Table 1. Experimental details.
For all structures: Z = 4. Experiments were carried out with Mo Kα radiation. H atoms were treated by a mixture of independent and constrained refinement.
| 1 | 2 | 3 | |
|---|---|---|---|
| Crystal data | |||
| Chemical formula | C10H8N2O2 | C11H10N2O2 | C18H24N2O2 |
| M r | 188.18 | 202.21 | 300.39 |
| Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P n a21 | Triclinic, P
|
| Temperature (K) | 210 | 120 | 120 |
| a, b, c (Å) | 4.5999 (5), 10.2684 (10), 18.711 (2) | 20.5584 (7), 10.0468 (4), 4.6417 (2) | 10.8955 (5), 10.9571 (4), 14.8329 (6) |
| α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 82.335 (3), 88.326 (4), 75.178 (3) |
| V (Å3) | 883.79 (16) | 958.73 (7) | 1696.56 (12) |
| μ (mm−1) | 0.10 | 0.10 | 0.08 |
| Crystal size (mm) | 0.3 × 0.08 × 0.05 | 0.49 × 0.24 × 0.09 | 0.6 × 0.31 × 0.18 |
| Data collection | |||
| Diffractometer | Bruker SMART APEXII area detector | Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) | Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) |
| Absorption correction | Multi-scan (SADABS; Bruker, 2012 ▸) | Analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▸) | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▸) |
| T min, T max | 0.654, 0.746 | 0.969, 0.991 | 0.833, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10497, 2166, 1978 | 6756, 2021, 1819 | 14901, 6942, 5078 |
| R int | 0.020 | 0.040 | 0.037 |
| (sin θ/λ)max (Å−1) | 0.667 | 0.641 | 0.625 |
| Refinement | |||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.032, 0.083, 1.08 | 0.037, 0.081, 1.05 | 0.049, 0.119, 1.02 |
| No. of reflections | 2166 | 2021 | 6942 |
| No. of parameters | 131 | 141 | 447 |
| No. of restraints | 0 | 1 | 0 |
| Δρmax, Δρmin (e Å−3) | 0.18, −0.14 | 0.16, −0.17 | 0.26, −0.22 |