Literature DB >> 21589492

(E)-6-Chloro-2-(furan-2-yl-methyl-idene)-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(17)H(12)ClNO(2), the carbazole unit is nearly planar [maximum deviation = 0.052 (1) Å]. The pyrrole ring makes dihedral angles of 1.92 (8) and 4.71 (11)° with the benzene and furan rings, respectively. Inter-molecular N-H⋯O hydrogen bonds form R(2) (2)(10) rings in the crystal structure.

Entities:  

Year:  2010        PMID： 21589492      PMCID： PMC3011405          DOI： 10.1107/S1600536810046714

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


Related literature

For the pharmaceutical inter­est of heteroaryl annulated derivatives of carbazoles, see: Knölker & Reddy (2002 ▶, 2008 ▶). For the preparation of various hetero-annulated carbazoles, see: Sridharan et al. (2008 ▶); Danish & Rajendra Prasad (2004 ▶, 2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H12ClNO2 M = 297.73 Monoclinic, a = 15.0985 (2) Å b = 6.1553 (1) Å c = 15.3887 (2) Å β = 104.319 (1)° V = 1385.73 (3) Å3 Z = 4 Cu Kα radiation μ = 2.47 mm−1 T = 295 K 0.48 × 0.34 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.389, T max = 1.000 8660 measured reflections 2834 independent reflections 2676 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.139 S = 1.10 2834 reflections 194 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.28 e Å−3 Δρmin = −0.28 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/S1600536810046714/bq2253sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046714/bq2253Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H12ClNO2F(000) = 616
Mr = 297.73Dx = 1.427 Mg m−3
Monoclinic, P21/cMelting point: 501 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54184 Å
a = 15.0985 (2) ÅCell parameters from 6923 reflections
b = 6.1553 (1) Åθ = 4.7–75.4°
c = 15.3887 (2) ŵ = 2.47 mm−1
β = 104.319 (1)°T = 295 K
V = 1385.73 (3) Å3Prism, pale-yellow
Z = 40.48 × 0.34 × 0.12 mm
Oxford Diffraction Xcalibur Ruby Gemini diffractometer2834 independent reflections
Radiation source: Enhance (Cu) X-ray Source2676 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 10.5081 pixels mm-1θmax = 75.6°, θmin = 5.9°
ω scansh = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −5→7
Tmin = 0.389, Tmax = 1.000l = −19→18
8660 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.10w = 1/[σ2(Fo2) + (0.0845P)2 + 0.264P] where P = (Fo2 + 2Fc2)/3
