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Acta Cryst. (2007). E63, m1152    [ doi:10.1107/S1600536807012329 ]

Tetrakis(1,10-phenanthrolinium) hexachloridoeuropate(III) chloride

W. Clegg and R. W. Harrington

Abstract top

In the title compound, (C12H9N)4[EuCl6]Cl, the EuIII atom has slightly distorted octahedral coordination. The longest Eu—Cl bond (Table 1) is to a Cl atom that serves as acceptor of a hydrogen bond from one of the four crystallographically independent singly-protonated 1,10-phenanthrolinium cations. The other three cations all form hydrogen bonds to the uncoordinated chloride anion, which is surrounded approximately in a trigonal plane by the three donors (Table 2). There is extensive π-stacking of the planar cations, with interplanar distances in the range 3.3–3.7 Å.

Related literature top

Two other salts of [EuCl6]3- have been reported with organic cations. Both have protonated amines as the counterion, and one (the first of the cited references) also contains uncoordinated chloride and four cations [Petriček, 2005; Hallfeldt, 2003 (included as REFCODE UNEQAF in the Cambridge Structural Database, Version 5.27; Allen, 2002)].

Refinement top

N-bound H atoms were located in a difference map and refined with a restrained N—H distance of 0.87 (2) Å. Other H atoms were positioned geometrically and refined with a riding model (C—H = 0.93 Å). For all H atoms, Uiso(H) = 1.2Ueq(N,C). The most significant features of the final residual density map are located close to the Eu atom.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker 2001); data reduction: Bruker SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2003) and local programs.

Figures top
[Figure 1] Fig. 1. . The asymmetric unit with atom labels and 50% probability ellipsoids for non-H atoms. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted.
Tetrakis(1,10-phenanthrolinium) hexachloridooeuropate(III) chloride top
Crystal data top
(C12H9N2)4[EuCl6]ClF000 = 2248
Mr = 1124.96Dx = 1.685 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
a = 17.6308 (5) ÅCell parameters from 26437 reflections
b = 11.2069 (3) Åθ = 2.2–29.0º
c = 24.0726 (7) ŵ = 1.88 mm−1
β = 111.197 (2)ºT = 160 (2) K
V = 4434.6 (2) Å3Block, colourless
Z = 40.38 × 0.30 × 0.25 mm
Data collection top
Bruker SMART 1K CCD
diffractometer		7803 independent reflections
Radiation source: sealed tube6822 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
Detector resolution: 8.192 pixels mm-1θmax = 25.0º
T = 160(2) Kθmin = 1.8º
thin–slice ω scansh = −20→20
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		k = −13→13
Tmin = 0.530, Tmax = 0.650l = −28→28
31682 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053  w = 1/[σ2(Fo2) + (0.0056P)2 + 19.2232P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.001
S = 1.30Δρmax = 0.86 e Å−3
7803 reflectionsΔρmin = −1.82 e Å−3
589 parametersExtinction correction: none
162 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Crystal data top
(C12H9N2)4[EuCl6]ClV = 4434.6 (2) Å3
Mr = 1124.96Z = 4
Monoclinic, P21/cMo Kα
a = 17.6308 (5) ŵ = 1.88 mm−1
b = 11.2069 (3) ÅT = 160 (2) K
c = 24.0726 (7) Å0.38 × 0.30 × 0.25 mm
β = 111.197 (2)º
Data collection top
Bruker SMART 1K CCD
diffractometer		7803 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		6822 reflections with I > 2σ(I)
Tmin = 0.530, Tmax = 0.650Rint = 0.048
31682 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053  w = 1/[σ2(Fo2) + (0.0056P)2 + 19.2232P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092Δρmax = 0.86 e Å−3
S = 1.30Δρmin = −1.82 e Å−3
7803 reflectionsAbsolute structure: ?
589 parametersFlack parameter: ?
162 restraintsRogers parameter: ?
H atoms treated by a mixture of
independent and constrained refinement
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Eu0.715425 (16)0.51035 (2)0.405963 (12)0.01302 (8)
Cl10.61670 (9)0.60313 (13)0.30368 (6)0.0250 (3)
Cl20.74559 (9)0.73182 (12)0.45410 (7)0.0244 (3)
Cl30.67986 (9)0.28636 (12)0.36491 (6)0.0252 (3)
Cl40.59307 (8)0.49166 (12)0.44632 (6)0.0203 (3)
Cl50.84137 (9)0.52383 (14)0.36861 (7)0.0288 (3)
Cl60.81255 (8)0.41411 (12)0.51454 (6)0.0207 (3)
Cl70.79884 (8)−0.18435 (12)0.63937 (6)0.0189 (3)
N10.7993 (3)−0.3601 (4)0.7363 (2)0.0214 (11)
H10.813 (4)−0.324 (5)0.710 (2)0.026*
N20.9261 (3)−0.4517 (4)0.7076 (2)0.0222 (11)
N30.7145 (3)0.4527 (4)0.6003 (2)0.0165 (10)
