Di-μ-ethano-lato-bis-[diethano-lato(2-methyl-quinolin-8-olato)titanium(IV)].

In the centrosymmetric dinuclear title compound, [Ti(2)(C(10)H(8)NO)(2)(C(2)H(5)O)(6)], the Ti atom is bonded to an N,O-bidentate quinolin-8-olate ligand, two terminal ethano-late anions and two bridging ethano-late anions in a distorted TiNO(5) octa-hedral geometry. An intra-molecular C-H⋯O hydrogen bond occurs; in the crystal, inter-molecular C-H⋯O inter-actions help to establish the packing.

Related literature

For TiIV–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 = 682.51

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.097

wR(F 2) = 0.197

S = 1.14

4503 reflections

203 parameters

H-atom parameters constrained

Δρmax = 1.26 e Å−3

Δρmin = −1.14 e Å−3

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 ▶).

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

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

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

[Ti2(C10H8NO)2(C2H5O)6]	F(000) = 720
Mr = 682.51	Dx = 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

Stoe IPDS II diffractometer	4503 independent reflections
Radiation source: fine-focus sealed tube	3540 reflections with I > 2σ(I)
graphite	Rint = 0.099
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.1°
rotation method scans	h = −12→12
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	k = −17→17
Tmin = 0.686, Tmax = 0.905	l = −19→15
12962 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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.1579P)2 + 0.3709P] where P = (Fo2 + 2Fc2)/3
4503 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 1.26 e Å−3
0 restraints	Δρmin = −1.14 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
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)

	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)

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)

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

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) .

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) ; (ii) .