4-Amino-3,5-dimethyl-4H1-,2,4-triazole-water (2/3).

The asymmetric unit of the title compound, 2C(4)H(8)N(4)·3H(2)O, contains two crystallographically independent 4-amino-3,5-dimethyl-1,2,4-triazole mol-ecules and three water mol-ecules. The structure exhibits N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Wang et al. (2006 ▶); Zachara et al. 2004 ▶). For related literature, see: Beckmann & Brooker (2003 ▶); Bentiss et al. (1999 ▶); Collin et al. (2003 ▶); Curtis (2004 ▶).

Experimental

Crystal data

2C4H8N4·3H2O

M = 278.34

Triclinic,

a = 7.194 (4) Å

b = 8.680 (4) Å

c = 13.592 (7) Å

α = 72.332 (8)°

β = 84.993 (8)°

γ = 68.936 (7)°

V = 754.5 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.981, T max = 0.984

5166 measured reflections

2904 independent reflections

2447 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.137

S = 1.03

2904 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028146/bt2782sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028146/bt2782Isup2.hkl

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

2C4H8N4·3H2O	Z = 2
Mr = 278.34	F(000) = 300
Triclinic, P1	Dx = 1.225 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.194 (4) Å	Cell parameters from 785 reflections
b = 8.680 (4) Å	θ = 2.4–28.0°
c = 13.592 (7) Å	µ = 0.10 mm−1
α = 72.332 (8)°	T = 293 K
β = 84.993 (8)°	Block, colourless
γ = 68.936 (7)°	0.20 × 0.18 × 0.17 mm
V = 754.5 (6) Å3

Bruker APEX CCD diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2447 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scan	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −8→8
Tmin = 0.981, Tmax = 0.984	k = −10→10
5166 measured reflections	l = −16→12

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0782P)2 + 0.0952P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2904 reflections	Δρmax = 0.27 e Å−3
213 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.151 (12)

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
C1	0.2307 (2)	0.21698 (19)	0.03818 (12)	0.0464 (4)
C2	0.2155 (3)	0.3435 (2)	0.09351 (15)	0.0675 (5)
H2A	0.2195	0.4487	0.0448	0.101*
H2B	0.3249	0.2973	0.1422	0.101*
H2C	0.0922	0.3666	0.1295	0.101*
C3	0.2508 (2)	−0.02273 (19)	0.01050 (12)	0.0450 (4)
C4	0.2584 (3)	−0.2021 (2)	0.02881 (14)	0.0574 (4)
H4A	0.2743	−0.2287	−0.0357	0.086*
H4B	0.1369	−0.2134	0.0596	0.086*
H4C	0.3691	−0.2805	0.0744	0.086*
C5	0.2491 (2)	0.3310 (2)	−0.54342 (13)	0.0518 (4)
C6	0.2507 (4)	0.2018 (3)	−0.59340 (17)	0.0790 (6)
H6A	0.2633	0.0947	−0.5416	0.119*
H6B	0.3612	0.1843	−0.6389	0.119*
H6C	0.1286	0.2421	−0.6324	0.119*
C7	0.2362 (2)	0.5735 (2)	−0.52294 (12)	0.0500 (4)
C8	0.2197 (3)	0.7564 (2)	−0.54624 (15)	0.0691 (5)
H8A	0.2259	0.7821	−0.4830	0.104*
H8B	0.0951	0.8304	−0.5817	0.104*
H8C	0.3274	0.7752	−0.5892	0.104*
N1	0.2638 (2)	0.08533 (18)	−0.07827 (10)	0.0528 (4)
N2	0.2508 (2)	0.23853 (17)	−0.06052 (10)	0.0533 (4)
N3	0.22893 (18)	0.05496 (15)	0.08561 (9)	0.0433 (3)
N4	0.2136 (3)	−0.02566 (19)	0.19138 (10)	0.0543 (4)
H4D	0.100 (3)	0.047 (3)	0.2139 (15)	0.071 (6)*
H4E	0.320 (3)	−0.030 (3)	0.2220 (15)	0.071 (6)*
N5	0.2546 (2)	0.46293 (18)	−0.43183 (10)	0.0568 (4)
N6	0.2637 (2)	0.30785 (18)	−0.44498 (11)	0.0579 (4)
N7	0.2326 (2)	0.49581 (17)	−0.59485 (9)	0.0511 (4)
N8	0.2096 (4)	0.5651 (3)	−0.70320 (12)	0.0790 (6)
H8D	0.105 (4)	0.659 (4)	−0.710 (2)	0.109 (10)*
H8E	0.325 (5)	0.589 (4)	−0.726 (2)	0.119 (10)*
O1W	−0.1595 (3)	0.1723 (3)	0.26863 (18)	0.1022 (7)
H1WA	−0.219 (5)	0.280 (4)	0.254 (2)	0.132 (12)*
H1WB	−0.248 (5)	0.128 (4)	0.254 (2)	0.131 (11)*
O2W	0.3524 (2)	0.47375 (18)	−0.23848 (12)	0.0706 (4)
H2WA	0.308 (4)	0.412 (3)	−0.186 (2)	0.090 (7)*
H2WB	0.308 (4)	0.466 (3)	−0.296 (2)	0.101 (8)*
O3W	0.3962 (2)	0.02300 (16)	−0.26616 (11)	0.0610 (4)
H3WA	0.341 (3)	0.055 (3)	−0.2121 (18)	0.079 (6)*
H3WB	0.349 (4)	0.114 (3)	−0.321 (2)	0.093 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0471 (8)	0.0429 (8)	0.0438 (8)	−0.0139 (6)	−0.0002 (6)	−0.0069 (6)
C2	0.0849 (13)	0.0529 (10)	0.0645 (11)	−0.0241 (9)	−0.0015 (10)	−0.0161 (9)
C3	0.0393 (7)	0.0485 (8)	0.0455 (8)	−0.0143 (6)	0.0017 (6)	−0.0128 (7)
C4	0.0574 (10)	0.0543 (10)	0.0636 (11)	−0.0213 (8)	0.0020 (8)	−0.0198 (8)
C5	0.0514 (9)	0.0550 (9)	0.0478 (9)	−0.0184 (7)	0.0075 (7)	−0.0152 (7)
C6	0.0942 (15)	0.0765 (13)	0.0778 (14)	−0.0334 (11)	0.0145 (11)	−0.0378 (11)
C7	0.0513 (9)	0.0539 (9)	0.0444 (9)	−0.0212 (7)	0.0050 (7)	−0.0115 (7)
C8	0.0833 (13)	0.0610 (11)	0.0660 (12)	−0.0345 (10)	0.0060 (10)	−0.0129 (9)
N1	0.0571 (8)	0.0584 (8)	0.0431 (7)	−0.0227 (6)	0.0055 (6)	−0.0134 (6)
N2	0.0589 (8)	0.0512 (8)	0.0455 (8)	−0.0221 (6)	0.0029 (6)	−0.0053 (6)
N3	0.0445 (7)	0.0430 (7)	0.0374 (7)	−0.0144 (5)	0.0013 (5)	−0.0060 (5)
N4	0.0632 (9)	0.0543 (8)	0.0378 (7)	−0.0206 (7)	0.0038 (7)	−0.0034 (6)
N5	0.0697 (9)	0.0578 (8)	0.0427 (8)	−0.0249 (7)	0.0031 (6)	−0.0119 (6)
N6	0.0709 (9)	0.0516 (8)	0.0467 (8)	−0.0213 (7)	0.0030 (6)	−0.0086 (6)
N7	0.0565 (8)	0.0584 (8)	0.0368 (7)	−0.0242 (6)	0.0045 (6)	−0.0080 (6)
N8	0.1082 (16)	0.0910 (14)	0.0374 (8)	−0.0448 (13)	0.0018 (9)	−0.0062 (8)
O1W	0.0737 (10)	0.0831 (12)	0.170 (2)	−0.0312 (9)	0.0195 (10)	−0.0655 (13)
O2W	0.1040 (11)	0.0668 (9)	0.0514 (8)	−0.0482 (8)	−0.0005 (7)	−0.0090 (6)
O3W	0.0781 (9)	0.0496 (7)	0.0488 (7)	−0.0161 (6)	0.0067 (6)	−0.0143 (6)

