2-[3-(Methyl-diphenyl-silyl)prop-yl]isoindoline-1,3-dione.

In the title compound, C(24)H(23)NO(2)Si, the dihedral angle between the planes of the phenyl rings attached to the Si atom is 80.78 (10)°. In the crystal, the mol-ecules form sheets lying perpendicular to [101] via C-H⋯O inter-actions. These sheets are stacked and linked in a three-dimensional framework by additional C-H⋯O inter-actions in the [10] direction.

Related literature

For literature related to drug design see: Bains & Tacke (2003 ▶); Gately & West (2007 ▶); Guzei et al. (2010a ▶,b ▶); Lee et al. (1996 ▶); Tsuge et al. (1985 ▶); Yoon et al. (1991 ▶); Zakai et al. (2010 ▶). 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 ▶).

Experimental

Crystal data

C24H23NO2Si

M = 385.52

Monoclinic,

a = 19.277 (3) Å

b = 13.238 (2) Å

c = 19.272 (3) Å

β = 116.987 (6)°

V = 4382.5 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 300 K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.964

15551 measured reflections

4470 independent reflections

2693 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.175

S = 1.02

4470 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 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/S1600536809054117/zs2024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054117/zs2024Isup2.hkl

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

C24H23NO2Si	F(000) = 1632
Mr = 385.52	Dx = 1.169 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3839 reflections
a = 19.277 (3) Å	θ = 2.4–22.8°
b = 13.238 (2) Å	µ = 0.13 mm−1
c = 19.272 (3) Å	T = 300 K
β = 116.987 (6)°	Block, colourless
V = 4382.5 (12) Å3	0.30 × 0.30 × 0.30 mm
Z = 8

Bruker SMART X2S diffractometer	4470 independent reflections
Radiation source: micro-focus sealed tube	2693 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.051
ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→21
Tmin = 0.964, Tmax = 0.964	k = −16→16
15551 measured reflections	l = −20→24

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.102P)2] where P = (Fo2 + 2Fc2)/3
4470 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−3
0 constraints

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	0.49123 (4)	0.69714 (5)	0.07188 (4)	0.0625 (2)
O1	0.22870 (10)	0.74572 (11)	0.13602 (10)	0.0738 (5)
O2	0.28657 (14)	0.41221 (13)	0.16823 (14)	0.1108 (8)
N1	0.26255 (10)	0.57953 (12)	0.13731 (11)	0.0566 (5)
C1	0.52300 (14)	0.67920 (17)	−0.00584 (15)	0.0653 (6)
C2	0.47118 (17)	0.6588 (2)	−0.08206 (16)	0.0812 (8)
H2	0.4186	0.6520	−0.0956	0.097*
C3	0.4956 (2)	0.6483 (2)	−0.13887 (18)	0.0995 (10)
H3	0.4593	0.6351	−0.1900	0.119*
C4	0.5722 (2)	0.6569 (2)	−0.1209 (2)	0.0993 (10)
H4	0.5881	0.6496	−0.1596	0.119*
C5	0.6249 (2)	0.6761 (2)	−0.0473 (2)	0.0980 (10)
H5	0.6773	0.6816	−0.0349	0.118*
C6	0.60125 (16)	0.6874 (2)	0.01005 (19)	0.0855 (8)
H6	0.6384	0.7010	0.0608	0.103*
C7	0.47864 (13)	0.8354 (2)	0.08261 (14)	0.0651 (6)
C8	0.5175 (2)	0.8887 (3)	0.15175 (19)	0.1228 (12)
H8	0.5505	0.8541	0.1967	0.147*
C9	0.5085 (3)	0.9920 (4)	0.1554 (3)	0.1427 (17)
H9	0.5362	1.0256	0.2025	0.171*
C10	0.4601 (2)	1.0448 (3)	0.0918 (3)	0.1084 (12)
H10	0.4534	1.1139	0.09050	0.130*
C11	0.42195 (19)	0.9959 (2)	0.0240 (2)	0.1046 (10)
H11	0.3888	1.0313	−0.0205	0.126*
C12	0.43174 (16)	0.8933 (2)	0.01984 (18)	0.0872 (8)
H12	0.4050	0.8617	−0.0282	0.105*
C13	0.56729 (17)	0.6463 (3)	0.16613 (16)	0.1021 (10)
H13A	0.6151	0.6823	0.1808	0.153*
H13B	0.5753	0.5758	0.1603	0.153*
H13C	0.5506	0.6545	0.2057	0.153*
C14	0.39646 (13)	0.63048 (18)	0.04274 (12)	0.0603 (6)
H14A	0.3568	0.6634	−0.0030	0.072*
H14B	0.4014	0.5616	0.0284	0.072*
C15	0.36934 (13)	0.62798 (19)	0.10561 (13)	0.0630 (6)
H15A	0.4053	0.5873	0.1489	0.076*
H15B	0.3704	0.6960	0.1247	0.076*
C16	0.28795 (13)	0.58526 (18)	0.07650 (14)	0.0635 (6)
H16A	0.2518	0.6273	0.0344	0.076*
H16B	0.2865	0.5181	0.0557	0.076*
C17	0.23600 (12)	0.66153 (16)	0.16301 (13)	0.0539 (5)
C18	0.21922 (11)	0.62472 (16)	0.22621 (13)	0.0542 (5)
C19	0.19309 (15)	0.67446 (19)	0.27256 (16)	0.0721 (7)
H19	0.1810	0.7429	0.2658	0.086*
C20	0.18555 (18)	0.6191 (2)	0.32939 (17)	0.0896 (8)
H20	0.1681	0.6508	0.3616	0.108*
C21	0.2033 (2)	0.5187 (3)	0.33913 (19)	0.0996 (10)
H21	0.1974	0.4831	0.3777	0.120*
C22	0.22994 (18)	0.4688 (2)	0.29304 (19)	0.0908 (9)
H22	0.2424	0.4005	0.3002	0.109*
C23	0.23748 (13)	0.52346 (17)	0.23615 (15)	0.0636 (6)
C24	0.26513 (14)	0.49367 (18)	0.17894 (16)	0.0691 (7)

	U11	U22	U33	U12	U13	U23
Si1	0.0530 (4)	0.0846 (5)	0.0515 (4)	0.0067 (3)	0.0251 (3)	0.0098 (3)
O1	0.0954 (13)	0.0496 (10)	0.0769 (11)	0.0033 (8)	0.0396 (10)	0.0045 (8)
O2	0.158 (2)	0.0577 (11)	0.180 (2)	0.0346 (11)	0.1325 (19)	0.0264 (12)
N1	0.0634 (11)	0.0494 (10)	0.0682 (11)	0.0020 (8)	0.0397 (10)	0.0031 (9)
C1	0.0648 (15)	0.0681 (15)	0.0721 (16)	0.0150 (11)	0.0390 (13)	0.0143 (12)
C2	0.0806 (18)	0.105 (2)	0.0716 (17)	0.0091 (15)	0.0464 (15)	0.0002 (15)
C3	0.124 (3)	0.115 (2)	0.078 (2)	0.015 (2)	0.062 (2)	−0.0006 (17)
C4	0.128 (3)	0.096 (2)	0.118 (3)	0.030 (2)	0.095 (3)	0.017 (2)
C5	0.089 (2)	0.101 (2)	0.137 (3)	0.0220 (17)	0.079 (2)	0.024 (2)
C6	0.0721 (18)	0.106 (2)	0.094 (2)	0.0130 (14)	0.0510 (16)	0.0172 (16)
C7	0.0525 (13)	0.0877 (17)	0.0616 (14)	−0.0116 (11)	0.0314 (12)	−0.0121 (12)
C8	0.155 (3)	0.119 (3)	0.073 (2)	−0.012 (2)	0.033 (2)	−0.0198 (19)
C9	0.204 (5)	0.115 (3)	0.110 (3)	−0.040 (3)	0.072 (3)	−0.056 (3)
C10	0.114 (3)	0.086 (2)	0.155 (4)	−0.017 (2)	0.087 (3)	−0.035 (2)
C11	0.082 (2)	0.079 (2)	0.132 (3)	−0.0013 (16)	0.031 (2)	−0.014 (2)
C12	0.0730 (17)	0.0759 (19)	0.088 (2)	−0.0038 (14)	0.0153 (15)	−0.0160 (15)
C13	0.0762 (19)	0.147 (3)	0.0691 (18)	0.0160 (18)	0.0204 (16)	0.0311 (18)
C14	0.0647 (14)	0.0678 (14)	0.0523 (12)	0.0030 (11)	0.0300 (11)	0.0069 (10)
C15	0.0629 (14)	0.0735 (15)	0.0577 (13)	−0.0023 (11)	0.0318 (12)	0.0032 (11)
C16	0.0670 (15)	0.0629 (14)	0.0661 (15)	−0.0037 (11)	0.0349 (13)	−0.0027 (11)
C17	0.0511 (12)	0.0451 (12)	0.0595 (13)	−0.0003 (9)	0.0198 (10)	−0.0006 (10)
C18	0.0479 (12)	0.0533 (12)	0.0636 (13)	−0.0007 (9)	0.0272 (11)	−0.0002 (10)
C19	0.0773 (17)	0.0658 (15)	0.0805 (17)	0.0008 (12)	0.0422 (15)	−0.0088 (13)
C20	0.101 (2)	0.101 (2)	0.090 (2)	0.0022 (17)	0.0634 (18)	−0.0063 (17)
C21	0.117 (3)	0.112 (3)	0.101 (2)	0.0117 (19)	0.077 (2)	0.0269 (19)
C22	0.104 (2)	0.0776 (18)	0.121 (2)	0.0234 (15)	0.078 (2)	0.0353 (17)
C23	0.0628 (14)	0.0561 (13)	0.0859 (16)	0.0079 (10)	0.0461 (13)	0.0131 (12)
C24	0.0741 (16)	0.0513 (14)	0.1020 (19)	0.0119 (11)	0.0577 (15)	0.0121 (12)

Si1—C13	1.867 (3)	C10—H10	0.9300
Si1—C7	1.870 (3)	C11—C12	1.378 (4)
Si1—C14	1.871 (2)	C11—H11	0.9300
Si1—C1	1.873 (3)	C12—H12	0.9300
O1—C17	1.211 (2)	C13—H13A	0.9600
O2—C24	1.206 (3)	C13—H13B	0.9600
N1—C24	1.379 (3)	C13—H13C	0.9600
N1—C17	1.384 (3)	C14—C15	1.522 (3)
N1—C16	1.463 (3)	C14—H14A	0.9700
C1—C2	1.377 (4)	C14—H14B	0.9700
C1—C6	1.401 (4)	C15—C16	1.516 (3)
C2—C3	1.381 (4)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.360 (4)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.342 (5)	C17—C18	1.478 (3)
C4—H4	0.9300	C18—C19	1.376 (3)
C5—C6	1.382 (4)	C18—C23	1.377 (3)
C5—H5	0.9300	C19—C20	1.379 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—C12	1.369 (4)	C20—C21	1.364 (4)
C7—C8	1.389 (4)	C20—H20	0.9300
C8—C9	1.384 (5)	C21—C22	1.379 (4)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.351 (5)	C22—C23	1.375 (3)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.340 (5)	C23—C24	1.479 (3)
C13—Si1—C7	109.25 (14)	H13A—C13—H13B	109.5
C13—Si1—C14	110.53 (12)	Si1—C13—H13C	109.5
C7—Si1—C14	109.68 (11)	H13A—C13—H13C	109.5
C13—Si1—C1	109.56 (13)	H13B—C13—H13C	109.5
C7—Si1—C1	108.56 (10)	C15—C14—Si1	114.37 (15)
C14—Si1—C1	109.22 (11)	C15—C14—H14A	108.7
C24—N1—C17	111.09 (19)	Si1—C14—H14A	108.7
C24—N1—C16	124.89 (18)	C15—C14—H14B	108.7
C17—N1—C16	123.95 (18)	Si1—C14—H14B	108.7
C2—C1—C6	115.9 (2)	H14A—C14—H14B	107.6
C2—C1—Si1	122.39 (19)	C16—C15—C14	112.66 (18)
C6—C1—Si1	121.7 (2)	C16—C15—H15A	109.1
C1—C2—C3	121.5 (3)	C14—C15—H15A	109.1
C1—C2—H2	119.3	C16—C15—H15B	109.1
C3—C2—H2	119.3	C14—C15—H15B	109.1
C4—C3—C2	120.8 (3)	H15A—C15—H15B	107.8
C4—C3—H3	119.6	N1—C16—C15	112.92 (18)
C2—C3—H3	119.6	N1—C16—H16A	109.0
C5—C4—C3	119.8 (3)	C15—C16—H16A	109.0
C5—C4—H4	120.1	N1—C16—H16B	109.0
C3—C4—H4	120.1	C15—C16—H16B	109.0
C4—C5—C6	120.1 (3)	H16A—C16—H16B	107.8
C4—C5—H5	120.0	O1—C17—N1	123.9 (2)
C6—C5—H5	120.0	O1—C17—C18	129.1 (2)
C5—C6—C1	122.0 (3)	N1—C17—C18	106.93 (18)
C5—C6—H6	119.0	C19—C18—C23	121.4 (2)
C1—C6—H6	119.0	C19—C18—C17	131.2 (2)
C12—C7—C8	114.6 (3)	C23—C18—C17	107.33 (19)
C12—C7—Si1	121.12 (19)	C18—C19—C20	117.6 (2)
C8—C7—Si1	124.2 (2)	C18—C19—H19	121.2
C9—C8—C7	121.7 (4)	C20—C19—H19	121.2
C9—C8—H8	119.2	C21—C20—C19	121.1 (3)
C7—C8—H8	119.2	C21—C20—H20	119.5
C10—C9—C8	121.0 (3)	C19—C20—H20	119.5
C10—C9—H9	119.5	C20—C21—C22	121.4 (3)
C8—C9—H9	119.5	C20—C21—H21	119.3
C11—C10—C9	118.9 (4)	C22—C21—H21	119.3
C11—C10—H10	116.0	C23—C22—C21	117.8 (3)
C9—C10—H10	125.0	C23—C22—H22	121.1
C10—C11—C12	120.2 (4)	C21—C22—H22	121.1
C10—C11—H11	119.9	C22—C23—C18	120.7 (2)
C12—C11—H11	119.9	C22—C23—C24	131.1 (2)
C7—C12—C11	123.6 (3)	C18—C23—C24	108.15 (19)
C7—C12—H12	118.2	O2—C24—N1	124.2 (2)
C11—C12—H12	118.2	O2—C24—C23	129.3 (2)
Si1—C13—H13A	109.5	N1—C24—C23	106.49 (19)
Si1—C13—H13B	109.5
C13—Si1—C1—C2	145.6 (2)	Si1—C14—C15—C16	172.75 (17)
C7—Si1—C1—C2	−95.1 (2)	C24—N1—C16—C15	−98.5 (3)
C14—Si1—C1—C2	24.4 (2)	C17—N1—C16—C15	78.4 (3)
C13—Si1—C1—C6	−35.4 (3)	C14—C15—C16—N1	178.08 (18)
C7—Si1—C1—C6	83.8 (2)	C24—N1—C17—O1	179.8 (2)
C14—Si1—C1—C6	−156.6 (2)	C16—N1—C17—O1	2.5 (3)
C6—C1—C2—C3	−0.6 (4)	C24—N1—C17—C18	−0.7 (2)
Si1—C1—C2—C3	178.4 (2)	C16—N1—C17—C18	−177.91 (18)
C1—C2—C3—C4	0.6 (5)	O1—C17—C18—C19	−1.8 (4)
C2—C3—C4—C5	−0.1 (5)	N1—C17—C18—C19	178.6 (2)
C3—C4—C5—C6	−0.4 (5)	O1—C17—C18—C23	−179.6 (2)
C4—C5—C6—C1	0.3 (4)	N1—C17—C18—C23	0.9 (2)
C2—C1—C6—C5	0.2 (4)	C23—C18—C19—C20	−0.2 (4)
Si1—C1—C6—C5	−178.8 (2)	C17—C18—C19—C20	−177.7 (2)
C13—Si1—C7—C12	173.6 (2)	C18—C19—C20—C21	−0.1 (4)
C14—Si1—C7—C12	−65.2 (2)	C19—C20—C21—C22	0.4 (5)
C1—Si1—C7—C12	54.1 (2)	C20—C21—C22—C23	−0.5 (5)
C13—Si1—C7—C8	−3.2 (3)	C21—C22—C23—C18	0.3 (4)
C14—Si1—C7—C8	118.1 (3)	C21—C22—C23—C24	178.8 (3)
C1—Si1—C7—C8	−122.6 (3)	C19—C18—C23—C22	0.1 (4)
C12—C7—C8—C9	0.1 (5)	C17—C18—C23—C22	178.1 (2)
Si1—C7—C8—C9	177.1 (3)	C19—C18—C23—C24	−178.8 (2)
C7—C8—C9—C10	1.2 (7)	C17—C18—C23—C24	−0.8 (2)
C8—C9—C10—C11	−1.6 (7)	C17—N1—C24—O2	−179.6 (3)
C9—C10—C11—C12	0.6 (6)	C16—N1—C24—O2	−2.4 (4)
C8—C7—C12—C11	−1.2 (4)	C17—N1—C24—C23	0.2 (3)
Si1—C7—C12—C11	−178.2 (2)	C16—N1—C24—C23	177.42 (18)
C10—C11—C12—C7	0.9 (5)	C22—C23—C24—O2	1.4 (5)
C13—Si1—C14—C15	52.0 (2)	C18—C23—C24—O2	−179.9 (3)
C7—Si1—C14—C15	−68.50 (19)	C22—C23—C24—N1	−178.4 (3)
C1—Si1—C14—C15	172.63 (15)	C18—C23—C24—N1	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.93	2.63	3.366 (4)	137
C14—H14A···O1ii	0.97	2.63	3.582 (3)	169
C19—H19···O2iii	0.93	2.51	3.310 (3)	144
C22—H22···O1iv	0.93	2.32	3.200 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.63	3.366 (4)	137
C14—H14A⋯O1ii	0.97	2.63	3.582 (3)	169
C19—H19⋯O2iii	0.93	2.51	3.310 (3)	144
C22—H22⋯O1iv	0.93	2.32	3.200 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .