Bis(5-chloro­quinolin-8-olato-κ2N,O)bis­(propan-2-olato-κO)titanium(IV)

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

doi:10.1107/S1600536809004383

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m271

doi:10.1107/S1600536809004383

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Bis(5-chloroquinolin-8-olato-κ²N,O)bis(propan-2-olato-κO)titanium(IV)

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

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 February 2009; accepted 6 February 2009; online 13 February 2009)

The Ti^IV atom in the title compound, [Ti(C₉H₅ClNO)₂(C₃H₇O)₂], is chelated by the substituted quinolin-8-olate anions in a distorted octahedral geometry. The N-donor atoms are in a cis alignment as are the O atoms of the propan-2-olate groups; the O atoms of the quinolin-8-olate groups are trans to each other. One C atom of one propan-2-olate group is disordered over two positions with occupancies of 0.733 (8):0.267 (8).

Related literature

For diisoproxidobis(quinolin-8-olato)titanium(IV), see: Zeng et al. (2002 ). For diisopropoxidobis(2-methylquinolin-8-olato)titanium(IV), see: Fazaeli et al. (2008 ).

Experimental

Crystal data

[Ti(C₉H₅ClNO)₂(C₃H₇O)₂]
M_r = 523.25
Triclinic, $[P \overline 1]$
a = 8.2170 (2) Å
b = 12.1847 (3) Å
c = 13.8113 (3) Å
α = 109.555 (1)°
β = 105.090 (1)°
γ = 103.785 (1)°
V = 1174.89 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 100 (2) K
0.40 × 0.08 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.788, T_max = 0.952
9665 measured reflections
5285 independent reflections
4126 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.04
5285 reflections
308 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004383/bt2867sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004383/bt2867Isup2.hkl

checkCIF report

Related literature top

For diisoproxidobis(quinolin-8-olato)titanium, see: Zeng et al. (2002). For diisopropoxidobis(2-methylquinolin-8-olato)titanium, see: Fazaeli et al. (2008).

Experimental top

5-Chloro-8-hydroxyquinoline (1.79 g, 10 mmol) was added to titanium isoproxide (2.84 g, 10 mmol) in toluene (20 ml).The mixture was stirred for a day and the solvent then removed under reduced pressure to furnish a deep yellow solid. The solid was crystallized from a dichloromethane/n-hexane to give yellow crystals, m.p. 439 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Ti(C₃H₇O)₂(C₉H₅ClNO)₂(C₃H₇O)₂; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius. Only the major occupied site of the disordered atom is shown.

Bis(5-chloroquinolin-8-olato-κ²N,O)bis(propan-2-olato- κO)titanium(IV) top

Crystal data top

[Ti(C₉H₅ClNO)₂(C₃H₇O)₂]	Z = 2
M_r = 523.25	F(000) = 540
Triclinic, P1	D_x = 1.479 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2170 (2) Å	Cell parameters from 2883 reflections
b = 12.1847 (3) Å	θ = 2.6–28.1°
c = 13.8113 (3) Å	µ = 0.63 mm⁻¹
α = 109.555 (1)°	T = 100 K
β = 105.090 (1)°	Prism, yellow
γ = 103.785 (1)°	0.40 × 0.08 × 0.08 mm
V = 1174.89 (5) Å³

Data collection top

Bruker SMART APEX diffractometer	5285 independent reflections
Radiation source: fine-focus sealed tube	4126 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.788, T_max = 0.952	k = −15→15
9665 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0434P)² + 0.5978P] where P = (F_o² + 2F_c²)/3
5285 reflections	(Δ/σ)_max = 0.001
308 parameters	Δρ_max = 0.35 e Å⁻³
18 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Ti(C₉H₅ClNO)₂(C₃H₇O)₂]	γ = 103.785 (1)°
M_r = 523.25	V = 1174.89 (5) Å³
Triclinic, P1	Z = 2
a = 8.2170 (2) Å	Mo Kα radiation
b = 12.1847 (3) Å	µ = 0.63 mm⁻¹
c = 13.8113 (3) Å	T = 100 K
α = 109.555 (1)°	0.40 × 0.08 × 0.08 mm
β = 105.090 (1)°

