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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 8| Part 9| September 2023| x230780
https://doi.org/10.1107/S2414314623007800

(2,4-Di­chloro­benzyl­­idene)[2-(1H-indol-3-yl)eth­yl]amine

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Suganya Murugan,a Anaglit Catherine Paul,b Themmila Khamrang,c Savaridasan Jose Kavitha,b Venkatachalam Rajakannand and Madhukar Hemamalinib*

aDepartment of Chemistry, Government Arts and Science College for Women, Kodaikanal, Tamil Nadu, India, bDepartment of Chemistry, Mother Teresa Women's University, Kodaikanal, Tamil Nadu, India, cAssistant Professor, Department of Chemistry, DM College of Science, Dhanamanjuri University, Imphal, Manipur-795 001, India, and dDepartment of Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-600 025, Tamil Nadu, India
*Correspondence e-mail: hemamalini2k3@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 29 August 2023; accepted 6 September 2023; online 12 September 2023)

In the title compound, C17H14Cl2N2, the mol­ecule exists in an E configuration with respect to the C=N bond of the Schiff base fragment. The dihedral angle between the indole ring system and the benzene ring is 80.86 (12)°. In the crystal, mol­ecules are connected by N—H⋯N hydrogen bonds, generating a C(7) chain extending along the a-axis direction. No aromatic π–π stacking occurs but weak C—H⋯π inter­actions are observed.

CCDC reference: 2290063

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Schiff bases are widely used as catalysts, corrosion inhibitors and inter­mediates in organic synthesis, and also play a potential role in the development of coordination chemistry (Muralisankar et al., 2016[Muralisankar, M., Haribabu, J., Bhuvanesh, N. S. P., Karvembu, R. & Sreekanth, A. (2016). Inorg. Chim. Acta, 449, 82-95.]). Indole and its derivatives are useful staring compounds to derive pharmaceutical (Nalli et al., 2020[Nalli, M., Armijos Rivera, J. I., Masci, D., Coluccia, A., Badia, R., Riveira-Muñoz, E., Brambilla, A., Cinquina, E., Turriziani, O., Falasca, F., Catalano, M., Limatola, C., Esté, J. A., Maga, G., Silvestri, R., Crespan, E. & La Regina, G. (2020). Eur. J. Med. Chem. 208, 112696.]) and biological (Arumugam et al., 2021[Arumugam, N., Almansour, A. I., Kumar, R. S., Yeswanthkumar, S., Padmanaban, R., Arun, Y., Kansız, S., Dege, N., Manohar, T. S. & Venketesh, S. (2021). J. Mol. Struct. 1225, 129165-129166.]) mat­erials. In the present study, the hydrogen-bonding inter­actions and C—H⋯π inter­actions of the title compound are investigated.

The asymmetric unit of the title compound is shown in Fig. 1[link]. The C=N double bond adopts an E configuration. The bond lengths and angles in the title mol­ecule are normal and agree with those in other indole–imine compounds (e.g., Suresh et al., 2016[Suresh, D., Ferreira, B., Lopes, P. S., Gomes, C. S. B., Krishnamoorthy, P., Charas, A., Vila-Viçosa, D., Morgado, J., Calhorda, M. J., Maçanita, A. L. & Gomes, P. T. (2016). Dalton Trans. 45, 15603-15620.]; Ho et al., 2006[Ho, J. J., Black, D. St C., Messerle, B. A., Clegg, J. K. & Turner, P. T. (2006). Organometallics, 25, 5800-5810.]). The dihedral angle between the C1–C8/N1 indole ring system and the C12–C17 benzene ring is 80.86 (10)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing 50% displacement ellipsoids.

In the extended structure, the N1—H5 group is a hydrogen-bond donor to atom N2 of the imino group (Table 1[link]). These hydrogen bonds generate a C(7) chain extending along the a-axis direction, as shown in Fig. 2[link]. There are no π–π inter­actions in this crystal structure but weak C—H⋯π inter­actions occur.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H5⋯N2i 0.83 (3) 2.17 (3) 2.971 (3) 163 (2)
Symmetry code: (i) [x-1, y, z].
[Figure 2]
Figure 2
Partial packing diagram for the title compound showing the formation of [100] hydrogen-bonded chains.

A search of the Cambridge Structural Database (Version 5.43, update November 2022; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for the benzyl­idene)-[2-(1H-indol-3-yl)-eth­yl]-amine skeleton yielded the hits 1-(anthracen-9-yl)-N-[2-(1H- indol-3-yl)eth­yl]methanimine (CSD refcode TEGJIB; Faizi et al., 2017[Faizi, M. S. H., Dege, N., Malinkin, S. & Sliva, T. Y. (2017). Acta Cryst. E73, 1329-1332.]), 2-[2-(1H-indol-3-yl­ethyl­imino­meth­yl)]-5-methyl­phenol (PEVXEW; Brink et al., 2018[Brink, A., Kroon, R. E., Visser, H. G., van Rensburg, C. E. J. & Roodt, A. (2018). New J. Chem. 42, 5193-5203.]), rac-4-{(E)-[1-cyano-1-cyclo­hexyl-2-(1H-indol-yl)eth­yl]imino­meth­yl} benzo­nitrile (OCEWIE; Letessier et al., 2011[Letessier, J., Schollmeyer, D., Detert, H. & Opatz, T. (2011). Acta Cryst. E67, o3435.]), 1H-indole-3-ethyl­enesalicylaldimine (FAJVIV; Rodriguez et al., 1987[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.]) and 1-(4-chloro­phen­yl)-2-{[2-(1H-indol-3-yl) eth­yl]imino}-2-(4-meth­oxy­phen­yl)ethan-1-one (AZUYUS; Li et al., 2021[Li, L., Zhang, S., Deng, X., Li, G., Tang, Z. & Zhao, G. (2021). Org. Lett. 23, 6819-6824.]).

Synthesis and crystallization

The title compound was synthesized by condensing tryptamine, 2-(1H-indol-3-yl)ethan-1-amine (0.01 mmol) and 2,4-di­chloro­benzaldehyde (0.01 mmol), which were taken separately, dissolved in 40 ml of ethanol, then mixed, and heated on a water bath for one h, then kept for crystallization. After a few days, colourless plate-shaped crystals were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C17H14Cl2N2
Mr 317.20
Crystal system, space group Monoclinic, P21/n
Temperature (K) 296
a, b, c (Å) 7.2107 (8), 10.2179 (13), 20.863 (3)
β (°) 90.562 (4)
V (Å3) 1537.1 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.42
Crystal size (mm) 0.52 × 0.34 × 0.13
 
Data collection
Diffractometer Agilent Xcalibur, Atlas, Gemini
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.631, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 68672, 3872, 1946
Rint 0.091
(sin θ/λ)max (Å−1) 0.671
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.134, 1.01
No. of reflections 3872
No. of parameters 246
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.20, −0.27
Computer programs: CrysAlis PRO and CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, England.]), SHELXT2018/2 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]).

Structural data

CCDC reference: 2290063

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314623007800/hb4446sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623007800/hb4446Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623007800/hb4446Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: PLATON (Spek, 2020).

(2,4-Dichlorobenzylidene)[2-(1H-indol-3-yl)ethyl]amine top
Crystal data top
C17H14Cl2N2F(000) = 656
Mr = 317.20Dx = 1.371 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2107 (8) ÅCell parameters from 3778 reflections
b = 10.2179 (13) Åθ = 2.6–29.9°
c = 20.863 (3) ŵ = 0.42 mm−1
β = 90.562 (4)°T = 296 K
V = 1537.1 (3) Å3Plate, colourless
Z = 40.52 × 0.34 × 0.13 mm
Data collection top
Agilent Xcalibur, Atlas, Gemini
diffractometer		1946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
ω scansθmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		h = −9→9
Tmin = 0.631, Tmax = 0.746k = −13→13
68672 measured reflectionsl = −27→27
3872 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048All H-atom parameters refined
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0498P)2 + 0.4436P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3872 reflectionsΔρmax = 0.20 e Å−3
246 parametersΔρmin = −0.26 e Å−3
0 restraints
Special details top

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.

