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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o846-o847

2-(2,6-Di­chloro­phen­yl)-1-pentyl-4,5-di­phenyl-1H-imidazole

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Sccience, Mini University, 61519 El-Minia, Egypt, dDepartment of Chemistry, University of Leicester, Leicester, England, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 22 April 2013; accepted 26 April 2013; online 11 May 2013)

The title compound, C26H24Cl2N2, crystallizes with two independent mol­ecules (1 and 2) in the asymmetric unit. In mol­ecule 1, the two phenyl and 2,6-di­chloro­phenyl rings are inclined to the imidazole ring at angles of 74.12 (14), 26.13 (14) and 67.30 (14)°, respectively. In mol­ecule 2, due to the different mol­ecular environment in the crystal, the corresponding angles are different, viz. 71.72 (15), 16.14 (15) and 80.41 (15)°, respectively. In the crystal, mol­ecules 1 and 2 are linked by C—H⋯Cl inter­actions, and inversion-related 2 mol­ecules are linked by C—H⋯π inter­actions. There are no other significant inter­molecular inter­actions present.

Related literature

For some biological applications of imidazoles, see: Prabhu & Radha (2012[Prabhu, M. & Radha, R. (2012). Asian J. Pharm. Clin. Res. 5, 154-159.]); Sharma et al. (2009[Sharma, D., Narasimhan, B., Kumar, P., Judge, V., Narang, R., De Clercq, E. & Balzarini, J. (2009). Eur. J. Med. Chem. 44, 2347-2353.], 2010[Sharma, G. K., Kumar, S. & Pathak, D. (2010). Pharma Lett. 2, 223-230.]); Pandey et al. (2009[Pandey, J., Tiwari, V. K., Verma, S. S., Chaturvedi, V., Bhatnagar, S. & Sinha, S. (2009). Eur. J. Med. Chem. 44, 3350-3355.]); Sisko & Mellinger (2002[Sisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349-1357.]); Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. 15, 1083-1090.]). For the synthesis of imidazole-containing compounds and a similar structure, see: Simpson et al. (2013[Simpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5-o6.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24Cl2N2

  • Mr = 435.37

  • Monoclinic, P 21 /c

  • a = 20.172 (6) Å

  • b = 15.947 (5) Å

  • c = 14.500 (5) Å

  • β = 105.293 (7)°

  • V = 4499 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 150 K

  • 0.34 × 0.16 × 0.11 mm

Data collection
  • Bruker APEX 2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.516, Tmax = 0.928

  • 34900 measured reflections

  • 8837 independent reflections

  • 5052 reflections with I > 2σ(I)

  • Rint = 0.123

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.098

  • S = 0.84

  • 8837 reflections

  • 543 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C12A—H12A⋯Cl1i 0.95 2.70 3.512 (4) 143
C21—H21⋯Cg1ii 0.95 2.88 3.734 (3) 151
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Imidazoles are considered as an important pharmacophore in medicinal chemistry encompassing wide spectrum of biological activities (Prabhu & Radha, 2012) such as antibacterial, antiviral (Sharma et al., 2009, 2010), antirheumatoid arthritis, anticancer (Sisko & Mellinger, 2002), antitubercular (Pandey et al., 2009) and anti-inflammatory (Puratchikody & Doble, 2007). The title compound has been synthesized among series of imidazole derivatives according to our on going study in green synthesis of multi-substituted imidazoles via a multicomponent reactions method using ionic liquid as a recyclable catalyst.

In the title compound (Fig. 1), the asymmetric unit contains two independent molecules; 1 (with N1) and 2 (with N1A). In molecule 1, the two phenyl (C10–C15 and C16–C21) and 2,6-dichlorophenyl (C4–C9) rings are inclined to the N1/N2/C1–C3 imidazole ring at angles of 74.12 (14), 26.13 (14) and 67.30 (14)°, respectively. In molecule 2, the corresponding angles are 71.72 (15), 16.14 (15) and 80.41 (15)°, respectively (the atom labels of molecule 2 are with the extra suffix A). The differences between the corresponding angles arises due to the intra- and intermolecular interactions of the different molecular environments. They are different from those reported in a similar structure (Simpson et al., 2013).

In the crystal, molecules 1 and 2 are linked by C—H···Cl interactions, and inversion related 2 molecules are linked by C—H···π interactions (Table 1 and Fig. 2). There are no other significant intermolecular interactions present.

Related literature top

For some biological applications of imidazoles, see: Prabhu & Radha (2012); Sharma et al. (2009, 2010); Pandey et al. (2009); Sisko & Mellinger (2002); Puratchikody & Doble (2007). For the synthesis of imidazole-containing compounds and a similar structure, see: Simpson et al. (2013).

Experimental top

The title compound was synthesized following the previously reported procedure (Simpson et al., 2013). Block-like colourless crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of an ethanol solution of the title compound.

Refinement top

All H-atoms were included in calculated positions and refined using a riding model: C—H = 0.95, 0.99 and 0.98 Å, for CH(aromatic), CH2 and CH3 H atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms. One reflection (1 0 0) has been omitted in the final refinement cycles.

