(VI)	(VII)	(VIII)	(IX)	(X)
Crystal data
Chemical formula	C11H17N2O+·C7H4BrO2 −	C11H17N2O+·C7H4IO2 −	C11H17N2O+·C8H7O2 −	C11H17N2O+·C7H6NO2 −	C11H17N2O+·C7H4NO4 −
M r	393.28	440.27	328.40	329.39	359.38
Crystal system, space group	Orthorhombic, P212121	Orthorhombic, P212121	Triclinic, P	Monoclinic, P21/c	Monoclinic, P21/c
Temperature (K)	293	293	296	296	296
a, b, c (Å)	6.9824 (2), 13.2292 (4), 19.4903 (7)	7.0101 (4), 13.3796 (6), 19.5524 (6)	7.826 (1), 10.320 (2), 12.055 (3)	14.922 (1), 7.6951 (5), 15.560 (1)	7.5174 (5), 7.9761 (5), 29.860 (2)
α, β, γ (°)	90, 90, 90	90, 90, 90	78.37 (2), 78.27 (2), 73.83 (2)	90, 106.911 (8), 90	90, 97.322 (6), 90
V (Å3)	1800.35 (10)	1833.87 (14)	904.6 (3)	1709.4 (2)	1775.8 (2)
Z	4	4	2	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm−1)	2.30	1.76	0.08	0.09	0.10
Crystal size (mm)	0.50 × 0.50 × 0.48	0.50 × 0.50 × 0.48	0.48 × 0.48 × 0.40	0.48 × 0.44 × 0.16	0.50 × 0.50 × 0.40
Data collection
Diffractometer	Oxford Diffraction Xcalibur with Sapphire CCD	Oxford Diffraction Xcalibur with Sapphire CCD	Oxford Diffraction Xcalibur with Sapphire CCD	Oxford Diffraction Xcalibur with Sapphire CCD	Oxford Diffraction Xcalibur with Sapphire CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)
T min, T max	0.297, 0.331	0.373, 0.431	0.883, 0.968	0.830, 0.986	0.855, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	13089, 3895, 2640	7500, 3735, 3036	6091, 3838, 2600	6720, 3668, 2606	13660, 3934, 2879
R int	0.033	0.019	0.013	0.014	0.019
(sin θ/λ)max (Å−1)	0.654	0.655	0.653	0.651	0.658
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.035, 0.077, 0.94	0.032, 0.071, 1.05	0.042, 0.119, 1.06	0.039, 0.112, 1.10	0.040, 0.111, 1.03
No. of reflections	3895	3735	3838	3668	3934
No. of parameters	224	237	226	231	242
No. of restraints	0	17	0	0	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H-atom parameters constrained	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)	0.29, −0.53	0.46, −0.65	0.16, −0.16	0.15, −0.25	0.17, −0.15
Absolute structure	Flack x determined using 919 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)	Flack x determined using 1045 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)	–	–	–
Absolute structure parameter	0.004 (5)	0.004 (10)	–	–	–