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All the non-hydrogen atoms of the title compound, C6H8N4O2, are almost coplanar, except for the —NH—NH2 moiety of the carbazoyl group, forming a conjugated system. There are π–π interactions between neighboring parallel aromatic rings, and intermolecular N—H...N and N—H...O hydrogen bonds lead to a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007165/ob6228sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007165/ob6228Isup2.hkl
Contains datablock I

CCDC reference: 214594

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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








Comment top

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 N1N2 has double-bond character by the conjugation. There are ππ 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).

Experimental top

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.

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. View of the title compound, (I), with ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A view of the crystal packing of (I).
3-Carbazoyl-5-methylpyridazin-6(1H)-one top
Crystal data top
C6H8N4O2F(000) = 352
Mr = 168.16Dx = 1.508 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2289 reflections
a = 7.359 (1) Åθ = 2.9–27.9°
b = 10.261 (1) ŵ = 0.12 mm1
c = 10.005 (1) ÅT = 293 K
β = 101.30 (1)°Block, colourless
V = 740.84 (15) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1190 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.037
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
ϕ and ω scansh = 88
3540 measured reflectionsk = 128
1288 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-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 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C6H8N4O2V = 740.84 (15) Å3
Mr = 168.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.359 (1) ŵ = 0.12 mm1
b = 10.261 (1) ÅT = 293 K
c = 10.005 (1) Å0.3 × 0.2 × 0.2 mm
β = 101.30 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1190 reflections with I > 2σ(I)
3540 measured reflectionsRint = 0.037
1288 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.09Δρmax = 0.19 e Å3
1288 reflectionsΔρmin = 0.31 e Å3
110 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6462 (2)1.10492 (15)0.93705 (15)0.0331 (4)
C20.6365 (2)1.01960 (15)0.82030 (15)0.0335 (4)
C30.7220 (2)0.90300 (16)0.83869 (14)0.0330 (4)
H30.71440.84570.76580.040*
C40.82370 (19)0.86762 (14)0.96930 (14)0.0294 (4)
C50.9347 (2)0.74530 (14)0.99118 (14)0.0309 (4)
C60.5319 (3)1.06692 (19)0.68705 (17)0.0518 (5)
H6A0.59471.14060.65810.078*
H6B0.40941.09220.69630.078*
H6C0.52400.99860.62060.078*
N10.74384 (17)1.05510 (12)1.05700 (12)0.0332 (3)
H10.74751.10251.12840.040*
N20.83389 (17)0.94146 (12)1.07576 (12)0.0317 (3)
N31.00494 (19)0.71739 (13)1.12063 (12)0.0380 (4)
H3A0.96980.76231.18360.046*
N41.1351 (2)0.61732 (13)1.15884 (13)0.0418 (4)
H4A1.08030.54061.13830.063*
H4C1.22730.62661.11380.063*
O10.57526 (16)1.21336 (11)0.93482 (12)0.0454 (3)
O20.96260 (16)0.67886 (11)0.89503 (11)0.0419 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0318 (8)0.0322 (9)0.0356 (8)0.0042 (6)0.0072 (6)0.0007 (6)
C20.0347 (8)0.0364 (9)0.0285 (8)0.0040 (7)0.0041 (6)0.0024 (6)
C30.0391 (8)0.0342 (9)0.0256 (8)0.0042 (7)0.0062 (6)0.0026 (6)
C40.0323 (8)0.0305 (8)0.0256 (7)0.0052 (6)0.0061 (6)0.0004 (6)
C50.0386 (8)0.0286 (8)0.0257 (8)0.0058 (6)0.0067 (6)0.0004 (6)
C60.0660 (12)0.0495 (11)0.0353 (9)0.0054 (9)0.0014 (8)0.0059 (8)
N10.0394 (7)0.0314 (7)0.0282 (7)0.0001 (5)0.0050 (5)0.0068 (5)
N20.0354 (7)0.0310 (7)0.0284 (7)0.0026 (5)0.0051 (5)0.0010 (5)
N30.0525 (8)0.0357 (8)0.0258 (7)0.0094 (6)0.0077 (6)0.0023 (5)
N40.0569 (9)0.0336 (8)0.0334 (7)0.0083 (6)0.0054 (6)0.0069 (6)
O10.0493 (7)0.0344 (7)0.0509 (7)0.0067 (5)0.0060 (5)0.0015 (5)
O20.0611 (8)0.0348 (6)0.0288 (6)0.0063 (5)0.0062 (5)0.0022 (5)
Geometric parameters (Å, º) top
C1—O11.2275 (19)C5—N31.3281 (19)
C1—N11.3711 (19)C6—H6A0.9600
C1—C21.450 (2)C6—H6B0.9600
C2—C31.348 (2)C6—H6C0.9600
C2—C61.484 (2)N1—N21.3362 (18)
C3—C41.420 (2)N1—H10.8600
C3—H30.9300N3—N41.4054 (19)
C4—N21.2972 (19)N3—H3A0.8600
C4—C51.490 (2)N4—H4A0.8900
C5—O21.2286 (18)N4—H4C0.8900
O1—C1—N1120.13 (14)C2—C6—H6B109.5
O1—C1—C2125.38 (14)H6A—C6—H6B109.5
N1—C1—C2114.50 (13)C2—C6—H6C109.5
C3—C2—C1118.56 (13)H6A—C6—H6C109.5
C3—C2—C6124.00 (15)H6B—C6—H6C109.5
C1—C2—C6117.44 (15)N2—N1—C1127.49 (12)
C2—C3—C4120.03 (14)N2—N1—H1116.3
C2—C3—H3120.0C1—N1—H1116.2
C4—C3—H3120.0C4—N2—N1116.56 (12)
N2—C4—C3122.79 (14)C5—N3—N4122.48 (13)
N2—C4—C5115.44 (12)C5—N3—H3A118.9
C3—C4—C5121.70 (13)N4—N3—H3A118.6
O2—C5—N3123.44 (14)N3—N4—H4A109.2
O2—C5—C4121.55 (13)N3—N4—H4C109.3
N3—C5—C4114.97 (13)H4A—N4—H4C109.5
C2—C6—H6A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.862.142.8794 (17)144
N3—H3A···O2ii0.862.213.0171 (17)156
N4—H4A···O2iii0.892.293.1452 (19)161
N4—H4C···O1iv0.892.313.037 (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 formulaC6H8N4O2
Mr168.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.359 (1), 10.261 (1), 10.005 (1)
β (°) 101.30 (1)
V3)740.84 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3540, 1288, 1190
Rint0.037
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 1.09
No. of reflections1288
No. of parameters110
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.31

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.

Selected bond lengths (Å) top
C1—O11.2275 (19)C4—C51.490 (2)
C1—N11.3711 (19)C5—O21.2286 (18)
C1—C21.450 (2)C5—N31.3281 (19)
C2—C31.348 (2)N1—N21.3362 (18)
C3—C41.420 (2)N3—N41.4054 (19)
C4—N21.2972 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.862.142.8794 (17)144
N3—H3A···O2ii0.862.213.0171 (17)156
N4—H4A···O2iii0.892.293.1452 (19)161
N4—H4C···O1iv0.892.313.037 (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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