Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007165/ob6228sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007165/ob6228Isup2.hkl |
CCDC reference: 214594
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.102
- Data-to-parameter ratio = 11.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound, (I), was prepared from hydrazine and pyruvic acid by a one-step reaction. Hydrazine (1 mmol) was added slowly to pyruvic acid (1 mmol) and the resulting solution stirred at room temperature for 4 h. After cooling, the product was kept at room temperature and crystals of (I) suitable for single-crystal X-ray diffraction analysis appeared after several days.
The positions of all H atoms were fixed geometrically (C—H = 0.93 and 0.96 Å, and N—H = 0.86 and 0.89 Å).
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. View of the title compound, (I), with ellipsoids at the 50% probability level. | |
Fig. 2. A view of the crystal packing of (I). |
C6H8N4O2 | F(000) = 352 |
Mr = 168.16 | Dx = 1.508 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2289 reflections |
a = 7.359 (1) Å | θ = 2.9–27.9° |
b = 10.261 (1) Å | µ = 0.12 mm−1 |
c = 10.005 (1) Å | T = 293 K |
β = 101.30 (1)° | Block, colourless |
V = 740.84 (15) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 1190 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 25.0°, θmin = 2.8° |
ϕ and ω scans | h = −8→8 |
3540 measured reflections | k = −12→8 |
1288 independent reflections | l = −11→11 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3 |
1288 reflections | (Δ/σ)max < 0.001 |
110 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C6H8N4O2 | V = 740.84 (15) Å3 |
Mr = 168.16 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.359 (1) Å | µ = 0.12 mm−1 |
b = 10.261 (1) Å | T = 293 K |
c = 10.005 (1) Å | 0.3 × 0.2 × 0.2 mm |
β = 101.30 (1)° |
Bruker SMART CCD area-detector diffractometer | 1190 reflections with I > 2σ(I) |
3540 measured reflections | Rint = 0.037 |
1288 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.19 e Å−3 |
1288 reflections | Δρmin = −0.31 e Å−3 |
110 parameters |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.3769 (0.0013) x + 4.7665 (0.0022) y − 3.4896 (0.0047) z = 6.0871 (0.0056) * 0.0304 (0.0013) C1 * −0.0307 (0.0014) C2 * −0.1054 (0.0013) C3 * −0.0815 (0.0013) C4 * −0.0031 (0.0011) N1 * −0.0360 (0.0011) N2 * −0.0328 (0.0012) C5 * 0.1638 (0.0010) O2 * −0.0073 (0.0011) C6 * 0.1026 (0.0010) O1 Rms deviation of fitted atoms = 0.0771 |
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 | ||
C1 | 0.6462 (2) | 1.10492 (15) | 0.93705 (15) | 0.0331 (4) | |
C2 | 0.6365 (2) | 1.01960 (15) | 0.82030 (15) | 0.0335 (4) | |
C3 | 0.7220 (2) | 0.90300 (16) | 0.83869 (14) | 0.0330 (4) | |
H3 | 0.7144 | 0.8457 | 0.7658 | 0.040* | |
C4 | 0.82370 (19) | 0.86762 (14) | 0.96930 (14) | 0.0294 (4) | |
C5 | 0.9347 (2) | 0.74530 (14) | 0.99118 (14) | 0.0309 (4) | |
C6 | 0.5319 (3) | 1.06692 (19) | 0.68705 (17) | 0.0518 (5) | |
H6A | 0.5947 | 1.1406 | 0.6581 | 0.078* | |
H6B | 0.4094 | 1.0922 | 0.6963 | 0.078* | |
H6C | 0.5240 | 0.9986 | 0.6206 | 0.078* | |
N1 | 0.74384 (17) | 1.05510 (12) | 1.05700 (12) | 0.0332 (3) | |
H1 | 0.7475 | 1.1025 | 1.1284 | 0.040* | |
N2 | 0.83389 (17) | 0.94146 (12) | 1.07576 (12) | 0.0317 (3) | |
N3 | 1.00494 (19) | 0.71739 (13) | 1.12063 (12) | 0.0380 (4) | |
H3A | 0.9698 | 0.7623 | 1.1836 | 0.046* | |
N4 | 1.1351 (2) | 0.61732 (13) | 1.15884 (13) | 0.0418 (4) | |
H4A | 1.0803 | 0.5406 | 1.1383 | 0.063* | |
H4C | 1.2273 | 0.6266 | 1.1138 | 0.063* | |
O1 | 0.57526 (16) | 1.21336 (11) | 0.93482 (12) | 0.0454 (3) | |
O2 | 0.96260 (16) | 0.67886 (11) | 0.89503 (11) | 0.0419 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0318 (8) | 0.0322 (9) | 0.0356 (8) | −0.0042 (6) | 0.0072 (6) | 0.0007 (6) |
C2 | 0.0347 (8) | 0.0364 (9) | 0.0285 (8) | −0.0040 (7) | 0.0041 (6) | 0.0024 (6) |
C3 | 0.0391 (8) | 0.0342 (9) | 0.0256 (8) | −0.0042 (7) | 0.0062 (6) | −0.0026 (6) |
C4 | 0.0323 (8) | 0.0305 (8) | 0.0256 (7) | −0.0052 (6) | 0.0061 (6) | −0.0004 (6) |
C5 | 0.0386 (8) | 0.0286 (8) | 0.0257 (8) | −0.0058 (6) | 0.0067 (6) | 0.0004 (6) |
C6 | 0.0660 (12) | 0.0495 (11) | 0.0353 (9) | 0.0054 (9) | −0.0014 (8) | 0.0059 (8) |
N1 | 0.0394 (7) | 0.0314 (7) | 0.0282 (7) | 0.0001 (5) | 0.0050 (5) | −0.0068 (5) |
N2 | 0.0354 (7) | 0.0310 (7) | 0.0284 (7) | −0.0026 (5) | 0.0051 (5) | −0.0010 (5) |
N3 | 0.0525 (8) | 0.0357 (8) | 0.0258 (7) | 0.0094 (6) | 0.0077 (6) | 0.0023 (5) |
N4 | 0.0569 (9) | 0.0336 (8) | 0.0334 (7) | 0.0083 (6) | 0.0054 (6) | 0.0069 (6) |
O1 | 0.0493 (7) | 0.0344 (7) | 0.0509 (7) | 0.0067 (5) | 0.0060 (5) | −0.0015 (5) |
O2 | 0.0611 (8) | 0.0348 (6) | 0.0288 (6) | 0.0063 (5) | 0.0062 (5) | −0.0022 (5) |
C1—O1 | 1.2275 (19) | C5—N3 | 1.3281 (19) |
C1—N1 | 1.3711 (19) | C6—H6A | 0.9600 |
C1—C2 | 1.450 (2) | C6—H6B | 0.9600 |
C2—C3 | 1.348 (2) | C6—H6C | 0.9600 |
C2—C6 | 1.484 (2) | N1—N2 | 1.3362 (18) |
C3—C4 | 1.420 (2) | N1—H1 | 0.8600 |
C3—H3 | 0.9300 | N3—N4 | 1.4054 (19) |
C4—N2 | 1.2972 (19) | N3—H3A | 0.8600 |
C4—C5 | 1.490 (2) | N4—H4A | 0.8900 |
C5—O2 | 1.2286 (18) | N4—H4C | 0.8900 |
O1—C1—N1 | 120.13 (14) | C2—C6—H6B | 109.5 |
O1—C1—C2 | 125.38 (14) | H6A—C6—H6B | 109.5 |
N1—C1—C2 | 114.50 (13) | C2—C6—H6C | 109.5 |
C3—C2—C1 | 118.56 (13) | H6A—C6—H6C | 109.5 |
C3—C2—C6 | 124.00 (15) | H6B—C6—H6C | 109.5 |
C1—C2—C6 | 117.44 (15) | N2—N1—C1 | 127.49 (12) |
C2—C3—C4 | 120.03 (14) | N2—N1—H1 | 116.3 |
C2—C3—H3 | 120.0 | C1—N1—H1 | 116.2 |
C4—C3—H3 | 120.0 | C4—N2—N1 | 116.56 (12) |
N2—C4—C3 | 122.79 (14) | C5—N3—N4 | 122.48 (13) |
N2—C4—C5 | 115.44 (12) | C5—N3—H3A | 118.9 |
C3—C4—C5 | 121.70 (13) | N4—N3—H3A | 118.6 |
O2—C5—N3 | 123.44 (14) | N3—N4—H4A | 109.2 |
O2—C5—C4 | 121.55 (13) | N3—N4—H4C | 109.3 |
N3—C5—C4 | 114.97 (13) | H4A—N4—H4C | 109.5 |
C2—C6—H6A | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 | 2.14 | 2.8794 (17) | 144 |
N3—H3A···O2ii | 0.86 | 2.21 | 3.0171 (17) | 156 |
N4—H4A···O2iii | 0.89 | 2.29 | 3.1452 (19) | 161 |
N4—H4C···O1iv | 0.89 | 2.31 | 3.037 (2) | 139 |
Symmetry codes: (i) −x+2, y+1/2, −z+5/2; (ii) x, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+2; (iv) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C6H8N4O2 |
Mr | 168.16 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.359 (1), 10.261 (1), 10.005 (1) |
β (°) | 101.30 (1) |
V (Å3) | 740.84 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3540, 1288, 1190 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.102, 1.09 |
No. of reflections | 1288 |
No. of parameters | 110 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.31 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
C1—O1 | 1.2275 (19) | C4—C5 | 1.490 (2) |
C1—N1 | 1.3711 (19) | C5—O2 | 1.2286 (18) |
C1—C2 | 1.450 (2) | C5—N3 | 1.3281 (19) |
C2—C3 | 1.348 (2) | N1—N2 | 1.3362 (18) |
C3—C4 | 1.420 (2) | N3—N4 | 1.4054 (19) |
C4—N2 | 1.2972 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 | 2.14 | 2.8794 (17) | 144 |
N3—H3A···O2ii | 0.86 | 2.21 | 3.0171 (17) | 156 |
N4—H4A···O2iii | 0.89 | 2.29 | 3.1452 (19) | 161 |
N4—H4C···O1iv | 0.89 | 2.31 | 3.037 (2) | 139 |
Symmetry codes: (i) −x+2, y+1/2, −z+5/2; (ii) x, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+2; (iv) −x+2, −y+2, −z+2. |
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Pyridazinone derivatives were found to possess widespread pharmacological applications (Hamad et al., 2000; Ingec et al., 2000; Nabaweya, 1999). Some pyridazinones can be used as insecticides in vegetable, melon and other crops (Zou et al., 2002). In order to better understand the structural characteristics of these pyridazinone derivatives, we have synthesized the title compound, (I), and investigated its crystal structure.
All the atoms of (I) are located almost in a plane, except for the N3 and N4 atoms, which form a conjugated system (Fig. 1). The bond lengths N1—N2 and N3—N4 are 1.3362 (18) and 1.4054 (19) Å, respectively (Table 1). This means that N3—N4 is a single bond and the N1═N2 has double-bond character by the conjugation. There are π–π interactions between adjacent molecules, the distance between neighboring parallel aromatic ring planes being 3.26 (1) Å. There are also N—H···N and N—H···O intermolecular hydrogen bonds (Table 2), which lead to a three-dimensional framework (Fig. 2).