Literature DB >> 21587930

2-(2,3,4,9-Tetra-hydro-1H-carbazol-1-ylidene)propane-dinitrile.

R Archana, K Prabakaran, K J Rajendra Prasad, A Thiruvalluvar, R J Butcher.   

Abstract

In the title mol-ecule, C(15)H(11)N(3), the dihedral angle between the benzene ring and the fused pyrrole ring is 1.07 (5)°. The cyclo-hexene ring adopts an envelope conformation: the dicyano-methyl-ene group at position 1 has a coplanar orientation. An intra-molecular N-H⋯N hydrogen bond generates an S(7) ring motif. Inter-molecular N-H⋯N hydrogen bonds form an R(2) (2)(14) ring in the crystal. A C-H⋯π inter-action involving the benzene ring is also found in the structure.

Entities:  

Year:  2010        PMID： 21587930      PMCID： PMC3006716          DOI： 10.1107/S1600536810022671

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


Related literature

For naturally occurring carbazole alkaloids see: Scott et al. (2006 ▶). For the biological activity of carbazole alkaloids see: Ramsewak et al.(1999 ▶); Tachibana et al. (2001 ▶); Nakahara et al. (2002 ▶). For the crystal structures of substituted carbazole derivatives see: Gunaseelan et al. (2007a ▶,b ▶, 2009 ▶); Thiruvalluvar et al. (2007 ▶); Sridharan et al. (2008 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11N3 M = 233.27 Monoclinic, a = 8.4794 (3) Å b = 10.5542 (4) Å c = 13.0575 (5) Å β = 97.366 (3)° V = 1158.92 (8) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 110 K 0.53 × 0.38 × 0.31 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.939, T max = 1.000 8311 measured reflections 3822 independent reflections 2854 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.115 S = 0.98 3822 reflections 167 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.40 e Å−3 Δρmin = −0.24 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/S1600536810022671/dn2576sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022671/dn2576Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H11N3F(000) = 488
Mr = 233.27Dx = 1.337 Mg m−3
Monoclinic, P21/nMelting point: 470 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.4794 (3) ÅCell parameters from 4130 reflections
b = 10.5542 (4) Åθ = 4.7–32.6°
c = 13.0575 (5) ŵ = 0.08 mm−1
β = 97.366 (3)°T = 110 K
V = 1158.92 (8) Å3Prism, pale-yellow
Z = 40.53 × 0.38 × 0.31 mm
Oxford Diffraction Xcalibur Ruby Gemini diffractometer3822 independent reflections
Radiation source: Enhance (Mo) X-ray Source2854 reflections with I > 2σ(I)
graphiteRint = 0.021
Detector resolution: 10.5081 pixels mm-1θmax = 32.6°, θmin = 4.7°
ω scansh = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −15→15
Tmin = 0.939, Tmax = 1.000l = −19→16
