2-{[(4-Methoxy-phen-yl)dimethyl-silyl]meth-yl}isoindoline-1,3-dione.

In the course of our studies of silicon-containing anti-cancer compounds, the title compound, C(18)H(19)NO(3)Si, was synthesized. The mol-ecular geometry including bond distances and angles involving the Si atoms are typical. Torsion angles associated with the isoindoline ring and the silyl group [C-N-C(methyl-ene)-Si = 90.5 (2) and -93.1 (2)°] indicate that there is no inter-action between the O and Si atoms despite silicon's high affinity for oxygen.

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 ▶); Latxague & Leger (2004 ▶); Lee et al. (1993 ▶, 1996 ▶); Murai et al. (1998 ▶); 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., 2004 ▶).

Experimental

Crystal data

C18H19NO3Si

M = 325.43

Monoclinic,

a = 10.2713 (16) Å

b = 14.061 (3) Å

c = 12.069 (2) Å

β = 103.355 (6)°

V = 1695.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 300 K

0.50 × 0.40 × 0.23 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.928, T max = 0.966

11394 measured reflections

3197 independent reflections

2338 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.131

S = 0.96

3197 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.26 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/S1600536809054129/zs2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054129/zs2023Isup2.hkl

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

C18H19NO3Si	F(000) = 688
Mr = 325.43	Dx = 1.275 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3201 reflections
a = 10.2713 (16) Å	θ = 2.3–24.8°
b = 14.061 (3) Å	µ = 0.15 mm−1
c = 12.069 (2) Å	T = 300 K
β = 103.355 (6)°	Block, colourless
V = 1695.9 (5) Å3	0.50 × 0.40 × 0.23 mm
Z = 4

Bruker SMART X2S diffractometer	3197 independent reflections
Radiation source: micro-focus sealed tube	2338 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.042
ω scans	θmax = 25.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.928, Tmax = 0.966	k = −17→17
11394 measured reflections	l = −11→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0812P)2 + 0.1363P] where P = (Fo2 + 2Fc2)/3
3197 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 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	−0.00370 (6)	0.19378 (4)	0.82075 (5)	0.0462 (2)
O1	−0.34928 (17)	0.48107 (11)	0.99174 (16)	0.0762 (5)
O2	0.14405 (16)	−0.05076 (11)	0.93970 (14)	0.0674 (5)
O3	0.38001 (16)	0.20812 (11)	0.87061 (17)	0.0779 (5)
N1	0.23597 (15)	0.09334 (11)	0.90879 (13)	0.0439 (4)
C1	−0.3261 (3)	0.57979 (18)	0.9894 (3)	0.0880 (9)
H1A	−0.2364	0.5935	1.0307	0.132*
H1B	−0.3884	0.6127	1.0240	0.132*
H1C	−0.3377	0.6004	0.9119	0.132*
C2	−0.2647 (2)	0.42125 (15)	0.95212 (18)	0.0518 (5)
C3	−0.2964 (2)	0.32606 (16)	0.9526 (2)	0.0603 (6)
H3	−0.3712	0.3068	0.9779	0.072*
C4	−0.2182 (2)	0.25971 (15)	0.91604 (18)	0.0532 (5)
H4	−0.2403	0.1958	0.9189	0.064*
C5	−0.10617 (18)	0.28429 (13)	0.87447 (16)	0.0426 (5)
C6	−0.0790 (2)	0.38081 (15)	0.87433 (18)	0.0521 (5)
H6	−0.0060	0.4007	0.8470	0.063*
C7	−0.1555 (2)	0.44937 (15)	0.91292 (19)	0.0552 (6)
H7	−0.1330	0.5134	0.9122	0.066*
C8	−0.1060 (2)	0.08665 (17)	0.7693 (2)	0.0682 (7)
H8A	−0.1350	0.0579	0.8316	0.102*
H8B	−0.0531	0.0419	0.7385	0.102*
H8C	−0.1827	0.1048	0.7112	0.102*
C9	0.0661 (3)	0.2458 (2)	0.7055 (2)	0.0755 (7)
H9A	−0.0049	0.2730	0.6484	0.113*
H9B	0.1098	0.1969	0.6719	0.113*
H9C	0.1297	0.2944	0.7367	0.113*
C10	0.1385 (2)	0.15592 (15)	0.94299 (17)	0.0494 (5)
H10A	0.1844	0.2123	0.9785	0.059*
H10B	0.1014	0.1235	0.9996	0.059*
C11	0.2303 (2)	−0.00539 (14)	0.91102 (16)	0.0449 (5)
C12	0.34907 (19)	−0.03966 (14)	0.87220 (16)	0.0466 (5)
C13	0.3901 (2)	−0.13083 (17)	0.85585 (19)	0.0637 (6)
H13	0.3418	−0.1836	0.8699	0.076*
C14	0.5067 (3)	−0.1404 (2)	0.8175 (2)	0.0792 (8)
H14	0.5375	−0.2009	0.8055	0.095*
C15	0.5775 (3)	−0.0621 (2)	0.7968 (2)	0.0838 (9)
H15	0.6555	−0.0710	0.7715	0.101*
C16	0.5365 (2)	0.0289 (2)	0.8124 (2)	0.0713 (7)
H16	0.5847	0.0815	0.7977	0.086*
C17	0.4204 (2)	0.03886 (15)	0.85097 (17)	0.0498 (5)
C18	0.34950 (19)	0.12526 (16)	0.87585 (17)	0.0515 (5)

