PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2017 September 1; 73(Pt 9): 1329–1332.
Published online 2017 August 11. doi:  10.1107/S2056989017011483
PMCID: PMC5588573

Crystal structure and DFT study of (E)-N-[2-(1H-indol-3-yl)eth­yl]-1-(anthracen-9-yl)methanimine

Abstract

The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 63.56 (8)° with the anthracene ring (r.m.s. deviation = 0.023 Å). There is a short intra­molecular C—H(...)N inter­action present, and a C—H(...)π inter­action involving the two ring systems. In the crystal, the indole H atom forms an inter­molecular N—H(...)π inter­action, linking mol­ecules to form chains along the b-axis direction. There are also C—H(...)π inter­actions present, involving the central and terminal rings of the anthracene unit, linking the chains to form an overall two-dimensional layered structure, with the layers parallel to the bc plane. The density functional theory (DFT) optimized structure, at the B3LYP/6-311 G(d,p) level, is compared with the experimentally determined mol­ecular structure in the solid state.

Keywords: crystal structure, anthracene, indole, Schiff base, tryptamine, methanamine, N—H(...)π inter­actions, C—H(...)π inter­actions

Chemical context  

Tryptamine is a biogenic serotonin-related indo­amine and is the deca­rboxylation product of the amino acid tryptophan. 2-(1H-Indol-3-yl)ethanamine is an alkaloid found in plants and fungi and is a possible inter­mediate in the biosynthetic pathway to the plant hormone indole-3-acetic acid (Takahashi, 1986  ). It is also found in trace amounts in the mammalian brain, possibly acting as a neuromodulator or neurotransmitter (Jones, 1982  ). There are seven known families of serotonin receptors, which are tryptamine derivatives. All of them are neurotransmitters. Hallucinogens all have a high affinity for certain serotonin receptor subtypes and the relative hallucinogenic potencies of various drugs can be gauged by their affinities for these receptors (Glennon et al., 1984  ; Nichols & Sanders-Bush, 2001  ; Johnson et al., 1987  ; Krebs-Thomson et al., 1998  ). The structures of many hallucinogens are similar to serotonin and have a tryptamine core. Indole analogues, especially of tryptamine derivatives, have been found to be polyamine site antagonists at the N-methyl-d-aspartate receptor (NMDAR; Worthen et al., 2001  ). Indole and its derivatives are secondary metabolites that are present in most plants (such as unripe bananas, broccoli and clove), almost all flower oils (e.g. jasmine and orange blossoms) and coal tar (Waseem & Mark 2005  ; Lee et al., 2003  ). In the pharmaceutical field, it has been discovered that it has anti­microbial and anti-inflammatory properties (Mohammad & Moutaery, 2005  ). The present work is part of an ongoing structural study of Schiff bases and their utilization in the synthesis of new organic and polynuclear coordination compounds, and their application in fluorescence sensors (Faizi & Sen, 2014  ; Faizi et al., 2016  ). We report herein the crystal structure of (E)-N-[2-(1H-indol-3-yl)eth­yl]-1-(an­thra­cen-9-yl)methanimine, (I), and its DFT computational calculation. Calculations by density functional theory (DFT) on (I), carried out at the B3LYP/6-311 G(d,p) level, are compared with the experimentally determined mol­ecular structure in the solid state.

An external file that holds a picture, illustration, etc.
Object name is e-73-01329-scheme1.jpg

Structural commentary  

The mol­ecular structure of compound (I) is illustrated in Fig. 1  . The mol­ecule adopts a nonplanar geometry, with the dihedral angle between the planes of the indole and anthracene rings being 63.56 (8)°. The conformation about the azomethine C15=N1 bond [1.272 (10) Å] is E, with the C14—N2—C12—C13 torsion angle being 179.0 (1)°. The mol­ecule is stabilized by a weak intra­molecular hydrogen bond (C12—H12(...)N1) and a C—H(...)π inter­action (C2—H2(...)Cg5; Cg5 is the centroid of the C19–C24 ring); see Table 1  .

Figure 1
The mol­ecular structure of compound (I), with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Table 1
Hydrogen-bond geometry (Å, °)

Supra­molecular features  

In the crystal, the indole H atom forms an inter­molecular N—H(...)π inter­action, linking mol­ecules to form chains along the b-axis direction (Fig. 2  and Table 1  ). There are also C—H(...)π inter­actions present, involving the central ring and terminal rings of the anthracene unit, linking the chains to form layers parallel to the bc plane (Fig. 2  and Table 1  ).

