[13,27-Dichloro-3,6,9,17,20,23-hexa-azatetracyclo-[23.3.1.1.0]triaconta-1(29),9,11,13,15(30),16,23,25,27-nona-ene-29,30-diol-κN,N,N,O,O]bis-(nitrato-κO,O')europium(III) nitrate methanol hemisolvate.

The title compound, [Eu(III)(NO(3))(2)(C(24)H(28)Cl(2)N(6)O(2))]NO(3)·0.5CH(3)OH, is isostructural with the Gd(III) and Ho(III) complexes of the analogous macrocyclic ligand, with both Cl atoms replaced by methyl groups. The Eu atom exhibits a nine-coordinate distorted tricapped trigonal-prismatic coordination geometry. The methanol solvent mol-ecule is disordered about a twofold rotation axis with occupancies of 0.543 (12):0.457 (12).

Related literature

For applications of macrocyclic lanthanide complexes, see: Alexander (1995 ▶); Bunzli & Piguet (2002 ▶). For related structures, see: Hu, Chen et al. (2007 ▶); Hu, Qiu, Yuan & Pan (2007 ▶); Hu, Qiu, Zhao & Pan (2007 ▶).

Experimental

Crystal data

[Eu(NO3)2(C24H28Cl2N6O2)]NO3·0.5CH4O

M = 857.44

Monoclinic,

a = 23.7371 (16) Å

b = 14.3327 (10) Å

c = 19.3880 (13) Å

β = 91.804 (1)°

V = 6592.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 2.14 mm−1

T = 293 K

0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.58, T max = 0.66

18638 measured reflections

6469 independent reflections

5337 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.02

6469 reflections

453 parameters

62 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.37 e Å−3

Δρmin = −0.81 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013440/bi2359sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013440/bi2359Isup2.hkl

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

[Eu(NO3)2(C24H28Cl2N6O2)]NO3·0.5CH4O	F(000) = 3432
Mr = 857.44	Dx = 1.728 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8071 reflections
a = 23.7371 (16) Å	θ = 2.6–27.9°
b = 14.3327 (10) Å	µ = 2.14 mm−1
c = 19.3880 (13) Å	T = 293 K
β = 91.804 (1)°	Block, yellow
V = 6592.9 (8) Å3	0.30 × 0.22 × 0.20 mm
Z = 8

Bruker SMART CCD diffractometer	6469 independent reflections
Radiation source: sealed tube	5337 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −28→29
Tmin = 0.58, Tmax = 0.66	k = −13→17
18638 measured reflections	l = −16→23

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0424P)2 + 14.6115P] where P = (Fo2 + 2Fc2)/3
6469 reflections	(Δ/σ)max = 0.001
453 parameters	Δρmax = 1.37 e Å−3
62 restraints	Δρmin = −0.81 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	Occ. (<1)
Eu1	0.132267 (7)	0.505891 (12)	0.114103 (11)	0.04946 (8)
Cl1	−0.09862 (5)	0.87749 (10)	0.19253 (8)	0.0924 (4)
Cl2	0.44821 (4)	0.56791 (11)	0.04485 (7)	0.0868 (4)
N1	0.02753 (14)	0.4948 (2)	0.1406 (2)	0.0578 (9)
N2	0.08955 (15)	0.3511 (3)	0.0744 (2)	0.0720 (11)
H2	0.1009	0.3075	0.1060	0.086*
N3	0.20067 (15)	0.3992 (3)	0.0512 (2)	0.0682 (10)
N4	0.24192 (12)	0.7536 (2)	0.16799 (16)	0.0532 (8)
N5	0.25996 (14)	0.6549 (3)	0.25521 (17)	0.0677 (10)
H5A	0.2367	0.6078	0.2429	0.081*
H5B	0.2859	0.6335	0.2862	0.081*
N6	0.14960 (12)	0.8091 (2)	0.09364 (17)	0.0500 (7)
H6	0.1482 (19)	0.750 (4)	0.093 (2)	0.075 (15)*
O1	0.22095 (10)	0.5406 (2)	0.15231 (14)	0.0581 (7)
O2	0.09634 (10)	0.65382 (18)	0.12070 (15)	0.0543 (6)
C1	0.05213 (14)	0.7012 (3)	0.13456 (18)	0.0448 (8)
C2	0.05371 (14)	0.7998 (3)	0.13119 (19)	0.0479 (8)
C3	0.00702 (16)	0.8538 (3)	0.1483 (2)	0.0576 (10)
H3	0.0087	0.9186	0.1459	0.069*
C4	−0.04138 (16)	0.8101 (3)	0.1685 (2)	0.0602 (10)
C5	−0.04490 (15)	0.7141 (3)	0.1701 (2)	0.0584 (10)
H5	−0.0783	0.6861	0.1831	0.070*
C6	0.00017 (14)	0.6583 (3)	0.15280 (19)	0.0497 (9)
C7	−0.00850 (15)	0.5575 (3)	0.1519 (2)	0.0576 (10)
H7	−0.0447	0.5370	0.1607	0.069*
C8	0.00742 (19)	0.3978 (3)	0.1386 (3)	0.0761 (14)
H8A	−0.0334	0.3967	0.1393	0.091*
H8B	0.0221	0.3642	0.1787	0.091*
C9	0.02697 (18)	0.3523 (3)	0.0740 (3)	0.0811 (15)
H9A	0.0127	0.2889	0.0712	0.097*
H9B	0.0126	0.3864	0.0340	0.097*
C10	0.1133 (2)	0.3240 (4)	0.0092 (3)	0.0850 (15)
H10A	0.1036	0.3703	−0.0257	0.102*
H10B	0.0974	0.2647	−0.0056	0.102*
C11	0.1762 (2)	0.3157 (4)	0.0168 (3)	0.0911 (17)
H11A	0.1858	0.2606	0.0437	0.109*
H11B	0.1921	0.3087	−0.0284	0.109*
C12	0.25325 (19)	0.4135 (3)	0.0422 (3)	0.0697 (12)
H12	0.2708	0.3721	0.0128	0.084*
C13	0.28854 (17)	0.4860 (3)	0.0720 (2)	0.0586 (10)
