6-Oxo-1,6-dihydro-pyridazine-3-carbaldehyde monohydrate.

In the title hydrate, C(5)H(4)N(2)O(2)·H(2)O, 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 mol-ecules 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 = 142.12

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 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

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031674/jj2141sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031674/jj2141Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031674/jj2141Isup3.cml

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

C5H4N2O2·H2O	F(000) = 296
Mr = 142.12	Dx = 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

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

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(Fo2) + (0.0736P)2 + 0.3841P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1190 reflections	Δρmax = 0.30 e Å−3
92 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .