2-(1-Ethyl-5-meth-oxy-1H-indol-3-yl)-N-isopropyl-2-oxoacetamide.

In the title compound, C(16)H(20)N(2)O(3), the crystal packing is stabilized by weak π-π stacking inter-actions [centroid-centroid distances = 3.577 (9) and 3.693 (9) Å] and inter-molecular C-H⋯O and N-H⋯O hydrogen-bond inter-actions. The C atoms of the N-isopropyl group are disordered over two sets of sites with occupancies of 0.61(3) and 0.39(3).

Related literature

For the biological activity of the title compound and its derivatives, see: Souli et al. (2008 ▶); Chai et al. (2006 ▶); Radwan et al. (2007 ▶); Karthikeyan et al. (2009 ▶). For the preparation, see: Bacher et al. (2001 ▶). For bond lengths and angles in similar structures, see: Feng et al. (2008 ▶); Sonar et al. (2006 ▶).

Experimental

Crystal data

C16H20N2O3

M = 288.34

Orthorhombic,

a = 11.593 (3) Å

b = 9.182 (2) Å

c = 27.796 (6) Å

V = 2958.8 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.30 × 0.24 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.974, T max = 0.991

25486 measured reflections

3527 independent reflections

3320 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.12

3527 reflections

204 parameters

39 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012815/hg5020sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012815/hg5020Isup2.hkl

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

C16H20N2O3	F(000) = 1232
Mr = 288.34	Dx = 1.295 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9914 reflections
a = 11.593 (3) Å	θ = 1.9–27.9°
b = 9.182 (2) Å	µ = 0.09 mm−1
c = 27.796 (6) Å	T = 113 K
V = 2958.8 (11) Å3	Prism, colorless
Z = 8	0.30 × 0.24 × 0.10 mm

Rigaku Saturn CCD area-detector diffractometer	3527 independent reflections
Radiation source: rotating anode	3320 reflections with I > 2σ(I)
multilayer	Rint = 0.053
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.5°
ω and φ scans	h = −14→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→9
Tmin = 0.974, Tmax = 0.991	l = −36→36
25486 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.8297P] where P = (Fo2 + 2Fc2)/3
3527 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.32 e Å−3
39 restraints	Δρmin = −0.28 e Å−3