Data collection top

Bruker SMART APEX diffractometer	5285 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4126 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.952	R_int = 0.024
9665 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	18 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
5285 reflections	Δρ_min = −0.32 e Å⁻³
308 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ti1	0.36699 (5)	0.46368 (4)	0.21132 (3)	0.02005 (11)
Cl1	−0.42848 (9)	0.06005 (6)	0.18350 (5)	0.03744 (17)
Cl2	0.23370 (8)	1.01980 (5)	0.47176 (5)	0.02848 (15)
O1	0.3245 (2)	0.35579 (15)	0.28814 (13)	0.0251 (4)
O2	0.3248 (2)	0.59246 (14)	0.16226 (12)	0.0222 (3)
O3	0.6063 (2)	0.52223 (15)	0.27602 (14)	0.0283 (4)
O4	0.3252 (2)	0.34879 (15)	0.07709 (13)	0.0257 (4)
N1	0.0664 (2)	0.40036 (17)	0.17023 (15)	0.0199 (4)
N2	0.3560 (2)	0.60873 (17)	0.35960 (15)	0.0196 (4)
C1	0.1581 (3)	0.2891 (2)	0.27005 (18)	0.0217 (5)
C2	0.1141 (3)	0.1993 (2)	0.30843 (19)	0.0260 (5)
H2	0.2072	0.1836	0.3529	0.031*
C3	−0.0671 (4)	0.1311 (2)	0.28229 (19)	0.0286 (5)
H3	−0.0945	0.0692	0.3089	0.034*
C4	−0.2052 (3)	0.1516 (2)	0.21957 (19)	0.0259 (5)
C5	−0.1694 (3)	0.2452 (2)	0.18031 (18)	0.0218 (5)
C6	0.0136 (3)	0.3111 (2)	0.20600 (18)	0.0197 (4)
C7	−0.2991 (3)	0.2793 (2)	0.11910 (19)	0.0259 (5)
H7	−0.4240	0.2386	0.1009	0.031*
C8	−0.2436 (3)	0.3709 (2)	0.08642 (19)	0.0260 (5)
H8	−0.3296	0.3954	0.0465	0.031*
C9	−0.0594 (3)	0.4286 (2)	0.11196 (19)	0.0233 (5)
H9	−0.0231	0.4904	0.0865	0.028*
C10	0.3085 (3)	0.6930 (2)	0.22925 (18)	0.0191 (4)
C11	0.2780 (3)	0.7874 (2)	0.20186 (19)	0.0240 (5)
H11	0.2710	0.7842	0.1311	0.029*
C12	0.2573 (3)	0.8885 (2)	0.2785 (2)	0.0238 (5)
H12	0.2338	0.9518	0.2578	0.029*
C13	0.2702 (3)	0.8977 (2)	0.38176 (19)	0.0213 (5)
C14	0.3095 (3)	0.8066 (2)	0.41672 (18)	0.0191 (4)
C15	0.3243 (3)	0.7044 (2)	0.33780 (18)	0.0179 (4)
C16	0.3405 (3)	0.8113 (2)	0.52348 (18)	0.0223 (5)
H16	0.3349	0.8796	0.5798	0.027*
