Di-μ-oxido-bis­({2,2′-[ethane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato}titanium(IV)) chloro­form disolvate

Zaitsev, K.V.; Karlov, S.S.; Zaitseva, G.S.; Lermontova, E.K.; Churakov, A.V.

doi:10.1107/S1600536813029371

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages m626-m627

doi:10.1107/S1600536813029371

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Di-μ-oxido-bis({2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}titanium(IV)) chloroform disolvate

Kirill V. Zaitsev,^a Sergey S. Karlov,^a Galina S. Zaitseva,^a Elmira Kh. Lermontova ^b and Andrei V. Churakov ^b ^*

^aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation, and ^bInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation
^*Correspondence e-mail: churakov@igic.ras.ru.ru

(Received 18 October 2013; accepted 24 October 2013; online 31 October 2013)

In the title compound, [Ti₂(C₁₆H₁₄N₂O₂)₂O₂]·2CHCl₃, the Ti^IV atom in the centrosymmetric complex has a distorted octahedral N₂O₄ coordination environment and is linked via two μ₂-oxido bridges into a dinuclear centrosymmetric complex, with a Ti⋯Ti separation of 2.7794 (8) Å. In the salen (N,N′-ethylenebis(salicylimine)) ligand, the two salicylimine units make a dihedral angle of 45.31 (5)°. The complex molecules are stacked parallel to [100], forming channels in which the solvent chloroform molecules are located. C—H⋯O hydrogen-bonding interactions between the complex molecules and the solvent molecules consolidate the crystal packing.

CCDC reference: 968536

Related literature

For general background to the chemistry of titanium complexes based on salen-type ligands, see: Gupta & Sutar (2008 ); Tsuchimoto (2001 ). For our previous work on titanium(IV) complexes with polydentate N,O-chelating ligands, see: Zaitsev et al. (2006 , 2008 ).

Experimental

Crystal data

[Ti₂(C₁₆H₁₄N₂O₂)₂O₂]·2CHCl₃
M_r = 899.12
Monoclinic, P 2₁ /n
a = 8.8115 (10) Å
b = 11.4587 (13) Å
c = 18.785 (2) Å
β = 98.226 (2)°
V = 1877.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 150 K
0.25 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.806, T_max = 0.948
16236 measured reflections
3677 independent reflections
3119 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.084
S = 1.04
3677 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	1.00	2.08	3.029 (3)	157

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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.

Supporting information

CCDC reference: 968536

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813029371/wm2780sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029371/wm2780Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029371/wm2780Isup3.mol

checkCIF report

Comment top

As a part of our investigation on the chemistry of titanium complexes based on tridentate or tetradentate ligands (Zaitsev et al., 2006, 2008) we obtained and studied the structure of the title compound, [Ti(O)(C₁₆H₁₄N₂O₂)]₂ (or [Ti(O)(salen)]₂) that crystallizes with two chloroform solvent molecules. For general background to the chemistry of titanium complexes based on salen-type ligands, see: Gupta & Sutar (2008).

The title salen complex is centrosymmetric. The Ti(IV) atoms are linked by µ₂-oxido bridges and possess a distorted octahedral N₂O₄ coordination environment with cis interligand angles ranging from 82.20 (6) to 106.51 (7) °. In the central Ti₂(µ₂-O)₂ fragment, the metal–oxygen distances are significantly different (1.8029 (14) and 1.9029 (15) Å). The opposite N–Ti bond lengths also vary by approximately 0.1 Å (2.1502 (17) and 2.2555 (17) Å). The same structural feature was previously reported for another solvatomorph of this complex (Tsuchimoto, 2001). In the ligand, the two salicylimine fragmets form a dihedral angle of 45.31 (5) ° (Fig. 1).

