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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Aug 17;67(Pt 9):o2341. doi: 10.1107/S1600536811032107

5-Benzyl-5H-pyrido[3,2-b]indole

Julien Letessier a, Dieter Schollmeyer a, Heiner Detert a,*
PMCID: PMC3200621  PMID: 22058962

Abstract

The title compound, C18H14N2, was prepared by twofold Pd-catalyzed aryl­amination of a cyclic pyrido–benzo–iodo­lium salt. In the crystal, two mol­ecules of 9-benzyl-δ-carboline form centrosymmetrical dimers with distances of 3.651 (2) Å between the centroids of the pyridine rings and 3.961 (2) Å between the centroids of the pyrrole and pyridine rings. The phenyl rings point to the other mol­ecule in the dimer and the carboline core is essentially planar [maximum deviation of 0.027 (2) Å].

Related literature

For δ-Carboline, see: Subbaraju et al. (2004 ▶); Paulo et al. (2000 ▶); Chernyshev et al. (2001 ▶); Namjoshi et al. (2011 ▶); Qu et al. (2009 ▶); Masterova et al. (2008 ▶). For synthetic strategies to carbolines, see: Späth & Eiter (1940 ▶); Sakamoto et al. (1999 ▶); Franck et al. (2008 ▶). For the transition-metal-catalyzed synthesis of carbazoles, see: Letessier (2011 ▶); Nemkovich et al. (2009 ▶). For the transition-metal-catalyzed synthesis of carbolines, see: Nissen et al. (2011 ▶), Dassonneville et al. (2010 ▶). For β-carboline, see: Torreiles et al. (1985 ▶); Love (2006 ▶); Dassonneville et al. (2011 ▶); Nissen & Detert (2011 ▶). For the synthesis of the title compound, see: Letessier & Detert (2011 ▶). graphic file with name e-67-o2341-scheme1.jpg

Experimental

Crystal data

  • C18H14N2

  • M r = 258.1

  • Monoclinic, Inline graphic

  • a = 11.295 (4) Å

  • b = 10.482 (4) Å

  • c = 11.961 (4) Å

  • β = 110.387 (11)°

  • V = 1327.4 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.51 × 0.25 × 0.02 mm

Data collection

  • Bruker SMART CCD diffractometer

  • 15877 measured reflections

  • 3149 independent reflections

  • 1444 reflections with I > 2σ(I)

  • R int = 0.128

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055

  • wR(F 2) = 0.149

  • S = 0.98

  • 3149 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032107/bt5607sup1.cif

e-67-o2341-sup1.cif (18.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032107/bt5607Isup2.hkl

e-67-o2341-Isup2.hkl (154.5KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811032107/bt5607Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to Heinz Kolshorn for invaluable discussions and the NMR spectra.

supplementary crystallographic information

Comment

The title compound was prepared as a part of a project focused on the transition metal catalyzed synthesis of carbazoles, see: Letessier (2011) and Nemkovich et al. (2009), carbolines, see: Nissen, Schollmeyer & Detert (2011) and related indolo-annulated heterocycles, see: Dassonneville et al. (2010). Whereas the β-carboline is the core of a large group of alkaloids (see: Torreiles et al. (1985); Love (2006)), only a few natural δ-carbolines are known. With Rh- or Ru-catalyzed [2 + 2+2] cycloadditions of alkynyl-ynamides we recently reported a new access to β- and γ-carbolines (Dassonneville et al., 2011), Nissen & Detert (2011), but this approach is not suitable for the synthesis of the δ-isomers. These can now be prepared in a twofold Pd-catalyzed arylation of primary amines with cyclic pyrido-benzo iodolium salts. This unique 9-substituted δ-carboline crystallizes in form of centrosymmetrical dimers. The phenyl group, pointing in the direction of the second molecule, is nearly orthogonal to the essentially planar carboline core (maximal deviations of 0.027 (2) Å from the least square plane). Short distances of the centroid of a pyridine ring of one molecule to the centroid of the pyridine of its counterpart of 3.65 Å and to the pyrrole centroid of 3.96 Å indicate a π-π interaction between the heterocycles.

