Tris(N-benzyl-N-methyl­dithio­carbamato-κ2S,S′)(1,10-phenanthroline-κ2N,N′)europium(III)

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

doi:10.1107/S160053680904135X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1376

https://doi.org/10.1107/S160053680904135X

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Tris(N-benzyl-N-methyldithiocarbamato-κ²S,S′)(1,10-phenanthroline-κ²N,N′)europium(III)

Ibrahim Baba,^a Indah Raya,^a Bohari M. Yamin ^a and Seik Weng Ng ^b ^*

^aSchool of Chemical Sciences, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor Darul Ehsan, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 9 October 2009; accepted 9 October 2009; online 17 October 2009)

In the title compound, [Eu(C₉H₁₀NS₂)₃(C₁₂H₈N₂)], the Eu^III 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 ); Su et al. (1996 ); Varand et al. (1996 ).

Experimental

Crystal data

[Eu(C₉H₁₀NS₂)₃(C₁₂H₈N₂)]
M_r = 921.06
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 1.08
8695 reflections
463 parameters
H-atom parameters constrained
Δρ_max = 3.56 e Å⁻³
Δρ_min = −1.65 e Å⁻³

Table 1
Selected bond lengths (Å)

Eu1—N5	2.540 (4)
Eu1—N4	2.569 (4)
Eu1—S4	2.8451 (13)
Eu1—S3	2.8523 (14)
Eu1—S2	2.8627 (13)
Eu1—S5	2.8781 (12)
Eu1—S6	2.8859 (12)
Eu1—S1	2.8970 (12)

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904135X/xu2634Isup2.hkl

checkCIF report

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.

Structure description 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).

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

	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.

Tris(N-benzyl-N-methyldithiocarbamato- κ²S,S')(1,10-phenanthroline- κ²N,N')europium(III) top

Crystal data top

[Eu(C₉H₁₀NS₂)₃(C₁₂H₈N₂)]	Z = 2
M_r = 921.06	F(000) = 932
Triclinic, P1	D_x = 1.574 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.691 (1) Å	Cell parameters from 946 reflections
b = 12.288 (1) Å	θ = 2.3–28.1°
c = 16.553 (2) Å	µ = 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 tube	7425 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 1.3°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→15
T_min = 0.451, T_max = 0.694	l = −21→21
21775 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0982P)²] where P = (F_o² + 2F_c²)/3
8695 reflections	(Δ/σ)_max = 0.001
463 parameters	Δρ_max = 3.56 e Å⁻³
0 restraints	Δρ_min = −1.65 e Å⁻³

Crystal data top

[Eu(C₉H₁₀NS₂)₃(C₁₂H₈N₂)]	γ = 71.629 (2)°
M_r = 921.06	V = 1943.5 (3) Å³
Triclinic, P1	Z = 2
a = 10.691 (1) Å	Mo Kα radiation
b = 12.288 (1) Å	µ = 1.97 mm⁻¹
c = 16.553 (2) Å	T = 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)
T_min = 0.451, T_max = 0.694	R_int = 0.040
21775 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.08	Δρ_max = 3.56 e Å⁻³
8695 reflections	Δρ_min = −1.65 e Å⁻³
463 parameters

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

	x	y	z	U_iso*/U_eq
Eu1	0.74676 (2)	0.689048 (17)	0.257329 (13)	0.03679 (10)
S1	0.66925 (12)	0.77165 (10)	0.09104 (7)	0.0440 (3)
S2	0.81829 (16)	0.89432 (12)	0.14613 (9)	0.0563 (3)
S3	0.58827 (15)	0.68170 (17)	0.42600 (9)	0.0732 (5)
S4	0.46969 (14)	0.81089 (12)	0.27570 (8)	0.0568 (3)
S5	0.88318 (12)	0.48647 (10)	0.36901 (8)	0.0437 (2)
S6	0.97198 (13)	0.70423 (10)	0.31481 (8)	0.0460 (3)
N1	0.7477 (4)	0.9584 (3)	−0.0077 (2)	0.0444 (8)
N2	0.3278 (4)	0.7922 (4)	0.4342 (3)	0.0479 (9)
N3	1.1131 (4)	0.5000 (3)	0.3939 (2)	0.0439 (8)
N4	0.9334 (4)	0.5677 (3)	0.1596 (2)	0.0393 (8)
N5	0.6988 (4)	0.5086 (3)	0.2389 (2)	0.0389 (8)
C1	0.7458 (4)	0.8818 (4)	0.0689 (3)	0.0407 (9)
C2	0.6808 (6)	0.9534 (5)	−0.0728 (3)	0.0577 (13)
H2A	0.6126	0.9121	−0.0458	0.087*
H2B	0.7455	0.9132	−0.1143	0.087*
H2C	0.6403	1.0318	−0.1008	0.087*
C3	0.8156 (5)	1.0535 (4)	−0.0322 (3)	0.0526 (12)
H3A	0.8786	1.0477	−0.0860	0.063*
H3B	0.8660	1.0445	0.0112	0.063*
C4	0.7169 (5)	1.1726 (4)	−0.0420 (3)	0.0465 (10)
C5	0.6238 (6)	1.2077 (5)	0.0273 (3)	0.0554 (12)
H5	0.6231	1.1579	0.0813	0.066*
C6	0.5311 (6)	1.3166 (5)	0.0173 (4)	0.0627 (14)
H6	0.4688	1.3392	0.0646	0.075*
C7	0.5309 (6)	1.3905 (5)	−0.0613 (5)	0.0666 (15)
H7	0.4679	1.4631	−0.0680	0.080*
C8	0.6242 (7)	1.3573 (5)	−0.1307 (4)	0.0667 (15)
H8	0.6256	1.4082	−0.1842	0.080*
C9	0.7156 (6)	1.2490 (5)	−0.1215 (3)	0.0551 (12)
H9	0.7772	1.2269	−0.1692	0.066*
C10	0.4478 (5)	0.7666 (4)	0.3853 (3)	0.0414 (9)
C11	0.2099 (6)	0.8641 (6)	0.3984 (4)	0.0676 (16)
H11A	0.2361	0.9200	0.3479	0.101*
H11B	0.1466	0.9051	0.4400	0.101*
H11C	0.1694	0.8148	0.3836	0.101*
C12	0.3024 (6)	0.7410 (4)	0.5268 (3)	0.0590 (14)
H12A	0.3876	0.6988	0.5443	0.071*
H12B	0.2505	0.6846	0.5374	0.071*
C13	0.2287 (5)	0.8296 (4)	0.5812 (3)	0.0501 (11)
C14	0.1026 (6)	0.8280 (5)	0.6291 (3)	0.0581 (13)
H14	0.0611	0.7740	0.6254	0.070*
C15	0.0368 (7)	0.9051 (5)	0.6825 (4)	0.0694 (16)
H15	−0.0477	0.9021	0.7154	0.083*
C16	0.0970 (9)	0.9863 (6)	0.6868 (4)	0.086 (2)
H16	0.0530	1.0383	0.7229	0.103*
C17	0.2201 (10)	0.9912 (7)	0.6387 (5)	0.091 (2)
H17	0.2589	1.0481	0.6407	0.110*
C18	0.2885 (7)	0.9115 (6)	0.5866 (4)	0.0727 (17)
H18	0.3743	0.9131	0.5554	0.087*
C19	1.0011 (4)	0.5575 (4)	0.3627 (3)	0.0364 (8)
C20	1.2179 (5)	0.5553 (5)	0.3872 (4)	0.0560 (12)
H20A	1.2487	0.5880	0.3279	0.084*
H20B	1.2915	0.4979	0.4104	0.084*
H20C	1.1830	0.6168	0.4186	0.084*
C21	1.1386 (5)	0.3742 (4)	0.4357 (3)	0.0471 (11)
H21A	1.0532	0.3546	0.4591	0.057*
H21B	1.1829	0.3602	0.4832	0.057*
C22	1.2240 (5)	0.2934 (4)	0.3764 (3)	0.0437 (10)
C23	1.3054 (7)	0.1868 (5)	0.4098 (4)	0.0637 (15)
H23	1.3098	0.1671	0.4676	0.076*
C24	1.3804 (8)	0.1091 (5)	0.3577 (5)	0.0799 (19)
H24	1.4345	0.0375	0.3811	0.096*
C25	1.3762 (7)	0.1359 (5)	0.2727 (4)	0.0694 (16)
H25	1.4265	0.0832	0.2381	0.083*
C26	1.2970 (6)	0.2412 (6)	0.2395 (4)	0.0661 (15)
H26	1.2938	0.2605	0.1814	0.079*
C27	1.2210 (5)	0.3205 (5)	0.2903 (3)	0.0553 (12)
H27	1.1678	0.3922	0.2662	0.066*
C28	0.5873 (5)	0.4759 (4)	0.2804 (3)	0.0488 (11)
H28	0.5237	0.5229	0.3155	0.059*
C29	0.5608 (5)	0.3747 (5)	0.2739 (4)	0.0550 (12)
H29	0.4805	0.3563	0.3031	0.066*
C30	0.6523 (6)	0.3040 (4)	0.2252 (3)	0.0540 (12)
H30	0.6361	0.2358	0.2211	0.065*
C31	0.7737 (5)	0.3339 (4)	0.1800 (3)	0.0438 (10)
C32	0.7923 (4)	0.4368 (4)	0.1904 (3)	0.0376 (9)
C33	0.8754 (6)	0.2628 (4)	0.1285 (3)	0.0550 (13)
H33	0.8613	0.1956	0.1211	0.066*
C34	0.9919 (6)	0.2908 (4)	0.0902 (3)	0.0537 (12)
H34	1.0576	0.2424	0.0571	0.064*
C35	1.0163 (5)	0.3941 (4)	0.0998 (3)	0.0443 (10)
C36	0.9166 (4)	0.4682 (4)	0.1487 (3)	0.0372 (9)
C37	1.1370 (5)	0.4265 (5)	0.0607 (3)	0.0520 (12)
H37	1.2053	0.3799	0.0276	0.062*
C38	1.1533 (5)	0.5270 (5)	0.0718 (3)	0.0529 (12)
H38	1.2324	0.5498	0.0464	0.063*
C39	1.0476 (5)	0.5953 (5)	0.1225 (3)	0.0459 (10)
H39	1.0591	0.6634	0.1302	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.03964 (14)	0.02894 (13)	0.04105 (14)	−0.00537 (9)	−0.00616 (9)	−0.01192 (9)
S1	0.0525 (6)	0.0400 (6)	0.0444 (6)	−0.0150 (5)	−0.0092 (5)	−0.0136 (4)
S2	0.0776 (9)	0.0503 (7)	0.0541 (7)	−0.0315 (7)	−0.0285 (6)	−0.0003 (5)
S3	0.0493 (8)	0.1024 (13)	0.0442 (7)	0.0127 (7)	−0.0121 (6)	−0.0132 (7)
S4	0.0528 (7)	0.0582 (8)	0.0435 (6)	0.0107 (6)	−0.0115 (5)	−0.0126 (5)
S5	0.0435 (6)	0.0329 (5)	0.0548 (6)	−0.0110 (4)	−0.0120 (5)	−0.0060 (4)
S6	0.0527 (7)	0.0319 (5)	0.0566 (7)	−0.0130 (5)	−0.0139 (5)	−0.0089 (5)
N1	0.049 (2)	0.0374 (19)	0.044 (2)	−0.0091 (16)	−0.0110 (17)	−0.0051 (15)
N2	0.041 (2)	0.045 (2)	0.051 (2)	−0.0045 (17)	−0.0038 (17)	−0.0131 (17)
N3	0.045 (2)	0.042 (2)	0.047 (2)	−0.0088 (16)	−0.0111 (16)	−0.0130 (16)
N4	0.0377 (19)	0.0356 (18)	0.0443 (19)	−0.0076 (15)	−0.0053 (15)	−0.0126 (15)
N5	0.0360 (18)	0.0360 (18)	0.0449 (19)	−0.0065 (14)	−0.0098 (15)	−0.0105 (15)
C1	0.043 (2)	0.037 (2)	0.042 (2)	−0.0056 (18)	−0.0112 (18)	−0.0116 (17)
C2	0.073 (4)	0.058 (3)	0.046 (3)	−0.012 (3)	−0.022 (2)	−0.012 (2)
C3	0.047 (3)	0.049 (3)	0.055 (3)	−0.015 (2)	−0.010 (2)	0.001 (2)