In the crystal, solvent chloroform molecule are linked via C—H···O hydrogen bonding interactions with the main molecule (Table 1). The solvent molecules fill channels spreading parallel to [100] (Fig. 2). The adjacent titanium complexes are connected by T-shaped C—H···π interactions. However, no π···π- stacking interactions are observed in this structure.

Related literature top

For general background to the chemistry of titanium complexes based on salen-type ligands, see: Gupta & Sutar (2008); Tsuchimoto (2001). For our previous work on titanium(IV) complexes with polydentate N,O-chelating ligands, see: Zaitsev et al. (2006, 2008).

Experimental top

The title compound was obtained from reaction of equimolar amounts of Ti(O-iPr)₄ and salen in chloroform as a solid which is insoluble in common organic solvents. The crystals suitable for X-Ray analysis crystallized from the reaction mixture.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms and the solvent molecules were omitted for clarity. [Symmetry code A) 1 - x, 2 - y, 1 - z.]
	Fig. 2. Channels extending parallel to [100], filled with chloroform solvent molecules. Cl₃C—H···O hydrogen bonding interactions are shown as dashed lines.

Di-µ-oxido-bis({2,2'-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}titanium(IV)) chloroform disolvate top

Crystal data top

[Ti₂(C₁₆H₁₄N₂O₂)₂O₂]·2CHCl₃	F(000) = 912
M_r = 899.12	D_x = 1.591 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5413 reflections
a = 8.8115 (10) Å	θ = 2.4–29.6°
b = 11.4587 (13) Å	µ = 0.90 mm⁻¹
c = 18.785 (2) Å	T = 150 K
β = 98.226 (2)°	Block, colourless
V = 1877.2 (4) Å³	0.25 × 0.08 × 0.06 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3677 independent reflections
Radiation source: fine-focus sealed tube	3119 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.806, T_max = 0.948	k = −14→14
16236 measured reflections	l = −22→23

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0415P)² + 1.1985P] where P = (F_o² + 2F_c²)/3
3677 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Ti₂(C₁₆H₁₄N₂O₂)₂O₂]·2CHCl₃	V = 1877.2 (4) Å³
M_r = 899.12	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.8115 (10) Å	µ = 0.90 mm⁻¹
b = 11.4587 (13) Å	T = 150 K
c = 18.785 (2) Å	0.25 × 0.08 × 0.06 mm
β = 98.226 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3677 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3119 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.948	R_int = 0.028
16236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
3677 reflections	Δρ_min = −0.28 e Å⁻³
235 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
Ti1	0.55329 (4)	0.89882 (3)	0.471151 (19)	0.02192 (11)
O3	0.38110 (15)	0.94635 (12)	0.50409 (7)	0.0250 (3)
O1	0.44879 (16)	0.76247 (12)	0.42307 (7)	0.0266 (3)
O2	0.66652 (16)	0.81354 (14)	0.54587 (8)	0.0292 (3)
N1	0.50499 (19)	0.96203 (15)	0.36249 (9)	0.0256 (4)
N2	0.77616 (19)	0.89426 (14)	0.42525 (9)	0.0241 (4)
C11	0.3151 (2)	0.76229 (18)	0.38023 (11)	0.0255 (4)
C12	0.2143 (3)	0.6677 (2)	0.38226 (12)	0.0329 (5)
H12	0.2425	0.6046	0.4142	0.039*
C13	0.0748 (3)	0.6657 (2)	0.33826 (13)	0.0374 (6)
H13	0.0062	0.6025	0.3413	0.045*
C14	0.0334 (3)	0.7561 (2)	0.28908 (12)	0.0362 (5)
H14	−0.0625	0.7540	0.2587	0.043*
C15	0.1313 (2)	0.8470 (2)	0.28506 (12)	0.0328 (5)
H15	0.1036	0.9074	0.2510	0.039*
C16	0.2732 (2)	0.85321 (19)	0.33048 (11)	0.0274 (5)
C17	0.3830 (2)	0.94051 (19)	0.31813 (12)	0.0299 (5)
H17	0.3647	0.9847	0.2750	0.036*
C18	0.6317 (3)	1.0275 (2)	0.34028 (12)	0.0317 (5)
H18A	0.6505	1.0999	0.3690	0.038*
H18B	0.6091	1.0487	0.2888	0.038*
C21	0.8128 (2)	0.79353 (18)	0.57183 (11)	0.0267 (4)
C22	0.8487 (3)	0.7483 (2)	0.64094 (13)	0.0370 (6)
H22	0.7693	0.7355	0.6693	0.044*
C23	0.9989 (3)	0.7218 (2)	0.66894 (13)	0.0399 (6)
H23	1.0214	0.6916	0.7164	0.048*
C24	1.1163 (3)	0.7389 (2)	0.62846 (13)	0.0360 (5)
H24	1.2185	0.7180	0.6472	0.043*
C25	1.0835 (2)	0.78687 (19)	0.56034 (12)	0.0311 (5)
H25	1.1645	0.8006	0.5330	0.037*
C26	0.9329 (2)	0.81553 (18)	0.53108 (11)	0.0248 (4)
C27	0.9073 (2)	0.86562 (18)	0.45940 (11)	0.0251 (4)
H27	0.9946	0.8781	0.4360	0.030*
C28	0.7706 (2)	0.9466 (2)	0.35350 (11)	0.0303 (5)
H28A	0.7620	0.8846	0.3164	0.036*
H28B	0.8657	0.9913	0.3507	0.036*
C1	0.6290 (3)	0.54038 (19)	0.40993 (12)	0.0301 (5)
H1	0.5673	0.6049	0.4273	0.036*
Cl1	0.81195 (7)	0.54170 (5)	0.46134 (3)	0.04022 (16)
Cl2	0.53362 (6)	0.40740 (5)	0.42008 (3)	0.03615 (15)
Cl3	0.64366 (8)	0.56598 (6)	0.31832 (3)	0.04712 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ti1	0.01996 (19)	0.0259 (2)	0.02059 (19)	0.00184 (14)	0.00518 (14)	0.00209 (14)
O3	0.0203 (7)	0.0296 (8)	0.0263 (8)	−0.0016 (6)	0.0078 (6)	−0.0015 (6)
O1	0.0258 (7)	0.0272 (8)	0.0259 (8)	0.0027 (6)	0.0008 (6)	0.0007 (6)
O2	0.0211 (7)	0.0387 (9)	0.0284 (8)	0.0015 (6)	0.0051 (6)	0.0092 (6)
N1	0.0260 (9)	0.0274 (9)	0.0241 (9)	0.0040 (7)	0.0056 (7)	0.0017 (7)
N2	0.0263 (9)	0.0240 (9)	0.0231 (9)	0.0030 (7)	0.0078 (7)	0.0001 (7)
C11	0.0239 (10)	0.0294 (11)	0.0234 (10)	0.0043 (8)	0.0040 (8)	−0.0058 (8)
C12	0.0357 (12)	0.0347 (12)	0.0282 (12)	−0.0003 (10)	0.0047 (10)	−0.0015 (9)
C13	0.0327 (12)	0.0462 (14)	0.0341 (13)	−0.0095 (11)	0.0074 (10)	−0.0124 (11)
C14	0.0254 (11)	0.0503 (15)	0.0311 (12)	0.0020 (10)	−0.0017 (9)	−0.0127 (11)
C15	0.0306 (12)	0.0409 (13)	0.0259 (11)	0.0104 (10)	0.0012 (9)	−0.0045 (10)
C16	0.0269 (11)	0.0331 (11)	0.0226 (10)	0.0058 (9)	0.0047 (8)	−0.0036 (9)
C17	0.0322 (12)	0.0334 (12)	0.0238 (11)	0.0072 (9)	0.0031 (9)	0.0042 (9)
C18	0.0347 (12)	0.0344 (12)	0.0273 (11)	0.0004 (10)	0.0087 (9)	0.0088 (9)
C21	0.0239 (10)	0.0249 (11)	0.0304 (11)	−0.0028 (8)	0.0014 (9)	0.0023 (8)
C22	0.0295 (12)	0.0474 (14)	0.0341 (13)	−0.0033 (10)	0.0046 (10)	0.0141 (10)
C23	0.0377 (13)	0.0441 (14)	0.0350 (13)	−0.0075 (11)	−0.0051 (10)	0.0141 (11)
C24	0.0240 (11)	0.0355 (13)	0.0453 (14)	−0.0017 (9)	−0.0059 (10)	0.0028 (10)
C25	0.0240 (11)	0.0334 (12)	0.0351 (12)	−0.0017 (9)	0.0018 (9)	−0.0044 (10)
C26	0.0246 (10)	0.0223 (10)	0.0275 (11)	−0.0019 (8)	0.0038 (8)	−0.0032 (8)
C27	0.0229 (10)	0.0260 (10)	0.0276 (11)	−0.0009 (8)	0.0078 (8)	−0.0054 (8)
C28	0.0296 (11)	0.0376 (12)	0.0260 (11)	0.0025 (9)	0.0115 (9)	0.0028 (9)
C1	0.0340 (12)	0.0290 (11)	0.0280 (11)	−0.0003 (9)	0.0070 (9)	0.0014 (9)
Cl1	0.0384 (3)	0.0407 (3)	0.0393 (3)	−0.0079 (3)	−0.0021 (3)	0.0001 (2)
Cl2	0.0354 (3)	0.0328 (3)	0.0417 (3)	−0.0068 (2)	0.0105 (2)	−0.0009 (2)
Cl3	0.0518 (4)	0.0621 (4)	0.0276 (3)	−0.0147 (3)	0.0063 (3)	0.0046 (3)

Geometric parameters (Å, º) top

Ti1—O3	1.8029 (14)	C16—C17	1.433 (3)
Ti1—O2	1.8760 (15)	C17—H17	0.9500
Ti1—O3ⁱ	1.9029 (15)	C18—C28	1.527 (3)
Ti1—O1	1.9664 (15)	C18—H18A	0.9900
Ti1—N1	2.1502 (17)	C18—H18B	0.9900
Ti1—N2	2.2555 (17)	C21—C22	1.391 (3)
Ti1—Ti1ⁱ	2.7794 (8)	C21—C26	1.415 (3)
O3—Ti1ⁱ	1.9029 (15)	C22—C23	1.386 (3)
O1—C11	1.328 (2)	C22—H22	0.9500
O2—C21	1.331 (2)	C23—C24	1.382 (3)
N1—C17	1.287 (3)	C23—H23	0.9500
N1—C18	1.455 (3)	C24—C25	1.384 (3)
N2—C27	1.282 (3)	C24—H24	0.9500
N2—C28	1.470 (3)	C25—C26	1.401 (3)
C11—C12	1.405 (3)	C25—H25	0.9500
C11—C16	1.413 (3)	C26—C27	1.451 (3)
C12—C13	1.380 (3)	C27—H27	0.9500
C12—H12	0.9500	C28—H28A	0.9900
C13—C14	1.401 (4)	C28—H28B	0.9900
C13—H13	0.9500	C1—Cl1	1.756 (2)
C14—C15	1.361 (3)	C1—Cl2	1.764 (2)
C14—H14	0.9500	C1—Cl3	1.768 (2)
C15—C16	1.411 (3)	C1—H1	1.0000
C15—H15	0.9500

O3—Ti1—O2	106.51 (7)	N1—C17—C16	123.4 (2)
O3—Ti1—O3ⁱ	82.86 (6)	N1—C17—H17	118.3
O2—Ti1—O3ⁱ	101.09 (7)	C16—C17—H17	118.3
O3—Ti1—O1	92.06 (6)	N1—C18—C28	105.69 (17)
O2—Ti1—O1	95.38 (6)	N1—C18—H18A	110.6
O3ⁱ—Ti1—O1	163.53 (6)	C28—C18—H18A	110.6
O3—Ti1—N1	99.33 (7)	N1—C18—H18B	110.6
O2—Ti1—N1	153.83 (7)	C28—C18—H18B	110.6
O3ⁱ—Ti1—N1	85.98 (6)	H18A—C18—H18B	108.7
O1—Ti1—N1	79.37 (6)	O2—C21—C22	119.04 (19)
O3—Ti1—N2	163.69 (6)	O2—C21—C26	122.08 (19)
O2—Ti1—N2	82.82 (6)	C22—C21—C26	118.87 (19)
O3ⁱ—Ti1—N2	82.20 (6)	C23—C22—C21	120.9 (2)
O1—Ti1—N2	100.49 (6)	C23—C22—H22	119.6
N1—Ti1—N2	73.13 (6)	C21—C22—H22	119.6
Ti1—O3—Ti1ⁱ	97.15 (6)	C24—C23—C22	120.6 (2)
C11—O1—Ti1	126.58 (13)	C24—C23—H23	119.7
C21—O2—Ti1	138.36 (13)	C22—C23—H23	119.7
C17—N1—C18	121.17 (18)	C23—C24—C25	119.4 (2)
C17—N1—Ti1	125.73 (15)	C23—C24—H24	120.3
C18—N1—Ti1	112.97 (13)	C25—C24—H24	120.3
C27—N2—C28	118.22 (18)	C24—C25—C26	121.1 (2)
C27—N2—Ti1	125.92 (14)	C24—C25—H25	119.5
C28—N2—Ti1	115.12 (13)	C26—C25—H25	119.5
O1—C11—C12	119.60 (19)	C25—C26—C21	119.08 (19)
O1—C11—C16	121.65 (19)	C25—C26—C27	117.97 (19)
C12—C11—C16	118.72 (19)	C21—C26—C27	122.94 (18)
C13—C12—C11	120.6 (2)	N2—C27—C26	125.07 (19)
C13—C12—H12	119.7	N2—C27—H27	117.5
C11—C12—H12	119.7	C26—C27—H27	117.5
C12—C13—C14	120.5 (2)	N2—C28—C18	108.51 (17)
C12—C13—H13	119.7	N2—C28—H28A	110.0
C14—C13—H13	119.7	C18—C28—H28A	110.0
C15—C14—C13	119.7 (2)	N2—C28—H28B	110.0
C15—C14—H14	120.2	C18—C28—H28B	110.0
C13—C14—H14	120.2	H28A—C28—H28B	108.4
C14—C15—C16	121.3 (2)	Cl1—C1—Cl2	111.23 (12)
C14—C15—H15	119.4	Cl1—C1—Cl3	110.17 (12)
C16—C15—H15	119.4	Cl2—C1—Cl3	110.53 (12)
C15—C16—C11	119.2 (2)	Cl1—C1—H1	108.3
C15—C16—C17	119.8 (2)	Cl2—C1—H1	108.3
C11—C16—C17	120.21 (19)	Cl3—C1—H1	108.3

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	1.00	2.08	3.029 (3)	157

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	1.00	2.08	3.029 (3)	157.3

Acknowledgements

This work was partially supported by a grant from the President of the Russian Federation to support the research of young Russian scientists and doctors (MD-3634.2012.3).

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Volume 69| Part 11| November 2013| Pages m626-m627

doi:10.1107/S1600536813029371

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di-μ-oxido-bis­­({2,2′-[ethane-1,2-diylbis(nitrilo­methanylyl­­idene)]diphenolato}titanium(IV)) chloro­form disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Di-μ-oxido-bis({2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}titanium(IV)) chloroform disolvate