research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Crystal structures of pure 3-(4-bromo-2-chloro­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one and contaminated with 3-(4-bromo­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

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aFaculty of Pharmacy, Department of Pharmaceutical Chemistry, Alazhar University-Gaza, Gaza Strip, Palestinian Territories, bFaculty of Science, Chemistry Department, Islamic University of Gaza Strip, Gaza Strip, Palestinian Territories, cDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany, dHochschule Furtwangen (HFU), Fakultät Medical and Life Sciences, Jakob-Kienzle Strasse 17, 78054 Villingen-Schwenningen, Germany, and eFraunhofer IZI, EXIM Rostock, Perlickstrasse 1, 04103 Leipzig, Germany
*Correspondence e-mail: deigner@gmx.de

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 7 August 2017; accepted 10 August 2017; online 15 August 2017)

The side product of the cyclo­condensation reaction between ethyl benzimidazole-2-carboxyl­ate and the nitrile imine of the corresponding hydrazonyl chloride, C20H11BrClN5O, crystallized in two crystal forms. Form (1) is a co-crystal of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromo­phenyl group, C20H12BrN5O·0.143C20H11BrClN5O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by ππ inter­actions.

1. Chemical context

Compounds containing a benzimidazole core have been tackled in the area of pharmaceuticals (Karpin'ska 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 areas (Biron, 2006[Biron, K. K. (2006). Antiviral Res. 71, 154-163.]; Pescovitz, 2008[Pescovitz, M. D. (2008). Future Virol. 3, 435-443.]), as well as commercial drugs such as omeprazole (prilosec), pantoprazole (protonix), vermox and mibefradil (Karpińska et al., 2011[Karpińka, M. M., Matysiak, J. & Niewiadomy, A. (2011). Arch. Pharm. Res. 34, 1639-1647.]). 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.]), and some of them exhibit 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 efficiency of imidazole-based compounds as anti-cancer agents promoted this study of synthesizing a masked benzimidazole in a triazine ring as a new scaffold with potential anti-cancer candidates. The first and the second derivative of this series afforded good crystals and have been published previously (Abu Thaher et al., 2016a[Abu Thaher, B. A., Schollmeyer, D., Qeshta, B. & Deigner, H.-P. (2016a). IUCrData, 1, x161380.],b[Abu Thaher, B. A., Schollmeyer, D., Qeshta, B., Wahedy, K. M., Almasri, I. M., Morjan, R. Y. & Deigner, H. (2016b). IUCrData, 1, x161529.]). The aim of this study was to prepare 3-(4-bromo­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imid­azo[1,2-d][1,2,4]-triazin-4(3H)-one.

2. Structural commentary

During crystallization of the product from a bi-solvent mixture of n-heptane and EtAc, two types of crystals were obtained. The biggest and highest quality blocks among them, (1) (Fig. 1[link]), were obtained as a co-crystal of the target compound and a side product containing a chlorine atom in position 2 of the bromo­phenyl group. The chlorine atom in it is attached to the bromo­phenyl group as a side product obtained during preparation of the starting material, namely hydrazonoyl chloride, via chlorination of the corresponding hydrazone. The quantitative ratio between the side:target product is 1:7. The second type of crystals, (2), nice column-like crystals, turned out to contain the pure side product (Fig. 2[link]). Furthermore, crystals of (2) contain two independent mol­ecules (A and B) in the asymmetric unit. Their geometry is almost identical but different from (1) (see Table 1[link]). The r.m.s. fit of all non-hydrogen atoms from molecule A onto B is 0.116 Å. The fused 13-membered ring system in (1) and (2) is nearly planar with an r.m.s. deviation of 0.025 Å in (1) and an r.m.s. deviation of 0.100 Å for mol­ecule A and 0.089 Å for mol­ecule B of (2).

[Scheme 1]

Table 1
Torsion angles (°)

Compound N13—N1—C14—C15 N13—C12—C21—C26
(1) −42.3 (4) 53.6 (5)
(2A) −53.3 (5) −45.9 (6)
(2B) −53.7 (5) −56.8 (6)
[Figure 1]
Figure 1
The crystal structure of (1), with the atom labelling and displacement ellipsoids drawn at the 50% probability level. The Cl atom has a site-occupation factor of only 1/8.
[Figure 2]
Figure 2
The crystal structure of (2) with the atom labelling. Displacement ellipsoids drawn at the 50% probability level. The two independent mol­ecules are labelled with suffixes A and B.

3. Supra­molecular features

The packing of (1) and (2) is dominated by ππ inter­actions. In (1), the 13-membered rings related by a centre of inversion are stacked with a distance of 3.513 (2) Å between the centroids of two five-membered rings (symmetry operator: [{1\over 2}] − x, [{3\over 2}] − y, 1 − z). In (2), the six-membered ring C14A–C19A shows a short ππ inter­action of 3.848 (3) Å with its inversion-related equivalent (symmetry operator: 2 − x, 1 − y, 1 − z). In addition, weak C—H⋯O and C—H⋯Br hydrogen bonds stabilize the crystal packing in (1) (see Table 2[link]).

Table 2
Hydrogen-bond geometry (Å, °) for (1)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O20i 0.95 2.53 3.258 (5) 134
C15—H15⋯O20ii 0.95 2.30 3.219 (5) 162
C23—H23⋯Br1iii 0.95 2.97 3.417 (4) 110
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) [-x, y+1, -z+{\script{3\over 2}}].

4. Database survey

Two similar structures have been published previously (Abu Thaher et al., 2016a[Abu Thaher, B. A., Schollmeyer, D., Qeshta, B. & Deigner, H.-P. (2016a). IUCrData, 1, x161380.],b[Abu Thaher, B. A., Schollmeyer, D., Qeshta, B., Wahedy, K. M., Almasri, I. M., Morjan, R. Y. & Deigner, H. (2016b). IUCrData, 1, x161529.]). All crystal structures show the typical ππ inter­action of the fused 13-membered ring system. The angles between the least-squares planes through the pyridine ring and the 13-membered ring vary from 50.38 (17) to 79.98 (7)°, probably depending on the mol­ecular packing, while the angles between the substituted phenyl ring and the 13-membered ring range from 43.13 (15) to 78.64 (9)° depending on the size of the substituent.

5. Synthesis and crystallization

50.4 mg of NaH was added slowly to a solution of 399.4 mg of ethyl-2-benzimidazolcarboxyl­ate in 30 ml dry THF and stirring continued at 298 K for 20 min. Then, 694 mg of N-(4-bromo­phen­yl)-4-pyridine­carbohydrazonoyl chloride·HCl was added slowly in a portion-wise manner; in parallel 0.5 ml of Et3N was added dropwise. The reaction was stirred overnight (about 12 h); the reaction mixture was filtered and concentrated under vacuum. The solid residue was purified by column chromatography (SiO2, hepta­ne:ethyl acetate; 2:1, then 1:1). Suitable crystals for X-ray were obtained by slow evaporation of hepta­ne/ethyl acetate (1:1).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (Csp3 atom). All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom). The s.o.f. for the chlorine atom in (1) was initially refined and then fixed at 0.125.

