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The title compound, C10H10N2O, is of pharmacological interest. It contains a keto-tetra­hydro­pyridazine ring carrying a phenyl ring para to the carbonyl group. In the crystal structure, hydrogen-bonded centrosymmetric dimers are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010018/na6233sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010018/na6233Isup2.hkl
Contains datablock I

CCDC reference: 214826

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.098
  • Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Pyridazine compounds homologous to the title compound, (I), are known and particularly interesting as antidepressive agents (Biziere et al., 1988). This kind of compound has also been used for the treatment of Alzheimers disease (Passeri et al., 1985).

The geometric parameters of (I) are normal. The hydropyridazine ring adopts a half-chair conformation, with atoms C1, N2, N3 and C4 in a common plane and C5 0.222 (2) Å and C6 0.262 (2) Å on opposite sides of this plane. The plane is almost coplanar with the phenyl ring; the dihedral angle between the two planes is 1.73 (9) Å. In the crystal structure, hydrogen-bonded centrosymmetric dimers are observed.

Experimental top

142.4 g (8 mmol) of benzoylpropionic acid was dissolved in 170 ml e thanol. 43 g (8.6 mmol) of hydrazine hydrate was then added to this mixture and it was refluxed for 1 h. After cooling to room temperature, yellow crystals rose from the solution and were filtered off and dried.

Refinement top

H atoms bonded to C atoms were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C)] using a riding model with C—H = 0.99 Å or methylene C—H = 0.98 Å, respectively. The H atom bonded to N was refined freely.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Perspective view of the asymmetric unit of the title compound with the the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
(I) top
Crystal data top
C10H10N2OZ = 2
Mr = 174.20F(000) = 184
Triclinic, P1Dx = 1.351 Mg m3
a = 5.6712 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1749 (14) ÅCell parameters from 10040 reflections
c = 10.1055 (17) Åθ = 3.7–25.1°
α = 104.740 (14)°µ = 0.09 mm1
β = 104.392 (13)°T = 173 K
γ = 98.097 (14)°Block, colourless
V = 428.33 (13) Å30.44 × 0.38 × 0.36 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 3.8°
ω scansh = 66
5318 measured reflectionsk = 99
1483 independent reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0639P)2 + 0.0435P]
where P = (Fo2 + 2Fc2)/3
1483 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C10H10N2Oγ = 98.097 (14)°
Mr = 174.20V = 428.33 (13) Å3
Triclinic, P1Z = 2
a = 5.6712 (10) ÅMo Kα radiation
b = 8.1749 (14) ŵ = 0.09 mm1
c = 10.1055 (17) ÅT = 173 K
α = 104.740 (14)°0.44 × 0.38 × 0.36 mm
β = 104.392 (13)°
Data collection top
Stoe IPDS II two-circle
diffractometer
1318 reflections with I > 2σ(I)
5318 measured reflectionsRint = 0.025
1483 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.18 e Å3
1483 reflectionsΔρmin = 0.16 e Å3
122 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
C10.5763 (2)0.31939 (14)0.59845 (12)0.0250 (3)
N20.43300 (17)0.31959 (13)0.67873 (10)0.0294 (3)
N30.53050 (18)0.41628 (13)0.82212 (10)0.0313 (3)
H30.427 (3)0.4001 (19)0.8708 (16)0.039 (4)*
C40.7413 (2)0.54048 (14)0.88306 (12)0.0265 (3)
O40.79927 (15)0.62575 (11)1.01032 (8)0.0341 (3)
C50.8911 (2)0.57185 (14)0.78552 (12)0.0276 (3)
H5A1.07050.60140.83970.033*
H5B0.85140.67270.75430.033*
C60.8435 (2)0.41769 (16)0.65411 (13)0.0345 (3)
H6A0.88840.45880.57770.041*
H6B0.95250.33840.67830.041*
C110.4697 (2)0.20674 (14)0.44823 (12)0.0261 (3)
C120.2314 (2)0.09882 (15)0.40342 (13)0.0303 (3)
H120.13820.10000.46970.036*
C130.1304 (2)0.00889 (15)0.26482 (13)0.0347 (3)
H130.03170.08070.23650.042*
C140.2632 (2)0.01347 (16)0.16624 (13)0.0369 (3)
H140.19360.08830.07080.044*
C150.4979 (3)0.09226 (19)0.20861 (14)0.0433 (3)
H150.59010.09030.14180.052*
C160.6003 (2)0.20142 (17)0.34804 (13)0.0365 (3)
H160.76190.27350.37540.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0232 (5)0.0267 (6)0.0256 (6)0.0050 (4)0.0078 (4)0.0086 (5)
N20.0248 (5)0.0353 (5)0.0243 (5)0.0024 (4)0.0077 (4)0.0042 (4)
N30.0269 (5)0.0395 (6)0.0233 (5)0.0013 (4)0.0111 (4)0.0033 (4)
C40.0267 (6)0.0277 (6)0.0240 (6)0.0057 (4)0.0062 (5)0.0073 (5)
O40.0337 (5)0.0382 (5)0.0248 (5)0.0003 (3)0.0101 (3)0.0026 (4)
C50.0270 (6)0.0287 (6)0.0256 (6)0.0006 (4)0.0077 (5)0.0088 (5)
C60.0265 (6)0.0391 (7)0.0312 (7)0.0019 (5)0.0119 (5)0.0011 (5)
C110.0260 (6)0.0267 (5)0.0255 (6)0.0066 (4)0.0068 (5)0.0081 (5)
C120.0306 (6)0.0299 (6)0.0297 (6)0.0015 (5)0.0095 (5)0.0103 (5)
C130.0334 (6)0.0289 (6)0.0344 (7)0.0009 (5)0.0036 (5)0.0072 (5)
C140.0403 (7)0.0358 (6)0.0260 (6)0.0068 (5)0.0054 (5)0.0003 (5)
C150.0378 (7)0.0547 (8)0.0310 (7)0.0056 (6)0.0147 (6)0.0004 (6)
C160.0265 (6)0.0458 (7)0.0305 (7)0.0011 (5)0.0102 (5)0.0020 (5)
Geometric parameters (Å, º) top
C1—N21.2830 (15)C6—H6B0.9900
C1—C111.4811 (16)C11—C161.3911 (17)
C1—C61.5038 (15)C11—C121.4022 (16)
N2—N31.3877 (14)C12—C131.3772 (17)
N3—C41.3464 (15)C12—H120.9500
N3—H30.870 (16)C13—C141.3868 (18)
C4—O41.2316 (14)C13—H130.9500
C4—C51.4976 (15)C14—C151.3807 (19)
C5—C61.5163 (16)C14—H140.9500
C5—H5A0.9900C15—C161.3879 (17)
C5—H5B0.9900C15—H150.9500
C6—H6A0.9900C16—H160.9500
N2—C1—C11116.27 (10)C5—C6—H6B109.1
N2—C1—C6122.62 (10)H6A—C6—H6B107.8
C11—C1—C6120.98 (10)C16—C11—C12117.79 (11)
C1—N2—N3117.98 (9)C16—C11—C1122.10 (10)
C4—N3—N2127.23 (9)C12—C11—C1120.10 (10)
C4—N3—H3120.1 (10)C13—C12—C11121.04 (11)
N2—N3—H3112.1 (10)C13—C12—H12119.5
O4—C4—N3121.02 (10)C11—C12—H12119.5
O4—C4—C5123.01 (10)C12—C13—C14120.56 (11)
N3—C4—C5115.92 (10)C12—C13—H13119.7
C4—C5—C6113.40 (9)C14—C13—H13119.7
C4—C5—H5A108.9C15—C14—C13119.11 (11)
C6—C5—H5A108.9C15—C14—H14120.4
C4—C5—H5B108.9C13—C14—H14120.4
C6—C5—H5B108.9C14—C15—C16120.57 (11)
H5A—C5—H5B107.7C14—C15—H15119.7
C1—C6—C5112.69 (9)C16—C15—H15119.7
C1—C6—H6A109.1C15—C16—C11120.93 (11)
C5—C6—H6A109.1C15—C16—H16119.5
C1—C6—H6B109.1C11—C16—H16119.5
C11—C1—N2—N3176.62 (9)C6—C1—C11—C167.37 (17)
C6—C1—N2—N30.61 (17)N2—C1—C11—C124.45 (16)
C1—N2—N3—C415.45 (18)C6—C1—C11—C12171.63 (10)
N2—N3—C4—O4174.89 (10)C16—C11—C12—C130.06 (18)
N2—N3—C4—C52.66 (17)C1—C11—C12—C13178.99 (10)
O4—C4—C5—C6159.18 (11)C11—C12—C13—C140.25 (18)
N3—C4—C5—C623.33 (14)C12—C13—C14—C150.37 (19)
N2—C1—C6—C525.72 (16)C13—C14—C15—C160.2 (2)
C11—C1—C6—C5158.46 (10)C14—C15—C16—C110.1 (2)
C4—C5—C6—C135.60 (14)C12—C11—C16—C150.24 (19)
N2—C1—C11—C16176.55 (10)C1—C11—C16—C15178.78 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.870 (16)1.990 (16)2.8587 (13)177.1 (14)
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC10H10N2O
Mr174.20
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)5.6712 (10), 8.1749 (14), 10.1055 (17)
α, β, γ (°)104.740 (14), 104.392 (13), 98.097 (14)
V3)428.33 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.44 × 0.38 × 0.36
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5318, 1483, 1318
Rint0.025
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.098, 1.08
No. of reflections1483
No. of parameters122
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.16

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.

Selected geometric parameters (Å, º) top
C1—N21.2830 (15)N3—C41.3464 (15)
N2—N31.3877 (14)C4—O41.2316 (14)
C1—N2—N3117.98 (9)C4—N3—N2127.23 (9)
C1—N2—N3—C415.45 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.870 (16)1.990 (16)2.8587 (13)177.1 (14)
Symmetry code: (i) x+1, y+1, z+2.
 

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