Bis(isopropoxido-κO)bis­(2-methyl­quinolin-8-olato-κ2N,O)titanium(IV)

Fazaeli, Y.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536808035460

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1509

doi:10.1107/S1600536808035460

Open

access

Bis(isopropoxido-κO)bis(2-methylquinolin-8-olato-κ²N,O)titanium(IV)

Yousef Fazaeli,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Shahid Beheshti University, Tehran, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 October 2008; accepted 29 October 2008; online 8 November 2008)

The two 2-methylquinolin-8-olate anions in the title complex, [Ti(C₁₀H₈NO)₂(C₃H₇O)₂], chelate the Ti^IV atom, which shows an all-cis distorted octahedral N₂O₄ coordination geometry.

Related literature

For the synthesis, see: Bickley & Nick (1979 ); Harrod & Taylor (1975 ). For the crystal structure of bis(isopropoxy)bis(quinolin-8-olato)titanium, see: Zeng et al. (2002 ).

Experimental

Crystal data

[Ti(C₁₀H₈NO)₂(C₃H₇O)₂]
M_r = 482.42
Monoclinic, P 2₁ /c
a = 9.5851 (2) Å
b = 13.5768 (2) Å
c = 18.7779 (3) Å
β = 102.559 (1)°
V = 2385.19 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 100 (2) K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.875, T_max = 0.943
16391 measured reflections
5467 independent reflections
4651 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.03
5467 reflections
304 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035460/tk2320sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035460/tk2320Isup2.hkl

checkCIF report

Related literature top

For the synthesis, see: Bickley & Nick (1979); Harrod & Taylor (1975). For the crystal structure of bis(isopropoxy)bis(quinolin-8-olato)titanium, see: Zeng et al. (2002).

Experimental top

8-Hydroxy-2-methylquinoline (1.59 g, 10 mmol) was added to the titanium isopropoxide (2.84 g, 10 mmol) in toluene (20 ml) at room temperature. The mixture was stirred for a day and than solvent was removed under reduced pressure to furnish an orange solid. The solid was crystallized from dichloromethane and n-hexane (1:1) to give yellow crystals, m.p. 445 K. IR (KBr, cm^-1): 1575 (C═C, C═N), 1236 (C—O). ¹H NMR (CDCl₃, p.p.m.): 0.94 (CH₃, doublet), 1.14 (CH₃, doublet), 2.83 (CH₃, singlet), 4.61 (CH, quartet), 6.9–8.58 (aromatic H atoms).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ti(C₁₀H₈NO)₂(C₃H₇O)₂ at the 70% probability level showing atom labelling. Hydrogen atoms are drawn as spheres of arbitrary radius.

Bis(isopropoxido-κO)bis(2-methylquinolin-8-olato- κ²N,O)titanium(IV) top

Crystal data top

[Ti(C₁₀H₈NO)₂(C₃H₇O)₂]	F(000) = 1016
M_r = 482.42	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6457 reflections
a = 9.5851 (2) Å	θ = 2.2–28.3°
b = 13.5768 (2) Å	µ = 0.39 mm⁻¹
c = 18.7779 (3) Å	T = 100 K
β = 102.559 (1)°	Irregular chip, yellow
V = 2385.19 (7) Å³	0.35 × 0.25 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5467 independent reflections
Radiation source: fine-focus sealed tube	4651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.875, T_max = 0.943	k = −17→17
16391 measured reflections	l = −24→24

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0394P)² + 1.3426P] where P = (F_o² + 2F_c²)/3
5467 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ti(C₁₀H₈NO)₂(C₃H₇O)₂]	V = 2385.19 (7) Å³
M_r = 482.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5851 (2) Å	µ = 0.39 mm⁻¹
b = 13.5768 (2) Å	T = 100 K
c = 18.7779 (3) Å	0.35 × 0.25 × 0.15 mm
β = 102.559 (1)°

