Two ionic hydrogen-bonded organic frameworks (iHOFs) assembled from 4-cyano-
N-(4-cyanobenzyl)pyridinium, have been crystallized with Br
− and antimony(III) pentabromide, [SbBr
5]
2−, as counter-ions and characterized. These are 4-cyano-
N-(4-cyanobenzyl)pyridinium bromide, C
14H
10N
3+·Br
−, and bis[4-cyano-
N-(4-cyanobenzyl)pyridinium] antimony(III) pentabromide, (C
14H
10N
3)
2[SbBr
5]. The CH
NC interactions induced by templating anions construct disparate frameworks. Hirshfeld surface analysis indicated that these crystals exhibit two types of hydrogen-bonding interactions, specifically CH
NC and CH
Br. Consecutive reverse-parallel CH
NC hydrogen-bonding interactions in these crystals induced the formation of a large number of CH
NC bonds which exhibit both
cis and
trans configurations.
Supporting information
CCDC references: 2351706; 2351705
4-Cyano-
N-(4-cyanobenzyl)pyridinium bromide (iHOFI)
top
Crystal data top
C14H10N3+·Br− | Dx = 1.630 Mg m−3 |
Mr = 300.16 | Ga Kα radiation, λ = 1.34138 Å |
Orthorhombic, Pnma | Cell parameters from 6776 reflections |
a = 8.7734 (4) Å | θ = 3.9–59.4° |
b = 7.0554 (3) Å | µ = 2.94 mm−1 |
c = 19.7544 (10) Å | T = 150 K |
V = 1222.79 (10) Å3 | Block, colourless |
Z = 4 | 0.1 × 0.08 × 0.05 mm |
F(000) = 600 | |
Data collection top
Bruker D8 VENTURE PHOTON III diffractometer | 1245 reflections with I > 2σ(I) |
Radiation source: MetalJet | Rint = 0.055 |
φ and ω scans | θmax = 59.4°, θmin = 3.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −11→11 |
Tmin = 0.657, Tmax = 0.752 | k = −8→9 |
15238 measured reflections | l = −24→25 |
1461 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.0252P)2 + 1.2992P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1461 reflections | Δρmax = 0.83 e Å−3 |
97 parameters | Δρmin = −0.59 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Br1 | 0.65349 (4) | 0.750000 | 0.24449 (2) | 0.02461 (12) | |
N1 | 0.3682 (3) | 0.250000 | 0.19981 (12) | 0.0191 (5) | |
N2 | 0.7171 (4) | 0.250000 | −0.01965 (15) | 0.0355 (7) | |
N3 | 0.7791 (4) | 0.250000 | 0.53003 (14) | 0.0349 (7) | |
C1 | 0.4120 (2) | 0.4177 (3) | 0.17268 (10) | 0.0231 (5) | |