Refinement. All the H atoms were located in a difference Fourier map and allowed to refine freely (C—H = 0.93–0.96 and N—H = 0.83 Å).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl20.82313 (10)0.46440 (8)0.37941 (3)0.0896 (3)
Cl10.65404 (13)0.74406 (7)0.58638 (4)0.1034 (3)
N20.6843 (2)0.3930 (2)0.69593 (9)0.0656 (5)
N10.0458 (3)0.2537 (2)0.70118 (10)0.0701 (6)
C50.3287 (3)0.1772 (2)0.68119 (11)0.0628 (6)
C80.3389 (3)0.2540 (2)0.73804 (11)0.0648 (6)
C60.1440 (3)0.1792 (2)0.65910 (11)0.0631 (6)
C120.6934 (3)0.4814 (2)0.58989 (12)0.0593 (6)
C70.1639 (3)0.2993 (3)0.74787 (13)0.0680 (7)
C130.6992 (3)0.5929 (2)0.55222 (12)0.0641 (6)
C140.7393 (3)0.5892 (3)0.48855 (14)0.0683 (7)
C150.7767 (3)0.4709 (3)0.46026 (12)0.0648 (6)
C170.7315 (3)0.3640 (3)0.55950 (14)0.0675 (7)
C110.6416 (3)0.4833 (3)0.65769 (13)0.0661 (7)
C160.7732 (3)0.3571 (3)0.49571 (14)0.0707 (7)
C40.4574 (4)0.1057 (3)0.64506 (16)0.0818 (8)
C100.6134 (4)0.4015 (3)0.76114 (14)0.0785 (8)
C10.0861 (5)0.1121 (3)0.60482 (14)0.0836 (8)
C30.4003 (6)0.0415 (3)0.59108 (17)0.0979 (11)
C90.5055 (4)0.2801 (3)0.77920 (14)0.0796 (8)
C20.2174 (6)0.0439 (3)0.57140 (17)0.0972 (10)
H120.720 (3)0.289 (3)0.5830 (12)0.082 (8)*
H110.573 (3)0.556 (2)0.6692 (10)0.065 (7)*
H100.543 (4)0.476 (3)0.7641 (12)0.081 (9)*
H90.726 (4)0.407 (3)0.7916 (13)0.099 (9)*
H80.586 (4)0.201 (3)0.7761 (12)0.091 (9)*
H40.579 (4)0.105 (3)0.6598 (12)0.083 (9)*
H130.797 (3)0.275 (3)0.4752 (12)0.076 (8)*
H140.743 (3)0.663 (3)0.4649 (12)0.082 (8)*
H70.470 (3)0.290 (2)0.8258 (12)0.078 (7)*
H60.126 (3)0.357 (2)0.7814 (10)0.068 (7)*
H1−0.045 (4)0.108 (3)0.5888 (13)0.106 (10)*
H30.489 (4)−0.005 (3)0.5634 (15)0.119 (11)*
H20.177 (5)−0.006 (4)0.5331 (17)0.132 (13)*
H5−0.060 (4)0.282 (3)0.6933 (12)0.082 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0795 (5)0.1146 (6)0.0746 (5)0.0090 (4)0.0029 (3)0.0035 (4)
Cl10.1558 (8)0.0600 (4)0.0939 (6)0.0151 (4)−0.0242 (5)−0.0064 (4)
N20.0525 (11)0.0758 (14)0.0685 (13)0.0038 (10)−0.0010 (9)0.0048 (11)
N10.0601 (13)0.0747 (15)0.0757 (15)0.0114 (12)0.0050 (11)0.0011 (11)
C50.0652 (15)0.0551 (14)0.0681 (15)0.0121 (11)0.0125 (11)0.0153 (12)
C80.0605 (14)0.0739 (16)0.0602 (14)0.0068 (12)0.0087 (11)0.0181 (13)
