Tetrakis[μ-3-(3-pyridyl)acrylato-κO:O']bis{(1,10-phenanthroline-κN,N')[3-(3-pyridyl)acrylato-κO,O']europium(III)} pentahydrate.

The europium(III) ion in the title compound, [Eu(2)(C(8)H(6)NO(2))(6)(C(12)H(8)N(2))(2)]·5H(2)O, is coordinated by seven carboxyl-ate O atoms and two N atoms from one phenanthroline mol-ecule. The carboxyl-ate groups of 3-(3-pyrid-yl)acrylate link pairs of europium(III) ions, forming centrosymmetric dinuclear units, which further assemble into a sheet parallel to the (001) plane through hydrogen-bonding inter-actions involving the uncoordinated water mol-ecules. One water molecule is disordered.

Related literature

For related literature, see: Gunning & Cahill (2005 ▶); Liu et al. (2006 ▶); Ye et al. (2005 ▶).

Experimental

Crystal data

[Eu2(C8H6NO2)6(C12H8N2)2]·5H2O

M = 1643.24

Monoclinic,

a = 25.434 (2) Å

b = 12.320 (10) Å

c = 22.595 (19) Å

β = 100.330 (10)°

V = 6965.4 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.86 mm−1

T = 293 (2) K

0.32 × 0.27 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.585, T max = 0.791

25928 measured reflections

6480 independent reflections

5721 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.044

S = 1.03

6480 reflections

460 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶)and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066263/dn2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066263/dn2276Isup2.hkl

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

[Eu2(C8H6NO2)6(C12H8N2)2]·5H2O	F000 = 3304
Mr = 1643.24	Dx = 1.567 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7048 reflections
a = 25.434 (2) Å	θ = 2.7–28.1º
b = 12.320 (10) Å	µ = 1.86 mm−1
c = 22.595 (19) Å	T = 293 (2) K
β = 100.330 (10)º	Block, colorless
V = 6965.4 (10) Å3	0.32 × 0.27 × 0.13 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	6480 independent reflections
Radiation source: fine-focus sealed tube	5721 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 293(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −30→30
Tmin = 0.585, Tmax = 0.791	k = −14→14
25928 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019	H-atom parameters constrained
wR(F2) = 0.044	w = 1/[σ2(Fo2) + (0.0183P)2 + 8.1685P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.006
6480 reflections	Δρmax = 0.34 e Å−3
460 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Eu1	0.528205 (4)	0.611291 (8)	0.562535 (4)	0.02456 (4)
O5	0.58593 (7)	0.57165 (15)	0.66055 (7)	0.0457 (4)
O6	0.62759 (6)	0.62061 (13)	0.58772 (7)	0.0417 (4)
N3	0.82161 (9)	0.3750 (2)	0.77152 (12)	0.0627 (7)
N4	0.55055 (7)	0.81740 (14)	0.56748 (8)	0.0312 (4)
N5	0.48983 (7)	0.72683 (15)	0.64279 (8)	0.0311 (4)
C17	0.62845 (9)	0.58151 (19)	0.63974 (11)	0.0375 (6)
C18	0.68033 (10)	0.5427 (2)	0.67463 (12)	0.0442 (6)
H18	0.7110	0.5515	0.6581	0.053*
C19	0.68467 (10)	0.4966 (2)	0.72778 (11)	0.0430 (6)
H19	0.6538	0.4954	0.7444	0.052*
C20	0.73241 (10)	0.4467 (2)	0.76421 (11)	0.0415 (6)
C21	0.73315 (12)	0.4186 (3)	0.82349 (13)	0.0589 (8)
H21	0.7035	0.4319	0.8412	0.071*
C22	0.77820 (14)	0.3705 (3)	0.85628 (14)	0.0729 (10)
H22	0.7796	0.3521	0.8964	0.087*
C23	0.82070 (13)	0.3506 (3)	0.82849 (15)	0.0664 (9)
H23	0.8508	0.3179	0.8509	0.080*
C24	0.77778 (10)	0.4222 (2)	0.74091 (12)	0.0500 (7)
H24	0.7777	0.4400	0.7009	0.060*
C25	0.58064 (10)	0.8617 (2)	0.53183 (11)	0.0418 (6)
H25	0.5997	0.8160	0.5106	0.050*
C26	0.58516 (12)	0.9740 (2)	0.52446 (12)	0.0531 (7)
H26	0.6067	1.0017	0.4988	0.064*
C27	0.55780 (12)	1.0418 (2)	0.55515 (13)	0.0562 (7)
H27	0.5599	1.1165	0.5501	0.067*
C28	0.52609 (10)	0.99896 (19)	0.59464 (12)	0.0450 (6)
C29	0.49626 (13)	1.0650 (2)	0.62910 (15)	0.0629 (8)
H29	0.4973	1.1401	0.6255	0.076*
C30	0.46693 (12)	1.0205 (2)	0.66633 (15)	0.0611 (8)
H30	0.4485	1.0655	0.6886	0.073*
C31	0.46320 (10)	0.9054 (2)	0.67276 (12)	0.0435 (6)
C32	0.43288 (10)	0.8555 (2)	0.71132 (12)	0.0505 (7)
H32	0.4134	0.8978	0.7338	0.061*
C33	0.43197 (10)	0.7457 (2)	0.71572 (11)	0.0472 (6)
H33	0.4124	0.7120	0.7415	0.057*
C34	0.46102 (9)	0.6843 (2)	0.68077 (10)	0.0395 (6)
H34	0.4602	0.6091	0.6842	0.047*
C35	0.49140 (8)	0.83702 (18)	0.63913 (10)	0.0318 (5)
C36	0.52348 (9)	0.88490 (17)	0.59938 (10)	0.0331 (5)
O1	0.44766 (7)	0.35404 (12)	0.53195 (7)	0.0375 (4)
O2	0.47138 (6)	0.48567 (12)	0.60014 (7)	0.0389 (4)
O3	0.44546 (6)	0.55841 (12)	0.47089 (7)	0.0367 (4)
O4	0.44788 (6)	0.71259 (12)	0.51991 (7)	0.0382 (4)
N1	0.40521 (14)	0.2529 (3)	0.83252 (12)	0.0830 (9)
N2	0.21675 (9)	0.92111 (19)	0.44666 (11)	0.0541 (6)
C1	0.44874 (9)	0.39752 (17)	0.58251 (10)	0.0328 (5)
C2	0.42104 (10)	0.33633 (19)	0.62482 (10)	0.0395 (5)
H2	0.3976	0.2814	0.6090	0.047*
C3	0.42757 (10)	0.35487 (19)	0.68318 (11)	0.0390 (6)
H3	0.4495	0.4129	0.6979	0.047*
C4	0.40369 (11)	0.2931 (2)	0.72740 (11)	0.0428 (6)
C5	0.36142 (13)	0.2224 (2)	0.71075 (14)	0.0632 (8)
H5	0.3466	0.2118	0.6704	0.076*
C6	0.34154 (17)	0.1676 (3)	0.75602 (19)	0.0866 (12)
H6	0.3129	0.1199	0.7466	0.104*
C7	0.36502 (18)	0.1855 (3)	0.81466 (18)	0.0882 (12)
H7	0.3516	0.1473	0.8442	0.106*
C8	0.42271 (12)	0.3066 (3)	0.78849 (12)	0.0584 (8)
H8	0.4498	0.3571	0.7997	0.070*
C9	0.42372 (9)	0.64675 (17)	0.48230 (9)	0.0295 (5)
C10	0.36825 (9)	0.67176 (18)	0.45216 (10)	0.0336 (5)
H10	0.3514	0.6266	0.4216	0.040*
C11	0.34228 (9)	0.75715 (18)	0.46803 (10)	0.0346 (5)
H11	0.3607	0.7998	0.4989	0.041*
C12	0.28771 (9)	0.79227 (19)	0.44256 (11)	0.0392 (6)
C13	0.25486 (11)	0.7384 (3)	0.39657 (14)	0.0658 (9)
H13	0.2674	0.6777	0.3789	0.079*
C14	0.20331 (12)	0.7750 (3)	0.37698 (17)	0.0795 (11)
H14	0.1807	0.7390	0.3464	0.095*
C15	0.18612 (11)	0.8654 (3)	0.40342 (15)	0.0651 (9)
H15	0.1512	0.8888	0.3904	0.078*
C16	0.26665 (10)	0.8837 (2)	0.46531 (12)	0.0457 (6)
H16	0.2886	0.9220	0.4956	0.055*
O1W	0.69847 (9)	0.61683 (17)	0.50760 (12)	0.0848 (8)
H11W	0.6788	0.6122	0.5340	0.127*
H12W	0.6986	0.5565	0.4895	0.127*
O2W	0.30658 (11)	0.1792 (3)	0.55009 (14)	0.1219 (11)
H21W	0.2805	0.2095	0.5594	0.183*
H22W	0.2973	0.1433	0.5193	0.183*
O3W	0.3341 (3)	0.9915 (5)	0.6047 (3)	0.133 (2)	0.50
H32W	0.3035	1.0082	0.6078	0.199*	0.50
H31W	0.3521	1.0410	0.5944	0.199*	0.50