H1 | 0.379092 | 0.533022 | 0.192725 | 0.028* | |
C2 | 0.5038 (2) | 0.4218 (3) | 0.11626 (10) | 0.0232 (4) | |
H2 | 0.535449 | 0.538883 | 0.097130 | 0.028* | |
C3 | 0.5492 (3) | 0.250000 | 0.08783 (14) | 0.0208 (6) | |
C4 | 0.6446 (4) | 0.250000 | 0.02813 (15) | 0.0264 (7) | |
C5 | 0.2776 (3) | 0.250000 | 0.26353 (14) | 0.0212 (6) | |
H5A | 0.211507 | 0.136349 | 0.264955 | 0.025* | 0.5 |
H5B | 0.211507 | 0.363651 | 0.264955 | 0.025* | 0.5 |
C6 | 0.3826 (3) | 0.250000 | 0.32356 (14) | 0.0199 (6) | |
C7 | 0.4332 (2) | 0.4210 (3) | 0.35092 (11) | 0.0248 (5) | |
H7 | 0.397935 | 0.537574 | 0.332593 | 0.030* | |
C8 | 0.5343 (3) | 0.4217 (3) | 0.40457 (11) | 0.0264 (5) | |
H8 | 0.568918 | 0.538316 | 0.423071 | 0.032* | |
C9 | 0.5850 (3) | 0.250000 | 0.43138 (15) | 0.0233 (7) | |
C10 | 0.6925 (4) | 0.250000 | 0.48684 (16) | 0.0276 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02063 (17) | 0.01648 (17) | 0.03671 (19) | 0.000 | −0.00149 (13) | 0.000 |
N1 | 0.0165 (12) | 0.0193 (13) | 0.0216 (11) | 0.000 | −0.0025 (9) | 0.000 |
N2 | 0.0462 (18) | 0.0288 (17) | 0.0315 (15) | 0.000 | 0.0072 (13) | 0.000 |
N3 | 0.0394 (17) | 0.0338 (18) | 0.0317 (15) | 0.000 | −0.0054 (13) | 0.000 |
C1 | 0.0240 (10) | 0.0182 (12) | 0.0272 (10) | 0.0016 (9) | −0.0015 (8) | 0.0000 (8) |
C2 | 0.0266 (11) | 0.0175 (11) | 0.0256 (10) | −0.0016 (9) | −0.0027 (8) | 0.0008 (8) |
C3 | 0.0195 (14) | 0.0231 (17) | 0.0197 (13) | 0.000 | −0.0030 (11) | 0.000 |
C4 | 0.0323 (17) | 0.0207 (17) | 0.0261 (15) | 0.000 | −0.0029 (14) | 0.000 |
C5 | 0.0170 (13) | 0.0191 (14) | 0.0276 (15) | 0.000 | 0.0033 (11) | 0.000 |
C6 | 0.0180 (14) | 0.0190 (16) | 0.0228 (14) | 0.000 | 0.0045 (10) | 0.000 |
C7 | 0.0264 (11) | 0.0170 (12) | 0.0310 (11) | −0.0007 (9) | 0.0024 (9) | 0.0015 (8) |
C8 | 0.0301 (12) | 0.0209 (12) | 0.0283 (10) | −0.0029 (10) | 0.0011 (9) | −0.0027 (8) |
C9 | 0.0210 (15) | 0.0258 (18) | 0.0232 (14) | 0.000 | 0.0044 (11) | 0.000 |
C10 | 0.0312 (17) | 0.0240 (18) | 0.0275 (16) | 0.000 | 0.0067 (13) | 0.000 |
Geometric parameters (Å, º) top
N1—C1i | 1.354 (3) | C5—H5A | 0.9900 |
N1—C1 | 1.354 (3) | C5—H5B | 0.9900 |
N1—C5 | 1.489 (4) | C5—C6 | 1.502 (4) |