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	Occ. (<1)
O1	0.47198 (9)	0.63365 (11)	0.45512 (3)	0.0265 (2)
O2	0.65875 (8)	0.73051 (10)	0.62010 (3)	0.0242 (2)
O3	0.64406 (8)	1.05760 (10)	0.68489 (3)	0.0233 (2)
N1	0.37396 (10)	1.06105 (12)	0.58694 (4)	0.0201 (2)
N2	0.75248 (11)	0.85420 (14)	0.69650 (4)	0.0247 (3)
C1	0.38287 (11)	0.95977 (14)	0.54960 (4)	0.0188 (3)
C2	0.31491 (12)	0.94441 (14)	0.50881 (4)	0.0208 (3)
H2A	0.2511	1.0070	0.5031	0.025*
C3	0.34338 (11)	0.83450 (15)	0.47660 (5)	0.0210 (3)
H3A	0.2987	0.8211	0.4483	0.025*
C4	0.43820 (11)	0.74299 (14)	0.48577 (4)	0.0200 (3)
C5	0.50502 (11)	0.75732 (14)	0.52708 (4)	0.0198 (3)
H5A	0.5681	0.6938	0.5330	0.024*
C6	0.47675 (11)	0.86775 (14)	0.55956 (4)	0.0177 (3)
C7	0.52557 (11)	0.91743 (14)	0.60485 (4)	0.0185 (3)
C8	0.45861 (11)	1.03582 (14)	0.61905 (4)	0.0191 (3)
H8A	0.4710	1.0911	0.6475	0.023*
C9	0.27776 (12)	1.16154 (15)	0.59397 (5)	0.0244 (3)
H9A	0.2564	1.2055	0.5627	0.029*
H9B	0.3020	1.2411	0.6158	0.029*
C10	0.17353 (13)	1.08439 (16)	0.61518 (5)	0.0284 (3)
H10A	0.1105	1.1544	0.6194	0.043*
H10B	0.1941	1.0425	0.6464	0.043*
H10C	0.1487	1.0066	0.5934	0.043*
C11	0.40229 (13)	0.60947 (16)	0.41358 (5)	0.0261 (3)
H11A	0.4349	0.5295	0.3946	0.039*
H11B	0.4003	0.6982	0.3940	0.039*
H11C	0.3238	0.5841	0.4236	0.039*
C12	0.61865 (11)	0.85066 (14)	0.63061 (4)	0.0180 (3)
C13	0.67303 (11)	0.93253 (14)	0.67372 (4)	0.0189 (3)
C15	0.9362 (6)	0.9639 (14)	0.7211 (3)	0.0447 (16)	0.61 (3)
H15A	0.9270	1.0323	0.6943	0.067*	0.61 (3)
H15B	0.9831	0.8809	0.7106	0.067*	0.61 (3)
H15C	0.9746	1.0132	0.7479	0.067*	0.61 (3)
C14	0.81996 (14)	0.91109 (16)	0.73695 (5)	0.0291 (3)	0.61 (3)
H14A	0.7777	0.9993	0.7485	0.035*	0.61 (3)
C15'	0.9489 (8)	0.911 (2)	0.7214 (5)	0.048 (3)	0.39 (3)
H15D	0.9596	0.9779	0.6943	0.072*	0.39 (3)
H15E	0.9712	0.8122	0.7115	0.072*	0.39 (3)
H15F	0.9971	0.9418	0.7485	0.072*	0.39 (3)
C14'	0.81996 (14)	0.91109 (16)	0.73695 (5)	0.0291 (3)	0.39 (3)
