Literature DB >> 21589063

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

R Archana, E Yamuna, K J Rajendra Prasad, A Thiruvalluvar, R J Butcher.   

Abstract

In the title mol-ecule, C(15)H(17)NO, the dihedral angle between the benzene and pyrrole rings is 1.45 (13)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds are found.

Entities:  

Year:  2010        PMID： 21589063      PMCID： PMC3009033          DOI： 10.1107/S1600536810041772

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


Related literature

For the importance of the indole nucleus, see: Satoshi & Tominari (2001 ▶). For the synthesis of fused cyclo­hept[b]indole derivatives, see: Butin et al. (2010 ▶); Fujimori & Yamane (1978 ▶); Wahlström et al. (2007 ▶). For heteroannulated cyclo­hept[b]indole derivatives, see: Kavitha & Prasad (1999 ▶, 2001 ▶). For crystallographic studies of cyclo­hept[b]indoles, see: Sridharan et al. (2008a ▶,b ▶, 2009 ▶); Yamuna et al. (2010 ▶).

Experimental

Crystal data

C15H17NO M = 227.30 Orthorhombic, a = 15.5889 (3) Å b = 10.5707 (2) Å c = 7.5388 (2) Å V = 1242.29 (5) Å3 Z = 4 Cu Kα radiation μ = 0.59 mm−1 T = 295 K 0.49 × 0.32 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.887, T max = 1.000 1327 measured reflections 1327 independent reflections 1285 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.129 S = 1.09 1327 reflections 156 parameters 1 restraint H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.16 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041772/hg2724sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041772/hg2724Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H17NODx = 1.215 Mg m−3
Mr = 227.30Melting point: 346 K
Orthorhombic, Pca21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2acCell parameters from 2494 reflections
a = 15.5889 (3) Åθ = 5.1–73.7°
b = 10.5707 (2) ŵ = 0.59 mm−1
c = 7.5388 (2) ÅT = 295 K
V = 1242.29 (5) Å3Plate, pale yellow-orange
Z = 40.49 × 0.32 × 0.12 mm
F(000) = 488
Oxford Diffraction Xcalibur Ruby Gemini diffractometer1327 independent reflections
Radiation source: Enhance (Cu) X-ray Source1285 reflections with I > 2σ(I)
graphiteRint = 0.0000
Detector resolution: 10.5081 pixels mm-1θmax = 73.8°, θmin = 5.1°
ω scansh = 0→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = 0→13
Tmin = 0.887, Tmax = 1.000l = 0→9
1327 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.097P)2 + 0.041P] where P = (Fo2 + 2Fc2)/3
1327 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.17 e Å−3
1 restraintΔρmin = −0.16 e Å−3
