Ethyl 2-(5-meth-oxy-2-methyl-1H-indol-3-yl)acetate.

In the title compound, C14H17NO3, the nine-membered 1H-indole ring system is essentially planar [maximum deviation = 0.019 (1) Å]. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains along [001]. These chains are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming a two-dimensional network lying parallel to the ac plane.

Related literature

For medicinal applications of the drug indomethacin (systematic name: 2-{1-[(4-chloro­phen­yl)carbon­yl]-5-meth­oxy-2-methyl-1H-indol-3-yl}acetic acid), see: Paneth (1995 ▶); McIntyre et al. (2001 ▶); Abou-Ghannam et al. (2012 ▶). For the synthesis and reactions of indomethacin with other non-steroidal anti-inflammatory mol­ecules, see: Mohamed et al. (2012 ▶).

Experimental

Crystal data

C14H17NO3

M = 247.29

Monoclinic,

a = 7.8117 (5) Å

b = 17.1953 (12) Å

c = 9.9003 (7) Å

β = 106.756 (1)°

V = 1273.39 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.23 × 0.21 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.84, T max = 1.00

22947 measured reflections

3374 independent reflections

2889 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.08

3374 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018618/su2618sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018618/su2618Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018618/su2618Isup3.cml

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

C14H17NO3	F(000) = 528
Mr = 247.29	Dx = 1.290 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9989 reflections
a = 7.8117 (5) Å	θ = 2.4–29.1°
b = 17.1953 (12) Å	µ = 0.09 mm−1
c = 9.9003 (7) Å	T = 150 K
β = 106.756 (1)°	Plate, colourless
V = 1273.39 (15) Å3	0.23 × 0.21 × 0.06 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2889 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.3660 pixels mm-1	θmax = 29.1°, θmin = 2.4°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −23→23
Tmin = 0.84, Tmax = 1.00	l = −13→13
22947 measured reflections

Refinement on F2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	W = 1/[Σ2(Fo2) + (0.0539P)2 + 0.3155P] where P = (Fo2 + 2Fc2)/3
3374 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. Spectroscopic data for the title compound: IR (KBr cm-1): (C=O ester 1728), (NH 3317), (C—H aliphatic, 2833–2924), (C—H, Ar, 2975–3002). 1H-NMR: (DMSO-D6) δ at 1.3(t, 3H, CH3 of ethyl group), 4.0(q, 2H, –CH2 aliphatic in ethyl group), 2.3(s, 3H, CH3), 3.4(s, –CH2), 3.7(s, 3H, –OCH3), 10.8(s, 1H, –NH), 6.8(s, 1H, Ar), 6.6(d, 1H, Ar), 7.2(d, 1H, Ar). 13C-NMR: 171 (C=O ester), 11(CH3 in indole), 14(CH3 of ethyl group), 29(–CH2), 55 (–OCH3), 59(–CH2 of ethyl group). 99, 103, 109, 110, 128, 129, 133,152 (8 C, aromatics). There are two signals at 29 and 59 p.p.m. oriented downward in the DEPT spectrum confirming the existence of two –CH2 groups.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.17116 (13)	0.36046 (6)	−0.24184 (10)	0.0376 (3)
O2	0.75724 (12)	0.08270 (5)	−0.02263 (9)	0.0312 (3)
O3	0.75501 (11)	0.01325 (4)	0.16773 (9)	0.0251 (2)
N1	0.65214 (13)	0.29386 (6)	0.27056 (11)	0.0264 (3)
C1	0.47230 (14)	0.25588 (6)	0.05968 (12)	0.0216 (3)
C2	0.34868 (15)	0.26677 (6)	−0.07390 (13)	0.0240 (3)
C3	0.29070 (16)	0.34165 (7)	−0.11378 (13)	0.0282 (3)
C4	0.35262 (18)	0.40558 (7)	−0.02372 (15)	0.0336 (4)
C5	0.47322 (17)	0.39589 (7)	0.10729 (15)	0.0309 (3)
C6	0.53295 (15)	0.32062 (6)	0.14800 (13)	0.0245 (3)
C7	0.09045 (18)	0.29785 (9)	−0.33106 (15)	0.0367 (4)
C8	0.66375 (15)	0.21415 (7)	0.26458 (12)	0.0243 (3)
C9	0.55670 (14)	0.18869 (6)	0.13595 (12)	0.0220 (3)
C10	0.77677 (16)	0.16917 (8)	0.38672 (13)	0.0312 (4)
C11	0.52395 (15)	0.10556 (6)	0.08854 (13)	0.0258 (3)
C12	0.68958 (14)	0.06698 (6)	0.06967 (12)	0.0224 (3)
C13	0.91945 (15)	−0.02529 (7)	0.16271 (13)	0.0272 (3)
C14	0.98064 (19)	−0.07392 (8)	0.29348 (16)	0.0395 (4)
H1	0.700 (2)	0.3250 (10)	0.347 (2)	0.052 (5)*
H2	0.30620	0.22390	−0.13500	0.0290*
H4	0.31030	0.45630	−0.05410	0.0400*
H5	0.51440	0.43900	0.16800	0.0370*
H7A	0.18300	0.26750	−0.35610	0.0550*
H7B	0.00600	0.31840	−0.41700	0.0550*
H7C	0.02660	0.26440	−0.28160	0.0550*
H10A	0.72640	0.11700	0.38710	0.0470*
H10B	0.77960	0.19600	0.47470	0.0470*
H10C	0.89850	0.16500	0.37860	0.0470*
H11A	0.42780	0.10380	−0.00200	0.0310*
H11B	0.48250	0.07610	0.15910	0.0310*
H13A	1.01170	0.01370	0.16000	0.0330*
H13B	0.89690	−0.05840	0.07760	0.0330*
H14A	1.00740	−0.04020	0.37670	0.0590*
H14B	1.08850	−0.10270	0.29240	0.0590*
H14C	0.88610	−0.11070	0.29690	0.0590*