C1—N2	1.300 (2)	C7—N7	1.352 (2)
C1—N3	1.362 (2)	C7—C8	1.483 (2)
C1—C2	1.478 (2)	C8—H8A	0.9600
C2—H2A	0.9600	C8—H8B	0.9600
C2—H2B	0.9600	C8—H8C	0.9600
C2—H2C	0.9600	N1—N2	1.391 (2)
C3—N1	1.304 (2)	N3—N4	1.4091 (18)
C3—N3	1.355 (2)	N4—H4D	0.93 (2)
C3—C4	1.482 (2)	N4—H4E	0.88 (2)
C4—H4A	0.9600	N5—N6	1.389 (2)
C4—H4B	0.9600	N7—N8	1.411 (2)
C4—H4C	0.9600	N8—H8D	0.88 (3)
C5—N6	1.299 (2)	N8—H8E	0.93 (3)
C5—N7	1.354 (2)	O1W—H1WA	0.84 (3)
C5—C6	1.474 (3)	O1W—H1WB	0.92 (3)
C6—H6A	0.9600	O2W—H2WA	0.87 (3)
C6—H6B	0.9600	O2W—H2WB	0.90 (3)
C6—H6C	0.9600	O3W—H3WA	0.88 (2)
C7—N5	1.299 (2)	O3W—H3WB	0.89 (3)
N2—C1—N3	109.30 (14)	N5—C7—C8	126.38 (16)
N2—C1—C2	126.85 (15)	N7—C7—C8	124.62 (15)
N3—C1—C2	123.85 (15)	C7—C8—H8A	109.5
C1—C2—H2A	109.5	C7—C8—H8B	109.5
C1—C2—H2B	109.5	H8A—C8—H8B	109.5
H2A—C2—H2B	109.5	C7—C8—H8C	109.5
C1—C2—H2C	109.5	H8A—C8—H8C	109.5
H2A—C2—H2C	109.5	H8B—C8—H8C	109.5
H2B—C2—H2C	109.5	C3—N1—N2	107.78 (13)
N1—C3—N3	109.02 (14)	C1—N2—N1	107.36 (12)
N1—C3—C4	126.61 (15)	C3—N3—C1	106.55 (13)
N3—C3—C4	124.37 (14)	C3—N3—N4	124.23 (13)
C3—C4—H4A	109.5	C1—N3—N4	129.20 (13)
C3—C4—H4B	109.5	N3—N4—H4D	106.6 (12)
H4A—C4—H4B	109.5	N3—N4—H4E	105.8 (13)
C3—C4—H4C	109.5	H4D—N4—H4E	109.1 (17)
H4A—C4—H4C	109.5	C7—N5—N6	107.56 (14)
H4B—C4—H4C	109.5	C5—N6—N5	107.64 (13)
N6—C5—N7	108.89 (15)	C7—N7—C5	106.91 (14)
N6—C5—C6	126.70 (17)	C7—N7—N8	129.47 (15)
N7—C5—C6	124.41 (16)	C5—N7—N8	123.59 (15)
C5—C6—H6A	109.5	N7—N8—H8D	102.0 (18)
C5—C6—H6B	109.5	N7—N8—H8E	105.6 (17)
H6A—C6—H6B	109.5	H8D—N8—H8E	112 (3)
C5—C6—H6C	109.5	H1WA—O1W—H1WB	106 (3)
H6A—C6—H6C	109.5	H2WA—O2W—H2WB	107 (2)
H6B—C6—H6C	109.5	H3WA—O3W—H3WB	107 (2)
N5—C7—N7	109.00 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4D···O1W	0.93 (2)	2.00 (2)	2.924 (3)	170.9 (18)
N4—H4E···O3Wi	0.88 (2)	2.21 (2)	3.078 (3)	168.3 (18)
N8—H8E···O2Wii	0.93 (3)	2.23 (3)	3.104 (3)	156 (2)
O1W—H1WA···O2Wiii	0.84 (3)	1.95 (3)	2.793 (3)	173 (3)
O1W—H1WB···O3Wiv	0.92 (3)	1.93 (3)	2.810 (2)	160 (3)
O2W—H2WA···N2	0.87 (3)	2.02 (3)	2.885 (2)	171 (2)
O2W—H2WB···N5	0.90 (3)	1.93 (3)	2.816 (2)	168 (2)
O3W—H3WA···N1	0.88 (2)	1.92 (2)	2.787 (2)	168 (2)
O3W—H3WB···N6	0.89 (3)	1.93 (3)	2.827 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4D⋯O1W	0.93 (2)	2.00 (2)	2.924 (3)	170.9 (18)
N4—H4E⋯O3Wi	0.88 (2)	2.21 (2)	3.078 (3)	168.3 (18)
N8—H8E⋯O2Wii	0.93 (3)	2.23 (3)	3.104 (3)	156 (2)
O1W—H1WA⋯O2Wiii	0.84 (3)	1.95 (3)	2.793 (3)	173 (3)
O1W—H1WB⋯O3Wiv	0.92 (3)	1.93 (3)	2.810 (2)	160 (3)
O2W—H2WA⋯N2	0.87 (3)	2.02 (3)	2.885 (2)	171 (2)
O2W—H2WB⋯N5	0.90 (3)	1.93 (3)	2.816 (2)	168 (2)
O3W—H3WA⋯N1	0.88 (2)	1.92 (2)	2.787 (2)	168 (2)
O3W—H3WB⋯N6	0.89 (3)	1.93 (3)	2.827 (2)	176 (2)

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