metal-organic compounds
The structure of {3-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-ylidene}{1-[2-(4-methoxyphenyl)ethyl]-4-piperidin-1-io}ammonium tetrachlorocobaltate(II), (C28H33FN4O)[CoCl4], is isomorphous with its CuCl42− analogue. It contains diprotonated cations of astemizole hydrogen-bonded to three Cl atoms in two different CoCl42− anions, with ClN distances in the range 3.109 (5)–3.212 (5) Å. One of the Cl atoms in the CoCl42− anion is disordered and the geometry around cobalt is distorted tetrahedral. The phenylethyl C atoms of the (4-methoxyphenyl)ethyl group attached to the piperidine ring are disordered, indicating the presence of two conformers in the crystal.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007743/lh6193sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007743/lh6193Isup2.hkl |
CCDC reference: 239049
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
{3-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-ylidene}{1-[2-(4-
methoxyphenyl)ethyl]-4-piperidin-1-io}ammonium tetrachlorocobaltate(II) top
Crystal data top
(C28H33FN4O)[CoCl4] | F(000) = 1364 |
Mr = 661.31 | Dx = 1.465 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9625 reflections |
a = 9.327 (3) Å | θ = 2.5–25.0° |
b = 15.836 (6) Å | µ = 0.96 mm−1 |
c = 20.691 (9) Å | T = 170 K |
β = 101.186 (14)° | Prism, blue |
V = 2998 (2) Å3 | 0.10 × 0.08 × 0.06 mm |
Z = 4 |
Data collection top
Nonius KappaCCD diffractometer | 5205 independent reflections |
Radiation source: fine-focus sealed tube | 2899 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
ω and φ scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −11→11 |
Tmin = 0.91, Tmax = 0.94 | k = −17→18 |
9625 measured reflections | l = −24→24 |
Refinement top
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.062P)2 + 2.13P] where P = (Fo2 + 2Fc2)/3 |
5205 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.44 e Å−3 |
4 restraints | Δρmin = −0.55 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Co1 | 0.79619 (8) | 0.01356 (4) | 0.23763 (3) | 0.0316 (2) | |
Cl1 | 0.936 (3) | −0.1012 (10) | 0.2373 (3) | 0.055 (4) | 0.65 (6) |
Cl1' | 0.874 (4) | −0.1199 (14) | 0.2414 (10) | 0.054 (4) | 0.35 (6) |
Cl2 | 0.9301 (2) | 0.13013 (10) | 0.22853 (8) | 0.0655 (5) | |
Cl3 | 0.61643 (15) | 0.01524 (9) | 0.14424 (6) | 0.0462 (4) | |
Cl4 | 0.71713 (17) | 0.02805 (13) | 0.33399 (7) | 0.0652 (5) | |
F1 | 0.5850 (5) | 0.4120 (3) | −0.0490 (2) | 0.1018 (15) | |
