Literature DB >> 21589444

(E)-2-(Furan-2-yl-methyl-idene)-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 mol-ecule, C(18)H(15)NO(2), the carbazole unit is not planar [maximum deviation from mean plane = 0.236 (2) Å]. The pyrrole ring makes dihedral angles of 1.21 (10) and 16.74 (12)° with the benzene and the furan rings, respectively. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(10) loops.

Entities:  

Year:  2010        PMID： 21589444      PMCID： PMC3011638          DOI： 10.1107/S1600536810045599

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


Related literature

For the synthesis of hetero-annulated carbazoles, see: Knölker & Reddy (2002 ▶). For the derivation of various hetero-annulated carbazoles, see: Sridharan et al. (2008 ▶); Danish & Rajendra Prasad (2004 ▶, 2005 ▶); Periyasami et al. (2008 ▶, 2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H15NO2 M = 277.31 Orthorhombic, a = 6.7353 (1) Å b = 16.1393 (3) Å c = 25.9549 (4) Å V = 2821.38 (8) Å3 Z = 8 Cu Kα radiation μ = 0.68 mm−1 T = 295 K 0.44 × 0.28 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.888, T max = 1.000 6361 measured reflections 2736 independent reflections 2201 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.157 S = 1.05 2736 reflections 195 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.26 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/S1600536810045599/si2306sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045599/si2306Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H15NO2Dx = 1.306 Mg m−3
Mr = 277.31Melting point: 505 K
Orthorhombic, PbcaCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2abCell parameters from 3160 reflections
a = 6.7353 (1) Åθ = 4.4–72.5°
b = 16.1393 (3) ŵ = 0.68 mm−1
c = 25.9549 (4) ÅT = 295 K
V = 2821.38 (8) Å3Prism, pale-yellow
Z = 80.44 × 0.28 × 0.12 mm
F(000) = 1168
Oxford Diffraction Xcalibur Ruby Gemini diffractometer2736 independent reflections
Radiation source: Enhance (Cu) X-ray Source2201 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 10.5081 pixels mm-1θmax = 72.7°, θmin = 5.7°
ω scansh = −5→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −19→13
Tmin = 0.888, Tmax = 1.000l = −31→31
6361 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0921P)2 + 0.408P] where P = (Fo2 + 2Fc2)/3
2736 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.26 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
O10.3691 (2)0.06478 (9)−0.04131 (5)0.0638 (5)
O110.0871 (3)0.21485 (11)−0.18520 (6)0.0810 (6)
N90.2678 (2)0.02422 (9)0.06403 (5)0.0489 (4)
C10.2176 (3)0.09332 (11)−0.02148 (6)0.0475 (5)
C20.0821 (2)0.15134 (10)−0.04916 (7)0.0473 (5)
C3−0.0829 (3)0.19426 (12)−0.01982 (8)0.0605 (6)
C4−0.1653 (3)0.14925 (13)0.02677 (8)0.0615 (6)
C4A−0.0102 (3)0.10045 (11)0.05422 (7)0.0508 (5)
