Bis[6-meth-oxy-2-[(4-methyl-phen-yl)iminiometh-yl]phenolate-κO]tris-(nitrato-κO,O')ytterbium(III) monohydrate.

The crystal structure of title compound, [Yb(NO(3))(3)(C(15)H(15)NO(2))(2)]·H(2)O, contains two Schiff base 2-[(4-methyl-phen-yl)imino-meth-yl]-6-methoxy-phenol (HL) ligands, three independent nitrate ions that chelate to the ytterbium(III) ion in an O,O'-bidentate manner and an uncoordinated water mol-ecule. The coordination number of the Yb(III) ion is eight. The HL ligands chelate with a strong Yb-O(phenolate) bond and a weak Yb-O(meth-oxy) contact. The latter augments the coordination polyhedron to give a YbO(10) bicapped square antiprism. Classical inter-molecular O-H⋯O and N-H⋯O hydrogen bonds as well as weak C-H⋯O contacts contribute to the stability of the structure.

Related literature

For the crystal structure of a zinc(II) complex with two chelating HL ligands, see: Xian et al. (2008 ▶). For a related terbium(III) complex, see: Zhao et al. (2007 ▶). For the zigzag chain cadmium(II) complex bridged by chloride, see: Li et al. (2008 ▶). For iron(III) and cobalt(III) complexes of some N-salicylideneamino acids, see: Burrows & Bailar (1966 ▶). For a heterodimetallic (Yb, La) complex, see: Costes et al. (1998 ▶). For the syntheses of rare earth complexes with Schiff bases derived from o-vanillin and adamantaneamine, see: Zhao et al. (2005 ▶).

Experimental

Crystal data

[Yb(NO3)3(C15H15NO2)2]·H2O

M = 859.65

Triclinic,

a = 9.6878 (1) Å

b = 9.9210 (2) Å

c = 18.5998 (3) Å

α = 97.341 (1)°

β = 101.929 (1)°

γ = 106.593 (1)°

V = 1642.63 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.92 mm−1

T = 296 K

0.27 × 0.16 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.576, T max = 0.757

24571 measured reflections

7543 independent reflections

6122 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.095

S = 0.99

7543 reflections

457 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.88 e Å−3

Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041361/si2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041361/si2199Isup2.hkl

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

[Yb(NO3)3(C15H15NO2)2]·H2O	Z = 2
Mr = 859.65	F(000) = 858
Triclinic, P1	Dx = 1.738 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6878 (1) Å	Cell parameters from 9270 reflections
b = 9.9210 (2) Å	θ = 2.2–27.6°
c = 18.5998 (3) Å	µ = 2.92 mm−1
α = 97.341 (1)°	T = 296 K
β = 101.929 (1)°	Block, red
γ = 106.593 (1)°	0.27 × 0.16 × 0.10 mm
V = 1642.63 (5) Å3

Bruker APEXII area-detector diffractometer	7543 independent reflections
Radiation source: fine-focus sealed tube	6122 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.576, Tmax = 0.757	k = −11→12
24571 measured reflections	l = −24→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3718P] where P = (Fo2 + 2Fc2)/3
7543 reflections	(Δ/σ)max = 0.001
457 parameters	Δρmax = 1.88 e Å−3
4 restraints	Δρmin = −0.76 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Yb	0.968710 (17)	0.805760 (19)	0.249140 (10)	0.04617 (8)
N1	1.4545 (4)	1.0479 (4)	0.27759 (19)	0.0459 (8)
H1A	1.3655	1.0118	0.2820	0.055*
N2	0.5165 (4)	0.4795 (4)	0.22488 (19)	0.0456 (8)
H2A	0.6045	0.5268	0.2226	0.055*
N3	0.8386 (5)	0.7186 (5)	0.0937 (2)	0.0606 (10)
N4	1.1154 (5)	0.7510 (6)	0.3852 (3)	0.0664 (12)
N5	0.9364 (6)	1.0733 (5)	0.2322 (3)	0.0681 (12)
O1	1.2019 (3)	0.8427 (3)	0.24032 (17)	0.0530 (8)
O2	1.0387 (3)	0.5841 (4)	0.1676 (2)	0.0643 (9)
O3	0.7601 (3)	0.7075 (3)	0.28207 (17)	0.0517 (7)
O4	0.8875 (3)	0.9622 (4)	0.36941 (19)	0.0654 (9)
O5	0.7806 (3)	0.6609 (4)	0.14198 (19)	0.0614 (9)
O6	0.9582 (4)	0.8237 (4)	0.12055 (19)	0.0621 (8)
O7	0.7843 (6)	0.6766 (5)	0.0273 (2)	0.0980 (14)
O8	1.1297 (5)	0.8765 (5)	0.3772 (2)	0.0729 (10)
O9	1.0374 (4)	0.6518 (4)	0.3277 (2)	0.0716 (10)
O10	1.1715 (5)	0.7193 (5)	0.4431 (2)	0.0904 (13)
O11	0.8255 (4)	0.9634 (4)	0.2118 (2)	0.0700 (9)
O12	1.0607 (4)	1.0550 (3)	0.2605 (2)	0.0611 (9)
O13	0.9282 (6)	1.1912 (5)	0.2263 (3)	0.1144 (18)
C1	1.3997 (4)	0.8384 (5)	0.1834 (2)	0.0429 (9)
C2	1.2576 (4)	0.7763 (5)	0.1938 (2)	0.0439 (9)
C3	1.1733 (5)	0.6369 (5)	0.1516 (2)	0.0480 (10)
C4	1.2283 (5)	0.5683 (5)	0.1010 (3)	0.0554 (11)
H4A	1.1713	0.4774	0.0732	0.067*
C5	1.3693 (6)	0.6341 (5)	0.0912 (3)	0.0600 (12)
H5A	1.4049	0.5870	0.0563	0.072*
C6	1.4543 (5)	0.7647 (5)	0.1316 (2)	0.0527 (11)
H6A	1.5490	0.8065	0.1255	0.063*
C7	1.4944 (5)	0.9742 (5)	0.2276 (2)	0.0467 (10)
H7A	1.5889	1.0115	0.2203	0.056*
C8	0.9538 (7)	0.4397 (6)	0.1344 (4)	0.092 (2)
H8A	1.0138	0.3791	0.1452	0.139*
