2 (1H Indol 3 yl­methyl­ene)­indane 1 one

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Structure Reports

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ISSN 1600-5368

2-(1

H

-Indol-3-ylmethylene)indane-1-one

G. Vasuki,a_{V. Parthasarathi,}a_* K. Ramamurthi,a_{S. Mohane} Coumarb_{and D. P. Jindal}b_²

a_{Department of Physics, Bharathidasan}

University, Tiruchirappalli 620 024, India, and b_{University Institute of Pharmaceutical Sciences,}

Panjab University, Chandigarh 160 014, India

² Deceased

Correspondence e-mail: sarati@yahoo.com

Key indicators

Single-crystal X-ray study

T= 293 K

Mean(C±C) = 0.007 AÊ

Rfactor = 0.043

wRfactor = 0.099 Data-to-parameter ratio = 6.8

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved

The indole and indane moieties of the title molecule, C18H13NO, form a dihedral angle of 10.2 (2). In the crystal

structure, symmetry-related molecules are linked by

inter-molecular NÐH O and CÐH O hydrogen bonds to form

in®nite one-dimensional chains along the baxis. This chain

structure is further stabilized by±and CÐH

interac-tions.

Comment

The X-ray structure determination of the title compound, (I), was undertaken to study the stereochemistry of the molecule and the nature of the hydrogen bonding. In (I), the indole ring is planar within 0.028 (4) AÊ and the indane ring system is also planar, with C19 deviating by a maximum of 0.027 (4) AÊ. The dihedral angle between the indole and indane moieties is

10.2 (2)_{. The widening of the exocyclic angle C3ÐC10ÐC19}

[130.0 (4)_{] from 120 may be due to the steric repulsion}

between atoms H2 and H18A (H2 H18A = 2.40 AÊ). The

dihedral angle of 7.68 _{between the O11/C11/C19/C10 and}

C10/C3/C2/N1 planes indicates that there is possibile delocalization of electrons from O11 to N1 (O11 C11Ð C19 C10ÐC3 C2ÐN1). As a result of this conjugation, the C10ÐC3 [1.437 (6) AÊ] bond distance is shortened from the normal value of 1.478 (14) AÊ (Allenet al., 1987). The N atom issp2_-hybridized.

In the crystal structure, glide-related molecules are linked

by intermolecular NÐH O and CÐH O hydrogen bonds

(Table 1) to form in®nite one-dimensional chains along theb

axis. Within a chain, molecules related by translation

symmetry are stacked with signi®cant ± interactions and

intermolecular CÐH interactions involving atom C18 and

the C12±C17 aromatic ring [H18B Cg= 2.69 AÊ, C18 Cg=

3.567 (6) AÊ and C18ÐH18B Cg = 150_{, where Cg is the}

centroid of the C12±C17 ring at (x,yÿ1,z)].

Experimental

Indol-3-carboxaldehyde (0.25 g, 1.72 mmol) was added to a solution of 1-indanone (0.2 g, 1.51 mmol) in methanol (25 ml) and the solution was stirred manually for 15 min. Sodium hydroxide (0.4 g, 10 mmol) was then added and the solution was stirred for 30 min and re¯uxed for 8 h. The completion of reaction was monitored with thin-layer

chromatography. The reaction mixture was then concentrated to about 5 ml and crushed ice was added. It was allowed to stand overnight and was then ®ltered. The product was crystallized from methanol and needle-shaped crystals of (I) were obtained (yield 0.076 g, 21%, m.p. 526±528 K).

Crystal data

C18H13NO

Mr= 259.29 Orthorhombic,Pca21

a= 12.3964 (17) AÊ

b= 4.961 (4) AÊ

c= 21.330 (4) AÊ

V= 1311.7 (10) AÊ3

Z= 4

Dx= 1.313 Mg mÿ3

Mo Kradiation Cell parameters from 25

re¯ections

= 10±15 = 0.08 mmÿ1

T= 293 (2) K Needle, brown 0.400.200.05 mm

Data collection

Enraf±Nonius CAD-4 diffractometer

!±2scans

Absorption correction: scan (Northet al., 1968)

Tmin= 0.968,Tmax= 0.996 1686 measured re¯ections 1244 independent re¯ections 848 re¯ections withI> 2(I)

Rint= 0.026

max= 25.0

h=ÿ1!14

k=ÿ1!5

l=ÿ25!1 2 standard re¯ections

frequency: 120 min intensity decay: none

Re®nement

Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.043}

wR(F2_{) = 0.099}

S= 1.19 1244 re¯ections 182 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0239P)2 + 0.4636P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.15 e AÊÿ3

min=ÿ0.16 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.0077 (13)

Table 1

Hydrogen-bonding geometry (AÊ,_).

