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

Clegg, W.; Harrington, R.W.

doi:10.1107/S1600536807012329

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

W. Clegg and R. W. Harrington

In the title compound, (C₁₂H₉N)₄[EuCl₆]Cl, the Eu^III 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 3.3–3.7Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012329/wn2129sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012329/wn2129Isup2.hkl Contains datablock I

CCDC reference: 643664

checkCIF report

Key indicators

Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.008 Å
R factor = 0.053
wR factor = 0.092
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom C5      has ADP max/min Ratio .............       4.60 oblat
PLAT432_ALERT_2_B Short Inter X...Y Contact  Cl4    ..  C13     ..       3.12 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Eu     -   Cl3     ..       6.35 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Eu     -   Cl4     ..       7.58 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  Cl4    ..  C15     ..       3.24 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.86(6), Rep     0.87(2) ......       3.00 su-Ra
              N1   -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.87(5), Rep   0.872(19) ......       2.63 su-Ra
              N3   -H3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.87(5), Rep   0.863(19) ......       2.63 su-Ra
              N6   -H6      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.87(6), Rep   0.863(19) ......       3.16 su-Ra
              N8   -H8      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(6), Rep     0.87(2) ......       3.00 su-Ra
              N1   -H1      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(5), Rep   0.872(19) ......       2.63 su-Ra
              N3   -H3      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(5), Rep   0.863(19) ......       2.63 su-Ra
              N6   -H6      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(6), Rep   0.863(19) ......       3.16 su-Ra
              N8   -H8      1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C12 H9 N2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          6
              Cl

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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)].

Structure description top

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

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]Cl	F(000) = 2248
M_r = 1124.96	D_x = 1.685 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.6308 (5) Å	Cell parameters from 26437 reflections
b = 11.2069 (3) Å	θ = 2.2–29.0°
c = 24.0726 (7) Å	µ = 1.88 mm⁻¹
β = 111.197 (2)°	T = 160 K
V = 4434.6 (2) Å³	Block, colourless
Z = 4	0.38 × 0.30 × 0.25 mm

Data collection top

Bruker SMART 1K CCD diffractometer	7803 independent reflections
Radiation source: sealed tube	6822 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
thin–slice ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −13→13
T_min = 0.530, T_max = 0.650	l = −28→28
31682 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)] = 0.053	Hydrogen site location: mixed
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ²(F_o²) + (0.0056P)² + 19.2232P] where P = (F_o² + 2F_c²)/3
7803 reflections	(Δ/σ)_max = 0.001
589 parameters	Δρ_max = 0.86 e Å⁻³
162 restraints	Δρ_min = −1.82 e Å⁻³

Crystal data top

(C₁₂H₉N₂)₄[EuCl₆]Cl	V = 4434.6 (2) Å³
M_r = 1124.96	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.6308 (5) Å	µ = 1.88 mm⁻¹
b = 11.2069 (3) Å	T = 160 K
c = 24.0726 (7) Å	0.38 × 0.30 × 0.25 mm
β = 111.197 (2)°

