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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

μ-Oxido-bis­­{bis­­[(penta­fluoro­phen­yl)methano­lato](η5-penta­methyl­cyclo­penta­dien­yl)titanium(IV)}

aDepartment of Chemistry, Chonnam National University, Gwangju 500-757, Republic of Korea, and bDepartment of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Republic of Korea
*Correspondence e-mail: ykim@chungbuk.ac.kr

(Received 21 June 2011; accepted 11 July 2011; online 16 July 2011)

The dinuclear title complex, [Ti2(C10H15)2(C7H2F5O)4O], features two TiIV atoms bridged by an O atom. Each Ti atom is bonded to a η5-penta­methyl­cyclo­penta­dienyl ring, two (penta­fluoro­phen­yl)methano­late anions and to the bridging O atom. The environment around each Ti atom can be considered as a distorted tetra­hedron.

Related literature

For related titanium complexes, Cp*Ti(OCH2C6F5)3 and Cp*Ti(OC6F5)3, see: Lee et al. (2007[Lee, J., Do, Y. & Kim, Y. (2007). J. Organomet. Chem. 692, 3593-3598.]). For other related structures, see: Gowik et al. (1990[Gowik, P., Klaotke, T. & Pickardt, J. (1990). J. Organomet. Chem. 393, 343-348.]); Thewalt & Schomburg (1977[Thewalt, U. & Schomburg, D. (1977). J. Organomet. Chem. 127, 169-174.]). For the use of dinuclear titanium complexes containing a cyclo­penta­dienyl ligand in organometallic catalysis, see: Noh et al. (2006[Noh, S. K., Jung, W., Oh, H., Lee, Y. R. & Lyoo, W. S. (2006). J. Organomet. Chem. 691, 5000-5006.]); Wu et al. (2009[Wu, Q. L., Li, G. H., Ye, L., Gao, W. & Mu, Y. (2009). Polyhedron, 26, 3063-3068.]); Yoon et al. (2011[Yoon, S. W., Kim, Y., Kim, S. K., Kim, S. Y., Do, Y. & Park, S. (2011). Macromol. Chem. Phys. 212, 785-789.]).

[Scheme 1]

Experimental

Crystal data
  • [Ti2(C10H15)2(C7H2F5O)4O]

  • Mr = 1170.58

  • Monoclinic, P 21 /n

  • a = 11.371 (2) Å

  • b = 16.113 (3) Å

  • c = 27.340 (6) Å

  • β = 90.75 (3)°

  • V = 5008.8 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 293 K

  • 0.15 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.94, Tmax = 0.96

  • 28465 measured reflections

  • 11233 independent reflections

  • 5333 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.075

  • wR(F2) = 0.221

  • S = 1.03

  • 11233 reflections

  • 686 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Dinuclear titanium complexes containing a cyclopentadienyl ligand have attracted considerable attention in the fields of organometallic catalysis (Noh et al., 2006; Wu et al., 2009; Yoon et al., 2011). Recently, we have reported the facile synthesis of Cp*Ti(OCH2C6F5)3 and Cp*Ti(OC6F5)3 (Cp* = η5-pentamethylcyclopentadienyl). (Lee et al., 2007) In continuation of our systematic studies on bimetallic pentamethylcyclopentadienyltitanium derivative using previously synthesized Cp*Ti(OCH2C6F5)3, the title complex (I) has been investigated.

The title compound (I) is the main product of the reaction of Cp*Ti(OCH2C6F5)3 with water in dichloromethane solution. In (I) (Fig. 1), the dinuclear structure shows two Ti atoms bridged by an oxygen atom, with approximately C2 symmetry. The Ti—C and Ti—O distances are in the range of 2.345 (5) - 2.400 (5) Å and 1.795 (3) - 1.819 (4) Å, respectively. The Ti—O—Ti angle of 163.1 (2) ° falls within the observed range (154 - 180°) for the previous reported compounds (Wu et al., 2009; Thewalt & Schomburg, 1977; Gowik et al., 1990). The dihedral angle between the pentamethylcyclopentadienyl rings is 38.3 (3) ° . In addition, three of the four dihedral angles between each Cp* ring and the benzene ring of the pentafluorobenzyloxy moieties attached to the same titanium atom are in the expected range, 72.4 (4)-78.0 (3)°.However, the remaining dihedral angle between Cp* ring (C1-C10) and benzene ring (C12-C17) is abnormally low, 5.6 (3)°.

Related literature top

For related titanium complexes, Cp* T i(OCH2C6F5)3 and Cp*Ti(OC6F5)3 , see: Lee et al. (2007). For other related structures, see: Gowik et al. (1990); Thewalt & Schomburg (1977). For the use of dinuclear titanium complexes containing a cyclopentadienyl ligand in organometallic catalysis, see: Noh et al. (2006); Wu et al. (2009); Yoon et al. (2011).

Experimental top

Complex (I) was synthesized by hydrolysis of Cp*Ti(OCH2C6F5)3. Crystals were obtained by slow evaporation, in the refrigerator, using methylene chloride as solvent.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I). Displacement ellipsoids are drawn at the 15% probability level. H atoms are omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of compound (I). H atoms are omitted for clarity.
µ-Oxido-bis{bis[(pentafluorophenyl)methanolato](η5- pentamethylcyclopentadienyl)titanium(IV)} top
Crystal data top
[Ti2(C10H15)2(C7H2F5O)4O]F(000) = 2360
Mr = 1170.58Dx = 1.552 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.371 (2) ÅCell parameters from 11233 reflections
b = 16.113 (3) Åθ = 1.5–28.4°
c = 27.340 (6) ŵ = 0.44 mm1
β = 90.75 (3)°T = 293 K
V = 5008.8 (17) Å3Block, yellow
Z = 40.15 × 0.12 × 0.10 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
11233 independent reflections
Radiation source: fine-focus sealed tube5333 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
profile data from /ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1414
Tmin = 0.94, Tmax = 0.96k = 2018
28465 measured reflectionsl = 3536
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0816P)2 + 3.8803P]
where P = (Fo2 + 2Fc2)/3
11233 reflections(Δ/σ)max = 0.093
686 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
[Ti2(C10H15)2(C7H2F5O)4O]V = 5008.8 (17) Å3
Mr = 1170.58Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.371 (2) ŵ = 0.44 mm1
b = 16.113 (3) ÅT = 293 K
c = 27.340 (6) Å0.15 × 0.12 × 0.10 mm
β = 90.75 (3)°
Data collection top
Bruker SMART 1K CCD
diffractometer
11233 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
5333 reflections with I > 2σ(I)
Tmin = 0.94, Tmax = 0.96Rint = 0.042
28465 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0750 restraints
wR(F2) = 0.221H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
11233 reflectionsΔρmin = 0.37 e Å3
686 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
xyzUiso*/Ueq
Ti10.69905 (7)0.70860 (5)0.55446 (3)0.0610 (2)
O20.8245 (4)0.7653 (2)0.52971 (14)0.1012 (12)
O30.5859 (3)0.78829 (19)0.55607 (12)0.0817 (10)
C10.7536 (6)0.6170 (3)0.48979 (19)0.0849 (15)
C20.7485 (5)0.5714 (3)0.53312 (18)0.0754 (13)
C30.6306 (5)0.5716 (3)0.54909 (18)0.0737 (13)
C40.5607 (5)0.6174 (3)0.5159 (2)0.0789 (14)
C50.6388 (6)0.6466 (3)0.47879 (19)0.0864 (16)
C60.8620 (7)0.6320 (4)0.4601 (2)0.125 (2)
H6A0.87090.58800.43680.187*
H6B0.92970.63370.48140.187*
H6C0.85460.68400.44320.187*
C70.8491 (6)0.5271 (4)0.5581 (2)0.1062 (19)
H7A0.92180.55330.54960.159*
H7B0.85020.47010.54790.159*
H7C0.83930.52970.59290.159*
C80.5845 (6)0.5283 (3)0.5939 (2)0.108 (2)
H8A0.57240.47060.58680.162*
H8B0.51120.55310.60310.162*
H8C0.64050.53380.62030.162*
C90.4290 (5)0.6286 (4)0.5177 (3)0.116 (2)
H9A0.40850.65430.54810.175*
H9B0.39120.57550.51520.175*
H9C0.40360.66320.49100.175*
C100.6041 (7)0.6995 (4)0.4354 (2)0.128 (3)
H10A0.52550.71990.43960.192*
H10B0.60720.66670.40610.192*
H10C0.65730.74540.43290.192*
C110.8684 (5)0.8437 (4)0.54140 (19)0.0925 (17)
H11A0.91060.84150.57240.111*
H11B0.80390.88270.54450.111*
C120.9504 (5)0.8725 (3)0.50152 (17)0.0759 (14)
C130.9147 (6)0.9216 (4)0.4638 (2)0.0933 (16)
C140.9891 (8)0.9446 (4)0.4263 (2)0.106 (2)
C151.1016 (7)0.9178 (4)0.4267 (2)0.0913 (17)
C161.1403 (6)0.8705 (4)0.4621 (2)0.1034 (19)
C171.0658 (6)0.8480 (5)0.4991 (2)0.107 (2)
C180.5031 (5)0.8380 (3)0.5324 (2)0.0943 (18)
H18A0.43860.80400.52040.113*
H18B0.53870.86530.50470.113*
C190.4570 (5)0.9025 (3)0.56781 (18)0.0741 (13)
C200.5065 (5)0.9798 (3)0.57017 (17)0.0717 (13)
C210.4703 (6)1.0389 (3)0.6014 (2)0.0881 (16)
C220.3829 (7)1.0218 (5)0.6323 (2)0.108 (2)
C230.3295 (6)0.9449 (6)0.6332 (3)0.112 (2)
C240.3685 (5)0.8864 (4)0.6001 (2)0.0929 (17)
F10.8044 (4)0.9505 (3)0.46415 (17)0.1629 (18)
F20.9501 (5)0.9957 (4)0.39154 (18)0.204 (2)
F31.1743 (4)0.9407 (3)0.39052 (12)0.1376 (15)
F41.2526 (4)0.8409 (4)0.46138 (18)0.181 (2)
F51.1099 (4)0.7965 (4)0.53375 (18)0.198 (3)
F60.5955 (3)0.9989 (2)0.54001 (12)0.1019 (9)
F70.5204 (4)1.1147 (2)0.60132 (13)0.1307 (13)
F80.3461 (5)1.0802 (3)0.66365 (16)0.174 (2)
F90.2437 (4)0.9261 (4)0.66401 (18)0.179 (2)
F100.3191 (3)0.8103 (3)0.60010 (17)0.1395 (15)
O10.7342 (3)0.69325 (18)0.61865 (9)0.0667 (8)
Ti20.81195 (7)0.68839 (5)0.67745 (3)0.0597 (2)
O40.8194 (4)0.57809 (19)0.69042 (12)0.1022 (13)
O50.9614 (3)0.7123 (2)0.66251 (14)0.0936 (11)
C310.6899 (5)0.7044 (3)0.74743 (17)0.0774 (14)
C320.8021 (5)0.7342 (3)0.76018 (17)0.0824 (15)
C330.8252 (5)0.8052 (3)0.7312 (2)0.0831 (15)
C340.7267 (4)0.8178 (3)0.69964 (16)0.0660 (12)
C350.6423 (4)0.7559 (3)0.71042 (16)0.0694 (12)
C360.6248 (6)0.6332 (4)0.7709 (2)0.119 (2)
H36A0.56410.65470.79130.179*
H36B0.67880.60080.79030.179*
H36C0.59030.59880.74580.179*
C370.8847 (7)0.6981 (4)0.7996 (2)0.134 (3)
H37A0.96440.70110.78860.201*
H37B0.86420.64130.80560.201*
H37C0.87720.72950.82920.201*
C380.9330 (5)0.8588 (4)0.7340 (3)0.122 (2)
H38A0.99960.82570.74350.183*
H38B0.92150.90200.75770.183*
H38C0.94680.88320.70250.183*
C390.7106 (5)0.8856 (3)0.66303 (19)0.0887 (16)
H39A0.65270.92400.67450.133*
H39B0.68480.86230.63240.133*
H39C0.78390.91400.65870.133*
C400.5229 (4)0.7467 (4)0.6860 (2)0.0907 (16)
H40A0.46720.78180.70210.136*
H40B0.49760.69000.68820.136*
H40C0.52790.76240.65230.136*
C410.8105 (7)0.5068 (4)0.7180 (2)0.125 (3)
H41A0.73030.48630.71600.150*
H41B0.82830.51950.75190.150*
C420.8924 (7)0.4408 (3)0.7007 (2)0.0924 (18)
C430.8583 (9)0.3820 (5)0.6683 (3)0.122 (3)
C440.9326 (15)0.3222 (6)0.6522 (4)0.168 (6)
C451.040 (2)0.3138 (8)0.6691 (6)0.227 (12)
C461.0770 (10)0.3707 (8)0.7006 (5)0.167 (5)
C471.0072 (9)0.4328 (5)0.7174 (3)0.116 (2)
C481.0701 (6)0.7212 (4)0.6445 (3)0.131 (3)
H48A1.09950.77580.65350.157*
H48B1.06520.71900.60910.157*
C491.1562 (5)0.6578 (4)0.6617 (2)0.0864 (15)
C501.1885 (6)0.5919 (5)0.6337 (3)0.116 (2)
C511.2669 (8)0.5338 (6)0.6502 (5)0.147 (4)
C521.3168 (7)0.5416 (6)0.6956 (6)0.153 (5)
C531.2846 (7)0.6067 (9)0.7226 (4)0.147 (4)
C541.2078 (6)0.6612 (5)0.7071 (3)0.109 (2)
F110.7497 (6)0.3814 (3)0.6495 (2)0.188 (2)