H30.751 (3)0.414 (4)0.591 (2)0.020*
N40.7667 (3)0.2306 (4)0.6471 (2)0.0172 (10)
N50.5691 (3)−0.0867 (4)0.6198 (2)0.0192 (10)
N60.6617 (3)−0.0215 (4)0.5547 (2)0.0179 (10)
H60.676 (3)−0.078 (4)0.581 (2)0.022*
N70.9429 (3)0.0504 (4)0.6021 (2)0.0224 (11)
N80.9310 (3)−0.1915 (4)0.5828 (2)0.0166 (10)
H80.897 (3)−0.156 (5)0.596 (2)0.020*
C10.7423 (4)−0.3075 (5)0.7520 (3)0.0290 (14)
H1A0.7254−0.22850.73900.035*
C20.7079 (4)−0.3674 (6)0.7870 (3)0.0303 (14)
H20.6682−0.32960.79910.036*
C30.7318 (3)−0.4824 (6)0.8042 (3)0.0259 (13)
H3A0.7075−0.52470.82770.031*
C40.7911 (3)−0.5379 (5)0.7876 (2)0.0191 (12)
C50.8268 (3)−0.4715 (5)0.7540 (2)0.0154 (11)
C60.8938 (3)−0.5200 (5)0.7405 (2)0.0193 (11)
C70.9236 (3)−0.6337 (5)0.7627 (2)0.0191 (12)
C80.9936 (3)−0.6726 (5)0.7541 (3)0.0231 (13)
H8A1.0173−0.74720.76980.028*
C91.0281 (3)−0.6029 (5)0.7231 (3)0.0245 (13)
H91.0764−0.62760.71760.029*
C100.9913 (3)−0.4955 (5)0.6999 (3)0.0279 (13)
H101.0146−0.45000.67670.033*
C110.8193 (3)−0.6566 (5)0.8059 (2)0.0203 (12)
H110.7932−0.70400.82650.024*
C120.8832 (3)−0.7011 (5)0.7939 (2)0.0204 (12)
H120.9016−0.77960.80680.024*
C130.6944 (3)0.5615 (5)0.5780 (2)0.0199 (12)
H130.72020.59500.55320.024*
C140.6357 (3)0.6265 (5)0.5909 (3)0.0236 (13)
H140.62300.70570.57650.028*
C150.5964 (3)0.5757 (5)0.6244 (2)0.0195 (12)
H150.55440.61830.63180.023*
C160.6178 (3)0.4600 (5)0.6480 (2)0.0177 (11)
C170.6787 (3)0.3997 (5)0.6358 (2)0.0160 (11)
C180.7053 (3)0.2832 (5)0.6596 (2)0.0157 (11)
C190.6669 (3)0.2311 (5)0.6960 (2)0.0184 (12)
C200.6950 (4)0.1188 (5)0.7205 (2)0.0232 (13)
H200.67110.07970.74510.028*
C210.7570 (4)0.0667 (5)0.7085 (3)0.0241 (13)
H210.7774−0.00880.72520.029*
C220.7908 (3)0.1250 (5)0.6712 (3)0.0222 (13)
H220.83340.08620.66290.027*
C230.5787 (3)0.4028 (5)0.6839 (3)0.0230 (13)
H230.53600.44240.69190.028*
C240.6025 (3)0.2932 (5)0.7063 (3)0.0242 (13)
H240.57570.25620.72970.029*
C250.5260 (4)−0.1128 (5)0.6531 (3)0.0241 (13)
H250.5361−0.18670.67380.029*
C260.4662 (4)−0.0372 (6)0.6594 (3)0.0279 (14)
H260.4375−0.05900.68450.033*
C270.4500 (4)0.0676 (6)0.6291 (3)0.0253 (13)
H270.40920.11920.63270.030*
C280.4930 (3)0.0998 (5)0.5926 (2)0.0159 (11)
C290.5534 (3)0.0196 (5)0.5906 (2)0.0167 (11)
C300.6009 (3)0.0513 (5)0.5555 (2)0.0165 (11)
C310.5867 (3)0.1583 (5)0.5231 (2)0.0168 (11)
C320.6346 (3)0.1823 (5)0.4885 (3)0.0216 (12)
H320.62660.25400.46600.026*
C330.6924 (4)0.1025 (5)0.4871 (3)0.0259 (13)
H330.72280.11680.46230.031*
C340.7069 (3)0.0009 (5)0.5219 (2)0.0249 (12)
H340.7489−0.05280.52250.030*
C350.4813 (3)0.2099 (5)0.5607 (3)0.0217 (12)
H350.44140.26430.56320.026*
C360.5256 (3)0.2385 (5)0.5272 (3)0.0213 (12)
H360.51630.31210.50620.026*
C370.9497 (4)0.1675 (5)0.6094 (3)0.0259 (14)
H370.90910.20860.61930.031*
C381.0139 (4)0.2347 (5)0.6033 (3)0.0294 (14)
H381.01620.31860.60940.035*
C391.0725 (4)0.1785 (5)0.5888 (2)0.0229 (13)
H391.11700.22210.58570.027*
C401.0661 (3)0.0532 (5)0.5783 (2)0.0178 (11)
C411.0003 (3)−0.0065 (5)0.5862 (2)0.0181 (11)
C420.9926 (3)−0.1312 (5)0.5748 (2)0.0157 (11)
C431.0464 (3)−0.1926 (5)0.5551 (2)0.0159 (11)
C441.0333 (3)−0.3157 (5)0.5437 (3)0.0235 (13)
H441.0697−0.36000.53080.028*
C450.9689 (3)−0.3721 (5)0.5510 (3)0.0226 (13)
H450.9595−0.45470.54230.027*
C460.9177 (3)−0.3068 (5)0.5714 (2)0.0208 (12)
H460.8729−0.34460.57710.025*
C471.1219 (3)−0.0107 (5)0.5591 (2)0.0228 (12)
H471.16640.03010.55440.027*
C481.1123 (3)−0.1299 (5)0.5474 (2)0.0202 (12)
H481.1496−0.17130.53410.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu0.01412 (13)0.01092 (13)0.01640 (14)0.00049 (12)0.00837 (10)0.00054 (12)
Cl10.0229 (8)0.0307 (8)0.0211 (8)0.0023 (6)0.0076 (6)0.0054 (6)
Cl20.0256 (8)0.0185 (7)0.0313 (8)−0.0029 (6)0.0129 (7)−0.0067 (6)
Cl30.0386 (9)0.0185 (7)0.0253 (8)−0.0038 (6)0.0198 (7)−0.0039 (6)
Cl40.0175 (6)0.0197 (7)0.0256 (7)−0.0003 (6)0.0102 (6)0.0005 (6)
Cl50.0251 (8)0.0322 (8)0.0371 (9)−0.0019 (6)0.0207 (7)−0.0003 (7)
Cl60.0178 (7)0.0255 (7)0.0210 (7)0.0048 (6)0.0095 (6)0.0034 (6)
Cl70.0165 (7)0.0196 (7)0.0231 (7)0.0023 (5)0.0101 (6)0.0040 (6)
N10.021 (3)0.025 (3)0.022 (3)0.002 (2)0.013 (2)0.004 (2)
N20.023 (3)0.021 (2)0.027 (3)−0.003 (2)0.013 (2)0.004 (2)
N30.012 (2)0.021 (2)0.015 (2)−0.0033 (19)0.003 (2)−0.0027 (19)
N40.016 (2)0.022 (2)0.019 (3)−0.0009 (19)0.011 (2)0.0000 (19)
N50.022 (3)0.015 (2)0.020 (3)−0.0031 (19)0.007 (2)−0.0013 (19)
N60.022 (2)0.013 (2)0.019 (2)0.0051 (19)0.008 (2)0.0028 (19)
N70.027 (3)0.021 (2)0.025 (3)0.000 (2)0.016 (2)−0.003 (2)
N80.012 (2)0.023 (2)0.014 (2)0.0046 (19)0.004 (2)0.0005 (19)
C10.026 (3)0.022 (3)0.041 (4)0.001 (3)0.015 (3)−0.001 (3)
C20.025 (3)0.038 (4)0.033 (4)0.002 (3)0.016 (3)−0.010 (3)
C30.023 (3)0.038 (3)0.021 (3)−0.003 (3)0.014 (3)−0.005 (3)
C40.023 (3)0.021 (3)0.008 (3)−0.003 (2)−0.001 (2)−0.001 (2)
C50.014 (2)0.020 (2)0.006 (2)0.0038 (19)−0.0038 (18)0.0067 (19)
C60.020 (3)0.018 (3)0.017 (3)−0.005 (2)0.003 (2)−0.001 (2)
C70.016 (3)0.023 (3)0.013 (3)−0.001 (2)−0.002 (2)−0.002 (2)
C80.018 (3)0.023 (3)0.023 (3)0.001 (2)0.002 (2)−0.002 (2)
C90.018 (3)0.031 (3)0.027 (3)0.003 (2)0.012 (3)−0.003 (3)
C100.028 (3)0.023 (3)0.038 (4)0.000 (3)0.018 (3)0.001 (3)
C110.022 (3)0.022 (3)0.015 (3)−0.009 (2)0.005 (2)0.004 (2)
C120.026 (3)0.019 (3)0.012 (3)0.000 (2)0.002 (2)0.005 (2)
C130.015 (3)0.023 (3)0.014 (3)−0.004 (2)−0.004 (2)−0.001 (2)
C140.016 (3)0.023 (3)0.027 (3)0.002 (2)0.001 (3)0.000 (2)
C150.009 (3)0.022 (3)0.023 (3)0.001 (2)0.000 (2)−0.008 (2)
C160.011 (3)0.023 (3)0.015 (3)−0.005 (2)0.001 (2)−0.007 (2)
C170.015 (3)0.018 (3)0.015 (3)−0.004 (2)0.006 (2)0.000 (2)
C180.015 (3)0.017 (3)0.015 (3)−0.004 (2)0.005 (2)−0.005 (2)
C190.016 (3)0.023 (3)0.015 (3)−0.006 (2)0.005 (2)−0.005 (2)
C200.034 (4)0.022 (3)0.015 (3)−0.011 (2)0.011 (3)−0.002 (2)
C210.029 (3)0.021 (3)0.020 (3)−0.002 (2)0.007 (3)0.004 (2)
C220.019 (3)0.023 (3)0.026 (3)−0.001 (2)0.010 (3)−0.002 (2)
C230.017 (3)0.032 (3)0.025 (3)−0.003 (2)0.012 (3)−0.009 (3)
C240.020 (3)0.035 (3)0.021 (3)−0.008 (3)0.011 (3)−0.008 (3)
C250.027 (3)0.026 (3)0.019 (3)−0.005 (2)0.009 (3)0.000 (2)
C260.028 (3)0.039 (4)0.021 (3)0.000 (3)0.013 (3)0.003 (3)
C270.022 (3)0.034 (3)0.023 (3)0.003 (3)0.013 (3)−0.004 (3)
C280.013 (3)0.016 (3)0.017 (3)−0.001 (2)0.004 (2)−0.004 (2)
C290.016 (3)0.016 (3)0.014 (3)0.002 (2)0.001 (2)−0.002 (2)
C300.017 (3)0.018 (3)0.015 (3)0.004 (2)0.006 (2)0.003 (2)
C310.017 (3)0.015 (3)0.017 (3)−0.002 (2)0.005 (2)−0.001 (2)
C320.026 (3)0.020 (3)0.021 (3)−0.003 (2)0.011 (3)0.004 (2)
C330.026 (3)0.033 (3)0.023 (3)−0.002 (3)0.014 (3)0.003 (3)
C340.025 (3)0.027 (3)0.025 (3)0.006 (3)0.012 (2)0.000 (3)
C350.017 (3)0.021 (3)0.026 (3)0.005 (2)0.005 (3)−0.002 (2)
C360.021 (3)0.017 (3)0.023 (3)0.004 (2)0.004 (3)0.003 (2)
C370.034 (4)0.024 (3)0.022 (3)0.005 (3)0.014 (3)−0.002 (3)
C380.043 (4)0.024 (3)0.028 (4)−0.005 (3)0.020 (3)−0.004 (3)
C390.028 (3)0.024 (3)0.016 (3)−0.007 (2)0.007 (3)−0.001 (2)
C400.020 (3)0.022 (3)0.008 (3)−0.004 (2)0.002 (2)0.001 (2)
C410.019 (3)0.021 (3)0.014 (3)−0.001 (2)0.006 (2)−0.004 (2)
C420.013 (3)0.023 (3)0.010 (3)−0.002 (2)0.003 (2)−0.001 (2)
C430.011 (3)0.027 (3)0.008 (3)0.005 (2)0.001 (2)0.004 (2)
C440.020 (3)0.029 (3)0.022 (3)0.009 (2)0.008 (3)0.000 (3)
C450.022 (3)0.018 (3)0.027 (3)0.002 (2)0.008 (3)−0.003 (2)
C460.015 (3)0.024 (3)0.021 (3)−0.001 (2)0.005 (2)0.001 (2)
C470.019 (3)0.029 (3)0.021 (3)0.001 (3)0.007 (2)0.004 (3)
C480.015 (3)0.035 (3)0.014 (3)0.008 (2)0.009 (2)0.003 (2)
Geometric parameters (Å, °) top
Eu—Cl12.6596 (14)C16—C231.437 (8)
Eu—Cl22.7092 (14)C17—C181.434 (7)
Eu—Cl32.6876 (14)C18—C191.411 (7)
Eu—Cl42.6753 (13)C19—C201.403 (8)
Eu—Cl52.6844 (14)C19—C241.429 (8)
Eu—Cl62.7731 (14)C20—H200.9500
N1—H10.87 (2)C20—C211.358 (8)
N1—C11.331 (7)C21—H210.9500
N1—C51.351 (7)C21—C221.406 (8)
N2—C61.364 (7)C22—H220.9500
N2—C101.325 (7)C23—H230.9500
N3—H30.872 (19)C23—C241.346 (8)
N3—C131.328 (7)C24—H240.9500
N3—C171.367 (7)C25—H250.9500
N4—C181.360 (7)C25—C261.404 (8)
N4—C221.319 (7)C26—H260.9500
N5—C251.321 (7)C26—C271.357 (8)
N5—C291.360 (7)C27—H270.9500
N6—H60.863 (19)C27—C281.400 (8)
N6—C301.352 (7)C28—C291.408 (7)
N6—C341.333 (7)C28—C351.428 (8)
N7—C371.324 (7)C29—C301.434 (7)
N7—C411.363 (7)C30—C311.402 (7)
N8—H80.863 (19)C31—C321.412 (8)
N8—C421.351 (7)C31—C361.432 (8)
N8—C461.324 (7)C32—H320.9500
C1—H1A0.9500C32—C331.365 (8)
C1—C21.378 (9)C33—H330.9500
C2—H20.9500C33—C341.381 (8)
C2—C31.372 (9)C34—H340.9500
C3—H3A0.9500C35—H350.9500
C3—C41.394 (8)C35—C361.349 (8)
C4—C51.404 (7)C36—H360.9500
C4—C111.432 (8)C37—H370.9500
C5—C61.442 (7)C37—C381.410 (8)
C6—C71.408 (8)C38—H380.9500
C7—C81.393 (8)C38—C391.359 (8)
C7—C121.425 (8)C39—H390.9500
C8—H8A0.9500C39—C401.424 (8)
C8—C91.366 (8)C40—C411.411 (7)
C9—H90.9500C40—C471.423 (8)
C9—C101.386 (8)C41—C421.420 (8)
C10—H100.9500C42—C431.387 (7)
C11—H110.9500C43—C441.409 (8)
C11—C121.355 (8)C43—C481.426 (8)
C12—H120.9500C44—H440.9500
C13—H130.9500C44—C451.364 (8)
C13—C141.390 (8)C45—H450.9500
C14—H140.9500C45—C461.382 (8)
C14—C151.362 (8)C46—H460.9500
C15—H150.9500C47—H470.9500
C15—C161.412 (8)C47—C481.363 (8)
C16—C171.387 (7)C48—H480.9500
Cl1—Eu—Cl289.96 (5)C19—C20—H20120.5
Cl1—Eu—Cl392.13 (5)C19—C20—C21119.0 (5)
Cl1—Eu—Cl491.32 (4)H20—C20—C21120.5
Cl1—Eu—Cl590.67 (5)C20—C21—H21120.1
Cl1—Eu—Cl6177.37 (4)C20—C21—C22119.7 (5)
Cl2—Eu—Cl3175.24 (4)H21—C21—C22120.1
Cl2—Eu—Cl488.61 (4)N4—C22—C21123.7 (5)
Cl2—Eu—Cl591.92 (5)N4—C22—H22118.1
Cl2—Eu—Cl689.68 (4)C21—C22—H22118.1
Cl3—Eu—Cl487.07 (4)C16—C23—H23120.0
Cl3—Eu—Cl592.33 (5)C16—C23—C24120.0 (5)
Cl3—Eu—Cl688.04 (4)H23—C23—C24120.0
Cl4—Eu—Cl5177.94 (5)C19—C24—C23121.8 (5)
Cl4—Eu—Cl686.07 (4)C19—C24—H24119.1
Cl5—Eu—Cl691.94 (4)C23—C24—H24119.1
H1—N1—C1116 (4)N5—C25—H25118.2
H1—N1—C5120 (4)N5—C25—C26123.5 (6)
C1—N1—C5122.8 (5)H25—C25—C26118.2
C6—N2—C10116.0 (5)C25—C26—H26120.5
H3—N3—C13118 (4)C25—C26—C27119.0 (5)
H3—N3—C17120 (4)H26—C26—C27120.5
C13—N3—C17122.4 (5)C26—C27—H27119.9
C18—N4—C22116.5 (5)C26—C27—C28120.3 (6)
C25—N5—C29116.9 (5)H27—C27—C28119.9
H6—N6—C30118 (4)C27—C28—C29116.4 (5)
H6—N6—C34119 (4)C27—C28—C35123.7 (5)
C30—N6—C34122.8 (5)C29—C28—C35119.8 (5)
C37—N7—C41117.4 (5)N5—C29—C28123.9 (5)
H8—N8—C42121 (4)N5—C29—C30117.9 (5)
H8—N8—C46116 (4)C28—C29—C30118.2 (5)
C42—N8—C46123.3 (5)N6—C30—C29119.6 (5)
N1—C1—H1A120.0N6—C30—C31119.5 (5)
N1—C1—C2120.1 (6)C29—C30—C31120.9 (5)
H1A—C1—C2120.0C30—C31—C32117.7 (5)
C1—C2—H2120.4C30—C31—C36119.2 (5)
C1—C2—C3119.1 (6)C32—C31—C36123.1 (5)
H2—C2—C3120.4C31—C32—H32120.0
C2—C3—H3A119.5C31—C32—C33120.1 (5)
C2—C3—C4120.9 (6)H32—C32—C33120.0
H3A—C3—C4119.5C32—C33—H33119.9
C3—C4—C5117.8 (5)C32—C33—C34120.1 (5)
C3—C4—C11122.6 (5)H33—C33—C34119.9
C5—C4—C11119.5 (5)N6—C34—C33119.6 (5)
N1—C5—C4119.1 (5)N6—C34—H34120.2
N1—C5—C6120.5 (5)C33—C34—H34120.2
C4—C5—C6120.3 (5)C28—C35—H35119.1
N2—C6—C5117.9 (5)C28—C35—C36121.7 (5)
N2—C6—C7123.5 (5)H35—C35—C36119.1
C5—C6—C7118.6 (5)C31—C36—C35120.2 (5)
C6—C7—C8117.1 (5)C31—C36—H36119.9
C6—C7—C12119.4 (5)C35—C36—H36119.9
C8—C7—C12123.5 (5)N7—C37—H37118.2
C7—C8—H8A120.2N7—C37—C38123.6 (6)
C7—C8—C9119.7 (5)H37—C37—C38118.2
H8A—C8—C9120.2C37—C38—H38120.3
C8—C9—H9120.6C37—C38—C39119.5 (6)
C8—C9—C10118.8 (5)H38—C38—C39120.3
H9—C9—C10120.6C38—C39—H39120.5
N2—C10—C9124.6 (5)C38—C39—C40119.0 (5)
N2—C10—H10117.7H39—C39—C40120.5
C9—C10—H10117.7C39—C40—C41117.4 (5)
C4—C11—H11120.0C39—C40—C47122.3 (5)
C4—C11—C12120.0 (5)C41—C40—C47120.3 (5)
H11—C11—C12120.0N7—C41—C40123.1 (5)
C7—C12—C11122.0 (5)N7—C41—C42119.1 (5)
C7—C12—H12119.0C40—C41—C42117.8 (5)
C11—C12—H12119.0N8—C42—C41119.3 (5)
N3—C13—H13120.0N8—C42—C43119.0 (5)
N3—C13—C14120.1 (5)C41—C42—C43121.7 (5)
H13—C13—C14120.0C42—C43—C44117.9 (5)
C13—C14—H14120.2C42—C43—C48119.3 (5)
C13—C14—C15119.5 (5)C44—C43—C48122.8 (5)
H14—C14—C15120.2C43—C44—H44119.5
C14—C15—H15119.9C43—C44—C45121.0 (5)
C14—C15—C16120.1 (5)H44—C44—C45119.5
H15—C15—C16119.9C44—C45—H45120.7
C15—C16—C17118.5 (5)C44—C45—C46118.7 (5)
C15—C16—C23122.3 (5)H45—C45—C46120.7
C17—C16—C23119.1 (5)N8—C46—C45120.2 (5)
N3—C17—C16119.2 (5)N8—C46—H46119.9
N3—C17—C18119.2 (5)C45—C46—H46119.9
C16—C17—C18121.6 (5)C40—C47—H47119.6
N4—C18—C17118.4 (5)C40—C47—C48120.7 (5)
N4—C18—C19123.9 (5)H47—C47—C48119.6
C17—C18—C19117.6 (5)C43—C48—C47120.2 (5)
C18—C19—C20117.2 (5)C43—C48—H48119.9
C18—C19—C24119.7 (5)C47—C48—H48119.9
C20—C19—C24123.1 (5)
C5—N1—C1—C2−1.0 (9)C29—N5—C25—C260.0 (8)
N1—C1—C2—C3−1.5 (9)N5—C25—C26—C271.3 (9)
C1—C2—C3—C41.2 (9)C25—C26—C27—C28−0.6 (9)
C2—C3—C4—C51.5 (8)C26—C27—C28—C29−1.3 (8)
C2—C3—C4—C11178.3 (5)C26—C27—C28—C35−178.0 (5)
C1—N1—C5—C43.7 (8)C25—N5—C29—C28−2.1 (8)
C1—N1—C5—C6−174.1 (5)C25—N5—C29—C30178.4 (5)
C3—C4—C5—N1−3.8 (8)C27—C28—C29—N52.7 (8)
C3—C4—C5—C6174.0 (5)C27—C28—C29—C30−177.8 (5)
C11—C4—C5—N1179.3 (5)C35—C28—C29—N5179.6 (5)
C11—C4—C5—C6−2.9 (8)C35—C28—C29—C30−0.9 (8)
C10—N2—C6—C5175.2 (5)C34—N6—C30—C29178.3 (5)
C10—N2—C6—C7−3.6 (8)C34—N6—C30—C31−3.5 (8)
N1—C5—C6—N2−2.4 (8)N5—C29—C30—N6−3.2 (8)
N1—C5—C6—C7176.4 (5)N5—C29—C30—C31178.5 (5)
C4—C5—C6—N2179.8 (5)C28—C29—C30—N6177.2 (5)
C4—C5—C6—C7−1.3 (7)C28—C29—C30—C31−1.0 (8)
N2—C6—C7—C85.3 (8)N6—C30—C31—C323.2 (8)
N2—C6—C7—C12−176.7 (5)N6—C30—C31—C36−176.0 (5)
C5—C6—C7—C8−173.4 (5)C29—C30—C31—C32−178.6 (5)
C5—C6—C7—C124.6 (8)C29—C30—C31—C362.2 (8)
C6—C7—C8—C9−2.7 (8)C30—C31—C32—C330.0 (8)
C12—C7—C8—C9179.4 (5)C36—C31—C32—C33179.2 (5)
C7—C8—C9—C10−1.2 (9)C31—C32—C33—C34−3.1 (9)
C6—N2—C10—C9−0.7 (9)C30—N6—C34—C330.4 (8)
C8—C9—C10—N23.1 (9)C32—C33—C34—N63.0 (9)
C3—C4—C11—C12−172.8 (5)C27—C28—C35—C36178.3 (6)
C5—C4—C11—C124.0 (8)C29—C28—C35—C361.7 (8)
C4—C11—C12—C7−0.7 (8)C28—C35—C36—C31−0.5 (9)
C6—C7—C12—C11−3.6 (8)C30—C31—C36—C35−1.4 (8)
C8—C7—C12—C11174.2 (5)C32—C31—C36—C35179.4 (5)
C17—N3—C13—C140.7 (8)C41—N7—C37—C38−2.0 (9)
N3—C13—C14—C15−2.9 (8)N7—C37—C38—C390.5 (10)
C13—C14—C15—C162.9 (8)C37—C38—C39—C401.9 (9)
C14—C15—C16—C17−0.6 (8)C38—C39—C40—C41−2.7 (8)
C14—C15—C16—C23179.5 (5)C38—C39—C40—C47175.8 (5)
C13—N3—C17—C161.5 (8)C37—N7—C41—C401.1 (8)
C13—N3—C17—C18−178.3 (5)C37—N7—C41—C42−176.7 (5)
C15—C16—C17—N3−1.5 (7)C39—C40—C41—N71.2 (8)
C15—C16—C17—C18178.3 (5)C39—C40—C41—C42179.0 (5)
C23—C16—C17—N3178.3 (5)C47—C40—C41—N7−177.2 (5)
C23—C16—C17—C18−1.9 (8)C47—C40—C41—C420.5 (8)
C22—N4—C18—C17178.2 (5)C46—N8—C42—C41177.7 (5)
C22—N4—C18—C19−0.4 (8)C46—N8—C42—C43−1.6 (8)
N3—C17—C18—N41.4 (7)N7—C41—C42—N8−3.1 (8)
N3—C17—C18—C19−179.9 (5)N7—C41—C42—C43176.1 (5)
C16—C17—C18—N4−178.4 (5)C40—C41—C42—N8179.0 (5)
C16—C17—C18—C190.3 (8)C40—C41—C42—C43−1.7 (8)
N4—C18—C19—C200.5 (8)N8—C42—C43—C440.6 (8)
N4—C18—C19—C24−179.7 (5)N8—C42—C43—C48−179.1 (5)
C17—C18—C19—C20−178.1 (5)C41—C42—C43—C44−178.7 (5)
C17—C18—C19—C241.7 (8)C41—C42—C43—C481.7 (8)
C18—C19—C20—C210.3 (8)C42—C43—C44—C451.0 (8)
C24—C19—C20—C21−179.6 (5)C48—C43—C44—C45−179.3 (5)
C19—C20—C21—C22−1.0 (8)C43—C44—C45—C46−1.6 (9)
C18—N4—C22—C21−0.4 (8)C42—N8—C46—C451.0 (8)
C20—C21—C22—N41.1 (9)C44—C45—C46—N80.6 (9)
C15—C16—C23—C24−178.7 (5)C39—C40—C47—C48−177.6 (5)
C17—C16—C23—C241.4 (8)C41—C40—C47—C480.8 (8)
C16—C23—C24—C190.6 (9)C40—C47—C48—C43−0.8 (8)
C18—C19—C24—C23−2.2 (8)C42—C43—C48—C47−0.4 (8)
C20—C19—C24—C23177.6 (5)C44—C43—C48—C47−180.0 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl70.87 (2)2.25 (3)3.052 (5)154 (5)
N3—H3···Cl60.872 (19)2.45 (4)3.166 (5)140 (5)
N6—H6···Cl70.863 (19)2.42 (4)3.125 (5)139 (5)
N8—H8···Cl70.863 (19)2.35 (4)3.095 (5)145 (5)
Selected geometric parameters (Å) top
Eu—Cl12.6596 (14)Eu—Cl42.6753 (13)
Eu—Cl22.7092 (14)Eu—Cl52.6844 (14)
Eu—Cl32.6876 (14)Eu—Cl62.7731 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl70.87 (2)2.25 (3)3.052 (5)154 (5)
N3—H3···Cl60.872 (19)2.45 (4)3.166 (5)140 (5)
N6—H6···Cl70.863 (19)2.42 (4)3.125 (5)139 (5)
N8—H8···Cl70.863 (19)2.35 (4)3.095 (5)145 (5)
Acknowledgements top

We thank the EPSRC for financial support.

references
References top

Allen, F. H. (2002). Acta Cryst. B58, 380–388.

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wi., U.S.A.

Hallfeldt, J. (2003). Thesis, University of Hannover, Germany.

Petriček, S. (2005). Acta Chim. Slov. 52, 398–403.

Sheldrick, G. M. (2001). SHELXTL Version 5. Bruker AXS Inc., Madison, Wisconsin, U.S.A.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.