1-Ethyl-2-phenyl-3-[2-(tri-methyl-sil-yl)ethyn-yl]-1H-indole.

The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with tri-methyl-silyl-acetyl-ene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C-H⋯π inter-actions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the tri-methyl-silyl unit are equally disordered over two sets of sites.

Related literature

For background to indoles, see: Huang et al. (2004 ▶); Seferoğlu et al. (2007a ▶,b ▶). For the synthesis and properties of indoles, see: Ruiz et al. (2012 ▶); Shiri (2012 ▶); Hussain et al. (2011 ▶); Prateeptongkum et al. (2010 ▶); Rives et al. (2012 ▶).

Experimental

Crystal data

C21H23NSi

M = 317.51

Monoclinic,

a = 12.6271 (6) Å

b = 9.3928 (5) Å

c = 16.6616 (8) Å

β = 111.954 (2)°

V = 1832.83 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.20 × 0.20 × 0.06 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.90, T max = 0.99

26426 measured reflections

4320 independent reflections

3254 reflections with I > 2.0σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.039

S = 1.12

3032 reflections

235 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012671/xu5700sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012671/xu5700Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012671/xu5700Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012671/xu5700Isup4.cml

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

C21H23NSi	F(000) = 680
Mr = 317.51	Dx = 1.151 Mg m−3
Monoclinic, P21/n	Melting point: 359 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.6271 (6) Å	Cell parameters from 9299 reflections
b = 9.3928 (5) Å	θ = 3–28°
c = 16.6616 (8) Å	µ = 0.13 mm−1
β = 111.954 (2)°	T = 100 K
V = 1832.83 (16) Å3	Planar, colourless
Z = 4	0.20 × 0.20 × 0.06 mm

Bruker Kappa APEXII diffractometer	3254 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 28.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.90, Tmax = 0.99	k = −12→12
26426 measured reflections	l = −22→21
4320 independent reflections

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.039	[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are 0.191, 0.134 and 0.621E-01, and x = F /Fmax
S = 1.12	(Δ/σ)max = 0.001
3032 reflections	Δρmax = 0.31 e Å−3
235 parameters	Δρmin = −0.30 e Å−3
6 restraints

Refinement. Structure was refined by full-matrix least-squares procedures on F using the programs of the PC version of CRYSTALS, with 3032 reflexions [I>3.0σ(I)].

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.99268 (10)	0.72549 (13)	0.49251 (8)	0.0196
C2	0.93192 (11)	0.79040 (15)	0.53618 (9)	0.0184
C3	0.98715 (12)	0.76670 (15)	0.62446 (9)	0.0195
C4	1.08714 (12)	0.68318 (16)	0.63574 (9)	0.0207
C5	1.08685 (11)	0.65774 (16)	0.55223 (9)	0.0211
C6	1.17008 (13)	0.57357 (17)	0.53885 (10)	0.0267
C7	1.25572 (13)	0.51899 (18)	0.61168 (11)	0.0299
C8	1.25924 (13)	0.54708 (17)	0.69552 (10)	0.0284
C9	1.17547 (13)	0.62798 (16)	0.70832 (10)	0.0243
C10	0.96037 (13)	0.71346 (17)	0.39867 (9)	0.0241
C11	1.03390 (14)	0.80491 (19)	0.36501 (10)	0.0309
C12	0.82652 (11)	0.87255 (15)	0.49367 (9)	0.0183
C13	0.73271 (13)	0.84517 (17)	0.51658 (11)	0.0261
C14	0.63450 (13)	0.92593 (18)	0.48225 (12)	0.0315
C15	0.62723 (13)	1.03523 (16)	0.42414 (11)	0.0278
C16	0.71982 (12)	1.06377 (16)	0.40118 (10)	0.0236
C17	0.81897 (12)	0.98331 (16)	0.43583 (9)	0.0206
C18	0.95193 (12)	0.81975 (15)	0.69075 (9)	0.0209
C19	0.91972 (13)	0.86562 (16)	0.74527 (9)	0.0235
Si20	0.85785 (3)	0.94562 (4)	0.81844 (3)	0.0218
C23	0.9113 (3)	1.1387 (3)	0.8372 (2)	0.0240	0.5000
C230	0.9514 (3)	1.0854 (4)	0.8847 (2)	0.0301	0.5000
C220	0.8439 (3)	0.7986 (4)	0.8949 (2)	0.0293	0.5000
C22	0.9054 (3)	0.8510 (4)	0.9200 (2)	0.0302	0.5000
C210	0.7149 (4)	1.0146 (5)	0.7538 (3)	0.0464	0.5000
C21	0.7003 (3)	0.9480 (5)	0.7620 (3)	0.0345	0.5000
H61	1.1681	0.5558	0.4825	0.0324*
H71	1.3139	0.4604	0.6047	0.0374*
H81	1.3203	0.5084	0.7444	0.0353*
H91	1.1767	0.6449	0.7647	0.0307*
H102	0.9687	0.6133	0.3855	0.0301*
H101	0.8813	0.7425	0.3710	0.0299*
H111	1.0099	0.7914	0.3042	0.0467*
H112	1.1132	0.7787	0.3925	0.0468*
H113	1.0230	0.9044	0.3756	0.0470*
H131	0.7377	0.7680	0.5565	0.0325*
H141	0.5703	0.9070	0.4976	0.0385*
H151	0.5591	1.0887	0.4017	0.0332*
H161	0.7156	1.1379	0.3613	0.0296*
H171	0.8831	1.0045	0.4207	0.0257*
H211	0.6822	0.9988	0.7107	0.0406*	0.5000
H212	0.6671	0.9920	0.7969	0.0406*	0.5000
H213	0.6727	0.8555	0.7497	0.0406*	0.5000
H2101	0.6698	0.9412	0.7211	0.0595*	0.5000
H2102	0.6816	1.0516	0.7905	0.0595*	0.5000
H2103	0.7212	1.0859	0.7171	0.0595*	0.5000
H231	0.8869	1.1873	0.7848	0.0306*	0.5000
H232	0.9907	1.1381	0.8613	0.0306*	0.5000
H233	0.8833	1.1838	0.8749	0.0306*	0.5000
H2301	0.9584	1.1579	0.8489	0.0395*	0.5000
H2302	1.0230	1.0473	0.9158	0.0395*	0.5000
H2303	0.9201	1.1220	0.9228	0.0395*	0.5000
H221	0.8782	0.7581	0.9102	0.0387*	0.5000
H222	0.9848	0.8500	0.9442	0.0387*	0.5000
H223	0.8773	0.8957	0.9578	0.0387*	0.5000
H2201	0.7966	0.7265	0.8625	0.0367*	0.5000
H2202	0.9160	0.7618	0.9260	0.0367*	0.5000
H2203	0.8131	0.8365	0.9330	0.0367*	0.5000

	U11	U22	U33	U12	U13	U23
N1	0.0187 (5)	0.0257 (6)	0.0131 (6)	0.0054 (5)	0.0045 (4)	−0.0013 (5)
C2	0.0192 (6)	0.0204 (7)	0.0163 (7)	−0.0005 (5)	0.0073 (5)	−0.0032 (5)
C3	0.0211 (6)	0.0193 (7)	0.0174 (7)	−0.0013 (5)	0.0064 (5)	−0.0019 (5)
C4	0.0214 (7)	0.0211 (7)	0.0180 (7)	−0.0004 (5)	0.0054 (5)	−0.0022 (5)
C5	0.0186 (6)	0.0257 (7)	0.0161 (7)	0.0021 (6)	0.0031 (5)	−0.0008 (6)
C6	0.0232 (7)	0.0334 (9)	0.0225 (8)	0.0066 (6)	0.0074 (6)	−0.0021 (6)
C7	0.0214 (7)	0.0335 (9)	0.0317 (9)	0.0081 (6)	0.0063 (6)	−0.0017 (7)
C8	0.0212 (7)	0.0299 (8)	0.0247 (8)	0.0040 (6)	−0.0022 (6)	0.0017 (7)
C9	0.0258 (7)	0.0250 (7)	0.0160 (7)	−0.0006 (6)	0.0007 (5)	−0.0006 (6)
C10	0.0253 (7)	0.0314 (8)	0.0133 (7)	0.0077 (6)	0.0044 (6)	−0.0040 (6)
C11	0.0327 (8)	0.0436 (10)	0.0181 (8)	0.0098 (7)	0.0114 (6)	0.0030 (7)
C12	0.0172 (6)	0.0197 (6)	0.0164 (6)	0.0002 (5)	0.0045 (5)	−0.0045 (5)
C13	0.0244 (7)	0.0233 (7)	0.0341 (8)	0.0027 (6)	0.0147 (6)	0.0031 (6)
C14	0.0220 (7)	0.0311 (9)	0.0460 (10)	0.0015 (6)	0.0179 (7)	0.0030 (7)
C15	0.0198 (7)	0.0257 (8)	0.0353 (9)	0.0051 (6)	0.0073 (6)	−0.0019 (6)
C16	0.0228 (7)	0.0241 (7)	0.0199 (7)	−0.0001 (6)	0.0034 (5)	−0.0004 (6)
C17	0.0171 (6)	0.0275 (7)	0.0161 (7)	−0.0011 (5)	0.0049 (5)	−0.0018 (6)
C18	0.0239 (7)	0.0195 (7)	0.0179 (7)	−0.0017 (5)	0.0061 (6)	−0.0004 (5)
C19	0.0300 (7)	0.0220 (7)	0.0194 (7)	−0.0014 (6)	0.0102 (6)	−0.0011 (6)
Si20	0.02245 (19)	0.0247 (2)	0.0181 (2)	0.00257 (17)	0.00724 (15)	−0.00369 (17)
C23	0.0307 (15)	0.0225 (15)	0.0230 (16)	−0.0008 (13)	0.0148 (13)	−0.0054 (13)
C230	0.0341 (17)	0.0319 (18)	0.0258 (18)	−0.0038 (14)	0.0130 (14)	−0.0090 (15)
C220	0.0286 (16)	0.0391 (19)	0.0237 (17)	−0.0033 (15)	0.0139 (14)	−0.0031 (14)
C22	0.0373 (18)	0.0333 (18)	0.0224 (17)	−0.0011 (16)	0.0139 (15)	0.0016 (14)
C210	0.037 (2)	0.031 (2)	0.050 (3)	0.009 (2)	−0.0083 (19)	−0.012 (2)
C21	0.0283 (18)	0.036 (2)	0.039 (2)	−0.001 (2)	0.0127 (15)	0.000 (2)

N1—C2	1.3811 (17)	C15—H151	0.945
N1—C5	1.3872 (18)	C16—C17	1.390 (2)
N1—C10	1.4653 (18)	C16—H161	0.951
C2—C3	1.3901 (19)	C17—H171	0.954
C2—C12	1.4709 (19)	C18—C19	1.205 (2)
C3—C4	1.438 (2)	C19—Si20	1.8366 (15)
C3—C18	1.426 (2)	Si20—C23	1.920 (3)
C4—C5	1.410 (2)	Si20—C230	1.834 (3)
C4—C9	1.402 (2)	Si20—C220	1.930 (3)
C5—C6	1.398 (2)	Si20—C22	1.804 (3)
C6—C7	1.387 (2)	Si20—C210	1.839 (4)
C6—H61	0.944	Si20—C21	1.856 (4)
C7—C8	1.406 (2)	C23—H231	0.930
C7—H71	0.960	C23—H232	0.930
C8—C9	1.382 (2)	C23—H233	0.930
C8—H81	0.959	C230—H2301	0.930
C9—H91	0.946	C230—H2302	0.930
C10—C11	1.518 (2)	C230—H2303	0.930
C10—H102	0.981	C220—H2201	0.930
C10—H101	0.969	C220—H2202	0.930
C11—H111	0.951	C220—H2203	0.930
C11—H112	0.965	C22—H221	0.930
C11—H113	0.971	C22—H222	0.930
C12—C13	1.3974 (19)	C22—H223	0.930
C12—C17	1.397 (2)	C210—H2101	0.930
C13—C14	1.382 (2)	C210—H2102	0.930
C13—H131	0.970	C210—H2103	0.930
C14—C15	1.390 (2)	C21—H211	0.930
C14—H141	0.953	C21—H212	0.930
C15—C16	1.385 (2)	C21—H213	0.930
C2—N1—C5	108.70 (11)	C16—C17—H171	119.9
C2—N1—C10	127.47 (11)	C3—C18—C19	178.42 (15)
C5—N1—C10	123.51 (11)	C18—C19—Si20	173.57 (14)
N1—C2—C3	109.21 (12)	C19—Si20—C23	106.48 (10)
N1—C2—C12	123.97 (12)	C19—Si20—C230	110.76 (12)
C3—C2—C12	126.81 (12)	C19—Si20—C220	108.16 (11)
C2—C3—C4	107.12 (12)	C23—Si20—C220	132.96 (15)
C2—C3—C18	125.82 (13)	C230—Si20—C220	108.21 (17)
C4—C3—C18	127.04 (13)	C19—Si20—C22	110.27 (12)
C3—C4—C5	106.57 (12)	C23—Si20—C22	109.80 (16)
C3—C4—C9	133.70 (14)	C230—Si20—C22	82.80 (18)
C5—C4—C9	119.73 (13)	C19—Si20—C210	108.84 (18)
C4—C5—N1	108.38 (12)	C230—Si20—C210	111.74 (18)
C4—C5—C6	121.89 (13)	C220—Si20—C210	109.0 (2)
N1—C5—C6	129.71 (13)	C22—Si20—C210	129.2 (2)
C5—C6—C7	117.15 (14)	C19—Si20—C21	108.08 (15)
C5—C6—H61	121.1	C23—Si20—C21	108.43 (18)
C7—C6—H61	121.8	C230—Si20—C21	128.55 (18)
C6—C7—C8	121.64 (14)	C220—Si20—C21	89.87 (18)
C6—C7—H71	119.2	C22—Si20—C21	113.51 (18)
C8—C7—H71	119.1	Si20—C23—H231	109.7
C7—C8—C9	120.98 (14)	Si20—C23—H232	108.8
C7—C8—H81	119.3	H231—C23—H232	109.5
C9—C8—H81	119.7	Si20—C23—H233	109.9
C4—C9—C8	118.56 (14)	H231—C23—H233	109.5
C4—C9—H91	120.4	H232—C23—H233	109.5
C8—C9—H91	121.0	Si20—C230—H2301	109.5
N1—C10—C11	112.70 (13)	Si20—C230—H2302	109.4
N1—C10—H102	107.6	H2301—C230—H2302	109.5
C11—C10—H102	109.2	Si20—C230—H2303	109.5
N1—C10—H101	108.2	H2301—C230—H2303	109.5
C11—C10—H101	109.2	H2302—C230—H2303	109.5
H102—C10—H101	110.0	Si20—C220—H2201	109.7
C10—C11—H111	108.8	Si20—C220—H2202	108.8
C10—C11—H112	110.5	H2201—C220—H2202	109.5
H111—C11—H112	109.4	Si20—C220—H2203	110.0
C10—C11—H113	109.3	H2201—C220—H2203	109.5
H111—C11—H113	108.2	H2202—C220—H2203	109.5
H112—C11—H113	110.6	Si20—C22—H221	109.0
C2—C12—C13	118.60 (13)	Si20—C22—H222	109.8
C2—C12—C17	122.61 (12)	H221—C22—H222	109.5
C13—C12—C17	118.64 (13)	Si20—C22—H223	109.6
C12—C13—C14	120.46 (15)	H221—C22—H223	109.5
C12—C13—H131	118.7	H222—C22—H223	109.5
C14—C13—H131	120.8	Si20—C210—H2101	109.6
C13—C14—C15	120.59 (14)	Si20—C210—H2102	109.4
C13—C14—H141	120.5	H2101—C210—H2102	109.5
C15—C14—H141	118.9	Si20—C210—H2103	109.4
C14—C15—C16	119.49 (14)	H2101—C210—H2103	109.5
C14—C15—H151	118.8	H2102—C210—H2103	109.5
C16—C15—H151	121.7	Si20—C21—H211	108.7
C15—C16—C17	120.15 (14)	Si20—C21—H212	109.7
C15—C16—H161	120.2	H211—C21—H212	109.5
C17—C16—H161	119.7	Si20—C21—H213	110.0
C12—C17—C16	120.67 (13)	H211—C21—H213	109.5
C12—C17—H171	119.5	H212—C21—H213	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C10—H102···Cg5i	0.98	2.66	3.3512 (18)	128
C16—H161···Cg5ii	0.95	2.79	3.5122 (17)	133
C17—H171···Cg4ii	0.95	2.81	3.4515 (17)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the pyrrole and benzene rings, respectively, of indole ring system.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H102⋯Cg5i	0.98	2.66	3.3512 (18)	128
C16—H161⋯Cg5ii	0.95	2.79	3.5122 (17)	133
C17—H171⋯Cg4ii	0.95	2.81	3.4515 (17)	125

Symmetry codes: (i) ; (ii) .