catena-Poly[[[triaqua-europium(III)]-μ-(1H-benzimidazole-5,6-dicarboxyl-ato-κO:O)-μ-(1H,3H-benzimidazol-3-ium-5,6-dicarboxyl-ato-κO:O,O)] dihydrate].

In the title one-dimensional coordination polymer, {[Eu(C(9)H(4)N(2)O(4))(C(9)H(5)N(2)O(4))(H(2)O)(3)]·2H(2)O}(n), one of the 1H-benzimidazole-5,6-dicarboxyl-ate (Hbdc) ligands is protonated at the imidazole group (H(2)bdc). The Eu(III) ion is eight-coordinated by two O atoms from two Hbdc ligands, three O atoms from two H(2)bdc ligands and three water mol-ecules, showing a distorted square-anti-prismatic geometry. The Eu(III) ions are bridged by the carboxyl-ate groups of the Hbdc and H(2)bdc ligands, forming a chain along [110], with an Eu⋯Eu separation of 5.4594 (3) Å. These chains are further connected by inter-molecular O-H⋯O, N-H⋯O and N-H⋯N hydrogen bonds, as well as π-π inter-actions between the imidazole and benzene rings [centroid-centroid distances = 3.558 (3), 3.906 (2), 3.397 (3), 3.796 (2) and 3.898 (2) Å], into a three-dimensional supra-molecular network.

Related literature

For background to 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Fu et al. (2009 ▶); Huang et al. (2009 ▶); Pan et al. (2010 ▶); Wei et al. (2009 ▶); Yao et al. (2008 ▶).

Experimental

Crystal data

[Eu(C9H4N2O4)(C9H5N2O4)(H2O)3]·2H2O

M = 651.33

Triclinic,

a = 8.4530 (4) Å

b = 10.9757 (6) Å

c = 12.7124 (7) Å

α = 112.112 (1)°

β = 91.614 (1)°

γ = 104.453 (1)°

V = 1048.25 (10) Å3

Z = 2

Mo Kα radiation

μ = 3.08 mm−1

T = 298 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.526, T max = 0.578

5435 measured reflections

3711 independent reflections

3454 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.057

S = 1.04

3711 reflections

328 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, glogal. DOI: 10.1107/S1600536811033496/hy2459sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033496/hy2459Isup2.hkl

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

[Eu(C9H4N2O4)(C9H5N2O4)(H2O)3]·2H2O	Z = 2
Mr = 651.33	F(000) = 644
Triclinic, P1	Dx = 2.064 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4530 (4) Å	Cell parameters from 3764 reflections
b = 10.9757 (6) Å	θ = 2.8–25.2°
c = 12.7124 (7) Å	µ = 3.08 mm−1
α = 112.112 (1)°	T = 298 K
β = 91.614 (1)°	Block, colorless
γ = 104.453 (1)°	0.24 × 0.22 × 0.20 mm
V = 1048.25 (10) Å3