N2—C4 | 1.138 (4) | C6—C7 | 1.395 (3) |
N3—C10 | 1.143 (4) | C6—C7i | 1.395 (3) |
C1—H1 | 0.9500 | C7—H7 | 0.9500 |
C1—C2 | 1.375 (3) | C7—C8 | 1.382 (3) |
C2—H2 | 0.9500 | C8—H8 | 0.9500 |
C2—C3 | 1.394 (3) | C8—C9 | 1.395 (3) |
C3—C4 | 1.446 (4) | C9—C10 | 1.445 (5) |
| | | |
C1i—N1—C1 | 121.7 (3) | H5A—C5—H5B | 108.2 |
C1—N1—C5 | 119.08 (13) | C6—C5—H5A | 109.7 |
C1i—N1—C5 | 119.07 (13) | C6—C5—H5B | 109.7 |
N1—C1—H1 | 119.8 | C7i—C6—C5 | 120.07 (14) |
N1—C1—C2 | 120.3 (2) | C7—C6—C5 | 120.07 (14) |
C2—C1—H1 | 119.8 | C7—C6—C7i | 119.8 (3) |
C1—C2—H2 | 120.8 | C6—C7—H7 | 119.9 |
C1—C2—C3 | 118.4 (2) | C8—C7—C6 | 120.3 (2) |
C3—C2—H2 | 120.8 | C8—C7—H7 | 119.9 |
C2i—C3—C2 | 120.8 (3) | C7—C8—H8 | 120.2 |
C2—C3—C4 | 119.60 (13) | C7—C8—C9 | 119.5 (2) |
C2i—C3—C4 | 119.60 (13) | C9—C8—H8 | 120.2 |
N2—C4—C3 | 178.6 (4) | C8i—C9—C8 | 120.5 (3) |
N1—C5—H5A | 109.7 | C8—C9—C10 | 119.73 (14) |
N1—C5—H5B | 109.7 | C8i—C9—C10 | 119.73 (14) |
N1—C5—C6 | 109.9 (2) | N3—C10—C9 | 179.0 (3) |
| | | |
N1—C1—C2—C3 | 0.4 (3) | C1—C2—C3—C4 | 179.5 (2) |
N1—C5—C6—C7 | 89.1 (2) | C5—N1—C1—C2 | 175.9 (2) |
N1—C5—C6—C7i | −89.1 (2) | C5—C6—C7—C8 | −177.6 (2) |
C1i—N1—C1—C2 | −0.3 (4) | C6—C7—C8—C9 | −0.2 (4) |
C1—N1—C5—C6 | −88.1 (2) | C7i—C6—C7—C8 | 0.7 (4) |
C1i—N1—C5—C6 | 88.1 (2) | C7—C8—C9—C8i | −0.2 (4) |
C1—C2—C3—C2i | −0.6 (4) | C7—C8—C9—C10 | 179.1 (2) |
Symmetry code: (i) x, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Br1ii | 0.95 | 2.79 | 3.649 (2) | 151 |
C2—H2···N3iii | 0.95 | 2.57 | 3.448 (3) | 153 |
C5—H5A···Br1iv | 0.99 | 2.78 | 3.6953 (9) | 154 |
C5—H5B···Br1ii | 0.99 | 2.78 | 3.6953 (9) | 154 |
C8—H8···N2v | 0.95 | 2.65 | 3.516 (3) | 151 |
Symmetry codes: (ii) x−1/2, −y+3/2, −z+1/2; (iii) −x+3/2, −y+1, z−1/2; (iv) x−1/2, −y+1/2, −z+1/2; (v) −x+3/2, −y+1, z+1/2. |
Bis[4-cyano-
N-(4-cyanobenzyl)pyridinium] antimony(III) pentabromide (iHOFII)
top
Crystal data top
(C14H10N3)2[SbBr5] | Dx = 1.536 Mg m−3 |
Mr = 959.80 | Ga Kα radiation, λ = 1.34138 Å |
Tetragonal, I4/m | Cell parameters from 9796 reflections |
a = 23.8054 (12) Å | θ = 4.6–59.4° |
c = 7.3222 (4) Å | µ = 7.57 mm−1 |
V = 4149.5 (5) Å3 | T = 150 K |
