Pyrimidine-2,4-diamine acetone monosolvate.

In the title compound, C(4)H(6)N(4)·C(3)H(6)O, the pyrimidine-2,4-diamine mol-ecule is nearly planar (r.m.s. deviation = 0.005 Å), with the endocyclic angles covering the range 114.36 (10)-126.31 (10)°. In the crystal, N-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into ribbons along [101], and weak C-H⋯π inter-actions consolidate further the crystal packing.

Related literature

For the biological activity of pyrimidine derivatives, see: Hall et al. (1993 ▶); Gengeliczki et al. (2011 ▶). For the crystal structures of related compounds, see: Bertolasi et al. (2002 ▶); Draguta et al. (2012 ▶). For bond lengths in organic compounds, see: Allen et al. (1987 ▶). For hydrogen-bonding graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C4H6N4·C3H6O

M = 168.21

Monoclinic,

a = 8.1594 (15) Å

b = 12.728 (2) Å

c = 8.7663 (16) Å

β = 99.395 (3)°

V = 898.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.974, T max = 0.982

9693 measured reflections

2170 independent reflections

1752 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.07

2170 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001025/cv5381sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001025/cv5381Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001025/cv5381Isup3.cml

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

C4H6N4·C3H6O	F(000) = 360
Mr = 168.21	Dx = 1.244 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8851 reflections
a = 8.1594 (15) Å	θ = 2.3–32.1°
b = 12.728 (2) Å	µ = 0.09 mm−1
c = 8.7663 (16) Å	T = 296 K
β = 99.395 (3)°	Prism, colourless
V = 898.2 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	2170 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.974, Tmax = 0.982	k = −16→16
9693 measured reflections	l = −11→11

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0884P)2] where P = (Fo2 + 2Fc2)/3
2170 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.28 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
N1	0.12301 (13)	0.39554 (8)	0.11848 (12)	0.0224 (3)
C2	0.19664 (15)	0.47490 (9)	0.20658 (14)	0.0191 (3)
N2	0.14277 (14)	0.57309 (9)	0.16744 (13)	0.0255 (3)
H2A	0.0691 (19)	0.5838 (13)	0.0852 (18)	0.025 (4)*
H2B	0.197 (2)	0.6249 (13)	0.2183 (19)	0.033 (4)*
N3	0.31691 (12)	0.46530 (8)	0.33213 (12)	0.0187 (3)
C4	0.36727 (15)	0.36728 (9)	0.37483 (14)	0.0190 (3)
N4	0.48650 (14)	0.35701 (8)	0.49903 (13)	0.0240 (3)
H4A	0.5237 (19)	0.2944 (14)	0.5294 (18)	0.033 (4)*
H4B	0.539 (2)	0.4120 (14)	0.5498 (19)	0.031 (4)*
C5	0.29627 (16)	0.27903 (10)	0.29098 (15)	0.0245 (3)
H5	0.3283	0.2109	0.3202	0.029*
C6	0.17840 (16)	0.29891 (10)	0.16502 (15)	0.0248 (3)
H6	0.1329	0.2417	0.1070	0.030*
O1	0.28515 (12)	0.78374 (7)	0.30884 (11)	0.0285 (3)
C7	0.30086 (19)	0.97014 (11)	0.31631 (19)	0.0333 (4)
H7A	0.3699	0.9583	0.4144	0.050*
H7B	0.2067	1.0120	0.3308	0.050*
H7C	0.3635	1.0063	0.2489	0.050*
C8	0.24238 (15)	0.86704 (9)	0.24592 (14)	0.0223 (3)
C9	0.12660 (17)	0.86932 (11)	0.09351 (16)	0.0297 (3)
H9A	0.1316	0.8032	0.0418	0.045*
H9B	0.1592	0.9246	0.0303	0.045*
H9C	0.0151	0.8816	0.1112	0.045*

	U11	U22	U33	U12	U13	U23
N1	0.0249 (6)	0.0168 (5)	0.0226 (5)	−0.0012 (4)	−0.0046 (4)	−0.0021 (4)
C2	0.0203 (6)	0.0162 (6)	0.0199 (6)	−0.0007 (4)	0.0003 (5)	−0.0009 (4)
N2	0.0304 (6)	0.0153 (6)	0.0260 (6)	−0.0001 (4)	−0.0093 (5)	0.0003 (4)
N3	0.0209 (5)	0.0125 (5)	0.0212 (5)	−0.0003 (4)	−0.0012 (4)	0.0001 (4)
C4	0.0190 (6)	0.0155 (6)	0.0217 (6)	−0.0001 (4)	0.0006 (4)	0.0003 (4)
N4	0.0255 (6)	0.0134 (5)	0.0288 (6)	0.0008 (4)	−0.0080 (4)	0.0012 (4)
C5	0.0270 (7)	0.0138 (6)	0.0303 (7)	0.0007 (5)	−0.0025 (5)	−0.0011 (5)
C6	0.0279 (7)	0.0162 (6)	0.0277 (6)	−0.0012 (5)	−0.0027 (5)	−0.0046 (5)
O1	0.0325 (5)	0.0184 (5)	0.0314 (5)	0.0024 (4)	−0.0042 (4)	0.0037 (4)
C7	0.0376 (8)	0.0210 (7)	0.0424 (8)	−0.0053 (6)	0.0099 (6)	−0.0066 (6)
C8	0.0217 (6)	0.0182 (6)	0.0268 (6)	0.0007 (5)	0.0029 (5)	0.0014 (5)
C9	0.0271 (7)	0.0311 (7)	0.0289 (7)	0.0032 (5)	−0.0017 (5)	0.0059 (5)

N1—C6	1.3503 (16)	C5—H5	0.9300
N1—C2	1.3513 (16)	C6—H6	0.9300
C2—N2	1.3505 (16)	O1—C8	1.2196 (15)
C2—N3	1.3552 (16)	C7—C8	1.4948 (18)
N2—H2A	0.871 (16)	C7—H7A	0.9600
N2—H2B	0.875 (18)	C7—H7B	0.9600
N3—C4	1.3474 (15)	C7—H7C	0.9600
C4—N4	1.3428 (16)	C8—C9	1.5054 (18)
C4—C5	1.4137 (17)	C9—H9A	0.9600
N4—H4A	0.879 (17)	C9—H9B	0.9600
N4—H4B	0.900 (18)	C9—H9C	0.9600
C5—C6	1.3644 (18)
C6—N1—C2	114.36 (11)	N1—C6—H6	117.6
N2—C2—N1	116.78 (11)	C5—C6—H6	117.6
N2—C2—N3	116.88 (11)	C8—C7—H7A	109.5
N1—C2—N3	126.32 (11)	C8—C7—H7B	109.5
C2—N2—H2A	120.5 (11)	H7A—C7—H7B	109.5
C2—N2—H2B	116.9 (11)	C8—C7—H7C	109.5
H2A—N2—H2B	121.8 (15)	H7A—C7—H7C	109.5
C4—N3—C2	117.17 (10)	H7B—C7—H7C	109.5
N4—C4—N3	117.59 (11)	O1—C8—C7	121.87 (12)
N4—C4—C5	121.69 (11)	O1—C8—C9	120.66 (11)
N3—C4—C5	120.71 (11)	C7—C8—C9	117.47 (12)
C4—N4—H4A	120.2 (11)	C8—C9—H9A	109.5
C4—N4—H4B	123.3 (10)	C8—C9—H9B	109.5
H4A—N4—H4B	116.2 (15)	H9A—C9—H9B	109.5
C6—C5—C4	116.64 (12)	C8—C9—H9C	109.5
C6—C5—H5	121.7	H9A—C9—H9C	109.5
C4—C5—H5	121.7	H9B—C9—H9C	109.5
N1—C6—C5	124.78 (11)
C6—N1—C2—N2	−178.34 (11)	C2—N3—C4—C5	−0.04 (18)
C6—N1—C2—N3	0.25 (19)	N4—C4—C5—C6	−178.77 (12)
N2—C2—N3—C4	177.85 (11)	N3—C4—C5—C6	1.21 (19)
N1—C2—N3—C4	−0.75 (19)	C2—N1—C6—C5	1.10 (19)
C2—N3—C4—N4	179.95 (11)	C4—C5—C6—N1	−1.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.875 (18)	2.191 (18)	3.0608 (18)	177.3 (15)
N2—H2B···O1	0.871 (16)	2.247 (19)	3.0990 (17)	164.7 (16)
N4—H4A···O1ii	0.879 (17)	2.170 (18)	2.9141 (16)	142.2 (15)
N4—H4B···N3ii	0.900 (18)	2.120 (19)	3.0171 (17)	174.9 (15)
C9—H9C···Cgiii	0.96	2.63	3.5484 (17)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the pyrimidine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.875 (18)	2.191 (18)	3.0608 (18)	177.3 (15)
N2—H2B⋯O1	0.871 (16)	2.247 (19)	3.0990 (17)	164.7 (16)
N4—H4A⋯O1ii	0.879 (17)	2.170 (18)	2.9141 (16)	142.2 (15)
N4—H4B⋯N3ii	0.900 (18)	2.120 (19)	3.0171 (17)	174.9 (15)
C9—H9C⋯Cg iii	0.96	2.63	3.5484 (17)	159

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