8311 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0736P)2] where P = (Fo2 + 2Fc2)/3
3822 reflections(Δ/σ)max = 0.001
167 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.24 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
N90.20402 (9)0.52842 (7)0.07142 (6)0.0170 (2)
N120.27359 (12)0.01410 (9)−0.03875 (8)0.0333 (3)
N130.42310 (11)0.40137 (9)−0.08917 (7)0.0351 (3)
C10.14687 (10)0.29269 (9)0.07178 (6)0.0152 (2)
C20.05668 (11)0.19571 (9)0.12634 (7)0.0194 (2)
C3−0.09527 (10)0.24541 (10)0.16360 (7)0.0219 (3)
C4−0.06619 (11)0.36476 (10)0.22890 (7)0.0212 (3)
C4A0.03186 (10)0.45589 (9)0.17735 (6)0.0166 (2)
C4B0.04943 (10)0.58875 (9)0.19177 (7)0.0179 (2)
C5−0.01638 (11)0.67652 (10)0.25578 (8)0.0238 (3)
C60.02314 (12)0.80254 (10)0.24880 (8)0.0275 (3)
C70.12868 (12)0.84267 (10)0.18004 (8)0.0264 (3)
C80.19716 (11)0.75911 (9)0.11745 (7)0.0221 (2)
C8A0.15696 (10)0.63122 (9)0.12427 (7)0.0173 (2)
C9A0.12894 (10)0.42084 (8)0.10364 (6)0.0151 (2)
C110.24383 (10)0.25207 (9)0.00157 (7)0.0178 (2)
C120.25910 (11)0.12004 (10)−0.02084 (7)0.0222 (3)
C130.34255 (11)0.33496 (10)−0.04916 (7)0.0226 (2)
H2A0.127680.162850.186580.0232*
H2B0.028720.123770.078800.0232*
H3A−0.174570.264020.103010.0262*
H3B−0.140070.178880.204850.0262*
H4A−0.169180.404350.238350.0255*
H4B−0.010560.342460.297870.0255*
H5−0.086400.649360.302660.0286*
H6−0.021150.863130.290740.0330*
H70.153430.930250.176730.0317*
H80.268480.787270.071760.0265*
H90.2890 (16)0.5317 (13)0.0351 (11)0.043 (4)*
U11U22U33U12U13U23
N90.0188 (3)0.0158 (4)0.0172 (3)−0.0019 (3)0.0052 (3)−0.0004 (3)
N120.0414 (5)0.0225 (4)0.0389 (5)−0.0017 (4)0.0158 (4)−0.0055 (4)
N130.0396 (5)0.0323 (5)0.0383 (5)−0.0131 (4)0.0240 (4)−0.0134 (4)
C10.0148 (4)0.0166 (4)0.0140 (4)−0.0015 (3)0.0007 (3)0.0009 (3)
C20.0228 (4)0.0177 (4)0.0181 (4)−0.0047 (3)0.0046 (3)0.0012 (4)
C30.0198 (4)0.0262 (5)0.0205 (4)−0.0062 (4)0.0057 (3)0.0006 (4)
C40.0185 (4)0.0271 (5)0.0194 (4)−0.0021 (4)0.0074 (3)−0.0002 (4)
C4A0.0144 (4)0.0204 (4)0.0149 (4)0.0006 (3)0.0018 (3)0.0004 (3)
C4B0.0149 (4)0.0208 (4)0.0176 (4)0.0022 (3)0.0002 (3)−0.0015 (4)
C50.0179 (4)0.0290 (5)0.0240 (4)0.0059 (4)0.0007 (3)−0.0076 (4)
C60.0250 (5)0.0263 (5)0.0293 (5)0.0096 (4)−0.0040 (4)−0.0107 (4)
C70.0292 (5)0.0179 (4)0.0290 (5)0.0037 (4)−0.0081 (4)−0.0037 (4)
C80.0255 (4)0.0175 (4)0.0218 (4)−0.0003 (4)−0.0028 (3)0.0007 (4)
C8A0.0181 (4)0.0169 (4)0.0160 (4)0.0014 (3)−0.0013 (3)−0.0009 (3)
C9A0.0153 (4)0.0157 (4)0.0143 (4)−0.0015 (3)0.0023 (3)0.0013 (3)
C110.0189 (4)0.0166 (4)0.0183 (4)−0.0025 (3)0.0044 (3)−0.0026 (3)
C120.0238 (4)0.0220 (5)0.0219 (4)−0.0014 (4)0.0067 (3)−0.0026 (4)
C130.0236 (4)0.0221 (4)0.0238 (4)−0.0037 (4)0.0097 (4)−0.0081 (4)
N9—C8A1.3723 (12)C6—C71.4115 (15)
N9—C9A1.3929 (11)C7—C81.3801 (14)
N12—C121.1521 (14)C8—C8A1.3978 (13)
N13—C131.1499 (14)C11—C121.4331 (14)
N9—H90.913 (14)C11—C131.4307 (13)
C1—C21.5099 (13)C2—H2A0.9900
C1—C111.3760 (12)C2—H2B0.9900
C1—C9A1.4289 (13)C3—H3A0.9900
C2—C31.5273 (13)C3—H3B0.9900
C3—C41.5234 (14)C4—H4A0.9900
C4—C4A1.4876 (13)C4—H4B0.9900
C4A—C9A1.3943 (12)C5—H50.9500
C4A—C4B1.4201 (13)C6—H60.9500
C4B—C51.4099 (14)C7—H70.9500
C4B—C8A1.4196 (13)C8—H80.9500
C5—C61.3775 (15)
N9···N133.2626 (12)C8A···H2Avii2.9000
N9···C132.9158 (13)C9A···H3A3.0600
N9···N13i3.2267 (12)C11···H93.001 (14)
N9···C9Aii3.4392 (11)C12···H2A3.0900
N12···C3iii3.4371 (14)C12···H2B2.4800
N13···N93.2626 (12)C13···H92.420 (14)
N13···N9i3.2267 (12)H2A···C123.0900
N13···N13i3.2679 (13)H2A···H7iv2.4700
N12···H2Biii2.9400H2A···C4Bvi3.0800
N12···H8iv2.8000H2A···C8vi2.9700
N13···H92.508 (14)H2A···C8Avi2.9000
N13···H9i2.553 (14)H2B···C122.4800
N13···H3Bv2.8100H2B···H7iv2.5600
C1···C6vi3.4129 (13)H2B···N12iii2.9400
C1···C7vi3.5806 (13)H3A···C9A3.0600
C1···C8Aii3.4849 (12)H3A···C8ii2.8700
C3···N12iii3.4371 (14)H3A···H8ii2.3800
C4A···C7vi3.4360 (13)H3B···C5viii3.0200
C6···C9Avii3.5380 (13)H3B···H5viii2.3300
C6···C1vii3.4129 (13)H3B···N13x2.8100
C7···C9Avii3.3756 (13)H4B···C8vi2.8800
C7···C1vii3.5806 (13)H4B···H8vi2.5600
C7···C4Avii3.4360 (13)H5···C3ix2.9700
C8A···C1ii3.4849 (12)H5···H3Bix2.3300
C9A···N9ii3.4392 (11)H7···C2xi2.9700
C9A···C6vi3.5380 (13)H7···H2Axi2.4700
C9A···C7vi3.3756 (13)H7···H2Bxi2.5600
C13···N92.9158 (13)H7···C4Avii3.0900
C2···H7iv2.9700H8···N12xi2.8000
C3···H5viii2.9700H8···H4Bvii2.5600
C4A···H7vi3.0900H8···H3Aii2.3800
C4B···H2Avii3.0800H9···N132.508 (14)
C5···H3Bix3.0200H9···C113.001 (14)
C8···H3Aii2.8700H9···C132.420 (14)
C8···H2Avii2.9700H9···N13i2.553 (14)
C8···H4Bvii2.8800
C8A—N9—C9A108.60 (7)C12—C11—C13115.24 (8)
C9A—N9—H9127.6 (9)N12—C12—C11179.07 (10)
C8A—N9—H9122.1 (9)N13—C13—C11179.33 (10)
C2—C1—C11119.03 (8)C1—C2—H2A109.00
C2—C1—C9A115.16 (7)C1—C2—H2B109.00
C9A—C1—C11125.72 (8)C3—C2—H2A109.00
C1—C2—C3114.61 (8)C3—C2—H2B109.00
C2—C3—C4112.31 (8)H2A—C2—H2B108.00
C3—C4—C4A109.95 (7)C2—C3—H3A109.00
C4—C4A—C9A123.68 (8)C2—C3—H3B109.00
C4B—C4A—C9A107.00 (8)C4—C3—H3A109.00
C4—C4A—C4B129.32 (8)C4—C3—H3B109.00
C5—C4B—C8A119.68 (9)H3A—C3—H3B108.00
C4A—C4B—C5133.21 (8)C3—C4—H4A110.00
C4A—C4B—C8A107.11 (8)C3—C4—H4B110.00
C4B—C5—C6118.49 (9)C4A—C4—H4A110.00
C5—C6—C7120.75 (10)C4A—C4—H4B110.00
C6—C7—C8122.29 (10)H4A—C4—H4B108.00
C7—C8—C8A117.05 (9)C4B—C5—H5121.00
N9—C8A—C4B108.30 (8)C6—C5—H5121.00
N9—C8A—C8129.97 (8)C5—C6—H6120.00
C4B—C8A—C8121.72 (8)C7—C6—H6120.00
N9—C9A—C1127.87 (8)C6—C7—H7119.00
C1—C9A—C4A123.12 (8)C8—C7—H7119.00
N9—C9A—C4A108.99 (8)C7—C8—H8121.00
C1—C11—C13123.57 (9)C8A—C8—H8121.00
C1—C11—C12121.09 (8)
C9A—N9—C8A—C4B−0.03 (12)C4—C4A—C4B—C8A179.76 (8)
C9A—N9—C8A—C8−178.67 (9)C9A—C4A—C4B—C5−179.41 (10)
C8A—N9—C9A—C1−177.78 (8)C9A—C4A—C4B—C8A0.72 (10)
C8A—N9—C9A—C4A0.48 (10)C4—C4A—C9A—N9−179.85 (8)
C9A—C1—C2—C328.90 (11)C4—C4A—C9A—C1−1.49 (13)
C11—C1—C2—C3−154.52 (8)C4B—C4A—C9A—N9−0.75 (9)
C2—C1—C9A—N9176.14 (8)C4B—C4A—C9A—C1177.62 (8)
C2—C1—C9A—C4A−1.90 (12)C4A—C4B—C5—C6−178.23 (10)
C11—C1—C9A—N9−0.17 (14)C8A—C4B—C5—C61.62 (14)
C11—C1—C9A—C4A−178.21 (8)C4A—C4B—C8A—N9−0.44 (10)
C2—C1—C11—C120.52 (13)C4A—C4B—C8A—C8178.34 (8)
C2—C1—C11—C13−175.65 (8)C5—C4B—C8A—N9179.67 (8)
C9A—C1—C11—C12176.71 (8)C5—C4B—C8A—C8−1.55 (14)
C9A—C1—C11—C130.54 (14)C4B—C5—C6—C7−0.78 (15)
C1—C2—C3—C4−52.67 (10)C5—C6—C7—C8−0.22 (16)
C2—C3—C4—C4A46.84 (10)C6—C7—C8—C8A0.34 (15)
C3—C4—C4A—C4B159.52 (9)C7—C8—C8A—N9179.04 (9)
C3—C4—C4A—C9A−21.59 (12)C7—C8—C8A—C4B0.55 (14)
C4—C4A—C4B—C5−0.37 (17)
Cg1 is the centroid of the C4B,C5–C8,C8A ring.
D—H···AD—HH···AD···AD—H···A
N9—H9···N130.913 (14)2.508 (14)3.2626 (12)140.3 (11)
N9—H9···N13i0.913 (14)2.553 (14)3.2267 (12)131.1 (11)
C2—H2A···Cg1vi0.992.793.6244 (10)142
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4B,C5–C8,C8A ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N9—H9⋯N130.913 (14)2.508 (14)3.2626 (12)140.3 (11)
N9—H9⋯N13i0.913 (14)2.553 (14)3.2267 (12)131.1 (11)
C2—H2A⋯Cg1ii0.992.793.6244 (10)142

Symmetry codes: (i) ; (ii) .

  7 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.  Antioxidative activity of carbazoles from Murraya koenigii leaves.

Authors:  Y Tachibana; H Kikuzaki; N H Lajis; N Nakatani
Journal:  J Agric Food Chem       Date:  2001-11       Impact factor: 5.279

3.  Biologically active carbazole alkaloids from Murraya koenigii.

Authors:  R S Ramsewak; M G Nair; G M Strasburg; D L DeWitt; J L Nitiss
Journal:  J Agric Food Chem       Date:  1999-02       Impact factor: 5.279

4.  Antimutagenicity of some edible Thai plants, and a bioactive carbazole alkaloid, mahanine, isolated from Micromelum minutum.

Authors:  Kazuhiko Nakahara; Gassinee Trakoontivakorn; Najeeb S Alzoreky; Hiroshi Ono; Mayumi Onishi-Kameyama; Mitsuru Yoshida
Journal:  J Agric Food Chem       Date:  2002-08-14       Impact factor: 5.279

5.  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

6.  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

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  9-p-Tolyl-9H-carbazole-3-carbonitrile.

Authors:  C Ramathilagam; N Venkatesan; P Rajakumar; P R Umarani; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-30
  1 in total

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