Tricarbon­yl[η⁶-1-methyl-4-(trimethyl­silyl)benzene]chromium(0)

The mol­ecule of the title compound, [Cr(C₁₀H₁₆Si)(CO)₃], has an eclipsed orientation of the Cr(CO)₃ group relative to three benzene ring atoms. The atoms attached to the benzene ring show very small deviations from the benzene plane in the direction towards the Cr atom.

Key indicators

• Single-crystal X-ray study
• T = 149 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.100
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C13     ..       7.42 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cr     -   C13     ..      10.37 su

Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          4
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr     -   C11     ..       6.36 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr     -   C12     ..       7.09 su

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.

Tricarbonyl[η⁶-1-methyl-4-(trimethylsilyl)benzene]chromium(0)

Crystal data

[Cr(C10H16Si)(CO)3]	F(000) = 624
Mr = 300.35	Dx = 1.403 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 84 reflections
a = 6.8929 (16) Å	θ = 3–23°
b = 17.747 (3) Å	µ = 0.89 mm^−1
c = 11.848 (3) Å	T = 149 K
β = 101.19 (2)°	Plate, yellow
V = 1421.8 (6) Å^3	0.28 × 0.20 × 0.04 mm
Z = 4

Data collection

Siemens SMART 1K CCD area-detector diffractometer	4283 independent reflections
Radiation source: normal-focus sealed tube	2645 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
ω scans	θmax = 30.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→9
Tmin = 0.864, Tmax = 0.965	k = −24→25
23158 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
4283 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.49 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
Cr	0.79020 (6)	0.154707 (19)	0.54042 (3)	0.01608 (11)
Si	0.74155 (10)	0.36061 (3)	0.50316 (6)	0.02025 (16)
O1	0.6882 (3)	0.18098 (11)	0.77179 (15)	0.0367 (5)
O2	1.2133 (3)	0.18919 (11)	0.64332 (16)	0.0383 (5)
O3	0.8782 (3)	−0.00544 (9)	0.61244 (15)	0.0307 (4)
C1	0.6933 (4)	0.26179 (12)	0.44687 (19)	0.0182 (5)
C2	0.5248 (4)	0.22024 (13)	0.4646 (2)	0.0190 (5)
C3	0.4921 (4)	0.14529 (13)	0.4279 (2)	0.0201 (5)
C4	0.6284 (4)	0.10752 (12)	0.37378 (19)	0.0190 (5)
C5	0.7935 (4)	0.14764 (13)	0.3530 (2)	0.0205 (5)
C6	0.8254 (4)	0.22267 (13)	0.3898 (2)	0.0203 (5)
