Literature DB >> 21588950

3-(1,2-Diphenyl-ethen-yl)-2-phenyl-1H-indole.

P A Abdullah Mahaboob, M Nizammohideen, G Bhaskar, P T Perumal.   

Abstract

In the title compound, C(28)H(21)N, the planar pyrrole ring makes dihedral angles of 1.5 (2), 42.4 (2), 65.4 (2) and 79.7 (1)°, with the least squares planes of the four phenyl rings. The mol-ecular structure and crystal packing are stabilized by weak inter- and intra-molecular C-H⋯π inter-actions.

Entities:  

Year:  2010        PMID： 21588950      PMCID： PMC3009176          DOI： 10.1107/S1600536810039309

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


Related literature

For applications of heteroarenes, see: Ritleng et al. (2002 ▶). For their pharmaceutical properties and related reactions, see: Sundberg (1996 ▶); Ferrer et al. (2007 ▶); Nair et al. (2004 ▶; Sakai et al. (2006 ▶, 2008 ▶); Cheng et al. (2007 ▶); For standard bond lengths, see: Allen et al. (1987 ▶). For bond distances and angles in related structures, see: NizamMohideen et al. (2010a ▶,b ▶).

Experimental

Crystal data

C28H21N M = 371.46 Monoclinic, a = 11.4227 (6) Å b = 8.6998 (5) Å c = 20.6203 (13) Å β = 94.413 (4)° V = 2043.1 (2) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 298 K 0.32 × 0.28 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer’ Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.978, T max = 0.985 14625 measured reflections 4674 independent reflections 1701 reflections with I > 2σ(I) R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.070 wR(F 2) = 0.221 S = 1.01 4674 reflections 266 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.30 e Å−3 Δρmin = −0.14 e Å−3 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); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039309/jj2059sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039309/jj2059Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C28H21NF(000) = 784
Mr = 371.46Dx = 1.208 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1461 reflections
a = 11.4227 (6) Åθ = 2.5–18.8°
b = 8.6998 (5) ŵ = 0.07 mm−1
c = 20.6203 (13) ÅT = 298 K
β = 94.413 (4)°Block, colourless
V = 2043.1 (2) Å30.32 × 0.28 × 0.22 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer'4674 independent reflections
Radiation source: fine-focus sealed tube1701 reflections with I > 2σ(I)
graphiteRint = 0.057
ω and φ scansθmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −15→13
Tmin = 0.978, Tmax = 0.985k = −11→10
14625 measured reflectionsl = −27→27
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0923P)2] where P = (Fo2 + 2Fc2)/3
4674 reflections(Δ/σ)max < 0.001
266 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
