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

Mohamed, S.K.; Akkurt, M.; Marzouk, A.A.; Singh, K.; Albayati, M.R.

doi:10.1107/S1600536813031759

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

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

doi:10.1107/S1600536813031759

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

Shaaban K. Mohamed,^a,^b Mehmet Akkurt,^c Adel A. Marzouk,^d Kuldip Singh ^e and Mustafa R. Albayati ^f ^*

^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 π–π stacking interactions [centroid–centroid distance = 3.760 (2) Å] and C—H⋯π contacts, forming a three-dimensional network.

CCDC reference: 973035

Related literature

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

Crystal data

C₂₈H₃₀N₂O₂
M_r = 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 ) T_min = 0.668, T_max = 0.981
8350 measured reflections
3953 independent reflections
2219 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.127
S = 0.87
3953 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −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	D⋯A	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—H27A⋯Cg1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; 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 ).

Supporting information

CCDC reference: 973035

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813031759/sj5371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031759/sj5371Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031759/sj5371Isup3.cml

checkCIF report

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.

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

	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.
	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

C₂₈H₃₀N₂O₂	Z = 2
M_r = 426.54	F(000) = 456
Triclinic, P1	D_x = 1.252 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.900 (2) Å	Cell parameters from 856 reflections
b = 11.915 (3) Å	θ = 2.5–20.8°
c = 12.009 (3) Å	µ = 0.08 mm⁻¹
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 tube	2219 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −10→10
T_min = 0.668, T_max = 0.981	k = −13→14
8350 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0391P)²] where P = (F_o² + 2F_c²)/3
3953 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₈H₃₀N₂O₂	γ = 108.170 (6)°
M_r = 426.54	V = 1131.8 (5) Å³
Triclinic, P1	Z = 2
a = 8.900 (2) Å	Mo Kα radiation
b = 11.915 (3) Å	µ = 0.08 mm⁻¹
c = 12.009 (3) Å	T = 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)
T_min = 0.668, T_max = 0.981	R_int = 0.086
8350 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.87	Δρ_max = 0.25 e Å⁻³
3953 reflections	Δρ_min = −0.25 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	1.0678 (2)	1.23924 (16)	1.28583 (16)	0.0391 (7)
O2	1.0748 (2)	1.05208 (17)	1.34508 (16)	0.0404 (7)
N1	0.5735 (2)	0.70894 (19)	0.89430 (18)	0.0259 (8)
N2	0.7629 (2)	0.66063 (19)	0.98101 (18)	0.0278 (8)
C1	0.7160 (3)	0.7530 (2)	0.9748 (2)	0.0262 (9)
C2	0.6472 (3)	0.5534 (2)	0.9023 (2)	0.0257 (9)
C3	0.5296 (3)	0.5811 (2)	0.8472 (2)	0.0272 (9)
C4	0.8031 (3)	0.8829 (2)	1.0501 (2)	0.0268 (9)
C5	0.8063 (3)	0.9857 (2)	1.0185 (2)	0.0305 (9)
C6	0.8932 (3)	1.1059 (2)	1.0950 (2)	0.0316 (10)
C7	0.9794 (3)	1.1250 (2)	1.2033 (2)	0.0287 (9)
C8	0.9822 (3)	1.0229 (2)	1.2361 (2)	0.0291 (9)
C9	0.8945 (3)	0.9045 (2)	1.1609 (2)	0.0282 (9)
C10	0.4779 (3)	0.7773 (2)	0.8591 (2)	0.0302 (9)
C11	0.5026 (3)	0.7972 (3)	0.7431 (2)	0.0338 (10)
C12	0.3887 (4)	0.8550 (3)	0.7021 (2)	0.0409 (11)
C13	0.4153 (4)	0.8893 (3)	0.5935 (3)	0.0567 (12)
C14	0.3796 (5)	0.7783 (3)	0.4835 (3)	0.0731 (16)
C15	0.6611 (3)	0.4312 (2)	0.8838 (2)	0.0269 (9)
C16	0.8124 (3)	0.4217 (2)	0.9029 (2)	0.0306 (9)
C17	0.8291 (3)	0.3083 (3)	0.8889 (2)	0.0348 (10)
C18	0.6946 (4)	0.2014 (3)	0.8543 (2)	0.0355 (10)
C19	0.5440 (3)	0.2083 (3)	0.8336 (2)	0.0360 (10)
C20	0.5276 (3)	0.3225 (2)	0.8490 (2)	0.0316 (10)
C21	0.3856 (3)	0.5008 (2)	0.7528 (2)	0.0285 (9)
C22	0.4042 (3)	0.4467 (3)	0.6400 (2)	0.0371 (10)
C23	0.2726 (4)	0.3681 (3)	0.5509 (3)	0.0432 (11)
C24	0.1200 (4)	0.3430 (3)	0.5736 (3)	0.0392 (11)
C25	0.0999 (3)	0.3960 (3)	0.6849 (2)	0.0370 (10)
C26	0.2314 (3)	0.4741 (2)	0.7744 (2)	0.0330 (10)
C27	1.0564 (3)	1.3462 (2)	1.2624 (2)	0.0410 (11)
C28	1.0836 (4)	0.9506 (3)	1.3800 (2)	0.0448 (11)
H5	0.74750	0.97340	0.94260	0.0370*
H6	0.89280	1.17570	1.07190	0.0380*
H9	0.89540	0.83510	1.18430	0.0340*
H10A	0.50770	0.86000	0.92220	0.0360*
H10B	0.36180	0.73020	0.85150	0.0360*
H11A	0.48440	0.71550	0.68170	0.0410*
H11B	0.61570	0.85280	0.75310	0.0410*
H12A	0.27640	0.79520	0.68590	0.0490*
H12B	0.39940	0.93160	0.76790	0.0490*
H13A	0.52930	0.94520	0.60760	0.0680*
H13B	0.34560	0.93680	0.58040	0.0680*
H14A	0.45340	0.73410	0.49350	0.1100*
H14B	0.39440	0.80680	0.41520	0.1100*
H14C	0.26760	0.72140	0.46970	0.1100*
H16	0.90650	0.49540	0.92620	0.0370*
H17	0.93380	0.30400	0.90320	0.0420*
H18	0.70560	0.12260	0.84460	0.0430*
H19	0.45050	0.13390	0.80840	0.0430*
H20	0.42250	0.32630	0.83550	0.0380*
H22	0.50970	0.46410	0.62370	0.0450*
H23	0.28690	0.33090	0.47340	0.0520*
H24	0.02840	0.28870	0.51160	0.0470*
H25	−0.00590	0.37880	0.70060	0.0440*
H26	0.21640	0.51020	0.85200	0.0400*
H27A	1.09610	1.35060	1.19010	0.0610*
H27B	1.12200	1.42190	1.32970	0.0610*
H27C	0.94320	1.34030	1.25110	0.0610*
H28A	0.97510	0.89910	1.38300	0.0670*
H28B	1.15480	0.98290	1.45900	0.0670*
H28C	1.12690	0.89930	1.32240	0.0670*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0477 (13)	0.0262 (12)	0.0363 (12)	0.0116 (10)	−0.0006 (10)	0.0057 (10)
O2	0.0492 (13)	0.0345 (12)	0.0327 (12)	0.0150 (10)	−0.0060 (10)	0.0095 (10)
N1	0.0273 (13)	0.0266 (13)	0.0258 (13)	0.0145 (11)	0.0038 (10)	0.0073 (10)
N2	0.0298 (13)	0.0273 (13)	0.0285 (13)	0.0127 (11)	0.0052 (11)	0.0102 (11)
C1	0.0301 (16)	0.0270 (16)	0.0233 (15)	0.0122 (13)	0.0046 (13)	0.0094 (13)
C2	0.0266 (15)	0.0259 (15)	0.0257 (15)	0.0119 (13)	0.0053 (12)	0.0079 (13)
C3	0.0313 (16)	0.0249 (16)	0.0255 (15)	0.0129 (13)	0.0068 (13)	0.0054 (13)
C4	0.0268 (15)	0.0273 (16)	0.0264 (16)	0.0130 (13)	0.0065 (12)	0.0056 (13)
C5	0.0304 (16)	0.0346 (17)	0.0267 (16)	0.0136 (14)	0.0020 (13)	0.0100 (14)
C6	0.0310 (16)	0.0291 (17)	0.0357 (17)	0.0119 (14)	0.0064 (14)	0.0114 (14)
C7	0.0278 (16)	0.0226 (16)	0.0303 (16)	0.0092 (13)	0.0040 (13)	0.0017 (13)
C8	0.0308 (16)	0.0304 (17)	0.0243 (15)	0.0138 (14)	0.0023 (13)	0.0047 (13)
C9	0.0304 (16)	0.0282 (16)	0.0295 (16)	0.0140 (13)	0.0081 (13)	0.0105 (13)
C10	0.0317 (16)	0.0296 (16)	0.0332 (16)	0.0178 (13)	0.0050 (13)	0.0096 (13)
C11	0.0352 (17)	0.0371 (17)	0.0342 (17)	0.0185 (14)	0.0072 (14)	0.0137 (14)
C12	0.053 (2)	0.0359 (18)	0.0388 (18)	0.0242 (16)	0.0055 (15)	0.0127 (15)
C13	0.072 (2)	0.062 (2)	0.049 (2)	0.032 (2)	0.0108 (19)	0.0298 (19)
C14	0.097 (3)	0.094 (3)	0.046 (2)	0.054 (3)	0.018 (2)	0.027 (2)
C15	0.0303 (16)	0.0279 (16)	0.0258 (15)	0.0145 (13)	0.0057 (13)	0.0096 (13)
C16	0.0292 (16)	0.0297 (16)	0.0320 (16)	0.0125 (13)	0.0016 (13)	0.0088 (13)
C17	0.0357 (18)	0.0369 (18)	0.0384 (18)	0.0208 (15)	0.0080 (14)	0.0141 (15)
C18	0.0472 (19)	0.0318 (17)	0.0375 (18)	0.0230 (16)	0.0131 (15)	0.0154 (14)
C19	0.0410 (19)	0.0280 (17)	0.0423 (18)	0.0120 (14)	0.0129 (15)	0.0159 (14)
C20	0.0297 (16)	0.0314 (17)	0.0378 (17)	0.0139 (14)	0.0096 (14)	0.0137 (14)
C21	0.0329 (16)	0.0265 (16)	0.0291 (16)	0.0163 (13)	0.0038 (13)	0.0086 (13)
C22	0.0347 (17)	0.0388 (18)	0.0362 (18)	0.0152 (15)	0.0061 (15)	0.0086 (15)
C23	0.043 (2)	0.049 (2)	0.0300 (18)	0.0180 (17)	0.0035 (15)	0.0021 (15)
C24	0.0372 (19)	0.0351 (18)	0.0375 (19)	0.0095 (15)	−0.0021 (15)	0.0083 (15)
C25	0.0298 (17)	0.0424 (19)	0.0365 (18)	0.0100 (15)	0.0039 (14)	0.0143 (15)
C26	0.0339 (17)	0.0326 (17)	0.0321 (16)	0.0131 (14)	0.0059 (14)	0.0094 (14)
C27	0.050 (2)	0.0277 (17)	0.0433 (19)	0.0128 (15)	0.0063 (16)	0.0117 (15)
C28	0.060 (2)	0.046 (2)	0.0379 (18)	0.0316 (18)	0.0031 (16)	0.0171 (16)

Geometric parameters (Å, º) top

O1—C7	1.358 (3)	C24—C25	1.361 (4)
O1—C27	1.413 (3)	C25—C26	1.368 (4)
O2—C8	1.359 (3)	C5—H5	0.9500
O2—C28	1.410 (4)	C6—H6	0.9500
N1—C1	1.362 (3)	C9—H9	0.9500
N1—C3	1.371 (3)	C10—H10A	0.9900
N1—C10	1.457 (3)	C10—H10B	0.9900
N2—C1	1.311 (3)	C11—H11A	0.9900
N2—C2	1.366 (3)	C11—H11B	0.9900
C1—C4	1.453 (3)	C12—H12A	0.9900
C2—C3	1.356 (4)	C12—H12B	0.9900
C2—C15	1.455 (4)	C13—H13A	0.9900
C3—C21	1.466 (4)	C13—H13B	0.9900
C4—C5	1.376 (3)	C14—H14A	0.9800
C4—C9	1.394 (3)	C14—H14B	0.9800
C5—C6	1.377 (3)	C14—H14C	0.9800
C6—C7	1.358 (3)	C16—H16	0.9500
C7—C8	1.389 (3)	C17—H17	0.9500
C8—C9	1.359 (3)	C18—H18	0.9500
C10—C11	1.506 (3)	C19—H19	0.9500
C11—C12	1.507 (5)	C20—H20	0.9500
C12—C13	1.495 (4)	C22—H22	0.9500
C13—C14	1.496 (5)	C23—H23	0.9500
C15—C16	1.387 (4)	C24—H24	0.9500
C15—C20	1.374 (4)	C25—H25	0.9500
C16—C17	1.370 (4)	C26—H26	0.9500
C17—C18	1.367 (5)	C27—H27A	0.9800
C18—C19	1.370 (5)	C27—H27B	0.9800
C19—C20	1.375 (4)	C27—H27C	0.9800
C21—C22	1.374 (3)	C28—H28A	0.9800
C21—C26	1.379 (4)	C28—H28B	0.9800
C22—C23	1.367 (4)	C28—H28C	0.9800
C23—C24	1.371 (5)

C7—O1—C27	117.52 (19)	C11—C10—H10B	109.00
C8—O2—C28	116.8 (2)	H10A—C10—H10B	108.00
C1—N1—C3	107.2 (2)	C10—C11—H11A	109.00
C1—N1—C10	129.6 (2)	C10—C11—H11B	109.00
C3—N1—C10	123.3 (2)	C12—C11—H11A	109.00
C1—N2—C2	106.1 (2)	C12—C11—H11B	109.00
N1—C1—N2	110.8 (2)	H11A—C11—H11B	108.00
N1—C1—C4	126.0 (2)	C11—C12—H12A	108.00
N2—C1—C4	123.1 (2)	C11—C12—H12B	108.00
N2—C2—C3	110.3 (2)	C13—C12—H12A	109.00
N2—C2—C15	121.4 (2)	C13—C12—H12B	109.00
C3—C2—C15	128.3 (2)	H12A—C12—H12B	108.00
N1—C3—C2	105.7 (2)	C12—C13—H13A	109.00
N1—C3—C21	123.1 (2)	C12—C13—H13B	109.00
C2—C3—C21	131.1 (2)	C14—C13—H13A	109.00
C1—C4—C5	124.9 (2)	C14—C13—H13B	109.00
C1—C4—C9	117.4 (2)	H13A—C13—H13B	108.00
C5—C4—C9	117.7 (2)	C13—C14—H14A	109.00
C4—C5—C6	121.1 (2)	C13—C14—H14B	109.00
C5—C6—C7	120.2 (2)	C13—C14—H14C	110.00
O1—C7—C6	125.0 (2)	H14A—C14—H14B	109.00
O1—C7—C8	115.1 (2)	H14A—C14—H14C	109.00
C6—C7—C8	119.9 (2)	H14B—C14—H14C	109.00
O2—C8—C7	115.3 (2)	C15—C16—H16	119.00
O2—C8—C9	125.1 (2)	C17—C16—H16	119.00
C7—C8—C9	119.7 (2)	C16—C17—H17	120.00
C4—C9—C8	121.3 (2)	C18—C17—H17	120.00
N1—C10—C11	112.6 (2)	C17—C18—H18	120.00
C10—C11—C12	111.4 (2)	C19—C18—H18	120.00
C11—C12—C13	115.0 (3)	C18—C19—H19	120.00
C12—C13—C14	113.5 (3)	C20—C19—H19	120.00
C2—C15—C16	120.2 (2)	C15—C20—H20	120.00
C2—C15—C20	122.1 (2)	C19—C20—H20	120.00
C16—C15—C20	117.8 (2)	C21—C22—H22	120.00
C15—C16—C17	121.5 (2)	C23—C22—H22	120.00
C16—C17—C18	119.8 (3)	C22—C23—H23	120.00
C17—C18—C19	119.8 (3)	C24—C23—H23	120.00
C18—C19—C20	120.3 (3)	C23—C24—H24	120.00
C15—C20—C19	120.9 (3)	C25—C24—H24	120.00
C3—C21—C22	119.3 (2)	C24—C25—H25	120.00
C3—C21—C26	122.0 (2)	C26—C25—H25	120.00
C22—C21—C26	118.6 (2)	C21—C26—H26	120.00
C21—C22—C23	120.7 (3)	C25—C26—H26	120.00
C22—C23—C24	120.0 (3)	O1—C27—H27A	109.00
C23—C24—C25	119.9 (3)	O1—C27—H27B	109.00
C24—C25—C26	120.3 (3)	O1—C27—H27C	110.00
C21—C26—C25	120.5 (2)	H27A—C27—H27B	109.00
C4—C5—H5	119.00	H27A—C27—H27C	109.00
C6—C5—H5	120.00	H27B—C27—H27C	109.00
C5—C6—H6	120.00	O2—C28—H28A	109.00
C7—C6—H6	120.00	O2—C28—H28B	109.00
C4—C9—H9	119.00	O2—C28—H28C	109.00
C8—C9—H9	119.00	H28A—C28—H28B	109.00
N1—C10—H10A	109.00	H28A—C28—H28C	109.00
N1—C10—H10B	109.00	H28B—C28—H28C	110.00
C11—C10—H10A	109.00

C27—O1—C7—C6	6.7 (4)	C2—C3—C21—C26	109.2 (3)
C27—O1—C7—C8	−173.8 (2)	C1—C4—C5—C6	−179.5 (3)
C28—O2—C8—C7	−178.5 (3)	C9—C4—C5—C6	−1.8 (4)
C28—O2—C8—C9	2.2 (4)	C1—C4—C9—C8	178.7 (3)
C3—N1—C1—N2	−0.3 (3)	C5—C4—C9—C8	0.9 (4)
C3—N1—C1—C4	−177.0 (2)	C4—C5—C6—C7	0.8 (4)
C10—N1—C1—N2	179.9 (2)	C5—C6—C7—O1	−179.3 (3)
C10—N1—C1—C4	3.2 (4)	C5—C6—C7—C8	1.2 (4)
C1—N1—C3—C2	0.5 (3)	O1—C7—C8—O2	−1.0 (3)
C1—N1—C3—C21	−177.1 (2)	O1—C7—C8—C9	178.4 (2)
C10—N1—C3—C2	−179.6 (2)	C6—C7—C8—O2	178.6 (2)
C10—N1—C3—C21	2.8 (4)	C6—C7—C8—C9	−2.0 (4)
C1—N1—C10—C11	100.4 (3)	O2—C8—C9—C4	−179.7 (3)
C3—N1—C10—C11	−79.4 (3)	C7—C8—C9—C4	1.0 (4)
C2—N2—C1—N1	−0.1 (3)	N1—C10—C11—C12	173.6 (2)
C2—N2—C1—C4	176.7 (2)	C10—C11—C12—C13	174.5 (3)
C1—N2—C2—C3	0.5 (3)	C11—C12—C13—C14	66.4 (4)
C1—N2—C2—C15	178.9 (2)	C2—C15—C16—C17	178.5 (2)
N1—C1—C4—C5	−33.0 (4)	C20—C15—C16—C17	−0.7 (3)
N1—C1—C4—C9	149.3 (3)	C2—C15—C20—C19	−179.2 (2)
N2—C1—C4—C5	150.7 (3)	C16—C15—C20—C19	−0.1 (3)
N2—C1—C4—C9	−27.0 (4)	C15—C16—C17—C18	0.6 (4)
N2—C2—C3—N1	−0.6 (3)	C16—C17—C18—C19	0.1 (4)
N2—C2—C3—C21	176.7 (2)	C17—C18—C19—C20	−0.9 (4)
C15—C2—C3—N1	−178.9 (2)	C18—C19—C20—C15	0.8 (4)
C15—C2—C3—C21	−1.5 (5)	C3—C21—C22—C23	177.9 (3)
N2—C2—C15—C16	−27.4 (3)	C26—C21—C22—C23	0.1 (5)
N2—C2—C15—C20	151.7 (2)	C3—C21—C26—C25	−178.2 (3)
C3—C2—C15—C16	150.8 (3)	C22—C21—C26—C25	−0.5 (4)
C3—C2—C15—C20	−30.2 (4)	C21—C22—C23—C24	0.3 (5)
N1—C3—C21—C22	108.4 (3)	C22—C23—C24—C25	−0.3 (5)
N1—C3—C21—C26	−73.9 (3)	C23—C24—C25—C26	−0.1 (5)
C2—C3—C21—C22	−68.5 (4)	C24—C25—C26—C21	0.5 (5)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	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—H27A···Cg1ⁱⁱ	0.98	2.77	3.608 (3)	144

Symmetry codes: (i) x−1, y−1, z−1; (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···A	D—H	H···A	D···A	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—H27A···Cg1ⁱⁱ	0.98	2.77	3.608 (3)	144

Symmetry codes: (i) x−1, y−1, z−1; (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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