Table 3
Experimental details

  (1) (2)
Crystal data
Chemical formula C20H12BrN5O·0.143C20H11BrClN5O C20H11BrClN5O
Mr 422.56 452.70
Crystal system, space group Monoclinic, C2/c Monoclinic, P21/c
Temperature (K) 193 173
a, b, c (Å) 25.7608 (18), 11.0507 (5), 12.2709 (10) 7.1074 (7), 32.754 (3), 16.1505 (15)
β (°) 90.955 (6) 98.914 (3)
V3) 3492.7 (4) 3714.4 (6)
Z 8 8
Radiation type Mo Kα Mo Kα
μ (mm−1) 2.39 2.38
Crystal size (mm) 0.28 × 0.26 × 0.12 0.28 × 0.03 × 0.02
 
Data collection
Diffractometer Stoe IPDS 2T Bruker SMART APEXII
Absorption correction Integration (X-RED32; Stoe & Cie 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.488, 0.744 0.872, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections 11699, 4317, 2369 31679, 8805, 3614
Rint 0.041 0.152
(sin θ/λ)max−1) 0.666 0.657
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.142, 1.03 0.047, 0.089, 0.72
No. of reflections 4317 8805
No. of parameters 253 505
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.65, −0.69 0.42, −0.49
Computer programs: X-AREA and X-RED32 (Stoe & Cie 2006[Stoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SMART and SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]a) and SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]b).

Supporting information


Computing details top

Data collection: X-AREA (Stoe & Cie 2006) for (1); SMART and SAINT (Bruker, 1997) for (2). Cell refinement: X-AREA (Stoe & Cie 2006) for (1); SMART and SAINT (Bruker, 1997) for (2). Data reduction: X-RED32 (Stoe & Cie 2006) for (1); SMART and SAINT (Bruker, 1997) for (2). For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

3-(4-Bromo-2-chlorophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one–3-(4-bromophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one (1/7) (1) top
Crystal data top
C20H12BrN5O·0.143C20H11BrClN5OF(000) = 1696
Mr = 422.56Dx = 1.607 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 25.7608 (18) ÅCell parameters from 9637 reflections
b = 11.0507 (5) Åθ = 2.0–28.2°
c = 12.2709 (10) ŵ = 2.39 mm1
β = 90.955 (6)°T = 193 K
V = 3492.7 (4) Å3Needle, colourless
Z = 80.28 × 0.26 × 0.12 mm
Data collection top
Stoe IPDS 2T
diffractometer
4317 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2369 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.041
rotation method scansθmax = 28.3°, θmin = 2.6°
Absorption correction: integration
(X-RED32; Stoe & Cie 2006)
h = 3434
Tmin = 0.488, Tmax = 0.744k = 1414
11699 measured reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0663P)2 + 0.855P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4317 reflectionsΔρmax = 0.65 e Å3
253 parametersΔρmin = 0.69 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*/UeqOcc. (<1)
Br10.02345 (2)0.15248 (4)0.54904 (4)0.06608 (19)
N10.11796 (12)0.5865 (3)0.4925 (2)0.0379 (7)
C20.14764 (14)0.6114 (4)0.4030 (3)0.0390 (8)
C30.17585 (14)0.7263 (4)0.4112 (3)0.0399 (8)
N40.20640 (12)0.7717 (3)0.3376 (3)0.0467 (8)
C50.22548 (14)0.8765 (4)0.3860 (3)0.0448 (9)
C60.25926 (16)0.9629 (5)0.3428 (4)0.0548 (11)
H60.27270.95400.27170.066*
C70.27228 (16)1.0608 (5)0.4064 (4)0.0580 (12)
H70.29451.12130.37790.070*
C80.25371 (17)1.0735 (4)0.5117 (4)0.0558 (11)
H80.26421.14200.55340.067*
C90.22053 (15)0.9903 (4)0.5579 (3)0.0483 (10)
H90.20840.99870.63020.058*
C100.20604 (14)0.8931 (4)0.4914 (3)0.0421 (9)
N110.17314 (11)0.7939 (3)0.5062 (2)0.0366 (7)
C120.14121 (14)0.7566 (3)0.5906 (3)0.0361 (8)
N130.11540 (11)0.6577 (3)0.5851 (2)0.0374 (6)
C140.08654 (14)0.4794 (3)0.5007 (3)0.0385 (8)
C150.08749 (17)0.4173 (4)0.5986 (3)0.0481 (9)
H150.11040.44140.65600.058*
C160.05456 (17)0.3193 (4)0.6119 (4)0.0523 (10)
H160.05450.27610.67880.063*
C170.02186 (16)0.2848 (4)0.5275 (4)0.0485 (9)
C180.02157 (15)0.3456 (4)0.4294 (3)0.0467 (9)
H180.00090.32030.37170.056*
C190.05422 (15)0.4436 (4)0.4156 (3)0.0441 (9)
H190.05440.48600.34830.053*0.875
O200.15031 (10)0.5434 (3)0.3248 (2)0.0490 (7)
Cl10.0394 (3)0.5181 (8)0.3084 (6)0.0457 (17)0.125
C210.13313 (13)0.8320 (3)0.6879 (3)0.0366 (8)
C220.11511 (16)0.9496 (4)0.6782 (3)0.0461 (9)
H220.11020.98620.60880.055*
C230.10454 (18)1.0123 (4)0.7731 (4)0.0550 (11)
H230.09231.09310.76630.066*
N240.11042 (14)0.9671 (3)0.8731 (3)0.0533 (9)
C250.12787 (16)0.8544 (4)0.8800 (3)0.0479 (9)
H250.13280.82060.95060.057*
C260.13934 (14)0.7828 (3)0.7911 (3)0.0414 (8)
H260.15120.70200.80060.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0666 (3)0.0435 (2)0.0878 (4)0.0127 (2)0.0093 (2)0.0036 (2)
N10.0417 (16)0.0385 (16)0.0337 (15)0.0010 (14)0.0011 (13)0.0041 (13)
C20.0370 (19)0.051 (2)0.0291 (18)0.0038 (17)0.0010 (14)0.0004 (16)
C30.0360 (18)0.051 (2)0.0334 (18)0.0052 (17)0.0037 (15)0.0040 (16)
N40.0416 (17)0.059 (2)0.0402 (17)0.0040 (16)0.0064 (14)0.0069 (16)
C50.0339 (18)0.060 (3)0.040 (2)0.0046 (18)0.0047 (15)0.0128 (18)
C60.042 (2)0.072 (3)0.051 (2)0.000 (2)0.0030 (18)0.023 (2)
C70.043 (2)0.066 (3)0.066 (3)0.008 (2)0.001 (2)0.029 (2)
C80.049 (2)0.056 (3)0.063 (3)0.013 (2)0.006 (2)0.015 (2)
C90.044 (2)0.054 (2)0.047 (2)0.0078 (19)0.0043 (17)0.0080 (19)
C100.0340 (18)0.046 (2)0.047 (2)0.0005 (16)0.0012 (16)0.0134 (17)
N110.0346 (15)0.0443 (17)0.0309 (14)0.0018 (14)0.0033 (12)0.0035 (13)
C120.0374 (18)0.0374 (19)0.0336 (18)0.0012 (16)0.0028 (14)0.0028 (15)
N130.0421 (16)0.0377 (16)0.0325 (14)0.0008 (15)0.0029 (12)0.0019 (13)
C140.0402 (19)0.0352 (18)0.0401 (19)0.0040 (16)0.0012 (15)0.0012 (15)
C150.056 (2)0.047 (2)0.041 (2)0.0043 (19)0.0080 (18)0.0052 (17)
C160.061 (3)0.045 (2)0.051 (2)0.006 (2)0.007 (2)0.0074 (18)
C170.045 (2)0.038 (2)0.063 (3)0.0010 (18)0.0004 (19)0.0059 (19)
C180.042 (2)0.048 (2)0.050 (2)0.0033 (19)0.0043 (17)0.0087 (19)
C190.044 (2)0.048 (2)0.0399 (19)0.0084 (18)0.0026 (16)0.0065 (17)
O200.0469 (15)0.0637 (18)0.0365 (13)0.0008 (14)0.0049 (12)0.0113 (13)
Cl10.044 (4)0.055 (5)0.038 (4)0.007 (3)0.000 (3)0.008 (3)
C210.0357 (17)0.0354 (19)0.0387 (18)0.0030 (15)0.0029 (14)0.0012 (15)
C220.057 (2)0.038 (2)0.044 (2)0.0027 (18)0.0002 (18)0.0005 (16)
C230.066 (3)0.038 (2)0.061 (3)0.003 (2)0.002 (2)0.0052 (19)
N240.055 (2)0.050 (2)0.054 (2)0.0016 (17)0.0052 (17)0.0159 (17)
C250.051 (2)0.049 (2)0.043 (2)0.006 (2)0.0061 (17)0.0021 (19)
C260.045 (2)0.040 (2)0.0388 (19)0.0022 (17)0.0018 (16)0.0001 (16)
Geometric parameters (Å, º) top
Br1—C171.892 (4)C14—C191.381 (5)
N1—C21.377 (4)C14—C151.384 (5)
N1—N131.384 (4)C15—C161.387 (6)
N1—C141.439 (5)C15—H150.9500
C2—O201.221 (4)C16—C171.378 (6)
C2—C31.465 (5)C16—H160.9500
C3—N41.308 (4)C17—C181.377 (6)
C3—N111.388 (5)C18—C191.384 (6)
N4—C51.387 (5)C18—H180.9500
C5—C61.401 (6)C19—Cl11.593 (8)
C5—C101.407 (5)C19—H190.9500
C6—C71.372 (7)Cl1—Cl1i2.467 (15)
C6—H60.9500C21—C221.384 (5)
C7—C81.392 (7)C21—C261.385 (5)
C7—H70.9500C22—C231.386 (6)
C8—C91.384 (6)C22—H220.9500
C8—H80.9500C23—N241.331 (6)
C9—C101.396 (6)C23—H230.9500
C9—H90.9500N24—C251.327 (5)
C10—N111.399 (5)C25—C261.383 (5)
N11—C121.395 (4)C25—H250.9500
C12—N131.281 (5)C26—H260.9500
C12—C211.474 (5)
C2—N1—N13125.2 (3)C19—C14—N1121.0 (3)
C2—N1—C14122.7 (3)C15—C14—N1117.8 (3)
N13—N1—C14112.1 (3)C14—C15—C16119.2 (4)
O20—C2—N1122.9 (4)C14—C15—H15120.4
O20—C2—C3123.6 (3)C16—C15—H15120.4
N1—C2—C3113.6 (3)C17—C16—C15119.7 (4)
N4—C3—N11114.4 (4)C17—C16—H16120.2
N4—C3—C2126.1 (3)C15—C16—H16120.2
N11—C3—C2119.5 (3)C18—C17—C16121.1 (4)
C3—N4—C5103.8 (3)C18—C17—Br1120.3 (3)
N4—C5—C6128.7 (4)C16—C17—Br1118.6 (3)
N4—C5—C10111.9 (3)C17—C18—C19119.6 (4)
C6—C5—C10119.4 (4)C17—C18—H18120.2
C7—C6—C5118.0 (4)C19—C18—H18120.2
C7—C6—H6121.0C14—C19—C18119.4 (4)
C5—C6—H6121.0C14—C19—Cl1127.5 (4)
C6—C7—C8121.5 (4)C18—C19—Cl1111.6 (4)
C6—C7—H7119.3C14—C19—H19120.3
C8—C7—H7119.3C18—C19—H19120.3
C9—C8—C7122.5 (5)C19—Cl1—Cl1i131.6 (5)
C9—C8—H8118.7C22—C21—C26118.7 (3)
C7—C8—H8118.7C22—C21—C12120.9 (3)
C8—C9—C10115.6 (4)C26—C21—C12120.2 (3)
C8—C9—H9122.2C21—C22—C23117.9 (4)
C10—C9—H9122.2C21—C22—H22121.1
C9—C10—N11133.1 (3)C23—C22—H22121.1
C9—C10—C5122.8 (4)N24—C23—C22124.5 (4)
N11—C10—C5104.1 (3)N24—C23—H23117.8
C3—N11—C12120.2 (3)C22—C23—H23117.8
C3—N11—C10105.9 (3)C25—N24—C23116.4 (3)
C12—N11—C10133.9 (3)N24—C25—C26124.3 (4)
N13—C12—N11121.7 (3)N24—C25—H25117.9
N13—C12—C21116.4 (3)C26—C25—H25117.9
N11—C12—C21121.8 (3)C25—C26—C21118.3 (4)
C12—N13—N1119.7 (3)C25—C26—H26120.9
C19—C14—C15121.0 (4)C21—C26—H26120.9
N13—N1—C2—O20176.9 (3)N11—C12—N13—N11.5 (5)
C14—N1—C2—O201.5 (6)C21—C12—N13—N1175.2 (3)
N13—N1—C2—C32.5 (5)C2—N1—N13—C121.5 (5)
C14—N1—C2—C3179.0 (3)C14—N1—N13—C12179.9 (3)
O20—C2—C3—N41.0 (6)C2—N1—C14—C1947.3 (5)
N1—C2—C3—N4179.5 (4)N13—N1—C14—C19134.1 (3)
O20—C2—C3—N11175.8 (4)C2—N1—C14—C15136.3 (4)
N1—C2—C3—N113.7 (5)N13—N1—C14—C1542.3 (4)
N11—C3—N4—C50.0 (4)C19—C14—C15—C161.4 (6)
C2—C3—N4—C5176.9 (4)N1—C14—C15—C16174.9 (4)
C3—N4—C5—C6178.4 (4)C14—C15—C16—C170.5 (6)
C3—N4—C5—C100.5 (4)C15—C16—C17—C180.5 (6)
N4—C5—C6—C7179.2 (4)C15—C16—C17—Br1178.9 (3)
C10—C5—C6—C70.4 (6)C16—C17—C18—C190.7 (6)
C5—C6—C7—C81.5 (7)Br1—C17—C18—C19178.8 (3)
C6—C7—C8—C91.2 (7)C15—C14—C19—C181.3 (5)
C7—C8—C9—C101.0 (6)N1—C14—C19—C18175.0 (3)
C8—C9—C10—N11178.3 (4)C15—C14—C19—Cl1166.3 (5)
C8—C9—C10—C52.9 (6)N1—C14—C19—Cl110.0 (6)
N4—C5—C10—C9178.3 (4)C17—C18—C19—C140.2 (6)
C6—C5—C10—C92.7 (6)C17—C18—C19—Cl1167.5 (4)
N4—C5—C10—N110.8 (4)C14—C19—Cl1—Cl1i150.2 (4)
C6—C5—C10—N11178.3 (3)C18—C19—Cl1—Cl1i15.8 (7)
N4—C3—N11—C12178.9 (3)N13—C12—C21—C22120.9 (4)
C2—C3—N11—C124.0 (5)N11—C12—C21—C2255.7 (5)
N4—C3—N11—C100.5 (4)N13—C12—C21—C2653.6 (5)
C2—C3—N11—C10176.7 (3)N11—C12—C21—C26129.7 (4)
C9—C10—N11—C3178.2 (4)C26—C21—C22—C230.4 (6)
C5—C10—N11—C30.7 (4)C12—C21—C22—C23175.1 (4)
C9—C10—N11—C122.6 (7)C21—C22—C23—N240.2 (7)
C5—C10—N11—C12178.5 (4)C22—C23—N24—C250.3 (7)
C3—N11—C12—N132.9 (5)C23—N24—C25—C260.8 (6)
C10—N11—C12—N13178.0 (4)N24—C25—C26—C211.1 (6)
C3—N11—C12—C21173.6 (3)C22—C21—C26—C250.9 (5)
C10—N11—C12—C215.5 (6)C12—C21—C26—C25175.6 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O20ii0.952.533.258 (5)134
C15—H15···O20iii0.952.303.219 (5)162
C23—H23···Br1iv0.952.973.417 (4)110
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z+1/2; (iv) x, y+1, z+3/2.
3-(4-Bromo-2-chlorophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one (2) top
Crystal data top
C20H11BrClN5OF(000) = 1808
Mr = 452.70Dx = 1.619 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.1074 (7) ÅCell parameters from 1476 reflections
b = 32.754 (3) Åθ = 2.5–19.7°
c = 16.1505 (15) ŵ = 2.38 mm1
β = 98.914 (3)°T = 173 K
V = 3714.4 (6) Å3Column, colourless
Z = 80.28 × 0.03 × 0.02 mm
Data collection top
Bruker SMART APEXII
diffractometer
3614 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.152
CCD scanθmax = 27.8°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.872, Tmax = 0.947k = 4142
31679 measured reflectionsl = 2121
8805 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.012P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.72(Δ/σ)max = 0.001
8805 reflectionsΔρmax = 0.42 e Å3
505 parametersΔρmin = 0.49 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
Br1A0.96493 (8)0.44476 (2)0.31444 (3)0.04310 (17)
Cl1A1.36103 (18)0.46317 (5)0.63345 (8)0.0432 (4)
N1A0.9964 (5)0.43502 (10)0.6924 (2)0.0173 (9)
C2A1.0976 (6)0.40286 (13)0.7334 (3)0.0176 (11)
C3A1.0808 (6)0.40069 (13)0.8227 (3)0.0165 (11)
N4A1.1804 (5)0.37751 (11)0.8789 (2)0.0208 (9)
C5A1.1249 (6)0.38977 (13)0.9538 (3)0.0170 (11)
C6A1.1926 (6)0.37608 (14)1.0348 (3)0.0236 (12)
