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Acta Cryst. (2009). E65, m1376    [ doi:10.1107/S160053680904135X ]

Tris(N-benzyl-N-methyldithiocarbamato-[kappa]2S,S')(1,10-phenanthroline-[kappa]2N,N')europium(III)

I. Baba, I. Raya, B. M. Yamin and S. W. Ng

Abstract top

In the title compound, [Eu(C9H10NS2)3(C12H8N2)], the EuIII atom exists in a distorted square-antiprismatic coordination geometry. Both dithiocarbamate and the N-heterocyclic ligands function in a chelating mode.

Related literature top

For the crystal structures of other europium dithiocarbamate–1,10-phenanthroline adducts see: Regulacio et al. (2005); Su et al. (1996); Varand et al. (1996).

Experimental top

Eeuropium(III) chloride (10 mmol) was reacted with 1,10-phenanthroline (10 mmol) in boiling water (15 ml). The solution was then cooled to 280 K. Separately, benzylmethylamine (30 mmol), carbon disulfide (30 mmol) and potassium hydroxide (30 mmol) were reacted in ethanol (15 ml) at 280 K. The two solutions were mixed. The white solid that precipitated was collected and recrystallized from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The final difference Fourier map has a large peak/deep hole in the vicinity of Eu1.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Eu(C12H8N2)(C9H8NS2)3 at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Eight-coordinate coordination geometry of Eu.
Tris(N-benzyl-N-methyldithiocarbamato- κ2S,S')(1,10-phenanthroline- κ2N,N')europium(III) top
Crystal data top
[Eu(C9H10NS2)3(C12H8N2)]Z = 2
Mr = 921.06F(000) = 932
Triclinic, P1Dx = 1.574 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.691 (1) ÅCell parameters from 946 reflections
b = 12.288 (1) Åθ = 2.3–28.1°
c = 16.553 (2) ŵ = 1.97 mm−1
α = 73.652 (2)°T = 293 K
β = 74.720 (2)°Block, brown
γ = 71.629 (2)°0.48 × 0.35 × 0.20 mm
V = 1943.5 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer		8695 independent reflections
Radiation source: fine-focus sealed tube7425 reflections with I > 2σ(I)
graphiteRint = 0.040
Detector resolution: 8.33 pixels mm-1θmax = 27.5°, θmin = 1.3°
φ and ω scansh = −13→13
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −15→15
Tmin = 0.451, Tmax = 0.694l = −21→21
21775 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0982P)2]
where P = (Fo2 + 2Fc2)/3
8695 reflections(Δ/σ)max = 0.001
463 parametersΔρmax = 3.56 e Å−3
0 restraintsΔρmin = −1.65 e Å−3
Crystal data top
[Eu(C9H10NS2)3(C12H8N2)]γ = 71.629 (2)°
Mr = 921.06V = 1943.5 (3) Å3
Triclinic, P1Z = 2
a = 10.691 (1) ÅMo Kα radiation
b = 12.288 (1) ŵ = 1.97 mm−1
c = 16.553 (2) ÅT = 293 K
α = 73.652 (2)°0.48 × 0.35 × 0.20 mm
β = 74.720 (2)°
Data collection top
Bruker SMART APEX
diffractometer		8695 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7425 reflections with I > 2σ(I)
Tmin = 0.451, Tmax = 0.694Rint = 0.040
21775 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.141Δρmax = 3.56 e Å−3
S = 1.08Δρmin = −1.65 e Å−3
8695 reflectionsAbsolute structure: ?