H14B	0.7935	1.0102	0.7470	0.035*	0.39 (3)
C16	0.81764 (17)	0.8043 (2)	0.77817 (5)	0.0408 (4)
H16A	0.7405	0.7968	0.7907	0.049*
H16B	0.8425	0.7108	0.7667	0.049*
H16C	0.8685	0.8368	0.8027	0.049*
H2B	0.7703 (15)	0.765 (2)	0.6858 (6)	0.031 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0291 (5)	0.0292 (5)	0.0212 (5)	0.0041 (4)	−0.0062 (4)	−0.0094 (4)
O2	0.0260 (5)	0.0223 (5)	0.0243 (5)	0.0028 (4)	−0.0032 (4)	−0.0065 (4)
O3	0.0265 (5)	0.0199 (5)	0.0234 (5)	−0.0003 (4)	−0.0028 (4)	−0.0050 (4)
N1	0.0251 (6)	0.0172 (5)	0.0181 (5)	0.0007 (4)	−0.0016 (4)	−0.0008 (4)
N2	0.0303 (6)	0.0212 (6)	0.0227 (5)	0.0025 (5)	−0.0089 (5)	−0.0065 (5)
C1	0.0229 (6)	0.0165 (6)	0.0171 (6)	−0.0022 (5)	0.0016 (5)	0.0011 (5)
C2	0.0235 (7)	0.0206 (6)	0.0183 (6)	0.0003 (5)	−0.0015 (5)	0.0026 (5)
C3	0.0232 (7)	0.0220 (6)	0.0178 (6)	−0.0030 (5)	−0.0025 (5)	0.0010 (5)
C4	0.0228 (6)	0.0196 (6)	0.0176 (6)	−0.0027 (5)	0.0007 (5)	−0.0018 (5)
C5	0.0199 (6)	0.0206 (6)	0.0189 (6)	−0.0011 (5)	−0.0002 (5)	−0.0005 (5)
C6	0.0188 (6)	0.0181 (6)	0.0162 (5)	−0.0046 (5)	0.0009 (4)	0.0006 (5)
C7	0.0208 (6)	0.0188 (6)	0.0157 (5)	−0.0042 (5)	0.0014 (4)	−0.0003 (5)
C8	0.0226 (6)	0.0181 (6)	0.0165 (6)	−0.0031 (5)	0.0000 (5)	0.0002 (5)
C9	0.0318 (7)	0.0185 (6)	0.0228 (6)	0.0059 (5)	−0.0032 (5)	−0.0005 (5)
C10	0.0274 (7)	0.0273 (7)	0.0304 (7)	0.0082 (6)	−0.0016 (6)	−0.0013 (6)
C11	0.0308 (7)	0.0286 (7)	0.0189 (6)	−0.0015 (6)	−0.0052 (5)	−0.0062 (5)
C12	0.0189 (6)	0.0197 (6)	0.0154 (5)	−0.0038 (5)	0.0024 (4)	−0.0011 (4)
C13	0.0204 (6)	0.0208 (6)	0.0154 (5)	−0.0035 (5)	0.0015 (5)	−0.0013 (4)
C15	0.053 (2)	0.049 (4)	0.0325 (17)	−0.027 (2)	−0.0132 (15)	0.002 (2)
C14	0.0383 (8)	0.0248 (7)	0.0240 (7)	0.0002 (6)	−0.0138 (6)	−0.0066 (5)
C15'	0.051 (4)	0.059 (6)	0.035 (3)	−0.032 (4)	−0.009 (3)	−0.002 (4)
C14'	0.0383 (8)	0.0248 (7)	0.0240 (7)	0.0002 (6)	−0.0138 (6)	−0.0066 (5)
C16	0.0567 (11)	0.0436 (10)	0.0222 (7)	−0.0091 (8)	−0.0086 (7)	−0.0035 (6)