Data collection top

Bruker SMART APEX diffractometer	5467 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4651 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.943	R_int = 0.025
16391 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
5467 reflections	Δρ_min = −0.39 e Å⁻³
304 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Ti1	0.36712 (3)	0.433571 (18)	0.241664 (14)	0.01288 (8)
O1	0.26537 (11)	0.55637 (7)	0.23824 (6)	0.0166 (2)
O2	0.46090 (11)	0.31617 (7)	0.28355 (5)	0.0153 (2)
O3	0.49414 (11)	0.48288 (8)	0.19514 (6)	0.0187 (2)
O4	0.24248 (11)	0.37144 (8)	0.16802 (5)	0.0171 (2)
N1	0.19366 (13)	0.41035 (9)	0.31601 (6)	0.0142 (2)
N2	0.51257 (13)	0.48222 (9)	0.35581 (6)	0.0145 (2)
C1	0.16171 (16)	0.57482 (11)	0.27306 (8)	0.0169 (3)
C2	0.09311 (17)	0.66473 (12)	0.27024 (9)	0.0219 (3)
H2	0.1206	0.7172	0.2427	0.026*
C3	−0.01715 (18)	0.67913 (12)	0.30789 (9)	0.0261 (4)
H3	−0.0628	0.7415	0.3055	0.031*
C4	−0.05984 (17)	0.60535 (13)	0.34771 (9)	0.0259 (4)
H4	−0.1351	0.6164	0.3724	0.031*
C5	0.00847 (16)	0.51221 (12)	0.35212 (8)	0.0204 (3)
C6	0.12004 (15)	0.49752 (11)	0.31484 (8)	0.0155 (3)
C7	−0.02862 (17)	0.43106 (13)	0.39098 (9)	0.0244 (3)
H7	−0.1022	0.4370	0.4174	0.029*
C8	0.04179 (17)	0.34421 (13)	0.39039 (9)	0.0228 (3)
H8	0.0155	0.2890	0.4157	0.027*
C9	0.15426 (16)	0.33490 (11)	0.35243 (8)	0.0170 (3)
C10	0.22910 (17)	0.23783 (11)	0.35446 (9)	0.0210 (3)
H10A	0.2668	0.2303	0.3102	0.032*
H10B	0.1615	0.1845	0.3570	0.032*
H10C	0.3081	0.2352	0.3975	0.032*
C11	0.54608 (15)	0.31020 (11)	0.34980 (8)	0.0151 (3)
C12	0.60985 (17)	0.22382 (12)	0.37911 (8)	0.0197 (3)
H12	0.5961	0.1647	0.3514	0.024*
C13	0.69565 (17)	0.22374 (12)	0.45060 (9)	0.0226 (3)
H13	0.7381	0.1638	0.4706	0.027*
C14	0.71930 (17)	0.30763 (12)	0.49184 (9)	0.0215 (3)
H14	0.7760	0.3054	0.5401	0.026*
C15	0.65868 (16)	0.39776 (12)	0.46212 (8)	0.0170 (3)
C16	0.57156 (15)	0.39851 (11)	0.39100 (8)	0.0145 (3)
C17	0.68312 (16)	0.49006 (12)	0.49736 (8)	0.0199 (3)
H17	0.7367	0.4940	0.5462	0.024*
C18	0.62969 (17)	0.57309 (11)	0.46108 (8)	0.0197 (3)
H18	0.6493	0.6353	0.4842	0.024*
C19	0.54487 (16)	0.56820 (11)	0.38889 (8)	0.0171 (3)
C20	0.49429 (18)	0.66222 (11)	0.35024 (9)	0.0235 (3)
H20A	0.4595	0.6491	0.2981	0.035*
H20B	0.5736	0.7093	0.3570	0.035*
H20C	0.4166	0.6899	0.3704	0.035*
C21	0.63093 (17)	0.48966 (12)	0.17852 (9)	0.0199 (3)
H21	0.6754	0.5535	0.1980	0.024*
C22	0.6130 (2)	0.48986 (15)	0.09632 (9)	0.0321 (4)
H22A	0.5505	0.5445	0.0754	0.048*
H22B	0.5703	0.4274	0.0764	0.048*
H22C	0.7066	0.4978	0.0840	0.048*
C23	0.72535 (18)	0.40664 (13)	0.21459 (10)	0.0274 (4)
H23A	0.7328	0.4091	0.2674	0.041*
H23B	0.8207	0.4135	0.2042	0.041*
H23C	0.6838	0.3434	0.1956	0.041*
C24	0.17566 (17)	0.41249 (11)	0.09929 (8)	0.0181 (3)
H24	0.2249	0.4755	0.0922	0.022*
C25	0.1915 (2)	0.34129 (13)	0.03960 (9)	0.0308 (4)
H25A	0.2932	0.3306	0.0411	0.046*
H25B	0.1451	0.3687	−0.0079	0.046*
H25C	0.1464	0.2784	0.0470	0.046*
C26	0.02027 (18)	0.43437 (14)	0.09889 (10)	0.0279 (4)
H26A	0.0150	0.4809	0.1381	0.042*
H26B	−0.0286	0.3731	0.1065	0.042*
H26C	−0.0259	0.4632	0.0518	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ti1	0.01437 (14)	0.01316 (13)	0.01128 (13)	0.00042 (10)	0.00319 (9)	0.00035 (9)
O1	0.0175 (5)	0.0147 (5)	0.0178 (5)	0.0012 (4)	0.0042 (4)	0.0013 (4)
O2	0.0170 (5)	0.0156 (5)	0.0125 (5)	0.0015 (4)	0.0016 (4)	−0.0008 (4)
O3	0.0177 (5)	0.0219 (5)	0.0178 (5)	0.0005 (4)	0.0068 (4)	0.0032 (4)
O4	0.0201 (5)	0.0170 (5)	0.0130 (5)	−0.0005 (4)	0.0013 (4)	0.0005 (4)
N1	0.0133 (6)	0.0169 (6)	0.0119 (6)	−0.0007 (5)	0.0017 (5)	−0.0018 (4)
N2	0.0132 (6)	0.0164 (6)	0.0144 (6)	−0.0013 (5)	0.0041 (5)	0.0001 (5)
C1	0.0155 (7)	0.0176 (7)	0.0158 (7)	−0.0004 (6)	−0.0006 (5)	−0.0037 (5)
C2	0.0216 (8)	0.0172 (7)	0.0240 (8)	0.0025 (6)	−0.0016 (6)	−0.0030 (6)
C3	0.0224 (8)	0.0231 (8)	0.0296 (9)	0.0087 (7)	−0.0013 (7)	−0.0095 (7)
C4	0.0170 (8)	0.0343 (9)	0.0262 (8)	0.0060 (7)	0.0039 (6)	−0.0099 (7)
C5	0.0136 (7)	0.0289 (8)	0.0177 (7)	0.0009 (6)	0.0011 (6)	−0.0054 (6)
C6	0.0131 (7)	0.0185 (7)	0.0133 (7)	0.0000 (6)	−0.0005 (5)	−0.0034 (5)
C7	0.0162 (8)	0.0388 (10)	0.0197 (8)	−0.0011 (7)	0.0071 (6)	−0.0023 (7)
C8	0.0192 (8)	0.0305 (9)	0.0189 (8)	−0.0048 (7)	0.0049 (6)	0.0035 (6)
C9	0.0154 (7)	0.0214 (7)	0.0129 (7)	−0.0034 (6)	0.0003 (5)	0.0001 (5)
C10	0.0216 (8)	0.0205 (8)	0.0214 (8)	−0.0019 (6)	0.0056 (6)	0.0045 (6)
C11	0.0128 (7)	0.0189 (7)	0.0139 (7)	0.0002 (5)	0.0034 (5)	0.0007 (5)
C12	0.0196 (8)	0.0188 (7)	0.0205 (8)	0.0022 (6)	0.0042 (6)	0.0016 (6)
C13	0.0208 (8)	0.0237 (8)	0.0223 (8)	0.0055 (6)	0.0025 (6)	0.0077 (6)
C14	0.0173 (8)	0.0296 (8)	0.0164 (7)	0.0009 (6)	0.0010 (6)	0.0047 (6)
C15	0.0136 (7)	0.0240 (8)	0.0140 (7)	−0.0016 (6)	0.0042 (6)	0.0013 (6)
C16	0.0122 (7)	0.0182 (7)	0.0141 (7)	−0.0002 (5)	0.0049 (5)	0.0014 (5)
C17	0.0152 (7)	0.0301 (8)	0.0142 (7)	−0.0047 (6)	0.0030 (6)	−0.0032 (6)
C18	0.0183 (8)	0.0221 (8)	0.0191 (7)	−0.0062 (6)	0.0052 (6)	−0.0061 (6)
C19	0.0151 (7)	0.0188 (7)	0.0182 (7)	−0.0037 (6)	0.0057 (6)	−0.0018 (6)
C20	0.0278 (9)	0.0167 (7)	0.0238 (8)	−0.0025 (6)	0.0009 (7)	−0.0008 (6)
C21	0.0189 (8)	0.0216 (8)	0.0210 (8)	−0.0041 (6)	0.0081 (6)	−0.0003 (6)
C22	0.0325 (10)	0.0447 (11)	0.0233 (9)	0.0086 (8)	0.0156 (7)	0.0071 (8)
C23	0.0180 (8)	0.0340 (9)	0.0305 (9)	0.0017 (7)	0.0059 (7)	0.0053 (7)
C24	0.0218 (8)	0.0189 (7)	0.0130 (7)	0.0004 (6)	0.0024 (6)	0.0019 (5)
C25	0.0447 (11)	0.0302 (9)	0.0160 (8)	0.0091 (8)	0.0031 (7)	−0.0011 (7)
C26	0.0225 (9)	0.0362 (10)	0.0245 (8)	0.0057 (7)	0.0037 (7)	0.0071 (7)

Geometric parameters (Å, º) top

Ti1—O3	1.7766 (11)	C12—C13	1.414 (2)
Ti1—O4	1.8255 (10)	C12—H12	0.9500
Ti1—O2	1.9130 (10)	C13—C14	1.368 (2)
Ti1—O1	1.9255 (10)	C13—H13	0.9500
Ti1—N2	2.3822 (12)	C14—C15	1.416 (2)
Ti1—N1	2.4130 (12)	C14—H14	0.9500
O1—C1	1.3266 (18)	C15—C16	1.413 (2)
O2—C11	1.3338 (17)	C15—C17	1.413 (2)
O3—C21	1.4153 (18)	C17—C18	1.359 (2)
O4—C24	1.4239 (17)	C17—H17	0.9500
N1—C9	1.3311 (19)	C18—C19	1.422 (2)
N1—C6	1.3756 (19)	C18—H18	0.9500
N2—C19	1.3270 (19)	C19—C20	1.496 (2)
N2—C16	1.3731 (19)	C20—H20A	0.9800
C1—C2	1.382 (2)	C20—H20B	0.9800
C1—C6	1.419 (2)	C20—H20C	0.9800
C2—C3	1.407 (2)	C21—C23	1.511 (2)
C2—H2	0.9500	C21—C22	1.515 (2)
C3—C4	1.365 (3)	C21—H21	1.0000
C3—H3	0.9500	C22—H22A	0.9800
C4—C5	1.418 (2)	C22—H22B	0.9800
C4—H4	0.9500	C22—H22C	0.9800
C5—C7	1.409 (2)	C23—H23A	0.9800
C5—C6	1.414 (2)	C23—H23B	0.9800
C7—C8	1.360 (2)	C23—H23C	0.9800
C7—H7	0.9500	C24—C25	1.512 (2)
C8—C9	1.421 (2)	C24—C26	1.517 (2)
C8—H8	0.9500	C24—H24	1.0000
C9—C10	1.497 (2)	C25—H25A	0.9800
C10—H10A	0.9800	C25—H25B	0.9800
C10—H10B	0.9800	C25—H25C	0.9800
C10—H10C	0.9800	C26—H26A	0.9800
C11—C12	1.380 (2)	C26—H26B	0.9800
C11—C16	1.419 (2)	C26—H26C	0.9800

O3—Ti1—O4	101.96 (5)	C14—C13—C12	121.83 (15)
O3—Ti1—O2	101.84 (5)	C14—C13—H13	119.1
O4—Ti1—O2	95.62 (4)	C12—C13—H13	119.1
O3—Ti1—O1	93.07 (5)	C13—C14—C15	119.54 (14)
O4—Ti1—O1	97.56 (5)	C13—C14—H14	120.2
O2—Ti1—O1	157.58 (4)	C15—C14—H14	120.2
O3—Ti1—N2	90.48 (5)	C16—C15—C17	116.11 (14)
O4—Ti1—N2	165.52 (4)	C16—C15—C14	119.09 (14)
O2—Ti1—N2	74.36 (4)	C17—C15—C14	124.74 (14)
O1—Ti1—N2	89.03 (4)	N2—C16—C15	123.90 (14)
O3—Ti1—N1	164.98 (5)	N2—C16—C11	115.65 (13)
O4—Ti1—N1	87.60 (4)	C15—C16—C11	120.37 (14)
O2—Ti1—N1	88.54 (4)	C18—C17—C15	119.67 (14)
O1—Ti1—N1	74.02 (4)	C18—C17—H17	120.2
N2—Ti1—N1	81.82 (4)	C15—C17—H17	120.2
C1—O1—Ti1	125.12 (9)	C17—C18—C19	120.95 (14)
C11—O2—Ti1	124.87 (9)	C17—C18—H18	119.5
C21—O3—Ti1	154.13 (10)	C19—C18—H18	119.5
C24—O4—Ti1	126.66 (9)	N2—C19—C18	120.93 (14)
C9—N1—C6	117.94 (13)	N2—C19—C20	120.36 (14)
C9—N1—Ti1	134.90 (10)	C18—C19—C20	118.70 (13)
C6—N1—Ti1	107.09 (9)	C19—C20—H20A	109.5
C19—N2—C16	118.24 (13)	C19—C20—H20B	109.5
C19—N2—Ti1	134.14 (10)	H20A—C20—H20B	109.5
C16—N2—Ti1	107.62 (9)	C19—C20—H20C	109.5
O1—C1—C2	123.29 (14)	H20A—C20—H20C	109.5
O1—C1—C6	117.65 (13)	H20B—C20—H20C	109.5
C2—C1—C6	119.06 (14)	O3—C21—C23	110.24 (12)
C1—C2—C3	120.43 (15)	O3—C21—C22	108.63 (13)
C1—C2—H2	119.8	C23—C21—C22	112.47 (14)
C3—C2—H2	119.8	O3—C21—H21	108.5
C4—C3—C2	121.38 (15)	C23—C21—H21	108.5
C4—C3—H3	119.3	C22—C21—H21	108.5
C2—C3—H3	119.3	C21—C22—H22A	109.5
C3—C4—C5	119.79 (15)	C21—C22—H22B	109.5
C3—C4—H4	120.1	H22A—C22—H22B	109.5
C5—C4—H4	120.1	C21—C22—H22C	109.5
C7—C5—C6	116.69 (14)	H22A—C22—H22C	109.5
C7—C5—C4	124.21 (15)	H22B—C22—H22C	109.5
C6—C5—C4	119.09 (15)	C21—C23—H23A	109.5
N1—C6—C5	123.64 (14)	C21—C23—H23B	109.5
N1—C6—C1	116.11 (13)	H23A—C23—H23B	109.5
C5—C6—C1	120.24 (14)	C21—C23—H23C	109.5
C8—C7—C5	119.49 (15)	H23A—C23—H23C	109.5
C8—C7—H7	120.3	H23B—C23—H23C	109.5
C5—C7—H7	120.3	O4—C24—C25	108.89 (12)
C7—C8—C9	120.86 (15)	O4—C24—C26	109.19 (12)
C7—C8—H8	119.6	C25—C24—C26	112.20 (14)
C9—C8—H8	119.6	O4—C24—H24	108.8
N1—C9—C8	121.34 (14)	C25—C24—H24	108.8
N1—C9—C10	120.18 (13)	C26—C24—H24	108.8
C8—C9—C10	118.48 (13)	C24—C25—H25A	109.5
C9—C10—H10A	109.5	C24—C25—H25B	109.5
C9—C10—H10B	109.5	H25A—C25—H25B	109.5
H10A—C10—H10B	109.5	C24—C25—H25C	109.5
C9—C10—H10C	109.5	H25A—C25—H25C	109.5
H10A—C10—H10C	109.5	H25B—C25—H25C	109.5
H10B—C10—H10C	109.5	C24—C26—H26A	109.5
O2—C11—C12	123.48 (13)	C24—C26—H26B	109.5
O2—C11—C16	117.07 (13)	H26A—C26—H26B	109.5
C12—C11—C16	119.45 (13)	C24—C26—H26C	109.5
C11—C12—C13	119.68 (15)	H26A—C26—H26C	109.5
C11—C12—H12	120.2	H26B—C26—H26C	109.5
C13—C12—H12	120.2

O3—Ti1—O1—C1	−171.18 (11)	Ti1—N1—C6—C1	−0.15 (14)
O4—Ti1—O1—C1	86.32 (11)	C7—C5—C6—N1	−1.2 (2)
O2—Ti1—O1—C1	−39.19 (19)	C4—C5—C6—N1	179.55 (14)
N2—Ti1—O1—C1	−80.75 (11)	C7—C5—C6—C1	178.57 (14)
N1—Ti1—O1—C1	1.02 (11)	C4—C5—C6—C1	−0.6 (2)
O3—Ti1—O2—C11	91.30 (11)	O1—C1—C6—N1	0.93 (19)
O4—Ti1—O2—C11	−165.20 (11)	C2—C1—C6—N1	−179.29 (13)
O1—Ti1—O2—C11	−39.37 (18)	O1—C1—C6—C5	−178.89 (13)
N2—Ti1—O2—C11	4.16 (10)	C2—C1—C6—C5	0.9 (2)
N1—Ti1—O2—C11	−77.75 (11)	C6—C5—C7—C8	−0.6 (2)
O4—Ti1—O3—C21	−112.2 (2)	C4—C5—C7—C8	178.58 (15)
O2—Ti1—O3—C21	−13.8 (2)	C5—C7—C8—C9	1.4 (2)
O1—Ti1—O3—C21	149.4 (2)	C6—N1—C9—C8	−1.4 (2)
N2—Ti1—O3—C21	60.3 (2)	Ti1—N1—C9—C8	−177.92 (10)
N1—Ti1—O3—C21	119.1 (2)	C6—N1—C9—C10	178.99 (13)
O3—Ti1—O4—C24	−50.83 (12)	Ti1—N1—C9—C10	2.4 (2)
O2—Ti1—O4—C24	−154.22 (11)	C7—C8—C9—N1	−0.4 (2)
O1—Ti1—O4—C24	43.96 (12)	C7—C8—C9—C10	179.26 (15)
N2—Ti1—O4—C24	160.41 (16)	Ti1—O2—C11—C12	178.57 (11)
N1—Ti1—O4—C24	117.49 (11)	Ti1—O2—C11—C16	−1.88 (18)
O3—Ti1—N1—C9	−152.04 (17)	O2—C11—C12—C13	−178.34 (14)
O4—Ti1—N1—C9	77.85 (14)	C16—C11—C12—C13	2.1 (2)
O2—Ti1—N1—C9	−17.84 (14)	C11—C12—C13—C14	−0.8 (2)
O1—Ti1—N1—C9	176.41 (14)	C12—C13—C14—C15	−1.1 (2)
N2—Ti1—N1—C9	−92.25 (14)	C13—C14—C15—C16	1.7 (2)
O3—Ti1—N1—C6	31.1 (2)	C13—C14—C15—C17	−175.58 (15)
O4—Ti1—N1—C6	−98.96 (9)	C19—N2—C16—C15	3.5 (2)
O2—Ti1—N1—C6	165.34 (9)	Ti1—N2—C16—C15	−176.65 (11)
O1—Ti1—N1—C6	−0.40 (9)	C19—N2—C16—C11	−173.27 (13)
N2—Ti1—N1—C6	90.94 (9)	Ti1—N2—C16—C11	6.53 (14)
O3—Ti1—N2—C19	71.95 (14)	C17—C15—C16—N2	0.4 (2)
O4—Ti1—N2—C19	−138.53 (18)	C14—C15—C16—N2	−177.12 (13)
O2—Ti1—N2—C19	174.12 (14)	C17—C15—C16—C11	177.10 (13)
O1—Ti1—N2—C19	−21.11 (14)	C14—C15—C16—C11	−0.4 (2)
N1—Ti1—N2—C19	−95.11 (14)	O2—C11—C16—N2	−4.13 (19)
O3—Ti1—N2—C16	−107.81 (9)	C12—C11—C16—N2	175.45 (13)
O4—Ti1—N2—C16	41.7 (2)	O2—C11—C16—C15	178.93 (12)
O2—Ti1—N2—C16	−5.64 (9)	C12—C11—C16—C15	−1.5 (2)
O1—Ti1—N2—C16	159.13 (9)	C16—C15—C17—C18	−3.3 (2)
N1—Ti1—N2—C16	85.13 (9)	C14—C15—C17—C18	174.09 (15)
Ti1—O1—C1—C2	178.74 (11)	C15—C17—C18—C19	2.3 (2)
Ti1—O1—C1—C6	−1.49 (18)	C16—N2—C19—C18	−4.6 (2)
O1—C1—C2—C3	179.34 (14)	Ti1—N2—C19—C18	175.66 (10)
C6—C1—C2—C3	−0.4 (2)	C16—N2—C19—C20	174.44 (13)
C1—C2—C3—C4	−0.3 (2)	Ti1—N2—C19—C20	−5.3 (2)
C2—C3—C4—C5	0.6 (2)	C17—C18—C19—N2	1.8 (2)
C3—C4—C5—C7	−179.23 (16)	C17—C18—C19—C20	−177.27 (14)
C3—C4—C5—C6	−0.1 (2)	Ti1—O3—C21—C23	8.2 (3)
C9—N1—C6—C5	2.2 (2)	Ti1—O3—C21—C22	131.9 (2)
Ti1—N1—C6—C5	179.66 (12)	Ti1—O4—C24—C25	132.10 (12)
C9—N1—C6—C1	−177.60 (13)	Ti1—O4—C24—C26	−105.08 (14)

Experimental details

Crystal data
Chemical formula	[Ti(C₁₀H₈NO)₂(C₃H₇O)₂]
M_r	482.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5851 (2), 13.5768 (2), 18.7779 (3)
β (°)	102.559 (1)
V (Å³)	2385.19 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.875, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	16391, 5467, 4651
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.03
No. of reflections	5467
No. of parameters	304
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

The authors thank the Vice-President's Office for Research Affairs of Shahid Beheshti University and the University of Malaya for supporting this work.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bickley, D. G. & Nick, S. (1979). Inorg. Chem. 18, 2200–2204. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Harrod, J. F. & Taylor, K. R. (1975). Inorg. Chem. 14, 1541–1545. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
Zeng, W. F., Chen, Y. S., Chiang, M. Y., Chern, S. S. & Cheng, C. P. (2002). Polyhedron, 21, 1081–1087. Web of Science CSD CrossRef CAS Google Scholar