H6A1.28280.35451.04430.028*
C7A1.1243 (6)0.39487 (15)1.1007 (3)0.0276 (12)
H7A1.16820.38611.15640.033*
C8A0.9922 (6)0.42647 (14)1.0869 (3)0.0260 (12)
H8A0.94780.43871.13360.031*
C9A0.9232 (6)0.44073 (14)1.0073 (3)0.0244 (12)
H9A0.83560.46280.99840.029*
C10A0.9887 (6)0.42112 (13)0.9411 (3)0.0173 (11)
N11A0.9589 (5)0.42773 (10)0.8541 (2)0.0155 (9)
C12A0.8362 (6)0.45263 (13)0.8002 (3)0.0148 (10)
N13A0.8534 (5)0.45672 (10)0.7225 (2)0.0180 (9)
C14A0.9909 (6)0.43961 (13)0.6034 (3)0.0179 (11)
C15A0.8217 (7)0.43142 (14)0.5505 (3)0.0256 (12)
H15A0.71110.42420.57350.031*
C16A0.8132 (7)0.43367 (13)0.4648 (3)0.0236 (12)
H16A0.69730.42810.42870.028*
C17A0.9736 (7)0.44400 (15)0.4324 (3)0.0257 (12)
C18A1.1435 (7)0.45322 (14)0.4828 (3)0.0260 (12)
H18A1.25250.46110.45930.031*
C19A1.1500 (6)0.45062 (14)0.5696 (3)0.0218 (11)
O20A1.1978 (4)0.38045 (9)0.69899 (18)0.0270 (8)
C21A0.6743 (6)0.47361 (13)0.8297 (3)0.0148 (10)
C22A0.5556 (6)0.45303 (14)0.8762 (3)0.0210 (11)
H22A0.57740.42520.89090.025*
C23A0.4048 (6)0.47409 (15)0.9007 (3)0.0252 (12)
H23A0.32700.46000.93420.030*
N24A0.3612 (5)0.51258 (13)0.8807 (2)0.0304 (11)
C25A0.4749 (7)0.53165 (15)0.8346 (3)0.0297 (13)
H25A0.44650.55920.81890.036*
C26A0.6319 (6)0.51357 (14)0.8083 (3)0.0241 (12)
H26A0.70910.52860.77600.029*
Br1B0.47931 (8)0.36336 (2)0.29334 (3)0.03770 (16)
Cl1B0.84923 (18)0.30274 (4)0.59237 (8)0.0411 (4)
N1B0.4871 (5)0.32230 (11)0.6617 (2)0.0166 (9)
C2B0.5946 (6)0.34732 (14)0.7198 (3)0.0196 (11)
C3B0.5793 (6)0.33619 (14)0.8071 (3)0.0201 (11)
N4B0.6815 (5)0.35077 (11)0.8745 (2)0.0201 (9)
C5B0.6216 (6)0.32841 (14)0.9391 (3)0.0197 (11)
C6B0.6875 (7)0.33113 (15)1.0247 (3)0.0277 (12)
H6B0.78270.35041.04610.033*
C7B0.6107 (7)0.30507 (15)1.0773 (3)0.0303 (13)
H7B0.65370.30641.13590.036*
C8B0.4708 (7)0.27673 (14)1.0461 (3)0.0263 (12)
H8B0.42110.25921.08420.032*
C9B0.4024 (6)0.27336 (14)0.9619 (3)0.0220 (11)
H9B0.30880.25370.94100.026*
C10B0.4779 (6)0.30041 (14)0.9083 (3)0.0200 (11)
N11B0.4492 (5)0.30633 (10)0.8217 (2)0.0155 (8)
C12B0.3257 (6)0.28919 (13)0.7551 (3)0.0170 (11)
N13B0.3423 (5)0.29650 (11)0.6775 (2)0.0189 (9)
C14B0.4850 (6)0.33054 (13)0.5739 (3)0.0160 (10)
C15B0.3200 (6)0.34514 (13)0.5259 (3)0.0225 (12)
H15B0.20880.34880.55110.027*
C16B0.3145 (7)0.35454 (14)0.4419 (3)0.0277 (12)
H16B0.20200.36500.40920.033*
C17B0.4782 (7)0.34825 (14)0.4070 (3)0.0222 (11)
C18B0.6421 (6)0.33246 (13)0.4522 (3)0.0216 (11)
H18B0.75130.32780.42630.026*
C19B0.6451 (6)0.32348 (13)0.5359 (3)0.0185 (11)
O20B0.6995 (4)0.37385 (9)0.70109 (18)0.0276 (8)
C21B0.1679 (6)0.26314 (14)0.7722 (3)0.0195 (11)
C22B0.0357 (6)0.27684 (15)0.8214 (3)0.0271 (12)
H22B0.04250.30360.84430.033*
C23B0.1051 (7)0.24998 (16)0.8354 (3)0.0347 (14)
H23B0.19530.25960.86850.042*
N24B0.1270 (6)0.21199 (13)0.8073 (3)0.0349 (11)
C25B0.0011 (7)0.19985 (15)0.7593 (3)0.0365 (14)
H25B0.01260.17300.73690.044*
C26B0.1469 (6)0.22436 (14)0.7400 (3)0.0271 (12)
H26B0.23220.21430.70500.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0516 (4)0.0607 (4)0.0186 (3)0.0114 (3)0.0105 (3)0.0025 (3)
Cl1A0.0284 (8)0.0656 (11)0.0359 (8)0.0056 (7)0.0059 (7)0.0006 (7)
N1A0.018 (2)0.020 (2)0.016 (2)0.0015 (18)0.0088 (17)0.0006 (16)
C2A0.018 (3)0.015 (3)0.021 (3)0.001 (2)0.003 (2)0.001 (2)
C3A0.016 (2)0.018 (3)0.016 (3)0.002 (2)0.003 (2)0.004 (2)
N4A0.020 (2)0.026 (3)0.017 (2)0.0050 (19)0.0047 (18)0.0014 (17)
C5A0.014 (2)0.019 (3)0.017 (3)0.002 (2)0.001 (2)0.002 (2)
C6A0.016 (3)0.027 (3)0.027 (3)0.006 (2)0.003 (2)0.003 (2)
C7A0.024 (3)0.041 (4)0.017 (3)0.006 (3)0.002 (2)0.006 (2)
C8A0.024 (3)0.034 (3)0.021 (3)0.002 (2)0.008 (2)0.005 (2)
C9A0.017 (3)0.033 (3)0.023 (3)0.003 (2)0.003 (2)0.001 (2)
C10A0.019 (3)0.020 (3)0.013 (2)0.002 (2)0.004 (2)0.001 (2)
N11A0.013 (2)0.019 (2)0.016 (2)0.0031 (17)0.0055 (17)0.0021 (16)
C12A0.009 (2)0.014 (3)0.021 (3)0.002 (2)0.002 (2)0.002 (2)
N13A0.017 (2)0.018 (2)0.020 (2)0.0024 (18)0.0047 (18)0.0010 (17)
C14A0.018 (3)0.016 (3)0.020 (3)0.002 (2)0.006 (2)0.000 (2)
C15A0.023 (3)0.032 (3)0.024 (3)0.006 (2)0.010 (2)0.003 (2)
C16A0.024 (3)0.023 (3)0.021 (3)0.004 (2)0.006 (2)0.000 (2)
C17A0.033 (3)0.031 (3)0.015 (2)0.002 (3)0.012 (2)0.001 (2)
C18A0.026 (3)0.029 (3)0.027 (3)0.001 (2)0.016 (2)0.004 (2)
C19A0.014 (3)0.027 (3)0.024 (3)0.003 (2)0.000 (2)0.006 (2)
O20A0.031 (2)0.029 (2)0.0237 (19)0.0132 (16)0.0131 (16)0.0014 (15)
C21A0.013 (2)0.017 (3)0.013 (2)0.002 (2)0.004 (2)0.0012 (19)
C22A0.018 (3)0.021 (3)0.025 (3)0.000 (2)0.008 (2)0.000 (2)
C23A0.016 (3)0.028 (3)0.033 (3)0.001 (2)0.010 (2)0.002 (2)
N24A0.024 (2)0.031 (3)0.040 (3)0.008 (2)0.015 (2)0.001 (2)
C25A0.033 (3)0.017 (3)0.041 (3)0.004 (2)0.012 (3)0.003 (2)
C26A0.016 (3)0.028 (3)0.030 (3)0.000 (2)0.006 (2)0.000 (2)
Br1B0.0445 (4)0.0483 (4)0.0207 (3)0.0002 (3)0.0061 (3)0.0076 (3)
Cl1B0.0281 (8)0.0597 (11)0.0365 (8)0.0102 (7)0.0084 (6)0.0071 (7)
N1B0.017 (2)0.017 (2)0.017 (2)0.0045 (18)0.0068 (18)0.0012 (17)
