3-Hy-droxy-1-[(morpholin-4-yl)meth-yl]pyridazin-6(1H)-one.

In the title compound, C9H13N3O3, the morpholine ring adopts a chair conformation and its mean plane makes a dihedral angle of 68.00 (11)° with the pyridazine ring. The carbonyl O atom deviates from the plane of the pyridazine ring by 0.0482 (12) Å. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds, forming chains along [1-10].

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010 ▶); Raparti et al. (2009 ▶). For a related structure, see: Wang et al. (2012 ▶).

Experimental

Crystal data

C9H13N3O3

M = 211.22

Triclinic,

a = 5.2110 (3) Å

b = 5.4165 (4) Å

c = 18.4544 (12) Å

α = 87.232 (2)°

β = 83.993 (6)°

γ = 80.862 (4)°

V = 511.18 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.969, T max = 0.979

8839 measured reflections

2530 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.158

S = 1.07

2530 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010477/pv2627sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010477/pv2627Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010477/pv2627Isup3.cml

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

C9H13N3O3	Z = 2
Mr = 211.22	F(000) = 224
Triclinic, P1	Dx = 1.372 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2110 (3) Å	Cell parameters from 2530 reflections
b = 5.4165 (4) Å	θ = 1.1–28.4°
c = 18.4544 (12) Å	µ = 0.11 mm−1
α = 87.232 (2)°	T = 293 K
β = 83.993 (6)°	Block, colourless
γ = 80.862 (4)°	0.30 × 0.25 × 0.20 mm
V = 511.18 (6) Å3

Bruker SMART APEXII area-detector diffractometer	2530 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 28.4°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.969, Tmax = 0.979	k = −7→7
8839 measured reflections	l = −24→24

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0734P)2 + 0.1237P] where P = (Fo2 + 2Fc2)/3
2530 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.2321 (3)	0.5749 (3)	0.10380 (9)	0.0350 (4)
C2	0.3128 (3)	0.3529 (3)	0.06412 (9)	0.0393 (4)
H2	0.2234	0.3183	0.0257	0.047*
C3	0.5197 (3)	0.1956 (3)	0.08329 (9)	0.0397 (4)
H3	0.5754	0.0493	0.0580	0.048*
C4	0.6579 (3)	0.2491 (3)	0.14265 (9)	0.0341 (4)
C5	0.6847 (3)	0.5467 (3)	0.23871 (9)	0.0382 (4)
H5A	0.8698	0.4820	0.2316	0.046*
H5B	0.6670	0.7278	0.2356	0.046*
C6	0.6498 (5)	0.2102 (4)	0.32915 (12)	0.0650 (6)
H6A	0.8343	0.1520	0.3166	0.078*
H6B	0.5510	0.1163	0.3018	0.078*
C7	0.5809 (7)	0.1687 (6)	0.40974 (14)	0.0896 (9)
H7A	0.6172	−0.0086	0.4221	0.108*
H7B	0.6888	0.2541	0.4367	0.108*
C8	0.2589 (6)	0.5165 (7)	0.41244 (14)	0.0896 (9)
H8A	0.3627	0.6065	0.4394	0.107*
H8B	0.0761	0.5767	0.4269	0.107*
C9	0.3172 (4)	0.5693 (5)	0.33187 (11)	0.0609 (6)
H9A	0.2066	0.4883	0.3046	0.073*
H9B	0.2821	0.7480	0.3214	0.073*
N1	0.3486 (3)	0.6309 (2)	0.15815 (7)	0.0350 (3)
N2	0.5574 (2)	0.4640 (2)	0.17747 (7)	0.0326 (3)
N3	0.5895 (3)	0.4751 (3)	0.31060 (8)	0.0430 (4)
O1	0.0275 (2)	0.7323 (2)	0.08280 (7)	0.0511 (4)
H1	−0.0028	0.8530	0.1092	0.077*
O2	0.8565 (2)	0.1128 (2)	0.16258 (7)	0.0484 (4)
O3	0.3137 (5)	0.2588 (5)	0.43038 (10)	0.1016 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0322 (8)	0.0339 (8)	0.0352 (8)	0.0063 (6)	−0.0032 (6)	−0.0019 (6)
C2	0.0397 (9)	0.0387 (9)	0.0382 (9)	0.0042 (7)	−0.0095 (7)	−0.0088 (7)
C3	0.0432 (10)	0.0327 (9)	0.0403 (9)	0.0070 (7)	−0.0066 (7)	−0.0111 (7)
C4	0.0337 (8)	0.0291 (8)	0.0366 (8)	0.0037 (6)	−0.0019 (6)	−0.0027 (6)
C5	0.0377 (9)	0.0374 (9)	0.0411 (9)	−0.0050 (7)	−0.0100 (7)	−0.0064 (7)
C6	0.0911 (17)	0.0508 (13)	0.0530 (12)	−0.0103 (12)	−0.0110 (11)	0.0064 (10)
C7	0.132 (3)	0.0806 (19)	0.0567 (15)	−0.0218 (18)	−0.0130 (16)	0.0188 (13)
C8	0.0836 (19)	0.125 (3)	0.0571 (15)	−0.0191 (18)	0.0134 (13)	−0.0112 (16)
C9	0.0515 (12)	0.0807 (16)	0.0503 (12)	−0.0107 (11)	0.0010 (9)	−0.0100 (11)
N1	0.0349 (7)	0.0299 (7)	0.0373 (7)	0.0065 (5)	−0.0063 (6)	−0.0043 (5)
N2	0.0314 (7)	0.0292 (7)	0.0353 (7)	0.0039 (5)	−0.0066 (5)	−0.0042 (5)
N3	0.0480 (9)	0.0448 (9)	0.0375 (8)	−0.0066 (7)	−0.0093 (6)	−0.0049 (6)
O1	0.0495 (8)	0.0477 (8)	0.0504 (8)	0.0227 (6)	−0.0192 (6)	−0.0131 (6)
O2	0.0417 (7)	0.0458 (7)	0.0523 (8)	0.0175 (6)	−0.0137 (6)	−0.0091 (6)
O3	0.1169 (18)	0.1262 (19)	0.0662 (12)	−0.0507 (15)	0.0097 (11)	0.0167 (12)

C1—N1	1.297 (2)	C6—H6A	0.9700
C1—O1	1.3341 (18)	C6—H6B	0.9700
C1—C2	1.421 (2)	C7—O3	1.419 (4)
C2—C3	1.331 (2)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.437 (2)	C8—O3	1.410 (4)
C3—H3	0.9300	C8—C9	1.509 (3)
C4—O2	1.2497 (18)	C8—H8A	0.9700
C4—N2	1.360 (2)	C8—H8B	0.9700
C5—N3	1.425 (2)	C9—N3	1.449 (3)
C5—N2	1.4892 (19)	C9—H9A	0.9700
C5—H5A	0.9700	C9—H9B	0.9700
C5—H5B	0.9700	N1—N2	1.3660 (17)
C6—N3	1.452 (3)	O1—H1	0.8200
C6—C7	1.508 (3)
N1—C1—O1	119.33 (14)	C6—C7—H7A	109.4
N1—C1—C2	123.26 (14)	O3—C7—H7B	109.4
O1—C1—C2	117.41 (14)	C6—C7—H7B	109.4
C3—C2—C1	118.37 (15)	H7A—C7—H7B	108.0
C3—C2—H2	120.8	O3—C8—C9	111.8 (2)
C1—C2—H2	120.8	O3—C8—H8A	109.3
C2—C3—C4	120.80 (14)	C9—C8—H8A	109.3
C2—C3—H3	119.6	O3—C8—H8B	109.3
C4—C3—H3	119.6	C9—C8—H8B	109.3
O2—C4—N2	120.60 (14)	H8A—C8—H8B	107.9
O2—C4—C3	124.21 (14)	N3—C9—C8	108.85 (19)
N2—C4—C3	115.19 (13)	N3—C9—H9A	109.9
N3—C5—N2	116.93 (13)	C8—C9—H9A	109.9
N3—C5—H5A	108.1	N3—C9—H9B	109.9
N2—C5—H5A	108.1	C8—C9—H9B	109.9
N3—C5—H5B	108.1	H9A—C9—H9B	108.3
N2—C5—H5B	108.1	C1—N1—N2	117.12 (12)
H5A—C5—H5B	107.3	C4—N2—N1	125.20 (13)
N3—C6—C7	109.2 (2)	C4—N2—C5	121.09 (13)
N3—C6—H6A	109.8	N1—N2—C5	113.57 (12)
C7—C6—H6A	109.8	C5—N3—C9	115.28 (15)
N3—C6—H6B	109.8	C5—N3—C6	115.05 (15)
C7—C6—H6B	109.8	C9—N3—C6	110.95 (18)
H6A—C6—H6B	108.3	C1—O1—H1	109.5
O3—C7—C6	111.4 (2)	C8—O3—C7	109.8 (2)
O3—C7—H7A	109.4
N1—C1—C2—C3	−0.6 (3)	C1—N1—N2—C4	2.5 (2)
O1—C1—C2—C3	178.72 (16)	C1—N1—N2—C5	178.12 (14)
C1—C2—C3—C4	0.0 (3)	N3—C5—N2—C4	−94.05 (18)
C2—C3—C4—O2	−178.44 (17)	N3—C5—N2—N1	90.12 (17)
C2—C3—C4—N2	1.7 (2)	N2—C5—N3—C9	−61.2 (2)
N3—C6—C7—O3	57.7 (3)	N2—C5—N3—C6	69.9 (2)
O3—C8—C9—N3	−58.1 (3)	C8—C9—N3—C5	−170.26 (19)
O1—C1—N1—N2	−179.85 (14)	C8—C9—N3—C6	56.7 (2)
C2—C1—N1—N2	−0.5 (2)	C7—C6—N3—C5	170.00 (19)
O2—C4—N2—N1	177.10 (14)	C7—C6—N3—C9	−56.9 (3)
C3—C4—N2—N1	−3.0 (2)	C9—C8—O3—C7	59.2 (3)
O2—C4—N2—C5	1.8 (2)	C6—C7—O3—C8	−58.9 (3)
C3—C4—N2—C5	−178.32 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.77	2.5777 (16)	167
C2—H2···O1ii	0.93	2.55	3.478 (2)	175
C5—H5A···O2	0.97	2.44	2.772 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.77	2.5777 (16)	167
C2—H2⋯O1ii	0.93	2.55	3.478 (2)	175
C5—H5A⋯O2	0.97	2.44	2.772 (2)	100

Symmetry codes: (i) ; (ii) .