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ISSN: 2056-9890

6-Oxo-1,6-di­hydro­pyridazine-3-carbaldehyde monohydrate

aSchool of Chemistry and Chemical Engineering, Linyi University, Linyi 276005, People's Republic of China
*Correspondence e-mail: linyiwangcao@163.com

(Received 25 May 2012; accepted 11 July 2012; online 18 July 2012)

In the title hydrate, C5H4N2O2·H2O, the pyridazine ring is essentially planar, with an r.m.s. deviation of 0.0025 Å. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the mol­ecules into a one-dimensional chain.

Related literature

For the biological functions of pyridazine and its derivatives, see: Heinisch & Kopelent (1992[Heinisch, G. & Kopelent, H. (1992). Prog. Med. Chem., 29, 141-183.]). For bond lengths and angles in related compounds, see: Sarkhel & Desiraju (2004[Sarkhel, S. & Desiraju, G. R. (2004). Proteins, 54, 247-259. ]).

[Scheme 1]

Experimental

Crystal data
  • C5H4N2O2·H2O

  • Mr = 142.12

  • Monoclinic, P 21 /c

  • a = 8.978 (2) Å

  • b = 6.4150 (16) Å

  • c = 11.354 (3) Å

  • β = 101.696 (3)°

  • V = 640.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 296 K

  • 0.20 × 0.18 × 0.11 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.987

  • 3981 measured reflections

  • 1190 independent reflections

  • 862 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.159

  • S = 1.06

  • 1190 reflections

  • 92 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H1⋯O3i 0.86 1.91 2.745 (3) 165
O3—H1W⋯O2ii 0.80 2.00 2.794 (3) 173
O3—H2W⋯O2iii 0.78 2.01 2.790 (2) 172
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z-1; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Pyridazine derivatives are a family of very important compounds due to their antiinflammatory, antimicrobial, insecticidal and herbicidal activities. Compounds with different activity can be obtained when different groups are introduced into pyridazine structures (Heinisch & Kopelent, 1992). Hydrogen bonds have been shown to play important roles in the physical, chemical, and biological properties of many chemical processes. In the title compound, (I), N—H..O and O—H···O hydrogen bonds have been observed. The title compound, C5H4N2O2.H2O, crystallizes with an organic molecule and a water molecule in the asymmetric unit (Fig. 1). The pyridazine ring is essential planar, with an r.m.s. deviation of 0.0025 Å. The O2, C5 and O1 substituents are coplanar with the mean plane of the pryidazine ring [displacements = 0.0364, -0.0058 and -0.0146 Å, respectively]. Bond lengths and angles are within normal ranges (Sarkhel & Desiraju, 2004). In the crystal, O—H···O and N—H···O hydrogen bonds (Table 1) link the molecules into a one-dimensional chain (Fig. 2).

Related literature top

For the biological functions of pyridazine and its derivatives, see: Heinisch & Kopelent (1992). For bond lengths and angles in related compounds, see: Sarkhel & Desiraju (2004).

Experimental top

To a solid of 3-Chloro-6-methylpyridazine (5 mmol) in dry dioxane was added SeO2 (1.5 g). The mixture was stirred for 6 h at the reflux temperature of dioxane. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (ethyl acetate) to afford the title compound as a light yellow solid (497 mg, yield 70%). The title compound was recrystallized from methanol at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Refinement top

H1W and H2W were located by a difference map and refined isotropically. All of the remaining H atoms were positioned geometrically and treated as riding, with C—H bonding lengths constrained to 0.93 Å (aromatic CH) or 0.97 Å (methylene CH2), and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methylene C).

Structure description top

Pyridazine derivatives are a family of very important compounds due to their antiinflammatory, antimicrobial, insecticidal and herbicidal activities. Compounds with different activity can be obtained when different groups are introduced into pyridazine structures (Heinisch & Kopelent, 1992). Hydrogen bonds have been shown to play important roles in the physical, chemical, and biological properties of many chemical processes. In the title compound, (I), N—H..O and O—H···O hydrogen bonds have been observed. The title compound, C5H4N2O2.H2O, crystallizes with an organic molecule and a water molecule in the asymmetric unit (Fig. 1). The pyridazine ring is essential planar, with an r.m.s. deviation of 0.0025 Å. The O2, C5 and O1 substituents are coplanar with the mean plane of the pryidazine ring [displacements = 0.0364, -0.0058 and -0.0146 Å, respectively]. Bond lengths and angles are within normal ranges (Sarkhel & Desiraju, 2004). In the crystal, O—H···O and N—H···O hydrogen bonds (Table 1) link the molecules into a one-dimensional chain (Fig. 2).

For the biological functions of pyridazine and its derivatives, see: Heinisch & Kopelent (1992). For bond lengths and angles in related compounds, see: Sarkhel & Desiraju (2004).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The molecular packing for (I) viewed along the a axis. O—H···O and N—H···O hydrogen bonds are shown by dashed lines linking the molecules into a one-dimensional chain.
6-Oxo-1,6-dihydropyridazine-3-carbaldehyde monohydrate top
Crystal data top
C5H4N2O2·H2OF(000) = 296
Mr = 142.12Dx = 1.474 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1099 reflections
a = 8.978 (2) Åθ = 3.7–25.6°
b = 6.4150 (16) ŵ = 0.12 mm1
c = 11.354 (3) ÅT = 296 K
β = 101.696 (3)°Block, colourless
V = 640.4 (3) Å30.20 × 0.18 × 0.11 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1190 independent reflections
Radiation source: fine-focus sealed tube862 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.976, Tmax = 0.987k = 77
3981 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.3841P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1190 reflectionsΔρmax = 0.30 e Å3
92 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (5)
Crystal data top
C5H4N2O2·H2OV = 640.4 (3) Å3
Mr = 142.12Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.978 (2) ŵ = 0.12 mm1
b = 6.4150 (16) ÅT = 296 K
c = 11.354 (3) Å0.20 × 0.18 × 0.11 mm
β = 101.696 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1190 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
862 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.987Rint = 0.024
3981 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.06Δρmax = 0.30 e Å3
1190 reflectionsΔρmin = 0.21 e Å3
92 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
xyzUiso*/Ueq
N10.2572 (2)1.0090 (3)0.98272 (18)0.0477 (6)
N20.1866 (2)0.9050 (3)1.05760 (18)0.0452 (6)
H10.14620.97881.10610.054*
O10.4654 (3)0.9374 (4)0.7609 (2)0.0853 (8)
O20.0999 (2)0.6205 (3)1.13746 (18)0.0611 (6)
O30.0862 (3)0.2000 (3)0.19846 (18)0.0672 (7)
H1W0.09110.31730.17550.101*
H2W0.03890.18580.24850.101*
C10.3210 (3)0.8957 (4)0.9111 (2)0.0456 (7)
C20.3184 (3)0.6758 (4)0.9111 (2)0.0524 (7)
H20.36610.60120.85900.063*
C30.2468 (3)0.5760 (4)0.9866 (2)0.0528 (7)
H30.24530.43110.98850.063*
C40.1722 (3)0.6946 (4)1.0650 (2)0.0461 (7)
C50.4022 (3)1.0224 (4)0.8288 (2)0.0410 (6)
H50.40171.16730.83230.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0609 (14)0.0400 (12)0.0494 (12)0.0020 (10)0.0286 (11)0.0013 (9)
N20.0585 (13)0.0379 (12)0.0486 (12)0.0005 (10)0.0332 (10)0.0021 (9)
O10.1000 (18)0.0802 (17)0.0927 (16)0.0064 (14)0.0598 (15)0.0048 (14)
O20.0840 (14)0.0454 (11)0.0703 (13)0.0035 (10)0.0541 (11)0.0018 (9)
O30.1018 (17)0.0420 (11)0.0768 (14)0.0021 (10)0.0626 (13)0.0010 (9)
C10.0521 (15)0.0438 (15)0.0459 (14)0.0015 (12)0.0218 (12)0.0003 (11)
C20.0645 (17)0.0477 (16)0.0545 (16)0.0049 (13)0.0342 (14)0.0041 (12)
C30.0706 (18)0.0361 (14)0.0623 (16)0.0006 (13)0.0383 (14)0.0041 (12)
C40.0567 (16)0.0379 (15)0.0508 (14)0.0009 (12)0.0276 (12)0.0012 (11)
C50.0474 (13)0.0441 (14)0.0389 (12)0.0028 (11)0.0260 (11)0.0014 (10)
Geometric parameters (Å, º) top
N1—C11.306 (3)C1—C21.410 (4)
N1—N21.337 (3)C1—C51.531 (3)
N2—C41.360 (3)C2—C31.335 (4)
N2—H10.8600C2—H20.9300
O1—C51.179 (3)C3—C41.435 (3)
O2—C41.241 (3)C3—H30.9300
O3—H1W0.8002C5—H50.9300
O3—H2W0.7808
C1—N1—N2116.3 (2)C1—C2—H2120.3
N1—N2—C4126.68 (19)C2—C3—C4119.3 (2)
N1—N2—H1116.7C2—C3—H3120.3
C4—N2—H1116.7C4—C3—H3120.3
H1W—O3—H2W114.8O2—C4—N2119.3 (2)
N1—C1—C2123.2 (2)O2—C4—C3125.5 (2)
N1—C1—C5114.1 (2)N2—C4—C3115.2 (2)
C2—C1—C5122.8 (2)O1—C5—C1120.3 (3)
C3—C2—C1119.3 (2)O1—C5—H5119.8
C3—C2—H2120.3C1—C5—H5119.8
C1—N1—N2—C41.4 (4)N1—N2—C4—O2178.3 (2)
N2—N1—C1—C20.4 (4)N1—N2—C4—C32.7 (4)
N2—N1—C1—C5179.1 (2)C2—C3—C4—O2178.7 (3)
N1—C1—C2—C30.5 (5)C2—C3—C4—N22.3 (4)
C5—C1—C2—C3179.1 (2)N1—C1—C5—O1179.3 (3)
C1—C2—C3—C40.9 (4)C2—C1—C5—O10.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O3i0.861.912.745 (3)165
O3—H1W···O2ii0.802.002.794 (3)173
O3—H2W···O2iii0.782.012.790 (2)172
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z1; (iii) x, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC5H4N2O2·H2O
Mr142.12
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.978 (2), 6.4150 (16), 11.354 (3)
β (°) 101.696 (3)
V3)640.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.20 × 0.18 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.976, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
3981, 1190, 862
Rint0.024
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.159, 1.06
No. of reflections1190
No. of parameters92
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.21

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O3i0.861.912.745 (3)164.8
O3—H1W···O2ii0.802.002.794 (3)173.3
O3—H2W···O2iii0.782.012.790 (2)172.2
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z1; (iii) x, y1/2, z+3/2.
 

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHeinisch, G. & Kopelent, H. (1992). Prog. Med. Chem., 29, 141–183.  CrossRef PubMed CAS Google Scholar
First citationSarkhel, S. & Desiraju, G. R. (2004). Proteins, 54, 247–259.   Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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