2-[3-(Methyl­diphenyl­silyl)prop­yl]isoindoline-1,3-dione

Guzei, I.A.; Spencer, L.C.; Zakai, U.I.; Lynch, D.C.

doi:10.1107/S1600536809054117

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o221-o222

doi:10.1107/S1600536809054117

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2-[3-(Methyldiphenylsilyl)propyl]isoindoline-1,3-dione

Ilia A. Guzei,^a ^* Lara C. Spencer,^a Uzma I. Zakai ^a and Daniel C. Lynch ^a

^aDepartment of Chemistry, University of Wisconsin–Madison, 1101 University Ave, Madison, Wisconsin 53706, USA
^*Correspondence e-mail: iguzei@chem.wisc.edu

(Received 24 November 2009; accepted 15 December 2009; online 24 December 2009)

In the title compound, C₂₄H₂₃NO₂Si, the dihedral angle between the planes of the phenyl rings attached to the Si atom is 80.78 (10)°. In the crystal, the molecules form sheets lying perpendicular to [101] via C—H⋯O interactions. These sheets are stacked and linked in a three-dimensional framework by additional C—H⋯O interactions in the [10 $[\overline{1}]$ ] 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_r = 385.52
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.175
S = 1.02
4470 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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⋯O1^iv	0.93	2.32	3.200 (3)	157
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054117/zs2024sup1.cif

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

checkCIF report

Comment top

Sila phthalimides have been used in photocyclization reactions (Yoon et al., 1991), as protecting groups stabilizing reactive intermediates (Tsuge et al., 1985), and as reactants that undergo intramolecular hydrogen-abstraction (Lee et al., 1996). In our laboratory the title compound C₂₄H₂₃NO₂Si (I) was isolated as an intermediate in the synthesis of the respective sila amine. It is a congener of 2-(((4-methoxyphenyl)dimethylsilyl)methyl)isoindoline-1,3-dione (Guzei et al., 2010a) and 2-(2-(trimethylsilyl)ethyl)isoindoline-1,3-dione (Guzei et al., 2010b) recently reported by us. These sila amines were subsequently coupled with a selection of pharmaceutical agents containing a carboxylic acid, including indomethacin and N-acetyl L-cysteine (Zakai et al., 2010) as part of our continuing efforts at drug repurposing (Gately & West, 2007) using silicon chemistry (Bains & Tacke, 2003).

In the structure of (I) the bond distances and angles are typical as confirmed by the Mogul structural check (Bruno et al., 2002). The average Si—C distance of 1.870 (3) Å for compound (I) is statistically similar to the 1.88 (2) Å average of 41 measurements for 10 related compounds in the Cambridge Structural Database (CSD; Version 1.11, September 2009 release; Allen, 2002). The Si atom exhibits a slightly imperfect tetrahedral geometry with angles ranging from 108.56 (10)° to 110.53 (12)°. The phthalate entity is expectedly planar within 0.0085 Å. The two phenyl groups exhibit a windmill-like geometry about the central silicon atom. The planes of the two phenyl groups form an angle of 80.78 (10)°. For 33 compounds in the CSD that have a central silicon atom with a methyl group, two phenyl groups and another arbitrary group attached, the planes between the two phenyl groups averaged 73 (9)°, similar to that of (I).

Each oxygen atom participates in two C—H···O interactions (Table 1) which help form the three-dimensional structure of (I). These weak interactions involving O2 form sheets of (I) perpendicular to [1 0 1]. These sheets are stacked and linked in the three-dimensional framework by the interactions involving O1 in the [1 0 1] direction.

Related literature top

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 top

The protocol described by Tsuge and co-workers (Tsuge et al., 1985) was adopted. The required amount of potassium phthalimide (7.42 g, 40 mmol, 1.1 equiv) was placed into a 250 ml round-bottom flask, which was then sealed and flushed with nitrogen three times. Dry DMF (56 ml) was syringed into the flask followed by the addition of chloropropyldiphenylmethylsilane (10 g, 36.46 mmol, 1 equiv.) The reaction was heated at 60°C for 6 h. The resulting mixture was allowed to cool to room temperature. This slurry was poured onto a minimal quantity of water and extracted 3–5 times with diethyl ether. The organic extracts were subsequently collected, dried with magnesium sulfate, and filtered. The filtrate was mixed with silica gel and evaporated under reduced pressure to afford a powder of silica gel. This powder was then loaded onto a dry-packed silica gel column and eluted using a gradient column. The fractions of interest were usually drawn out using a 8:2 hexane:ethyl acetate mixture. The fractions were then combined to afford the title compound. Further recrystallization from dichloromethane afforded large lusterous white crystals (12.47 g, 32.35 mmol, 89% yield) for X-ray crystallography. Manipulation of air and moisture sensitive compounds was performed using standard high-vacuum line techniques. All solvents and reagents were obtained from Aldrich. Chloropropyldiphenylmethylsilane was purchased from Gelest. ¹H NMR spectra were obtained on a Varian Unity 500 spectrometer, ¹³C {H} NMR spectra were obtained on a Varian 500 spectrometer operating at 125 MHz, ²⁹Si {H} NMR spectra were obtained on a Varian Unity spectrometer operating at 99 MHz. Mass spectra were determined on a Waters (Micromass) AutoSpec mass spectrometer. Melting points were determined on a Mel-Temp Laboratory Device. mp 57–58° C; ¹H NMR (500 MHz, CDCl₃) δ 0.52 (s, 3H, Me), 1.08 (m, 2H, CH₂), 1.73 (m, 2H, CH₂), 3.67 (t, J=7.3 Hz, 2H, CH₂), 7.33 (m, 6H, ArH), 7.47 (dd, J=7.4, 1.5 Hz, 4H, ArH), 7.68 (dd, J=5.5, 3.0 Hz, 2H, ArH), 7.80 (dd, J=5.4, 3.1 Hz, 2H, ArH); ¹³C NMR (125 MHz, CDCl₃) δ -4.6 (SiCH₃), 11.5 (CH₂), 23.2 (CH₂), 40.9 (CH₂), 123.1 (CH), 127.9 (CH), 129.2 (CH), 132.1 (CH), 133.8 (CH), 134.4 (CH), 136.6 (CH), 168.4 (CO); ²⁹Si NMR (99 MHz, CDCl₃) δ -7.62 (SiMePh₂); MS (EI⁺) m/z (rel. intensity %) 385 (M⁺, 5), 370 (M—Me, 21), 308 (100), 266 (70), 197 (96), 160 (62): HRMS (EI⁺): calcd. for C₂₄H₂₃NO₂Si (M⁺) 385.1493, found (M—Me)⁺ 370. 1258.

Computing details top

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

Figures top

Fig. 1. Molecular structure of (I). The thermal ellipsoids are shown at 50% probability level.

2-[3-(Methyldiphenylsilyl)propyl]isoindoline-1,3-dione top

Crystal data top

C₂₄H₂₃NO₂Si	F(000) = 1632
M_r = 385.52	D_x = 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

Data collection top

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

Refinement top

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 = 1.02	w = 1/[σ²(F_o²) + (0.102P)²] where P = (F_o² + 2F_c²)/3
4470 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³
0 constraints

Crystal data top

C₂₄H₂₃NO₂Si	V = 4382.5 (12) Å³
M_r = 385.52	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.277 (3) Å	µ = 0.13 mm⁻¹
b = 13.238 (2) Å	T = 300 K
c = 19.272 (3) Å	0.30 × 0.30 × 0.30 mm
β = 116.987 (6)°

Data collection top

Bruker SMART X2S diffractometer	4470 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2693 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.964	R_int = 0.051
15551 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
4470 reflections	Δρ_min = −0.22 e Å⁻³
254 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.32	3.200 (3)	157

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, −y+3/2, −z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₃NO₂Si
M_r	385.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	300
a, b, c (Å)	19.277 (3), 13.238 (2), 19.272 (3)
β (°)	116.987 (6)
V (Å³)	4382.5 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART X2S diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.964, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	15551, 4470, 2693
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.175, 1.02
No. of reflections	4470
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: GIS (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and FCF_filter (Guzei, 2007), SHELXTL (Sheldrick, 2008), modiCIFer (Guzei, 2007) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.32	3.200 (3)	157

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, −y+3/2, −z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

We thank Dr N. J. Hill (UW-Madison) for acquiring the data and Professor R. West (UW-Madison) for his support. We gratefully acknowledge Bruker sponsorship of this publication and also acknowledge grants NIH 1 S10 RRO 8389–01 and NSF CHE-9629688 for providing NMR spectrometers, and grant NSF CHE-9304546 for providing the mass spectrometer for this work.

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