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

Wang, L.

doi:10.1107/S1600536812031674

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2483

https://doi.org/10.1107/S1600536812031674

Open

access

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

Lei Wang ^a ^*

^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 ). For bond lengths and angles in related compounds, see: Sarkhel & Desiraju (2004 ).

Experimental

Crystal data

C₅H₄N₂O₂·H₂O
M_r = 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 ) T_min = 0.976, T_max = 0.987
3981 measured reflections
1190 independent reflections
862 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.159
S = 1.06
1190 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SMART; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031674/jj2141sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031674/jj2141Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031674/jj2141Isup3.cml

checkCIF report

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.

Structure description 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).

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

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	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·H₂O	F(000) = 296
M_r = 142.12	D_x = 1.474 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1099 reflections
a = 8.978 (2) Å	θ = 3.7–25.6°
b = 6.4150 (16) Å	µ = 0.12 mm⁻¹
c = 11.354 (3) Å	T = 296 K
β = 101.696 (3)°	Block, colourless
V = 640.4 (3) Å³	0.20 × 0.18 × 0.11 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1190 independent reflections
Radiation source: fine-focus sealed tube	862 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.976, T_max = 0.987	k = −7→7
3981 measured reflections	l = −13→13

Refinement top

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0736P)² + 0.3841P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1190 reflections	Δρ_max = 0.30 e Å⁻³
92 parameters	Δρ_min = −0.21 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: 0.009 (5)

Crystal data top

C₅H₄N₂O₂·H₂O	V = 640.4 (3) Å³
M_r = 142.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.978 (2) Å	µ = 0.12 mm⁻¹
b = 6.4150 (16) Å	T = 296 K
c = 11.354 (3) Å	0.20 × 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)
T_min = 0.976, T_max = 0.987	R_int = 0.024
3981 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
1190 reflections	Δρ_min = −0.21 e Å⁻³
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

	x	y	z	U_iso*/U_eq
N1	0.2572 (2)	1.0090 (3)	0.98272 (18)	0.0477 (6)
N2	0.1866 (2)	0.9050 (3)	1.05760 (18)	0.0452 (6)
H1	0.1462	0.9788	1.1061	0.054*
O1	0.4654 (3)	0.9374 (4)	0.7609 (2)	0.0853 (8)
O2	0.0999 (2)	0.6205 (3)	1.13746 (18)	0.0611 (6)
O3	0.0862 (3)	0.2000 (3)	0.19846 (18)	0.0672 (7)
H1W	0.0911	0.3173	0.1755	0.101*
H2W	0.0389	0.1858	0.2485	0.101*
C1	0.3210 (3)	0.8957 (4)	0.9111 (2)	0.0456 (7)
C2	0.3184 (3)	0.6758 (4)	0.9111 (2)	0.0524 (7)
H2	0.3661	0.6012	0.8590	0.063*
C3	0.2468 (3)	0.5760 (4)	0.9866 (2)	0.0528 (7)
H3	0.2453	0.4311	0.9885	0.063*
C4	0.1722 (3)	0.6946 (4)	1.0650 (2)	0.0461 (7)
C5	0.4022 (3)	1.0224 (4)	0.8288 (2)	0.0410 (6)
H5	0.4017	1.1673	0.8323	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0609 (14)	0.0400 (12)	0.0494 (12)	−0.0020 (10)	0.0286 (11)	0.0013 (9)
N2	0.0585 (13)	0.0379 (12)	0.0486 (12)	−0.0005 (10)	0.0332 (10)	−0.0021 (9)
O1	0.1000 (18)	0.0802 (17)	0.0927 (16)	−0.0064 (14)	0.0598 (15)	0.0048 (14)
O2	0.0840 (14)	0.0454 (11)	0.0703 (13)	−0.0035 (10)	0.0541 (11)	0.0018 (9)
O3	0.1018 (17)	0.0420 (11)	0.0768 (14)	0.0021 (10)	0.0626 (13)	−0.0010 (9)
C1	0.0521 (15)	0.0438 (15)	0.0459 (14)	−0.0015 (12)	0.0218 (12)	0.0003 (11)
C2	0.0645 (17)	0.0477 (16)	0.0545 (16)	0.0049 (13)	0.0342 (14)	−0.0041 (12)
C3	0.0706 (18)	0.0361 (14)	0.0623 (16)	0.0006 (13)	0.0383 (14)	−0.0041 (12)
C4	0.0567 (16)	0.0379 (15)	0.0508 (14)	0.0009 (12)	0.0276 (12)	0.0012 (11)
C5	0.0474 (13)	0.0441 (14)	0.0389 (12)	−0.0028 (11)	0.0260 (11)	0.0014 (10)

Geometric parameters (Å, º) top

N1—C1	1.306 (3)	C1—C2	1.410 (4)
N1—N2	1.337 (3)	C1—C5	1.531 (3)
N2—C4	1.360 (3)	C2—C3	1.335 (4)
N2—H1	0.8600	C2—H2	0.9300
O1—C5	1.179 (3)	C3—C4	1.435 (3)
O2—C4	1.241 (3)	C3—H3	0.9300
O3—H1W	0.8002	C5—H5	0.9300
O3—H2W	0.7808

C1—N1—N2	116.3 (2)	C1—C2—H2	120.3
N1—N2—C4	126.68 (19)	C2—C3—C4	119.3 (2)
N1—N2—H1	116.7	C2—C3—H3	120.3
C4—N2—H1	116.7	C4—C3—H3	120.3
H1W—O3—H2W	114.8	O2—C4—N2	119.3 (2)
N1—C1—C2	123.2 (2)	O2—C4—C3	125.5 (2)
N1—C1—C5	114.1 (2)	N2—C4—C3	115.2 (2)
C2—C1—C5	122.8 (2)	O1—C5—C1	120.3 (3)
C3—C2—C1	119.3 (2)	O1—C5—H5	119.8
C3—C2—H2	120.3	C1—C5—H5	119.8

C1—N1—N2—C4	−1.4 (4)	N1—N2—C4—O2	−178.3 (2)
N2—N1—C1—C2	−0.4 (4)	N1—N2—C4—C3	2.7 (4)
N2—N1—C1—C5	−179.1 (2)	C2—C3—C4—O2	178.7 (3)
N1—C1—C2—C3	0.5 (5)	C2—C3—C4—N2	−2.3 (4)
C5—C1—C2—C3	179.1 (2)	N1—C1—C5—O1	179.3 (3)
C1—C2—C3—C4	0.9 (4)	C2—C1—C5—O1	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₅H₄N₂O₂·H₂O
M_r	142.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.978 (2), 6.4150 (16), 11.354 (3)
β (°)	101.696 (3)
V (Å³)	640.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.18 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	3981, 1190, 862
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.159, 1.06
No. of reflections	1190
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N2—H1···O3ⁱ	0.86	1.91	2.745 (3)	164.8
O3—H1W···O2ⁱⁱ	0.80	2.00	2.794 (3)	173.3
O3—H2W···O2ⁱⁱⁱ	0.78	2.01	2.790 (2)	172.2

Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z−1; (iii) −x, y−1/2, −z+3/2.

References

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2483

https://doi.org/10.1107/S1600536812031674

Open

access