C4B−0.0102 (3)0.06700 (11)0.10466 (7)0.0537 (6)
C5−0.1417 (3)0.07341 (14)0.14698 (8)0.0679 (7)
C6−0.0955 (4)0.03192 (16)0.19083 (9)0.0735 (8)
C70.0762 (3)−0.01716 (14)0.19432 (8)0.0681 (7)
C80.2108 (3)−0.02535 (12)0.15467 (7)0.0561 (6)
C8A0.1646 (3)0.01922 (10)0.10952 (6)0.0497 (5)
C9A0.1612 (3)0.07363 (10)0.03084 (6)0.0466 (5)
C100.1218 (3)0.16433 (11)−0.09919 (7)0.0518 (5)
C12−0.0226 (4)0.27239 (15)−0.21183 (9)0.0775 (8)
C13−0.1434 (4)0.31065 (15)−0.18050 (9)0.0736 (8)
C14−0.1132 (3)0.27681 (12)−0.13083 (7)0.0586 (6)
C150.0280 (3)0.21920 (11)−0.13515 (7)0.0551 (6)
C180.3917 (3)−0.07814 (15)0.15847 (8)0.0718 (8)
H3A−0.191530.20433−0.043550.0725*
H3B−0.034170.24784−0.008560.0725*
H4A−0.222230.189370.050350.0738*
H4B−0.270670.112280.015790.0738*
H5−0.256540.105190.144800.0815*
H6−0.179300.036070.219190.0882*
H70.10015−0.045520.224890.0818*
H90.382 (4)−0.0012 (13)0.0577 (9)0.063 (6)*
H100.225760.13304−0.112520.0622*
H12−0.012220.28261−0.246990.0931*
H13−0.232670.35233−0.189210.0884*
H14−0.179370.29187−0.100800.0704*
H18A0.39152−0.106870.190850.1077*
H18B0.50785−0.043890.156170.1077*
H18C0.39214−0.117660.130830.1077*
U11U22U33U12U13U23
O10.0598 (8)0.0799 (9)0.0517 (7)0.0239 (7)0.0087 (6)0.0061 (6)
O110.0930 (12)0.0872 (11)0.0627 (9)0.0242 (9)0.0049 (8)0.0038 (8)
N90.0503 (8)0.0537 (8)0.0428 (7)0.0025 (7)0.0021 (6)−0.0015 (6)
C10.0486 (9)0.0478 (9)0.0460 (9)0.0025 (7)0.0006 (7)−0.0052 (7)
C20.0471 (9)0.0464 (8)0.0485 (9)0.0012 (7)−0.0018 (7)−0.0039 (7)
C30.0562 (10)0.0619 (11)0.0633 (12)0.0158 (9)0.0043 (9)0.0010 (9)
C40.0534 (10)0.0664 (11)0.0647 (12)0.0118 (9)0.0092 (9)−0.0047 (9)
C4A0.0500 (9)0.0496 (9)0.0528 (10)−0.0019 (7)0.0042 (7)−0.0084 (8)
C4B0.0550 (10)0.0557 (10)0.0503 (10)−0.0077 (8)0.0080 (8)−0.0092 (8)
C50.0656 (12)0.0755 (13)0.0627 (12)−0.0084 (10)0.0200 (10)−0.0104 (10)
C60.0797 (15)0.0856 (15)0.0553 (12)−0.0232 (12)0.0225 (11)−0.0094 (11)
C70.0816 (15)0.0771 (13)0.0457 (10)−0.0289 (12)0.0024 (10)0.0011 (9)
C80.0672 (11)0.0566 (10)0.0444 (9)−0.0180 (9)−0.0046 (8)−0.0018 (8)
C8A0.0546 (9)0.0514 (9)0.0431 (9)−0.0118 (8)0.0025 (7)−0.0072 (7)
C9A0.0491 (8)0.0462 (8)0.0446 (9)0.0009 (7)−0.0007 (7)−0.0055 (7)
C100.0548 (9)0.0478 (9)0.0529 (10)0.0049 (8)−0.0025 (8)−0.0045 (7)
C120.0962 (16)0.0823 (14)0.0541 (12)0.0093 (13)−0.0067 (12)0.0136 (11)
C130.0794 (14)0.0662 (13)0.0753 (15)0.0177 (11)−0.0178 (12)0.0001 (11)
C140.0643 (11)0.0643 (11)0.0473 (10)0.0131 (9)−0.0024 (8)−0.0073 (8)
C150.0623 (10)0.0526 (9)0.0505 (10)−0.0036 (8)−0.0064 (8)−0.0008 (8)
C180.0778 (14)0.0819 (15)0.0556 (12)−0.0085 (12)−0.0087 (10)0.0123 (10)
O1—C11.232 (2)C8—C8A1.410 (2)
O11—C121.373 (3)C10—C151.433 (3)
O11—C151.361 (2)C12—C131.306 (4)
N9—C8A1.373 (2)C13—C141.415 (3)
N9—C9A1.376 (2)C14—C151.335 (3)
N9—H90.89 (3)C3—H3A0.9700
C1—C21.492 (2)C3—H3B0.9700
C1—C9A1.446 (2)C4—H4A0.9700
C2—C31.515 (3)C4—H4B0.9700
C2—C101.342 (3)C5—H50.9300
C3—C41.516 (3)C6—H60.9300
C4—C4A1.490 (3)C7—H70.9300
C4A—C9A1.374 (3)C10—H100.9300
C4A—C4B1.416 (3)C12—H120.9300
C4B—C51.415 (3)C13—H130.9300
C4B—C8A1.413 (3)C14—H140.9300
C5—C61.357 (3)C18—H18A0.9600
C6—C71.405 (3)C18—H18B0.9600
C7—C81.378 (3)C18—H18C0.9600
C8—C181.490 (3)
O1···N92.8930 (19)C14···H5iii3.0900
O1···N9i2.8969 (19)C14···H3A2.6000
O11···C7ii3.383 (3)C15···H3A2.8100
O1···H92.78 (2)C18···H92.90 (2)
O1···H9i2.01 (3)C18···H10i2.9700
O1···H102.3600H3A···C142.6000
N9···O12.8930 (19)H3A···C152.8100
N9···O1i2.8969 (19)H3A···H142.0500
C1···C4Aii3.529 (3)H3B···C4iii3.0300
C2···C8Aii3.577 (2)H3B···H4Aiii2.5700
C3···C143.181 (3)H4A···C2iv2.8900
C4A···C1ii3.529 (3)H4A···C10iv2.8800
C7···O11ii3.383 (3)H4A···H3Biv2.5700
C8···C15ii3.554 (3)H5···C13iv3.0800
C8···C10ii3.482 (3)H5···C14iv3.0900
C8A···C10ii3.545 (3)H6···C7vii2.9100
C8A···C2ii3.577 (2)H6···H7vii2.4600
C8A···C13iii3.550 (3)H7···H18A2.3700
C9A···C9Aii3.595 (2)H7···H6vi2.4600
C10···C8Aii3.545 (3)H9···O12.78 (2)
C10···C8ii3.482 (3)H9···C182.90 (2)
C13···C8Aiv3.550 (3)H9···O1i2.01 (3)
C14···C33.181 (3)H10···O12.3600
C15···C8ii3.554 (3)H10···C18i2.9700
C2···H4Aiii2.8900H10···H18Bi2.5600
C3···H142.7100H13···C6iv3.0800
C4···H3Biv3.0300H13···C7iv2.9600
C4A···H14iii3.0700H13···C8iv2.9600
C5···H18Bv3.0400H13···C8Aiv3.0100
C6···H18Bv3.0700H14···C32.7100
C6···H13iii3.0800H14···H3A2.0500
C7···H6vi2.9100H14···C4Aiv3.0700
C7···H13iii2.9600H14···C9Aiv3.0300
C8···H13iii2.9600H18A···H72.3700
C8A···H13iii3.0100H18B···C5viii3.0400
C9A···H14iii3.0300H18B···C6viii3.0700
C10···H4Aiii2.8800H18B···H10i2.5600
C13···H5iii3.0800
C12—O11—C15106.75 (18)C10—C15—C14133.61 (18)
C8A—N9—C9A107.96 (14)O11—C15—C10117.45 (17)
C9A—N9—H9127.2 (15)O11—C15—C14108.94 (17)
C8A—N9—H9124.8 (15)C2—C3—H3A108.00
O1—C1—C9A121.86 (17)C2—C3—H3B108.00
O1—C1—C2122.69 (15)C4—C3—H3A108.00
C2—C1—C9A115.44 (16)C4—C3—H3B108.00
C3—C2—C10124.13 (16)H3A—C3—H3B107.00
C1—C2—C3119.58 (16)C3—C4—H4A109.00
C1—C2—C10116.23 (15)C3—C4—H4B109.00
C2—C3—C4116.77 (16)C4A—C4—H4A109.00
C3—C4—C4A112.22 (17)C4A—C4—H4B109.00
C4B—C4A—C9A106.75 (16)H4A—C4—H4B108.00
C4—C4A—C4B130.07 (18)C4B—C5—H5121.00
C4—C4A—C9A122.99 (16)C6—C5—H5121.00
C5—C4B—C8A119.49 (17)C5—C6—H6119.00
C4A—C4B—C5133.62 (19)C7—C6—H6119.00
C4A—C4B—C8A106.89 (16)C6—C7—H7118.00
C4B—C5—C6118.1 (2)C8—C7—H7118.00
C5—C6—C7121.4 (2)C2—C10—H10115.00
C6—C7—C8123.2 (2)C15—C10—H10115.00
C7—C8—C8A115.26 (18)O11—C12—H12125.00
C8A—C8—C18121.82 (17)C13—C12—H12125.00
C7—C8—C18122.92 (18)C12—C13—H13126.00
N9—C8A—C8129.29 (17)C14—C13—H13126.00
C4B—C8A—C8122.45 (17)C13—C14—H14126.00
N9—C8A—C4B108.25 (14)C15—C14—H14126.00
C1—C9A—C4A124.50 (17)C8—C18—H18A109.00
N9—C9A—C1125.34 (17)C8—C18—H18B109.00
N9—C9A—C4A110.15 (14)C8—C18—H18C109.00
C2—C10—C15129.69 (17)H18A—C18—H18B109.00
O11—C12—C13110.0 (2)H18A—C18—H18C109.00
C12—C13—C14107.2 (2)H18B—C18—H18C109.00
C13—C14—C15107.15 (18)
C15—O11—C12—C130.0 (3)C9A—C4A—C4B—C8A−0.8 (2)
C12—O11—C15—C10179.89 (19)C4—C4A—C9A—N9−174.75 (17)
C12—O11—C15—C140.2 (2)C4—C4A—C9A—C14.0 (3)
C9A—N9—C8A—C4B−0.28 (19)C4B—C4A—C9A—N90.6 (2)
C9A—N9—C8A—C8178.49 (18)C4B—C4A—C9A—C1179.32 (17)
C8A—N9—C9A—C1−178.91 (17)C4A—C4B—C5—C6179.8 (2)
C8A—N9—C9A—C4A−0.2 (2)C8A—C4B—C5—C6−1.0 (3)
O1—C1—C2—C3−170.47 (17)C4A—C4B—C8A—N90.7 (2)
O1—C1—C2—C107.0 (3)C4A—C4B—C8A—C8−178.22 (17)
C9A—C1—C2—C38.5 (2)C5—C4B—C8A—N9−178.77 (17)
C9A—C1—C2—C10−174.06 (16)C5—C4B—C8A—C82.4 (3)
O1—C1—C9A—N91.6 (3)C4B—C5—C6—C7−0.9 (3)
O1—C1—C9A—C4A−176.90 (18)C5—C6—C7—C81.5 (4)
C2—C1—C9A—N9−177.39 (15)C6—C7—C8—C8A−0.1 (3)
C2—C1—C9A—C4A4.1 (3)C6—C7—C8—C18−179.4 (2)
C1—C2—C3—C4−28.3 (2)C7—C8—C8A—N9179.62 (18)
C10—C2—C3—C4154.45 (18)C7—C8—C8A—C4B−1.8 (3)
C1—C2—C10—C15−176.11 (18)C18—C8—C8A—N9−1.1 (3)
C3—C2—C10—C151.2 (3)C18—C8—C8A—C4B177.53 (18)
C2—C3—C4—C4A33.9 (2)C2—C10—C15—O11−174.38 (19)
C3—C4—C4A—C4B162.79 (19)C2—C10—C15—C145.2 (4)
C3—C4—C4A—C9A−23.0 (3)O11—C12—C13—C14−0.2 (3)
C4—C4A—C4B—C5−6.5 (4)C12—C13—C14—C150.4 (3)
C4—C4A—C4B—C8A174.15 (19)C13—C14—C15—O11−0.4 (2)
C9A—C4A—C4B—C5178.5 (2)C13—C14—C15—C10−180.0 (2)
D—H···AD—HH···AD···AD—H···A
N9—H9···O1i0.89 (3)2.01 (3)2.8969 (19)176 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N9—H9⋯O1i0.89 (3)2.01 (3)2.8969 (19)176 (2)

Symmetry code: (i) .

  5 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 novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens.

Authors:  Govindasami Periyasami; Raghavachary Raghunathan; Gangadharan Surendiran; Narayanasamy Mathivanan
Journal:  Bioorg Med Chem Lett       Date:  2008-03-04       Impact factor: 2.823

4.  Regioselective synthesis and antimicrobial screening of novel ketocarbazolodispiropyrrolidine derivatives.

Authors:  Govindasami Periyasami; Raghavachary Raghunathan; Gangadharan Surendiran; Narayanasamy Mathivanan
Journal:  Eur J Med Chem       Date:  2008-07-18       Impact factor: 6.514

5.  Structure validation in chemical crystallography.

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

1.  (E)-2-[(Furan-2-yl)methyl-idene]-7-methyl-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

Authors:  A Thiruvalluvar; R Archana; E Yamuna; K J Rajendra Prasad; R J Butcher; Sushil K Gupta; Sema Oztürk Yildirim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-01-04

2.  Crystal structure of (E)-2-(furan-2-yl-methyl-idene)-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

Authors:  A Thiruvalluvar; M Sridharan; K J Rajendra Prasad; M Zeller
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-01-01
  2 in total

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