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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1376.
Published online 2009 October 17. doi:  10.1107/S160053680904135X
PMCID: PMC2971428

Tris(N-benzyl-N-methyl­dithio­carbamato-κ2 S,S′)(1,10-phenanthroline-κ2 N,N′)europium(III)

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-65-m1376-scheme1.jpg

Experimental

Crystal data

  • [Eu(C9H10NS2)3(C12H8N2)]
  • M r = 921.06
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1376-efi1.jpg
  • a = 10.691 (1) Å
  • b = 12.288 (1) Å
  • c = 16.553 (2) Å
  • α = 73.652 (2)°
  • β = 74.720 (2)°
  • γ = 71.629 (2)°
  • V = 1943.5 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.97 mm−1
  • T = 293 K
  • 0.48 × 0.35 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.451, T max = 0.694
  • 21775 measured reflections
  • 8695 independent reflections
  • 7425 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.141
  • S = 1.08
  • 8695 reflections
  • 463 parameters
  • H-atom parameters constrained
  • Δρmax = 3.56 e Å−3
  • Δρmin = −1.65 e Å−3

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

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904135X/xu2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904135X/xu2634Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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.

Figures

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.
Fig. 2.
Eight-coordinate coordination geometry of Eu.

Crystal data

[Eu(C9H10NS2)3(C12H8N2)]Z = 2
Mr = 921.06F(000) = 932
Triclinic, P1Dx = 1.574 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer8695 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°
[var phi] 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

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 = 1.08w = 1/[σ2(Fo2) + (0.0982P)2] where P = (Fo2 + 2Fc2)/3
8695 reflections(Δ/σ)max = 0.001
463 parametersΔρmax = 3.56 e Å3
0 restraintsΔρmin = −1.65 e Å3

Special details

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)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2634).

References

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