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

Journal logoIUCrDATA
ISSN: 2414-3146

1-(Pyridin-4-yl)-3-(2,4,6-tri­chloro­phen­yl)benz[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

CROSSMARK_Color_square_no_text.svg

aFaculty of Science, Chemistry Department, Islamic University of Gaza Strip, Gaza Strip, Palestinian Territories, bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany, cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Alazhar University-Gaza, Gaza Strip, Palestinian Territories, dDeparyment of Organic Chemistry, The Islamic University of Gaza Strip, Gaza Strip, Palestinian Territories, eHochschule Furtwangen (HFU), Fakultät Medical and Life Sciences, Jakob-Kienzle Strasse 17, 78054 Villingen-Schwenningen, Germany, and fFraunhofer IZI, Perlickstrasse 1, 04103 Leipzig, Germany
*Correspondence e-mail: dei@hs-furtwangen.de

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 27 September 2016; accepted 28 September 2016; online 4 October 2016)

In the title compound, C20H10Cl3N5O, the 13-membered ring system makes dihedral angles of 78.64 (9)° with the tri­chloro­phenyl ring and 62.60 (10)° with the pyridine ring. The crystal packing is dominated by ππ inter­actions between the 13-membered ring systems [centroid–centroid distance = 3.6655 (11)°].

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

Structure description

Compounds containing a benzimidazole core have been investigated as pharmaceuticals (Karpińka et al., 2011[Karpińka, M. M., Matysiak, J. & Niewiadomy, A. (2011). Arch. Pharm. Res. 34, 1639-1647.]; Singh et al., 2010[Singh, S., Ojha, H., Tiwari, A. K., Kumar, N., Singh, B. & Mishra, A. K. (2010). Cancer Biother. Radiopharm. 25, 245-250.]) and therapeutic agents (Biron, 2006[Biron, K. K. (2006). Antivir. Res. 71, 154-163.]; Pescovitz, 2008[Pescovitz, M. D. (2008). Future Virol. 3, 435-443.]), and feature as commercial drugs such as omeprazole (Prilosec), pantoprazole (Protonix), vermox and mibefradil (Karpin'ska et al., 2011). Several benzimidazole based compounds show anti-cancer activity (Thomas et al., 2007[Thomas, H. D., Calabrese, C. R., Batey, M. A., Canan, S., Hostomsky, Z., Kyle, S., Maegley, K. A., Newell, D. R., Skalitzky, D., Wang, L. Z., Webber, S. E. & Curtin, N. J. (2007). Mol. Cancer Ther. 6, 945-956.]), some exhibiting cytotoxic effects against a panel of human cancer cell lines (Refaat, 2010[Refaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949-2956.]). For example, benzimidazole-4,7-diones exhibit cytotoxicity against colon, breast and lung cell lines (Gellis et al., 2008[Gellis, A., Kovacic, H., Boufatah, N. & Vanelle, P. (2008). Eur. J. Med. Chem. 43, 1858-1864.]). The good efficacy of imidazole-based compounds as anti-cancer agents promoted our work to synthesize a masked benzimidazole in a triazine ring as a new scaffold of a potential anti-cancer candidate. The first derivative of this series gave a good crystal and its structure has been published (Abu Thaher et al., 2016[Abu Thaher, B. A., Schollmeyer, D., Qeshta, B. & Deigner, H.-P. (2016). IUCrData, 1, x161380.]).

In the title compound (Fig. 1[link]), the central 13-membered ring is essentially planar with a maximum deviation of 0.133 (2) Å for atom N1 and makes dihedral angles of 78.64 (9)° with the tri­chloro­phenyl ring and 62.60 (10)° with the pyridine ring. In the crystal, two mol­ecules related by a centre of inversion show a ππ inter­action. The distance between centroids of the C7–C12 and N1/C5/N6/C7/C12([{1\over 2}] − x, [{1\over 2}] − y, 1 − z) rings is 3.6655 (11)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

Synthesis and crystallization

3.1 mmol of NaH was added slowly to a solution of 3.1 mmol of ethyl-2- benzimidazolcarboxyl­ate in 30 ml dry THF and stirring continued at room temperature for about 20 minutes. To this flask, 3.0 mmol of N-(2,4,6-tri­chloro­phen­yl)-4-pyridine­carbohydrazonoyl chloride was added slowly portionwise and in parallel 0.5 ml of Et3N was added drop wise. The reaction was left stirring overnight, monitored by TLC until it had finished. The reaction was filtered and concentrated under vacuum. The solid residue was purified by column chromatography (hexa­ne:ethyl acetate; 2:1, then 1:1). Yield: 20%. Suitable crystals for X-ray analysis were obtained by slow evaporation of a hexa­ne/ethyl acetate solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula C20H10Cl3N5O
Mr 442.68
Crystal system, space group Monoclinic, C2/c
Temperature (K) 193
a, b, c (Å) 19.5521 (12), 15.1072 (5), 15.5543 (9)
β (°) 126.057 (4)
V3) 3714.2 (4)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.52
Crystal size (mm) 0.35 × 0.21 × 0.20
 
Data collection
Diffractometer Stoe IPDS 2T
No. of measured, independent and observed [I > 2σ(I)] reflections 11381, 4574, 3437
Rint 0.022
(sin θ/λ)max−1) 0.665
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.113, 1.04
No. of reflections 4574
No. of parameters 262
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.89, −0.98
Computer programs: X-AREA (Stoe & Cie, 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), X-AREA (Stoe & Cie, 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), X-RED32 (Stoe & Cie, 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SIR2004 (Altomare et al., 1995[Altomare, A., Burla, M. C., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G. & Polidori, G. (1995). J. Appl. Cryst. 28, 842-846.]) and SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2006a); cell refinement: X-AREA (Stoe & Cie, 2006); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR2004 (Altomare et al., 1995); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

1-(Pyridin-4-yl)-3-(2,4,6-trichlorophenyl)benz[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one top
Crystal data top
C20H10Cl3N5OF(000) = 1792
Mr = 442.68Dx = 1.583 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 19.5521 (12) ÅCell parameters from 12681 reflections
b = 15.1072 (5) Åθ = 2.6–28.3°
c = 15.5543 (9) ŵ = 0.52 mm1
β = 126.057 (4)°T = 193 K
V = 3714.2 (4) Å3Plate, colourless
Z = 80.35 × 0.21 × 0.20 mm
Data collection top
Stoe IPDS 2T
diffractometer
3437 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusRint = 0.022
Detector resolution: 6.67 pixels mm-1θmax = 28.2°, θmin = 2.6°
rotation method scansh = 2520
11381 measured reflectionsk = 2018
4574 independent reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.051P)2 + 3.9605P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4574 reflectionsΔρmax = 0.89 e Å3
262 parametersΔρmin = 0.98 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.32853 (6)0.12694 (4)0.13199 (6)0.0620 (2)
Cl20.43245 (5)0.39787 (5)0.01324 (6)0.0644 (2)
Cl30.34201 (5)0.45705 (4)0.27335 (5)0.05540 (18)
O10.18165 (10)0.29896 (13)0.14004 (12)0.0496 (4)
N10.27697 (10)0.17190 (11)0.37941 (11)0.0276 (3)
N20.37972 (10)0.20832 (11)0.35279 (12)0.0300 (3)
N30.31780 (11)0.25749 (12)0.26496 (12)0.0336 (4)
C10.35845 (11)0.16738 (12)0.40623 (13)0.0272 (4)
C40.23280 (13)0.25910 (15)0.22150 (14)0.0359 (4)
C50.21233 (12)0.21304 (14)0.28666 (14)0.0316 (4)
N60.13953 (10)0.21308 (12)0.27260 (12)0.0346 (4)
C70.15680 (12)0.17234 (13)0.36360 (14)0.0303 (4)
C80.10192 (12)0.16098 (14)0.39282 (15)0.0336 (4)
H80.04420.17820.34690.040*
C90.13499 (13)0.12388 (14)0.49083 (15)0.0345 (4)
H90.09940.11570.51310.041*
C100.21982 (13)0.09796 (14)0.55831 (15)0.0338 (4)
H100.24010.07220.62510.041*
C110.27507 (12)0.10858 (13)0.53118 (14)0.0305 (4)
H110.33270.09100.57750.037*
C120.24185 (11)0.14642 (12)0.43222 (13)0.0271 (4)
C130.42283 (11)0.11300 (12)0.49832 (13)0.0264 (4)
C140.40997 (13)0.02308 (13)0.50356 (17)0.0344 (4)
H140.35950.00540.44790.041*
C150.47300 (15)0.02355 (15)0.59233 (19)0.0429 (5)
H150.46470.08510.59540.051*
N160.54470 (12)0.01269 (14)0.67379 (15)0.0459 (5)
C170.55553 (14)0.09801 (16)0.66609 (16)0.0415 (5)
H170.60640.12480.72310.050*
C180.49758 (12)0.15087 (13)0.58041 (14)0.0317 (4)
H180.50910.21160.57830.038*
C190.34486 (13)0.29350 (14)0.20419 (15)0.0344 (4)
C200.35514 (14)0.23695 (14)0.14171 (16)0.0389 (5)
C210.38352 (15)0.26848 (16)0.08389 (18)0.0442 (5)
H210.39180.22950.04280.053*
C220.39927 (15)0.35738 (17)0.08770 (18)0.0441 (5)
C230.38711 (16)0.41627 (16)0.14555 (17)0.0440 (5)
H230.39710.47780.14550.053*
C240.35979 (14)0.38281 (15)0.20364 (16)0.0381 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1095 (6)0.0359 (3)0.0802 (4)0.0179 (3)0.0779 (5)0.0153 (3)
Cl20.0942 (5)0.0645 (4)0.0793 (4)0.0099 (4)0.0760 (4)0.0183 (3)
Cl30.0916 (5)0.0457 (3)0.0555 (3)0.0027 (3)0.0581 (4)0.0002 (3)
O10.0444 (9)0.0751 (12)0.0349 (7)0.0228 (8)0.0265 (7)0.0253 (7)
N10.0283 (7)0.0344 (8)0.0220 (6)0.0037 (6)0.0159 (6)0.0034 (6)
N20.0303 (8)0.0341 (8)0.0271 (7)0.0074 (7)0.0178 (6)0.0073 (6)
N30.0364 (9)0.0420 (9)0.0293 (7)0.0113 (7)0.0232 (7)0.0133 (7)
C10.0289 (9)0.0283 (9)0.0263 (8)0.0017 (7)0.0174 (7)0.0009 (7)
C40.0377 (11)0.0473 (12)0.0277 (8)0.0121 (9)0.0220 (8)0.0099 (8)
C50.0300 (9)0.0411 (11)0.0231 (8)0.0076 (8)0.0152 (7)0.0055 (7)
N60.0319 (8)0.0461 (10)0.0274 (7)0.0078 (7)0.0182 (7)0.0063 (7)
C70.0330 (9)0.0339 (10)0.0265 (8)0.0025 (8)0.0189 (7)0.0001 (7)
C80.0314 (9)0.0405 (11)0.0323 (9)0.0027 (8)0.0206 (8)0.0006 (8)
C90.0382 (10)0.0396 (11)0.0357 (9)0.0021 (9)0.0272 (9)0.0030 (8)
C100.0417 (11)0.0360 (10)0.0295 (9)0.0002 (9)0.0241 (8)0.0017 (8)
C110.0335 (9)0.0341 (10)0.0252 (8)0.0027 (8)0.0181 (7)0.0017 (7)
C120.0300 (9)0.0302 (9)0.0253 (8)0.0002 (7)0.0185 (7)0.0011 (7)
C130.0280 (8)0.0286 (9)0.0264 (8)0.0030 (7)0.0181 (7)0.0038 (7)
C140.0325 (10)0.0297 (10)0.0456 (10)0.0014 (8)0.0256 (9)0.0025 (8)
C150.0469 (12)0.0328 (11)0.0631 (14)0.0107 (9)0.0402 (12)0.0177 (10)
N160.0430 (10)0.0521 (12)0.0448 (10)0.0175 (9)0.0270 (9)0.0224 (9)
C170.0361 (11)0.0492 (13)0.0293 (9)0.0055 (10)0.0137 (8)0.0048 (9)
C180.0321 (9)0.0322 (10)0.0289 (9)0.0027 (8)0.0169 (8)0.0020 (7)
C190.0394 (10)0.0410 (11)0.0321 (9)0.0118 (9)0.0262 (8)0.0125 (8)
C200.0501 (12)0.0373 (11)0.0414 (10)0.0165 (9)0.0336 (10)0.0152 (9)
C210.0599 (14)0.0460 (13)0.0458 (11)0.0210 (11)0.0416 (11)0.0167 (10)
C220.0533 (13)0.0531 (14)0.0437 (11)0.0105 (11)0.0384 (11)0.0161 (10)
C230.0576 (14)0.0431 (13)0.0443 (11)0.0027 (10)0.0373 (11)0.0078 (9)
C240.0450 (12)0.0444 (12)0.0328 (9)0.0070 (9)0.0273 (9)0.0064 (8)
Geometric parameters (Å, º) top
Cl1—C201.721 (2)C10—H100.9500
Cl2—C221.738 (2)C11—C121.393 (2)
Cl3—C241.732 (2)C11—H110.9500
O1—C41.215 (2)C13—C181.377 (3)
N1—C51.385 (2)C13—C141.393 (3)
N1—C11.391 (2)C14—C151.385 (3)
N1—C121.400 (2)C14—H140.9500
N2—C11.286 (2)C15—N161.334 (3)
N2—N31.392 (2)C15—H150.9500
N3—C41.377 (3)N16—C171.323 (3)
N3—C191.435 (2)C17—C181.386 (3)
C1—C131.479 (2)C17—H170.9500
C4—C51.466 (3)C18—H180.9500
C5—N61.307 (2)C19—C241.382 (3)
N6—C71.391 (2)C19—C201.395 (3)
C7—C81.400 (3)C20—C211.390 (3)
C7—C121.403 (3)C21—C221.371 (3)
C8—C91.377 (3)C21—H210.9500
C8—H80.9500C22—C231.382 (3)
C9—C101.399 (3)C23—C241.388 (3)
C9—H90.9500C23—H230.9500
C10—C111.381 (3)
C5—N1—C1121.08 (15)C18—C13—C14118.72 (17)
C5—N1—C12105.83 (15)C18—C13—C1120.06 (17)
C1—N1—C12132.97 (15)C14—C13—C1121.22 (17)
C1—N2—N3117.77 (16)C15—C14—C13117.98 (19)
C4—N3—N2126.33 (16)C15—C14—H14121.0
C4—N3—C19118.44 (15)C13—C14—H14121.0
N2—N3—C19113.84 (15)N16—C15—C14124.0 (2)
N2—C1—N1122.12 (16)N16—C15—H15118.0
N2—C1—C13118.59 (16)C14—C15—H15118.0
N1—C1—C13119.29 (15)C17—N16—C15116.66 (18)
O1—C4—N3122.37 (18)N16—C17—C18124.4 (2)
O1—C4—C5124.34 (19)N16—C17—H17117.8
N3—C4—C5113.19 (15)C18—C17—H17117.8
N6—C5—N1114.25 (16)C13—C18—C17118.23 (19)
N6—C5—C4126.71 (17)C13—C18—H18120.9
N1—C5—C4118.69 (17)C17—C18—H18120.9
C5—N6—C7103.98 (15)C24—C19—C20118.44 (18)
N6—C7—C8127.68 (18)C24—C19—N3122.39 (18)
N6—C7—C12111.52 (16)C20—C19—N3119.16 (19)
C8—C7—C12120.69 (17)C21—C20—C19121.1 (2)
C9—C8—C7117.32 (18)C21—C20—Cl1119.30 (17)
C9—C8—H8121.3C19—C20—Cl1119.51 (16)
C7—C8—H8121.3C22—C21—C20118.2 (2)
C8—C9—C10121.43 (18)C22—C21—H21120.9
C8—C9—H9119.3C20—C21—H21120.9
C10—C9—H9119.3C21—C22—C23122.57 (19)
C11—C10—C9122.24 (17)C21—C22—Cl2118.58 (17)
C11—C10—H10118.9C23—C22—Cl2118.82 (19)
C9—C10—H10118.9C22—C23—C24118.0 (2)
C10—C11—C12116.45 (17)C22—C23—H23121.0
C10—C11—H11121.8C24—C23—H23121.0
C12—C11—H11121.8C19—C24—C23121.6 (2)
C11—C12—N1133.68 (17)C19—C24—Cl3120.51 (15)
C11—C12—C7121.88 (17)C23—C24—Cl3117.90 (18)
N1—C12—C7104.36 (15)
C1—N2—N3—C47.9 (3)C8—C7—C12—C110.1 (3)
C1—N2—N3—C19174.11 (18)N6—C7—C12—N10.7 (2)
N3—N2—C1—N10.7 (3)C8—C7—C12—N1177.00 (18)
N3—N2—C1—C13178.54 (16)N2—C1—C13—C1857.3 (2)
C5—N1—C1—N27.2 (3)N1—C1—C13—C18123.43 (19)
C12—N1—C1—N2168.14 (19)N2—C1—C13—C14121.9 (2)
C5—N1—C1—C13172.08 (17)N1—C1—C13—C1457.3 (2)
C12—N1—C1—C1312.6 (3)C18—C13—C14—C150.8 (3)
N2—N3—C4—O1174.6 (2)C1—C13—C14—C15179.91 (17)
C19—N3—C4—O19.0 (3)C13—C14—C15—N161.0 (3)
N2—N3—C4—C58.9 (3)C14—C15—N16—C171.7 (3)
C19—N3—C4—C5174.55 (18)C15—N16—C17—C180.5 (3)
C1—N1—C5—N6179.24 (17)C14—C13—C18—C171.9 (3)
C12—N1—C5—N62.8 (2)C1—C13—C18—C17178.83 (17)
C1—N1—C5—C45.5 (3)N16—C17—C18—C131.3 (3)
C12—N1—C5—C4170.92 (17)C4—N3—C19—C2484.0 (3)
O1—C4—C5—N65.5 (4)N2—N3—C19—C24108.6 (2)
N3—C4—C5—N6170.9 (2)C4—N3—C19—C2094.8 (2)
O1—C4—C5—N1178.4 (2)N2—N3—C19—C2072.6 (2)
N3—C4—C5—N12.0 (3)C24—C19—C20—C213.0 (3)
N1—C5—N6—C72.3 (2)N3—C19—C20—C21178.17 (19)
C4—C5—N6—C7170.8 (2)C24—C19—C20—Cl1174.58 (16)
C5—N6—C7—C8175.1 (2)N3—C19—C20—Cl14.3 (3)
C5—N6—C7—C121.0 (2)C19—C20—C21—C221.6 (3)
N6—C7—C8—C9175.5 (2)Cl1—C20—C21—C22175.98 (18)
C12—C7—C8—C90.2 (3)C20—C21—C22—C230.7 (4)
C7—C8—C9—C100.4 (3)C20—C21—C22—Cl2178.54 (18)
C8—C9—C10—C110.5 (3)C21—C22—C23—C241.6 (4)
C9—C10—C11—C120.2 (3)Cl2—C22—C23—C24179.36 (18)
C10—C11—C12—N1176.0 (2)C20—C19—C24—C232.1 (3)
C10—C11—C12—C70.0 (3)N3—C19—C24—C23179.1 (2)
C5—N1—C12—C11174.6 (2)C20—C19—C24—Cl3176.14 (16)
C1—N1—C12—C111.2 (4)N3—C19—C24—Cl32.7 (3)
C5—N1—C12—C71.9 (2)C22—C23—C24—C190.1 (3)
C1—N1—C12—C7177.75 (19)C22—C23—C24—Cl3178.39 (18)
N6—C7—C12—C11176.42 (18)
 

Acknowledgements

BAT thanks the Palestinian Research Council (Ramallah) for funding and HFU (Germany) for hosting.

References

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