Di-μ-ethano­lato-bis­[diethano­lato(2-methyl­quinolin-8-olato)titanium(IV)]

Fazaeli, Y.; Najafi, E.; Amini, M.M.; Khavasi, H.R.

doi:10.1107/S1600536809045796

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1531

doi:10.1107/S1600536809045796

Open

access

Di-μ-ethanolato-bis[diethanolato(2-methylquinolin-8-olato)titanium(IV)]

Yousef Fazaeli,^a Ezzatollah Najafi,^a Mostafa M. Amini ^a and Hamid Reza Khavasi ^a ^*

^aDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: m-pouramini@cc.sbu.ac.ir

(Received 21 October 2009; accepted 31 October 2009; online 7 November 2009)

In the centrosymmetric dinuclear title compound, [Ti₂(C₁₀H₈NO)₂(C₂H₅O)₆], the Ti atom is bonded to an N,O-bidentate quinolin-8-olate ligand, two terminal ethanolate anions and two bridging ethanolate anions in a distorted TiNO₅ octahedral geometry. An intramolecular C—H⋯O hydrogen bond occurs; in the crystal, intermolecular C—H⋯O interactions help to establish the packing.

Related literature

For Ti^IV–8-hydroxyquinolinates, see: Amini et al. (2004 ); Birdet et al. (1973 ); Studd & Swallow (1968 ). For a related structure, see: Fazaeli et al. (2008 ).

Experimental

Crystal data

[Ti₂(C₁₀H₈NO)₂(C₂H₅O)₆]
M_r = 682.51
Monoclinic, P 2₁ /n
a = 9.0497 (18) Å
b = 13.086 (3) Å
c = 14.189 (3) Å
β = 95.21 (3)°
V = 1673.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 120 K
0.45 × 0.28 × 0.23 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.686, T_max = 0.905
12962 measured reflections
4503 independent reflections
3540 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.097
wR(F²) = 0.197
S = 1.14
4503 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 1.26 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Table 1
Selected bond lengths (Å)

Ti1—N1	2.387 (3)
Ti1—O1	1.950 (3)
Ti1—O2	1.808 (3)
Ti1—O3	1.817 (3)
Ti1—O4ⁱ	2.008 (3)
Ti1—O4	2.061 (2)
Symmetry code: (i) -x+2, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1	0.97	2.46	3.061 (5)	120
C1—H1C⋯O3ⁱ	0.96	2.38	3.292 (5)	159
C3—H3⋯O1ⁱⁱ	0.93	2.41	3.310 (5)	163
Symmetry codes: (i) -x+2, -y+2, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045796/hb5165sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045796/hb5165Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives are reagents for the gravimetric analysis of metal ions and the crystal structures of a large number of metal 8-hydroxyquinolinates have been documented. However, for Ti^IV, only three 8-hydroxyquinolinates are known (Amini et al., 2004), (Birdet et al., 1973; Studd & Swallow, 1968). Recently, we have reported the structure of 2-methyl-8-hydroxyquinoline (Fazaeli et al., 2008). In continuation our work in preparation of 8-hydroxyquinoline derivatives of transition metal elements from corresponding alkoxides, here we report synthesis and characterization of the title compound, (I).

This molecule lie across crystallographic inversion centre and the assymetric unit therefore contains one-half of a molecule. The 8-hydroxy-2-methylquinolinate anion chelates to Ti in the triethanolate derivative; however, the coordination number is raised to six as two of the four ethanolate groups are bridging (Table 1) (Fig. 1).

Related literature top

For Ti^IV–8-hydroxyquinolinates, see: Amini et al. (2004); Birdet et al. (1973); Studd & Swallow (1968). For a related structure, see: Fazaeli et al. (2008).

Experimental top

Manipulations were carried out under nitrogen, using standard Schlenk techniques. Titanium^IV tetraethoxide was prepared from titanium^IV tetrapropoxide (Fluka) and dry ethanol by the alkoxide exchange method and it was puried by vacuum distillation. 8-Hydroxyquinoline (1.6 g, 10 mmol) was added to the reagent (2.28 g, 10 mmol) in toluene (10 ml). The mixture was stirred for a day and the solvent then removed under reduced pressure to furnish a yellow solid. The solid was crystallized from a dichloromethane n-hexane mixture to give yellow prisms of (I).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. Atoms with the suffix a are generated by (2–x, 2–y, –z).

Di-µ-ethanolato-bis[diethanolato(2-methylquinolin-8-olato)titanium(IV)] top

Crystal data top

[Ti₂(C₁₀H₈NO)₂(C₂H₅O)₆]	F(000) = 720
M_r = 682.51	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1633 reflections
a = 9.0497 (18) Å	θ = 2.1–29.2°
b = 13.086 (3) Å	µ = 0.53 mm⁻¹
c = 14.189 (3) Å	T = 120 K
β = 95.21 (3)°	Prism, yellow
V = 1673.4 (6) Å³	0.45 × 0.28 × 0.23 mm
Z = 2

Data collection top

Stoe IPDS II diffractometer	4503 independent reflections
Radiation source: fine-focus sealed tube	3540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 2.1°
rotation method scans	h = −12→12
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	k = −17→17
T_min = 0.686, T_max = 0.905	l = −19→15
12962 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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.1579P)² + 0.3709P] where P = (F_o² + 2F_c²)/3
4503 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 1.26 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

[Ti₂(C₁₀H₈NO)₂(C₂H₅O)₆]	V = 1673.4 (6) Å³
M_r = 682.51	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0497 (18) Å	µ = 0.53 mm⁻¹
b = 13.086 (3) Å	T = 120 K
c = 14.189 (3) Å	0.45 × 0.28 × 0.23 mm
β = 95.21 (3)°

Data collection top

Stoe IPDS II diffractometer	4503 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	3540 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.905	R_int = 0.099
12962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.097	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.14	Δρ_max = 1.26 e Å⁻³
4503 reflections	Δρ_min = −1.14 e Å⁻³
203 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
C1	0.7281 (4)	0.8994 (3)	−0.1775 (3)	0.0353 (7)
H1A	0.6738	0.9058	−0.1227	0.053*
H1B	0.6598	0.8914	−0.2329	0.053*
H1C	0.7869	0.9596	−0.1839	0.053*
C2	0.8274 (3)	0.8079 (3)	−0.1667 (2)	0.0306 (7)
C3	0.8266 (4)	0.7345 (3)	−0.2396 (3)	0.0354 (7)
H3	0.7650	0.7436	−0.2950	0.042*
C4	0.9155 (4)	0.6503 (3)	−0.2294 (3)	0.0349 (7)
H4	0.9165	0.6032	−0.2784	0.042*
C5	1.0064 (4)	0.6351 (3)	−0.1439 (2)	0.0310 (6)
C6	1.0989 (4)	0.5492 (3)	−0.1246 (3)	0.0356 (7)
H6	1.1049	0.4985	−0.1700	0.043*
C7	1.1805 (4)	0.5410 (3)	−0.0376 (3)	0.0380 (8)
H7	1.2414	0.4844	−0.0252	0.046*
C8	1.1734 (4)	0.6166 (3)	0.0329 (3)	0.0349 (7)
H8	1.2298	0.6094	0.0907	0.042*
C9	1.0831 (4)	0.7011 (3)	0.0164 (2)	0.0305 (7)
C10	0.9996 (3)	0.7110 (3)	−0.0735 (2)	0.0284 (6)
C11	0.6511 (5)	0.7812 (4)	0.0572 (4)	0.0516 (11)
H11A	0.6560	0.7490	−0.0040	0.062*
H11B	0.5557	0.8149	0.0573	0.062*
C12	0.6658 (9)	0.7025 (4)	0.1327 (6)	0.081 (2)
H12A	0.7618	0.6710	0.1340	0.122*
H12B	0.5903	0.6515	0.1202	0.122*
H12C	0.6549	0.7340	0.1928	0.122*
C13	0.9606 (5)	0.8822 (4)	0.2620 (3)	0.0431 (9)
H13A	0.9889	0.8109	0.2585	0.052*
H13B	0.8540	0.8853	0.2650	0.052*
C14	1.0373 (5)	0.9294 (4)	0.3496 (3)	0.0512 (11)
H14A	1.1427	0.9274	0.3462	0.077*
H14B	1.0125	0.8918	0.4042	0.077*
H14C	1.0057	0.9990	0.3547	0.077*
C15	1.2662 (4)	0.9251 (3)	−0.0154 (3)	0.0347 (7)
H15A	1.2825	0.8655	0.0249	0.042*
H15B	1.3421	0.9750	0.0042	0.042*
C16	1.2818 (4)	0.8944 (3)	−0.1167 (3)	0.0444 (9)
H16A	1.2054	0.8464	−0.1371	0.067*
H16B	1.3772	0.8636	−0.1210	0.067*
H16C	1.2728	0.9539	−0.1565	0.067*
N1	0.9147 (3)	0.7980 (2)	−0.0847 (2)	0.0284 (6)
O1	1.0681 (3)	0.7744 (2)	0.07988 (17)	0.0338 (5)
O2	0.7640 (3)	0.8529 (2)	0.07192 (19)	0.0356 (6)
O3	0.9989 (3)	0.9345 (2)	0.17872 (19)	0.0364 (6)
O4	1.1230 (2)	0.96763 (19)	−0.00251 (17)	0.0302 (5)
Ti1	0.94929 (6)	0.89765 (5)	0.05650 (4)	0.0280 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0283 (15)	0.0410 (18)	0.0341 (17)	0.0002 (13)	−0.0110 (13)	0.0000 (13)
C2	0.0241 (13)	0.0379 (16)	0.0286 (15)	−0.0053 (12)	−0.0048 (11)	0.0032 (12)
C3	0.0296 (15)	0.0430 (18)	0.0320 (17)	−0.0047 (13)	−0.0059 (12)	0.0010 (14)
C4	0.0361 (16)	0.0386 (18)	0.0288 (16)	−0.0035 (14)	−0.0032 (13)	−0.0046 (13)
C5	0.0260 (13)	0.0359 (16)	0.0312 (16)	−0.0044 (12)	0.0024 (11)	0.0014 (13)
C6	0.0354 (16)	0.0327 (16)	0.0387 (18)	0.0010 (13)	0.0034 (14)	−0.0022 (14)
C7	0.0332 (16)	0.0360 (17)	0.044 (2)	0.0052 (14)	0.0013 (14)	0.0007 (15)
C8	0.0311 (15)	0.0390 (18)	0.0331 (17)	0.0036 (13)	−0.0055 (13)	0.0010 (13)
C9	0.0254 (13)	0.0358 (17)	0.0293 (16)	−0.0001 (12)	−0.0031 (11)	0.0016 (12)
C10	0.0237 (13)	0.0350 (16)	0.0258 (14)	−0.0027 (12)	−0.0007 (11)	−0.0008 (12)
C11	0.0382 (19)	0.061 (3)	0.056 (3)	−0.0186 (19)	0.0044 (18)	−0.009 (2)
C12	0.112 (5)	0.039 (3)	0.101 (5)	−0.006 (3)	0.055 (4)	0.002 (3)
C13	0.0396 (18)	0.060 (2)	0.0292 (17)	−0.0043 (17)	0.0005 (14)	0.0001 (16)
C14	0.045 (2)	0.076 (3)	0.0309 (19)	0.013 (2)	−0.0030 (16)	−0.0061 (19)
C15	0.0218 (13)	0.0404 (18)	0.0420 (19)	0.0031 (12)	0.0028 (12)	−0.0011 (14)
C16	0.0322 (17)	0.056 (2)	0.046 (2)	−0.0024 (16)	0.0101 (16)	−0.0103 (18)
N1	0.0224 (11)	0.0346 (14)	0.0269 (13)	−0.0025 (10)	−0.0045 (10)	0.0011 (10)
O1	0.0329 (11)	0.0380 (13)	0.0287 (12)	0.0023 (10)	−0.0073 (9)	−0.0014 (9)
O2	0.0270 (11)	0.0408 (14)	0.0385 (13)	−0.0043 (10)	0.0009 (9)	−0.0014 (10)
O3	0.0329 (12)	0.0463 (15)	0.0295 (12)	−0.0052 (10)	0.0000 (9)	−0.0013 (10)
O4	0.0217 (9)	0.0372 (12)	0.0313 (12)	0.0014 (9)	0.0008 (8)	−0.0026 (9)
Ti1	0.0224 (3)	0.0344 (4)	0.0264 (3)	−0.0008 (2)	−0.0020 (2)	−0.0018 (2)

Geometric parameters (Å, º) top

C1—C2	1.496 (5)	C12—H12A	0.9600
C1—H1A	0.9600	C12—H12B	0.9600
C1—H1B	0.9600	C12—H12C	0.9600
C1—H1C	0.9600	C13—O3	1.435 (5)
C2—N1	1.352 (4)	C13—C14	1.501 (6)
C2—C3	1.411 (5)	C13—H13A	0.9700
C3—C4	1.364 (5)	C13—H13B	0.9700
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.417 (5)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.414 (5)	C15—O4	1.438 (4)
C5—C10	1.414 (5)	C15—C16	1.512 (6)
C6—C7	1.384 (5)	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C7—C8	1.412 (5)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—C9	1.383 (5)	C16—H16C	0.9600
C8—H8	0.9300	Ti1—N1	2.387 (3)
C9—O1	1.331 (4)	Ti1—O1	1.950 (3)
C9—C10	1.428 (4)	Ti1—O2	1.808 (3)
C10—N1	1.375 (4)	Ti1—O3	1.817 (3)
C11—O2	1.389 (5)	Ti1—O4ⁱ	2.008 (3)
C11—C12	1.483 (9)	Ti1—O4	2.061 (2)
C11—H11A	0.9700	Ti1—Ti1ⁱ	3.2948 (13)
C11—H11B	0.9700

C2—C1—H1A	109.5	C14—C13—H13A	109.4
C2—C1—H1B	109.5	O3—C13—H13B	109.4
H1A—C1—H1B	109.5	C14—C13—H13B	109.4
C2—C1—H1C	109.5	H13A—C13—H13B	108.0
H1A—C1—H1C	109.5	C13—C14—H14A	109.5
H1B—C1—H1C	109.5	C13—C14—H14B	109.5
N1—C2—C3	121.9 (3)	H14A—C14—H14B	109.5
N1—C2—C1	117.6 (3)	C13—C14—H14C	109.5
C3—C2—C1	120.4 (3)	H14A—C14—H14C	109.5
C4—C3—C2	120.6 (3)	H14B—C14—H14C	109.5
C4—C3—H3	119.7	O4—C15—C16	112.8 (3)
C2—C3—H3	119.7	O4—C15—H15A	109.0
C3—C4—C5	119.6 (3)	C16—C15—H15A	109.0
C3—C4—H4	120.2	O4—C15—H15B	109.0
C5—C4—H4	120.2	C16—C15—H15B	109.0
C6—C5—C10	119.0 (3)	H15A—C15—H15B	107.8
C6—C5—C4	124.4 (3)	C15—C16—H16A	109.5
C10—C5—C4	116.6 (3)	C15—C16—H16B	109.5
C7—C6—C5	119.5 (3)	H16A—C16—H16B	109.5
C7—C6—H6	120.2	C15—C16—H16C	109.5
C5—C6—H6	120.2	H16A—C16—H16C	109.5
C6—C7—C8	121.5 (3)	H16B—C16—H16C	109.5
C6—C7—H7	119.2	C2—N1—C10	117.1 (3)
C8—C7—H7	119.2	C2—N1—Ti1	133.8 (2)
C9—C8—C7	120.3 (3)	C10—N1—Ti1	109.0 (2)
C9—C8—H8	119.9	C9—O1—Ti1	124.7 (2)
C7—C8—H8	119.9	C11—O2—Ti1	151.4 (3)
O1—C9—C8	123.8 (3)	C13—O3—Ti1	127.0 (2)
O1—C9—C10	117.4 (3)	C15—O4—Ti1ⁱ	123.9 (2)
C8—C9—C10	118.7 (3)	C15—O4—Ti1	127.5 (2)
N1—C10—C5	124.0 (3)	Ti1ⁱ—O4—Ti1	108.13 (10)
N1—C10—C9	115.0 (3)	O2—Ti1—O3	97.01 (12)
C5—C10—C9	120.9 (3)	O2—Ti1—O1	102.40 (12)
O2—C11—C12	110.1 (5)	O3—Ti1—O1	88.43 (12)
O2—C11—H11A	109.6	O2—Ti1—O4ⁱ	93.27 (11)
C12—C11—H11A	109.6	O3—Ti1—O4ⁱ	100.06 (12)
O2—C11—H11B	109.6	O1—Ti1—O4ⁱ	161.18 (11)
C12—C11—H11B	109.6	O2—Ti1—O4	160.52 (12)
H11A—C11—H11B	108.2	O3—Ti1—O4	97.94 (11)
C11—C12—H12A	109.5	O1—Ti1—O4	90.44 (10)
C11—C12—H12B	109.5	O4ⁱ—Ti1—O4	71.87 (10)
H12A—C12—H12B	109.5	O2—Ti1—N1	82.66 (11)
C11—C12—H12C	109.5	O3—Ti1—N1	161.53 (12)
H12A—C12—H12C	109.5	O1—Ti1—N1	73.70 (10)
H12B—C12—H12C	109.5	O4ⁱ—Ti1—N1	98.39 (10)
O3—C13—C14	111.0 (4)	O4—Ti1—N1	87.05 (10)
O3—C13—H13A	109.4

N1—C2—C3—C4	−0.2 (5)	C11—O2—Ti1—N1	27.3 (6)
C1—C2—C3—C4	−179.1 (3)	C11—O2—Ti1—Ti1ⁱ	115.5 (6)
C2—C3—C4—C5	1.7 (5)	C13—O3—Ti1—O2	38.1 (3)
C3—C4—C5—C6	177.8 (3)	C13—O3—Ti1—O1	−64.2 (3)
C3—C4—C5—C10	−0.7 (5)	C13—O3—Ti1—O4ⁱ	132.7 (3)
C10—C5—C6—C7	0.1 (5)	C13—O3—Ti1—O4	−154.4 (3)
C4—C5—C6—C7	−178.5 (4)	C13—O3—Ti1—N1	−49.7 (5)
C5—C6—C7—C8	0.2 (6)	C13—O3—Ti1—Ti1ⁱ	169.8 (3)
C6—C7—C8—C9	0.3 (6)	C9—O1—Ti1—O2	81.3 (3)
C7—C8—C9—O1	178.5 (3)	C9—O1—Ti1—O3	178.2 (3)
C7—C8—C9—C10	−1.0 (5)	C9—O1—Ti1—O4ⁱ	−64.3 (4)
C6—C5—C10—N1	179.4 (3)	C9—O1—Ti1—O4	−83.9 (3)
C4—C5—C10—N1	−1.9 (5)	C9—O1—Ti1—N1	2.9 (2)
C6—C5—C10—C9	−0.8 (5)	C9—O1—Ti1—Ti1ⁱ	−79.3 (3)
C4—C5—C10—C9	177.9 (3)	C15—O4—Ti1—O2	−130.7 (4)
O1—C9—C10—N1	1.5 (4)	Ti1ⁱ—O4—Ti1—O2	41.8 (4)
C8—C9—C10—N1	−178.9 (3)	C15—O4—Ti1—O3	89.5 (3)
O1—C9—C10—C5	−178.3 (3)	Ti1ⁱ—O4—Ti1—O3	−98.04 (13)
C8—C9—C10—C5	1.3 (5)	C15—O4—Ti1—O1	1.0 (3)
C3—C2—N1—C10	−2.3 (5)	Ti1ⁱ—O4—Ti1—O1	173.48 (12)
C1—C2—N1—C10	176.6 (3)	C15—O4—Ti1—O4ⁱ	−172.5 (3)
C3—C2—N1—Ti1	−178.5 (2)	Ti1ⁱ—O4—Ti1—O4ⁱ	0.0
C1—C2—N1—Ti1	0.5 (5)	C15—O4—Ti1—N1	−72.7 (3)
C5—C10—N1—C2	3.4 (5)	Ti1ⁱ—O4—Ti1—N1	99.83 (12)
C9—C10—N1—C2	−176.4 (3)	C15—O4—Ti1—Ti1ⁱ	−172.5 (3)
C5—C10—N1—Ti1	−179.5 (3)	C2—N1—Ti1—O2	69.3 (3)
C9—C10—N1—Ti1	0.7 (3)	C10—N1—Ti1—O2	−107.0 (2)
C8—C9—O1—Ti1	176.8 (3)	C2—N1—Ti1—O3	159.5 (3)
C10—C9—O1—Ti1	−3.6 (4)	C10—N1—Ti1—O3	−16.8 (4)
C12—C11—O2—Ti1	88.3 (7)	C2—N1—Ti1—O1	174.6 (3)
C14—C13—O3—Ti1	173.2 (3)	C10—N1—Ti1—O1	−1.8 (2)
C16—C15—O4—Ti1ⁱ	−67.7 (4)	C2—N1—Ti1—O4ⁱ	−22.9 (3)
C16—C15—O4—Ti1	103.7 (3)	C10—N1—Ti1—O4ⁱ	160.7 (2)
C11—O2—Ti1—O3	−134.1 (6)	C2—N1—Ti1—O4	−94.1 (3)
C11—O2—Ti1—O1	−44.2 (6)	C10—N1—Ti1—O4	89.6 (2)
C11—O2—Ti1—O4ⁱ	125.3 (6)	C2—N1—Ti1—Ti1ⁱ	−59.2 (3)
C11—O2—Ti1—O4	85.9 (7)	C10—N1—Ti1—Ti1ⁱ	124.4 (2)

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1	0.97	2.46	3.061 (5)	120
C1—H1C···O3ⁱ	0.96	2.38	3.292 (5)	159
C3—H3···O1ⁱⁱ	0.93	2.41	3.310 (5)	163

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ti₂(C₁₀H₈NO)₂(C₂H₅O)₆]
M_r	682.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	9.0497 (18), 13.086 (3), 14.189 (3)
β (°)	95.21 (3)
V (Å³)	1673.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.45 × 0.28 × 0.23

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.686, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	12962, 4503, 3540
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.097, 0.197, 1.14
No. of reflections	4503
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.26, −1.14

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Ti1—N1	2.387 (3)	Ti1—O3	1.817 (3)
Ti1—O1	1.950 (3)	Ti1—O4ⁱ	2.008 (3)
Ti1—O2	1.808 (3)	Ti1—O4	2.061 (2)

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1	0.97	2.46	3.061 (5)	120
C1—H1C···O3ⁱ	0.96	2.38	3.292 (5)	159
C3—H3···O1ⁱⁱ	0.93	2.41	3.310 (5)	163

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x−1/2, −y+3/2, z−1/2.

Acknowledgements

We are grateful to Shahid Beheshti University for financial support.

References

Amini, M. M., Mirzaee, M. & Ng, S. W. (2004). Acta Cryst. E60, m145–m146. Web of Science CSD CrossRef IUCr Journals Google Scholar
Birdet, P. H., Fraser, A. R. & Lau, C. F. (1973). Inorg. Chem. 12, 1322–1328. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fazaeli, Y., Amini, M. M., Gao, S. & Ng, S. W. (2008). Acta Cryst. E64, o97. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar
Studd, B. F. & Swallow, A. G. (1968). J. Chem. Soc. A, pp. 1961–1967. CSD CrossRef Google Scholar