Difluoro­(η⁵,η⁵-propane-2,2-diyldicyclo­pentadienyl)titanium(IV)

In the title compound, [Ti(C₁₃H₁₄)F₂], the coordination polyhedron around the Ti atom is a distorted tetra­hedron defined by the centroids of the cyclo­penta­dien­yl rings and the two F atoms. The Ti–ring centroid (Cg) distances are 2.0558 (7) and 2.0567 (8) Å. The presence of a short carbon bridge linking the cyclo­penta­dien­yl rings constrains the Cg—Ti—Cg angle to a value of 121.50 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.030
• wR factor = 0.087
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Difluoro(η⁵,η⁵-propane-2,2-diyldicyclopentadienyl)titanium(IV)

Crystal data

[Ti(C13H14)F2]	F(000) = 528
Mr = 256.14	Dx = 1.577 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2549 reflections
a = 7.9700 (2) Å	θ = 1–27.5°
b = 14.3740 (3) Å	µ = 0.79 mm^−1
c = 9.5750 (2) Å	T = 150 K
β = 100.3350 (15)°	Prism, orange
V = 1079.12 (4) Å^3	0.25 × 0.25 × 0.14 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	2163 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 9.091 pixels mm^-1	h = −10→10
φ and ω scans to fill the Ewald sphere	k = −18→18
17813 measured reflections	l = −12→12
2478 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.5257P] where P = (Fo^2 + 2Fc^2)/3
2478 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ti1	0.28927 (3)	−0.004903 (17)	0.20313 (3)	0.01659 (11)
F1	0.49923 (12)	−0.06172 (7)	0.26205 (11)	0.0276 (2)
F2	0.21765 (12)	−0.07025 (6)	0.03474 (9)	0.0225 (2)
C1	0.24140 (19)	0.15229 (10)	0.23886 (16)	0.0181 (3)
C2	0.4208 (2)	0.13866 (10)	0.26719 (18)	0.0228 (3)
H2	0.4908	0.1435	0.3557	0.027*
C3	0.4752 (2)	0.11658 (11)	0.1387 (2)	0.0274 (4)
H3	0.5870	0.1055	0.1277	0.033*
C4	0.3317 (2)	0.11435 (11)	0.03067 (18)	0.0255 (3)
H4	0.3315	0.1018	−0.0646	0.031*
C5	0.1865 (2)	0.13451 (10)	0.09170 (16)	0.0201 (3)
H5	0.0742	0.1359	0.0436	0.024*
C6	0.11436 (19)	0.04372 (10)	0.36068 (16)	0.0178 (3)
C7	0.2419 (2)	−0.01386 (11)	0.43924 (16)	0.0209 (3)
H7	0.3277	0.0055	0.5125	0.025*
C8	0.2161 (2)	−0.10609 (11)	0.38693 (17)	0.0241 (3)
H8	0.2812	−0.1577	0.4207	0.029*
C9	0.0757 (2)	−0.10586 (10)	0.27569 (17)	0.0228 (3)
H9	0.0311	−0.1574	0.2231	0.027*
C10	0.0132 (2)	−0.01344 (10)	0.25701 (17)	0.0203 (3)
H10	−0.0780	0.0063	0.1889	0.024*
C11	0.1261 (2)	0.14966 (10)	0.34971 (16)	0.0187 (3)
C12	−0.0471 (2)	0.19505 (11)	0.29601 (18)	0.0248 (3)
H12A	−0.0314	0.2601	0.2799	0.037*
H12B	−0.1190	0.1875	0.3656	0.037*
H12C	−0.0997	0.1660	0.2088	0.037*
C13	0.2107 (2)	0.19457 (11)	0.48930 (17)	0.0252 (3)
H13A	0.3179	0.1646	0.5233	0.038*
H13B	0.1378	0.1879	0.5583	0.038*
H13C	0.2296	0.2594	0.4740	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ti1	0.01849 (17)	0.01446 (15)	0.01660 (17)	0.00030 (9)	0.00254 (11)	−0.00073 (9)
F1	0.0235 (5)	0.0268 (5)	0.0311 (5)	0.0064 (4)	0.0014 (4)	0.0005 (4)
F2	0.0280 (5)	0.0204 (4)	0.0190 (4)	−0.0014 (4)	0.0039 (4)	−0.0028 (3)
C1	0.0234 (7)	0.0105 (6)	0.0202 (7)	−0.0014 (5)	0.0036 (6)	0.0006 (5)
C2	0.0219 (8)	0.0175 (7)	0.0281 (8)	−0.0036 (6)	0.0023 (6)	−0.0024 (6)
C3	0.0253 (8)	0.0208 (7)	0.0390 (10)	−0.0045 (6)	0.0135 (7)	−0.0012 (7)
C4	0.0342 (9)	0.0196 (7)	0.0257 (8)	−0.0040 (6)	0.0134 (7)	0.0004 (6)
C5	0.0260 (8)	0.0159 (7)	0.0185 (7)	−0.0004 (6)	0.0038 (6)	0.0027 (5)
C6	0.0202 (7)	0.0192 (7)	0.0151 (7)	−0.0008 (6)	0.0059 (6)	0.0002 (5)
C7	0.0266 (8)	0.0210 (7)	0.0143 (7)	−0.0002 (6)	0.0019 (6)	0.0019 (6)
C8	0.0338 (9)	0.0170 (7)	0.0219 (8)	0.0019 (6)	0.0065 (7)	0.0042 (6)
C9	0.0312 (8)	0.0174 (7)	0.0213 (8)	−0.0056 (6)	0.0085 (6)	−0.0005 (6)
C10	0.0208 (8)	0.0206 (7)	0.0200 (8)	−0.0035 (6)	0.0054 (6)	0.0006 (6)
C11	0.0231 (7)	0.0155 (7)	0.0175 (7)	0.0009 (5)	0.0036 (6)	−0.0007 (5)
C12	0.0258 (8)	0.0237 (8)	0.0258 (8)	0.0052 (6)	0.0072 (6)	0.0025 (6)
C13	0.0335 (9)	0.0206 (7)	0.0215 (8)	−0.0009 (6)	0.0049 (7)	−0.0035 (6)

