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

Li, D.-F.; Zhu, X.-F.; Guan, S.; Hou, R.-B.

doi:10.1107/S1600536811046745

organic compounds

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Volume 67| Part 12| December 2011| Page o3290

https://doi.org/10.1107/S1600536811046745

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

Dong-Feng Li,^a ^* Xiao-Fei Zhu,^a Shuang Guan ^a and Rui-Bin Hou ^a

^aSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: lidongfeng@mail.ccut.edu.cn

(Received 30 October 2011; accepted 5 November 2011; online 12 November 2011)

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, P 2₁ /c
a = 5.884 (3) Å
b = 7.923 (5) Å
c = 21.898 (13) Å
β = 93.54 (3)°
V = 1018.9 (10) Å³
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[F² > 2σ(F²)] = 0.042
wR(F²) = 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

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) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046745/cv5189sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046745/cv5189Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046745/cv5189Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacemnet ellipsoids.

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

Crystal data top

C₁₂H₁₁NO₂	F(000) = 424
M_r = 201.22	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0781P)² + 0.0624P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2333 reflections	Δρ_max = 0.20 e Å⁻³
138 parameters	Δρ_min = −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)

Crystal data top

C₁₂H₁₁NO₂	V = 1018.9 (10) Å³
M_r = 201.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.884 (3) Å	µ = 0.09 mm⁻¹
b = 7.923 (5) Å	T = 288 K
c = 21.898 (13) Å	0.43 × 0.26 × 0.22 mm
β = 93.54 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2333 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1730 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.980	R_int = 0.031
9616 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.08	Δρ_max = 0.20 e Å⁻³
2333 reflections	Δρ_min = −0.18 e Å⁻³
138 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NO₂
M_r	201.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	288
a, b, c (Å)	5.884 (3), 7.923 (5), 21.898 (13)
β (°)	93.54 (3)
V (Å³)	1018.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.26 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.963, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	9616, 2333, 1730
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.136, 1.08
No. of reflections	2333
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	165.0
C12—H12B···O1ⁱⁱ	0.96	2.63	3.540 (3)	158.5
N1—H1A···Cgⁱⁱⁱ	0.86	2.52	3.189 (3)	134.6

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

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of Jilin Province (grant No. 20101548).

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3290

https://doi.org/10.1107/S1600536811046745

Open

access