Bis(2-naphthyl-meth-yl)diphenyl-silane.

The title compound, C(34)H(28)Si, was prepared as an inter-nal standard for diffusion-ordered NMR spectroscopy. The four ligands are arranged tetra-hedrally around the Si atom. The two naphthalene systems are nearly perpendicular, making an angle of 86.42 (4)° with one another. A naphthalene system and a phenyl ring are also nearly perpendicular, making an angle of 86.18 (6)° with one another. In the crystal, the mol-ecules pack in columns parallel to the a axis, and exhibit arene C-H⋯π(arene) inter-actions both within and between columns.

Related literature

For applications of the title compound related to NMR spectroscopy, see: Li et al. (2009 ▶). A search of the Cambridge Structural Database (Allen, 2002 ▶; CONQUEST; Bruno et al., 2002 ▶) yielded no comparable structures.

Experimental

Crystal data

C34H28Si

M = 464.65

Triclinic,

a = 9.4884 (14) Å

b = 11.0673 (13) Å

c = 13.3450 (15) Å

α = 75.820 (9)°

β = 83.767 (11)°

γ = 70.575 (11)°

V = 1280.8 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.94 mm−1

T = 295 K

0.36 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: analytical (Alcock, 1970 ▶) T min = 0.814, T max = 0.954

9101 measured reflections

4618 independent reflections

3060 reflections with I > 2σ(I)

R int = 0.045

3 standard reflections every 165 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.01

4618 reflections

333 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047412/fl2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047412/fl2263Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C34H28Si	Z = 2
Mr = 464.65	F(000) = 492
Triclinic, P1	Dx = 1.205 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.4884 (14) Å	Cell parameters from 25 reflections
b = 11.0673 (13) Å	θ = 9.7–40.3°
c = 13.3450 (15) Å	µ = 0.94 mm−1
α = 75.820 (9)°	T = 295 K
β = 83.767 (11)°	Prism, colorless
γ = 70.575 (11)°	0.36 × 0.20 × 0.05 mm
V = 1280.8 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.045
Non–profiled ω/2θ scans	θmax = 67.4°, θmin = 3.4°
Absorption correction: analytical (see. N.W. Alcock (1970))	h = −11→11
Tmin = 0.814, Tmax = 0.954	k = −13→13
9101 measured reflections	l = −15→15
4618 independent reflections	3 standard reflections every 165 reflections
3060 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.1595P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4618 reflections	Δρmax = 0.17 e Å−3
333 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (4)

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
H24B	0.231 (2)	0.353 (2)	0.7647 (17)	0.069 (7)*
H13A	0.348 (2)	0.458 (2)	0.5907 (16)	0.067 (7)*
H24A	0.117 (3)	0.479 (2)	0.7954 (16)	0.063 (6)*
H13B	0.422 (3)	0.572 (2)	0.5734 (18)	0.085 (8)*
Si	0.34325 (6)	0.51722 (5)	0.74770 (4)	0.04382 (15)
C1	0.5414 (2)	0.42670 (17)	0.78451 (14)	0.0431 (4)
C7	0.2828 (2)	0.67956 (18)	0.78528 (13)	0.0429 (4)
C14	0.1897 (2)	0.64223 (19)	0.55711 (14)	0.0484 (5)
C25	0.2299 (2)	0.34952 (18)	0.91925 (15)	0.0468 (5)
C12	0.3864 (2)	0.73768 (19)	0.80112 (15)	0.0507 (5)
H12	0.4880	0.6936	0.7945	0.061*
C22	−0.0752 (2)	0.7066 (2)	0.52307 (14)	0.0500 (5)
C27	0.2921 (2)	0.15022 (19)	1.05667 (16)	0.0489 (5)
C32	0.2569 (2)	0.22750 (19)	1.13133 (15)	0.0481 (5)
C34	0.1945 (2)	0.42439 (19)	0.99582 (16)	0.0554 (5)
H34	0.1610	0.5156	0.9760	0.067*
C26	0.2781 (2)	0.21659 (19)	0.94994 (16)	0.0520 (5)
H26	0.3030	0.1668	0.8999	0.062*
C23	0.0584 (2)	0.6132 (2)	0.56567 (15)	0.0511 (5)
H23	0.0574	0.5296	0.6005	0.061*
C24	0.2150 (3)	0.4184 (2)	0.80615 (17)	0.0561 (5)
C6	0.6578 (2)	0.3999 (2)	0.71170 (16)	0.0559 (5)
H6	0.6359	0.4249	0.6419	0.067*
C33	0.2086 (2)	0.3654 (2)	1.09779 (16)	0.0556 (5)
H33	0.1859	0.4171	1.1465	0.067*
C8	0.1324 (2)	0.75053 (19)	0.79637 (16)	0.0533 (5)
H8	0.0602	0.7154	0.7860	0.064*
C2	0.5820 (2)	0.38502 (19)	0.88809 (15)	0.0534 (5)
H2	0.5081	0.4005	0.9395	0.064*
C17	−0.0733 (2)	0.8326 (2)	0.46839 (15)	0.0538 (5)
C11	0.3415 (2)	0.8586 (2)	0.82632 (17)	0.0610 (6)
H11	0.4128	0.8951	0.8359	0.073*
C13	0.3323 (2)	0.5450 (2)	0.60306 (15)	0.0533 (5)
C5	0.8042 (2)	0.3374 (2)	0.73991 (18)	0.0667 (6)
H5	0.8793	0.3220	0.6892	0.080*
C9	0.0876 (2)	0.8709 (2)	0.82220 (17)	0.0610 (6)
H9	−0.0138	0.9155	0.8294	0.073*
C31	0.2693 (2)	0.1627 (2)	1.23757 (16)	0.0594 (5)
H31	0.2464	0.2119	1.2880	0.071*
C10	0.1923 (2)	0.9257 (2)	0.83749 (17)	0.0608 (6)
H10	0.1623	1.0070	0.8551	0.073*
C3	0.7281 (2)	0.3218 (2)	0.91611 (17)	0.0593 (5)
H3	0.7513	0.2951	0.9857	0.071*
C4	0.8400 (2)	0.2979 (2)	0.84222 (18)	0.0630 (6)
H4	0.9389	0.2554	0.8613	0.076*
C15	0.1884 (2)	0.7688 (2)	0.50217 (16)	0.0590 (5)
H15	0.2761	0.7905	0.4955	0.071*
C21	−0.2121 (3)	0.6793 (2)	0.5334 (2)	0.0698 (6)
H21	−0.2162	0.5970	0.5690	0.084*
C16	0.0625 (3)	0.8597 (2)	0.45870 (17)	0.0627 (6)
H16	0.0662	0.9416	0.4217	0.075*
C28	0.3387 (2)	0.0136 (2)	1.08931 (19)	0.0642 (6)
H28	0.3629	−0.0377	1.0403	0.077*
C30	0.3144 (2)	0.0290 (2)	1.26605 (18)	0.0678 (7)
H30	0.3221	−0.0127	1.3357	0.081*
C29	0.3492 (3)	−0.0456 (2)	1.1907 (2)	0.0709 (7)
H29	0.3799	−0.1368	1.2107	0.085*
C18	−0.2061 (3)	0.9261 (2)	0.42547 (18)	0.0712 (6)
H18	−0.2051	1.0090	0.3891	0.085*
C20	−0.3378 (3)	0.7729 (3)	0.4914 (2)	0.0857 (8)
H20	−0.4274	0.7541	0.4993	0.103*
C19	−0.3347 (3)	0.8966 (3)	0.4365 (2)	0.0856 (8)
H19	−0.4214	0.9590	0.4075	0.103*

	U11	U22	U33	U12	U13	U23
Si	0.0394 (3)	0.0496 (3)	0.0420 (3)	−0.0157 (2)	−0.0023 (2)	−0.0067 (2)
C1	0.0433 (11)	0.0416 (10)	0.0431 (10)	−0.0136 (8)	−0.0019 (8)	−0.0067 (8)
C7	0.0369 (10)	0.0512 (10)	0.0399 (10)	−0.0163 (8)	−0.0019 (8)	−0.0052 (8)
C14	0.0488 (12)	0.0609 (12)	0.0367 (10)	−0.0181 (10)	−0.0011 (8)	−0.0121 (8)
C25	0.0392 (11)	0.0510 (11)	0.0520 (11)	−0.0213 (9)	0.0014 (9)	−0.0061 (9)
C12	0.0329 (10)	0.0570 (12)	0.0618 (12)	−0.0129 (9)	0.0000 (9)	−0.0150 (9)
C22	0.0469 (12)	0.0643 (12)	0.0448 (11)	−0.0203 (10)	−0.0008 (9)	−0.0200 (9)
C27	0.0386 (11)	0.0518 (11)	0.0584 (12)	−0.0198 (9)	0.0030 (9)	−0.0104 (9)
C32	0.0334 (10)	0.0538 (11)	0.0573 (12)	−0.0175 (8)	0.0023 (8)	−0.0091 (9)
C34	0.0508 (13)	0.0489 (11)	0.0638 (13)	−0.0159 (9)	0.0040 (10)	−0.0099 (10)
C26	0.0490 (12)	0.0548 (12)	0.0590 (12)	−0.0244 (9)	0.0057 (9)	−0.0172 (10)
C23	0.0532 (12)	0.0548 (11)	0.0481 (11)	−0.0210 (10)	−0.0029 (9)	−0.0106 (9)
C24	0.0560 (14)	0.0611 (13)	0.0546 (13)	−0.0276 (12)	−0.0042 (10)	−0.0055 (10)
C6	0.0466 (12)	0.0663 (13)	0.0483 (11)	−0.0115 (10)	0.0003 (9)	−0.0110 (10)
C33	0.0512 (13)	0.0582 (12)	0.0603 (13)	−0.0190 (10)	0.0083 (10)	−0.0207 (10)
C8	0.0355 (11)	0.0580 (12)	0.0670 (13)	−0.0161 (9)	−0.0042 (9)	−0.0121 (10)
C2	0.0482 (12)	0.0630 (12)	0.0472 (11)	−0.0156 (10)	−0.0017 (9)	−0.0115 (9)
C17	0.0507 (12)	0.0613 (12)	0.0473 (11)	−0.0143 (10)	−0.0038 (9)	−0.0122 (9)
C11	0.0490 (13)	0.0616 (13)	0.0800 (15)	−0.0246 (11)	−0.0027 (11)	−0.0195 (11)
C13	0.0482 (13)	0.0628 (13)	0.0471 (11)	−0.0156 (10)	−0.0037 (9)	−0.0104 (10)
C5	0.0463 (13)	0.0776 (15)	0.0668 (15)	−0.0077 (11)	0.0054 (11)	−0.0188 (12)
C9	0.0388 (12)	0.0584 (13)	0.0793 (16)	−0.0065 (10)	−0.0044 (11)	−0.0151 (11)
C31	0.0437 (12)	0.0820 (15)	0.0564 (13)	−0.0271 (11)	0.0035 (10)	−0.0146 (11)
C10	0.0523 (13)	0.0514 (12)	0.0764 (15)	−0.0097 (10)	−0.0052 (11)	−0.0179 (11)
C3	0.0554 (13)	0.0637 (13)	0.0557 (12)	−0.0169 (11)	−0.0148 (10)	−0.0051 (10)
C4	0.0443 (12)	0.0586 (13)	0.0793 (16)	−0.0061 (10)	−0.0128 (11)	−0.0126 (11)
C15	0.0510 (13)	0.0677 (14)	0.0594 (13)	−0.0259 (11)	0.0018 (10)	−0.0078 (11)
C21	0.0592 (15)	0.0777 (16)	0.0843 (17)	−0.0321 (13)	−0.0011 (13)	−0.0252 (13)
C16	0.0600 (15)	0.0583 (13)	0.0653 (14)	−0.0217 (11)	−0.0031 (11)	−0.0012 (10)
C28	0.0576 (14)	0.0535 (12)	0.0812 (16)	−0.0199 (11)	0.0014 (12)	−0.0130 (11)
C30	0.0491 (13)	0.0839 (17)	0.0618 (14)	−0.0294 (12)	−0.0085 (11)	0.0142 (13)
C29	0.0606 (15)	0.0563 (13)	0.0880 (18)	−0.0216 (11)	−0.0068 (13)	0.0045 (13)
C18	0.0607 (16)	0.0724 (15)	0.0703 (15)	−0.0084 (12)	−0.0149 (12)	−0.0095 (12)
C20	0.0470 (15)	0.106 (2)	0.116 (2)	−0.0242 (14)	−0.0099 (14)	−0.0429 (18)
C19	0.0596 (17)	0.0880 (19)	0.104 (2)	−0.0052 (14)	−0.0254 (15)	−0.0265 (16)

Si—C1	1.868 (2)	C8—H8	0.9300
Si—C7	1.8714 (19)	C2—C3	1.375 (3)
Si—C24	1.883 (2)	C2—H2	0.9300
Si—C13	1.887 (2)	C17—C16	1.402 (3)
C1—C6	1.393 (3)	C17—C18	1.409 (3)
C1—C2	1.399 (3)	C11—C10	1.373 (3)
C7—C8	1.393 (3)	C11—H11	0.9300
C7—C12	1.399 (3)	C13—H13A	0.98 (2)
C14—C23	1.373 (3)	C13—H13B	1.00 (3)
C14—C15	1.409 (3)	C5—C4	1.371 (3)
C14—C13	1.501 (3)	C5—H5	0.9300
C25—C26	1.356 (3)	C9—C10	1.379 (3)
C25—C34	1.414 (3)	C9—H9	0.9300
C25—C24	1.513 (3)	C31—C30	1.362 (3)
C12—C11	1.376 (3)	C31—H31	0.9300
C12—H12	0.9300	C10—H10	0.9300
C22—C17	1.412 (3)	C3—C4	1.372 (3)
C22—C23	1.413 (3)	C3—H3	0.9300
C22—C21	1.415 (3)	C4—H4	0.9300
C27—C28	1.395 (3)	C15—C16	1.357 (3)
C27—C32	1.411 (3)	C15—H15	0.9300
C27—C26	1.432 (3)	C21—C20	1.360 (3)
C32—C33	1.409 (3)	C21—H21	0.9300
C32—C31	1.421 (3)	C16—H16	0.9300
C34—C33	1.357 (3)	C28—C29	1.349 (3)
C34—H34	0.9300	C28—H28	0.9300
C26—H26	0.9300	C30—C29	1.398 (3)
C23—H23	0.9300	C30—H30	0.9300
C24—H24B	0.98 (2)	C29—H29	0.9300
C24—H24A	0.95 (2)	C18—C19	1.348 (3)
C6—C5	1.378 (3)	C18—H18	0.9300
C6—H6	0.9300	C20—C19	1.393 (4)
C33—H33	0.9300	C20—H20	0.9300
C8—C9	1.375 (3)	C19—H19	0.9300
C1—Si—C7	109.26 (8)	C16—C17—C18	122.4 (2)
C1—Si—C24	111.99 (10)	C16—C17—C22	118.1 (2)
C7—Si—C24	111.63 (10)	C18—C17—C22	119.5 (2)
C1—Si—C13	108.42 (9)	C10—C11—C12	120.6 (2)
C7—Si—C13	109.40 (9)	C10—C11—H11	119.7
C24—Si—C13	106.01 (11)	C12—C11—H11	119.7
C6—C1—C2	115.99 (18)	C14—C13—Si	115.41 (14)
C6—C1—Si	122.70 (15)	C14—C13—H13A	111.2 (13)
C2—C1—Si	121.28 (14)	Si—C13—H13A	104.7 (12)
C8—C7—C12	116.43 (17)	C14—C13—H13B	111.9 (14)
C8—C7—Si	121.88 (15)	Si—C13—H13B	105.3 (14)
C12—C7—Si	121.67 (14)	H13A—C13—H13B	107.8 (18)
C23—C14—C15	117.76 (19)	C4—C5—C6	120.4 (2)
C23—C14—C13	122.66 (19)	C4—C5—H5	119.8
C15—C14—C13	119.57 (19)	C6—C5—H5	119.8
C26—C25—C34	118.44 (18)	C8—C9—C10	120.23 (19)
C26—C25—C24	121.77 (19)	C8—C9—H9	119.9
C34—C25—C24	119.78 (18)	C10—C9—H9	119.9
C11—C12—C7	121.53 (18)	C30—C31—C32	120.4 (2)
C11—C12—H12	119.2	C30—C31—H31	119.8
C7—C12—H12	119.2	C32—C31—H31	119.8
C17—C22—C23	119.21 (19)	C11—C10—C9	119.1 (2)
C17—C22—C21	118.3 (2)	C11—C10—H10	120.4
C23—C22—C21	122.5 (2)	C9—C10—H10	120.4
C28—C27—C32	119.16 (19)	C4—C3—C2	120.5 (2)
C28—C27—C26	122.86 (19)	C4—C3—H3	119.7
C32—C27—C26	117.98 (17)	C2—C3—H3	119.7
C33—C32—C27	118.82 (18)	C5—C4—C3	119.1 (2)
C33—C32—C31	122.68 (19)	C5—C4—H4	120.4
C27—C32—C31	118.49 (18)	C3—C4—H4	120.4
C33—C34—C25	121.15 (18)	C16—C15—C14	121.7 (2)
C33—C34—H34	119.4	C16—C15—H15	119.2
C25—C34—H34	119.4	C14—C15—H15	119.2
C25—C26—C27	122.31 (18)	C20—C21—C22	120.2 (2)
C25—C26—H26	118.8	C20—C21—H21	119.9
C27—C26—H26	118.8	C22—C21—H21	119.9
C14—C23—C22	121.84 (19)	C15—C16—C17	121.3 (2)
C14—C23—H23	119.1	C15—C16—H16	119.3
C22—C23—H23	119.1	C17—C16—H16	119.3
C25—C24—Si	118.49 (15)	C29—C28—C27	121.2 (2)
C25—C24—H24B	108.9 (13)	C29—C28—H28	119.4
Si—C24—H24B	106.1 (13)	C27—C28—H28	119.4
C25—C24—H24A	109.2 (13)	C31—C30—C29	120.1 (2)
Si—C24—H24A	104.8 (13)	C31—C30—H30	119.9
H24B—C24—H24A	109.1 (18)	C29—C30—H30	119.9
C5—C6—C1	122.0 (2)	C28—C29—C30	120.6 (2)
C5—C6—H6	119.0	C28—C29—H29	119.7
C1—C6—H6	119.0	C30—C29—H29	119.7
C34—C33—C32	121.29 (19)	C19—C18—C17	120.7 (2)
C34—C33—H33	119.4	C19—C18—H18	119.6
C32—C33—H33	119.4	C17—C18—H18	119.6
C9—C8—C7	122.04 (19)	C21—C20—C19	121.1 (2)
C9—C8—H8	119.0	C21—C20—H20	119.4
C7—C8—H8	119.0	C19—C20—H20	119.4
C3—C2—C1	121.88 (19)	C18—C19—C20	120.2 (3)
C3—C2—H2	119.1	C18—C19—H19	119.9
C1—C2—H2	119.1	C20—C19—H19	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1i	0.93	2.66	3.569 (2)	166
C5—H5···Cg2ii	0.93	2.88	3.664 (2)	143
C9—H9···Cg3iii	0.93	2.76	3.577 (2)	148

Table 1

Arene C—H⋯π (arene) packing interactions (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.93	2.66	3.569 (2)	166
C5—H5⋯Cg2ii	0.93	2.88	3.664 (2)	143
C9—H9⋯Cg3iii	0.93	2.76	3.577 (2)	148

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2, and Cg3 are the centroids of the C7–C12, C14–C17/C22/C23 and C27–C32 rings, respectively.