Methyl 2-(1H-indole-3-carboxamido)-acetate.

The title compound, C(12)H(12)N(2)O(3), was synthesized by condensation of methyl amino-acetate with 3-trichloro-acetyl-indole. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the b axis. The chains are further connected into a three-dimensional network by N-H⋯O hydrogen bonds involving the indole N atom. In the molecule, the indole skeleton is nearly planar [maximum deviation = 0.012 (1) Å] and the mean plane of the amido group is twisted from the mean plane of indole ring by 17.2 (1)°.

Related literature

For the bioactivity of indole derivatives, see: Di Fabio et al. (2007 ▶); Sharma & Tepe (2004 ▶). For related structures, see: Huang et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C12H12N2O3

M = 232.24

Orthorhombic,

a = 8.0024 (2) Å

b = 9.1279 (2) Å

c = 15.9767 (3) Å

V = 1167.02 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 150 K

0.49 × 0.17 × 0.12 mm

Data collection

Oxford Gemini S Ultra area-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) ▶ T min = 0.694, T max = 0.910

2269 measured reflections

1642 independent reflections

1613 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.05

1642 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 568 Friedel pairs

Flack parameter: −0.2 (3)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811006660/rz2556sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006660/rz2556Isup2.hkl

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

C12H12N2O3	Dx = 1.322 Mg m−3
Mr = 232.24	Melting point: 448 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1985 reflections
a = 8.0024 (2) Å	θ = 4.8–62.6°
b = 9.1279 (2) Å	µ = 0.80 mm−1
c = 15.9767 (3) Å	T = 150 K
V = 1167.02 (4) Å3	Prism, light yellow
Z = 4	0.49 × 0.17 × 0.12 mm
F(000) = 488

Oxford Gemini S Ultra area-detector diffractometer	1642 independent reflections
Radiation source: fine-focus sealed tube	1613 reflections with I > 2σ(I)
mirror	Rint = 0.016
φ and ω scans	θmax = 62.7°, θmin = 5.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −5→9
Tmin = 0.694, Tmax = 0.910	k = −10→8
2269 measured reflections	l = −18→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.0803P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.011
1642 reflections	Δρmax = 0.13 e Å−3
155 parameters	Δρmin = −0.14 e Å−3
0 restraints	Absolute structure: Flack (1983), 568 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.2 (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
C1	0.8259 (2)	0.08538 (18)	0.12627 (10)	0.0418 (4)
H1	0.9222	0.0261	0.1184	0.050*
N1	0.68538 (19)	0.07824 (16)	0.07961 (9)	0.0491 (4)
H1A	0.6691	0.0180	0.0374	0.059*
C8	0.5711 (2)	0.17992 (19)	0.10821 (10)	0.0451 (4)
C3	0.6450 (2)	0.25391 (16)	0.17586 (9)	0.0400 (4)
C4	0.5524 (2)	0.36258 (18)	0.21720 (11)	0.0498 (4)
H4	0.5985	0.4145	0.2633	0.060*
C5	0.3925 (3)	0.3921 (2)	0.18931 (12)	0.0608 (5)
H5	0.3288	0.4657	0.2167	0.073*
C6	0.3219 (3)	0.3166 (3)	0.12172 (14)	0.0660 (6)
H6	0.2115	0.3397	0.1044	0.079*
C7	0.4094 (3)	0.2099 (2)	0.08007 (12)	0.0593 (5)
H7	0.3621	0.1586	0.0341	0.071*
C9	0.9272 (2)	0.22893 (16)	0.25277 (10)	0.0383 (4)
C10	1.1689 (2)	0.1685 (2)	0.33471 (10)	0.0432 (4)
H10A	1.2129	0.2687	0.3260	0.052*
H10B	1.2642	0.0995	0.3315	0.052*
C11	1.0915 (2)	0.15897 (18)	0.42041 (10)	0.0394 (4)
C12	1.1129 (3)	0.2444 (3)	0.55958 (11)	0.0767 (7)
H12A	1.1425	0.1492	0.5839	0.115*
H12B	0.9915	0.2577	0.5621	0.115*
H12C	1.1680	0.3226	0.5912	0.115*
C2	0.8088 (2)	0.19136 (16)	0.18683 (10)	0.0380 (4)
N2	1.05189 (17)	0.13476 (14)	0.26902 (8)	0.0419 (3)
H2	1.0620	0.0534	0.2399	0.050*
O1	0.91340 (16)	0.34378 (12)	0.29446 (7)	0.0476 (3)
O2	0.97901 (16)	0.07845 (14)	0.43919 (8)	0.0561 (4)
O3	1.16709 (15)	0.24943 (15)	0.47336 (7)	0.0549 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0480 (9)	0.0397 (8)	0.0377 (8)	0.0024 (8)	−0.0025 (8)	−0.0015 (7)
N1	0.0594 (9)	0.0479 (8)	0.0401 (7)	0.0050 (8)	−0.0094 (7)	−0.0091 (7)
C8	0.0508 (10)	0.0442 (9)	0.0404 (9)	0.0019 (8)	−0.0013 (8)	0.0033 (8)
C3	0.0511 (9)	0.0351 (8)	0.0339 (7)	0.0003 (7)	0.0034 (8)	0.0053 (7)
C4	0.0644 (11)	0.0433 (8)	0.0417 (9)	0.0059 (9)	0.0127 (9)	0.0024 (8)
C5	0.0680 (12)	0.0583 (11)	0.0561 (11)	0.0205 (10)	0.0158 (11)	0.0109 (9)
C6	0.0540 (11)	0.0778 (14)	0.0662 (13)	0.0175 (11)	0.0044 (11)	0.0201 (12)
C7	0.0564 (11)	0.0669 (12)	0.0546 (11)	0.0039 (11)	−0.0117 (10)	0.0074 (10)
C9	0.0491 (9)	0.0338 (7)	0.0319 (7)	−0.0079 (7)	0.0056 (7)	0.0023 (7)
C10	0.0386 (8)	0.0511 (9)	0.0398 (8)	−0.0043 (8)	0.0017 (8)	−0.0026 (8)
C11	0.0371 (8)	0.0409 (8)	0.0403 (9)	−0.0010 (8)	−0.0037 (7)	0.0024 (7)
C12	0.0694 (13)	0.1237 (19)	0.0370 (9)	−0.0244 (14)	0.0026 (10)	−0.0143 (12)
C2	0.0483 (9)	0.0319 (8)	0.0337 (8)	−0.0024 (7)	0.0030 (7)	0.0011 (6)
N2	0.0491 (8)	0.0394 (6)	0.0372 (7)	−0.0002 (6)	0.0000 (6)	−0.0061 (6)
O1	0.0636 (7)	0.0346 (5)	0.0446 (6)	−0.0035 (6)	−0.0024 (6)	−0.0080 (5)
O2	0.0574 (7)	0.0629 (7)	0.0481 (7)	−0.0217 (7)	0.0045 (6)	0.0062 (6)
O3	0.0528 (7)	0.0742 (8)	0.0376 (6)	−0.0197 (7)	−0.0002 (6)	−0.0072 (7)

