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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1833-o1834

2-(3,4-Di­meth­­oxy­phen­yl)-1-pentyl-4,5-di­phenyl-1H-imidazole

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, eDepartment of Chemistry, University of Leicester, Leicester, England, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 20 November 2013; accepted 21 November 2013; online 27 November 2013)

The central imidazole ring in the title compound, C28H30N2O2, makes dihedral angles of 28.42 (13), 71.22 (15) and 29.50 (14)°, respectively, with the phenyl rings in the 4- and 5-positions and the 3,4-di­meth­oxy­phenyl group. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds, weak ππ stacking inter­actions [centroid–centroid distance = 3.760 (2) Å] and C—H⋯π contacts, forming a three-dimensional network.

Related literature

For medicinal and industrial applications of imidazole-containing compounds see: Oyeka & Gugnani (1992[Oyeka, C. A. & Gugnani, H. C. (1992). Mycoses, 35, 357-61.]); Schrekker et al. (2013[Schrekker, H. S., Donato, R. K., Fuentefri, A. M., Bergamo, V., Oliveira, L. F. & Machado, M. M. (2013). MedChemComm, 4, 1457-1460.]); Mital (2009[Mital, A. (2009). Sci. Pharm. 77, 497-520.]); Juchau (1989[Juchau, M. R. (1989). Annu. Rev. Pharmacol. Toxicol. 29, 165-167.]); Rondu et al. (1997[Rondu, F., Le Bihan, G., Wang, X., Lamouri, A., Touboul, E., Dive, G., Bellahsene, T., Pfeiffer, B., Renard, P., Guardiola-L, B., Manechez, D., Penicaud, L., Ktorza, A. & Godfroid, J. J. (1997). J. Med. Chem. 40, 3793-3803.]); Bousquet & Feldman (1999[Bousquet, P. & Feldman, J. (1999). Drugs, 58, 799-812.]); Ueno et al. (1995[Ueno, M., Imaizumi, K., Sugita, T., Takata, I. & Takeshita, M. (1995). Int. J. Immunopharmacol. 17, 597-603.]); Jung & Huang (2000[Jung, M. E. & Huang, A. (2000). Org. Lett. 2, 2659-2661.]); Isobe et al. (2001[Isobe, T., Fukuda, K., Araki, Y. & Ishikawa, T. (2001). Chem. Commun. pp. 243-244.]). For similar structures, see: Akkurt et al. (2013[Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o846-o847.]); Mohamed et al. (2013[Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1417.]).

[Scheme 1]

Experimental

Crystal data
  • C28H30N2O2

  • Mr = 426.54

  • Triclinic, [P \overline 1]

  • a = 8.900 (2) Å

  • b = 11.915 (3) Å

  • c = 12.009 (3) Å

  • α = 106.757 (6)°

  • β = 96.007 (5)°

  • γ = 108.170 (6)°

  • V = 1131.8 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 150 K

  • 0.24 × 0.21 × 0.11 mm

Data collection
  • Bruker APEX2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.668, Tmax = 0.981

  • 8350 measured reflections

  • 3953 independent reflections

  • 2219 reflections with I > 2σ(I)

  • Rint = 0.086

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.127

  • S = 0.87

  • 3953 reflections

  • 292 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.25 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
C23—H23⋯O1i 0.95 2.53 3.168 (4) 125
C27—H27A⋯N2ii 0.98 2.51 3.474 (3) 168
C27—H27ACg1ii 0.98 2.77 3.608 (3) 144
Symmetry codes: (i) x-1, y-1, z-1; (ii) -x+2, -y+2, -z+2.

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

Many drugs contain an imidazole ring. Examples include butoconazole, clomidazole, clotrimazole, croconazole, econazole, fenticonazole, ketoconazole, isoconazole miconazole, neticonazole, omoconazole, oxiconazole, sertaconazole, sulconazole and tioconazole all of which act as antifungal drugs (Oyeka & Gugnani, 1992, Schrekker et al., 2013). Antibiotic drugs such as metronidazole, tinidazole and nimorazole also contain imidazoles (Mital, 2009; Juchau, 1989). Moreover, 2-substituted imidazolines are used as synthetic intermediates (Rondu et al., 1997), catalysts (Bousquet & Feldman, 1999), chiral auxiliaries (Ueno et al., 1995), chiral catalysts (Jung & Huang, 2000) and ligands for asymmetric catalysis (Isobe et al., 2001)in various synthetic reactions. Based on such facts, and as an extension of our work concerning the production bio-active heterocyclic compounds, we report in this study the synthesis and crystal structure of another imidazole derivative.

In the non-planar title compound (I), (Fig. 1), the dihedral angles between the (N1/N2/C1–C3) imidazole ring, and the two phenyl rings (C15–C20 and C21–C26) and the 3,4-dimethoxyphenyl group (C4–C9) are 28.42 (13), 71.22 (15) and 29.50 (14)°, respectively.

The N1–C10–C11–C12 and C11–C12–C13–C14 torsion angles are 173.6 (2) and 66.4 (4)°, respectively. The bond lengths and bond angles in (I) are normal and comparable to those reported for the similar compounds (Akkurt et al., 2013; Mohamed et al., 2013).

The crystal structure is stabilized by the intermolecular C—H···O, C—H···N hydrogen bonds (Table 1, Fig. 2), weak π-π stacking interactions [Cg2···Cg2 (2 - x, 2 - y, 2 - z) = 3.760 (2) Å] between the benzene rings of adjacent 3,4-dimethoxyphenyl groups and C—H···π contacts (Table 1).

Related literature top

For medicinal and industrial applications of imidazole-containing compounds see: Oyeka & Gugnani (1992); Schrekker et al. (2013); Mital (2009); Juchau (1989); Rondu et al. (1997); Bousquet & Feldman (1999); Ueno et al. (1995); Jung & Huang (2000); Isobe et al. (2001). For similar structures, see: Akkurt et al. (2013); Mohamed et al. (2013).

Experimental top

The title compound was prepared by our previously reported method (Mohamed et al., 2013). Single crystals sutiable for X-ray difraction were grown up by the slow evaporation method from an ethanolic solution of (I). M.p. 424 K and 83% yield.

Refinement top

H atoms were included in calculated positions and refined using a riding model with C—H = 0.95 - 0.99 Å and Uiso(H) = 1.5Ueq(Cmethyl) and = 1.2Ueq(C) for other H atoms. One reflection (0 0 1) was affected by the beam stop and was omitted from the refinement.

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 title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
2-(3,4-Dimethoxyphenyl)-1-pentyl-4,5-diphenyl-1H-imidazole top
Crystal data top
C28H30N2O2Z = 2
Mr = 426.54F(000) = 456
Triclinic, P1Dx = 1.252 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.900 (2) ÅCell parameters from 856 reflections
b = 11.915 (3) Åθ = 2.5–20.8°
c = 12.009 (3) ŵ = 0.08 mm1
α = 106.757 (6)°T = 150 K
β = 96.007 (5)°Block, colourless
γ = 108.170 (6)°0.24 × 0.21 × 0.11 mm
V = 1131.8 (5) Å3
Data collection top
Bruker APEX2000 CCD area-detector
diffractometer
3953 independent reflections
Radiation source: fine-focus sealed tube2219 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
h = 1010
Tmin = 0.668, Tmax = 0.981k = 1314
8350 measured reflectionsl = 1414
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0391P)2]
where P = (Fo2 + 2Fc2)/3
3953 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C28H30N2O2γ = 108.170 (6)°
Mr = 426.54V = 1131.8 (5) Å3
Triclinic, P1Z = 2
a = 8.900 (2) ÅMo Kα radiation
b = 11.915 (3) ŵ = 0.08 mm1
c = 12.009 (3) ÅT = 150 K
α = 106.757 (6)°0.24 × 0.21 × 0.11 mm
β = 96.007 (5)°
Data collection top
Bruker APEX2000 CCD area-detector
diffractometer
3953 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
2219 reflections with I > 2σ(I)
Tmin = 0.668, Tmax = 0.981Rint = 0.086
8350 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 0.87Δρmax = 0.25 e Å3
3953 reflectionsΔρmin = 0.25 e Å3
292 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
O11.0678 (2)1.23924 (16)1.28583 (16)0.0391 (7)
O21.0748 (2)1.05208 (17)1.34508 (16)0.0404 (7)
N10.5735 (2)0.70894 (19)0.89430 (18)0.0259 (8)
N20.7629 (2)0.66063 (19)0.98101 (18)0.0278 (8)
C10.7160 (3)0.7530 (2)0.9748 (2)0.0262 (9)
C20.6472 (3)0.5534 (2)0.9023 (2)0.0257 (9)
C30.5296 (3)0.5811 (2)0.8472 (2)0.0272 (9)
C40.8031 (3)0.8829 (2)1.0501 (2)0.0268 (9)
C50.8063 (3)0.9857 (2)1.0185 (2)0.0305 (9)
C60.8932 (3)1.1059 (2)1.0950 (2)0.0316 (10)
C70.9794 (3)1.1250 (2)1.2033 (2)0.0287 (9)
C80.9822 (3)1.0229 (2)1.2361 (2)0.0291 (9)
C90.8945 (3)0.9045 (2)1.1609 (2)0.0282 (9)
C100.4779 (3)0.7773 (2)0.8591 (2)0.0302 (9)
C110.5026 (3)0.7972 (3)0.7431 (2)0.0338 (10)
C120.3887 (4)0.8550 (3)0.7021 (2)0.0409 (11)
C130.4153 (4)0.8893 (3)0.5935 (3)0.0567 (12)
C140.3796 (5)0.7783 (3)0.4835 (3)0.0731 (16)
C150.6611 (3)0.4312 (2)0.8838 (2)0.0269 (9)
C160.8124 (3)0.4217 (2)0.9029 (2)0.0306 (9)
C170.8291 (3)0.3083 (3)0.8889 (2)0.0348 (10)
C180.6946 (4)0.2014 (3)0.8543 (2)0.0355 (10)
C190.5440 (3)0.2083 (3)0.8336 (2)0.0360 (10)
C200.5276 (3)0.3225 (2)0.8490 (2)0.0316 (10)
C210.3856 (3)0.5008 (2)0.7528 (2)0.0285 (9)
C220.4042 (3)0.4467 (3)0.6400 (2)0.0371 (10)
C230.2726 (4)0.3681 (3)0.5509 (3)0.0432 (11)
C240.1200 (4)0.3430 (3)0.5736 (3)0.0392 (11)
C250.0999 (3)0.3960 (3)0.6849 (2)0.0370 (10)
C260.2314 (3)0.4741 (2)0.7744 (2)0.0330 (10)
C271.0564 (3)1.3462 (2)1.2624 (2)0.0410 (11)
C281.0836 (4)0.9506 (3)1.3800 (2)0.0448 (11)
H50.747500.973400.942600.0370*
H60.892801.175701.071900.0380*
H90.895400.835101.184300.0340*
H10A0.507700.860000.922200.0360*
H10B0.361800.730200.851500.0360*
H11A0.484400.715500.681700.0410*
H11B0.615700.852800.753100.0410*
H12A0.276400.795200.685900.0490*
H12B0.399400.931600.767900.0490*
H13A0.529300.945200.607600.0680*
H13B0.345600.936800.580400.0680*
H14A0.453400.734100.493500.1100*
H14B0.394400.806800.415200.1100*
H14C0.267600.721400.469700.1100*
H160.906500.495400.926200.0370*
H170.933800.304000.903200.0420*
H180.705600.122600.844600.0430*
H190.450500.133900.808400.0430*
H200.422500.326300.835500.0380*
H220.509700.464100.623700.0450*
H230.286900.330900.473400.0520*
H240.028400.288700.511600.0470*
H250.005900.378800.700600.0440*
H260.216400.510200.852000.0400*
H27A1.096101.350601.190100.0610*
H27B1.122001.421901.329700.0610*
H27C0.943201.340301.251100.0610*
H28A0.975100.899101.383000.0670*
H28B1.154800.982901.459000.0670*
H28C1.126900.899301.322400.0670*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0477 (13)0.0262 (12)0.0363 (12)0.0116 (10)0.0006 (10)0.0057 (10)
O20.0492 (13)0.0345 (12)0.0327 (12)0.0150 (10)0.0060 (10)0.0095 (10)
N10.0273 (13)0.0266 (13)0.0258 (13)0.0145 (11)0.0038 (10)0.0073 (10)
N20.0298 (13)0.0273 (13)0.0285 (13)0.0127 (11)0.0052 (11)0.0102 (11)
C10.0301 (16)0.0270 (16)0.0233 (15)0.0122 (13)0.0046 (13)0.0094 (13)
C20.0266 (15)0.0259 (15)0.0257 (15)0.0119 (13)0.0053 (12)0.0079 (13)
C30.0313 (16)0.0249 (16)0.0255 (15)0.0129 (13)0.0068 (13)0.0054 (13)
C40.0268 (15)0.0273 (16)0.0264 (16)0.0130 (13)0.0065 (12)0.0056 (13)
C50.0304 (16)0.0346 (17)0.0267 (16)0.0136 (14)0.0020 (13)0.0100 (14)
C60.0310 (16)0.0291 (17)0.0357 (17)0.0119 (14)0.0064 (14)0.0114 (14)
C70.0278 (16)0.0226 (16)0.0303 (16)0.0092 (13)0.0040 (13)0.0017 (13)
C80.0308 (16)0.0304 (17)0.0243 (15)0.0138 (14)0.0023 (13)0.0047 (13)
C90.0304 (16)0.0282 (16)0.0295 (16)0.0140 (13)0.0081 (13)0.0105 (13)
C100.0317 (16)0.0296 (16)0.0332 (16)0.0178 (13)0.0050 (13)0.0096 (13)
C110.0352 (17)0.0371 (17)0.0342 (17)0.0185 (14)0.0072 (14)0.0137 (14)
C120.053 (2)0.0359 (18)0.0388 (18)0.0242 (16)0.0055 (15)0.0127 (15)
C130.072 (2)0.062 (2)0.049 (2)0.032 (2)0.0108 (19)0.0298 (19)
C140.097 (3)0.094 (3)0.046 (2)0.054 (3)0.018 (2)0.027 (2)
C150.0303 (16)0.0279 (16)0.0258 (15)0.0145 (13)0.0057 (13)0.0096 (13)
C160.0292 (16)0.0297 (16)0.0320 (16)0.0125 (13)0.0016 (13)0.0088 (13)
C170.0357 (18)0.0369 (18)0.0384 (18)0.0208 (15)0.0080 (14)0.0141 (15)
C180.0472 (19)0.0318 (17)0.0375 (18)0.0230 (16)0.0131 (15)0.0154 (14)
C190.0410 (19)0.0280 (17)0.0423 (18)0.0120 (14)0.0129 (15)0.0159 (14)
C200.0297 (16)0.0314 (17)0.0378 (17)0.0139 (14)0.0096 (14)0.0137 (14)
C210.0329 (16)0.0265 (16)0.0291 (16)0.0163 (13)0.0038 (13)0.0086 (13)
C220.0347 (17)0.0388 (18)0.0362 (18)0.0152 (15)0.0061 (15)0.0086 (15)
C230.043 (2)0.049 (2)0.0300 (18)0.0180 (17)0.0035 (15)0.0021 (15)
C240.0372 (19)0.0351 (18)0.0375 (19)0.0095 (15)0.0021 (15)0.0083 (15)
C250.0298 (17)0.0424 (19)0.0365 (18)0.0100 (15)0.0039 (14)0.0143 (15)
C260.0339 (17)0.0326 (17)0.0321 (16)0.0131 (14)0.0059 (14)0.0094 (14)
C270.050 (2)0.0277 (17)0.0433 (19)0.0128 (15)0.0063 (16)0.0117 (15)
C280.060 (2)0.046 (2)0.0379 (18)0.0316 (18)0.0031 (16)0.0171 (16)
Geometric parameters (Å, º) top
O1—C71.358 (3)C24—C251.361 (4)
O1—C271.413 (3)C25—C261.368 (4)
O2—C81.359 (3)C5—H50.9500
O2—C281.410 (4)C6—H60.9500
N1—C11.362 (3)C9—H90.9500
N1—C31.371 (3)C10—H10A0.9900
N1—C101.457 (3)C10—H10B0.9900
N2—C11.311 (3)C11—H11A0.9900
N2—C21.366 (3)C11—H11B0.9900
C1—C41.453 (3)C12—H12A0.9900
C2—C31.356 (4)C12—H12B0.9900
C2—C151.455 (4)C13—H13A0.9900
C3—C211.466 (4)C13—H13B0.9900
C4—C51.376 (3)C14—H14A0.9800
C4—C91.394 (3)C14—H14B0.9800
C5—C61.377 (3)C14—H14C0.9800
C6—C71.358 (3)C16—H160.9500
C7—C81.389 (3)C17—H170.9500
C8—C91.359 (3)C18—H180.9500
C10—C111.506 (3)C19—H190.9500
C11—C121.507 (5)C20—H200.9500
C12—C131.495 (4)C22—H220.9500
C13—C141.496 (5)C23—H230.9500
C15—C161.387 (4)C24—H240.9500
C15—C201.374 (4)C25—H250.9500
C16—C171.370 (4)C26—H260.9500
C17—C181.367 (5)C27—H27A0.9800
C18—C191.370 (5)C27—H27B0.9800
C19—C201.375 (4)C27—H27C0.9800
C21—C221.374 (3)C28—H28A0.9800
C21—C261.379 (4)C28—H28B0.9800
C22—C231.367 (4)C28—H28C0.9800
C23—C241.371 (5)
C7—O1—C27117.52 (19)C11—C10—H10B109.00
C8—O2—C28116.8 (2)H10A—C10—H10B108.00
C1—N1—C3107.2 (2)C10—C11—H11A109.00
C1—N1—C10129.6 (2)C10—C11—H11B109.00
C3—N1—C10123.3 (2)C12—C11—H11A109.00
C1—N2—C2106.1 (2)C12—C11—H11B109.00
N1—C1—N2110.8 (2)H11A—C11—H11B108.00
N1—C1—C4126.0 (2)C11—C12—H12A108.00
N2—C1—C4123.1 (2)C11—C12—H12B108.00
N2—C2—C3110.3 (2)C13—C12—H12A109.00
N2—C2—C15121.4 (2)C13—C12—H12B109.00
C3—C2—C15128.3 (2)H12A—C12—H12B108.00
N1—C3—C2105.7 (2)C12—C13—H13A109.00
N1—C3—C21123.1 (2)C12—C13—H13B109.00
C2—C3—C21131.1 (2)C14—C13—H13A109.00
C1—C4—C5124.9 (2)C14—C13—H13B109.00
C1—C4—C9117.4 (2)H13A—C13—H13B108.00
C5—C4—C9117.7 (2)C13—C14—H14A109.00
C4—C5—C6121.1 (2)C13—C14—H14B109.00
C5—C6—C7120.2 (2)C13—C14—H14C110.00
O1—C7—C6125.0 (2)H14A—C14—H14B109.00
O1—C7—C8115.1 (2)H14A—C14—H14C109.00
C6—C7—C8119.9 (2)H14B—C14—H14C109.00
O2—C8—C7115.3 (2)C15—C16—H16119.00
O2—C8—C9125.1 (2)C17—C16—H16119.00
C7—C8—C9119.7 (2)C16—C17—H17120.00
C4—C9—C8121.3 (2)C18—C17—H17120.00
N1—C10—C11112.6 (2)C17—C18—H18120.00
C10—C11—C12111.4 (2)C19—C18—H18120.00
C11—C12—C13115.0 (3)C18—C19—H19120.00
C12—C13—C14113.5 (3)C20—C19—H19120.00
C2—C15—C16120.2 (2)C15—C20—H20120.00
C2—C15—C20122.1 (2)C19—C20—H20120.00
C16—C15—C20117.8 (2)C21—C22—H22120.00
C15—C16—C17121.5 (2)C23—C22—H22120.00
C16—C17—C18119.8 (3)C22—C23—H23120.00
C17—C18—C19119.8 (3)C24—C23—H23120.00
C18—C19—C20120.3 (3)C23—C24—H24120.00
C15—C20—C19120.9 (3)C25—C24—H24120.00
C3—C21—C22119.3 (2)C24—C25—H25120.00
C3—C21—C26122.0 (2)C26—C25—H25120.00
C22—C21—C26118.6 (2)C21—C26—H26120.00
C21—C22—C23120.7 (3)C25—C26—H26120.00
C22—C23—C24120.0 (3)O1—C27—H27A109.00
C23—C24—C25119.9 (3)O1—C27—H27B109.00
C24—C25—C26120.3 (3)O1—C27—H27C110.00
C21—C26—C25120.5 (2)H27A—C27—H27B109.00
C4—C5—H5119.00H27A—C27—H27C109.00
C6—C5—H5120.00H27B—C27—H27C109.00
C5—C6—H6120.00O2—C28—H28A109.00
C7—C6—H6120.00O2—C28—H28B109.00
C4—C9—H9119.00O2—C28—H28C109.00
C8—C9—H9119.00H28A—C28—H28B109.00
N1—C10—H10A109.00H28A—C28—H28C109.00
N1—C10—H10B109.00H28B—C28—H28C110.00
C11—C10—H10A109.00
C27—O1—C7—C66.7 (4)C2—C3—C21—C26109.2 (3)
C27—O1—C7—C8173.8 (2)C1—C4—C5—C6179.5 (3)
C28—O2—C8—C7178.5 (3)C9—C4—C5—C61.8 (4)
C28—O2—C8—C92.2 (4)C1—C4—C9—C8178.7 (3)
C3—N1—C1—N20.3 (3)C5—C4—C9—C80.9 (4)
C3—N1—C1—C4177.0 (2)C4—C5—C6—C70.8 (4)
C10—N1—C1—N2179.9 (2)C5—C6—C7—O1179.3 (3)
C10—N1—C1—C43.2 (4)C5—C6—C7—C81.2 (4)
C1—N1—C3—C20.5 (3)O1—C7—C8—O21.0 (3)
C1—N1—C3—C21177.1 (2)O1—C7—C8—C9178.4 (2)
C10—N1—C3—C2179.6 (2)C6—C7—C8—O2178.6 (2)
C10—N1—C3—C212.8 (4)C6—C7—C8—C92.0 (4)
C1—N1—C10—C11100.4 (3)O2—C8—C9—C4179.7 (3)
C3—N1—C10—C1179.4 (3)C7—C8—C9—C41.0 (4)
C2—N2—C1—N10.1 (3)N1—C10—C11—C12173.6 (2)
C2—N2—C1—C4176.7 (2)C10—C11—C12—C13174.5 (3)
C1—N2—C2—C30.5 (3)C11—C12—C13—C1466.4 (4)
C1—N2—C2—C15178.9 (2)C2—C15—C16—C17178.5 (2)
N1—C1—C4—C533.0 (4)C20—C15—C16—C170.7 (3)
N1—C1—C4—C9149.3 (3)C2—C15—C20—C19179.2 (2)
N2—C1—C4—C5150.7 (3)C16—C15—C20—C190.1 (3)
N2—C1—C4—C927.0 (4)C15—C16—C17—C180.6 (4)
N2—C2—C3—N10.6 (3)C16—C17—C18—C190.1 (4)
N2—C2—C3—C21176.7 (2)C17—C18—C19—C200.9 (4)
C15—C2—C3—N1178.9 (2)C18—C19—C20—C150.8 (4)
C15—C2—C3—C211.5 (5)C3—C21—C22—C23177.9 (3)
N2—C2—C15—C1627.4 (3)C26—C21—C22—C230.1 (5)
N2—C2—C15—C20151.7 (2)C3—C21—C26—C25178.2 (3)
C3—C2—C15—C16150.8 (3)C22—C21—C26—C250.5 (4)
C3—C2—C15—C2030.2 (4)C21—C22—C23—C240.3 (5)
N1—C3—C21—C22108.4 (3)C22—C23—C24—C250.3 (5)
N1—C3—C21—C2673.9 (3)C23—C24—C25—C260.1 (5)
C2—C3—C21—C2268.5 (4)C24—C25—C26—C210.5 (5)
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
C23—H23···O1i0.952.533.168 (4)125
C27—H27A···N2ii0.982.513.474 (3)168
C27—H27A···Cg1ii0.982.773.608 (3)144
Symmetry codes: (i) x1, y1, z1; (ii) x+2, y+2, z+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
C23—H23···O1i0.952.533.168 (4)125
C27—H27A···N2ii0.982.513.474 (3)168
C27—H27A···Cg1ii0.982.773.608 (3)144
Symmetry codes: (i) x1, y1, z1; (ii) x+2, y+2, z+2.
 

Acknowledgements

Manchester Metropolitan University, Erciyes University and Alazhar University are gratefully acknowledged for supporting this study.

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Volume 69| Part 12| December 2013| Pages o1833-o1834
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