O1—C4	1.3739 (15)	C9—C10	1.520 (2)
O1—C11	1.4264 (16)	C9—H9A	0.9900
O2—C12	1.2323 (16)	C9—H9B	0.9900
O3—C13	1.2361 (16)	C10—H10A	0.9800
N1—C8	1.3465 (16)	C10—H10B	0.9800
N1—C1	1.3974 (16)	C10—H10C	0.9800
N1—C9	1.4606 (17)	C11—H11A	0.9800
N2—C13	1.3291 (18)	C11—H11B	0.9800
N2—C14	1.4659 (17)	C11—H11C	0.9800
N2—H2B	0.894 (19)	C12—C13	1.5487 (17)
C1—C2	1.3879 (18)	C15—C14	1.499 (5)
C1—C6	1.4053 (18)	C15—H15A	0.9800
C2—C3	1.3888 (18)	C15—H15B	0.9800
C2—H2A	0.9500	C15—H15C	0.9800
C3—C4	1.4069 (19)	C14—C16	1.508 (2)
C3—H3A	0.9500	C14—H14A	1.0000
C4—C5	1.3913 (18)	C15'—H15D	0.9800
C5—C6	1.3966 (17)	C15'—H15E	0.9800
C5—H5A	0.9500	C15'—H15F	0.9800
C6—C7	1.4537 (17)	C16—H16A	0.9632
C7—C8	1.3928 (18)	C16—H16B	0.9595
C7—C12	1.4329 (18)	C16—H16C	0.9502
C8—H8A	0.9500
C4—O1—C11	117.02 (11)	C9—C10—H10B	109.5
C8—N1—C1	108.90 (11)	H10A—C10—H10B	109.5
C8—N1—C9	125.21 (11)	C9—C10—H10C	109.5
C1—N1—C9	125.18 (11)	H10A—C10—H10C	109.5
C13—N2—C14	122.84 (12)	H10B—C10—H10C	109.5
C13—N2—H2B	119.8 (12)	O1—C11—H11A	109.5
C14—N2—H2B	117.2 (12)	O1—C11—H11B	109.5
C2—C1—N1	129.23 (12)	H11A—C11—H11B	109.5
C2—C1—C6	122.64 (12)	O1—C11—H11C	109.5
N1—C1—C6	108.12 (11)	H11A—C11—H11C	109.5
C1—C2—C3	117.75 (12)	H11B—C11—H11C	109.5
C1—C2—H2A	121.1	O2—C12—C7	123.27 (12)
C3—C2—H2A	121.1	O2—C12—C13	117.68 (11)
C2—C3—C4	120.19 (12)	C7—C12—C13	119.05 (11)
C2—C3—H3A	119.9	O3—C13—N2	124.85 (12)
C4—C3—H3A	119.9	O3—C13—C12	122.32 (12)
O1—C4—C5	114.98 (12)	N2—C13—C12	112.83 (11)
O1—C4—C3	123.14 (11)	C14—C15—H15A	109.5
C5—C4—C3	121.88 (12)	C14—C15—H15B	109.5
C4—C5—C6	118.12 (12)	H15A—C15—H15B	109.5
C4—C5—H5A	120.9	C14—C15—H15C	109.5
C6—C5—H5A	120.9	H15A—C15—H15C	109.5
C5—C6—C1	119.40 (12)	H15B—C15—H15C	109.5
C5—C6—C7	134.12 (12)	N2—C14—C15	111.7 (3)
C1—C6—C7	106.47 (11)	N2—C14—C16	109.97 (12)
C8—C7—C12	127.74 (11)	C15—C14—C16	116.8 (4)
C8—C7—C6	105.86 (11)	N2—C14—H14A	105.9
C12—C7—C6	126.28 (12)	C15—C14—H14A	105.9
N1—C8—C7	110.65 (11)	C16—C14—H14A	105.9
N1—C8—H8A	124.7	H15D—C15'—H15E	109.5
C7—C8—H8A	124.7	H15D—C15'—H15F	109.5
N1—C9—C10	111.38 (11)	H15E—C15'—H15F	109.5
N1—C9—H9A	109.4	C14—C16—H16A	109.8
C10—C9—H9A	109.4	C14—C16—H16B	109.0
N1—C9—H9B	109.4	H16A—C16—H16B	109.6
C10—C9—H9B	109.4	C14—C16—H16C	109.3
H9A—C9—H9B	108.0	H16A—C16—H16C	109.7
C9—C10—H10A	109.5	H16B—C16—H16C	109.5
C8—N1—C1—C2	−179.77 (13)	C5—C6—C7—C12	−5.2 (2)
C9—N1—C1—C2	9.5 (2)	C1—C6—C7—C12	175.99 (12)
C8—N1—C1—C6	0.47 (14)	C1—N1—C8—C7	−0.64 (15)
C9—N1—C1—C6	−170.26 (12)	C9—N1—C8—C7	170.09 (12)
N1—C1—C2—C3	179.21 (12)	C12—C7—C8—N1	−175.62 (12)
C6—C1—C2—C3	−1.05 (19)	C6—C7—C8—N1	0.54 (14)
C1—C2—C3—C4	0.07 (19)	C8—N1—C9—C10	−92.41 (15)
C11—O1—C4—C5	176.62 (12)	C1—N1—C9—C10	76.84 (16)
C11—O1—C4—C3	−3.38 (19)	C8—C7—C12—O2	165.58 (13)
C2—C3—C4—O1	−179.06 (12)	C6—C7—C12—O2	−9.8 (2)
C2—C3—C4—C5	0.9 (2)	C8—C7—C12—C13	−14.81 (19)
O1—C4—C5—C6	179.04 (11)	C6—C7—C12—C13	169.78 (11)
C3—C4—C5—C6	−0.96 (19)	C14—N2—C13—O3	−3.0 (2)
C4—C5—C6—C1	−0.01 (18)	C14—N2—C13—C12	176.90 (12)
C4—C5—C6—C7	−178.74 (13)	O2—C12—C13—O3	174.90 (12)
C2—C1—C6—C5	1.04 (19)	C7—C12—C13—O3	−4.74 (18)
N1—C1—C6—C5	−179.18 (11)	O2—C12—C13—N2	−4.97 (17)
C2—C1—C6—C7	−179.92 (12)	C7—C12—C13—N2	175.39 (12)
N1—C1—C6—C7	−0.13 (14)	C13—N2—C14—C15	−97.9 (6)
C5—C6—C7—C8	178.61 (14)	C13—N2—C14—C16	130.80 (15)
C1—C6—C7—C8	−0.23 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.95	2.54	3.4874 (17)	172
N2—H2B···O3ii	0.894 (19)	2.149 (19)	2.9933 (17)	157.2 (16)
Cg1—···.Cg2iii	.	.	3.693 (9)	.
Cg2—···.Cg2iii	.	.	3.577 (9)	.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.95	2.54	3.4874 (17)	172
N2—H2B⋯O3ii	0.894 (19)	2.149 (19)	2.9933 (17)	157.2 (16)

Symmetry codes: (i) ; (ii) .