	U11	U22	U33	U12	U13	U23
Eu1	0.02668 (6)	0.02120 (6)	0.02471 (6)	−0.00104 (4)	0.00168 (4)	−0.00081 (4)
O5	0.0382 (10)	0.0595 (11)	0.0366 (9)	0.0112 (8)	−0.0010 (8)	0.0015 (8)
O6	0.0356 (9)	0.0442 (10)	0.0416 (10)	−0.0015 (7)	−0.0026 (7)	0.0035 (8)
N3	0.0460 (14)	0.0697 (17)	0.0676 (17)	0.0169 (12)	−0.0031 (12)	0.0009 (13)
N4	0.0331 (10)	0.0262 (10)	0.0332 (10)	−0.0044 (8)	0.0026 (8)	−0.0031 (8)
N5	0.0327 (10)	0.0322 (10)	0.0270 (9)	−0.0002 (8)	0.0018 (8)	−0.0025 (8)
C17	0.0348 (13)	0.0324 (13)	0.0411 (14)	0.0016 (10)	−0.0045 (11)	−0.0092 (10)
C18	0.0327 (13)	0.0459 (15)	0.0499 (15)	0.0015 (11)	−0.0033 (11)	−0.0014 (12)
C19	0.0366 (13)	0.0420 (14)	0.0471 (15)	0.0007 (11)	−0.0016 (11)	−0.0039 (12)
C20	0.0400 (14)	0.0367 (13)	0.0431 (14)	0.0008 (11)	−0.0057 (11)	−0.0026 (11)
C21	0.0577 (18)	0.068 (2)	0.0492 (17)	0.0100 (15)	0.0041 (14)	0.0027 (14)
C22	0.079 (2)	0.084 (2)	0.0483 (18)	0.0120 (19)	−0.0102 (17)	0.0169 (16)
C23	0.0566 (19)	0.0612 (19)	0.070 (2)	0.0155 (15)	−0.0192 (16)	0.0079 (16)
C24	0.0455 (15)	0.0541 (16)	0.0469 (15)	0.0046 (13)	−0.0013 (12)	0.0001 (12)
C25	0.0464 (15)	0.0380 (14)	0.0418 (14)	−0.0111 (11)	0.0102 (11)	−0.0053 (11)
C26	0.0648 (18)	0.0425 (15)	0.0533 (17)	−0.0208 (14)	0.0140 (14)	0.0019 (13)
C27	0.0678 (19)	0.0272 (14)	0.072 (2)	−0.0109 (13)	0.0082 (16)	0.0033 (13)
C28	0.0483 (15)	0.0273 (12)	0.0564 (16)	−0.0001 (11)	0.0012 (12)	−0.0037 (11)
C29	0.070 (2)	0.0292 (14)	0.090 (2)	0.0054 (14)	0.0161 (18)	−0.0103 (15)
C30	0.0621 (19)	0.0410 (16)	0.082 (2)	0.0117 (14)	0.0170 (17)	−0.0203 (15)
C31	0.0387 (14)	0.0424 (15)	0.0483 (15)	0.0069 (11)	0.0048 (11)	−0.0116 (11)
C32	0.0383 (14)	0.0632 (18)	0.0511 (16)	0.0081 (13)	0.0110 (12)	−0.0178 (14)
C33	0.0389 (14)	0.0665 (19)	0.0373 (14)	−0.0032 (13)	0.0099 (11)	−0.0062 (13)
C34	0.0429 (14)	0.0412 (14)	0.0346 (13)	−0.0038 (11)	0.0077 (11)	−0.0019 (10)
C35	0.0298 (11)	0.0306 (12)	0.0322 (12)	0.0016 (9)	−0.0025 (9)	−0.0049 (10)
C36	0.0326 (12)	0.0288 (12)	0.0348 (12)	0.0001 (10)	−0.0024 (9)	−0.0040 (10)
O1	0.0497 (10)	0.0332 (8)	0.0308 (8)	−0.0102 (7)	0.0099 (7)	−0.0043 (7)
O2	0.0511 (10)	0.0324 (9)	0.0353 (9)	−0.0135 (8)	0.0136 (8)	−0.0048 (7)
O3	0.0388 (9)	0.0252 (8)	0.0454 (9)	0.0047 (7)	0.0059 (7)	−0.0021 (7)
O4	0.0359 (9)	0.0310 (8)	0.0426 (9)	0.0043 (7)	−0.0074 (7)	−0.0062 (7)
N1	0.102 (2)	0.097 (2)	0.0588 (17)	0.014 (2)	0.0373 (17)	0.0253 (17)
N2	0.0400 (13)	0.0515 (14)	0.0725 (16)	0.0131 (11)	0.0148 (12)	0.0069 (12)
C1	0.0365 (12)	0.0291 (12)	0.0329 (12)	−0.0023 (10)	0.0064 (10)	0.0012 (10)
C2	0.0475 (14)	0.0341 (13)	0.0392 (13)	−0.0128 (11)	0.0136 (11)	−0.0034 (11)
C3	0.0453 (14)	0.0330 (13)	0.0413 (14)	−0.0038 (11)	0.0145 (11)	0.0005 (10)
C4	0.0541 (16)	0.0347 (13)	0.0443 (15)	0.0045 (11)	0.0215 (12)	0.0046 (11)
C5	0.085 (2)	0.0511 (18)	0.0599 (19)	−0.0153 (16)	0.0310 (17)	0.0009 (14)
C6	0.110 (3)	0.063 (2)	0.099 (3)	−0.032 (2)	0.053 (3)	0.003 (2)
C7	0.121 (3)	0.080 (3)	0.079 (3)	0.008 (2)	0.060 (3)	0.028 (2)
C8	0.0684 (19)	0.068 (2)	0.0432 (16)	0.0044 (15)	0.0209 (14)	0.0110 (14)
C9	0.0330 (12)	0.0250 (11)	0.0299 (11)	0.0008 (9)	0.0038 (9)	0.0039 (9)
C10	0.0329 (12)	0.0299 (12)	0.0354 (12)	−0.0021 (10)	−0.0011 (10)	−0.0044 (10)
C11	0.0327 (12)	0.0337 (12)	0.0354 (12)	−0.0028 (10)	0.0009 (10)	−0.0018 (10)
C12	0.0321 (13)	0.0388 (13)	0.0456 (14)	0.0026 (10)	0.0045 (11)	0.0012 (11)
C13	0.0437 (16)	0.065 (2)	0.080 (2)	0.0141 (14)	−0.0149 (15)	−0.0226 (17)
C14	0.0462 (18)	0.082 (2)	0.098 (3)	0.0138 (17)	−0.0224 (17)	−0.025 (2)
C15	0.0340 (15)	0.072 (2)	0.085 (2)	0.0112 (14)	−0.0021 (15)	0.0104 (18)
C16	0.0371 (13)	0.0432 (14)	0.0565 (16)	0.0046 (12)	0.0078 (12)	0.0001 (12)
O1W	0.0709 (15)	0.0684 (15)	0.128 (2)	−0.0128 (12)	0.0522 (15)	−0.0190 (14)
O2W	0.093 (2)	0.123 (3)	0.140 (3)	−0.0135 (19)	−0.0045 (19)	0.010 (2)
O3W	0.139 (5)	0.103 (5)	0.133 (5)	−0.017 (4)	−0.036 (4)	0.009 (4)