O1 | 0.6535 (4) | 0.1665 (3) | 0.73968 (16) | 0.0538 (11) | |
N1 | 0.2122 (5) | 0.1057 (3) | 0.0308 (2) | 0.0362 (11) | |
N2 | 0.0640 (5) | 0.1242 (3) | 0.0998 (2) | 0.0362 (11) | |
H2 | 0.0323 | 0.1317 | 0.1368 | 0.043* | |
N3 | 0.3185 (5) | 0.1169 (3) | 0.1442 (2) | 0.0376 (11) | |
H3 | 0.4050 | 0.1058 | 0.1352 | 0.045* | |
N4 | 0.4391 (6) | 0.1258 (3) | 0.35295 (18) | 0.0452 (13) | |
H4 | 0.5190 | 0.0917 | 0.3502 | 0.054* | |
C1 | 0.2036 (7) | 0.1153 (3) | 0.0950 (3) | 0.0346 (13) | |
C2 | −0.0241 (6) | 0.1196 (3) | 0.0371 (2) | 0.0336 (13) | |
C3 | −0.1726 (7) | 0.1222 (3) | 0.0171 (3) | 0.0437 (15) | |
H3A | −0.2357 | 0.1306 | 0.0475 | 0.052* | |
C4 | −0.2267 (7) | 0.1117 (4) | −0.0501 (3) | 0.0475 (16) | |
H4A | −0.3293 | 0.1124 | −0.0662 | 0.057* | |
C5 | −0.1320 (7) | 0.1003 (3) | −0.0943 (3) | 0.0419 (15) | |
H5 | −0.1716 | 0.0948 | −0.1400 | 0.050* | |
C6 | 0.0173 (7) | 0.0968 (3) | −0.0731 (3) | 0.0378 (14) | |
H6 | 0.0810 | 0.0876 | −0.1031 | 0.045* | |
C7 | 0.0705 (6) | 0.1070 (3) | −0.0066 (2) | 0.0339 (13) | |
C8 | 0.3475 (6) | 0.0993 (4) | 0.0043 (3) | 0.0425 (15) | |
H8A | 0.3274 | 0.0659 | −0.0369 | 0.051* | |
H8B | 0.4221 | 0.0687 | 0.0363 | 0.051* | |
C9 | 0.4075 (6) | 0.1838 (4) | −0.0096 (3) | 0.0416 (15) | |
C10 | 0.4951 (7) | 0.2303 (4) | 0.0396 (3) | 0.0532 (17) | |
H10 | 0.5154 | 0.2085 | 0.0832 | 0.064* | |
C11 | 0.5539 (7) | 0.3077 (5) | 0.0270 (4) | 0.0654 (19) | |
H11 | 0.6130 | 0.3393 | 0.0611 | 0.079* | |
C12 | 0.5234 (8) | 0.3368 (5) | −0.0367 (4) | 0.066 (2) | |
C13 | 0.4395 (7) | 0.2944 (5) | −0.0870 (4) | 0.065 (2) | |
H13 | 0.4206 | 0.3166 | −0.1305 | 0.078* | |
C14 | 0.3828 (7) | 0.2182 (4) | −0.0729 (3) | 0.0505 (16) | |
H14 | 0.3241 | 0.1876 | −0.1077 | 0.061* | |
C15 | 0.3104 (7) | 0.1360 (3) | 0.2124 (2) | 0.0385 (14) | |
H15 | 0.2224 | 0.1719 | 0.2129 | 0.046* | |
C16 | 0.2993 (7) | 0.0561 (3) | 0.2526 (2) | 0.0425 (15) | |
H16A | 0.2071 | 0.0262 | 0.2345 | 0.051* | |
H16B | 0.3817 | 0.0179 | 0.2495 | 0.051* | |
C17 | 0.3031 (7) | 0.0790 (4) | 0.3243 (3) | 0.0478 (16) | |
H17A | 0.2171 | 0.1143 | 0.3274 | 0.057* | |
H17B | 0.2974 | 0.0268 | 0.3500 | 0.057* | |
C18 | 0.4498 (8) | 0.2058 (3) | 0.3146 (3) | 0.0552 (18) | |
H18A | 0.3671 | 0.2435 | 0.3182 | 0.066* | |
H18B | 0.5418 | 0.2356 | 0.3333 | 0.066* | |
C19 | 0.4468 (7) | 0.1855 (3) | 0.2432 (3) | 0.0473 (16) | |
H19A | 0.5346 | 0.1521 | 0.2396 | 0.057* | |
H19B | 0.4501 | 0.2387 | 0.2184 | 0.057* | |
C20 | 0.425 (3) | 0.1320 (15) | 0.4246 (5) | 0.040 (4) | 0.508 (4) |
H20A | 0.3472 | 0.1724 | 0.4294 | 0.048* | 0.508 (4) |
H20B | 0.4007 | 0.0762 | 0.4409 | 0.048* | 0.508 (4) |
C21 | 0.5706 (12) | 0.1621 (7) | 0.4637 (5) | 0.038 (2) | 0.508 (4) |
H21A | 0.5854 | 0.2216 | 0.4517 | 0.046* | 0.508 (4) |
H21B | 0.6496 | 0.1282 | 0.4508 | 0.046* | 0.508 (4) |
C22 | 0.5844 (9) | 0.1566 (5) | 0.5378 (3) | 0.035 (2) | 0.508 (4) |
C23 | 0.4698 (8) | 0.1752 (5) | 0.5695 (3) | 0.0317 (19) | 0.508 (4) |
H23 | 0.3765 | 0.1896 | 0.5444 | 0.038* | 0.508 (4) |
C24 | 0.4917 (11) | 0.1727 (6) | 0.6378 (4) | 0.040 (3) | 0.508 (4) |
H24 | 0.4134 | 0.1854 | 0.6595 | 0.049* | 0.508 (4) |
C25 | 0.6282 (14) | 0.1517 (8) | 0.6745 (3) | 0.0271 (18) | 0.508 (4) |
C26 | 0.7428 (10) | 0.1331 (9) | 0.6428 (5) | 0.031 (3) | 0.508 (4) |
H26 | 0.8361 | 0.1187 | 0.6678 | 0.037* | 0.508 (4) |
C27 | 0.7209 (8) | 0.1356 (7) | 0.5744 (5) | 0.0456 (19) | 0.508 (4) |
H27 | 0.7993 | 0.1229 | 0.5527 | 0.055* | 0.508 (4) |
C20' | 0.478 (3) | 0.1546 (16) | 0.4236 (5) | 0.040 (4) | 0.492 (4) |
H20C | 0.3964 | 0.1867 | 0.4356 | 0.048* | 0.492 (4) |
H20D | 0.5654 | 0.1917 | 0.4298 | 0.048* | 0.492 (4) |
C21' | 0.5100 (13) | 0.0778 (7) | 0.4659 (5) | 0.038 (2) | 0.492 (4) |
H21C | 0.5926 | 0.0462 | 0.4539 | 0.046* | 0.492 (4) |
H21D | 0.4233 | 0.0404 | 0.4588 | 0.046* | 0.492 (4) |
C22' | 0.5497 (9) | 0.1054 (5) | 0.5406 (3) | 0.035 (2) | 0.492 (4) |
C23' | 0.4369 (7) | 0.1080 (5) | 0.5758 (3) | 0.0317 (19) | 0.492 (4) |
H23' | 0.3410 | 0.0915 | 0.5552 | 0.038* | 0.492 (4) |
C24' | 0.4646 (12) | 0.1347 (6) | 0.6410 (3) | 0.040 (3) | 0.492 (4) |
H24' | 0.3875 | 0.1365 | 0.6650 | 0.049* | 0.492 (4) |
C25' | 0.6050 (14) | 0.1588 (8) | 0.6711 (3) | 0.0271 (18) | 0.492 (4) |
C26' | 0.7177 (10) | 0.1562 (9) | 0.6360 (5) | 0.031 (3) | 0.492 (4) |
H26' | 0.8137 | 0.1727 | 0.6566 | 0.037* | 0.492 (4) |
C27' | 0.6901 (8) | 0.1295 (7) | 0.5707 (5) | 0.0456 (19) | 0.492 (4) |
H27' | 0.7671 | 0.1277 | 0.5467 | 0.055* | 0.492 (4) |
C28 | 0.5393 (7) | 0.1650 (4) | 0.7760 (3) | 0.0501 (16) | |
H28A | 0.5801 | 0.1736 | 0.8228 | 0.075* | |
H28B | 0.4895 | 0.1102 | 0.7699 | 0.075* | |
H28C | 0.4691 | 0.2101 | 0.7603 | 0.075* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0312 (5) | 0.0337 (4) | 0.0303 (4) | 0.0020 (3) | 0.0071 (3) | −0.0014 (3) |
Cl1 | 0.086 (10) | 0.041 (4) | 0.0395 (18) | 0.032 (5) | 0.014 (3) | 0.0037 (16) |
Cl1' | 0.054 (9) | 0.049 (5) | 0.056 (4) | 0.012 (6) | 0.003 (5) | −0.001 (3) |
Cl2 | 0.0880 (14) | 0.0670 (11) | 0.0481 (10) | −0.0386 (10) | 0.0297 (9) | −0.0149 (8) |
Cl3 | 0.0395 (9) | 0.0659 (9) | 0.0312 (8) | 0.0039 (7) | 0.0022 (6) | 0.0031 (7) |
Cl4 | 0.0413 (10) | 0.1254 (15) | 0.0326 (9) | 0.0078 (10) | 0.0163 (8) | 0.0039 (9) |
F1 | 0.078 (3) | 0.113 (4) | 0.121 (4) | −0.024 (3) | 0.036 (3) | 0.044 (3) |
O1 | 0.049 (3) | 0.076 (3) | 0.035 (3) | −0.005 (2) | 0.003 (2) | −0.015 (2) |
N1 | 0.037 (3) | 0.045 (3) | 0.027 (3) | 0.011 (2) | 0.007 (2) | 0.006 (2) |
N2 | 0.041 (3) | 0.042 (3) | 0.027 (3) | 0.008 (2) | 0.008 (2) | 0.002 (2) |
N3 | 0.040 (3) | 0.047 (3) | 0.026 (3) | 0.002 (2) | 0.006 (2) | 0.003 (2) |
N4 | 0.068 (4) | 0.037 (3) | 0.025 (3) | 0.018 (2) | −0.006 (2) | −0.005 (2) |
C1 | 0.041 (4) | 0.034 (3) | 0.029 (3) | 0.006 (3) | 0.007 (3) | 0.009 (2) |
C2 | 0.035 (4) | 0.035 (3) | 0.030 (3) | 0.013 (3) | 0.005 (3) | 0.004 (2) |
C3 | 0.043 (4) | 0.054 (4) | 0.038 (4) | 0.016 (3) | 0.016 (3) | 0.010 (3) |
C4 | 0.041 (4) | 0.054 (4) | 0.044 (4) | 0.008 (3) | 0.000 (3) | 0.008 (3) |
C5 | 0.055 (5) | 0.043 (4) | 0.027 (3) | 0.008 (3) | 0.007 (3) | 0.004 (2) |
C6 | 0.048 (4) | 0.039 (3) | 0.028 (3) | 0.008 (3) | 0.011 (3) | 0.003 (2) |
C7 | 0.040 (4) | 0.032 (3) | 0.029 (3) | 0.008 (2) | 0.004 (3) | 0.000 (2) |
C8 | 0.039 (4) | 0.062 (4) | 0.027 (3) | 0.018 (3) | 0.006 (3) | 0.010 (3) |
C9 | 0.023 (3) | 0.068 (4) | 0.037 (4) | 0.015 (3) | 0.014 (3) | 0.008 (3) |
C10 | 0.031 (4) | 0.085 (5) | 0.047 (4) | 0.005 (3) | 0.015 (3) | 0.022 (4) |
C11 | 0.040 (4) | 0.096 (6) | 0.065 (5) | −0.009 (4) | 0.021 (4) | 0.008 (4) |
C12 | 0.041 (5) | 0.085 (5) | 0.081 (6) | 0.002 (4) | 0.032 (4) | 0.030 (5) |
C13 | 0.050 (5) | 0.091 (6) | 0.056 (5) | 0.017 (4) | 0.017 (4) | 0.027 (4) |
C14 | 0.039 (4) | 0.072 (5) | 0.042 (4) | 0.020 (3) | 0.013 (3) | 0.011 (3) |
C15 | 0.057 (4) | 0.028 (3) | 0.028 (3) | 0.001 (3) | 0.001 (3) | −0.001 (2) |
C16 | 0.068 (5) | 0.027 (3) | 0.033 (3) | 0.001 (3) | 0.012 (3) | −0.004 (2) |
C17 | 0.071 (5) | 0.044 (4) | 0.030 (3) | 0.013 (3) | 0.014 (3) | 0.006 (3) |
C18 | 0.083 (5) | 0.024 (3) | 0.047 (4) | 0.008 (3) | −0.015 (3) | −0.007 (3) |
C19 | 0.068 (5) | 0.031 (3) | 0.039 (4) | 0.000 (3) | −0.001 (3) | 0.004 (3) |
C20 | 0.043 (16) | 0.032 (12) | 0.036 (4) | 0.003 (7) | −0.015 (5) | −0.020 (4) |
C21 | 0.046 (6) | 0.044 (5) | 0.029 (5) | 0.001 (4) | 0.019 (4) | −0.004 (4) |
C22 | 0.048 (6) | 0.028 (6) | 0.032 (4) | 0.000 (5) | 0.013 (4) | 0.012 (5) |
C23 | 0.019 (4) | 0.044 (5) | 0.031 (4) | −0.004 (4) | 0.003 (4) | 0.001 (4) |