	U11	U22	U33	U12	U13	U23
Si1	0.0503 (4)	0.0469 (3)	0.0444 (3)	0.0088 (2)	0.0174 (3)	0.0027 (2)
O1	0.0752 (11)	0.0601 (10)	0.1004 (13)	0.0179 (8)	0.0350 (10)	−0.0101 (9)
O2	0.0723 (11)	0.0521 (9)	0.0872 (12)	0.0016 (8)	0.0377 (9)	0.0162 (8)
O3	0.0658 (11)	0.0540 (11)	0.1174 (15)	−0.0131 (8)	0.0284 (10)	0.0015 (9)
N1	0.0430 (9)	0.0418 (9)	0.0487 (9)	0.0035 (7)	0.0143 (7)	0.0013 (7)
C1	0.0881 (19)	0.0571 (16)	0.116 (2)	0.0182 (14)	0.0166 (17)	−0.0252 (15)
C2	0.0478 (12)	0.0503 (12)	0.0567 (13)	0.0113 (10)	0.0112 (10)	−0.0017 (10)
C3	0.0551 (13)	0.0580 (14)	0.0758 (16)	0.0070 (11)	0.0316 (12)	0.0077 (11)
C4	0.0581 (13)	0.0403 (11)	0.0665 (13)	0.0034 (10)	0.0253 (11)	0.0063 (10)
C5	0.0425 (11)	0.0424 (11)	0.0420 (10)	0.0042 (8)	0.0080 (8)	0.0054 (8)
C6	0.0450 (11)	0.0482 (12)	0.0646 (13)	−0.0004 (9)	0.0156 (10)	0.0031 (10)
C7	0.0550 (13)	0.0365 (11)	0.0704 (14)	0.0007 (9)	0.0069 (11)	−0.0012 (10)
C8	0.0661 (15)	0.0660 (15)	0.0713 (15)	0.0044 (12)	0.0136 (12)	−0.0197 (12)
C9	0.0809 (17)	0.0925 (19)	0.0626 (15)	0.0215 (15)	0.0363 (13)	0.0217 (14)
C10	0.0564 (12)	0.0448 (11)	0.0501 (12)	0.0086 (9)	0.0187 (10)	−0.0041 (9)
C11	0.0504 (12)	0.0418 (11)	0.0430 (11)	0.0051 (9)	0.0116 (9)	0.0052 (9)
C12	0.0459 (11)	0.0519 (12)	0.0389 (11)	0.0082 (9)	0.0033 (9)	−0.0011 (9)
C13	0.0690 (15)	0.0558 (14)	0.0628 (14)	0.0159 (12)	0.0077 (12)	−0.0073 (11)
C14	0.0711 (17)	0.085 (2)	0.0755 (17)	0.0336 (15)	0.0050 (14)	−0.0252 (15)
C15	0.0519 (15)	0.119 (3)	0.0816 (18)	0.0232 (17)	0.0187 (13)	−0.0206 (18)
C16	0.0421 (12)	0.095 (2)	0.0787 (17)	0.0064 (12)	0.0175 (11)	−0.0080 (14)
C17	0.0388 (11)	0.0629 (14)	0.0456 (11)	0.0041 (9)	0.0053 (9)	−0.0016 (10)
C18	0.0440 (11)	0.0517 (13)	0.0569 (13)	−0.0012 (10)	0.0080 (9)	0.0019 (10)

Si1—C9	1.856 (2)	C6—H6	0.9300
Si1—C8	1.859 (2)	C7—H7	0.9300
Si1—C5	1.8609 (19)	C8—H8A	0.9600
Si1—C10	1.897 (2)	C8—H8B	0.9600
O1—C2	1.372 (2)	C8—H8C	0.9600
O1—C1	1.410 (3)	C9—H9A	0.9600
O2—C11	1.205 (2)	C9—H9B	0.9600
O3—C18	1.212 (2)	C9—H9C	0.9600
N1—C11	1.390 (3)	C10—H10A	0.9700
N1—C18	1.390 (2)	C10—H10B	0.9700
N1—C10	1.462 (2)	C11—C12	1.485 (3)
C1—H1A	0.9600	C12—C13	1.378 (3)
C1—H1B	0.9600	C12—C17	1.381 (3)
C1—H1C	0.9600	C13—C14	1.386 (3)
C2—C7	1.372 (3)	C13—H13	0.9300
C2—C3	1.378 (3)	C14—C15	1.374 (4)
C3—C4	1.369 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.373 (4)
C4—C5	1.400 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.383 (3)
C5—C6	1.386 (3)	C16—H16	0.9300
C6—C7	1.390 (3)	C17—C18	1.482 (3)
C9—Si1—C8	110.81 (13)	H8A—C8—H8C	109.5
C9—Si1—C5	109.82 (10)	H8B—C8—H8C	109.5
C8—Si1—C5	110.42 (10)	Si1—C9—H9A	109.5
C9—Si1—C10	109.38 (11)	Si1—C9—H9B	109.5
C8—Si1—C10	107.86 (10)	H9A—C9—H9B	109.5
C5—Si1—C10	108.48 (8)	Si1—C9—H9C	109.5
C2—O1—C1	118.2 (2)	H9A—C9—H9C	109.5
C11—N1—C18	111.69 (16)	H9B—C9—H9C	109.5
C11—N1—C10	124.13 (16)	N1—C10—Si1	113.82 (13)
C18—N1—C10	124.10 (17)	N1—C10—H10A	108.8
O1—C1—H1A	109.5	Si1—C10—H10A	108.8
O1—C1—H1B	109.5	N1—C10—H10B	108.8
H1A—C1—H1B	109.5	Si1—C10—H10B	108.8
O1—C1—H1C	109.5	H10A—C10—H10B	107.7
H1A—C1—H1C	109.5	O2—C11—N1	124.82 (18)
H1B—C1—H1C	109.5	O2—C11—C12	129.12 (19)
O1—C2—C7	125.3 (2)	N1—C11—C12	106.06 (17)
O1—C2—C3	115.12 (19)	C13—C12—C17	121.6 (2)
C7—C2—C3	119.63 (19)	C13—C12—C11	130.4 (2)
C4—C3—C2	120.2 (2)	C17—C12—C11	108.00 (17)
C4—C3—H3	119.9	C12—C13—C14	117.0 (2)
C2—C3—H3	119.9	C12—C13—H13	121.5
C3—C4—C5	122.63 (19)	C14—C13—H13	121.5
C3—C4—H4	118.7	C15—C14—C13	121.1 (2)
C5—C4—H4	118.7	C15—C14—H14	119.4
C6—C5—C4	115.11 (18)	C13—C14—H14	119.4
C6—C5—Si1	122.64 (15)	C16—C15—C14	122.0 (2)
C4—C5—Si1	122.24 (15)	C16—C15—H15	119.0
C5—C6—C7	123.3 (2)	C14—C15—H15	119.0
C5—C6—H6	118.3	C15—C16—C17	117.1 (3)
C7—C6—H6	118.3	C15—C16—H16	121.4
C2—C7—C6	119.06 (19)	C17—C16—H16	121.4
C2—C7—H7	120.5	C12—C17—C16	121.1 (2)
C6—C7—H7	120.5	C12—C17—C18	108.11 (18)
Si1—C8—H8A	109.5	C16—C17—C18	130.8 (2)
Si1—C8—H8B	109.5	O3—C18—N1	124.7 (2)
H8A—C8—H8B	109.5	O3—C18—C17	129.2 (2)
Si1—C8—H8C	109.5	N1—C18—C17	106.09 (18)
C1—O1—C2—C7	2.1 (3)	C18—N1—C11—C12	−2.0 (2)
C1—O1—C2—C3	−177.5 (2)	C10—N1—C11—C12	−178.81 (15)
O1—C2—C3—C4	−179.3 (2)	O2—C11—C12—C13	1.9 (4)
C7—C2—C3—C4	1.1 (3)	N1—C11—C12—C13	−178.2 (2)
C2—C3—C4—C5	−1.6 (3)	O2—C11—C12—C17	−178.8 (2)
C3—C4—C5—C6	0.8 (3)	N1—C11—C12—C17	1.1 (2)
C3—C4—C5—Si1	−178.04 (17)	C17—C12—C13—C14	0.2 (3)
C9—Si1—C5—C6	−30.5 (2)	C11—C12—C13—C14	179.45 (19)
C8—Si1—C5—C6	−153.00 (17)	C12—C13—C14—C15	0.0 (4)
C10—Si1—C5—C6	88.99 (18)	C13—C14—C15—C16	−0.3 (4)
C9—Si1—C5—C4	148.23 (18)	C14—C15—C16—C17	0.4 (4)
C8—Si1—C5—C4	25.73 (19)	C13—C12—C17—C16	−0.1 (3)
C10—Si1—C5—C4	−92.27 (18)	C11—C12—C17—C16	−179.46 (18)
C4—C5—C6—C7	0.4 (3)	C13—C12—C17—C18	179.50 (18)
Si1—C5—C6—C7	179.23 (16)	C11—C12—C17—C18	0.1 (2)
O1—C2—C7—C6	−179.48 (19)	C15—C16—C17—C12	−0.3 (3)
C3—C2—C7—C6	0.0 (3)	C15—C16—C17—C18	−179.7 (2)
C5—C6—C7—C2	−0.8 (3)	C11—N1—C18—O3	−177.6 (2)
C11—N1—C10—Si1	−93.1 (2)	C10—N1—C18—O3	−0.8 (3)
C18—N1—C10—Si1	90.5 (2)	C11—N1—C18—C17	2.1 (2)
C9—Si1—C10—N1	−53.22 (18)	C10—N1—C18—C17	178.88 (16)
C8—Si1—C10—N1	67.39 (17)	C12—C17—C18—O3	178.3 (2)
C5—Si1—C10—N1	−172.99 (14)	C16—C17—C18—O3	−2.2 (4)
C18—N1—C11—O2	177.87 (19)	C12—C17—C18—N1	−1.3 (2)
C10—N1—C11—O2	1.1 (3)	C16—C17—C18—N1	178.2 (2)