Literature DB >> 21588650

8-Methyl-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

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

Abstract

In the title compound, C(13)H(13)NO, the dihedral angle between the benzene ring and the fused pyrrole ring is 0.96 (7)°. The cyclohexenone ring adopts an envelope conformation. Inter-molecular N-H⋯O hydrogen bonds form R(2) (2)(10) ring motifs in the crystal structure. Weak C-H⋯π inter-actions involving the benzene ring also occur.

Entities:  

Year:  2010        PMID： 21588650      PMCID： PMC3007954          DOI： 10.1107/S1600536810031545

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


Related literature

For tetra­hydro­carbazolones, see: Bringmann et al. (1995 ▶); Chakravarty et al. (2001 ▶); Knölker & Reddy (2002 ▶); Lin & Zhang (2000 ▶); Matsuo & Ishida (1994 ▶); Miki & Hachiken (1993 ▶); Scott et al. (2006 ▶). For biologically active carbazoles, see: Jean et al. (2004 ▶); Knölker & Reddy (2008 ▶). For the preparation of 1-oxo compounds via their corresponding hydrazones, see: Rajendra Prasad & Vijayalakshmi (1994 ▶). For crystal structures of substituted carbazole derivatives, see: Thomas Gunaseelan et al. (2009 ▶); Sridharan et al. (2008 ▶); Thiruvalluvar et al. (2007 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H13NO M = 199.24 Monoclinic, a = 10.5245 (2) Å b = 7.1564 (1) Å c = 13.5870 (3) Å β = 93.960 (2)° V = 1020.90 (3) Å3 Z = 4 Cu Kα radiation μ = 0.65 mm−1 T = 110 K 0.51 × 0.42 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.751, T max = 1.000 3655 measured reflections 2005 independent reflections 1882 reflections with I > 2σ(I) R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.120 S = 1.05 2005 reflections 141 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.33 e Å−3 Δρmin = −0.30 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031545/jj2046sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031545/jj2046Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H13NOF(000) = 424
Mr = 199.24Dx = 1.296 Mg m−3
Monoclinic, P21/nMelting point: 443 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54184 Å
a = 10.5245 (2) ÅCell parameters from 3169 reflections
b = 7.1564 (1) Åθ = 5.5–74.0°
c = 13.5870 (3) ŵ = 0.65 mm−1
β = 93.960 (2)°T = 110 K
V = 1020.90 (3) Å3Prism, colourless
Z = 40.51 × 0.42 × 0.34 mm
Oxford Diffraction Xcalibur Ruby Gemini diffractometer2005 independent reflections
Radiation source: Enhance (Cu) X-ray Source1882 reflections with I > 2σ(I)
graphiteRint = 0.016
Detector resolution: 10.5081 pixels mm-1θmax = 74.1°, θmin = 5.5°
ω scansh = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −8→8
Tmin = 0.751, Tmax = 1.000l = −16→12
3655 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0737P)2 + 0.4222P] where P = (Fo2 + 2Fc2)/3
2005 reflections(Δ/σ)max = 0.001
141 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.30 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
O1−0.14139 (9)0.43448 (14)0.05682 (7)0.0252 (3)
N90.11062 (10)0.26331 (16)0.07724 (8)0.0180 (3)
C1−0.12572 (12)0.27613 (18)0.09016 (9)0.0180 (3)
C2−0.23534 (12)0.15732 (18)0.11989 (9)0.0188 (3)
C3−0.19848 (12)0.01890 (19)0.20323 (10)0.0211 (4)
C4−0.08735 (12)−0.10760 (18)0.17805 (9)0.0202 (3)
C4A0.01788 (12)0.00943 (17)0.14160 (9)0.0171 (3)
C4B0.15114 (12)−0.02537 (18)0.13993 (9)0.0177 (3)
C50.22998 (13)−0.17717 (18)0.16994 (9)0.0207 (4)
C60.35880 (13)−0.16125 (19)0.15961 (10)0.0229 (4)
C70.41100 (12)0.00095 (19)0.11902 (10)0.0215 (4)
C80.33738 (12)0.15274 (18)0.08785 (9)0.0194 (4)
C8A0.20563 (12)0.13615 (17)0.09939 (9)0.0174 (3)
C9A−0.00264 (12)0.18558 (18)0.10250 (9)0.0171 (3)
C180.39245 (13)0.3254 (2)0.04456 (11)0.0274 (4)
H2A−0.303480.240340.141240.0226*
H2B−0.270400.086650.061530.0226*
H3A−0.174100.089180.264400.0254*
H3B−0.27315−0.059600.215690.0254*
H4A−0.11694−0.198660.126600.0242*
H4B−0.05557−0.178030.237450.0242*
H50.19525−0.287230.196510.0248*
H60.41364−0.261370.180200.0275*
H70.500300.006020.112880.0258*
H90.1191 (16)0.367 (3)0.0455 (13)0.028 (4)*
H18A0.484450.309320.040720.0411*
H18B0.352360.34649−0.021770.0411*
H18C0.376480.433170.086480.0411*
U11U22U33U12U13U23
O10.0232 (5)0.0218 (5)0.0312 (5)0.0037 (4)0.0057 (4)0.0081 (4)
N90.0179 (5)0.0162 (5)0.0203 (5)0.0005 (4)0.0034 (4)0.0027 (4)
C10.0204 (6)0.0198 (6)0.0140 (6)0.0004 (5)0.0021 (4)−0.0001 (5)
C20.0171 (6)0.0201 (6)0.0195 (6)0.0003 (5)0.0026 (5)−0.0010 (5)
C30.0209 (6)0.0217 (7)0.0214 (6)−0.0013 (5)0.0059 (5)0.0027 (5)
C40.0218 (6)0.0181 (6)0.0210 (6)−0.0010 (5)0.0042 (5)0.0034 (5)
C4A0.0201 (6)0.0178 (6)0.0136 (6)−0.0005 (5)0.0019 (4)−0.0002 (4)
C4B0.0211 (6)0.0186 (6)0.0133 (6)0.0003 (5)0.0016 (4)−0.0008 (4)
C50.0252 (7)0.0189 (6)0.0179 (6)0.0016 (5)0.0013 (5)0.0030 (5)
C60.0239 (7)0.0224 (7)0.0220 (6)0.0060 (5)−0.0017 (5)0.0018 (5)
C70.0173 (6)0.0260 (7)0.0209 (6)0.0022 (5)−0.0003 (5)−0.0019 (5)
C80.0193 (6)0.0209 (7)0.0181 (6)−0.0005 (5)0.0016 (5)−0.0017 (5)
C8A0.0196 (6)0.0181 (6)0.0145 (6)0.0014 (5)0.0006 (4)−0.0008 (4)
C9A0.0179 (6)0.0183 (6)0.0154 (6)−0.0010 (5)0.0031 (4)0.0001 (4)
C180.0191 (7)0.0248 (7)0.0385 (8)−0.0009 (5)0.0045 (5)0.0046 (6)
O1—C11.2273 (16)C7—C81.3836 (18)
N9—C8A1.3700 (17)C8—C8A1.4112 (18)
N9—C9A1.3801 (17)C8—C181.5019 (19)
N9—H90.87 (2)C2—H2A0.9900
C1—C9A1.4478 (18)C2—H2B0.9900
C1—C21.5105 (18)C3—H3A0.9900
C2—C31.5340 (18)C3—H3B0.9900
C3—C41.5362 (18)C4—H4A0.9900
C4—C4A1.4997 (18)C4—H4B0.9900
C4A—C4B1.4262 (18)C5—H50.9500
C4A—C9A1.3792 (18)C6—H60.9500
C4B—C8A1.4185 (18)C7—H70.9500
C4B—C51.4100 (18)C18—H18A0.9800
C5—C61.3773 (19)C18—H18B0.9800
C6—C71.4125 (19)C18—H18C0.9800
O1···N92.9173 (14)H2A···H18Avii2.5800
O1···C18i3.3659 (17)H2A···C3vi2.9000
O1···N9i2.8603 (15)H2A···C4vi2.9900
O1···H92.798 (17)H2A···H3Bvi2.5000
O1···H4Aii2.8000H2A···H4Bvi2.3700
O1···H9i2.01 (2)H2B···C7iii2.8500
O1···H18Bi2.7300H2B···C8iii2.7100
N9···O12.9173 (14)H2B···C8Aiii2.8300
N9···O1i2.8603 (15)H3A···C9A3.0200
N9···H4Aiii2.8100H3A···H3Bvi2.5900
C1···C4Biii3.5986 (18)H3B···C2viii3.0100
C4A···C9Aiii3.5916 (17)H3B···H2Aviii2.5000
C4B···C1iii3.5986 (18)H3B···H3Aviii2.5900
C5···C8Aiv3.4312 (17)H4A···O1ix2.8000
C8A···C5v3.4312 (17)H4A···N9iii2.8100
C9A···C4Aiii3.5916 (17)H4B···H2Aviii2.3700
C18···O1i3.3659 (17)H5···C8iv3.0000
C2···H3Bvi3.0100H5···C8Aiv2.9500
C2···H7vii2.9800H6···H18Cix2.5500
C3···H2Aviii2.9000H6···C4Aiv2.9700
C4···H2Aviii2.9900H6···C9Aiv3.0600
C4A···H6v2.9700H7···C2x2.9800
C6···H18Cix3.0800H7···H18A2.3800
C7···H2Biii2.8500H9···O12.798 (17)
C8···H2Biii2.7100H9···C182.893 (17)
C8···H5v3.0000H9···O1i2.01 (2)
C8A···H5v2.9500H18A···H2Ax2.5800
C8A···H2Biii2.8300H18A···H72.3800
C9A···H3A3.0200H18B···O1i2.7300
C9A···H6v3.0600H18C···C6ii3.0800
C18···H92.893 (17)H18C···H6ii2.5500
C8A—N9—C9A107.91 (11)C1—C2—H2A109.00
C9A—N9—H9126.1 (11)C1—C2—H2B109.00
C8A—N9—H9125.4 (11)C3—C2—H2A109.00
O1—C1—C9A123.53 (12)C3—C2—H2B109.00
O1—C1—C2122.20 (11)H2A—C2—H2B108.00
C2—C1—C9A114.26 (11)C2—C3—H3A109.00
C1—C2—C3113.70 (10)C2—C3—H3B109.00
C2—C3—C4111.95 (11)C4—C3—H3A109.00
C3—C4—C4A109.60 (10)C4—C3—H3B109.00
C4B—C4A—C9A106.35 (11)H3A—C3—H3B108.00
C4—C4A—C4B131.09 (11)C3—C4—H4A110.00
C4—C4A—C9A122.55 (11)C3—C4—H4B110.00
C5—C4B—C8A119.64 (12)C4A—C4—H4A110.00
C4A—C4B—C8A106.76 (11)C4A—C4—H4B110.00
C4A—C4B—C5133.60 (12)H4A—C4—H4B108.00
C4B—C5—C6118.07 (12)C4B—C5—H5121.00
C5—C6—C7121.33 (12)C6—C5—H5121.00
C6—C7—C8122.68 (12)C5—C6—H6119.00
C7—C8—C18122.87 (12)C7—C6—H6119.00
C7—C8—C8A115.70 (11)C6—C7—H7119.00
C8A—C8—C18121.43 (11)C8—C7—H7119.00
N9—C8A—C8128.87 (11)C8—C18—H18A109.00
C4B—C8A—C8122.58 (11)C8—C18—H18B109.00
N9—C8A—C4B108.55 (11)C8—C18—H18C109.00
C1—C9A—C4A124.67 (12)H18A—C18—H18B109.00
N9—C9A—C1124.89 (11)H18A—C18—H18C109.00
N9—C9A—C4A110.44 (11)H18B—C18—H18C109.00
C9A—N9—C8A—C4B−0.22 (14)C4—C4A—C9A—N9178.50 (11)
C9A—N9—C8A—C8−179.22 (12)C4—C4A—C9A—C1−1.27 (19)
C8A—N9—C9A—C1−179.79 (12)C4B—C4A—C9A—N9−0.48 (14)
C8A—N9—C9A—C4A0.45 (14)C4B—C4A—C9A—C1179.75 (12)
O1—C1—C2—C3−150.62 (12)C4A—C4B—C5—C6−178.27 (13)
C9A—C1—C2—C330.63 (15)C8A—C4B—C5—C60.78 (18)
O1—C1—C9A—N9−1.1 (2)C4A—C4B—C8A—N9−0.07 (14)
O1—C1—C9A—C4A178.62 (12)C4A—C4B—C8A—C8179.00 (11)
C2—C1—C9A—N9177.62 (11)C5—C4B—C8A—N9−179.35 (11)
C2—C1—C9A—C4A−2.64 (18)C5—C4B—C8A—C8−0.28 (19)
C1—C2—C3—C4−55.14 (14)C4B—C5—C6—C7−0.81 (19)
C2—C3—C4—C4A48.86 (14)C5—C6—C7—C80.3 (2)
C3—C4—C4A—C4B156.41 (13)C6—C7—C8—C8A0.20 (19)
C3—C4—C4A—C9A−22.29 (16)C6—C7—C8—C18−179.93 (14)
C4—C4A—C4B—C50.6 (2)C7—C8—C8A—N9178.66 (12)
C4—C4A—C4B—C8A−178.52 (12)C7—C8—C8A—C4B−0.21 (18)
C9A—C4A—C4B—C5179.47 (14)C18—C8—C8A—N9−1.2 (2)
C9A—C4A—C4B—C8A0.33 (14)C18—C8—C8A—C4B179.92 (12)
Cg3 is the centroid of the C4B,C5–C8,C8A ring.
D—H···AD—HH···AD···AD—H···A
N9—H9···O1i0.87 (2)2.01 (2)2.8603 (15)165.9 (18)
C2—H2B···Cg3iii0.992.643.5429 (13)152
C5—H5···Cg3iv0.952.863.6414 (14)140
Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4B,C5–C8,C8A ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N9—H9⋯O1i0.87 (2)2.01 (2)2.8603 (15)165.9 (18)
C2—H2B⋯Cg3ii0.992.643.5429 (13)152
C5—H5⋯Cg3iii0.952.863.6414 (14)140

Symmetry codes: (i) ; (ii) ; (iii) .

  7 in total

Review 1.  Isolation and synthesis of biologically active carbazole alkaloids.

Authors:  Hans-Joachim Knölker; Kethiri R Reddy
Journal:  Chem Rev       Date:  2002-11       Impact factor: 60.622

2.  A short history of SHELX.

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

3.  Synthesis of murrayaquinone-A.

Authors:  K Matsuo; S Ishida
Journal:  Chem Pharm Bull (Tokyo)       Date:  1994-06       Impact factor: 1.645

4.  6-Meth-oxy-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

Authors:  M Sridharan; K J Rajendra Prasad; A Thomas Gunaseelan; A Thiruvalluvar; A Linden
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-29

5.  3-Methyl-3,4-dihydro-9H-carbazol-1(2H)-one.

Authors:  A Thomas Gunaseelan; K Prabakaran; K J Rajendra Prasad; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-22

6.  1,2,3,4-tetrahydrocarbazoles as 5-HT6 serotonin receptor ligands.

Authors:  Jean Chang-Fong; Jagadeesh B Rangisetty; Małgorzata Dukat; Vincent Setola; Thomas Raffay; Bryan Roth; Richard A Glennon
Journal:  Bioorg Med Chem Lett       Date:  2004-04-19       Impact factor: 2.823

7.  Structure validation in chemical crystallography.

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

1.  6-Methyl-2,3,4,9-tetra-hydro-1H-carbazole-1-thione.

Authors:  R Archana; K Prabakaran; K J Rajendra Prasad; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-11
  1 in total

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