Methyl 4-(trimethyl-silylethyn-yl)benzoate.

The title compound, C(13)H(16)O(2)Si, was synthesized as a precursor for ethynylarene derivatives and crystallized from hexane. In the crystal structure, mol-ecules are linked by weak C-H⋯O hydrogen bonds to form chains that pack in layers in a herringbone fashion.

Related literature

For related literature, see: Eddaoudi et al. (2001 ▶); Dybtsev et al. (2004 ▶); Kesanli et al. (2005 ▶); Zhao et al. (2004 ▶); Allen et al. (1987 ▶); Fasina et al. (2005 ▶).

Experimental

Crystal data

C13H16O2Si

M = 232.35

Orthorhombic,

a = 6.1983 (11) Å

b = 7.1194 (12) Å

c = 29.530 (5) Å

V = 1303.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 100 (2) K

0.25 × 0.24 × 0.08 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.960, T max = 0.987

8160 measured reflections

3050 independent reflections

2643 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.114

S = 1.10

3050 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1136 Friedel pairs

Flack parameter: −0.01 (19)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808008192/ez2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008192/ez2120Isup2.hkl

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

C13H16O2Si	F000 = 496
Mr = 232.35	Dx = 1.184 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 1456 reflections
a = 6.1983 (11) Å	θ = 2.8–23.3º
b = 7.1194 (12) Å	µ = 0.16 mm−1
c = 29.530 (5) Å	T = 100 (2) K
V = 1303.1 (4) Å3	Plate, colourless
Z = 4	0.25 × 0.24 × 0.08 mm

Bruker APEX CCD area-detector diffractometer	3050 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.054
T = 100(2) K	θmax = 28.3º
/w scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −7→8
Tmin = 0.960, Tmax = 0.987	k = −8→9
8160 measured reflections	l = −37→32

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.2577P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.37 e Å−3
3050 reflections	Δρmin = −0.30 e Å−3
149 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1136 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (19)

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.

	x	y	z	Uiso*/Ueq
Si1	0.68188 (11)	0.55394 (11)	0.42983 (2)	0.01481 (17)
O1	0.1541 (3)	0.5852 (3)	0.12946 (6)	0.0236 (5)
O2	−0.1514 (3)	0.4974 (3)	0.16417 (6)	0.0182 (4)
C1	0.1563 (4)	0.5421 (4)	0.20957 (8)	0.0138 (5)
C2	0.3623 (4)	0.6175 (4)	0.21449 (9)	0.0138 (5)
H2	0.4368	0.6646	0.1888	0.017*
C3	0.4582 (4)	0.6241 (4)	0.25659 (9)	0.0146 (5)
H3	0.5981	0.6770	0.2598	0.017*
C4	0.3507 (4)	0.5533 (4)	0.29466 (8)	0.0133 (5)
C5	0.1428 (4)	0.4787 (4)	0.28942 (8)	0.0137 (5)
H5	0.0673	0.4322	0.3151	0.016*
C6	0.0467 (4)	0.4724 (3)	0.24702 (8)	0.0138 (5)
H6	−0.0936	0.4206	0.2436	0.017*
C7	0.0588 (4)	0.5439 (4)	0.16347 (8)	0.0145 (5)
C8	−0.2620 (4)	0.5084 (4)	0.12112 (9)	0.0220 (7)
H8A	−0.2696	0.6397	0.1113	0.033*
H8B	−0.4084	0.4581	0.1244	0.033*
H8C	−0.1831	0.4347	0.0985	0.033*
C9	0.4551 (4)	0.5535 (4)	0.33826 (8)	0.0149 (5)
C10	0.5448 (4)	0.5509 (4)	0.37428 (8)	0.0169 (5)
C11	0.9744 (4)	0.5113 (5)	0.42078 (10)	0.0299 (8)
H11A	0.9953	0.3856	0.4080	0.045*
H11B	1.0505	0.5202	0.4498	0.045*
H11C	1.0318	0.6055	0.3998	0.045*
C12	0.6371 (5)	0.7888 (4)	0.45560 (9)	0.0219 (6)
H12A	0.6989	0.8858	0.4360	0.033*
H12B	0.7068	0.7937	0.4854	0.033*
H12C	0.4819	0.8108	0.4591	0.033*
C13	0.5661 (5)	0.3652 (4)	0.46578 (10)	0.0272 (7)
H13A	0.4092	0.3806	0.4676	0.041*
H13B	0.6281	0.3728	0.4962	0.041*
H13C	0.5999	0.2426	0.4525	0.041*

	U11	U22	U33	U12	U13	U23
Si1	0.0106 (3)	0.0178 (4)	0.0160 (3)	0.0025 (3)	−0.0022 (3)	−0.0019 (3)
O1	0.0155 (9)	0.0366 (12)	0.0188 (10)	−0.0016 (10)	0.0001 (8)	0.0049 (9)
O2	0.0108 (9)	0.0249 (11)	0.0189 (9)	−0.0047 (8)	−0.0051 (7)	0.0009 (7)
C1	0.0119 (11)	0.0130 (13)	0.0166 (12)	0.0010 (12)	−0.0024 (9)	−0.0018 (11)
C2	0.0115 (12)	0.0129 (13)	0.0171 (14)	0.0011 (10)	0.0019 (10)	0.0008 (10)
C3	0.0085 (12)	0.0145 (13)	0.0208 (14)	−0.0016 (10)	−0.0010 (10)	−0.0032 (11)
C4	0.0119 (11)	0.0115 (12)	0.0164 (12)	0.0039 (12)	−0.0024 (9)	−0.0016 (11)
C5	0.0127 (12)	0.0123 (13)	0.0162 (12)	−0.0025 (11)	0.0024 (9)	0.0015 (10)
C6	0.0115 (12)	0.0086 (13)	0.0213 (13)	0.0009 (10)	0.0001 (10)	−0.0019 (11)
C7	0.0124 (11)	0.0110 (12)	0.0199 (13)	0.0007 (11)	−0.0024 (10)	0.0001 (12)
C8	0.0181 (14)	0.0266 (17)	0.0212 (14)	−0.0029 (11)	−0.0079 (11)	−0.0028 (12)
C9	0.0134 (11)	0.0112 (12)	0.0202 (13)	−0.0005 (12)	−0.0010 (10)	−0.0013 (12)
C10	0.0122 (12)	0.0167 (14)	0.0218 (14)	−0.0009 (12)	0.0016 (10)	−0.0021 (12)
C11	0.0186 (14)	0.0392 (19)	0.0320 (18)	0.0086 (13)	−0.0050 (12)	−0.0188 (14)
C12	0.0231 (16)	0.0255 (16)	0.0171 (15)	0.0053 (12)	−0.0037 (12)	−0.0011 (12)
C13	0.0223 (16)	0.0280 (17)	0.0313 (18)	0.0039 (13)	−0.0063 (13)	0.0061 (14)

Si1—C10	1.848 (3)	C5—H5	0.9500
Si1—C13	1.857 (3)	C6—H6	0.9500
Si1—C11	1.858 (3)	C8—H8A	0.9800
Si1—C12	1.858 (3)	C8—H8B	0.9800
O1—C7	1.202 (3)	C8—H8C	0.9800
O2—C7	1.344 (3)	C9—C10	1.200 (3)
O2—C8	1.447 (3)	C9—C4	1.441 (3)
C1—C6	1.390 (3)	C11—H11A	0.9800
C1—C2	1.392 (3)	C11—H11B	0.9800
C1—C7	1.490 (3)	C11—H11C	0.9800
C2—H2	0.9500	C12—H12A	0.9800
C3—C2	1.379 (4)	C12—H12B	0.9800
C3—H3	0.9500	C12—H12C	0.9800
C4—C3	1.401 (3)	C13—H13A	0.9800
C4—C5	1.403 (3)	C13—H13B	0.9800
C5—C6	1.387 (3)	C13—H13C	0.9800
C10—Si1—C13	108.75 (14)	O1—C7—O2	123.3 (2)
C10—Si1—C11	108.62 (12)	O1—C7—C1	124.5 (2)
C13—Si1—C11	109.95 (15)	O2—C7—C1	112.2 (2)
C10—Si1—C12	107.78 (13)	Si1—C11—H11A	109.5
C13—Si1—C12	111.06 (14)	Si1—C11—H11B	109.5
C11—Si1—C12	110.61 (14)	H11A—C11—H11B	109.5
C7—O2—C8	115.63 (19)	Si1—C11—H11C	109.5
C10—C9—C4	178.7 (3)	H11A—C11—H11C	109.5
C3—C4—C5	119.0 (2)	H11B—C11—H11C	109.5
C3—C4—C9	120.2 (2)	O2—C8—H8A	109.5
C5—C4—C9	120.8 (2)	O2—C8—H8B	109.5
C6—C1—C2	120.2 (2)	H8A—C8—H8B	109.5
C6—C1—C7	122.1 (2)	O2—C8—H8C	109.5
C2—C1—C7	117.7 (2)	H8A—C8—H8C	109.5
C2—C3—C4	120.4 (2)	H8B—C8—H8C	109.5
C2—C3—H3	119.8	Si1—C12—H12A	109.5
C4—C3—H3	119.8	Si1—C12—H12B	109.5
C3—C2—C1	120.2 (2)	H12A—C12—H12B	109.5
C3—C2—H2	119.9	Si1—C12—H12C	109.5
C1—C2—H2	119.9	H12A—C12—H12C	109.5
C9—C10—Si1	178.4 (3)	H12B—C12—H12C	109.5
C6—C5—C4	120.4 (2)	Si1—C13—H13A	109.5
C6—C5—H5	119.8	Si1—C13—H13B	109.5
C4—C5—H5	119.8	H13A—C13—H13B	109.5
C5—C6—C1	119.8 (2)	Si1—C13—H13C	109.5
C5—C6—H6	120.1	H13A—C13—H13C	109.5
C1—C6—H6	120.1	H13B—C13—H13C	109.5
C5—C4—C3—C2	−1.1 (4)	C2—C1—C6—C5	0.2 (4)
C9—C4—C3—C2	177.5 (2)	C7—C1—C6—C5	−178.3 (2)
C4—C3—C2—C1	0.7 (4)	C8—O2—C7—O1	−2.8 (4)
C6—C1—C2—C3	−0.2 (4)	C8—O2—C7—C1	175.9 (2)
C7—C1—C2—C3	178.3 (2)	C6—C1—C7—O1	−172.3 (3)
C3—C4—C5—C6	1.1 (4)	C2—C1—C7—O1	9.2 (4)
C9—C4—C5—C6	−177.5 (2)	C6—C1—C7—O2	9.0 (4)
C4—C5—C6—C1	−0.6 (4)	C2—C1—C7—O2	−169.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.98	2.58	3.470 (4)	151
C12—H12A···O1ii	0.98	2.57	3.527 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.98	2.58	3.470 (4)	151
C12—H12A⋯O1ii	0.98	2.57	3.527 (3)	167

Symmetry codes: (i) ; (ii) .