2834 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.28 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
Cl6−0.40900 (3)0.76934 (9)0.02641 (5)0.0804 (2)
O10.10076 (8)0.13185 (18)0.07979 (8)0.0510 (3)
O110.38257 (9)0.4505 (3)0.24198 (10)0.0751 (5)
N9−0.09205 (9)0.2203 (2)0.03653 (8)0.0441 (4)
C10.07175 (10)0.2982 (2)0.10858 (9)0.0376 (4)
C20.13341 (10)0.4564 (2)0.16694 (8)0.0383 (4)
C30.09534 (11)0.6580 (2)0.20028 (10)0.0457 (4)
C4−0.00564 (12)0.7036 (3)0.17066 (13)0.0560 (5)
C4A−0.06155 (10)0.5338 (2)0.11436 (8)0.0373 (4)
C4B−0.15750 (10)0.5216 (2)0.07663 (9)0.0394 (4)
C5−0.23081 (11)0.6625 (3)0.07672 (10)0.0476 (5)
C6−0.31602 (11)0.5984 (3)0.02964 (12)0.0535 (5)
C7−0.33227 (11)0.3997 (3)−0.01636 (12)0.0559 (5)
C8−0.26184 (12)0.2604 (3)−0.01737 (11)0.0524 (5)
C8A−0.17369 (10)0.3230 (3)0.02874 (9)0.0420 (4)
C9A−0.02410 (10)0.3493 (2)0.08760 (8)0.0374 (4)
C100.22300 (11)0.4106 (3)0.18622 (10)0.0463 (4)
C120.44470 (14)0.5930 (5)0.28938 (17)0.0812 (8)
C130.40378 (15)0.7606 (4)0.31507 (16)0.0731 (7)
C140.30864 (14)0.7275 (3)0.28188 (14)0.0621 (6)
C150.29763 (11)0.5361 (3)0.23740 (10)0.0496 (5)
H3A0.126890.781950.183100.0548*
H3B0.111730.652440.265290.0548*
H4A−0.014360.839060.137420.0672*
H4B−0.028550.724420.223660.0672*
H5−0.221780.793800.107520.0571*
H7−0.391590.36229−0.046500.0671*
H8−0.272260.12849−0.047690.0629*
H9−0.0853 (14)0.102 (4)0.0073 (14)0.060 (5)*
H100.238670.280200.163360.0556*
H120.507730.574470.301940.0974*
H130.431900.878460.348650.0877*
H140.262370.820100.289280.0746*
U11U22U33U12U13U23
Cl60.0463 (3)0.0751 (4)0.1142 (5)0.0130 (2)0.0090 (3)0.0023 (3)
O10.0491 (6)0.0413 (6)0.0619 (6)0.0001 (4)0.0123 (5)−0.0157 (5)
O110.0436 (7)0.0848 (10)0.0917 (10)0.0015 (6)0.0071 (6)−0.0262 (8)
N90.0461 (7)0.0415 (6)0.0439 (6)−0.0039 (5)0.0094 (5)−0.0113 (5)
C10.0457 (8)0.0334 (6)0.0347 (6)−0.0031 (5)0.0121 (5)−0.0023 (5)
C20.0441 (7)0.0355 (7)0.0357 (6)−0.0033 (5)0.0106 (5)−0.0015 (5)
C30.0483 (8)0.0383 (7)0.0485 (8)−0.0044 (6)0.0084 (6)−0.0116 (6)
C40.0495 (9)0.0438 (8)0.0696 (10)0.0021 (7)0.0049 (8)−0.0228 (7)
C4A0.0427 (7)0.0362 (7)0.0326 (6)−0.0011 (5)0.0088 (5)0.0002 (5)
C4B0.0432 (7)0.0401 (7)0.0348 (6)−0.0018 (5)0.0094 (5)0.0009 (5)
C50.0476 (8)0.0445 (8)0.0502 (8)0.0019 (6)0.0113 (6)−0.0001 (6)
C60.0438 (8)0.0574 (9)0.0578 (9)0.0045 (7)0.0097 (7)0.0074 (7)
C70.0424 (8)0.0650 (10)0.0563 (9)−0.0074 (7)0.0044 (7)−0.0001 (8)
C80.0491 (9)0.0553 (9)0.0501 (8)−0.0104 (7)0.0070 (7)−0.0082 (7)
C8A0.0445 (8)0.0439 (7)0.0372 (6)−0.0037 (6)0.0093 (5)−0.0017 (5)
C9A0.0449 (7)0.0358 (7)0.0316 (6)−0.0045 (5)0.0094 (5)−0.0030 (5)
C100.0467 (8)0.0452 (8)0.0473 (7)−0.0023 (6)0.0120 (6)−0.0080 (6)
C120.0431 (9)0.1089 (19)0.0868 (14)−0.0143 (11)0.0071 (9)−0.0239 (14)
C130.0570 (11)0.0854 (14)0.0749 (12)−0.0234 (10)0.0127 (9)−0.0238 (11)
C140.0527 (10)0.0670 (11)0.0673 (10)−0.0102 (8)0.0160 (8)−0.0205 (9)
C150.0418 (8)0.0585 (9)0.0484 (8)−0.0023 (7)0.0112 (6)−0.0053 (7)
Cl6—C61.7452 (18)C6—C71.404 (3)
O1—C11.2380 (17)C7—C81.369 (3)
O11—C121.358 (3)C8—C8A1.399 (2)
O11—C151.372 (2)C10—C151.431 (2)
N9—C8A1.364 (2)C12—C131.313 (4)
N9—C9A1.3791 (19)C13—C141.415 (3)
N9—H90.88 (2)C14—C151.352 (3)
C1—C9A1.438 (2)C3—H3A0.9700
C1—C21.4859 (19)C3—H3B0.9700
C2—C31.5098 (19)C4—H4A0.9700
C2—C101.341 (2)C4—H4B0.9700
C3—C41.506 (3)C5—H50.9300
C4—C4A1.481 (2)C7—H70.9300
C4A—C4B1.423 (2)C8—H80.9300
C4A—C9A1.3763 (18)C10—H100.9300
C4B—C8A1.417 (2)C12—H120.9300
C4B—C51.407 (2)C13—H130.9300
C5—C61.369 (2)C14—H140.9300
Cl6···C12i3.613 (3)C3···H142.7400
O1···N92.8733 (19)C5···H14v3.0700
O1···N9ii2.7935 (17)C9A···H4Bv2.9200
O1···H3Aiii2.6500C14···H3A2.8100
O1···H92.76 (2)C14···H3B2.9600
O1···H102.3400C15···H3B3.0300
O1···H4Aiii2.8000C15···H3A2.9300
O1···H9ii1.94 (2)H3A···O1vi2.6500
N9···O12.8733 (19)H3A···C142.8100
N9···O1ii2.7935 (17)H3A···C152.9300
N9···H4Aiii2.9000H3A···H142.2900
C1···C4Aiv3.5499 (18)H3B···C142.9600
C1···C4Biv3.585 (2)H3B···C153.0300
C2···C8Aiv3.4910 (19)H3B···H142.4400
C3···C143.183 (3)H4A···O1vi2.8000
C4A···C1iv3.5499 (18)H4A···N9vi2.9000
C4B···C1iv3.585 (2)H4A···H9vi2.5900
C7···C15iv3.589 (2)H4B···C1i2.8500
C8···C10iv3.457 (2)H4B···C2i2.9500
C8···C15iv3.524 (2)H4B···C9Ai2.9200
C8A···C2iv3.4910 (19)H9···O12.76 (2)
C9A···C9Aiv3.4944 (18)H9···H4Aiii2.5900
C10···C8iv3.457 (2)H9···O1ii1.94 (2)
C12···Cl6v3.613 (3)H9···C1ii3.08 (2)
C14···C33.183 (3)H10···O12.3400
C15···C8iv3.524 (2)H14···C32.7400
C15···C7iv3.589 (2)H14···H3A2.2900
C1···H4Bv2.8500H14···H3B2.4400
C1···H9ii3.08 (2)H14···C5i3.0700
C2···H4Bv2.9500
C12—O11—C15107.00 (18)O11—C12—C13110.8 (2)
C8A—N9—C9A108.18 (12)C12—C13—C14106.8 (2)
C9A—N9—H9127.4 (14)C13—C14—C15107.15 (18)
C8A—N9—H9123.9 (14)C10—C15—C14136.93 (18)
O1—C1—C9A121.75 (13)O11—C15—C10114.82 (16)
O1—C1—C2122.28 (14)O11—C15—C14108.20 (16)
C2—C1—C9A115.97 (11)C2—C3—H3A107.00
C3—C2—C10123.06 (13)C2—C3—H3B107.00
C1—C2—C3120.65 (13)C4—C3—H3A107.00
C1—C2—C10116.28 (13)C4—C3—H3B107.00
C2—C3—C4119.50 (13)H3A—C3—H3B107.00
C3—C4—C4A115.69 (14)C3—C4—H4A108.00
C4B—C4A—C9A106.65 (11)C3—C4—H4B108.00
C4—C4A—C4B130.64 (13)C4A—C4—H4A108.00
C4—C4A—C9A122.71 (14)C4A—C4—H4B108.00
C5—C4B—C8A119.86 (14)H4A—C4—H4B107.00
C4A—C4B—C5133.55 (13)C4B—C5—H5121.00
C4A—C4B—C8A106.56 (12)C6—C5—H5121.00
C4B—C5—C6117.29 (16)C6—C7—H7120.00
C5—C6—C7122.82 (16)C8—C7—H7120.00
Cl6—C6—C5119.03 (14)C7—C8—H8121.00
Cl6—C6—C7118.15 (13)C8A—C8—H8121.00
C6—C7—C8120.79 (16)C2—C10—H10116.00
C7—C8—C8A117.78 (16)C15—C10—H10116.00
N9—C8A—C8130.00 (16)O11—C12—H12125.00
C4B—C8A—C8121.44 (15)C13—C12—H12125.00
N9—C8A—C4B108.55 (13)C12—C13—H13127.00
C1—C9A—C4A125.36 (12)C14—C13—H13127.00
N9—C9A—C1124.59 (12)C13—C14—H14126.00
N9—C9A—C4A110.05 (13)C15—C14—H14126.00
C2—C10—C15128.47 (16)
C15—O11—C12—C130.5 (3)C9A—C4A—C4B—C8A0.88 (15)
C12—O11—C15—C10177.58 (17)C4—C4A—C9A—N9179.63 (13)
C12—O11—C15—C14−0.2 (2)C4—C4A—C9A—C1−1.0 (2)
C9A—N9—C8A—C4B−0.48 (16)C4B—C4A—C9A—N9−1.21 (15)
C9A—N9—C8A—C8178.81 (16)C4B—C4A—C9A—C1178.14 (12)
C8A—N9—C9A—C1−178.29 (13)C4A—C4B—C5—C6177.85 (15)
C8A—N9—C9A—C4A1.07 (15)C8A—C4B—C5—C60.2 (2)
O1—C1—C2—C3179.69 (13)C4A—C4B—C8A—N9−0.25 (16)
O1—C1—C2—C100.7 (2)C4A—C4B—C8A—C8−179.62 (14)
C9A—C1—C2—C3−0.52 (18)C5—C4B—C8A—N9177.96 (13)
C9A—C1—C2—C10−179.50 (13)C5—C4B—C8A—C8−1.4 (2)
O1—C1—C9A—N91.5 (2)C4B—C5—C6—Cl6−179.12 (12)
O1—C1—C9A—C4A−177.73 (13)C4B—C5—C6—C71.1 (3)
C2—C1—C9A—N9−178.27 (12)Cl6—C6—C7—C8179.00 (14)
C2—C1—C9A—C4A2.48 (19)C5—C6—C7—C8−1.2 (3)
C1—C2—C3—C4−2.7 (2)C6—C7—C8—C8A−0.1 (3)
C10—C2—C3—C4176.20 (15)C7—C8—C8A—N9−177.91 (16)
C1—C2—C10—C15177.45 (15)C7—C8—C8A—C4B1.3 (2)
C3—C2—C10—C15−1.5 (2)C2—C10—C15—O11−177.11 (16)
C2—C3—C4—C4A4.0 (2)C2—C10—C15—C14−0.1 (3)
C3—C4—C4A—C4B178.72 (14)O11—C12—C13—C14−0.5 (3)
C3—C4—C4A—C9A−2.3 (2)C12—C13—C14—C150.4 (3)
C4—C4A—C4B—C52.1 (3)C13—C14—C15—O11−0.1 (2)
C4—C4A—C4B—C8A179.97 (15)C13—C14—C15—C10−177.2 (2)
C9A—C4A—C4B—C5−176.98 (15)
D—H···AD—HH···AD···AD—H···A
N9—H9···O1ii0.88 (2)1.94 (2)2.7935 (17)164 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N9—H9⋯O1i0.88 (2)1.94 (2)2.7935 (17)164 (2)

Symmetry code: (i) .

  3 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.  Structure validation in chemical crystallography.

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

1.  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
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.