



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809018376/bg2256sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809018376/bg2256Isup2.hkl |
CCDC reference: 738249
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.121
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 -- C15 .. 5.39 su
Alert level G PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c .... P21/n
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
α-benzylidene-γ-tolylbutenolide (1) was synthesized according to the literature procedure (Filler & Piasek, 1973). (0.036 g, 1.125 mmol) of hydrazine was added to a solution of (1) (0.2 g, 0.76 mmol) in toluene (25 ml) and the mixture was stirred at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was recrystallized from ethanol, and purified by chromatography on silica gel (eluant: ethyl acetate / hexane: 20 / 80). The pyridazinone was recrystallized from ethanol.
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.99 Å (methylene), 0.98Å (methyl) or 0.95 Å (aromatic) and N—H =0.88 Å with Uiso(H) = 1.2Ueq(C or N)or Uiso(H) = 1.5Ueq(Cmethyl).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C18H16N2O | F(000) = 584 |
Mr = 276.33 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3436 reflections |
a = 7.2487 (4) Å | θ = 2.8–32.0° |
b = 10.4469 (5) Å | µ = 0.08 mm−1 |
c = 19.1869 (9) Å | T = 180 K |
β = 99.598 (5)° | Fragment, colourless |
V = 1432.62 (12) Å3 | 0.50 × 0.48 × 0.08 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer | 2914 independent reflections |
Radiation source: fine-focus sealed tube | 1622 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 8.2632 pixels mm-1 | θmax = 26.4°, θmin = 2.9° |
ω and ϕ scans | h = −7→9 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −12→13 |
Tmin = 0.965, Tmax = 0.993 | l = −23→23 |
10925 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0125P] where P = (Fo2 + 2Fc2)/3 |
2914 reflections | (Δ/σ)max = 0.008 |
190 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C18H16N2O | V = 1432.62 (12) Å3 |
Mr = 276.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2487 (4) Å | µ = 0.08 mm−1 |
b = 10.4469 (5) Å | T = 180 K |
c = 19.1869 (9) Å | 0.50 × 0.48 × 0.08 mm |
β = 99.598 (5)° |
Oxford Diffraction Xcalibur diffractometer | 2914 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 1622 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.993 | Rint = 0.044 |
10925 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.20 e Å−3 |
2914 reflections | Δρmin = −0.20 e Å−3 |
190 parameters |
Experimental. All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.97 Å (methylene), 0.98Å (methyl) and N—H = 0.86 Å with Uiso(H) = xUeq(C or N) where x=1.2 or 1.5(methyl). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlis RED (Oxford Diffraction, 2006) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.58992 (17) | −0.03563 (12) | 0.42289 (6) | 0.0387 (4) | |
N1 | 0.8190 (2) | 0.19591 (14) | 0.54067 (8) | 0.0336 (4) | |
N2 | 0.7005 (2) | 0.10629 (14) | 0.50803 (7) | 0.0335 (4) | |
H2 | 0.6067 | 0.0848 | 0.5294 | 0.040* | |
C1 | 0.9570 (3) | 0.22886 (16) | 0.50837 (9) | 0.0296 (4) | |
C2 | 0.7092 (3) | 0.04582 (17) | 0.44647 (9) | 0.0297 (4) | |
C3 | 0.8621 (2) | 0.08373 (17) | 0.41181 (9) | 0.0296 (4) | |
C4 | 0.9807 (2) | 0.17325 (17) | 0.44281 (9) | 0.0309 (4) | |
H4 | 1.0821 | 0.1999 | 0.4206 | 0.037* | |
C11 | 1.0846 (3) | 0.32907 (17) | 0.54285 (9) | 0.0314 (5) | |
C12 | 1.0234 (3) | 0.41994 (17) | 0.58693 (9) | 0.0360 (5) | |
H12 | 0.8983 | 0.4168 | 0.5956 | 0.043* | |
C13 | 1.1423 (3) | 0.51460 (18) | 0.61821 (10) | 0.0398 (5) | |
H13 | 1.0974 | 0.5757 | 0.6480 | 0.048* | |
C14 | 1.3252 (3) | 0.52198 (18) | 0.60691 (10) | 0.0392 (5) | |
C15 | 1.3863 (3) | 0.43020 (19) | 0.56396 (10) | 0.0414 (5) | |
H15 | 1.5122 | 0.4326 | 0.5561 | 0.050* | |
C16 | 1.2684 (3) | 0.33473 (18) | 0.53210 (9) | 0.0372 (5) | |
H16 | 1.3141 | 0.2731 | 0.5028 | 0.045* | |
C17 | 1.4555 (3) | 0.6246 (2) | 0.64031 (11) | 0.0547 (6) | |
H17A | 1.5780 | 0.6138 | 0.6259 | 0.082* | 0.50 |
H17B | 1.4691 | 0.6182 | 0.6919 | 0.082* | 0.50 |
H17C | 1.4044 | 0.7087 | 0.6250 | 0.082* | 0.50 |
H17D | 1.3897 | 0.6800 | 0.6693 | 0.082* | 0.50 |
H17E | 1.4986 | 0.6756 | 0.6033 | 0.082* | 0.50 |
H17F | 1.5633 | 0.5851 | 0.6702 | 0.082* | 0.50 |
C31 | 0.8735 (3) | 0.02039 (18) | 0.34214 (9) | 0.0359 (5) | |
H31A | 0.9169 | −0.0688 | 0.3513 | 0.043* | |
H31B | 0.7463 | 0.0170 | 0.3138 | 0.043* | |
C32 | 1.0013 (3) | 0.08604 (17) | 0.29952 (9) | 0.0292 (4) | |
C33 | 0.9342 (3) | 0.18115 (18) | 0.25246 (9) | 0.0376 (5) | |
H33 | 0.8063 | 0.2054 | 0.2473 | 0.045* | |
C34 | 1.0500 (3) | 0.2416 (2) | 0.21276 (10) | 0.0438 (5) | |
H34 | 1.0024 | 0.3074 | 0.1806 | 0.053* | |
C35 | 1.2341 (3) | 0.20623 (19) | 0.21994 (11) | 0.0467 (6) | |
H35 | 1.3142 | 0.2470 | 0.1923 | 0.056* | |
C36 | 1.3030 (3) | 0.11236 (19) | 0.26684 (11) | 0.0454 (6) | |
H36 | 1.4309 | 0.0881 | 0.2719 | 0.054* | |
C37 | 1.1874 (3) | 0.05337 (18) | 0.30651 (10) | 0.0358 (5) | |
H37 | 1.2363 | −0.0111 | 0.3394 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0398 (8) | 0.0418 (8) | 0.0372 (8) | −0.0120 (7) | 0.0141 (6) | −0.0062 (7) |
N1 | 0.0369 (10) | 0.0355 (9) | 0.0299 (8) | −0.0082 (7) | 0.0094 (7) | −0.0015 (7) |
N2 | 0.0344 (9) | 0.0379 (9) | 0.0311 (8) | −0.0100 (8) | 0.0139 (7) | −0.0040 (8) |
C1 | 0.0326 (11) | 0.0290 (10) | 0.0281 (10) | −0.0032 (8) | 0.0076 (8) | 0.0052 (8) |
C2 | 0.0331 (11) | 0.0289 (11) | 0.0278 (10) | −0.0029 (9) | 0.0071 (8) | 0.0012 (9) |
C3 | 0.0306 (11) | 0.0313 (11) | 0.0285 (10) | 0.0012 (8) | 0.0093 (8) | 0.0027 (8) |
C4 | 0.0315 (11) | 0.0336 (11) | 0.0293 (10) | −0.0036 (9) | 0.0100 (8) | 0.0014 (9) |
C11 | 0.0364 (12) | 0.0327 (11) | 0.0254 (9) | −0.0034 (9) | 0.0064 (8) | 0.0064 (9) |
C12 | 0.0373 (12) | 0.0382 (12) | 0.0336 (11) | −0.0028 (9) | 0.0088 (9) | 0.0027 (10) |
C13 | 0.0497 (14) | 0.0344 (12) | 0.0340 (11) | −0.0034 (10) | 0.0034 (10) | 0.0020 (9) |
C14 | 0.0464 (13) | 0.0354 (12) | 0.0326 (11) | −0.0070 (10) | −0.0028 (9) | 0.0077 (9) |
C15 | 0.0336 (12) | 0.0472 (13) | 0.0420 (12) | −0.0084 (10) | 0.0019 (9) | 0.0116 (11) |
C16 | 0.0395 (13) | 0.0390 (12) | 0.0341 (11) | −0.0023 (10) | 0.0087 (9) | 0.0041 (9) |
C17 | 0.0584 (16) | 0.0471 (14) | 0.0534 (14) | −0.0177 (11) | −0.0058 (11) | 0.0017 (11) |
C31 | 0.0388 (12) | 0.0403 (12) | 0.0307 (10) | −0.0067 (9) | 0.0119 (9) | −0.0046 (9) |
C32 | 0.0354 (12) | 0.0307 (11) | 0.0227 (9) | −0.0041 (8) | 0.0085 (8) | −0.0046 (8) |
C33 | 0.0390 (12) | 0.0408 (12) | 0.0328 (11) | 0.0043 (9) | 0.0056 (9) | −0.0016 (9) |
C34 | 0.0649 (16) | 0.0374 (12) | 0.0303 (11) | −0.0026 (11) | 0.0111 (10) | 0.0051 (9) |
C35 | 0.0588 (16) | 0.0452 (13) | 0.0422 (12) | −0.0158 (11) | 0.0257 (11) | −0.0073 (11) |
C36 | 0.0353 (13) | 0.0461 (13) | 0.0575 (14) | −0.0009 (10) | 0.0162 (11) | −0.0041 (12) |
C37 | 0.0368 (12) | 0.0366 (12) | 0.0349 (11) | 0.0014 (9) | 0.0087 (9) | 0.0002 (9) |
O1—C2 | 1.243 (2) | C16—H16 | 0.9500 |
N1—C1 | 1.308 (2) | C17—H17A | 0.9800 |
N1—N2 | 1.3515 (19) | C17—H17B | 0.9800 |
N2—C2 | 1.350 (2) | C17—H17C | 0.9800 |
N2—H2 | 0.8800 | C17—H17D | 0.9800 |
C1—C4 | 1.422 (2) | C17—H17E | 0.9800 |
C1—C11 | 1.478 (2) | C17—H17F | 0.9800 |
C2—C3 | 1.440 (2) | C31—C32 | 1.500 (2) |
C3—C4 | 1.341 (2) | C31—H31A | 0.9900 |
C3—C31 | 1.506 (2) | C31—H31B | 0.9900 |
C4—H4 | 0.9500 | C32—C37 | 1.376 (3) |
C11—C16 | 1.383 (3) | C32—C33 | 1.376 (2) |
C11—C12 | 1.392 (2) | C33—C34 | 1.377 (3) |
C12—C13 | 1.381 (2) | C33—H33 | 0.9500 |
C12—H12 | 0.9500 | C34—C35 | 1.369 (3) |
C13—C14 | 1.381 (3) | C34—H34 | 0.9500 |
C13—H13 | 0.9500 | C35—C36 | 1.368 (3) |
C14—C15 | 1.384 (3) | C35—H35 | 0.9500 |
C14—C17 | 1.500 (3) | C36—C37 | 1.369 (3) |
C15—C16 | 1.387 (2) | C36—H36 | 0.9500 |
C15—H15 | 0.9500 | C37—H37 | 0.9500 |
C1—N1—N2 | 116.10 (15) | C14—C17—H17D | 109.5 |
C2—N2—N1 | 127.66 (15) | H17A—C17—H17D | 141.1 |
C2—N2—H2 | 116.2 | H17B—C17—H17D | 56.3 |
N1—N2—H2 | 116.2 | H17C—C17—H17D | 56.3 |
N1—C1—C4 | 121.77 (17) | C14—C17—H17E | 109.5 |
N1—C1—C11 | 116.46 (16) | H17A—C17—H17E | 56.3 |
C4—C1—C11 | 121.76 (16) | H17B—C17—H17E | 141.1 |
O1—C2—N2 | 120.52 (16) | H17C—C17—H17E | 56.3 |
O1—C2—C3 | 124.21 (16) | H17D—C17—H17E | 109.5 |
N2—C2—C3 | 115.27 (16) | C14—C17—H17F | 109.5 |
C4—C3—C2 | 118.24 (16) | H17A—C17—H17F | 56.3 |
C4—C3—C31 | 125.03 (17) | H17B—C17—H17F | 56.3 |
C2—C3—C31 | 116.72 (16) | H17C—C17—H17F | 141.1 |
C3—C4—C1 | 120.96 (17) | H17D—C17—H17F | 109.5 |
C3—C4—H4 | 119.5 | H17E—C17—H17F | 109.5 |
C1—C4—H4 | 119.5 | C32—C31—C3 | 114.42 (15) |
C16—C11—C12 | 118.29 (17) | C32—C31—H31A | 108.7 |
C16—C11—C1 | 120.67 (17) | C3—C31—H31A | 108.7 |
C12—C11—C1 | 121.03 (17) | C32—C31—H31B | 108.7 |
C13—C12—C11 | 120.87 (18) | C3—C31—H31B | 108.7 |
C13—C12—H12 | 119.6 | H31A—C31—H31B | 107.6 |
C11—C12—H12 | 119.6 | C37—C32—C33 | 118.48 (17) |
C14—C13—C12 | 121.16 (19) | C37—C32—C31 | 121.19 (17) |
C14—C13—H13 | 119.4 | C33—C32—C31 | 120.33 (17) |
C12—C13—H13 | 119.4 | C32—C33—C34 | 120.83 (18) |
C13—C14—C15 | 117.75 (18) | C32—C33—H33 | 119.6 |
C13—C14—C17 | 121.70 (19) | C34—C33—H33 | 119.6 |
C15—C14—C17 | 120.6 (2) | C35—C34—C33 | 119.65 (19) |
C14—C15—C16 | 121.71 (19) | C35—C34—H34 | 120.2 |
C14—C15—H15 | 119.1 | C33—C34—H34 | 120.2 |
C16—C15—H15 | 119.1 | C36—C35—C34 | 120.14 (19) |
C11—C16—C15 | 120.20 (18) | C36—C35—H35 | 119.9 |
C11—C16—H16 | 119.9 | C34—C35—H35 | 119.9 |
C15—C16—H16 | 119.9 | C35—C36—C37 | 119.89 (19) |
C14—C17—H17A | 109.5 | C35—C36—H36 | 120.1 |
C14—C17—H17B | 109.5 | C37—C36—H36 | 120.1 |
H17A—C17—H17B | 109.5 | C36—C37—C32 | 121.01 (19) |
C14—C17—H17C | 109.5 | C36—C37—H37 | 119.5 |
H17A—C17—H17C | 109.5 | C32—C37—H37 | 119.5 |
H17B—C17—H17C | 109.5 | ||
C1—N1—N2—C2 | 0.8 (3) | C12—C13—C14—C15 | −0.9 (3) |
N2—N1—C1—C4 | −0.1 (2) | C12—C13—C14—C17 | 179.75 (17) |
N2—N1—C1—C11 | 178.59 (14) | C13—C14—C15—C16 | 1.0 (3) |
N1—N2—C2—O1 | 179.62 (16) | C17—C14—C15—C16 | −179.62 (17) |
N1—N2—C2—C3 | −0.9 (3) | C12—C11—C16—C15 | −0.9 (3) |
O1—C2—C3—C4 | 179.72 (16) | C1—C11—C16—C15 | 179.14 (16) |
N2—C2—C3—C4 | 0.3 (2) | C14—C15—C16—C11 | −0.1 (3) |
O1—C2—C3—C31 | 0.8 (3) | C4—C3—C31—C32 | −14.1 (3) |
N2—C2—C3—C31 | −178.64 (15) | C2—C3—C31—C32 | 164.73 (16) |
C2—C3—C4—C1 | 0.3 (3) | C3—C31—C32—C37 | 90.5 (2) |
C31—C3—C4—C1 | 179.16 (17) | C3—C31—C32—C33 | −89.3 (2) |
N1—C1—C4—C3 | −0.5 (3) | C37—C32—C33—C34 | 0.6 (3) |
C11—C1—C4—C3 | −179.06 (16) | C31—C32—C33—C34 | −179.63 (17) |
N1—C1—C11—C16 | 153.12 (17) | C32—C33—C34—C35 | 0.3 (3) |
C4—C1—C11—C16 | −28.2 (3) | C33—C34—C35—C36 | −0.7 (3) |
N1—C1—C11—C12 | −26.8 (2) | C34—C35—C36—C37 | 0.2 (3) |
C4—C1—C11—C12 | 151.86 (17) | C35—C36—C37—C32 | 0.7 (3) |
C16—C11—C12—C13 | 1.0 (2) | C33—C32—C37—C36 | −1.1 (3) |
C1—C11—C12—C13 | −179.02 (16) | C31—C32—C37—C36 | 179.14 (17) |
C11—C12—C13—C14 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.88 | 1.89 | 2.7686 (19) | 178 |