Data collection top

Bruker SMART 1K CCD diffractometer	7803 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	6822 reflections with I > 2σ(I)
T_min = 0.530, T_max = 0.650	R_int = 0.048
31682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	162 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ²(F_o²) + (0.0056P)² + 19.2232P] where P = (F_o² + 2F_c²)/3
7803 reflections	Δρ_max = 0.86 e Å⁻³
589 parameters	Δρ_min = −1.82 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Eu	0.715425 (16)	0.51035 (2)	0.405963 (12)	0.01302 (8)
Cl1	0.61670 (9)	0.60313 (13)	0.30368 (6)	0.0250 (3)
Cl2	0.74559 (9)	0.73182 (12)	0.45410 (7)	0.0244 (3)
Cl3	0.67986 (9)	0.28636 (12)	0.36491 (6)	0.0252 (3)
Cl4	0.59307 (8)	0.49166 (12)	0.44632 (6)	0.0203 (3)
Cl5	0.84137 (9)	0.52383 (14)	0.36861 (7)	0.0288 (3)
Cl6	0.81255 (8)	0.41411 (12)	0.51454 (6)	0.0207 (3)
Cl7	0.79884 (8)	−0.18435 (12)	0.63937 (6)	0.0189 (3)
N1	0.7993 (3)	−0.3601 (4)	0.7363 (2)	0.0214 (11)
H1	0.813 (4)	−0.324 (5)	0.710 (2)	0.026*
N2	0.9261 (3)	−0.4517 (4)	0.7076 (2)	0.0222 (11)
N3	0.7145 (3)	0.4527 (4)	0.6003 (2)	0.0165 (10)
H3	0.751 (3)	0.414 (4)	0.591 (2)	0.020*
N4	0.7667 (3)	0.2306 (4)	0.6471 (2)	0.0172 (10)
N5	0.5691 (3)	−0.0867 (4)	0.6198 (2)	0.0192 (10)
N6	0.6617 (3)	−0.0215 (4)	0.5547 (2)	0.0179 (10)
H6	0.676 (3)	−0.078 (4)	0.581 (2)	0.022*
N7	0.9429 (3)	0.0504 (4)	0.6021 (2)	0.0224 (11)
N8	0.9310 (3)	−0.1915 (4)	0.5828 (2)	0.0166 (10)
H8	0.897 (3)	−0.156 (5)	0.596 (2)	0.020*
C1	0.7423 (4)	−0.3075 (5)	0.7520 (3)	0.0290 (14)
H1A	0.7254	−0.2285	0.7390	0.035*
C2	0.7079 (4)	−0.3674 (6)	0.7870 (3)	0.0303 (14)
H2	0.6682	−0.3296	0.7991	0.036*
C3	0.7318 (3)	−0.4824 (6)	0.8042 (3)	0.0259 (13)
H3A	0.7075	−0.5247	0.8277	0.031*
C4	0.7911 (3)	−0.5379 (5)	0.7876 (2)	0.0191 (12)
C5	0.8268 (3)	−0.4715 (5)	0.7540 (2)	0.0154 (11)
C6	0.8938 (3)	−0.5200 (5)	0.7405 (2)	0.0193 (11)
C7	0.9236 (3)	−0.6337 (5)	0.7627 (2)	0.0191 (12)
C8	0.9936 (3)	−0.6726 (5)	0.7541 (3)	0.0231 (13)
H8A	1.0173	−0.7472	0.7698	0.028*
C9	1.0281 (3)	−0.6029 (5)	0.7231 (3)	0.0245 (13)
H9	1.0764	−0.6276	0.7176	0.029*
C10	0.9913 (3)	−0.4955 (5)	0.6999 (3)	0.0279 (13)
H10	1.0146	−0.4500	0.6767	0.033*
C11	0.8193 (3)	−0.6566 (5)	0.8059 (2)	0.0203 (12)
H11	0.7932	−0.7040	0.8265	0.024*
C12	0.8832 (3)	−0.7011 (5)	0.7939 (2)	0.0204 (12)
H12	0.9016	−0.7796	0.8068	0.024*
C13	0.6944 (3)	0.5615 (5)	0.5780 (2)	0.0199 (12)
H13	0.7202	0.5950	0.5532	0.024*
C14	0.6357 (3)	0.6265 (5)	0.5909 (3)	0.0236 (13)
H14	0.6230	0.7057	0.5765	0.028*
C15	0.5964 (3)	0.5757 (5)	0.6244 (2)	0.0195 (12)
H15	0.5544	0.6183	0.6318	0.023*
C16	0.6178 (3)	0.4600 (5)	0.6480 (2)	0.0177 (11)
C17	0.6787 (3)	0.3997 (5)	0.6358 (2)	0.0160 (11)
C18	0.7053 (3)	0.2832 (5)	0.6596 (2)	0.0157 (11)
C19	0.6669 (3)	0.2311 (5)	0.6960 (2)	0.0184 (12)
C20	0.6950 (4)	0.1188 (5)	0.7205 (2)	0.0232 (13)
H20	0.6711	0.0797	0.7451	0.028*
C21	0.7570 (4)	0.0667 (5)	0.7085 (3)	0.0241 (13)
H21	0.7774	−0.0088	0.7252	0.029*
C22	0.7908 (3)	0.1250 (5)	0.6712 (3)	0.0222 (13)
H22	0.8334	0.0862	0.6629	0.027*
C23	0.5787 (3)	0.4028 (5)	0.6839 (3)	0.0230 (13)
H23	0.5360	0.4424	0.6919	0.028*
C24	0.6025 (3)	0.2932 (5)	0.7063 (3)	0.0242 (13)
H24	0.5757	0.2562	0.7297	0.029*
C25	0.5260 (4)	−0.1128 (5)	0.6531 (3)	0.0241 (13)
H25	0.5361	−0.1867	0.6738	0.029*
C26	0.4662 (4)	−0.0372 (6)	0.6594 (3)	0.0279 (14)
H26	0.4375	−0.0590	0.6845	0.033*
C27	0.4500 (4)	0.0676 (6)	0.6291 (3)	0.0253 (13)
H27	0.4092	0.1192	0.6327	0.030*
C28	0.4930 (3)	0.0998 (5)	0.5926 (2)	0.0159 (11)
C29	0.5534 (3)	0.0196 (5)	0.5906 (2)	0.0167 (11)
C30	0.6009 (3)	0.0513 (5)	0.5555 (2)	0.0165 (11)
C31	0.5867 (3)	0.1583 (5)	0.5231 (2)	0.0168 (11)
C32	0.6346 (3)	0.1823 (5)	0.4885 (3)	0.0216 (12)
H32	0.6266	0.2540	0.4660	0.026*
C33	0.6924 (4)	0.1025 (5)	0.4871 (3)	0.0259 (13)
H33	0.7228	0.1168	0.4623	0.031*
C34	0.7069 (3)	0.0009 (5)	0.5219 (2)	0.0249 (12)
H34	0.7489	−0.0528	0.5225	0.030*
C35	0.4813 (3)	0.2099 (5)	0.5607 (3)	0.0217 (12)
H35	0.4414	0.2643	0.5632	0.026*
C36	0.5256 (3)	0.2385 (5)	0.5272 (3)	0.0213 (12)
H36	0.5163	0.3121	0.5062	0.026*
C37	0.9497 (4)	0.1675 (5)	0.6094 (3)	0.0259 (14)
H37	0.9091	0.2086	0.6193	0.031*
C38	1.0139 (4)	0.2347 (5)	0.6033 (3)	0.0294 (14)
H38	1.0162	0.3186	0.6094	0.035*
C39	1.0725 (4)	0.1785 (5)	0.5888 (2)	0.0229 (13)
H39	1.1170	0.2221	0.5857	0.027*
C40	1.0661 (3)	0.0532 (5)	0.5783 (2)	0.0178 (11)
C41	1.0003 (3)	−0.0065 (5)	0.5862 (2)	0.0181 (11)
C42	0.9926 (3)	−0.1312 (5)	0.5748 (2)	0.0157 (11)
C43	1.0464 (3)	−0.1926 (5)	0.5551 (2)	0.0159 (11)
C44	1.0333 (3)	−0.3157 (5)	0.5437 (3)	0.0235 (13)
H44	1.0697	−0.3600	0.5308	0.028*
C45	0.9689 (3)	−0.3721 (5)	0.5510 (3)	0.0226 (13)
H45	0.9595	−0.4547	0.5423	0.027*
C46	0.9177 (3)	−0.3068 (5)	0.5714 (2)	0.0208 (12)
H46	0.8729	−0.3446	0.5771	0.025*
C47	1.1219 (3)	−0.0107 (5)	0.5591 (2)	0.0228 (12)
H47	1.1664	0.0301	0.5544	0.027*
C48	1.1123 (3)	−0.1299 (5)	0.5474 (2)	0.0202 (12)
H48	1.1496	−0.1713	0.5341	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu	0.01412 (13)	0.01092 (13)	0.01640 (14)	0.00049 (12)	0.00837 (10)	0.00054 (12)
Cl1	0.0229 (8)	0.0307 (8)	0.0211 (8)	0.0023 (6)	0.0076 (6)	0.0054 (6)
Cl2	0.0256 (8)	0.0185 (7)	0.0313 (8)	−0.0029 (6)	0.0129 (7)	−0.0067 (6)
Cl3	0.0386 (9)	0.0185 (7)	0.0253 (8)	−0.0038 (6)	0.0198 (7)	−0.0039 (6)
Cl4	0.0175 (6)	0.0197 (7)	0.0256 (7)	−0.0003 (6)	0.0102 (6)	0.0005 (6)
Cl5	0.0251 (8)	0.0322 (8)	0.0371 (9)	−0.0019 (6)	0.0207 (7)	−0.0003 (7)
Cl6	0.0178 (7)	0.0255 (7)	0.0210 (7)	0.0048 (6)	0.0095 (6)	0.0034 (6)
Cl7	0.0165 (7)	0.0196 (7)	0.0231 (7)	0.0023 (5)	0.0101 (6)	0.0040 (6)
N1	0.021 (3)	0.025 (3)	0.022 (3)	0.002 (2)	0.013 (2)	0.004 (2)
N2	0.023 (3)	0.021 (2)	0.027 (3)	−0.003 (2)	0.013 (2)	0.004 (2)
N3	0.012 (2)	0.021 (2)	0.015 (2)	−0.0033 (19)	0.003 (2)	−0.0027 (19)
N4	0.016 (2)	0.022 (2)	0.019 (3)	−0.0009 (19)	0.011 (2)	0.0000 (19)
N5	0.022 (3)	0.015 (2)	0.020 (3)	−0.0031 (19)	0.007 (2)	−0.0013 (19)
N6	0.022 (2)	0.013 (2)	0.019 (2)	0.0051 (19)	0.008 (2)	0.0028 (19)
N7	0.027 (3)	0.021 (2)	0.025 (3)	0.000 (2)	0.016 (2)	−0.003 (2)
N8	0.012 (2)	0.023 (2)	0.014 (2)	0.0046 (19)	0.004 (2)	0.0005 (19)
C1	0.026 (3)	0.022 (3)	0.041 (4)	0.001 (3)	0.015 (3)	−0.001 (3)
C2	0.025 (3)	0.038 (4)	0.033 (4)	0.002 (3)	0.016 (3)	−0.010 (3)