Z = 4 | NEEDLE, brown |
F(000) = 1820 | 0.08 × 0.03 × 0.02 mm |
Data collection top
Bruker D8 VENTURE PHOTON III diffractometer | 2327 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.056 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 59.3°, θmin = 4.6° |
Tmin = 0.022, Tmax = 0.098 | h = −27→30 |
32444 measured reflections | k = −26→30 |
2447 independent reflections | l = −9→8 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.132P)2 + 37.369P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
2447 reflections | Δρmax = 2.40 e Å−3 |
150 parameters | Δρmin = −1.75 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.4835 (2) | 0.3428 (3) | 0.5000 | 0.0304 (12) | |
N2 | 0.6685 (4) | 0.2200 (4) | 0.5000 | 0.058 (2) | |
N3 | 0.2405 (4) | 0.1467 (4) | 0.5000 | 0.061 (2) | |
C1 | 0.5073 (2) | 0.3297 (2) | 0.6587 (7) | 0.0358 (11) | |
H1 | 0.4903 | 0.3414 | 0.7696 | 0.043* | |
C2 | 0.5568 (2) | 0.2991 (3) | 0.6635 (8) | 0.0394 (12) | |
H2 | 0.5740 | 0.2893 | 0.7762 | 0.047* | |
C3 | 0.5802 (3) | 0.2833 (3) | 0.5000 | 0.0328 (15) | |
C4 | 0.6308 (3) | 0.2486 (4) | 0.5000 | 0.0414 (18) | |
C5 | 0.4262 (3) | 0.3677 (3) | 0.5000 | 0.0314 (14) | |
H5A | 0.4210 | 0.3915 | 0.3903 | 0.038* | 0.5 |
H5B | 0.4210 | 0.3915 | 0.6097 | 0.038* | 0.5 |
C6 | 0.3839 (3) | 0.3206 (3) | 0.5000 | 0.0309 (14) | |
C7 | 0.3658 (2) | 0.2980 (2) | 0.3359 (7) | 0.0362 (11) | |
H7 | 0.3782 | 0.3138 | 0.2237 | 0.043* | |
C8 | 0.3294 (2) | 0.2522 (2) | 0.3351 (8) | 0.0402 (12) | |
H8 | 0.3167 | 0.2366 | 0.2231 | 0.048* | |
C9 | 0.3120 (3) | 0.2298 (3) | 0.5000 | 0.0369 (16) | |
C10 | 0.2730 (4) | 0.1835 (4) | 0.5000 | 0.046 (2) | |
Sb1 | 0.47999 (9) | 0.11701 (9) | 0.2488 (3) | 0.0244 (5) | 0.125 |
Br1 | 0.46859 (15) | 0.18576 (12) | 0.5000 | 0.0377 (7) | 0.25 |
Br2 | 0.46397 (16) | 0.21197 (16) | 0.0000 | 0.0418 (8) | 0.25 |
Br3 | 0.4986 (2) | 0.03254 (14) | 0.5000 | 0.0523 (9) | 0.25 |
Br4 | 0.5934 (5) | 0.1320 (6) | 0.218 (2) | 0.068 (3) | 0.125 |
Br4A | 0.3678 (5) | 0.0819 (8) | 0.257 (3) | 0.113 (7) | 0.125 |
Sb2 | 0.5000 | 0.5000 | 0.05741 (14) | 0.0210 (3) | 0.5 |
Br5 | 0.41593 (3) | 0.41812 (3) | 0.0000 | 0.0347 (3) | 0.9 |
