Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002692/rz6044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002692/rz6044Isup2.hkl |
CCDC reference: 269853
Data collection: APEX2 (Bruker–Nonius, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[VClO(C16H22N4)]ClO4 | F(000) = 972 |
Mr = 472.22 | Dx = 1.540 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3078 reflections |
a = 13.3031 (6) Å | θ = 2.5–27.1° |
b = 8.9874 (4) Å | µ = 0.79 mm−1 |
c = 17.7551 (9) Å | T = 180 K |
β = 106.408 (1)° | Block, blue |
V = 2036.35 (17) Å3 | 0.34 × 0.20 × 0.20 mm |
Z = 4 |
Bruker–Nonius X8APEX-II CCD diffractometer | 4263 independent reflections |
Radiation source: fine-focus sealed tube | 2835 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
thin–slice ω and φ scans | θmax = 28.3°, θmin = 3.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −17→17 |
Tmin = 0.719, Tmax = 0.859 | k = −9→9 |
8836 measured reflections | l = −23→9 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0546P)2] where P = (Fo2 + 2Fc2)/3 |
4263 reflections | (Δ/σ)max = 0.001 |
255 parameters | Δρmax = 0.82 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Experimental. Ratio of minimum to maximum apparent transmission: 0.837449 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.8286 (0.0111) x - 1.3261 (0.0086) y + 12.9051 (0.0113) z = 3.9044 (0.0072) * -0.0087 (0.0015) N1 * 0.0008 (0.0017) C1 * 0.0063 (0.0017) C2 * -0.0056 (0.0017) C3 * -0.0022 (0.0017) C4 * 0.0094 (0.0016) C5 Rms deviation of fitted atoms = 0.0063 5.1880 (0.0139) x + 7.4753 (0.0060) y + 4.7733 (0.0191) z = 8.4508 (0.0034) * -0.0001 (0.0017) N2 * 0.0077 (0.0019) C12 * -0.0107 (0.0021) C13 * 0.0064 (0.0022) C14 * 0.0011 (0.0023) C15 * -0.0044 (0.0021) C16 Rms deviation of fitted atoms = 0.0063 Angle to previous plane (with approximate e.s.d.) = 66.52 (0.09) |
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 | ||
V1 | 0.32565 (3) | 0.76248 (5) | 0.22463 (2) | 0.02974 (14) | |
Cl1 | 0.45080 (5) | 0.64760 (9) | 0.32580 (4) | 0.0499 (2) | |
O1 | 0.33757 (13) | 0.93676 (19) | 0.24415 (10) | 0.0414 (5) | |
N1 | 0.20724 (15) | 0.7375 (2) | 0.28407 (11) | 0.0288 (5) | |
