organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-Benzyl-3-(1,2-di­phenyl­ethen­yl)-1H-indole

aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India, and bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India
*Correspondence e-mail: mnizam_new@yahoo.in

(Received 7 August 2010; accepted 28 August 2010; online 4 September 2010)

In the title compound, C29H23N, the planar [maximum deviation from the least squares plane = 0.056 (1) Å] indole ring makes dihedral angles of 83.4 (4), 69.9 (1) and 59.9 (1)°, with the least-squares planes of three benzene rings. The mol­ecular packing is stabilized by weak inter­molecular C—H⋯π inter­actions.

Related literature

For applications of heteroarenes, see: Dyker (1999[Dyker, G. (1999). Angew Chem. Int. Ed. 38, 1698-1712.]); Ritleng et al. (2002[Ritleng, V., Sirlin, C. & Pfeffer, M. (2002). Chem. Rev. 102, 1731-1769.]). For their pharmaceutical properties and for related reactions, see: Sundberg (1996[Sundberg, R. J. (1996). Indoles. London: Academic Press.]); Ferrer et al. 2007[Ferrer, C., Amijs, C. H. M. & Echavarren, A. M. (2007). Chem. Eur. J. pp. 1358-1373.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C29H23N

  • Mr = 385.48

  • Monoclinic, P 21 /n

  • a = 9.6513 (7) Å

  • b = 11.1857 (10) Å

  • c = 20.0026 (14) Å

  • β = 101.636 (4)°

  • V = 2115.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 298 K

  • 0.22 × 0.19 × 0.16 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.985, Tmax = 0.989

  • 14333 measured reflections

  • 4736 independent reflections

  • 1944 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.164

  • S = 0.96

  • 4736 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1/C2/C3/C8 and C17–C22 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9BCg1i 0.97 2.79 3.619 (3) 144
C28—H28⋯Cg2ii 0.93 2.92 3.830 (3) 165
Symmetry codes: (i) -x+2, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.])'.

Supporting information


Comment top

Development of heteroarene functionalization are useful applications such as fluorescent dyes, synthetic analogues of natural products, and pharmaceuticals (Ritleng et al., 2002; Dyker, 1999). The indole ring system exists ubiquitously in natural products, and exhibits important biological and pharmaceutical properties (Sundberg et al., 1996). A systematic investigation on the gold-catalyzed intra- and intermolecular addition of indoles to alkynes is reported (Ferrer et al., 2007). Against this background the structure of the title compound, C29H23N, is determined.

In the title compound, the indole ring is planar, the maximum deviation from the least squares plane being 0.056 (1)Å for atom C3 (Fig. 1). All bond lengths and angles are within normal ranges (Allen et al., 1987). The sum of bond angles around N1 is 350.8 (2)°, indicating sp2 hybridization. The dihedral angle formed by the least squares planes of the indole ring and the three benzene rings is 83.4 (4)° (C10—C15), 69.9 (0)° (C17–C21) and 59.9 (0)° (C24–C29), respectively. The dihedral angle between benzene rings C10—C15 vs C17–C21 and rings C10—C15 vs C24–C29 is 36.7 (6)°. The molecular packing is stabilized by weak intermolecular C—H···Cg π-ring interactions (Table 1).

Related literature top

For applications of heteroarenes, see: Dyker (1999); Ritleng et al. (2002). For their pharmaceutical properties and for related reactions, see: Sundberg et al. (1996); Ferrer et al. 2007). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of diphenylacetylene (2.4 mmol),1-benzyl indole (2 mmol), indium tribromide (0.2 mmol) in toluene (4 ml) was stirred at 383° K for 2 hr. After completion of the reaction as indicated by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (Merck,100–200 mesh) to afford the desired product after crystallization.

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93–0.98 Å and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, C29H23N, with the atom numbering scheme and 50% probability displacement ellipsoids. H atoms are presented as a small spheres of arbitrary radius.
1-Benzyl-3-(1,2-diphenylethenyl)-1H-indole top
Crystal data top
C29H23NF(000) = 816
Mr = 385.48Dx = 1.211 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1467 reflections
a = 9.6513 (7) Åθ = 2.6–20.8°
b = 11.1857 (10) ŵ = 0.07 mm1
c = 20.0026 (14) ÅT = 298 K
β = 101.636 (4)°Block, colourless
V = 2115.0 (3) Å30.22 × 0.19 × 0.16 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4736 independent reflections
Radiation source: fine-focus sealed tube1944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ω and ϕ scanθmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1211
Tmin = 0.985, Tmax = 0.989k = 1313
14333 measured reflectionsl = 2520
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.069P)2]
where P = (Fo2 + 2Fc2)/3
4736 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C29H23NV = 2115.0 (3) Å3
Mr = 385.48Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6513 (7) ŵ = 0.07 mm1
b = 11.1857 (10) ÅT = 298 K
c = 20.0026 (14) Å0.22 × 0.19 × 0.16 mm
β = 101.636 (4)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4736 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
1944 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.989Rint = 0.057
14333 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 0.96Δρmax = 0.15 e Å3
4736 reflectionsΔρmin = 0.17 e Å3
271 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8730 (2)0.1329 (2)0.39886 (12)0.0542 (7)
H10.90180.12470.35740.065*
C20.7345 (2)0.1302 (2)0.40656 (12)0.0491 (6)
C30.7395 (2)0.1442 (2)0.47796 (11)0.0491 (6)
C40.6392 (3)0.1373 (3)0.51975 (13)0.0663 (8)
H40.54400.12600.50060.080*
C50.6829 (3)0.1474 (3)0.58865 (14)0.0832 (9)
H50.61590.14370.61610.100*
C60.8239 (3)0.1629 (3)0.61903 (14)0.0806 (9)
H60.84940.17120.66620.097*
C70.9262 (3)0.1662 (2)0.58053 (13)0.0659 (8)
H71.02130.17470.60060.079*
C80.8821 (2)0.1563 (2)0.51037 (12)0.0503 (6)
C91.1159 (2)0.1514 (2)0.47240 (13)0.0592 (7)
H9A1.14580.12220.43190.071*
H9B1.15240.09670.50940.071*
C101.1807 (2)0.2726 (2)0.49003 (12)0.0499 (6)
C111.3105 (2)0.2806 (3)0.53319 (12)0.0631 (7)
H111.35310.21210.55430.076*
C121.3780 (3)0.3894 (4)0.54542 (16)0.0867 (10)
H121.46640.39360.57420.104*
C131.3161 (4)0.4907 (3)0.51563 (19)0.0918 (11)
H131.36220.56390.52400.110*
C141.1867 (4)0.4845 (3)0.47361 (18)0.0918 (10)
H141.14350.55350.45350.110*
C151.1194 (3)0.3754 (3)0.46090 (15)0.0755 (8)
H151.03100.37180.43200.091*
C160.6105 (2)0.1190 (2)0.35057 (11)0.0515 (6)
C170.6344 (2)0.0550 (2)0.28908 (11)0.0484 (6)
C180.7060 (2)0.0527 (3)0.29393 (13)0.0628 (7)
H180.73170.08920.33640.075*
C190.7404 (3)0.1075 (3)0.23813 (16)0.0745 (8)
H190.78830.18010.24290.089*
C200.7036 (3)0.0545 (3)0.17518 (16)0.0785 (9)
H200.72780.09050.13720.094*
C210.6326 (3)0.0498 (3)0.16852 (13)0.0719 (8)
H210.60790.08550.12580.086*
C220.5959 (3)0.1044 (3)0.22447 (13)0.0640 (7)
H220.54460.17530.21870.077*
C230.4864 (2)0.1698 (2)0.35701 (13)0.0618 (7)
H230.49190.21610.39610.074*
C240.3455 (2)0.1647 (3)0.31340 (12)0.0562 (7)
C250.2926 (3)0.0713 (3)0.27103 (15)0.0827 (9)
H250.35140.00710.26680.099*
C260.1547 (3)0.0700 (3)0.23466 (16)0.0942 (11)
H260.12170.00560.20650.113*
C270.0660 (3)0.1649 (4)0.24024 (17)0.0891 (10)
H270.02640.16600.21520.107*
C280.1159 (3)0.2566 (3)0.28288 (16)0.0820 (9)
H280.05650.32010.28760.098*
C290.2521 (3)0.2569 (3)0.31884 (13)0.0702 (8)
H290.28320.32070.34780.084*
N10.96186 (19)0.14922 (18)0.46014 (10)0.0531 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0569 (15)0.0496 (18)0.0525 (15)0.0052 (13)0.0023 (12)0.0001 (12)
C20.0393 (13)0.0439 (17)0.0594 (15)0.0035 (11)0.0009 (11)0.0010 (12)
C30.0490 (14)0.0434 (17)0.0524 (15)0.0013 (12)0.0046 (11)0.0014 (12)
C40.0513 (15)0.077 (2)0.0687 (19)0.0006 (14)0.0067 (14)0.0074 (15)
C50.077 (2)0.109 (3)0.0635 (19)0.0081 (19)0.0151 (16)0.0050 (18)
C60.088 (2)0.094 (3)0.0565 (17)0.0118 (19)0.0061 (17)0.0085 (16)
C70.0630 (17)0.062 (2)0.0637 (18)0.0053 (14)0.0086 (14)0.0053 (14)
C80.0466 (14)0.0391 (17)0.0623 (16)0.0009 (12)0.0038 (12)0.0002 (12)
C90.0430 (14)0.0535 (19)0.0767 (17)0.0046 (13)0.0018 (12)0.0007 (14)
C100.0411 (14)0.0489 (19)0.0594 (15)0.0035 (13)0.0096 (12)0.0018 (13)
C110.0459 (15)0.070 (2)0.0721 (17)0.0049 (14)0.0088 (13)0.0033 (15)
C120.0548 (18)0.106 (3)0.097 (2)0.029 (2)0.0089 (16)0.010 (2)
C130.092 (3)0.072 (3)0.122 (3)0.030 (2)0.047 (2)0.017 (2)
C140.092 (2)0.054 (2)0.130 (3)0.001 (2)0.025 (2)0.009 (2)
C150.0668 (18)0.057 (2)0.096 (2)0.0027 (17)0.0005 (16)0.0042 (18)
C160.0485 (14)0.0480 (17)0.0537 (15)0.0026 (13)0.0001 (11)0.0043 (13)
C170.0416 (13)0.0454 (17)0.0522 (15)0.0009 (12)0.0047 (11)0.0038 (13)
C180.0595 (16)0.058 (2)0.0643 (17)0.0064 (15)0.0043 (13)0.0011 (15)
C190.0684 (18)0.059 (2)0.089 (2)0.0113 (15)0.0013 (17)0.0144 (19)
C200.078 (2)0.079 (3)0.077 (2)0.0152 (19)0.0120 (16)0.026 (2)
C210.092 (2)0.065 (2)0.0541 (18)0.0093 (18)0.0034 (15)0.0006 (16)
C220.0698 (17)0.0533 (19)0.0616 (18)0.0034 (14)0.0040 (14)0.0019 (14)
C230.0535 (16)0.066 (2)0.0613 (16)0.0058 (14)0.0001 (12)0.0008 (13)
C240.0477 (14)0.060 (2)0.0586 (15)0.0095 (14)0.0051 (12)0.0085 (14)
C250.0544 (17)0.083 (3)0.102 (2)0.0073 (16)0.0058 (16)0.0126 (19)
C260.0613 (19)0.097 (3)0.113 (3)0.000 (2)0.0087 (18)0.013 (2)
C270.0467 (17)0.122 (3)0.092 (2)0.012 (2)0.0033 (16)0.021 (2)
C280.057 (2)0.090 (3)0.097 (2)0.0196 (18)0.0126 (17)0.012 (2)
C290.0536 (17)0.078 (2)0.0779 (18)0.0092 (16)0.0114 (14)0.0061 (16)
N10.0412 (11)0.0516 (15)0.0620 (13)0.0013 (10)0.0001 (10)0.0011 (10)
Geometric parameters (Å, º) top
C1—N11.359 (3)C14—H140.9300
C1—C21.377 (3)C15—H150.9300
C1—H10.9300C16—C231.355 (3)
C2—C31.428 (3)C16—C171.481 (3)
C2—C161.470 (3)C17—C181.382 (3)
C3—C41.403 (3)C17—C221.386 (3)
C3—C81.405 (3)C18—C191.372 (3)
C4—C51.362 (3)C18—H180.9300
C4—H40.9300C19—C201.372 (4)
C5—C61.385 (4)C19—H190.9300
C5—H50.9300C20—C211.345 (4)
C6—C71.370 (3)C20—H200.9300
C6—H60.9300C21—C221.383 (4)
C7—C81.386 (3)C21—H210.9300
C7—H70.9300C22—H220.9300
C8—N11.386 (3)C23—C241.461 (3)
C9—N11.457 (3)C23—H230.9300
C9—C101.505 (3)C24—C251.377 (4)
C9—H9A0.9700C24—C291.389 (3)
C9—H9B0.9700C25—C261.382 (3)
C10—C151.369 (4)C25—H250.9300
C10—C111.373 (3)C26—C271.383 (4)
C11—C121.379 (4)C26—H260.9300
C11—H110.9300C27—C281.359 (4)
C12—C131.361 (4)C27—H270.9300
C12—H120.9300C28—C291.365 (3)
C13—C141.359 (4)C28—H280.9300
C13—H130.9300C29—H290.9300
C14—C151.381 (4)
N1—C1—C2110.6 (2)C14—C15—H15119.4
N1—C1—H1124.7C23—C16—C2119.4 (2)
C2—C1—H1124.7C23—C16—C17124.8 (2)
C1—C2—C3105.7 (2)C2—C16—C17115.79 (19)
C1—C2—C16125.2 (2)C18—C17—C22116.7 (2)
C3—C2—C16129.0 (2)C18—C17—C16121.5 (2)
C4—C3—C8117.4 (2)C22—C17—C16121.6 (2)
C4—C3—C2134.5 (2)C19—C18—C17122.1 (3)
C8—C3—C2107.75 (19)C19—C18—H18118.9
C5—C4—C3119.2 (2)C17—C18—H18118.9
C5—C4—H4120.4C18—C19—C20119.6 (3)
C3—C4—H4120.4C18—C19—H19120.2
C4—C5—C6122.0 (3)C20—C19—H19120.2
C4—C5—H5119.0C21—C20—C19119.8 (3)
C6—C5—H5119.0C21—C20—H20120.1
C7—C6—C5120.9 (3)C19—C20—H20120.1
C7—C6—H6119.6C20—C21—C22120.8 (3)
C5—C6—H6119.6C20—C21—H21119.6
C6—C7—C8117.3 (2)C22—C21—H21119.6
C6—C7—H7121.4C21—C22—C17120.9 (3)
C8—C7—H7121.4C21—C22—H22119.5
N1—C8—C7129.5 (2)C17—C22—H22119.5
N1—C8—C3107.19 (19)C16—C23—C24131.4 (2)
C7—C8—C3123.2 (2)C16—C23—H23114.3
N1—C9—C10114.6 (2)C24—C23—H23114.3
N1—C9—H9A108.6C25—C24—C29116.5 (2)
C10—C9—H9A108.6C25—C24—C23125.6 (2)
N1—C9—H9B108.6C29—C24—C23117.7 (3)
C10—C9—H9B108.6C24—C25—C26122.0 (3)
H9A—C9—H9B107.6C24—C25—H25119.0
C15—C10—C11118.3 (3)C26—C25—H25119.0
C15—C10—C9122.3 (2)C25—C26—C27119.7 (3)
C11—C10—C9119.3 (2)C25—C26—H26120.1
C10—C11—C12120.5 (3)C27—C26—H26120.1
C10—C11—H11119.8C28—C27—C26118.9 (3)
C12—C11—H11119.8C28—C27—H27120.6
C13—C12—C11120.5 (3)C26—C27—H27120.6
C13—C12—H12119.7C27—C28—C29121.0 (3)
C11—C12—H12119.7C27—C28—H28119.5
C14—C13—C12119.7 (3)C29—C28—H28119.5
C14—C13—H13120.2C28—C29—C24121.9 (3)
C12—C13—H13120.2C28—C29—H29119.1
C13—C14—C15119.9 (3)C24—C29—H29119.1
C13—C14—H14120.0C1—N1—C8108.66 (18)
C15—C14—H14120.0C1—N1—C9126.2 (2)
C10—C15—C14121.1 (3)C8—N1—C9125.02 (19)
C10—C15—H15119.4
N1—C1—C2—C30.9 (3)C2—C16—C17—C1846.9 (3)
N1—C1—C2—C16177.3 (2)C23—C16—C17—C2249.6 (4)
C1—C2—C3—C4172.3 (3)C2—C16—C17—C22128.0 (2)
C16—C2—C3—C49.6 (5)C22—C17—C18—C191.3 (4)
C1—C2—C3—C80.7 (3)C16—C17—C18—C19173.8 (2)
C16—C2—C3—C8177.4 (2)C17—C18—C19—C200.3 (4)
C8—C3—C4—C52.6 (4)C18—C19—C20—C210.9 (4)
C2—C3—C4—C5175.2 (3)C19—C20—C21—C220.0 (4)
C3—C4—C5—C60.8 (5)C20—C21—C22—C171.7 (4)
C4—C5—C6—C71.4 (5)C18—C17—C22—C212.3 (4)
C5—C6—C7—C81.5 (4)C16—C17—C22—C21172.9 (2)
C6—C7—C8—N1175.4 (2)C2—C16—C23—C24174.0 (2)
C6—C7—C8—C30.5 (4)C17—C16—C23—C248.5 (4)
C4—C3—C8—N1174.1 (2)C16—C23—C24—C2528.5 (4)
C2—C3—C8—N10.3 (3)C16—C23—C24—C29157.1 (3)
C4—C3—C8—C72.6 (4)C29—C24—C25—C261.3 (4)
C2—C3—C8—C7177.0 (2)C23—C24—C25—C26175.7 (3)
N1—C9—C10—C1536.5 (3)C24—C25—C26—C270.2 (5)
N1—C9—C10—C11148.1 (2)C25—C26—C27—C281.5 (5)
C15—C10—C11—C121.4 (4)C26—C27—C28—C291.2 (5)
C9—C10—C11—C12174.2 (2)C27—C28—C29—C240.3 (4)
C10—C11—C12—C130.9 (4)C25—C24—C29—C281.6 (4)
C11—C12—C13—C140.1 (5)C23—C24—C29—C28176.5 (2)
C12—C13—C14—C150.6 (5)C2—C1—N1—C80.7 (3)
C11—C10—C15—C140.9 (4)C2—C1—N1—C9177.1 (2)
C9—C10—C15—C14174.6 (3)C7—C8—N1—C1176.2 (2)
C13—C14—C15—C100.1 (5)C3—C8—N1—C10.3 (3)
C1—C2—C16—C23149.8 (3)C7—C8—N1—C90.2 (4)
C3—C2—C16—C2327.9 (4)C3—C8—N1—C9176.7 (2)
C1—C2—C16—C1727.9 (4)C10—C9—N1—C1109.4 (3)
C3—C2—C16—C17154.3 (2)C10—C9—N1—C874.8 (3)
C23—C16—C17—C18135.6 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1/C1/C2/C3/C8 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9B···Cg1i0.972.793.619 (3)144
C28—H28···Cg2ii0.932.923.830 (3)165
Symmetry codes: (i) x+2, y, z+1; (ii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC29H23N
Mr385.48
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.6513 (7), 11.1857 (10), 20.0026 (14)
β (°) 101.636 (4)
V3)2115.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.22 × 0.19 × 0.16
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.985, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
14333, 4736, 1944
Rint0.057
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.164, 0.96
No. of reflections4736
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.17

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'.

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1/C1/C2/C3/C8 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9B···Cg1i0.972.793.619 (3)144
C28—H28···Cg2ii0.932.923.830 (3)165
Symmetry codes: (i) x+2, y, z+1; (ii) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

MNM thanks the Management of The New College (Autonomous), Chennai, India, for providing the necessary facilities.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDyker, G. (1999). Angew Chem. Int. Ed. 38, 1698–1712.  CrossRef Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFerrer, C., Amijs, C. H. M. & Echavarren, A. M. (2007). Chem. Eur. J. pp. 1358–1373.  Web of Science CSD CrossRef Google Scholar
First citationRitleng, V., Sirlin, C. & Pfeffer, M. (2002). Chem. Rev. 102, 1731–1769.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSundberg, R. J. (1996). Indoles. London: Academic Press.  Google Scholar

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