Br6 | 0.5000 | 0.5000 | −0.2922 (2) | 0.0239 (4) | 0.45 |
Br7 | 0.5000 | 0.5000 | 0.5000 | 0.0259 (6) | 0.45 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.025 (3) | 0.034 (3) | 0.032 (3) | −0.003 (2) | 0.000 | 0.000 |
N2 | 0.053 (5) | 0.060 (5) | 0.060 (5) | 0.023 (4) | 0.000 | 0.000 |
N3 | 0.069 (6) | 0.054 (5) | 0.061 (5) | −0.028 (4) | 0.000 | 0.000 |
C1 | 0.032 (2) | 0.048 (3) | 0.028 (2) | 0.003 (2) | −0.002 (2) | −0.006 (2) |
C2 | 0.035 (3) | 0.053 (3) | 0.030 (3) | 0.004 (2) | −0.004 (2) | −0.002 (2) |
C3 | 0.029 (3) | 0.033 (3) | 0.037 (4) | 0.004 (3) | 0.000 | 0.000 |
C4 | 0.037 (4) | 0.045 (4) | 0.042 (4) | 0.010 (3) | 0.000 | 0.000 |
C5 | 0.025 (3) | 0.033 (3) | 0.035 (4) | 0.001 (3) | 0.000 | 0.000 |
C6 | 0.026 (3) | 0.032 (3) | 0.035 (4) | −0.002 (3) | 0.000 | 0.000 |
C7 | 0.038 (3) | 0.041 (3) | 0.029 (3) | −0.007 (2) | 0.003 (2) | 0.000 (2) |
C8 | 0.041 (3) | 0.043 (3) | 0.036 (3) | −0.011 (2) | 0.000 (2) | −0.005 (2) |
C9 | 0.039 (4) | 0.034 (4) | 0.038 (4) | −0.003 (3) | 0.000 | 0.000 |
C10 | 0.053 (5) | 0.046 (5) | 0.037 (4) | −0.015 (4) | 0.000 | 0.000 |
Sb1 | 0.0232 (10) | 0.0202 (10) | 0.0299 (12) | 0.0005 (8) | −0.0056 (9) | −0.0091 (8) |
Br1 | 0.0503 (18) | 0.0232 (13) | 0.0396 (17) | 0.0016 (12) | 0.000 | 0.000 |
Br2 | 0.0516 (19) | 0.0536 (19) | 0.0202 (13) | 0.0145 (15) | 0.000 | 0.000 |
Br3 | 0.070 (3) | 0.0273 (17) | 0.060 (2) | 0.0023 (16) | 0.000 | 0.000 |
Br4 | 0.034 (3) | 0.089 (8) | 0.080 (6) | 0.009 (3) | 0.016 (3) | 0.018 (5) |
Br4A | 0.047 (6) | 0.112 (12) | 0.180 (17) | −0.026 (6) | −0.045 (8) | 0.012 (10) |
Sb2 | 0.0235 (4) | 0.0235 (4) | 0.0159 (5) | 0.000 | 0.000 | 0.000 |
Br5 | 0.0232 (4) | 0.0253 (4) | 0.0555 (6) | −0.0053 (3) | 0.000 | 0.000 |
Br6 | 0.0301 (6) | 0.0301 (6) | 0.0113 (9) | 0.000 | 0.000 | 0.000 |
Br7 | 0.0278 (9) | 0.0278 (9) | 0.0222 (14) | 0.000 | 0.000 | 0.000 |
Geometric parameters (Å, º) top
N1—C1i | 1.330 (6) | Sb1—Br4ii | 2.736 (15) |
N1—C1 | 1.330 (6) | Sb1—Br4 | 2.733 (11) |
N1—C5 | 1.488 (9) | Sb1—Br4Aiii | 2.453 (19) |
N2—C4 | 1.127 (11) | Sb1—Br4A | 2.800 (14) |
N3—C10 | 1.169 (12) | Br1—Sb1i | 2.477 (3) |
C1—H1 | 0.9500 | Br2—Sb1iv | 2.928 (4) |
C1—C2 | 1.386 (8) | Br3—Sb1i | 2.761 (3) |
C2—H2 | 0.9500 | Br3—Br3v | 1.550 (7) |
C2—C3 | 1.372 (7) | Br4—Sb1iii | 2.736 (15) |
C3—C2i | 1.372 (7) | Br4—Br4Aiii | 0.33 (3) |
C3—C4 | 1.461 (10) | Br4A—Sb1ii | 2.454 (19) |
C5—H5A | 0.9900 | Br4A—Br4ii | 0.33 (3) |
C5—H5B | 0.9900 | Sb2—Sb2vi | 0.841 (2) |
C5—C6 | 1.507 (10) | Sb2—Br5vii | 2.8251 (8) |
C6—C7 | 1.386 (6) | Sb2—Br5 | 2.8251 (8) |
C6—C7i | 1.386 (6) | Sb2—Br5vi | 2.8251 (8) |
C7—H7 | 0.9500 | Sb2—Br5viii | 2.8251 (8) |
C7—C8 | 1.394 (7) | Sb2—Br6 | 2.560 (2) |
C8—H8 | 0.9500 | Sb2—Br6vi | 1.719 (2) |
C8—C9 | 1.383 (7) | Br5—Sb2vi | 2.8251 (8) |
C9—C8i | 1.383 (7) | Br6—Sb2vi | 1.719 (2) |
C9—C10 | 1.442 (11) | Br6—Br7ix | 1.5213 (18) |
Sb1—Br1 | 2.477 (3) | Br7—Br6vi | 1.5214 (18) |
Sb1—Br2 | 2.928 (4) | Br7—Br6x | 1.5214 (18) |
Sb1—Br3 | 2.761 (3) | | |
| | | |
C1i—N1—C1 | 121.7 (6) | Br4ii—Sb1—Br4A | 6.8 (5) |
C1i—N1—C5 | 119.0 (3) | Br4Aiii—Sb1—Br1 | 91.3 (4) |
C1—N1—C5 | 119.0 (3) | Br4A—Sb1—Br2 | 96.8 (4) |
N1—C1—H1 | 119.7 | Br4Aiii—Sb1—Br2 | 90.3 (5) |
N1—C1—C2 | 120.5 (5) | Br4Aiii—Sb1—Br3 | 87.7 (5) |
C2—C1—H1 | 119.7 | Br4Aiii—Sb1—Br4ii | 174.6 (7) |
C1—C2—H2 | 121.1 | Br4Aiii—Sb1—Br4 | 4.0 (7) |
C3—C2—C1 | 117.8 (5) | Br4Aiii—Sb1—Br4A | 171.1 (5) |
C3—C2—H2 | 121.1 | Sb1i—Br1—Sb1 | 95.89 (15) |
C2—C3—C2i | 121.5 (7) | Sb1iv—Br2—Sb1 | 76.95 (12) |
C2i—C3—C4 | 119.3 (4) | Sb1—Br3—Sb1i | 83.54 (13) |
C2—C3—C4 | 119.3 (4) | Br3v—Br3—Sb1i | 137.27 (10) |
N2—C4—C3 | 177.3 (10) | Br3v—Br3—Sb1 | 137.27 (10) |
N1—C5—H5A | 110.0 | Sb1—Br4—Sb1iii | 93.9 (4) |
N1—C5—H5B | 110.0 | Br4Aiii—Br4—Sb1 | 31 (6) |
N1—C5—C6 | 108.3 (6) | Br4Aiii—Br4—Sb1iii | 98 (5) |
H5A—C5—H5B | 108.4 | Sb1ii—Br4A—Sb1 | 98.8 (5) |
C6—C5—H5A | 110.0 | Br4ii—Br4A—Sb1 | 76 (5) |
C6—C5—H5B | 110.0 | Br4ii—Br4A—Sb1ii | 145 (6) |
C7i—C6—C5 | 119.8 (3) | Sb2vi—Sb2—Br5vii | 81.44 (2) |
C7—C6—C5 | 119.8 (3) | Sb2vi—Sb2—Br5viii | 81.44 (2) |
C7i—C6—C7 | 120.3 (7) | Sb2vi—Sb2—Br5 | 81.44 (2) |
C6—C7—H7 | 120.0 | Sb2vi—Sb2—Br5vi | 81.44 (2) |
C6—C7—C8 | 120.1 (5) | Sb2vi—Sb2—Br6vi | 180.0 |
C8—C7—H7 | 120.0 | Sb2vi—Sb2—Br6 | 0.000 (1) |
C7—C8—H8 | 120.5 | Br5vii—Sb2—Br5 | 88.731 (6) |