Figure 2
A view along the a axis of the crystal packing of compound (I), showing the layer-like structure. Weak N—H(...)π and C—H(...)π inter­actions are shown as blue dashed lines (see Table 1  ...

Database survey  

A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2017; Groom et al., 2016  ) revealed the structures of several similar compounds containing a phenol group [(II) (CSD refcode FAJVIV; Rodriguez et al., 1987  ) and (III) (TANNOL; Ishida et al., 1992  )] and nitro­benzene moieties [(IV), GEYPEF; Törnroos, 1988  ]. All compounds are 2-indole-substituted derivatives which have two aromatic units linked via an aliphatic chain. In (I), the dihedral angle between indole and anthracene rings is 63.56 (8)°, which is similar for (III) and (IV), viz. 71.52 and 64.21°, respectively. In compounds (I) and (II), the conformation about the azomethine C15=N1 bond is E.

DFT study  

Calculations by density functional theory DFT-B3LYP, with basis set 6-311 G(d,p), of bond lengths and angles were performed. These values are compared with the experimental values for the title system (see Table 2  ). From these results we can conclude that basis set 6-311 G(d,p) is better suited in its approach to the experimental data.

Table 2
Comparison of selected geometric data for (I) (Å, °) from X-ray and calculated (DFT) data

The LUMO and HOMO orbital energy parameters are considerably answerable for the charge transfer, chemical reactivity and kinetic/thermodynamic stability of (I). The DFT study of (I) revealed that the HOMO and LUMO are localized in the plane extending from the whole anthracene ring to the indole ring, and electron distribution of the HOMO-1, HOMO, LUMO and LUMO+1 energy levels are shown in Fig. 3  . The mol­ecular orbital of HOMO contains both σ and π character, whereas HOMO-1 is dominated by π-orbital density. The LUMO is mainly composed of σ density, while LUMO+1 has both σ and π electronic density. The HOMO–LUMO gap for (I) was found to be 0.12325 a.u. and the frontier mol­ecular orbital energies, E HOMO and E LUMO, were found to be −0.196412 and −0.07087 a.u., respectively.

Figure 3
Electron distribution of the HOMO-1, HOMO, LUMO and LUMO+1 energy levels for compound (I).

Synthesis and crystallization  

80 mg (0.435 mmol) of 2-(1H-indol-3-yl)ethanamine (tryptamine) were dissolved in 10 ml of absolute ethanol. To this solution, 89 mg (0.434 mmol) of anthracene-9-carbaldehyde in 5 ml of absolute ethanol were added dropwise under stirring. The mixture was stirred for 10 min, two drops of glacial acetic acid were added and the mixture was refluxed for a further 2 h. The resulting yellow precipitate was recovered by filtration, washed several times with small portions of ice-cold ethanol and then with diethyl ether to give 140 mg (87%) of compound (I). Dark-yellow block-like crystals suitable for X-ray analysis were obtained within 3 d by slow evaporation of a solution in methanol.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 3  . The N—H H atom was located from a difference-Fourier map and constrained to ride on the parent atom: N—H = 0.86 Å and U iso(H) = 1.2U eq(N). All C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and U iso(H) = 1.2U eq(C).

Table 3
Experimental details

The DFT quantum-chemical calculations were performed at the B3LYP/6-311 G(d,p) level (Becke, 1993  ; Lee et al., 2003  ) as implemented in GAUSSIAN09 (Frisch et al., 2009  ). DFT structure optimization of (I) was performed starting from the X-ray geometry.

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989017011483/su5387sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017011483/su5387Isup2.hkl

CCDC reference: 1537222

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the Ondokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, Turkey, for X-ray data collection, and Department of Chemistry, National Taras Shevchenko University of Kiev.

supplementary crystallographic information

Crystal data

C25H20N2Dx = 1.308 Mg m3
Mr = 348.43Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 5148 reflections
a = 6.0044 (3) Åθ = 2.6–27.4°
b = 16.4721 (7) ŵ = 0.08 mm1
c = 17.8957 (9) ÅT = 100 K
V = 1769.98 (15) Å3Needle, yellow
Z = 40.20 × 0.15 × 0.13 mm
F(000) = 736

Data collection

Bruker SMART APEX CCD diffractometer3127 independent reflections
Radiation source: fine-focus sealed tube2577 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2003)h = −7→7
Tmin = 0.875, Tmax = 0.990k = −19→19
14169 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.093w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3127 reflectionsΔρmax = 0.15 e Å3
245 parametersΔρmin = −0.20 e Å3
0 restraintsAbsolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.9441 (4)0.37168 (13)0.28719 (12)0.0239 (6)
N20.6749 (4)0.30313 (14)0.06673 (12)0.0282 (6)
H2A0.5469020.3034630.0451360.034*
C180.9807 (5)0.34812 (16)0.12665 (15)0.0239 (7)
C10.5718 (5)0.20309 (15)0.32067 (14)0.0199 (6)
C80.3608 (5)0.30172 (16)0.42939 (14)0.0216 (6)
C150.8796 (5)0.30043 (16)0.30408 (14)0.0219 (6)
H150.9758920.2579900.2926470.026*
C130.5640 (5)0.32872 (15)0.39461 (15)0.0216 (6)
C140.6662 (5)0.27861 (15)0.34017 (14)0.0206 (6)
C70.2732 (5)0.22659 (16)0.41038 (14)0.0235 (7)
H70.1443660.2089370.4341850.028*
C90.2567 (5)0.35163 (17)0.48380 (15)0.0265 (7)
H90.1247120.3344650.5059540.032*
C191.0013 (5)0.26179 (15)0.11461 (15)0.0227 (7)
C60.3713 (5)0.17673 (16)0.35700 (14)0.0226 (7)
C20.6601 (5)0.15155 (15)0.26395 (14)0.0247 (7)
H20.7881580.1674240.2386040.030*
C50.2749 (5)0.10058 (16)0.33667 (15)0.0274 (7)
H50.1463200.0831370.3607770.033*
C201.1624 (5)0.20388 (17)0.13290 (15)0.0256 (7)
H201.2933140.2192440.1568040.031*
C240.8068 (5)0.23616 (17)0.07725 (15)0.0250 (7)
C230.7688 (5)0.15516 (17)0.05852 (15)0.0267 (7)
H230.6399910.1392600.0336420.032*
C30.5619 (5)0.07970 (16)0.24594 (16)0.0276 (7)
H30.6240240.0475030.2086760.033*
C40.3669 (5)0.05321 (16)0.28300 (15)0.0292 (7)
H40.3023710.0036800.2706200.035*
C120.6514 (5)0.40513 (15)0.41843 (15)0.0260 (7)
H120.7831190.4241840.3974510.031*
C110.5466 (5)0.45039 (17)0.47086 (15)0.0294 (7)
H110.6078180.4998410.4852630.035*
C250.7808 (5)0.36954 (17)0.09638 (15)0.0279 (7)
H250.7239850.4220580.0958870.033*
C161.1623 (5)0.37629 (16)0.25049 (15)0.0257 (7)
H16A1.2343100.3236250.2525150.031*
H16B1.2558710.4149550.2766770.031*
C100.3465 (5)0.42396 (17)0.50402 (16)0.0293 (7)
H100.2760830.4560230.5396810.035*
C220.9296 (5)0.09975 (18)0.07835 (16)0.0312 (7)
H220.9082440.0451840.0671110.037*
C171.1358 (5)0.40255 (16)0.16908 (15)0.0268 (7)
H17A1.0792620.4576820.1675520.032*
H17B1.2805750.4021830.1450200.032*
C211.1245 (5)0.12360 (16)0.11501 (16)0.0306 (7)
H211.2303680.0846990.1275400.037*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0244 (13)0.0239 (13)0.0233 (13)−0.0025 (11)−0.0001 (11)0.0016 (10)
N20.0235 (13)0.0334 (14)0.0277 (12)0.0037 (13)−0.0039 (11)0.0010 (11)
C180.0264 (17)0.0259 (16)0.0194 (14)0.0018 (14)0.0041 (13)0.0033 (12)
C10.0216 (15)0.0179 (14)0.0201 (14)0.0003 (13)−0.0036 (12)0.0038 (12)
C80.0233 (16)0.0231 (15)0.0184 (13)0.0026 (15)−0.0044 (12)0.0048 (12)
C150.0233 (16)0.0198 (15)0.0225 (14)0.0034 (14)−0.0035 (12)−0.0026 (12)
C130.0240 (15)0.0208 (15)0.0201 (15)0.0008 (13)−0.0051 (12)0.0042 (11)
C140.0213 (15)0.0215 (15)0.0190 (13)0.0002 (13)−0.0038 (12)0.0053 (11)
C70.0215 (15)0.0280 (17)0.0210 (15)0.0002 (13)−0.0001 (12)0.0068 (12)
C90.0256 (16)0.0310 (18)0.0230 (16)0.0052 (15)0.0006 (13)0.0040 (13)
C190.0260 (17)0.0246 (16)0.0177 (14)−0.0010 (14)0.0037 (13)−0.0001 (12)
C60.0238 (16)0.0259 (16)0.0179 (15)−0.0011 (14)−0.0046 (12)0.0048 (11)
C20.0244 (15)0.0245 (15)0.0252 (15)0.0009 (14)0.0032 (13)0.0041 (12)
C50.0305 (17)0.0260 (16)0.0257 (15)−0.0071 (15)−0.0019 (13)0.0036 (13)
C200.0228 (15)0.0287 (16)0.0253 (15)−0.0012 (15)0.0002 (13)−0.0008 (13)
C240.0254 (16)0.0301 (16)0.0193 (14)0.0014 (14)0.0026 (13)0.0027 (12)
C230.0252 (17)0.0345 (18)0.0202 (14)−0.0052 (15)−0.0006 (12)−0.0011 (13)
C30.0342 (18)0.0203 (15)0.0283 (16)0.0027 (15)0.0020 (14)0.0005 (12)
C40.0359 (18)0.0233 (16)0.0284 (16)−0.0070 (15)−0.0023 (15)0.0015 (13)
C120.0274 (16)0.0237 (15)0.0270 (15)−0.0007 (15)−0.0010 (14)0.0035 (12)
C110.0409 (19)0.0211 (15)0.0262 (16)−0.0018 (15)−0.0046 (14)−0.0021 (13)
C250.0339 (18)0.0250 (16)0.0247 (15)0.0030 (15)0.0034 (14)0.0029 (12)
C160.0235 (15)0.0214 (14)0.0323 (16)−0.0059 (14)−0.0021 (14)−0.0005 (12)
C100.0371 (18)0.0284 (17)0.0223 (14)0.0081 (16)0.0001 (15)−0.0008 (12)
C220.0411 (19)0.0263 (16)0.0264 (16)−0.0058 (16)0.0035 (15)−0.0029 (13)
C170.0267 (16)0.0208 (15)0.0328 (16)−0.0011 (14)0.0063 (14)0.0026 (13)
C210.0352 (18)0.0270 (17)0.0296 (16)0.0055 (15)0.0037 (15)0.0014 (13)