C2B0.014 (3)0.026 (3)0.019 (3)0.003 (2)0.005 (2)0.002 (2)
C3B0.020 (3)0.020 (3)0.022 (3)0.005 (2)0.010 (2)0.002 (2)
N4B0.021 (2)0.021 (2)0.018 (2)0.0038 (18)0.0020 (18)0.0006 (17)
C5B0.018 (3)0.022 (3)0.018 (3)0.005 (2)0.001 (2)0.001 (2)
C6B0.023 (3)0.034 (3)0.026 (3)0.001 (2)0.001 (2)0.007 (2)
C7B0.034 (3)0.042 (4)0.012 (3)0.007 (3)0.004 (2)0.003 (2)
C8B0.031 (3)0.026 (3)0.026 (3)0.005 (3)0.018 (2)0.008 (2)
C9B0.028 (3)0.020 (3)0.020 (3)0.001 (2)0.009 (2)0.002 (2)
C10B0.022 (3)0.022 (3)0.017 (3)0.005 (2)0.004 (2)0.003 (2)
N11B0.015 (2)0.019 (2)0.013 (2)0.0006 (18)0.0045 (17)0.0005 (17)
C12B0.011 (2)0.021 (3)0.019 (3)0.001 (2)0.003 (2)0.000 (2)
N13B0.017 (2)0.020 (2)0.021 (2)0.0023 (18)0.0067 (18)0.0003 (17)
C14B0.020 (3)0.015 (3)0.015 (2)0.001 (2)0.006 (2)0.0019 (19)
C15B0.013 (3)0.031 (3)0.025 (3)0.005 (2)0.008 (2)0.001 (2)
C16B0.022 (3)0.036 (3)0.025 (3)0.007 (2)0.002 (2)0.002 (2)
C17B0.031 (3)0.021 (3)0.015 (3)0.002 (2)0.008 (2)0.002 (2)
C18B0.018 (3)0.028 (3)0.019 (3)0.000 (2)0.007 (2)0.000 (2)
C19B0.018 (3)0.018 (3)0.020 (3)0.004 (2)0.004 (2)0.003 (2)
O20B0.030 (2)0.030 (2)0.0238 (19)0.0150 (17)0.0078 (16)0.0011 (15)
C21B0.021 (3)0.017 (3)0.020 (3)0.005 (2)0.003 (2)0.001 (2)
C22B0.026 (3)0.027 (3)0.030 (3)0.001 (2)0.011 (2)0.003 (2)
C23B0.021 (3)0.042 (4)0.044 (4)0.002 (3)0.015 (3)0.003 (3)
N24B0.027 (3)0.037 (3)0.043 (3)0.007 (2)0.013 (2)0.000 (2)
C25B0.045 (4)0.023 (3)0.043 (4)0.008 (3)0.015 (3)0.011 (3)
C26B0.026 (3)0.029 (3)0.029 (3)0.005 (3)0.013 (2)0.001 (2)
Geometric parameters (Å, º) top
Br1A—C17A1.896 (4)Br1B—C17B1.902 (4)
Cl1A—C19A1.733 (4)Cl1B—C19B1.729 (4)
N1A—C2A1.385 (5)N1B—C2B1.383 (5)
N1A—N13A1.389 (4)N1B—N13B1.385 (4)
N1A—C14A1.439 (5)N1B—C14B1.442 (5)
C2A—O20A1.215 (5)C2B—O20B1.213 (5)
C2A—C3A1.467 (6)C2B—C3B1.476 (6)
C3A—N4A1.305 (5)C3B—N4B1.302 (5)
C3A—N11A1.389 (5)C3B—N11B1.391 (5)
N4A—C5A1.389 (5)N4B—C5B1.394 (5)
C5A—C6A1.396 (6)C5B—C6B1.391 (6)
C5A—C10A1.404 (6)C5B—C10B1.405 (6)
C6A—C7A1.381 (6)C6B—C7B1.375 (6)
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.392 (6)C7B—C8B1.396 (6)
C7A—H7A0.9500C7B—H7B0.9500
C8A—C9A1.384 (6)C8B—C9B1.376 (6)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.387 (6)C9B—C10B1.402 (6)
C9A—H9A0.9500C9B—H9B0.9500
C10A—N11A1.405 (5)C10B—N11B1.395 (5)
N11A—C12A1.396 (5)N11B—C12B1.397 (5)
C12A—N13A1.285 (5)C12B—N13B1.299 (5)
C12A—C21A1.482 (5)C12B—C21B1.469 (6)
C14A—C19A1.378 (6)C14B—C15B1.386 (6)
C14A—C15A1.390 (6)C14B—C19B1.393 (5)
C15A—C16A1.377 (6)C15B—C16B1.387 (6)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.369 (6)C16B—C17B1.385 (6)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.382 (6)C17B—C18B1.376 (6)
C18A—C19A1.397 (6)C18B—C19B1.380 (5)
C18A—H18A0.9500C18B—H18B0.9500
C21A—C26A1.375 (6)C21B—C26B1.372 (6)
C21A—C22A1.388 (5)C21B—C22B1.395 (6)
C22A—C23A1.383 (6)C22B—C23B1.377 (6)
C22A—H22A0.9500C22B—H22B0.9500
C23A—N24A1.326 (5)C23B—N24B1.326 (6)
C23A—H23A0.9500C23B—H23B0.9500
N24A—C25A1.336 (5)N24B—C25B1.332 (6)
C25A—C26A1.387 (6)C25B—C26B1.396 (6)
C25A—H25A0.9500C25B—H25B0.9500
C26A—H26A0.9500C26B—H26B0.9500
C2A—N1A—N13A125.1 (3)C2B—N1B—N13B125.8 (3)
C2A—N1A—C14A119.2 (3)C2B—N1B—C14B118.5 (4)
N13A—N1A—C14A112.9 (3)N13B—N1B—C14B113.6 (3)
O20A—C2A—N1A122.6 (4)O20B—C2B—N1B123.5 (4)
O20A—C2A—C3A124.2 (4)O20B—C2B—C3B123.6 (4)
N1A—C2A—C3A113.0 (4)N1B—C2B—C3B112.8 (4)
N4A—C3A—N11A114.8 (4)N4B—C3B—N11B114.5 (4)
N4A—C3A—C2A126.5 (4)N4B—C3B—C2B126.4 (4)
N11A—C3A—C2A118.6 (4)N11B—C3B—C2B119.0 (4)
C3A—N4A—C5A104.0 (4)C3B—N4B—C5B103.7 (4)
N4A—C5A—C6A128.3 (4)C6B—C5B—N4B127.9 (4)
N4A—C5A—C10A111.5 (4)C6B—C5B—C10B120.5 (4)
C6A—C5A—C10A120.1 (4)N4B—C5B—C10B111.6 (4)
C7A—C6A—C5A117.9 (4)C7B—C6B—C5B117.9 (4)
C7A—C6A—H6A121.1C7B—C6B—H6B121.0
C5A—C6A—H6A121.1C5B—C6B—H6B121.0
C6A—C7A—C8A121.1 (4)C6B—C7B—C8B121.2 (4)
C6A—C7A—H7A119.5C6B—C7B—H7B119.4
C8A—C7A—H7A119.5C8B—C7B—H7B119.4
C9A—C8A—C7A122.2 (4)C9B—C8B—C7B122.2 (4)
C9A—C8A—H8A118.9C9B—C8B—H8B118.9
C7A—C8A—H8A118.9C7B—C8B—H8B118.9
C8A—C9A—C10A116.5 (4)C8B—C9B—C10B116.7 (4)
C8A—C9A—H9A121.7C8B—C9B—H9B121.7
C10A—C9A—H9A121.7C10B—C9B—H9B121.7
C9A—C10A—C5A122.2 (4)N11B—C10B—C9B134.1 (4)
C9A—C10A—N11A133.0 (4)N11B—C10B—C5B104.5 (4)
C5A—C10A—N11A104.6 (4)C9B—C10B—C5B121.4 (4)
C3A—N11A—C12A120.6 (4)C3B—N11B—C10B105.7 (4)
C3A—N11A—C10A105.1 (3)C3B—N11B—C12B120.5 (4)
C12A—N11A—C10A134.2 (4)C10B—N11B—C12B133.9 (4)
N13A—C12A—N11A121.6 (4)N13B—C12B—N11B121.9 (4)
N13A—C12A—C21A117.5 (4)N13B—C12B—C21B118.3 (4)
N11A—C12A—C21A120.8 (4)N11B—C12B—C21B119.7 (4)
C12A—N13A—N1A118.3 (3)C12B—N13B—N1B118.1 (4)
C19A—C14A—C15A119.4 (4)C15B—C14B—C19B119.3 (4)
C19A—C14A—N1A121.7 (4)C15B—C14B—N1B119.5 (4)
C15A—C14A—N1A118.8 (4)C19B—C14B—N1B121.1 (4)
C16A—C15A—C14A120.5 (4)C14B—C15B—C16B121.1 (4)
C16A—C15A—H15A119.8C14B—C15B—H15B119.4
C14A—C15A—H15A119.8C16B—C15B—H15B119.4
C17A—C16A—C15A119.2 (4)C17B—C16B—C15B117.9 (4)
C17A—C16A—H16A120.4C17B—C16B—H16B121.1
C15A—C16A—H16A120.4C15B—C16B—H16B121.1
C16A—C17A—C18A122.1 (4)C18B—C17B—C16B122.4 (4)
C16A—C17A—Br1A119.3 (4)C18B—C17B—Br1B118.7 (3)
C18A—C17A—Br1A118.6 (3)C16B—C17B—Br1B118.9 (4)
C17A—C18A—C19A117.9 (4)C17B—C18B—C19B118.9 (4)
C17A—C18A—H18A121.0C17B—C18B—H18B120.5
C19A—C18A—H18A121.0C19B—C18B—H18B120.5
C14A—C19A—C18A120.8 (4)C18B—C19B—C14B120.4 (4)
C14A—C19A—Cl1A120.9 (3)C18B—C19B—Cl1B119.0 (3)
C18A—C19A—Cl1A118.3 (3)C14B—C19B—Cl1B120.6 (3)
C26A—C21A—C22A118.1 (4)C26B—C21B—C22B118.0 (4)
C26A—C21A—C12A120.7 (4)C26B—C21B—C12B120.5 (4)
C22A—C21A—C12A121.1 (4)C22B—C21B—C12B121.4 (4)
C23A—C22A—C21A118.4 (4)C23B—C22B—C21B117.3 (5)
C23A—C22A—H22A120.8C23B—C22B—H22B121.3
C21A—C22A—H22A120.8C21B—C22B—H22B121.3
N24A—C23A—C22A124.6 (4)N24B—C23B—C22B126.3 (5)
N24A—C23A—H23A117.7N24B—C23B—H23B116.8
C22A—C23A—H23A117.7C22B—C23B—H23B116.8
C23A—N24A—C25A116.2 (4)C23B—N24B—C25B115.2 (4)
N24A—C25A—C26A123.8 (5)N24B—C25B—C26B123.7 (5)
N24A—C25A—H25A118.1N24B—C25B—H25B118.1
C26A—C25A—H25A118.1C26B—C25B—H25B118.1
C21A—C26A—C25A119.0 (4)C21B—C26B—C25B119.3 (4)
C21A—C26A—H26A120.5C21B—C26B—H26B120.3
C25A—C26A—H26A120.5C25B—C26B—H26B120.3
N13A—N1A—C2A—O20A167.2 (4)N13B—N1B—C2B—O20B168.4 (4)
C14A—N1A—C2A—O20A7.3 (6)C14B—N1B—C2B—O20B6.1 (6)
N13A—N1A—C2A—C3A16.7 (6)N13B—N1B—C2B—C3B16.1 (6)
C14A—N1A—C2A—C3A176.5 (4)C14B—N1B—C2B—C3B178.3 (4)
O20A—C2A—C3A—N4A6.3 (8)O20B—C2B—C3B—N4B4.7 (8)
N1A—C2A—C3A—N4A169.7 (4)N1B—C2B—C3B—N4B170.8 (4)
O20A—C2A—C3A—N11A179.0 (4)O20B—C2B—C3B—N11B177.6 (4)
N1A—C2A—C3A—N11A4.9 (6)N1B—C2B—C3B—N11B6.8 (6)
N11A—C3A—N4A—C5A0.7 (5)N11B—C3B—N4B—C5B2.0 (5)
C2A—C3A—N4A—C5A174.1 (4)C2B—C3B—N4B—C5B175.7 (4)
C3A—N4A—C5A—C6A177.2 (5)C3B—N4B—C5B—C6B178.7 (4)
C3A—N4A—C5A—C10A0.1 (5)C3B—N4B—C5B—C10B1.0 (5)
N4A—C5A—C6A—C7A175.7 (4)N4B—C5B—C6B—C7B178.2 (4)
C10A—C5A—C6A—C7A1.3 (7)C10B—C5B—C6B—C7B1.4 (7)
C5A—C6A—C7A—C8A0.0 (7)C5B—C6B—C7B—C8B0.1 (7)
C6A—C7A—C8A—C9A0.2 (7)C6B—C7B—C8B—C9B0.1 (7)
C7A—C8A—C9A—C10A1.7 (7)C7B—C8B—C9B—C10B1.1 (7)
C8A—C9A—C10A—C5A3.0 (7)C8B—C9B—C10B—N11B179.0 (4)
C8A—C9A—C10A—N11A176.8 (4)C8B—C9B—C10B—C5B2.4 (7)
N4A—C5A—C10A—C9A174.5 (4)C6B—C5B—C10B—N11B179.9 (4)
C6A—C5A—C10A—C9A2.9 (7)N4B—C5B—C10B—N11B0.4 (5)
N4A—C5A—C10A—N11A0.8 (5)C6B—C5B—C10B—C9B2.6 (7)
C6A—C5A—C10A—N11A178.2 (4)N4B—C5B—C10B—C9B177.0 (4)
N4A—C3A—N11A—C12A176.3 (4)N4B—C3B—N11B—C10B2.3 (5)
C2A—C3A—N11A—C12A8.5 (6)C2B—C3B—N11B—C10B175.6 (4)
N4A—C3A—N11A—C10A1.2 (5)N4B—C3B—N11B—C12B177.6 (4)
C2A—C3A—N11A—C10A174.0 (4)C2B—C3B—N11B—C12B4.5 (6)
C9A—C10A—N11A—C3A173.4 (5)C9B—C10B—N11B—C3B175.4 (5)
C5A—C10A—N11A—C3A1.1 (4)C5B—C10B—N11B—C3B1.5 (4)
C9A—C10A—N11A—C12A9.6 (8)C9B—C10B—N11B—C12B4.6 (8)
C5A—C10A—N11A—C12A175.9 (4)C5B—C10B—N11B—C12B178.4 (4)
C3A—N11A—C12A—N13A12.1 (6)C3B—N11B—C12B—N13B8.6 (6)
C10A—N11A—C12A—N13A171.3 (4)C10B—N11B—C12B—N13B171.5 (4)
C3A—N11A—C12A—C21A164.6 (4)C3B—N11B—C12B—C21B169.4 (4)
C10A—N11A—C12A—C21A12.1 (7)C10B—N11B—C12B—C21B10.5 (7)
N11A—C12A—N13A—N1A1.2 (6)N11B—C12B—N13B—N1B0.4 (6)
C21A—C12A—N13A—N1A175.6 (4)C21B—C12B—N13B—N1B177.7 (4)
C2A—N1A—N13A—C12A14.2 (6)C2B—N1B—N13B—C12B13.0 (6)
C14A—N1A—N13A—C12A175.2 (4)C14B—N1B—N13B—C12B176.0 (4)
C2A—N1A—C14A—C19A69.0 (6)C2B—N1B—C14B—C15B110.7 (5)
N13A—N1A—C14A—C19A128.8 (4)N13B—N1B—C14B—C15B53.7 (5)
C2A—N1A—C14A—C15A108.9 (5)C2B—N1B—C14B—C19B70.4 (5)
N13A—N1A—C14A—C15A53.3 (5)N13B—N1B—C14B—C19B125.3 (4)
C19A—C14A—C15A—C16A1.0 (7)C19B—C14B—C15B—C16B2.9 (7)
N1A—C14A—C15A—C16A177.0 (4)N1B—C14B—C15B—C16B178.1 (4)
C14A—C15A—C16A—C17A0.1 (7)C14B—C15B—C16B—C17B1.0 (7)
C15A—C16A—C17A—C18A1.6 (7)C15B—C16B—C17B—C18B1.3 (7)
C15A—C16A—C17A—Br1A177.2 (3)C15B—C16B—C17B—Br1B176.9 (3)
C16A—C17A—C18A—C19A1.8 (7)C16B—C17B—C18B—C19B1.6 (7)
Br1A—C17A—C18A—C19A177.0 (3)Br1B—C17B—C18B—C19B176.6 (3)
C15A—C14A—C19A—C18A0.7 (7)C17B—C18B—C19B—C14B0.4 (7)
N1A—C14A—C19A—C18A177.3 (4)C17B—C18B—C19B—Cl1B178.8 (3)
C15A—C14A—C19A—Cl1A177.3 (3)C15B—C14B—C19B—C18B2.6 (7)
N1A—C14A—C19A—Cl1A4.8 (6)N1B—C14B—C19B—C18B178.4 (4)
C17A—C18A—C19A—C14A0.7 (7)C15B—C14B—C19B—Cl1B176.5 (3)
C17A—C18A—C19A—Cl1A178.7 (4)N1B—C14B—C19B—Cl1B2.4 (6)
N13A—C12A—C21A—C26A45.9 (6)N13B—C12B—C21B—C26B56.8 (6)
N11A—C12A—C21A—C26A137.3 (4)N11B—C12B—C21B—C26B125.1 (5)
N13A—C12A—C21A—C22A130.9 (4)N13B—C12B—C21B—C22B123.3 (5)
N11A—C12A—C21A—C22A45.9 (6)N11B—C12B—C21B—C22B54.8 (6)
C26A—C21A—C22A—C23A2.0 (6)C26B—C21B—C22B—C23B1.2 (7)
C12A—C21A—C22A—C23A178.9 (4)C12B—C21B—C22B—C23B178.7 (4)
C21A—C22A—C23A—N24A2.1 (7)C21B—C22B—C23B—N24B0.6 (8)
C22A—C23A—N24A—C25A0.8 (7)C22B—C23B—N24B—C25B1.7 (8)
C23A—N24A—C25A—C26A0.6 (7)C23B—N24B—C25B—C26B1.1 (8)
C22A—C21A—C26A—C25A0.7 (7)C22B—C21B—C26B—C25B1.7 (7)
C12A—C21A—C26A—C25A177.6 (4)C12B—C21B—C26B—C25B178.2 (4)
N24A—C25A—C26A—C21A0.6 (7)N24B—C25B—C26B—C21B0.6 (8)
Torsion angles (°) top
CompoundN13—N1—C14—C15N13—C12—C21—C26
(1)-42.3 (4)53.6 (5)
(2A)-53.3 (5)-45.9 (6)
(2B)-53.7 (5)-56.8 (6)
 