C9—C8—C7 | 119.0 (5) | Br5vi—Sb2—Br5viii | 88.731 (6) |
C9—C8—H8 | 120.5 | Br5vi—Sb2—Br5vii | 88.731 (6) |
C8i—C9—C8 | 121.6 (7) | Br5viii—Sb2—Br5 | 88.732 (6) |
C8—C9—C10 | 119.2 (4) | Br5vi—Sb2—Br5 | 162.89 (4) |
C8i—C9—C10 | 119.2 (4) | Br5vii—Sb2—Br5viii | 162.89 (4) |
N3—C10—C9 | 178.7 (11) | Br6—Sb2—Br5viii | 81.44 (2) |
Br1—Sb1—Br2 | 86.42 (9) | Br6vi—Sb2—Br5 | 98.56 (2) |
Br1—Sb1—Br3 | 90.25 (10) | Br6—Sb2—Br5vii | 81.44 (2) |
Br1—Sb1—Br4 | 94.8 (3) | Br6vi—Sb2—Br5viii | 98.56 (2) |
Br1—Sb1—Br4ii | 87.8 (3) | Br6—Sb2—Br5 | 81.44 (2) |
Br1—Sb1—Br4A | 94.4 (4) | Br6vi—Sb2—Br5vii | 98.56 (2) |
Br3—Sb1—Br2 | 176.05 (12) | Br6—Sb2—Br5vi | 81.44 (2) |
Br3—Sb1—Br4A | 85.5 (4) | Br6vi—Sb2—Br5vi | 98.56 (2) |
Br4—Sb1—Br2 | 88.6 (3) | Br6vi—Sb2—Br6 | 180.0 |
Br4ii—Sb1—Br2 | 95.0 (3) | Sb2—Br5—Sb2vi | 17.11 (4) |
Br4—Sb1—Br3 | 89.6 (3) | Sb2vi—Br6—Sb2 | 0.0 |
Br4ii—Sb1—Br3 | 87.0 (3) | Br7ix—Br6—Sb2 | 180.0 |
Br4—Sb1—Br4ii | 175.6 (4) | Br7ix—Br6—Sb2vi | 180.0 |
Br4—Sb1—Br4A | 169.5 (5) | Br6vi—Br7—Br6x | 180.0 |
| | | |
N1—C1—C2—C3 | 0.4 (9) | C1—C2—C3—C4 | −176.9 (7) |
N1—C5—C6—C7i | 88.2 (6) | C5—N1—C1—C2 | 170.6 (6) |
N1—C5—C6—C7 | −88.2 (6) | C5—C6—C7—C8 | 176.1 (6) |
C1i—N1—C1—C2 | −3.4 (11) | C6—C7—C8—C9 | −0.2 (10) |
C1i—N1—C5—C6 | 87.1 (5) | C7i—C6—C7—C8 | −0.2 (11) |
C1—N1—C5—C6 | −87.1 (5) | C7—C8—C9—C8i | 0.7 (12) |
C1—C2—C3—C2i | 2.6 (12) | C7—C8—C9—C10 | 178.1 (7) |
Symmetry codes: (i) x, y, −z+1; (ii) −y+1/2, x−1/2, −z+1/2; (iii) y+1/2, −x+1/2, −z+1/2; (iv) x, y, −z; (v) −x+1, −y, −z+1; (vi) −x+1, −y+1, −z; (vii) y, −x+1, −z; (viii) −y+1, x, z; (ix) x, y, z−1; (x) x, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Br5x | 0.95 | 3.05 | 3.924 (4) | 153 |
C2—H2···N3xi | 0.95 | 2.49 | 3.397 (7) | 160 |
C5—H5A···Br5 | 0.99 | 2.93 | 3.8568 (19) | 157 |
C5—H5A···Br6xii | 0.99 | 3.27 | 3.910 (5) | 124 |
C5—H5B···Br5 | 0.99 | 2.93 | 3.8568 (19) | 157 |
C5—H5B···Br6 | 0.99 | 3.27 | 3.910 (5) | 124 |
C7—H7···Br5 | 0.95 | 3.11 | 3.960 (4) | 149 |
C8—H8···N2xiii | 0.95 | 2.46 | 3.371 (6) | 161 |
Symmetry codes: (x) x, y, z+1; (xi) y+1/2, −x+1/2, z+1/2; (xii) −x+1, −y+1, z; (xiii) −y+1/2, x−1/2, z−1/2. |