The unsymmetrical N-heterocyclic ligand 1-[(benzotriazol-1-yl)methyl]-1H-1,3-imidazole (bmi) has three potential N-atom donors and can act in monodentate or bridging coordination modes in the construction of complexes. In addition, the bmi ligand can adopt different coordination conformations, resulting in complexes with different structures due to the presence of the flexible methylene spacer. Two new complexes, namely bis{1-[(benzotriazol-1-yl)methyl]-1H-1,3-imidazole-κN3}dibromidomercury(II), [HgBr2(C10H9N5)2], and bis{1-[(benzotriazol-1-yl)methyl]-1H-1,3-imidazole-κN3}diiodidomercury(II), [HgI2(C10H9N5)2], have been synthesized through the self-assembly of bmi with HgBr2 or HgI2. Single-crystal X-ray diffraction shows that both complexes are mononuclear structures, in which the bmi ligands coordinate to the HgII ions in monodentate modes. In the solid state, both complexes display three-dimensional networks formed by a combination of hydrogen bonds and π–π interactions. The IR spectra and PXRD patterns of both complexes have also been recorded.
Supporting information
CCDC references: 998622; 1421140
For both compounds, data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).
(I) Bis{1-[(benzotriazol-1-yl)methyl]-1
H-1,3-imidazole-
κN3}dibromidomercury(II)
top
Crystal data top
[HgBr2(C10H9N5)2] | Dx = 2.094 Mg m−3 |
Mr = 758.85 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 5603 reflections |
a = 11.756 (2) Å | θ = 1.7–27.9° |
b = 11.764 (2) Å | µ = 9.74 mm−1 |
c = 17.407 (4) Å | T = 293 K |
V = 2407.4 (8) Å3 | Platelike, colourless |
Z = 4 | 0.15 × 0.13 × 0.07 mm |
F(000) = 1432 | |
Data collection top
Rigaku Saturn diffractometer | 2372 independent reflections |
Radiation source: fine-focus sealed tube | 1975 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.045 |
ω scans | θmax = 26.0°, θmin = 2.5° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | h = −14→12 |
Tmin = 0.496, Tmax = 1.000 | k = −11→14 |
11136 measured reflections | l = −21→20 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0335P)2 + 0.7321P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
2372 reflections | Δρmax = 0.80 e Å−3 |
150 parameters | Δρmin = −0.62 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Hg1 | 0.0000 | 0.62301 (3) | 0.2500 | 0.04596 (14) | |
Br1 | 0.06282 (6) | 0.52696 (6) | 0.12758 (4) | 0.0646 (2) | |
N1 | 0.1434 (4) | 0.7396 (4) | 0.2938 (3) | 0.0440 (12) | |
N2 | 0.2530 (4) | 0.8229 (4) | 0.3785 (3) | 0.0411 (11) | |
N3 | 0.2289 (4) | 0.9279 (4) | 0.4960 (3) | 0.0399 (11) | |
N4 | 0.2346 (5) | 1.0433 (4) | 0.4865 (3) | 0.0546 (14) | |
N5 | 0.1585 (5) | 1.0884 (4) | 0.5313 (4) | 0.0609 (16) | |
C1 | 0.1755 (5) | 0.7416 (4) | 0.3665 (4) | 0.0421 (13) | |
H1A | 0.1479 | 0.6930 | 0.4042 | 0.050* | |
C2 | 0.2040 (5) | 0.8238 (6) | 0.2580 (3) | 0.0505 (16) | |
H2A | 0.1988 | 0.8422 | 0.2062 | 0.061* | |
C3 | 0.2719 (6) | 0.8754 (5) | 0.3088 (4) | 0.0540 (17) | |
H3A | 0.3219 | 0.9349 | 0.2990 | 0.065* | |
C4 | 0.3041 (5) | 0.8545 (4) | 0.4523 (3) | 0.0421 (14) | |
H4A | 0.3199 | 0.7863 | 0.4817 | 0.051* | |
H4B | 0.3756 | 0.8933 | 0.4432 | 0.051* | |
C5 | 0.1484 (5) | 0.9003 (4) | 0.5488 (3) | 0.0383 (13) | |
C6 | 0.1110 (5) | 0.7979 (5) | 0.5792 (4) | 0.0482 (15) | |
H6A | 0.1414 | 0.7287 | 0.5636 | 0.058* | |
C7 | 0.0272 (6) | 0.8044 (6) | 0.6330 (5) | 0.064 (2) | |
H7A | 0.0015 | 0.7379 | 0.6561 | 0.076* | |
C8 | −0.0214 (6) | 0.9088 (7) | 0.6548 (5) | 0.065 (2) | |
H8A | −0.0803 | 0.9094 | 0.6905 | 0.079* | |
C9 | 0.0151 (6) | 1.0077 (6) | 0.6252 (5) | 0.061 (2) | |
H9A | −0.0165 | 1.0766 | 0.6405 | 0.074* | |
C10 | 0.1025 (5) | 1.0037 (4) | 0.5703 (4) | 0.0467 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.0504 (2) | 0.0485 (2) | 0.0389 (2) | 0.000 | −0.00576 (16) | 0.000 |
Br1 | 0.0626 (4) | 0.0751 (4) | 0.0561 (5) | −0.0083 (3) | 0.0163 (4) | −0.0203 (4) |
N1 | 0.046 (3) | 0.046 (3) | 0.040 (3) | −0.004 (2) | −0.009 (2) | 0.001 (2) |
N2 | 0.043 (3) | 0.038 (2) | 0.042 (3) | −0.002 (2) | −0.005 (2) | 0.002 (2) |
N3 | 0.048 (3) | 0.032 (2) | 0.040 (3) | −0.005 (2) | −0.006 (2) | −0.001 (2) |
N4 | 0.069 (4) | 0.035 (3) | 0.059 (4) | −0.009 (3) | −0.014 (3) | 0.007 (3) |
N5 | 0.081 (4) | 0.038 (3) | 0.063 (4) | 0.001 (3) | −0.023 (3) | −0.001 (3) |
C1 | 0.048 (3) | 0.035 (3) | 0.043 (4) | −0.009 (2) | 0.003 (3) | 0.000 (3) |
C2 | 0.050 (4) | 0.065 (4) | 0.037 (4) | −0.007 (3) | −0.004 (3) | 0.011 (3) |
C3 | 0.061 (4) | 0.057 (4) | 0.045 (4) | −0.020 (3) | 0.004 (3) | 0.015 (3) |
C4 | 0.038 (3) | 0.050 (3) | 0.038 (4) | −0.001 (2) | −0.008 (3) | 0.000 (3) |
C5 | 0.042 (3) | 0.040 (3) | 0.033 (3) | −0.001 (2) | −0.010 (3) | −0.004 (3) |
C6 | 0.051 (3) | 0.045 (3) | 0.048 (4) | −0.001 (3) | −0.004 (3) | −0.001 (3) |
C7 | 0.067 (4) | 0.065 (5) | 0.059 (5) | −0.011 (4) | −0.002 (4) | 0.008 (4) |
C8 | 0.057 (4) | 0.092 (6) | 0.047 (5) | 0.006 (4) | −0.001 (3) | −0.007 (4) |
C9 | 0.059 (4) | 0.065 (4) | 0.061 (5) | 0.021 (3) | −0.017 (4) | −0.024 (4) |
C10 | 0.058 (4) | 0.039 (3) | 0.043 (4) | 0.005 (3) | −0.020 (3) | −0.007 (3) |
Geometric parameters (Å, º) top
Hg1—N1 | 2.304 (4) | C2—C3 | 1.337 (9) |
Hg1—N1i | 2.304 (4) | C2—H2A | 0.9300 |
Hg1—Br1i | 2.5225 (8) | C3—H3A | 0.9300 |
Hg1—Br1 | 2.5226 (8) | C4—H4A | 0.9700 |
N1—C1 | 1.320 (7) | C4—H4B | 0.9700 |
N1—C2 | 1.370 (7) | C5—C10 | 1.382 (7) |
N2—C1 | 1.338 (6) | C5—C6 | 1.386 (7) |
N2—C3 | 1.380 (7) | C6—C7 | 1.362 (9) |
N2—C4 | 1.465 (7) | C6—H6A | 0.9300 |
N3—C5 | 1.360 (7) | C7—C8 | 1.407 (10) |
N3—N4 | 1.369 (6) | C7—H7A | 0.9300 |
N3—C4 | 1.451 (7) | C8—C9 | 1.343 (10) |
N4—N5 | 1.300 (7) | C8—H8A | 0.9300 |
N5—C10 | 1.374 (8) | C9—C10 | 1.403 (10) |
C1—H1A | 0.9300 | C9—H9A | 0.9300 |
| | | |
N1—Hg1—N1i | 106.9 (2) | N2—C3—H3A | 126.8 |
N1—Hg1—Br1i | 101.61 (13) | N3—C4—N2 | 111.2 (4) |
N1i—Hg1—Br1i | 109.40 (13) | N3—C4—H4A | 109.4 |
N1—Hg1—Br1 | 109.41 (13) | N2—C4—H4A | 109.4 |
N1i—Hg1—Br1 | 101.61 (13) | N3—C4—H4B | 109.4 |
Br1i—Hg1—Br1 | 126.78 (4) | N2—C4—H4B | 109.4 |
C1—N1—C2 | 106.0 (5) | H4A—C4—H4B | 108.0 |
C1—N1—Hg1 | 122.5 (4) | N3—C5—C10 | 104.2 (5) |
C2—N1—Hg1 | 131.3 (4) | N3—C5—C6 | 133.3 (5) |
C1—N2—C3 | 106.9 (5) | C10—C5—C6 | 122.5 (6) |
C1—N2—C4 | 126.7 (5) | C7—C6—C5 | 116.3 (6) |
C3—N2—C4 | 126.3 (5) | C7—C6—H6A | 121.9 |
C5—N3—N4 | 110.7 (5) | C5—C6—H6A | 121.9 |
C5—N3—C4 | 129.5 (5) | C6—C7—C8 | 121.9 (6) |
N4—N3—C4 | 119.8 (5) | C6—C7—H7A | 119.0 |
N5—N4—N3 | 107.4 (5) | C8—C7—H7A | 119.0 |
N4—N5—C10 | 109.3 (5) | C9—C8—C7 | 121.5 (7) |
N1—C1—N2 | 110.9 (5) | C9—C8—H8A | 119.2 |
N1—C1—H1A | 124.5 | C7—C8—H8A | 119.2 |
N2—C1—H1A | 124.5 | C8—C9—C10 | 117.7 (6) |
C3—C2—N1 | 109.7 (6) | C8—C9—H9A | 121.1 |
C3—C2—H2A | 125.1 | C10—C9—H9A | 121.1 |
N1—C2—H2A | 125.1 | N5—C10—C5 | 108.5 (6) |
C2—C3—N2 | 106.4 (5) | N5—C10—C9 | 131.5 (6) |
C2—C3—H3A | 126.8 | C5—C10—C9 | 120.0 (6) |
| | | |
C5—N3—N4—N5 | −0.9 (6) | C4—N3—C5—C10 | −179.0 (5) |
C4—N3—N4—N5 | 179.4 (5) | N4—N3—C5—C6 | −179.1 (6) |
N3—N4—N5—C10 | 0.0 (6) | C4—N3—C5—C6 | 0.6 (10) |
C2—N1—C1—N2 | 0.2 (6) | N3—C5—C6—C7 | 179.3 (6) |
Hg1—N1—C1—N2 | −174.6 (3) | C10—C5—C6—C7 | −1.3 (9) |
C3—N2—C1—N1 | −0.4 (6) | C5—C6—C7—C8 | 2.1 (10) |
C4—N2—C1—N1 | 176.7 (5) | C6—C7—C8—C9 | −2.2 (11) |
C1—N1—C2—C3 | 0.1 (7) | C7—C8—C9—C10 | 1.2 (10) |
Hg1—N1—C2—C3 | 174.3 (4) | N4—N5—C10—C5 | 0.9 (7) |
N1—C2—C3—N2 | −0.4 (7) | N4—N5—C10—C9 | 179.4 (7) |
C1—N2—C3—C2 | 0.5 (7) | N3—C5—C10—N5 | −1.4 (6) |
C4—N2—C3—C2 | −176.7 (5) | C6—C5—C10—N5 | 179.1 (5) |
C5—N3—C4—N2 | 91.4 (7) | N3—C5—C10—C9 | 180.0 (6) |
N4—N3—C4—N2 | −89.0 (5) | C6—C5—C10—C9 | 0.4 (9) |
C1—N2—C4—N3 | −80.6 (6) | C8—C9—C10—N5 | −178.6 (6) |
C3—N2—C4—N3 | 96.0 (7) | C8—C9—C10—C5 | −0.3 (9) |
N4—N3—C5—C10 | 1.4 (6) | | |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···N4ii | 0.93 | 2.66 | 3.305 (8) | 127 |
C4—H4A···N5ii | 0.97 | 2.50 | 3.448 (8) | 167 |
C4—H4B···Br1iii | 0.97 | 2.97 | 3.912 (6) | 163 |
Symmetry codes: (ii) −x+1/2, y−1/2, z; (iii) x+1/2, y+1/2, −z+1/2. |
(II) Bis{1-[(benzotriazol-1-yl)methyl]-1
H-1,3-imidazole-
κN3}diiodidomercury(II)
top
Crystal data top
[HgI2(C10H9N5)2] | Dx = 2.215 Mg m−3 |
Mr = 852.83 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 5903 reflections |
a = 12.103 (2) Å | θ = 2.0–27.9° |
b = 11.827 (2) Å | µ = 8.46 mm−1 |
c = 17.862 (4) Å | T = 293 K |
V = 2556.8 (9) Å3 | Prism, colourless |
Z = 4 | 0.16 × 0.15 × 0.11 mm |
F(000) = 1576 | |
Data collection top
Rigaku Saturn diffractometer | 2519 independent reflections |
Radiation source: fine-focus sealed tube | 2381 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.044 |
ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | h = −11→14 |
Tmin = 0.703, Tmax = 1.000 | k = −12→14 |
18126 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0289P)2 + 3.5625P] where P = (Fo2 + 2Fc2)/3 |
S = 1.28 | (Δ/σ)max < 0.001 |
2519 reflections | Δρmax = 0.53 e Å−3 |
150 parameters | Δρmin = −0.87 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Hg1 | 1.0000 | 0.61838 (3) | 0.2500 | 0.04677 (14) | |
I1 | 0.93007 (4) | 0.52533 (5) | 0.12259 (3) | 0.06414 (19) | |
N1 | 0.8619 (5) | 0.7401 (5) | 0.2936 (3) | 0.0487 (14) | |
N2 | 0.7533 (4) | 0.8218 (5) | 0.3753 (3) | 0.0461 (13) | |
N3 | 0.7754 (5) | 0.9297 (4) | 0.4882 (3) | 0.0484 (14) | |
N4 | 0.7665 (6) | 1.0422 (5) | 0.4772 (4) | 0.068 (2) | |
N5 | 0.8361 (6) | 1.0922 (6) | 0.5220 (4) | 0.074 (2) | |
C1 | 0.8304 (6) | 0.7427 (5) | 0.3636 (4) | 0.0493 (17) | |
H1A | 0.8581 | 0.6953 | 0.4007 | 0.059* | |
C2 | 0.8006 (6) | 0.8208 (7) | 0.2579 (4) | 0.063 (2) | |
H2A | 0.8041 | 0.8371 | 0.2070 | 0.075* | |
C3 | 0.7352 (6) | 0.8726 (7) | 0.3072 (4) | 0.067 (2) | |
H3A | 0.6867 | 0.9317 | 0.2974 | 0.080* | |
C4 | 0.7053 (6) | 0.8534 (6) | 0.4465 (4) | 0.0509 (17) | |
H4A | 0.6344 | 0.8893 | 0.4379 | 0.061* | |
H4B | 0.6926 | 0.7857 | 0.4760 | 0.061* | |
C5 | 0.8522 (6) | 0.9065 (5) | 0.5415 (4) | 0.0464 (17) | |
C6 | 0.8921 (7) | 1.0115 (7) | 0.5622 (5) | 0.059 (2) | |
C7 | 0.9732 (9) | 1.0203 (10) | 0.6179 (6) | 0.084 (3) | |
H7A | 1.0011 | 1.0900 | 0.6328 | 0.101* | |
C8 | 1.0092 (7) | 0.9227 (11) | 0.6491 (6) | 0.086 (3) | |
H8A | 1.0630 | 0.9260 | 0.6862 | 0.104* | |
C9 | 0.9686 (8) | 0.8185 (10) | 0.6278 (6) | 0.083 (3) | |
H9A | 0.9965 | 0.7539 | 0.6507 | 0.100* | |
C10 | 0.8889 (6) | 0.8072 (7) | 0.5744 (4) | 0.062 (2) | |
H10A | 0.8608 | 0.7369 | 0.5608 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.0496 (2) | 0.0518 (2) | 0.0389 (2) | 0.000 | 0.00187 (17) | 0.000 |
I1 | 0.0600 (3) | 0.0779 (4) | 0.0545 (3) | 0.0034 (3) | −0.0164 (2) | −0.0170 (3) |
N1 | 0.052 (3) | 0.050 (3) | 0.044 (3) | 0.009 (3) | 0.006 (3) | −0.001 (3) |
N2 | 0.050 (3) | 0.045 (3) | 0.043 (3) | 0.011 (3) | 0.005 (3) | 0.004 (3) |
N3 | 0.061 (4) | 0.034 (3) | 0.050 (4) | 0.006 (3) | 0.017 (3) | 0.006 (3) |
N4 | 0.091 (5) | 0.039 (3) | 0.074 (5) | 0.013 (3) | 0.033 (4) | 0.013 (3) |
N5 | 0.093 (6) | 0.044 (4) | 0.085 (6) | −0.005 (4) | 0.043 (5) | −0.006 (4) |
C1 | 0.055 (4) | 0.040 (4) | 0.053 (5) | 0.012 (3) | 0.003 (3) | 0.001 (3) |
C2 | 0.063 (5) | 0.078 (5) | 0.047 (5) | 0.014 (4) | 0.003 (4) | 0.017 (4) |
C3 | 0.066 (5) | 0.081 (6) | 0.053 (5) | 0.034 (4) | 0.005 (4) | 0.016 (4) |
C4 | 0.050 (4) | 0.048 (4) | 0.055 (5) | 0.008 (3) | 0.007 (3) | 0.005 (3) |
C5 | 0.049 (4) | 0.039 (4) | 0.051 (4) | −0.001 (3) | 0.017 (3) | −0.008 (3) |
C6 | 0.060 (5) | 0.059 (5) | 0.059 (5) | −0.010 (4) | 0.027 (4) | −0.018 (4) |
C7 | 0.077 (6) | 0.096 (8) | 0.080 (7) | −0.039 (6) | 0.030 (5) | −0.039 (6) |
C8 | 0.061 (6) | 0.137 (10) | 0.060 (6) | −0.010 (6) | 0.003 (4) | −0.018 (7) |
C9 | 0.071 (6) | 0.105 (8) | 0.073 (7) | 0.010 (6) | −0.004 (5) | −0.006 (6) |
C10 | 0.070 (5) | 0.058 (5) | 0.057 (5) | 0.002 (4) | −0.002 (4) | 0.003 (4) |
Geometric parameters (Å, º) top
Hg1—N1 | 2.340 (5) | C2—C3 | 1.333 (10) |
Hg1—N1i | 2.340 (5) | C2—H2A | 0.9300 |
Hg1—I1i | 2.6658 (7) | C3—H3A | 0.9300 |
Hg1—I1 | 2.6659 (6) | C4—H4A | 0.9700 |
N1—C1 | 1.307 (8) | C4—H4B | 0.9700 |
N1—C2 | 1.366 (9) | C5—C6 | 1.383 (9) |
N2—C1 | 1.338 (8) | C5—C10 | 1.386 (10) |
N2—C3 | 1.374 (9) | C6—C7 | 1.401 (13) |
N2—C4 | 1.448 (8) | C7—C8 | 1.353 (14) |
N3—N4 | 1.350 (8) | C7—H7A | 0.9300 |
N3—C5 | 1.358 (9) | C8—C9 | 1.380 (15) |
N3—C4 | 1.446 (9) | C8—H8A | 0.9300 |
N4—N5 | 1.303 (10) | C9—C10 | 1.363 (11) |
N5—C6 | 1.374 (11) | C9—H9A | 0.9300 |
C1—H1A | 0.9300 | C10—H10A | 0.9300 |
| | | |
N1—Hg1—N1i | 104.0 (3) | N2—C3—H3A | 126.6 |
N1—Hg1—I1i | 101.36 (15) | N3—C4—N2 | 112.2 (6) |
N1i—Hg1—I1i | 108.13 (15) | N3—C4—H4A | 109.2 |
N1—Hg1—I1 | 108.14 (15) | N2—C4—H4A | 109.2 |
N1i—Hg1—I1 | 101.36 (15) | N3—C4—H4B | 109.2 |
I1i—Hg1—I1 | 131.23 (3) | N2—C4—H4B | 109.2 |
C1—N1—C2 | 105.8 (6) | H4A—C4—H4B | 107.9 |
C1—N1—Hg1 | 122.7 (5) | N3—C5—C6 | 104.2 (7) |
C2—N1—Hg1 | 131.5 (5) | N3—C5—C10 | 133.4 (7) |
C1—N2—C3 | 106.2 (6) | C6—C5—C10 | 122.3 (8) |
C1—N2—C4 | 126.7 (6) | N5—C6—C5 | 108.1 (8) |
C3—N2—C4 | 127.0 (6) | N5—C6—C7 | 131.7 (9) |
N4—N3—C5 | 110.8 (6) | C5—C6—C7 | 120.1 (9) |
N4—N3—C4 | 119.6 (6) | C8—C7—C6 | 117.0 (9) |
C5—N3—C4 | 129.5 (5) | C8—C7—H7A | 121.5 |
N5—N4—N3 | 107.8 (7) | C6—C7—H7A | 121.5 |
N4—N5—C6 | 109.0 (6) | C7—C8—C9 | 122.2 (10) |
N1—C1—N2 | 111.6 (6) | C7—C8—H8A | 118.9 |
N1—C1—H1A | 124.2 | C9—C8—H8A | 118.9 |
N2—C1—H1A | 124.2 | C10—C9—C8 | 122.2 (10) |
C3—C2—N1 | 109.6 (7) | C10—C9—H9A | 118.9 |
C3—C2—H2A | 125.2 | C8—C9—H9A | 118.9 |
N1—C2—H2A | 125.2 | C9—C10—C5 | 116.1 (8) |
C2—C3—N2 | 106.8 (6) | C9—C10—H10A | 121.9 |
C2—C3—H3A | 126.6 | C5—C10—H10A | 121.9 |
| | | |
C5—N3—N4—N5 | 0.3 (7) | C4—N3—C5—C6 | −179.2 (6) |
C4—N3—N4—N5 | 178.7 (6) | N4—N3—C5—C10 | 177.4 (7) |
N3—N4—N5—C6 | 0.5 (8) | C4—N3—C5—C10 | −0.7 (12) |
C2—N1—C1—N2 | −1.0 (8) | N4—N5—C6—C5 | −1.2 (8) |
Hg1—N1—C1—N2 | 177.7 (4) | N4—N5—C6—C7 | −178.7 (8) |
C3—N2—C1—N1 | 0.1 (8) | N3—C5—C6—N5 | 1.3 (8) |
C4—N2—C1—N1 | −175.6 (6) | C10—C5—C6—N5 | −177.3 (7) |
C1—N1—C2—C3 | 1.5 (9) | N3—C5—C6—C7 | 179.2 (7) |
Hg1—N1—C2—C3 | −177.0 (5) | C10—C5—C6—C7 | 0.5 (11) |
N1—C2—C3—N2 | −1.5 (10) | N5—C6—C7—C8 | 177.4 (8) |
C1—N2—C3—C2 | 0.9 (9) | C5—C6—C7—C8 | 0.1 (12) |
C4—N2—C3—C2 | 176.5 (7) | C6—C7—C8—C9 | −0.1 (14) |
N4—N3—C4—N2 | 88.1 (7) | C7—C8—C9—C10 | −0.6 (15) |
C5—N3—C4—N2 | −94.0 (8) | C8—C9—C10—C5 | 1.1 (13) |
C1—N2—C4—N3 | 80.9 (8) | N3—C5—C10—C9 | −179.4 (8) |
C3—N2—C4—N3 | −93.8 (9) | C6—C5—C10—C9 | −1.1 (11) |
N4—N3—C5—C6 | −1.0 (7) | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···N4ii | 0.93 | 2.72 | 3.334 (9) | 124 |
C4—H4B···N5ii | 0.97 | 2.46 | 3.408 (10) | 167 |
C4—H4A···I1iii | 0.97 | 3.14 | 4.093 (7) | 167 |
Symmetry codes: (ii) −x+3/2, y−1/2, z; (iii) x−1/2, y+1/2, −z+1/2. |