C17	0.3787 (3)	0.7167 (2)	0.54536 (19)	0.0229 (5)
H17	0.4029	0.7196	0.6175	0.027*
C18	0.3819 (3)	0.6154 (2)	0.46011 (18)	0.0217 (5)
H18	0.4036	0.5487	0.4754	0.026*
C19	0.7545 (4)	0.6058 (3)	0.3799 (3)	0.0259 (11)	0.733 (8)
H19	0.7047	0.6190	0.4400	0.031*	0.733 (8)
C19'	0.7943 (8)	0.5966 (6)	0.3237 (6)	0.017 (2)	0.267 (8)
H19'	0.8420	0.5836	0.2628	0.020*	0.267 (8)
C20	0.8248 (4)	0.7275 (2)	0.3771 (3)	0.0434 (7)
H20A	0.7250	0.7564	0.3565	0.065*	0.733 (8)
H20B	0.8825	0.7187	0.3225	0.065*	0.733 (8)
H20C	0.9135	0.7882	0.4503	0.065*	0.733 (8)
H20D	0.7137	0.7423	0.3483	0.065*	0.267 (8)
H20E	0.9214	0.7755	0.3621	0.065*	0.267 (8)
H20F	0.8600	0.7537	0.4571	0.065*	0.267 (8)
C21	0.8883 (3)	0.5458 (2)	0.4018 (2)	0.0340 (6)
H21A	0.9928	0.6047	0.4691	0.051*	0.733 (8)
H21B	0.9275	0.5215	0.3390	0.051*	0.733 (8)
H21C	0.8333	0.4716	0.4116	0.051*	0.733 (8)
H21D	0.9897	0.6148	0.4651	0.051*	0.267 (8)
H21E	0.9331	0.4846	0.3617	0.051*	0.267 (8)
H21F	0.8019	0.5060	0.4280	0.051*	0.267 (8)
C22	0.1934 (3)	0.2575 (2)	−0.0269 (2)	0.0297 (5)
H22	0.0879	0.2846	−0.0447	0.036*
C23	0.1300 (4)	0.1341 (2)	−0.0203 (2)	0.0415 (7)
H23A	0.0799	0.1439	0.0379	0.062*
H23B	0.2322	0.1064	−0.0029	0.062*
H23C	0.0368	0.0718	−0.0915	0.062*
C24	0.2717 (4)	0.2478 (3)	−0.1150 (2)	0.0473 (8)
H24A	0.3114	0.3294	−0.1168	0.071*
H24B	0.1797	0.1868	−0.1871	0.071*
H24C	0.3750	0.2210	−0.0987	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ti1	0.0143 (2)	0.0191 (2)	0.0242 (2)	0.00694 (16)	0.00535 (16)	0.00694 (17)
Cl1	0.0332 (4)	0.0336 (4)	0.0379 (4)	−0.0009 (3)	0.0177 (3)	0.0117 (3)
Cl2	0.0310 (3)	0.0203 (3)	0.0383 (3)	0.0130 (2)	0.0161 (3)	0.0121 (3)
O1	0.0194 (8)	0.0224 (8)	0.0315 (9)	0.0097 (7)	0.0038 (7)	0.0118 (7)
O2	0.0233 (8)	0.0226 (8)	0.0226 (8)	0.0087 (7)	0.0102 (7)	0.0100 (7)
O3	0.0164 (8)	0.0224 (9)	0.0354 (10)	0.0067 (7)	0.0038 (7)	0.0045 (7)
O4	0.0188 (8)	0.0233 (8)	0.0267 (8)	0.0074 (7)	0.0057 (7)	0.0033 (7)
N1	0.0181 (10)	0.0209 (10)	0.0229 (9)	0.0088 (8)	0.0078 (8)	0.0103 (8)