C34—H34···O1ii | 0.95 | 2.57 | 3.512 (2) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H16N2O |
Mr | 276.33 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 180 |
a, b, c (Å) | 7.2487 (4), 10.4469 (5), 19.1869 (9) |
β (°) | 99.598 (5) |
V (Å3) | 1432.62 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.48 × 0.08 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.965, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10925, 2914, 1622 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.121, 0.94 |
No. of reflections | 2914 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.88 | 1.89 | 2.7686 (19) | 178.3 |
C34—H34···O1ii | 0.95 | 2.57 | 3.512 (2) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2. |
In recent years a number of 6-arylpyridazin-3(2H)-ones have been reported to possess antimicrobial (Sayed et al., 2002), anti-inflammatory (Frolov et al., 2004), herbicidal (Piaz et al.,1994), antiplatelet activities (Coelho et al., 2004), anticancer effects (Malinka et al., 2004), antifeedant (Cao et al., 2003), antihypertensive (Ogretir et al.,2002), potent analgesic (Okcelik et al., 2003) and other anticipated biological(Youssef et al., 2005) and pharmacological properties (Sotelo et al., 2003).
In previous papers treating the reactivity of lactones bearing an exocyclic carbon-carbon double bond with 1,3-dipoles (Fihi et al., 1995; Roussel et al., 2000, 2003; Daran et al., 2006), we reported that cycloaddition reactions lead to spiroheterocyclic compounds or evolutive products. In this paper, we describe the synthesis of a new dihydro-2 H– pyridazin-3-onederivative. The condensation ofα-benzylidene-γ-tolylbutenolide(1) and hydrazine (2) in reflux in toluene leads in one step to pyridazin-3-one(3). (Scheme).
Since the 1H and 13CNMR studies did not provide unambiguous information, a single-crystal of (3) was subjected to X-ray diffraction analysis to determine the structure of the product.
The molecule is not planar, the tolyl and the pyridazin rings are twisted to each other making a dihedral angle of 27.35 (9)° and the phenyl ring is nearly perpendicular to the pyridazin ring with a dihedral angle of 85.24 (5)° (Fig. 1).
The molecules are connected two by two through N—H···O hydrogen bonds with a R22(8) graph set motif (Bernstein et al., 1995) then building a pseudo dimer arranged around the inversion center (Fig. 1, Table 1). Weak C—H···O hydrogen bonds and weak offset π-π stacking stabilize the packing. The π-π stacking occurs between the pyridazin rings of symmetry related molecules with centroid-to-centroid distance of 3.748 Å and interplanar distance of 3.605Å and a slippage of 1.024 Å.