Bruker APEXII CCD diffractometer	3711 independent reflections
Radiation source: fine-focus sealed tube	3454 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.526, Tmax = 0.578	k = −13→7
5435 measured reflections	l = −13→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0269P)2 + 1.5288P] where P = (Fo2 + 2Fc2)/3
3711 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.67 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.0343 (4)	0.0408 (4)	−0.2244 (3)	0.0189 (8)
C2	−0.1313 (4)	−0.0377 (4)	−0.2964 (3)	0.0187 (8)
C3	−0.1457 (5)	−0.0513 (4)	−0.4085 (3)	0.0244 (9)
H3	−0.051 (5)	−0.019 (4)	−0.434 (3)	0.029*
C4	−0.3019 (5)	−0.1056 (4)	−0.4725 (3)	0.0232 (8)
C5	−0.5240 (5)	−0.1795 (4)	−0.5977 (3)	0.0299 (9)
H5	−0.5915	−0.2033	−0.6655	0.036*
C6	−0.4412 (4)	−0.1460 (4)	−0.4248 (3)	0.0213 (8)
C7	−0.4269 (4)	−0.1359 (4)	−0.3119 (3)	0.0210 (8)
H7	−0.5196	−0.1642	−0.2801	0.025*
C8	−0.2722 (4)	−0.0831 (4)	−0.2488 (3)	0.0171 (7)
C9	−0.2606 (4)	−0.0819 (4)	−0.1297 (3)	0.0185 (8)
C10	0.5024 (4)	0.4467 (4)	0.2501 (3)	0.0198 (8)
C11	0.6702 (4)	0.5243 (4)	0.3216 (3)	0.0174 (7)
C12	0.6891 (4)	0.5302 (4)	0.4319 (3)	0.0219 (8)
H12	0.6019	0.4883	0.4609	0.026*
C13	0.8420 (4)	0.6003 (4)	0.4979 (3)	0.0198 (8)
C14	1.0585 (5)	0.7001 (4)	0.6311 (3)	0.0271 (9)
H14	1.1247	0.7334	0.7012	0.033*
C15	0.9760 (4)	0.6562 (4)	0.4530 (3)	0.0190 (8)
C16	0.9601 (4)	0.6502 (4)	0.3422 (3)	0.0198 (8)
H16	1.0501	0.6869	0.3122	0.024*
C17	0.8053 (4)	0.5876 (4)	0.2777 (3)	0.0174 (7)
C18	0.7878 (4)	0.6050 (4)	0.1667 (3)	0.0174 (7)
Eu1	0.24165 (2)	0.308010 (18)	0.021383 (14)	0.01508 (7)
N1	−0.3591 (4)	−0.1283 (4)	−0.5833 (3)	0.0302 (8)
H1	−0.3003	−0.1126	−0.6334	0.036*
N2	−0.5797 (4)	−0.1922 (4)	−0.5056 (3)	0.0271 (8)
N3	1.1094 (4)	0.7157 (3)	0.5386 (3)	0.0239 (7)
H3A	1.2081	0.7556	0.5326	0.029*
N4	0.8992 (4)	0.6303 (3)	0.6108 (3)	0.0248 (7)
H4	0.8422	0.6080	0.6591	0.030*
O1	0.1619 (3)	0.0246 (3)	−0.2694 (2)	0.0282 (6)
O2	0.0329 (3)	0.1254 (3)	−0.1235 (2)	0.0218 (6)
O3	−0.1766 (3)	−0.1539 (3)	−0.1112 (2)	0.0232 (6)
O4	−0.3436 (3)	−0.0182 (3)	−0.0613 (2)	0.0286 (6)
O5	0.5008 (3)	0.3761 (3)	0.1434 (2)	0.0233 (6)
O6	0.3781 (3)	0.4550 (3)	0.2988 (3)	0.0357 (7)
O7	0.8941 (3)	0.5849 (3)	0.1007 (2)	0.0251 (6)
O8	0.6729 (3)	0.6529 (3)	0.1488 (2)	0.0217 (6)
O1W	0.3986 (3)	0.1495 (3)	−0.0826 (2)	0.0225 (6)
H1WA	0.3469	0.0936	−0.1481	0.027*
H1WB	0.4122	0.1032	−0.0442	0.027*
O2W	0.3436 (3)	0.5492 (3)	0.1002 (3)	0.0327 (7)
H2WA	0.4404	0.5907	0.1361	0.039*
H2WB	0.3295	0.5815	0.0506	0.039*
O3W	0.0181 (3)	0.3743 (3)	0.1123 (2)	0.0277 (6)
H3WA	−0.0036	0.4498	0.1257	0.033*
H3WB	−0.0456	0.3322	0.1459	0.033*
O4W	0.2568 (4)	0.7730 (3)	0.1413 (3)	0.0389 (7)
H4WA	0.1577	0.7772	0.1398	0.047*
H4WB	0.3140	0.8382	0.1259	0.047*
O5W	0.7262 (3)	0.2225 (3)	0.1315 (2)	0.0302 (6)
H5WA	0.6621	0.2706	0.1300	0.036*
H5WB	0.7262	0.1686	0.0628	0.036*