C7	0.5962 (4)	0.02624 (12)	0.3356 (2)	0.0251 (6)
H7A	0.5082	0.0244	0.2600	0.038*
H7B	0.5361	−0.0015	0.3916	0.038*
H7C	0.7236	0.0033	0.3306	0.038*
C8	0.6129 (4)	0.42802 (13)	0.3932 (2)	0.0342 (7)
H8A	0.4698	0.4199	0.3816	0.051*
H8B	0.6575	0.4199	0.3205	0.051*
H8C	0.6437	0.4797	0.4197	0.051*
C9	1.0130 (4)	0.37872 (15)	0.5305 (2)	0.0342 (7)
H9A	1.0807	0.3421	0.5865	0.051*
H9B	1.0396	0.4298	0.5611	0.051*
H9C	1.0614	0.3738	0.4584	0.051*
C10	0.6425 (4)	0.37036 (14)	0.6378 (2)	0.0293 (6)
H10A	0.7141	0.3363	0.6966	0.044*
H10B	0.5016	0.3575	0.6224	0.044*
H10C	0.6598	0.4224	0.6655	0.044*
C11	0.7255 (4)	0.17113 (13)	0.6824 (2)	0.0234 (6)
C12	1.0489 (4)	0.17695 (13)	0.6035 (2)	0.0235 (6)
C13	0.8450 (4)	0.05652 (14)	0.5847 (2)	0.0223 (5)
H2	0.444 (3)	0.2425 (12)	0.5078 (19)	0.016 (3)*
H3	0.391 (3)	0.1219 (12)	0.4446 (19)	0.016 (3)*
H5	0.887 (3)	0.1240 (12)	0.3222 (19)	0.016 (3)*
H6	0.942 (4)	0.2480 (12)	0.3786 (19)	0.016 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr	0.0150 (2)	0.01905 (18)	0.01495 (19)	0.00059 (16)	0.00484 (14)	0.00157 (15)
Si	0.0223 (4)	0.0201 (3)	0.0186 (3)	−0.0012 (3)	0.0045 (3)	−0.0004 (2)
O1	0.0371 (12)	0.0555 (12)	0.0202 (10)	0.0159 (10)	0.0123 (9)	0.0045 (9)
O2	0.0203 (11)	0.0595 (13)	0.0339 (12)	−0.0065 (9)	0.0020 (9)	0.0030 (9)
O3	0.0312 (11)	0.0225 (9)	0.0382 (11)	0.0042 (8)	0.0061 (9)	0.0066 (8)
C1	0.0185 (13)	0.0209 (11)	0.0149 (12)	0.0000 (10)	0.0027 (10)	0.0023 (9)
C2	0.0176 (13)	0.0224 (12)	0.0174 (13)	0.0048 (10)	0.0043 (10)	0.0014 (9)
C3	0.0177 (13)	0.0227 (12)	0.0196 (12)	−0.0018 (10)	0.0027 (10)	0.0028 (10)
C4	0.0208 (13)	0.0202 (11)	0.0145 (12)	0.0012 (10)	−0.0008 (10)	0.0022 (9)
C5	0.0241 (14)	0.0232 (12)	0.0155 (12)	0.0045 (11)	0.0069 (10)	0.0008 (9)
C6	0.0202 (14)	0.0241 (12)	0.0178 (12)	−0.0028 (10)	0.0068 (11)	0.0045 (10)
C7	0.0265 (15)	0.0243 (12)	0.0239 (13)	0.0002 (11)	0.0030 (11)	−0.0044 (10)
C8	0.0497 (19)	0.0209 (12)	0.0283 (15)	−0.0034 (12)	−0.0013 (13)	0.0015 (11)
C9	0.0294 (16)	0.0349 (15)	0.0400 (17)	−0.0105 (12)	0.0108 (13)	−0.0120 (12)
C10	0.0368 (17)	0.0290 (13)	0.0246 (14)	−0.0013 (12)	0.0119 (13)	−0.0038 (10)
C11	0.0187 (14)	0.0283 (13)	0.0236 (14)	0.0072 (10)	0.0052 (11)	0.0046 (10)
C12	0.0261 (15)	0.0274 (13)	0.0176 (13)	−0.0005 (11)	0.0059 (11)	0.0041 (10)
C13	0.0157 (13)	0.0314 (13)	0.0196 (12)	−0.0024 (11)	0.0027 (10)	−0.0013 (11)

Geometric parameters (Å, º)

Cr—C13	1.838 (2)	C3—C4	1.406 (3)
Cr—C12	1.838 (3)	C3—H3	0.87 (2)
Cr—C11	1.845 (3)	C4—C5	1.404 (3)
Cr—C6	2.206 (2)	C4—C7	1.515 (3)
Cr—C2	2.207 (2)	C5—C6	1.405 (3)
Cr—C3	2.228 (3)	C5—H5	0.91 (2)
Cr—C5	2.228 (2)	C6—H6	0.95 (2)
Cr—C4	2.234 (2)	C7—H7A	0.9800
Cr—C1	2.236 (2)	C7—H7B	0.9800
Si—C10	1.861 (3)	C7—H7C	0.9800
Si—C8	1.862 (3)	C8—H8A	0.9800
Si—C9	1.864 (3)	C8—H8B	0.9800
Si—C1	1.883 (2)	C8—H8C	0.9800
O1—C11	1.151 (3)	C9—H9A	0.9800
O2—C12	1.160 (3)	C9—H9B	0.9800
O3—C13	1.158 (3)	C9—H9C	0.9800
C1—C6	1.417 (3)	C10—H10A	0.9800
C1—C2	1.425 (3)	C10—H10B	0.9800
C2—C3	1.404 (3)	C10—H10C	0.9800
C2—H2	0.92 (2)
C13—Cr—C12	87.60 (10)	Cr—C2—H2	123.1 (14)
C13—Cr—C11	87.85 (10)	C2—C3—C4	120.8 (2)
C12—Cr—C11	89.00 (11)	C2—C3—Cr	70.73 (14)
C13—Cr—C6	134.46 (10)	C4—C3—Cr	71.85 (14)
C12—Cr—C6	87.77 (10)	C2—C3—H3	118.1 (15)
C11—Cr—C6	137.31 (10)	C4—C3—H3	121.0 (15)
C13—Cr—C2	136.40 (10)	Cr—C3—H3	126.1 (15)
C12—Cr—C2	135.63 (10)	C5—C4—C3	118.3 (2)
C11—Cr—C2	87.70 (10)	C5—C4—C7	120.5 (2)
C6—Cr—C2	66.11 (9)	C3—C4—C7	121.2 (2)
C13—Cr—C3	102.37 (10)	C5—C4—Cr	71.46 (13)
C12—Cr—C3	165.68 (10)	C3—C4—Cr	71.41 (14)
C11—Cr—C3	101.49 (10)	C7—C4—Cr	129.78 (16)
C6—Cr—C3	77.91 (9)	C4—C5—C6	120.7 (2)
C2—Cr—C3	36.90 (8)	C4—C5—Cr	71.86 (14)
C13—Cr—C5	100.93 (10)	C6—C5—Cr	70.66 (14)
C12—Cr—C5	102.75 (10)	C4—C5—H5	120.2 (14)
C11—Cr—C5	165.51 (10)	C6—C5—H5	118.8 (14)
C6—Cr—C5	36.95 (8)	Cr—C5—H5	125.0 (14)
C2—Cr—C5	77.98 (9)	C5—C6—C1	122.4 (2)
C3—Cr—C5	65.55 (9)	C5—C6—Cr	72.39 (13)
C13—Cr—C4	86.35 (9)	C1—C6—Cr	72.55 (13)
C12—Cr—C4	135.95 (10)	C5—C6—H6	119.3 (13)
C11—Cr—C4	134.22 (10)	C1—C6—H6	118.3 (13)
C6—Cr—C4	66.70 (9)	Cr—C6—H6	126.8 (13)
C2—Cr—C4	66.75 (9)	C4—C7—H7A	109.5
C3—Cr—C4	36.74 (9)	C4—C7—H7B	109.5
C5—Cr—C4	36.67 (9)	H7A—C7—H7B	109.5
C13—Cr—C1	166.53 (10)	C4—C7—H7C	109.5
C12—Cr—C1	101.07 (10)	H7A—C7—H7C	109.5
C11—Cr—C1	102.46 (9)	H7B—C7—H7C	109.5
C6—Cr—C1	37.20 (9)	Si—C8—H8A	109.5
C2—Cr—C1	37.42 (9)	Si—C8—H8B	109.5
C3—Cr—C1	67.35 (9)	H8A—C8—H8B	109.5
