Acetoguanamine N,N-dimethyl-formamide solvate.

The structure of acetoguanamine (or 2,4-diamino-6-methyl-1,3,5-triazine) has been determined as the N,N-dimethyl-formamide solvate, C(4)H(7)N(5)·C(3)H(7)NO. The mol-ecular components are associated in the crystal structure to form ribbons stabilized by three N-H⋯N and one N-H⋯O hydrogen bonds which involve NH groups as donors and the N atoms of the heterocyclic ring and the carbonyl O atom of the solvent as acceptors.

Related literature

For related literature, see: Portalone & Colapietro (2007a ▶). For a general approach to the use of multiple-hydrogen-bonding DNA/RNA nucleobases as potential supra­molecular reagents, see: Portalone et al. (1999 ▶); Portalone & Colapietro (2007a ▶,b ▶ and references therein). For the computation of ring patterns formed by hydrogen bonds in crystal structures, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶); Motherwell et al. (1999 ▶).

Experimental

Crystal data

C4H7N5·C3H7NO

M = 198.24

Orthorhombic,

a = 25.548 (2) Å

b = 23.0626 (19) Å

c = 7.2689 (9) Å

V = 4282.8 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.15 × 0.14 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.985, T max = 0.990

27177 measured reflections

1127 independent reflections

698 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.127

S = 0.91

1127 reflections

132 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3? (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023842/tk2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023842/tk2285Isup2.hkl

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

C4H7N5·C3H7NO	F000 = 1696
Mr = 198.24	Dx = 1.230 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 11018 reflections
a = 25.548 (2) Å	θ = 3.0–25.6º
b = 23.0626 (19) Å	µ = 0.09 mm−1
c = 7.2689 (9) Å	T = 298 (2) K
V = 4282.8 (7) Å3	Tablets, colourless
Z = 16	0.15 × 0.14 × 0.14 mm

Oxford Diffraction Xcalibur S CCD diffractometer	1127 independent reflections
Radiation source: Enhance (Mo) X-ray source	698 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.064
Detector resolution: 16.0696 pixels mm-1	θmax = 25.9º
T = 298(2) K	θmin = 3.0º
ω and φ scans	h = −31→31
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2006)	k = −27→28
Tmin = 0.985, Tmax = 0.990	l = −8→8
27177 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0841P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max < 0.001
1127 reflections	Δρmax = 0.15 e Å−3
132 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
N1	0.63312 (11)	0.10945 (11)	0.5765 (4)	0.0495 (9)
C2	0.58170 (12)	0.10315 (14)	0.6030 (6)	0.0431 (9)
N3	0.55453 (10)	0.05414 (12)	0.5797 (4)	0.0447 (8)
C4	0.58328 (13)	0.00862 (13)	0.5267 (5)	0.0416 (9)
N5	0.63552 (11)	0.01049 (12)	0.4927 (5)	0.0471 (8)
C6	0.65836 (13)	0.06118 (15)	0.5210 (5)	0.0463 (9)
N6	0.55533 (11)	0.15017 (12)	0.6581 (5)	0.0592 (10)
H6A	0.5721	0.1836	0.6753	0.071*
H6B	0.5210	0.14808	0.6776	0.071*
N7	0.55992 (11)	−0.04163 (11)	0.5010 (5)	0.0598 (10)
H7A	0.5282	−0.04463	0.5175	0.072*
H7B	0.5771	−0.0700	0.4684	0.072*
C8	0.71557 (14)	0.06575 (18)	0.4923 (7)	0.0710 (13)
H8A	0.7319	0.0329	0.5395	0.106*
H8B	0.7282	0.0985	0.5522	0.106*
H8C	0.7226	0.0687	0.3671	0.106*
O1	0.44754 (15)	0.1783 (2)	0.7397 (7)	0.1196 (16)
N8	0.36343 (14)	0.20435 (17)	0.7802 (5)	0.0738 (11)
C9	0.4016 (3)	0.1667 (3)	0.7697 (9)	0.113 (2)
H9	0.3931	0.1279	0.7864	0.226*
C10	0.3107 (3)	0.1868 (4)	0.8156 (11)	0.160 (4)
H10A	0.2905	0.1891	0.7028	0.319*
H10B	0.2954	0.2122	0.9074	0.319*
H10C	0.3105	0.1472	0.8606	0.319*
C11	0.3722 (4)	0.2647 (2)	0.7568 (11)	0.140 (3)
H11A	0.3839	0.2813	0.8722	0.279*
H11B	0.3399	0.2833	0.7189	0.279*
H11C	0.3988	0.2706	0.6634	0.279*

	U11	U22	U33	U12	U13	U23
N1	0.0426 (16)	0.0337 (16)	0.072 (2)	−0.0041 (13)	−0.0033 (15)	−0.0092 (16)
C2	0.0385 (18)	0.0307 (18)	0.060 (2)	−0.0004 (15)	−0.0048 (19)	−0.0032 (16)
N3	0.0391 (14)	0.0311 (14)	0.0638 (19)	−0.0001 (13)	−0.0004 (15)	−0.0059 (14)
C4	0.0400 (19)	0.0273 (17)	0.057 (2)	−0.0005 (14)	0.0046 (18)	−0.0045 (15)
N5	0.0406 (16)	0.0310 (15)	0.070 (2)	−0.0008 (12)	−0.0009 (16)	−0.0103 (15)
C6	0.0399 (17)	0.0381 (19)	0.061 (2)	−0.0037 (16)	−0.0027 (18)	−0.0038 (18)
N6	0.0457 (17)	0.0298 (15)	0.102 (3)	0.0009 (13)	−0.0020 (18)	−0.0156 (17)
N7	0.0414 (16)	0.0319 (15)	0.106 (3)	−0.0013 (13)	0.0115 (19)	−0.0126 (18)
C8	0.042 (2)	0.062 (2)	0.108 (4)	−0.0064 (19)	0.006 (3)	−0.019 (3)
O1	0.063 (2)	0.153 (4)	0.143 (4)	0.013 (2)	−0.005 (3)	−0.037 (3)
N8	0.070 (2)	0.072 (3)	0.079 (3)	0.006 (2)	0.0083 (19)	−0.012 (2)
C9	0.133 (6)	0.109 (5)	0.096 (5)	0.018 (5)	−0.008 (4)	−0.017 (4)
C10	0.101 (5)	0.266 (10)	0.112 (5)	−0.053 (6)	0.036 (4)	−0.050 (6)
C11	0.242 (9)	0.073 (4)	0.104 (5)	−0.002 (4)	0.001 (5)	0.008 (4)

N1—C2	1.336 (4)	C8—H8B	0.9300
N1—C6	1.348 (5)	C8—H8C	0.9300
C2—N3	1.337 (4)	O1—C9	1.223 (7)
C2—N6	1.338 (4)	N8—C9	1.307 (7)
N3—C4	1.338 (4)	N8—C11	1.419 (6)
C4—N7	1.317 (4)	N8—C10	1.429 (7)
C4—N5	1.358 (4)	C9—H9	0.9300
N5—C6	1.323 (4)	C10—H10A	0.9700
C6—C8	1.480 (5)	C10—H10B	0.9700
N6—H6A	0.8907	C10—H10C	0.9700
N6—H6B	0.8907	C11—H11A	0.9700
N7—H7A	0.8226	C11—H11B	0.9700
N7—H7B	0.8226	C11—H11C	0.9700
C8—H8A	0.9300
C2—N1—C6	115.1 (3)	C6—C8—H8C	109.5
N1—C2—N3	125.8 (3)	H8A—C8—H8C	109.5
N1—C2—N6	116.8 (3)	H8B—C8—H8C	109.5
N3—C2—N6	117.5 (3)	C9—N8—C11	121.7 (6)
C2—N3—C4	114.5 (3)	C9—N8—C10	121.7 (6)
N7—C4—N3	118.9 (3)	C11—N8—C10	116.6 (6)
N7—C4—N5	116.6 (3)	O1—C9—N8	125.6 (7)
N3—C4—N5	124.5 (3)	O1—C9—H9	117.2
C6—N5—C4	115.7 (3)	N8—C9—H9	117.2
N5—C6—N1	124.4 (3)	N8—C10—H10A	109.5
N5—C6—C8	118.5 (3)	N8—C10—H10B	109.5
N1—C6—C8	117.1 (3)	H10A—C10—H10B	109.5
C2—N6—H6A	120.0	N8—C10—H10C	109.5
C2—N6—H6B	120.0	H10A—C10—H10C	109.5
H6A—N6—H6B	120.0	H10B—C10—H10C	109.5
C4—N7—H7A	120.0	N8—C11—H11A	109.5
C4—N7—H7B	120.0	N8—C11—H11B	109.5
H7A—N7—H7B	120.0	H11A—C11—H11B	109.5
C6—C8—H8A	109.5	N8—C11—H11C	109.5
C6—C8—H8B	109.5	H11A—C11—H11C	109.5
H8A—C8—H8B	109.5	H11B—C11—H11C	109.5
C6—N1—C2—N3	0.2 (6)	N3—C4—N5—C6	2.1 (5)
C6—N1—C2—N6	180.0 (4)	C4—N5—C6—N1	−1.2 (6)
N1—C2—N3—C4	0.6 (6)	C4—N5—C6—C8	178.1 (4)
N6—C2—N3—C4	−179.2 (3)	C2—N1—C6—N5	0.2 (6)
C2—N3—C4—N7	179.7 (4)	C2—N1—C6—C8	−179.2 (4)
C2—N3—C4—N5	−1.8 (5)	C11—N8—C9—O1	0.0 (10)
N7—C4—N5—C6	−179.4 (4)	C10—N8—C9—O1	179.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6B···O1	0.89	2.05	2.890 (5)	157
N6—H6A···N5i	0.89	2.13	3.022 (4)	174
N7—H7B···N1ii	0.82	2.18	2.989 (4)	168
N7—H7A···N3iii	0.82	2.17	2.993 (4)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6B⋯O1	0.89	2.05	2.890 (5)	157
N6—H6A⋯N5i	0.89	2.13	3.022 (4)	174
N7—H7B⋯N1ii	0.82	2.18	2.989 (4)	168
N7—H7A⋯N3iii	0.82	2.17	2.993 (4)	176

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