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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1697.
Published online 2008 August 6. doi:  10.1107/S160053680802463X
PMCID: PMC2960645

7,8,9,10-Tetra­hydro­cyclo­hepta­[b]indol-6(5H)-one

Abstract

In the title mol­ecule, C13H13NO, the dihedral angle between the benzene and pyrrole rings is 1.05 (5)°. The cyclo­heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter­molecular N—H(...)O hydrogen bonds form centrosymmetric dimers. A C—H(...)π inter­action, involving the benzene ring, is also found in the structure.

Related literature

For a related structure, see: Sridharan et al. (2008 [triangle]).

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Object name is e-64-o1697-scheme1.jpg

Experimental

Crystal data

  • C13H13NO
  • M r = 199.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1697-efi1.jpg
  • a = 14.0914 (4) Å
  • b = 8.0883 (2) Å
  • c = 9.2503 (3) Å
  • β = 108.937 (3)°
  • V = 997.24 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 200 (2) K
  • 0.56 × 0.38 × 0.31 mm

Data collection

  • Oxford Diffraction Gemini R diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.985, T max = 1.000 (expected range = 0.960–0.974)
  • 15925 measured reflections
  • 4127 independent reflections
  • 3036 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.145
  • S = 1.01
  • 4127 reflections
  • 140 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802463X/wn2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802463X/wn2274Isup2.hkl

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

Acknowledgments

MS thanks the UGC, New Delhi, India, for the award of a research fellowship. KJR acknowledges the UGC, New Delhi, India, for the award of Major Research Project Grant No. F.No.31–122/2005. AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF-MRI program for funding to purchase the X-ray CCD diffractometer.

supplementary crystallographic information

Comment

Sridharan et al. (2008) have reported the crystal structure of 7,8,9,10-tetrahydro-2-methylcyclohepta[b]indol-6(5H)-one, in which the cycloheptene ring adopts a slightly distorted envelope conformation. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The dihedral angle between the benzene ring and the pyrrole ring is 1.05 (5)°. The cycloheptene ring adopts a slightly distorted boat conformation. Intermolecular N5—H5···O6 (-x, -y, 1 - z) hydrogen bonds form centrosymmetric dimers in the crystal structure (Fig. 2). A C—H···π interaction, involving the benzene ring, is also found in the structure.

Experimental

A solution of 2-(2-(4-phenyl)hydrazono)cycloheptanone (0.216 g, 0.001 mol) in a mixture of acetic acid (20 ml) and concentrated hydrochloric acid (5 ml) was refluxed on an oil bath pre-heated to 398–403 K for 2 h. The reaction was monitored by TLC. After the completion of reaction the contents were cooled and poured into ice water with stirring. The separated brown solid was filtered and purified by passing through a column of silica gel and eluting with petroleum ether-ethyl acetate (95:5 v/v) mixture to yield the title compound (0.129 g, 61%). The product thus obtained was recrystallized using ethanol.

Refinement

The H atom bonded to N5 was located in a difference Fourier map and refined isotropically [N5—H5 = 0.891 (16) Å]. Other H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.99 Å and Uiso(H) = 1.2Ueq(parent atom).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.
Fig. 2.
The molecular packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C13H13NOF000 = 424
Mr = 199.24Dx = 1.327 Mg m3
Monoclinic, P21/cMelting point: 425(1) K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 14.0914 (4) ÅCell parameters from 7034 reflections
b = 8.0883 (2) Åθ = 5.0–34.8º
c = 9.2503 (3) ŵ = 0.08 mm1
β = 108.937 (3)ºT = 200 (2) K
V = 997.24 (5) Å3Chunk, pale-yellow
Z = 40.56 × 0.38 × 0.31 mm

Data collection

Oxford Diffraction R Gemini diffractometer4127 independent reflections
Radiation source: fine-focus sealed tube3036 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
Detector resolution: 10.5081 pixels mm-1θmax = 34.9º
T = 200(2) Kθmin = 5.0º
[var phi] and ω scansh = −22→22
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)k = −12→12
Tmin = 0.985, Tmax = 1.000l = −11→14
15925 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145  w = 1/[σ2(Fo2) + (0.097P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4127 reflectionsΔρmax = 0.31 e Å3
140 parametersΔρmin = −0.35 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
O6−0.00855 (5)0.08244 (11)0.30591 (9)0.0440 (2)
N50.15340 (5)−0.04196 (9)0.54651 (8)0.0256 (2)
C10.42047 (7)−0.01523 (11)0.66953 (11)0.0298 (2)
C20.44834 (7)−0.08626 (12)0.81195 (11)0.0343 (3)
C30.37614 (7)−0.14708 (12)0.87403 (11)0.0332 (3)
C40.27498 (7)−0.13868 (10)0.79473 (10)0.0284 (2)
C4A0.24673 (6)−0.06767 (10)0.64909 (9)0.0232 (2)
C5A0.16322 (6)0.03677 (10)0.41960 (10)0.0242 (2)
C60.07608 (6)0.08971 (11)0.29509 (10)0.0280 (2)
C70.09234 (7)0.15126 (12)0.15191 (11)0.0321 (3)
C80.16098 (8)0.03791 (13)0.09678 (11)0.0349 (3)
C90.27357 (7)0.06922 (12)0.16778 (11)0.0312 (2)
C100.30600 (6)0.14407 (11)0.32855 (10)0.0293 (2)
C10A0.26382 (6)0.05963 (10)0.43769 (10)0.0235 (2)
C10B0.31807 (6)−0.00584 (10)0.58454 (10)0.0235 (2)
H10.469630.026830.629200.0357*
H20.51753−0.094560.869700.0412*
H30.39782−0.195110.973110.0398*
H40.22650−0.179340.837110.0340*
H50.0970 (11)−0.0616 (16)0.5673 (16)0.049 (4)*
H7A0.026620.160530.070220.0385*
H7B0.122330.263140.170840.0385*
H8A0.142770.04968−0.015460.0419*
H8B0.14723−0.078000.118110.0419*
H9A0.30934−0.036930.171930.0375*
H9B0.295030.144420.099810.0375*
H10A0.285420.261650.320520.0351*
H10B0.380140.140720.371100.0351*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O60.0248 (3)0.0711 (5)0.0371 (4)0.0026 (3)0.0116 (3)0.0130 (4)
N50.0247 (3)0.0298 (3)0.0240 (3)−0.0015 (3)0.0102 (3)0.0031 (3)
C10.0252 (4)0.0355 (4)0.0284 (4)−0.0014 (3)0.0084 (3)−0.0035 (3)
C20.0296 (4)0.0410 (5)0.0283 (4)0.0012 (4)0.0038 (3)−0.0013 (4)
C30.0391 (5)0.0331 (4)0.0239 (4)0.0006 (3)0.0055 (3)0.0021 (3)
C40.0358 (4)0.0266 (4)0.0231 (4)−0.0022 (3)0.0101 (3)0.0008 (3)
C4A0.0262 (3)0.0217 (3)0.0224 (4)−0.0004 (3)0.0088 (3)−0.0016 (3)
C5A0.0252 (4)0.0256 (3)0.0229 (4)−0.0003 (3)0.0094 (3)0.0017 (3)
C60.0262 (4)0.0316 (4)0.0268 (4)0.0006 (3)0.0096 (3)0.0035 (3)
C70.0308 (4)0.0386 (5)0.0270 (4)0.0031 (3)0.0097 (3)0.0091 (3)
C80.0370 (5)0.0436 (5)0.0250 (4)−0.0005 (4)0.0113 (4)−0.0009 (4)
C90.0358 (4)0.0367 (4)0.0261 (4)0.0016 (3)0.0168 (3)0.0049 (3)
C100.0295 (4)0.0326 (4)0.0289 (4)−0.0038 (3)0.0139 (3)0.0023 (3)
C10A0.0257 (4)0.0240 (3)0.0230 (4)−0.0010 (3)0.0109 (3)−0.0006 (3)
C10B0.0247 (3)0.0238 (3)0.0226 (4)−0.0007 (3)0.0087 (3)−0.0024 (3)

Geometric parameters (Å, °)

O6—C61.2301 (12)C9—C101.5316 (13)
N5—C4A1.3650 (11)C10—C10A1.4928 (12)
N5—C5A1.3814 (11)C10A—C10B1.4269 (12)
N5—H50.891 (16)C1—H10.9500
C1—C10B1.4035 (14)C2—H20.9500
C1—C21.3726 (14)C3—H30.9500
C2—C31.4093 (14)C4—H40.9500
C3—C41.3770 (14)C7—H7A0.9900
C4—C4A1.3983 (12)C7—H7B0.9900
C4A—C10B1.4166 (12)C8—H8A0.9900
C5A—C61.4491 (12)C8—H8B0.9900
C5A—C10A1.3849 (13)C9—H9A0.9900
C6—C71.5005 (13)C9—H9B0.9900
C7—C81.5350 (15)C10—H10A0.9900
C8—C91.5285 (15)C10—H10B0.9900
O6···N52.8066 (11)H2···H9Bvii2.6000
O6···N5i2.8188 (11)H3···C1v2.9200
O6···H52.661 (14)H3···C10Bv2.9900
O6···H5i1.976 (16)H5···O62.661 (14)
N5···O62.8066 (11)H5···O6i1.976 (16)
N5···O6i2.8188 (11)H5···H7Bii2.5800
N5···H7Bii2.6300H7A···C8vi3.0500
C2···C2iii3.5893 (14)H7A···H8Bvi2.5900
C1···H10B2.9200H7B···C102.7000
C1···H3iv2.9200H7B···C10A3.1000
C3···H2iii3.0600H7B···H10A2.2700
C4···H8Bv3.0400H7B···N5viii2.6300
C4···H9Av2.9600H7B···C4Aviii3.0700
C4···H10Aii3.0600H7B···C5Aviii3.0400
C4A···H7Bii3.0700H7B···H5viii2.5800
C4A···H10Aii2.8900H8B···C5A2.8800
C5A···H8B2.8800H8B···C10A3.0900
C5A···H7Bii3.0400H8B···H7Avi2.5900
C7···H10A2.8100H8B···C4iv3.0400
C8···H7Avi3.0500H9A···C4iv2.9600
C9···H2vii3.0800H9B···H2vii2.6000
C10···H7B2.7000H9B···C10viii3.0800
C10···H9Bii3.0800H9B···C10Aviii2.7800
C10A···H7B3.1000H9B···C10Bviii2.9500
C10A···H8B3.0900H10A···C72.8100
C10A···H9Bii2.7800H10A···H7B2.2700
C10B···H3iv2.9900H10A···C4viii3.0600
C10B···H9Bii2.9500H10A···C4Aviii2.8900
C10B···H10Aii3.0900H10A···C10Bviii3.0900
H1···H10B2.4900H10B···C12.9200
H1···H10Bvii2.5100H10B···H12.4900
H2···C3iii3.0600H10B···H1vii2.5100
H2···C9vii3.0800
C4A—N5—C5A108.75 (7)C10B—C1—H1121.00
C4A—N5—H5123.3 (9)C1—C2—H2119.00
C5A—N5—H5127.5 (9)C3—C2—H2119.00
C2—C1—C10B118.83 (9)C2—C3—H3119.00
C1—C2—C3121.18 (9)C4—C3—H3119.00
C2—C3—C4121.68 (9)C3—C4—H4121.00
C3—C4—C4A117.09 (9)C4A—C4—H4121.00
N5—C4A—C4129.88 (8)C6—C7—H7A109.00
N5—C4A—C10B107.98 (7)C6—C7—H7B109.00
C4—C4A—C10B122.14 (8)C8—C7—H7A109.00
N5—C5A—C6121.26 (8)C8—C7—H7B109.00
C6—C5A—C10A128.81 (8)H7A—C7—H7B108.00
N5—C5A—C10A109.86 (8)C7—C8—H8A108.00
O6—C6—C7121.16 (8)C7—C8—H8B108.00
C5A—C6—C7117.83 (8)C9—C8—H8A108.00
O6—C6—C5A121.00 (8)C9—C8—H8B108.00
C6—C7—C8112.85 (8)H8A—C8—H8B107.00
C7—C8—C9115.87 (8)C8—C9—H9A109.00
C8—C9—C10115.07 (8)C8—C9—H9B108.00
C9—C10—C10A114.65 (8)C10—C9—H9A109.00
C5A—C10A—C10B106.06 (8)C10—C9—H9B109.00
C10—C10A—C10B127.28 (8)H9A—C9—H9B108.00
C5A—C10A—C10126.58 (8)C9—C10—H10A109.00
C4A—C10B—C10A107.34 (8)C9—C10—H10B109.00
C1—C10B—C4A119.08 (8)C10A—C10—H10A109.00
C1—C10B—C10A133.56 (8)C10A—C10—H10B109.00
C2—C1—H1121.00H10A—C10—H10B108.00
C5A—N5—C4A—C4178.26 (8)C10A—C5A—C6—O6−168.79 (9)
C5A—N5—C4A—C10B−0.94 (9)C10A—C5A—C6—C712.09 (14)
C4A—N5—C5A—C6−176.03 (8)N5—C5A—C10A—C10−178.13 (8)
C4A—N5—C5A—C10A1.30 (10)N5—C5A—C10A—C10B−1.11 (9)
C2—C1—C10B—C10A179.18 (9)C6—C5A—C10A—C10−1.05 (15)
C2—C1—C10B—C4A0.89 (13)C6—C5A—C10A—C10B175.96 (8)
C10B—C1—C2—C3−0.89 (14)O6—C6—C7—C8−132.19 (10)
C1—C2—C3—C40.30 (15)C5A—C6—C7—C846.93 (11)
C2—C3—C4—C4A0.29 (13)C6—C7—C8—C9−85.91 (11)
C3—C4—C4A—C10B−0.27 (12)C7—C8—C9—C1027.65 (12)
C3—C4—C4A—N5−179.36 (9)C8—C9—C10—C10A48.32 (11)
N5—C4A—C10B—C1178.95 (8)C9—C10—C10A—C5A−57.72 (12)
C4—C4A—C10B—C10A−179.02 (8)C9—C10—C10A—C10B125.89 (9)
N5—C4A—C10B—C10A0.25 (9)C5A—C10A—C10B—C1−177.91 (9)
C4—C4A—C10B—C1−0.32 (12)C5A—C10A—C10B—C4A0.53 (9)
N5—C5A—C6—O67.99 (13)C10—C10A—C10B—C1−0.92 (16)
N5—C5A—C6—C7−171.13 (8)C10—C10A—C10B—C4A177.51 (8)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) x, −y−1/2, z−1/2; (v) x, −y−1/2, z+1/2; (vi) −x, −y, −z; (vii) −x+1, −y, −z+1; (viii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N5—H5···O6i0.891 (16)1.976 (16)2.8188 (11)157.3 (13)
C10—H10A···Cgviii0.992.903.7087 (10)139

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2274).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008). Acta Cryst. E64, o1207. [PMC free article] [PubMed]

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