C5—Cr—C1	67.27 (9)	Si—C8—H8C	109.5
C4—Cr—C1	80.24 (8)	H8A—C8—H8C	109.5
C10—Si—C8	109.64 (13)	H8B—C8—H8C	109.5
C10—Si—C9	110.96 (13)	Si—C9—H9A	109.5
C8—Si—C9	109.67 (13)	Si—C9—H9B	109.5
C10—Si—C1	108.74 (11)	H9A—C9—H9B	109.5
C8—Si—C1	108.86 (11)	Si—C9—H9C	109.5
C9—Si—C1	108.94 (11)	H9A—C9—H9C	109.5
C6—C1—C2	115.8 (2)	H9B—C9—H9C	109.5
C6—C1—Si	122.65 (18)	Si—C10—H10A	109.5
C2—C1—Si	121.52 (18)	Si—C10—H10B	109.5
C6—C1—Cr	70.26 (13)	H10A—C10—H10B	109.5
C2—C1—Cr	70.18 (13)	Si—C10—H10C	109.5
Si—C1—Cr	126.93 (12)	H10A—C10—H10C	109.5
C3—C2—C1	122.1 (2)	H10B—C10—H10C	109.5
C3—C2—Cr	72.36 (14)	O1—C11—Cr	178.8 (2)
C1—C2—Cr	72.40 (13)	O2—C12—Cr	178.4 (2)
C3—C2—H2	120.1 (14)	O3—C13—Cr	179.6 (2)
C1—C2—H2	117.5 (14)
C10—Si—C1—C6	−145.6 (2)	Cr—C3—C4—C5	−55.80 (19)
C8—Si—C1—C6	95.0 (2)	C2—C3—C4—C7	179.0 (2)
C9—Si—C1—C6	−24.6 (2)	Cr—C3—C4—C7	125.8 (2)
C10—Si—C1—C2	31.2 (2)	C2—C3—C4—Cr	53.2 (2)
C8—Si—C1—C2	−88.2 (2)	C13—Cr—C4—C5	−113.82 (15)
C9—Si—C1—C2	152.20 (19)	C12—Cr—C4—C5	−31.1 (2)
C10—Si—C1—Cr	−56.76 (18)	C11—Cr—C4—C5	162.76 (15)
C8—Si—C1—Cr	−176.15 (15)	C6—Cr—C4—C5	28.53 (14)
C9—Si—C1—Cr	64.29 (18)	C2—Cr—C4—C5	101.38 (15)
C13—Cr—C1—C6	−58.2 (5)	C3—Cr—C4—C5	129.8 (2)
C12—Cr—C1—C6	71.12 (16)	C1—Cr—C4—C5	64.82 (15)
C11—Cr—C1—C6	162.56 (15)	C13—Cr—C4—C3	116.37 (15)
C2—Cr—C1—C6	−128.3 (2)	C12—Cr—C4—C3	−160.88 (15)
C3—Cr—C1—C6	−100.04 (16)	C11—Cr—C4—C3	32.95 (19)
C5—Cr—C1—C6	−28.19 (14)	C6—Cr—C4—C3	−101.29 (15)
C4—Cr—C1—C6	−64.07 (15)	C2—Cr—C4—C3	−28.43 (13)
C13—Cr—C1—C2	70.1 (5)	C5—Cr—C4—C3	−129.8 (2)
C12—Cr—C1—C2	−160.56 (15)	C1—Cr—C4—C3	−64.99 (14)
C11—Cr—C1—C2	−69.12 (16)	C13—Cr—C4—C7	0.8 (2)
C6—Cr—C1—C2	128.3 (2)	C12—Cr—C4—C7	83.6 (3)
C3—Cr—C1—C2	28.28 (14)	C11—Cr—C4—C7	−82.6 (2)
C5—Cr—C1—C2	100.13 (15)	C6—Cr—C4—C7	143.2 (2)
C4—Cr—C1—C2	64.25 (15)	C2—Cr—C4—C7	−144.0 (2)
C13—Cr—C1—Si	−174.8 (4)	C3—Cr—C4—C7	−115.5 (3)
C12—Cr—C1—Si	−45.45 (17)	C5—Cr—C4—C7	114.7 (3)
C11—Cr—C1—Si	45.99 (17)	C1—Cr—C4—C7	179.5 (2)