C60.0695 (15)0.0528 (14)0.0671 (15)0.0071 (12)0.0078 (12)0.0093 (12)
C120.0467 (12)0.0621 (15)0.0690 (15)0.0059 (11)−0.0094 (10)−0.0004 (12)
C70.0707 (16)0.0718 (17)0.0617 (15)0.0074 (13)0.0119 (13)0.0002 (13)
C130.0644 (14)0.0555 (15)0.0721 (16)0.0053 (11)−0.0151 (12)0.0018 (13)
C140.0659 (16)0.0587 (16)0.0800 (19)−0.0008 (12)−0.0136 (13)0.0104 (15)
C150.0478 (13)0.0780 (18)0.0684 (15)0.0042 (12)−0.0071 (10)0.0065 (14)
C170.0659 (15)0.0596 (16)0.0769 (18)0.0066 (12)−0.0027 (12)0.0089 (14)
C110.0534 (14)0.0663 (17)0.0783 (18)0.0082 (12)−0.0057 (12)−0.0042 (14)
C160.0676 (16)0.0640 (17)0.0803 (19)0.0123 (13)−0.0014 (13)−0.0037 (15)
C40.079 (2)0.0709 (18)0.096 (2)0.0228 (15)0.0201 (17)0.0209 (17)
C100.0702 (18)0.096 (2)0.0690 (18)0.0042 (17)−0.0010 (14)−0.0028 (16)
C10.102 (2)0.0655 (17)0.083 (2)0.0028 (17)−0.0044 (17)−0.0025 (16)
C30.138 (3)0.0652 (19)0.091 (2)0.031 (2)0.032 (2)−0.0007 (17)
C90.0741 (18)0.098 (2)0.0663 (18)0.0031 (16)−0.0018 (14)0.0154 (16)
C20.137 (3)0.0653 (19)0.090 (2)0.010 (2)0.006 (2)−0.0077 (17)
Geometric parameters (Å, º) top
Cl2—C151.724 (3)C14—H140.90 (3)
Cl1—C131.733 (2)C15—C161.378 (4)
N2—C111.256 (3)C17—C161.369 (4)
N2—C101.461 (3)C17—H120.92 (3)
N1—C61.365 (3)C11—H110.92 (2)
N1—C71.369 (3)C16—H130.95 (3)
N1—H50.83 (3)C4—C31.364 (5)
C5—C61.405 (3)C4—H40.93 (3)
C5—C41.406 (4)C10—C91.514 (4)
C5—C81.424 (3)C10—H100.92 (3)
C8—C71.362 (3)C10—H91.03 (3)
C8—C91.494 (4)C1—C21.371 (4)
C6—C11.385 (4)C1—H11.00 (3)
C12—C131.385 (3)C3—C21.377 (5)
C12—C171.386 (3)C3—H30.99 (3)
C12—C111.467 (3)C9—H81.00 (3)
C7—H60.96 (2)C9—H71.01 (2)
C13—C141.363 (4)C2—H20.99 (4)
C14—C151.373 (4)
C11—N2—C10117.5 (2)N2—C11—C12122.7 (2)
C6—N1—C7108.9 (2)N2—C11—H11123.5 (14)
C6—N1—H5123.4 (18)C12—C11—H11113.8 (14)
C7—N1—H5125.7 (19)C17—C16—C15118.9 (3)
C6—C5—C4117.4 (3)C17—C16—H13121.4 (15)
C6—C5—C8107.8 (2)C15—C16—H13119.6 (15)
C4—C5—C8134.7 (3)C3—C4—C5119.8 (3)
C7—C8—C5105.8 (2)C3—C4—H4123.2 (17)
C7—C8—C9126.5 (3)C5—C4—H4117.0 (17)
C5—C8—C9127.7 (2)N2—C10—C9111.6 (3)
N1—C6—C1130.4 (3)N2—C10—H10108.1 (16)
N1—C6—C5107.1 (2)C9—C10—H10112.3 (17)
C1—C6—C5122.5 (2)N2—C10—H9107.3 (15)
C13—C12—C17116.5 (2)C9—C10—H9107.4 (16)
C13—C12—C11123.1 (2)H10—C10—H9110 (2)
C17—C12—C11120.4 (2)C2—C1—C6117.6 (3)
C8—C7—N1110.4 (2)C2—C1—H1117.6 (17)
C8—C7—H6126.3 (14)C6—C1—H1124.7 (17)
N1—C7—H6123.3 (13)C4—C3—C2121.2 (3)
C14—C13—C12122.5 (2)C4—C3—H3121.5 (19)
C14—C13—Cl1117.9 (2)C2—C3—H3117.2 (19)
C12—C13—Cl1119.5 (2)C8—C9—C10114.6 (2)
C13—C14—C15119.2 (3)C8—C9—H8106.5 (16)
C13—C14—H14121.4 (17)C10—C9—H8110.3 (15)
C15—C14—H14119.4 (17)C8—C9—H7111.0 (13)
C14—C15—C16120.5 (3)C10—C9—H7107.0 (14)
C14—C15—Cl2119.7 (2)H8—C9—H7107 (2)
C16—C15—Cl2119.8 (2)C1—C2—C3121.4 (3)
C16—C17—C12122.4 (3)C1—C2—H2118 (2)
C16—C17—H12120.0 (17)C3—C2—H2121 (2)
C12—C17—H12117.5 (16)
C6—C5—C8—C7−0.3 (3)C13—C14—C15—Cl2178.70 (17)
C4—C5—C8—C7179.1 (3)C13—C12—C17—C160.2 (3)
C6—C5—C8—C9179.4 (2)C11—C12—C17—C16177.4 (2)
C4—C5—C8—C9−1.1 (4)C10—N2—C11—C12−175.7 (2)
C7—N1—C6—C1179.5 (3)C13—C12—C11—N2−159.7 (2)
C7—N1—C6—C50.9 (3)C17—C12—C11—N223.3 (4)
C4—C5—C6—N1−179.9 (2)C12—C17—C16—C15−0.3 (4)
C8—C5—C6—N1−0.4 (3)C14—C15—C16—C170.1 (4)
C4—C5—C6—C11.4 (4)Cl2—C15—C16—C17−178.35 (18)
C8—C5—C6—C1−179.1 (2)C6—C5—C4—C3−0.3 (4)
C5—C8—C7—N10.9 (3)C8—C5—C4—C3−179.7 (3)
C9—C8—C7—N1−178.9 (2)C11—N2—C10—C9124.4 (3)
C6—N1—C7—C8−1.1 (3)N1—C6—C1—C2−179.7 (3)
C17—C12—C13—C140.2 (3)C5—C6—C1—C2−1.4 (4)
C11—C12—C13—C14−176.9 (2)C5—C4—C3—C2−0.7 (5)
C17—C12—C13—Cl1−179.82 (17)C7—C8—C9—C10−89.3 (3)
C11—C12—C13—Cl13.1 (3)C5—C8—C9—C1091.0 (3)
C12—C13—C14—C15−0.4 (4)N2—C10—C9—C8−60.8 (4)
Cl1—C13—C14—C15179.62 (17)C6—C1—C2—C30.3 (5)
C13—C14—C15—C160.2 (4)C4—C3—C2—C10.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H5···N2i0.83 (3)2.17 (3)2.971 (3)163 (2)
Symmetry code: (i) x−1, y, z.
 

Acknowledgements

MH thanks SERB-IRE for financial support (Ref. No. SIR/2022/000011]. SJK thanks TANSCHE for financial support (File No. RGP/2019–20/MTWU/ HECP-0080).

Funding information

Funding for this research was provided by: Department of Science and Technology, Ministry of Science and Technology, India, Science and Engineering Research Board (grant No. SIR/2022/000011); Tamil Nadu State Council for Higher Education (grant No. RGP/2019-20/MTWU/HECP-0080).

References

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Volume 8| Part 9| September 2023| x230780
https://doi.org/10.1107/S2414314623007800