Geometric parameters (Å, º)

N1—C151.272 (3)C2—H20.9300
N1—C161.468 (4)C5—C41.355 (4)
N2—C241.371 (4)C5—H50.9300
N2—C251.372 (3)C20—C211.380 (4)
N2—H2A0.8600C20—H200.9300
C18—C251.363 (4)C24—C231.395 (4)
C18—C191.444 (3)C23—C221.375 (4)
C18—C171.499 (4)C23—H230.9300
C1—C141.411 (4)C3—C41.415 (4)
C1—C21.426 (3)C3—H30.9300
C1—C61.436 (4)C4—H40.9300
C8—C71.387 (4)C12—C111.354 (4)
C8—C91.420 (4)C12—H120.9300
C8—C131.440 (4)C11—C101.409 (4)
C15—C141.479 (4)C11—H110.9300
C15—H150.9300C25—H250.9300
C13—C141.417 (4)C16—C171.528 (4)
C13—C121.429 (4)C16—H16A0.9700
C7—C61.391 (4)C16—H16B0.9700
C7—H70.9300C10—H100.9300
C9—C101.357 (4)C22—C211.398 (4)
C9—H90.9300C22—H220.9300
C19—C201.397 (4)C17—H17A0.9700
C19—C241.411 (4)C17—H17B0.9700
C6—C51.428 (4)C21—H210.9300
C2—C31.361 (4)
C15—N1—C16115.2 (2)N2—C24—C23130.0 (3)
C24—N2—C25108.7 (2)N2—C24—C19107.6 (2)
C24—N2—H2A125.7C23—C24—C19122.4 (3)
C25—N2—H2A125.7C22—C23—C24117.3 (3)
C25—C18—C19105.7 (3)C22—C23—H23121.4
C25—C18—C17126.4 (2)C24—C23—H23121.4
C19—C18—C17127.7 (3)C2—C3—C4121.1 (3)
C14—C1—C2123.5 (2)C2—C3—H3119.5
C14—C1—C6119.4 (2)C4—C3—H3119.5
C2—C1—C6117.0 (2)C5—C4—C3119.5 (3)
C7—C8—C9121.2 (3)C5—C4—H4120.3
C7—C8—C13119.4 (2)C3—C4—H4120.3
C9—C8—C13119.4 (2)C11—C12—C13121.4 (3)
N1—C15—C14126.3 (3)C11—C12—H12119.3
N1—C15—H15116.9C13—C12—H12119.3
C14—C15—H15116.9C12—C11—C10121.2 (3)
C14—C13—C12124.0 (3)C12—C11—H11119.4
C14—C13—C8119.0 (2)C10—C11—H11119.4
C12—C13—C8117.0 (2)C18—C25—N2110.8 (2)
C1—C14—C13120.7 (2)C18—C25—H25124.6
C1—C14—C15117.0 (2)N2—C25—H25124.6
C13—C14—C15122.3 (2)N1—C16—C17110.4 (2)
C8—C7—C6122.3 (3)N1—C16—H16A109.6
C8—C7—H7118.8C17—C16—H16A109.6
C6—C7—H7118.8N1—C16—H16B109.6
C10—C9—C8121.1 (3)C17—C16—H16B109.6
C10—C9—H9119.5H16A—C16—H16B108.1
C8—C9—H9119.5C9—C10—C11119.9 (3)
C20—C19—C24118.7 (2)C9—C10—H10120.1
C20—C19—C18134.2 (3)C11—C10—H10120.1
C24—C19—C18107.1 (2)C23—C22—C21121.5 (3)
C7—C6—C5121.5 (2)C23—C22—H22119.3
C7—C6—C1119.2 (2)C21—C22—H22119.3
C5—C6—C1119.3 (2)C18—C17—C16112.2 (2)
C3—C2—C1121.7 (3)C18—C17—H17A109.2
C3—C2—H2119.2C16—C17—H17A109.2
C1—C2—H2119.2C18—C17—H17B109.2
C4—C5—C6121.4 (3)C16—C17—H17B109.2
C4—C5—H5119.3H17A—C17—H17B107.9
C6—C5—H5119.3C20—C21—C22121.1 (3)
C21—C20—C19119.1 (3)C20—C21—H21119.5
C21—C20—H20120.5C22—C21—H21119.5
C19—C20—H20120.5
C16—N1—C15—C14−179.0 (2)C7—C6—C5—C4177.9 (3)
C7—C8—C13—C141.7 (3)C1—C6—C5—C4−1.0 (4)
C9—C8—C13—C14−179.8 (2)C24—C19—C20—C21−1.1 (4)
C7—C8—C13—C12−177.6 (2)C18—C19—C20—C21177.4 (3)
C9—C8—C13—C120.9 (3)C25—N2—C24—C23178.3 (3)
C2—C1—C14—C13176.9 (2)C25—N2—C24—C19−0.1 (3)
C6—C1—C14—C13−0.5 (4)C20—C19—C24—N2179.1 (2)
C2—C1—C14—C15−5.9 (4)C18—C19—C24—N20.2 (3)
C6—C1—C14—C15176.6 (2)C20—C19—C24—C230.6 (4)
C12—C13—C14—C1178.7 (2)C18—C19—C24—C23−178.3 (3)
C8—C13—C14—C1−0.5 (4)N2—C24—C23—C22−177.8 (3)
C12—C13—C14—C151.8 (4)C19—C24—C23—C220.3 (4)
C8—C13—C14—C15−177.5 (2)C1—C2—C3—C40.1 (4)
N1—C15—C14—C1147.8 (3)C6—C5—C4—C3−0.3 (4)
N1—C15—C14—C13−35.1 (4)C2—C3—C4—C50.8 (4)
C9—C8—C7—C6179.6 (2)C14—C13—C12—C11−179.9 (3)
C13—C8—C7—C6−1.9 (4)C8—C13—C12—C11−0.6 (4)
C7—C8—C9—C10177.9 (2)C13—C12—C11—C10−0.1 (4)
C13—C8—C9—C10−0.6 (4)C19—C18—C25—N20.3 (3)
C25—C18—C19—C20−178.9 (3)C17—C18—C25—N2−175.1 (2)
C17—C18—C19—C20−3.6 (5)C24—N2—C25—C18−0.2 (3)
C25—C18—C19—C24−0.3 (3)C15—N1—C16—C17111.3 (3)
C17—C18—C19—C24175.0 (3)C8—C9—C10—C11−0.1 (4)
C8—C7—C6—C5−178.2 (2)C12—C11—C10—C90.5 (4)
C8—C7—C6—C10.8 (4)C24—C23—C22—C21−0.7 (4)
C14—C1—C6—C70.5 (4)C25—C18—C17—C16115.4 (3)
C2—C1—C6—C7−177.2 (2)C19—C18—C17—C16−59.1 (4)
C14—C1—C6—C5179.4 (2)N1—C16—C17—C18−55.6 (3)
C2—C1—C6—C51.8 (4)C19—C20—C21—C220.7 (4)
C14—C1—C2—C3−178.9 (3)C23—C22—C21—C200.2 (4)
C6—C1—C2—C3−1.3 (4)

Hydrogen-bond geometry (Å, º)

Cg3, Cg4 and Cg5 are the centroids rings C1/C6–C8/C13/C14, C8–C13 and C19–C24, respectively.

D—H···AD—HH···AD···AD—H···A
C12—H12···N10.932.362.9845 (2)124
C2—H2···Cg50.932.773.5505 (2)142
N2—H2A···Cg5i0.862.593.1855 (2)127
C7—H7···Cg4ii0.932.753.5777 (2)148
C9—H9···Cg3ii0.932.733.5077 (2)142
C16—H16A···Cg3iii0.972.863.5375 (2)128

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1, y, z.

References

  • Becke, A. D. (1993). J. Chem. Phys. 98, 5648–5652.
  • Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Faizi, M. S. H., Gupta, S., Mohan, V. K., Jain, K. V. & Sen, P. (2016). Sens. Actuators B, 222, 15–20.
  • Faizi, M. S. H. & Sen, P. (2014). Acta Cryst. E70, m206–m207. [PMC free article] [PubMed]
  • Frisch, M. J., et al. (2009). GAUSSIAN09. Gaussian Inc., Wallingford, CT, USA.
  • Glennon, R. A., Titeler, M. & McKenney, J. D. (1984). Life Sci. 35, 2505–2511. [PubMed]
  • Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [PMC free article] [PubMed]
  • Ishida, T., Negi, A., In, Y. & Inoue, M. (1992). Acta Cryst. C48, 193–194.
  • Johnson, M. P., Hoffman, A. J., Nichols, D. E. & Mathis, C. A. (1987). Neuropharmacology, 26, 1803–1806. [PubMed]
  • Jones, R. S. G. (1982). Prog. Neurobiol. 19, 117–139. [PubMed]
  • Krebs-Thomson, K., Paulus, M. P. & Geyer, M. A. (1998). Neuropsychopharmacology, 18, 339–351. [PubMed]
  • Lee, S. K., Yi, K. Y., Kim, S. K., Suh, J., Kim, N. J., Yoo, S., Lee, B. H., Seo, H. W., Kim, S. O. & Lim, H. (2003). Eur. J. Med. Chem. 38, 459–471. [PubMed]
  • Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
  • Mohammad, T. & Moutaery, A. A. (2005). Exp. Tox. Path. 56, 119–129.
  • Nichols, C. D. & Sanders-Bush, E. (2001). Heffter Rev. Psychedelic Res. 2, 73–79.
  • Rodriguez, M. L., Medina de la Rosa, E., Gili, P., Zarza, P. M., Reyes, M. G. M., Medina, A. & Díaz González, M. C. (1987). Acta Cryst. C43, 134–136.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. [PMC free article] [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Takahashi, N. (1986). In Chemistry of Plant Hormones. Florida: CRC Press.
  • Törnroos, K. W. (1988). Acta Cryst. C44, 1238–1240.
  • Waseem, G. & Mark, T. H. (2005). Life Sci. 78, 442–453. [PMC free article] [PubMed]
  • Worthen, D. R., Gibson, D. A., Rogers, D. T., Bence, A. K., Fu, M., Littleton, J. M. & Crooks, P. A. (2001). Brain Res. 890, 343–346. [PubMed]

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography