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The title compound, [Cr(C13H21)2] or [η5-1,3-(Me3C)2C5H3]2Cr, a substituted chromocene, crystallizes with two independent half-mol­ecules in the asymmetric unit, the molecules having twofold rotation symmetry. The compound is isostructural with the iron and cobalt analogues and is a bent metallocene.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059491/sg2205sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059491/sg2205Isup2.hkl
Contains datablock I

CCDC reference: 672709

Key indicators

  • Single-crystal X-ray study
  • T = 134 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.114
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.90 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... CP1 CR1 CP1 PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... CP2 CR2 CP2 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CP1 CP1 CR1 CP1 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CP2 CP2 CR2 CP2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The properties of metallocenes vary widely depending on the substituents on the cyclopentadienyl ring. The bulky ligand [1,3-(Me3C)2C5H3]- has been found to have electronic properties similar to (Me5C5)- in ytterbocenes (Schultz et al., 2001), but quite different steric properties leading to different solid state packing arrangements in the base-free metallocenes (Schultz et al., 2000). The chromocene of this ligand, the title compound (I), was prepared as part of a study of first row metallocenes with bulky substituents.

The compound (I) crystallizes with two half-molecules in the asymmetric unit and the metals lying on special positions. The compound is isostructural with the iron and cobalt analogues, which are the only other base-free transition metal metallocenes with this ligand that have been structurally characterized (Boese et al., 1993), (Schneider et al., 1997). Table 1 gives selected bond distances and angles for (I); Cg1 and Cg2 are the calculated centroids of the rings C1 - C5 and C6 - C10, respectively. Figure 1 is an ORTEP diagram showing the atom labelling scheme.

Compound (I) is the first example of a bent chromocene, with centroid - metal - centroid angle 173°. The metallocenes [1,3-(Me3C)2C5H3]2Fe and [1,3-(Me3C)2C5H3]2Co are also unusual examples of bent metallocenes of those metals. This is presumably due to the steric bulk of the four tertiary butyl groups, which force the rings to bend back although there are no close metal - carbon distances indicating agostic metal - hydrogen interactions.

The twist angle of a metallocene is defined as the mean value of the five angles between a ring carbon atom on the upper ring and the closest one on the lower ring. The angles are measured between the planes defined by the two centroids and each ring carbon atom. Thus, it can vary from zero (perfectly eclipsed), in which the rings lie directly above one another, to 36° (completely staggered), in which the plane containing the lower carbon atom bisects the 72° angle between two carbon atoms of the upper ring. The cyclopentadienyl rings of the two unique molecules in (I) are close to being eclipsed (twist angle molecule 1: 14.4°; molecule 2: 13.2°) and are oriented so that the tertiary butyl groups lie on alternating positions on each ring, presumably to minimize steric repulsions.

It is informative to compare the structural parameters for (I) with those of the five other base-free chromium(II) metallocenes that have been structurally characterized (excluding ansa-bridged examples). In the structures of unsubstituted (C5H5)2Cr (Flower & Hitchcock, 1996), (1,2,3,4-Ph4C5H)2Cr (Castellani et al., 1987) and [1,2,4-(Me2CH)3C5H2]2Cr (Overby et al., 1998), the chromium metal lies on a crystallographic inversion centre and the cyclopentadienyl rings are therefore exactly parallel and perfectly staggered (twist angles 36°). In (Me5C5)2Cr (Blümel et al., 1996) and (MeC5H4)2Cr (Benetollo et al., 1994), the centroid-metal-centroid angles are 179/180° (two unique molecules) and 178°, respectively, and the twist angles are 17/7° and 3°. Thus, (I) is the only significantly bent chromocene, although the twist angles in (I) are not unusual. The metal - ring centroid distances in all of these structures lie between 1.78 and 1.81 Å, except for (1,2,3,4-Ph4C5H)2Cr (1.832 Å), which shows elongated metal - ring distances due to the extreme bulk of the ligand in that case.

Related literature top

The corresponding iron and cobalt metallocenes are isostructural (Boese et al., 1993; Schneider et al., 1997). Five other chromocenes have been structurally characterized (Flower & Hitchcock, 1996; Castellani et al., 1987; Overby et al., 1998; Blümel et al., 1996; Benetollo et al., 1994). For related literature, see: Schultz et al. (2000, 2001).

