Dichloridobis(methanol-κO)[cis-(±)-2,4,5-tris-(pyridin-2-yl)-2-imidazoline-κ(3)N(2),N(3),N(4)]ytterbium(III) chloride.

In the crystal structure of the title complex, [YbCl(2)(C(18)H(15)N(5))(CH(3)OH)(2)]Cl, the pseudo-penta-gonal-bipyramidal coordination geometry of the Yb(III) cation is composed of three N atoms from one cis-(±)-2,4,5-tris-(pyridin-2-yl)imidazoline (HL) ligand, two O atoms from two methanol mol-ecules and two Cl(-) anions. Chains are formed along [010] through N-H⋯Cl, O-H⋯Cl and O-H⋯N hydrogen bonds.

Related literature

For background to the synthesis of HL, see: Later et al. (1998 ▶); Fernandes et al. (2007 ▶). For metal complexes with HL, see: Parra-Hake et al. (2000 ▶); Campos-Gaxiola et al. (2007 ▶, 2008 ▶, 2010 ▶). For related Yb (III) complexes, see: Li et al. (2007 ▶); Xu et al. (2009 ▶); Stojanovic et al. (2010 ▶); Okawara et al. (2012 ▶). For potential applications of polypyridyl chelating ligands in magnetic, electronic and luminescent devices, see: Freidzon et al. (2011 ▶); Maynard et al. (2009 ▶); Thomas et al. (2012 ▶).

Experimental

Crystal data

[YbCl2(C18H15N5)(CH4O)2]Cl

M = 644.82

Triclinic,

a = 9.2401 (13) Å

b = 9.8390 (14) Å

c = 13.3765 (19) Å

α = 99.978 (2)°

β = 94.616 (2)°

γ = 92.145 (2)°

V = 1192.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 4.29 mm−1

T = 293 K

0.34 × 0.29 × 0.24 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.32, T max = 0.43

11582 measured reflections

4178 independent reflections

3995 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.08

4178 reflections

292 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.10 e Å−3

Δρmin = −1.35 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus-NT (Bruker 2001 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022052/fj2554sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022052/fj2554Isup2.hkl

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

[YbCl2(C18H15N5)(CH4O)2]Cl	Z = 2
Mr = 644.82	F(000) = 630
Triclinic, P1	Dx = 1.796 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2401 (13) Å	Cell parameters from 7905 reflections
b = 9.8390 (14) Å	θ = 2.2–28.3°
c = 13.3765 (19) Å	µ = 4.29 mm−1
α = 99.978 (2)°	T = 293 K
β = 94.616 (2)°	Rectangular prism, colorless
γ = 92.145 (2)°	0.34 × 0.29 × 0.24 mm
V = 1192.2 (3) Å3

Bruker APEX CCD area-detector diffractometer	4178 independent reflections
Radiation source: fine-focus sealed tube	3995 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.3 pixels mm-1	θmax = 25.0°, θmin = 1.6°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.32, Tmax = 0.43	l = −15→15
11582 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0428P)2 + 3.5218P] where P = (Fo2 + 2Fc2)/3
4178 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 1.10 e Å−3
3 restraints	Δρmin = −1.35 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
Yb1	0.21176 (3)	0.30381 (2)	0.204195 (19)	0.02770 (10)
Cl1	0.3560 (2)	0.3299 (2)	0.37530 (14)	0.0560 (5)
Cl2	0.05316 (18)	0.26855 (19)	0.03273 (13)	0.0444 (4)
Cl3	0.57461 (18)	0.96378 (19)	0.21144 (15)	0.0486 (4)
N1	0.2212 (5)	0.5280 (5)	0.1839 (4)	0.0333 (12)
N2	0.3278 (6)	0.7350 (5)	0.1816 (5)	0.0383 (13)
H2'	0.400 (5)	0.794 (6)	0.199 (6)	0.057*
N3	0.4539 (6)	0.3892 (5)	0.1471 (4)	0.0381 (13)
N4	0.0248 (6)	0.4541 (6)	0.2944 (4)	0.0406 (13)
N5	0.1688 (7)	0.9593 (6)	0.3636 (4)	0.0458 (14)
O1	0.0623 (5)	0.1401 (5)	0.2518 (4)	0.0382 (10)
H10'	0.099 (8)	0.097 (7)	0.296 (4)	0.057*
O2	0.3170 (5)	0.1033 (5)	0.1423 (4)	0.0411 (11)
H20'	0.380 (6)	0.076 (8)	0.182 (5)	0.062*
C1	0.3387 (7)	0.5981 (6)	0.1703 (5)	0.0343 (14)
C2	0.1917 (7)	0.7706 (6)	0.2265 (5)	0.0339 (14)
H2	0.1415	0.8351	0.1894	0.041*
C3	0.1082 (6)	0.6265 (6)	0.2014 (5)	0.0331 (14)
H3	0.0496	0.6223	0.1364	0.040*
C4	0.4686 (7)	0.5258 (6)	0.1447 (5)	0.0343 (14)
C5	0.5934 (7)	0.5880 (7)	0.1193 (5)	0.0394 (15)
H5	0.6006	0.6827	0.1198	0.047*
C6	0.7078 (7)	0.5061 (8)	0.0931 (5)	0.0443 (17)
H6	0.7925	0.5443	0.0739	0.053*
C7	0.6944 (8)	0.3692 (8)	0.0961 (6)	0.0490 (18)
H7	0.7709	0.3131	0.0795	0.059*
C8	0.5684 (7)	0.3130 (8)	0.1235 (6)	0.0476 (18)
H8	0.5619	0.2190	0.1258	0.057*
C9	0.0099 (7)	0.5825 (7)	0.2750 (5)	0.0362 (14)
C10	−0.0956 (8)	0.6658 (7)	0.3153 (6)	0.0475 (18)
H10	−0.1044	0.7539	0.2998	0.057*
C11	−0.1872 (9)	0.6178 (8)	0.3785 (7)	0.061 (2)
H11	−0.2592	0.6727	0.4058	0.073*
C12	−0.1719 (10)	0.4893 (9)	0.4010 (7)	0.066 (2)
H12	−0.2320	0.4550	0.4444	0.079*
C13	−0.0643 (9)	0.4108 (8)	0.3574 (6)	0.057 (2)
H13	−0.0535	0.3230	0.3730	0.068*
C14	0.2201 (7)	0.8352 (7)	0.3373 (5)	0.0366 (14)
C15	0.2982 (9)	0.7722 (8)	0.4064 (6)	0.0537 (19)
H15	0.3318	0.6847	0.3863	0.064*
C16	0.3266 (10)	0.8398 (10)	0.5062 (6)	0.068 (2)
H16	0.3800	0.7994	0.5541	0.082*
C17	0.2734 (11)	0.9683 (10)	0.5321 (6)	0.072 (3)
H17	0.2910	1.0173	0.5982	0.087*
C18	0.1945 (12)	1.0233 (9)	0.4596 (6)	0.072 (3)
H18	0.1571	1.1096	0.4783	0.087*
C19	−0.0775 (8)	0.0814 (9)	0.2119 (7)	0.064 (2)
H19A	−0.1374	0.1524	0.1938	0.096*
H19B	−0.1211	0.0390	0.2625	0.096*
H19C	−0.0684	0.0128	0.1526	0.096*
C20	0.2876 (9)	0.0171 (8)	0.0451 (6)	0.060 (2)
H20A	0.1852	−0.0063	0.0328	0.090*
H20B	0.3396	−0.0658	0.0437	0.090*
H20C	0.3183	0.0654	−0.0067	0.090*

	U11	U22	U33	U12	U13	U23
Yb1	0.02727 (15)	0.02462 (15)	0.03167 (16)	0.00041 (10)	0.00363 (10)	0.00598 (10)
Cl1	0.0528 (11)	0.0726 (13)	0.0401 (10)	0.0067 (9)	−0.0046 (8)	0.0065 (9)
Cl2	0.0398 (9)	0.0511 (10)	0.0430 (9)	−0.0013 (7)	−0.0055 (7)	0.0154 (8)
Cl3	0.0381 (9)	0.0455 (10)	0.0607 (11)	−0.0070 (7)	−0.0054 (8)	0.0111 (8)
N1	0.030 (3)	0.027 (3)	0.044 (3)	0.002 (2)	0.006 (2)	0.006 (2)
N2	0.038 (3)	0.026 (3)	0.053 (3)	−0.003 (2)	0.007 (3)	0.013 (3)
N3	0.036 (3)	0.034 (3)	0.046 (3)	−0.001 (2)	0.007 (2)	0.010 (2)
N4	0.042 (3)	0.039 (3)	0.042 (3)	0.006 (3)	0.010 (3)	0.007 (3)
N5	0.065 (4)	0.033 (3)	0.037 (3)	0.006 (3)	−0.006 (3)	0.003 (2)
O1	0.035 (2)	0.036 (3)	0.045 (3)	0.0003 (19)	0.000 (2)	0.016 (2)
O2	0.041 (3)	0.035 (3)	0.043 (3)	0.005 (2)	−0.002 (2)	−0.004 (2)
C1	0.040 (4)	0.032 (3)	0.033 (3)	−0.002 (3)	0.004 (3)	0.009 (3)
C2	0.039 (3)	0.029 (3)	0.035 (3)	0.006 (3)	0.000 (3)	0.009 (3)
C3	0.030 (3)	0.031 (3)	0.038 (3)	0.001 (3)	0.000 (3)	0.006 (3)
C4	0.035 (3)	0.033 (3)	0.035 (3)	−0.001 (3)	0.004 (3)	0.006 (3)
C5	0.036 (4)	0.042 (4)	0.039 (4)	−0.007 (3)	0.003 (3)	0.007 (3)
C6	0.027 (3)	0.057 (5)	0.048 (4)	−0.007 (3)	0.002 (3)	0.009 (3)
C7	0.037 (4)	0.058 (5)	0.055 (5)	0.011 (3)	0.010 (3)	0.014 (4)
C8	0.041 (4)	0.039 (4)	0.067 (5)	0.010 (3)	0.016 (3)	0.014 (4)
C9	0.030 (3)	0.035 (4)	0.041 (4)	0.002 (3)	0.001 (3)	−0.001 (3)
C10	0.043 (4)	0.038 (4)	0.059 (5)	0.005 (3)	0.012 (3)	−0.003 (3)
C11	0.058 (5)	0.051 (5)	0.071 (6)	0.009 (4)	0.033 (4)	−0.007 (4)
C12	0.073 (6)	0.058 (5)	0.071 (6)	−0.001 (4)	0.045 (5)	0.007 (4)
C13	0.065 (5)	0.049 (5)	0.062 (5)	0.008 (4)	0.025 (4)	0.018 (4)
C14	0.040 (4)	0.032 (3)	0.038 (4)	−0.004 (3)	−0.003 (3)	0.010 (3)
C15	0.064 (5)	0.047 (4)	0.050 (4)	0.012 (4)	−0.007 (4)	0.013 (4)
C16	0.079 (6)	0.079 (6)	0.048 (5)	0.003 (5)	−0.013 (4)	0.024 (4)
C17	0.107 (8)	0.065 (6)	0.040 (5)	−0.004 (5)	−0.008 (5)	0.004 (4)
C18	0.128 (9)	0.043 (5)	0.043 (5)	0.013 (5)	−0.002 (5)	0.000 (4)
C19	0.044 (4)	0.063 (5)	0.088 (6)	−0.017 (4)	−0.010 (4)	0.036 (5)
C20	0.071 (5)	0.057 (5)	0.049 (5)	0.024 (4)	−0.003 (4)	0.001 (4)

Yb1—Cl1	2.5220 (19)	C5—C6	1.384 (10)
Yb1—Cl2	2.5834 (18)	C5—H5	0.93
Yb1—N1	2.268 (5)	C6—C7	1.355 (11)
Yb1—N3	2.579 (5)	C6—H6	0.93
Yb1—N4	2.556 (6)	C7—C8	1.373 (10)
Yb1—O1	2.289 (5)	C7—H7	0.9301
Yb1—O2	2.287 (5)	C8—H8	0.9303
N1—C1	1.306 (8)	C9—C10	1.380 (10)
N1—C3	1.457 (8)	C10—C11	1.370 (12)
N2—C1	1.338 (8)	C10—H10	0.9302
N2—C2	1.465 (9)	C11—C12	1.359 (12)
N2—H2'	0.86 (6)	C11—H11	0.9302
N3—C4	1.352 (9)	C12—C13	1.386 (12)
N3—C8	1.346 (9)	C12—H12	0.9294
N4—C13	1.333 (10)	C13—H13	0.9303
N4—C9	1.343 (9)	C14—C15	1.373 (10)
N5—C14	1.326 (9)	C15—C16	1.384 (11)
N5—C18	1.327 (10)	C15—H15	0.9294
O1—C19	1.419 (9)	C16—C17	1.372 (14)
O1—H10'	0.84 (6)	C16—H16	0.9303
O2—C20	1.424 (10)	C17—C18	1.365 (13)
O2—H20'	0.84 (6)	C17—H17	0.9295
C1—C4	1.453 (9)	C18—H18	0.9304
C2—C14	1.506 (9)	C19—H19A	0.9601
C2—C3	1.559 (9)	C19—H19B	0.9598
C2—H2	0.9797	C19—H19C	0.9595
C3—C9	1.496 (9)	C20—H20A	0.96
C3—H3	0.9797	C20—H20B	0.9599
C4—C5	1.379 (9)	C20—H20C	0.96
N1—Yb1—O2	138.18 (18)	N1—C3—H3	107.27
N1—Yb1—O1	141.84 (17)	C2—C3—H3	107.27
O2—Yb1—O1	77.76 (17)	C9—C3—H3	107.29
N1—Yb1—Cl1	99.05 (14)	N3—C4—C5	123.1 (6)
O2—Yb1—Cl1	92.85 (12)	N3—C4—C1	112.6 (5)
O1—Yb1—Cl1	89.06 (12)	C5—C4—C1	124.3 (6)
N1—Yb1—N4	64.63 (18)	C4—C5—C6	118.3 (6)
O2—Yb1—N4	156.52 (18)	C4—C5—H5	120.84
O1—Yb1—N4	78.77 (17)	C6—C5—H5	120.83
Cl1—Yb1—N4	87.06 (14)	C7—C6—C5	118.9 (6)
N1—Yb1—N3	65.20 (17)	C5—C6—H6	120.5
O2—Yb1—N3	76.74 (17)	C7—C6—H6	120.57
O1—Yb1—N3	152.94 (17)	C6—C7—C8	120.3 (7)
Cl1—Yb1—N3	83.32 (13)	C6—C7—H7	119.81
N4—Yb1—N3	126.44 (17)	C8—C7—H7	119.9
N1—Yb1—Cl2	83.18 (14)	N3—C8—C7	122.3 (7)
O2—Yb1—Cl2	86.99 (12)	N3—C8—H8	118.86
O1—Yb1—Cl2	87.74 (12)	C7—C8—H8	118.87
Cl1—Yb1—Cl2	176.75 (6)	N4—C9—C10	122.1 (6)
N4—Yb1—Cl2	91.79 (13)	N4—C9—C3	115.9 (5)
N3—Yb1—Cl2	99.79 (13)	C10—C9—C3	121.9 (6)
N1—Yb1—C1	19.51 (17)	C11—C10—C9	119.5 (7)
O2—Yb1—C1	121.66 (17)	C9—C10—H10	120.28
O1—Yb1—C1	160.52 (16)	C11—C10—H10	120.24
Cl1—Yb1—C1	91.30 (12)	C12—C11—C10	119.4 (7)
N4—Yb1—C1	81.80 (17)	C10—C11—H11	120.3
N3—Yb1—C1	46.10 (16)	C12—C11—H11	120.28
Cl2—Yb1—C1	91.55 (12)	C11—C12—C13	118.2 (7)
C1—N1—C3	106.9 (5)	C11—C12—H12	120.93
C1—N1—Yb1	125.0 (4)	C13—C12—H12	120.96
C3—N1—Yb1	127.2 (4)	N4—C13—C12	123.6 (7)
C1—N2—H2'	124 (4)	N4—C13—H13	118.21
C2—N2—H2'	116 (4)	C12—C13—H13	118.1
C1—N2—C2	108.6 (5)	N5—C14—C15	121.8 (6)
C8—N3—C4	117.0 (6)	N5—C14—C2	115.8 (5)
C8—N3—Yb1	126.7 (4)	C15—C14—C2	122.4 (6)
C4—N3—Yb1	116.2 (4)	C14—C15—C16	119.7 (7)
C13—N4—C9	117.2 (6)	C14—C15—H15	120.18
C13—N4—Yb1	123.8 (5)	C16—C15—H15	120.2
C9—N4—Yb1	119.0 (4)	C17—C16—C15	117.8 (8)
C14—N5—C18	118.5 (6)	C15—C16—H16	121.05
C19—O1—Yb1	132.4 (4)	C17—C16—H16	121.09
Yb1—O1—H10'	116 (5)	C18—C17—C16	119.2 (8)
C19—O1—H10'	111 (5)	C16—C17—H17	120.4
C20—O2—Yb1	128.2 (4)	C18—C17—H17	120.42
Yb1—O2—H20'	116 (5)	N5—C18—C17	122.9 (8)
C20—O2—H20'	116 (5)	O1—C19—H19C	109.45
N1—C1—N2	115.4 (6)	H19A—C19—H19C	109.51
N1—C1—C4	119.7 (6)	H19B—C19—H19C	109.53
N2—C1—C4	124.9 (6)	O1—C19—H19B	109.44
N2—C2—C14	111.0 (5)	H19A—C19—H19B	109.48
N2—C2—C3	99.8 (5)	O1—C19—H19A	109.42
C14—C2—C3	117.1 (5)	O2—C20—H20C	109.44
N2—C2—H2	109.54	H20A—C20—H20C	109.47
C3—C2—H2	109.5	H20B—C20—H20C	109.47
C14—C2—H2	109.48	O2—C20—H20B	109.48
N1—C3—C9	109.5 (5)	H20A—C20—H20B	109.48
N1—C3—C2	104.6 (5)	O2—C20—H20A	109.48
C9—C3—C2	120.3 (5)
O2—Yb1—N1—C1	−37.1 (6)	N4—Yb1—C1—N1	−27.2 (5)
O1—Yb1—N1—C1	167.7 (4)	N3—Yb1—C1—N1	166.5 (6)
Cl1—Yb1—N1—C1	67.6 (5)	C1—N2—C2—C14	104.9 (6)
N4—Yb1—N1—C1	150.0 (6)	C1—N2—C2—C3	−19.3 (6)
N3—Yb1—N1—C1	−10.7 (5)	C1—N1—C3—C9	−146.0 (5)
Cl2—Yb1—N1—C1	−114.8 (5)	Yb1—N1—C3—C9	23.8 (7)
O2—Yb1—N1—C3	154.9 (4)	C1—N1—C3—C2	−15.8 (6)
O1—Yb1—N1—C3	−0.3 (6)	Yb1—N1—C3—C2	154.0 (4)
Cl1—Yb1—N1—C3	−100.4 (5)	N2—C2—C3—N1	20.8 (6)
N4—Yb1—N1—C3	−18.1 (5)	C14—C2—C3—N1	−99.1 (6)
N3—Yb1—N1—C3	−178.7 (5)	N2—C2—C3—C9	144.2 (6)
Cl2—Yb1—N1—C3	77.2 (5)	C14—C2—C3—C9	24.4 (8)
N1—Yb1—N3—C8	−176.1 (6)	C8—N3—C4—C5	0.1 (10)
O2—Yb1—N3—C8	−13.8 (6)	Yb1—N3—C4—C5	177.6 (5)
O1—Yb1—N3—C8	6.1 (8)	C8—N3—C4—C1	179.4 (6)
Cl1—Yb1—N3—C8	80.7 (6)	Yb1—N3—C4—C1	−3.0 (7)
N4—Yb1—N3—C8	162.1 (5)	N1—C1—C4—N3	−5.8 (9)
Cl2—Yb1—N3—C8	−98.3 (6)	N2—C1—C4—N3	174.4 (6)
N1—Yb1—N3—C4	6.7 (4)	N1—C1—C4—C5	173.5 (6)
O2—Yb1—N3—C4	168.9 (5)	N2—C1—C4—C5	−6.3 (10)
O1—Yb1—N3—C4	−171.1 (4)	N3—C4—C5—C6	1.4 (10)
Cl1—Yb1—N3—C4	−96.5 (4)	C1—C4—C5—C6	−177.9 (6)
N4—Yb1—N3—C4	−15.2 (5)	C4—C5—C6—C7	−1.8 (10)
Cl2—Yb1—N3—C4	84.4 (4)	C5—C6—C7—C8	0.7 (11)
N1—Yb1—N4—C13	−173.7 (7)	C4—N3—C8—C7	−1.2 (11)
O2—Yb1—N4—C13	18.1 (9)	Yb1—N3—C8—C7	−178.4 (5)
O1—Yb1—N4—C13	17.3 (6)	C6—C7—C8—N3	0.8 (12)
Cl1—Yb1—N4—C13	−72.3 (6)	C13—N4—C9—C10	−2.0 (10)
N3—Yb1—N4—C13	−151.8 (6)	Yb1—N4—C9—C10	175.4 (5)
Cl2—Yb1—N4—C13	104.7 (6)	C13—N4—C9—C3	−178.1 (6)
N1—Yb1—N4—C9	9.0 (4)	Yb1—N4—C9—C3	−0.7 (7)
O2—Yb1—N4—C9	−159.1 (4)	N1—C3—C9—N4	−12.3 (8)
O1—Yb1—N4—C9	−159.9 (5)	C2—C3—C9—N4	−133.4 (6)
Cl1—Yb1—N4—C9	110.5 (5)	N1—C3—C9—C10	171.6 (6)
N3—Yb1—N4—C9	31.0 (6)	C2—C3—C9—C10	50.5 (9)
Cl2—Yb1—N4—C9	−72.5 (5)	N4—C9—C10—C11	1.0 (11)
N1—Yb1—O1—C19	60.5 (8)	C3—C9—C10—C11	176.9 (7)
O2—Yb1—O1—C19	−102.9 (7)	C9—C10—C11—C12	0.5 (13)
Cl1—Yb1—O1—C19	164.0 (7)	C10—C11—C12—C13	−0.9 (14)
N4—Yb1—O1—C19	76.8 (7)	C9—N4—C13—C12	1.7 (12)
N3—Yb1—O1—C19	−122.7 (7)	Yb1—N4—C13—C12	−175.6 (7)
Cl2—Yb1—O1—C19	−15.4 (7)	C11—C12—C13—N4	−0.2 (14)
N1—Yb1—O2—C20	−75.2 (7)	C18—N5—C14—C15	0.0 (11)
O1—Yb1—O2—C20	89.4 (6)	C18—N5—C14—C2	−177.9 (7)
Cl1—Yb1—O2—C20	177.9 (6)	N2—C2—C14—N5	123.6 (6)
N4—Yb1—O2—C20	88.7 (7)	C3—C2—C14—N5	−122.8 (6)
N3—Yb1—O2—C20	−99.7 (6)	N2—C2—C14—C15	−54.3 (8)
Cl2—Yb1—O2—C20	1.1 (6)	C3—C2—C14—C15	59.4 (9)
C3—N1—C1—N2	3.7 (8)	N5—C14—C15—C16	−0.9 (12)
Yb1—N1—C1—N2	−166.4 (4)	C2—C14—C15—C16	176.9 (7)
C3—N1—C1—C4	−176.1 (5)	C14—C15—C16—C17	0.5 (13)
Yb1—N1—C1—C4	13.8 (8)	C15—C16—C17—C18	0.6 (15)
C2—N2—C1—N1	11.2 (8)	C14—N5—C18—C17	1.2 (14)
C2—N2—C1—C4	−169.0 (6)	C16—C17—C18—N5	−1.5 (16)
Cl1—Yb1—C1—N1	−114.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10′···N5i	0.84	1.86	2.681 (3)	164
O2—H20′···Cl3i	0.84	2.19	2.956 (3)	152
N2—H2′···Cl3	0.86	2.25	3.096 (3)	167

Table 1

Selected bond lengths (Å)

Yb1—Cl1	2.5220 (19)
Yb1—Cl2	2.5834 (18)
Yb1—N1	2.268 (5)
Yb1—N3	2.579 (5)
Yb1—N4	2.556 (6)
Yb1—O1	2.289 (5)
Yb1—O2	2.287 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H10′⋯N5i	0.84	1.86	2.681 (3)	164
O2—H20′⋯Cl3i	0.84	2.19	2.956 (3)	152
N2—H2′⋯Cl3	0.86	2.25	3.096 (3)	167

Symmetry code: (i) .