N2 | 0.41997 (16) | 0.7453 (2) | 0.14671 (12) | 0.0325 (5) | |
N3 | 0.24933 (15) | 0.5305 (2) | 0.18843 (11) | 0.0305 (5) | |
N4 | 0.21611 (15) | 0.8098 (2) | 0.11067 (11) | 0.0306 (5) | |
C1 | 0.16784 (19) | 0.8531 (3) | 0.31447 (14) | 0.0334 (6) | |
H1A | 0.1962 | 0.9493 | 0.3118 | 0.040* | |
C2 | 0.08846 (19) | 0.8383 (3) | 0.34922 (14) | 0.0340 (6) | |
H2A | 0.0629 | 0.9225 | 0.3704 | 0.041* | |
C3 | 0.0466 (2) | 0.7001 (3) | 0.35302 (14) | 0.0351 (6) | |
H3A | −0.0092 | 0.6873 | 0.3761 | 0.042* | |
C4 | 0.08674 (18) | 0.5801 (3) | 0.32281 (14) | 0.0325 (6) | |
H4A | 0.0589 | 0.4834 | 0.3250 | 0.039* | |
C5 | 0.16740 (18) | 0.6011 (3) | 0.28944 (13) | 0.0291 (6) | |
C6 | 0.2174 (2) | 0.4759 (3) | 0.25705 (14) | 0.0356 (6) | |
H6A | 0.2795 | 0.4389 | 0.2979 | 0.043* | |
H6B | 0.1671 | 0.3928 | 0.2409 | 0.043* | |
C7 | 0.3185 (2) | 0.4166 (3) | 0.16737 (15) | 0.0422 (7) | |
H7A | 0.2838 | 0.3194 | 0.1613 | 0.063* | |
H7B | 0.3849 | 0.4110 | 0.2091 | 0.063* | |
H7C | 0.3324 | 0.4447 | 0.1179 | 0.063* | |
C8 | 0.15448 (19) | 0.5577 (3) | 0.12166 (13) | 0.0337 (6) | |
H8A | 0.0968 | 0.5946 | 0.1418 | 0.040* | |
H8B | 0.1315 | 0.4634 | 0.0931 | 0.040* | |
C9 | 0.17835 (19) | 0.6698 (3) | 0.06702 (14) | 0.0331 (6) | |
H9A | 0.2328 | 0.6303 | 0.0442 | 0.040* | |
H9B | 0.1145 | 0.6902 | 0.0236 | 0.040* | |
C10 | 0.12610 (19) | 0.9033 (3) | 0.11502 (16) | 0.0403 (7) | |
H10A | 0.0882 | 0.9377 | 0.0623 | 0.060* | |
H10B | 0.1517 | 0.9894 | 0.1489 | 0.060* | |
H10C | 0.0788 | 0.8446 | 0.1368 | 0.060* | |
C11 | 0.27989 (19) | 0.8947 (3) | 0.06853 (15) | 0.0398 (6) | |
H11A | 0.2928 | 0.9966 | 0.0902 | 0.048* | |
H11B | 0.2414 | 0.9023 | 0.0121 | 0.048* | |
C12 | 0.38166 (19) | 0.8169 (3) | 0.07791 (14) | 0.0361 (6) | |
C13 | 0.4328 (2) | 0.8158 (3) | 0.02008 (16) | 0.0485 (7) | |
H13A | 0.4029 | 0.8645 | −0.0286 | 0.058* | |
C14 | 0.5272 (2) | 0.7440 (3) | 0.03363 (18) | 0.0562 (9) | |
H14A | 0.5645 | 0.7446 | −0.0048 | 0.067* | |
C15 | 0.5670 (2) | 0.6706 (4) | 0.10414 (17) | 0.0561 (9) | |
H15A | 0.6319 | 0.6190 | 0.1145 | 0.067* | |
C16 | 0.5123 (2) | 0.6727 (3) | 0.15918 (15) | 0.0448 (7) | |
H16A | 0.5402 | 0.6216 | 0.2074 | 0.054* | |
Cl2 | 0.83748 (5) | 0.77174 (7) | 0.55878 (4) | 0.03751 (18) | |
O2 | 0.77474 (14) | 0.90186 (19) | 0.53530 (10) | 0.0452 (5) | |
O3 | 0.90724 (15) | 0.7906 (2) | 0.63649 (11) | 0.0490 (5) | |
O4 | 0.76814 (16) | 0.6490 (2) | 0.56127 (13) | 0.0636 (7) | |
O5 | 0.8937 (2) | 0.7377 (3) | 0.50394 (15) | 0.0876 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.0304 (2) | 0.0366 (3) | 0.0247 (2) | −0.00381 (19) | 0.01184 (17) | −0.00313 (18) |
Cl1 | 0.0409 (4) | 0.0833 (6) | 0.0252 (3) | 0.0040 (4) | 0.0090 (3) | 0.0063 (3) |
O1 | 0.0480 (11) | 0.0398 (11) | 0.0440 (11) | −0.0162 (8) | 0.0251 (9) | −0.0097 (8) |
N1 | 0.0331 (11) | 0.0281 (13) | 0.0275 (11) | −0.0036 (9) | 0.0122 (9) | −0.0030 (9) |
N2 | 0.0319 (11) | 0.0404 (13) | 0.0275 (11) | 0.0000 (10) | 0.0123 (9) | 0.0024 (9) |
N3 | 0.0354 (11) | 0.0322 (12) | 0.0268 (11) | 0.0057 (9) | 0.0137 (9) | −0.0003 (9) |
N4 | 0.0319 (11) | 0.0308 (12) | 0.0310 (11) | 0.0009 (9) | 0.0120 (9) | 0.0030 (9) |
C1 | 0.0410 (14) | 0.0283 (15) | 0.0344 (14) | −0.0067 (12) | 0.0163 (12) | −0.0076 (11) |
C2 | 0.0390 (14) | 0.0326 (16) | 0.0335 (14) | 0.0005 (12) | 0.0152 (12) | −0.0080 (11) |
C3 | 0.0335 (13) | 0.0426 (16) | 0.0321 (14) | −0.0033 (12) | 0.0142 (11) | 0.0002 (12) |
C4 | 0.0359 (14) | 0.0295 (15) | 0.0336 (14) | −0.0032 (11) | 0.0125 (11) | 0.0043 (11) |
C5 | 0.0356 (14) | 0.0280 (15) | 0.0239 (13) | −0.0005 (11) | 0.0085 (10) | 0.0021 (10) |
C6 | 0.0451 (15) | 0.0324 (15) | 0.0336 (14) | 0.0032 (12) | 0.0182 (12) | 0.0033 (11) |
C7 | 0.0538 (17) | 0.0369 (16) | 0.0418 (16) | 0.0107 (13) | 0.0230 (13) | −0.0007 (13) |
C8 | 0.0352 (14) | 0.0331 (15) | 0.0321 (14) | −0.0018 (11) | 0.0082 (11) | −0.0083 (11) |
C9 | 0.0365 (14) | 0.0356 (15) | 0.0271 (13) | 0.0027 (11) | 0.0089 (11) | −0.0015 (11) |
C10 | 0.0364 (15) | 0.0392 (16) | 0.0471 (16) | 0.0098 (12) | 0.0150 (12) | 0.0018 (13) |
C11 | 0.0423 (15) | 0.0447 (17) | 0.0345 (15) | 0.0016 (13) | 0.0145 (12) | 0.0117 (12) |
C12 | 0.0367 (14) | 0.0439 (17) | 0.0299 (14) | −0.0029 (12) | 0.0132 (11) | 0.0037 (12) |
C13 | 0.0462 (16) | 0.073 (2) | 0.0307 (15) | 0.0029 (15) | 0.0178 (13) | 0.0120 (14) |
C14 | 0.0478 (17) | 0.086 (3) | 0.0434 (17) | 0.0022 (17) | 0.0278 (14) | 0.0061 (16) |
C15 | 0.0405 (16) | 0.090 (3) | 0.0440 (18) | 0.0219 (16) | 0.0213 (14) | 0.0082 (17) |
C16 | 0.0357 (14) | 0.068 (2) | 0.0327 (15) | 0.0106 (14) | 0.0134 (12) | 0.0081 (14) |
Cl2 | 0.0426 (4) | 0.0362 (4) | 0.0334 (3) | 0.0049 (3) | 0.0102 (3) | 0.0026 (3) |
O2 | 0.0499 (11) | 0.0371 (11) | 0.0485 (12) | 0.0097 (9) | 0.0139 (9) | 0.0108 (9) |
O3 | 0.0552 (12) | 0.0396 (11) | 0.0418 (11) | −0.0022 (9) | −0.0031 (10) | −0.0012 (9) |
O4 | 0.0669 (14) | 0.0388 (13) | 0.0723 (16) | −0.0129 (10) | −0.0013 (12) | 0.0028 (10) |
O5 | 0.0863 (18) | 0.129 (2) | 0.0595 (15) | 0.0525 (16) | 0.0397 (14) | 0.0198 (14) |
V1—O1 | 1.6024 (18) | C7—H7A | 0.980 |
V1—N2 | 2.120 (2) | C7—H7B | 0.980 |
V1—N1 | 2.141 (2) | C7—H7C | 0.980 |
V1—N4 | 2.1755 (19) | C8—C9 | 1.494 (3) |
V1—Cl1 | 2.3184 (8) | C8—H8A | 0.990 |
V1—N3 | 2.329 (2) | C8—H8B | 0.990 |
N1—C1 | 1.343 (3) | C9—H9A | 0.990 |
N1—C5 | 1.350 (3) | C9—H9B | 0.990 |
N2—C12 | 1.347 (3) | C10—H10A | 0.980 |
N2—C16 | 1.353 (3) | C10—H10B | 0.980 |
N3—C6 | 1.482 (3) | C10—H10C | 0.980 |
N3—C8 | 1.487 (3) | C11—C12 | 1.491 (3) |
N3—C7 | 1.493 (3) | C11—H11A | 0.990 |
N4—C10 | 1.483 (3) | C11—H11B | 0.990 |
N4—C9 | 1.489 (3) | C12—C13 | 1.383 (3) |
N4—C11 | 1.490 (3) | C13—C14 | 1.371 (4) |
C1—C2 | 1.372 (3) | C13—H13A | 0.950 |
C1—H1A | 0.950 | C14—C15 | 1.381 (4) |
C2—C3 | 1.370 (3) | C14—H14A | 0.950 |
C2—H2A | 0.950 | C15—C16 | 1.374 (4) |
C3—C4 | 1.378 (3) | C15—H15A | 0.950 |
C3—H3A | 0.950 | C16—H16A | 0.950 |
C4—C5 | 1.377 (3) | Cl2—O5 | 1.419 (2) |
C4—H4A | 0.950 | Cl2—O2 | 1.4288 (18) |
C5—C6 | 1.502 (3) | Cl2—O3 | 1.4387 (18) |
C6—H6A | 0.990 | Cl2—O4 | 1.446 (2) |
C6—H6B | 0.990 | ||
O1—V1—N2 | 99.88 (8) | H6A—C6—H6B | 108.3 |
O1—V1—N1 | 92.14 (8) | N3—C7—H7A | 109.5 |
N2—V1—N1 | 165.39 (8) | N3—C7—H7B | 109.5 |
O1—V1—N4 | 90.54 (8) | H7A—C7—H7B | 109.5 |
N2—V1—N4 | 76.80 (8) | N3—C7—H7C | 109.5 |
N1—V1—N4 | 94.94 (7) | H7A—C7—H7C | 109.5 |
O1—V1—Cl1 | 105.20 (7) | H7B—C7—H7C | 109.5 |
N2—V1—Cl1 | 92.60 (6) | N3—C8—C9 | 109.92 (19) |
N1—V1—Cl1 | 92.22 (6) | N3—C8—H8A | 109.7 |
N4—V1—Cl1 | 162.45 (6) | C9—C8—H8A | 109.7 |
O1—V1—N3 | 160.69 (8) | N3—C8—H8B | 109.7 |
N2—V1—N3 | 92.70 (7) | C9—C8—H8B | 109.7 |
N1—V1—N3 | 73.63 (7) | H8A—C8—H8B | 108.2 |
N4—V1—N3 | 78.06 (7) | N4—C9—C8 | 109.54 (19) |
Cl1—V1—N3 | 88.67 (5) | N4—C9—H9A | 109.8 |
C1—N1—C5 | 117.9 (2) | C8—C9—H9A | 109.8 |
C1—N1—V1 | 122.83 (16) | N4—C9—H9B | 109.8 |
C5—N1—V1 | 119.22 (15) | C8—C9—H9B | 109.8 |
C12—N2—C16 | 118.2 (2) | H9A—C9—H9B | 108.2 |
C12—N2—V1 | 114.53 (16) | N4—C10—H10A | 109.5 |
C16—N2—V1 | 127.28 (17) | N4—C10—H10B | 109.5 |
C6—N3—C8 | 109.52 (19) | H10A—C10—H10B | 109.5 |
C6—N3—C7 | 108.62 (18) | N4—C10—H10C | 109.5 |
C8—N3—C7 | 110.94 (19) | H10A—C10—H10C | 109.5 |
C6—N3—V1 | 105.85 (14) | H10B—C10—H10C | 109.5 |
C8—N3—V1 | 106.15 (14) | N4—C11—C12 | 109.4 (2) |
C7—N3—V1 | 115.54 (15) | N4—C11—H11A | 109.8 |
C10—N4—C9 | 110.32 (19) | C12—C11—H11A | 109.8 |
C10—N4—C11 | 108.59 (19) | N4—C11—H11B | 109.8 |
C9—N4—C11 | 109.13 (19) | C12—C11—H11B | 109.8 |
C10—N4—V1 | 113.64 (15) | H11A—C11—H11B | 108.2 |
C9—N4—V1 | 110.97 (14) | N2—C12—C13 | 122.0 (2) |
C11—N4—V1 | 103.90 (14) | N2—C12—C11 | 115.1 (2) |
N1—C1—C2 | 122.9 (2) | C13—C12—C11 | 122.8 (2) |
N1—C1—H1A | 118.6 | C14—C13—C12 | 119.4 (3) |
C2—C1—H1A | 118.6 | C14—C13—H13A | 120.3 |
C3—C2—C1 | 119.0 (2) | C12—C13—H13A | 120.3 |
C3—C2—H2A | 120.5 | C13—C14—C15 | 118.8 (3) |
C1—C2—H2A | 120.5 | C13—C14—H14A | 120.6 |
C2—C3—C4 | 118.8 (2) | C15—C14—H14A | 120.6 |
C2—C3—H3A | 120.6 | C16—C15—C14 | 119.6 (3) |
C4—C3—H3A | 120.6 | C16—C15—H15A | 120.2 |
C5—C4—C3 | 119.7 (2) | C14—C15—H15A | 120.2 |
C5—C4—H4A | 120.2 | N2—C16—C15 | 122.0 (2) |
C3—C4—H4A | 120.2 | N2—C16—H16A | 119.0 |
N1—C5—C4 | 121.6 (2) | C15—C16—H16A | 119.0 |
N1—C5—C6 | 115.4 (2) | O5—Cl2—O2 | 110.73 (13) |
C4—C5—C6 | 123.0 (2) | O5—Cl2—O3 | 111.17 (14) |
N3—C6—C5 | 109.13 (19) | O2—Cl2—O3 | 110.40 (11) |
N3—C6—H6A | 109.9 | O5—Cl2—O4 | 108.72 (16) |
C5—C6—H6A | 109.9 | O2—Cl2—O4 | 107.94 (12) |
N3—C6—H6B | 109.9 | O3—Cl2—O4 | 107.76 (12) |
C5—C6—H6B | 109.9 | ||
O1—V1—N1—C1 | 4.77 (19) | O1—V1—N4—C11 | 63.72 (16) |
N2—V1—N1—C1 | −140.7 (3) | N2—V1—N4—C11 | −36.30 (15) |
N4—V1—N1—C1 | −85.96 (19) | N1—V1—N4—C11 | 155.91 (15) |
Cl1—V1—N1—C1 | 110.08 (18) | Cl1—V1—N4—C11 | −90.4 (2) |
N3—V1—N1—C1 | −162.0 (2) | N3—V1—N4—C11 | −131.99 (16) |
O1—V1—N1—C5 | −177.42 (17) | C5—N1—C1—C2 | −1.1 (4) |
N2—V1—N1—C5 | 37.1 (4) | V1—N1—C1—C2 | 176.77 (18) |
N4—V1—N1—C5 | 91.85 (17) | N1—C1—C2—C3 | −0.4 (4) |
Cl1—V1—N1—C5 | −72.11 (16) | C1—C2—C3—C4 | 1.0 (4) |
N3—V1—N1—C5 | 15.85 (16) | C2—C3—C4—C5 | −0.2 (4) |
O1—V1—N2—C12 | −66.81 (19) | C1—N1—C5—C4 | 1.9 (3) |
N1—V1—N2—C12 | 78.1 (4) | V1—N1—C5—C4 | −176.02 (17) |
N4—V1—N2—C12 | 21.41 (18) | C1—N1—C5—C6 | −177.8 (2) |
Cl1—V1—N2—C12 | −172.73 (17) | V1—N1—C5—C6 | 4.2 (3) |
N3—V1—N2—C12 | 98.48 (18) | C3—C4—C5—N1 | −1.3 (4) |
O1—V1—N2—C16 | 112.7 (2) | C3—C4—C5—C6 | 178.4 (2) |
N1—V1—N2—C16 | −102.4 (4) | C8—N3—C6—C5 | −70.6 (2) |
N4—V1—N2—C16 | −159.1 (2) | C7—N3—C6—C5 | 168.06 (19) |
Cl1—V1—N2—C16 | 6.8 (2) | V1—N3—C6—C5 | 43.4 (2) |
N3—V1—N2—C16 | −82.0 (2) | N1—C5—C6—N3 | −33.9 (3) |
O1—V1—N3—C6 | −75.7 (3) | C4—C5—C6—N3 | 146.3 (2) |
N2—V1—N3—C6 | 153.43 (14) | C6—N3—C8—C9 | 155.42 (19) |
N1—V1—N3—C6 | −31.83 (14) | C7—N3—C8—C9 | −84.7 (2) |
N4—V1—N3—C6 | −130.67 (15) | V1—N3—C8—C9 | 41.6 (2) |
Cl1—V1—N3—C6 | 60.89 (14) | C10—N4—C9—C8 | −84.1 (2) |
O1—V1—N3—C8 | 40.6 (3) | C11—N4—C9—C8 | 156.66 (19) |
N2—V1—N3—C8 | −90.23 (14) | V1—N4—C9—C8 | 42.8 (2) |
N1—V1—N3—C8 | 84.52 (14) | N3—C8—C9—N4 | −57.6 (3) |
N4—V1—N3—C8 | −14.33 (14) | C10—N4—C11—C12 | 168.3 (2) |
Cl1—V1—N3—C8 | 177.23 (14) | C9—N4—C11—C12 | −71.4 (2) |
O1—V1—N3—C7 | 164.0 (2) | V1—N4—C11—C12 | 47.1 (2) |
N2—V1—N3—C7 | 33.19 (16) | C16—N2—C12—C13 | 1.1 (4) |
N1—V1—N3—C7 | −152.06 (17) | V1—N2—C12—C13 | −179.4 (2) |
N4—V1—N3—C7 | 109.09 (16) | C16—N2—C12—C11 | −179.8 (2) |
Cl1—V1—N3—C7 | −59.35 (15) | V1—N2—C12—C11 | −0.3 (3) |
O1—V1—N4—C10 | −54.11 (17) | N4—C11—C12—N2 | −32.9 (3) |
N2—V1—N4—C10 | −154.14 (17) | N4—C11—C12—C13 | 146.2 (3) |
N1—V1—N4—C10 | 38.08 (17) | N2—C12—C13—C14 | −2.1 (4) |
Cl1—V1—N4—C10 | 151.81 (17) | C11—C12—C13—C14 | 178.8 (3) |
N3—V1—N4—C10 | 110.18 (17) | C12—C13—C14—C15 | 1.9 (5) |
O1—V1—N4—C9 | −179.12 (15) | C13—C14—C15—C16 | −0.8 (5) |
N2—V1—N4—C9 | 80.85 (15) | C12—N2—C16—C15 | 0.1 (4) |
N1—V1—N4—C9 | −86.93 (15) | V1—N2—C16—C15 | −179.4 (2) |
Cl1—V1—N4—C9 | 26.8 (3) | C14—C15—C16—N2 | −0.2 (5) |
N3—V1—N4—C9 | −14.83 (14) |