Methyl 3-[(1-butyl-1H-indol-3-yl)carbonyl-amino]propionate.

In the title mol-ecule, C(17)H(22)N(2)O(3), the mean plane of the terminal (C=O)OMe fragment and the indole plane form a dihedral angle of 78.94 (3)°. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains extended along the c axis. The crystal packing exhibits π-π inter-actions, indicated by the short distance of 3.472 (2) Å between the centroids of the five-membered heterocycles of neighbouring mol-ecules.

Related literature

For the bioactivity of indole derivatives, see: Fabio et al. (2007 ▶); Sharma et al. (2004 ▶). For related structures, see: Zeng et al. (2005 ▶); Siddiquee et al. (2009 ▶).

Experimental

Crystal data

C17H22N2O3

M = 302.37

Monoclinic,

a = 14.144 (3) Å

b = 12.685 (3) Å

c = 9.198 (2) Å

β = 107.151 (4)°

V = 1576.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.46 × 0.42 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.985

7760 measured reflections

3093 independent reflections

2169 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.05

3093 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker,1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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/S1600536809029973/cv2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029973/cv2594Isup2.hkl

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

C17H22N2O3	Dx = 1.274 Mg m−3
Mr = 302.37	Melting point: 367 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.144 (3) Å	Cell parameters from 2799 reflections
b = 12.685 (3) Å	θ = 2.8–26.9°
c = 9.198 (2) Å	µ = 0.09 mm−1
β = 107.151 (4)°	T = 173 K
V = 1576.8 (6) Å3	Plate, colourless
Z = 4	0.46 × 0.42 × 0.17 mm
F(000) = 648

Bruker SMART 1K CCD area-detector diffractometer	3093 independent reflections
Radiation source: fine-focus sealed tube	2169 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→9
Tmin = 0.961, Tmax = 0.985	k = −15→13
7760 measured reflections	l = −11→10

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.3821P] where P = (Fo2 + 2Fc2)/3
3093 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.27 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
O1	0.32207 (9)	0.17769 (11)	1.18054 (15)	0.0326 (3)
N2	0.27815 (11)	0.22657 (13)	0.93470 (18)	0.0286 (4)
H2	0.2944	0.2301	0.8495	0.034*
N1	0.56995 (11)	0.12769 (12)	0.95991 (17)	0.0271 (4)
O2	0.07347 (10)	0.00166 (12)	0.83159 (18)	0.0431 (4)
C1	0.47775 (13)	0.16910 (14)	0.9284 (2)	0.0255 (4)
H1	0.4419	0.1987	0.8331	0.031*
C2	0.44315 (13)	0.16250 (14)	1.0527 (2)	0.0251 (4)
O3	0.06776 (13)	0.13614 (14)	0.67382 (18)	0.0545 (5)
C3	0.52016 (13)	0.11227 (14)	1.1707 (2)	0.0259 (4)
C9	0.34451 (13)	0.19061 (15)	1.0605 (2)	0.0258 (4)
C4	0.53054 (14)	0.07969 (15)	1.3199 (2)	0.0300 (4)
H4	0.4797	0.0931	1.3659	0.036*
C12	0.08303 (14)	0.10345 (18)	0.8007 (2)	0.0343 (5)
C14	0.62646 (14)	0.11611 (16)	0.8515 (2)	0.0292 (4)
H14A	0.5822	0.1302	0.7479	0.035*
H14B	0.6494	0.0422	0.8539	0.035*
C7	0.68374 (14)	0.03955 (15)	1.1879 (2)	0.0312 (5)
H7	0.7354	0.0266	1.1436	0.037*
C8	0.59785 (13)	0.09149 (14)	1.1080 (2)	0.0255 (4)
C11	0.11220 (14)	0.16838 (17)	0.9426 (2)	0.0328 (5)
H11A	0.1460	0.1225	1.0294	0.039*
H11B	0.0517	0.1965	0.9619	0.039*
C10	0.18006 (13)	0.25988 (16)	0.9350 (2)	0.0310 (5)
H10A	0.1496	0.3012	0.8416	0.037*
H10B	0.1862	0.3068	1.0234	0.037*
C15	0.71526 (14)	0.18848 (16)	0.8815 (2)	0.0300 (5)
H15A	0.7627	0.1708	0.9813	0.036*
H15B	0.6936	0.2623	0.8862	0.036*
C16	0.76656 (15)	0.17862 (17)	0.7580 (2)	0.0364 (5)
H16A	0.7164	0.1870	0.6576	0.044*
H16B	0.8146	0.2371	0.7698	0.044*
C5	0.61526 (15)	0.02801 (16)	1.3987 (2)	0.0345 (5)
H5	0.6227	0.0055	1.4999	0.041*
C6	0.69128 (15)	0.00763 (16)	1.3333 (2)	0.0353 (5)
H6	0.7489	−0.0288	1.3906	0.042*
C17	0.82035 (16)	0.07542 (19)	0.7591 (3)	0.0455 (6)
H17A	0.8722	0.0676	0.8564	0.068*
H17B	0.8504	0.0749	0.6757	0.068*
H17C	0.7734	0.0169	0.7461	0.068*
C13	0.04133 (18)	−0.0678 (2)	0.7031 (3)	0.0564 (7)
H13A	−0.0213	−0.0421	0.6344	0.085*
H13B	0.0319	−0.1389	0.7382	0.085*
H13C	0.0915	−0.0698	0.6489	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0298 (7)	0.0442 (9)	0.0277 (7)	−0.0011 (6)	0.0144 (6)	−0.0037 (6)
N2	0.0250 (8)	0.0355 (9)	0.0278 (9)	0.0011 (7)	0.0117 (7)	−0.0009 (7)
N1	0.0256 (8)	0.0307 (9)	0.0281 (9)	0.0003 (7)	0.0124 (7)	−0.0005 (7)
O2	0.0347 (8)	0.0382 (9)	0.0536 (10)	−0.0014 (7)	0.0088 (7)	−0.0073 (7)
C1	0.0233 (9)	0.0261 (10)	0.0274 (10)	0.0004 (8)	0.0078 (8)	0.0002 (8)
C2	0.0251 (9)	0.0247 (10)	0.0266 (10)	−0.0027 (8)	0.0095 (8)	−0.0022 (8)
O3	0.0636 (11)	0.0652 (12)	0.0348 (9)	−0.0229 (9)	0.0148 (8)	−0.0042 (8)
C3	0.0255 (10)	0.0233 (9)	0.0301 (10)	−0.0034 (8)	0.0100 (8)	−0.0026 (8)
C9	0.0269 (10)	0.0252 (10)	0.0272 (10)	−0.0047 (8)	0.0107 (8)	−0.0061 (8)
C4	0.0307 (10)	0.0299 (10)	0.0312 (10)	−0.0062 (8)	0.0122 (8)	−0.0014 (8)
C12	0.0216 (10)	0.0450 (13)	0.0387 (12)	−0.0051 (9)	0.0128 (9)	−0.0032 (10)
C14	0.0282 (10)	0.0329 (11)	0.0307 (11)	0.0002 (8)	0.0152 (8)	−0.0041 (8)
C7	0.0273 (10)	0.0287 (10)	0.0385 (12)	0.0001 (8)	0.0109 (9)	−0.0005 (9)
C8	0.0254 (10)	0.0221 (9)	0.0297 (10)	−0.0039 (7)	0.0089 (8)	−0.0034 (8)
C11	0.0255 (10)	0.0413 (12)	0.0341 (11)	−0.0018 (9)	0.0129 (8)	−0.0013 (9)
C10	0.0246 (10)	0.0323 (11)	0.0377 (11)	0.0024 (8)	0.0116 (8)	−0.0032 (9)
C15	0.0303 (10)	0.0304 (10)	0.0333 (11)	−0.0004 (8)	0.0158 (8)	−0.0008 (8)
C16	0.0354 (11)	0.0419 (12)	0.0371 (12)	−0.0047 (9)	0.0187 (9)	0.0014 (9)
C5	0.0388 (12)	0.0337 (11)	0.0293 (11)	−0.0044 (9)	0.0074 (9)	0.0054 (9)
C6	0.0321 (11)	0.0300 (11)	0.0401 (12)	0.0014 (9)	0.0049 (9)	0.0055 (9)
C17	0.0348 (12)	0.0590 (16)	0.0483 (14)	0.0078 (11)	0.0211 (11)	−0.0015 (11)
C13	0.0407 (13)	0.0510 (15)	0.0742 (18)	−0.0051 (11)	0.0118 (12)	−0.0255 (13)

