Bis(2,6-dihy-droxy-benzoato-κO,O)(nitrato-κO,O')bis-(1,10-phenanthroline-κN,N')europium(III).

The title mononuclear complex, [Eu(C(7)H(5)O(3))(2)(NO(3))(C(12)H(8)N(2))(2)], is isostructural with those of other lanthanides. The Eu atom is in a pseudo-bicapped square-anti-prismatic geometry, formed by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and by six O atoms, four from two 2,6-dihy-droxy-benzoate (DHB) ligands and the other two from a nitrate anion. π-π stacking inter-actions between phen and DHB ligands [centroid-centroid distances = 3.5312 (19) and 3.8347 (16) Å], and between phen and phen ligands [face-to-face separation = 3.433 (4) Å] of adjacent complexes stabilize the crystal structure. Intra-molecular O-H⋯O hydrogen bonds are observed in the DHB ligands.

Related literature

For background and details of a related structure, see: Zheng et al. (2010 ▶).

Experimental

Crystal data

[Eu(C7H5O3)2(NO3)(C12H8N2)2]

M = 880.60

Monoclinic,

a = 11.1855 (2) Å

b = 26.7682 (5) Å

c = 14.3286 (4) Å

β = 127.557 (2)°

V = 3401.05 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.92 mm−1

T = 298 K

0.40 × 0.36 × 0.35 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan [ABSPACK in CrysAlis PRO RED (Oxford Diffraction, 2006 ▶)] T min = 0.514, T max = 0.553

22346 measured reflections

6936 independent reflections

5281 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.043

S = 1.05

6936 reflections

496 parameters

8 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047148/su2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047148/su2227Isup2.hkl

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

[Eu(C7H5O3)2(NO3)(C12H8N2)2]	F(000) = 1760
Mr = 880.60	Dx = 1.720 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11999 reflections
a = 11.1855 (2) Å	θ = 2.9–29.1°
b = 26.7682 (5) Å	µ = 1.92 mm−1
c = 14.3286 (4) Å	T = 298 K
β = 127.557 (2)°	Block, orange
V = 3401.05 (16) Å3	0.40 × 0.36 × 0.35 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	6936 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5281 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 15.9149 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −13→10
Absorption correction: multi-scan [ABSPACK in CrysAlis PRO RED (Oxford Diffraction, 2006)]	k = −33→32
Tmin = 0.514, Tmax = 0.553	l = −11→17
22346 measured reflections

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) = 0.043	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0144P)2] where P = (Fo2 + 2Fc2)/3
6936 reflections	(Δ/σ)max = 0.001
496 parameters	Δρmax = 0.36 e Å−3
8 restraints	Δρmin = −0.49 e Å−3

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
Eu1	0.430778 (13)	0.861975 (4)	0.720853 (12)	0.03240 (4)
O1	0.19590 (17)	0.81211 (6)	0.63374 (15)	0.0437 (5)
O2	0.16583 (18)	0.89279 (7)	0.59806 (16)	0.0492 (5)
O3	−0.01921 (19)	0.75869 (7)	0.60271 (16)	0.0535 (5)
H31	0.0624	0.7641	0.6166	0.080*
O4	−0.0800 (2)	0.93598 (7)	0.5290 (2)	0.0750 (7)
H27	0.0062	0.9333	0.5499	0.113*
O5	0.34598 (18)	0.83820 (7)	0.52114 (15)	0.0447 (5)
O6	0.38918 (18)	0.91856 (6)	0.55787 (15)	0.0448 (5)
O7	0.2549 (2)	0.80247 (7)	0.32044 (17)	0.0606 (5)
H38	0.2789	0.8021	0.3871	0.091*
O8	0.3356 (3)	0.97889 (7)	0.39552 (19)	0.0816 (7)
H34	0.3566	0.9705	0.4590	0.122*
O9	0.45362 (19)	0.80112 (6)	0.87237 (16)	0.0469 (4)
O10	0.34644 (19)	0.87175 (7)	0.84764 (17)	0.0503 (5)
O11	0.3634 (2)	0.81721 (9)	0.96677 (19)	0.0823 (7)
N1	0.5570 (2)	0.77913 (7)	0.73843 (17)	0.0347 (5)
N2	0.6809 (2)	0.86747 (7)	0.74804 (18)	0.0370 (5)
N3	0.4755 (2)	0.95459 (7)	0.79134 (19)	0.0370 (5)
N4	0.6651 (2)	0.88072 (7)	0.93947 (18)	0.0355 (5)
N5	0.3879 (2)	0.82911 (9)	0.8983 (2)	0.0463 (5)
C1	0.4920 (3)	0.73535 (10)	0.7235 (2)	0.0427 (7)
H1	0.3946	0.7352	0.7013	0.051*
C2	0.5611 (3)	0.68954 (10)	0.7391 (2)	0.0478 (7)
H2	0.5095	0.6598	0.7246	0.057*
C3	0.7046 (3)	0.68922 (10)	0.7756 (2)	0.0480 (7)
H3	0.7532	0.6590	0.7877	0.058*
C4	0.7801 (3)	0.73409 (10)	0.7951 (2)	0.0417 (7)
C5	0.7001 (3)	0.77846 (9)	0.7716 (2)	0.0347 (6)
C6	0.9345 (3)	0.73719 (12)	0.8396 (2)	0.0526 (8)
H6	0.9904	0.7080	0.8605	0.063*
C7	1.0004 (3)	0.78094 (12)	0.8518 (2)	0.0538 (8)
H7	1.1009	0.7816	0.8812	0.065*
C8	0.9179 (3)	0.82669 (11)	0.8201 (2)	0.0437 (7)
C9	0.7677 (3)	0.82588 (10)	0.7813 (2)	0.0360 (6)
C10	0.7415 (3)	0.91061 (10)	0.7505 (2)	0.0470 (7)
H10	0.6829	0.9393	0.7266	0.056*
C11	0.8890 (3)	0.91501 (12)	0.7871 (3)	0.0552 (8)
H11	0.9270	0.9459	0.7871	0.066*
C12	0.9755 (3)	0.87350 (12)	0.8224 (3)	0.0549 (8)
H12	1.0744	0.8761	0.8486	0.066*
C13	0.3819 (3)	0.99087 (10)	0.7204 (3)	0.0465 (7)
H13	0.3059	0.9833	0.6418	0.056*
C14	0.3929 (3)	1.03979 (10)	0.7587 (3)	0.0532 (8)
H14	0.3254	1.0640	0.7062	0.064*
C15	0.5022 (3)	1.05169 (10)	0.8724 (3)	0.0520 (8)
H15	0.5099	1.0842	0.8985	0.062*
C16	0.6039 (3)	1.01513 (9)	0.9512 (3)	0.0406 (7)
C17	0.5851 (3)	0.96642 (9)	0.9062 (2)	0.0341 (6)
C18	0.6860 (3)	0.92762 (9)	0.9847 (2)	0.0337 (6)
C19	0.8009 (3)	0.93855 (10)	1.1035 (2)	0.0393 (6)
C20	0.8156 (3)	0.98871 (11)	1.1446 (3)	0.0507 (8)
H20	0.8923	0.9962	1.2231	0.061*
C21	0.7213 (3)	1.02491 (11)	1.0723 (3)	0.0509 (8)
H21	0.7326	1.0570	1.1017	0.061*
C22	0.8964 (3)	0.89993 (11)	1.1759 (3)	0.0501 (8)
H22	0.9733	0.9060	1.2552	0.060*
C23	0.8775 (3)	0.85332 (11)	1.1308 (2)	0.0477 (7)
H23	0.9415	0.8273	1.1780	0.057*
C24	0.7604 (3)	0.84565 (10)	1.0125 (2)	0.0418 (7)
H24	0.7479	0.8137	0.9825	0.050*
C25	0.1141 (3)	0.85088 (10)	0.5999 (2)	0.0405 (7)
C26	−0.0402 (3)	0.84766 (10)	0.5660 (2)	0.0388 (7)
C27	−0.1308 (3)	0.89040 (12)	0.5326 (3)	0.0521 (8)
C28	−0.2734 (3)	0.88738 (13)	0.5031 (3)	0.0586 (8)
H28	−0.3331	0.9158	0.4806	0.070*
C29	−0.3250 (3)	0.84196 (14)	0.5077 (3)	0.0586 (9)
H29	−0.4210	0.8400	0.4878	0.070*
C30	−0.2418 (3)	0.79931 (12)	0.5402 (2)	0.0516 (8)
H30	−0.2807	0.7690	0.5422	0.062*
C31	−0.0983 (3)	0.80167 (11)	0.5701 (2)	0.0414 (7)
C32	0.3466 (3)	0.88224 (11)	0.4875 (2)	0.0368 (6)
C33	0.2975 (2)	0.89004 (10)	0.3666 (2)	0.0361 (6)
C34	0.2936 (3)	0.93810 (11)	0.3255 (3)	0.0499 (7)
C35	0.2441 (3)	0.94544 (12)	0.2110 (3)	0.0641 (9)
H35	0.2395	0.9775	0.1840	0.077*
C36	0.2023 (3)	0.90549 (13)	0.1386 (3)	0.0609 (8)
H36	0.1703	0.9107	0.0623	0.073*
C37	0.2059 (3)	0.85796 (12)	0.1748 (2)	0.0520 (7)
H37	0.1767	0.8313	0.1235	0.062*
C38	0.2537 (3)	0.84956 (10)	0.2888 (2)	0.0409 (7)

	U11	U22	U33	U12	U13	U23
Eu1	0.03389 (7)	0.02771 (7)	0.03845 (8)	0.00054 (6)	0.02352 (6)	−0.00013 (7)
O1	0.0357 (9)	0.0386 (11)	0.0556 (12)	0.0033 (8)	0.0273 (10)	0.0001 (9)
O2	0.0405 (10)	0.0420 (12)	0.0621 (13)	0.0030 (9)	0.0297 (10)	0.0085 (10)
O3	0.0439 (11)	0.0508 (13)	0.0675 (14)	0.0003 (9)	0.0348 (11)	0.0069 (11)
O4	0.0591 (13)	0.0547 (14)	0.1005 (19)	0.0183 (11)	0.0431 (13)	0.0140 (13)
O5	0.0501 (11)	0.0397 (11)	0.0416 (12)	−0.0016 (9)	0.0265 (10)	0.0019 (10)
O6	0.0564 (11)	0.0396 (11)	0.0391 (11)	−0.0023 (9)	0.0296 (10)	−0.0027 (9)
O7	0.0716 (13)	0.0416 (12)	0.0486 (13)	−0.0009 (10)	0.0262 (11)	−0.0062 (10)
O8	0.140 (2)	0.0422 (13)	0.0585 (15)	−0.0165 (13)	0.0586 (16)	−0.0025 (12)
O9	0.0533 (11)	0.0388 (10)	0.0519 (12)	0.0002 (8)	0.0337 (10)	0.0046 (8)
O10	0.0594 (11)	0.0476 (10)	0.0605 (13)	0.0028 (8)	0.0451 (11)	−0.0043 (9)
O11	0.0823 (15)	0.128 (2)	0.0583 (14)	−0.0063 (14)	0.0539 (14)	0.0139 (15)
N1	0.0360 (12)	0.0318 (12)	0.0384 (13)	0.0002 (9)	0.0237 (11)	−0.0006 (10)
N2	0.0396 (11)	0.0371 (13)	0.0393 (13)	−0.0055 (10)	0.0266 (11)	−0.0033 (11)
N3	0.0479 (13)	0.0266 (12)	0.0450 (14)	0.0023 (10)	0.0327 (13)	0.0031 (10)
N4	0.0355 (11)	0.0332 (12)	0.0380 (13)	0.0019 (9)	0.0226 (11)	−0.0005 (10)
N5	0.0444 (13)	0.0586 (13)	0.0406 (14)	−0.0066 (10)	0.0283 (12)	−0.0014 (10)
C1	0.0478 (15)	0.0354 (17)	0.0466 (18)	−0.0015 (13)	0.0296 (15)	−0.0042 (13)
C2	0.0647 (19)	0.0301 (16)	0.0493 (18)	0.0017 (13)	0.0350 (17)	−0.0018 (13)
C3	0.0651 (19)	0.0364 (17)	0.0438 (18)	0.0136 (14)	0.0340 (17)	0.0025 (14)
C4	0.0456 (16)	0.0502 (18)	0.0327 (16)	0.0122 (13)	0.0256 (15)	0.0043 (13)
C5	0.0372 (14)	0.0394 (16)	0.0321 (15)	0.0023 (11)	0.0235 (13)	−0.0010 (12)
C6	0.0502 (18)	0.063 (2)	0.0441 (19)	0.0221 (15)	0.0284 (16)	0.0057 (16)
C7	0.0343 (15)	0.085 (2)	0.0408 (18)	0.0103 (16)	0.0225 (15)	0.0000 (17)
C8	0.0352 (15)	0.064 (2)	0.0330 (16)	−0.0059 (14)	0.0212 (14)	−0.0075 (15)
C9	0.0338 (14)	0.0464 (17)	0.0315 (15)	−0.0006 (12)	0.0217 (13)	−0.0023 (13)
C10	0.0507 (17)	0.0450 (17)	0.0501 (18)	−0.0075 (13)	0.0331 (15)	−0.0038 (15)
C11	0.0535 (18)	0.057 (2)	0.063 (2)	−0.0255 (15)	0.0395 (18)	−0.0108 (17)
C12	0.0379 (16)	0.083 (3)	0.0469 (18)	−0.0156 (16)	0.0276 (15)	−0.0108 (17)
C13	0.0572 (17)	0.0358 (17)	0.0544 (19)	0.0067 (13)	0.0381 (16)	0.0061 (14)
C14	0.072 (2)	0.0307 (17)	0.077 (2)	0.0110 (14)	0.055 (2)	0.0121 (16)
C15	0.078 (2)	0.0277 (16)	0.083 (2)	−0.0057 (15)	0.065 (2)	−0.0058 (16)
C16	0.0485 (16)	0.0307 (15)	0.063 (2)	−0.0079 (12)	0.0446 (17)	−0.0059 (14)
C17	0.0390 (14)	0.0311 (15)	0.0476 (18)	−0.0050 (11)	0.0343 (15)	−0.0015 (13)
C18	0.0353 (14)	0.0344 (15)	0.0443 (17)	−0.0052 (11)	0.0309 (14)	−0.0043 (13)
C19	0.0358 (14)	0.0451 (17)	0.0438 (17)	−0.0078 (12)	0.0278 (15)	−0.0076 (14)
C20	0.0481 (17)	0.058 (2)	0.0510 (19)	−0.0212 (15)	0.0329 (16)	−0.0210 (17)
C21	0.0608 (19)	0.0393 (18)	0.073 (2)	−0.0197 (15)	0.051 (2)	−0.0208 (17)
C22	0.0344 (15)	0.067 (2)	0.0441 (18)	−0.0054 (14)	0.0215 (15)	−0.0055 (16)
C23	0.0399 (15)	0.055 (2)	0.0453 (18)	0.0058 (13)	0.0246 (15)	0.0067 (15)
C24	0.0468 (16)	0.0373 (16)	0.0457 (18)	0.0033 (12)	0.0305 (16)	0.0011 (13)
C25	0.0392 (15)	0.0458 (19)	0.0357 (16)	0.0008 (12)	0.0225 (14)	0.0008 (13)
C26	0.0311 (14)	0.0479 (18)	0.0332 (15)	0.0050 (11)	0.0173 (13)	0.0018 (12)
C27	0.0479 (17)	0.056 (2)	0.0490 (19)	0.0092 (15)	0.0276 (16)	0.0075 (16)
C28	0.0417 (17)	0.079 (2)	0.052 (2)	0.0234 (16)	0.0270 (16)	0.0071 (18)
C29	0.0315 (15)	0.100 (3)	0.0434 (19)	0.0068 (17)	0.0222 (15)	0.0006 (18)
C30	0.0381 (16)	0.077 (2)	0.0431 (18)	−0.0037 (15)	0.0263 (15)	0.0016 (16)
C31	0.0345 (14)	0.0577 (19)	0.0290 (15)	0.0024 (13)	0.0178 (13)	0.0011 (14)
C32	0.0294 (13)	0.0420 (16)	0.0394 (17)	0.0022 (12)	0.0212 (13)	0.0022 (14)
C33	0.0283 (13)	0.0411 (16)	0.0367 (16)	0.0014 (11)	0.0188 (13)	0.0018 (13)
C34	0.0619 (18)	0.0447 (19)	0.0458 (19)	−0.0078 (14)	0.0342 (17)	−0.0021 (15)
C35	0.087 (2)	0.058 (2)	0.051 (2)	−0.0151 (18)	0.044 (2)	0.0030 (18)
C36	0.066 (2)	0.076 (2)	0.0427 (19)	−0.0080 (17)	0.0346 (17)	0.0005 (18)
C37	0.0486 (16)	0.063 (2)	0.0440 (18)	−0.0028 (15)	0.0280 (15)	−0.0130 (17)
C38	0.0293 (13)	0.0459 (19)	0.0410 (17)	0.0016 (11)	0.0182 (14)	−0.0014 (13)

Eu1—O5	2.4869 (17)	C8—C12	1.400 (4)
Eu1—O2	2.4904 (16)	C8—C9	1.413 (3)
Eu1—O1	2.4989 (16)	C10—C11	1.399 (3)
Eu1—O10	2.5196 (17)	C10—H10	0.9300
Eu1—N1	2.5574 (19)	C11—C12	1.352 (4)
Eu1—O6	2.5767 (17)	C11—H11	0.9300
Eu1—N2	2.5830 (18)	C12—H12	0.9300
Eu1—O9	2.5991 (17)	C13—C14	1.396 (3)
Eu1—N3	2.608 (2)	C13—H13	0.9300
Eu1—N4	2.632 (2)	C14—C15	1.350 (4)
Eu1—C25	2.856 (3)	C14—H14	0.9300
Eu1—C32	2.919 (3)	C15—C16	1.400 (4)
O1—C25	1.269 (3)	C15—H15	0.9300
O2—C25	1.270 (3)	C16—C17	1.412 (3)
O3—C31	1.349 (3)	C16—C21	1.424 (4)
O3—H31	0.8199	C17—C18	1.439 (3)
O4—C27	1.361 (3)	C18—C19	1.403 (3)
O4—H27	0.8200	C19—C22	1.391 (3)
O5—C32	1.275 (3)	C19—C20	1.435 (4)
O6—C32	1.266 (3)	C20—C21	1.339 (4)
O7—C38	1.337 (3)	C20—H20	0.9300
O7—H38	0.8200	C21—H21	0.9300
O8—C34	1.358 (3)	C22—C23	1.361 (4)
O8—H34	0.8200	C22—H22	0.9300
O9—N5	1.254 (3)	C23—C24	1.387 (4)
O10—N5	1.278 (3)	C23—H23	0.9300
O11—N5	1.211 (3)	C24—H24	0.9300
N1—C1	1.326 (3)	C25—C26	1.482 (3)
N1—C5	1.365 (3)	C26—C27	1.405 (3)
N2—C10	1.329 (3)	C26—C31	1.411 (3)
N2—C9	1.358 (3)	C27—C28	1.381 (3)
N3—C13	1.332 (3)	C28—C29	1.365 (4)
N3—C17	1.361 (3)	C28—H28	0.9300
N4—C24	1.324 (3)	C29—C30	1.363 (4)
N4—C18	1.366 (3)	C29—H29	0.9300
C1—C2	1.393 (3)	C30—C31	1.387 (3)
C1—H1	0.9300	C30—H30	0.9300
C2—C3	1.352 (3)	C32—C33	1.479 (3)
C2—H2	0.9300	C33—C34	1.405 (3)
C3—C4	1.395 (4)	C33—C38	1.411 (3)
C3—H3	0.9300	C34—C35	1.390 (4)
C4—C5	1.399 (3)	C35—C36	1.359 (4)
C4—C6	1.433 (3)	C35—H35	0.9300
C5—C9	1.440 (3)	C36—C37	1.365 (4)
C6—C7	1.337 (4)	C36—H36	0.9300
C6—H6	0.9300	C37—C38	1.394 (4)
C7—C8	1.430 (4)	C37—H37	0.9300
C7—H7	0.9300
O5—Eu1—O2	79.45 (6)	N1—C5—C9	117.2 (2)
O5—Eu1—O1	74.99 (6)	C4—C5—C9	120.3 (2)
O2—Eu1—O1	52.27 (6)	C7—C6—C4	121.8 (3)
O5—Eu1—O10	143.94 (6)	C7—C6—H6	119.1
O2—Eu1—O10	70.59 (6)	C4—C6—H6	119.1
O1—Eu1—O10	70.97 (6)	C6—C7—C8	120.7 (2)
O5—Eu1—N1	72.05 (6)	C6—C7—H7	119.6
O2—Eu1—N1	134.78 (6)	C8—C7—H7	119.6
O1—Eu1—N1	86.28 (6)	C12—C8—C9	116.3 (3)
O10—Eu1—N1	116.47 (6)	C12—C8—C7	124.1 (2)
O5—Eu1—O6	51.40 (6)	C9—C8—C7	119.6 (2)
O2—Eu1—O6	71.65 (5)	N2—C9—C8	123.3 (2)
O1—Eu1—O6	107.90 (6)	N2—C9—C5	117.9 (2)
O10—Eu1—O6	130.72 (6)	C8—C9—C5	118.7 (2)
N1—Eu1—O6	112.52 (6)	N2—C10—C11	123.3 (3)
O5—Eu1—N2	78.84 (6)	N2—C10—H10	118.3
O2—Eu1—N2	143.20 (6)	C11—C10—H10	118.3
O1—Eu1—N2	144.89 (6)	C12—C11—C10	118.8 (3)
O10—Eu1—N2	137.10 (6)	C12—C11—H11	120.6
N1—Eu1—N2	63.42 (6)	C10—C11—H11	120.6
O6—Eu1—N2	71.57 (6)	C11—C12—C8	120.9 (2)
O5—Eu1—O9	125.11 (6)	C11—C12—H12	119.6
O2—Eu1—O9	105.46 (6)	C8—C12—H12	119.6
O1—Eu1—O9	67.70 (6)	N3—C13—C14	122.9 (3)
O10—Eu1—O9	49.62 (6)	N3—C13—H13	118.5
N1—Eu1—O9	66.85 (6)	C14—C13—H13	118.5
O6—Eu1—O9	175.49 (5)	C15—C14—C13	119.6 (3)
N2—Eu1—O9	111.33 (6)	C15—C14—H14	120.2
O5—Eu1—N3	122.52 (6)	C13—C14—H14	120.2
O2—Eu1—N3	79.83 (6)	C14—C15—C16	120.1 (3)
O1—Eu1—N3	126.60 (6)	C14—C15—H15	120.0
O10—Eu1—N3	71.92 (6)	C16—C15—H15	120.0
N1—Eu1—N3	145.31 (6)	C15—C16—C17	117.1 (3)
O6—Eu1—N3	71.23 (6)	C15—C16—C21	123.1 (3)
N2—Eu1—N3	87.31 (6)	C17—C16—C21	119.8 (3)
O9—Eu1—N3	111.98 (6)	N3—C17—C16	122.7 (2)
O5—Eu1—N4	145.39 (6)	N3—C17—C18	118.5 (2)
O2—Eu1—N4	132.12 (6)	C16—C17—C18	118.8 (2)
O1—Eu1—N4	132.65 (6)	N4—C18—C19	122.2 (2)
O10—Eu1—N4	70.18 (6)	N4—C18—C17	117.8 (2)
N1—Eu1—N4	87.63 (6)	C19—C18—C17	120.0 (2)
O6—Eu1—N4	117.73 (6)	C22—C19—C18	118.0 (2)
N2—Eu1—N4	66.94 (6)	C22—C19—C20	123.1 (3)
O9—Eu1—N4	66.78 (6)	C18—C19—C20	119.0 (3)
N3—Eu1—N4	62.68 (6)	C21—C20—C19	121.4 (3)
O5—Eu1—C25	79.24 (6)	C21—C20—H20	119.3
O2—Eu1—C25	26.36 (6)	C19—C20—H20	119.3
O1—Eu1—C25	26.34 (6)	C20—C21—C16	121.1 (3)
O10—Eu1—C25	64.98 (7)	C20—C21—H21	119.4
N1—Eu1—C25	112.06 (7)	C16—C21—H21	119.4
O6—Eu1—C25	92.25 (6)	C23—C22—C19	120.1 (3)
N2—Eu1—C25	157.87 (7)	C23—C22—H22	120.0
O9—Eu1—C25	84.01 (7)	C19—C22—H22	120.0
N3—Eu1—C25	102.00 (7)	C22—C23—C24	118.2 (3)
N4—Eu1—C25	135.16 (7)	C22—C23—H23	120.9
O5—Eu1—C32	25.73 (6)	C24—C23—H23	120.9
O2—Eu1—C32	73.44 (6)	N4—C24—C23	124.5 (2)
O1—Eu1—C32	91.15 (6)	N4—C24—H24	117.7
O10—Eu1—C32	143.64 (6)	C23—C24—H24	117.7
N1—Eu1—C32	92.71 (7)	O1—C25—O2	119.9 (2)
O6—Eu1—C32	25.68 (6)	O1—C25—C26	120.1 (2)
N2—Eu1—C32	74.09 (6)	O2—C25—C26	119.9 (2)
O9—Eu1—C32	150.69 (7)	O1—C25—Eu1	60.92 (12)
N3—Eu1—C32	96.82 (7)	O2—C25—Eu1	60.54 (12)
N4—Eu1—C32	136.05 (6)	C26—C25—Eu1	165.99 (18)
C25—Eu1—C32	84.81 (7)	C27—C26—C31	118.0 (2)
C25—O1—Eu1	92.74 (14)	C27—C26—C25	121.2 (2)
C25—O2—Eu1	93.09 (15)	C31—C26—C25	120.8 (2)
C31—O3—H31	109.5	O4—C27—C28	118.2 (3)
C27—O4—H27	109.4	O4—C27—C26	120.7 (2)
C32—O5—Eu1	96.44 (16)	C28—C27—C26	121.1 (3)
C32—O6—Eu1	92.45 (15)	C29—C28—C27	118.7 (3)
C38—O7—H38	109.5	C29—C28—H28	120.6
C34—O8—H34	109.5	C27—C28—H28	120.6
N5—O9—Eu1	95.51 (15)	C30—C29—C28	122.8 (3)
N5—O10—Eu1	98.68 (14)	C30—C29—H29	118.6
C1—N1—C5	117.1 (2)	C28—C29—H29	118.6
C1—N1—Eu1	122.35 (16)	C29—C30—C31	119.2 (3)
C5—N1—Eu1	120.37 (15)	C29—C30—H30	120.4
C10—N2—C9	117.3 (2)	C31—C30—H30	120.4
C10—N2—Eu1	122.81 (17)	O3—C31—C30	117.3 (2)
C9—N2—Eu1	118.85 (15)	O3—C31—C26	122.5 (2)
C13—N3—C17	117.6 (2)	C30—C31—C26	120.2 (3)
C13—N3—Eu1	121.43 (17)	O6—C32—O5	119.7 (2)
C17—N3—Eu1	120.54 (15)	O6—C32—C33	121.0 (2)
C24—N4—C18	117.0 (2)	O5—C32—C33	119.3 (2)
C24—N4—Eu1	122.93 (16)	O6—C32—Eu1	61.87 (13)
C18—N4—Eu1	119.89 (16)	O5—C32—Eu1	57.83 (13)
O11—N5—O9	123.1 (3)	C33—C32—Eu1	176.62 (19)
O11—N5—O10	120.8 (2)	C34—C33—C38	117.7 (2)
O9—N5—O10	116.2 (2)	C34—C33—C32	121.0 (2)
O11—N5—Eu1	176.5 (2)	C38—C33—C32	121.3 (2)
O9—N5—Eu1	59.84 (12)	O8—C34—C35	117.9 (3)
O10—N5—Eu1	56.35 (12)	O8—C34—C33	121.2 (3)
N1—C1—C2	123.8 (2)	C35—C34—C33	120.9 (3)
N1—C1—H1	118.1	C36—C35—C34	119.6 (3)
C2—C1—H1	118.1	C36—C35—H35	120.2
C3—C2—C1	118.7 (3)	C34—C35—H35	120.2
C3—C2—H2	120.7	C35—C36—C37	121.8 (3)
C1—C2—H2	120.7	C35—C36—H36	119.1
C2—C3—C4	120.2 (2)	C37—C36—H36	119.1
C2—C3—H3	119.9	C36—C37—C38	119.8 (3)
C4—C3—H3	119.9	C36—C37—H37	120.1
C3—C4—C5	117.6 (2)	C38—C37—H37	120.1
C3—C4—C6	123.9 (2)	O7—C38—C37	117.9 (3)
C5—C4—C6	118.6 (3)	O7—C38—C33	122.0 (2)
N1—C5—C4	122.5 (2)	C37—C38—C33	120.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H34···O6	0.82	1.86	2.585 (3)	148
O4—H27···O2	0.82	1.83	2.561 (2)	148
O7—H38···O5	0.82	1.85	2.579 (3)	147
O3—H31···O1	0.82	1.87	2.594 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H34⋯O6	0.82	1.86	2.585 (3)	148
O4—H27⋯O2	0.82	1.83	2.561 (2)	148
O7—H38⋯O5	0.82	1.85	2.579 (3)	147
O3—H31⋯O1	0.82	1.87	2.594 (2)	147