Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039748/cs2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039748/cs2041Isup2.hkl |
CCDC reference: 660310
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.056
- wR factor = 0.148
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C13
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.751 1.000 Tmin(prime) and Tmax expected: 0.934 0.961 RR(prime) = 0.773 Please check that your absorption correction is appropriate. RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.131 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT213_ALERT_2_C Atom F2' has ADP max/min Ratio ............. 3.60 oblat PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 19.80 Deg. F1' -C13 -F1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.00 Deg. F3 -C13 -F3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 21.30 Deg. F2' -C13 -F2 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.961 Tmax scaled 0.961 Tmin scaled 0.722 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Perhydropyridazine-1-carboxylic acid (3-trifluoromethylphenyl)-amide was prepared as described by Li et al. (2007). To a solution of perhydropyridazine-1-carboxylic acid (3-trifluoromethylphenyl)-amide (1.37 g, 5 mmol) in 1.2-dichloroethane (10 ml) were added the solution of bis(trichloromethyl)carbonate (0.59 g, 2 mmol) and pyridine (0.79 g, 10 mmol) in 1.2-dichloroethane (10 ml). The mixture was stirred at room temperature for 24 h. After the completion of the reaction, the mixture was washed with water and extracted with diethyl ether. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluant: petroleum ether-ethyl acetate, 1:1). Single crystals were obtained by slow evaporation of a petroleum ether-ethyl acetate solution (v/v: 1/1) (m.p. 417–418 K).
All H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C). The trifluoromethyl group was treated as disordered between two orientations with refined occupancies of 0.52 (2) and 0.48 (2), respectively. All C—F bonds lengths were restrained to 1.33 (1) Å and the displacement parameters of the disordered F atoms were restrained to an approximately isotropic behaviour. The large values of atomic displacement parameters for the disordered F atoms indicate further unresolved disorder of the trifluoromethyl group. The high value of Rint is due to the poor quality of the crystal.
The title compound, (I), shows pesticidal activity. X-ray analysis was undertaken in order to establish its structure. The tetrahydropyridazine ring adopts a chair conformation and the five-membered ring lies close to the plane of the molecule. The C1—N1—C7—C12 torsion angle is 27.3 (2)°.