Computing details top

Data collection: SMART (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the two independent molecules (1 and 2-with suffix A) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the b axis. Hydrogen bonds are drawn as dashed lines (see Table 1 for details).
2-(2,6-Dichlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole top
Crystal data top
C26H24Cl2N2F(000) = 1824
Mr = 435.37Dx = 1.285 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 792 reflections
a = 20.172 (6) Åθ = 2.5–24.2°
b = 15.947 (5) ŵ = 0.30 mm1
c = 14.500 (5) ÅT = 150 K
β = 105.293 (7)°Block, colourless
V = 4499 (2) Å30.34 × 0.16 × 0.11 mm
Z = 8
Data collection top
Bruker APEX 2000 CCD area-detector
diffractometer
8837 independent reflections
Radiation source: fine-focus sealed tube5052 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.123
phi and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
h = 2424
Tmin = 0.516, Tmax = 0.928k = 1919
34900 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0212P)2]
where P = (Fo2 + 2Fc2)/3
8837 reflections(Δ/σ)max = 0.001
543 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C26H24Cl2N2V = 4499 (2) Å3
Mr = 435.37Z = 8
Monoclinic, P21/cMo Kα radiation
a = 20.172 (6) ŵ = 0.30 mm1
b = 15.947 (5) ÅT = 150 K
c = 14.500 (5) Å0.34 × 0.16 × 0.11 mm
β = 105.293 (7)°
Data collection top
Bruker APEX 2000 CCD area-detector
diffractometer
8837 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
5052 reflections with I > 2σ(I)
Tmin = 0.516, Tmax = 0.928Rint = 0.123
34900 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 0.84Δρmax = 0.29 e Å3
8837 reflectionsΔρmin = 0.39 e Å3
543 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.29823 (3)0.30921 (5)0.37517 (5)0.0297 (3)
Cl20.46202 (4)0.10547 (5)0.23512 (5)0.0328 (2)
N10.46666 (10)0.19189 (13)0.45220 (15)0.0205 (7)
N20.36928 (10)0.11983 (13)0.43427 (14)0.0204 (8)
C10.40305 (13)0.17285 (16)0.39371 (18)0.0200 (9)
C20.41270 (13)0.10305 (16)0.52403 (18)0.0195 (9)
C30.47296 (13)0.14686 (16)0.53614 (18)0.0202 (9)
C40.37540 (13)0.20741 (17)0.29671 (18)0.0210 (9)
C50.39632 (13)0.17906 (17)0.21808 (19)0.0241 (9)
C60.36586 (14)0.20696 (18)0.1261 (2)0.0289 (10)
C70.31307 (14)0.26443 (18)0.1118 (2)0.0295 (10)
C80.29128 (14)0.29496 (17)0.18758 (19)0.0274 (10)
C90.32282 (13)0.26701 (17)0.27873 (18)0.0227 (9)
C100.38985 (13)0.04658 (17)0.58975 (18)0.0213 (9)
C110.34051 (14)0.01395 (18)0.5538 (2)0.0298 (10)
C120.31617 (15)0.06537 (19)0.6145 (2)0.0382 (11)
C130.34109 (15)0.05737 (19)0.7124 (2)0.0348 (11)
C140.39050 (14)0.00240 (18)0.7488 (2)0.0308 (11)
C150.41468 (14)0.05382 (17)0.68861 (19)0.0264 (10)
C160.53813 (13)0.14413 (17)0.61316 (18)0.0203 (9)
C170.56398 (14)0.21282 (18)0.67047 (19)0.0296 (10)
C180.62524 (15)0.20745 (19)0.7407 (2)0.0346 (11)
C190.66190 (15)0.1337 (2)0.7538 (2)0.0365 (11)
C200.63697 (14)0.0648 (2)0.6983 (2)0.0356 (11)
C210.57527 (14)0.07020 (18)0.62853 (19)0.0280 (10)
C220.51523 (13)0.25222 (16)0.43213 (19)0.0226 (9)
C230.49632 (14)0.34200 (17)0.4496 (2)0.0289 (10)
C240.54602 (13)0.40739 (17)0.43014 (19)0.0287 (10)
C250.61807 (13)0.40211 (18)0.49662 (19)0.0317 (10)
C260.66054 (15)0.47987 (19)0.4898 (2)0.0425 (11)
Cl1A0.04153 (4)0.60347 (5)0.77291 (5)0.0408 (3)
Cl2A0.19909 (4)0.82158 (5)1.02289 (5)0.0462 (3)
N1A0.12565 (11)0.63396 (14)1.03916 (15)0.0237 (8)
N2A0.02673 (11)0.69733 (14)0.97245 (15)0.0240 (8)
C1A0.09269 (14)0.68241 (17)0.96875 (19)0.0229 (9)
C2A0.07903 (13)0.61583 (17)1.09207 (18)0.0230 (9)
C3A0.01745 (13)0.65406 (17)1.05079 (18)0.0229 (9)
C4A0.12283 (13)0.71366 (17)0.89307 (18)0.0227 (9)
C5A0.10486 (14)0.68040 (17)0.80107 (19)0.0272 (10)
C6A0.13600 (14)0.70545 (18)0.7313 (2)0.0312 (10)
C7A0.18707 (14)0.76503 (18)0.7527 (2)0.0316 (11)
C8A0.20691 (14)0.79964 (18)0.84299 (19)0.0307 (10)
C9A0.17463 (14)0.77444 (18)0.91125 (19)0.0261 (9)
C10A0.10028 (14)0.56404 (17)1.17776 (19)0.0235 (9)
C11A0.16101 (15)0.51845 (19)1.1938 (2)0.0374 (11)
C12A0.18591 (17)0.4736 (2)1.2769 (2)0.0458 (12)
C13A0.14991 (16)0.47077 (19)1.3459 (2)0.0400 (11)
C14A0.08958 (15)0.51536 (18)1.3310 (2)0.0333 (11)
C15A0.06511 (14)0.56180 (17)1.24883 (19)0.0280 (10)
C16A0.05062 (13)0.65026 (18)1.07212 (18)0.0241 (9)
C17A0.07410 (14)0.71327 (19)1.1209 (2)0.0324 (11)
C18A0.13809 (15)0.7079 (2)1.1390 (2)0.0375 (11)
C19A0.17886 (15)0.6386 (2)1.1090 (2)0.0376 (11)
C20A0.15554 (15)0.5749 (2)1.0622 (2)0.0429 (11)
C21A0.09166 (15)0.58025 (19)1.0439 (2)0.0364 (11)
C22A0.02348 (14)0.75371 (17)0.91036 (19)0.0285 (10)
C23A0.01743 (15)0.84245 (18)0.9496 (2)0.0372 (11)
C24A0.07254 (15)0.9019 (2)0.8910 (2)0.0421 (12)
C25A0.14530 (15)0.8789 (2)0.8894 (2)0.0483 (14)
C26A0.19694 (17)0.9481 (2)0.8481 (2)0.0665 (17)
H60.381200.186700.073600.0350*
H70.291500.283200.048900.0350*
H80.255000.334800.177300.0330*
H110.323200.020300.486600.0360*
H120.282200.106400.588700.0460*
H130.324400.092600.754200.0420*
H140.408000.008200.816100.0370*
H150.448700.094700.714800.0320*
H170.539200.264100.661200.0360*
H180.642000.254600.779900.0420*
H190.704500.130300.801300.0440*
H200.662000.013700.707900.0430*
H210.558200.022400.590600.0340*
H22A0.516500.246200.364700.0270*
H22B0.561800.239800.473200.0270*
H23A0.494500.347300.516800.0350*
H23B0.449800.354000.408300.0350*
H24A0.548900.400900.363400.0340*
H24B0.527200.463900.436000.0340*
H25A0.641500.351900.480100.0380*
H25B0.615000.395600.563300.0380*
H26A0.663200.487000.423800.0640*
H26B0.707000.473300.532000.0640*
H26C0.638800.529300.509400.0640*
H6A0.122200.681700.669100.0370*
H7A0.208700.782400.705100.0380*
H8A0.242500.840400.858100.0370*
H11A0.185800.518301.146500.0450*
H12A0.228200.444201.286800.0550*
H13A0.166500.438701.402500.0480*
H14A0.064500.514101.378000.0400*
H15A0.023700.592701.240400.0340*
H17A0.046000.760901.142300.0390*
H18A0.153800.751901.172100.0450*
H19A0.223000.634901.120600.0450*
H20A0.183400.526801.042300.0520*
H21A0.075900.535701.011700.0440*
H22C0.070500.732400.904700.0340*
H22D0.015900.754200.845600.0340*
H23C0.028500.864800.950600.0450*
H23D0.021100.841001.016300.0450*
H24C0.063100.959200.917400.0500*
H24D0.068600.903200.824400.0500*
H25C0.147500.866300.955400.0580*
H25D0.158400.827400.850800.0580*
H26D0.186700.997800.889200.1000*
H26E0.243500.928500.844900.1000*
H26F0.193800.962500.783700.1000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0307 (4)0.0309 (5)0.0279 (4)0.0085 (4)0.0082 (3)0.0019 (3)
Cl20.0339 (4)0.0290 (4)0.0374 (4)0.0071 (4)0.0127 (3)0.0001 (4)
N10.0176 (12)0.0162 (13)0.0271 (13)0.0001 (10)0.0047 (10)0.0034 (11)
N20.0194 (12)0.0186 (14)0.0236 (13)0.0003 (11)0.0063 (10)0.0013 (10)
