(E)-Methyl 3-(1H-indol-3-yl)acrylate

Abstract

In the title compound, C₁₂H₁₁NO₂, the indole and methyl acrylate mean planes are inclined at an angle of 10.6 (1)°. In the crystal, N—H⋯π inter­actions link mol­ecules into chains along [010] and weak inter­molecular C—H⋯O hydrogen bonds further consolidate the crystal packing.

Related literature

For general background to the synthesis of 3-substituted indole derivatives as precursors of potent anti-inflammatory and analgesic agents, see Radwan et al. (1997 ▶). For details of the synthesis, see García-Rubia et al. (2010 ▶). For related structures, see: Bhella et al. (2009 ▶); Hou & Li (2011 ▶).

Experimental

Crystal data

• C₁₂H₁₁NO₂

• M _r = 201.22

• Monoclinic,

• a = 5.884 (3) Å

• b = 7.923 (5) Å

• c = 21.898 (13) Å

• β = 93.54 (3)°

• V = 1018.9 (10) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 288 K

• 0.43 × 0.26 × 0.22 mm

Data collection

• Rigaku R-AXIS RAPID diffractometer

• Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.963, T _max = 0.980

• 9616 measured reflections

• 2333 independent reflections

• 1730 reflections with I > 2σ(I)

• R _int = 0.031

Refinement

• R[F ² > 2σ(F ²)] = 0.042

• wR(F ²) = 0.136

• S = 1.08

• 2333 reflections

• 138 parameters

• H-atom parameters constrained

• Δρ_max = 0.20 e Å⁻³

• Δρ_min = −0.18 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811046745/cv5189Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.65	3.558 (2)	165
C12—H12B⋯O1ii	0.96	2.63	3.540 (3)	159
N1—H1A⋯Cgiii	0.86	2.52	3.189 (3)	135

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

supplementary crystallographic information

Comment

Indole skeleton is a key component of many biologically active compounds. Radwan et al. (1997) have synthesized and evaluated of 3-substituted indole derivatives as precursors of potent anti-inflammatory and analgesic agents. Recently, Bhella et al. (2009) reported a series of compounds with the similar structures. In this paper, we report the crystal structure of the title compound.

In the tiltle compound (Fig. 1), all bond lengths and angles are normal and comparable with those reported for close structures (Bhella et al., 2009; Hou & Li, 2011). The dihedral angle between the indole and methyl acrylate mean planes is 10.6 (1)°. In the crystal structure, N—H···π interactions (Table 1) link molecules into chians along [010], and weak intermolecular C—H···O hydrogen bonds (Table 1) consolidate further the crystal packing.

Experimental

The title compound was prepared according to the literature (García-Rubia et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of dichloromethane and petroleum (60–90 °C) at room temperature.

Refinement

C-bound H atoms were placed in calculated positions (C—H 0.93 and 0.96 Å) and were included in the refinement in the riding model with U_iso(H) = 1.2 and 1.5 U_eq(C). The N-bound H atom was placed in calculated position with N—H = 0.86 Å and refined with U_iso(H) = 1.2 U_eq(N).

Figures

Fig. 1.

The molecular structure of the title compound showing the atomic numbering and 50% probability displacemnet ellipsoids.

Crystal data

C12H11NO2	F(000) = 424
Mr = 201.22	Dx = 1.312 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6974 reflections
a = 5.884 (3) Å	θ = 3.2–27.5°
b = 7.923 (5) Å	µ = 0.09 mm−1
c = 21.898 (13) Å	T = 288 K
β = 93.54 (3)°	Block, colourless
V = 1018.9 (10) Å3	0.43 × 0.26 × 0.22 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2333 independent reflections
Radiation source: fine-focus sealed tube	1730 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→7
Tmin = 0.963, Tmax = 0.980	k = −10→10
9616 measured reflections	l = −28→28

Refinement

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0781P)2 + 0.0624P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2333 reflections	Δρmax = 0.20 e Å−3
138 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (5)

Special details

Experimental. (See detailed section in the paper)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9472 (2)	0.64568 (18)	0.23712 (6)	0.0434 (3)
H1	1.0528	0.7010	0.2143	0.052*
C2	0.9795 (3)	0.63514 (19)	0.30016 (7)	0.0502 (4)
H2	1.1092	0.6829	0.3195	0.060*
C3	0.8210 (3)	0.55410 (19)	0.33566 (7)	0.0534 (4)
H3	0.8461	0.5510	0.3780	0.064*
C4	0.6291 (3)	0.47926 (19)	0.30863 (7)	0.0524 (4)
H4	0.5245	0.4244	0.3319	0.063*
C5	0.5973 (2)	0.48890 (17)	0.24505 (7)	0.0434 (3)
C6	0.7520 (2)	0.57135 (16)	0.20809 (6)	0.0379 (3)
C7	0.6584 (2)	0.55697 (17)	0.14540 (6)	0.0428 (3)
C8	0.4580 (2)	0.46741 (19)	0.14818 (7)	0.0503 (4)
H8	0.3616	0.4387	0.1145	0.060*
C9	0.7440 (3)	0.61468 (18)	0.08871 (7)	0.0461 (4)
H9	0.6473	0.6000	0.0539	0.055*
C10	0.9444 (3)	0.68641 (19)	0.07991 (6)	0.0474 (4)
H10	1.0461	0.7067	0.1133	0.057*
C11	1.0071 (3)	0.73389 (19)	0.01826 (6)	0.0462 (4)
C12	1.3035 (3)	0.8419 (3)	−0.03879 (8)	0.0621 (5)
H12A	1.2504	0.7638	−0.0700	0.093*
H12B	1.4669	0.8430	−0.0359	0.093*
H12C	1.2477	0.9528	−0.0490	0.093*
N1	0.4222 (2)	0.42746 (16)	0.20675 (6)	0.0520 (4)
H1A	0.3071	0.3719	0.2184	0.062*
O1	0.8851 (2)	0.72446 (18)	−0.02800 (5)	0.0711 (4)
O2	1.22147 (19)	0.79075 (16)	0.01910 (5)	0.0607 (3)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0429 (7)	0.0419 (7)	0.0452 (8)	0.0007 (6)	0.0015 (6)	−0.0008 (6)
C2	0.0524 (8)	0.0507 (8)	0.0463 (8)	0.0032 (7)	−0.0077 (7)	−0.0025 (6)
C3	0.0702 (10)	0.0491 (8)	0.0404 (7)	0.0101 (7)	−0.0006 (7)	0.0023 (6)
C4	0.0644 (10)	0.0426 (7)	0.0517 (8)	0.0047 (7)	0.0149 (7)	0.0057 (6)
C5	0.0441 (7)	0.0340 (7)	0.0521 (8)	0.0027 (6)	0.0037 (6)	−0.0018 (6)
C6	0.0396 (7)	0.0316 (6)	0.0426 (7)	0.0043 (5)	0.0018 (6)	−0.0013 (5)
C7	0.0439 (7)	0.0387 (7)	0.0452 (7)	0.0032 (6)	−0.0012 (6)	−0.0043 (6)
C8	0.0449 (8)	0.0497 (8)	0.0553 (9)	−0.0006 (6)	−0.0049 (7)	−0.0077 (7)
C9	0.0496 (8)	0.0454 (8)	0.0423 (7)	0.0048 (6)	−0.0055 (6)	−0.0036 (6)
C10	0.0535 (8)	0.0499 (8)	0.0379 (7)	0.0033 (7)	−0.0037 (6)	−0.0035 (6)
C11	0.0471 (8)	0.0499 (8)	0.0412 (7)	0.0063 (6)	0.0001 (6)	−0.0032 (6)
C12	0.0568 (9)	0.0772 (11)	0.0535 (9)	0.0000 (9)	0.0116 (8)	0.0016 (8)
N1	0.0453 (7)	0.0484 (7)	0.0625 (8)	−0.0086 (5)	0.0057 (6)	−0.0025 (6)
O1	0.0614 (8)	0.1069 (10)	0.0435 (6)	−0.0047 (7)	−0.0078 (5)	0.0081 (6)
O2	0.0550 (7)	0.0826 (8)	0.0444 (6)	−0.0088 (6)	0.0013 (5)	−0.0001 (5)

Geometric parameters (Å, °)

C1—C2	1.384 (2)	C8—N1	1.350 (2)
C1—C6	1.407 (2)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.334 (2)
C2—C3	1.406 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.470 (2)
C3—C4	1.376 (2)	C10—H10	0.9300
C3—H3	0.9300	C11—O1	1.2075 (18)
C4—C5	1.396 (2)	C11—O2	1.338 (2)
C4—H4	0.9300	C12—O2	1.442 (2)
C5—N1	1.377 (2)	C12—H12A	0.9600
C5—C6	1.415 (2)	C12—H12B	0.9600
C6—C7	1.452 (2)	C12—H12C	0.9600
C7—C8	1.380 (2)	N1—H1A	0.8600
C7—C9	1.443 (2)
C2—C1—C6	118.88 (14)	N1—C8—H8	124.9
C2—C1—H1	120.6	C7—C8—H8	124.9
C6—C1—H1	120.6	C10—C9—C7	128.21 (14)
C1—C2—C3	121.62 (14)	C10—C9—H9	115.9
C1—C2—H2	119.2	C7—C9—H9	115.9
C3—C2—H2	119.2	C9—C10—C11	121.07 (13)
C4—C3—C2	120.92 (15)	C9—C10—H10	119.5
C4—C3—H3	119.5	C11—C10—H10	119.5
C2—C3—H3	119.5	O1—C11—O2	122.92 (15)
C3—C4—C5	117.46 (15)	O1—C11—C10	125.77 (16)
C3—C4—H4	121.3	O2—C11—C10	111.31 (12)
C5—C4—H4	121.3	O2—C12—H12A	109.5
N1—C5—C4	129.60 (14)	O2—C12—H12B	109.5
N1—C5—C6	107.38 (14)	H12A—C12—H12B	109.5
C4—C5—C6	123.02 (14)	O2—C12—H12C	109.5
C1—C6—C5	118.10 (13)	H12A—C12—H12C	109.5
C1—C6—C7	135.37 (13)	H12B—C12—H12C	109.5
C5—C6—C7	106.53 (12)	C8—N1—C5	109.94 (13)
C8—C7—C9	123.06 (13)	C8—N1—H1A	125.0
C8—C7—C6	105.90 (13)	C5—N1—H1A	125.0
C9—C7—C6	131.02 (13)	C11—O2—C12	116.66 (12)
N1—C8—C7	110.25 (13)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.65	3.558 (2)	165.
C12—H12B···O1ii	0.96	2.63	3.540 (3)	159.
N1—H1A···Cgiii	0.86	2.52	3.189 (3)	135.

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+1/2.