Dibromo­(η⁵,η⁵-propane-2,2-diyldicyclo­penta­dien­yl)zirconium(IV)

The title compound, [ZrBr₂(C₁₃H₂₄)], contains a pseudo-tetra­hedral Zr^IV centre involving two η⁵-bonded cyclo­penta­dienyl rings [Zr—Cg = 2.1843 (12) Å; Cg is the centroid of a cyclo­penta­dienyl ring] and two Br atoms [Zr—Br = 2.5828 (5) and 2.5879 (6) Å]. The angle Cg1—Zr—Cg2 is constrained to a value of 116.80 (5)° due to the presence of a short inter­annular 2,2-propyl­idene bridge. The Zr and Br atoms lie on a crystallographic mirror plane, which bisects the organic ligand.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.027
• wR factor = 0.065
• Data-to-parameter ratio = 19.9

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: enCIFer (Allen et al., 2004).

Dibromo(η⁵,η⁵-propane-2,2-diyldicyclopentadienyl)zirconium(IV)

Crystal data

[ZrBr2(C13H14)]	F(000) = 404
Mr = 421.28	Dx = 2.107 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 7302 reflections
a = 7.3360 (3) Å	θ = 1–27.5°
b = 8.7470 (4) Å	µ = 6.82 mm^−1
c = 10.3500 (3) Å	T = 150 K
β = 90.763 (2)°	Plate, green
V = 664.08 (5) Å^3	0.14 × 0.05 × 0.05 mm
Z = 2

Data collection

Nonius KappaCCD area-detector diffractometer	1635 independent reflections
Radiation source: fine-focus sealed tube	1421 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans to fill the Ewald sphere	h = −9→9
Absorption correction: gaussian (Coppens, 1970)	k = −11→11
Tmin = 0.398, Tmax = 0.759	l = −13→13
11528 measured 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0312P)^2 + 0.607P] where P = (Fo^2 + 2Fc^2)/3
1635 reflections	(Δ/σ)max = 0.001
82 parameters	Δρmax = 0.81 e Å^−3
0 restraints	Δρmin = −0.73 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	Occ. (<1)
Zr1	0.32145 (5)	0.2500	0.82417 (3)	0.01509 (11)
Br1	0.19024 (6)	0.2500	1.05450 (4)	0.02553 (13)
Br2	0.66735 (6)	0.2500	0.87665 (4)	0.02717 (13)
C1	0.1953 (4)	0.1169 (3)	0.6358 (3)	0.0181 (6)
C2	0.3765 (4)	0.0628 (3)	0.6522 (3)	0.0226 (7)
H2	0.4729	0.0836	0.5975	0.027*
C3	0.3866 (4)	−0.0281 (3)	0.7653 (3)	0.0253 (7)
H3	0.4896	−0.0788	0.7966	0.030*
C4	0.2147 (4)	−0.0280 (3)	0.8216 (3)	0.0232 (6)
H4	0.1830	−0.0788	0.8970	0.028*
C5	0.0972 (4)	0.0629 (3)	0.7441 (3)	0.0198 (6)
H5	−0.0244	0.0838	0.7612	0.024*
C6	0.1371 (6)	0.2500	0.5497 (4)	0.0214 (9)
C7	0.2374 (7)	0.2500	0.4206 (4)	0.0325 (11)
H7A	0.2050	0.1600	0.3725	0.049*	0.50
H7B	0.3666	0.2500	0.4367	0.049*
H7C	0.2035	0.3392	0.3719	0.049*	0.50
C8	−0.0693 (6)	0.2500	0.5235 (5)	0.0297 (10)
H8A	−0.1024	0.3370	0.4745	0.045*	0.50
H8B	−0.1324	0.2500	0.6041	0.045*
H8C	−0.1021	0.1580	0.4748	0.045*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zr1	0.0162 (2)	0.0162 (2)	0.0129 (2)	0.000	0.00122 (14)	0.000
Br1	0.0255 (2)	0.0344 (3)	0.0168 (2)	0.000	0.00589 (16)	0.000
Br2	0.0177 (2)	0.0356 (3)	0.0283 (3)	0.000	−0.00042 (17)	0.000
C1	0.0240 (15)	0.0150 (14)	0.0151 (14)	0.0001 (11)	−0.0012 (11)	−0.0043 (11)
C2	0.0281 (16)	0.0189 (15)	0.0210 (16)	0.0005 (12)	0.0053 (12)	−0.0062 (12)
C3	0.0289 (17)	0.0197 (16)	0.0273 (17)	0.0042 (13)	−0.0058 (13)	−0.0044 (13)
C4	0.0301 (16)	0.0173 (15)	0.0223 (16)	−0.0024 (13)	−0.0006 (12)	0.0036 (12)
C5	0.0202 (14)	0.0182 (15)	0.0209 (15)	−0.0002 (12)	−0.0012 (11)	−0.0007 (12)
C6	0.026 (2)	0.021 (2)	0.017 (2)	0.000	−0.0023 (17)	0.000
C7	0.050 (3)	0.036 (3)	0.011 (2)	0.000	0.003 (2)	0.000
C8	0.032 (3)	0.028 (2)	0.029 (3)	0.000	−0.010 (2)	0.000

Geometric parameters (Å, º)

Zr1—C1^i	2.443 (3)	C2—H2	0.9300
Zr1—C1	2.443 (3)	C3—C4	1.396 (4)
Zr1—C2	2.456 (3)	C3—H3	0.9300
Zr1—C2^i	2.456 (3)	C4—C5	1.415 (4)
Zr1—C5	2.457 (3)	C4—H4	0.9300
Zr1—C5^i	2.457 (3)	C5—H5	0.9300
Zr1—C3	2.554 (3)	C6—C1^i	1.524 (4)
Zr1—C3^i	2.554 (3)	C6—C7	1.533 (6)
Zr1—C4	2.554 (3)	C6—C8	1.534 (6)
Zr1—C4^i	2.554 (3)	C7—H7A	0.9600
Zr1—Br1	2.5828 (5)	C7—H7B	0.9600
Zr1—Br2	2.5879 (6)	C7—H7C	0.9600
C1—C2	1.419 (4)	C8—H8A	0.9448
C1—C5	1.421 (4)	C8—H8B	0.9590
C1—C6	1.524 (4)	C8—H8C	0.9787
C2—C3	1.416 (4)
C1^i—Zr1—C1	56.94 (13)	C2—Zr1—Br2	88.96 (7)
C1^i—Zr1—C2	78.67 (10)	C2^i—Zr1—Br2	88.96 (7)
C1—Zr1—C2	33.67 (10)	C5—Zr1—Br2	136.15 (7)
C1^i—Zr1—C2^i	33.67 (10)	C5^i—Zr1—Br2	136.15 (7)
C1—Zr1—C2^i	78.67 (10)	C3—Zr1—Br2	82.17 (7)
C2—Zr1—C2^i	83.65 (14)	C3^i—Zr1—Br2	82.17 (7)
C1^i—Zr1—C5	78.66 (9)	C4—Zr1—Br2	107.56 (7)
C1—Zr1—C5	33.72 (9)	C4^i—Zr1—Br2	107.56 (7)
C2—Zr1—C5	55.04 (10)	Br1—Zr1—Br2	100.530 (19)
C2^i—Zr1—C5	108.39 (10)	C2—C1—C5	106.1 (3)
C1^i—Zr1—C5^i	33.72 (9)	C2—C1—C6	125.4 (3)
C1—Zr1—C5^i	78.66 (9)	C5—C1—C6	125.0 (3)
C2—Zr1—C5^i	108.39 (10)	C2—C1—Zr1	73.68 (16)
C2^i—Zr1—C5^i	55.04 (10)	C5—C1—Zr1	73.69 (16)
C5—Zr1—C5^i	83.55 (14)	C6—C1—Zr1	101.70 (18)
C1^i—Zr1—C3	109.49 (10)	C3—C2—C1	109.0 (3)
C1—Zr1—C3	54.95 (10)	C3—C2—Zr1	77.43 (17)
C2—Zr1—C3	32.76 (10)	C1—C2—Zr1	72.65 (16)
C2^i—Zr1—C3	115.41 (10)	C3—C2—H2	125.5
C5—Zr1—C3	53.97 (10)	C1—C2—H2	125.5
C5^i—Zr1—C3	132.89 (10)	Zr1—C2—H2	116.4
C1^i—Zr1—C3^i	54.95 (10)	C4—C3—C2	107.9 (3)
C1—Zr1—C3^i	109.49 (10)	C4—C3—Zr1	74.14 (17)
C2—Zr1—C3^i	115.41 (10)	C2—C3—Zr1	69.81 (16)
C2^i—Zr1—C3^i	32.76 (10)	C4—C3—H3	126.1
C5—Zr1—C3^i	132.89 (10)	C2—C3—H3	126.1
C5^i—Zr1—C3^i	53.97 (10)	Zr1—C3—H3	121.7
C3—Zr1—C3^i	144.46 (14)	C3—C4—C5	108.1 (3)
C1^i—Zr1—C4	109.44 (10)	C3—C4—Zr1	74.13 (17)
C1—Zr1—C4	54.91 (10)	C5—C4—Zr1	69.85 (16)
C2—Zr1—C4	53.92 (10)	C3—C4—H4	125.9
C2^i—Zr1—C4	132.89 (10)	C5—C4—H4	125.9
C5—Zr1—C4	32.72 (9)	Zr1—C4—H4	121.7
C5^i—Zr1—C4	115.27 (10)	C4—C5—C1	108.8 (3)
C3—Zr1—C4	31.73 (10)	C4—C5—Zr1	77.43 (17)
C3^i—Zr1—C4	164.22 (10)	C1—C5—Zr1	72.59 (16)
C1^i—Zr1—C4^i	54.91 (9)	C4—C5—H5	125.6
C1—Zr1—C4^i	109.44 (10)	C1—C5—H5	125.6
C2—Zr1—C4^i	132.89 (10)	Zr1—C5—H5	116.4
C2^i—Zr1—C4^i	53.92 (10)	C1^i—C6—C1	99.7 (3)
C5—Zr1—C4^i	115.27 (10)	C1^i—C6—C7	112.0 (3)
C5^i—Zr1—C4^i	32.72 (9)	C1—C6—C7	112.0 (2)
C3—Zr1—C4^i	164.22 (10)	C1^i—C6—C8	111.8 (2)
C3^i—Zr1—C4^i	31.72 (10)	C1—C6—C8	111.8 (2)
C4—Zr1—C4^i	144.30 (14)	C7—C6—C8	109.3 (4)
C1^i—Zr1—Br1	126.51 (7)	C6—C7—H7A	109.5
C1—Zr1—Br1	126.51 (7)	C6—C7—H7B	109.5
C2—Zr1—Br1	137.37 (7)	H7A—C7—H7B	109.1
C2^i—Zr1—Br1	137.37 (7)	C6—C7—H7C	109.5
C5—Zr1—Br1	93.17 (7)	H7A—C7—H7C	109.5
C5^i—Zr1—Br1	93.17 (7)	H7B—C7—H7C	109.8
C3—Zr1—Br1	107.06 (7)	C6—C8—H8A	109.9
C3^i—Zr1—Br1	107.06 (7)	C6—C8—H8B	109.5
C4—Zr1—Br1	83.78 (7)	H8A—C8—H8B	110.1
C4^i—Zr1—Br1	83.78 (7)	C6—C8—H8C	109.1
C1^i—Zr1—Br2	121.84 (7)	H8A—C8—H8C	109.0
C1—Zr1—Br2	121.83 (7)	H8B—C8—H8C	109.3

Symmetry code: (i) x, −y+1/2, z.