Experimental top

The sodium salt Na[1,3-(Me3C)2C5H3] (2.71 g, 0.0135 mol) and Cr2(OAc)4 (1.15 g, 3.39 mmol) were weighed into a Schlenk flask equipped with a magnetic stirrer under a flow of dinitrogen. THF (180 ml) was added and the slurry was stirred at room temperature for one hour, then heated to reflux and stirred at reflux overnight. The solvent was then removed under reduced pressure and the residue was extracted to pentane (100 ml). The volume of solvent was reduced and the solution was cooled to -80°C. Large red air-sensitive crystals formed in 77% yield. mp 183–184°C. 1H NMR (C6D6, 23°C): δ 0.2 (ν1/2 = 250 Hz, Me3C) (ring protons not observed). The molecule sublimes under dynamic vacuum. The synthesis of compound (I) has also been reported by a different route (Overby et al., 1998). For data collection, a red crystal was placed in Paratone N hydrocarbon oil and then mounted on a glass fiber.

Computing details top

Data collection: SMART (Siemens, 1995a); cell refinement: XPREP (Sheldrick, 1995); data reduction: SAINT (Siemens, 1995b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: XP in SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules of (I) showing the atom labelling scheme for one ring of each molecule (the second ring on each molecule is generated by symmetry). Hydrogen atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level.
Bis(η5-1,3-di-tert-butylcyclopentadienyl)chromium(II) top
Crystal data top
[Cr(C13H21)2]Dx = 1.133 Mg m3
Mr = 406.60Melting point: not measured K
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 5151 reflections
a = 11.7750 (6) Åθ = 1.5–44.3°
b = 12.4122 (6) ŵ = 0.49 mm1
c = 32.621 (2) ÅT = 134 K
V = 4767.7 (4) Å3Block, red
Z = 80.21 × 0.19 × 0.08 mm
F(000) = 1776
Data collection top
Bruker SMART 1K CCD
diffractometer
4385 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
ω–scanθmax = 26.3°, θmin = 1.3°
Absorption correction: multi-scan
(XPREP; Sheldrick, 1995)
h = 1213
Tmin = 0.905, Tmax = 0.962k = 1415
21800 measured reflectionsl = 2939
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0517P)2 + 1.131P]
where P = (Fo2 + 2Fc2)/3
4385 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
[Cr(C13H21)2]V = 4767.7 (4) Å3
Mr = 406.60Z = 8
Orthorhombic, PccnMo Kα radiation
a = 11.7750 (6) ŵ = 0.49 mm1
b = 12.4122 (6) ÅT = 134 K
c = 32.621 (2) Å0.21 × 0.19 × 0.08 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
4385 independent reflections
Absorption correction: multi-scan
(XPREP; Sheldrick, 1995)
2665 reflections with I > 2σ(I)
Tmin = 0.905, Tmax = 0.962Rint = 0.077
21800 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.02Δρmax = 0.29 e Å3
4385 reflectionsΔρmin = 0.26 e Å3
257 parameters
Special details top

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
Cr10.25000.75000.044372 (18)0.01940 (17)
Cr20.25000.25000.181375 (18)0.01916 (17)
C10.3177 (2)0.5946 (2)0.02512 (9)0.0212 (7)
C20.3437 (2)0.6067 (2)0.06750 (8)0.0207 (7)
H20.31880.55940.08860.025*
C30.4122 (2)0.6995 (2)0.07379 (8)0.0222 (7)
C40.4290 (2)0.7466 (2)0.03457 (8)0.0234 (6)
H40.47120.81020.02920.028*
C50.3721 (2)0.6824 (2)0.00459 (9)0.0220 (7)
H50.37060.69570.02410.026*
C60.2885 (2)0.4079 (2)0.21043 (9)0.0228 (7)
C70.3923 (2)0.3517 (2)0.20460 (9)0.0230 (7)
H70.44390.33320.22590.028*
C80.4079 (2)0.3272 (2)0.16259 (9)0.0213 (7)
C90.3112 (2)0.3702 (2)0.14162 (9)0.0221 (7)
H90.29810.36690.11290.026*
C100.2378 (3)0.4189 (2)0.17099 (9)0.0252 (7)
H100.16730.45280.16530.030*
C110.2585 (3)0.4994 (2)0.00510 (8)0.0239 (6)
C120.1652 (3)0.4525 (2)0.03243 (9)0.0309 (8)
H12A0.19780.43150.05890.046*
H12B0.13200.38920.01910.046*
H12C0.10610.50690.03680.046*
C130.3488 (3)0.4123 (2)0.00243 (11)0.0428 (9)
H13A0.40740.44060.02080.064*
H13B0.31310.34910.01500.064*
H13C0.38340.39160.02370.064*
C140.2046 (3)0.5316 (3)0.03600 (9)0.0365 (8)
H14A0.14710.58730.03130.055*
H14B0.16880.46840.04850.055*
H14C0.26350.55960.05440.055*
C610.2435 (3)0.4578 (2)0.25000 (9)0.0271 (7)
C620.2590 (3)0.5806 (2)0.24669 (10)0.0371 (8)
H62A0.33960.59720.24260.056*
H62B0.23220.61490.27200.056*
H62C0.21510.60780.22340.056*
C630.3097 (3)0.4167 (3)0.28684 (9)0.0359 (8)
H63A0.30360.33810.28830.054*
H63B0.27840.44850.31190.054*
H63C0.38970.43720.28410.054*
C640.1172 (3)0.4333 (3)0.25587 (10)0.0394 (9)
H64A0.07460.45920.23200.059*
H64B0.08970.46970.28060.059*
H64C0.10650.35540.25870.059*
C310.4666 (2)0.7361 (2)0.11388 (9)0.0256 (7)
C320.4532 (3)0.8584 (2)0.11985 (10)0.0368 (8)
H32A0.48520.89620.09610.055*
H32B0.49340.88060.14470.055*
H32C0.37240.87620.12250.055*
C330.4152 (3)0.6778 (3)0.15074 (9)0.0361 (8)
H33A0.33340.69190.15190.054*
H33B0.45110.70390.17600.054*
H33C0.42820.60010.14800.054*
C340.5942 (3)0.7094 (3)0.11186 (10)0.0371 (8)
H34A0.60400.63260.10590.056*
H34B0.62980.72660.13820.056*
H34C0.62990.75220.09010.056*
C810.5135 (2)0.2797 (2)0.14232 (9)0.0234 (7)
C820.5899 (3)0.3743 (3)0.12892 (10)0.0350 (8)
H82A0.65750.34610.11500.053*
H82B0.61300.41570.15310.053*
H82C0.54770.42110.11010.053*
C830.4825 (3)0.2132 (2)0.10470 (9)0.0340 (8)
H83A0.43450.15250.11300.051*
H83B0.55190.18590.09180.051*
H83C0.44110.25840.08510.051*
C840.5793 (2)0.2087 (3)0.17218 (9)0.0316 (8)
H84A0.53050.14970.18160.047*
H84B0.60350.25180.19580.047*
