3,5-Dimethyl-4-nitroso-1H-pyrazole

Safyanova, I.; Dudarenko, N.M.; Pavlenko, V.A.; Iskenderov, T.S.; Haukka, M.

doi:10.1107/S1600536811033794

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2520-o2521

doi:10.1107/S1600536811033794

Open

access

3,5-Dimethyl-4-nitroso-1H-pyrazole

Inna Safyanova,^a ^* Nikolay M. Dudarenko,^a Vadim A. Pavlenko,^a Turganbay S. Iskenderov ^a and Matti Haukka ^b

^aDepartment of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Str. 64, 01601 Kiev, Ukraine, and ^bDepartment of Chemistry, University of Joensuu, PO Box, 111, FI-80101 Joensuu, Finland
^*Correspondence e-mail: safyanova_inna@mail.ru

(Received 26 July 2011; accepted 18 August 2011; online 31 August 2011)

In the unit cell of the title compound, C₅H₇N₃O, there are two conformers (A and B) which differ in the position of the oxime group with respect to the protonated pyrazole nitrogen (trans in the A conformer and cis in the B conformer) and in the geometric parameters. The oxime group exists in the nitroso form in both conformers. In the crystal, molecules are linked by intermolecular N—H⋯O and N—H⋯N hydrogen bonds into zigzag-like chains along the b axis.

Related literature

For the use of pyrazole-based ligands, see: Mullins & Pecoraro (2008 ); Mukhopadhyay et al. (2004 ). For the magnetic properties of pyrazolate complexes, see: Aromi & Brechin (2006 ); Gatteschi et al. (2006 ). For the use of oxime substituents in the synthesis of polynuclear ligands, see: Petrusenko et al. (1997 ); Kanderal et al. (2005 ); Sachse et al. (2008 ); Moroz et al. (2010 ). For the use of 4-nitropyrazoles as ligands, see: Halcrow (2005 ). For related structures, see: Fletcher et al. (1997 ); Kovbasyuk et al. (2004 ); Mokhir et al. (2002 ); Sliva et al. (1997 ); Wörl, Fritsky et al. (2005 ); Wörl, Pritzkow et al. (2005 ). For the synthesis of the title compound, see: Cameron et al. (1996 ).

Experimental

Crystal data

C₅H₇N₃O
M_r = 125.14
Monoclinic, P 2₁ /c
a = 4.0268 (2) Å
b = 15.3793 (7) Å
c = 19.6627 (9) Å
β = 94.613 (3)°
V = 1213.75 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.46 × 0.33 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.955, T_max = 0.987
9003 measured reflections
2747 independent reflections
1866 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.03
2747 reflections
175 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1B⋯O1Aⁱ	0.954 (18)	1.802 (18)	2.7526 (16)	174.0 (15)
N1A—H1A⋯N2Bⁱⁱ	0.915 (19)	1.95 (2)	2.8544 (18)	171.5 (16)
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811033794/jh2317sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033794/jh2317Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033794/jh2317Isup3.cml

checkCIF report

Comment top

Pyrazole-based ligands are widely used in bioinorganic chemistry, molecular magnetism and supramolecular chemistry, as they are able to form different architectures, ranging from polynuclear clusters to metallocycles (Mullins, et al., 2008; Mukhopadhyay, et al., 2004). In addition to the ability to bridge two or more metal ions, pyrazole ligands also provide an effective magnetic exchange pathway between them (Aromi et al. 2006; Gatteschi, et al., 2006). The incorporation of other coordinating groups to the pyrazole ring can increase the variety of polynuclear compounds that can be formed. For example, introduction of the potentially bridging oxime group in the molecules of the ligands already having bridging moieties (such as pyrazolates) can lead to increase of nuclearity and complexity of the metal complexes on their basis (Petrusenko et al., 1997; Kanderal et al., 2005; Sachse et al., 2008; Moroz et al., 2010). In this work, we report the crystal structure of the title compound which contains the oxime group in the 4-position of the pyrazole ring. Unlike 4-nitropyrazoles which have been widely used for preparation of oligonuclear metal complexes (Halcrow et al., 2005), 4-nitrosopyrazoles have never been studied as ligands, and no metal complexes based on this type of ligands have been reported up to date. Crystal and molecular structures of only two 4-nitrosopyrazoles have been reported before (Cameron et al., 1996; Fletcher et al., 1997).