DÐH A DÐH H A D A DÐH A

N1ÐH1 O11i _{0.86 2.16 2.829 (5) 134} C18ÐH18A O11ii _{0.97 2.42 3.371 (6) 168}

Symmetry codes: (i)1

2‡x;ÿy;z; (ii)21‡x;1ÿy;z.

All H atoms were ®xed geometrically and allowed to ride on the parent non-H atoms, with aromatic NÐH = 0.86 AÊ, CÐH = 0.93 AÊ and methylene CÐH = 0.97 AÊ. The displacement parametersUiso(H)

were set equal to 1.2Ueq. The Friedel opposites were not merged

during the re®nement.

Data collection: CAD-4 EXPRESS (Enraf±Nonius, 1994); cell re®nement:CAD-4EXPRESS; data reduction:MolEN(Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication:SHELXL97.

MC thanks CSIR, India, for ®nancial assistance and GV thanks the UGC, India, for the award of an FIP fellowship (1999±2001).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).J. Chem. Soc. Perkin Trans.2, pp. S1±19.

Enraf±Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf±Nonius, Delft, The Netherlands.

Fair, C. K. (1990).MolEN.Enraf±Nonius, Delft, The Netherlands.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Zsolnai, L. (1997).ZORTEP. University of Heidelberg, Germany.

Figure 1

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Acta Cryst. (2002). E58, o1222–o1223

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Acta Cryst. (2002). E58, o1222–o1223 [https://doi.org/10.1107/S1600536802017774]

2-(1

H

-Indol-3-ylmethylene)indane-1-one

G. Vasuki, V. Parthasarathi, K. Ramamurthi, S. Mohane Coumar and D. P. Jindal

2-(1H-indol-3-ylmethylene)indane-1-one

Crystal data

C18H13NO

Mr = 259.29

Orthorhombic, Pca21 Hall symbol: P 2c -2ac

a = 12.3964 (17) Å

b = 4.961 (4) Å

c = 21.330 (4) Å

V = 1311.7 (10) Å3

Z = 4

F(000) = 544

Dx = 1.313 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections

θ = 10–15°

µ = 0.08 mm−1

T = 293 K Needle, brown 0.40 × 0.20 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω–2θ scans

Absorption correction: ψ scan (North et al., 1968)

Tmin = 0.968, Tmax = 0.996 1686 measured reflections

1244 independent reflections 848 reflections with I > 2σ(I)

Rint = 0.026

θmax = 25.0°, θmin = 3.3°

h = −1→14

k = −1→5

l = −25→1

2 standard reflections every 120 min intensity decay: none

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.043}

wR(F2_{) = 0.099}

S = 1.19 1244 reflections 182 parameters 1 restraint

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0239P)2 + 0.4636P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.15 e Å−3 Δρmin = −0.16 e Å−3

Special details

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 F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

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Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

N1 0.037 (2) 0.050 (2) 0.061 (3) 0.0016 (19) −0.005 (2) −0.001 (3) C2 0.047 (3) 0.042 (3) 0.042 (3) −0.005 (2) −0.003 (2) −0.002 (3) C3 0.031 (2) 0.038 (3) 0.043 (3) 0.001 (2) 0.000 (2) 0.007 (2) C4 0.039 (2) 0.036 (2) 0.032 (2) −0.003 (2) −0.001 (2) 0.002 (2) C5 0.049 (3) 0.041 (3) 0.051 (3) −0.002 (3) −0.009 (3) −0.002 (3) C6 0.065 (3) 0.048 (3) 0.051 (3) −0.006 (3) −0.010 (3) 0.004 (3) C7 0.075 (3) 0.037 (3) 0.046 (3) −0.008 (3) 0.004 (3) −0.003 (2) C8 0.059 (3) 0.044 (3) 0.052 (3) −0.004 (3) 0.008 (3) 0.002 (3) C9 0.046 (3) 0.032 (2) 0.041 (2) −0.002 (2) 0.004 (2) 0.004 (3) C10 0.037 (2) 0.040 (3) 0.040 (3) −0.009 (2) −0.001 (2) 0.004 (3) C11 0.033 (2) 0.044 (3) 0.049 (3) −0.008 (2) 0.002 (2) 0.000 (3) O11 0.0371 (17) 0.064 (2) 0.072 (2) 0.0023 (17) −0.0036 (18) −0.018 (2) C12 0.052 (3) 0.046 (3) 0.046 (3) −0.014 (3) 0.006 (3) −0.005 (3) C13 0.078 (4) 0.048 (3) 0.055 (3) −0.008 (3) 0.021 (3) −0.006 (3) C14 0.122 (6) 0.057 (4) 0.058 (4) −0.017 (4) 0.033 (4) −0.014 (3) C15 0.132 (6) 0.063 (4) 0.046 (3) −0.024 (4) 0.000 (4) −0.006 (4) C16 0.098 (5) 0.065 (4) 0.050 (3) −0.018 (4) −0.014 (4) 0.013 (3) C17 0.067 (3) 0.043 (3) 0.033 (2) −0.016 (3) −0.003 (3) 0.003 (2) C18 0.049 (3) 0.045 (3) 0.044 (3) 0.001 (3) −0.002 (2) 0.004 (3) C19 0.036 (2) 0.039 (3) 0.042 (3) −0.004 (2) −0.001 (2) 0.004 (3)

Geometric parameters (Å, º)

N1—C2 1.358 (6) C10—H10 0.93 N1—C9 1.388 (5) C11—O11 1.232 (5) N1—H1 0.86 C11—C12 1.464 (6) C2—C3 1.375 (5) C11—C19 1.469 (6) C2—H2 0.93 C12—C17 1.376 (7) C3—C10 1.437 (6) C12—C13 1.392 (7) C3—C4 1.446 (6) C13—C14 1.380 (7) C4—C5 1.386 (6) C13—H13 0.93 C4—C9 1.399 (6) C14—C15 1.364 (8) C5—C6 1.383 (6) C14—H14 0.93 C5—H5 0.93 C15—C16 1.377 (9) C6—C7 1.407 (7) C15—H15 0.93 C6—H6 0.93 C16—C17 1.395 (7) C7—C8 1.362 (6) C16—H16 0.93 C7—H7 0.93 C17—C18 1.505 (7) C8—C9 1.396 (6) C18—C19 1.500 (6) C8—H8 0.93 C18—H18A 0.97 C10—C19 1.348 (5) C18—H18B 0.97

N1—C2—C3 110.0 (4) C17—C12—C13 121.6 (5) N1—C2—H2 125.0 C17—C12—C11 109.2 (4) C3—C2—H2 125.0 C13—C12—C11 129.2 (5) C2—C3—C10 129.3 (4) C14—C13—C12 117.8 (6) C2—C3—C4 106.4 (4) C14—C13—H13 121.1 C10—C3—C4 124.2 (4) C12—C13—H13 121.1 C5—C4—C9 119.3 (4) C15—C14—C13 120.8 (6) C5—C4—C3 134.0 (4) C15—C14—H14 119.6 C9—C4—C3 106.7 (4) C13—C14—H14 119.6 C6—C5—C4 118.7 (5) C14—C15—C16 121.7 (6) C6—C5—H5 120.6 C14—C15—H15 119.2 C4—C5—H5 120.6 C16—C15—H15 119.2 C5—C6—C7 121.0 (5) C15—C16—C17 118.4 (6) C5—C6—H6 119.5 C15—C16—H16 120.8 C7—C6—H6 119.5 C17—C16—H16 120.8 C8—C7—C6 121.1 (5) C12—C17—C16 119.6 (5) C8—C7—H7 119.4 C12—C17—C18 111.8 (4) C6—C7—H7 119.4 C16—C17—C18 128.6 (5) C7—C8—C9 117.5 (5) C19—C18—C17 102.9 (4) C7—C8—H8 121.2 C19—C18—H18A 111.2 C9—C8—H8 121.2 C17—C18—H18A 111.2 N1—C9—C8 129.9 (4) C19—C18—H18B 111.2 N1—C9—C4 107.8 (4) C17—C18—H18B 111.2 C8—C9—C4 122.3 (5) H18A—C18—H18B 109.1 C19—C10—C3 130.0 (4) C10—C19—C11 121.9 (4) C19—C10—H10 115.0 C10—C19—C18 129.2 (4) C3—C10—H10 115.0 C11—C19—C18 108.9 (4)

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C2—C3—C10—C19 −7.3 (7) C17—C18—C19—C11 2.3 (5) C4—C3—C10—C19 173.8 (4) C11—C19—C10—H10 0.1 O11—C11—C12—C17 −178.5 (5) C18—C19—C10—H10 179.3 C19—C11—C12—C17 1.8 (5) H13—C13—C12—C11 −0.1 O11—C11—C12—C13 2.4 (8) H10—C10—C3—C2 172.7 C19—C11—C12—C13 −177.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N1—H1···O11i _{0.86 2.16 2.829 (5) 134} C18—H18A···O11ii _{0.97 2.42 3.371 (6) 168}