N2	0.0147 (9)	0.0205 (10)	0.0244 (10)	0.0069 (8)	0.0063 (8)	0.0107 (8)
C1	0.0251 (12)	0.0156 (11)	0.0212 (11)	0.0084 (9)	0.0077 (9)	0.0042 (9)
C2	0.0327 (14)	0.0216 (12)	0.0229 (12)	0.0118 (10)	0.0072 (10)	0.0093 (10)
C3	0.0412 (15)	0.0214 (12)	0.0250 (12)	0.0093 (11)	0.0147 (11)	0.0115 (10)
C4	0.0284 (13)	0.0206 (12)	0.0238 (12)	0.0027 (10)	0.0133 (10)	0.0053 (10)
C5	0.0238 (12)	0.0210 (11)	0.0207 (11)	0.0080 (10)	0.0114 (9)	0.0064 (9)
C6	0.0209 (11)	0.0176 (11)	0.0197 (11)	0.0080 (9)	0.0076 (9)	0.0062 (9)
C7	0.0165 (11)	0.0302 (13)	0.0251 (12)	0.0066 (10)	0.0076 (10)	0.0062 (10)
C8	0.0199 (12)	0.0335 (13)	0.0262 (12)	0.0124 (10)	0.0079 (10)	0.0130 (11)
C9	0.0210 (12)	0.0270 (12)	0.0257 (12)	0.0103 (10)	0.0086 (10)	0.0145 (10)
C10	0.0140 (10)	0.0195 (11)	0.0234 (11)	0.0039 (9)	0.0071 (9)	0.0100 (9)
C11	0.0216 (12)	0.0262 (12)	0.0266 (12)	0.0065 (10)	0.0088 (10)	0.0154 (10)
C12	0.0206 (12)	0.0228 (12)	0.0330 (13)	0.0089 (10)	0.0094 (10)	0.0171 (10)
C13	0.0174 (11)	0.0169 (11)	0.0284 (12)	0.0059 (9)	0.0087 (9)	0.0081 (9)
C14	0.0134 (10)	0.0181 (11)	0.0247 (11)	0.0049 (9)	0.0061 (9)	0.0088 (9)
C15	0.0137 (10)	0.0190 (11)	0.0228 (11)	0.0050 (9)	0.0068 (9)	0.0114 (9)
C16	0.0199 (11)	0.0212 (11)	0.0231 (11)	0.0060 (9)	0.0076 (9)	0.0074 (9)
C17	0.0200 (11)	0.0283 (12)	0.0224 (11)	0.0071 (10)	0.0084 (9)	0.0139 (10)
C18	0.0186 (11)	0.0244 (12)	0.0252 (12)	0.0092 (9)	0.0066 (9)	0.0143 (10)
C19	0.0175 (17)	0.0293 (18)	0.0232 (19)	0.0073 (14)	0.0032 (14)	0.0064 (14)
C19'	0.013 (4)	0.026 (4)	0.015 (4)	0.006 (3)	0.010 (3)	0.008 (3)
C20	0.0372 (16)	0.0251 (14)	0.0494 (17)	0.0050 (12)	−0.0017 (13)	0.0123 (13)
C21	0.0277 (14)	0.0329 (14)	0.0380 (15)	0.0077 (11)	0.0046 (11)	0.0190 (12)
C22	0.0214 (12)	0.0307 (13)	0.0245 (12)	0.0076 (11)	0.0023 (10)	0.0034 (10)
C23	0.0440 (17)	0.0293 (14)	0.0328 (14)	−0.0005 (12)	0.0151 (13)	0.0006 (12)
C24	0.0478 (18)	0.0468 (18)	0.0278 (14)	0.0001 (14)	0.0102 (13)	0.0080 (13)