C3	0.023 (3)	0.038 (3)	0.021 (3)	−0.003 (3)	0.014 (3)	−0.005 (3)
C4	0.023 (3)	0.021 (3)	0.008 (3)	−0.003 (2)	−0.001 (2)	−0.001 (2)
C5	0.014 (2)	0.020 (2)	0.006 (2)	0.0038 (19)	−0.0038 (18)	0.0067 (19)
C6	0.020 (3)	0.018 (3)	0.017 (3)	−0.005 (2)	0.003 (2)	−0.001 (2)
C7	0.016 (3)	0.023 (3)	0.013 (3)	−0.001 (2)	−0.002 (2)	−0.002 (2)
C8	0.018 (3)	0.023 (3)	0.023 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C9	0.018 (3)	0.031 (3)	0.027 (3)	0.003 (2)	0.012 (3)	−0.003 (3)
C10	0.028 (3)	0.023 (3)	0.038 (4)	0.000 (3)	0.018 (3)	0.001 (3)
C11	0.022 (3)	0.022 (3)	0.015 (3)	−0.009 (2)	0.005 (2)	0.004 (2)
C12	0.026 (3)	0.019 (3)	0.012 (3)	0.000 (2)	0.002 (2)	0.005 (2)
C13	0.015 (3)	0.023 (3)	0.014 (3)	−0.004 (2)	−0.004 (2)	−0.001 (2)
C14	0.016 (3)	0.023 (3)	0.027 (3)	0.002 (2)	0.001 (3)	0.000 (2)
C15	0.009 (3)	0.022 (3)	0.023 (3)	0.001 (2)	0.000 (2)	−0.008 (2)
C16	0.011 (3)	0.023 (3)	0.015 (3)	−0.005 (2)	0.001 (2)	−0.007 (2)
C17	0.015 (3)	0.018 (3)	0.015 (3)	−0.004 (2)	0.006 (2)	0.000 (2)
C18	0.015 (3)	0.017 (3)	0.015 (3)	−0.004 (2)	0.005 (2)	−0.005 (2)
C19	0.016 (3)	0.023 (3)	0.015 (3)	−0.006 (2)	0.005 (2)	−0.005 (2)
C20	0.034 (4)	0.022 (3)	0.015 (3)	−0.011 (2)	0.011 (3)	−0.002 (2)
C21	0.029 (3)	0.021 (3)	0.020 (3)	−0.002 (2)	0.007 (3)	0.004 (2)
C22	0.019 (3)	0.023 (3)	0.026 (3)	−0.001 (2)	0.010 (3)	−0.002 (2)
C23	0.017 (3)	0.032 (3)	0.025 (3)	−0.003 (2)	0.012 (3)	−0.009 (3)
C24	0.020 (3)	0.035 (3)	0.021 (3)	−0.008 (3)	0.011 (3)	−0.008 (3)
C25	0.027 (3)	0.026 (3)	0.019 (3)	−0.005 (2)	0.009 (3)	0.000 (2)
C26	0.028 (3)	0.039 (4)	0.021 (3)	0.000 (3)	0.013 (3)	0.003 (3)
C27	0.022 (3)	0.034 (3)	0.023 (3)	0.003 (3)	0.013 (3)	−0.004 (3)
C28	0.013 (3)	0.016 (3)	0.017 (3)	−0.001 (2)	0.004 (2)	−0.004 (2)
C29	0.016 (3)	0.016 (3)	0.014 (3)	0.002 (2)	0.001 (2)	−0.002 (2)
C30	0.017 (3)	0.018 (3)	0.015 (3)	0.004 (2)	0.006 (2)	0.003 (2)
C31	0.017 (3)	0.015 (3)	0.017 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C32	0.026 (3)	0.020 (3)	0.021 (3)	−0.003 (2)	0.011 (3)	0.004 (2)
C33	0.026 (3)	0.033 (3)	0.023 (3)	−0.002 (3)	0.014 (3)	0.003 (3)
C34	0.025 (3)	0.027 (3)	0.025 (3)	0.006 (3)	0.012 (2)	0.000 (3)
C35	0.017 (3)	0.021 (3)	0.026 (3)	0.005 (2)	0.005 (3)	−0.002 (2)
C36	0.021 (3)	0.017 (3)	0.023 (3)	0.004 (2)	0.004 (3)	0.003 (2)
C37	0.034 (4)	0.024 (3)	0.022 (3)	0.005 (3)	0.014 (3)	−0.002 (3)
C38	0.043 (4)	0.024 (3)	0.028 (4)	−0.005 (3)	0.020 (3)	−0.004 (3)
C39	0.028 (3)	0.024 (3)	0.016 (3)	−0.007 (2)	0.007 (3)	−0.001 (2)
C40	0.020 (3)	0.022 (3)	0.008 (3)	−0.004 (2)	0.002 (2)	0.001 (2)
C41	0.019 (3)	0.021 (3)	0.014 (3)	−0.001 (2)	0.006 (2)	−0.004 (2)
C42	0.013 (3)	0.023 (3)	0.010 (3)	−0.002 (2)	0.003 (2)	−0.001 (2)
C43	0.011 (3)	0.027 (3)	0.008 (3)	0.005 (2)	0.001 (2)	0.004 (2)
C44	0.020 (3)	0.029 (3)	0.022 (3)	0.009 (2)	0.008 (3)	0.000 (3)
C45	0.022 (3)	0.018 (3)	0.027 (3)	0.002 (2)	0.008 (3)	−0.003 (2)
C46	0.015 (3)	0.024 (3)	0.021 (3)	−0.001 (2)	0.005 (2)	0.001 (2)
C47	0.019 (3)	0.029 (3)	0.021 (3)	0.001 (3)	0.007 (2)	0.004 (3)
C48	0.015 (3)	0.035 (3)	0.014 (3)	0.008 (2)	0.009 (2)	0.003 (2)

Geometric parameters (Å, º) top

Eu—Cl1	2.6596 (14)	C16—C23	1.437 (8)
Eu—Cl2	2.7092 (14)	C17—C18	1.434 (7)
Eu—Cl3	2.6876 (14)	C18—C19	1.411 (7)
Eu—Cl4	2.6753 (13)	C19—C20	1.403 (8)
Eu—Cl5	2.6844 (14)	C19—C24	1.429 (8)
Eu—Cl6	2.7731 (14)	C20—H20	0.9500
N1—H1	0.87 (2)	C20—C21	1.358 (8)
N1—C1	1.331 (7)	C21—H21	0.9500
N1—C5	1.351 (7)	C21—C22	1.406 (8)
N2—C6	1.364 (7)	C22—H22	0.9500
N2—C10	1.325 (7)	C23—H23	0.9500
N3—H3	0.872 (19)	C23—C24	1.346 (8)
N3—C13	1.328 (7)	C24—H24	0.9500
N3—C17	1.367 (7)	C25—H25	0.9500
N4—C18	1.360 (7)	C25—C26	1.404 (8)
N4—C22	1.319 (7)	C26—H26	0.9500
N5—C25	1.321 (7)	C26—C27	1.357 (8)
N5—C29	1.360 (7)	C27—H27	0.9500
N6—H6	0.863 (19)	C27—C28	1.400 (8)
N6—C30	1.352 (7)	C28—C29	1.408 (7)
N6—C34	1.333 (7)	C28—C35	1.428 (8)
N7—C37	1.324 (7)	C29—C30	1.434 (7)
N7—C41	1.363 (7)	C30—C31	1.402 (7)
N8—H8	0.863 (19)	C31—C32	1.412 (8)
N8—C42	1.351 (7)	C31—C36	1.432 (8)
N8—C46	1.324 (7)	C32—H32	0.9500
C1—H1A	0.9500	C32—C33	1.365 (8)
C1—C2	1.378 (9)	C33—H33	0.9500
C2—H2	0.9500	C33—C34	1.381 (8)
C2—C3	1.372 (9)	C34—H34	0.9500
C3—H3A	0.9500	C35—H35	0.9500
C3—C4	1.394 (8)	C35—C36	1.349 (8)
C4—C5	1.404 (7)	C36—H36	0.9500
C4—C11	1.432 (8)	C37—H37	0.9500
C5—C6	1.442 (7)	C37—C38	1.410 (8)
C6—C7	1.408 (8)	C38—H38	0.9500
C7—C8	1.393 (8)	C38—C39	1.359 (8)
C7—C12	1.425 (8)	C39—H39	0.9500
C8—H8A	0.9500	C39—C40	1.424 (8)
C8—C9	1.366 (8)	C40—C41	1.411 (7)
C9—H9	0.9500	C40—C47	1.423 (8)
C9—C10	1.386 (8)	C41—C42	1.420 (8)
C10—H10	0.9500	C42—C43	1.387 (7)
C11—H11	0.9500	C43—C44	1.409 (8)
C11—C12	1.355 (8)	C43—C48	1.426 (8)
C12—H12	0.9500	C44—H44	0.9500
C13—H13	0.9500	C44—C45	1.364 (8)
C13—C14	1.390 (8)	C45—H45	0.9500
C14—H14	0.9500	C45—C46	1.382 (8)
C14—C15	1.362 (8)	C46—H46	0.9500
C15—H15	0.9500	C47—H47	0.9500
C15—C16	1.412 (8)	C47—C48	1.363 (8)
C16—C17	1.387 (7)	C48—H48	0.9500

Cl1—Eu—Cl2	89.96 (5)	C19—C20—H20	120.5
Cl1—Eu—Cl3	92.13 (5)	C19—C20—C21	119.0 (5)
Cl1—Eu—Cl4	91.32 (4)	H20—C20—C21	120.5
Cl1—Eu—Cl5	90.67 (5)	C20—C21—H21	120.1
Cl1—Eu—Cl6	177.37 (4)	C20—C21—C22	119.7 (5)
Cl2—Eu—Cl3	175.24 (4)	H21—C21—C22	120.1
Cl2—Eu—Cl4	88.61 (4)	N4—C22—C21	123.7 (5)
Cl2—Eu—Cl5	91.92 (5)	N4—C22—H22	118.1
Cl2—Eu—Cl6	89.68 (4)	C21—C22—H22	118.1
Cl3—Eu—Cl4	87.07 (4)	C16—C23—H23	120.0
Cl3—Eu—Cl5	92.33 (5)	C16—C23—C24	120.0 (5)
Cl3—Eu—Cl6	88.04 (4)	H23—C23—C24	120.0
Cl4—Eu—Cl5	177.94 (5)	C19—C24—C23	121.8 (5)
Cl4—Eu—Cl6	86.07 (4)	C19—C24—H24	119.1
Cl5—Eu—Cl6	91.94 (4)	C23—C24—H24	119.1
H1—N1—C1	116 (4)	N5—C25—H25	118.2
H1—N1—C5	120 (4)	N5—C25—C26	123.5 (6)
C1—N1—C5	122.8 (5)	H25—C25—C26	118.2
C6—N2—C10	116.0 (5)	C25—C26—H26	120.5
H3—N3—C13	118 (4)	C25—C26—C27	119.0 (5)
H3—N3—C17	120 (4)	H26—C26—C27	120.5
C13—N3—C17	122.4 (5)	C26—C27—H27	119.9
C18—N4—C22	116.5 (5)	C26—C27—C28	120.3 (6)
C25—N5—C29	116.9 (5)	H27—C27—C28	119.9
H6—N6—C30	118 (4)	C27—C28—C29	116.4 (5)
H6—N6—C34	119 (4)	C27—C28—C35	123.7 (5)
C30—N6—C34	122.8 (5)	C29—C28—C35	119.8 (5)
C37—N7—C41	117.4 (5)	N5—C29—C28	123.9 (5)
H8—N8—C42	121 (4)	N5—C29—C30	117.9 (5)
H8—N8—C46	116 (4)	C28—C29—C30	118.2 (5)
C42—N8—C46	123.3 (5)	N6—C30—C29	119.6 (5)
N1—C1—H1A	120.0	N6—C30—C31	119.5 (5)
N1—C1—C2	120.1 (6)	C29—C30—C31	120.9 (5)
H1A—C1—C2	120.0	C30—C31—C32	117.7 (5)
C1—C2—H2	120.4	C30—C31—C36	119.2 (5)
C1—C2—C3	119.1 (6)	C32—C31—C36	123.1 (5)
H2—C2—C3	120.4	C31—C32—H32	120.0
C2—C3—H3A	119.5	C31—C32—C33	120.1 (5)
C2—C3—C4	120.9 (6)	H32—C32—C33	120.0
H3A—C3—C4	119.5	C32—C33—H33	119.9
C3—C4—C5	117.8 (5)	C32—C33—C34	120.1 (5)
C3—C4—C11	122.6 (5)	H33—C33—C34	119.9
C5—C4—C11	119.5 (5)	N6—C34—C33	119.6 (5)
N1—C5—C4	119.1 (5)	N6—C34—H34	120.2
N1—C5—C6	120.5 (5)	C33—C34—H34	120.2
C4—C5—C6	120.3 (5)	C28—C35—H35	119.1
N2—C6—C5	117.9 (5)	C28—C35—C36	121.7 (5)
N2—C6—C7	123.5 (5)	H35—C35—C36	119.1
C5—C6—C7	118.6 (5)	C31—C36—C35	120.2 (5)
C6—C7—C8	117.1 (5)	C31—C36—H36	119.9
C6—C7—C12	119.4 (5)	C35—C36—H36	119.9
C8—C7—C12	123.5 (5)	N7—C37—H37	118.2
C7—C8—H8A	120.2	N7—C37—C38	123.6 (6)
C7—C8—C9	119.7 (5)	H37—C37—C38	118.2
H8A—C8—C9	120.2	C37—C38—H38	120.3
C8—C9—H9	120.6	C37—C38—C39	119.5 (6)
C8—C9—C10	118.8 (5)	H38—C38—C39	120.3
H9—C9—C10	120.6	C38—C39—H39	120.5
N2—C10—C9	124.6 (5)	C38—C39—C40	119.0 (5)
N2—C10—H10	117.7	H39—C39—C40	120.5
C9—C10—H10	117.7	C39—C40—C41	117.4 (5)
C4—C11—H11	120.0	C39—C40—C47	122.3 (5)
C4—C11—C12	120.0 (5)	C41—C40—C47	120.3 (5)
H11—C11—C12	120.0	N7—C41—C40	123.1 (5)
C7—C12—C11	122.0 (5)	N7—C41—C42	119.1 (5)
C7—C12—H12	119.0	C40—C41—C42	117.8 (5)
C11—C12—H12	119.0	N8—C42—C41	119.3 (5)
N3—C13—H13	120.0	N8—C42—C43	119.0 (5)
N3—C13—C14	120.1 (5)	C41—C42—C43	121.7 (5)
H13—C13—C14	120.0	C42—C43—C44	117.9 (5)
C13—C14—H14	120.2	C42—C43—C48	119.3 (5)
C13—C14—C15	119.5 (5)	C44—C43—C48	122.8 (5)
H14—C14—C15	120.2	C43—C44—H44	119.5
C14—C15—H15	119.9	C43—C44—C45	121.0 (5)
C14—C15—C16	120.1 (5)	H44—C44—C45	119.5
H15—C15—C16	119.9	C44—C45—H45	120.7
C15—C16—C17	118.5 (5)	C44—C45—C46	118.7 (5)
C15—C16—C23	122.3 (5)	H45—C45—C46	120.7
C17—C16—C23	119.1 (5)	N8—C46—C45	120.2 (5)
N3—C17—C16	119.2 (5)	N8—C46—H46	119.9
N3—C17—C18	119.2 (5)	C45—C46—H46	119.9
C16—C17—C18	121.6 (5)	C40—C47—H47	119.6
N4—C18—C17	118.4 (5)	C40—C47—C48	120.7 (5)
N4—C18—C19	123.9 (5)	H47—C47—C48	119.6
C17—C18—C19	117.6 (5)	C43—C48—C47	120.2 (5)
C18—C19—C20	117.2 (5)	C43—C48—H48	119.9
C18—C19—C24	119.7 (5)	C47—C48—H48	119.9
C20—C19—C24	123.1 (5)

C5—N1—C1—C2	−1.0 (9)	C29—N5—C25—C26	0.0 (8)
N1—C1—C2—C3	−1.5 (9)	N5—C25—C26—C27	1.3 (9)
C1—C2—C3—C4	1.2 (9)	C25—C26—C27—C28	−0.6 (9)
C2—C3—C4—C5	1.5 (8)	C26—C27—C28—C29	−1.3 (8)
C2—C3—C4—C11	178.3 (5)	C26—C27—C28—C35	−178.0 (5)
C1—N1—C5—C4	3.7 (8)	C25—N5—C29—C28	−2.1 (8)
C1—N1—C5—C6	−174.1 (5)	C25—N5—C29—C30	178.4 (5)
C3—C4—C5—N1	−3.8 (8)	C27—C28—C29—N5	2.7 (8)
C3—C4—C5—C6	174.0 (5)	C27—C28—C29—C30	−177.8 (5)
C11—C4—C5—N1	179.3 (5)	C35—C28—C29—N5	179.6 (5)
C11—C4—C5—C6	−2.9 (8)	C35—C28—C29—C30	−0.9 (8)
C10—N2—C6—C5	175.2 (5)	C34—N6—C30—C29	178.3 (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—C7	176.4 (5)	N5—C29—C30—C31	178.5 (5)
C4—C5—C6—N2	179.8 (5)	C28—C29—C30—N6	177.2 (5)
C4—C5—C6—C7	−1.3 (7)	C28—C29—C30—C31	−1.0 (8)
N2—C6—C7—C8	5.3 (8)	N6—C30—C31—C32	3.2 (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—C12	4.6 (8)	C29—C30—C31—C36	2.2 (8)
C6—C7—C8—C9	−2.7 (8)	C30—C31—C32—C33	0.0 (8)
C12—C7—C8—C9	179.4 (5)	C36—C31—C32—C33	179.2 (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—C33	0.4 (8)
C8—C9—C10—N2	3.1 (9)	C32—C33—C34—N6	3.0 (9)
C3—C4—C11—C12	−172.8 (5)	C27—C28—C35—C36	178.3 (6)
C5—C4—C11—C12	4.0 (8)	C29—C28—C35—C36	1.7 (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—C11	174.2 (5)	C32—C31—C36—C35	179.4 (5)
C17—N3—C13—C14	0.7 (8)	C41—N7—C37—C38	−2.0 (9)
N3—C13—C14—C15	−2.9 (8)	N7—C37—C38—C39	0.5 (10)
C13—C14—C15—C16	2.9 (8)	C37—C38—C39—C40	1.9 (9)
C14—C15—C16—C17	−0.6 (8)	C38—C39—C40—C41	−2.7 (8)
C14—C15—C16—C23	179.5 (5)	C38—C39—C40—C47	175.8 (5)
C13—N3—C17—C16	1.5 (8)	C37—N7—C41—C40	1.1 (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—N7	1.2 (8)
C15—C16—C17—C18	178.3 (5)	C39—C40—C41—C42	179.0 (5)
C23—C16—C17—N3	178.3 (5)	C47—C40—C41—N7	−177.2 (5)
C23—C16—C17—C18	−1.9 (8)	C47—C40—C41—C42	0.5 (8)
C22—N4—C18—C17	178.2 (5)	C46—N8—C42—C41	177.7 (5)
C22—N4—C18—C19	−0.4 (8)	C46—N8—C42—C43	−1.6 (8)
N3—C17—C18—N4	1.4 (7)	N7—C41—C42—N8	−3.1 (8)
N3—C17—C18—C19	−179.9 (5)	N7—C41—C42—C43	176.1 (5)
C16—C17—C18—N4	−178.4 (5)	C40—C41—C42—N8	179.0 (5)
C16—C17—C18—C19	0.3 (8)	C40—C41—C42—C43	−1.7 (8)
N4—C18—C19—C20	0.5 (8)	N8—C42—C43—C44	0.6 (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—C24	1.7 (8)	C41—C42—C43—C48	1.7 (8)
C18—C19—C20—C21	0.3 (8)	C42—C43—C44—C45	1.0 (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—C45	1.0 (8)
C20—C21—C22—N4	1.1 (9)	C44—C45—C46—N8	0.6 (9)
C15—C16—C23—C24	−178.7 (5)	C39—C40—C47—C48	−177.6 (5)
C17—C16—C23—C24	1.4 (8)	C41—C40—C47—C48	0.8 (8)
C16—C23—C24—C19	0.6 (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—C23	177.6 (5)	C44—C43—C48—C47	−180.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl7	0.87 (2)	2.25 (3)	3.052 (5)	154 (5)
N3—H3···Cl6	0.87 (2)	2.45 (4)	3.166 (5)	140 (5)
N6—H6···Cl7	0.86 (2)	2.42 (4)	3.125 (5)	139 (5)
N8—H8···Cl7	0.86 (2)	2.35 (4)	3.095 (5)	145 (5)