C10.0191 (15)0.0162 (16)0.0250 (15)0.0016 (13)0.0063 (12)0.0001 (13)
C20.0213 (15)0.0159 (15)0.0224 (15)0.0006 (13)0.0075 (12)0.0009 (13)
C30.0216 (16)0.0148 (16)0.0245 (15)0.0042 (13)0.0064 (12)0.0018 (12)
C40.0199 (15)0.0190 (16)0.0240 (15)0.0055 (13)0.0059 (12)0.0018 (13)
C50.0238 (16)0.0192 (17)0.0301 (16)0.0030 (13)0.0087 (13)0.0024 (13)
C60.0330 (18)0.0276 (19)0.0268 (16)0.0058 (15)0.0093 (14)0.0037 (14)
C70.0335 (18)0.0290 (19)0.0236 (16)0.0049 (15)0.0031 (14)0.0052 (14)
C80.0261 (17)0.0247 (18)0.0296 (17)0.0029 (14)0.0042 (13)0.0052 (14)
C90.0224 (16)0.0199 (17)0.0265 (16)0.0022 (13)0.0076 (13)0.0015 (13)
C100.0173 (15)0.0182 (16)0.0290 (16)0.0042 (13)0.0073 (12)0.0042 (13)
C110.0288 (18)0.0318 (19)0.0273 (17)0.0042 (15)0.0048 (14)0.0021 (14)
C120.0352 (19)0.036 (2)0.044 (2)0.0140 (16)0.0117 (16)0.0020 (16)
C130.0347 (19)0.036 (2)0.0376 (19)0.0047 (16)0.0167 (15)0.0106 (16)
C140.0308 (18)0.035 (2)0.0269 (17)0.0040 (15)0.0083 (14)0.0052 (15)
C150.0231 (16)0.0275 (18)0.0296 (17)0.0016 (14)0.0085 (13)0.0018 (14)
C160.0182 (15)0.0195 (16)0.0250 (15)0.0015 (13)0.0088 (12)0.0016 (13)
C170.0318 (18)0.0206 (18)0.0343 (18)0.0033 (14)0.0050 (14)0.0002 (14)
C180.0360 (19)0.030 (2)0.0335 (18)0.0097 (16)0.0015 (15)0.0054 (15)
C190.0249 (17)0.046 (2)0.0322 (18)0.0039 (16)0.0038 (14)0.0039 (16)
C200.0259 (18)0.035 (2)0.0420 (19)0.0063 (15)0.0019 (15)0.0047 (16)
C210.0266 (17)0.0257 (18)0.0305 (17)0.0022 (14)0.0052 (14)0.0029 (14)
C220.0209 (16)0.0213 (17)0.0270 (16)0.0014 (13)0.0089 (13)0.0058 (13)
C230.0248 (17)0.0226 (18)0.0400 (18)0.0002 (14)0.0096 (14)0.0059 (14)
C240.0289 (17)0.0221 (17)0.0339 (17)0.0019 (14)0.0064 (14)0.0057 (14)
C250.0293 (17)0.0292 (19)0.0337 (17)0.0020 (15)0.0031 (14)0.0012 (15)
C260.0318 (19)0.034 (2)0.058 (2)0.0081 (16)0.0054 (16)0.0036 (17)
Cl1A0.0438 (5)0.0379 (5)0.0407 (5)0.0129 (4)0.0112 (4)0.0081 (4)
Cl2A0.0511 (5)0.0586 (6)0.0299 (4)0.0256 (5)0.0126 (4)0.0098 (4)
N1A0.0219 (13)0.0264 (15)0.0236 (13)0.0004 (11)0.0072 (10)0.0015 (11)
N2A0.0204 (13)0.0262 (15)0.0248 (13)0.0044 (11)0.0048 (10)0.0041 (11)
C1A0.0213 (16)0.0221 (17)0.0258 (16)0.0012 (13)0.0072 (13)0.0010 (13)
C2A0.0234 (16)0.0216 (17)0.0248 (15)0.0002 (14)0.0079 (13)0.0002 (13)
C3A0.0221 (16)0.0225 (17)0.0247 (15)0.0027 (13)0.0070 (13)0.0002 (13)
C4A0.0207 (16)0.0244 (17)0.0236 (15)0.0066 (13)0.0070 (12)0.0047 (13)
C5A0.0283 (17)0.0236 (18)0.0302 (17)0.0003 (14)0.0085 (14)0.0016 (14)
C6A0.0335 (18)0.036 (2)0.0250 (16)0.0035 (16)0.0093 (14)0.0014 (14)
C7A0.0291 (18)0.034 (2)0.0350 (18)0.0031 (15)0.0142 (15)0.0077 (15)
C8A0.0251 (17)0.036 (2)0.0311 (17)0.0013 (15)0.0076 (14)0.0043 (15)
C9A0.0253 (16)0.0313 (18)0.0225 (15)0.0006 (14)0.0076 (13)0.0005 (14)
C10A0.0242 (16)0.0191 (17)0.0285 (16)0.0002 (13)0.0094 (13)0.0003 (13)
C11A0.042 (2)0.038 (2)0.0353 (19)0.0124 (17)0.0158 (16)0.0044 (16)
C12A0.052 (2)0.046 (2)0.041 (2)0.0273 (18)0.0150 (18)0.0110 (17)
C13A0.055 (2)0.034 (2)0.0287 (18)0.0092 (18)0.0070 (16)0.0118 (15)
C14A0.0377 (19)0.034 (2)0.0285 (17)0.0076 (16)0.0093 (15)0.0004 (15)
C15A0.0246 (17)0.0280 (18)0.0315 (17)0.0017 (14)0.0076 (14)0.0030 (14)
C16A0.0210 (16)0.0288 (18)0.0228 (15)0.0048 (14)0.0065 (12)0.0039 (14)
C17A0.0257 (17)0.0298 (19)0.0428 (19)0.0002 (15)0.0111 (15)0.0011 (15)
C18A0.0298 (19)0.041 (2)0.046 (2)0.0076 (17)0.0176 (16)0.0000 (17)