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.
xyzUiso*/Ueq
C10.6739 (3)0.0471 (4)0.09769 (15)0.0597 (9)
C20.7394 (3)0.1773 (4)0.11004 (14)0.0567 (8)
C30.6655 (3)0.2848 (4)0.14155 (14)0.0553 (8)
C40.6798 (3)0.4337 (4)0.16344 (16)0.0663 (9)
H40.75070.48420.15950.080*
C50.5896 (3)0.5078 (4)0.19108 (15)0.0716 (10)
H50.60000.60820.20590.086*
C60.4831 (3)0.4337 (5)0.19703 (17)0.0770 (11)
H60.42300.48420.21630.092*
C70.4662 (3)0.2860 (5)0.17452 (17)0.0755 (11)
H70.39510.23560.17770.091*
C80.5580 (3)0.2157 (4)0.14725 (16)0.0606 (9)
C90.7056 (3)−0.1003 (4)0.06783 (15)0.0594 (9)
C100.6325 (3)−0.1789 (5)0.02351 (19)0.0823 (11)
H100.5589−0.13830.01110.099*
C110.6650 (4)−0.3161 (5)−0.0031 (2)0.0910 (12)
H110.6136−0.3684−0.03250.109*
C120.7729 (5)−0.3737 (5)0.0142 (2)0.0926 (13)
H120.7963−0.4649−0.00450.111*
C130.8484 (3)−0.3000 (5)0.0588 (2)0.0807 (11)
H130.9214−0.34260.07120.097*
C140.8157 (3)−0.1631 (4)0.08506 (17)0.0687 (10)
H140.8675−0.11190.11460.082*
C150.8582 (3)0.2075 (4)0.09030 (17)0.0633 (9)
C160.8850 (3)0.1954 (4)0.02908 (16)0.0647 (9)
H160.96490.19980.02330.078*
C170.8091 (3)0.1761 (4)−0.03113 (15)0.0558 (8)
C180.6996 (3)0.2448 (4)−0.04003 (16)0.0598 (9)
H180.66740.2921−0.00510.072*
C190.6376 (3)0.2438 (4)−0.1002 (2)0.0757 (10)
H190.56480.2918−0.10590.091*
C200.6835 (4)0.1720 (5)−0.15140 (19)0.0947 (13)
H200.64190.1727−0.19200.114*
C210.7894 (4)0.0995 (5)−0.1438 (2)0.0995 (13)
H210.81890.0484−0.17870.119*
C220.8522 (3)0.1024 (4)−0.08424 (19)0.0801 (11)
H220.92490.0541−0.07930.096*
C230.9520 (3)0.2436 (4)0.14166 (17)0.0627 (9)
C241.0480 (3)0.3370 (5)0.1295 (2)0.0875 (12)
H241.05140.38050.08850.105*
C251.1354 (3)0.3657 (5)0.1754 (2)0.1007 (14)
H251.19770.42870.16620.121*
C261.1321 (4)0.3016 (6)0.2357 (2)0.1003 (14)
H261.19420.31740.26690.120*
C271.0389 (4)0.2150 (5)0.2505 (2)0.0953 (13)
H271.03620.17390.29200.114*
C280.9482 (3)0.1884 (4)0.20368 (19)0.0793 (11)
H280.88340.13200.21440.095*
N10.5641 (3)0.0706 (4)0.11907 (15)0.0738 (9)
H1N0.506 (3)0.001 (5)0.1187 (18)0.107 (15)*
U11U22U33U12U13U23
C10.051 (2)0.076 (3)0.053 (2)0.0087 (17)0.0059 (15)0.0111 (17)
C20.061 (2)0.065 (2)0.0440 (19)0.0007 (18)0.0009 (15)−0.0004 (16)
C30.0518 (19)0.070 (2)0.0433 (19)−0.0028 (17)−0.0002 (14)0.0064 (17)
C40.067 (2)0.072 (3)0.060 (2)−0.0061 (19)0.0086 (17)0.0030 (19)
C50.081 (3)0.073 (2)0.061 (2)0.008 (2)0.0041 (19)−0.0043 (19)
C60.064 (2)0.106 (3)0.062 (2)0.025 (2)0.0081 (18)0.001 (2)
C70.053 (2)0.104 (3)0.070 (3)−0.004 (2)0.0087 (17)0.016 (2)
C80.059 (2)0.063 (2)0.059 (2)0.0065 (18)−0.0016 (16)0.0055 (18)
C90.065 (2)0.061 (2)0.053 (2)−0.0056 (18)0.0043 (17)0.0070 (17)
C100.076 (3)0.085 (3)0.083 (3)−0.013 (2)−0.010 (2)0.004 (2)
C110.112 (4)0.076 (3)0.083 (3)−0.020 (3)−0.008 (3)−0.017 (2)
C120.124 (4)0.072 (3)0.086 (3)−0.013 (3)0.036 (3)−0.011 (2)
C130.084 (3)0.071 (3)0.089 (3)0.000 (2)0.020 (2)0.009 (2)
C140.076 (3)0.064 (2)0.067 (2)−0.0036 (19)0.0091 (19)0.0002 (19)
C150.058 (2)0.074 (2)0.058 (2)0.0023 (16)0.0013 (17)−0.0049 (18)
C160.060 (2)0.073 (2)0.061 (2)−0.0035 (17)0.0036 (18)−0.0031 (18)
C170.0472 (19)0.068 (2)0.051 (2)−0.0121 (16)−0.0044 (15)−0.0015 (17)
C180.066 (2)0.060 (2)0.052 (2)−0.0105 (17)−0.0013 (17)−0.0002 (16)
C190.079 (2)0.072 (3)0.073 (3)−0.0073 (19)−0.012 (2)0.010 (2)
C200.115 (4)0.113 (3)0.052 (3)−0.021 (3)−0.011 (2)−0.007 (2)
C210.100 (3)0.136 (4)0.063 (3)−0.016 (3)0.008 (2)−0.032 (3)
C220.065 (2)0.100 (3)0.076 (3)0.000 (2)0.009 (2)−0.022 (2)
C230.053 (2)0.071 (2)0.062 (2)0.0034 (17)−0.0091 (17)−0.0047 (18)
C240.063 (2)0.128 (4)0.071 (3)−0.006 (2)0.002 (2)−0.018 (2)
C250.058 (3)0.152 (4)0.091 (3)−0.008 (2)−0.002 (2)−0.023 (3)
C260.062 (3)0.146 (4)0.089 (4)0.014 (3)−0.016 (2)−0.030 (3)
C270.091 (3)0.129 (4)0.063 (3)0.005 (3)−0.011 (2)−0.012 (2)
C280.076 (3)0.092 (3)0.067 (3)−0.004 (2)−0.013 (2)0.000 (2)
N10.060 (2)0.083 (2)0.078 (2)−0.0147 (18)0.0016 (16)0.0084 (18)
C1—C21.370 (4)C15—C161.326 (4)
C1—N11.376 (4)C15—C231.481 (5)
C1—C91.479 (4)C16—C171.468 (4)
C2—C31.446 (4)C16—H160.9300
C2—C151.470 (4)C17—C181.386 (4)
C3—C41.377 (4)C17—C221.391 (4)
C3—C81.380 (4)C18—C191.381 (5)
C4—C51.376 (4)C18—H180.9300
C4—H40.9300C19—C201.365 (5)
C5—C61.392 (5)C19—H190.9300
C5—H50.9300C20—C211.362 (5)
C6—C71.374 (5)C20—H200.9300
C6—H60.9300C21—C221.375 (5)
C7—C81.372 (4)C21—H210.9300
C7—H70.9300C22—H220.9300
C8—N11.393 (4)C23—C281.370 (5)
C9—C101.372 (5)C23—C241.404 (5)
C9—C141.392 (4)C24—C251.345 (5)
C10—C111.377 (5)C24—H240.9300
C10—H100.9300C25—C261.365 (6)
C11—C121.352 (5)C25—H250.9300
C11—H110.9300C26—C271.358 (5)
C12—C131.371 (5)C26—H260.9300
C12—H120.9300C27—C281.380 (5)
C13—C141.372 (5)C27—H270.9300
C13—H130.9300C28—H280.9300
C14—H140.9300N1—H1N0.89 (4)
C2—C1—N1108.4 (3)C2—C15—C23118.2 (3)
C2—C1—C9130.3 (3)C15—C16—C17130.5 (3)
N1—C1—C9121.4 (3)C15—C16—H16114.8
C1—C2—C3106.8 (3)C17—C16—H16114.8
C1—C2—C15126.7 (3)C18—C17—C22117.7 (3)
C3—C2—C15126.3 (3)C18—C17—C16122.1 (3)
C4—C3—C8117.8 (3)C22—C17—C16119.8 (3)
C4—C3—C2134.2 (3)C19—C18—C17120.8 (3)
C8—C3—C2108.0 (3)C19—C18—H18119.6
C5—C4—C3120.2 (3)C17—C18—H18119.6
C5—C4—H4119.9C20—C19—C18119.8 (4)
C3—C4—H4119.9C20—C19—H19120.1
C4—C5—C6120.5 (3)C18—C19—H19120.1
C4—C5—H5119.8C21—C20—C19120.9 (4)
C6—C5—H5119.8C21—C20—H20119.5
C7—C6—C5120.3 (3)C19—C20—H20119.5
C7—C6—H6119.9C20—C21—C22119.4 (4)
C5—C6—H6119.9C20—C21—H21120.3
C8—C7—C6117.6 (3)C22—C21—H21120.3
C8—C7—H7121.2C21—C22—C17121.3 (4)
C6—C7—H7121.2C21—C22—H22119.3
C7—C8—C3123.6 (3)C17—C22—H22119.3
C7—C8—N1129.8 (3)C28—C23—C24116.8 (3)
C3—C8—N1106.6 (3)C28—C23—C15121.4 (3)
C10—C9—C14117.7 (3)C24—C23—C15121.8 (3)
C10—C9—C1123.6 (3)C25—C24—C23122.0 (4)
C14—C9—C1118.6 (3)C25—C24—H24119.0
C9—C10—C11121.9 (4)C23—C24—H24119.0
C9—C10—H10119.0C24—C25—C26119.6 (4)
C11—C10—H10119.0C24—C25—H25120.2
C12—C11—C10119.0 (4)C26—C25—H25120.2
C12—C11—H11120.5C27—C26—C25120.5 (4)
C10—C11—H11120.5C27—C26—H26119.7
C11—C12—C13121.1 (4)C25—C26—H26119.7
C11—C12—H12119.4C26—C27—C28119.7 (4)
C13—C12—H12119.4C26—C27—H27120.2
C12—C13—C14119.6 (4)C28—C27—H27120.2
C12—C13—H13120.2C23—C28—C27121.3 (4)
C14—C13—H13120.2C23—C28—H28119.4
C13—C14—C9120.5 (4)C27—C28—H28119.4
C13—C14—H14119.7C1—N1—C8110.1 (3)
C9—C14—H14119.7C1—N1—H1N126 (2)
C16—C15—C2122.4 (3)C8—N1—H1N124 (2)
C16—C15—C23119.4 (3)
N1—C1—C2—C30.9 (3)C3—C2—C15—C16−120.7 (4)
C9—C1—C2—C3−178.4 (3)C1—C2—C15—C23−122.5 (3)
N1—C1—C2—C15−174.5 (3)C3—C2—C15—C2363.0 (4)
C9—C1—C2—C156.2 (5)C2—C15—C16—C1710.5 (6)
C1—C2—C3—C4−177.6 (3)C23—C15—C16—C17−173.2 (3)
C15—C2—C3—C4−2.2 (6)C15—C16—C17—C1835.3 (5)
C1—C2—C3—C80.1 (3)C15—C16—C17—C22−152.4 (4)
C15—C2—C3—C8175.5 (3)C22—C17—C18—C19−2.0 (4)
C8—C3—C4—C51.2 (4)C16—C17—C18—C19170.4 (3)
C2—C3—C4—C5178.8 (3)C17—C18—C19—C201.2 (5)
C3—C4—C5—C6−0.2 (5)C18—C19—C20—C210.8 (6)
C4—C5—C6—C7−0.9 (5)C19—C20—C21—C22−1.8 (6)
C5—C6—C7—C80.9 (5)C20—C21—C22—C170.9 (6)
C6—C7—C8—C30.2 (5)C18—C17—C22—C211.0 (5)
C6—C7—C8—N1−177.8 (3)C16—C17—C22—C21−171.6 (3)
C4—C3—C8—C7−1.3 (5)C16—C15—C23—C28−148.1 (3)
C2—C3—C8—C7−179.4 (3)C2—C15—C23—C2828.3 (5)
C4—C3—C8—N1177.1 (3)C16—C15—C23—C2432.6 (5)
C2—C3—C8—N1−1.0 (3)C2—C15—C23—C24−150.9 (3)
C2—C1—C9—C10−138.1 (4)C28—C23—C24—C253.1 (5)
N1—C1—C9—C1042.6 (5)C15—C23—C24—C25−177.6 (3)
C2—C1—C9—C1441.5 (5)C23—C24—C25—C260.5 (6)
N1—C1—C9—C14−137.8 (3)C24—C25—C26—C27−3.0 (7)
C14—C9—C10—C110.6 (5)C25—C26—C27—C281.7 (6)
C1—C9—C10—C11−179.8 (3)C24—C23—C28—C27−4.4 (5)
C9—C10—C11—C12−1.1 (6)C15—C23—C28—C27176.3 (3)
C10—C11—C12—C131.8 (6)C26—C27—C28—C232.1 (6)
C11—C12—C13—C14−2.0 (6)C2—C1—N1—C8−1.6 (4)
C12—C13—C14—C91.4 (5)C9—C1—N1—C8177.8 (3)
C10—C9—C14—C13−0.7 (5)C7—C8—N1—C1179.9 (3)
C1—C9—C14—C13179.6 (3)C3—C8—N1—C11.6 (4)
C1—C2—C15—C1653.8 (5)
Cg1 and Cg2 are the centroids of the N1/C1/C2/C3/C8 and C3–C8 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C18—H18···Cg10.932.923.562 (2)127
C20—H20···Cg2i0.932.923.825 (2)164
Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C18—H18⋯Cg10.932.923.562 (2)127
C20—H20⋯Cg2i0.932.923.825 (2)164

Symmetry code: (i) .

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