H84C0.64630.17890.15840.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0175 (3)0.0205 (3)0.0202 (4)0.0028 (3)0.0000.000
Cr20.0189 (3)0.0191 (3)0.0195 (3)0.0008 (3)0.0000.000
C10.0182 (16)0.0217 (15)0.0237 (17)0.0048 (13)0.0014 (13)0.0011 (13)
C20.0205 (16)0.0207 (15)0.0208 (16)0.0032 (13)0.0000 (13)0.0015 (13)
C30.0176 (15)0.0264 (16)0.0227 (17)0.0032 (13)0.0001 (13)0.0017 (14)
C40.0186 (14)0.0208 (14)0.0308 (16)0.0001 (14)0.0038 (12)0.0007 (15)
C50.0184 (15)0.0250 (16)0.0225 (17)0.0041 (13)0.0042 (13)0.0001 (13)
C60.0226 (15)0.0218 (15)0.0241 (17)0.0014 (13)0.0007 (13)0.0006 (13)
C70.0240 (16)0.0239 (15)0.0210 (17)0.0032 (13)0.0051 (13)0.0025 (13)
C80.0215 (16)0.0200 (15)0.0225 (16)0.0054 (13)0.0012 (13)0.0012 (13)
C90.0271 (17)0.0194 (15)0.0198 (17)0.0032 (13)0.0005 (13)0.0033 (13)
C100.0241 (17)0.0192 (14)0.0322 (17)0.0015 (14)0.0014 (14)0.0025 (13)
C110.0256 (16)0.0224 (14)0.0236 (15)0.0009 (14)0.0006 (15)0.0023 (12)
C120.0351 (19)0.0294 (17)0.0281 (19)0.0065 (15)0.0056 (15)0.0023 (15)
C130.039 (2)0.0292 (18)0.060 (2)0.0042 (16)0.0033 (18)0.0139 (18)
C140.046 (2)0.038 (2)0.0246 (19)0.0098 (16)0.0054 (15)0.0028 (15)
C310.0210 (15)0.0266 (17)0.0292 (17)0.0015 (14)0.0045 (13)0.0037 (14)
C320.039 (2)0.0331 (19)0.039 (2)0.0012 (16)0.0122 (16)0.0095 (16)
C330.040 (2)0.043 (2)0.0256 (19)0.0033 (16)0.0072 (16)0.0005 (16)
C340.0281 (18)0.044 (2)0.039 (2)0.0013 (15)0.0122 (16)0.0042 (16)
C610.0242 (16)0.0265 (16)0.0306 (17)0.0005 (16)0.0003 (16)0.0067 (13)
C620.044 (2)0.0304 (17)0.0374 (19)0.0014 (18)0.0040 (17)0.0119 (15)
C630.0387 (19)0.042 (2)0.0271 (19)0.0016 (17)0.0016 (16)0.0069 (16)
C640.0309 (19)0.049 (2)0.038 (2)0.0016 (17)0.0084 (16)0.0178 (17)
C810.0197 (15)0.0263 (17)0.0242 (17)0.0006 (12)0.0026 (13)0.0008 (13)
C820.0292 (18)0.0374 (19)0.038 (2)0.0041 (15)0.0093 (16)0.0024 (16)
C830.0324 (18)0.0415 (19)0.0280 (18)0.0009 (15)0.0050 (15)0.0053 (15)
C840.0248 (17)0.0380 (18)0.0321 (19)0.0036 (15)0.0027 (15)0.0003 (15)
Geometric parameters (Å, º) top
Cr1—C1i2.180 (3)C12—H12A0.9800
Cr1—C12.180 (3)C12—H12B0.9800
Cr1—C2i2.225 (3)C12—H12C0.9800
Cr1—C22.225 (3)C13—H13A0.9800
Cr1—C3i2.228 (3)C13—H13B0.9800
Cr1—C32.228 (3)C13—H13C0.9800
Cr1—C4i2.133 (3)C14—H14A0.9800
Cr1—C42.133 (3)C14—H14B0.9800
Cr1—C5i2.111 (3)C14—H14C0.9800
Cr1—C52.111 (3)C61—C631.520 (4)
Cr1—Cg11.807C61—C641.529 (4)
Cr2—C62.224 (3)C61—C621.539 (4)
Cr2—C6ii2.224 (3)C62—H62A0.9800
Cr2—C72.230 (3)C62—H62B0.9800
Cr2—C7ii2.230 (3)C62—H62C0.9800
Cr2—C8ii2.179 (3)C63—H63A0.9800
Cr2—C82.179 (3)C63—H63B0.9800
Cr2—C9ii2.104 (3)C63—H63C0.9800
Cr2—C92.104 (3)C64—H64A0.9800
Cr2—C102.128 (3)C64—H64B0.9800
Cr2—C10ii2.128 (3)C64—H64C0.9800
Cr2—Cg21.805C31—C331.529 (4)
C1—C21.424 (4)C31—C321.538 (4)
C1—C51.430 (4)C31—C341.540 (4)
C1—C111.520 (4)C32—H32A0.9800
C2—C31.422 (4)C32—H32B0.9800
C2—H20.9500C32—H32C0.9800
C3—C41.420 (4)C33—H33A0.9800
C3—C311.525 (4)C33—H33B0.9800
C4—C51.429 (4)C33—H33C0.9800
C4—H40.9500C34—H34A0.9800
C5—H50.9500C34—H34B0.9800
C6—C71.420 (4)C34—H34C0.9800
C6—C101.425 (4)C81—C831.524 (4)
C6—C611.526 (4)C81—C841.525 (4)
C7—C81.416 (4)C81—C821.541 (4)
C7—H70.9500C82—H82A0.9800
C8—C91.432 (4)C82—H82B0.9800
C8—C811.527 (4)C82—H82C0.9800
C9—C101.424 (4)C83—H83A0.9800
C9—H90.9500C83—H83B0.9800
C10—H100.9500C83—H83C0.9800
C11—C121.529 (4)C84—H84A0.9800
C11—C141.536 (4)C84—H84B0.9800
C11—C131.536 (4)C84—H84C0.9800
Cg1i—Cr1—Cg1173.3C10—C6—C61125.4 (3)
Cg2ii—Cr2—Cg2173.1C7—C6—Cr271.66 (16)
C5i—Cr1—C5104.13 (16)C10—C6—Cr267.29 (15)
C5i—Cr1—C4i39.34 (10)C61—C6—Cr2130.32 (19)
C5—Cr1—C4i126.08 (11)C8—C7—C6110.3 (2)
C5i—Cr1—C4126.08 (11)C8—C7—Cr269.33 (15)
C5—Cr1—C439.34 (10)C6—C7—Cr271.16 (16)
C4i—Cr1—C4162.75 (15)C8—C7—H7124.8
C5i—Cr1—C1i38.89 (10)C6—C7—H7124.8
C5—Cr1—C1i115.10 (11)Cr2—C7—H7126.3
C4i—Cr1—C1i65.00 (11)C7—C8—C9106.2 (2)
C4—Cr1—C1i109.65 (11)C7—C8—C81127.4 (2)
C5i—Cr1—C1115.09 (11)C9—C8—C81125.8 (3)
C5—Cr1—C138.89 (10)C7—C8—Cr273.23 (16)
C4i—Cr1—C1109.65 (11)C9—C8—Cr267.67 (15)
C4—Cr1—C165.00 (11)C81—C8—Cr2130.35 (19)
C1i—Cr1—C1146.51 (15)C10—C9—C8108.6 (3)
C5i—Cr1—C2i63.43 (10)C10—C9—Cr271.23 (15)
C5—Cr1—C2i149.79 (10)C8—C9—Cr273.33 (15)
C4i—Cr1—C2i62.92 (11)C10—C9—H9125.7
C4—Cr1—C2i123.85 (11)C8—C9—H9125.7
C1i—Cr1—C2i37.70 (10)Cr2—C9—H9121.4
C1—Cr1—C2i170.62 (10)C9—C10—C6108.3 (3)
C5i—Cr1—C2149.79 (10)C9—C10—Cr269.44 (15)
C5—Cr1—C263.43 (10)C6—C10—Cr274.57 (16)
C4i—Cr1—C2123.85 (11)C9—C10—H10125.9
C4—Cr1—C262.92 (11)C6—C10—H10125.9
C1i—Cr1—C2170.62 (10)Cr2—C10—H10121.8
C1—Cr1—C237.70 (10)C1—C11—C12112.0 (2)
C2i—Cr1—C2140.35 (14)C1—C11—C14111.3 (2)
C5i—Cr1—C3i64.46 (11)C12—C11—C14108.1 (2)
C5—Cr1—C3i163.88 (11)C1—C11—C13107.3 (2)
C4i—Cr1—C3i37.93 (10)C12—C11—C13108.8 (2)
C4—Cr1—C3i156.62 (11)C14—C11—C13109.2 (3)
C1i—Cr1—C3i63.98 (10)C11—C12—H12A109.5
C1—Cr1—C3i133.38 (10)C11—C12—H12B109.5
C2i—Cr1—C3i37.24 (10)H12A—C12—H12B109.5
C2—Cr1—C3i120.26 (10)C11—C12—H12C109.5
C5i—Cr1—C3163.88 (11)H12A—C12—H12C109.5
C5—Cr1—C364.46 (11)H12B—C12—H12C109.5
C4i—Cr1—C3156.62 (11)C11—C13—H13A109.5
C4—Cr1—C337.93 (10)C11—C13—H13B109.5
C1i—Cr1—C3133.38 (10)H13A—C13—H13B109.5
C1—Cr1—C363.98 (10)C11—C13—H13C109.5
C2i—Cr1—C3120.26 (10)H13A—C13—H13C109.5
C2—Cr1—C337.24 (10)H13B—C13—H13C109.5
C3i—Cr1—C3128.98 (14)C11—C14—H14A109.5
C9ii—Cr2—C9103.90 (16)C11—C14—H14B109.5
C9ii—Cr2—C10125.26 (11)H14A—C14—H14B109.5
C9—Cr2—C1039.32 (11)C11—C14—H14C109.5
C9ii—Cr2—C10ii39.32 (11)H14A—C14—H14C109.5
C9—Cr2—C10ii125.26 (11)H14B—C14—H14C109.5
C10—Cr2—C10ii161.68 (16)C63—C61—C6110.8 (2)
C9ii—Cr2—C8ii39.01 (10)C63—C61—C64109.4 (3)
C9—Cr2—C8ii115.49 (11)C6—C61—C64111.3 (2)
C10—Cr2—C8ii109.31 (11)C63—C61—C62109.1 (2)
C10ii—Cr2—C8ii65.15 (11)C6—C61—C62107.5 (2)
C9ii—Cr2—C8115.49 (11)C64—C61—C62108.7 (3)
C9—Cr2—C839.01 (10)C61—C62—H62A109.5
C10—Cr2—C865.15 (11)C61—C62—H62B109.5
C10ii—Cr2—C8109.31 (11)H62A—C62—H62B109.5
C8ii—Cr2—C8147.33 (15)C61—C62—H62C109.5
C9ii—Cr2—C6163.24 (11)H62A—C62—H62C109.5
C9—Cr2—C664.40 (11)H62B—C62—H62C109.5
C10—Cr2—C638.14 (10)C61—C63—H63A109.5
C10ii—Cr2—C6157.26 (11)C61—C63—H63B109.5
C8ii—Cr2—C6132.93 (10)H63A—C63—H63B109.5
C8—Cr2—C663.81 (10)C61—C63—H63C109.5
C9ii—Cr2—C6ii64.40 (11)H63A—C63—H63C109.5
C9—Cr2—C6ii163.24 (11)H63B—C63—H63C109.5
C10—Cr2—C6ii157.26 (11)C61—C64—H64A109.5
C10ii—Cr2—C6ii38.14 (10)C61—C64—H64B109.5
C8ii—Cr2—C6ii63.81 (10)H64A—C64—H64B109.5
C8—Cr2—C6ii132.93 (10)C61—C64—H64C109.5
C6—Cr2—C6ii129.54 (15)H64A—C64—H64C109.5
C9ii—Cr2—C7150.22 (11)H64B—C64—H64C109.5
C9—Cr2—C763.31 (11)C3—C31—C33111.6 (2)
C10—Cr2—C763.07 (11)C3—C31—C32111.1 (2)
C10ii—Cr2—C7124.13 (11)C33—C31—C32109.1 (2)
C8ii—Cr2—C7170.09 (10)C3—C31—C34108.0 (2)
C8—Cr2—C737.44 (10)C33—C31—C34108.5 (2)
C6—Cr2—C737.18 (10)C32—C31—C34108.5 (2)
C6ii—Cr2—C7120.48 (10)C31—C32—H32A109.5
C9ii—Cr2—C7ii63.31 (11)C31—C32—H32B109.5
C9—Cr2—C7ii150.22 (11)H32A—C32—H32B109.5
C10—Cr2—C7ii124.13 (11)C31—C32—H32C109.5
C10ii—Cr2—C7ii63.07 (11)H32A—C32—H32C109.5
C8ii—Cr2—C7ii37.44 (10)H32B—C32—H32C109.5
C8—Cr2—C7ii170.09 (10)C31—C33—H33A109.5
C6—Cr2—C7ii120.48 (10)C31—C33—H33B109.5
C6ii—Cr2—C7ii37.18 (10)H33A—C33—H33B109.5
C7—Cr2—C7ii140.28 (15)C31—C33—H33C109.5
C2—C1—C5106.2 (2)H33A—C33—H33C109.5
C2—C1—C11126.7 (2)H33B—C33—H33C109.5
C5—C1—C11126.6 (3)C31—C34—H34A109.5
C2—C1—Cr172.89 (15)C31—C34—H34B109.5
C5—C1—Cr167.96 (15)H34A—C34—H34B109.5
C11—C1—Cr1130.08 (19)C31—C34—H34C109.5
C3—C2—C1110.3 (2)H34A—C34—H34C109.5
C3—C2—Cr171.48 (16)H34B—C34—H34C109.5
C1—C2—Cr169.41 (15)C83—C81—C84108.8 (2)
C3—C2—H2124.8C83—C81—C8111.2 (2)
C1—C2—H2124.8C84—C81—C8111.1 (2)
Cr1—C2—H2125.9C83—C81—C82108.9 (2)
C4—C3—C2106.4 (2)C84—C81—C82109.0 (2)
C4—C3—C31126.3 (3)C8—C81—C82107.7 (2)
C2—C3—C31127.1 (3)C81—C82—H82A109.5
C4—C3—Cr167.41 (15)C81—C82—H82B109.5
C2—C3—Cr171.28 (15)H82A—C82—H82B109.5
C31—C3—Cr1130.19 (19)C81—C82—H82C109.5
C3—C4—C5108.8 (3)H82A—C82—H82C109.5
C3—C4—Cr174.66 (16)H82B—C82—H82C109.5
C5—C4—Cr169.49 (15)C81—C83—H83A109.5
C3—C4—H4125.6C81—C83—H83B109.5
C5—C4—H4125.6H83A—C83—H83B109.5
Cr1—C4—H4121.9C81—C83—H83C109.5
C4—C5—C1108.3 (3)H83A—C83—H83C109.5
C4—C5—Cr171.16 (15)H83B—C83—H83C109.5
C1—C5—Cr173.16 (16)C81—C84—H84A109.5
C4—C5—H5125.8C81—C84—H84B109.5
C1—C5—H5125.8H84A—C84—H84B109.5
Cr1—C5—H5121.6C81—C84—H84C109.5
C7—C6—C10106.6 (3)H84A—C84—H84C109.5
C7—C6—C61127.7 (3)H84B—C84—H84C109.5
C1—C2—C3—C40.2 (3)C7—C6—C61—C6314.4 (4)
C1—C2—C3—C31174.6 (3)C10—C6—C61—C63172.3 (3)
C2—C3—C4—C50.5 (3)Cr2—C6—C61—C6383.3 (3)
C31—C3—C4—C5174.3 (2)C7—C6—C61—C64136.4 (3)
C3—C4—C5—C10.6 (3)C10—C6—C61—C6450.3 (4)
C2—C1—C5—C40.5 (3)C7—C6—C61—C62104.7 (3)
C6—C7—C8—C90.5 (3)C10—C6—C61—C6268.7 (4)
C6—C7—C8—C81172.1 (3)C4—C3—C31—C33171.3 (3)
C7—C8—C9—C100.7 (3)C2—C3—C31—C3314.9 (4)
C81—C8—C9—C10172.6 (2)C4—C3—C31—C3249.4 (4)
C8—C9—C10—C60.7 (3)C2—C3—C31—C32136.8 (3)
C7—C6—C10—C90.4 (3)C4—C3—C31—C3469.5 (4)
C61—C6—C10—C9174.1 (2)C2—C3—C31—C34104.3 (3)
C2—C1—C11—C1236.7 (4)C7—C8—C81—C83150.6 (3)
C5—C1—C11—C12152.6 (3)C9—C8—C81—C8339.3 (4)
C2—C1—C11—C14157.9 (3)C7—C8—C81—C8429.2 (4)
C5—C1—C11—C1431.4 (4)C9—C8—C81—C84160.7 (3)
C2—C1—C11—C1382.7 (3)C7—C8—C81—C8290.1 (3)
C5—C1—C11—C1388.0 (3)C9—C8—C81—C8280.0 (3)
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Cr(C13H21)2]
Mr406.60
Crystal system, space groupOrthorhombic, Pccn
Temperature (K)134
a, b, c (Å)11.7750 (6), 12.4122 (6), 32.621 (2)
V3)4767.7 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.49
Crystal size (mm)0.21 × 0.19 × 0.08
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(XPREP; Sheldrick, 1995)
Tmin, Tmax0.905, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections
21800, 4385, 2665
Rint0.077
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.114, 1.02
No. of reflections4385
No. of parameters257
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.26

Computer programs: SMART (Siemens, 1995a), XPREP (Sheldrick, 1995), SAINT (Siemens, 1995b), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), XP in SHELXTL (Sheldrick, 1998).

Selected geometric parameters (Å, º) top
Cr1—C12.180 (3)Cr2—C62.224 (3)
Cr1—C22.225 (3)Cr2—C72.230 (3)
Cr1—C32.228 (3)Cr2—C82.179 (3)
Cr1—C42.133 (3)Cr2—C92.104 (3)
Cr1—C52.111 (3)Cr2—C102.128 (3)
Cr1—Cg11.807Cr2—Cg21.805
Cg1i—Cr1—Cg1173.3Cg2ii—Cr2—Cg2173.1
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1/2, y+1/2, z.
 

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