In the unit cell there are two types of conformers (A and B) of the title compound which differs significantly by the geometrical parameters and by the position of the oxime group with respect to the protonated pyrazole nitrogen (Fig. 1). In the conformer A, the oxime group is trans- with respect to the pyrazole hydrogen, while in the conformer B the oxime-group is cis-situated. In the conformers A and B the bond lengths markedly differs, first of all it is noticeable upon comparing the interatomic distances within the oxime groups. In the conformer B, the difference in bond lengths between C—N (1.3902 (19) Å) and N=O (1.2412 (16) Å) bonds of the oxime groups is quite large (ca 0.15 Å) while in the conformer A (C—N 1.3553 (19) Å and N=O 1.2701 (16) Å) it is much less pronounced (less than 0.08 Å). This clearly indicates that the CNO moiety in both conformers exists in the nitroso-form (Sliva et al. (1997); Mokhir et al., 2002), however, in the conformer A there is a noticeable contribution of the isonitroso-form. Such a difference can be a consequence of the involvement of the oxime oxygen O1A in formation of the intermolecular H-bond, while O1B does not participate in any H-bond (Table 1).

The differences in geometrical and electronic structure of the oxime groups significantly influence on the C—C, C—N, N—N bond lengths within the pyrazole rings which are deviated from normal values (Kovbasyuk et al., 2004; Wörl, Fritsky et al., 2005; Wörl, Pritzkow et al., 2005). Thus, there are signs of conjugation of the C(3B)—C(4B) bond with the O(1B)—N(3B) bond which results in noticeable shortening of the former (1.405 (2) Å) as compare to that observed in the conformer A, C(3)—C(4) = 1.442 (2) Å.

In the crystal, the molecules are linked by intermolecular N—H···O and N—H···N hydrogen bonds building zigzag chains along the b axis (Fig.2, Table 1). The translational along a axis chains form walls which are united into the crystal by van der Waals interactions.

Related literature top

For the use of pyrazole-based ligands, see: Mullins et al. (2008); Mukhopadhyay et al. (2004). For the magnetic properties of pyrazolate complexes, see: Aromi & Brechin (2006); Gatteschi et al. (2006). For the use of oxime substituents in the synthesis of polynucleative ligands, see: Petrusenko et al. (1997); Kanderal et al. (2005); Sachse et al. (2008); Moroz et al. (2010). For the use of 4-nitropyrazoles as ligands, see: Halcrow (2005). For related structures, see: Fletcher et al. (1997); Kovbasyuk et al. (2004); Mokhir et al. (2002); Sliva et al. (1997); Wörl, Fritsky et al. (2005); Wörl, Pritzkow et al. (2005). For the synthesis of the title compound, see: Cameron et al. (1996).

Experimental top

3,5-dimethyl-4-nitrozo-1H-pyrazole was synthesized by using a literature procedure (Cameron et al., 1996) from acetylacetone, sodium nitrite and hydrazine hydrate in aqueous hydrochloric acid. The crude product was collected by filtration and purified by recrystallization from benzene. Colorless crystals suitable for the X-ray diffraction were obtained after several hours (yield 78%).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The two independent molecules of (I) in the unit cell, showing the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound showing the intermolecular hydrogen bonds by dashed lines.

3,5-Dimethyl-4-nitroso-1H-pyrazole top

Crystal data top

C₅H₇N₃O	F(000) = 528
M_r = 125.14	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4238 reflections
a = 4.0268 (2) Å	θ = 1.0–27.5°
b = 15.3793 (7) Å	µ = 0.10 mm⁻¹
c = 19.6627 (9) Å	T = 120 K
β = 94.613 (3)°	Plate, blue
V = 1213.75 (10) Å³	0.46 × 0.33 × 0.13 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	2747 independent reflections
Radiation source: fine-focus sealed tube	1866 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.040
Detector resolution: 9 pixels mm^-1	θ_max = 27.4°, θ_min = 2.5°
ϕ scans and ω scans with κ offset	h = −4→5
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −18→19
T_min = 0.955, T_max = 0.987	l = −25→25
9003 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0516P)² + 0.0988P] where P = (F_o² + 2F_c²)/3
2747 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₅H₇N₃O	V = 1213.75 (10) Å³
M_r = 125.14	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.0268 (2) Å	µ = 0.10 mm⁻¹
b = 15.3793 (7) Å	T = 120 K
c = 19.6627 (9) Å	0.46 × 0.33 × 0.13 mm
β = 94.613 (3)°

Data collection top

Nonius KappaCCD diffractometer	2747 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	1866 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.987	R_int = 0.040
9003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
2747 reflections	Δρ_min = −0.25 e Å⁻³
175 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
O1A	−0.1796 (3)	0.16615 (7)	0.22546 (5)	0.0279 (3)
N1A	0.3665 (3)	−0.05073 (9)	0.32527 (7)	0.0241 (3)
N2A	0.4403 (3)	0.02548 (8)	0.36162 (6)	0.0243 (3)
N3A	−0.1316 (3)	0.08489 (8)	0.22016 (7)	0.0240 (3)
C1A	0.2710 (3)	0.08712 (10)	0.32773 (8)	0.0210 (4)
C2A	0.2872 (4)	0.17879 (10)	0.35059 (8)	0.0258 (4)
H2A	0.4408	0.1837	0.3917	0.039*
H2B	0.0648	0.1981	0.3609	0.039*
H2C	0.3667	0.2152	0.3144	0.039*
C3A	0.0867 (4)	0.05016 (9)	0.26876 (8)	0.0202 (4)
C4A	0.1598 (4)	−0.03950 (10)	0.27044 (8)	0.0225 (4)
C5A	0.0466 (4)	−0.11093 (10)	0.22306 (9)	0.0308 (4)
H5A	0.1902	−0.1133	0.1852	0.046*
H5B	−0.1839	−0.1001	0.2052	0.046*
H5C	0.0589	−0.1664	0.2476	0.046*
O1B	−0.2132 (3)	0.13230 (7)	−0.04852 (6)	0.0356 (3)
N1B	0.3699 (3)	0.21423 (8)	0.11942 (7)	0.0216 (3)
N2B	0.3158 (3)	0.30207 (8)	0.10938 (7)	0.0226 (3)
N3B	−0.1646 (3)	0.20960 (9)	−0.03253 (7)	0.0275 (3)
C1B	0.1150 (4)	0.30759 (10)	0.05258 (8)	0.0214 (4)
C2B	0.0044 (4)	0.39331 (10)	0.02337 (8)	0.0267 (4)
H2B1	0.0884	0.4400	0.0540	0.040*
H2B2	−0.2395	0.3953	0.0182	0.040*
H2B3	0.0918	0.4009	−0.0213	0.040*
C3B	0.0397 (4)	0.22318 (10)	0.02693 (7)	0.0201 (3)
C4B	0.2123 (4)	0.16456 (10)	0.07173 (8)	0.0208 (4)
C5B	0.2411 (4)	0.06867 (10)	0.07173 (8)	0.0264 (4)
H5B1	0.3957	0.0502	0.1100	0.040*
H5B2	0.3250	0.0494	0.0288	0.040*
H5B3	0.0216	0.0428	0.0763	0.040*
H1A	0.453 (4)	−0.1013 (13)	0.3437 (9)	0.040 (5)*
H1B	0.515 (4)	0.1949 (11)	0.1572 (9)	0.035 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0312 (6)	0.0231 (6)	0.0288 (7)	0.0049 (5)	−0.0017 (5)	0.0031 (5)
N1A	0.0283 (7)	0.0183 (7)	0.0252 (8)	0.0026 (6)	−0.0006 (6)	0.0023 (6)
N2A	0.0268 (7)	0.0221 (8)	0.0236 (7)	0.0000 (6)	0.0000 (6)	0.0000 (6)
N3A	0.0240 (7)	0.0244 (8)	0.0236 (7)	0.0010 (6)	0.0024 (6)	0.0034 (6)
C1A	0.0187 (8)	0.0230 (9)	0.0216 (8)	0.0002 (6)	0.0028 (6)	0.0019 (6)
C2A	0.0259 (8)	0.0246 (9)	0.0261 (9)	0.0004 (7)	−0.0024 (7)	−0.0031 (7)
C3A	0.0198 (8)	0.0204 (8)	0.0205 (8)	−0.0002 (6)	0.0023 (6)	0.0010 (6)
C4A	0.0224 (8)	0.0218 (9)	0.0235 (9)	−0.0005 (7)	0.0039 (7)	0.0021 (6)
C5A	0.0352 (9)	0.0228 (9)	0.0337 (10)	−0.0011 (7)	−0.0005 (8)	−0.0046 (7)
O1B	0.0459 (7)	0.0269 (7)	0.0328 (7)	−0.0057 (6)	−0.0044 (6)	−0.0041 (5)
N1B	0.0249 (7)	0.0172 (7)	0.0222 (7)	0.0014 (6)	−0.0014 (6)	0.0019 (5)
N2B	0.0270 (7)	0.0153 (7)	0.0250 (7)	0.0008 (5)	−0.0008 (6)	0.0011 (5)
N3B	0.0295 (7)	0.0247 (8)	0.0280 (8)	−0.0038 (6)	0.0007 (6)	−0.0014 (6)
C1B	0.0220 (8)	0.0203 (8)	0.0223 (8)	0.0005 (6)	0.0037 (7)	0.0001 (6)
C2B	0.0308 (9)	0.0205 (8)	0.0282 (9)	0.0013 (7)	−0.0010 (7)	0.0030 (7)
C3B	0.0212 (8)	0.0194 (8)	0.0198 (8)	−0.0005 (6)	0.0020 (6)	0.0002 (6)
C4B	0.0204 (8)	0.0211 (8)	0.0214 (8)	−0.0018 (6)	0.0041 (7)	−0.0013 (6)
C5B	0.0313 (9)	0.0184 (8)	0.0294 (9)	0.0012 (7)	0.0017 (7)	−0.0003 (7)

Geometric parameters (Å, º) top

O1A—N3A	1.2701 (16)	O1B—N3B	1.2412 (16)
N1A—C4A	1.319 (2)	N1B—C4B	1.330 (2)
N1A—N2A	1.3922 (18)	N1B—N2B	1.3801 (17)
N1A—H1A	0.915 (19)	N1B—H1B	0.954 (18)
N2A—C1A	1.3170 (19)	N2B—C1B	1.3279 (19)
N3A—C3A	1.3553 (19)	N3B—C3B	1.3902 (19)
C1A—C3A	1.442 (2)	C1B—C3B	1.417 (2)
C1A—C2A	1.479 (2)	C1B—C2B	1.492 (2)
C2A—H2A	0.9800	C2B—H2B1	0.9800
C2A—H2B	0.9800	C2B—H2B2	0.9800
C2A—H2C	0.9800	C2B—H2B3	0.9800
C3A—C4A	1.410 (2)	C3B—C4B	1.405 (2)
C4A—C5A	1.488 (2)	C4B—C5B	1.479 (2)
C5A—H5A	0.9800	C5B—H5B1	0.9800
C5A—H5B	0.9800	C5B—H5B2	0.9800
C5A—H5C	0.9800	C5B—H5B3	0.9800

C4A—N1A—N2A	113.82 (13)	C4B—N1B—N2B	113.61 (12)
C4A—N1A—H1A	129.1 (11)	C4B—N1B—H1B	126.7 (10)
N2A—N1A—H1A	116.9 (11)	N2B—N1B—H1B	119.7 (10)
C1A—N2A—N1A	105.42 (12)	C1B—N2B—N1B	105.14 (12)
O1A—N3A—C3A	115.11 (12)	O1B—N3B—C3B	115.32 (13)
N2A—C1A—C3A	109.56 (13)	N2B—C1B—C3B	109.83 (13)
N2A—C1A—C2A	121.60 (13)	N2B—C1B—C2B	121.54 (13)
C3A—C1A—C2A	128.84 (13)	C3B—C1B—C2B	128.62 (14)
C1A—C2A—H2A	109.5	C1B—C2B—H2B1	109.5
C1A—C2A—H2B	109.5	C1B—C2B—H2B2	109.5
H2A—C2A—H2B	109.5	H2B1—C2B—H2B2	109.5
C1A—C2A—H2C	109.5	C1B—C2B—H2B3	109.5
H2A—C2A—H2C	109.5	H2B1—C2B—H2B3	109.5
H2B—C2A—H2C	109.5	H2B2—C2B—H2B3	109.5
N3A—C3A—C4A	121.63 (13)	N3B—C3B—C4B	131.33 (14)
N3A—C3A—C1A	132.39 (14)	N3B—C3B—C1B	122.16 (14)
C4A—C3A—C1A	105.89 (13)	C4B—C3B—C1B	106.50 (13)
N1A—C4A—C3A	105.30 (13)	N1B—C4B—C3B	104.92 (13)
N1A—C4A—C5A	123.80 (14)	N1B—C4B—C5B	122.65 (14)
C3A—C4A—C5A	130.89 (14)	C3B—C4B—C5B	132.42 (14)
C4A—C5A—H5A	109.5	C4B—C5B—H5B1	109.5
C4A—C5A—H5B	109.5	C4B—C5B—H5B2	109.5
H5A—C5A—H5B	109.5	H5B1—C5B—H5B2	109.5
C4A—C5A—H5C	109.5	C4B—C5B—H5B3	109.5
H5A—C5A—H5C	109.5	H5B1—C5B—H5B3	109.5
H5B—C5A—H5C	109.5	H5B2—C5B—H5B3	109.5

C4A—N1A—N2A—C1A	0.03 (17)	C4B—N1B—N2B—C1B	−0.10 (17)
N1A—N2A—C1A—C3A	−0.15 (16)	N1B—N2B—C1B—C3B	0.46 (17)
N1A—N2A—C1A—C2A	−179.56 (13)	N1B—N2B—C1B—C2B	−178.40 (13)
O1A—N3A—C3A—C4A	178.61 (13)	O1B—N3B—C3B—C4B	2.4 (2)
O1A—N3A—C3A—C1A	2.4 (2)	O1B—N3B—C3B—C1B	−179.01 (14)
N2A—C1A—C3A—N3A	176.84 (15)	N2B—C1B—C3B—N3B	−179.59 (13)
C2A—C1A—C3A—N3A	−3.8 (3)	C2B—C1B—C3B—N3B	−0.8 (2)
N2A—C1A—C3A—C4A	0.22 (16)	N2B—C1B—C3B—C4B	−0.65 (17)
C2A—C1A—C3A—C4A	179.57 (15)	C2B—C1B—C3B—C4B	178.11 (15)
N2A—N1A—C4A—C3A	0.11 (17)	N2B—N1B—C4B—C3B	−0.30 (16)
N2A—N1A—C4A—C5A	179.38 (14)	N2B—N1B—C4B—C5B	178.69 (13)
N3A—C3A—C4A—N1A	−177.26 (14)	N3B—C3B—C4B—N1B	179.36 (15)
C1A—C3A—C4A—N1A	−0.19 (16)	C1B—C3B—C4B—N1B	0.56 (16)
N3A—C3A—C4A—C5A	3.5 (3)	N3B—C3B—C4B—C5B	0.5 (3)
C1A—C3A—C4A—C5A	−179.39 (16)	C1B—C3B—C4B—C5B	−178.29 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O1Aⁱ	0.954 (18)	1.802 (18)	2.7526 (16)	174.0 (15)
N1A—H1A···N2Bⁱⁱ	0.915 (19)	1.95 (2)	2.8544 (18)	171.5 (16)

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

Experimental details

Crystal data
Chemical formula	C₅H₇N₃O
M_r	125.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	4.0268 (2), 15.3793 (7), 19.6627 (9)
β (°)	94.613 (3)
V (Å³)	1213.75 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.46 × 0.33 × 0.13

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.955, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	9003, 2747, 1866
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.03
No. of reflections	2747
No. of parameters	175
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

Computer programs: COLLECT (Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O1Aⁱ	0.954 (18)	1.802 (18)	2.7526 (16)	174.0 (15)
N1A—H1A···N2Bⁱⁱ	0.915 (19)	1.95 (2)	2.8544 (18)	171.5 (16)

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

Acknowledgements

Financial support from the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041) and the Swedish Institute (Visby Program) is gratefully acknowledged.

References

Aromi, G. & Brechin, E. K. (2006). Struct. Bonding (Berlin), 122, 1–67. CAS Google Scholar
Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cameron, M., Gowenlock, B. G. & Boyd, A. S. F. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 2271–2274. Google Scholar
Fletcher, D. A., Gowenlock, B. G., Orrell, K. G., Šik, V., Hibbs, D. E., Hursthouse, M. B. & Abdul Malik, K. M. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 721–728. Google Scholar
Gatteschi, D., Sessoli, R. & Villain, J. (2006). Molecular Nanomagnets. Oxford University Press. Google Scholar
Halcrow, M. A. (2005). Coord. Chem. Rev. 249, 2880–2908. Web of Science CSD CrossRef CAS Google Scholar
Kanderal, O. M., Kozłowski, H., Dobosz, A., Świątek-Kozłowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428–1437. Web of Science CrossRef PubMed Google Scholar
Kovbasyuk, L., Pritzkow, H., Krämer, R. & Fritsky, I. O. (2004). Chem. Commun. pp. 880–881. Web of Science CrossRef Google Scholar
Mokhir, A. A., Gumienna-Kontecka, E. S., Świątek-Kozłowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Yu. (2002). Inorg. Chim. Acta, 329, 113–121. Web of Science CSD CrossRef CAS Google Scholar
Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750–4752. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mukhopadhyay, S., Mandal, S. K., Bhaduri, S. & Armstrong, W. H. (2004). Chem. Rev. 104, 3981–4026. Web of Science CrossRef PubMed CAS Google Scholar
Mullins, C. S. & Pecoraro, V. L. (2008). Coord. Chem. Rev. 252, 416–443. Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Petrusenko, S. R., Kokozay, V. N. & Fritsky, I. O. (1997). Polyhedron, 16, 267–274. CSD CrossRef CAS Web of Science Google Scholar
Sachse, A., Penkova, L., Noel, G., Dechert, S., Varzatskii, O. A., Fritsky, I. O. & Meyer, F. (2008). Synthesis, pp. 800–806. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Głowiak, T., Onindo, C. O., Fritsky, I. O. & Kozłowski, H. (1997). J. Inorg. Biochem. 65, 287–294. CSD CrossRef CAS Web of Science Google Scholar
Wörl, S., Fritsky, I. O., Hellwinkel, D., Pritzkow, H. & Krämer, R. (2005). Eur. J. Inorg. Chem. pp. 759–765. Google Scholar
Wörl, S., Pritzkow, H., Fritsky, I. O. & Krämer, R. (2005). Dalton Trans. pp. 27–29. Google Scholar