Geometric parameters (Å, º) top

Ti1—O3	1.7788 (16)	C12—H12	0.9500
Ti1—O4	1.7936 (16)	C13—C14	1.420 (3)
Ti1—O1	1.9707 (16)	C14—C16	1.408 (3)
Ti1—O2	1.9723 (16)	C14—C15	1.410 (3)
Ti1—N2	2.2527 (18)	C16—C17	1.369 (3)
Ti1—N1	2.2554 (18)	C16—H16	0.9500
Cl1—C4	1.742 (2)	C17—C18	1.403 (3)
Cl2—C13	1.738 (2)	C17—H17	0.9500
O1—C1	1.323 (3)	C18—H18	0.9500
O2—C10	1.327 (3)	C19—C20	1.475 (4)
O3—C19'	1.430 (6)	C19—C21	1.481 (4)
O3—C19	1.449 (3)	C19—H19	1.0000
O4—C22	1.421 (3)	C19'—C20	1.441 (7)
N1—C9	1.325 (3)	C19'—C21	1.543 (6)
N1—C6	1.365 (3)	C19'—H19'	1.0000
N2—C18	1.319 (3)	C20—H20A	0.9800
N2—C15	1.362 (3)	C20—H20B	0.9800
C1—C2	1.381 (3)	C20—H20C	0.9800
C1—C6	1.424 (3)	C20—H20D	0.9800
C2—C3	1.402 (4)	C20—H20E	0.9800
C2—H2	0.9500	C20—H20F	0.9800
C3—C4	1.367 (3)	C21—H21A	0.9800
C3—H3	0.9500	C21—H21B	0.9800
C4—C5	1.421 (3)	C21—H21C	0.9800
C5—C6	1.410 (3)	C21—H21D	0.9800
C5—C7	1.414 (3)	C21—H21E	0.9800
C7—C8	1.364 (3)	C21—H21F	0.9800
C7—H7	0.9500	C22—C24	1.503 (4)
C8—C9	1.400 (3)	C22—C23	1.512 (4)
C8—H8	0.9500	C22—H22	1.0000
C9—H9	0.9500	C23—H23A	0.9800
C10—C11	1.381 (3)	C23—H23B	0.9800
C10—C15	1.427 (3)	C23—H23C	0.9800
C11—C12	1.410 (3)	C24—H24A	0.9800
C11—H11	0.9500	C24—H24B	0.9800
C12—C13	1.366 (3)	C24—H24C	0.9800