C24 | 0.020 (6) | 0.070 (11) | 0.036 (4) | −0.016 (6) | 0.018 (4) | −0.002 (5) |
C25 | 0.027 (5) | 0.023 (3) | 0.031 (3) | −0.001 (3) | 0.005 (3) | 0.007 (2) |
C26 | 0.022 (5) | 0.010 (8) | 0.060 (5) | 0.007 (5) | 0.009 (4) | −0.002 (4) |
C27 | 0.045 (5) | 0.048 (4) | 0.051 (4) | −0.006 (4) | 0.027 (4) | 0.002 (3) |
C20' | 0.043 (16) | 0.032 (12) | 0.036 (4) | 0.003 (7) | −0.015 (5) | −0.020 (4) |
C21' | 0.046 (6) | 0.044 (5) | 0.029 (5) | 0.001 (4) | 0.019 (4) | −0.004 (4) |
C22' | 0.048 (6) | 0.028 (6) | 0.032 (4) | 0.000 (5) | 0.013 (4) | 0.012 (5) |
C23' | 0.019 (4) | 0.044 (5) | 0.031 (4) | −0.004 (4) | 0.003 (4) | 0.001 (4) |
C24' | 0.020 (6) | 0.070 (11) | 0.036 (4) | −0.016 (6) | 0.018 (4) | −0.002 (5) |
C25' | 0.027 (5) | 0.023 (3) | 0.031 (3) | −0.001 (3) | 0.005 (3) | 0.007 (2) |
C26' | 0.022 (5) | 0.010 (8) | 0.060 (5) | 0.007 (5) | 0.009 (4) | −0.002 (4) |
C27' | 0.045 (5) | 0.048 (4) | 0.051 (4) | −0.006 (4) | 0.027 (4) | 0.002 (3) |
C28 | 0.066 (5) | 0.060 (4) | 0.027 (3) | 0.010 (3) | 0.015 (3) | 0.004 (3) |
Geometric parameters (Å, º) top
Co1—Cl1' | 2.232 (14) | C15—C16 | 1.528 (7) |
Co1—Cl1 | 2.240 (8) | C15—H15 | 1.0000 |
Co1—Cl2 | 2.257 (2) | C16—C17 | 1.521 (7) |
Co1—Cl4 | 2.268 (2) | C16—H16A | 0.9900 |
Co1—Cl3 | 2.300 (2) | C16—H16B | 0.9900 |
F1—C12 | 1.367 (8) | C17—H17A | 0.9900 |
O1—C25 | 1.344 (6) | C17—H17B | 0.9900 |
O1—C25' | 1.409 (6) | C18—C19 | 1.506 (8) |
O1—C28 | 1.418 (7) | C18—H18A | 0.9900 |
N1—C1 | 1.353 (6) | C18—H18B | 0.9900 |
N1—C7 | 1.397 (7) | C19—H19A | 0.9900 |
N1—C8 | 1.473 (7) | C19—H19B | 0.9900 |
N2—C1 | 1.333 (7) | C20—C21 | 1.51 (2) |
N2—C2 | 1.397 (6) | C20—H20A | 0.9900 |
N2—H2 | 0.8800 | C20—H20B | 0.9900 |
N3—C1 | 1.329 (6) | C21—C22 | 1.516 (11) |
N3—C15 | 1.459 (7) | C21—H21A | 0.9900 |
N3—H3 | 0.8800 | C21—H21B | 0.9900 |
N4—C20' | 1.507 (8) | C22—C23 | 1.3900 |
N4—C17 | 1.489 (7) | C22—C27 | 1.3900 |
N4—C18 | 1.509 (7) | C23—C24 | 1.3900 |
N4—C20 | 1.515 (8) | C23—H23 | 0.9500 |
N4—H4 | 0.9300 | C24—C25 | 1.3900 |
C2—C3 | 1.367 (7) | C24—H24 | 0.9500 |
C2—C7 | 1.395 (7) | C25—C26 | 1.3900 |
C3—C4 | 1.395 (8) | C26—C27 | 1.3900 |
C3—H3A | 0.9500 | C26—H26 | 0.9500 |
C4—C5 | 1.401 (8) | C27—H27 | 0.9500 |
C4—H4A | 0.9500 | C20'—C21' | 1.49 (3) |
C5—C6 | 1.377 (8) | C20'—H20C | 0.9900 |
C5—H5 | 0.9500 | C20'—H20D | 0.9900 |
C6—C7 | 1.379 (7) | C21'—C22' | 1.581 (12) |
C6—H6 | 0.9500 | C21'—H21C | 0.9900 |
C8—C9 | 1.499 (8) | C21'—H21D | 0.9900 |
C8—H8A | 0.9900 | C22'—C23' | 1.3900 |
C8—H8B | 0.9900 | C22'—C27' | 1.3900 |
C9—C10 | 1.387 (8) | C23'—C24' | 1.3900 |
C9—C14 | 1.396 (8) | C23'—H23' | 0.9500 |
C10—C11 | 1.389 (9) | C24'—C25' | 1.3900 |
C10—H10 | 0.9500 | C24'—H24' | 0.9500 |
C11—C12 | 1.373 (9) | C25'—C26' | 1.3900 |
C11—H11 | 0.9500 | C26'—C27' | 1.3900 |
C12—C13 | 1.353 (9) | C26'—H26' | 0.9500 |
C13—C14 | 1.371 (9) | C27'—H27' | 0.9500 |
C13—H13 | 0.9500 | C28—H28A | 0.9800 |
C14—H14 | 0.9500 | C28—H28B | 0.9800 |
C15—C19 | 1.524 (7) | C28—H28C | 0.9800 |
Cl1'—Co1—Cl2 | 126.6 (11) | H16A—C16—H16B | 108.2 |
Cl1—Co1—Cl2 | 109.3 (9) | N4—C17—C16 | 111.3 (5) |
Cl1'—Co1—Cl4 | 102.9 (9) | N4—C17—H17A | 109.4 |
Cl1—Co1—Cl4 | 112.0 (3) | C16—C17—H17A | 109.4 |
Cl2—Co1—Cl4 | 105.68 (7) | N4—C17—H17B | 109.4 |
Cl1'—Co1—Cl3 | 102.7 (4) | C16—C17—H17B | 109.4 |
Cl1—Co1—Cl3 | 109.7 (5) | H17A—C17—H17B | 108.0 |
Cl2—Co1—Cl3 | 104.21 (7) | C19—C18—N4 | 110.2 (4) |
Cl4—Co1—Cl3 | 115.42 (7) | C19—C18—H18A | 109.6 |
C25—O1—C28 | 121.6 (7) | N4—C18—H18A | 109.6 |
C25'—O1—C28 | 113.8 (7) | C19—C18—H18B | 109.6 |
C1—N1—C7 | 108.2 (4) | N4—C18—H18B | 109.6 |
C1—N1—C8 | 126.2 (5) | H18A—C18—H18B | 108.1 |
C7—N1—C8 | 125.5 (4) | C18—C19—C15 | 112.0 (5) |
C1—N2—C2 | 109.3 (4) | C18—C19—H19A | 109.2 |
C1—N2—H2 | 125.3 | C15—C19—H19A | 109.2 |
C2—N2—H2 | 125.3 | C18—C19—H19B | 109.2 |
C1—N3—C15 | 124.1 (5) | C15—C19—H19B | 109.2 |
C1—N3—H3 | 117.9 | H19A—C19—H19B | 107.9 |
C15—N3—H3 | 117.9 | C21—C20—N4 | 107.9 (11) |
C20'—N4—C17 | 124.4 (8) | C21—C20—H20A | 110.1 |
C20'—N4—C18 | 103.1 (9) | N4—C20—H20A | 110.1 |
C17—N4—C18 | 110.3 (4) | C21—C20—H20B | 110.1 |
C17—N4—C20 | 101.3 (7) | N4—C20—H20B | 110.1 |
C18—N4—C20 | 119.1 (10) | H20A—C20—H20B | 108.4 |
C20'—N4—H4 | 100.8 | C20—C21—C22 | 114.5 (8) |
C17—N4—H4 | 108.6 | C20—C21—H21A | 108.6 |
C18—N4—H4 | 108.6 | C22—C21—H21A | 108.6 |
C20—N4—H4 | 108.6 | C20—C21—H21B | 108.6 |
N3—C1—N2 | 126.5 (5) | C22—C21—H21B | 108.6 |
N3—C1—N1 | 124.2 (5) | H21A—C21—H21B | 107.6 |
N2—C1—N1 | 109.3 (5) | C23—C22—C27 | 120.0 |
C3—C2—C7 | 122.7 (5) | C23—C22—C21 | 122.9 (7) |
C3—C2—N2 | 131.1 (5) | C27—C22—C21 | 117.1 (7) |
C7—C2—N2 | 106.2 (5) | C24—C23—C22 | 120.0 |
C2—C3—C4 | 116.5 (5) | C24—C23—H23 | 120.0 |
C2—C3—H3A | 121.7 | C22—C23—H23 | 120.0 |
C4—C3—H3A | 121.7 | C23—C24—C25 | 120.0 |
C3—C4—C5 | 121.0 (6) | C23—C24—H24 | 120.0 |
C3—C4—H4A | 119.5 | C25—C24—H24 | 120.0 |
C5—C4—H4A | 119.5 | O1—C25—C26 | 120.6 (9) |
C6—C5—C4 | 121.6 (5) | O1—C25—C24 | 118.0 (9) |
C6—C5—H5 | 119.2 | C26—C25—C24 | 120.0 |
C4—C5—H5 | 119.2 | C25—C26—C27 | 120.0 |
C5—C6—C7 | 117.3 (5) | C25—C26—H26 | 120.0 |
C5—C6—H6 | 121.3 | C27—C26—H26 | 120.0 |
C7—C6—H6 | 121.3 | C26—C27—C22 | 120.0 |
C6—C7—C2 | 120.9 (5) | C26—C27—H27 | 120.0 |
C6—C7—N1 | 132.1 (5) | C22—C27—H27 | 120.0 |
C2—C7—N1 | 107.0 (4) | N4—C20'—C21' | 107.7 (14) |
N1—C8—C9 | 112.9 (4) | N4—C20'—H20C | 110.2 |
N1—C8—H8A | 109.0 | C21'—C20'—H20C | 110.2 |
C9—C8—H8A | 109.0 | N4—C20'—H20D | 110.2 |
N1—C8—H8B | 109.0 | C21'—C20'—H20D | 110.2 |
C9—C8—H8B | 109.0 | H20C—C20'—H20D | 108.5 |
H8A—C8—H8B | 107.8 | C20'—C21'—C22' | 109.3 (8) |
C10—C9—C14 | 116.6 (6) | C20'—C21'—H21C | 109.8 |
C10—C9—C8 | 121.4 (5) | C22'—C21'—H21C | 109.8 |
C14—C9—C8 | 122.0 (6) | C20'—C21'—H21D | 109.8 |
C9—C10—C11 | 121.9 (6) | C22'—C21'—H21D | 109.8 |
C9—C10—H10 | 119.1 | H21C—C21'—H21D | 108.3 |
C11—C10—H10 | 119.1 | C23'—C22'—C27' | 120.0 |
C12—C11—C10 | 117.5 (7) | C23'—C22'—C21' | 117.5 (7) |
C12—C11—H11 | 121.3 | C27'—C22'—C21' | 122.4 (7) |
C10—C11—H11 | 121.3 | C24'—C23'—C22' | 120.0 |
C13—C12—F1 | 119.3 (7) | C24'—C23'—H23' | 120.0 |
C13—C12—C11 | 123.6 (7) | C22'—C23'—H23' | 120.0 |
F1—C12—C11 | 117.0 (7) | C25'—C24'—C23' | 120.0 |
C12—C13—C14 | 117.5 (6) | C25'—C24'—H24' | 120.0 |
C12—C13—H13 | 121.3 | C23'—C24'—H24' | 120.0 |
C14—C13—H13 | 121.3 | C26'—C25'—C24' | 120.0 |
C13—C14—C9 | 123.0 (6) | C26'—C25'—O1 | 113.7 (9) |
C13—C14—H14 | 118.5 | C24'—C25'—O1 | 124.5 (8) |
C9—C14—H14 | 118.5 | C25'—C26'—C27' | 120.0 |
N3—C15—C19 | 108.4 (5) | C25'—C26'—H26' | 120.0 |
N3—C15—C16 | 112.1 (4) | C27'—C26'—H26' | 120.0 |
C19—C15—C16 | 109.7 (4) | C26'—C27'—C22' | 120.0 |
N3—C15—H15 | 108.9 | C26'—C27'—H27' | 120.0 |
C19—C15—H15 | 108.9 | C22'—C27'—H27' | 120.0 |
C16—C15—H15 | 108.9 | O1—C28—H28A | 109.5 |
C17—C16—C15 | 110.0 (4) | O1—C28—H28B | 109.5 |
C17—C16—H16A | 109.7 | H28A—C28—H28B | 109.5 |
C15—C16—H16A | 109.7 | O1—C28—H28C | 109.5 |
C17—C16—H16B | 109.7 | H28A—C28—H28C | 109.5 |
C15—C16—H16B | 109.7 | H28B—C28—H28C | 109.5 |
Cl2—Co1—Cl1—Cl1' | 178 (2) | C18—N4—C17—C16 | 59.2 (6) |
Cl4—Co1—Cl1—Cl1' | 61 (2) | C20—N4—C17—C16 | −173.8 (12) |
Cl3—Co1—Cl1—Cl1' | −68.5 (19) | C15—C16—C17—N4 | −58.2 (6) |
Cl2—Co1—Cl1'—Cl1 | −3 (2) | C20'—N4—C18—C19 | 167.4 (11) |
Cl4—Co1—Cl1'—Cl1 | −124 (2) | C17—N4—C18—C19 | −57.8 (6) |
Cl3—Co1—Cl1'—Cl1 | 116.1 (18) | C20—N4—C18—C19 | −174.2 (11) |
C15—N3—C1—N2 | −5.4 (8) | N4—C18—C19—C15 | 56.8 (7) |
C15—N3—C1—N1 | 173.4 (4) | N3—C15—C19—C18 | −178.3 (4) |
C2—N2—C1—N3 | 179.4 (5) | C16—C15—C19—C18 | −55.6 (6) |
C2—N2—C1—N1 | 0.6 (6) | C20'—N4—C20—C21 | −20 (4) |
C7—N1—C1—N3 | 180.0 (5) | C17—N4—C20—C21 | 168.4 (14) |
C8—N1—C1—N3 | −2.9 (8) | C18—N4—C20—C21 | −71 (2) |
C7—N1—C1—N2 | −1.1 (5) | N4—C20—C21—C22 | −169.4 (11) |
C8—N1—C1—N2 | 176.0 (4) | C20—C21—C22—C23 | −38.8 (16) |
C1—N2—C2—C3 | 177.4 (5) | C20—C21—C22—C27 | 144.2 (13) |
C1—N2—C2—C7 | 0.2 (5) | C27—C22—C23—C24 | 0.0 |
C7—C2—C3—C4 | −0.2 (8) | C21—C22—C23—C24 | −177.0 (8) |
N2—C2—C3—C4 | −177.0 (5) | C22—C23—C24—C25 | 0.0 |
C2—C3—C4—C5 | −0.7 (8) | C25'—O1—C25—C26 | 157 (6) |
C3—C4—C5—C6 | 1.6 (8) | C28—O1—C25—C26 | −164.2 (5) |
C4—C5—C6—C7 | −1.5 (8) | C25'—O1—C25—C24 | −9 (5) |
C5—C6—C7—C2 | 0.6 (7) | C28—O1—C25—C24 | 29.2 (10) |
C5—C6—C7—N1 | 178.8 (5) | C23—C24—C25—O1 | 166.7 (9) |
C3—C2—C7—C6 | 0.3 (8) | C23—C24—C25—C26 | 0.0 |
N2—C2—C7—C6 | 177.7 (4) | O1—C25—C26—C27 | −166.3 (9) |
C3—C2—C7—N1 | −178.4 (5) | C24—C25—C26—C27 | 0.0 |
N2—C2—C7—N1 | −0.9 (5) | C25—C26—C27—C22 | 0.0 |
C1—N1—C7—C6 | −177.2 (5) | C23—C22—C27—C26 | 0.0 |
C8—N1—C7—C6 | 5.7 (8) | C21—C22—C27—C26 | 177.1 (7) |
C1—N1—C7—C2 | 1.3 (5) | C17—N4—C20'—C21' | 68 (2) |
C8—N1—C7—C2 | −175.9 (4) | C18—N4—C20'—C21' | −165.3 (12) |
C1—N1—C8—C9 | −86.4 (6) | C20—N4—C20'—C21' | 59 (5) |
C7—N1—C8—C9 | 90.2 (6) | N4—C20'—C21'—C22' | −179.2 (11) |
N1—C8—C9—C10 | 83.6 (6) | C20'—C21'—C22'—C23' | 93.2 (13) |
N1—C8—C9—C14 | −98.8 (6) | C20'—C21'—C22'—C27' | −84.5 (13) |
C14—C9—C10—C11 | 0.8 (9) | C27'—C22'—C23'—C24' | 0.0 |
C8—C9—C10—C11 | 178.6 (5) | C21'—C22'—C23'—C24' | −177.7 (8) |
C9—C10—C11—C12 | −0.6 (10) | C22'—C23'—C24'—C25' | 0.0 |
C10—C11—C12—C13 | 0.3 (11) | C23'—C24'—C25'—C26' | 0.0 |
C10—C11—C12—F1 | −178.3 (6) | C23'—C24'—C25'—O1 | −163.5 (11) |
F1—C12—C13—C14 | 178.4 (5) | C25—O1—C25'—C26' | −32 (5) |
C11—C12—C13—C14 | −0.1 (11) | C28—O1—C25'—C26' | −177.0 (5) |
C12—C13—C14—C9 | 0.3 (9) | C25—O1—C25'—C24' | 132 (6) |
C10—C9—C14—C13 | −0.6 (9) | C28—O1—C25'—C24' | −12.7 (11) |
C8—C9—C14—C13 | −178.4 (5) | C24'—C25'—C26'—C27' | 0.0 |
C1—N3—C15—C19 | −144.2 (5) | O1—C25'—C26'—C27' | 165.2 (9) |
C1—N3—C15—C16 | 94.5 (6) | C25'—C26'—C27'—C22' | 0.0 |
N3—C15—C16—C17 | 175.6 (5) | C23'—C22'—C27'—C26' | 0.0 |
C19—C15—C16—C17 | 55.2 (6) | C21'—C22'—C27'—C26' | 177.6 (8) |
C20'—N4—C17—C16 | −177.7 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cl2i | 0.88 | 2.28 | 3.154 (5) | 170 |
N3—H3···Cl3 | 0.88 | 2.42 | 3.212 (5) | 150 |
N4—H4···Cl4 | 0.93 | 2.19 | 3.109 (5) | 171 |
Symmetry code: (i) x−1, y, z. |