3-Meth­oxy-4-methyl-1H-1,2,4-triazol-5(4H)-one monohydrate

Abstract

In the title hydrate, C₄H₇N₃O₂·H₂O, all the non-H atoms lie on a crystallographic mirror plane. The H atoms of both methyl groups are disordered over two sets of sites. In the crystal, N—H⋯O_w and O_w—H⋯O_k (w = water and k = ketone) hydrogen bonds link the components into (010) sheets.

Related literature  

For related structures, see: Jin et al. (2011 ▶); Liu & Liu (2011 ▶); Liu et al. (2011 ▶, 2012 ▶); Ustabaş et al. (2010) ▶. For bioactivity data, see Tan et al. (2012 ▶).

Experimental  

Crystal data  

• C₄H₇N₃O₂·H₂O

• M _r = 147.14

• Orthorhombic,

• a = 6.810 (4) Å

• b = 6.506 (4) Å

• c = 15.277 (9) Å

• V = 676.9 (7) ų

• Z = 4

• Mo Kα radiation

• μ = 0.12 mm⁻¹

• T = 113 K

• 0.20 × 0.18 × 0.14 mm

Data collection  

• Rigaku Saturn724 CCD diffractometer

• Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.976, T _max = 0.983

• 6611 measured reflections

• 873 independent reflections

• 727 reflections with I > 2σ(I)

• R _int = 0.048

Refinement  

• R[F ² > 2σ(F ²)] = 0.032

• wR(F ²) = 0.090

• S = 1.01

• 873 reflections

• 72 parameters

• 4 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.23 e Å⁻³

• Δρ_min = −0.26 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812023380/hb6806Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.90 (1)	1.85 (1)	2.7520 (15)	174 (1)
O3—H3A⋯O1i	0.87 (1)	1.89 (1)	2.7518 (18)	174 (1)
O3—H3B⋯O1ii	0.86 (1)	1.94 (1)	2.8024 (18)	179 (1)

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

Sulfur and nitrogen heterocyclic compounds have received considerable attention in recent years because of their medicinal and pesticidal importance, such as 1,3,4-thiadiazoles, pyrimidines, 1,2,4-triazoles (Jin et al. 2011; Liu & Liu, 2011; Liu et al. 2011; Liu et al., 2012; Tan et al., 2011; Ustabaş et al., 2010).

Single-crystal X-ray diffraction analysis reveals that the title compound crystallizes in the orthorhombic space group Pnma. As shown in Fig. 2, the crystal structure features intermolecular hydrogen bonds O-H···O and N-H···O.

Experimental

The tite compound was available commercially. The crystals were grown from ethanol as colourless prisms

Refinement

All the H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Figures

Fig. 1.

The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Fig. 2.

The crystal packing for (I).

Crystal data

C4H7N3O2·H2O	Dx = 1.444 Mg m−3
Mr = 147.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 2353 reflections
a = 6.810 (4) Å	θ = 3.0–27.8°
b = 6.506 (4) Å	µ = 0.12 mm−1
c = 15.277 (9) Å	T = 113 K
V = 676.9 (7) Å3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.14 mm
F(000) = 312

Data collection

Rigaku Saturn724 CCD diffractometer	873 independent reflections
Radiation source: rotating anode	727 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.048
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 3.3°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −8→7
Tmin = 0.976, Tmax = 0.983	l = −20→20
6611 measured reflections