	U11	U22	U33	U12	U13	U23
O1	0.0347 (5)	0.0333 (5)	0.0417 (5)	0.0089 (4)	0.0059 (4)	0.0110 (4)
O2	0.0383 (5)	0.0288 (4)	0.0283 (4)	0.0066 (4)	0.0124 (4)	0.0065 (3)
O3	0.0260 (4)	0.0219 (4)	0.0277 (4)	0.0049 (3)	0.0084 (3)	0.0047 (3)
N1	0.0275 (5)	0.0268 (5)	0.0265 (5)	−0.0049 (4)	0.0104 (4)	−0.0073 (4)
C1	0.0206 (5)	0.0194 (5)	0.0273 (5)	−0.0005 (4)	0.0111 (4)	−0.0010 (4)
C2	0.0233 (5)	0.0217 (5)	0.0283 (6)	0.0017 (4)	0.0093 (4)	−0.0001 (4)
C3	0.0258 (5)	0.0269 (6)	0.0340 (6)	0.0052 (4)	0.0122 (5)	0.0067 (5)
C4	0.0348 (6)	0.0200 (5)	0.0503 (8)	0.0051 (5)	0.0191 (6)	0.0048 (5)
C5	0.0352 (6)	0.0196 (5)	0.0432 (7)	−0.0024 (5)	0.0198 (6)	−0.0048 (5)
C6	0.0251 (5)	0.0222 (5)	0.0299 (6)	−0.0027 (4)	0.0140 (4)	−0.0039 (4)
C7	0.0297 (6)	0.0455 (8)	0.0335 (7)	0.0111 (5)	0.0071 (5)	0.0055 (6)
C8	0.0227 (5)	0.0268 (5)	0.0255 (5)	−0.0017 (4)	0.0104 (4)	−0.0018 (4)
C9	0.0199 (5)	0.0205 (5)	0.0265 (5)	−0.0002 (4)	0.0080 (4)	−0.0006 (4)
C10	0.0282 (6)	0.0394 (7)	0.0249 (6)	0.0023 (5)	0.0058 (5)	0.0005 (5)
C11	0.0216 (5)	0.0191 (5)	0.0345 (6)	−0.0002 (4)	0.0047 (4)	−0.0003 (4)
C12	0.0239 (5)	0.0164 (5)	0.0243 (5)	−0.0006 (4)	0.0027 (4)	−0.0016 (4)
C13	0.0244 (5)	0.0247 (5)	0.0323 (6)	0.0060 (4)	0.0080 (5)	0.0028 (5)
C14	0.0364 (7)	0.0369 (7)	0.0444 (8)	0.0134 (6)	0.0106 (6)	0.0145 (6)

O1—C3	1.3789 (16)	C11—C12	1.5128 (16)
O1—C7	1.4198 (18)	C13—C14	1.4990 (19)
O2—C12	1.2108 (15)	C2—H2	0.9500
O3—C12	1.3309 (13)	C4—H4	0.9500
O3—C13	1.4590 (15)	C5—H5	0.9500
N1—C6	1.3782 (16)	C7—H7A	0.9800
N1—C8	1.3760 (16)	C7—H7B	0.9800
N1—H1	0.914 (18)	C7—H7C	0.9800
C1—C2	1.4072 (17)	C10—H10A	0.9800
C1—C6	1.4105 (15)	C10—H10B	0.9800
C1—C9	1.4327 (15)	C10—H10C	0.9800
C2—C3	1.3841 (16)	C11—H11A	0.9900
C3—C4	1.4102 (18)	C11—H11B	0.9900
C4—C5	1.376 (2)	C13—H13A	0.9900
C5—C6	1.3953 (16)	C13—H13B	0.9900
C8—C9	1.3779 (16)	C14—H14A	0.9800
C8—C10	1.4914 (17)	C14—H14B	0.9800
C9—C11	1.5033 (15)	C14—H14C	0.9800
C3—O1—C7	117.11 (11)	C5—C4—H4	119.00
C12—O3—C13	116.57 (9)	C4—C5—H5	121.00
C6—N1—C8	109.32 (10)	C6—C5—H5	121.00
C6—N1—H1	123.0 (11)	O1—C7—H7A	109.00
C8—N1—H1	127.1 (11)	O1—C7—H7B	109.00
C2—C1—C6	119.63 (10)	O1—C7—H7C	109.00
C6—C1—C9	106.77 (10)	H7A—C7—H7B	109.00
C2—C1—C9	133.59 (10)	H7A—C7—H7C	109.00
C1—C2—C3	118.12 (10)	H7B—C7—H7C	109.00
O1—C3—C2	124.03 (11)	C8—C10—H10A	109.00
O1—C3—C4	114.61 (11)	C8—C10—H10B	109.00
C2—C3—C4	121.36 (12)	C8—C10—H10C	109.00
C3—C4—C5	121.23 (11)	H10A—C10—H10B	109.00
C4—C5—C6	117.76 (12)	H10A—C10—H10C	109.00
C1—C6—C5	121.90 (11)	H10B—C10—H10C	109.00
N1—C6—C5	130.45 (11)	C9—C11—H11A	109.00
N1—C6—C1	107.65 (9)	C9—C11—H11B	109.00
N1—C8—C9	109.04 (10)	C12—C11—H11A	109.00
N1—C8—C10	120.84 (11)	C12—C11—H11B	109.00
C9—C8—C10	130.11 (11)	H11A—C11—H11B	108.00
C1—C9—C8	107.18 (10)	O3—C13—H13A	110.00
C8—C9—C11	126.44 (10)	O3—C13—H13B	110.00
C1—C9—C11	126.24 (10)	C14—C13—H13A	110.00
C9—C11—C12	112.39 (10)	C14—C13—H13B	110.00
O2—C12—O3	123.10 (11)	H13A—C13—H13B	109.00
O2—C12—C11	124.77 (10)	C13—C14—H14A	110.00
O3—C12—C11	112.13 (10)	C13—C14—H14B	109.00
O3—C13—C14	106.78 (10)	C13—C14—H14C	110.00
C1—C2—H2	121.00	H14A—C14—H14B	109.00
C3—C2—H2	121.00	H14A—C14—H14C	109.00
C3—C4—H4	119.00	H14B—C14—H14C	109.00
C7—O1—C3—C2	6.53 (18)	C6—C1—C9—C8	−0.25 (13)
C7—O1—C3—C4	−173.81 (12)	C6—C1—C9—C11	175.68 (11)
C13—O3—C12—O2	2.08 (16)	C1—C2—C3—O1	179.49 (11)
C13—O3—C12—C11	−177.50 (9)	C1—C2—C3—C4	−0.15 (19)
C12—O3—C13—C14	171.98 (10)	O1—C3—C4—C5	−179.64 (13)
C8—N1—C6—C1	−2.16 (14)	C2—C3—C4—C5	0.0 (2)
C8—N1—C6—C5	177.77 (13)	C3—C4—C5—C6	0.3 (2)
C6—N1—C8—C9	2.03 (14)	C4—C5—C6—N1	179.64 (13)
C6—N1—C8—C10	−176.93 (11)	C4—C5—C6—C1	−0.4 (2)
C6—C1—C2—C3	−0.02 (17)	N1—C8—C9—C1	−1.07 (13)
C9—C1—C2—C3	178.39 (13)	N1—C8—C9—C11	−176.98 (11)
C2—C1—C6—N1	−179.74 (11)	C10—C8—C9—C1	177.77 (12)
C2—C1—C6—C5	0.33 (18)	C10—C8—C9—C11	1.9 (2)
C9—C1—C6—N1	1.47 (13)	C1—C9—C11—C12	117.42 (13)
C9—C1—C6—C5	−178.47 (12)	C8—C9—C11—C12	−67.42 (15)
C2—C1—C9—C8	−178.81 (13)	C9—C11—C12—O2	−69.51 (15)
C2—C1—C9—C11	−2.9 (2)	C9—C11—C12—O3	110.07 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.914 (18)	2.013 (18)	2.8987 (14)	162.7 (16)
C7—H7B···O2ii	0.98	2.57	3.4271 (18)	146
C13—H13A···O1iii	0.99	2.55	3.4236 (16)	148
C7—H7A···Cg1iv	0.98	2.99	3.9550 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.914 (18)	2.013 (18)	2.8987 (14)	162.7 (16)
C7—H7B⋯O2ii	0.98	2.57	3.4271 (18)	146
C13—H13A⋯O1iii	0.99	2.55	3.4236 (16)	148
C7—H7A⋯Cg1iv	0.98	2.99	3.9550 (16)	169

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