Dichloridobis(methanol-κO)[cis-(±)-2,4,5-tris­(pyridin-2-yl)-2-imidazoline-κ3N2,N3,N4]ytterbium(III) chloride

Baez-Castro, A.; Höpfl, H.; Parra-Hake, M.; Cruz-Enriquez, A.; Campos-Gaxiola, J.J.

doi:10.1107/S1600536812022052

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m815-m816

doi:10.1107/S1600536812022052

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Dichloridobis(methanol-κO)[cis-(±)-2,4,5-tris(pyridin-2-yl)-2-imidazoline-κ³N²,N³,N⁴]ytterbium(III) chloride

Alberto Baez-Castro,^a Herbert Höpfl,^b Miguel Parra-Hake,^c Adriana Cruz-Enriquez ^a and Jose J. Campos-Gaxiola ^a ^*

^aFacultad de Ingenieria Mochis, Universidad Autonoma de Sinaloa, Fuente Poseidon y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, Mexico, ^bCentro de Investigaciones Quimicas, Universidad Autonoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, Mexico, and ^cCentro de Graduados del Instituto Tecnologico de Tijuana, Blvd. Industrial S/N, Col. Otay, CP 22500, Tijuana, BC, Mexico
^*Correspondence e-mail: gaxiolajose@yahoo.com.mx

(Received 7 May 2012; accepted 15 May 2012; online 26 May 2012)

In the crystal structure of the title complex, [YbCl₂(C₁₈H₁₅N₅)(CH₃OH)₂]Cl, the pseudo-pentagonal–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 molecules 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_r = 644.82
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.08
4178 reflections
292 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.10 e Å⁻³
Δρ_min = −1.35 e Å⁻³

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) x, y-1, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022052/fj2554sup1.cif

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

checkCIF report

Comment top

The synthesis and characterization of lanthanide complexes supported by polypiridyl chelating ligands has attracted continuous interest, due to the potential application of these compounds in magnetic, electronic and luminescent devices (Maynard et al., 2009; Freidzon et al., 2011; Thomas et al., 2012). A handful of transition metal complexes based on the HL ligand have been prepared (Parra-Hake et al. Campos-Gaxiola et al., 2007, 2008 and 2010), but to date there are no reports on complexes containing rare earth elements. Herein, we report on the structure of a mononuclear Yb^III complex (Scheme 1), which was synthesized by reaction of YbCl₃^.6H₂O with cis-(±)-2,4,5-tri(2-pyridyl)imidazoline at room temperature in methanol.

In the title complex, the central Yb^III ion is seven-coordinated by three nitrogen atoms from one tridentate chelate ligand, two oxygen atoms from two methanol molecules and two Cl^- anions [Yb—N, 2.268 (5)–2.579 (5) Å; Yb—O 2.287 (4)–2.289 (4) Å; Yb—Cl 2.5219 (18)–2.5834 (17) Å (Table 1)] and displays a pseudo-pentagonal-bipyramidal geometry (Fig. 1). In the crystal structure the complex molecules are linked through N—H···Cl, O—H···Cl and O—H···N hydrogen bonds to form linear supramolecular chains along [010] (Table 2, Fig 2).

Related literature top

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 polypiridyl chelating ligands in magnetic, electronic and

luminescent devices, see: Freidzon et al. (2011); Maynard et al. (2009); Thomas et al. (2012).

Experimental top

A mixture of cis-(±)-2,4,5-tri(2-pyridyl)imidazoline (HL) (0.05 g, 0.166 mmol) and YbCl₃^.6H₂O (0.063 g, 0.166 mmol) dissolved in methanol (3 ml) was stirred for 2 h at room temperature to give a colorless solution. The product was crystallized at room temperature by gas phase diffusion of diethyl ether into the reaction mixture, providing colorless crystals which were dried under vacuo. Yield: 71%. IR (KBr): 3320, 3060, 3155, 2894, 1631, 1592, 1471, 1437, 1338, 1280, 1260, 1162, 1007 and 691 cm^-1. TGA Calcd for 2CH₃OH: 9.94. Found: 8.76% (30–200 °C).

Computing details top

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

Figures top

	Fig. 1. Perspective view of the molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. Perspective view of a fragment of the linear supramolecular chain along [010] with the N—H···Cl, O—H···Cl and O—H···N hydrogen bonds shown as dashed lines.

Dichloridobis(methanol-κO)[cis-(±)-2,4,5-tris(pyridin-2-yl)-2- imidazoline-κ³N²,N³,N⁴]ytterbium(III) chloride top

Crystal data top

[YbCl₂(C₁₈H₁₅N₅)(CH₄O)₂]Cl	Z = 2
M_r = 644.82	F(000) = 630
Triclinic, P1	D_x = 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

Data collection top

Bruker APEX CCD area-detector diffractometer	4178 independent reflections
Radiation source: fine-focus sealed tube	3995 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.3 pixels mm^-1	θ_max = 25.0°, θ_min = 1.6°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.32, T_max = 0.43	l = −15→15
11582 measured reflections

Refinement top

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(F_o²) + (0.0428P)² + 3.5218P] where P = (F_o² + 2F_c²)/3
4178 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 1.10 e Å⁻³
3 restraints	Δρ_min = −1.35 e Å⁻³

Crystal data top

[YbCl₂(C₁₈H₁₅N₅)(CH₄O)₂]Cl	γ = 92.145 (2)°
M_r = 644.82	V = 1192.2 (3) Å³
Triclinic, P1	Z = 2
a = 9.2401 (13) Å	Mo Kα radiation
b = 9.8390 (14) Å	µ = 4.29 mm⁻¹
c = 13.3765 (19) Å	T = 293 K
α = 99.978 (2)°	0.34 × 0.29 × 0.24 mm
β = 94.616 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	4178 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3995 reflections with I > 2σ(I)
T_min = 0.32, T_max = 0.43	R_int = 0.031
11582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	3 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 1.10 e Å⁻³
4178 reflections	Δρ_min = −1.35 e Å⁻³
292 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[YbCl₂(C₁₈H₁₅N₅)(CH₄O)₂]Cl
M_r	644.82
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2401 (13), 9.8390 (14), 13.3765 (19)
α, β, γ (°)	99.978 (2), 94.616 (2), 92.145 (2)
V (Å³)	1192.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.29
Crystal size (mm)	0.34 × 0.29 × 0.24

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.32, 0.43
No. of measured, independent and observed [I > 2σ(I)] reflections	11582, 4178, 3995
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.08
No. of reflections	4178
No. of parameters	292
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.10, −1.35

Computer programs: SMART (Bruker, 2000), SAINT-Plus-NT (Bruker 2001), SHELXTL-NT (Sheldrick, 2008), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10'···N5ⁱ	0.840	1.864	2.681 (3)	164
O2—H20'···Cl3ⁱ	0.840	2.188	2.956 (3)	152
N2—H2'···Cl3	0.860	2.253	3.096 (3)	167

Symmetry code: (i) x, y−1, z.

Acknowledgements

This work was supported financially by the Secretaria de Educacion Publica (PROMEP-UAS, PTC-033) and the Universidad Autonoma de Sinaloa (PROFAPI 2011/033). AB-C thanks the Consejo Nacional de Ciencia y Tecnologia (CONACYT) for support in the form of a scholarship.

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