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

Gao, W.; Wang, X.-L.; Yang, J.; Wu, X.-F.

doi:10.1107/S1600536812023380

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1925

doi:10.1107/S1600536812023380

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

Wei Gao,^a ^* Xin-Ling Wang,^a Jing Yang ^a and Xue-Fen Wu ^a

^aSchool of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China
^*Correspondence e-mail: xiaojun801115@163.com

(Received 18 May 2012; accepted 22 May 2012; online 31 May 2012)

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, P n m a
a = 6.810 (4) Å
b = 6.506 (4) Å
c = 15.277 (9) Å
V = 676.9 (7) Å³
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[F² > 2σ(F²)] = 0.032
wR(F²) = 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

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) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023380/hb6806sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023380/hb6806Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023380/hb6806Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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

Computing details top

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

Figures top

	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).

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

Crystal data top

C₄H₇N₃O₂·H₂O	D_x = 1.444 Mg m⁻³
M_r = 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 top

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

Refinement top

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(F_o²) + (0.0616P)²] where P = (F_o² + 2F_c²)/3
873 reflections	(Δ/σ)_max = 0.003
72 parameters	Δρ_max = 0.23 e Å⁻³
4 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₄H₇N₃O₂·H₂O	V = 676.9 (7) Å³
M_r = 147.14	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 6.810 (4) Å	µ = 0.12 mm⁻¹
b = 6.506 (4) Å	T = 113 K
c = 15.277 (9) Å	0.20 × 0.18 × 0.14 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	873 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	727 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.983	R_int = 0.048
6611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	4 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
873 reflections	Δρ_min = −0.26 e Å⁻³
72 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₄H₇N₃O₂·H₂O
M_r	147.14
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	113
a, b, c (Å)	6.810 (4), 6.506 (4), 15.277 (9)
V (Å³)	676.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.976, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	6611, 873, 727
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.090, 1.01
No. of reflections	873
No. of parameters	72
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.901 (7)	1.854 (7)	2.7520 (15)	173.9 (9)
O3—H3A···O1ⁱ	0.867 (6)	1.887 (6)	2.7518 (18)	174.2 (9)
O3—H3B···O1ⁱⁱ	0.859 (6)	1.944 (6)	2.8024 (18)	178.8 (10)

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

Acknowledgements

We gratefully acknowledge the financial support from the Doctoral Research Fund of Henan University of Traditional Chinese Medicine.

References

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