F120.9017 (10)0.2631 (3)0.61979 (19)0.302 (6)
F131.1190 (9)0.2577 (4)0.6560 (3)0.299 (5)
F141.1894 (7)0.3709 (5)0.7238 (3)0.254 (4)
F151.0435 (5)0.4887 (3)0.7512 (2)0.183 (2)
F161.1434 (4)0.5844 (5)0.5889 (2)0.211 (3)
F171.2997 (5)0.4713 (4)0.6225 (4)0.292 (5)
F181.3946 (4)0.4883 (4)0.7126 (4)0.282 (5)
F191.3326 (4)0.6190 (5)0.7685 (2)0.236 (4)
F201.1797 (4)0.7275 (4)0.7355 (2)0.189 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ti10.0713 (5)0.0558 (5)0.0559 (4)0.0022 (4)0.0000 (4)0.0057 (3)
O20.117 (3)0.088 (3)0.100 (3)0.030 (2)0.037 (2)0.002 (2)
O30.097 (2)0.0652 (19)0.083 (2)0.0188 (18)0.0219 (18)0.0168 (16)
C10.107 (5)0.081 (3)0.067 (3)0.011 (3)0.006 (3)0.016 (3)
C20.092 (4)0.058 (3)0.076 (3)0.006 (3)0.004 (3)0.015 (2)
C30.091 (4)0.056 (3)0.073 (3)0.007 (3)0.007 (3)0.011 (2)
C40.083 (4)0.068 (3)0.086 (4)0.002 (3)0.010 (3)0.029 (3)
C50.126 (5)0.068 (3)0.065 (3)0.010 (3)0.015 (3)0.021 (2)
C60.148 (6)0.123 (5)0.104 (5)0.011 (5)0.052 (5)0.014 (4)
C70.120 (5)0.086 (4)0.111 (5)0.029 (4)0.011 (4)0.004 (3)
C80.134 (5)0.078 (4)0.112 (5)0.036 (4)0.013 (4)0.006 (3)
C90.094 (5)0.093 (4)0.162 (6)0.006 (4)0.030 (4)0.049 (4)
C100.206 (8)0.106 (5)0.072 (4)0.038 (5)0.032 (4)0.015 (3)
C110.103 (4)0.102 (4)0.073 (3)0.027 (3)0.015 (3)0.004 (3)
C120.091 (4)0.072 (3)0.065 (3)0.021 (3)0.001 (3)0.002 (2)
C130.090 (4)0.095 (4)0.095 (4)0.012 (3)0.003 (3)0.005 (3)
C140.139 (6)0.100 (4)0.077 (4)0.000 (4)0.013 (4)0.032 (3)
C150.125 (5)0.084 (4)0.065 (3)0.032 (4)0.008 (4)0.003 (3)
C160.073 (4)0.141 (6)0.097 (4)0.020 (4)0.003 (3)0.027 (4)
C170.085 (4)0.149 (6)0.086 (4)0.028 (4)0.015 (3)0.045 (4)
C180.117 (5)0.076 (3)0.090 (4)0.027 (3)0.035 (3)0.023 (3)
C190.082 (4)0.063 (3)0.076 (3)0.012 (3)0.026 (3)0.002 (2)
C200.077 (3)0.075 (3)0.063 (3)0.015 (3)0.009 (3)0.001 (2)
C210.117 (5)0.071 (3)0.077 (3)0.015 (3)0.018 (3)0.011 (3)
C220.133 (6)0.113 (5)0.079 (4)0.048 (5)0.006 (4)0.010 (4)
C230.097 (5)0.147 (7)0.093 (5)0.032 (5)0.011 (4)0.015 (5)
C240.075 (4)0.092 (4)0.112 (5)0.003 (3)0.013 (4)0.019 (4)
F10.138 (4)0.185 (4)0.166 (4)0.057 (3)0.015 (3)0.049 (3)
F20.241 (6)0.220 (5)0.152 (4)0.044 (5)0.006 (4)0.114 (4)
F30.179 (4)0.147 (3)0.088 (2)0.053 (3)0.040 (2)0.011 (2)
F40.089 (3)0.274 (6)0.180 (4)0.008 (3)0.018 (3)0.079 (4)
F50.116 (3)0.320 (7)0.160 (4)0.005 (4)0.004 (3)0.145 (5)
F60.110 (2)0.104 (2)0.092 (2)0.0002 (19)0.0026 (19)0.0058 (17)
F70.190 (4)0.075 (2)0.126 (3)0.008 (2)0.026 (3)0.0211 (19)
F80.221 (5)0.174 (4)0.127 (3)0.085 (4)0.029 (3)0.041 (3)
F90.122 (3)0.256 (6)0.160 (4)0.032 (4)0.055 (3)0.048 (4)
F100.110 (3)0.122 (3)0.185 (4)0.032 (2)0.029 (3)0.031 (3)
O10.080 (2)0.0655 (18)0.0538 (16)0.0010 (16)0.0096 (14)0.0077 (13)
Ti20.0718 (5)0.0506 (4)0.0566 (4)0.0001 (4)0.0018 (4)0.0008 (3)
O40.176 (4)0.0509 (19)0.080 (2)0.005 (2)0.013 (2)0.0099 (16)
O50.063 (2)0.115 (3)0.102 (3)0.003 (2)0.002 (2)0.004 (2)
C310.092 (4)0.082 (3)0.059 (3)0.002 (3)0.012 (3)0.001 (2)
C320.106 (4)0.082 (4)0.059 (3)0.020 (3)0.010 (3)0.016 (3)
C330.082 (4)0.077 (3)0.090 (4)0.000 (3)0.005 (3)0.031 (3)
C340.074 (3)0.057 (3)0.067 (3)0.005 (2)0.001 (2)0.010 (2)
C350.067 (3)0.080 (3)0.061 (3)0.009 (3)0.005 (2)0.007 (2)
C360.138 (6)0.120 (5)0.100 (4)0.015 (4)0.046 (4)0.030 (4)
C370.174 (7)0.145 (6)0.081 (4)0.046 (5)0.052 (4)0.012 (4)
C380.096 (5)0.093 (4)0.177 (7)0.010 (4)0.026 (4)0.054 (4)
C390.119 (5)0.057 (3)0.090 (4)0.014 (3)0.003 (3)0.003 (2)
C400.071 (3)0.102 (4)0.099 (4)0.003 (3)0.003 (3)0.007 (3)
C410.194 (7)0.071 (4)0.112 (5)0.021 (4)0.045 (5)0.031 (3)
C420.152 (6)0.047 (3)0.079 (4)0.004 (4)0.021 (4)0.018 (3)
C430.185 (9)0.074 (5)0.108 (5)0.005 (5)0.003 (5)0.032 (4)
C440.340 (19)0.064 (5)0.102 (6)0.036 (9)0.053 (9)0.023 (4)
C450.42 (3)0.079 (6)0.181 (14)0.107 (13)0.170 (18)0.049 (8)
C460.128 (8)0.133 (9)0.242 (13)0.042 (7)0.059 (8)0.101 (9)
C470.155 (8)0.081 (5)0.113 (5)0.020 (5)0.007 (5)0.025 (4)
C480.106 (5)0.121 (5)0.167 (7)0.028 (4)0.044 (5)0.057 (5)
C490.067 (3)0.088 (4)0.104 (4)0.001 (3)0.018 (3)0.012 (3)
C500.070 (4)0.134 (6)0.144 (6)0.011 (4)0.002 (4)0.025 (5)
C510.076 (5)0.111 (6)0.255 (12)0.000 (5)0.001 (6)0.041 (7)
C520.068 (5)0.099 (6)0.292 (15)0.009 (5)0.003 (7)0.060 (8)
C530.076 (5)0.228 (12)0.137 (7)0.024 (7)0.012 (5)0.093 (8)
C540.076 (4)0.127 (6)0.123 (6)0.012 (4)0.019 (4)0.000 (5)
F110.253 (6)0.120 (4)0.188 (5)0.047 (4)0.073 (5)0.051 (3)
F120.694 (18)0.092 (3)0.121 (4)0.030 (6)0.017 (6)0.031 (3)
F130.437 (12)0.187 (6)0.277 (8)0.160 (7)0.208 (9)0.088 (6)
F140.164 (6)0.216 (7)0.382 (11)0.019 (5)0.028 (6)0.118 (7)
F150.235 (6)0.135 (4)0.178 (4)0.060 (4)0.047 (4)0.035 (3)
F160.127 (4)0.337 (8)0.168 (4)0.035 (4)0.018 (3)0.103 (5)
F170.138 (4)0.182 (6)0.557 (14)0.023 (4)0.039 (6)0.180 (7)
F180.104 (3)0.214 (6)0.527 (13)0.029 (4)0.027 (5)0.192 (8)
F190.110 (4)0.446 (11)0.151 (4)0.004 (5)0.001 (3)0.090 (6)
F200.130 (4)0.260 (6)0.177 (5)0.009 (4)0.018 (3)0.088 (5)
Geometric parameters (Å, º) top
Ti1—O11.812 (3)O1—Ti21.826 (3)
Ti1—O31.819 (3)Ti2—O51.795 (4)
Ti1—O21.831 (4)Ti2—O41.814 (3)
Ti1—C32.345 (5)Ti2—C342.381 (4)
Ti1—C22.357 (5)Ti2—C322.383 (5)
Ti1—C42.389 (5)Ti2—C332.391 (5)
Ti1—C52.390 (5)Ti2—C312.392 (5)
Ti1—C12.392 (5)Ti2—C352.400 (5)
O2—C111.394 (6)O4—C411.378 (6)
O3—C181.389 (6)O5—C481.345 (7)
C1—C21.396 (7)C31—C321.403 (7)
C1—C51.419 (8)C31—C351.411 (6)
C1—C61.504 (8)C31—C361.512 (7)
C2—C31.415 (7)C32—C331.417 (7)
C2—C71.505 (7)C32—C371.534 (7)
C3—C41.408 (7)C33—C341.420 (7)
C3—C81.509 (7)C33—C381.501 (8)
C4—C51.437 (8)C34—C351.418 (6)
C4—C91.510 (8)C34—C391.491 (6)
C5—C101.509 (7)C35—C401.513 (7)
C6—H6A0.9600C36—H36A0.9600
C6—H6B0.9600C36—H36B0.9600
C6—H6C0.9600C36—H36C0.9600
C7—H7A0.9600C37—H37A0.9600
C7—H7B0.9600C37—H37B0.9600
C7—H7C0.9600C37—H37C0.9600
C8—H8A0.9600C38—H38A0.9600
C8—H8B0.9600C38—H38B0.9600
C8—H8C0.9600C38—H38C0.9600
C9—H9A0.9600C39—H39A0.9600
C9—H9B0.9600C39—H39B0.9600
C9—H9C0.9600C39—H39C0.9600
C10—H10A0.9600C40—H40A0.9600
C10—H10B0.9600C40—H40B0.9600
C10—H10C0.9600C40—H40C0.9600
C11—C121.517 (7)C41—H41A0.9700
C11—H11A0.9700C41—H41B0.9700
C11—H11B0.9700C41—C421.494 (8)
C11—C121.517 (7)C42—C431.351 (9)
C12—C131.357 (7)C42—C471.383 (10)
C12—C171.373 (8)C43—F111.331 (9)
C13—F11.338 (7)C43—C441.358 (14)
C13—C141.389 (8)C44—C451.31 (2)
C14—F21.329 (7)C44—F121.344 (13)
C14—C151.350 (9)C45—C461.32 (2)
C15—C161.304 (8)C45—F131.325 (13)
C15—F31.349 (6)C46—C471.361 (13)
C16—F41.363 (7)C46—F141.419 (14)
C16—C171.377 (8)C47—F151.351 (8)
C17—F51.351 (7)C48—C491.487 (8)
C18—C191.518 (7)C48—H48A0.9700
C18—H18A0.9700C48—H48B0.9700
C18—H18B0.9700C49—C501.362 (9)
C19—C201.368 (7)C49—C541.365 (9)
C19—C241.371 (8)C50—F161.327 (8)
C20—C211.347 (7)C50—C511.365 (12)
C20—F61.350 (6)C51—F171.318 (9)
C21—C221.341 (9)C51—C521.365 (14)
C21—F71.348 (6)C52—F181.314 (9)
C22—F81.344 (7)C52—C531.336 (14)
C22—C231.380 (10)C53—C541.305 (11)
C23—F91.332 (8)C53—F191.378 (10)
C23—C241.385 (9)C54—F201.361 (8)
C24—F101.348 (7)
O1—Ti1—O3102.73 (14)O5—Ti2—O4102.31 (19)
O1—Ti1—O2105.24 (17)O5—Ti2—O1103.83 (16)
O3—Ti1—O2102.19 (18)O4—Ti2—O1103.58 (16)
O1—Ti1—C390.05 (15)O5—Ti2—C34105.03 (17)
O3—Ti1—C3115.59 (18)O4—Ti2—C34145.72 (17)
O2—Ti1—C3134.94 (18)O1—Ti2—C3489.59 (14)
O1—Ti1—C293.52 (16)O5—Ti2—C32101.9 (2)
O3—Ti1—C2147.09 (18)O4—Ti2—C3296.93 (18)
O2—Ti1—C2100.80 (19)O1—Ti2—C32142.57 (17)
C3—Ti1—C235.04 (17)C34—Ti2—C3257.50 (17)
O1—Ti1—C4118.65 (18)O5—Ti2—C3385.32 (18)
O3—Ti1—C489.02 (17)O4—Ti2—C33130.43 (19)
O2—Ti1—C4130.99 (19)O1—Ti2—C33122.23 (17)
C3—Ti1—C434.60 (17)C34—Ti2—C3334.61 (16)
C2—Ti1—C458.09 (18)C32—Ti2—C3334.54 (18)
O1—Ti1—C5147.00 (17)O5—Ti2—C31136.03 (19)
O3—Ti1—C596.95 (18)O4—Ti2—C3188.59 (17)
O2—Ti1—C596.0 (2)O1—Ti2—C31114.87 (17)
C3—Ti1—C557.39 (18)C34—Ti2—C3157.29 (16)
C2—Ti1—C557.33 (18)C32—Ti2—C3134.17 (18)
C4—Ti1—C534.99 (18)C33—Ti2—C3157.06 (19)
O1—Ti1—C1125.14 (17)O5—Ti2—C35139.11 (18)
O3—Ti1—C1130.11 (18)O4—Ti2—C35113.96 (19)
O2—Ti1—C179.87 (19)O1—Ti2—C3585.94 (15)
C3—Ti1—C157.42 (19)C34—Ti2—C3534.51 (16)
C2—Ti1—C134.18 (17)C32—Ti2—C3557.00 (17)
C4—Ti1—C157.97 (19)C33—Ti2—C3557.13 (18)
C5—Ti1—C134.53 (18)C31—Ti2—C3534.24 (16)
C11—O2—Ti1130.3 (3)C41—O4—Ti2156.9 (4)
C18—O3—Ti1150.6 (3)C48—O5—Ti2169.8 (5)
C2—C1—C5108.0 (5)C32—C31—C35108.4 (5)
C2—C1—C6125.9 (6)C32—C31—C36127.1 (5)
C5—C1—C6126.1 (6)C35—C31—C36124.4 (5)
C2—C1—Ti171.5 (3)C32—C31—Ti272.6 (3)
C5—C1—Ti172.7 (3)C35—C31—Ti273.2 (3)
C6—C1—Ti1121.4 (4)C36—C31—Ti2123.3 (4)
C1—C2—C3108.1 (5)C31—C32—C33108.2 (5)
C1—C2—C7126.6 (5)C31—C32—C37126.2 (6)
C3—C2—C7125.3 (5)C33—C32—C37125.6 (6)
C1—C2—Ti174.3 (3)C31—C32—Ti273.3 (3)
C3—C2—Ti172.0 (3)C33—C32—Ti273.0 (3)
C7—C2—Ti1121.0 (3)C37—C32—Ti2120.9 (4)
C4—C3—C2109.4 (5)C32—C33—C34107.8 (5)
C4—C3—C8124.5 (5)C32—C33—C38126.4 (6)
C2—C3—C8126.2 (5)C34—C33—C38125.8 (6)
C4—C3—Ti174.4 (3)C32—C33—Ti272.4 (3)
C2—C3—Ti172.9 (3)C34—C33—Ti272.3 (3)
C8—C3—Ti1120.1 (3)C38—C33—Ti2122.0 (4)
C3—C4—C5106.1 (5)C35—C34—C33107.7 (4)
C3—C4—C9126.4 (6)C35—C34—C39125.3 (5)
C5—C4—C9127.4 (6)C33—C34—C39127.0 (5)
C3—C4—Ti171.0 (3)C35—C34—Ti273.5 (3)
C5—C4—Ti172.5 (3)C33—C34—Ti273.1 (3)
C9—C4—Ti1124.0 (3)C39—C34—Ti2121.1 (3)
C1—C5—C4108.4 (5)C31—C35—C34108.0 (4)
C1—C5—C10126.0 (6)C31—C35—C40126.3 (5)
C4—C5—C10125.6 (6)C34—C35—C40125.7 (5)