C4	0.048 (3)	0.044 (2)	0.051 (3)	−0.020 (2)	−0.014 (2)	−0.002 (2)
C5	0.064 (3)	0.056 (3)	0.051 (3)	−0.025 (3)	−0.009 (2)	−0.009 (2)
C6	0.061 (3)	0.062 (3)	0.073 (4)	−0.019 (3)	−0.005 (3)	−0.030 (3)
C7	0.069 (4)	0.043 (3)	0.097 (5)	−0.012 (3)	−0.031 (3)	−0.018 (3)
C8	0.082 (4)	0.047 (3)	0.073 (4)	−0.019 (3)	−0.032 (3)	0.002 (3)
C9	0.063 (3)	0.050 (3)	0.050 (3)	−0.017 (2)	−0.012 (2)	−0.005 (2)
C10	0.043 (2)	0.038 (2)	0.041 (2)	−0.0041 (18)	−0.0064 (18)	−0.0127 (17)
C11	0.047 (3)	0.071 (4)	0.080 (4)	0.001 (3)	−0.018 (3)	−0.022 (3)
C12	0.068 (3)	0.038 (3)	0.058 (3)	−0.009 (2)	0.006 (3)	−0.011 (2)
C13	0.062 (3)	0.035 (2)	0.047 (2)	−0.009 (2)	−0.006 (2)	−0.0068 (19)
C14	0.059 (3)	0.049 (3)	0.057 (3)	−0.003 (2)	−0.003 (2)	−0.016 (2)
C15	0.066 (4)	0.056 (3)	0.063 (3)	0.010 (3)	−0.005 (3)	−0.015 (3)
C16	0.136 (7)	0.045 (3)	0.065 (4)	0.001 (4)	−0.020 (4)	−0.021 (3)
C17	0.140 (7)	0.064 (4)	0.087 (5)	−0.042 (5)	−0.022 (5)	−0.027 (4)
C18	0.083 (4)	0.065 (4)	0.071 (4)	−0.032 (3)	−0.005 (3)	−0.011 (3)
C19	0.040 (2)	0.034 (2)	0.0358 (19)	−0.0082 (17)	−0.0032 (16)	−0.0135 (16)
C20	0.050 (3)	0.061 (3)	0.064 (3)	−0.017 (2)	−0.015 (2)	−0.017 (3)
C21	0.045 (2)	0.048 (3)	0.042 (2)	−0.004 (2)	−0.0115 (19)	−0.0051 (19)
C22	0.045 (2)	0.039 (2)	0.050 (2)	−0.0120 (19)	−0.011 (2)	−0.0097 (19)
C23	0.087 (4)	0.040 (3)	0.059 (3)	−0.004 (3)	−0.023 (3)	−0.007 (2)
C24	0.105 (5)	0.036 (3)	0.092 (5)	0.003 (3)	−0.031 (4)	−0.017 (3)
C25	0.073 (4)	0.051 (3)	0.085 (4)	−0.011 (3)	−0.005 (3)	−0.033 (3)
C26	0.073 (4)	0.065 (4)	0.058 (3)	−0.010 (3)	−0.008 (3)	−0.023 (3)
C27	0.053 (3)	0.052 (3)	0.052 (3)	−0.001 (2)	−0.009 (2)	−0.013 (2)
C28	0.043 (2)	0.047 (3)	0.058 (3)	−0.013 (2)	−0.007 (2)	−0.013 (2)
C29	0.050 (3)	0.049 (3)	0.069 (3)	−0.019 (2)	−0.014 (2)	−0.009 (2)
C30	0.068 (3)	0.038 (2)	0.065 (3)	−0.023 (2)	−0.020 (3)	−0.008 (2)
C31	0.056 (3)	0.032 (2)	0.047 (2)	−0.0099 (19)	−0.020 (2)	−0.0066 (18)
C32	0.042 (2)	0.0299 (19)	0.044 (2)	−0.0044 (16)	−0.0164 (18)	−0.0099 (16)
C33	0.077 (4)	0.037 (2)	0.057 (3)	−0.007 (2)	−0.024 (3)	−0.018 (2)
C34	0.064 (3)	0.041 (3)	0.053 (3)	0.002 (2)	−0.013 (2)	−0.022 (2)
C35	0.047 (2)	0.041 (2)	0.039 (2)	0.0018 (19)	−0.0105 (19)	−0.0123 (18)
C36	0.040 (2)	0.034 (2)	0.037 (2)	−0.0033 (17)	−0.0100 (17)	−0.0114 (16)
C37	0.042 (3)	0.061 (3)	0.048 (3)	0.003 (2)	−0.007 (2)	−0.024 (2)
C38	0.041 (2)	0.066 (3)	0.049 (3)	−0.013 (2)	0.000 (2)	−0.017 (2)
C39	0.039 (2)	0.052 (3)	0.047 (2)	−0.013 (2)	−0.0019 (19)	−0.016 (2)