C6—Cr—C1—Si	−116.6 (2)	C3—C4—C5—C6	2.6 (3)
C2—Cr—C1—Si	115.1 (2)	C7—C4—C5—C6	−179.0 (2)
C3—Cr—C1—Si	143.39 (18)	Cr—C4—C5—C6	−53.2 (2)
C5—Cr—C1—Si	−144.77 (18)	C3—C4—C5—Cr	55.78 (19)
C4—Cr—C1—Si	179.36 (17)	C7—C4—C5—Cr	−125.9 (2)
C6—C1—C2—C3	0.1 (3)	C13—Cr—C5—C4	68.42 (15)
Si—C1—C2—C3	−176.86 (18)	C12—Cr—C5—C4	158.41 (14)
Cr—C1—C2—C3	−55.0 (2)	C11—Cr—C5—C4	−58.1 (4)
C6—C1—C2—Cr	55.08 (18)	C6—Cr—C5—C4	−133.1 (2)
Si—C1—C2—Cr	−121.89 (16)	C2—Cr—C5—C4	−67.07 (14)
C13—Cr—C2—C3	−28.2 (2)	C3—Cr—C5—C4	−30.32 (13)
C12—Cr—C2—C3	161.12 (15)	C1—Cr—C5—C4	−104.77 (15)
C11—Cr—C2—C3	−112.66 (16)	C13—Cr—C5—C6	−158.45 (16)
C6—Cr—C2—C3	102.02 (16)	C12—Cr—C5—C6	−68.45 (16)
C5—Cr—C2—C3	65.09 (15)	C11—Cr—C5—C6	75.1 (4)
C4—Cr—C2—C3	28.32 (14)	C2—Cr—C5—C6	66.07 (15)
C1—Cr—C2—C3	133.3 (2)	C3—Cr—C5—C6	102.82 (16)
C13—Cr—C2—C1	−161.48 (15)	C4—Cr—C5—C6	133.1 (2)
C12—Cr—C2—C1	27.8 (2)	C1—Cr—C5—C6	28.37 (14)
C11—Cr—C2—C1	114.07 (15)	C4—C5—C6—C1	−1.3 (4)
C6—Cr—C2—C1	−31.25 (13)	Cr—C5—C6—C1	−55.0 (2)
C3—Cr—C2—C1	−133.3 (2)	C4—C5—C6—Cr	53.7 (2)
C5—Cr—C2—C1	−68.18 (14)	C2—C1—C6—C5	−0.1 (3)
C4—Cr—C2—C1	−104.95 (15)	Si—C1—C6—C5	176.80 (18)
C1—C2—C3—C4	1.3 (4)	Cr—C1—C6—C5	54.9 (2)
Cr—C2—C3—C4	−53.7 (2)	C2—C1—C6—Cr	−55.04 (18)
C1—C2—C3—Cr	55.0 (2)	Si—C1—C6—Cr	121.89 (17)
C13—Cr—C3—C2	160.51 (15)	C13—Cr—C6—C5	30.4 (2)
C12—Cr—C3—C2	−66.2 (4)	C12—Cr—C6—C5	114.79 (16)
C11—Cr—C3—C2	70.20 (16)	C11—Cr—C6—C5	−159.10 (16)
C6—Cr—C3—C2	−66.15 (15)	C2—Cr—C6—C5	−102.11 (16)
C5—Cr—C3—C2	−102.97 (16)	C3—Cr—C6—C5	−65.20 (15)
C4—Cr—C3—C2	−133.2 (2)	C4—Cr—C6—C5	−28.33 (14)
C1—Cr—C3—C2	−28.65 (14)	C1—Cr—C6—C5	−133.5 (2)
C13—Cr—C3—C4	−66.26 (15)	C13—Cr—C6—C1	163.89 (15)
C12—Cr—C3—C4	67.0 (4)	C12—Cr—C6—C1	−111.67 (16)
C11—Cr—C3—C4	−156.56 (14)	C11—Cr—C6—C1	−25.6 (2)
C6—Cr—C3—C4	67.09 (14)	C2—Cr—C6—C1	31.42 (14)
C2—Cr—C3—C4	133.2 (2)	C3—Cr—C6—C1	68.34 (14)
C5—Cr—C3—C4	30.26 (13)	C5—Cr—C6—C1	133.5 (2)
C1—Cr—C3—C4	104.59 (15)	C4—Cr—C6—C1	105.21 (16)
C2—C3—C4—C5	−2.6 (3)