	U11	U22	U33	U12	U13	U23
C1	0.0164 (18)	0.0202 (19)	0.0207 (19)	−0.0007 (15)	−0.0012 (14)	0.0129 (16)
C2	0.0184 (18)	0.0187 (19)	0.0173 (18)	0.0028 (15)	0.0028 (14)	0.0067 (15)
C3	0.0187 (19)	0.033 (2)	0.0191 (19)	0.0015 (17)	0.0035 (15)	0.0109 (17)
C4	0.0226 (19)	0.032 (2)	0.0153 (18)	0.0067 (17)	0.0029 (15)	0.0101 (16)
C5	0.025 (2)	0.041 (3)	0.019 (2)	0.0059 (18)	−0.0054 (16)	0.0098 (18)
C6	0.0217 (19)	0.022 (2)	0.0167 (18)	0.0034 (16)	−0.0014 (14)	0.0063 (15)
C7	0.0173 (18)	0.025 (2)	0.0215 (19)	0.0038 (16)	0.0048 (15)	0.0121 (16)
C8	0.0197 (18)	0.0151 (18)	0.0170 (18)	0.0041 (14)	0.0004 (14)	0.0077 (15)
C9	0.0188 (18)	0.0167 (18)	0.0170 (18)	−0.0018 (15)	−0.0015 (14)	0.0080 (15)
C10	0.0157 (18)	0.0199 (19)	0.023 (2)	0.0002 (15)	−0.0022 (15)	0.0109 (16)
C11	0.0139 (17)	0.0192 (19)	0.0152 (17)	0.0018 (14)	−0.0015 (13)	0.0046 (15)
C12	0.0168 (18)	0.026 (2)	0.023 (2)	0.0023 (16)	0.0042 (15)	0.0119 (17)
C13	0.0201 (18)	0.025 (2)	0.0155 (18)	0.0077 (16)	0.0029 (14)	0.0082 (16)
C14	0.029 (2)	0.028 (2)	0.018 (2)	0.0055 (18)	−0.0055 (16)	0.0060 (17)
C15	0.0159 (17)	0.0169 (19)	0.0201 (19)	0.0034 (15)	−0.0010 (14)	0.0038 (15)
C16	0.0170 (18)	0.0217 (19)	0.0204 (19)	0.0017 (15)	0.0030 (14)	0.0102 (16)
C17	0.0189 (18)	0.0171 (18)	0.0168 (18)	0.0042 (15)	0.0017 (14)	0.0080 (15)
C18	0.0144 (17)	0.0149 (18)	0.0190 (18)	−0.0025 (14)	−0.0023 (14)	0.0071 (15)
Eu1	0.01417 (10)	0.01681 (11)	0.01459 (10)	0.00295 (7)	0.00063 (6)	0.00757 (7)
N1	0.0256 (18)	0.049 (2)	0.0148 (16)	0.0055 (16)	0.0020 (13)	0.0141 (16)
N2	0.0207 (16)	0.035 (2)	0.0213 (17)	0.0029 (15)	−0.0044 (13)	0.0102 (15)
N3	0.0139 (15)	0.0304 (19)	0.0211 (17)	0.0001 (13)	−0.0064 (12)	0.0079 (14)
N4	0.0252 (17)	0.0329 (19)	0.0171 (16)	0.0051 (15)	0.0009 (13)	0.0129 (15)
O1	0.0166 (13)	0.0372 (17)	0.0244 (14)	0.0037 (12)	0.0034 (11)	0.0075 (13)
O2	0.0195 (13)	0.0199 (14)	0.0184 (13)	−0.0001 (11)	−0.0002 (10)	0.0032 (11)
O3	0.0231 (14)	0.0250 (14)	0.0281 (14)	0.0046 (11)	0.0029 (11)	0.0191 (12)
O4	0.0384 (16)	0.0338 (16)	0.0204 (14)	0.0179 (13)	0.0094 (12)	0.0128 (12)
O5	0.0226 (13)	0.0224 (14)	0.0220 (14)	0.0039 (11)	−0.0043 (11)	0.0077 (12)
O6	0.0157 (14)	0.052 (2)	0.0389 (17)	0.0044 (13)	0.0067 (12)	0.0197 (15)
O7	0.0228 (14)	0.0356 (16)	0.0224 (14)	0.0111 (12)	0.0055 (11)	0.0155 (12)
O8	0.0192 (13)	0.0260 (14)	0.0260 (14)	0.0080 (11)	0.0040 (10)	0.0160 (12)
O1W	0.0239 (14)	0.0249 (14)	0.0194 (13)	0.0065 (11)	0.0000 (10)	0.0099 (11)
O2W	0.0279 (15)	0.0213 (15)	0.0426 (18)	0.0016 (12)	−0.0120 (13)	0.0103 (13)
O3W	0.0262 (14)	0.0305 (16)	0.0355 (16)	0.0138 (12)	0.0128 (12)	0.0187 (13)
O4W	0.0299 (16)	0.0295 (17)	0.061 (2)	0.0109 (13)	0.0063 (14)	0.0200 (15)
O5W	0.0301 (15)	0.0324 (16)	0.0254 (15)	0.0093 (13)	0.0014 (12)	0.0084 (13)

C1—O1	1.256 (4)	C14—H14	0.9300
C1—O2	1.272 (4)	C15—N3	1.382 (4)
C1—C2	1.507 (5)	C15—C16	1.386 (5)
C2—C3	1.374 (5)	C16—C17	1.387 (5)
C2—C8	1.416 (5)	C16—H16	0.9300
C3—C4	1.394 (5)	C17—C18	1.502 (5)
C3—H3	0.91 (4)	C18—O7	1.249 (4)
C4—N1	1.385 (5)	C18—O8	1.267 (4)
C4—C6	1.391 (5)	Eu1—O3i	2.344 (2)
C5—N2	1.318 (5)	Eu1—O2W	2.360 (3)
C5—N1	1.345 (5)	Eu1—O3W	2.369 (3)
C5—H5	0.9300	Eu1—O2	2.407 (2)
C6—N2	1.388 (5)	Eu1—O5	2.425 (2)
C6—C7	1.396 (5)	Eu1—O8ii	2.453 (2)
C7—C8	1.379 (5)	Eu1—O1W	2.460 (2)
C7—H7	0.9300	Eu1—O7ii	2.656 (3)
C8—C9	1.509 (5)	N1—H1	0.8600
C9—O4	1.248 (4)	N3—H3A	0.8600
C9—O3	1.263 (4)	N4—H4	0.8600
C10—O6	1.239 (4)	O1W—H1WA	0.8500
C10—O5	1.282 (4)	O1W—H1WB	0.8500
C10—C11	1.518 (5)	O2W—H2WA	0.8500
C11—C12	1.382 (5)	O2W—H2WB	0.8498
C11—C17	1.424 (5)	O3W—H3WA	0.8500
C12—C13	1.387 (5)	O3W—H3WB	0.8500
C12—H12	0.9300	O4W—H4WA	0.8500
C13—N4	1.388 (5)	O4W—H4WB	0.8500
C13—C15	1.393 (5)	O5W—H5WA	0.8499
C14—N3	1.319 (5)	O5W—H5WB	0.8500
C14—N4	1.335 (5)
O1—C1—O2	125.0 (3)	O2W—Eu1—O5	70.78 (9)
O1—C1—C2	118.5 (3)	O3W—Eu1—O5	116.75 (9)
O2—C1—C2	116.3 (3)	O2—Eu1—O5	147.35 (9)
C3—C2—C8	120.3 (3)	O3i—Eu1—O8ii	147.47 (9)
C3—C2—C1	117.4 (3)	O2W—Eu1—O8ii	79.57 (10)
C8—C2—C1	122.0 (3)	O3W—Eu1—O8ii	123.60 (9)
C2—C3—C4	118.8 (3)	O2—Eu1—O8ii	80.30 (8)
C2—C3—H3	116 (3)	O5—Eu1—O8ii	103.24 (8)
C4—C3—H3	125 (3)	O3i—Eu1—O1W	81.33 (9)
N1—C4—C6	105.6 (3)	O2W—Eu1—O1W	124.88 (9)
N1—C4—C3	133.3 (3)	O3W—Eu1—O1W	156.77 (9)
C6—C4—C3	121.0 (3)	O2—Eu1—O1W	77.56 (8)
N2—C5—N1	112.8 (3)	O5—Eu1—O1W	73.73 (8)
N2—C5—H5	123.6	O8ii—Eu1—O1W	69.16 (8)
N1—C5—H5	123.6	O3i—Eu1—O7ii	142.44 (8)
N2—C6—C4	109.1 (3)	O2W—Eu1—O7ii	68.99 (9)
N2—C6—C7	130.4 (3)	O3W—Eu1—O7ii	72.82 (8)
C4—C6—C7	120.5 (3)	O2—Eu1—O7ii	71.98 (9)
C8—C7—C6	118.5 (3)	O5—Eu1—O7ii	135.26 (8)
C8—C7—H7	120.8	O8ii—Eu1—O7ii	50.84 (8)
C6—C7—H7	120.8	O1W—Eu1—O7ii	115.56 (8)
C7—C8—C2	120.9 (3)	O3i—Eu1—C18ii	154.10 (9)
C7—C8—C9	116.8 (3)	O2W—Eu1—C18ii	73.39 (10)
C2—C8—C9	122.2 (3)	O3W—Eu1—C18ii	98.19 (10)
O4—C9—O3	125.9 (3)	O2—Eu1—C18ii	73.86 (9)
O4—C9—C8	117.4 (3)	O5—Eu1—C18ii	121.97 (9)
O3—C9—C8	116.5 (3)	O8ii—Eu1—C18ii	25.48 (9)
O6—C10—O5	125.0 (3)	O1W—Eu1—C18ii	92.14 (9)
O6—C10—C11	118.1 (3)	O7ii—Eu1—C18ii	25.38 (9)
O5—C10—C11	116.9 (3)	O3i—Eu1—H2WB	146.1
C12—C11—C17	120.4 (3)	O2W—Eu1—H2WB	16.6
C12—C11—C10	117.4 (3)	O3W—Eu1—H2WB	80.6
C17—C11—C10	122.2 (3)	O2—Eu1—H2WB	125.6
C11—C12—C13	118.0 (3)	O5—Eu1—H2WB	83.6
C11—C12—H12	121.0	O8ii—Eu1—H2WB	65.6
C13—C12—H12	121.0	O1W—Eu1—H2WB	122.2
C12—C13—N4	132.5 (3)	O7ii—Eu1—H2WB	53.7
C12—C13—C15	121.4 (3)	C18ii—Eu1—H2WB	56.9
N4—C13—C15	106.1 (3)	C5—N1—C4	107.0 (3)
N3—C14—N4	111.0 (3)	C5—N1—H1	126.5
N3—C14—H14	124.5	C4—N1—H1	126.5
N4—C14—H14	124.5	C5—N2—C6	105.5 (3)
N3—C15—C16	131.3 (3)	C14—N3—C15	107.8 (3)
N3—C15—C13	107.3 (3)	C14—N3—H3A	126.1
C16—C15—C13	121.4 (3)	C15—N3—H3A	126.1
C15—C16—C17	117.6 (3)	C14—N4—C13	107.8 (3)
C15—C16—H16	121.2	C14—N4—H4	126.1
C17—C16—H16	121.2	C13—N4—H4	126.1
C16—C17—C11	121.0 (3)	C1—O2—Eu1	133.9 (2)
C16—C17—C18	115.4 (3)	C9—O3—Eu1i	129.4 (2)
C11—C17—C18	123.3 (3)	C10—O5—Eu1	116.1 (2)
O7—C18—O8	122.0 (3)	C18—O7—Eu1ii	88.9 (2)
O7—C18—C17	119.8 (3)	C18—O8—Eu1ii	98.1 (2)
O8—C18—C17	117.8 (3)	Eu1—O1W—H1WA	111.5
O7—C18—Eu1ii	65.67 (19)	Eu1—O1W—H1WB	108.5
O8—C18—Eu1ii	56.45 (17)	H1WA—O1W—H1WB	107.7
C17—C18—Eu1ii	169.2 (2)	Eu1—O2W—H2WA	122.2
O3i—Eu1—O2W	130.52 (10)	Eu1—O2W—H2WB	111.0
O3i—Eu1—O3W	80.33 (9)	H2WA—O2W—H2WB	107.7
O2W—Eu1—O3W	78.17 (10)	Eu1—O3W—H3WA	125.9
O3i—Eu1—O2	80.26 (9)	Eu1—O3W—H3WB	125.9
O2W—Eu1—O2	140.57 (9)	H3WA—O3W—H3WB	107.7
O3W—Eu1—O2	85.39 (9)	H4WA—O4W—H4WB	107.7
O3i—Eu1—O5	80.37 (9)	H5WA—O5W—H5WB	107.7
O1—C1—C2—C3	−39.6 (5)	C16—C17—C18—O7	47.4 (5)
O2—C1—C2—C3	136.4 (4)	C11—C17—C18—O7	−139.2 (4)
O1—C1—C2—C8	147.3 (4)	C16—C17—C18—O8	−125.8 (4)
O2—C1—C2—C8	−36.7 (5)	C11—C17—C18—O8	47.7 (5)
C8—C2—C3—C4	2.4 (6)	C16—C17—C18—Eu1ii	−70.7 (14)
C1—C2—C3—C4	−170.8 (4)	C11—C17—C18—Eu1ii	102.8 (12)
C2—C3—C4—N1	177.5 (4)	N2—C5—N1—C4	0.0 (5)
C2—C3—C4—C6	−0.2 (6)	C6—C4—N1—C5	0.0 (5)
N1—C4—C6—N2	0.0 (4)	C3—C4—N1—C5	−178.0 (5)
C3—C4—C6—N2	178.3 (4)	N1—C5—N2—C6	0.0 (5)
N1—C4—C6—C7	−179.8 (4)	C4—C6—N2—C5	0.0 (5)
C3—C4—C6—C7	−1.5 (6)	C7—C6—N2—C5	179.7 (4)
N2—C6—C7—C8	−178.7 (4)	N4—C14—N3—C15	1.6 (5)
C4—C6—C7—C8	1.0 (6)	C16—C15—N3—C14	176.2 (4)
C6—C7—C8—C2	1.1 (5)	C13—C15—N3—C14	−1.6 (4)
C6—C7—C8—C9	−176.4 (3)	N3—C14—N4—C13	−1.0 (5)
C3—C2—C8—C7	−2.9 (6)	C12—C13—N4—C14	179.4 (4)
C1—C2—C8—C7	170.0 (3)	C15—C13—N4—C14	0.0 (4)
C3—C2—C8—C9	174.5 (4)	O1—C1—O2—Eu1	8.7 (6)
C1—C2—C8—C9	−12.6 (5)	C2—C1—O2—Eu1	−166.9 (2)
C7—C8—C9—O4	−58.4 (5)	O3i—Eu1—O2—C1	−112.6 (3)
C2—C8—C9—O4	124.1 (4)	O2W—Eu1—O2—C1	101.4 (3)
C7—C8—C9—O3	116.7 (4)	O3W—Eu1—O2—C1	166.5 (3)
C2—C8—C9—O3	−60.7 (5)	O5—Eu1—O2—C1	−58.2 (4)
O6—C10—C11—C12	37.3 (5)	O8ii—Eu1—O2—C1	41.2 (3)
O5—C10—C11—C12	−142.0 (4)	O1W—Eu1—O2—C1	−29.4 (3)
O6—C10—C11—C17	−143.7 (4)	O7ii—Eu1—O2—C1	93.1 (3)
O5—C10—C11—C17	37.0 (5)	C18ii—Eu1—O2—C1	66.6 (3)
C17—C11—C12—C13	0.7 (6)	O4—C9—O3—Eu1i	41.5 (5)
C10—C11—C12—C13	179.8 (3)	C8—C9—O3—Eu1i	−133.1 (3)
C11—C12—C13—N4	176.6 (4)	O6—C10—O5—Eu1	17.8 (5)
C11—C12—C13—C15	−4.0 (6)	C11—C10—O5—Eu1	−163.0 (2)
C12—C13—C15—N3	−178.6 (3)	O3i—Eu1—O5—C10	−75.4 (2)
N4—C13—C15—N3	1.0 (4)	O2W—Eu1—O5—C10	63.8 (2)
C12—C13—C15—C16	3.4 (6)	O3W—Eu1—O5—C10	−1.4 (3)
N4—C13—C15—C16	−177.1 (3)	O2—Eu1—O5—C10	−129.7 (2)
N3—C15—C16—C17	−176.9 (4)	O8ii—Eu1—O5—C10	137.6 (2)
C13—C15—C16—C17	0.6 (5)	O1W—Eu1—O5—C10	−159.1 (3)
C15—C16—C17—C11	−3.8 (5)	O7ii—Eu1—O5—C10	90.8 (3)
C15—C16—C17—C18	169.9 (3)	C18ii—Eu1—O5—C10	118.8 (2)
C12—C11—C17—C16	3.2 (6)	O8—C18—O7—Eu1ii	3.3 (3)
C10—C11—C17—C16	−175.8 (3)	C17—C18—O7—Eu1ii	−169.6 (3)
C12—C11—C17—C18	−169.9 (3)	O7—C18—O8—Eu1ii	−3.6 (4)
C10—C11—C17—C18	11.1 (5)	C17—C18—O8—Eu1ii	169.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.85	1.95	2.727 (4)	152
O1W—H1WB···O4i	0.85	1.93	2.709 (4)	152
O2W—H2WA···O8	0.85	1.89	2.687 (4)	155
O2W—H2WB···O4W	0.85	2.23	2.608 (5)	107
O3W—H3WA···O7iii	0.85	2.01	2.815 (4)	159
O3W—H3WB···O5Wiii	0.85	1.96	2.685 (4)	142
O4W—H4WA···O2iv	0.85	2.19	2.968 (4)	153
O4W—H4WB···O1Wii	0.85	2.49	3.022 (4)	122
O4W—H4WB···O4iv	0.85	2.37	3.151 (4)	153
O5W—H5WA···O5	0.85	1.97	2.815 (4)	172
O5W—H5WB···O4v	0.85	1.99	2.757 (4)	150
N1—H1···O1vi	0.86	2.06	2.900 (4)	165
N3—H3A···N2vii	0.86	1.88	2.725 (5)	168
N4—H4···O6viii	0.86	1.98	2.750 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1	0.85	1.95	2.727 (4)	152
O1W—H1WB⋯O4i	0.85	1.93	2.709 (4)	152
O2W—H2WA⋯O8	0.85	1.89	2.687 (4)	155
O2W—H2WB⋯O4W	0.85	2.23	2.608 (5)	107
O3W—H3WA⋯O7ii	0.85	2.01	2.815 (4)	159
O3W—H3WB⋯O5Wii	0.85	1.96	2.685 (4)	142
O4W—H4WA⋯O2iii	0.85	2.19	2.968 (4)	153
O4W—H4WB⋯O1Wiv	0.85	2.49	3.022 (4)	122
O4W—H4WB⋯O4iii	0.85	2.37	3.151 (4)	153
O5W—H5WA⋯O5	0.85	1.97	2.815 (4)	172
O5W—H5WB⋯O4v	0.85	1.99	2.757 (4)	150
N1—H1⋯O1vi	0.86	2.06	2.900 (4)	165
N3—H3A⋯N2vii	0.86	1.88	2.725 (5)	168
N4—H4⋯O6viii	0.86	1.98	2.750 (4)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .