Literature DB >> 21201686

7,8,9,10-Tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

M Sridharan, K J Rajendra Prasad, A Thomas Gunaseelan, A Thiruvalluvar, R J Butcher.   

Abstract

In the title mol-ecule, C(13)H(13)NO, the dihedral angle between the benzene and pyrrole rings is 1.05 (5)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds form centrosymmetric dimers. A C-H⋯π inter-action, involving the benzene ring, is also found in the structure.

Entities:  

Year:  2008        PMID： 21201686      PMCID： PMC2960645          DOI： 10.1107/S160053680802463X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a related structure, see: Sridharan et al. (2008 ▶).

Experimental

Crystal data

C13H13NO M = 199.24 Monoclinic, 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 ▶) 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 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶). 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
C13H13NOF000 = 424
Mr = 199.24Dx = 1.327 Mg m−3
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 mm−1
β = 108.937 (3)ºT = 200 (2) K
V = 997.24 (5) Å3Chunk, pale-yellow
Z = 40.56 × 0.38 × 0.31 mm
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
φ 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 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 Å−3
140 parametersΔρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
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*
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)
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)
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
Table 1

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⋯Cgii0.992.903.7087 (10)139

Symmetry codes: (i) ; (ii) . Cg is the centroid of the benzene ring.

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  7,8,9,10-Tetra-hydro-2-methyl-cyclo-hepta-[b]indol-6(5H)-one.

Authors:  Makuteswaran Sridharan; Karnam J Rajendra Prasad; Aimable Ngendahimana; Matthias Zeller
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-07
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1.  2,5-Dimethyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Authors:  R Archana; E Yamuna; K J Rajendra Prasad; A Thiruvalluvar; R J Butcher
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