For related literature, see: Li et al. (2007).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
Fig. 1. The molecular structure of (I), showing the atom-labelling scheme with only one disorder component of the –CF3 group. Displacement ellipsoids are drawn at the 30% probability level. |
C13H12F3N3O2 | F(000) = 308 |
Mr = 299.26 | Dx = 1.514 Mg m−3 |
Triclinic, P1 | Melting point: 417 K |
a = 6.8348 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.0756 (11) Å | Cell parameters from 1670 reflections |
c = 12.0770 (17) Å | θ = 6.0–53.0° |
α = 90.994 (2)° | µ = 0.13 mm−1 |
β = 98.153 (2)° | T = 293 K |
γ = 95.630 (3)° | Prism, colourless |
V = 656.34 (15) Å3 | 0.50 × 0.37 × 0.30 mm |
Z = 2 |
Bruker SMART APEX diffractometer | 2409 independent reflections |
Radiation source: fine-focus sealed tube | 1887 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.131 |
φ and ω scans | θmax = 25.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→8 |
Tmin = 0.751, Tmax = 1.000 | k = −9→9 |
3486 measured reflections | l = −14→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.021 |
2409 reflections | Δρmax = 0.28 e Å−3 |
219 parameters | Δρmin = −0.27 e Å−3 |
6 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.37 (3) |
C13H12F3N3O2 | γ = 95.630 (3)° |
Mr = 299.26 | V = 656.34 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.8348 (9) Å | Mo Kα radiation |
b = 8.0756 (11) Å | µ = 0.13 mm−1 |
c = 12.0770 (17) Å | T = 293 K |
α = 90.994 (2)° | 0.50 × 0.37 × 0.30 mm |
β = 98.153 (2)° |
Bruker SMART APEX diffractometer | 2409 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1887 reflections with I > 2σ(I) |
Tmin = 0.751, Tmax = 1.000 | Rint = 0.131 |
3486 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 6 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.28 e Å−3 |
2409 reflections | Δρmin = −0.27 e Å−3 |
219 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 0.0262 (13) | 0.720 (3) | 0.0498 (10) | 0.156 (5) | 0.48 (2) |
F2 | −0.188 (2) | 0.8924 (8) | 0.0078 (9) | 0.145 (4) | 0.48 (2) |
F3 | −0.2579 (15) | 0.6501 (15) | −0.0441 (6) | 0.095 (3) | 0.48 (2) |
F1' | 0.0267 (11) | 0.7751 (13) | 0.0497 (7) | 0.099 (3) | 0.52 (2) |
F2' | −0.2280 (14) | 0.8564 (18) | −0.0211 (9) | 0.151 (4) | 0.52 (2) |
F3' | −0.185 (3) | 0.599 (2) | −0.0220 (14) | 0.164 (5) | 0.52 (2) |
O1 | 0.1920 (2) | 0.91691 (18) | 0.39839 (12) | 0.0596 (5) | |
O2 | −0.2422 (2) | 0.56464 (18) | 0.56622 (13) | 0.0639 (5) | |
N1 | −0.0668 (2) | 0.73406 (17) | 0.45001 (12) | 0.0402 (4) | |
N2 | 0.1823 (2) | 0.83107 (19) | 0.57773 (13) | 0.0468 (4) | |
N3 | 0.0621 (2) | 0.70819 (19) | 0.62498 (13) | 0.0478 (4) | |
C1 | 0.1134 (3) | 0.8360 (2) | 0.46708 (15) | 0.0429 (5) | |
C2 | −0.1003 (3) | 0.6587 (2) | 0.54966 (16) | 0.0444 (5) | |
C3 | 0.3904 (3) | 0.8445 (3) | 0.62633 (17) | 0.0532 (5) | |
H3A | 0.4637 | 0.9350 | 0.5931 | 0.064* | |
H3B | 0.4471 | 0.7422 | 0.6119 | 0.064* | |
C4 | 0.4049 (3) | 0.8771 (3) | 0.75127 (17) | 0.0573 (6) | |
H4A | 0.5414 | 0.8740 | 0.7860 | 0.069* | |
H4B | 0.3666 | 0.9872 | 0.7651 | 0.069* | |
C5 | 0.2722 (4) | 0.7491 (3) | 0.80320 (17) | 0.0581 (6) | |
H5A | 0.2747 | 0.7795 | 0.8815 | 0.070* | |
H5B | 0.3234 | 0.6416 | 0.7995 | 0.070* | |
C6 | 0.0601 (3) | 0.7350 (3) | 0.74499 (16) | 0.0558 (5) | |
H6A | −0.0170 | 0.6425 | 0.7738 | 0.067* | |
H6B | 0.0001 | 0.8362 | 0.7582 | 0.067* | |
C7 | −0.1960 (3) | 0.7115 (2) | 0.34650 (15) | 0.0397 (4) | |
C8 | −0.3976 (3) | 0.6728 (2) | 0.34434 (18) | 0.0488 (5) | |
H8 | −0.4502 | 0.6599 | 0.4110 | 0.059* | |
C9 | −0.5213 (3) | 0.6532 (2) | 0.24317 (19) | 0.0550 (5) | |
H9 | −0.6568 | 0.6252 | 0.2421 | 0.066* | |
C10 | −0.4459 (3) | 0.6747 (2) | 0.14363 (18) | 0.0533 (5) | |
H10 | −0.5299 | 0.6633 | 0.0757 | 0.064* | |
C11 | −0.2447 (3) | 0.7132 (2) | 0.14634 (16) | 0.0465 (5) | |
C12 | −0.1173 (3) | 0.7311 (2) | 0.24693 (15) | 0.0431 (5) | |
H12 | 0.0187 | 0.7558 | 0.2478 | 0.052* | |
C13 | −0.1607 (4) | 0.7390 (3) | 0.03994 (19) | 0.0678 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.080 (6) | 0.239 (15) | 0.068 (4) | 0.077 (8) | 0.036 (4) | 0.025 (7) |
F2 | 0.181 (12) | 0.073 (4) | 0.084 (5) | −0.024 (5) | 0.068 (6) | 0.030 (3) |
F3 | 0.101 (4) | 0.137 (6) | 0.034 (2) | −0.039 (3) | 0.004 (2) | −0.019 (3) |
F1' | 0.076 (5) | 0.169 (5) | 0.045 (3) | −0.041 (5) | 0.018 (3) | 0.015 (2) |
F2' | 0.131 (5) | 0.163 (13) | 0.069 (4) | 0.063 (6) | 0.011 (3) | 0.082 (5) |
F3' | 0.162 (13) | 0.134 (7) | 0.110 (7) | −0.058 (7) | 0.102 (7) | −0.063 (6) |
O1 | 0.0457 (8) | 0.0851 (10) | 0.0442 (8) | −0.0150 (7) | 0.0069 (6) | 0.0176 (7) |
O2 | 0.0486 (9) | 0.0841 (10) | 0.0579 (9) | −0.0113 (7) | 0.0145 (7) | 0.0199 (8) |
N1 | 0.0305 (8) | 0.0538 (9) | 0.0377 (8) | 0.0042 (6) | 0.0091 (6) | 0.0052 (6) |
N2 | 0.0362 (9) | 0.0661 (10) | 0.0383 (8) | −0.0009 (7) | 0.0095 (6) | 0.0085 (7) |
N3 | 0.0411 (9) | 0.0651 (10) | 0.0384 (9) | 0.0008 (7) | 0.0121 (7) | 0.0101 (7) |
C1 | 0.0336 (10) | 0.0569 (11) | 0.0391 (10) | 0.0034 (7) | 0.0083 (7) | 0.0050 (8) |
C2 | 0.0355 (10) | 0.0562 (10) | 0.0434 (10) | 0.0045 (8) | 0.0122 (8) | 0.0092 (8) |
C3 | 0.0367 (11) | 0.0726 (13) | 0.0494 (12) | 0.0034 (9) | 0.0046 (8) | 0.0050 (9) |
C4 | 0.0580 (13) | 0.0657 (12) | 0.0454 (11) | 0.0077 (10) | −0.0032 (9) | 0.0039 (9) |
C5 | 0.0684 (15) | 0.0678 (12) | 0.0393 (11) | 0.0164 (10) | 0.0048 (9) | 0.0073 (9) |
C6 | 0.0599 (13) | 0.0737 (13) | 0.0381 (11) | 0.0107 (10) | 0.0174 (9) | 0.0105 (9) |
C7 | 0.0339 (9) | 0.0452 (9) | 0.0413 (10) | 0.0065 (7) | 0.0079 (7) | 0.0036 (7) |
C8 | 0.0353 (10) | 0.0599 (11) | 0.0533 (12) | 0.0066 (8) | 0.0122 (8) | 0.0029 (9) |
C9 | 0.0312 (10) | 0.0677 (12) | 0.0643 (13) | 0.0034 (8) | 0.0027 (9) | 0.0014 (10) |
C10 | 0.0460 (11) | 0.0588 (12) | 0.0514 (12) | 0.0056 (8) | −0.0056 (9) | 0.0014 (9) |
C11 | 0.0458 (11) | 0.0500 (10) | 0.0431 (11) | 0.0041 (8) | 0.0043 (8) | 0.0031 (8) |
C12 | 0.0340 (10) | 0.0532 (10) | 0.0425 (10) | 0.0036 (7) | 0.0079 (8) | 0.0032 (8) |
C13 | 0.0696 (17) | 0.0860 (17) | 0.0429 (13) | −0.0120 (13) | 0.0051 (11) | 0.0021 (12) |
F1—C13 | 1.290 (9) | C4—C5 | 1.511 (3) |
F2—C13 | 1.327 (7) | C4—H4A | 0.9700 |
F3—C13 | 1.295 (7) | C4—H4B | 0.9700 |
F1'—C13 | 1.273 (7) | C5—C6 | 1.511 (3) |
F2'—C13 | 1.291 (7) | C5—H5A | 0.9700 |
F3'—C13 | 1.326 (10) | C5—H5B | 0.9700 |
O1—C1 | 1.217 (2) | C6—H6A | 0.9700 |
O2—C2 | 1.214 (2) | C6—H6B | 0.9700 |
N1—C2 | 1.396 (2) | C7—C8 | 1.380 (3) |
N1—C1 | 1.400 (2) | C7—C12 | 1.390 (2) |
N1—C7 | 1.422 (2) | C8—C9 | 1.381 (3) |
N2—C1 | 1.355 (3) | C8—H8 | 0.9300 |
N2—N3 | 1.406 (2) | C9—C10 | 1.381 (3) |
N2—C3 | 1.453 (3) | C9—H9 | 0.9300 |
N3—C2 | 1.354 (3) | C10—C11 | 1.376 (3) |
N3—C6 | 1.464 (3) | C10—H10 | 0.9300 |
C3—C4 | 1.515 (3) | C11—C12 | 1.387 (3) |
C3—H3A | 0.9700 | C11—C13 | 1.490 (3) |
C3—H3B | 0.9700 | C12—H12 | 0.9300 |
C2—N1—C1 | 109.80 (15) | C8—C7—C12 | 120.05 (18) |
C2—N1—C7 | 125.31 (15) | C8—C7—N1 | 120.65 (16) |
C1—N1—C7 | 124.89 (15) | C12—C7—N1 | 119.29 (16) |
C1—N2—N3 | 108.32 (15) | C7—C8—C9 | 119.93 (19) |
C1—N2—C3 | 125.36 (15) | C7—C8—H8 | 120.0 |
N3—N2—C3 | 114.04 (15) | C9—C8—H8 | 120.0 |
C2—N3—N2 | 109.04 (14) | C10—C9—C8 | 120.72 (19) |
C2—N3—C6 | 124.67 (16) | C10—C9—H9 | 119.6 |
N2—N3—C6 | 113.84 (17) | C8—C9—H9 | 119.6 |
O1—C1—N2 | 126.13 (18) | C11—C10—C9 | 119.07 (19) |
O1—C1—N1 | 127.85 (18) | C11—C10—H10 | 120.5 |
N2—C1—N1 | 106.00 (15) | C9—C10—H10 | 120.5 |
O2—C2—N3 | 126.31 (18) | C10—C11—C12 | 121.19 (18) |
O2—C2—N1 | 127.89 (19) | C10—C11—C13 | 119.88 (18) |
N3—C2—N1 | 105.78 (15) | C12—C11—C13 | 118.92 (18) |
N2—C3—C4 | 108.52 (15) | C11—C12—C7 | 119.03 (17) |
N2—C3—H3A | 110.0 | C11—C12—H12 | 120.5 |
C4—C3—H3A | 110.0 | C7—C12—H12 | 120.5 |
N2—C3—H3B | 110.0 | F1'—C13—F1 | 19.8 (11) |
C4—C3—H3B | 110.0 | F1'—C13—F2' | 102.7 (6) |
H3A—C3—H3B | 108.4 | F1—C13—F2' | 119.0 (9) |
C5—C4—C3 | 111.21 (18) | F1'—C13—F3 | 121.8 (6) |
C5—C4—H4A | 109.4 | F1—C13—F3 | 110.6 (8) |
C3—C4—H4A | 109.4 | F2'—C13—F3 | 80.6 (6) |
C5—C4—H4B | 109.4 | F1'—C13—F3' | 101.7 (9) |
C3—C4—H4B | 109.4 | F1—C13—F3' | 85.2 (8) |
H4A—C4—H4B | 108.0 | F2'—C13—F3' | 108.5 (8) |
C4—C5—C6 | 112.16 (17) | F3—C13—F3' | 31.0 (10) |
C4—C5—H5A | 109.2 | F1'—C13—F2 | 90.1 (7) |
C6—C5—H5A | 109.2 | F1—C13—F2 | 109.1 (9) |
C4—C5—H5B | 109.2 | F2'—C13—F2 | 21.3 (6) |
C6—C5—H5B | 109.2 | F3—C13—F2 | 101.7 (5) |
H5A—C5—H5B | 107.9 | F3'—C13—F2 | 128.5 (8) |
N3—C6—C5 | 108.21 (15) | F1'—C13—C11 | 116.0 (4) |
N3—C6—H6A | 110.1 | F1—C13—C11 | 113.0 (6) |
C5—C6—H6A | 110.1 | F2'—C13—C11 | 115.8 (5) |
N3—C6—H6B | 110.1 | F3—C13—C11 | 113.8 (5) |
C5—C6—H6B | 110.1 | F3'—C13—C11 | 110.9 (6) |
H6A—C6—H6B | 108.4 | F2—C13—C11 | 107.9 (4) |
C1—N2—N3—C2 | −10.91 (19) | C2—N3—C6—C5 | 166.81 (17) |
C3—N2—N3—C2 | −155.52 (16) | N2—N3—C6—C5 | −55.5 (2) |
C1—N2—N3—C6 | −155.05 (16) | C4—C5—C6—N3 | 52.4 (2) |
C3—N2—N3—C6 | 60.3 (2) | C2—N1—C7—C8 | 28.0 (3) |
N3—N2—C1—O1 | −172.91 (17) | C1—N1—C7—C8 | −151.84 (17) |
C3—N2—C1—O1 | −33.3 (3) | C2—N1—C7—C12 | −152.87 (16) |
N3—N2—C1—N1 | 8.75 (18) | C1—N1—C7—C12 | 27.3 (2) |
C3—N2—C1—N1 | 148.32 (18) | C12—C7—C8—C9 | 0.1 (3) |
C2—N1—C1—O1 | 177.87 (19) | N1—C7—C8—C9 | 179.26 (16) |
C7—N1—C1—O1 | −2.3 (3) | C7—C8—C9—C10 | −1.1 (3) |
C2—N1—C1—N2 | −3.83 (18) | C8—C9—C10—C11 | 1.1 (3) |
C7—N1—C1—N2 | 176.00 (14) | C9—C10—C11—C12 | −0.2 (3) |
N2—N3—C2—O2 | −173.49 (18) | C9—C10—C11—C13 | −179.22 (19) |
C6—N3—C2—O2 | −34.1 (3) | C10—C11—C12—C7 | −0.8 (3) |
N2—N3—C2—N1 | 8.17 (19) | C13—C11—C12—C7 | 178.26 (18) |
C6—N3—C2—N1 | 147.51 (17) | C8—C7—C12—C11 | 0.8 (3) |
C1—N1—C2—O2 | 178.92 (19) | N1—C7—C12—C11 | −178.35 (15) |
C7—N1—C2—O2 | −0.9 (3) | C10—C11—C13—F1 | −158.8 (11) |
C1—N1—C2—N3 | −2.77 (18) | C12—C11—C13—F1 | 22.2 (12) |
C7—N1—C2—N3 | 177.40 (15) | C10—C11—C13—F3 | −31.7 (7) |
C1—N2—C3—C4 | 165.83 (17) | C12—C11—C13—F3 | 149.3 (7) |
N3—N2—C3—C4 | −56.6 (2) | C10—C11—C13—F2 | 80.4 (7) |
N2—C3—C4—C5 | 52.8 (2) | C12—C11—C13—F2 | −98.6 (7) |
C3—C4—C5—C6 | −53.3 (2) |
Experimental details
Crystal data | |
Chemical formula | C13H12F3N3O2 |
Mr | 299.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.8348 (9), 8.0756 (11), 12.0770 (17) |
α, β, γ (°) | 90.994 (2), 98.153 (2), 95.630 (3) |
V (Å3) | 656.34 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.50 × 0.37 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART APEX |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.751, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3486, 2409, 1887 |
Rint | 0.131 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.148, 0.97 |
No. of reflections | 2409 |
No. of parameters | 219 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.27 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
The title compound, (I), shows pesticidal activity. X-ray analysis was undertaken in order to establish its structure. The tetrahydropyridazine ring adopts a chair conformation and the five-membered ring lies close to the plane of the molecule. The C1—N1—C7—C12 torsion angle is 27.3 (2)°.