C19A0.0238 (17)0.049 (2)0.043 (2)0.0011 (17)0.0143 (15)0.0089 (17)
C20A0.0290 (19)0.044 (2)0.057 (2)0.0136 (17)0.0135 (17)0.0056 (18)
C21A0.0307 (19)0.032 (2)0.049 (2)0.0039 (16)0.0147 (16)0.0089 (16)
C22A0.0244 (17)0.0307 (19)0.0292 (17)0.0050 (14)0.0049 (13)0.0086 (14)
C23A0.0373 (19)0.028 (2)0.0436 (19)0.0045 (16)0.0059 (16)0.0094 (16)
C24A0.043 (2)0.036 (2)0.047 (2)0.0094 (17)0.0113 (17)0.0104 (17)
C25A0.042 (2)0.057 (3)0.049 (2)0.0204 (19)0.0174 (17)0.0084 (18)
C26A0.054 (3)0.077 (3)0.070 (3)0.037 (2)0.019 (2)0.007 (2)
Geometric parameters (Å, º) top
Cl1—C91.738 (3)C24—H24A0.9900
Cl2—C51.738 (3)C24—H24B0.9900
Cl1A—C5A1.740 (3)C25—H25A0.9900
Cl2A—C9A1.734 (3)C25—H25B0.9900
N1—C31.390 (3)C26—H26A0.9800
N1—C11.373 (3)C26—H26B0.9800
N1—C221.456 (3)C26—H26C0.9800
N2—C21.390 (3)C1A—C4A1.475 (4)
N2—C11.318 (3)C2A—C3A1.371 (4)
N1A—C2A1.392 (4)C2A—C10A1.459 (4)
N1A—C1A1.313 (3)C3A—C16A1.486 (4)
N2A—C1A1.367 (4)C4A—C5A1.392 (4)
N2A—C3A1.383 (3)C4A—C9A1.398 (4)
N2A—C22A1.471 (4)C5A—C6A1.383 (4)
C1—C41.476 (4)C6A—C7A1.375 (4)
C2—C31.373 (4)C7A—C8A1.379 (4)
C2—C101.471 (4)C8A—C9A1.380 (4)
C3—C161.484 (4)C10A—C11A1.390 (4)
C4—C51.392 (4)C10A—C15A1.397 (4)
C4—C91.397 (4)C11A—C12A1.377 (4)
C5—C61.386 (4)C12A—C13A1.383 (4)
C6—C71.379 (4)C13A—C14A1.377 (4)
C7—C81.376 (4)C14A—C15A1.379 (4)
C8—C91.381 (4)C16A—C17A1.382 (4)
C10—C151.393 (4)C16A—C21A1.386 (4)
C10—C111.386 (4)C17A—C18A1.386 (4)
C11—C121.384 (4)C18A—C19A1.378 (4)
C12—C131.381 (4)C19A—C20A1.372 (4)
C13—C141.380 (4)C20A—C21A1.385 (4)
C14—C151.377 (4)C22A—C23A1.518 (4)
C16—C171.391 (4)C23A—C24A1.536 (4)
C16—C211.383 (4)C24A—C25A1.507 (4)
C17—C181.381 (4)C25A—C26A1.527 (5)
C18—C191.376 (4)C6A—H6A0.9500
C19—C201.376 (4)C7A—H7A0.9500
C20—C211.384 (4)C8A—H8A0.9500
C22—C231.520 (4)C11A—H11A0.9500
C23—C241.524 (4)C12A—H12A0.9500
C24—C251.520 (4)C13A—H13A0.9500
C25—C261.525 (4)C14A—H14A0.9500
C6—H60.9500C15A—H15A0.9500
C7—H70.9500C17A—H17A0.9500
C8—H80.9500C18A—H18A0.9500
C11—H110.9500C19A—H19A0.9500
C12—H120.9500C20A—H20A0.9500
C13—H130.9500C21A—H21A0.9500
C14—H140.9500C22A—H22C0.9900
C15—H150.9500C22A—H22D0.9900
C17—H170.9500C23A—H23C0.9900
C18—H180.9500C23A—H23D0.9900
C19—H190.9500C24A—H24C0.9900
C20—H200.9500C24A—H24D0.9900
C21—H210.9500C25A—H25C0.9900
C22—H22B0.9900C25A—H25D0.9900
C22—H22A0.9900C26A—H26D0.9800
C23—H23B0.9900C26A—H26E0.9800
C23—H23A0.9900C26A—H26F0.9800
C1—N1—C3106.4 (2)H26A—C26—H26B109.00
C1—N1—C22126.3 (2)C25—C26—H26A110.00
C3—N1—C22127.3 (2)C25—C26—H26B109.00
C1—N2—C2105.6 (2)C25—C26—H26C109.00
C1A—N1A—C2A105.9 (2)N1A—C1A—N2A111.8 (2)
C1A—N2A—C22A127.1 (2)N1A—C1A—C4A123.7 (3)
C3A—N2A—C22A125.9 (2)N2A—C1A—C4A124.6 (2)
C1A—N2A—C3A106.8 (2)N1A—C2A—C3A109.5 (2)
N2—C1—C4123.7 (2)N1A—C2A—C10A119.8 (2)
N1—C1—C4124.3 (2)C3A—C2A—C10A130.7 (3)
N1—C1—N2112.0 (2)N2A—C3A—C2A106.1 (2)
N2—C2—C10119.8 (2)N2A—C3A—C16A121.6 (2)
C3—C2—C10130.3 (2)C2A—C3A—C16A132.2 (2)
N2—C2—C3109.9 (2)C1A—C4A—C5A122.0 (2)
N1—C3—C2106.1 (2)C1A—C4A—C9A121.9 (2)
N1—C3—C16122.2 (2)C5A—C4A—C9A116.0 (2)
C2—C3—C16131.3 (2)Cl1A—C5A—C4A118.9 (2)
C1—C4—C5122.6 (2)Cl1A—C5A—C6A118.6 (2)
C1—C4—C9120.6 (2)C4A—C5A—C6A122.5 (3)
C5—C4—C9116.6 (2)C5A—C6A—C7A119.5 (3)
Cl2—C5—C6118.8 (2)C6A—C7A—C8A120.2 (3)
C4—C5—C6122.1 (3)C7A—C8A—C9A119.4 (3)
Cl2—C5—C4119.2 (2)Cl2A—C9A—C4A119.4 (2)
C5—C6—C7119.1 (3)Cl2A—C9A—C8A118.1 (2)
