organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-(2-Methyl­benz­yl)-1H-indole-3-carbaldehyde

aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, bWest China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China, and cState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
*Correspondence e-mail: hegu@scu.edu.cn

(Received 6 March 2012; accepted 8 March 2012; online 24 March 2012)

In the title compound, C17H15NO, the benzene ring and the indole system are almost perpendicular, making a dihedral angle of 87.82 (6)°. The crystal packing is stabilized by C—H⋯O and ππ stacking inter­actions with centroid–centroid distances of 3.592 (4) Å between the pyrrole and the benzene rings in the indole systems of neighboring mol­ecules.

Related literature

For general background to the chemistry and anti-inflammatory activity of carboxylic acid derivatives, see: Andreani et al. (1994[Andreani, A., Rambaldi, M., Locatelli, A. & Pofferi, G. (1994). Eur. J. Med. Chem. 29, 903-906.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15NO

  • Mr = 249.30

  • Monoclinic, P 21 /c

  • a = 10.5251 (3) Å

  • b = 15.4352 (5) Å

  • c = 8.2335 (2) Å

  • β = 99.214 (3)°

  • V = 1320.33 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.28 × 0.25 × 0.20 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, California, USA.]) Tmin = 0.981, Tmax = 1.000

  • 5468 measured reflections

  • 2699 independent reflections

  • 1928 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.117

  • S = 1.04

  • 2699 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16⋯O1i 0.93 2.56 3.418 (2) 154
Symmetry code: (i) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, California, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov, 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

1-(2-Methyl-benzyl)-1H-indole-3-carbaldehyde is of great importance owing to its wide biological properties (Andreani et al., 1994). The title compound is one of the key intermediates in our synthetic investigations of antibacterial drugs. We report here its crystal structure.

In the title compound, C17H15NO, as shown in Fig 1, the benzene ring with the methyl group in ortho position and the indole system are almost perpendicular, making dihedral angle of 87.82 (6)°. A combination of intermolecular C-H···O and ππ packing interaction plays an important role in the connection of neighbouring molecules. The centroid-centroid distance between the pyrrole ring and the benzene ring in the indole system of the neighbouring molecule is 3.592 (4) Å (symmetry operator: -x, -y, -z).

Related literature top

For general background to the chemistry and anti-inflammatory activity of indole carboxylic acid derivatives, see: Andreani et al. (1994).

Experimental top

1H-indole-3-carbaldehyde(14 mmol) was dissolved in dry DMF(25 ml)and treated portionwise,under stirring, with 20 mmol NaH. The mixture was stirred at room temperature for 10 min and treated with 20 mmol of 1-chloromethyl-2-methyl-benzene. After 1 h at 90°C under stirring, the mixture was poured onto ice. The resulting precipitate was collected by filtration and crystallized from ethanol with a yield of 70%. Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 or 1.5Ueq(C) for methyl H atoms.

Structure description top

1-(2-Methyl-benzyl)-1H-indole-3-carbaldehyde is of great importance owing to its wide biological properties (Andreani et al., 1994). The title compound is one of the key intermediates in our synthetic investigations of antibacterial drugs. We report here its crystal structure.

In the title compound, C17H15NO, as shown in Fig 1, the benzene ring with the methyl group in ortho position and the indole system are almost perpendicular, making dihedral angle of 87.82 (6)°. A combination of intermolecular C-H···O and ππ packing interaction plays an important role in the connection of neighbouring molecules. The centroid-centroid distance between the pyrrole ring and the benzene ring in the indole system of the neighbouring molecule is 3.592 (4) Å (symmetry operator: -x, -y, -z).

