9-(Chloro­dimethyl­silyl)fluorene

The title compound, C₁₅H₁₅ClSi, crystallizes with two mol­ecules in the asymmetric unit. The conformations of the mol­ecules are slightly different. The coordinaton around the Si atom is distorted tetra­hedral.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.063
• wR factor = 0.152
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

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Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C16    = ...          S

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

   3 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
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S1. Comment

The introduction of fluorenyl ligands in the coordination chemistry of early transition elements has opened up a rich domain of investigations (Kirillov et al., 2006)·Organometallic complexes that contain linked cyclopentadienyl-amido ligands have attracted considerable attention. Some of them have been used in polymerization catalysis (Kirillov et al.,2003, 2006). Herein we report the crystal structure of compound (I).

The molecular structure of compound (I) shows in Fig.1,There are two independent molecules in the asymmetric unit. The conformations of the two molecules are slightly different·The coordinatons aroud Si atoms are distorted tetrahedron. The Si1,Si2 atoms are outside the planes of fluorene with distance 1.700 Å and 1.693 Å, respectively·There is intermolecular interaction between C19H19 of fluorenyl ring and Cl2 with distance 2.945 Å·In the absence of classical hydrogen bonds, the crystal packing is stabilized by intermolecular interaction.

Related literature

For related literature, see: Kirillov et al. (2003, 2006); Okuda et al. (1995).

S2. Experimental

All experiments were performed under an argon atmosphere using Schlenk apparatus. Solvents were dried and distilled from CaH₂ (methylene chloride), K—Na (hexane) and Na (Et₂O). The title complex was synthesized according to literature methods (Okuda et al., 1995). To a solution of fluorene (14.99 g, 90 mmol) in diethyl ether (90 ml) was added at 273 K a solution of n-butyllithium (31.2 ml, 90 mmol, 2.88 M in hexane) within 1 hr. After stirring for 3 h at room temperature, the resulting orange solution was transferred to an addition funnel and added dropwise at 273 K within 1 hr to a solution of dichlorodimethylsilane (12 ml) in diethyl ether (200 ml). The resulting suspension was stirred for 30 min at room temperature, and the solvent and excess dichlorodimethylsilane was removed under vacuum. After precipitating lithium chloride with methylene chloride and filtering, followed by removal of the solvent, 18.6 g (80%) of a white solid was obtained. A solution of the white solid (0.52 g, 2.1 mmol) in hexane (10 ml) was concentrated carefully under vacuum, yielding colourless crystals of the title compound.

S3. Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.97 A°) and refined as riding, with U_iso(H) = 1.5Ueq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The structure of (I), showing the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.

9-(Chlorodimethylsilyl)fluorene

Crystal data

C15H15ClSi	F(000) = 1088
Mr = 258.81	Dx = 1.277 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.371 (9) Å	Cell parameters from 3020 reflections
b = 9.423 (5) Å	θ = 2.5–24.3°
c = 17.511 (9) Å	µ = 0.35 mm^−1
β = 110.065 (7)°	T = 213 K
V = 2692 (3) Å^3	Block, colorless
Z = 8	0.3 × 0.2 × 0.2 mm

Data collection

Siemens SMART CCD area-detector diffractometer	4753 independent reflections
Radiation source: fine-focus sealed tube	4122 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.903, Tmax = 0.934	k = −11→8
12768 measured reflections	l = −20→20

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 1.6658P] where P = (Fo^2 + 2Fc^2)/3
4753 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.26 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
Cl1	0.12013 (6)	0.47289 (10)	0.27171 (6)	0.0518 (3)
Cl2	0.26359 (6)	0.26572 (9)	0.62829 (6)	0.0474 (3)
Si1	0.09767 (5)	0.32326 (10)	0.18047 (5)	0.0320 (2)
Si2	0.17080 (5)	0.41633 (9)	0.60134 (5)	0.0318 (2)
C1	0.20671 (19)	0.5596 (3)	0.68047 (18)	0.0299 (7)
H1	0.2157	0.5230	0.7352	0.036*
C2	0.14297 (19)	0.6765 (3)	0.65773 (17)	0.0288 (7)
C3	0.0633 (2)	0.6761 (4)	0.6565 (2)	0.0366 (8)
H3	0.0420	0.5967	0.6737	0.044*
C4	0.0154 (2)	0.7956 (4)	0.6293 (2)	0.0402 (8)
H4	−0.0387	0.7956	0.6279	0.048*
C5	0.0466 (2)	0.9147 (4)	0.6044 (2)	0.0411 (8)
H5	0.0134	0.9936	0.5857	0.049*
C6	0.1270 (2)	0.9171 (4)	0.6071 (2)	0.0376 (8)
H6	0.1484	0.9977	0.5911	0.045*
C7	0.17534 (18)	0.7977 (3)	0.63405 (18)	0.0285 (7)
C8	0.26155 (19)	0.7714 (3)	0.64487 (18)	0.0298 (7)
C9	0.3199 (2)	0.8587 (4)	0.6323 (2)	0.0421 (8)
H9	0.3066	0.9501	0.6120	0.051*
C10	0.3989 (2)	0.8067 (4)	0.6506 (2)	0.0510 (10)
H10	0.4389	0.8635	0.6419	0.061*
C11	0.4188 (2)	0.6712 (4)	0.6816 (2)	0.0479 (10)
H11	0.4723	0.6387	0.6941	0.058*
C12	0.3608 (2)	0.5839 (4)	0.6942 (2)	0.0380 (8)
H12	0.3745	0.4929	0.7148	0.046*
C13	0.28135 (18)	0.6342 (3)	0.67555 (18)	0.0296 (7)
C14	0.0793 (2)	0.3221 (4)	0.6050 (2)	0.0504 (10)
H14A	0.0346	0.3877	0.5942	0.076*
H14B	0.0907	0.2812	0.6580	0.076*
H14C	0.0650	0.2483	0.5648	0.076*
C15	0.1567 (2)	0.4895 (4)	0.5002 (2)	0.0458 (9)
H15A	0.1377	0.4161	0.4601	0.069*
H15B	0.2079	0.5260	0.4992	0.069*
H15C	0.1170	0.5647	0.4883	0.069*
C16	0.18105 (18)	0.1852 (3)	0.21391 (19)	0.0300 (7)
H16	0.2350	0.2263	0.2215	0.036*
C17	0.18047 (18)	0.1071 (3)	0.28879 (18)	0.0300 (7)
C18	0.20171 (19)	0.1534 (4)	0.36798 (19)	0.0351 (8)
H18	0.2207	0.2454	0.3820	0.042*
C19	0.1943 (2)	0.0611 (4)	0.4261 (2)	0.0416 (9)
H19	0.2086	0.0914	0.4797	0.050*
C20	0.1661 (2)	−0.0760 (4)	0.4061 (2)	0.0446 (9)
H20	0.1614	−0.1363	0.4464	0.054*
C21	0.1448 (2)	−0.1240 (4)	0.3274 (2)	0.0371 (8)
H21	0.1256	−0.2160	0.3139	0.045*
C22	0.15257 (18)	−0.0322 (3)	0.26859 (18)	0.0291 (7)
C23	0.13895 (18)	−0.0551 (3)	0.18232 (18)	0.0290 (7)
C24	0.1135 (2)	−0.1740 (4)	0.13442 (19)	0.0357 (8)
H24	0.0997	−0.2566	0.1558	0.043*
C25	0.1090 (2)	−0.1685 (4)	0.0546 (2)	0.0431 (9)
H25	0.0914	−0.2476	0.0214	0.052*
C26	0.1307 (2)	−0.0460 (4)	0.0232 (2)	0.0433 (9)
H26	0.1280	−0.0443	−0.0308	0.052*
C27	0.1561 (2)	0.0732 (4)	0.0705 (2)	0.0379 (8)
H27	0.1704	0.1551	0.0490	0.046*
C28	0.15978 (18)	0.0693 (3)	0.15032 (18)	0.0288 (7)
C29	−0.00303 (19)	0.2408 (4)	0.1666 (2)	0.0381 (8)
H29A	−0.0452	0.3115	0.1488	0.057*
H29B	−0.0025	0.2012	0.2172	0.057*
H29C	−0.0135	0.1671	0.1264	0.057*
C30	0.0978 (2)	0.4220 (4)	0.0885 (2)	0.0395 (8)
H30A	0.0832	0.3587	0.0427	0.059*
H30B	0.1514	0.4601	0.0975	0.059*
H30C	0.0587	0.4980	0.0776	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0634 (6)	0.0378 (5)	0.0489 (6)	0.0006 (5)	0.0125 (5)	−0.0093 (4)
Cl2	0.0487 (5)	0.0335 (5)	0.0552 (6)	0.0103 (4)	0.0114 (4)	−0.0041 (4)
Si1	0.0329 (5)	0.0295 (5)	0.0320 (5)	−0.0021 (4)	0.0089 (4)	0.0000 (4)
Si2	0.0342 (5)	0.0277 (5)	0.0320 (5)	0.0007 (4)	0.0094 (4)	−0.0008 (4)
C1	0.0342 (17)	0.0309 (17)	0.0265 (16)	0.0004 (14)	0.0129 (14)	−0.0001 (13)
C2	0.0329 (16)	0.0306 (17)	0.0243 (16)	0.0009 (14)	0.0115 (13)	−0.0050 (13)
C3	0.0384 (18)	0.0360 (19)	0.0384 (19)	−0.0025 (16)	0.0172 (15)	−0.0020 (15)
C4	0.0310 (17)	0.051 (2)	0.0398 (19)	0.0053 (17)	0.0137 (15)	−0.0051 (17)
C5	0.043 (2)	0.040 (2)	0.0396 (19)	0.0131 (17)	0.0126 (16)	−0.0002 (16)
C6	0.043 (2)	0.0333 (19)	0.0383 (19)	0.0048 (16)	0.0164 (16)	0.0026 (15)
C7	0.0319 (16)	0.0295 (17)	0.0255 (16)	0.0003 (14)	0.0115 (13)	−0.0050 (13)
C8	0.0312 (16)	0.0317 (18)	0.0281 (16)	0.0002 (14)	0.0123 (13)	−0.0030 (13)
C9	0.041 (2)	0.038 (2)	0.050 (2)	−0.0017 (17)	0.0184 (17)	0.0007 (17)
C10	0.042 (2)	0.051 (2)	0.064 (3)	−0.0120 (19)	0.0246 (19)	−0.007 (2)
C11	0.0282 (18)	0.056 (3)	0.058 (2)	0.0025 (18)	0.0123 (17)	−0.0050 (19)
C12	0.0344 (18)	0.040 (2)	0.0365 (18)	0.0059 (16)	0.0075 (15)	−0.0039 (15)
C13	0.0286 (16)	0.0341 (18)	0.0249 (16)	0.0021 (14)	0.0076 (13)	−0.0043 (13)
C14	0.052 (2)	0.038 (2)	0.062 (3)	−0.0106 (18)	0.020 (2)	−0.0043 (18)
C15	0.048 (2)	0.050 (2)	0.0349 (19)	−0.0006 (18)	0.0077 (17)	−0.0011 (16)
C16	0.0260 (15)	0.0323 (18)	0.0338 (17)	−0.0038 (14)	0.0130 (14)	−0.0036 (14)
C17	0.0247 (15)	0.0360 (18)	0.0300 (17)	0.0029 (14)	0.0104 (13)	−0.0019 (14)
C18	0.0326 (17)	0.0382 (19)	0.0319 (17)	0.0033 (15)	0.0079 (14)	−0.0052 (15)
C19	0.043 (2)	0.052 (2)	0.0282 (17)	0.0133 (18)	0.0091 (15)	−0.0023 (16)
C20	0.056 (2)	0.046 (2)	0.0344 (19)	0.0118 (19)	0.0193 (17)	0.0090 (16)
C21	0.0430 (19)	0.0322 (18)	0.0378 (19)	0.0038 (16)	0.0159 (16)	0.0011 (15)
C22	0.0268 (15)	0.0300 (17)	0.0290 (16)	0.0052 (13)	0.0078 (13)	−0.0007 (13)
C23	0.0266 (16)	0.0328 (18)	0.0292 (16)	0.0060 (14)	0.0115 (13)	0.0024 (13)
C24	0.0414 (19)	0.0315 (18)	0.0341 (18)	−0.0018 (15)	0.0128 (15)	−0.0011 (14)
C25	0.051 (2)	0.039 (2)	0.0349 (19)	−0.0023 (17)	0.0095 (17)	−0.0105 (16)
C26	0.050 (2)	0.053 (2)	0.0263 (18)	0.0032 (18)	0.0132 (16)	−0.0030 (16)
C27	0.0427 (19)	0.038 (2)	0.0367 (19)	−0.0016 (16)	0.0187 (16)	0.0007 (15)
C28	0.0248 (15)	0.0331 (18)	0.0292 (16)	0.0009 (14)	0.0101 (13)	−0.0024 (13)
C29	0.0302 (17)	0.047 (2)	0.0369 (19)	−0.0048 (16)	0.0117 (15)	−0.0031 (16)
C30	0.047 (2)	0.0349 (19)	0.0377 (19)	0.0010 (16)	0.0167 (16)	0.0089 (15)

Geometric parameters (Å, º)

Cl1—Si1	2.0653 (15)	C14—H14C	0.9600
Cl2—Si2	2.0768 (15)	C15—H15A	0.9600
Si1—C29	1.852 (3)	C15—H15B	0.9600
Si1—C30	1.861 (3)	C15—H15C	0.9600
Si1—C16	1.885 (3)	C16—C17	1.506 (4)
Si2—C15	1.838 (4)	C16—C28	1.512 (4)
Si2—C14	1.840 (4)	C16—H16	0.9800
Si2—C1	1.881 (3)	C17—C18	1.378 (4)
C1—C13	1.503 (4)	C17—C22	1.402 (4)
C1—C2	1.515 (4)	C18—C19	1.378 (5)
C1—H1	0.9800	C18—H18	0.9300
C2—C3	1.376 (4)	C19—C20	1.383 (5)
C2—C7	1.397 (4)	C19—H19	0.9300
C3—C4	1.384 (5)	C20—C21	1.376 (5)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.381 (5)	C21—C22	1.387 (4)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.381 (5)	C22—C23	1.463 (4)
C5—H5	0.9300	C23—C24	1.378 (4)
C6—C7	1.387 (4)	C23—C28	1.400 (4)
C6—H6	0.9300	C24—C25	1.375 (5)
C7—C8	1.465 (4)	C24—H24	0.9300
C8—C9	1.381 (5)	C25—C26	1.385 (5)
C8—C13	1.397 (4)	C25—H25	0.9300
C9—C10	1.386 (5)	C26—C27	1.376 (5)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.384 (5)	C27—C28	1.377 (4)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.376 (5)	C29—H29A	0.9600
C11—H11	0.9300	C29—H29B	0.9600
C12—C13	1.388 (4)	C29—H29C	0.9600
C12—H12	0.9300	C30—H30A	0.9600
C14—H14A	0.9600	C30—H30B	0.9600
C14—H14B	0.9600	C30—H30C	0.9600
C29—Si1—C30	112.15 (16)	Si2—C15—H15A	109.5
C29—Si1—C16	109.99 (15)	Si2—C15—H15B	109.5
C30—Si1—C16	112.65 (15)	H15A—C15—H15B	109.5
C29—Si1—Cl1	107.90 (12)	Si2—C15—H15C	109.5
C30—Si1—Cl1	105.82 (13)	H15A—C15—H15C	109.5
C16—Si1—Cl1	108.06 (11)	H15B—C15—H15C	109.5
C15—Si2—C14	112.55 (18)	C17—C16—C28	102.4 (3)
C15—Si2—C1	109.99 (16)	C17—C16—Si1	111.9 (2)
C14—Si2—C1	113.10 (16)	C28—C16—Si1	107.6 (2)
C15—Si2—Cl2	108.19 (13)	C17—C16—H16	111.5
C14—Si2—Cl2	105.93 (14)	C28—C16—H16	111.5
C1—Si2—Cl2	106.71 (11)	Si1—C16—H16	111.5
C13—C1—C2	102.2 (2)	C18—C17—C22	120.0 (3)
C13—C1—Si2	111.6 (2)	C18—C17—C16	129.9 (3)
C2—C1—Si2	107.5 (2)	C22—C17—C16	110.0 (3)
C13—C1—H1	111.7	C19—C18—C17	118.8 (3)
C2—C1—H1	111.7	C19—C18—H18	120.6
Si2—C1—H1	111.7	C17—C18—H18	120.6
C3—C2—C7	120.1 (3)	C18—C19—C20	121.2 (3)
C3—C2—C1	130.0 (3)	C18—C19—H19	119.4
C7—C2—C1	109.9 (3)	C20—C19—H19	119.4
C2—C3—C4	119.1 (3)	C21—C20—C19	120.7 (3)
C2—C3—H3	120.4	C21—C20—H20	119.7
C4—C3—H3	120.4	C19—C20—H20	119.7
C5—C4—C3	120.9 (3)	C20—C21—C22	118.5 (3)
C5—C4—H4	119.5	C20—C21—H21	120.7
C3—C4—H4	119.5	C22—C21—H21	120.7
C6—C5—C4	120.3 (3)	C21—C22—C17	120.7 (3)
C6—C5—H5	119.8	C21—C22—C23	130.7 (3)
C4—C5—H5	119.8	C17—C22—C23	108.6 (3)
C5—C6—C7	119.0 (3)	C24—C23—C28	120.7 (3)
C5—C6—H6	120.5	C24—C23—C22	130.8 (3)
C7—C6—H6	120.5	C28—C23—C22	108.5 (3)
C6—C7—C2	120.4 (3)	C25—C24—C23	118.9 (3)
C6—C7—C8	130.9 (3)	C25—C24—H24	120.5
C2—C7—C8	108.7 (3)	C23—C24—H24	120.5
C9—C8—C13	121.0 (3)	C24—C25—C26	120.4 (3)
C9—C8—C7	130.8 (3)	C24—C25—H25	119.8
C13—C8—C7	108.2 (3)	C26—C25—H25	119.8
C8—C9—C10	118.4 (3)	C27—C26—C25	121.1 (3)
C8—C9—H9	120.8	C27—C26—H26	119.4
C10—C9—H9	120.8	C25—C26—H26	119.4
C11—C10—C9	120.7 (4)	C26—C27—C28	118.9 (3)
C11—C10—H10	119.6	C26—C27—H27	120.6
C9—C10—H10	119.6	C28—C27—H27	120.6
C12—C11—C10	121.0 (3)	C27—C28—C23	120.0 (3)
C12—C11—H11	119.5	C27—C28—C16	130.0 (3)
C10—C11—H11	119.5	C23—C28—C16	110.0 (3)
C11—C12—C13	118.8 (3)	Si1—C29—H29A	109.5
C11—C12—H12	120.6	Si1—C29—H29B	109.5
C13—C12—H12	120.6	H29A—C29—H29B	109.5
C12—C13—C8	120.0 (3)	Si1—C29—H29C	109.5
C12—C13—C1	129.4 (3)	H29A—C29—H29C	109.5
C8—C13—C1	110.6 (3)	H29B—C29—H29C	109.5
Si2—C14—H14A	109.5	Si1—C30—H30A	109.5
Si2—C14—H14B	109.5	Si1—C30—H30B	109.5
H14A—C14—H14B	109.5	H30A—C30—H30B	109.5
Si2—C14—H14C	109.5	Si1—C30—H30C	109.5
H14A—C14—H14C	109.5	H30A—C30—H30C	109.5
H14B—C14—H14C	109.5	H30B—C30—H30C	109.5