O3—Ti1—O4	103.15 (7)	O3—C19—H19	107.6
O3—Ti1—O1	95.29 (7)	C20—C19—H19	107.6
O4—Ti1—O1	100.15 (7)	C21—C19—H19	107.6
O3—Ti1—O2	101.90 (7)	O3—C19'—C20	111.7 (5)
O4—Ti1—O2	96.17 (7)	O3—C19'—C21	107.1 (4)
O1—Ti1—O2	152.90 (7)	C20—C19'—C21	113.8 (5)
O3—Ti1—N2	89.20 (7)	O3—C19'—H19'	108.0
O4—Ti1—N2	166.55 (7)	C20—C19'—H19'	108.0
O1—Ti1—N2	83.74 (7)	C21—C19'—H19'	108.0
O2—Ti1—N2	75.79 (6)	C19'—C20—C19	36.0 (3)
O3—Ti1—N1	166.54 (7)	C19'—C20—H20A	118.7
O4—Ti1—N1	88.50 (7)	C19—C20—H20A	109.5
O1—Ti1—N1	75.78 (6)	C19'—C20—H20B	73.8
O2—Ti1—N1	83.22 (7)	C19—C20—H20B	109.5
N2—Ti1—N1	79.93 (7)	H20A—C20—H20B	109.5
C1—O1—Ti1	120.40 (14)	C19'—C20—H20C	127.4
C10—O2—Ti1	120.95 (13)	C19—C20—H20C	109.5
C19'—O3—C19	36.5 (3)	H20A—C20—H20C	109.5
C19'—O3—Ti1	165.3 (3)	H20B—C20—H20C	109.5
C19—O3—Ti1	142.82 (19)	C19'—C20—H20D	109.5
C22—O4—Ti1	146.48 (15)	C19—C20—H20D	102.1
C9—N1—C6	118.54 (19)	H20A—C20—H20D	9.2
C9—N1—Ti1	130.57 (15)	H20B—C20—H20D	107.9
C6—N1—Ti1	110.63 (14)	H20C—C20—H20D	118.0
C18—N2—C15	118.38 (19)	C19'—C20—H20E	109.5
C18—N2—Ti1	130.30 (15)	C19—C20—H20E	141.0
C15—N2—Ti1	111.26 (14)	H20A—C20—H20E	104.6
O1—C1—C2	124.8 (2)	H20B—C20—H20E	39.1
O1—C1—C6	117.6 (2)	H20C—C20—H20E	75.3
C2—C1—C6	117.6 (2)	H20D—C20—H20E	109.5
C1—C2—C3	120.5 (2)	C19'—C20—H20F	109.5
C1—C2—H2	119.8	C19—C20—H20F	79.8
C3—C2—H2	119.8	H20A—C20—H20F	104.7
C4—C3—C2	121.7 (2)	H20B—C20—H20F	138.4
C4—C3—H3	119.2	H20C—C20—H20F	34.5
C2—C3—H3	119.2	H20D—C20—H20F	109.5
C3—C4—C5	120.7 (2)	H20E—C20—H20F	109.5
C3—C4—Cl1	120.28 (19)	C19—C21—C19'	34.6 (3)
C5—C4—Cl1	118.97 (19)	C19—C21—H21A	109.5
C6—C5—C7	117.1 (2)	C19'—C21—H21A	118.5
C6—C5—C4	116.6 (2)	C19—C21—H21B	109.5
C7—C5—C4	126.4 (2)	C19'—C21—H21B	75.1
N1—C6—C5	122.5 (2)	H21A—C21—H21B	109.5
N1—C6—C1	114.56 (19)	C19—C21—H21C	109.5
C5—C6—C1	122.9 (2)	C19'—C21—H21C	127.0
C8—C7—C5	119.6 (2)	H21A—C21—H21C	109.5
C8—C7—H7	120.2	H21B—C21—H21C	109.5
C5—C7—H7	120.2	C19—C21—H21D	102.1
C7—C8—C9	119.8 (2)	C19'—C21—H21D	109.5
C7—C8—H8	120.1	H21A—C21—H21D	9.1
C9—C8—H8	120.1	H21B—C21—H21D	108.2
N1—C9—C8	122.5 (2)	H21C—C21—H21D	117.7
N1—C9—H9	118.8	C19—C21—H21E	140.1
C8—C9—H9	118.8	C19'—C21—H21E	109.5
O2—C10—C11	124.9 (2)	H21A—C21—H21E	104.7
O2—C10—C15	117.33 (19)	H21B—C21—H21E	37.6
C11—C10—C15	117.7 (2)	H21C—C21—H21E	76.7
C10—C11—C12	120.2 (2)	H21D—C21—H21E	109.5
C10—C11—H11	119.9	C19—C21—H21F	81.1
C12—C11—H11	119.9	C19'—C21—H21F	109.5
C13—C12—C11	121.6 (2)	H21A—C21—H21F	104.8
C13—C12—H12	119.2	H21B—C21—H21F	137.4
C11—C12—H12	119.2	H21C—C21—H21F	33.1
C12—C13—C14	120.9 (2)	H21D—C21—H21F	109.5
C12—C13—Cl2	120.29 (17)	H21E—C21—H21F	109.5
C14—C13—Cl2	118.76 (17)	O4—C22—C24	109.4 (2)
C16—C14—C15	117.36 (19)	O4—C22—C23	109.6 (2)
C16—C14—C13	126.0 (2)	C24—C22—C23	111.8 (2)
C15—C14—C13	116.59 (19)	O4—C22—H22	108.7
N2—C15—C14	122.49 (19)	C24—C22—H22	108.7
N2—C15—C10	114.65 (19)	C23—C22—H22	108.7
C14—C15—C10	122.86 (19)	C22—C23—H23A	109.5
C17—C16—C14	119.4 (2)	C22—C23—H23B	109.5
C17—C16—H16	120.3	H23A—C23—H23B	109.5
C14—C16—H16	120.3	C22—C23—H23C	109.5
C16—C17—C18	119.3 (2)	H23A—C23—H23C	109.5
C16—C17—H17	120.4	H23B—C23—H23C	109.5
C18—C17—H17	120.4	C22—C24—H24A	109.5
N2—C18—C17	122.9 (2)	C22—C24—H24B	109.5
N2—C18—H18	118.5	H24A—C24—H24B	109.5
C17—C18—H18	118.5	C22—C24—H24C	109.5
O3—C19—C20	108.7 (3)	H24A—C24—H24C	109.5
O3—C19—C21	109.4 (2)	H24B—C24—H24C	109.5
C20—C19—C21	115.5 (3)

O3—Ti1—O1—C1	178.69 (16)	C4—C5—C6—N1	177.79 (19)
O4—Ti1—O1—C1	−76.91 (16)	C7—C5—C6—C1	177.9 (2)
O2—Ti1—O1—C1	49.2 (2)	C4—C5—C6—C1	−1.5 (3)
N2—Ti1—O1—C1	90.08 (16)	O1—C1—C6—N1	0.1 (3)
N1—Ti1—O1—C1	8.91 (15)	C2—C1—C6—N1	−179.7 (2)
O3—Ti1—O2—C10	−86.92 (16)	O1—C1—C6—C5	179.4 (2)
O4—Ti1—O2—C10	168.21 (15)	C2—C1—C6—C5	−0.4 (3)
O1—Ti1—O2—C10	41.3 (2)	C6—C5—C7—C8	1.1 (3)
N2—Ti1—O2—C10	−0.82 (15)	C4—C5—C7—C8	−179.5 (2)
N1—Ti1—O2—C10	80.46 (16)	C5—C7—C8—C9	1.2 (3)
O4—Ti1—O3—C19'	107.6 (14)	C6—N1—C9—C8	0.4 (3)
O1—Ti1—O3—C19'	−150.7 (14)	Ti1—N1—C9—C8	173.98 (17)
O2—Ti1—O3—C19'	8.3 (14)	C7—C8—C9—N1	−2.0 (4)
N2—Ti1—O3—C19'	−67.0 (14)	Ti1—O2—C10—C11	−179.65 (17)
N1—Ti1—O3—C19'	−103.0 (15)	Ti1—O2—C10—C15	0.5 (3)
O4—Ti1—O3—C19	−174.9 (3)	O2—C10—C11—C12	178.0 (2)
O1—Ti1—O3—C19	−73.2 (3)	C15—C10—C11—C12	−2.2 (3)
O2—Ti1—O3—C19	85.8 (3)	C10—C11—C12—C13	1.3 (3)
N2—Ti1—O3—C19	10.5 (3)	C11—C12—C13—C14	1.5 (3)
N1—Ti1—O3—C19	−25.5 (5)	C11—C12—C13—Cl2	−177.04 (17)
O3—Ti1—O4—C22	179.3 (3)	C12—C13—C14—C16	174.5 (2)
O1—Ti1—O4—C22	81.4 (3)	Cl2—C13—C14—C16	−6.9 (3)
O2—Ti1—O4—C22	−76.9 (3)	C12—C13—C14—C15	−3.3 (3)
N2—Ti1—O4—C22	−24.4 (5)	Cl2—C13—C14—C15	175.28 (16)
N1—Ti1—O4—C22	6.1 (3)	C18—N2—C15—C14	−3.2 (3)
O3—Ti1—N1—C9	128.4 (3)	Ti1—N2—C15—C14	179.36 (16)
O4—Ti1—N1—C9	−81.3 (2)	C18—N2—C15—C10	176.46 (19)
O1—Ti1—N1—C9	177.9 (2)	Ti1—N2—C15—C10	−1.0 (2)
O2—Ti1—N1—C9	15.1 (2)	C16—C14—C15—N2	4.1 (3)
N2—Ti1—N1—C9	91.8 (2)	C13—C14—C15—N2	−177.96 (19)
O3—Ti1—N1—C6	−57.6 (4)	C16—C14—C15—C10	−175.5 (2)
O4—Ti1—N1—C6	92.72 (15)	C13—C14—C15—C10	2.4 (3)
O1—Ti1—N1—C6	−8.15 (14)	O2—C10—C15—N2	0.4 (3)
O2—Ti1—N1—C6	−170.88 (15)	C11—C10—C15—N2	−179.40 (19)
N2—Ti1—N1—C6	−94.18 (14)	O2—C10—C15—C14	−179.95 (19)
O3—Ti1—N2—C18	−73.6 (2)	C11—C10—C15—C14	0.2 (3)
O4—Ti1—N2—C18	129.5 (3)	C15—C14—C16—C17	−1.6 (3)
O1—Ti1—N2—C18	21.80 (19)	C13—C14—C16—C17	−179.3 (2)
O2—Ti1—N2—C18	−176.1 (2)	C14—C16—C17—C18	−1.5 (3)
N1—Ti1—N2—C18	98.4 (2)	C15—N2—C18—C17	−0.2 (3)
O3—Ti1—N2—C15	103.48 (15)	Ti1—N2—C18—C17	176.69 (16)
O4—Ti1—N2—C15	−53.4 (4)	C16—C17—C18—N2	2.6 (3)
O1—Ti1—N2—C15	−161.11 (15)	C19'—O3—C19—C20	59.8 (5)
O2—Ti1—N2—C15	0.99 (14)	Ti1—O3—C19—C20	−95.6 (4)
N1—Ti1—N2—C15	−84.50 (14)	C19'—O3—C19—C21	−67.2 (5)
Ti1—O1—C1—C2	171.39 (17)	Ti1—O3—C19—C21	137.4 (2)
Ti1—O1—C1—C6	−8.4 (3)	C19—O3—C19'—C20	−64.4 (6)
O1—C1—C2—C3	−178.3 (2)	Ti1—O3—C19'—C20	32.8 (18)
C6—C1—C2—C3	1.5 (3)	C19—O3—C19'—C21	60.8 (5)
C1—C2—C3—C4	−0.7 (4)	Ti1—O3—C19'—C21	158.0 (10)
C2—C3—C4—C5	−1.3 (4)	O3—C19'—C20—C19	63.7 (5)
C2—C3—C4—Cl1	177.01 (18)	C21—C19'—C20—C19	−57.7 (5)
C3—C4—C5—C6	2.3 (3)	O3—C19—C20—C19'	−60.2 (5)
Cl1—C4—C5—C6	−176.04 (16)	C21—C19—C20—C19'	63.2 (5)
C3—C4—C5—C7	−177.1 (2)	O3—C19—C21—C19'	63.4 (5)
Cl1—C4—C5—C7	4.6 (3)	C20—C19—C21—C19'	−59.6 (5)
C9—N1—C6—C5	2.1 (3)	O3—C19'—C21—C19	−63.4 (5)
Ti1—N1—C6—C5	−172.73 (16)	C20—C19'—C21—C19	60.5 (5)
C9—N1—C6—C1	−178.61 (19)	Ti1—O4—C22—C24	150.1 (2)
Ti1—N1—C6—C1	6.6 (2)	Ti1—O4—C22—C23	−87.0 (3)
C7—C5—C6—N1	−2.8 (3)

Experimental details

Crystal data
Chemical formula	[Ti(C₉H₅ClNO)₂(C₃H₇O)₂]
M_r	523.25
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.2170 (2), 12.1847 (3), 13.8113 (3)
α, β, γ (°)	109.555 (1), 105.090 (1), 103.785 (1)
V (Å³)	1174.89 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.40 × 0.08 × 0.08

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.788, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	9665, 5285, 4126
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.04
No. of reflections	5285
No. of parameters	308
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

The authors thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fazaeli, Y., Amini, M. M. & Ng, S. W. (2008). Acta Cryst. E64, m1509. Web of Science CSD CrossRef IUCr Journals 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. (2009). 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