Geometric parameters (Å, º) top

Eu1—N5	2.540 (4)	C12—H12B	0.9700
Eu1—N4	2.569 (4)	C13—C14	1.375 (7)
Eu1—S4	2.8451 (13)	C13—C18	1.384 (8)
Eu1—S3	2.8523 (14)	C14—C15	1.377 (8)
Eu1—S2	2.8627 (13)	C14—H14	0.9300
Eu1—S5	2.8781 (12)	C15—C16	1.372 (10)
Eu1—S6	2.8859 (12)	C15—H15	0.9300
Eu1—S1	2.8970 (12)	C16—C17	1.357 (12)
S1—C1	1.702 (5)	C16—H16	0.9300
S2—C1	1.723 (5)	C17—C18	1.389 (10)
S3—C10	1.717 (5)	C17—H17	0.9300
S4—C10	1.716 (5)	C18—H18	0.9300
S5—C19	1.713 (4)	C20—H20A	0.9600
S6—C19	1.717 (4)	C20—H20B	0.9600
N1—C1	1.349 (6)	C20—H20C	0.9600
N1—C2	1.465 (6)	C21—C22	1.512 (7)
N1—C3	1.473 (6)	C21—H21A	0.9700
N2—C10	1.320 (6)	C21—H21B	0.9700
N2—C11	1.455 (7)	C22—C27	1.376 (7)
N2—C12	1.471 (7)	C22—C23	1.380 (7)
N3—C19	1.337 (6)	C23—C24	1.384 (9)
N3—C20	1.450 (6)	C23—H23	0.9300
N3—C21	1.475 (6)	C24—C25	1.360 (10)
N4—C39	1.315 (6)	C24—H24	0.9300
N4—C36	1.357 (5)	C25—C26	1.360 (9)
N5—C28	1.330 (6)	C25—H25	0.9300
N5—C32	1.357 (5)	C26—C27	1.385 (8)
C2—H2A	0.9600	C26—H26	0.9300
C2—H2B	0.9600	C27—H27	0.9300
C2—H2C	0.9600	C28—C29	1.397 (7)
C3—C4	1.505 (7)	C28—H28	0.9300
C3—H3A	0.9700	C29—C30	1.344 (8)
C3—H3B	0.9700	C29—H29	0.9300
C4—C5	1.377 (7)	C30—C31	1.419 (7)
C4—C9	1.386 (7)	C30—H30	0.9300
C5—C6	1.388 (8)	C31—C32	1.402 (6)
C5—H5	0.9300	C31—C33	1.415 (7)
C6—C7	1.361 (9)	C32—C36	1.443 (6)
C6—H6	0.9300	C33—C34	1.343 (8)
C7—C8	1.372 (9)	C33—H33	0.9300
C7—H7	0.9300	C34—C35	1.431 (7)
C8—C9	1.376 (8)	C34—H34	0.9300
C8—H8	0.9300	C35—C36	1.403 (6)
C9—H9	0.9300	C35—C37	1.408 (7)
C11—H11A	0.9600	C37—C38	1.367 (8)
C11—H11B	0.9600	C37—H37	0.9300
C11—H11C	0.9600	C38—C39	1.410 (7)
C12—C13	1.501 (7)	C38—H38	0.9300
C12—H12A	0.9700	C39—H39	0.9300

N5—Eu1—N4	64.41 (11)	N2—C12—H12A	108.7
N5—Eu1—S4	91.49 (9)	C13—C12—H12A	108.7
N4—Eu1—S4	141.09 (9)	N2—C12—H12B	108.7
N5—Eu1—S3	94.45 (9)	C13—C12—H12B	108.7
N4—Eu1—S3	144.46 (9)	H12A—C12—H12B	107.6
S4—Eu1—S3	61.51 (4)	C14—C13—C18	118.7 (5)
N5—Eu1—S2	136.16 (9)	C14—C13—C12	120.6 (5)
N4—Eu1—S2	87.66 (9)	C18—C13—C12	120.6 (5)
S4—Eu1—S2	90.73 (4)	C13—C14—C15	121.1 (6)
S3—Eu1—S2	124.44 (5)	C13—C14—H14	119.4
N5—Eu1—S5	71.80 (8)	C15—C14—H14	119.4
N4—Eu1—S5	73.60 (9)	C16—C15—C14	119.4 (6)
S4—Eu1—S5	129.73 (4)	C16—C15—H15	120.3
S3—Eu1—S5	72.65 (4)	C14—C15—H15	120.3
S2—Eu1—S5	134.15 (4)	C17—C16—C15	120.5 (6)
N5—Eu1—S6	128.70 (8)	C17—C16—H16	119.7
N4—Eu1—S6	82.53 (9)	C15—C16—H16	119.7
S4—Eu1—S6	134.30 (4)	C16—C17—C18	120.2 (7)
S3—Eu1—S6	90.97 (4)	C16—C17—H17	119.9
S2—Eu1—S6	75.11 (4)	C18—C17—H17	119.9
S5—Eu1—S6	61.43 (3)	C13—C18—C17	119.9 (7)
N5—Eu1—S1	78.24 (8)	C13—C18—H18	120.0
N4—Eu1—S1	75.12 (9)	C17—C18—H18	120.0
S4—Eu1—S1	70.08 (4)	N3—C19—S5	120.9 (3)
S3—Eu1—S1	130.85 (4)	N3—C19—S6	120.9 (3)
S2—Eu1—S1	61.59 (3)	S5—C19—S6	118.2 (3)
S5—Eu1—S1	143.61 (3)	N3—C20—H20A	109.5
S6—Eu1—S1	131.41 (3)	N3—C20—H20B	109.5
C1—S1—Eu1	89.39 (15)	H20A—C20—H20B	109.5
C1—S2—Eu1	90.12 (16)	N3—C20—H20C	109.5
C10—S3—Eu1	91.03 (16)	H20A—C20—H20C	109.5
C10—S4—Eu1	91.30 (16)	H20B—C20—H20C	109.5
C19—S5—Eu1	89.86 (15)	N3—C21—C22	113.9 (4)
C19—S6—Eu1	89.51 (15)	N3—C21—H21A	108.8
C1—N1—C2	122.1 (4)	C22—C21—H21A	108.8
C1—N1—C3	123.1 (4)	N3—C21—H21B	108.8
C2—N1—C3	114.8 (4)	C22—C21—H21B	108.8
C10—N2—C11	121.8 (4)	H21A—C21—H21B	107.7
C10—N2—C12	122.2 (4)	C27—C22—C23	118.3 (5)
C11—N2—C12	115.7 (4)	C27—C22—C21	122.5 (4)
C19—N3—C20	122.8 (4)	C23—C22—C21	119.2 (4)
C19—N3—C21	121.3 (4)	C24—C23—C22	120.4 (6)
C20—N3—C21	115.9 (4)	C24—C23—H23	119.8
C39—N4—C36	118.3 (4)	C22—C23—H23	119.8
C39—N4—Eu1	122.7 (3)	C25—C24—C23	121.0 (6)
C36—N4—Eu1	119.0 (3)	C25—C24—H24	119.5
C28—N5—C32	117.4 (4)	C23—C24—H24	119.5
C28—N5—Eu1	122.1 (3)	C26—C25—C24	118.7 (6)
C32—N5—Eu1	120.3 (3)	C26—C25—H25	120.6
N1—C1—S1	120.1 (3)	C24—C25—H25	120.6
N1—C1—S2	121.0 (3)	C25—C26—C27	121.3 (6)
S1—C1—S2	118.9 (3)	C25—C26—H26	119.3
N1—C2—H2A	109.5	C27—C26—H26	119.3
N1—C2—H2B	109.5	C22—C27—C26	120.2 (5)
H2A—C2—H2B	109.5	C22—C27—H27	119.9
N1—C2—H2C	109.5	C26—C27—H27	119.9
H2A—C2—H2C	109.5	N5—C28—C29	123.3 (5)
H2B—C2—H2C	109.5	N5—C28—H28	118.4
N1—C3—C4	111.7 (4)	C29—C28—H28	118.4
N1—C3—H3A	109.3	C30—C29—C28	119.6 (5)
C4—C3—H3A	109.3	C30—C29—H29	120.2
N1—C3—H3B	109.3	C28—C29—H29	120.2
C4—C3—H3B	109.3	C29—C30—C31	119.6 (4)
H3A—C3—H3B	107.9	C29—C30—H30	120.2
C5—C4—C9	118.2 (5)	C31—C30—H30	120.2
C5—C4—C3	121.1 (4)	C32—C31—C30	117.1 (4)
C9—C4—C3	120.7 (5)	C32—C31—C33	120.2 (5)
C4—C5—C6	120.7 (5)	C30—C31—C33	122.7 (4)
C4—C5—H5	119.7	N5—C32—C31	123.0 (4)
C6—C5—H5	119.7	N5—C32—C36	117.9 (4)
C7—C6—C5	120.4 (6)	C31—C32—C36	119.1 (4)
C7—C6—H6	119.8	C34—C33—C31	121.1 (5)
C5—C6—H6	119.8	C34—C33—H33	119.5
C6—C7—C8	119.5 (6)	C31—C33—H33	119.5
C6—C7—H7	120.3	C33—C34—C35	120.8 (4)
C8—C7—H7	120.3	C33—C34—H34	119.6
C9—C8—C7	120.5 (6)	C35—C34—H34	119.6
C9—C8—H8	119.8	C36—C35—C37	117.7 (4)
C7—C8—H8	119.8	C36—C35—C34	119.7 (4)
C8—C9—C4	120.7 (6)	C37—C35—C34	122.6 (4)
C8—C9—H9	119.6	N4—C36—C35	122.5 (4)
C4—C9—H9	119.6	N4—C36—C32	118.4 (4)
N2—C10—S4	121.0 (4)	C35—C36—C32	119.1 (4)
N2—C10—S3	122.7 (4)	C38—C37—C35	119.7 (4)
S4—C10—S3	116.2 (3)	C38—C37—H37	120.2
N2—C11—H11A	109.5	C35—C37—H37	120.2
N2—C11—H11B	109.5	C37—C38—C39	118.5 (5)
H11A—C11—H11B	109.5	C37—C38—H38	120.8
N2—C11—H11C	109.5	C39—C38—H38	120.8
H11A—C11—H11C	109.5	N4—C39—C38	123.4 (5)
H11B—C11—H11C	109.5	N4—C39—H39	118.3
N2—C12—C13	114.0 (4)	C38—C39—H39	118.3

N5—Eu1—S1—C1	−160.64 (18)	C4—C5—C6—C7	0.0 (8)
N4—Eu1—S1—C1	−94.29 (17)	C5—C6—C7—C8	−0.8 (9)
S4—Eu1—S1—C1	103.41 (16)	C6—C7—C8—C9	1.4 (9)
S3—Eu1—S1—C1	113.68 (16)	C7—C8—C9—C4	−1.2 (9)
S2—Eu1—S1—C1	1.20 (16)	C5—C4—C9—C8	0.4 (8)
S5—Eu1—S1—C1	−125.73 (16)	C3—C4—C9—C8	179.1 (5)
S6—Eu1—S1—C1	−28.73 (16)	C11—N2—C10—S4	−3.4 (7)
N5—Eu1—S2—C1	24.9 (2)	C12—N2—C10—S4	170.7 (4)
N4—Eu1—S2—C1	73.14 (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—C1	137.44 (15)	Eu1—S4—C10—S3	0.8 (3)
S6—Eu1—S2—C1	156.03 (16)	Eu1—S3—C10—N2	175.9 (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—C13	130.3 (5)
N4—Eu1—S3—C10	−139.3 (2)	C11—N2—C12—C13	−55.4 (7)
S4—Eu1—S3—C10	0.48 (17)	N2—C12—C13—C14	115.9 (6)
S2—Eu1—S3—C10	69.71 (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—C10	142.26 (17)	C12—C13—C14—C15	176.7 (6)
S1—Eu1—S3—C10	−10.51 (19)	C13—C14—C15—C16	1.3 (9)
N5—Eu1—S4—C10	93.77 (18)	C14—C15—C16—C17	0.2 (11)
N4—Eu1—S4—C10	142.8 (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—C10	26.39 (18)	C16—C17—C18—C13	2.5 (12)
S6—Eu1—S4—C10	−60.29 (17)	C20—N3—C19—S5	177.6 (4)
S1—Eu1—S4—C10	170.70 (17)	C21—N3—C19—S5	−0.7 (6)
N5—Eu1—S5—C19	152.45 (16)	C20—N3—C19—S6	−2.1 (6)
N4—Eu1—S5—C19	84.61 (16)	C21—N3—C19—S6	179.6 (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—S6	9.6 (2)
S2—Eu1—S5—C19	14.80 (15)	Eu1—S6—C19—N3	170.0 (3)
S6—Eu1—S5—C19	−5.74 (14)	Eu1—S6—C19—S5	−9.6 (2)
S1—Eu1—S5—C19	116.31 (14)	C19—N3—C21—C22	95.4 (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—C19	124.76 (14)	N3—C21—C22—C23	150.1 (5)
S3—Eu1—S6—C19	75.32 (14)	C27—C22—C23—C24	−0.7 (9)
S2—Eu1—S6—C19	−159.18 (14)	C21—C22—C23—C24	177.3 (6)
S5—Eu1—S6—C19	5.73 (14)	C22—C23—C24—C25	0.2 (11)
S1—Eu1—S6—C19	−132.17 (14)	C23—C24—C25—C26	0.3 (11)
N5—Eu1—N4—C39	−178.8 (4)	C24—C25—C26—C27	−0.3 (11)
S4—Eu1—N4—C39	124.3 (3)	C23—C22—C27—C26	0.8 (9)
S3—Eu1—N4—C39	−120.3 (3)	C21—C22—C27—C26	−177.3 (5)
S2—Eu1—N4—C39	36.1 (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—C39	97.3 (4)	N5—C28—C29—C30	1.5 (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—C32	1.1 (7)
S3—Eu1—N4—C36	56.6 (4)	C29—C30—C31—C33	179.0 (5)
S2—Eu1—N4—C36	−147.0 (3)	C28—N5—C32—C31	2.4 (6)
S5—Eu1—N4—C36	75.4 (3)	Eu1—N5—C32—C31	177.8 (3)
S6—Eu1—N4—C36	137.8 (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—C28	176.8 (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—C28	26.6 (4)	C30—C31—C32—C36	177.4 (4)
S2—Eu1—N5—C28	−127.5 (3)	C33—C31—C32—C36	−0.7 (6)
S5—Eu1—N5—C28	96.7 (4)	C32—C31—C33—C34	1.4 (7)
S6—Eu1—N5—C28	121.5 (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—C32	1.7 (3)	C33—C34—C35—C36	−1.0 (7)
S4—Eu1—N5—C32	150.0 (3)	C33—C34—C35—C37	−180.0 (5)
S3—Eu1—N5—C32	−148.5 (3)	C39—N4—C36—C35	0.3 (6)
S2—Eu1—N5—C32	57.4 (3)	Eu1—N4—C36—C35	−176.8 (3)
S5—Eu1—N5—C32	−78.4 (3)	C39—N4—C36—C32	179.1 (4)
S6—Eu1—N5—C32	−53.7 (3)	Eu1—N4—C36—C32	2.0 (5)
S1—Eu1—N5—C32	80.7 (3)	C37—C35—C36—N4	−0.5 (6)
C2—N1—C1—S1	2.4 (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—C32	1.7 (6)
C3—N1—C1—S2	2.8 (6)	N5—C32—C36—N4	−0.4 (6)
Eu1—S1—C1—N1	178.8 (4)	C31—C32—C36—N4	−179.7 (4)
Eu1—S1—C1—S2	−2.0 (3)	N5—C32—C36—C35	178.5 (4)
Eu1—S2—C1—N1	−178.8 (4)	C31—C32—C36—C35	−0.8 (6)
Eu1—S2—C1—S1	2.0 (3)	C36—C35—C37—C38	0.4 (7)
C1—N1—C3—C4	−113.7 (5)	C34—C35—C37—C38	179.4 (5)
C2—N1—C3—C4	65.9 (6)	C35—C37—C38—C39	0.0 (8)
N1—C3—C4—C5	64.9 (6)	C36—N4—C39—C38	0.1 (7)
N1—C3—C4—C9	−113.8 (5)	Eu1—N4—C39—C38	177.1 (4)
C9—C4—C5—C6	0.2 (8)	C37—C38—C39—N4	−0.3 (8)
C3—C4—C5—C6	−178.4 (5)

Experimental details

Crystal data
Chemical formula	[Eu(C₉H₁₀NS₂)₃(C₁₂H₈N₂)]
M_r	921.06
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.691 (1), 12.288 (1), 16.553 (2)
α, β, γ (°)	73.652 (2), 74.720 (2), 71.629 (2)
V (Å³)	1943.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.48 × 0.35 × 0.20

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.451, 0.694
No. of measured, independent and observed [I > 2σ(I)] reflections	21775, 8695, 7425
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.08
No. of reflections	8695
No. of parameters	463
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.56, −1.65

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Eu1—N5	2.540 (4)	Eu1—S2	2.8627 (13)
Eu1—N4	2.569 (4)	Eu1—S5	2.8781 (12)
Eu1—S4	2.8451 (13)	Eu1—S6	2.8859 (12)
Eu1—S3	2.8523 (14)	Eu1—S1	2.8970 (12)

Acknowledgements

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

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