Experimental

A solution of 400 mg (0.93 mmol) of benzo[4,5]iodolo[3,2-b]pyridin-5-ium trifluoromethanesulfonate (Letessier & Detert, 2011) in dry toluene (10 ml) was deaerated in a Schlenk flask. Under argon, Pd2(dba)3 (34 mg, 0.04 mmol), Xantphos (64 mg, 0.11 mmol), and Cs2CO3 (850 mg, 2.61 mmol) were added. The mixture was stirred for 5 min at 300 K before benzyl amine (120 mg, 1.12 mmol) was added. After stirring for 15 h at 383 K, the mixture was cooled to ambient temparature, filtered through celite and concentrated. Purification by column chromatography (petroleum ether / ethyl acetate = 4 / 1) gave 156 mg (65%) of the title compound as colorless crystals with m. p. > 415 K.

Refinement

Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (sp3 C-atom). All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom).

Figures

Fig. 1.

Fig. 1.

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View of compound I. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C18H14N2 F(000) = 544
Mr = 258.1 Dx = 1.293 Mg m−3
Monoclinic, P21/n Melting point: 415 K
Hall symbol: -P 2yn Mo Kα radiation, λ = 0.71073 Å
a = 11.295 (4) Å Cell parameters from 1161 reflections
b = 10.482 (4) Å θ = 2.6–22.3°
c = 11.961 (4) Å µ = 0.08 mm−1
β = 110.387 (11)° T = 173 K
V = 1327.4 (8) Å3 Plate, colourless
Z = 4 0.51 × 0.25 × 0.02 mm
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Data collection

Bruker SMART CCD diffractometer 1444 reflections with I > 2σ(I)
Radiation source: sealed Tube Rint = 0.128
graphite θmax = 27.9°, θmin = 2.1°
CCD scan h = −14→14
15877 measured reflections k = −13→13
3149 independent reflections l = −15→15
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055 H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2129P] where P = (Fo2 + 2Fc2)/3
S = 0.98 (Δ/σ)max < 0.001
3149 reflections Δρmax = 0.22 e Å−3
182 parameters Δρmin = −0.21 e Å−3
0 restraints Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.016 (2)
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Special details

Experimental. 1H-NMR (400 MHz, CDCl3): δ = 8.59 (dd, J = 4.7 Hz, J = 1.2 Hz, 1H, 2-H), 8.43 (d, J = 7.8 Hz, 1H, 9-H), 7.64 (dd, J = 8.2 Hz, J = 1.2 Hz, 1H, 6-H), 7.53 (td, J = 8.3 Hz, J = 1.2 Hz, 1H, 7-H), 7.42 (d, J = 8.2 Hz, 1H, 6-H), 7.26-7.34 (m, 5H, CH), 7.12 (m, 2H, CH), 5.52 (s, 2H, CH2). 13C-NMR (75 MHz, CDCl3): δ = 141.9 (d, C-2), 141.8 (s, C-9b), 141.4 (s, C-5a), 136.5 (s, C-1), 134.0 (s, C-4a), 128.9 (d, C-2), 127.9 (d, C-7), 127.7 (d, C-4), 126.3 (d, C-3), 122.2 (s, C-9a), 120.9 (d, C-3), 120.1 (d, C-9), 120.0 (d, C-8), 115.8 (d, C-4), 109.2 (d, C-6), 46.5 (t, CH2). IR (neat, ATR): ν = 1621 (w), 1588 (w), 1482 (m), 1451 (m), 1412 (s), 1334 (m), 1318 (s), 1242 (w), 1193 (m), 1115 (w), 1012 (w), 913 (w), 845 (m), 781 (s), 742 (vs), 730 (vs), 721 (vs), 695 (s)cm-1. FD-MS: m/z = 258.1 [C18H14N2]+.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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 > σ(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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 0.74211 (17) 0.47469 (18) 0.17200 (17) 0.0360 (5)
C2 0.7372 (2) 0.4852 (2) 0.2855 (2) 0.0334 (6)
C3 0.8208 (2) 0.5471 (2) 0.3853 (2) 0.0410 (6)
H3 0.8945 0.5885 0.3825 0.049*
C4 0.7916 (3) 0.5456 (2) 0.4876 (2) 0.0468 (7)
H4 0.8463 0.5873 0.5568 0.056*
C5 0.6848 (3) 0.4849 (2) 0.4923 (2) 0.0501 (7)
H5 0.6678 0.4861 0.5647 0.060*
C6 0.6034 (2) 0.4233 (2) 0.3955 (2) 0.0424 (7)
H6 0.5304 0.3817 0.3998 0.051*
C7 0.6295 (2) 0.4231 (2) 0.2914 (2) 0.0356 (6)
C8 0.5662 (2) 0.3720 (2) 0.1737 (2) 0.0365 (6)
N9 0.45662 (19) 0.3047 (2) 0.1336 (2) 0.0488 (6)
C10 0.4201 (2) 0.2725 (3) 0.0174 (3) 0.0514 (8)
H10 0.3436 0.2259 −0.0154 0.062*
C11 0.4853 (3) 0.3021 (2) −0.0574 (2) 0.0522 (8)
H11 0.4528 0.2755 −0.1384 0.063*
C12 0.5981 (2) 0.3703 (2) −0.0164 (2) 0.0452 (7)
H12 0.6447 0.3914 −0.0664 0.054*
C13 0.6378 (2) 0.4055 (2) 0.1036 (2) 0.0370 (6)
C14 0.8358 (2) 0.5335 (2) 0.1306 (2) 0.0409 (6)
H14A 0.8610 0.6162 0.1719 0.049*
H14B 0.7963 0.5513 0.0442 0.049*
C15 0.9524 (2) 0.4548 (2) 0.1502 (2) 0.0360 (6)
C16 1.0688 (2) 0.5125 (3) 0.1743 (2) 0.0475 (7)
H16 1.0757 0.6027 0.1820 0.057*
C17 1.1752 (2) 0.4406 (3) 0.1872 (2) 0.0548 (8)
H17 1.2544 0.4817 0.2035 0.066*
C18 1.1675 (3) 0.3100 (3) 0.1769 (2) 0.0583 (8)
H18 1.2407 0.2606 0.1857 0.070*
C19 1.0529 (3) 0.2523 (3) 0.1537 (3) 0.0606 (9)
H19 1.0468 0.1621 0.1471 0.073*
C20 0.9462 (2) 0.3233 (3) 0.1399 (2) 0.0487 (7)
H20 0.8673 0.2815 0.1232 0.058*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0301 (11) 0.0362 (12) 0.0403 (13) −0.0008 (9) 0.0106 (9) 0.0009 (9)
C2 0.0340 (13) 0.0264 (13) 0.0380 (15) 0.0064 (11) 0.0102 (11) 0.0032 (11)
C3 0.0415 (14) 0.0330 (14) 0.0454 (17) −0.0039 (12) 0.0113 (12) 0.0013 (12)
C4 0.0553 (17) 0.0366 (16) 0.0437 (17) −0.0044 (14) 0.0113 (13) −0.0011 (13)
C5 0.0628 (19) 0.0421 (16) 0.0487 (17) 0.0031 (15) 0.0234 (15) 0.0025 (14)
C6 0.0381 (15) 0.0372 (15) 0.0577 (19) 0.0002 (12) 0.0239 (14) 0.0030 (13)
C7 0.0313 (13) 0.0277 (13) 0.0459 (16) 0.0049 (11) 0.0112 (12) 0.0052 (11)
C8 0.0263 (12) 0.0303 (14) 0.0499 (16) 0.0017 (11) 0.0097 (11) 0.0029 (12)
N9 0.0354 (12) 0.0359 (13) 0.0652 (16) 0.0046 (11) 0.0050 (11) 0.0021 (12)
C10 0.0363 (15) 0.0358 (16) 0.066 (2) 0.0038 (12) −0.0024 (15) −0.0015 (14)
C11 0.0535 (18) 0.0396 (17) 0.0447 (17) 0.0077 (15) −0.0066 (14) −0.0034 (13)
C12 0.0494 (16) 0.0372 (15) 0.0442 (17) 0.0081 (13) 0.0102 (13) 0.0032 (12)
C13 0.0295 (13) 0.0314 (14) 0.0440 (16) 0.0058 (11) 0.0050 (12) −0.0006 (12)
C14 0.0408 (14) 0.0394 (15) 0.0438 (16) −0.0017 (12) 0.0161 (12) 0.0034 (12)
C15 0.0353 (14) 0.0397 (15) 0.0324 (14) −0.0023 (12) 0.0112 (11) −0.0013 (11)
C16 0.0444 (16) 0.0535 (17) 0.0422 (16) −0.0130 (14) 0.0123 (13) −0.0050 (13)
C17 0.0344 (15) 0.081 (2) 0.0485 (18) −0.0076 (16) 0.0140 (13) −0.0022 (16)
C18 0.0416 (17) 0.075 (2) 0.061 (2) 0.0133 (17) 0.0214 (14) 0.0001 (17)
C19 0.0534 (19) 0.0505 (19) 0.084 (2) 0.0045 (15) 0.0321 (17) −0.0043 (16)
C20 0.0379 (15) 0.0436 (16) 0.0663 (19) −0.0008 (13) 0.0202 (13) −0.0050 (14)
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Geometric parameters (Å, °)

N1—C2 1.382 (3) C11—C12 1.393 (4)
N1—C13 1.383 (3) C11—H11 0.9500
N1—C14 1.453 (3) C12—C13 1.395 (3)
C2—C3 1.397 (3) C12—H12 0.9500
C2—C7 1.403 (3) C14—C15 1.502 (3)
C3—C4 1.373 (3) C14—H14A 0.9900
C3—H3 0.9500 C14—H14B 0.9900
C4—C5 1.382 (4) C15—C16 1.383 (3)
C4—H4 0.9500 C15—C20 1.384 (3)
C5—C6 1.365 (3) C16—C17 1.380 (4)
C5—H5 0.9500 C16—H16 0.9500
C6—C7 1.376 (3) C17—C18 1.374 (4)
C6—H6 0.9500 C17—H17 0.9500
C7—C8 1.442 (3) C18—C19 1.366 (4)
C8—N9 1.358 (3) C18—H18 0.9500
C8—C13 1.398 (3) C19—C20 1.376 (4)
N9—C10 1.348 (3) C19—H19 0.9500
C10—C11 1.378 (4) C20—H20 0.9500
C10—H10 0.9500
C2—N1—C13 107.80 (19) C11—C12—C13 115.1 (3)
C2—N1—C14 125.75 (19) C11—C12—H12 122.4
C13—N1—C14 126.3 (2) C13—C12—H12 122.4
N1—C2—C3 129.1 (2) N1—C13—C12 130.5 (2)
N1—C2—C7 110.2 (2) N1—C13—C8 109.2 (2)
C3—C2—C7 120.8 (2) C12—C13—C8 120.3 (2)
C4—C3—C2 117.1 (2) N1—C14—C15 114.7 (2)
C4—C3—H3 121.4 N1—C14—H14A 108.6
C2—C3—H3 121.4 C15—C14—H14A 108.6
C3—C4—C5 121.7 (2) N1—C14—H14B 108.6
C3—C4—H4 119.1 C15—C14—H14B 108.6
C5—C4—H4 119.1 H14A—C14—H14B 107.6
C6—C5—C4 121.5 (3) C16—C15—C20 118.0 (2)
C6—C5—H5 119.2 C16—C15—C14 120.7 (2)
C4—C5—H5 119.2 C20—C15—C14 121.2 (2)
C5—C6—C7 118.4 (2) C17—C16—C15 120.7 (3)
C5—C6—H6 120.8 C17—C16—H16 119.6
C7—C6—H6 120.8 C15—C16—H16 119.6
C6—C7—C2 120.5 (2) C18—C17—C16 120.6 (3)
C6—C7—C8 133.9 (2) C18—C17—H17 119.7
C2—C7—C8 105.5 (2) C16—C17—H17 119.7
N9—C8—C13 124.4 (2) C19—C18—C17 119.0 (3)
N9—C8—C7 128.3 (2) C19—C18—H18 120.5
C13—C8—C7 107.4 (2) C17—C18—H18 120.5
C10—N9—C8 114.1 (2) C18—C19—C20 120.9 (3)
N9—C10—C11 124.9 (3) C18—C19—H19 119.6
N9—C10—H10 117.5 C20—C19—H19 119.6
C11—C10—H10 117.5 C19—C20—C15 120.8 (3)
C10—C11—C12 121.1 (3) C19—C20—H20 119.6
C10—C11—H11 119.4 C15—C20—H20 119.6
C12—C11—H11 119.4
C13—N1—C2—C3 −179.4 (2) C10—C11—C12—C13 −0.3 (4)
C14—N1—C2—C3 −3.2 (4) C2—N1—C13—C12 178.9 (2)
C13—N1—C2—C7 −0.1 (2) C14—N1—C13—C12 2.8 (4)
C14—N1—C2—C7 176.1 (2) C2—N1—C13—C8 0.1 (2)
N1—C2—C3—C4 178.4 (2) C14—N1—C13—C8 −176.1 (2)
C7—C2—C3—C4 −0.8 (3) C11—C12—C13—N1 −178.6 (2)
C2—C3—C4—C5 0.4 (4) C11—C12—C13—C8 0.2 (3)
C3—C4—C5—C6 0.2 (4) N9—C8—C13—N1 179.3 (2)
C4—C5—C6—C7 −0.3 (4) C7—C8—C13—N1 0.0 (3)
C5—C6—C7—C2 −0.2 (4) N9—C8—C13—C12 0.3 (4)
C5—C6—C7—C8 −178.6 (2) C7—C8—C13—C12 −179.0 (2)
N1—C2—C7—C6 −178.6 (2) C2—N1—C14—C15 88.4 (3)
C3—C2—C7—C6 0.7 (4) C13—N1—C14—C15 −96.1 (3)
N1—C2—C7—C8 0.1 (2) N1—C14—C15—C16 −146.8 (2)
C3—C2—C7—C8 179.5 (2) N1—C14—C15—C20 35.9 (3)
C6—C7—C8—N9 −0.8 (4) C20—C15—C16—C17 0.2 (4)
C2—C7—C8—N9 −179.3 (2) C14—C15—C16—C17 −177.2 (2)
C6—C7—C8—C13 178.4 (3) C15—C16—C17—C18 −0.3 (4)
C2—C7—C8—C13 −0.1 (2) C16—C17—C18—C19 −0.1 (4)
C13—C8—N9—C10 −0.6 (3) C17—C18—C19—C20 0.5 (4)
C7—C8—N9—C10 178.5 (2) C18—C19—C20—C15 −0.5 (4)
C8—N9—C10—C11 0.5 (4) C16—C15—C20—C19 0.2 (4)
N9—C10—C11—C12 −0.1 (4) C14—C15—C20—C19 177.6 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5607).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032107/bt5607sup1.cif

e-67-o2341-sup1.cif (18.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032107/bt5607Isup2.hkl

e-67-o2341-Isup2.hkl (154.5KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811032107/bt5607Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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