C6—C7—C8120.8 (3)C4A—C9A—C8A122.5 (2)
C7—C8—C9119.1 (3)C2A—C10A—C11A119.1 (3)
Cl1—C9—C8119.2 (2)C2A—C10A—C15A123.4 (3)
C4—C9—C8122.3 (2)C11A—C10A—C15A117.4 (2)
Cl1—C9—C4118.50 (19)C10A—C11A—C12A121.3 (3)
C2—C10—C11120.0 (2)C11A—C12A—C13A120.7 (3)
C2—C10—C15121.8 (2)C12A—C13A—C14A118.7 (3)
C11—C10—C15118.2 (2)C13A—C14A—C15A120.9 (3)
C10—C11—C12120.9 (3)C10A—C15A—C14A121.0 (3)
C11—C12—C13120.3 (3)C3A—C16A—C17A122.5 (3)
C12—C13—C14119.2 (3)C3A—C16A—C21A119.0 (3)
C13—C14—C15120.7 (3)C17A—C16A—C21A118.6 (3)
C10—C15—C14120.8 (3)C16A—C17A—C18A120.9 (3)
C3—C16—C17123.0 (2)C17A—C18A—C19A119.9 (3)
C17—C16—C21118.3 (2)C18A—C19A—C20A119.7 (3)
C3—C16—C21118.7 (2)C19A—C20A—C21A120.5 (3)
C16—C17—C18120.9 (3)C16A—C21A—C20A120.4 (3)
C17—C18—C19119.9 (3)N2A—C22A—C23A111.5 (2)
C18—C19—C20120.1 (3)C22A—C23A—C24A113.2 (2)
C19—C20—C21119.8 (3)C23A—C24A—C25A114.7 (3)
C16—C21—C20121.0 (3)C24A—C25A—C26A113.0 (3)
N1—C22—C23112.2 (2)C5A—C6A—H6A120.00
C22—C23—C24114.1 (2)C7A—C6A—H6A120.00
C23—C24—C25114.2 (2)C6A—C7A—H7A120.00
C24—C25—C26111.9 (2)C8A—C7A—H7A120.00
C5—C6—H6120.00C7A—C8A—H8A120.00
C7—C6—H6120.00C9A—C8A—H8A120.00
C8—C7—H7120.00C10A—C11A—H11A119.00
C6—C7—H7120.00C12A—C11A—H11A119.00
C7—C8—H8120.00C11A—C12A—H12A120.00
C9—C8—H8120.00C13A—C12A—H12A120.00
C10—C11—H11120.00C12A—C13A—H13A121.00
C12—C11—H11120.00C14A—C13A—H13A121.00
C13—C12—H12120.00C13A—C14A—H14A120.00
C11—C12—H12120.00C15A—C14A—H14A120.00
C14—C13—H13120.00C10A—C15A—H15A119.00
C12—C13—H13120.00C14A—C15A—H15A119.00
C13—C14—H14120.00C16A—C17A—H17A120.00
C15—C14—H14120.00C18A—C17A—H17A120.00
C10—C15—H15120.00C17A—C18A—H18A120.00
C14—C15—H15120.00C19A—C18A—H18A120.00
C16—C17—H17120.00C18A—C19A—H19A120.00
C18—C17—H17120.00C20A—C19A—H19A120.00
C19—C18—H18120.00C19A—C20A—H20A120.00
C17—C18—H18120.00C21A—C20A—H20A120.00
C18—C19—H19120.00C16A—C21A—H21A120.00
C20—C19—H19120.00C20A—C21A—H21A120.00
C21—C20—H20120.00N2A—C22A—H22C109.00
C19—C20—H20120.00N2A—C22A—H22D109.00
C16—C21—H21120.00C23A—C22A—H22C109.00
C20—C21—H21119.00C23A—C22A—H22D109.00
N1—C22—H22B109.00H22C—C22A—H22D108.00
C23—C22—H22A109.00C22A—C23A—H23C109.00
C23—C22—H22B109.00C22A—C23A—H23D109.00
N1—C22—H22A109.00C24A—C23A—H23C109.00
H22A—C22—H22B108.00C24A—C23A—H23D109.00
H23A—C23—H23B108.00H23C—C23A—H23D108.00
C22—C23—H23B109.00C23A—C24A—H24C109.00
C24—C23—H23B109.00C23A—C24A—H24D109.00
C22—C23—H23A109.00C25A—C24A—H24C109.00
C24—C23—H23A109.00C25A—C24A—H24D109.00
C23—C24—H24A109.00H24C—C24A—H24D108.00
H24A—C24—H24B108.00C24A—C25A—H25C109.00
C23—C24—H24B109.00C24A—C25A—H25D109.00
C25—C24—H24A109.00C26A—C25A—H25C109.00
C25—C24—H24B109.00C26A—C25A—H25D109.00
C24—C25—H25B109.00H25C—C25A—H25D108.00
C26—C25—H25A109.00C25A—C26A—H26D109.00
C26—C25—H25B109.00C25A—C26A—H26E110.00
C24—C25—H25A109.00C25A—C26A—H26F110.00
H25A—C25—H25B108.00H26D—C26A—H26E109.00
H26A—C26—H26C110.00H26D—C26A—H26F109.00
H26B—C26—H26C109.00H26E—C26A—H26F109.00
C3—N1—C1—N20.1 (3)C11—C12—C13—C140.0 (5)
C3—N1—C1—C4179.9 (2)C12—C13—C14—C150.2 (5)
C22—N1—C1—N2175.8 (2)C13—C14—C15—C100.1 (4)
C22—N1—C1—C44.2 (4)C3—C16—C21—C20178.8 (3)
C1—N1—C3—C20.1 (3)C3—C16—C17—C18179.4 (3)
C1—N1—C3—C16173.3 (2)C21—C16—C17—C180.2 (4)
C22—N1—C3—C2175.7 (2)C17—C16—C21—C200.8 (4)
C22—N1—C3—C1610.9 (4)C16—C17—C18—C190.8 (4)
C1—N1—C22—C2378.7 (3)C17—C18—C19—C201.3 (4)
C3—N1—C22—C2396.3 (3)C18—C19—C20—C210.7 (4)
C2—N2—C1—N10.1 (3)C19—C20—C21—C160.3 (4)
C2—N2—C1—C4180.0 (2)N1—C22—C23—C24179.6 (2)
C1—N2—C2—C30.1 (3)C22—C23—C24—C2564.9 (3)
C1—N2—C2—C10178.7 (2)C23—C24—C25—C26166.8 (2)
C2A—N1A—C1A—N2A0.1 (3)N1A—C1A—C4A—C5A104.6 (3)
C2A—N1A—C1A—C4A177.6 (2)N1A—C1A—C4A—C9A70.9 (4)
C1A—N1A—C2A—C3A0.6 (3)N2A—C1A—C4A—C5A72.8 (4)
C1A—N1A—C2A—C10A178.6 (2)N2A—C1A—C4A—C9A111.8 (3)
C3A—N2A—C1A—C4A177.0 (2)N1A—C2A—C3A—N2A1.0 (3)
C22A—N2A—C1A—N1A174.8 (2)N1A—C2A—C3A—C16A174.2 (3)
C3A—N2A—C22A—C23A86.8 (3)C10A—C2A—C3A—N2A178.1 (3)
C3A—N2A—C1A—N1A0.7 (3)C10A—C2A—C3A—C16A6.7 (5)
C1A—N2A—C22A—C23A88.0 (3)N1A—C2A—C10A—C11A14.2 (4)
C1A—N2A—C3A—C16A174.8 (2)N1A—C2A—C10A—C15A161.4 (3)
C22A—N2A—C1A—C4A7.5 (4)C3A—C2A—C10A—C11A166.8 (3)
C1A—N2A—C3A—C2A1.0 (3)C3A—C2A—C10A—C15A17.6 (5)
C22A—N2A—C3A—C2A174.6 (2)N2A—C3A—C16A—C17A83.2 (3)
C22A—N2A—C3A—C16A9.6 (4)N2A—C3A—C16A—C21A98.1 (3)
N2—C1—C4—C5103.4 (3)C2A—C3A—C16A—C17A102.2 (4)
N1—C1—C4—C9107.9 (3)C2A—C3A—C16A—C21A76.4 (4)
N1—C1—C4—C576.6 (4)C1A—C4A—C5A—Cl1A3.5 (4)
N2—C1—C4—C972.2 (4)C1A—C4A—C5A—C6A175.7 (3)
N2—C2—C10—C15152.3 (3)C9A—C4A—C5A—Cl1A179.2 (2)
N2—C2—C3—N10.2 (3)C9A—C4A—C5A—C6A0.0 (4)
N2—C2—C3—C16172.4 (3)C1A—C4A—C9A—Cl2A5.9 (4)
C10—C2—C3—N1178.5 (3)C1A—C4A—C9A—C8A175.0 (3)
C10—C2—C3—C168.9 (5)C5A—C4A—C9A—Cl2A178.4 (2)
N2—C2—C10—C1125.4 (4)C5A—C4A—C9A—C8A0.8 (4)
C3—C2—C10—C11156.0 (3)Cl1A—C5A—C6A—C7A178.8 (2)
C3—C2—C10—C1526.3 (4)C4A—C5A—C6A—C7A0.4 (4)
N1—C3—C16—C1770.2 (4)C5A—C6A—C7A—C8A0.2 (4)
C2—C3—C16—C2162.2 (4)C6A—C7A—C8A—C9A0.6 (4)
N1—C3—C16—C21109.4 (3)C7A—C8A—C9A—Cl2A178.1 (2)
C2—C3—C16—C17118.2 (3)C7A—C8A—C9A—C4A1.1 (4)
C1—C4—C5—C6174.5 (3)C2A—C10A—C11A—C12A175.1 (3)
C1—C4—C5—Cl24.8 (4)C15A—C10A—C11A—C12A0.7 (4)
C5—C4—C9—C82.0 (4)C2A—C10A—C15A—C14A176.3 (3)
C1—C4—C9—Cl18.0 (4)C11A—C10A—C15A—C14A0.7 (4)
C9—C4—C5—Cl2179.5 (2)C10A—C11A—C12A—C13A1.9 (5)
C9—C4—C5—C61.3 (4)C11A—C12A—C13A—C14A1.6 (5)
C1—C4—C9—C8173.8 (3)C12A—C13A—C14A—C15A0.3 (4)
C5—C4—C9—Cl1176.2 (2)C13A—C14A—C15A—C10A0.9 (4)
Cl2—C5—C6—C7179.1 (2)C3A—C16A—C17A—C18A179.6 (3)
C4—C5—C6—C70.2 (4)C21A—C16A—C17A—C18A1.8 (4)
C5—C6—C7—C81.0 (4)C3A—C16A—C21A—C20A179.7 (3)
C6—C7—C8—C90.3 (4)C17A—C16A—C21A—C20A1.7 (4)
C7—C8—C9—C41.3 (4)C16A—C17A—C18A—C19A0.7 (4)
C7—C8—C9—Cl1176.9 (2)C17A—C18A—C19A—C20A0.7 (4)
C11—C10—C15—C140.3 (4)C18A—C19A—C20A—C21A0.8 (4)
C2—C10—C15—C14177.4 (3)C19A—C20A—C21A—C16A0.4 (4)
C2—C10—C11—C12177.2 (3)N2A—C22A—C23A—C24A175.6 (2)
C15—C10—C11—C120.5 (4)C22A—C23A—C24A—C25A63.0 (3)
C10—C11—C12—C130.3 (5)C23A—C24A—C25A—C26A168.4 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.
D—H···AD—HH···AD···AD—H···A
C12A—H12A···Cl1i0.952.703.512 (4)143
C21—H21···Cg1ii0.952.883.734 (3)151
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC26H24Cl2N2
Mr435.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)20.172 (6), 15.947 (5), 14.500 (5)
β (°) 105.293 (7)
V3)4499 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.34 × 0.16 × 0.11
Data collection
DiffractometerBruker APEX 2000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2011)
Tmin, Tmax0.516, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
34900, 8837, 5052
Rint0.123
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.098, 0.84
No. of reflections8837
No. of parameters543
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.39

Computer programs: SMART (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.
D—H···AD—HH···AD···AD—H···A
C12A—H12A···Cl1i0.952.703.512 (4)143
C21—H21···Cg1ii0.952.883.734 (3)151
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.
 

Acknowledgements

The authors are grateful to Manchester Metropolitan University, the University of Leicester and Erciyes University for supporting this study.

References

First citationBruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationPandey, J., Tiwari, V. K., Verma, S. S., Chaturvedi, V., Bhatnagar, S. & Sinha, S. (2009). Eur. J. Med. Chem. 44, 3350–3355.  Web of Science CrossRef PubMed CAS
First citationPrabhu, M. & Radha, R. (2012). Asian J. Pharm. Clin. Res. 5, 154–159.  CAS
First citationPuratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. 15, 1083–1090.  Web of Science CrossRef PubMed CAS
First citationSharma, G. K., Kumar, S. & Pathak, D. (2010). Pharma Lett. 2, 223–230.  CAS
First citationSharma, D., Narasimhan, B., Kumar, P., Judge, V., Narang, R., De Clercq, E. & Balzarini, J. (2009). Eur. J. Med. Chem. 44, 2347–2353.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSimpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5–o6.  CSD CrossRef CAS IUCr Journals
First citationSisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349–1357.  Web of Science CrossRef CAS
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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Volume 69| Part 6| June 2013| Pages o846-o847
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