Refinement

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: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0616P)2] where P = (Fo2 + 2Fc2)/3
873 reflections	(Δ/σ)max = 0.003
72 parameters	Δρmax = 0.23 e Å−3
4 restraints	Δρmin = −0.26 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.64561 (9)	0.2500	0.35699 (4)	0.02165 (15)
O2	0.49415 (9)	0.2500	0.65038 (4)	0.02269 (16)
N1	0.62148 (10)	0.2500	0.50977 (4)	0.01766 (17)
N2	0.35229 (11)	0.2500	0.43609 (4)	0.01895 (17)
N3	0.29539 (11)	0.2500	0.52418 (5)	0.01921 (18)
C1	0.54905 (11)	0.2500	0.42578 (6)	0.0172 (2)
C2	0.46308 (12)	0.2500	0.56483 (6)	0.0169 (2)
C4	0.82847 (13)	0.2500	0.53342 (6)	0.0235 (2)
H4A	0.9060	0.1949	0.4847	0.035*	0.50
H4B	0.8481	0.1642	0.5854	0.035*	0.50
H4C	0.8707	0.3909	0.5461	0.035*	0.50
C3	0.31615 (14)	0.2500	0.70293 (6)	0.0257 (2)
H3D	0.2528	0.1151	0.6990	0.039*	0.50
H3E	0.2262	0.3558	0.6811	0.039*	0.50
H3C	0.3495	0.2791	0.7641	0.039*	0.50
O3	0.04758 (10)	0.2500	0.31776 (5)	0.0449 (2)
H2	0.2590 (12)	0.2500	0.3942 (6)	0.034 (3)*
H3A	0.0698 (13)	0.2500	0.2619 (4)	0.047 (4)*
H3B	−0.0752 (9)	0.2500	0.3306 (6)	0.063 (4)*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0167 (3)	0.0331 (3)	0.0152 (3)	0.000	0.0026 (2)	0.000
O2	0.0164 (3)	0.0380 (4)	0.0136 (3)	0.000	0.0014 (2)	0.000
N1	0.0116 (3)	0.0256 (4)	0.0158 (3)	0.000	0.0001 (3)	0.000
N2	0.0134 (3)	0.0301 (4)	0.0133 (3)	0.000	−0.0005 (3)	0.000
N3	0.0152 (3)	0.0273 (4)	0.0151 (3)	0.000	0.0014 (3)	0.000
C1	0.0154 (4)	0.0183 (4)	0.0179 (4)	0.000	−0.0004 (3)	0.000
C2	0.0149 (4)	0.0211 (4)	0.0147 (4)	0.000	0.0011 (3)	0.000
C4	0.0116 (4)	0.0377 (5)	0.0213 (4)	0.000	−0.0012 (3)	0.000
C3	0.0212 (4)	0.0394 (5)	0.0166 (4)	0.000	0.0074 (3)	0.000
O3	0.0155 (3)	0.1026 (7)	0.0165 (3)	0.000	−0.0008 (3)	0.000

Geometric parameters (Å, º)

O1—C1	1.2397 (12)	N3—C2	1.2999 (12)
O2—C2	1.3239 (13)	C4—H4A	0.9800
O2—C3	1.4540 (13)	C4—H4B	0.9800
N1—C2	1.3679 (12)	C4—H4C	0.9800
N1—C1	1.3746 (13)	C3—H3D	0.9800
N1—C4	1.4552 (14)	C3—H3E	0.9800
N2—C1	1.3492 (13)	C3—H3C	0.9800
N2—N3	1.4003 (12)	O3—H3A	0.867 (6)
N2—H2	0.901 (7)	O3—H3B	0.859 (6)
C2—O2—C3	114.32 (7)	N1—C4—H4A	109.5
C2—N1—C1	106.92 (8)	N1—C4—H4B	109.5
C2—N1—C4	127.68 (8)	H4A—C4—H4B	109.5
C1—N1—C4	125.41 (7)	N1—C4—H4C	109.5
C1—N2—N3	112.77 (7)	H4A—C4—H4C	109.5
C1—N2—H2	128.1 (6)	H4B—C4—H4C	109.5
N3—N2—H2	119.1 (6)	O2—C3—H3D	109.5
C2—N3—N2	102.47 (7)	O2—C3—H3E	109.5
O1—C1—N2	128.74 (8)	H3D—C3—H3E	109.5
O1—C1—N1	126.94 (8)	O2—C3—H3C	109.5
N2—C1—N1	104.32 (7)	H3D—C3—H3C	109.5
N3—C2—O2	127.74 (8)	H3E—C3—H3C	109.5
N3—C2—N1	113.52 (9)	H3A—O3—H3B	113.2 (8)
O2—C2—N1	118.75 (8)
C1—N2—N3—C2	0.0	N2—N3—C2—N1	0.0
N3—N2—C1—O1	180.0	C3—O2—C2—N3	0.0
N3—N2—C1—N1	0.0	C3—O2—C2—N1	180.0
C2—N1—C1—O1	180.0	C1—N1—C2—N3	0.0
C4—N1—C1—O1	0.0	C4—N1—C2—N3	180.0
C2—N1—C1—N2	0.0	C1—N1—C2—O2	180.0
C4—N1—C1—N2	180.0	C4—N1—C2—O2	0.0
N2—N3—C2—O2	180.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.90 (1)	1.85 (1)	2.7520 (15)	174 (1)
O3—H3A···O1i	0.87 (1)	1.89 (1)	2.7518 (18)	174 (1)
O3—H3B···O1ii	0.86 (1)	1.94 (1)	2.8024 (18)	179 (1)

Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1, y, z.