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 > 2σ(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
O60.18943 (11)0.4617 (2)0.5238 (5)0.1003 (11)
N50.29328 (12)0.68004 (18)0.4471 (3)0.0561 (6)
C10.51734 (15)0.75136 (19)0.4664 (3)0.0534 (6)
C20.52228 (19)0.8760 (2)0.4100 (4)0.0667 (8)
C30.4462 (2)0.9404 (2)0.3639 (5)0.0789 (9)
C40.3667 (2)0.8856 (2)0.3734 (4)0.0738 (9)
C4A0.36199 (15)0.7584 (2)0.4294 (3)0.0534 (6)
C50.20448 (16)0.7199 (3)0.4212 (5)0.0757 (9)
C5A0.32271 (11)0.56233 (19)0.5029 (3)0.0478 (5)
C60.26683 (13)0.4538 (2)0.5353 (3)0.0573 (6)
C70.30755 (16)0.3306 (2)0.5819 (5)0.0711 (9)
C80.37596 (17)0.2890 (3)0.4485 (6)0.0817 (12)
C90.46482 (15)0.3391 (2)0.4821 (4)0.0614 (7)
C100.46951 (13)0.46270 (19)0.5847 (4)0.0536 (6)
C10A0.41137 (11)0.56610 (16)0.5207 (3)0.0434 (5)
C10B0.43718 (13)0.69124 (18)0.4753 (3)0.0469 (5)
C210.6075 (3)0.9427 (3)0.3943 (6)0.0945 (13)
H10.566860.707860.498200.0640*
H30.450221.023720.325320.0947*
H40.317520.930660.343950.0886*
H5A0.202870.790650.341420.1136*
H5B0.180190.744100.533210.1136*
H5C0.172000.651200.372010.1136*
H7A0.263450.266050.588450.0853*
H7B0.333620.337650.698350.0853*
H8A0.378400.197260.448330.0980*
H8B0.358080.315610.331100.0980*
H9A0.493070.350960.368710.0737*
H9B0.496890.275430.546910.0737*
H10A0.456050.445400.707980.0643*
H10B0.528130.493340.580320.0643*
H21A0.652870.884800.422750.1418*
H21B0.609001.012910.475110.1418*
H21C0.614810.972960.275210.1418*
U11U22U33U12U13U23
O60.0441 (8)0.0967 (14)0.160 (3)−0.0048 (8)0.0028 (14)0.0057 (18)
N50.0518 (9)0.0564 (10)0.0600 (11)0.0183 (8)−0.0059 (8)−0.0087 (9)
C10.0627 (11)0.0451 (9)0.0524 (12)−0.0035 (8)0.0046 (9)−0.0064 (8)
C20.0934 (17)0.0432 (10)0.0636 (14)−0.0093 (10)0.0126 (13)−0.0110 (11)
C30.122 (2)0.0374 (9)0.0772 (18)−0.0010 (12)0.0128 (18)−0.0027 (12)
C40.1000 (19)0.0475 (12)0.0740 (17)0.0272 (12)−0.0020 (14)−0.0022 (12)
C4A0.0629 (12)0.0465 (10)0.0509 (10)0.0129 (8)0.0003 (9)−0.0069 (9)
C50.0588 (13)0.0851 (17)0.0833 (17)0.0332 (13)−0.0132 (13)−0.0156 (16)
C5A0.0438 (9)0.0511 (10)0.0485 (9)0.0080 (7)0.0005 (8)−0.0059 (9)
C60.0440 (9)0.0653 (11)0.0625 (12)−0.0037 (8)0.0062 (9)−0.0094 (11)
C70.0565 (11)0.0587 (12)0.098 (2)−0.0114 (10)0.0112 (13)0.0050 (15)
C80.0641 (13)0.0681 (14)0.113 (3)0.0050 (11)−0.0031 (16)−0.0378 (19)
C90.0596 (11)0.0469 (10)0.0777 (15)0.0111 (8)0.0124 (11)0.0058 (11)
C100.0425 (8)0.0492 (10)0.0691 (14)0.0037 (7)−0.0056 (9)0.0103 (10)
C10A0.0429 (8)0.0430 (9)0.0444 (9)0.0042 (7)−0.0001 (8)−0.0025 (8)
C10B0.0567 (10)0.0404 (9)0.0436 (9)0.0062 (7)0.0024 (8)−0.0033 (8)
C210.120 (3)0.0646 (15)0.099 (2)−0.0374 (17)0.018 (2)−0.0114 (17)
O6—C61.213 (3)C10A—C10B1.424 (3)
N5—C4A1.361 (3)C1—H10.9300
N5—C51.460 (3)C3—H30.9300
N5—C5A1.391 (3)C4—H40.9300
C1—C21.387 (3)C5—H5A0.9600
C1—C10B1.404 (3)C5—H5B0.9600
C2—C31.411 (4)C5—H5C0.9600
C2—C211.509 (5)C7—H7A0.9700
C3—C41.370 (4)C7—H7B0.9700
C4—C4A1.411 (3)C8—H8A0.9700
C4A—C10B1.413 (3)C8—H8B0.9700
C5A—C61.461 (3)C9—H9A0.9700
C5A—C10A1.389 (2)C9—H9B0.9700
C6—C71.491 (3)C10—H10A0.9700
C7—C81.530 (5)C10—H10B0.9700
C8—C91.505 (4)C21—H21A0.9600
C9—C101.520 (3)C21—H21B0.9600
C10—C10A1.500 (3)C21—H21C0.9600
O6···N52.878 (3)H1···O6viii2.6300
O6···C52.847 (4)H3···H8Avi2.3400
O6···H5C2.3200H4···C52.9000
O6···H7Bi2.8100H4···H5A2.3200
O6···H8Bii2.8800H5A···C42.7500
O6···H1iii2.6300H5A···H42.3200
O6···H10Biii2.5900H5B···C4ii3.0600
N5···O62.878 (3)H5B···C4Aii3.0600
C5···O62.847 (4)H5C···O62.3200
C5···C5Ai3.591 (4)H5C···C62.8400
C5A···C5ii3.591 (4)H5C···C5Ai2.9400
C1···H10Aiv2.8800H5C···C10Ai3.0800
C1···H10B2.8600H7B···C102.6400
C3···H21Bv3.0900H7B···C10A3.0200
C3···H8Avi2.9800H7B···H10A2.2200
C4···H5Bi3.0600H7B···O6ii2.8100
C4···H5A2.7500H8A···C3ix2.9800
C4A···H5Bi3.0600H8A···H3ix2.3400
C5···H42.9000H8B···C5A2.9600
C5A···H8B2.9600H8B···O6i2.8800
C5A···H5Cii2.9400H9A···C10iv2.9700
C6···H5C2.8400H9A···H10Aiv2.5900
C7···H10A2.7800H10A···C72.7800
C10···H13.0700H10A···H7B2.2200
C10···H7B2.6400H10A···C1vii2.8800
C10···H9Avii2.9700H10A···C10Bvii2.9900
C10A···H7B3.0200H10A···H9Avii2.5900
C10A···H5Cii3.0800H10B···C12.8600
C10B···H10Aiv2.9900H10B···H12.4300
H1···C103.0700H10B···O6viii2.5900
H1···H10B2.4300H21A···H12.3700
H1···H21A2.3700H21B···C3x3.0900
C4A—N5—C5123.9 (2)C4A—C4—H4121.00
C4A—N5—C5A108.33 (17)N5—C5—H5A109.00
C5—N5—C5A127.7 (2)N5—C5—H5B109.00
C2—C1—C10B119.6 (2)N5—C5—H5C109.00
C1—C2—C3119.2 (2)H5A—C5—H5B109.00
C1—C2—C21121.1 (3)H5A—C5—H5C109.00
C3—C2—C21119.7 (2)H5B—C5—H5C109.00
C2—C3—C4122.9 (2)C6—C7—H7A109.00
C3—C4—C4A117.8 (2)C6—C7—H7B109.00
N5—C4A—C4130.6 (2)C8—C7—H7A109.00
N5—C4A—C10B108.85 (18)C8—C7—H7B109.00
C4—C4A—C10B120.6 (2)H7A—C7—H7B108.00
N5—C5A—C6123.79 (17)C7—C8—H8A108.00
N5—C5A—C10A109.37 (17)C7—C8—H8B108.00
C6—C5A—C10A126.84 (18)C9—C8—H8A108.00
O6—C6—C5A121.8 (2)C9—C8—H8B108.00
O6—C6—C7120.1 (2)H8A—C8—H8B107.00
C5A—C6—C7118.13 (18)C8—C9—H9A108.00
C6—C7—C8113.1 (3)C8—C9—H9B108.00
C7—C8—C9115.5 (3)C10—C9—H9A108.00
C8—C9—C10115.6 (2)C10—C9—H9B108.00
C9—C10—C10A115.7 (2)H9A—C9—H9B107.00
C5A—C10A—C10127.70 (17)C9—C10—H10A108.00
C5A—C10A—C10B106.53 (16)C9—C10—H10B108.00
C10—C10A—C10B125.70 (16)C10A—C10—H10A108.00
C1—C10B—C4A119.95 (18)C10A—C10—H10B108.00
C1—C10B—C10A133.12 (19)H10A—C10—H10B107.00
C4A—C10B—C10A106.92 (17)C2—C21—H21A109.00
C2—C1—H1120.00C2—C21—H21B109.00
C10B—C1—H1120.00C2—C21—H21C109.00
C2—C3—H3119.00H21A—C21—H21B109.00
C4—C3—H3119.00H21A—C21—H21C110.00
C3—C4—H4121.00H21B—C21—H21C109.00
C5—N5—C4A—C4−5.0 (4)C4—C4A—C10B—C10A−178.4 (2)
C5—N5—C4A—C10B176.1 (3)N5—C5A—C6—O6−3.8 (4)
C5A—N5—C4A—C4178.6 (3)N5—C5A—C6—C7175.6 (2)
C5A—N5—C4A—C10B−0.4 (3)C10A—C5A—C6—O6176.5 (3)
C4A—N5—C5A—C6−179.7 (2)C10A—C5A—C6—C7−4.1 (4)
C4A—N5—C5A—C10A0.0 (3)N5—C5A—C10A—C10177.3 (2)
C5—N5—C5A—C64.0 (4)N5—C5A—C10A—C10B0.4 (3)
C5—N5—C5A—C10A−176.4 (3)C6—C5A—C10A—C10−3.1 (4)
C10B—C1—C2—C30.5 (4)C6—C5A—C10A—C10B−179.9 (2)
C10B—C1—C2—C21−178.4 (3)O6—C6—C7—C8126.1 (3)
C2—C1—C10B—C4A−0.9 (3)C5A—C6—C7—C8−53.3 (3)
C2—C1—C10B—C10A177.5 (3)C6—C7—C8—C986.9 (3)
C1—C2—C3—C40.5 (5)C7—C8—C9—C10−25.7 (4)
C21—C2—C3—C4179.5 (3)C8—C9—C10—C10A−48.2 (3)
C2—C3—C4—C4A−1.0 (5)C9—C10—C10A—C5A57.1 (3)
C3—C4—C4A—N5−178.3 (3)C9—C10—C10A—C10B−126.6 (2)
C3—C4—C4A—C10B0.6 (4)C5A—C10A—C10B—C1−179.3 (2)
N5—C4A—C10B—C1179.5 (2)C5A—C10A—C10B—C4A−0.7 (3)
N5—C4A—C10B—C10A0.6 (3)C10—C10A—C10B—C13.9 (4)
C4—C4A—C10B—C10.4 (3)C10—C10A—C10B—C4A−177.5 (2)
D—H···AD—HH···AD···AD—H···A
C10—H10B···O6viii0.972.593.550 (3)168
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C10—H10B⋯O6i0.972.593.550 (3)168

Symmetry code: (i) .

  6 in total

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-cyclo-hepta-[b]indol-6(5H)-one.

Authors:  M Sridharan; K J Rajendra Prasad; A Thomas Gunaseelan; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-06

3.  Synthetic applications of cyanoacetylated bisindoles: synthesis of novel cycloheptadiindoles, indolocarbazoles, and related aza analogues.

Authors:  Niklas Wahlström; Johnny Slätt; Birgitta Stensland; Anne Ertan; Jan Bergman; Tomasz Janosik
Journal:  J Org Chem       Date:  2007-06-22       Impact factor: 4.354

4.  4-Methyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Authors:  M Sridharan; K J Rajendra Prasad; A Thomas Gunaseelan; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-06

5.  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

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  2 in total

1.  5-Methyl-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
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-07

2.  2-Chloro-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; Sushil K Gupta; Sema Oztürk Yildirim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-26
  2 in total

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