H8B	0.9214	0.4305	0.0811	0.139*
H8C	0.8685	0.4114	0.1544	0.139*
C9	1.5409 (5)	1.1810 (4)	0.3256 (2)	0.0456 (9)
C10	1.6779 (5)	1.2602 (5)	0.3190 (3)	0.0576 (11)
H10A	1.7168	1.2282	0.2810	0.069*
C11	1.7572 (5)	1.3869 (5)	0.3689 (3)	0.0619 (12)
H11A	1.8502	1.4395	0.3643	0.074*
C12	1.7019 (6)	1.4379 (5)	0.4256 (3)	0.0603 (12)
C13	1.5647 (6)	1.3591 (6)	0.4309 (3)	0.0721 (15)
H13A	1.5257	1.3921	0.4686	0.087*
C14	1.4825 (6)	1.2312 (6)	0.3812 (3)	0.0673 (14)
H14A	1.3888	1.1795	0.3853	0.081*
C15	1.7903 (7)	1.5764 (6)	0.4809 (3)	0.0851 (18)
H15A	1.7900	1.5618	0.5309	0.128*
H15B	1.7462	1.6492	0.4705	0.128*
H15C	1.8910	1.6061	0.4764	0.128*
C16	0.5417 (4)	0.6699 (5)	0.3259 (2)	0.0442 (9)
C17	0.6855 (4)	0.7534 (5)	0.3255 (2)	0.0424 (9)
C18	0.7486 (5)	0.8889 (5)	0.3747 (2)	0.0481 (10)
C19	0.6746 (5)	0.9362 (5)	0.4222 (3)	0.0569 (11)
H19A	0.7185	1.0252	0.4544	0.068*
C20	0.5325 (6)	0.8503 (6)	0.4224 (3)	0.0696 (15)
H20A	0.4826	0.8825	0.4550	0.083*
C21	0.4670 (5)	0.7214 (5)	0.3758 (3)	0.0602 (12)
H21A	0.3720	0.6658	0.3762	0.072*
C22	0.4648 (5)	0.5359 (5)	0.2758 (2)	0.0476 (10)
H22A	0.3708	0.4851	0.2798	0.057*
C23	0.9660 (6)	1.0991 (5)	0.4183 (3)	0.0681 (14)
H23A	0.9765	1.0881	0.4695	0.102*
H23B	0.9111	1.1644	0.4085	0.102*
H23C	1.0628	1.1363	0.4097	0.102*
C24	0.4433 (4)	0.3477 (4)	0.1723 (2)	0.0443 (9)
C25	0.3097 (5)	0.2547 (5)	0.1744 (3)	0.0531 (11)
H25A	0.2642	0.2759	0.2118	0.064*
C26	0.2433 (5)	0.1309 (5)	0.1216 (3)	0.0589 (12)
H26A	0.1524	0.0688	0.1235	0.071*
C27	0.3079 (6)	0.0956 (5)	0.0654 (3)	0.0590 (12)
C28	0.4427 (6)	0.1890 (6)	0.0646 (3)	0.0708 (14)
H28A	0.4887	0.1667	0.0277	0.085*
C29	0.5122 (5)	0.3158 (6)	0.1174 (3)	0.0628 (13)
H29A	0.6033	0.3780	0.1158	0.075*
C30	0.2304 (5)	−0.0412 (5)	0.0060 (3)	0.0803 (16)
H30A	0.1376	−0.0919	0.0155	0.121*
H30B	0.2930	−0.1009	0.0077	0.121*
H30C	0.2117	−0.0171	−0.0427	0.121*
O1W	0.1609 (5)	0.4096 (5)	0.3221 (3)	0.207 (4)
H1WB	0.086 (11)	0.330 (10)	0.300 (8)	0.310*
H1WA	0.117 (14)	0.466 (10)	0.342 (5)	0.310*

	U11	U22	U33	U12	U13	U23
Yb	0.03135 (10)	0.04494 (13)	0.05706 (13)	0.00384 (8)	0.01277 (8)	0.00902 (9)
N1	0.0345 (17)	0.047 (2)	0.050 (2)	0.0088 (15)	0.0070 (15)	0.0024 (16)
N2	0.0332 (17)	0.049 (2)	0.050 (2)	0.0065 (15)	0.0106 (15)	0.0092 (16)
N3	0.062 (3)	0.061 (3)	0.058 (3)	0.026 (2)	0.011 (2)	0.002 (2)
N4	0.056 (3)	0.094 (4)	0.062 (3)	0.032 (3)	0.027 (2)	0.021 (3)
N5	0.089 (3)	0.061 (3)	0.082 (3)	0.039 (3)	0.051 (3)	0.029 (2)
O1	0.0361 (15)	0.061 (2)	0.0549 (17)	0.0093 (13)	0.0141 (13)	−0.0023 (15)
O2	0.0433 (17)	0.055 (2)	0.082 (2)	−0.0006 (15)	0.0122 (16)	0.0132 (18)
O3	0.0392 (15)	0.0500 (18)	0.0610 (18)	0.0054 (13)	0.0213 (14)	0.0007 (14)
O4	0.0477 (18)	0.059 (2)	0.072 (2)	−0.0028 (15)	0.0197 (16)	−0.0090 (17)
O5	0.0461 (17)	0.063 (2)	0.064 (2)	0.0046 (15)	0.0174 (15)	−0.0037 (17)
O6	0.062 (2)	0.055 (2)	0.066 (2)	0.0109 (17)	0.0205 (17)	0.0134 (17)
O7	0.130 (4)	0.096 (3)	0.050 (2)	0.036 (3)	−0.003 (2)	−0.004 (2)
O8	0.086 (3)	0.077 (3)	0.064 (2)	0.042 (2)	0.0200 (19)	0.008 (2)
O9	0.056 (2)	0.069 (2)	0.089 (3)	0.0118 (18)	0.0153 (19)	0.034 (2)
O10	0.096 (3)	0.136 (4)	0.064 (2)	0.064 (3)	0.025 (2)	0.042 (3)
O11	0.058 (2)	0.068 (2)	0.091 (3)	0.0236 (19)	0.0271 (19)	0.019 (2)
O12	0.059 (2)	0.0428 (18)	0.087 (2)	0.0130 (15)	0.0361 (18)	0.0134 (17)
O13	0.159 (5)	0.073 (3)	0.159 (5)	0.065 (3)	0.085 (4)	0.056 (3)
C1	0.0340 (19)	0.048 (2)	0.046 (2)	0.0135 (18)	0.0083 (17)	0.0095 (19)
C2	0.037 (2)	0.050 (3)	0.043 (2)	0.0160 (18)	0.0060 (17)	0.0066 (19)
C3	0.039 (2)	0.050 (3)	0.050 (2)	0.0103 (19)	0.0054 (18)	0.011 (2)
C4	0.062 (3)	0.041 (3)	0.055 (3)	0.013 (2)	0.005 (2)	0.002 (2)
C5	0.068 (3)	0.059 (3)	0.057 (3)	0.027 (3)	0.020 (2)	0.002 (2)
C6	0.048 (2)	0.060 (3)	0.052 (3)	0.021 (2)	0.017 (2)	0.005 (2)
C7	0.039 (2)	0.052 (3)	0.047 (2)	0.0164 (19)	0.0076 (18)	0.003 (2)
C8	0.069 (4)	0.052 (3)	0.143 (6)	−0.001 (3)	0.019 (4)	0.031 (4)
C9	0.044 (2)	0.040 (2)	0.047 (2)	0.0105 (18)	0.0046 (18)	0.0055 (19)
C10	0.049 (3)	0.053 (3)	0.068 (3)	0.010 (2)	0.020 (2)	0.007 (2)
C11	0.051 (3)	0.045 (3)	0.077 (3)	0.001 (2)	0.011 (2)	0.007 (2)
C12	0.063 (3)	0.043 (3)	0.060 (3)	0.006 (2)	−0.003 (2)	0.011 (2)
C13	0.082 (4)	0.055 (3)	0.067 (3)	0.009 (3)	0.026 (3)	−0.010 (3)
C14	0.060 (3)	0.055 (3)	0.075 (3)	0.003 (2)	0.025 (3)	−0.004 (3)
C15	0.098 (5)	0.049 (3)	0.076 (4)	0.003 (3)	−0.004 (3)	−0.007 (3)
C16	0.042 (2)	0.046 (2)	0.048 (2)	0.0147 (18)	0.0151 (18)	0.0130 (19)
C17	0.037 (2)	0.047 (2)	0.045 (2)	0.0138 (18)	0.0128 (17)	0.0111 (19)
C18	0.044 (2)	0.050 (3)	0.049 (2)	0.0122 (19)	0.0130 (19)	0.009 (2)
C19	0.059 (3)	0.050 (3)	0.064 (3)	0.020 (2)	0.020 (2)	0.006 (2)
C20	0.073 (3)	0.062 (3)	0.083 (4)	0.022 (3)	0.046 (3)	0.003 (3)
C21	0.052 (3)	0.060 (3)	0.076 (3)	0.017 (2)	0.036 (2)	0.011 (3)
C22	0.041 (2)	0.045 (2)	0.057 (3)	0.0079 (18)	0.0181 (19)	0.017 (2)
C23	0.060 (3)	0.054 (3)	0.070 (3)	0.000 (2)	0.008 (2)	−0.004 (3)
C24	0.043 (2)	0.039 (2)	0.048 (2)	0.0096 (18)	0.0101 (18)	0.0102 (18)
C25	0.049 (2)	0.049 (3)	0.055 (3)	0.004 (2)	0.017 (2)	0.009 (2)
C26	0.051 (3)	0.051 (3)	0.065 (3)	0.001 (2)	0.015 (2)	0.015 (2)
C27	0.061 (3)	0.052 (3)	0.056 (3)	0.014 (2)	0.004 (2)	0.011 (2)
C28	0.064 (3)	0.070 (4)	0.076 (3)	0.014 (3)	0.029 (3)	0.002 (3)
C29	0.045 (3)	0.061 (3)	0.076 (3)	0.007 (2)	0.025 (2)	0.001 (3)
C30	0.083 (4)	0.060 (3)	0.077 (4)	0.012 (3)	0.001 (3)	−0.004 (3)
O1W	0.172 (7)	0.191 (9)	0.248 (10)	0.041 (6)	0.078 (7)	0.018 (7)

Yb—O3	2.225 (3)	C8—H8B	0.9600
Yb—O1	2.228 (3)	C8—H8C	0.9600
Yb—O12	2.342 (3)	C9—C10	1.375 (6)
Yb—O5	2.373 (3)	C9—C14	1.383 (6)
Yb—O9	2.379 (4)	C10—C11	1.373 (6)
Yb—O6	2.404 (3)	C10—H10A	0.9300
Yb—O11	2.444 (4)	C11—C12	1.382 (7)
Yb—O8	2.451 (4)	C11—H11A	0.9300
Yb—N5	2.809 (5)	C12—C13	1.367 (7)
Yb—N3	2.815 (4)	C12—C15	1.510 (7)
Yb—O2	2.833 (4)	C13—C14	1.384 (7)
Yb—O4	2.927 (3)	C13—H13A	0.9300
Yb—N4	2.833 (5)	C14—H14A	0.9300
N1—C7	1.298 (5)	C15—H15A	0.9600
N1—C9	1.414 (5)	C15—H15B	0.9600
N1—H1A	0.8600	C15—H15C	0.9600
N2—C22	1.297 (5)	C16—C17	1.405 (5)
N2—C24	1.423 (5)	C16—C21	1.419 (6)
N2—H2A	0.8600	C16—C22	1.423 (6)
N3—O7	1.205 (5)	C17—C18	1.416 (6)
N3—O5	1.267 (5)	C18—C19	1.365 (6)
N3—O6	1.271 (5)	C19—C20	1.397 (7)
N4—O10	1.223 (6)	C19—H19A	0.9300
N4—O8	1.245 (6)	C20—C21	1.347 (7)
N4—O9	1.287 (6)	C20—H20A	0.9300
N5—O13	1.212 (6)	C21—H21A	0.9300
N5—O11	1.242 (6)	C22—H22A	0.9300
N5—O12	1.284 (6)	C23—H23A	0.9600
O1—C2	1.313 (5)	C23—H23B	0.9600
O2—C3	1.369 (5)	C23—H23C	0.9600
O2—C8	1.415 (6)	C24—C25	1.369 (5)
O3—C17	1.310 (5)	C24—C29	1.381 (6)
O4—C18	1.365 (5)	C25—C26	1.367 (6)
O4—C23	1.435 (5)	C25—H25A	0.9300
C1—C2	1.402 (5)	C26—C27	1.381 (7)
C1—C6	1.412 (6)	C26—H26A	0.9300
C1—C7	1.425 (6)	C27—C28	1.373 (7)
C2—C3	1.417 (6)	C27—C30	1.524 (7)
C3—C4	1.372 (6)	C28—C29	1.388 (7)
C4—C5	1.397 (7)	C28—H28A	0.9300
C4—H4A	0.9300	C29—H29A	0.9300
C5—C6	1.344 (6)	C30—H30A	0.9600
C5—H5A	0.9300	C30—H30B	0.9600
C6—H6A	0.9300	C30—H30C	0.9600
C7—H7A	0.9300	O1W—H1WB	0.88
C8—H8A	0.9600	O1W—H1WA	0.88
O3—Yb—O1	157.78 (13)	C2—C1—C6	120.7 (4)
O3—Yb—O12	119.91 (11)	C2—C1—C7	120.5 (4)
O1—Yb—O12	77.05 (11)	C6—C1—C7	118.7 (4)
O3—Yb—O5	70.20 (11)	O1—C2—C1	122.4 (4)
O1—Yb—O5	115.39 (10)	O1—C2—C3	120.0 (4)
O12—Yb—O5	120.65 (13)	C1—C2—C3	117.6 (4)
O3—Yb—O9	77.22 (12)	O2—C3—C4	126.4 (4)
O1—Yb—O9	80.67 (12)	O2—C3—C2	113.0 (4)
O12—Yb—O9	131.26 (14)	C4—C3—C2	120.6 (4)
O5—Yb—O9	108.04 (14)	C3—C4—C5	120.4 (4)
O3—Yb—O6	119.78 (11)	C3—C4—H4A	119.8
O1—Yb—O6	75.37 (11)	C5—C4—H4A	119.8
O12—Yb—O6	79.10 (12)	C6—C5—C4	120.8 (4)
O5—Yb—O6	53.28 (11)	C6—C5—H5A	119.6
O9—Yb—O6	135.12 (13)	C4—C5—H5A	119.6
O3—Yb—O11	78.88 (12)	C5—C6—C1	119.9 (4)
O1—Yb—O11	123.06 (12)	C5—C6—H6A	120.0
O12—Yb—O11	53.16 (12)	C1—C6—H6A	120.0
O5—Yb—O11	76.57 (13)	N1—C7—C1	122.9 (4)
O9—Yb—O11	152.18 (13)	N1—C7—H7A	118.6
O6—Yb—O11	70.21 (12)	C1—C7—H7A	118.6
O3—Yb—O8	95.26 (13)	O2—C8—H8A	109.5
O1—Yb—O8	72.75 (12)	O2—C8—H8B	109.5
O12—Yb—O8	79.24 (14)	H8A—C8—H8B	109.5
O5—Yb—O8	159.19 (15)	O2—C8—H8C	109.5
O9—Yb—O8	52.78 (14)	H8A—C8—H8C	109.5
O6—Yb—O8	144.64 (13)	H8B—C8—H8C	109.5
O11—Yb—O8	116.21 (13)	C10—C9—C14	119.7 (4)
O3—Yb—N5	99.59 (12)	C10—C9—N1	123.0 (4)
O1—Yb—N5	100.65 (13)	C14—C9—N1	117.3 (4)
O12—Yb—N5	26.97 (13)	C11—C10—C9	119.8 (4)
O5—Yb—N5	98.56 (14)	C11—C10—H10A	120.1
O9—Yb—N5	149.93 (15)	C9—C10—H10A	120.1
O6—Yb—N5	72.70 (12)	C10—C11—C12	121.5 (4)
O11—Yb—N5	26.20 (13)	C10—C11—H11A	119.3
O8—Yb—N5	98.52 (15)	C12—C11—H11A	119.3
O3—Yb—N3	95.23 (12)	C13—C12—C11	118.2 (4)
O1—Yb—N3	95.27 (12)	C13—C12—C15	120.6 (5)
O12—Yb—N3	100.83 (13)	C11—C12—C15	121.3 (5)
O5—Yb—N3	26.55 (11)	C12—C13—C14	121.5 (5)
O9—Yb—N3	124.08 (14)	C12—C13—H13A	119.3
O6—Yb—N3	26.74 (11)	C14—C13—H13A	119.3
O11—Yb—N3	72.08 (12)	C9—C14—C13	119.4 (5)
O8—Yb—N3	167.78 (12)	C9—C14—H14A	120.3
N5—Yb—N3	85.88 (13)	C13—C14—H14A	120.3
O3—Yb—O2	108.26 (10)	C12—C15—H15A	109.5
O1—Yb—O2	60.78 (10)	C12—C15—H15B	109.5
O12—Yb—O2	130.25 (10)	H15A—C15—H15B	109.5
O5—Yb—O2	63.94 (11)	C12—C15—H15C	109.5
O9—Yb—O2	68.91 (13)	H15A—C15—H15C	109.5
O6—Yb—O2	66.31 (11)	H15B—C15—H15C	109.5
O11—Yb—O2	133.11 (12)	C17—C16—C21	119.8 (4)
O8—Yb—O2	109.30 (11)	C17—C16—C22	122.1 (4)
N5—Yb—O2	137.96 (11)	C21—C16—C22	118.0 (4)
N3—Yb—O2	61.23 (11)	O3—C17—C16	121.6 (4)
O3—Yb—N4	85.22 (12)	O3—C17—C18	120.8 (3)
O1—Yb—N4	75.93 (11)	C16—C17—C18	117.5 (4)
O12—Yb—N4	105.01 (15)	C19—C18—O4	125.4 (4)
O5—Yb—N4	134.23 (15)	C19—C18—C17	121.6 (4)
O9—Yb—N4	26.82 (13)	O4—C18—C17	113.0 (4)
O6—Yb—N4	149.20 (11)	C18—C19—C20	119.8 (4)
O11—Yb—N4	136.87 (13)	C18—C19—H19A	120.1
O8—Yb—N4	25.98 (13)	C20—C19—H19A	120.1
N5—Yb—N4	123.86 (15)	C21—C20—C19	120.8 (4)
N3—Yb—N4	149.85 (14)	C21—C20—H20A	119.6
O2—Yb—N4	89.92 (12)	C19—C20—H20A	119.6
C7—N1—C9	127.4 (4)	C20—C21—C16	120.4 (4)
C7—N1—H1A	116.3	C20—C21—H21A	119.8
C9—N1—H1A	116.3	C16—C21—H21A	119.8
C22—N2—C24	127.0 (3)	N2—C22—C16	124.6 (4)
C22—N2—H2A	116.5	N2—C22—H22A	117.7
C24—N2—H2A	116.5	C16—C22—H22A	117.7
O7—N3—O5	122.4 (5)	O4—C23—H23A	109.5
O7—N3—O6	122.6 (5)	O4—C23—H23B	109.5
O5—N3—O6	115.1 (4)	H23A—C23—H23B	109.5
O7—N3—Yb	177.5 (4)	O4—C23—H23C	109.5
O5—N3—Yb	56.8 (2)	H23A—C23—H23C	109.5
O6—N3—Yb	58.3 (2)	H23B—C23—H23C	109.5
O10—N4—O8	123.9 (5)	C25—C24—C29	120.2 (4)
O10—N4—O9	120.0 (5)	C25—C24—N2	122.6 (4)
O8—N4—O9	116.0 (4)	C29—C24—N2	117.2 (4)
O10—N4—Yb	175.9 (4)	C26—C25—C24	120.0 (4)
O8—N4—Yb	59.6 (3)	C26—C25—H25A	120.0
O9—N4—Yb	56.5 (2)	C24—C25—H25A	120.0
O13—N5—O11	122.2 (5)	C25—C26—C27	121.6 (4)
O13—N5—O12	121.7 (5)	C25—C26—H26A	119.2
O11—N5—O12	116.1 (4)	C27—C26—H26A	119.2
O13—N5—Yb	177.5 (5)	C28—C27—C26	117.7 (5)
O11—N5—Yb	60.3 (2)	C28—C27—C30	121.5 (5)
O12—N5—Yb	55.8 (2)	C26—C27—C30	120.8 (4)
C2—O1—Yb	131.5 (3)	C27—C28—C29	121.9 (5)
C3—O2—C8	117.1 (4)	C27—C28—H28A	119.1
C3—O2—Yb	110.7 (3)	C29—C28—H28A	119.1
C8—O2—Yb	131.7 (3)	C24—C29—C28	118.6 (4)
C17—O3—Yb	135.2 (3)	C24—C29—H29A	120.7
C18—O4—C23	118.6 (4)	C28—C29—H29A	120.7
C18—O4—Yb	110.7 (2)	C27—C30—H30A	109.5
C23—O4—Yb	130.7 (3)	C27—C30—H30B	109.5
N3—O5—Yb	96.6 (3)	H30A—C30—H30B	109.5
N3—O6—Yb	95.0 (3)	C27—C30—H30C	109.5
N4—O8—Yb	94.4 (3)	H30A—C30—H30C	109.5
N4—O9—Yb	96.7 (3)	H30B—C30—H30C	109.5
N5—O11—Yb	93.5 (3)	H1WB—O1W—H1WA	103
N5—O12—Yb	97.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.89	2.590 (4)	138
N2—H2A···O3	0.86	1.99	2.668 (4)	135
O1W—H1WB···O13i	0.88	1.89 (13)	2.74133	162
O1W—H1WB···N5i	0.88	2.55 (11)	3.40359	163
O1W—H1WA···O9ii	0.88	2.22 (11)	2.97416	144
C22—H22A···O1W	0.93	2.29	3.1932	163
C4—H4A···O7iii	0.93	2.45	3.137 (7)	131

Table 1

Selected bond lengths (Å)

Yb—O3	2.225 (3)
Yb—O1	2.228 (3)
Yb—O12	2.342 (3)
Yb—O5	2.373 (3)
Yb—O9	2.379 (4)
Yb—O6	2.404 (3)
Yb—O11	2.444 (4)
Yb—O8	2.451 (4)
Yb—O2	2.833 (4)
Yb—O4	2.927 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.89	2.590 (4)	138
N2—H2A⋯O3	0.86	1.99	2.668 (4)	135
O1W—H1WB⋯O13i	0.88	1.89 (13)	2.741	162
O1W—H1WB⋯N5i	0.88	2.55 (11)	3.404	163
O1W—H1WA⋯O9ii	0.88	2.22 (11)	2.97416	144
C22—H22A⋯O1W	0.93	2.29	3.193	163
C4—H4A⋯O7iii	0.93	2.45	3.137 (7)	131

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