Eu1—O3i	2.3604 (15)	C32—H32	0.9300
Eu1—O1i	2.3638 (15)	C33—C34	1.397 (3)
Eu1—O2	2.3763 (15)	C33—H33	0.9300
Eu1—O4	2.4400 (15)	C34—H34	0.9300
Eu1—O5	2.4765 (16)	C35—C36	1.443 (3)
Eu1—O6	2.4922 (16)	O1—C1	1.258 (3)
Eu1—N4	2.6001 (18)	O1—Eu1i	2.3638 (15)
Eu1—N5	2.6272 (18)	O2—C1	1.260 (3)
Eu1—O3	2.7530 (16)	O3—C9	1.268 (3)
Eu1—C17	2.843 (2)	O3—Eu1i	2.3604 (15)
Eu1—C9	2.969 (2)	O4—C9	1.253 (3)
Eu1—Eu1i	4.0137 (3)	N1—C7	1.322 (5)
O5—C17	1.260 (3)	N1—C8	1.336 (4)
O6—C17	1.267 (3)	N2—C15	1.327 (4)
N3—C23	1.326 (4)	N2—C16	1.345 (3)
N3—C24	1.335 (3)	C1—C2	1.490 (3)
N4—C25	1.324 (3)	C2—C3	1.319 (3)
N4—C36	1.365 (3)	C2—H2	0.9300
N5—C34	1.332 (3)	C3—C4	1.471 (3)
N5—C35	1.361 (3)	C3—H3	0.9300
C17—C18	1.489 (3)	C4—C5	1.382 (4)
C18—C19	1.315 (3)	C4—C8	1.388 (4)
C18—H18	0.9300	C5—C6	1.394 (4)
C19—C20	1.474 (3)	C5—H5	0.9300
C19—H19	0.9300	C6—C7	1.370 (5)
C20—C21	1.380 (4)	C6—H6	0.9300
C20—C24	1.385 (4)	C7—H7	0.9300
C21—C22	1.381 (4)	C8—H8	0.9300
C21—H21	0.9300	C9—C10	1.485 (3)
C22—C23	1.366 (5)	C10—C11	1.325 (3)
C22—H22	0.9300	C10—H10	0.9300
C23—H23	0.9300	C11—C12	1.469 (3)
C24—H24	0.9300	C11—H11	0.9300
C25—C26	1.400 (3)	C12—C13	1.381 (4)
C25—H25	0.9300	C12—C16	1.385 (3)
C26—C27	1.355 (4)	C13—C14	1.382 (4)
C26—H26	0.9300	C13—H13	0.9300
C27—C28	1.408 (4)	C14—C15	1.371 (4)
C27—H27	0.9300	C14—H14	0.9300
C28—C36	1.412 (3)	C15—H15	0.9300
C28—C29	1.434 (4)	C16—H16	0.9300
C29—C30	1.338 (4)	O1W—H11W	0.8462
C29—H29	0.9300	O1W—H12W	0.8481
C30—C31	1.431 (4)	O2W—H21W	0.8204
C30—H30	0.9300	O2W—H22W	0.8227
C31—C32	1.404 (4)	O3W—H32W	0.8204
C31—C35	1.413 (3)	O3W—H31W	0.8198
C32—C33	1.357 (4)
O3i—Eu1—O1i	74.72 (5)	N3—C24—H24	117.5
O3i—Eu1—O2	76.31 (5)	C20—C24—H24	117.5
O1i—Eu1—O2	135.54 (5)	N4—C25—C26	123.3 (2)
O3i—Eu1—O4	126.32 (5)	N4—C25—H25	118.4
O1i—Eu1—O4	83.44 (6)	C26—C25—H25	118.4
O2—Eu1—O4	87.38 (6)	C27—C26—C25	119.2 (3)
O3i—Eu1—O5	87.40 (6)	C27—C26—H26	120.4
O1i—Eu1—O5	129.42 (6)	C25—C26—H26	120.4
O2—Eu1—O5	81.54 (6)	C26—C27—C28	119.9 (2)
O4—Eu1—O5	140.72 (5)	C26—C27—H27	120.1
O3i—Eu1—O6	77.26 (5)	C28—C27—H27	120.1
O1i—Eu1—O6	77.34 (6)	C27—C28—C36	117.5 (2)
O2—Eu1—O6	127.26 (6)	C27—C28—C29	123.4 (2)
O4—Eu1—O6	144.08 (5)	C36—C28—C29	119.1 (3)
O5—Eu1—O6	52.45 (6)	C30—C29—C28	121.2 (3)
O3i—Eu1—N4	143.74 (6)	C30—C29—H29	119.4
O1i—Eu1—N4	76.83 (5)	C28—C29—H29	119.4
O2—Eu1—N4	139.73 (5)	C29—C30—C31	121.6 (3)
O4—Eu1—N4	71.25 (5)	C29—C30—H30	119.2
O5—Eu1—N4	93.68 (6)	C31—C30—H30	119.2
O6—Eu1—N4	74.94 (6)	C32—C31—C35	117.5 (2)
O3i—Eu1—N5	149.61 (6)	C32—C31—C30	123.4 (2)
O1i—Eu1—N5	135.59 (5)	C35—C31—C30	119.1 (3)
O2—Eu1—N5	77.35 (5)	C33—C32—C31	120.0 (2)
O4—Eu1—N5	66.85 (5)	C33—C32—H32	120.0
O5—Eu1—N5	73.95 (6)	C31—C32—H32	120.0
O6—Eu1—N5	107.73 (5)	C32—C33—C34	118.8 (2)
N4—Eu1—N5	63.04 (6)	C32—C33—H33	120.6
O3i—Eu1—O3	76.84 (5)	C34—C33—H33	120.6
O1i—Eu1—O3	69.55 (5)	N5—C34—C33	124.0 (2)
O2—Eu1—O3	71.51 (5)	N5—C34—H34	118.0
O4—Eu1—O3	49.54 (5)	C33—C34—H34	118.0
O5—Eu1—O3	151.25 (6)	N5—C35—C31	122.6 (2)
O6—Eu1—O3	142.18 (5)	N5—C35—C36	118.14 (19)
N4—Eu1—O3	113.28 (5)	C31—C35—C36	119.3 (2)
N5—Eu1—O3	108.60 (5)	N4—C36—C28	122.1 (2)
O3i—Eu1—C17	78.89 (6)	N4—C36—C35	118.33 (19)
O1i—Eu1—C17	103.18 (7)	C28—C36—C35	119.6 (2)
O2—Eu1—C17	103.45 (7)	C1—O1—Eu1i	140.95 (14)
O4—Eu1—C17	154.62 (6)	C1—O2—Eu1	136.14 (14)
O5—Eu1—C17	26.26 (6)	C9—O3—Eu1i	169.88 (14)
O6—Eu1—C17	26.44 (6)	C9—O3—Eu1	86.92 (12)
N4—Eu1—C17	86.25 (6)	Eu1i—O3—Eu1	103.16 (5)
N5—Eu1—C17	92.85 (6)	C9—O4—Eu1	102.16 (13)
O3—Eu1—C17	155.71 (6)	C7—N1—C8	115.2 (3)
O3i—Eu1—C9	102.08 (6)	C15—N2—C16	116.7 (2)
O1i—Eu1—C9	76.75 (6)	O1—C1—O2	126.1 (2)
O2—Eu1—C9	77.23 (6)	O1—C1—C2	115.56 (19)
O4—Eu1—C9	24.37 (5)	O2—C1—C2	118.4 (2)
O5—Eu1—C9	153.82 (6)	C3—C2—C1	124.4 (2)
O6—Eu1—C9	153.25 (6)	C3—C2—H2	117.8
N4—Eu1—C9	92.72 (6)	C1—C2—H2	117.8
N5—Eu1—C9	86.51 (6)	C2—C3—C4	126.6 (2)
O3—Eu1—C9	25.25 (5)	C2—C3—H3	116.7
C17—Eu1—C9	178.95 (6)	C4—C3—H3	116.7
O3i—Eu1—Eu1i	41.90 (4)	C5—C4—C8	117.5 (2)
O1i—Eu1—Eu1i	66.76 (4)	C5—C4—C3	122.5 (2)
O2—Eu1—Eu1i	69.10 (4)	C8—C4—C3	120.0 (2)
O4—Eu1—Eu1i	84.45 (4)	C4—C5—C6	118.2 (3)
O5—Eu1—Eu1i	125.08 (4)	C4—C5—H5	120.9
O6—Eu1—Eu1i	114.34 (4)	C6—C5—H5	120.9
N4—Eu1—Eu1i	138.18 (4)	C7—C6—C5	118.6 (3)
N5—Eu1—Eu1i	136.55 (4)	C7—C6—H6	120.7
O3—Eu1—Eu1i	34.93 (3)	C5—C6—H6	120.7
C17—Eu1—Eu1i	120.79 (5)	N1—C7—C6	125.1 (3)
C9—Eu1—Eu1i	60.18 (4)	N1—C7—H7	117.4
C17—O5—Eu1	93.33 (14)	C6—C7—H7	117.4
C17—O6—Eu1	92.42 (14)	N1—C8—C4	125.3 (3)
C23—N3—C24	116.3 (3)	N1—C8—H8	117.4
C25—N4—C36	118.12 (19)	C4—C8—H8	117.4
C25—N4—Eu1	121.48 (15)	O4—C9—O3	120.99 (19)
C36—N4—Eu1	119.38 (14)	O4—C9—C10	119.13 (19)
C34—N5—C35	117.2 (2)	O3—C9—C10	119.86 (19)
C34—N5—Eu1	123.15 (15)	O4—C9—Eu1	53.47 (10)
C35—N5—Eu1	118.67 (14)	O3—C9—Eu1	67.83 (11)
O5—C17—O6	120.7 (2)	C10—C9—Eu1	169.61 (15)
O5—C17—C18	120.6 (2)	C11—C10—C9	121.3 (2)
O6—C17—C18	118.6 (2)	C11—C10—H10	119.4
O5—C17—Eu1	60.41 (12)	C9—C10—H10	119.4
O6—C17—Eu1	61.14 (12)	C10—C11—C12	127.6 (2)
C18—C17—Eu1	168.00 (16)	C10—C11—H11	116.2
C19—C18—C17	122.9 (2)	C12—C11—H11	116.2
C19—C18—H18	118.5	C13—C12—C16	116.6 (2)
C17—C18—H18	118.5	C13—C12—C11	123.7 (2)
C18—C19—C20	128.0 (3)	C16—C12—C11	119.7 (2)
C18—C19—H19	116.0	C12—C13—C14	119.7 (3)
C20—C19—H19	116.0	C12—C13—H13	120.2
C21—C20—C24	116.6 (2)	C14—C13—H13	120.2
C21—C20—C19	120.9 (2)	C15—C14—C13	119.0 (3)
C24—C20—C19	122.5 (2)	C15—C14—H14	120.5
C20—C21—C22	119.6 (3)	C13—C14—H14	120.5
C20—C21—H21	120.2	N2—C15—C14	123.4 (3)
C22—C21—H21	120.2	N2—C15—H15	118.3
C23—C22—C21	118.6 (3)	C14—C15—H15	118.3
C23—C22—H22	120.7	N2—C16—C12	124.6 (3)
C21—C22—H22	120.7	N2—C16—H16	117.7
N3—C23—C22	123.9 (3)	C12—C16—H16	117.7
N3—C23—H23	118.0	H11W—O1W—H12W	109.4
C22—C23—H23	118.0	H21W—O2W—H22W	109.8
N3—C24—C20	125.0 (3)	H32W—O3W—H31W	115.1

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O6	0.85	1.94	2.775 (3)	171
O1W—H12W···N2ii	0.85	2.02	2.856 (3)	167
O2W—H21W···O1Wiii	0.82	2.48	2.851 (4)	109
O3W—H31W···O2Wiv	0.82	2.20	2.655 (7)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O6	0.85	1.94	2.775 (3)	171
O1W—H12W⋯N2i	0.85	2.02	2.856 (3)	167
O2W—H21W⋯O1Wii	0.82	2.48	2.851 (4)	109
O3W—H31W⋯O2Wiii	0.82	2.20	2.655 (7)	116

Symmetry codes: (i) ; (ii) ; (iii) .