Experimental details

Crystal data
Chemical formula	(C₁₂H₉N₂)₄[EuCl₆]Cl
M_r	1124.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	160
a, b, c (Å)	17.6308 (5), 11.2069 (3), 24.0726 (7)
β (°)	111.197 (2)
V (Å³)	4434.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.38 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART 1K CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.530, 0.650
No. of measured, independent and observed [I > 2σ(I)] reflections	31682, 7803, 6822
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.092, 1.30
No. of reflections	7803
No. of parameters	589
No. of restraints	162
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0056P)² + 19.2232P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.86, −1.82

Computer programs: SMART (Bruker, 2001), SAINT (Bruker 2001), Bruker SAINT, SHELXTL (Sheldrick, 2001), SHELXTL, PLATON (Spek, 2003) and local programs.

Selected bond lengths (Å) top

Eu—Cl1	2.6596 (14)	Eu—Cl4	2.6753 (13)
Eu—Cl2	2.7092 (14)	Eu—Cl5	2.6844 (14)
Eu—Cl3	2.6876 (14)	Eu—Cl6	2.7731 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl7	0.87 (2)	2.25 (3)	3.052 (5)	154 (5)
N3—H3···Cl6	0.872 (19)	2.45 (4)	3.166 (5)	140 (5)
N6—H6···Cl7	0.863 (19)	2.42 (4)	3.125 (5)	139 (5)
N8—H8···Cl7	0.863 (19)	2.35 (4)	3.095 (5)	145 (5)

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