C1—N1	1.351 (2)	C7—H7	0.9500
C1—C2	1.375 (2)	C9—O1	1.2470 (19)
C1—H1	0.9500	C9—N2	1.342 (2)
N1—C8	1.381 (2)	C9—C2	1.458 (2)
N1—H1A	0.8800	C10—N2	1.440 (2)
C8—C7	1.397 (3)	C10—C11	1.505 (2)
C8—C3	1.405 (2)	C10—H10A	0.9900
C3—C4	1.403 (2)	C10—H10B	0.9900
C3—C2	1.440 (2)	C11—O2	1.2002 (19)
C4—C5	1.381 (3)	C11—O3	1.328 (2)
C4—H4	0.9500	C12—O3	1.445 (2)
C5—C6	1.400 (3)	C12—H12A	0.9800
C5—H5	0.9500	C12—H12B	0.9800
C6—C7	1.372 (3)	C12—H12C	0.9800
C6—H6	0.9500	N2—H2	0.8800
N1—C1—C2	109.84 (15)	O1—C9—C2	121.73 (15)
N1—C1—H1	125.1	N2—C9—C2	118.18 (13)
C2—C1—H1	125.1	N2—C10—C11	112.53 (13)
C1—N1—C8	109.64 (14)	N2—C10—H10A	109.1
C1—N1—H1A	125.2	C11—C10—H10A	109.1
C8—N1—H1A	125.2	N2—C10—H10B	109.1
N1—C8—C7	129.68 (17)	C11—C10—H10B	109.1
N1—C8—C3	107.41 (15)	H10A—C10—H10B	107.8
C7—C8—C3	122.90 (17)	O2—C11—O3	124.28 (16)
C4—C3—C8	118.67 (16)	O2—C11—C10	124.84 (15)
C4—C3—C2	134.70 (16)	O3—C11—C10	110.86 (14)
C8—C3—C2	106.61 (14)	O3—C12—H12A	109.5
C5—C4—C3	118.38 (18)	O3—C12—H12B	109.5
C5—C4—H4	120.8	H12A—C12—H12B	109.5
C3—C4—H4	120.8	O3—C12—H12C	109.5
C4—C5—C6	121.75 (18)	H12A—C12—H12C	109.5
C4—C5—H5	119.1	H12B—C12—H12C	109.5
C6—C5—H5	119.1	C1—C2—C3	106.50 (14)
C7—C6—C5	121.2 (2)	C1—C2—C9	127.52 (15)
C7—C6—H6	119.4	C3—C2—C9	125.89 (14)
C5—C6—H6	119.4	C9—N2—C10	119.16 (13)
C6—C7—C8	117.10 (19)	C9—N2—H2	120.4
C6—C7—H7	121.4	C10—N2—H2	120.4
C8—C7—H7	121.4	C11—O3—C12	116.79 (14)
O1—C9—N2	120.08 (15)
C2—C1—N1—C8	0.05 (19)	N1—C1—C2—C3	−0.22 (18)
C1—N1—C8—C7	−178.97 (19)	N1—C1—C2—C9	176.50 (15)
C1—N1—C8—C3	0.15 (19)	C4—C3—C2—C1	178.82 (17)
N1—C8—C3—C4	−179.08 (14)	C8—C3—C2—C1	0.30 (17)
C7—C8—C3—C4	0.1 (3)	C4—C3—C2—C9	2.0 (3)
N1—C8—C3—C2	−0.28 (18)	C8—C3—C2—C9	−176.48 (14)
C7—C8—C3—C2	178.92 (16)	O1—C9—C2—C1	166.46 (15)
C8—C3—C4—C5	−0.1 (2)	N2—C9—C2—C1	−14.7 (2)
C2—C3—C4—C5	−178.51 (18)	O1—C9—C2—C3	−17.4 (2)
C3—C4—C5—C6	0.2 (3)	N2—C9—C2—C3	161.42 (15)
C4—C5—C6—C7	−0.2 (3)	O1—C9—N2—C10	−0.2 (2)
C5—C6—C7—C8	0.2 (3)	C2—C9—N2—C10	−179.07 (14)
N1—C8—C7—C6	178.87 (18)	C11—C10—N2—C9	69.72 (19)
C3—C8—C7—C6	−0.1 (3)	O2—C11—O3—C12	2.6 (3)
N2—C10—C11—O2	30.2 (2)	C10—C11—O3—C12	−175.89 (17)
N2—C10—C11—O3	−151.31 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88	2.00	2.8566 (17)	164
N1—H1A···O2ii	0.88	2.15	2.9680 (18)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88	2.00	2.8566 (17)	164
N1—H1A⋯O2ii	0.88	2.15	2.9680 (18)	154

Symmetry codes: (i) ; (ii) .