (18)
O1	0.191 (2)	0.1244 (18)	0.1037 (15)	0.1172 (19)	0.0929 (16)	0.0885 (14)
O2	0.1068 (14)	0.1015 (14)	0.0864 (12)	0.0691 (12)	0.0541 (11)	0.0747 (11)
C9	0.0954 (18)	0.0668 (15)	0.0625 (14)	0.0436 (15)	0.0318 (13)	0.0433 (12)
C10	0.119 (2)	0.0733 (17)	0.0605 (14)	0.0492 (17)	0.0374 (14)	0.0455 (13)
C11	0.0651 (14)	0.0676 (15)	0.0638 (13)	0.0235 (12)	0.0200 (11)	0.0460 (12)
C12	0.0867 (18)	0.0665 (16)	0.0652 (14)	0.0271 (14)	0.0169 (12)	0.0453 (13)
C13	0.0751 (17)	0.092 (2)	0.102 (2)	0.0383 (16)	0.0352 (15)	0.0739 (18)
C14	0.099 (2)	0.093 (2)	0.128 (3)	0.0343 (18)	0.0218 (19)	0.087 (2)

O1—C9	1.214 (5)	C7—H7A	0.9600
O2—C9	1.296 (4)	C8—H8C	0.9600
O2—H2	0.99 (4)	C8—H8A	0.9600
N1—C2	1.355 (4)	C8—H8B	0.9600
N1—C6	1.331 (3)	C9—C10	1.468 (4)
N2—C2	1.323 (4)	C10—C11	1.311 (4)
N3—C4	1.330 (3)	C11—C12	1.445 (4)
N3—C2	1.349 (3)	C12—C13	1.293 (5)
N2—H2A	0.89 (3)	C13—C14	1.496 (5)
N2—H2B	0.86 (4)	C10—H10	0.9300
C4—C7	1.500 (4)	C11—H11	0.9300
C4—C5	1.378 (4)	C12—H12	0.9300
C5—C6	1.376 (4)	C13—H13	0.9300
C6—C8	1.504 (5)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C7—H7C	0.9600	C14—H14C	0.9600
C7—H7B	0.9600
O1···N2	2.946 (4)	H2···C8	2.88 (4)
O2···N1	2.674 (3)	H2···C6	2.64 (4)
O2···C8	3.351 (4)	H2A···N3iv	2.19 (3)
O1···H14Ai	2.9100	H2A···C4iv	3.09 (3)
O1···H2B	2.10 (4)	H2B···C9	2.92 (4)
O1···H14Cii	2.7200	H2B···O1	2.10 (4)
O1···H8Ciii	2.8400	H2B···H2	2.43 (6)
O2···H11	2.4600	H5···H7B	2.4700
N1···O2	2.674 (3)	H5···H8B	2.4100
N2···N3iv	3.076 (4)	H5···H13viii	2.4400
N2···O1	2.946 (4)	H7B···H5	2.4700
N3···N2iv	3.076 (4)	H7C···H8Aix	2.4900
N1···H2	1.70 (4)	H8A···H7Cix	2.4900
N2···H2	2.89 (4)	H8B···H5	2.4100
N3···H2Aiv	2.19 (3)	H8B···H11viii	2.4000
C2···C11iii	3.521 (3)	H8C···O1iii	2.8400
C7···C14v	3.425 (5)	H10···H12	2.4600
C8···O2	3.351 (4)	H10···H12i	2.5700
C11···C2iii	3.521 (3)	H11···O2	2.4600
C14···C7vi	3.425 (5)	H11···H13	2.4200
C2···H2	2.68 (4)	H11···H8Bviii	2.4000
C4···H2Aiv	3.09 (3)	H12···H10	2.4600
C6···H2	2.64 (4)	H12···H14A	2.4200
C8···H2	2.88 (4)	H12···H10i	2.5700
C9···H2B	2.92 (4)	H13···H11	2.4200
C10···H14Bvii	3.0700	H13···H5viii	2.4400
H2···N2	2.89 (4)	H14A···H12	2.4200
H2···C2	2.68 (4)	H14A···O1i	2.9100
H2···N1	1.70 (4)	H14B···C10vii	3.0700
H2···H2B	2.43 (6)	H14C···O1x	2.7200
C9—O2—H2	110 (2)	C6—C8—H8A	109.00
C2—N1—C6	117.4 (2)	H8A—C8—H8C	110.00
C2—N3—C4	116.8 (2)	H8B—C8—H8C	109.00
C2—N2—H2B	118 (2)	H8A—C8—H8B	109.00
H2A—N2—H2B	119 (3)	O1—C9—C10	121.9 (3)
C2—N2—H2A	123.3 (19)	O2—C9—C10	114.8 (3)
N1—C2—N2	117.8 (2)	O1—C9—O2	123.3 (3)
N2—C2—N3	117.5 (3)	C9—C10—C11	125.5 (3)
N1—C2—N3	124.7 (2)	C10—C11—C12	125.8 (3)
C5—C4—C7	121.6 (2)	C11—C12—C13	125.5 (3)
N3—C4—C7	116.8 (2)	C12—C13—C14	126.8 (3)
N3—C4—C5	121.7 (2)	C9—C10—H10	117.00
C4—C5—C6	118.6 (3)	C11—C10—H10	117.00
N1—C6—C8	116.8 (2)	C10—C11—H11	117.00
C5—C6—C8	122.3 (3)	C12—C11—H11	117.00
N1—C6—C5	120.9 (3)	C11—C12—H12	117.00
C6—C5—H5	121.00	C13—C12—H12	117.00
C4—C5—H5	121.00	C12—C13—H13	117.00
C4—C7—H7A	109.00	C14—C13—H13	117.00
C4—C7—H7C	109.00	C13—C14—H14A	109.00
H7A—C7—H7B	109.00	C13—C14—H14B	109.00
C4—C7—H7B	109.00	C13—C14—H14C	109.00
H7B—C7—H7C	109.00	H14A—C14—H14B	110.00
H7A—C7—H7C	110.00	H14A—C14—H14C	110.00
C6—C8—H8B	109.00	H14B—C14—H14C	109.00
C6—C8—H8C	109.00
C6—N1—C2—N2	178.8 (2)	C7—C4—C5—C6	179.5 (3)
C6—N1—C2—N3	−1.1 (3)	C4—C5—C6—N1	0.9 (4)
C2—N1—C6—C5	0.1 (3)	C4—C5—C6—C8	−179.3 (3)
C2—N1—C6—C8	−179.7 (2)	O1—C9—C10—C11	168.8 (3)
C4—N3—C2—N1	1.1 (3)	O2—C9—C10—C11	−10.4 (5)
C4—N3—C2—N2	−178.9 (2)	C9—C10—C11—C12	−178.1 (3)
C2—N3—C4—C5	0.0 (3)	C10—C11—C12—C13	175.5 (3)
C2—N3—C4—C7	179.6 (2)	C11—C12—C13—C14	−179.0 (3)
N3—C4—C5—C6	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.99 (4)	1.70 (4)	2.674 (3)	167 (4)
N2—H2A···N3iv	0.89 (3)	2.19 (3)	3.076 (4)	176 (2)
N2—H2B···O1	0.86 (4)	2.10 (4)	2.946 (4)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.99 (4)	1.70 (4)	2.674 (3)	167 (4)
N2—H2A⋯N3i	0.89 (3)	2.19 (3)	3.076 (4)	176 (2)
N2—H2B⋯O1	0.86 (4)	2.10 (4)	2.946 (4)	171 (3)

Symmetry code: (i) .