C1—C5—Ti172.8 (3)C31—C35—Ti272.6 (3)
C4—C5—Ti172.5 (3)C34—C35—Ti272.0 (3)
C10—C5—Ti1120.9 (4)C40—C35—Ti2120.8 (3)
C1—C6—H6A109.5C31—C36—H36A109.5
C1—C6—H6B109.5C31—C36—H36B109.5
H6A—C6—H6B109.5H36A—C36—H36B109.5
C1—C6—H6C109.5C31—C36—H36C109.5
H6A—C6—H6C109.5H36A—C36—H36C109.5
H6B—C6—H6C109.5H36B—C36—H36C109.5
C2—C7—H7A109.5C32—C37—H37A109.5
C2—C7—H7B109.5C32—C37—H37B109.5
H7A—C7—H7B109.5H37A—C37—H37B109.5
C2—C7—H7C109.5C32—C37—H37C109.5
H7A—C7—H7C109.5H37A—C37—H37C109.5
H7B—C7—H7C109.5H37B—C37—H37C109.5
C3—C8—H8A109.5C33—C38—H38A109.5
C3—C8—H8B109.5C33—C38—H38B109.5
H8A—C8—H8B109.5H38A—C38—H38B109.5
C3—C8—H8C109.5C33—C38—H38C109.5
H8A—C8—H8C109.5H38A—C38—H38C109.5
H8B—C8—H8C109.5H38B—C38—H38C109.5
C4—C9—H9A109.5C34—C39—H39A109.5
C4—C9—H9B109.5C34—C39—H39B109.5
H9A—C9—H9B109.5H39A—C39—H39B109.5
C4—C9—H9C109.5C34—C39—H39C109.5
H9A—C9—H9C109.5H39A—C39—H39C109.5
H9B—C9—H9C109.5H39B—C39—H39C109.5
C5—C10—H10A109.5C35—C40—H40A109.5
C5—C10—H10B109.5C35—C40—H40B109.5
H10A—C10—H10B109.5H40A—C40—H40B109.5
C5—C10—H10C109.5C35—C40—H40C109.5
H10A—C10—H10C109.5H40A—C40—H40C109.5
H10B—C10—H10C109.5H40B—C40—H40C109.5
O2—C11—C12109.5 (4)O4—C41—C42111.7 (5)
O2—C11—H11A109.8O4—C41—H41A109.3
C12—C11—H11A109.8C42—C41—H41A109.3
O2—C11—H11B109.8O4—C41—H41B109.3
C12—C11—H11B109.8C42—C41—H41B109.3
H11A—C11—H11B108.2H41A—C41—H41B107.9
C13—C12—C17114.1 (5)C43—C42—C47114.4 (7)
C13—C12—C11122.9 (6)C43—C42—C41122.1 (8)
C17—C12—C11122.9 (5)C47—C42—C41123.5 (7)
F1—C13—C12118.0 (6)F11—C43—C42121.0 (9)
F1—C13—C14119.5 (6)F11—C43—C44116.6 (10)
C12—C13—C14122.5 (6)C42—C43—C44122.4 (10)
F2—C14—C15120.8 (7)C45—C44—F12113.3 (15)
F2—C14—C13119.5 (7)C45—C44—C43122.8 (14)
C15—C14—C13119.6 (5)F12—C44—C43123.8 (15)
C16—C15—F3120.0 (7)C44—C45—C46116.3 (12)
C16—C15—C14120.3 (6)C44—C45—F13127 (2)
F3—C15—C14119.8 (6)C46—C45—F13116 (2)
C15—C16—F4120.1 (6)C45—C46—C47123.4 (13)
C15—C16—C17119.6 (6)C45—C46—F14124.5 (15)
F4—C16—C17120.2 (6)C47—C46—F14112.0 (15)
F5—C17—C12119.3 (5)F15—C47—C46123.1 (11)
F5—C17—C16116.8 (6)F15—C47—C42116.2 (8)
C12—C17—C16123.9 (5)C46—C47—C42120.6 (10)
O3—C18—C19109.6 (4)O5—C48—C49114.5 (5)
O3—C18—H18A109.7O5—C48—H48A108.6
C19—C18—H18A109.7C49—C48—H48A108.6
O3—C18—H18B109.7O5—C48—H48B108.6
C19—C18—H18B109.7C49—C48—H48B108.6
H18A—C18—H18B108.2H48A—C48—H48B107.6
C20—C19—C24116.6 (5)C50—C49—C54115.2 (7)
C20—C19—C18120.5 (5)C50—C49—C48122.6 (7)
C24—C19—C18122.9 (5)C54—C49—C48122.2 (7)
C21—C20—F6117.6 (5)F16—C50—C49119.1 (7)
C21—C20—C19123.0 (6)F16—C50—C51119.0 (8)
F6—C20—C19119.4 (5)C49—C50—C51121.9 (8)
C22—C21—C20119.3 (6)F17—C51—C50121.6 (11)
C22—C21—F7120.3 (6)F17—C51—C52118.4 (11)
C20—C21—F7120.5 (6)C50—C51—C52119.9 (9)
C21—C22—F8119.8 (8)F18—C52—C53120.5 (14)
C21—C22—C23121.7 (6)F18—C52—C51122.1 (14)
F8—C22—C23118.5 (8)C53—C52—C51117.4 (8)
F9—C23—C22122.8 (8)C54—C53—C52122.4 (10)
F9—C23—C24120.1 (8)C54—C53—F19117.1 (13)
C22—C23—C24117.1 (6)C52—C53—F19120.5 (12)
F10—C24—C19118.8 (6)C53—C54—F20120.2 (10)
F10—C24—C23118.8 (7)C53—C54—C49123.1 (9)
C19—C24—C23122.4 (6)F20—C54—C49116.7 (7)
Ti1—O1—Ti2163.1 (2)

Experimental details

Crystal data
Chemical formula[Ti2(C10H15)2(C7H2F5O)4O]
Mr1170.58
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.371 (2), 16.113 (3), 27.340 (6)
β (°) 90.75 (3)
V3)5008.8 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.94, 0.96
No. of measured, independent and
observed [I > 2σ(I)] reflections
28465, 11233, 5333
Rint0.042
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.075, 0.221, 1.03
No. of reflections11233
No. of parameters686
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.37

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MEST) (2010–0003141).

References

First citationBruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationGowik, P., Klaotke, T. & Pickardt, J. (1990). J. Organomet. Chem. 393, 343–348.  CSD CrossRef CAS Web of Science
First citationLee, J., Do, Y. & Kim, Y. (2007). J. Organomet. Chem. 692, 3593–3598.  Web of Science CSD CrossRef CAS
First citationNoh, S. K., Jung, W., Oh, H., Lee, Y. R. & Lyoo, W. S. (2006). J. Organomet. Chem. 691, 5000–5006.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationThewalt, U. & Schomburg, D. (1977). J. Organomet. Chem. 127, 169–174.  CSD CrossRef CAS Web of Science
First citationWu, Q. L., Li, G. H., Ye, L., Gao, W. & Mu, Y. (2009). Polyhedron, 26, 3063–3068.  Web of Science CSD CrossRef
First citationYoon, S. W., Kim, Y., Kim, S. K., Kim, S. Y., Do, Y. & Park, S. (2011). Macromol. Chem. Phys. 212, 785–789.  Web of Science CSD CrossRef CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds