2-[2-(Trimethyl-silyl)eth-yl]isoindoline-1,3-dione.

In the course of our studies of silicon-containing anti-cancer compounds, the title compound, C(13)H(17)NO(2)Si, was synthesized. The geometrical parameters including the geometry about the Si atom are typical. The mol-ecules form dimers via a weak C-H⋯O inter-action described by the graph set R(2) (2)(10). The dimers are assembled in rows stacked in the crystallographic b-axis direction via π-π inter-actions with a 3.332 (3) Å separation between the rows.

Related literature

For literature related to drug design see: Bains & Tacke (2003 ▶); Bikzhanova et al. (2007 ▶); Franz (2007 ▶); Franz et al. (2007 ▶); Gately & West (2007 ▶); Guzei,, Spencer, Zakai & Lynch (2010 ▶); Guzei, Spencer & Zakai (2010 ▶); Lee et al. (1993 ▶, 1996 ▶); Sen & Roach (1995 ▶); Showell & Mills (2003 ▶); Tacke & Zilch (1986 ▶); Tsuge et al. (1985 ▶); Yoon et al. (1991 ▶, 1992 ▶, 1997 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). Bond distances and angles were confirmed to be typical by a Mogul structural check (Bruno et al., 2002 ▶). For graph-set notation, see: Grell et al. (1999 ▶).

Experimental

Crystal data

C13H17NO2Si

M = 247.37

Monoclinic,

a = 11.562 (5) Å

b = 6.411 (2) Å

c = 19.445 (8) Å

β = 95.176 (14)°

V = 1435.5 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 300 K

0.89 × 0.40 × 0.30 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.875, T max = 0.955

9164 measured reflections

2701 independent reflections

1750 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.151

S = 0.99

2701 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 and GIS (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL, OLEX2 (Dolomanov et al., 2009 ▶) and FCF_filter (Guzei, 2007 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, modiCIFer (Guzei, 2007 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054105/zs2025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054105/zs2025Isup2.hkl

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

C13H17NO2Si	F(000) = 528
Mr = 247.37	Dx = 1.145 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2755 reflections
a = 11.562 (5) Å	θ = 3.4–23.7°
b = 6.411 (2) Å	µ = 0.16 mm−1
c = 19.445 (8) Å	T = 300 K
β = 95.176 (14)°	Needle, colourless
V = 1435.5 (10) Å3	0.89 × 0.40 × 0.30 mm
Z = 4

Bruker SMART X2S diffractometer	2701 independent reflections
Radiation source: micro-focus sealed tube	1750 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.036
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.875, Tmax = 0.955	k = −7→7
9164 measured reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0922P)2 + 0.0229P] where P = (Fo2 + 2Fc2)/3
2701 reflections	(Δ/σ)max = 0.010
157 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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	0.90115 (5)	0.20211 (9)	0.38252 (3)	0.0610 (3)
O1	0.75423 (19)	0.2215 (3)	0.61648 (12)	0.1052 (7)
O2	0.60178 (16)	0.7082 (3)	0.46280 (10)	0.0929 (6)
N1	0.68492 (15)	0.4340 (3)	0.52646 (10)	0.0686 (5)
C1	0.8769 (3)	−0.0839 (4)	0.38950 (16)	0.0987 (9)
H1A	0.9213	−0.1366	0.4299	0.148*
H1B	0.9009	−0.1522	0.3492	0.148*
H1C	0.7959	−0.1103	0.3930	0.148*
C2	1.0592 (2)	0.2585 (5)	0.37947 (16)	0.1010 (9)
H2A	1.1015	0.2083	0.4209	0.152*
H2B	1.0705	0.4063	0.3757	0.152*
H2C	1.0869	0.1900	0.3402	0.152*
C3	0.8170 (3)	0.3029 (5)	0.30296 (15)	0.1078 (10)
H3A	0.8418	0.2326	0.2632	0.162*
H3B	0.8302	0.4500	0.2989	0.162*
H3C	0.7357	0.2778	0.3058	0.162*
C4	0.85121 (18)	0.3403 (3)	0.45914 (11)	0.0615 (6)
H4A	0.8976	0.2924	0.5001	0.074*
H4B	0.8659	0.4883	0.4543	0.074*
C5	0.72357 (19)	0.3103 (4)	0.47001 (13)	0.0773 (7)
H5A	0.6770	0.3469	0.4277	0.093*
H5B	0.7100	0.1640	0.4792	0.093*
C6	0.7031 (2)	0.3775 (4)	0.59582 (14)	0.0758 (7)
C7	0.6491 (2)	0.5451 (4)	0.63477 (13)	0.0724 (6)
C8	0.6418 (3)	0.5693 (6)	0.70431 (16)	0.0995 (9)
H8	0.6728	0.4707	0.7359	0.119*
C9	0.5867 (3)	0.7459 (7)	0.72558 (18)	0.1135 (11)
H9	0.5795	0.7658	0.7724	0.136*
C10	0.5424 (3)	0.8922 (6)	0.67926 (19)	0.1061 (10)
H10	0.5059	1.0092	0.6955	0.127*
C11	0.5502 (2)	0.8714 (4)	0.60893 (15)	0.0847 (8)
H11	0.5206	0.9715	0.5775	0.102*
C12	0.60455 (18)	0.6934 (4)	0.58821 (12)	0.0659 (6)
C13	0.62725 (19)	0.6246 (4)	0.51808 (13)	0.0679 (6)

	U11	U22	U33	U12	U13	U23
Si1	0.0681 (4)	0.0500 (4)	0.0653 (4)	−0.0086 (3)	0.0081 (3)	−0.0030 (3)
O1	0.1094 (16)	0.0863 (13)	0.1218 (16)	0.0091 (12)	0.0198 (13)	0.0246 (12)
O2	0.0852 (13)	0.1100 (14)	0.0822 (13)	0.0171 (11)	−0.0001 (10)	0.0038 (10)
N1	0.0528 (11)	0.0727 (12)	0.0818 (13)	−0.0037 (9)	0.0134 (9)	−0.0067 (10)
C1	0.119 (2)	0.0547 (15)	0.125 (2)	−0.0060 (14)	0.0245 (19)	−0.0052 (15)
C2	0.0817 (19)	0.113 (2)	0.113 (2)	−0.0169 (17)	0.0352 (17)	−0.0301 (18)
C3	0.140 (3)	0.100 (2)	0.0790 (18)	−0.0160 (19)	−0.0120 (18)	0.0127 (15)
C4	0.0537 (13)	0.0573 (12)	0.0731 (14)	−0.0078 (10)	0.0040 (10)	−0.0068 (10)
C5	0.0557 (14)	0.0794 (16)	0.0971 (18)	−0.0096 (12)	0.0096 (13)	−0.0228 (13)
C6	0.0624 (15)	0.0761 (16)	0.0902 (18)	−0.0133 (13)	0.0135 (12)	0.0076 (14)
C7	0.0562 (13)	0.0845 (16)	0.0787 (16)	−0.0124 (12)	0.0180 (12)	0.0012 (13)
C8	0.088 (2)	0.129 (3)	0.0849 (19)	−0.0080 (18)	0.0235 (15)	0.0079 (18)
C9	0.091 (2)	0.167 (3)	0.086 (2)	−0.014 (2)	0.0268 (18)	−0.025 (2)
C10	0.078 (2)	0.124 (3)	0.120 (3)	−0.0098 (18)	0.0273 (19)	−0.045 (2)
C11	0.0559 (14)	0.0910 (18)	0.108 (2)	−0.0047 (13)	0.0119 (13)	−0.0201 (16)
C12	0.0427 (11)	0.0765 (15)	0.0791 (15)	−0.0121 (11)	0.0095 (10)	−0.0134 (13)
C13	0.0469 (12)	0.0777 (15)	0.0789 (16)	−0.0061 (11)	0.0040 (11)	−0.0031 (13)

Si1—C1	1.862 (2)	C4—C5	1.522 (3)
Si1—C2	1.869 (3)	C4—H4A	0.9700
Si1—C4	1.869 (2)	C4—H4B	0.9700
Si1—C3	1.867 (3)	C5—H5A	0.9700
O1—C6	1.212 (3)	C5—H5B	0.9700
O2—C13	1.213 (3)	C6—C7	1.484 (4)
N1—C6	1.394 (3)	C7—C8	1.371 (4)
N1—C13	1.395 (3)	C7—C12	1.380 (3)
N1—C5	1.457 (3)	C8—C9	1.381 (5)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.367 (5)
C1—H1C	0.9600	C9—H9	0.9300
C2—H2A	0.9600	C10—C11	1.385 (4)
C2—H2B	0.9600	C10—H10	0.9300
C2—H2C	0.9600	C11—C12	1.380 (3)
C3—H3A	0.9600	C11—H11	0.9300
C3—H3B	0.9600	C12—C13	1.479 (3)
C3—H3C	0.9600
C1—Si1—C2	110.31 (14)	H4A—C4—H4B	107.5
C1—Si1—C4	110.45 (11)	N1—C5—C4	113.77 (18)
C2—Si1—C4	107.87 (11)	N1—C5—H5A	108.8
C1—Si1—C3	109.30 (14)	C4—C5—H5A	108.8
C2—Si1—C3	110.16 (15)	N1—C5—H5B	108.8
C4—Si1—C3	108.73 (14)	C4—C5—H5B	108.8
C6—N1—C13	111.7 (2)	H5A—C5—H5B	107.7
C6—N1—C5	123.9 (2)	O1—C6—N1	124.2 (3)
C13—N1—C5	124.4 (2)	O1—C6—C7	130.1 (3)
Si1—C1—H1A	109.5	N1—C6—C7	105.8 (2)
Si1—C1—H1B	109.5	C8—C7—C12	121.1 (2)
H1A—C1—H1B	109.5	C8—C7—C6	130.6 (3)
Si1—C1—H1C	109.5	C12—C7—C6	108.3 (2)
H1A—C1—H1C	109.5	C7—C8—C9	117.3 (3)
H1B—C1—H1C	109.5	C7—C8—H8	121.3
Si1—C2—H2A	109.5	C9—C8—H8	121.3
Si1—C2—H2B	109.5	C10—C9—C8	121.4 (3)
H2A—C2—H2B	109.5	C10—C9—H9	119.3
Si1—C2—H2C	109.5	C8—C9—H9	119.3
H2A—C2—H2C	109.5	C9—C10—C11	122.1 (3)
H2B—C2—H2C	109.5	C9—C10—H10	119.0
Si1—C3—H3A	109.5	C11—C10—H10	119.0
Si1—C3—H3B	109.5	C10—C11—C12	116.1 (3)
H3A—C3—H3B	109.5	C10—C11—H11	122.0
Si1—C3—H3C	109.5	C12—C11—H11	122.0
H3A—C3—H3C	109.5	C11—C12—C7	122.1 (2)
H3B—C3—H3C	109.5	C11—C12—C13	129.7 (2)
C5—C4—Si1	115.09 (15)	C7—C12—C13	108.2 (2)
C5—C4—H4A	108.5	O2—C13—N1	124.5 (2)
Si1—C4—H4A	108.5	O2—C13—C12	129.5 (2)
C5—C4—H4B	108.5	N1—C13—C12	106.0 (2)
Si1—C4—H4B	108.5
C1—Si1—C4—C5	−59.0 (2)	C8—C9—C10—C11	0.1 (5)
C2—Si1—C4—C5	−179.61 (18)	C9—C10—C11—C12	0.5 (4)
C3—Si1—C4—C5	60.9 (2)	C10—C11—C12—C7	−0.3 (4)
C6—N1—C5—C4	−80.8 (3)	C10—C11—C12—C13	−179.8 (2)
C13—N1—C5—C4	98.0 (3)	C8—C7—C12—C11	−0.4 (3)
Si1—C4—C5—N1	−174.99 (17)	C6—C7—C12—C11	−178.9 (2)
C13—N1—C6—O1	−177.9 (2)	C8—C7—C12—C13	179.2 (2)
C5—N1—C6—O1	1.0 (4)	C6—C7—C12—C13	0.7 (2)
C13—N1—C6—C7	1.7 (2)	C6—N1—C13—O2	179.6 (2)
C5—N1—C6—C7	−179.43 (18)	C5—N1—C13—O2	0.7 (3)
O1—C6—C7—C8	−0.2 (5)	C6—N1—C13—C12	−1.3 (2)
N1—C6—C7—C8	−179.7 (2)	C5—N1—C13—C12	179.83 (18)
O1—C6—C7—C12	178.1 (3)	C11—C12—C13—O2	−1.0 (4)
N1—C6—C7—C12	−1.4 (2)	C7—C12—C13—O2	179.4 (2)
C12—C7—C8—C9	1.0 (4)	C11—C12—C13—N1	179.9 (2)
C6—C7—C8—C9	179.1 (3)	C7—C12—C13—N1	0.3 (2)
C7—C8—C9—C10	−0.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	0.93	2.57	3.443 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2i	0.93	2.57	3.443 (4)	156

Symmetry code: (i) .