Geometric parameters (Å, º)

Ti1—F1	1.8565 (9)	C4—H4	0.9300
Ti1—F2	1.8648 (9)	C5—H5	0.9300
Ti1—C1	2.3270 (14)	C6—C7	1.418 (2)
Ti1—C6	2.3371 (15)	C6—C10	1.422 (2)
Ti1—C2	2.3456 (15)	C6—C11	1.530 (2)
Ti1—C5	2.3477 (15)	C7—C8	1.419 (2)
Ti1—C10	2.3513 (16)	C7—H7	0.9300
Ti1—C7	2.3614 (16)	C8—C9	1.399 (2)
Ti1—C9	2.4308 (16)	C8—H8	0.9300
Ti1—C8	2.4333 (16)	C9—C10	1.419 (2)
Ti1—C3	2.4400 (16)	C9—H9	0.9300
Ti1—C4	2.4453 (16)	C10—H10	0.9300
C1—C2	1.420 (2)	C11—C13	1.528 (2)
C1—C5	1.422 (2)	C11—C12	1.531 (2)
C1—C11	1.524 (2)	C12—H12A	0.9600
C2—C3	1.412 (2)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.398 (2)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.417 (2)	C13—H13C	0.9600
F1—Ti1—F2	99.24 (4)	C3—C2—C1	108.68 (14)
F1—Ti1—C1	123.03 (5)	C3—C2—Ti1	76.53 (9)
F2—Ti1—C1	125.69 (5)	C1—C2—Ti1	71.59 (8)
F1—Ti1—C6	123.02 (5)	C3—C2—H2	125.7
F2—Ti1—C6	125.68 (5)	C1—C2—H2	125.7
C1—Ti1—C6	58.82 (5)	Ti1—C2—H2	118.1
F1—Ti1—C2	88.36 (5)	C4—C3—C2	108.15 (15)
F2—Ti1—C2	136.25 (5)	C4—C3—Ti1	73.58 (9)
C1—Ti1—C2	35.38 (5)	C2—C3—Ti1	69.21 (9)
C6—Ti1—C2	81.86 (6)	C4—C3—H3	125.9
F1—Ti1—C5	137.35 (5)	C2—C3—H3	125.9
F2—Ti1—C5	90.53 (5)	Ti1—C3—H3	122.9
C1—Ti1—C5	35.41 (5)	C3—C4—C5	108.10 (15)
C6—Ti1—C5	80.69 (5)	C3—C4—Ti1	73.17 (9)
C2—Ti1—C5	58.06 (6)	C5—C4—Ti1	69.07 (8)
F1—Ti1—C10	137.58 (5)	C3—C4—H4	126.0
F2—Ti1—C10	90.58 (5)	C5—C4—H4	126.0
C1—Ti1—C10	80.44 (5)	Ti1—C4—H4	123.4
C6—Ti1—C10	35.32 (5)	C4—C5—C1	108.46 (14)
C2—Ti1—C10	112.35 (5)	C4—C5—Ti1	76.62 (9)
C5—Ti1—C10	83.13 (5)	C1—C5—Ti1	71.50 (8)
F1—Ti1—C7	88.58 (5)	C4—C5—H5	125.8
F2—Ti1—C7	136.35 (5)	C1—C5—H5	125.8
C1—Ti1—C7	81.58 (5)	Ti1—C5—H5	118.0
C6—Ti1—C7	35.12 (5)	C7—C6—C10	107.20 (13)
C2—Ti1—C7	86.46 (6)	C7—C6—C11	124.77 (14)
C5—Ti1—C7	112.27 (5)	C10—C6—C11	124.12 (14)
C10—Ti1—C7	58.03 (6)	C7—C6—Ti1	73.38 (9)
F1—Ti1—C9	106.84 (5)	C10—C6—Ti1	72.89 (9)
F2—Ti1—C9	79.92 (5)	C11—C6—Ti1	101.67 (9)
C1—Ti1—C9	113.33 (5)	C6—C7—C8	108.26 (14)
C6—Ti1—C9	57.64 (5)	C6—C7—Ti1	71.50 (9)
C2—Ti1—C9	138.88 (6)	C8—C7—Ti1	75.58 (9)
C5—Ti1—C9	115.74 (5)	C6—C7—H7	125.9
C10—Ti1—C9	34.46 (5)	C8—C7—H7	125.9
C7—Ti1—C9	56.87 (5)	Ti1—C7—H7	118.9
F1—Ti1—C8	80.63 (5)	C9—C8—C7	108.18 (14)
F2—Ti1—C8	104.38 (5)	C9—C8—Ti1	73.18 (9)
C1—Ti1—C8	114.03 (6)	C7—C8—Ti1	70.03 (9)
C6—Ti1—C8	57.57 (5)	C9—C8—H8	125.9
C2—Ti1—C8	119.38 (6)	C7—C8—H8	125.9
C5—Ti1—C8	136.85 (6)	Ti1—C8—H8	122.5
C10—Ti1—C8	56.97 (6)	C8—C9—C10	108.23 (14)
C7—Ti1—C8	34.39 (5)	C8—C9—Ti1	73.38 (9)
C9—Ti1—C8	33.44 (6)	C10—C9—Ti1	69.70 (9)
F1—Ti1—C3	80.60 (5)	C8—C9—H9	125.9
F2—Ti1—C3	104.32 (5)	C10—C9—H9	125.9
C1—Ti1—C3	57.67 (5)	Ti1—C9—H9	122.7
C6—Ti1—C3	114.13 (6)	C9—C10—C6	108.10 (14)
C2—Ti1—C3	34.26 (6)	C9—C10—Ti1	75.83 (9)
C5—Ti1—C3	56.79 (6)	C6—C10—Ti1	71.79 (9)
C10—Ti1—C3	136.67 (6)	C9—C10—H10	126.0
C7—Ti1—C3	119.33 (6)	C6—C10—H10	126.0
C9—Ti1—C3	170.95 (5)	Ti1—C10—H10	118.3
C8—Ti1—C3	147.78 (6)	C1—C11—C13	111.85 (13)
F1—Ti1—C4	106.70 (5)	C1—C11—C6	97.16 (11)
F2—Ti1—C4	80.05 (5)	C13—C11—C6	112.54 (13)
C1—Ti1—C4	57.64 (5)	C1—C11—C12	112.07 (13)
C6—Ti1—C4	113.39 (5)	C13—C11—C12	110.11 (13)
C2—Ti1—C4	56.67 (6)	C6—C11—C12	112.61 (13)
C5—Ti1—C4	34.31 (6)	C11—C12—H12A	109.5
C10—Ti1—C4	115.65 (6)	C11—C12—H12B	109.5
C7—Ti1—C4	138.58 (5)	H12A—C12—H12B	109.5
C9—Ti1—C4	143.14 (6)	C11—C12—H12C	109.5
C8—Ti1—C4	170.93 (5)	H12A—C12—H12C	109.5
C3—Ti1—C4	33.25 (6)	H12B—C12—H12C	109.5
C2—C1—C5	106.56 (14)	C11—C13—H13A	109.5
C2—C1—C11	125.14 (14)	C11—C13—H13B	109.5
C5—C1—C11	124.69 (13)	H13A—C13—H13B	109.5
C2—C1—Ti1	73.03 (8)	C11—C13—H13C	109.5
C5—C1—Ti1	73.09 (8)	H13A—C13—H13C	109.5
C11—C1—Ti1	102.33 (9)	H13B—C13—H13C	109.5