Ethyl 1,3-dimethyl-1H-indole-2-carboxyl-ate.

In the title compound, C(13)H(15)NO(2), the plane of the indole ring forms a dihedral angle of 5.26 (6)° with the ester group and the ethyl side-chain C atoms. The crystal packing is stabilized by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For biological activities of indole derivatives, see: Okabe & Adachi (1998 ▶); Schollmeyer et al. (1995 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C13H15NO2

M = 217.26

Monoclinic,

a = 7.5511 (3) Å

b = 12.2476 (6) Å

c = 12.9449 (5) Å

β = 105.488 (2)°

V = 1153.71 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 (2) K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.983

15440 measured reflections

3620 independent reflections

2068 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.184

S = 1.03

3620 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034156/bq2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034156/bq2100Isup2.hkl

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

C13H15NO2	F(000) = 464
Mr = 217.26	Dx = 1.251 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4312 reflections
a = 7.5511 (3) Å	θ = 2.3–24.1°
b = 12.2476 (6) Å	µ = 0.08 mm−1
c = 12.9449 (5) Å	T = 295 K
β = 105.488 (2)°	Block, yellow
V = 1153.71 (9) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	3620 independent reflections
Radiation source: fine-focus sealed tube	2068 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 31.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.979, Tmax = 0.983	k = −17→17
15440 measured reflections	l = −18→18

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0844P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
3620 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.7616 (2)	−0.19859 (13)	0.57067 (13)	0.0527 (4)
C2	0.7747 (2)	−0.30504 (16)	0.61130 (15)	0.0653 (5)
H2	0.8324	−0.3194	0.6829	0.078*
C3	0.7003 (3)	−0.38637 (16)	0.54252 (18)	0.0750 (5)
H3	0.7075	−0.4577	0.5679	0.090*
C4	0.6132 (3)	−0.36648 (16)	0.43493 (18)	0.0738 (5)
H4	0.5646	−0.4246	0.3901	0.089*
C5	0.5983 (2)	−0.26368 (16)	0.39465 (14)	0.0655 (4)
H5	0.5386	−0.2510	0.3230	0.079*
C6	0.67448 (19)	−0.17669 (13)	0.46276 (12)	0.0525 (4)
C7	0.68784 (19)	−0.06336 (13)	0.44615 (11)	0.0501 (4)
C8	0.78272 (19)	−0.01966 (13)	0.54312 (11)	0.0512 (4)
C9	0.9305 (3)	−0.09425 (17)	0.73226 (14)	0.0757 (5)
H9A	0.9384	−0.1651	0.7650	0.114*
H9B	0.8689	−0.0449	0.7687	0.114*
H9C	1.0519	−0.0675	0.7371	0.114*
C10	0.6076 (2)	−0.00822 (15)	0.34166 (13)	0.0670 (5)
H10A	0.5464	0.0575	0.3534	0.100*
H10B	0.5209	−0.0561	0.2955	0.100*
H10C	0.7038	0.0095	0.3088	0.100*
C11	0.8333 (2)	0.09395 (14)	0.57069 (13)	0.0559 (4)
C12	0.8335 (2)	0.27250 (13)	0.50367 (14)	0.0644 (4)
H12A	0.9652	0.2837	0.5286	0.077*
H12B	0.7771	0.3007	0.5573	0.077*
C13	0.7583 (3)	0.32875 (18)	0.40024 (17)	0.0805 (6)
H13A	0.8079	0.2962	0.3465	0.121*
H13B	0.7913	0.4046	0.4077	0.121*
H13C	0.6269	0.3219	0.3793	0.121*
N1	0.82742 (18)	−0.10221 (11)	0.61980 (10)	0.0568 (4)
O1	0.9033 (2)	0.12730 (12)	0.65918 (10)	0.0943 (5)
O2	0.79272 (16)	0.15785 (9)	0.48555 (9)	0.0632 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0489 (7)	0.0561 (9)	0.0535 (9)	0.0029 (6)	0.0146 (6)	0.0022 (7)
C2	0.0636 (9)	0.0662 (11)	0.0666 (11)	0.0026 (8)	0.0182 (8)	0.0136 (9)
C3	0.0774 (12)	0.0564 (11)	0.0939 (15)	−0.0017 (9)	0.0278 (11)	0.0091 (10)
C4	0.0742 (11)	0.0606 (11)	0.0849 (14)	−0.0079 (9)	0.0183 (10)	−0.0079 (10)
C5	0.0627 (9)	0.0696 (11)	0.0595 (10)	−0.0025 (8)	0.0081 (7)	−0.0072 (9)
C6	0.0476 (7)	0.0574 (9)	0.0519 (8)	0.0043 (6)	0.0122 (6)	0.0002 (7)
C7	0.0499 (7)	0.0552 (9)	0.0439 (8)	0.0047 (6)	0.0104 (6)	−0.0002 (6)
C8	0.0529 (8)	0.0556 (9)	0.0459 (8)	0.0041 (6)	0.0144 (6)	0.0012 (7)
C9	0.0883 (13)	0.0815 (13)	0.0488 (9)	0.0011 (10)	0.0035 (9)	0.0088 (9)
C10	0.0770 (11)	0.0675 (11)	0.0492 (9)	0.0038 (9)	0.0043 (8)	0.0050 (8)
C11	0.0624 (9)	0.0597 (10)	0.0462 (8)	0.0004 (7)	0.0155 (7)	−0.0025 (7)
C12	0.0722 (10)	0.0549 (10)	0.0682 (11)	0.0016 (8)	0.0226 (8)	−0.0044 (8)
C13	0.0902 (13)	0.0688 (12)	0.0804 (13)	0.0093 (10)	0.0189 (11)	0.0097 (10)
N1	0.0588 (7)	0.0631 (9)	0.0467 (7)	0.0022 (6)	0.0109 (6)	0.0036 (6)
O1	0.1481 (14)	0.0728 (9)	0.0498 (7)	−0.0162 (9)	0.0050 (8)	−0.0092 (6)
O2	0.0805 (8)	0.0518 (7)	0.0536 (7)	−0.0007 (5)	0.0113 (6)	−0.0014 (5)

C1—N1	1.370 (2)	C9—N1	1.459 (2)
C1—C2	1.400 (2)	C9—H9A	0.9600
C1—C6	1.402 (2)	C9—H9B	0.9600
C2—C3	1.354 (3)	C9—H9C	0.9600
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.394 (3)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.356 (3)	C11—O1	1.198 (2)
C4—H4	0.9300	C11—O2	1.319 (2)
C5—C6	1.404 (2)	C12—O2	1.443 (2)
C5—H5	0.9300	C12—C13	1.478 (3)
C6—C7	1.412 (2)	C12—H12A	0.9700
C7—C8	1.377 (2)	C12—H12B	0.9700
C7—C10	1.488 (2)	C13—H13A	0.9600
C8—N1	1.394 (2)	C13—H13B	0.9600
C8—C11	1.462 (2)	C13—H13C	0.9600
N1—C1—C2	130.38 (16)	H9A—C9—H9C	109.5
N1—C1—C6	108.26 (14)	H9B—C9—H9C	109.5
C2—C1—C6	121.33 (16)	C7—C10—H10A	109.5
C3—C2—C1	117.57 (17)	C7—C10—H10B	109.5
C3—C2—H2	121.2	H10A—C10—H10B	109.5
C1—C2—H2	121.2	C7—C10—H10C	109.5
C2—C3—C4	122.06 (18)	H10A—C10—H10C	109.5
C2—C3—H3	119.0	H10B—C10—H10C	109.5
C4—C3—H3	119.0	O1—C11—O2	122.77 (16)
C5—C4—C3	121.00 (18)	O1—C11—C8	125.30 (16)
C5—C4—H4	119.5	O2—C11—C8	111.93 (14)
C3—C4—H4	119.5	O2—C12—C13	107.02 (15)
C4—C5—C6	119.02 (17)	O2—C12—H12A	110.3
C4—C5—H5	120.5	C13—C12—H12A	110.3
C6—C5—H5	120.5	O2—C12—H12B	110.3
C1—C6—C5	119.01 (15)	C13—C12—H12B	110.3
C1—C6—C7	107.83 (14)	H12A—C12—H12B	108.6
C5—C6—C7	133.16 (15)	C12—C13—H13A	109.5
C8—C7—C6	106.51 (13)	C12—C13—H13B	109.5
C8—C7—C10	129.70 (16)	H13A—C13—H13B	109.5
C6—C7—C10	123.78 (14)	C12—C13—H13C	109.5
C7—C8—N1	109.60 (14)	H13A—C13—H13C	109.5
C7—C8—C11	129.14 (14)	H13B—C13—H13C	109.5
N1—C8—C11	121.25 (14)	C1—N1—C8	107.79 (13)
N1—C9—H9A	109.5	C1—N1—C9	123.47 (14)
N1—C9—H9B	109.5	C8—N1—C9	128.70 (15)
H9A—C9—H9B	109.5	C11—O2—C12	116.72 (13)
N1—C9—H9C	109.5
N1—C1—C2—C3	−177.99 (16)	C6—C7—C8—C11	−179.58 (14)
C6—C1—C2—C3	0.1 (2)	C10—C7—C8—C11	−0.7 (3)
C1—C2—C3—C4	0.0 (3)	C7—C8—C11—O1	173.58 (17)
C2—C3—C4—C5	−0.5 (3)	N1—C8—C11—O1	−5.4 (3)
C3—C4—C5—C6	0.9 (3)	C7—C8—C11—O2	−6.4 (2)
N1—C1—C6—C5	178.77 (13)	N1—C8—C11—O2	174.65 (12)
C2—C1—C6—C5	0.3 (2)	C2—C1—N1—C8	178.04 (15)
N1—C1—C6—C7	−0.08 (16)	C6—C1—N1—C8	−0.24 (16)
C2—C1—C6—C7	−178.54 (14)	C2—C1—N1—C9	−0.1 (3)
C4—C5—C6—C1	−0.8 (2)	C6—C1—N1—C9	−178.40 (14)
C4—C5—C6—C7	177.72 (16)	C7—C8—N1—C1	0.48 (16)
C1—C6—C7—C8	0.37 (16)	C11—C8—N1—C1	179.62 (13)
C5—C6—C7—C8	−178.25 (16)	C7—C8—N1—C9	178.52 (15)
C1—C6—C7—C10	−178.61 (14)	C11—C8—N1—C9	−2.3 (2)
C5—C6—C7—C10	2.8 (3)	O1—C11—O2—C12	−1.2 (2)
C6—C7—C8—N1	−0.52 (15)	C8—C11—O2—C12	178.80 (13)
C10—C7—C8—N1	178.38 (15)	C13—C12—O2—C11	−173.84 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2	0.96	2.49	2.858 (2)	103
C2—H2···O1i	0.93	2.53	3.401 (2)	156
C12—H12A···Cg1ii	0.97	2.76	3.646 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.53	3.401 (2)	156
C12—H12A⋯Cg1ii	0.97	2.76	3.646 (2)	152

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1–C6 ring.