Crystal structure of (tert-butyl-dimethyl-sil-yl)tri-phenyl-germane, Ph3Ge-SiMe2(t-Bu).

In the title compound, Ph3Ge-SiMe2(t-Bu) or C24H30GeSi, the Si and Ge atoms both possess a tetra-hedral coordination environment with C-E-C (E = Si, Ge) angles in the range 104.47 (5)-114.67 (5)°. The mol-ecule adopts an eclipsed conformation, with three torsion angles less than 29.5°. In the crystal, neighbouring mol-ecules are combined to dimers by six T-shaped C-H⋯π inter-actions, forming sixfold phenyl embraces (6PE).

Related literature

For general background to the chemistry of Group 14 element catenated compounds, see: Marschner & Hlina (2013 ▸); Amadoruge & Weinert (2008 ▸); Párkányi et al. (1986 ▸); Leigh et al. (1997 ▸). As apart of our studies of the chemistry of oligogermanium compounds (Zaitsev et al. 2012 ▸, 2013 ▸, 2014a ▸,b ▸), the title compound was obtained and studied. For related crystal structures of silagermanes, see: Zaitsev et al. (2015 ▸). The 6PE inter­actions are intensively discussed in Scudder & Dance (2000 ▸); Steiner (2000 ▸); Churakov et al. (2005 ▸).

Experimental

Crystal data

C24H30GeSi

M = 419.16

Monoclinic,

a = 13.5332 (6) Å

b = 14.9825 (7) Å

c = 22.7179 (13) Å

β = 106.2048 (10)°

V = 4423.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 1.44 mm−1

T = 120 K

0.32 × 0.29 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.720, T max = 0.862

32242 measured reflections

7990 independent reflections

6137 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.071

S = 1.01

7990 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015022872/im2474sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022872/im2474Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022872/im2474Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022872/im2474Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015022872/im2474fig1.tif

Mol­ecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015022872/im2474fig2.tif

Dimers formed by 6PE inter­actions between adjacent mol­ecules.

CCDC reference: 1439529

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H30GeSi	F(000) = 1760
Mr = 419.16	Dx = 1.259 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5332 (6) Å	Cell parameters from 8565 reflections
b = 14.9825 (7) Å	θ = 2.5–31.7°
c = 22.7179 (13) Å	µ = 1.44 mm−1
β = 106.2048 (10)°	T = 120 K
V = 4423.3 (4) Å3	Irregular, colourless
Z = 8	0.32 × 0.29 × 0.24 mm

Bruker SMART APEXII CCD area-detector diffractometer	7990 independent reflections
Radiation source: sealed tube	6137 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8 pixels mm-1	θmax = 32.6°, θmin = 1.9°
ω and φ scans	h = −19→20
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −22→22
Tmin = 0.720, Tmax = 0.862	l = −33→34
32242 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0303P)2 + 1.8636P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
7990 reflections	Δρmax = 0.43 e Å−3
240 parameters	Δρmin = −0.37 e Å−3

Experimental. Absorption correctgion: SADABS2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0820 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.8344. The λ/2 correction factor is 0.0015.

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.

	x	y	z	Uiso*/Ueq
Ge1	0.36354 (2)	0.03558 (2)	0.37248 (2)	0.01369 (4)
Si1	0.26294 (3)	0.07258 (3)	0.27044 (2)	0.01566 (8)
C1	0.19468 (11)	−0.02626 (9)	0.22333 (7)	0.0193 (3)
C2	0.14760 (13)	−0.08808 (11)	0.26222 (8)	0.0280 (3)
H2A	0.2015	−0.1135	0.2947	0.042*
H2B	0.1099	−0.1350	0.2369	0.042*
H2C	0.1020	−0.0544	0.2794	0.042*
C3	0.10842 (13)	0.00982 (12)	0.16951 (8)	0.0286 (4)
H3A	0.0582	0.0399	0.1849	0.043*
H3B	0.0763	−0.0388	0.1437	0.043*
H3C	0.1368	0.0509	0.1462	0.043*
C4	0.26903 (13)	−0.08070 (11)	0.19725 (8)	0.0293 (4)
H4A	0.2967	−0.0432	0.1715	0.044*
H4B	0.2327	−0.1298	0.1737	0.044*
H4C	0.3241	−0.1032	0.2303	0.044*
C5	0.16501 (12)	0.15374 (11)	0.28177 (8)	0.0288 (4)
H5A	0.1152	0.1229	0.2971	0.043*
H5B	0.1311	0.1814	0.2433	0.043*
H5C	0.1984	0.1986	0.3107	0.043*
C6	0.34687 (14)	0.13018 (13)	0.22957 (8)	0.0340 (4)
H6A	0.3806	0.1798	0.2536	0.051*
H6B	0.3056	0.1512	0.1905	0.051*
H6C	0.3976	0.0891	0.2235	0.051*
C7	0.48101 (10)	0.11767 (9)	0.39511 (6)	0.0160 (3)
C8	0.46614 (12)	0.20997 (10)	0.38666 (7)	0.0244 (3)
H8	0.3997	0.2322	0.3713	0.029*
C9	0.54855 (13)	0.26859 (11)	0.40074 (8)	0.0287 (4)
H9	0.5371	0.3295	0.3948	0.034*
C10	0.64792 (12)	0.23684 (11)	0.42370 (7)	0.0258 (3)
H10	0.7032	0.2763	0.4332	0.031*
C11	0.66436 (11)	0.14632 (11)	0.43231 (7)	0.0223 (3)
H11	0.7310	0.1247	0.4475	0.027*
C12	0.58171 (11)	0.08718 (10)	0.41835 (6)	0.0185 (3)
H12	0.5939	0.0264	0.4246	0.022*
C13	0.28202 (11)	0.05273 (9)	0.43088 (6)	0.0159 (3)
C14	0.19262 (11)	0.00334 (10)	0.42642 (7)	0.0210 (3)
H14	0.1719	−0.0391	0.3956	0.025*
C15	0.13399 (12)	0.01638 (11)	0.46710 (7)	0.0254 (3)
H15	0.0750	−0.0174	0.4635	0.031*
C16	0.16361 (12)	0.07993 (11)	0.51311 (7)	0.0252 (3)
H16	0.1242	0.0891	0.5402	0.030*
C17	0.25164 (12)	0.12936 (11)	0.51847 (7)	0.0251 (3)
H17	0.2717	0.1719	0.5494	0.030*
C18	0.31062 (11)	0.11602 (10)	0.47793 (7)	0.0203 (3)
H18	0.3700	0.1497	0.4821	0.024*
C19	0.41975 (10)	−0.08517 (9)	0.38053 (6)	0.0151 (3)
C20	0.47948 (11)	−0.11181 (10)	0.34217 (7)	0.0192 (3)
H20	0.4907	−0.0719	0.3134	0.023*
C21	0.52196 (12)	−0.19630 (10)	0.34629 (7)	0.0238 (3)
H21	0.5611	−0.2128	0.3203	0.029*
C22	0.50633 (12)	−0.25642 (10)	0.38912 (7)	0.0250 (3)
H22	0.5351	−0.3132	0.3921	0.030*
C23	0.44760 (12)	−0.23154 (10)	0.42747 (7)	0.0247 (3)
H23	0.4366	−0.2718	0.4561	0.030*
C24	0.40487 (11)	−0.14636 (10)	0.42328 (7)	0.0194 (3)
H24	0.3659	−0.1302	0.4494	0.023*

	U11	U22	U33	U12	U13	U23
Ge1	0.01210 (7)	0.01250 (7)	0.01693 (7)	−0.00005 (6)	0.00481 (5)	−0.00168 (6)
Si1	0.01585 (18)	0.01453 (18)	0.01666 (18)	0.00156 (14)	0.00463 (14)	−0.00171 (14)
C1	0.0175 (6)	0.0189 (7)	0.0196 (7)	0.0025 (5)	0.0021 (5)	−0.0043 (5)
C2	0.0260 (8)	0.0266 (8)	0.0293 (8)	−0.0083 (7)	0.0042 (7)	−0.0038 (7)
C3	0.0249 (8)	0.0306 (9)	0.0245 (8)	0.0037 (7)	−0.0025 (6)	−0.0045 (7)
C4	0.0281 (8)	0.0279 (8)	0.0297 (9)	0.0060 (7)	0.0044 (7)	−0.0127 (7)
C5	0.0269 (8)	0.0245 (8)	0.0309 (9)	0.0112 (7)	0.0013 (7)	−0.0060 (7)
C6	0.0410 (10)	0.0391 (10)	0.0243 (8)	−0.0134 (8)	0.0132 (7)	−0.0001 (7)
C7	0.0152 (6)	0.0170 (6)	0.0161 (6)	−0.0019 (5)	0.0050 (5)	−0.0015 (5)
C8	0.0198 (7)	0.0182 (7)	0.0322 (8)	−0.0008 (6)	0.0024 (6)	−0.0008 (6)
C9	0.0291 (8)	0.0182 (7)	0.0356 (9)	−0.0064 (6)	0.0039 (7)	−0.0003 (7)
C10	0.0231 (7)	0.0305 (8)	0.0225 (7)	−0.0123 (6)	0.0040 (6)	−0.0018 (6)
C11	0.0148 (6)	0.0328 (8)	0.0178 (7)	−0.0026 (6)	0.0021 (5)	0.0009 (6)
C12	0.0176 (7)	0.0208 (7)	0.0168 (6)	−0.0004 (5)	0.0044 (5)	0.0014 (5)
C13	0.0151 (6)	0.0158 (6)	0.0167 (6)	0.0016 (5)	0.0044 (5)	−0.0001 (5)
C14	0.0220 (7)	0.0226 (7)	0.0199 (7)	−0.0051 (6)	0.0082 (6)	−0.0044 (6)
C15	0.0220 (7)	0.0318 (9)	0.0251 (8)	−0.0066 (6)	0.0108 (6)	−0.0023 (6)
C16	0.0249 (8)	0.0334 (9)	0.0206 (7)	0.0041 (7)	0.0117 (6)	−0.0005 (6)
C17	0.0277 (8)	0.0277 (8)	0.0200 (7)	0.0009 (6)	0.0069 (6)	−0.0073 (6)
C18	0.0189 (7)	0.0209 (7)	0.0209 (7)	−0.0017 (6)	0.0051 (6)	−0.0037 (6)
C19	0.0135 (6)	0.0123 (6)	0.0189 (6)	−0.0003 (5)	0.0034 (5)	−0.0023 (5)
C20	0.0184 (7)	0.0187 (7)	0.0215 (7)	0.0019 (5)	0.0073 (5)	0.0006 (6)
C21	0.0216 (7)	0.0216 (7)	0.0290 (8)	0.0051 (6)	0.0083 (6)	−0.0045 (6)
C22	0.0256 (8)	0.0124 (6)	0.0327 (8)	0.0033 (6)	0.0010 (6)	−0.0025 (6)
C23	0.0306 (8)	0.0173 (7)	0.0239 (8)	−0.0016 (6)	0.0038 (6)	0.0047 (6)
C24	0.0201 (7)	0.0183 (7)	0.0201 (7)	−0.0017 (6)	0.0060 (5)	−0.0009 (6)

Ge1—Si1	2.4026 (4)	C9—H9	0.9300
Ge1—C7	1.9618 (14)	C9—C10	1.384 (2)
Ge1—C13	1.9648 (14)	C10—H10	0.9300
Ge1—C19	1.9512 (13)	C10—C11	1.379 (2)
Si1—C1	1.9078 (15)	C11—H11	0.9300
Si1—C5	1.8687 (15)	C11—C12	1.393 (2)
Si1—C6	1.8670 (17)	C12—H12	0.9300
C1—C2	1.536 (2)	C13—C14	1.398 (2)
C1—C3	1.534 (2)	C13—C18	1.400 (2)
C1—C4	1.537 (2)	C14—H14	0.9300
C2—H2A	0.9600	C14—C15	1.389 (2)
C2—H2B	0.9600	C15—H15	0.9300
C2—H2C	0.9600	C15—C16	1.388 (2)
C3—H3A	0.9600	C16—H16	0.9300
C3—H3B	0.9600	C16—C17	1.379 (2)
C3—H3C	0.9600	C17—H17	0.9300
C4—H4A	0.9600	C17—C18	1.391 (2)
C4—H4B	0.9600	C18—H18	0.9300
C4—H4C	0.9600	C19—C20	1.4019 (19)
C5—H5A	0.9600	C19—C24	1.390 (2)
C5—H5B	0.9600	C20—H20	0.9300
C5—H5C	0.9600	C20—C21	1.383 (2)
C6—H6A	0.9600	C21—H21	0.9300
C6—H6B	0.9600	C21—C22	1.385 (2)
C6—H6C	0.9600	C22—H22	0.9300
C7—C8	1.403 (2)	C22—C23	1.384 (2)
C7—C12	1.3939 (19)	C23—H23	0.9300
C8—H8	0.9300	C23—C24	1.393 (2)
C8—C9	1.385 (2)	C24—H24	0.9300
C7—Ge1—Si1	107.93 (4)	C7—C8—H8	119.4
C7—Ge1—C13	107.92 (6)	C9—C8—C7	121.19 (15)
C13—Ge1—Si1	110.34 (4)	C9—C8—H8	119.4
C19—Ge1—Si1	113.92 (4)	C8—C9—H9	119.9
C19—Ge1—C7	106.89 (6)	C10—C9—C8	120.28 (15)
C19—Ge1—C13	109.61 (6)	C10—C9—H9	119.9
C1—Si1—Ge1	114.67 (5)	C9—C10—H10	120.2
C5—Si1—Ge1	104.47 (5)	C11—C10—C9	119.52 (14)
C5—Si1—C1	109.35 (7)	C11—C10—H10	120.2
C6—Si1—Ge1	109.08 (6)	C10—C11—H11	119.8
C6—Si1—C1	110.26 (7)	C10—C11—C12	120.39 (14)
C6—Si1—C5	108.72 (9)	C12—C11—H11	119.8
C2—C1—Si1	111.05 (10)	C7—C12—H12	119.5
C2—C1—C4	108.84 (13)	C11—C12—C7	121.06 (14)
C3—C1—Si1	108.38 (10)	C11—C12—H12	119.5
C3—C1—C2	109.00 (13)	C14—C13—Ge1	121.31 (10)
C3—C1—C4	108.31 (13)	C14—C13—C18	117.60 (13)
C4—C1—Si1	111.20 (10)	C18—C13—Ge1	121.09 (11)
C1—C2—H2A	109.5	C13—C14—H14	119.3
C1—C2—H2B	109.5	C15—C14—C13	121.38 (14)
C1—C2—H2C	109.5	C15—C14—H14	119.3
H2A—C2—H2B	109.5	C14—C15—H15	120.0
H2A—C2—H2C	109.5	C16—C15—C14	119.93 (15)
H2B—C2—H2C	109.5	C16—C15—H15	120.0
C1—C3—H3A	109.5	C15—C16—H16	120.1
C1—C3—H3B	109.5	C17—C16—C15	119.72 (14)
C1—C3—H3C	109.5	C17—C16—H16	120.1
H3A—C3—H3B	109.5	C16—C17—H17	119.8
H3A—C3—H3C	109.5	C16—C17—C18	120.36 (14)
H3B—C3—H3C	109.5	C18—C17—H17	119.8
C1—C4—H4A	109.5	C13—C18—H18	119.5
C1—C4—H4B	109.5	C17—C18—C13	121.01 (14)
C1—C4—H4C	109.5	C17—C18—H18	119.5
H4A—C4—H4B	109.5	C20—C19—Ge1	118.88 (10)
H4A—C4—H4C	109.5	C24—C19—Ge1	123.24 (10)
H4B—C4—H4C	109.5	C24—C19—C20	117.87 (13)
Si1—C5—H5A	109.5	C19—C20—H20	119.3
Si1—C5—H5B	109.5	C21—C20—C19	121.30 (14)
Si1—C5—H5C	109.5	C21—C20—H20	119.3
H5A—C5—H5B	109.5	C20—C21—H21	120.0
H5A—C5—H5C	109.5	C20—C21—C22	120.06 (14)
H5B—C5—H5C	109.5	C22—C21—H21	120.0
Si1—C6—H6A	109.5	C21—C22—H22	120.2
Si1—C6—H6B	109.5	C23—C22—C21	119.62 (14)
Si1—C6—H6C	109.5	C23—C22—H22	120.2
H6A—C6—H6B	109.5	C22—C23—H23	119.9
H6A—C6—H6C	109.5	C22—C23—C24	120.25 (14)
H6B—C6—H6C	109.5	C24—C23—H23	119.9
C8—C7—Ge1	120.48 (11)	C19—C24—C23	120.90 (14)
C12—C7—Ge1	121.93 (11)	C19—C24—H24	119.6
C12—C7—C8	117.57 (13)	C23—C24—H24	119.6
Ge1—C7—C8—C9	−178.11 (13)	C13—C14—C15—C16	0.4 (2)
Ge1—C7—C12—C11	177.92 (11)	C14—C13—C18—C17	−0.3 (2)
Ge1—C13—C14—C15	−178.96 (12)	C14—C15—C16—C17	−0.5 (3)
Ge1—C13—C18—C17	178.66 (12)	C15—C16—C17—C18	0.2 (2)
Ge1—C19—C20—C21	179.40 (11)	C16—C17—C18—C13	0.2 (2)
Ge1—C19—C24—C23	−179.38 (11)	C18—C13—C14—C15	0.0 (2)
C7—C8—C9—C10	−0.1 (3)	C19—C20—C21—C22	−0.3 (2)
C8—C7—C12—C11	−0.3 (2)	C20—C19—C24—C23	−0.4 (2)
C8—C9—C10—C11	0.2 (2)	C20—C21—C22—C23	0.3 (2)
C9—C10—C11—C12	−0.3 (2)	C21—C22—C23—C24	−0.3 (2)
C10—C11—C12—C7	0.4 (2)	C22—C23—C24—C19	0.4 (2)
C12—C7—C8—C9	0.2 (2)	C24—C19—C20—C21	0.3 (2)