Table 4. Experimental details.

	1	2	3
Crystal data
Chemical formula	C12H9N3O2	C12H8FN3O2	C12H7F2N3O2
M r	227.22	245.21	263.21
Crystal system, space group	Orthorhombic, P n a21	Orthorhombic, P n a21	Monoclinic, I2/a
Temperature (K)	100	100	100
a, b, c (Å)	16.2689 (6), 12.8086 (7), 4.9983 (2)	16.6058 (10), 12.9096 (7), 4.9153 (3)	6.7062 (3), 14.1190 (5), 11.2074 (5)
α, β, γ (°)	90, 90, 90	90, 90, 90	90, 97.140 (4), 90
V (Å3)	1041.56 (8)	1053.71 (11)	1052.94 (8)
Z	4	4	4
Radiation type	Cu Kα	Cu Kα	Cu Kα
μ (mm−1)	0.85	1.03	1.22
Crystal size (mm)	0.20 × 0.12 × 0.06	0.26 × 0.10 × 0.05	0.11 × 0.09 × 0.06
Data collection
Diffractometer	SuperNova, Dual, Cu at zero, Atlas	SuperNova, Dual, Cu at zero, Atlas	SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 ▸)	Gaussian (CrysAlis PRO; Rigaku OD, 2015 ▸)	Gaussian (CrysAlis PRO; Rigaku OD, 2015 ▸)
Tmin, Tmax	0.187, 0.563	0.983, 0.995	0.993, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	8626, 2028, 1831	5774, 1798, 1567	5200, 1083, 856
R int	0.076	0.054	0.069
(sin θ/λ)max (Å−1)	0.627	0.629	0.628
Refinement
R[F2 > 2σ(F 2)], wR(F 2), S	0.060, 0.170, 1.07	0.055, 0.152, 1.03	0.055, 0.161, 1.04
No. of reflections	2028	1798	1083
No. of parameters	157	176	88
No. of restraints	1	1	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)	0.32, −0.30	0.28, −0.28	0.29, −0.32
Absolute structure	Flack x determined using 673 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)	Flack x determined using 450 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)	–
Absolute structure parameter	0.0 (3)	0.2 (3)	–

Computer programs: CrysAlis PRO (Rigaku OD, 2015 ▸), SHELXS (Sheldrick, 2008 ▸), SHELXL (Sheldrick, 2015 ▸) and OLEX2 (Dolomanov et al., 2009 ▸).