Acknowledgements

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

References

First citationAbu Thaher, B. A., Schollmeyer, D., Qeshta, B. & Deigner, H.-P. (2016a). IUCrData, 1, x161380.  Google Scholar
First citationAbu Thaher, B. A., Schollmeyer, D., Qeshta, B., Wahedy, K. M., Almasri, I. M., Morjan, R. Y. & Deigner, H. (2016b). IUCrData, 1, x161529.  Google Scholar
First citationBiron, K. K. (2006). Antiviral Res. 71, 154–163.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGellis, A., Kovacic, H., Boufatah, N. & Vanelle, P. (2008). Eur. J. Med. Chem. 43, 1858–1864.  Web of Science CrossRef PubMed CAS Google Scholar
First citationKarpińka, M. M., Matysiak, J. & Niewiadomy, A. (2011). Arch. Pharm. Res. 34, 1639–1647.  Web of Science PubMed Google Scholar
First citationPescovitz, M. D. (2008). Future Virol. 3, 435–443.  Web of Science CrossRef CAS Google Scholar
First citationRefaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949–2956.  Web of Science CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSingh, S., Ojha, H., Tiwari, A. K., Kumar, N., Singh, B. & Mishra, A. K. (2010). Cancer Biother. Radiopharm. 25, 245–250.  Web of Science CrossRef CAS PubMed Google Scholar
First citationStoe & Cie (2006). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationThomas, 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.  Web of Science CrossRef PubMed CAS Google Scholar

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