463 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Eu10.74676 (2)0.689048 (17)0.257329 (13)0.03679 (10)
S10.66925 (12)0.77165 (10)0.09104 (7)0.0440 (3)
S20.81829 (16)0.89432 (12)0.14613 (9)0.0563 (3)
S30.58827 (15)0.68170 (17)0.42600 (9)0.0732 (5)
S40.46969 (14)0.81089 (12)0.27570 (8)0.0568 (3)
S50.88318 (12)0.48647 (10)0.36901 (8)0.0437 (2)
S60.97198 (13)0.70423 (10)0.31481 (8)0.0460 (3)
N10.7477 (4)0.9584 (3)−0.0077 (2)0.0444 (8)
N20.3278 (4)0.7922 (4)0.4342 (3)0.0479 (9)
N31.1131 (4)0.5000 (3)0.3939 (2)0.0439 (8)
N40.9334 (4)0.5677 (3)0.1596 (2)0.0393 (8)
N50.6988 (4)0.5086 (3)0.2389 (2)0.0389 (8)
C10.7458 (4)0.8818 (4)0.0689 (3)0.0407 (9)
C20.6808 (6)0.9534 (5)−0.0728 (3)0.0577 (13)
H2A0.61260.9121−0.04580.087*
H2B0.74550.9132−0.11430.087*
H2C0.64031.0318−0.10080.087*
C30.8156 (5)1.0535 (4)−0.0322 (3)0.0526 (12)
H3A0.87861.0477−0.08600.063*
H3B0.86601.04450.01120.063*
C40.7169 (5)1.1726 (4)−0.0420 (3)0.0465 (10)
C50.6238 (6)1.2077 (5)0.0273 (3)0.0554 (12)
H50.62311.15790.08130.066*
C60.5311 (6)1.3166 (5)0.0173 (4)0.0627 (14)
H60.46881.33920.06460.075*
C70.5309 (6)1.3905 (5)−0.0613 (5)0.0666 (15)
H70.46791.4631−0.06800.080*
C80.6242 (7)1.3573 (5)−0.1307 (4)0.0667 (15)
H80.62561.4082−0.18420.080*
C90.7156 (6)1.2490 (5)−0.1215 (3)0.0551 (12)
H90.77721.2269−0.16920.066*
C100.4478 (5)0.7666 (4)0.3853 (3)0.0414 (9)
C110.2099 (6)0.8641 (6)0.3984 (4)0.0676 (16)
H11A0.23610.92000.34790.101*
H11B0.14660.90510.44000.101*
H11C0.16940.81480.38360.101*
C120.3024 (6)0.7410 (4)0.5268 (3)0.0590 (14)
H12A0.38760.69880.54430.071*
H12B0.25050.68460.53740.071*
C130.2287 (5)0.8296 (4)0.5812 (3)0.0501 (11)
C140.1026 (6)0.8280 (5)0.6291 (3)0.0581 (13)
H140.06110.77400.62540.070*
C150.0368 (7)0.9051 (5)0.6825 (4)0.0694 (16)
H15−0.04770.90210.71540.083*
C160.0970 (9)0.9863 (6)0.6868 (4)0.086 (2)
H160.05301.03830.72290.103*
C170.2201 (10)0.9912 (7)0.6387 (5)0.091 (2)
H170.25891.04810.64070.110*
C180.2885 (7)0.9115 (6)0.5866 (4)0.0727 (17)
H180.37430.91310.55540.087*
C191.0011 (4)0.5575 (4)0.3627 (3)0.0364 (8)
C201.2179 (5)0.5553 (5)0.3872 (4)0.0560 (12)
H20A1.24870.58800.32790.084*
H20B1.29150.49790.41040.084*
H20C1.18300.61680.41860.084*
C211.1386 (5)0.3742 (4)0.4357 (3)0.0471 (11)
H21A1.05320.35460.45910.057*
H21B1.18290.36020.48320.057*
C221.2240 (5)0.2934 (4)0.3764 (3)0.0437 (10)
C231.3054 (7)0.1868 (5)0.4098 (4)0.0637 (15)
H231.30980.16710.46760.076*
C241.3804 (8)0.1091 (5)0.3577 (5)0.0799 (19)
H241.43450.03750.38110.096*
C251.3762 (7)0.1359 (5)0.2727 (4)0.0694 (16)
H251.42650.08320.23810.083*
C261.2970 (6)0.2412 (6)0.2395 (4)0.0661 (15)
H261.29380.26050.18140.079*
C271.2210 (5)0.3205 (5)0.2903 (3)0.0553 (12)
H271.16780.39220.26620.066*
C280.5873 (5)0.4759 (4)0.2804 (3)0.0488 (11)
H280.52370.52290.31550.059*
C290.5608 (5)0.3747 (5)0.2739 (4)0.0550 (12)
H290.48050.35630.30310.066*
C300.6523 (6)0.3040 (4)0.2252 (3)0.0540 (12)
H300.63610.23580.22110.065*
C310.7737 (5)0.3339 (4)0.1800 (3)0.0438 (10)
C320.7923 (4)0.4368 (4)0.1904 (3)0.0376 (9)
C330.8754 (6)0.2628 (4)0.1285 (3)0.0550 (13)
H330.86130.19560.12110.066*
C340.9919 (6)0.2908 (4)0.0902 (3)0.0537 (12)
H341.05760.24240.05710.064*
C351.0163 (5)0.3941 (4)0.0998 (3)0.0443 (10)
C360.9166 (4)0.4682 (4)0.1487 (3)0.0372 (9)
C371.1370 (5)0.4265 (5)0.0607 (3)0.0520 (12)
H371.20530.37990.02760.062*
C381.1533 (5)0.5270 (5)0.0718 (3)0.0529 (12)
H381.23240.54980.04640.063*
C391.0476 (5)0.5953 (5)0.1225 (3)0.0459 (10)
H391.05910.66340.13020.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.03964 (14)0.02894 (13)0.04105 (14)−0.00537 (9)−0.00616 (9)−0.01192 (9)
S10.0525 (6)0.0400 (6)0.0444 (6)−0.0150 (5)−0.0092 (5)−0.0136 (4)
S20.0776 (9)0.0503 (7)0.0541 (7)−0.0315 (7)−0.0285 (6)−0.0003 (5)
S30.0493 (8)0.1024 (13)0.0442 (7)0.0127 (7)−0.0121 (6)−0.0132 (7)
S40.0528 (7)0.0582 (8)0.0435 (6)0.0107 (6)−0.0115 (5)−0.0126 (5)
S50.0435 (6)0.0329 (5)0.0548 (6)−0.0110 (4)−0.0120 (5)−0.0060 (4)
S60.0527 (7)0.0319 (5)0.0566 (7)−0.0130 (5)−0.0139 (5)−0.0089 (5)
N10.049 (2)0.0374 (19)0.044 (2)−0.0091 (16)−0.0110 (17)−0.0051 (15)
N20.041 (2)0.045 (2)0.051 (2)−0.0045 (17)−0.0038 (17)−0.0131 (17)
N30.045 (2)0.042 (2)0.047 (2)−0.0088 (16)−0.0111 (16)−0.0130 (16)
N40.0377 (19)0.0356 (18)0.0443 (19)−0.0076 (15)−0.0053 (15)−0.0126 (15)
N50.0360 (18)0.0360 (18)0.0449 (19)−0.0065 (14)−0.0098 (15)−0.0105 (15)
C10.043 (2)0.037 (2)0.042 (2)−0.0056 (18)−0.0112 (18)−0.0116 (17)
C20.073 (4)0.058 (3)0.046 (3)−0.012 (3)−0.022 (2)−0.012 (2)
C30.047 (3)0.049 (3)0.055 (3)−0.015 (2)−0.010 (2)0.001 (2)
C40.048 (3)0.044 (2)0.051 (3)−0.020 (2)−0.014 (2)−0.002 (2)
C50.064 (3)0.056 (3)0.051 (3)−0.025 (3)−0.009 (2)−0.009 (2)