O1—C9	1.247 (2)	C7—C8	1.387 (3)
N2—C9	1.337 (2)	C7—H7	0.9500
N2—C10	1.451 (2)	C11—C10	1.521 (3)
N2—H2	0.8800	C11—H11A	0.9900
N1—C1	1.356 (2)	C11—H11B	0.9900
N1—C8	1.380 (2)	C10—H10A	0.9900
N1—C14	1.458 (2)	C10—H10B	0.9900
O2—C12	1.337 (3)	C15—C16	1.523 (3)
O2—C13	1.436 (3)	C15—H15A	0.9900
C1—C2	1.373 (3)	C15—H15B	0.9900
C1—H1	0.9500	C16—C17	1.513 (3)
C2—C3	1.440 (3)	C16—H16A	0.9900
C2—C9	1.462 (3)	C16—H16B	0.9900
O3—C12	1.197 (2)	C5—C6	1.402 (3)
C3—C4	1.399 (3)	C5—H5	0.9500
C3—C8	1.408 (3)	C6—H6	0.9500
C4—C5	1.371 (3)	C17—H17A	0.9800
C4—H4	0.9500	C17—H17B	0.9800
C12—C11	1.495 (3)	C17—H17C	0.9800
C14—C15	1.514 (3)	C13—H13A	0.9800
C14—H14A	0.9900	C13—H13B	0.9800
C14—H14B	0.9900	C13—H13C	0.9800
C7—C6	1.371 (3)
C9—N2—C10	121.69 (16)	C12—C11—H11B	108.9
C9—N2—H2	119.2	C10—C11—H11B	108.9
C10—N2—H2	119.2	H11A—C11—H11B	107.7
C1—N1—C8	108.50 (15)	N2—C10—C11	113.24 (16)
C1—N1—C14	125.40 (16)	N2—C10—H10A	108.9
C8—N1—C14	125.93 (16)	C11—C10—H10A	108.9
C12—O2—C13	116.39 (19)	N2—C10—H10B	108.9
N1—C1—C2	110.77 (16)	C11—C10—H10B	108.9
N1—C1—H1	124.6	H10A—C10—H10B	107.7
C2—C1—H1	124.6	C14—C15—C16	111.46 (16)
C1—C2—C3	106.16 (16)	C14—C15—H15A	109.3
C1—C2—C9	127.25 (17)	C16—C15—H15A	109.3
C3—C2—C9	126.32 (16)	C14—C15—H15B	109.3
C4—C3—C8	118.55 (17)	C16—C15—H15B	109.3
C4—C3—C2	135.00 (17)	H15A—C15—H15B	108.0
C8—C3—C2	106.41 (16)	C17—C16—C15	114.53 (17)
O1—C9—N2	120.95 (17)	C17—C16—H16A	108.6
O1—C9—C2	120.46 (17)	C15—C16—H16A	108.6
N2—C9—C2	118.54 (16)	C17—C16—H16B	108.6
C5—C4—C3	118.83 (18)	C15—C16—H16B	108.6
C5—C4—H4	120.6	H16A—C16—H16B	107.6
C3—C4—H4	120.6	C4—C5—C6	121.53 (19)
O3—C12—O2	122.8 (2)	C4—C5—H5	119.2
O3—C12—C11	125.8 (2)	C6—C5—H5	119.2
O2—C12—C11	111.45 (18)	C7—C6—C5	121.00 (18)
N1—C14—C15	113.98 (15)	C7—C6—H6	119.5
N1—C14—H14A	108.8	C5—C6—H6	119.5
C15—C14—H14A	108.8	C16—C17—H17A	109.5
N1—C14—H14B	108.8	C16—C17—H17B	109.5
C15—C14—H14B	108.8	H17A—C17—H17B	109.5
H14A—C14—H14B	107.7	C16—C17—H17C	109.5
C6—C7—C8	117.49 (18)	H17A—C17—H17C	109.5
C6—C7—H7	121.3	H17B—C17—H17C	109.5
C8—C7—H7	121.3	O2—C13—H13A	109.5
N1—C8—C7	129.22 (17)	O2—C13—H13B	109.5
N1—C8—C3	108.14 (16)	H13A—C13—H13B	109.5
C7—C8—C3	122.60 (18)	O2—C13—H13C	109.5
C12—C11—C10	113.33 (16)	H13A—C13—H13C	109.5
C12—C11—H11A	108.9	H13B—C13—H13C	109.5
C10—C11—H11A	108.9
C8—N1—C1—C2	0.6 (2)	C1—N1—C8—C7	177.15 (19)
C14—N1—C1—C2	176.18 (16)	C14—N1—C8—C7	1.6 (3)
N1—C1—C2—C3	−0.4 (2)	C1—N1—C8—C3	−0.6 (2)
N1—C1—C2—C9	−174.69 (17)	C14—N1—C8—C3	−176.13 (16)
C1—C2—C3—C4	−177.5 (2)	C6—C7—C8—N1	−177.13 (18)
C9—C2—C3—C4	−3.0 (3)	C6—C7—C8—C3	0.3 (3)
C1—C2—C3—C8	0.0 (2)	C4—C3—C8—N1	178.29 (16)
C9—C2—C3—C8	174.42 (17)	C2—C3—C8—N1	0.3 (2)
C10—N2—C9—O1	4.9 (3)	C4—C3—C8—C7	0.4 (3)
C10—N2—C9—C2	−177.58 (16)	C2—C3—C8—C7	−177.55 (17)
C1—C2—C9—O1	177.91 (18)	O3—C12—C11—C10	−35.6 (3)
C3—C2—C9—O1	4.7 (3)	O2—C12—C11—C10	145.76 (17)
C1—C2—C9—N2	0.4 (3)	C9—N2—C10—C11	−74.0 (2)
C3—C2—C9—N2	−172.86 (17)	C12—C11—C10—N2	−69.1 (2)
C8—C3—C4—C5	−0.6 (3)	N1—C14—C15—C16	−175.70 (16)
C2—C3—C4—C5	176.6 (2)	C14—C15—C16—C17	−70.2 (2)
C13—O2—C12—O3	−1.3 (3)	C3—C4—C5—C6	0.2 (3)
C13—O2—C12—C11	177.36 (17)	C8—C7—C6—C5	−0.7 (3)
C1—N1—C14—C15	110.6 (2)	C4—C5—C6—C7	0.5 (3)
C8—N1—C14—C15	−74.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88	2.07	2.860 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88	2.07	2.860 (2)	149

Symmetry code: (i) .