catena-Poly[sodium [[tris(3-methyl-pyridine-2-carboxylato)europate(III)]-μ-3-methylpyridine-2-carboxylato] trihydrate].

In the title structure, {Na[Eu(C(7)H(6)NO(2))(4)]·3H(2)O}(n), the Eu(III) atom is nine-coordin-ated within a slightly distorted tricapped trigonal-prismatic coordination geometry defined by five carboxyl-ate-O atoms and four pyridine-N atoms. One of the carboxyl-ate ligands bridges the Eu cations, forming a one-dimensional coordination polymer along the b axis. The Eu-O bond distances lie within the range 2.362 (4)-2.461 (4) Å. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the polymers into a three-dimensional network.

Related literature

For general background to pyridine carb­oxy­lic complexes, see: Seo et al. (2010 ▶); Kukovec et al. (2009 ▶); Hong et al. (2008 ▶); Soares-Santos et al. (2006 ▶). For the syntheses and structures of Eu complexes, see: Lis et al. (2009 ▶); Godlewska et al. (2008 ▶); Legendziewicz et al. (2002 ▶).

Experimental

Crystal data

Na[Eu(C7H6NO2)4]·3H2O

M = 773.51

Monoclinic,

a = 11.721 (3) Å

b = 12.615 (4) Å

c = 21.133 (6) Å

β = 96.585 (7)°

V = 3104.1 (16) Å3

Z = 4

Mo Kα radiation

μ = 2.10 mm−1

T = 233 K

0.22 × 0.15 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.583, T max = 0.741

25592 measured reflections

5782 independent reflections

4104 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.148

S = 1.05

5782 reflections

428 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.77 e Å−3

Δρmin = −1.63 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003151X/tk2695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003151X/tk2695Isup2.hkl

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

Na[Eu(C7H6NO2)4]·3H2O	F(000) = 1552
Mr = 773.51	Dx = 1.655 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3070 reflections
a = 11.721 (3) Å	θ = 2.5–20.6°
b = 12.615 (4) Å	µ = 2.10 mm−1
c = 21.133 (6) Å	T = 233 K
β = 96.585 (7)°	Block, colourless
V = 3104.1 (16) Å3	0.22 × 0.15 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4104 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.088
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θmax = 25.5°, θmin = 1.9°
Tmin = 0.583, Tmax = 0.741	h = −14→14
25592 measured reflections	k = −15→15
5782 independent reflections	l = −25→25

Refinement on F2	6 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + 1.5543P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 1.77 e Å−3
5782 reflections	Δρmin = −1.63 e Å−3
428 parameters

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.

	x	y	z	Uiso*/Ueq
Eu1	0.73313 (3)	0.28658 (2)	0.240306 (15)	0.02324 (14)
N1	0.9295 (5)	0.3407 (4)	0.3039 (3)	0.0301 (13)
C2	1.0234 (6)	0.2942 (5)	0.2843 (4)	0.0314 (17)
C3	1.1302 (7)	0.2917 (6)	0.3230 (4)	0.043 (2)
C4	1.1340 (8)	0.3421 (7)	0.3822 (4)	0.053 (2)
H4	1.2033	0.3425	0.4095	0.063*
C5	1.0396 (7)	0.3910 (6)	0.4014 (4)	0.044 (2)
H5	1.0435	0.4255	0.441	0.053*
C6	0.9388 (7)	0.3882 (6)	0.3610 (4)	0.0413 (19)
H6	0.8735	0.4212	0.3741	0.05*
C7	1.0039 (7)	0.2447 (6)	0.2190 (4)	0.0374 (18)
O8	0.9005 (4)	0.2233 (3)	0.1990 (2)	0.0311 (11)
O9	1.0864 (5)	0.2306 (5)	0.1881 (3)	0.067 (2)
C10	1.2366 (8)	0.2388 (8)	0.3051 (6)	0.069 (3)
H10A	1.2968	0.2429	0.3405	0.104*
H10B	1.2615	0.2743	0.2683	0.104*
H10C	1.2201	0.165	0.2947	0.104*
N11	0.5296 (5)	0.3202 (5)	0.1801 (3)	0.0291 (13)
C12	0.4908 (6)	0.2464 (5)	0.1358 (3)	0.0268 (15)
C13	0.3748 (7)	0.2430 (6)	0.1098 (4)	0.0355 (17)
C14	0.3025 (7)	0.3207 (6)	0.1293 (4)	0.043 (2)
H14	0.2244	0.32	0.1133	0.052*
C15	0.3431 (7)	0.3994 (7)	0.1720 (4)	0.051 (2)
H15	0.2951	0.4541	0.1836	0.061*
C16	0.4579 (6)	0.3936 (6)	0.1967 (4)	0.0381 (18)
H16	0.4863	0.4446	0.2269	0.046*
C17	0.5823 (6)	0.1697 (5)	0.1196 (3)	0.0312 (16)
O18	0.6691 (4)	0.1589 (3)	0.1622 (2)	0.0276 (10)
O19	0.5705 (5)	0.1243 (4)	0.0678 (2)	0.0409 (13)
C20	0.3256 (7)	0.1569 (6)	0.0649 (4)	0.052 (2)
H20A	0.3226	0.0908	0.0881	0.078*
H20B	0.374	0.1481	0.0309	0.078*
H20C	0.2487	0.1766	0.0468	0.078*
N21	0.5686 (5)	0.1796 (5)	0.2975 (3)	0.0313 (14)
C22	0.5719 (6)	0.2005 (5)	0.3608 (3)	0.0264 (15)
C23	0.5236 (7)	0.1327 (5)	0.4029 (3)	0.0357 (17)
C24	0.4677 (7)	0.0435 (6)	0.3758 (4)	0.0419 (19)
H24	0.4342	−0.0046	0.4022	0.05*
C25	0.4604 (7)	0.0241 (6)	0.3116 (4)	0.0416 (19)
H25	0.4195	−0.0348	0.2936	0.05*
C26	0.5146 (7)	0.0935 (6)	0.2739 (4)	0.0402 (19)
H26	0.5131	0.079	0.2302	0.048*
C27	0.6349 (6)	0.3030 (5)	0.3811 (3)	0.0296 (16)
O28	0.6793 (4)	0.3518 (3)	0.3374 (2)	0.0294 (11)
O29	0.6355 (5)	0.3339 (4)	0.4368 (2)	0.0386 (12)
C30	0.5320 (9)	0.1480 (7)	0.4743 (4)	0.060 (3)
H30A	0.6116	0.1599	0.491	0.09*
H30B	0.5037	0.0851	0.4938	0.09*
H30C	0.4862	0.2088	0.4838	0.09*
N31	0.7520 (5)	0.3872 (4)	0.1301 (3)	0.0317 (14)
C32	0.7060 (6)	0.4861 (5)	0.1258 (3)	0.0314 (16)
C33	0.6665 (7)	0.5319 (5)	0.0673 (3)	0.0371 (18)
C34	0.6810 (8)	0.4736 (6)	0.0131 (4)	0.048 (2)
H34	0.6543	0.5012	−0.0273	0.058*
C35	0.7342 (8)	0.3756 (6)	0.0175 (4)	0.051 (2)
H35	0.7467	0.338	−0.0195	0.061*
C36	0.7687 (7)	0.3338 (6)	0.0771 (4)	0.0407 (19)
H36	0.8043	0.267	0.0804	0.049*
C37	0.7039 (6)	0.5389 (5)	0.1895 (3)	0.0284 (15)
O38	0.7132 (4)	0.4795 (3)	0.2383 (2)	0.0270 (11)
O39	0.6971 (4)	0.6366 (3)	0.1914 (2)	0.0302 (11)
C40	0.6091 (8)	0.6392 (6)	0.0615 (4)	0.052 (2)
H40A	0.5529	0.6441	0.0917	0.079*
H40B	0.571	0.6481	0.0186	0.079*
H40C	0.6664	0.6942	0.0705	0.079*
Na1	0.8432 (2)	0.0484 (2)	0.16277 (12)	0.0320 (6)
O41	0.7863 (5)	0.0404 (4)	0.0495 (3)	0.0408 (13)
H41A	0.777 (7)	−0.022 (2)	0.058 (4)	0.049*
H41B	0.720 (3)	0.060 (6)	0.048 (4)	0.049*
O42	1.0436 (6)	0.0189 (5)	0.1588 (3)	0.0574 (16)
H42A	1.020 (9)	0.068 (5)	0.136 (4)	0.069*
H42B	1.073 (8)	−0.003 (8)	0.128 (3)	0.069*
O43	1.0969 (6)	−0.1006 (6)	0.0514 (3)	0.0682 (19)
H43A	1.111 (9)	−0.090 (8)	0.015 (2)	0.082*
H43B	1.028 (3)	−0.113 (8)	0.040 (5)	0.082*

	U11	U22	U33	U12	U13	U23
Eu1	0.0261 (2)	0.0200 (2)	0.0234 (2)	0.00011 (13)	0.00207 (15)	−0.00091 (13)
N1	0.032 (3)	0.023 (3)	0.035 (3)	−0.004 (3)	0.000 (3)	−0.005 (3)
C2	0.027 (4)	0.016 (3)	0.052 (5)	−0.004 (3)	0.006 (4)	0.001 (3)
C3	0.032 (4)	0.036 (4)	0.059 (6)	0.001 (3)	−0.007 (4)	0.008 (4)
C4	0.050 (6)	0.052 (5)	0.050 (5)	−0.002 (4)	−0.018 (4)	0.006 (4)
C5	0.047 (5)	0.041 (4)	0.041 (5)	−0.008 (4)	−0.009 (4)	−0.005 (4)
C6	0.048 (5)	0.030 (4)	0.045 (5)	−0.002 (3)	0.002 (4)	−0.003 (3)
C7	0.035 (5)	0.029 (4)	0.050 (5)	0.001 (3)	0.012 (4)	−0.001 (3)
O8	0.025 (3)	0.032 (3)	0.036 (3)	0.001 (2)	0.005 (2)	−0.005 (2)
O9	0.032 (3)	0.095 (5)	0.079 (5)	−0.023 (3)	0.030 (3)	−0.039 (4)
C10	0.040 (6)	0.073 (6)	0.093 (8)	0.014 (5)	−0.002 (6)	0.002 (6)
N11	0.020 (3)	0.035 (3)	0.033 (3)	0.005 (3)	0.002 (3)	−0.006 (3)
C12	0.025 (4)	0.029 (3)	0.026 (4)	0.003 (3)	−0.002 (3)	0.006 (3)
C13	0.034 (4)	0.037 (4)	0.035 (4)	0.001 (3)	−0.001 (4)	0.009 (3)
C14	0.033 (4)	0.043 (4)	0.054 (5)	0.007 (4)	0.003 (4)	0.005 (4)
C15	0.033 (5)	0.052 (5)	0.068 (6)	0.016 (4)	0.013 (4)	−0.004 (4)
C16	0.032 (4)	0.037 (4)	0.047 (5)	−0.003 (3)	0.010 (4)	0.002 (3)
C17	0.035 (4)	0.029 (4)	0.029 (4)	−0.003 (3)	−0.001 (3)	0.000 (3)
O18	0.025 (2)	0.026 (2)	0.029 (3)	−0.002 (2)	−0.005 (2)	−0.002 (2)
O19	0.048 (3)	0.040 (3)	0.032 (3)	−0.001 (2)	−0.002 (3)	−0.011 (2)
C20	0.043 (5)	0.048 (5)	0.059 (6)	0.000 (4)	−0.022 (4)	−0.005 (4)
N21	0.033 (3)	0.028 (3)	0.033 (3)	0.001 (3)	0.006 (3)	0.003 (3)
C22	0.030 (4)	0.021 (3)	0.028 (4)	0.001 (3)	0.005 (3)	0.007 (3)
C23	0.049 (5)	0.024 (4)	0.036 (4)	0.001 (3)	0.014 (4)	0.007 (3)
C24	0.042 (5)	0.031 (4)	0.054 (5)	−0.005 (3)	0.013 (4)	0.007 (4)
C25	0.039 (5)	0.034 (4)	0.053 (5)	−0.010 (3)	0.010 (4)	−0.006 (4)
C26	0.045 (5)	0.040 (4)	0.035 (4)	−0.009 (4)	0.003 (4)	−0.006 (3)
C27	0.030 (4)	0.033 (4)	0.025 (4)	0.008 (3)	0.003 (3)	0.001 (3)
O28	0.040 (3)	0.024 (2)	0.027 (2)	−0.002 (2)	0.015 (2)	−0.006 (2)
O29	0.049 (3)	0.040 (3)	0.027 (3)	−0.007 (3)	0.008 (2)	−0.001 (2)
C30	0.100 (8)	0.041 (5)	0.041 (5)	−0.026 (5)	0.018 (5)	0.005 (4)
N31	0.038 (4)	0.026 (3)	0.032 (3)	−0.004 (3)	0.007 (3)	−0.001 (2)
C32	0.039 (4)	0.023 (4)	0.033 (4)	−0.001 (3)	0.009 (3)	0.000 (3)
C33	0.045 (5)	0.035 (4)	0.031 (4)	−0.012 (3)	−0.002 (4)	0.005 (3)
C34	0.075 (6)	0.045 (5)	0.026 (4)	−0.016 (4)	0.005 (4)	0.001 (4)
C35	0.085 (7)	0.039 (5)	0.032 (4)	−0.011 (4)	0.019 (5)	−0.005 (4)
C36	0.062 (5)	0.027 (4)	0.037 (4)	−0.003 (4)	0.018 (4)	−0.003 (3)
C37	0.029 (4)	0.022 (4)	0.034 (4)	−0.003 (3)	0.000 (3)	0.001 (3)
O38	0.044 (3)	0.007 (2)	0.031 (3)	0.0076 (18)	0.009 (2)	0.0021 (18)
O39	0.039 (3)	0.022 (2)	0.029 (3)	−0.002 (2)	0.003 (2)	−0.006 (2)
C40	0.065 (6)	0.040 (5)	0.050 (5)	−0.005 (4)	−0.005 (5)	0.011 (4)
Na1	0.0388 (16)	0.0279 (14)	0.0295 (14)	0.0015 (12)	0.0048 (13)	−0.0019 (11)
O41	0.054 (4)	0.038 (3)	0.032 (3)	0.007 (3)	0.013 (3)	0.002 (2)
O42	0.057 (4)	0.058 (4)	0.061 (4)	0.007 (3)	0.020 (4)	−0.005 (3)
O43	0.049 (4)	0.107 (5)	0.052 (4)	−0.013 (4)	0.018 (4)	−0.001 (4)

Eu1—O28	2.362 (4)	N21—C22	1.360 (9)
Eu1—O18	2.366 (4)	C22—C23	1.399 (9)
Eu1—O8	2.375 (5)	C22—C27	1.526 (9)
Eu1—O38	2.445 (4)	C23—C24	1.392 (10)
Eu1—O39i	2.461 (4)	C23—C30	1.513 (11)
Eu1—N11	2.606 (5)	C24—C25	1.371 (11)
Eu1—N1	2.619 (6)	C24—H24	0.94
Eu1—N31	2.683 (6)	C25—C26	1.386 (10)
Eu1—N21	2.745 (6)	C25—H25	0.94
N1—C6	1.341 (9)	C26—H26	0.94
N1—C2	1.354 (9)	C27—O29	1.238 (8)
C2—C3	1.415 (11)	C27—O28	1.271 (8)
C2—C7	1.507 (11)	O28—Na1ii	2.495 (5)
C3—C4	1.399 (12)	C30—H30A	0.97
C3—C10	1.501 (12)	C30—H30B	0.97
C4—C5	1.368 (12)	C30—H30C	0.97
C4—H4	0.94	N31—C36	1.342 (9)
C5—C6	1.376 (11)	N31—C32	1.359 (8)
C5—H5	0.94	C32—C33	1.395 (10)
C6—H6	0.94	C32—C37	1.505 (9)
C7—O9	1.242 (9)	C33—C34	1.389 (10)
C7—O8	1.266 (9)	C33—C40	1.510 (11)
O8—Na1	2.405 (5)	C34—C35	1.382 (12)
C10—H10A	0.97	C34—H34	0.94
C10—H10B	0.97	C35—C36	1.382 (11)
C10—H10C	0.97	C35—H35	0.94
N11—C16	1.325 (9)	C36—H36	0.94
N11—C12	1.360 (9)	C37—O39	1.236 (7)
C12—C13	1.408 (10)	C37—O38	1.269 (8)
C12—C17	1.512 (10)	O38—Na1ii	2.425 (5)
C13—C14	1.389 (11)	O39—Eu1ii	2.461 (4)
C13—C20	1.513 (11)	C40—H40A	0.97
C14—C15	1.388 (12)	C40—H40B	0.97
C14—H14	0.94	C40—H40C	0.97
C15—C16	1.389 (11)	Na1—O42	2.390 (7)
C15—H15	0.94	Na1—O41	2.412 (6)
C16—H16	0.94	Na1—O38i	2.425 (5)
C17—O19	1.229 (8)	Na1—O28i	2.495 (5)
C17—O18	1.287 (8)	O41—H41A	0.82 (2)
O18—Na1	2.470 (5)	O41—H41B	0.81 (2)
C20—H20A	0.97	O42—H42A	0.81 (4)
C20—H20B	0.97	O42—H42B	0.82 (4)
C20—H20C	0.97	O43—H43A	0.82 (3)
N21—C26	1.326 (9)	O43—H43B	0.83 (2)
O28—Eu1—O18	138.38 (16)	H20A—C20—H20C	109.5
O28—Eu1—O8	138.64 (17)	H20B—C20—H20C	109.5
O18—Eu1—O8	73.99 (16)	C26—N21—C22	119.2 (6)
O28—Eu1—O38	68.54 (14)	C26—N21—Eu1	124.5 (5)
O18—Eu1—O38	130.08 (15)	C22—N21—Eu1	113.3 (4)
O8—Eu1—O38	114.16 (15)	N21—C22—C23	122.6 (6)
O28—Eu1—O39i	82.10 (15)	N21—C22—C27	113.5 (6)
O18—Eu1—O39i	86.72 (15)	C23—C22—C27	123.9 (6)
O8—Eu1—O39i	73.99 (16)	C24—C23—C22	116.0 (7)
O38—Eu1—O39i	143.12 (15)	C24—C23—C30	119.1 (7)
O28—Eu1—N11	92.68 (17)	C22—C23—C30	124.8 (7)
O18—Eu1—N11	64.57 (16)	C25—C24—C23	121.6 (7)
O8—Eu1—N11	128.55 (17)	C25—C24—H24	119.2
O38—Eu1—N11	75.50 (17)	C23—C24—H24	119.2
O39i—Eu1—N11	129.43 (17)	C24—C25—C26	118.3 (7)
O28—Eu1—N1	76.71 (17)	C24—C25—H25	120.8
O18—Eu1—N1	136.50 (16)	C26—C25—H25	120.8
O8—Eu1—N1	64.04 (17)	N21—C26—C25	122.2 (7)
O38—Eu1—N1	79.96 (16)	N21—C26—H26	118.9
O39i—Eu1—N1	71.71 (16)	C25—C26—H26	118.9
N11—Eu1—N1	155.41 (18)	O29—C27—O28	125.5 (7)
O28—Eu1—N31	130.23 (16)	O29—C27—C22	118.9 (6)
O18—Eu1—N31	76.59 (16)	O28—C27—C22	115.5 (6)
O8—Eu1—N31	71.71 (17)	C27—O28—Eu1	129.5 (4)
O38—Eu1—N31	62.05 (15)	C27—O28—Na1ii	115.5 (4)
O39i—Eu1—N31	144.81 (17)	Eu1—O28—Na1ii	112.56 (18)
N11—Eu1—N31	70.19 (18)	C23—C30—H30A	109.5
N1—Eu1—N31	99.62 (18)	C23—C30—H30B	109.5
O28—Eu1—N21	61.14 (16)	H30A—C30—H30B	109.5
O18—Eu1—N21	77.87 (17)	C23—C30—H30C	109.5
O8—Eu1—N21	130.42 (17)	H30A—C30—H30C	109.5
O38—Eu1—N21	115.25 (16)	H30B—C30—H30C	109.5
O39i—Eu1—N21	64.34 (17)	C36—N31—C32	120.0 (6)
N11—Eu1—N21	69.23 (18)	C36—N31—Eu1	121.5 (4)
N1—Eu1—N21	121.48 (18)	C32—N31—Eu1	114.9 (4)
N31—Eu1—N21	138.30 (18)	N31—C32—C33	121.9 (6)
O28—Eu1—Na1	143.49 (12)	N31—C32—C37	113.2 (6)
O18—Eu1—Na1	40.69 (11)	C33—C32—C37	124.9 (6)
O8—Eu1—Na1	39.15 (12)	C34—C33—C32	116.9 (7)
O38—Eu1—Na1	146.40 (11)	C34—C33—C40	120.2 (7)
O39i—Eu1—Na1	61.90 (11)	C32—C33—C40	122.8 (7)
N11—Eu1—Na1	105.07 (13)	C35—C34—C33	120.9 (7)
N1—Eu1—Na1	96.20 (13)	C35—C34—H34	119.5
N31—Eu1—Na1	86.14 (13)	C33—C34—H34	119.5
N21—Eu1—Na1	95.37 (13)	C36—C35—C34	119.1 (7)
O28—Eu1—Na1ii	34.76 (11)	C36—C35—H35	120.5
O18—Eu1—Na1ii	147.06 (11)	C34—C35—H35	120.5
O8—Eu1—Na1ii	134.53 (12)	N31—C36—C35	120.9 (7)
O38—Eu1—Na1ii	33.77 (11)	N31—C36—H36	119.5
O39i—Eu1—Na1ii	114.16 (11)	C35—C36—H36	119.5
N11—Eu1—Na1ii	82.61 (13)	O39—C37—O38	124.2 (6)
N1—Eu1—Na1ii	76.06 (13)	O39—C37—C32	118.5 (6)
N31—Eu1—Na1ii	95.64 (12)	O38—C37—C32	117.2 (5)
N21—Eu1—Na1ii	88.33 (13)	C37—O38—Na1ii	118.8 (4)
Na1—Eu1—Na1ii	172.242 (13)	C37—O38—Eu1	126.9 (4)
C6—N1—C2	119.0 (6)	Na1ii—O38—Eu1	112.13 (17)
C6—N1—Eu1	123.7 (5)	C37—O39—Eu1ii	140.1 (4)
C2—N1—Eu1	115.3 (4)	C33—C40—H40A	109.5
N1—C2—C3	121.9 (7)	C33—C40—H40B	109.5
N1—C2—C7	114.6 (6)	H40A—C40—H40B	109.5
C3—C2—C7	123.4 (7)	C33—C40—H40C	109.5
C4—C3—C2	116.3 (8)	H40A—C40—H40C	109.5
C4—C3—C10	119.1 (8)	H40B—C40—H40C	109.5
C2—C3—C10	124.7 (8)	O42—Na1—O8	85.1 (2)
C5—C4—C3	121.7 (8)	O42—Na1—O41	96.8 (2)
C5—C4—H4	119.2	O8—Na1—O41	112.9 (2)
C3—C4—H4	119.2	O42—Na1—O38i	109.9 (2)
C4—C5—C6	118.1 (8)	O8—Na1—O38i	98.53 (18)
C4—C5—H5	120.9	O41—Na1—O38i	140.2 (2)
C6—C5—H5	120.9	O42—Na1—O18	154.5 (2)
N1—C6—C5	123.0 (8)	O8—Na1—O18	71.62 (17)
N1—C6—H6	118.5	O41—Na1—O18	83.39 (18)
C5—C6—H6	118.5	O38i—Na1—O18	84.22 (17)
O9—C7—O8	124.5 (8)	O42—Na1—O28i	87.1 (2)
O9—C7—C2	119.8 (7)	O8—Na1—O28i	159.7 (2)
O8—C7—C2	115.7 (6)	O41—Na1—O28i	86.55 (18)
C7—O8—Eu1	127.2 (5)	O38i—Na1—O28i	66.77 (15)
C7—O8—Na1	121.6 (4)	O18—Na1—O28i	118.29 (18)
Eu1—O8—Na1	102.29 (19)	O42—Na1—Eu1	122.20 (18)
C3—C10—H10A	109.5	O8—Na1—Eu1	38.56 (12)
C3—C10—H10B	109.5	O41—Na1—Eu1	113.60 (15)
H10A—C10—H10B	109.5	O38i—Na1—Eu1	76.54 (12)
C3—C10—H10C	109.5	O18—Na1—Eu1	38.65 (11)
H10A—C10—H10C	109.5	O28i—Na1—Eu1	139.58 (14)
H10B—C10—H10C	109.5	O42—Na1—Eu1i	99.58 (18)
C16—N11—C12	119.2 (6)	O8—Na1—Eu1i	131.19 (15)
C16—N11—Eu1	123.9 (5)	O41—Na1—Eu1i	114.62 (15)
C12—N11—Eu1	116.1 (4)	O38i—Na1—Eu1i	34.09 (10)
N11—C12—C13	121.4 (6)	O18—Na1—Eu1i	103.45 (13)
N11—C12—C17	113.8 (6)	O28i—Na1—Eu1i	32.67 (10)
C13—C12—C17	124.8 (6)	Eu1—Na1—Eu1i	109.18 (7)
C14—C13—C12	117.2 (7)	O42—Na1—H41A	97 (2)
C14—C13—C20	119.5 (7)	O8—Na1—H41A	132.3 (6)
C12—C13—C20	123.3 (7)	O41—Na1—H41A	19.4 (6)
C15—C14—C13	121.5 (8)	O38i—Na1—H41A	124.4 (12)
C15—C14—H14	119.2	O18—Na1—H41A	91.5 (18)
C13—C14—H14	119.2	O28i—Na1—H41A	67.2 (7)
C14—C15—C16	116.8 (7)	Eu1—Na1—H41A	127.3 (16)
C14—C15—H15	121.6	Eu1i—Na1—H41A	95.6 (7)
C16—C15—H15	121.6	O42—Na1—H42A	19.9 (10)
N11—C16—C15	123.7 (7)	O8—Na1—H42A	75 (2)
N11—C16—H16	118.2	O41—Na1—H42A	85 (2)
C15—C16—H16	118.2	O38i—Na1—H42A	127.8 (14)
O19—C17—O18	125.0 (7)	O18—Na1—H42A	136.9 (11)
O19—C17—C12	119.3 (6)	O28i—Na1—H42A	102.2 (18)
O18—C17—C12	115.6 (6)	Eu1—Na1—H42A	114 (2)
C17—O18—Eu1	125.3 (4)	Eu1i—Na1—H42A	119.1 (8)
C17—O18—Na1	130.5 (4)	H41A—Na1—H42A	91 (3)
Eu1—O18—Na1	100.66 (17)	Na1—O41—H41B	101 (7)
C13—C20—H20A	109.5	H41A—O41—H41B	99 (8)
C13—C20—H20B	109.5	Na1—O42—H42B	126 (7)
H20A—C20—H20B	109.5	H42A—O42—H42B	86 (10)
C13—C20—H20C	109.5	H43A—O43—H43B	93 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O41—H41A···O29i	0.82 (2)	2.08 (6)	2.767 (7)	141 (8)
O41—H41B···O19	0.81 (2)	2.02 (3)	2.809 (8)	164 (9)
O42—H42A···O9	0.81 (4)	2.41 (10)	2.774 (9)	108 (8)
O42—H42B···O43	0.82 (4)	2.08 (4)	2.852 (10)	158 (10)
O43—H43A···O41iii	0.82 (3)	2.02 (6)	2.769 (9)	152 (11)
O43—H43B···O29i	0.83 (2)	2.14 (6)	2.884 (8)	149 (10)

Table 1

Selected bond lengths (Å)

Eu1—O28	2.362 (4)
Eu1—O18	2.366 (4)
Eu1—O8	2.375 (5)
Eu1—O38	2.445 (4)
Eu1—O39i	2.461 (4)
Eu1—N11	2.606 (5)
Eu1—N1	2.619 (6)
Eu1—N31	2.683 (6)
Eu1—N21	2.745 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O41—H41A⋯O29i	0.82 (2)	2.08 (6)	2.767 (7)	141 (8)
O41—H41B⋯O19	0.81 (2)	2.02 (3)	2.809 (8)	164 (9)
O42—H42A⋯O9	0.81 (4)	2.41 (10)	2.774 (9)	108 (8)
O42—H42B⋯O43	0.82 (4)	2.08 (4)	2.852 (10)	158 (10)
O43—H43A⋯O41ii	0.82 (3)	2.02 (6)	2.769 (9)	152 (11)
O43—H43B⋯O29i	0.83 (2)	2.14 (6)	2.884 (8)	149 (10)

Symmetry codes: (i) ; (ii) .