C14	0.34386 (19)	0.4933 (3)	0.0490 (2)	0.0660 (12)
H14	0.3567	0.4506	0.0170	0.079*
C15	0.37933 (16)	0.5622 (3)	0.0730 (2)	0.0625 (11)
C16	0.36114 (15)	0.6265 (3)	0.1197 (2)	0.0582 (10)
H16	0.3852	0.6741	0.1348	0.070*
C17	0.30710 (14)	0.6210 (3)	0.1445 (2)	0.0542 (9)
C18	0.27015 (14)	0.5485 (3)	0.1232 (2)	0.0520 (9)
C19	0.28796 (15)	0.6941 (3)	0.1932 (2)	0.0573 (10)
H19	0.3201	0.7329	0.2081	0.069*
C20	0.2276 (2)	0.7336 (4)	0.2848 (2)	0.0845 (16)
H20A	0.2458	0.7561	0.3271	0.101*
H20B	0.1894	0.7146	0.2943	0.101*
C21	0.22782 (18)	0.8080 (4)	0.2290 (2)	0.0702 (13)
H21A	0.1912	0.8374	0.2232	0.084*
H21B	0.2560	0.8555	0.2392	0.084*
C22	0.25275 (15)	0.8039 (3)	0.1050 (2)	0.0584 (10)
H22A	0.2638	0.7600	0.0698	0.070*
H22B	0.2839	0.8468	0.1134	0.070*
C23	0.20158 (16)	0.8584 (3)	0.0787 (2)	0.0608 (10)
H23A	0.2013	0.9193	0.1004	0.073*
H23B	0.2038	0.8674	0.0293	0.073*
C24	0.10390 (15)	0.8487 (3)	0.1123 (2)	0.0517 (9)
H24	0.1032	0.9136	0.1137	0.062*
N7	0.12585 (13)	0.6082 (3)	−0.01481 (18)	0.0570 (8)
O3	0.09247 (12)	0.5410 (2)	−0.00393 (16)	0.0666 (7)
O4	0.17132 (10)	0.6095 (2)	0.02117 (15)	0.0602 (7)
O5	0.11402 (13)	0.6698 (3)	−0.05529 (18)	0.0798 (9)
N8	0.14009 (18)	0.4670 (5)	0.2623 (3)	0.0941 (16)
O6	0.13883 (15)	0.4020 (3)	0.2184 (2)	0.0917 (12)
O7	0.13077 (13)	0.5480 (3)	0.24185 (17)	0.0784 (9)
O8	0.1559 (4)	0.4690 (9)	0.3256 (3)	0.099 (2)	0.543 (12)
O8'	0.1383 (5)	0.4232 (9)	0.3188 (5)	0.099 (2)	0.457 (12)
N9	0.36911 (18)	0.6104 (3)	0.3621 (2)	0.0765 (11)
O9	0.4091 (2)	0.5910 (4)	0.3993 (3)	0.1301 (16)
O10	0.3339 (3)	0.5519 (5)	0.3452 (4)	0.104 (2)	0.687 (7)
O11	0.3656 (3)	0.6888 (3)	0.3356 (3)	0.0957 (17)	0.687 (7)
O10'	0.3531 (7)	0.5516 (10)	0.3194 (7)	0.104 (2)	0.313 (7)
O11'	0.3356 (5)	0.6730 (8)	0.3750 (7)	0.0957 (17)	0.313 (7)
C1M	0.5000	0.6209 (14)	0.2500	0.220 (8)
H1MA	0.5386	0.6246	0.2370	0.330*	0.50
H1MB	0.4985	0.6041	0.2978	0.330*	0.50
H1MC	0.4808	0.5744	0.2224	0.330*	0.50
O1M	0.4733 (8)	0.7024 (13)	0.2367 (13)	0.295 (11)	0.50
H1WD	0.4442	0.7310	0.2458	0.442*	0.50

	U11	U22	U33	U12	U13	U23
Eu1	0.03538 (11)	0.04471 (12)	0.06810 (15)	0.00163 (7)	−0.00116 (8)	0.00535 (8)
Cl1	0.0600 (7)	0.0939 (9)	0.1253 (11)	0.0351 (6)	0.0364 (7)	0.0337 (8)
Cl2	0.0409 (5)	0.1263 (11)	0.0944 (9)	0.0189 (6)	0.0194 (5)	0.0119 (8)
N1	0.0387 (17)	0.0527 (19)	0.082 (2)	−0.0089 (14)	−0.0029 (16)	0.0151 (16)
N2	0.055 (2)	0.052 (2)	0.108 (3)	0.0004 (16)	−0.014 (2)	0.002 (2)
N3	0.059 (2)	0.055 (2)	0.091 (3)	0.0117 (17)	−0.0009 (19)	−0.0088 (18)
N4	0.0346 (15)	0.069 (2)	0.0562 (19)	−0.0009 (14)	0.0057 (13)	−0.0043 (15)
N5	0.0447 (18)	0.104 (3)	0.054 (2)	0.0002 (18)	−0.0010 (15)	0.0061 (19)
N6	0.0378 (15)	0.0477 (19)	0.065 (2)	−0.0017 (14)	0.0060 (14)	0.0057 (15)
O1	0.0344 (13)	0.0762 (19)	0.0637 (17)	0.0021 (12)	0.0033 (11)	−0.0021 (14)
O2	0.0368 (13)	0.0453 (14)	0.0814 (19)	0.0022 (11)	0.0128 (12)	0.0044 (13)
C1	0.0346 (16)	0.051 (2)	0.049 (2)	−0.0001 (14)	0.0021 (14)	0.0074 (15)
C2	0.0407 (18)	0.050 (2)	0.053 (2)	0.0026 (15)	0.0044 (15)	0.0061 (16)
C3	0.051 (2)	0.055 (2)	0.067 (3)	0.0102 (18)	0.0099 (18)	0.0108 (19)
C4	0.0405 (19)	0.071 (3)	0.070 (3)	0.0138 (18)	0.0092 (18)	0.016 (2)
C5	0.0366 (18)	0.072 (3)	0.067 (3)	0.0045 (18)	0.0066 (17)	0.020 (2)
C6	0.0334 (17)	0.060 (2)	0.056 (2)	−0.0001 (15)	0.0029 (15)	0.0144 (17)
C7	0.0327 (18)	0.065 (3)	0.076 (3)	−0.0073 (17)	0.0001 (17)	0.019 (2)
C8	0.050 (2)	0.058 (3)	0.120 (4)	−0.010 (2)	−0.003 (2)	0.021 (3)
C9	0.054 (2)	0.053 (3)	0.134 (5)	−0.008 (2)	−0.018 (3)	−0.003 (3)
C10	0.077 (3)	0.062 (3)	0.115 (4)	0.003 (2)	−0.013 (3)	−0.023 (3)
C11	0.077 (3)	0.063 (3)	0.132 (5)	0.009 (3)	0.000 (3)	−0.032 (3)
C12	0.061 (3)	0.060 (3)	0.088 (3)	0.022 (2)	0.005 (2)	−0.007 (2)
C13	0.046 (2)	0.062 (3)	0.068 (3)	0.0165 (18)	0.0005 (18)	0.0042 (19)
C14	0.051 (2)	0.080 (3)	0.068 (3)	0.030 (2)	0.006 (2)	0.005 (2)
C15	0.0349 (19)	0.085 (3)	0.068 (3)	0.017 (2)	0.0078 (18)	0.013 (2)
C16	0.0341 (18)	0.077 (3)	0.063 (2)	0.0057 (18)	0.0001 (16)	0.012 (2)
C17	0.0325 (17)	0.077 (3)	0.053 (2)	0.0058 (17)	−0.0008 (15)	0.0065 (19)
C18	0.0350 (17)	0.067 (2)	0.054 (2)	0.0120 (17)	0.0006 (15)	0.0077 (18)
C19	0.0350 (18)	0.084 (3)	0.053 (2)	−0.0041 (18)	−0.0018 (16)	−0.001 (2)
C20	0.063 (3)	0.131 (5)	0.061 (3)	0.010 (3)	0.010 (2)	−0.012 (3)
C21	0.048 (2)	0.093 (3)	0.071 (3)	−0.005 (2)	0.011 (2)	−0.022 (2)
C22	0.0402 (19)	0.068 (3)	0.068 (3)	−0.0038 (18)	0.0108 (18)	0.001 (2)
C23	0.048 (2)	0.051 (2)	0.084 (3)	−0.0066 (17)	0.015 (2)	0.007 (2)
C24	0.045 (2)	0.045 (2)	0.065 (2)	0.0000 (16)	0.0040 (17)	0.0054 (17)
N7	0.0444 (18)	0.062 (2)	0.065 (2)	0.0023 (15)	0.0068 (15)	0.0017 (17)
O3	0.0598 (17)	0.0610 (17)	0.078 (2)	−0.0098 (15)	−0.0092 (14)	0.0052 (15)
O4	0.0374 (13)	0.0713 (19)	0.0721 (18)	0.0014 (12)	0.0036 (12)	0.0033 (14)
O5	0.0617 (18)	0.089 (2)	0.088 (2)	−0.0007 (17)	−0.0002 (16)	0.0328 (19)
N8	0.058 (2)	0.149 (5)	0.076 (3)	0.031 (3)	0.017 (2)	0.045 (3)
O6	0.067 (2)	0.087 (3)	0.120 (3)	0.0060 (19)	0.000 (2)	0.043 (2)
O7	0.0608 (19)	0.105 (3)	0.070 (2)	0.0129 (19)	0.0101 (15)	0.015 (2)
O8	0.106 (3)	0.104 (4)	0.087 (3)	0.011 (3)	0.002 (2)	0.020 (3)
O8'	0.106 (3)	0.104 (4)	0.087 (3)	0.011 (3)	0.002 (2)	0.020 (3)
N9	0.074 (3)	0.065 (2)	0.089 (3)	0.005 (2)	−0.027 (2)	0.016 (2)
O9	0.110 (3)	0.139 (3)	0.138 (3)	−0.006 (3)	−0.044 (3)	0.035 (3)
O10	0.098 (3)	0.094 (3)	0.120 (4)	−0.015 (3)	−0.017 (3)	0.029 (3)
O11	0.100 (3)	0.082 (3)	0.103 (3)	−0.002 (2)	−0.026 (2)	0.003 (2)
O10'	0.098 (3)	0.094 (3)	0.120 (4)	−0.015 (3)	−0.017 (3)	0.029 (3)
O11'	0.100 (3)	0.082 (3)	0.103 (3)	−0.002 (2)	−0.026 (2)	0.003 (2)
C1M	0.218 (9)	0.221 (9)	0.222 (9)	0.000	0.009 (5)	0.000
O1M	0.294 (12)	0.290 (12)	0.300 (12)	−0.013 (5)	0.001 (5)	0.000 (5)

Eu1—O1	2.265 (2)	C10—H10A	0.970
Eu1—O2	2.290 (2)	C10—H10B	0.970
Eu1—O3	2.499 (3)	C11—H11A	0.970
Eu1—O4	2.533 (3)	C11—H11B	0.970
Eu1—O6	2.513 (4)	C12—C13	1.444 (6)
Eu1—O7	2.551 (3)	C12—H12	0.930
Eu1—N1	2.559 (3)	C13—C14	1.403 (6)
Eu1—N2	2.549 (4)	C13—C18	1.417 (6)
Eu1—N3	2.566 (4)	C14—C15	1.370 (7)
Cl1—C4	1.742 (4)	C14—H14	0.930
Cl2—C15	1.742 (4)	C15—C16	1.371 (6)
N1—C7	1.264 (5)	C16—C17	1.387 (5)
N1—C8	1.470 (5)	C16—H16	0.930
N2—C10	1.452 (7)	C17—C18	1.413 (6)
N2—C9	1.485 (5)	C17—C19	1.490 (6)
N2—H2	0.910	C19—H19	0.980
N3—C12	1.282 (6)	C20—C21	1.519 (7)
N3—C11	1.480 (6)	C20—H20A	0.970
N4—C22	1.448 (5)	C20—H20B	0.970
N4—C19	1.459 (5)	C21—H21A	0.970
N4—C21	1.465 (5)	C21—H21B	0.970
N5—C20	1.489 (6)	C22—C23	1.518 (6)
N5—C19	1.501 (5)	C22—H22A	0.970
N5—H5A	0.900	C22—H22B	0.970
N5—H5B	0.900	C23—H23A	0.970
N6—C24	1.286 (5)	C23—H23B	0.970
N6—C23	1.459 (5)	C24—H24	0.930
N6—H6	0.85 (5)	N7—O5	1.209 (4)
O1—C18	1.318 (4)	N7—O4	1.267 (4)
O2—C1	1.286 (4)	N7—O3	1.269 (4)
C1—C2	1.414 (5)	N8—O7	1.245 (7)
C1—C6	1.433 (5)	N8—O6	1.262 (7)
C2—C3	1.401 (5)	N8—O8'	1.265 (7)
C2—C24	1.440 (5)	N8—O8	1.273 (6)
C3—C4	1.376 (5)	N9—O9	1.206 (5)
C3—H3	0.930	N9—O10	1.221 (4)
C4—C5	1.380 (6)	N9—O11'	1.230 (5)
C5—C6	1.385 (5)	N9—O10'	1.233 (5)
C5—H5	0.930	N9—O11	1.238 (4)
C6—C7	1.459 (6)	C1M—O1Mi	1.351 (10)
C7—H7	0.930	C1M—O1M	1.351 (10)
C8—C9	1.499 (7)	C1M—H1MA	0.960
C8—H8A	0.970	C1M—H1MB	0.960
C8—H8B	0.970	C1M—H1MC	0.960
C9—H9A	0.970	O1M—O1Mi	1.35 (4)
C9—H9B	0.970	O1M—H1WD	0.826
C10—C11	1.501 (7)
O1—Eu1—O2	97.01 (10)	C8—C9—H9B	109.7
O1—Eu1—O3	125.16 (10)	H9A—C9—H9B	108.2
O2—Eu1—O3	74.57 (10)	N2—C10—C11	110.4 (4)
O1—Eu1—O6	80.42 (11)	N2—C10—H10A	109.6
O2—Eu1—O6	121.17 (14)	C11—C10—H10A	109.6
O3—Eu1—O6	150.28 (13)	N2—C10—H10B	109.6
O1—Eu1—O4	75.31 (9)	C11—C10—H10B	109.6
O2—Eu1—O4	69.04 (9)	H10A—C10—H10B	108.1
O3—Eu1—O4	50.72 (9)	N3—C11—C10	110.8 (4)
O6—Eu1—O4	154.86 (10)	N3—C11—H11A	109.5
O1—Eu1—N2	130.32 (11)	C10—C11—H11A	109.5
O2—Eu1—N2	132.66 (10)	N3—C11—H11B	109.5
O3—Eu1—N2	76.33 (12)	C10—C11—H11B	109.5
O6—Eu1—N2	74.98 (15)	H11A—C11—H11B	108.1
O4—Eu1—N2	116.53 (12)	N3—C12—C13	128.0 (4)
O1—Eu1—O7	70.82 (10)	N3—C12—H12	116.0
O2—Eu1—O7	73.14 (11)	C13—C12—H12	116.0
O3—Eu1—O7	145.58 (11)	C14—C13—C18	119.2 (4)
O6—Eu1—O7	50.30 (14)	C14—C13—C12	117.6 (4)
O4—Eu1—O7	124.64 (11)	C18—C13—C12	123.2 (4)
N2—Eu1—O7	118.80 (13)	C15—C14—C13	121.1 (4)
O1—Eu1—N1	147.85 (11)	C15—C14—H14	119.4
O2—Eu1—N1	71.36 (9)	C13—C14—H14	119.4
O3—Eu1—N1	81.65 (11)	C14—C15—C16	120.4 (4)
O6—Eu1—N1	80.66 (11)	C14—C15—Cl2	120.0 (4)
O4—Eu1—N1	123.97 (9)	C16—C15—Cl2	119.6 (4)
N2—Eu1—N1	68.09 (12)	C15—C16—C17	120.3 (4)
O7—Eu1—N1	77.08 (11)	C15—C16—H16	119.8
O1—Eu1—N3	72.00 (11)	C17—C16—H16	119.8
O2—Eu1—N3	145.13 (11)	C16—C17—C18	120.8 (4)
O3—Eu1—N3	84.94 (11)	C16—C17—C19	118.9 (4)
O6—Eu1—N3	90.28 (14)	C18—C17—C19	120.2 (3)
O4—Eu1—N3	76.13 (11)	O1—C18—C17	119.2 (4)
N2—Eu1—N3	65.76 (12)	O1—C18—C13	122.9 (4)
O7—Eu1—N3	129.10 (12)	C17—C18—C13	117.9 (3)
N1—Eu1—N3	133.76 (11)	N4—C19—C17	116.0 (3)
C7—N1—C8	117.1 (3)	N4—C19—N5	98.1 (3)
C7—N1—Eu1	131.1 (3)	C17—C19—N5	113.3 (4)
C8—N1—Eu1	111.7 (3)	N4—C19—H19	109.6
C10—N2—C9	114.4 (4)	C17—C19—H19	109.6
C10—N2—Eu1	109.5 (3)	N5—C19—H19	109.6
C9—N2—Eu1	112.3 (3)	N5—C20—C21	104.2 (3)
C10—N2—H2	106.7	N5—C20—H20A	110.9
C9—N2—H2	106.7	C21—C20—H20A	110.9
Eu1—N2—H2	106.7	N5—C20—H20B	110.9
C12—N3—C11	115.9 (4)	C21—C20—H20B	110.9
C12—N3—Eu1	127.1 (3)	H20A—C20—H20B	108.9
C11—N3—Eu1	116.8 (3)	N4—C21—C20	102.0 (4)
C22—N4—C19	115.0 (3)	N4—C21—H21A	111.4
C22—N4—C21	117.9 (4)	C20—C21—H21A	111.4
C19—N4—C21	103.2 (3)	N4—C21—H21B	111.4
C20—N5—C19	105.8 (4)	C20—C21—H21B	111.4
C20—N5—H5A	110.6	H21A—C21—H21B	109.2
C19—N5—H5A	110.6	N4—C22—C23	112.2 (3)
C20—N5—H5B	110.6	N4—C22—H22A	109.2
C19—N5—H5B	110.6	C23—C22—H22A	109.2
H5A—N5—H5B	108.7	N4—C22—H22B	109.2
C24—N6—C23	124.6 (4)	C23—C22—H22B	109.2
C24—N6—H6	114 (3)	H22A—C22—H22B	107.9
C23—N6—H6	121 (3)	N6—C23—C22	110.9 (3)
C18—O1—Eu1	134.9 (2)	N6—C23—H23A	109.5
C1—O2—Eu1	144.0 (2)	C22—C23—H23A	109.5
O2—C1—C2	119.7 (3)	N6—C23—H23B	109.5
O2—C1—C6	122.6 (3)	C22—C23—H23B	109.5
C2—C1—C6	117.7 (3)	H23A—C23—H23B	108.0
C3—C2—C1	121.3 (3)	N6—C24—C2	124.6 (4)
C3—C2—C24	117.3 (3)	N6—C24—H24	117.7
C1—C2—C24	121.4 (3)	C2—C24—H24	117.7
C4—C3—C2	119.3 (4)	O5—N7—O4	121.6 (4)
C4—C3—H3	120.3	O5—N7—O3	121.9 (3)
C2—C3—H3	120.3	O4—N7—O3	116.4 (3)
C3—C4—C5	120.8 (4)	N7—O3—Eu1	94.9 (2)
C3—C4—Cl1	119.3 (3)	N7—O4—Eu1	93.4 (2)
C5—C4—Cl1	119.9 (3)	O7—N8—O6	118.3 (4)
C4—C5—C6	121.5 (4)	O7—N8—O8'	136.8 (8)
C4—C5—H5	119.2	O6—N8—O8'	102.5 (9)
C6—C5—H5	119.2	O7—N8—O8	109.3 (8)
C5—C6—C1	119.3 (4)	O6—N8—O8	131.8 (7)
C5—C6—C7	117.7 (3)	N8—O6—Eu1	96.0 (3)
C1—C6—C7	123.0 (3)	N8—O7—Eu1	94.6 (3)
N1—C7—C6	127.6 (3)	O9—N9—O10	121.4 (5)
N1—C7—H7	116.2	O9—N9—O11'	123.3 (8)
C6—C7—H7	116.2	O9—N9—O10'	117.6 (10)
N1—C8—C9	109.0 (4)	O11'—N9—O10'	116.6 (11)
N1—C8—H8A	109.9	O9—N9—O11	119.9 (5)
C9—C8—H8A	109.9	O10—N9—O11	118.4 (5)
N1—C8—H8B	109.9	O1M—C1M—H1MA	110.4
C9—C8—H8B	109.9	O1M—C1M—H1MB	111.7
H8A—C8—H8B	108.3	H1MA—C1M—H1MB	109.5
N2—C9—C8	109.6 (4)	O1M—C1M—H1MC	106.3
N2—C9—H9A	109.7	H1MA—C1M—H1MC	109.5
C8—C9—H9A	109.7	H1MB—C1M—H1MC	109.5
N2—C9—H9B	109.7