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
CCDC reference: 214826
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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.
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.
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.
Crystal data top
C10H10N2O | Z = 2 |
Mr = 174.20 | F(000) = 184 |
Triclinic, P1 | Dx = 1.351 Mg m−3 |
a = 5.6712 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1749 (14) Å | Cell parameters from 10040 reflections |
c = 10.1055 (17) Å | θ = 3.7–25.1° |
α = 104.740 (14)° | µ = 0.09 mm−1 |
β = 104.392 (13)° | T = 173 K |
γ = 98.097 (14)° | Block, colourless |
V = 428.33 (13) Å3 | 0.44 × 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 tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 3.8° |
ω scans | h = −6→6 |
5318 measured reflections | k = −9→9 |
1483 independent reflections | l = −11→11 |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H 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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Crystal data top
C10H10N2O | γ = 98.097 (14)° |
Mr = 174.20 | V = 428.33 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.6712 (10) Å | Mo Kα radiation |
b = 8.1749 (14) Å | µ = 0.09 mm−1 |
c = 10.1055 (17) Å | T = 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 reflections | Rint = 0.025 |
1483 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.18 e Å−3 |
1483 reflections | Δρmin = −0.16 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.5763 (2) | 0.31939 (14) | 0.59845 (12) | 0.0250 (3) | |
N2 | 0.43300 (17) | 0.31959 (13) | 0.67873 (10) | 0.0294 (3) | |
N3 | 0.53050 (18) | 0.41628 (13) | 0.82212 (10) | 0.0313 (3) | |
H3 | 0.427 (3) | 0.4001 (19) | 0.8708 (16) | 0.039 (4)* | |
C4 | 0.7413 (2) | 0.54048 (14) | 0.88306 (12) | 0.0265 (3) | |
O4 | 0.79927 (15) | 0.62575 (11) | 1.01032 (8) | 0.0341 (3) | |
C5 | 0.8911 (2) | 0.57185 (14) | 0.78552 (12) | 0.0276 (3) | |
H5A | 1.0705 | 0.6014 | 0.8397 | 0.033* | |
H5B | 0.8514 | 0.6727 | 0.7543 | 0.033* | |
C6 | 0.8435 (2) | 0.41769 (16) | 0.65411 (13) | 0.0345 (3) | |
H6A | 0.8884 | 0.4588 | 0.5777 | 0.041* | |
H6B | 0.9525 | 0.3384 | 0.6783 | 0.041* | |
C11 | 0.4697 (2) | 0.20674 (14) | 0.44823 (12) | 0.0261 (3) | |
C12 | 0.2314 (2) | 0.09882 (15) | 0.40342 (13) | 0.0303 (3) | |
H12 | 0.1382 | 0.1000 | 0.4697 | 0.036* | |
C13 | 0.1304 (2) | −0.00889 (15) | 0.26482 (13) | 0.0347 (3) | |
H13 | −0.0317 | −0.0807 | 0.2365 | 0.042* | |
C14 | 0.2632 (2) | −0.01347 (16) | 0.16624 (13) | 0.0369 (3) | |
H14 | 0.1936 | −0.0883 | 0.0708 | 0.044* | |
C15 | 0.4979 (3) | 0.09226 (19) | 0.20861 (14) | 0.0433 (3) | |
H15 | 0.5901 | 0.0903 | 0.1418 | 0.052* | |
C16 | 0.6003 (2) | 0.20142 (17) | 0.34804 (13) | 0.0365 (3) | |
H16 | 0.7619 | 0.2735 | 0.3754 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0232 (5) | 0.0267 (6) | 0.0256 (6) | 0.0050 (4) | 0.0078 (4) | 0.0086 (5) |
N2 | 0.0248 (5) | 0.0353 (5) | 0.0243 (5) | 0.0024 (4) | 0.0077 (4) | 0.0042 (4) |
N3 | 0.0269 (5) | 0.0395 (6) | 0.0233 (5) | −0.0013 (4) | 0.0111 (4) | 0.0033 (4) |
C4 | 0.0267 (6) | 0.0277 (6) | 0.0240 (6) | 0.0057 (4) | 0.0062 (5) | 0.0073 (5) |
O4 | 0.0337 (5) | 0.0382 (5) | 0.0248 (5) | −0.0003 (3) | 0.0101 (3) | 0.0026 (4) |
C5 | 0.0270 (6) | 0.0287 (6) | 0.0256 (6) | 0.0006 (4) | 0.0077 (5) | 0.0088 (5) |
C6 | 0.0265 (6) | 0.0391 (7) | 0.0312 (7) | −0.0019 (5) | 0.0119 (5) | 0.0011 (5) |
C11 | 0.0260 (6) | 0.0267 (5) | 0.0255 (6) | 0.0066 (4) | 0.0068 (5) | 0.0081 (5) |
C12 | 0.0306 (6) | 0.0299 (6) | 0.0297 (6) | 0.0015 (5) | 0.0095 (5) | 0.0103 (5) |
C13 | 0.0334 (6) | 0.0289 (6) | 0.0344 (7) | −0.0009 (5) | 0.0036 (5) | 0.0072 (5) |
C14 | 0.0403 (7) | 0.0358 (6) | 0.0260 (6) | 0.0068 (5) | 0.0054 (5) | −0.0003 (5) |
C15 | 0.0378 (7) | 0.0547 (8) | 0.0310 (7) | 0.0056 (6) | 0.0147 (6) | 0.0004 (6) |
C16 | 0.0265 (6) | 0.0458 (7) | 0.0305 (7) | 0.0011 (5) | 0.0102 (5) | 0.0020 (5) |
Geometric parameters (Å, º) top
C1—N2 | 1.2830 (15) | C6—H6B | 0.9900 |
C1—C11 | 1.4811 (16) | C11—C16 | 1.3911 (17) |
C1—C6 | 1.5038 (15) | C11—C12 | 1.4022 (16) |
N2—N3 | 1.3877 (14) | C12—C13 | 1.3772 (17) |
N3—C4 | 1.3464 (15) | C12—H12 | 0.9500 |
N3—H3 | 0.870 (16) | C13—C14 | 1.3868 (18) |
C4—O4 | 1.2316 (14) | C13—H13 | 0.9500 |
C4—C5 | 1.4976 (15) | C14—C15 | 1.3807 (19) |
C5—C6 | 1.5163 (16) | C14—H14 | 0.9500 |
C5—H5A | 0.9900 | C15—C16 | 1.3879 (17) |
C5—H5B | 0.9900 | C15—H15 | 0.9500 |
C6—H6A | 0.9900 | C16—H16 | 0.9500 |
| | | |
N2—C1—C11 | 116.27 (10) | C5—C6—H6B | 109.1 |
N2—C1—C6 | 122.62 (10) | H6A—C6—H6B | 107.8 |
C11—C1—C6 | 120.98 (10) | C16—C11—C12 | 117.79 (11) |
C1—N2—N3 | 117.98 (9) | C16—C11—C1 | 122.10 (10) |
C4—N3—N2 | 127.23 (9) | C12—C11—C1 | 120.10 (10) |
C4—N3—H3 | 120.1 (10) | C13—C12—C11 | 121.04 (11) |
N2—N3—H3 | 112.1 (10) | C13—C12—H12 | 119.5 |
O4—C4—N3 | 121.02 (10) | C11—C12—H12 | 119.5 |
O4—C4—C5 | 123.01 (10) | C12—C13—C14 | 120.56 (11) |
N3—C4—C5 | 115.92 (10) | C12—C13—H13 | 119.7 |
C4—C5—C6 | 113.40 (9) | C14—C13—H13 | 119.7 |
C4—C5—H5A | 108.9 | C15—C14—C13 | 119.11 (11) |
C6—C5—H5A | 108.9 | C15—C14—H14 | 120.4 |
C4—C5—H5B | 108.9 | C13—C14—H14 | 120.4 |
C6—C5—H5B | 108.9 | C14—C15—C16 | 120.57 (11) |
H5A—C5—H5B | 107.7 | C14—C15—H15 | 119.7 |
C1—C6—C5 | 112.69 (9) | C16—C15—H15 | 119.7 |
C1—C6—H6A | 109.1 | C15—C16—C11 | 120.93 (11) |
C5—C6—H6A | 109.1 | C15—C16—H16 | 119.5 |
C1—C6—H6B | 109.1 | C11—C16—H16 | 119.5 |
| | | |
C11—C1—N2—N3 | 176.62 (9) | C6—C1—C11—C16 | −7.37 (17) |
C6—C1—N2—N3 | 0.61 (17) | N2—C1—C11—C12 | −4.45 (16) |
C1—N2—N3—C4 | 15.45 (18) | C6—C1—C11—C12 | 171.63 (10) |
N2—N3—C4—O4 | 174.89 (10) | C16—C11—C12—C13 | 0.06 (18) |
N2—N3—C4—C5 | −2.66 (17) | C1—C11—C12—C13 | −178.99 (10) |
O4—C4—C5—C6 | 159.18 (11) | C11—C12—C13—C14 | 0.25 (18) |
N3—C4—C5—C6 | −23.33 (14) | C12—C13—C14—C15 | −0.37 (19) |
N2—C1—C6—C5 | −25.72 (16) | C13—C14—C15—C16 | 0.2 (2) |
C11—C1—C6—C5 | 158.46 (10) | C14—C15—C16—C11 | 0.1 (2) |
C4—C5—C6—C1 | 35.60 (14) | C12—C11—C16—C15 | −0.24 (19) |
N2—C1—C11—C16 | 176.55 (10) | C1—C11—C16—C15 | 178.78 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O4i | 0.870 (16) | 1.990 (16) | 2.8587 (13) | 177.1 (14) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Experimental details
Crystal data |
Chemical formula | C10H10N2O |
Mr | 174.20 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 428.33 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.44 × 0.38 × 0.36 |
|
Data collection |
Diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5318, 1483, 1318 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.594 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.098, 1.08 |
No. of reflections | 1483 |
No. of parameters | 122 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.16 |
Selected geometric parameters (Å, º) topC1—N2 | 1.2830 (15) | N3—C4 | 1.3464 (15) |
N2—N3 | 1.3877 (14) | C4—O4 | 1.2316 (14) |
| | | |
C1—N2—N3 | 117.98 (9) | C4—N3—N2 | 127.23 (9) |
| | | |
C1—N2—N3—C4 | 15.45 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O4i | 0.870 (16) | 1.990 (16) | 2.8587 (13) | 177.1 (14) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
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.