C60.061 (3)0.062 (3)0.073 (4)−0.019 (3)−0.005 (3)−0.030 (3)
C70.069 (4)0.043 (3)0.097 (5)−0.012 (3)−0.031 (3)−0.018 (3)
C80.082 (4)0.047 (3)0.073 (4)−0.019 (3)−0.032 (3)0.002 (3)
C90.063 (3)0.050 (3)0.050 (3)−0.017 (2)−0.012 (2)−0.005 (2)
C100.043 (2)0.038 (2)0.041 (2)−0.0041 (18)−0.0064 (18)−0.0127 (17)
C110.047 (3)0.071 (4)0.080 (4)0.001 (3)−0.018 (3)−0.022 (3)
C120.068 (3)0.038 (3)0.058 (3)−0.009 (2)0.006 (3)−0.011 (2)
C130.062 (3)0.035 (2)0.047 (2)−0.009 (2)−0.006 (2)−0.0068 (19)
C140.059 (3)0.049 (3)0.057 (3)−0.003 (2)−0.003 (2)−0.016 (2)
C150.066 (4)0.056 (3)0.063 (3)0.010 (3)−0.005 (3)−0.015 (3)
C160.136 (7)0.045 (3)0.065 (4)0.001 (4)−0.020 (4)−0.021 (3)
C170.140 (7)0.064 (4)0.087 (5)−0.042 (5)−0.022 (5)−0.027 (4)
C180.083 (4)0.065 (4)0.071 (4)−0.032 (3)−0.005 (3)−0.011 (3)
C190.040 (2)0.034 (2)0.0358 (19)−0.0082 (17)−0.0032 (16)−0.0135 (16)
C200.050 (3)0.061 (3)0.064 (3)−0.017 (2)−0.015 (2)−0.017 (3)
C210.045 (2)0.048 (3)0.042 (2)−0.004 (2)−0.0115 (19)−0.0051 (19)
C220.045 (2)0.039 (2)0.050 (2)−0.0120 (19)−0.011 (2)−0.0097 (19)
C230.087 (4)0.040 (3)0.059 (3)−0.004 (3)−0.023 (3)−0.007 (2)
C240.105 (5)0.036 (3)0.092 (5)0.003 (3)−0.031 (4)−0.017 (3)
C250.073 (4)0.051 (3)0.085 (4)−0.011 (3)−0.005 (3)−0.033 (3)
C260.073 (4)0.065 (4)0.058 (3)−0.010 (3)−0.008 (3)−0.023 (3)
C270.053 (3)0.052 (3)0.052 (3)−0.001 (2)−0.009 (2)−0.013 (2)
C280.043 (2)0.047 (3)0.058 (3)−0.013 (2)−0.007 (2)−0.013 (2)
C290.050 (3)0.049 (3)0.069 (3)−0.019 (2)−0.014 (2)−0.009 (2)
C300.068 (3)0.038 (2)0.065 (3)−0.023 (2)−0.020 (3)−0.008 (2)
C310.056 (3)0.032 (2)0.047 (2)−0.0099 (19)−0.020 (2)−0.0066 (18)
C320.042 (2)0.0299 (19)0.044 (2)−0.0044 (16)−0.0164 (18)−0.0099 (16)
C330.077 (4)0.037 (2)0.057 (3)−0.007 (2)−0.024 (3)−0.018 (2)
C340.064 (3)0.041 (3)0.053 (3)0.002 (2)−0.013 (2)−0.022 (2)
C350.047 (2)0.041 (2)0.039 (2)0.0018 (19)−0.0105 (19)−0.0123 (18)
C360.040 (2)0.034 (2)0.037 (2)−0.0033 (17)−0.0100 (17)−0.0114 (16)
C370.042 (3)0.061 (3)0.048 (3)0.003 (2)−0.007 (2)−0.024 (2)
C380.041 (2)0.066 (3)0.049 (3)−0.013 (2)0.000 (2)−0.017 (2)
C390.039 (2)0.052 (3)0.047 (2)−0.013 (2)−0.0019 (19)−0.016 (2)
Geometric parameters (Å, °) top
Eu1—N52.540 (4)C12—H12B0.9700
Eu1—N42.569 (4)C13—C141.375 (7)
Eu1—S42.8451 (13)C13—C181.384 (8)
Eu1—S32.8523 (14)C14—C151.377 (8)
Eu1—S22.8627 (13)C14—H140.9300
Eu1—S52.8781 (12)C15—C161.372 (10)
Eu1—S62.8859 (12)C15—H150.9300
Eu1—S12.8970 (12)C16—C171.357 (12)
S1—C11.702 (5)C16—H160.9300
S2—C11.723 (5)C17—C181.389 (10)
S3—C101.717 (5)C17—H170.9300
S4—C101.716 (5)C18—H180.9300
S5—C191.713 (4)C20—H20A0.9600
S6—C191.717 (4)C20—H20B0.9600
N1—C11.349 (6)C20—H20C0.9600
N1—C21.465 (6)C21—C221.512 (7)
N1—C31.473 (6)C21—H21A0.9700
N2—C101.320 (6)C21—H21B0.9700
N2—C111.455 (7)C22—C271.376 (7)
N2—C121.471 (7)C22—C231.380 (7)
N3—C191.337 (6)C23—C241.384 (9)
N3—C201.450 (6)C23—H230.9300
N3—C211.475 (6)C24—C251.360 (10)
N4—C391.315 (6)C24—H240.9300
N4—C361.357 (5)C25—C261.360 (9)
N5—C281.330 (6)C25—H250.9300
N5—C321.357 (5)C26—C271.385 (8)
C2—H2A0.9600C26—H260.9300
C2—H2B0.9600C27—H270.9300
C2—H2C0.9600C28—C291.397 (7)
C3—C41.505 (7)C28—H280.9300
C3—H3A0.9700C29—C301.344 (8)
C3—H3B0.9700C29—H290.9300
C4—C51.377 (7)C30—C311.419 (7)
C4—C91.386 (7)C30—H300.9300
C5—C61.388 (8)C31—C321.402 (6)
C5—H50.9300C31—C331.415 (7)
C6—C71.361 (9)C32—C361.443 (6)
C6—H60.9300C33—C341.343 (8)
C7—C81.372 (9)C33—H330.9300
C7—H70.9300C34—C351.431 (7)
C8—C91.376 (8)C34—H340.9300
C8—H80.9300C35—C361.403 (6)
C9—H90.9300C35—C371.408 (7)
C11—H11A0.9600C37—C381.367 (8)
C11—H11B0.9600C37—H370.9300
C11—H11C0.9600C38—C391.410 (7)
C12—C131.501 (7)C38—H380.9300
C12—H12A0.9700C39—H390.9300
N5—Eu1—N464.41 (11)N2—C12—H12A108.7
N5—Eu1—S491.49 (9)C13—C12—H12A108.7
N4—Eu1—S4141.09 (9)N2—C12—H12B108.7
N5—Eu1—S394.45 (9)C13—C12—H12B108.7
N4—Eu1—S3144.46 (9)H12A—C12—H12B107.6
S4—Eu1—S361.51 (4)C14—C13—C18118.7 (5)
N5—Eu1—S2136.16 (9)C14—C13—C12120.6 (5)
N4—Eu1—S287.66 (9)C18—C13—C12120.6 (5)
S4—Eu1—S290.73 (4)C13—C14—C15121.1 (6)
S3—Eu1—S2124.44 (5)C13—C14—H14119.4
N5—Eu1—S571.80 (8)C15—C14—H14119.4
N4—Eu1—S573.60 (9)C16—C15—C14119.4 (6)
S4—Eu1—S5129.73 (4)C16—C15—H15120.3
S3—Eu1—S572.65 (4)C14—C15—H15120.3
S2—Eu1—S5134.15 (4)C17—C16—C15120.5 (6)
N5—Eu1—S6128.70 (8)C17—C16—H16119.7
N4—Eu1—S682.53 (9)C15—C16—H16119.7
S4—Eu1—S6134.30 (4)C16—C17—C18120.2 (7)
S3—Eu1—S690.97 (4)C16—C17—H17119.9
S2—Eu1—S675.11 (4)C18—C17—H17119.9
S5—Eu1—S661.43 (3)C13—C18—C17119.9 (7)
N5—Eu1—S178.24 (8)C13—C18—H18120.0
N4—Eu1—S175.12 (9)C17—C18—H18120.0
S4—Eu1—S170.08 (4)N3—C19—S5120.9 (3)
S3—Eu1—S1130.85 (4)N3—C19—S6120.9 (3)
S2—Eu1—S161.59 (3)S5—C19—S6118.2 (3)
S5—Eu1—S1143.61 (3)N3—C20—H20A109.5
S6—Eu1—S1131.41 (3)N3—C20—H20B109.5
C1—S1—Eu189.39 (15)H20A—C20—H20B109.5
C1—S2—Eu190.12 (16)N3—C20—H20C109.5
C10—S3—Eu191.03 (16)H20A—C20—H20C109.5
C10—S4—Eu191.30 (16)H20B—C20—H20C109.5
C19—S5—Eu189.86 (15)N3—C21—C22113.9 (4)
C19—S6—Eu189.51 (15)N3—C21—H21A108.8
C1—N1—C2122.1 (4)C22—C21—H21A108.8
C1—N1—C3123.1 (4)N3—C21—H21B108.8
C2—N1—C3114.8 (4)C22—C21—H21B108.8
C10—N2—C11121.8 (4)H21A—C21—H21B107.7
C10—N2—C12122.2 (4)C27—C22—C23118.3 (5)
C11—N2—C12115.7 (4)C27—C22—C21122.5 (4)
C19—N3—C20122.8 (4)C23—C22—C21119.2 (4)
C19—N3—C21121.3 (4)C24—C23—C22120.4 (6)
C20—N3—C21115.9 (4)C24—C23—H23119.8
C39—N4—C36118.3 (4)C22—C23—H23119.8
C39—N4—Eu1122.7 (3)C25—C24—C23121.0 (6)
C36—N4—Eu1119.0 (3)C25—C24—H24119.5
C28—N5—C32117.4 (4)C23—C24—H24119.5
C28—N5—Eu1122.1 (3)C26—C25—C24118.7 (6)
C32—N5—Eu1120.3 (3)C26—C25—H25120.6
N1—C1—S1120.1 (3)C24—C25—H25120.6
N1—C1—S2121.0 (3)C25—C26—C27121.3 (6)
S1—C1—S2118.9 (3)C25—C26—H26119.3
N1—C2—H2A109.5C27—C26—H26119.3
N1—C2—H2B109.5C22—C27—C26120.2 (5)
H2A—C2—H2B109.5C22—C27—H27119.9
N1—C2—H2C109.5C26—C27—H27119.9
H2A—C2—H2C109.5N5—C28—C29123.3 (5)
H2B—C2—H2C109.5N5—C28—H28118.4
N1—C3—C4111.7 (4)C29—C28—H28118.4
N1—C3—H3A109.3C30—C29—C28119.6 (5)
C4—C3—H3A109.3C30—C29—H29120.2
N1—C3—H3B109.3C28—C29—H29120.2
C4—C3—H3B109.3C29—C30—C31119.6 (4)
H3A—C3—H3B107.9C29—C30—H30120.2
C5—C4—C9118.2 (5)C31—C30—H30120.2
C5—C4—C3121.1 (4)C32—C31—C30117.1 (4)
C9—C4—C3120.7 (5)C32—C31—C33120.2 (5)
C4—C5—C6120.7 (5)C30—C31—C33122.7 (4)
C4—C5—H5119.7N5—C32—C31123.0 (4)
C6—C5—H5119.7N5—C32—C36117.9 (4)
C7—C6—C5120.4 (6)C31—C32—C36119.1 (4)
C7—C6—H6119.8C34—C33—C31121.1 (5)
C5—C6—H6119.8C34—C33—H33119.5
C6—C7—C8119.5 (6)C31—C33—H33119.5
C6—C7—H7120.3C33—C34—C35120.8 (4)
C8—C7—H7120.3C33—C34—H34119.6
C9—C8—C7120.5 (6)C35—C34—H34119.6
C9—C8—H8119.8C36—C35—C37117.7 (4)
C7—C8—H8119.8C36—C35—C34119.7 (4)
C8—C9—C4120.7 (6)C37—C35—C34122.6 (4)
C8—C9—H9119.6N4—C36—C35122.5 (4)
C4—C9—H9119.6N4—C36—C32118.4 (4)
N2—C10—S4121.0 (4)C35—C36—C32119.1 (4)
N2—C10—S3122.7 (4)C38—C37—C35119.7 (4)
S4—C10—S3116.2 (3)C38—C37—H37120.2
N2—C11—H11A109.5C35—C37—H37120.2
N2—C11—H11B109.5C37—C38—C39118.5 (5)
H11A—C11—H11B109.5C37—C38—H38120.8
N2—C11—H11C109.5C39—C38—H38120.8
H11A—C11—H11C109.5N4—C39—C38123.4 (5)
H11B—C11—H11C109.5N4—C39—H39118.3
N2—C12—C13114.0 (4)C38—C39—H39118.3
N5—Eu1—S1—C1−160.64 (18)C4—C5—C6—C70.0 (8)
N4—Eu1—S1—C1−94.29 (17)C5—C6—C7—C8−0.8 (9)
S4—Eu1—S1—C1103.41 (16)C6—C7—C8—C91.4 (9)
S3—Eu1—S1—C1113.68 (16)C7—C8—C9—C4−1.2 (9)
S2—Eu1—S1—C11.20 (16)C5—C4—C9—C80.4 (8)
S5—Eu1—S1—C1−125.73 (16)C3—C4—C9—C8179.1 (5)
S6—Eu1—S1—C1−28.73 (16)C11—N2—C10—S4−3.4 (7)
N5—Eu1—S2—C124.9 (2)C12—N2—C10—S4170.7 (4)
N4—Eu1—S2—C173.14 (18)C11—N2—C10—S3−179.8 (4)
S4—Eu1—S2—C1−67.97 (16)C12—N2—C10—S3−5.8 (7)
S3—Eu1—S2—C1−123.24 (16)Eu1—S4—C10—N2−175.9 (4)
S5—Eu1—S2—C1137.44 (15)Eu1—S4—C10—S30.8 (3)
S6—Eu1—S2—C1156.03 (16)Eu1—S3—C10—N2175.9 (4)
S1—Eu1—S2—C1−1.19 (15)Eu1—S3—C10—S4−0.8 (3)
N5—Eu1—S3—C10−88.80 (19)C10—N2—C12—C13130.3 (5)
N4—Eu1—S3—C10−139.3 (2)C11—N2—C12—C13−55.4 (7)
S4—Eu1—S3—C100.48 (17)N2—C12—C13—C14115.9 (6)
S2—Eu1—S3—C1069.71 (18)N2—C12—C13—C18−66.7 (7)
S5—Eu1—S3—C10−158.17 (18)C18—C13—C14—C15−0.8 (9)
S6—Eu1—S3—C10142.26 (17)C12—C13—C14—C15176.7 (6)
S1—Eu1—S3—C10−10.51 (19)C13—C14—C15—C161.3 (9)
N5—Eu1—S4—C1093.77 (18)C14—C15—C16—C170.2 (11)
N4—Eu1—S4—C10142.8 (2)C15—C16—C17—C18−2.0 (12)
S3—Eu1—S4—C10−0.48 (17)C14—C13—C18—C17−1.1 (10)
S2—Eu1—S4—C10−130.01 (17)C12—C13—C18—C17−178.5 (6)
S5—Eu1—S4—C1026.39 (18)C16—C17—C18—C132.5 (12)
S6—Eu1—S4—C10−60.29 (17)C20—N3—C19—S5177.6 (4)
S1—Eu1—S4—C10170.70 (17)C21—N3—C19—S5−0.7 (6)
N5—Eu1—S5—C19152.45 (16)C20—N3—C19—S6−2.1 (6)
N4—Eu1—S5—C1984.61 (16)C21—N3—C19—S6179.6 (3)
S4—Eu1—S5—C19−131.30 (14)Eu1—S5—C19—N3−170.0 (3)
S3—Eu1—S5—C19−106.71 (14)Eu1—S5—C19—S69.6 (2)
S2—Eu1—S5—C1914.80 (15)Eu1—S6—C19—N3170.0 (3)
S6—Eu1—S5—C19−5.74 (14)Eu1—S6—C19—S5−9.6 (2)
S1—Eu1—S5—C19116.31 (14)C19—N3—C21—C2295.4 (5)
N5—Eu1—S6—C19−21.16 (18)C20—N3—C21—C22−83.0 (5)
N4—Eu1—S6—C19−69.62 (16)N3—C21—C22—C27−31.9 (7)
S4—Eu1—S6—C19124.76 (14)N3—C21—C22—C23150.1 (5)
S3—Eu1—S6—C1975.32 (14)C27—C22—C23—C24−0.7 (9)
S2—Eu1—S6—C19−159.18 (14)C21—C22—C23—C24177.3 (6)
S5—Eu1—S6—C195.73 (14)C22—C23—C24—C250.2 (11)
S1—Eu1—S6—C19−132.17 (14)C23—C24—C25—C260.3 (11)
N5—Eu1—N4—C39−178.8 (4)C24—C25—C26—C27−0.3 (11)
S4—Eu1—N4—C39124.3 (3)C23—C22—C27—C260.8 (9)
S3—Eu1—N4—C39−120.3 (3)C21—C22—C27—C26−177.3 (5)
S2—Eu1—N4—C3936.1 (4)C25—C26—C27—C22−0.3 (10)
S5—Eu1—N4—C39−101.5 (4)C32—N5—C28—C29−2.2 (7)
S6—Eu1—N4—C39−39.2 (4)Eu1—N5—C28—C29−177.5 (4)
S1—Eu1—N4—C3997.3 (4)N5—C28—C29—C301.5 (8)
N5—Eu1—N4—C36−1.9 (3)C28—C29—C30—C31−0.9 (8)
S4—Eu1—N4—C36−58.7 (4)C29—C30—C31—C321.1 (7)
S3—Eu1—N4—C3656.6 (4)C29—C30—C31—C33179.0 (5)
S2—Eu1—N4—C36−147.0 (3)C28—N5—C32—C312.4 (6)
S5—Eu1—N4—C3675.4 (3)Eu1—N5—C32—C31177.8 (3)
S6—Eu1—N4—C36137.8 (3)C28—N5—C32—C36−176.8 (4)
S1—Eu1—N4—C36−85.8 (3)Eu1—N5—C32—C36−1.5 (5)
N4—Eu1—N5—C28176.8 (4)C30—C31—C32—N5−1.9 (6)
S4—Eu1—N5—C28−34.9 (3)C33—C31—C32—N5−179.9 (4)
S3—Eu1—N5—C2826.6 (4)C30—C31—C32—C36177.4 (4)
S2—Eu1—N5—C28−127.5 (3)C33—C31—C32—C36−0.7 (6)
S5—Eu1—N5—C2896.7 (4)C32—C31—C33—C341.4 (7)
S6—Eu1—N5—C28121.5 (3)C30—C31—C33—C34−176.6 (5)
S1—Eu1—N5—C28−104.2 (3)C31—C33—C34—C35−0.5 (8)
N4—Eu1—N5—C321.7 (3)C33—C34—C35—C36−1.0 (7)
S4—Eu1—N5—C32150.0 (3)C33—C34—C35—C37−180.0 (5)
S3—Eu1—N5—C32−148.5 (3)C39—N4—C36—C350.3 (6)
S2—Eu1—N5—C3257.4 (3)Eu1—N4—C36—C35−176.8 (3)
S5—Eu1—N5—C32−78.4 (3)C39—N4—C36—C32179.1 (4)
S6—Eu1—N5—C32−53.7 (3)Eu1—N4—C36—C322.0 (5)
S1—Eu1—N5—C3280.7 (3)C37—C35—C36—N4−0.5 (6)
C2—N1—C1—S12.4 (6)C34—C35—C36—N4−179.5 (4)
C3—N1—C1—S1−178.1 (4)C37—C35—C36—C32−179.3 (4)
C2—N1—C1—S2−176.7 (4)C34—C35—C36—C321.7 (6)
C3—N1—C1—S22.8 (6)N5—C32—C36—N4−0.4 (6)
Eu1—S1—C1—N1178.8 (4)C31—C32—C36—N4−179.7 (4)
Eu1—S1—C1—S2−2.0 (3)N5—C32—C36—C35178.5 (4)
Eu1—S2—C1—N1−178.8 (4)C31—C32—C36—C35−0.8 (6)
Eu1—S2—C1—S12.0 (3)C36—C35—C37—C380.4 (7)
C1—N1—C3—C4−113.7 (5)C34—C35—C37—C38179.4 (5)
C2—N1—C3—C465.9 (6)C35—C37—C38—C390.0 (8)
N1—C3—C4—C564.9 (6)C36—N4—C39—C380.1 (7)
N1—C3—C4—C9−113.8 (5)Eu1—N4—C39—C38177.1 (4)
C9—C4—C5—C60.2 (8)C37—C38—C39—N4−0.3 (8)
C3—C4—C5—C6−178.4 (5)
Table 1
Selected geometric parameters (Å) top
Eu1—N52.540 (4)Eu1—S22.8627 (13)
Eu1—N42.569 (4)Eu1—S52.8781 (12)
Eu1—S42.8451 (13)Eu1—S62.8859 (12)
Eu1—S32.8523 (14)Eu1—S12.8970 (12)
Acknowledgements top

We thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08–27-111 and 06–01-02-SF0539) and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2000). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Regulacio, M. D., Tomson, N. & Stoll, S. L. (2005). Chem. Mater. 17, 3114–3121.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Su, C.-Y., Tan, M.-Y., Tang, N., Gan, X.-M., Lu, W.-S. & Wang, X. (1996). J. Coord. Chem. 38, 207–218.

Varand, V. L., Glinskaya, L. A., Klevtsova, R. F. & Larionov, S. V. (1996). Zh. Strukt. Khim. 39, 300–309.

Westrip, S. P. (2009). publCIF. In preparation.