For general background to the chemistry and anti-inflammatory activity of indole carboxylic acid derivatives, see: Andreani et al. (1994).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov, 2009); software used to prepare material for publication: OLEX2 (Dolomanov, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound.
1-(2-Methylbenzyl)-1H-indole-3-carbaldehyde top
Crystal data top
C17H15NOF(000) = 528
Mr = 249.30Dx = 1.254 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
a = 10.5251 (3) ÅCell parameters from 1937 reflections
b = 15.4352 (5) Åθ = 3.2–29.1°
c = 8.2335 (2) ŵ = 0.08 mm1
β = 99.214 (3)°T = 293 K
V = 1320.33 (7) Å3Block, colorless
Z = 40.28 × 0.25 × 0.20 mm
Data collection top
Agilent Xcalibur Eos
diffractometer
2699 independent reflections
Radiation source: fine-focus sealed tube1928 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 16.0874 pixels mm-1θmax = 26.4°, θmin = 3.2°
ω scansh = 1113
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 1119
Tmin = 0.981, Tmax = 1.000l = 104
5468 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.2065P]
where P = (Fo2 + 2Fc2)/3
2699 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C17H15NOV = 1320.33 (7) Å3
Mr = 249.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.5251 (3) ŵ = 0.08 mm1
b = 15.4352 (5) ÅT = 293 K
c = 8.2335 (2) Å0.28 × 0.25 × 0.20 mm
β = 99.214 (3)°
Data collection top
Agilent Xcalibur Eos
diffractometer
2699 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
1928 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 1.000Rint = 0.016
5468 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.04Δρmax = 0.13 e Å3
2699 reflectionsΔρmin = 0.17 e Å3
173 parameters
Special details top

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
xyzUiso*/Ueq
O10.02058 (15)0.14964 (11)0.33644 (17)0.0895 (5)
N10.21128 (12)0.01830 (9)0.14071 (15)0.0439 (3)
C10.18887 (13)0.04418 (11)0.01839 (19)0.0404 (4)
C20.13295 (13)0.00278 (11)0.12762 (19)0.0415 (4)
C30.12187 (14)0.08699 (11)0.0886 (2)0.0457 (4)
C40.17018 (15)0.09542 (11)0.0760 (2)0.0475 (4)
H40.17390.14720.13440.057*
C50.10025 (15)0.05289 (13)0.2699 (2)0.0506 (4)
H50.06390.02730.36870.061*
C60.12281 (16)0.14068 (13)0.2611 (2)0.0573 (5)
H60.10100.17440.35490.069*
C70.17749 (16)0.17975 (12)0.1149 (2)0.0567 (5)
H70.19100.23930.11260.068*
C80.21221 (15)0.13246 (11)0.0266 (2)0.0503 (4)
H80.24990.15870.12420.060*
C90.06793 (18)0.15646 (14)0.1918 (3)0.0642 (5)
H90.06900.21130.14490.077*
C100.26384 (17)0.00142 (12)0.31387 (19)0.0536 (5)
H10A0.31530.05100.32100.064*
H10B0.19330.00820.37450.064*
C110.34564 (15)0.07493 (11)0.39236 (19)0.0455 (4)
C120.46514 (15)0.09284 (11)0.34816 (19)0.0448 (4)
C130.53745 (17)0.15965 (12)0.4283 (2)0.0565 (5)
H130.61760.17210.40020.068*
C140.4941 (2)0.20792 (14)0.5479 (2)0.0679 (6)
H140.54450.25250.59970.082*
C150.3765 (2)0.19041 (15)0.5909 (3)0.0744 (6)
H150.34670.22280.67220.089*
C160.30237 (18)0.12415 (14)0.5125 (2)0.0637 (5)
H160.22210.11250.54110.076*
C170.51550 (17)0.04237 (15)0.2160 (2)0.0666 (6)
H17A0.50750.01850.23600.100*
H17B0.60440.05650.21680.100*
H17C0.46670.05680.11080.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1027 (11)0.1071 (13)0.0562 (9)0.0489 (10)0.0050 (8)0.0189 (9)
N10.0436 (7)0.0468 (8)0.0395 (7)0.0044 (6)0.0014 (6)0.0004 (7)
C10.0344 (8)0.0448 (10)0.0419 (9)0.0048 (7)0.0059 (6)0.0003 (8)
C20.0307 (7)0.0519 (10)0.0418 (9)0.0009 (7)0.0059 (6)0.0016 (8)
C30.0377 (8)0.0520 (11)0.0471 (9)0.0042 (7)0.0054 (7)0.0049 (8)
C40.0461 (9)0.0446 (10)0.0515 (10)0.0020 (7)0.0070 (8)0.0009 (8)
C50.0386 (8)0.0719 (13)0.0404 (9)0.0027 (8)0.0031 (7)0.0013 (9)
C60.0509 (10)0.0663 (13)0.0550 (11)0.0111 (9)0.0098 (8)0.0169 (10)
C70.0570 (10)0.0472 (11)0.0663 (12)0.0060 (8)0.0109 (9)0.0063 (9)
C80.0495 (9)0.0482 (11)0.0523 (10)0.0042 (8)0.0052 (8)0.0054 (9)
C90.0626 (12)0.0655 (13)0.0659 (13)0.0204 (10)0.0145 (10)0.0106 (11)
C100.0586 (10)0.0626 (12)0.0381 (9)0.0110 (9)0.0031 (8)0.0043 (8)
C110.0486 (9)0.0514 (10)0.0348 (8)0.0002 (8)0.0020 (7)0.0014 (8)
C120.0459 (9)0.0520 (10)0.0345 (8)0.0019 (8)0.0004 (7)0.0041 (8)
C130.0511 (10)0.0644 (12)0.0505 (10)0.0082 (9)0.0028 (8)0.0026 (10)
C140.0765 (13)0.0592 (13)0.0622 (12)0.0081 (11)0.0073 (11)0.0119 (11)
C150.0856 (15)0.0753 (15)0.0612 (13)0.0110 (12)0.0082 (11)0.0251 (11)
C160.0579 (11)0.0806 (15)0.0541 (11)0.0017 (10)0.0133 (9)0.0112 (10)
C170.0572 (11)0.0863 (16)0.0584 (12)0.0029 (10)0.0161 (9)0.0093 (11)
Geometric parameters (Å, º) top
O1—C91.220 (2)C9—H90.9300
N1—C11.387 (2)C10—H10A0.9700
N1—C41.347 (2)C10—H10B0.9700
N1—C101.4677 (19)C10—C111.506 (2)
C1—C21.405 (2)C11—C121.392 (2)
C1—C81.384 (2)C11—C161.381 (2)
C2—C31.431 (2)C12—C131.385 (2)
C2—C51.400 (2)C12—C171.502 (2)
C3—C41.375 (2)C13—H130.9300
C3—C91.428 (2)C13—C141.370 (3)
C4—H40.9300C14—H140.9300
C5—H50.9300C14—C151.367 (3)
C5—C61.376 (3)C15—H150.9300
C6—H60.9300C15—C161.382 (3)
C6—C71.386 (3)C16—H160.9300
C7—H70.9300C17—H17A0.9600
C7—C81.374 (2)C17—H17B0.9600
C8—H80.9300C17—H17C0.9600
C1—N1—C10125.15 (14)N1—C10—H10A109.1
C4—N1—C1108.69 (13)N1—C10—H10B109.1
C4—N1—C10126.06 (14)N1—C10—C11112.57 (14)
N1—C1—C2107.72 (14)H10A—C10—H10B107.8
C8—C1—N1129.84 (15)C11—C10—H10A109.1
C8—C1—C2122.44 (15)C11—C10—H10B109.1
C1—C2—C3106.65 (14)C12—C11—C10121.05 (15)
C5—C2—C1118.56 (16)C16—C11—C10119.37 (16)
C5—C2—C3134.79 (16)C16—C11—C12119.57 (16)
C4—C3—C2106.38 (14)C11—C12—C17121.66 (15)
C4—C3—C9124.34 (17)C13—C12—C11118.30 (15)
C9—C3—C2129.24 (16)C13—C12—C17120.04 (16)
N1—C4—C3110.55 (15)C12—C13—H13119.1
N1—C4—H4124.7C14—C13—C12121.77 (17)
C3—C4—H4124.7C14—C13—H13119.1
C2—C5—H5120.6C13—C14—H14120.1
C6—C5—C2118.87 (16)C15—C14—C13119.88 (18)
C6—C5—H5120.6C15—C14—H14120.1
C5—C6—H6119.4C14—C15—H15120.3
C5—C6—C7121.23 (17)C14—C15—C16119.49 (18)
C7—C6—H6119.4C16—C15—H15120.3
C6—C7—H7119.3C11—C16—C15121.00 (18)
C8—C7—C6121.48 (18)C11—C16—H16119.5
C8—C7—H7119.3C15—C16—H16119.5
C1—C8—H8121.3C12—C17—H17A109.5
C7—C8—C1117.41 (16)C12—C17—H17B109.5
C7—C8—H8121.3C12—C17—H17C109.5
O1—C9—C3125.3 (2)H17A—C17—H17B109.5
O1—C9—H9117.4H17A—C17—H17C109.5
C3—C9—H9117.4H17B—C17—H17C109.5
N1—C1—C2—C30.28 (16)C5—C2—C3—C91.2 (3)
N1—C1—C2—C5179.55 (13)C5—C6—C7—C80.5 (3)
N1—C1—C8—C7178.63 (15)C6—C7—C8—C10.9 (2)
N1—C10—C11—C1269.9 (2)C8—C1—C2—C3179.02 (14)
N1—C10—C11—C16111.41 (18)C8—C1—C2—C50.3 (2)
C1—N1—C4—C30.86 (18)C9—C3—C4—N1178.46 (15)
C1—N1—C10—C11147.04 (15)C10—N1—C1—C2177.28 (13)
C1—C2—C3—C40.23 (16)C10—N1—C1—C81.9 (2)
C1—C2—C3—C9177.87 (16)C10—N1—C4—C3177.41 (13)
C1—C2—C5—C60.6 (2)C10—C11—C12—C13178.10 (15)
C2—C1—C8—C70.5 (2)C10—C11—C12—C172.5 (2)
C2—C3—C4—N10.67 (17)C10—C11—C16—C15178.00 (18)
C2—C3—C9—O10.0 (3)C11—C12—C13—C140.3 (3)
C2—C5—C6—C70.3 (2)C12—C11—C16—C150.7 (3)
C3—C2—C5—C6178.37 (16)C12—C13—C14—C150.1 (3)
C4—N1—C1—C20.69 (16)C13—C14—C15—C160.2 (3)
C4—N1—C1—C8178.54 (15)C14—C15—C16—C110.5 (3)
C4—N1—C10—C1137.0 (2)C16—C11—C12—C130.5 (2)
C4—C3—C9—O1177.28 (17)C16—C11—C12—C17178.81 (16)
C5—C2—C3—C4178.87 (16)C17—C12—C13—C14179.10 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.932.563.418 (2)154
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC17H15NO
Mr249.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.5251 (3), 15.4352 (5), 8.2335 (2)
β (°) 99.214 (3)
V3)1320.33 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.28 × 0.25 × 0.20
Data collection
DiffractometerAgilent Xcalibur Eos
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.981, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
5468, 2699, 1928
Rint0.016
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.117, 1.04
No. of reflections2699
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.17

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.93002.56003.418 (2)154.00
Symmetry code: (i) x, y, z+1.
 

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies Ltd, California, USA.  Google Scholar
First citationAndreani, A., Rambaldi, M., Locatelli, A. & Pofferi, G. (1994). Eur. J. Med. Chem. 29, 903–906.  CrossRef CAS Web of Science Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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