2-(2,5-Di­meth­oxy­phen­yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

Akkurt, M.; Mohamed, S.K.; Marzouk, A.A.; Abdelhamid, A.A.; Santoyo-Gonzalez, F.

doi:10.1107/S1600536813015936

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1098-o1099

https://doi.org/10.1107/S1600536813015936

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2-(2,5-Dimethoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

Mehmet Akkurt,^a Shaaban K. Mohamed,^b,^c Adel A. Marzouk,^d,^e Antar A. Abdelhamid ^f ^* and Francisco Santoyo-Gonzalez ^g

^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 Science, Mini University, 61519 El-Minia, Egypt, ^dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, ^eMamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, ^fChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^gDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 3 June 2013; accepted 7 June 2013; online 15 June 2013)

In the title compound, C₂₆H₂₄N₂O₂, the two phenyl and the 2,5-dimethoxyphenyl rings are inclined to the imidazole ring at dihedral angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. In the crystal, molecules are linked by pairs of C—H⋯O interactions into centrosymmetric dimers with graph-set notation R₂²(8). C—H⋯π interactions are also observed.

Related literature

For chemical properties and applications of imidazoles with an unsaturated side chain, see, for example: Koszykowska et al. (2009 ); Berezin et al. (2009 ); Rambo et al. (2010 ); Min et al. (2006 ). For similar structures, see: Akkurt et al. (2013a ,b ); Mohamed et al. (2013a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₂₄N₂O₂
M_r = 396.47
Triclinic, $[P \overline 1]$
a = 8.3117 (14) Å
b = 10.5217 (17) Å
c = 13.425 (2) Å
α = 105.938 (2)°
β = 101.846 (2)°
γ = 107.772 (2)°
V = 1020.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.26 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.979, T_max = 0.993
11527 measured reflections
4193 independent reflections
3184 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.125
S = 1.05
4193 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the N1/N2/C1–C3, C4–C9 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1ⁱ	0.95	2.54	3.354 (2)	143
C14—H14⋯Cg2ⁱⁱ	0.95	2.63	3.4083 (19)	139
C25—H25B⋯Cg1ⁱⁱⁱ	0.98	2.84	3.6337 (19)	139
C26—H26C⋯Cg4^iv	0.98	2.95	3.908 (2)	166
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015936/bx2444sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015936/bx2444Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015936/bx2444Isup3.cml

checkCIF report

Comment top

Recently, much attention has been devoted to vinyl and allyl N-substituted imidazole compunds due to their interesting properties and high reactivities. Such compounds in addition to threir flourecent properties (Berezin et al., 2009; Rambo et al., 2010) they can polymerize to obtain chromophoric polymers (Koszykowska et al., 2009). In addition their quaternery salts are acting as ionic catalists (Min et al., 2006) which are widely used in green chemistry applications. In this context the title compound has been synthesized among series of allyl imidazole derivatives and herein we report its crystal structure.

In the title compound (I, Fig. 1), the two phenyl (C4–C9 and C10–C15) and 2-(2,5-dimethoxyphenyl) (C19–C24) rings are inclined to the N1/N2/C1–C3 imidazole ring at angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. All bond lengths and angles are normal and are corresponding to those reported in a similar structure (Akkurt et al., 2013a,b; Mohamed et al., 2013a,b). In the crystal the molecules are linked by C— H··· O interactions into centrosymmetric dimers with graph-set notation R₂²(8) (Bernstein et al., 1995).C—H···π interactions are also observed,Table 1, Fig2.

Related literature top

For chemical properties and applications of imidazoles with an unsaturated side chain, see, for example: Koszykowska et al. (2009); Berezin et al. (2009); Rambo et al. (2010); Min et al. (2006). For similar structures, see: Akkurt et al. (2013a,b); Mohamed et al. (2013a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized according to our reported method (Mohamed et al. 2013a) in 85% yield. Colourless prisms suitable for X-ray analyses were obtained by slow evaporation of a solution of (I) in ethanol, m.p. 471–473 K.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 strcuture of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The hydrogen bonding and packing of the title compound viewing along the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-(2,5-Dimethoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole top

Crystal data top

C₂₆H₂₄N₂O₂	Z = 2
M_r = 396.47	F(000) = 420
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3117 (14) Å	Cell parameters from 2470 reflections
b = 10.5217 (17) Å	θ = 2.2–26.3°
c = 13.425 (2) Å	µ = 0.08 mm⁻¹
α = 105.938 (2)°	T = 100 K
β = 101.846 (2)°	Prism, colourless
γ = 107.772 (2)°	0.26 × 0.16 × 0.08 mm
V = 1020.1 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4193 independent reflections
Radiation source: sealed tube	3184 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
phi and ω scans	θ_max = 26.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.979, T_max = 0.993	k = −13→13
11527 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0613P)² + 0.1427P] where P = (F_o² + 2F_c²)/3
4193 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₆H₂₄N₂O₂	γ = 107.772 (2)°
M_r = 396.47	V = 1020.1 (3) Å³
Triclinic, P1	Z = 2
a = 8.3117 (14) Å	Mo Kα radiation
b = 10.5217 (17) Å	µ = 0.08 mm⁻¹
c = 13.425 (2) Å	T = 100 K
α = 105.938 (2)°	0.26 × 0.16 × 0.08 mm
β = 101.846 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4193 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3184 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.993	R_int = 0.036
11527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
4193 reflections	Δρ_min = −0.26 e Å⁻³
273 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	0.22127 (15)	0.57663 (13)	−0.01565 (9)	0.0294 (4)
O2	0.51365 (14)	0.51988 (12)	0.37054 (9)	0.0246 (3)
N1	0.03320 (16)	0.34760 (14)	0.28257 (10)	0.0200 (4)
N2	0.19265 (16)	0.21885 (14)	0.23560 (10)	0.0197 (4)
C1	0.1675 (2)	0.34409 (16)	0.24524 (12)	0.0187 (4)
C2	0.0647 (2)	0.13719 (17)	0.26932 (12)	0.0191 (5)
C3	−0.0325 (2)	0.21832 (16)	0.29722 (12)	0.0187 (5)
C4	−0.1839 (2)	0.18601 (17)	0.34015 (12)	0.0196 (5)
C5	−0.2095 (2)	0.29766 (17)	0.41145 (13)	0.0221 (5)
C6	−0.3463 (2)	0.26861 (19)	0.45693 (13)	0.0244 (5)
C7	−0.4602 (2)	0.12872 (19)	0.43134 (14)	0.0257 (5)
C8	−0.4395 (2)	0.01733 (19)	0.35825 (14)	0.0253 (5)
C9	−0.3029 (2)	0.04563 (17)	0.31312 (13)	0.0219 (5)
C10	0.05668 (19)	−0.00280 (17)	0.27544 (13)	0.0194 (4)
C11	0.0409 (2)	−0.11491 (17)	0.18480 (13)	0.0234 (5)
C12	0.0405 (2)	−0.24371 (18)	0.19320 (14)	0.0264 (5)
C13	0.0564 (2)	−0.26260 (18)	0.29232 (14)	0.0248 (5)
C14	0.0700 (2)	−0.15270 (17)	0.38256 (13)	0.0228 (5)
C15	0.0696 (2)	−0.02425 (17)	0.37420 (13)	0.0210 (5)
C16	0.3286 (2)	0.18032 (18)	0.19444 (13)	0.0229 (5)
C17	0.2732 (2)	0.12340 (19)	0.07169 (14)	0.0280 (5)
C18	0.2775 (3)	0.0033 (2)	0.01278 (16)	0.0392 (7)
C19	0.2772 (2)	0.45508 (16)	0.21242 (13)	0.0199 (5)
C20	0.2057 (2)	0.47090 (17)	0.11627 (13)	0.0221 (5)
C21	0.3087 (2)	0.56926 (17)	0.08016 (13)	0.0220 (5)
C22	0.4852 (2)	0.65115 (17)	0.14076 (14)	0.0238 (5)
C23	0.5580 (2)	0.63844 (17)	0.23932 (13)	0.0233 (5)
C24	0.4555 (2)	0.54150 (16)	0.27547 (13)	0.0202 (5)
C25	0.6880 (2)	0.61529 (18)	0.44233 (14)	0.0292 (5)
C26	0.3278 (2)	0.64720 (19)	−0.07022 (15)	0.0303 (6)
H5	−0.13280	0.39400	0.42890	0.0270*
H6	−0.36170	0.34510	0.50580	0.0290*
H7	−0.55200	0.10910	0.46370	0.0310*
H8	−0.51920	−0.07860	0.33910	0.0300*
H9	−0.28980	−0.03130	0.26320	0.0260*
H11	0.03020	−0.10310	0.11640	0.0280*
H12	0.02920	−0.31920	0.13060	0.0320*
H13	0.05790	−0.35020	0.29830	0.0300*
H14	0.07970	−0.16520	0.45070	0.0270*
H15	0.07820	0.05010	0.43670	0.0250*
H16A	0.35140	0.10690	0.22150	0.0270*
H16B	0.44100	0.26590	0.22340	0.0270*
H17	0.23240	0.17810	0.03450	0.0340*
H18A	0.31760	−0.05390	0.04740	0.0470*
H18B	0.24060	−0.02650	−0.06460	0.0470*
H20	0.08470	0.41400	0.07420	0.0270*
H22	0.55700	0.71610	0.11540	0.0290*
H23	0.67860	0.69670	0.28170	0.0280*
H25A	0.77680	0.59950	0.40780	0.0440*
H25B	0.70890	0.59740	0.51080	0.0440*
H25C	0.69790	0.71440	0.45760	0.0440*
H26A	0.39130	0.74890	−0.02480	0.0450*
H26B	0.25120	0.63740	−0.14020	0.0450*
H26C	0.41400	0.60380	−0.08310	0.0450*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0266 (6)	0.0360 (7)	0.0281 (7)	0.0075 (5)	0.0080 (5)	0.0209 (6)
O2	0.0216 (6)	0.0252 (6)	0.0223 (6)	0.0044 (5)	0.0028 (5)	0.0098 (5)
N1	0.0190 (7)	0.0203 (7)	0.0193 (7)	0.0059 (6)	0.0055 (6)	0.0074 (6)
N2	0.0188 (7)	0.0205 (7)	0.0210 (7)	0.0079 (6)	0.0073 (6)	0.0080 (6)
C1	0.0183 (7)	0.0192 (8)	0.0169 (8)	0.0064 (6)	0.0042 (6)	0.0059 (7)
C2	0.0181 (8)	0.0204 (8)	0.0156 (8)	0.0047 (7)	0.0040 (6)	0.0060 (7)
C3	0.0189 (8)	0.0187 (8)	0.0167 (8)	0.0058 (6)	0.0046 (6)	0.0062 (6)
C4	0.0189 (8)	0.0233 (9)	0.0193 (8)	0.0092 (7)	0.0060 (6)	0.0106 (7)
C5	0.0215 (8)	0.0219 (9)	0.0253 (9)	0.0090 (7)	0.0080 (7)	0.0108 (7)
C6	0.0245 (8)	0.0308 (9)	0.0249 (9)	0.0160 (8)	0.0102 (7)	0.0125 (8)
C7	0.0202 (8)	0.0357 (10)	0.0300 (9)	0.0133 (8)	0.0119 (7)	0.0189 (8)
C8	0.0177 (8)	0.0282 (9)	0.0298 (9)	0.0054 (7)	0.0051 (7)	0.0159 (8)
C9	0.0202 (8)	0.0221 (9)	0.0226 (9)	0.0078 (7)	0.0050 (7)	0.0086 (7)
C10	0.0152 (7)	0.0200 (8)	0.0215 (8)	0.0058 (6)	0.0044 (6)	0.0073 (7)
C11	0.0237 (8)	0.0248 (9)	0.0213 (9)	0.0090 (7)	0.0068 (7)	0.0085 (7)
C12	0.0296 (9)	0.0217 (9)	0.0248 (9)	0.0100 (7)	0.0080 (7)	0.0043 (7)
C13	0.0241 (8)	0.0206 (9)	0.0326 (10)	0.0099 (7)	0.0093 (7)	0.0123 (8)
C14	0.0205 (8)	0.0256 (9)	0.0236 (9)	0.0073 (7)	0.0077 (7)	0.0121 (7)
C15	0.0180 (8)	0.0216 (9)	0.0226 (8)	0.0068 (7)	0.0069 (7)	0.0072 (7)
C16	0.0194 (8)	0.0249 (9)	0.0260 (9)	0.0093 (7)	0.0084 (7)	0.0096 (7)
C17	0.0249 (9)	0.0345 (10)	0.0263 (9)	0.0113 (8)	0.0113 (7)	0.0114 (8)
C18	0.0452 (12)	0.0426 (12)	0.0293 (10)	0.0187 (10)	0.0155 (9)	0.0073 (9)
C19	0.0194 (8)	0.0190 (8)	0.0224 (8)	0.0073 (7)	0.0100 (7)	0.0067 (7)
C20	0.0197 (8)	0.0213 (8)	0.0234 (9)	0.0056 (7)	0.0057 (7)	0.0088 (7)
C21	0.0243 (8)	0.0246 (9)	0.0202 (8)	0.0111 (7)	0.0073 (7)	0.0104 (7)
C22	0.0253 (8)	0.0201 (8)	0.0293 (9)	0.0078 (7)	0.0132 (7)	0.0115 (7)
C23	0.0206 (8)	0.0222 (9)	0.0249 (9)	0.0062 (7)	0.0069 (7)	0.0077 (7)
C24	0.0214 (8)	0.0198 (8)	0.0201 (8)	0.0092 (7)	0.0070 (7)	0.0063 (7)
C25	0.0243 (9)	0.0263 (9)	0.0281 (9)	0.0045 (8)	−0.0003 (7)	0.0087 (8)
C26	0.0363 (10)	0.0328 (10)	0.0315 (10)	0.0149 (8)	0.0173 (8)	0.0193 (8)

Geometric parameters (Å, º) top

O1—C21	1.376 (2)	C20—C21	1.394 (3)
O1—C26	1.427 (2)	C21—C22	1.382 (2)
O2—C24	1.374 (2)	C22—C23	1.397 (2)
O2—C25	1.430 (2)	C23—C24	1.383 (2)
N1—C1	1.320 (2)	C5—H5	0.9500
N1—C3	1.387 (2)	C6—H6	0.9500
N2—C1	1.372 (2)	C7—H7	0.9500
N2—C2	1.388 (2)	C8—H8	0.9500
N2—C16	1.470 (2)	C9—H9	0.9500
C1—C19	1.479 (2)	C11—H11	0.9500
C2—C3	1.375 (2)	C12—H12	0.9500
C2—C10	1.480 (3)	C13—H13	0.9500
C3—C4	1.475 (2)	C14—H14	0.9500
C4—C5	1.400 (2)	C15—H15	0.9500
C4—C9	1.399 (3)	C16—H16A	0.9900
C5—C6	1.391 (3)	C16—H16B	0.9900
C6—C7	1.385 (3)	C17—H17	0.9500
C7—C8	1.388 (3)	C18—H18A	0.9500
C8—C9	1.386 (3)	C18—H18B	0.9500
C10—C11	1.393 (2)	C20—H20	0.9500
C10—C15	1.393 (2)	C22—H22	0.9500
C11—C12	1.390 (3)	C23—H23	0.9500
C12—C13	1.385 (3)	C25—H25A	0.9800
C13—C14	1.383 (2)	C25—H25B	0.9800
C14—C15	1.388 (3)	C25—H25C	0.9800
C16—C17	1.505 (2)	C26—H26A	0.9800
C17—C18	1.309 (3)	C26—H26B	0.9800
C19—C20	1.382 (2)	C26—H26C	0.9800
C19—C24	1.407 (2)

C21—O1—C26	117.36 (14)	C5—C6—H6	120.00
C24—O2—C25	116.87 (14)	C7—C6—H6	120.00
C1—N1—C3	105.42 (14)	C6—C7—H7	120.00
C1—N2—C2	107.22 (14)	C8—C7—H7	120.00
C1—N2—C16	125.18 (15)	C7—C8—H8	120.00
C2—N2—C16	127.58 (15)	C9—C8—H8	120.00
N1—C1—N2	111.60 (15)	C4—C9—H9	120.00
N1—C1—C19	126.41 (16)	C8—C9—H9	120.00
N2—C1—C19	121.96 (15)	C10—C11—H11	120.00
N2—C2—C3	105.17 (15)	C12—C11—H11	120.00
N2—C2—C10	122.53 (15)	C11—C12—H12	120.00
C3—C2—C10	132.23 (16)	C13—C12—H12	120.00
N1—C3—C2	110.59 (15)	C12—C13—H13	120.00
N1—C3—C4	120.32 (15)	C14—C13—H13	120.00
C2—C3—C4	129.08 (16)	C13—C14—H14	120.00
C3—C4—C5	119.76 (16)	C15—C14—H14	120.00
C3—C4—C9	121.91 (15)	C10—C15—H15	120.00
C5—C4—C9	118.32 (16)	C14—C15—H15	120.00
C4—C5—C6	120.51 (17)	N2—C16—H16A	109.00
C5—C6—C7	120.36 (16)	N2—C16—H16B	109.00
C6—C7—C8	119.68 (17)	C17—C16—H16A	109.00
C7—C8—C9	120.17 (18)	C17—C16—H16B	109.00
C4—C9—C8	120.90 (16)	H16A—C16—H16B	108.00
C2—C10—C11	121.70 (15)	C16—C17—H17	118.00
C2—C10—C15	120.15 (15)	C18—C17—H17	118.00
C11—C10—C15	118.13 (16)	C17—C18—H18A	120.00
C10—C11—C12	120.84 (16)	C17—C18—H18B	120.00
C11—C12—C13	120.37 (16)	H18A—C18—H18B	120.00
C12—C13—C14	119.31 (17)	C19—C20—H20	120.00
C13—C14—C15	120.39 (16)	C21—C20—H20	120.00
C10—C15—C14	120.96 (15)	C21—C22—H22	120.00
N2—C16—C17	112.28 (14)	C23—C22—H22	120.00
C16—C17—C18	124.22 (18)	C22—C23—H23	120.00
C1—C19—C20	119.57 (15)	C24—C23—H23	120.00
C1—C19—C24	121.05 (15)	O2—C25—H25A	109.00
C20—C19—C24	119.34 (16)	O2—C25—H25B	109.00
C19—C20—C21	120.92 (16)	O2—C25—H25C	109.00
O1—C21—C20	115.32 (15)	H25A—C25—H25B	109.00
O1—C21—C22	125.10 (16)	H25A—C25—H25C	109.00
C20—C21—C22	119.58 (16)	H25B—C25—H25C	109.00
C21—C22—C23	120.05 (16)	O1—C26—H26A	109.00
C22—C23—C24	120.34 (16)	O1—C26—H26B	109.00
O2—C24—C19	115.12 (15)	O1—C26—H26C	109.00
O2—C24—C23	125.15 (15)	H26A—C26—H26B	109.00
C19—C24—C23	119.74 (15)	H26A—C26—H26C	109.00
C4—C5—H5	120.00	H26B—C26—H26C	109.00
C6—C5—H5	120.00

C26—O1—C21—C22	15.8 (2)	C2—C3—C4—C5	148.45 (17)
C26—O1—C21—C20	−164.74 (15)	N1—C3—C4—C5	−29.8 (2)
C25—O2—C24—C19	−173.84 (15)	C3—C4—C5—C6	−176.81 (15)
C25—O2—C24—C23	6.6 (2)	C3—C4—C9—C8	177.09 (16)
C1—N1—C3—C2	0.58 (17)	C9—C4—C5—C6	2.2 (2)
C1—N1—C3—C4	179.16 (14)	C5—C4—C9—C8	−1.9 (2)
C3—N1—C1—N2	−0.36 (17)	C4—C5—C6—C7	−0.7 (3)
C3—N1—C1—C19	177.32 (15)	C5—C6—C7—C8	−1.3 (3)
C16—N2—C1—C19	0.9 (2)	C6—C7—C8—C9	1.6 (3)
C16—N2—C2—C10	4.5 (2)	C7—C8—C9—C4	0.0 (3)
C2—N2—C1—C19	−177.79 (14)	C2—C10—C11—C12	177.49 (17)
C16—N2—C2—C3	−178.34 (14)	C11—C10—C15—C14	1.2 (3)
C1—N2—C2—C10	−176.80 (14)	C2—C10—C15—C14	−177.22 (16)
C16—N2—C1—N1	178.73 (13)	C15—C10—C11—C12	−0.9 (3)
C2—N2—C16—C17	97.69 (19)	C10—C11—C12—C13	−0.2 (3)
C1—N2—C16—C17	−80.8 (2)	C11—C12—C13—C14	1.0 (3)
C2—N2—C1—N1	0.00 (17)	C12—C13—C14—C15	−0.7 (3)
C1—N2—C2—C3	0.34 (16)	C13—C14—C15—C10	−0.4 (3)
N1—C1—C19—C20	−72.9 (2)	N2—C16—C17—C18	−129.1 (2)
N1—C1—C19—C24	109.5 (2)	C1—C19—C24—C23	176.09 (16)
N2—C1—C19—C20	104.59 (19)	C20—C19—C24—O2	178.86 (15)
N2—C1—C19—C24	−73.1 (2)	C1—C19—C24—O2	−3.5 (2)
N2—C2—C10—C15	121.30 (18)	C24—C19—C20—C21	1.2 (3)
C3—C2—C10—C11	126.7 (2)	C20—C19—C24—C23	−1.6 (3)
C3—C2—C10—C15	−55.0 (3)	C1—C19—C20—C21	−176.52 (16)
N2—C2—C10—C11	−57.0 (2)	C19—C20—C21—C22	0.6 (3)
N2—C2—C3—C4	−178.98 (15)	C19—C20—C21—O1	−178.89 (16)
N2—C2—C3—N1	−0.57 (17)	C20—C21—C22—C23	−2.0 (3)
C10—C2—C3—N1	176.17 (16)	O1—C21—C22—C23	177.44 (16)
C10—C2—C3—C4	−2.3 (3)	C21—C22—C23—C24	1.6 (3)
C2—C3—C4—C9	−30.5 (3)	C22—C23—C24—C19	0.2 (3)
N1—C3—C4—C9	151.19 (15)	C22—C23—C24—O2	179.71 (16)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg4 are the centroids of the N1/N2/C1–C3, C4–C9 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ⁱ	0.95	2.54	3.354 (2)	143
C14—H14···Cg2ⁱⁱ	0.95	2.63	3.4083 (19)	139
C25—H25B···Cg1ⁱⁱⁱ	0.98	2.84	3.6337 (19)	139
C26—H26C···Cg4^iv	0.98	2.95	3.908 (2)	166

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₂
M_r	396.47
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.3117 (14), 10.5217 (17), 13.425 (2)
α, β, γ (°)	105.938 (2), 101.846 (2), 107.772 (2)
V (Å³)	1020.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.979, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	11527, 4193, 3184
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.125, 1.05
No. of reflections	4193
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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, Cg2 and Cg4 are the centroids of the N1/N2/C1–C3, C4–C9 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ⁱ	0.95	2.54	3.354 (2)	143
C14—H14···Cg2ⁱⁱ	0.95	2.63	3.4083 (19)	139
C25—H25B···Cg1ⁱⁱⁱ	0.98	2.84	3.6337 (19)	139
C26—H26C···Cg4^iv	0.98	2.95	3.908 (2)	166

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z.

Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

Akkurt, M., Fronczek, F. R., Mohamed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013a). Acta Cryst. E69, o527–o528. CSD CrossRef CAS IUCr Journals Google Scholar
Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013b). Acta Cryst. E69, o846–o847. CSD CrossRef CAS IUCr Journals Google Scholar
Berezin, M. Y., Jeff, K. & Achilefu, S. (2009). Chemistry, 15, 3560–3566. Web of Science CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Koszykowska, M., Tokarek, M. & Kucharski, S. (2009). Mater. Sci. Pol. 27, 699–708. CAS Google Scholar
Min, G.-H., Yim, T., Lee, H. Y., Huh, D. H., Lee, E., Mun, J., Oh, S. M. & Kim, Y. G. (2006). Bull. Korean Chem. Soc. 27, 847–852. CAS Google Scholar
Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013a). Acta Cryst. E69, o474–o475. CSD CrossRef CAS IUCr Journals Google Scholar
Mohamed, S. K., Akkurt, M., Marzouk, A. A. E., Santoyo-Gonzalez, F. & Elremaily, M. A. A. (2013b). Acta Cryst. E69, o875–o876. CSD CrossRef CAS IUCr Journals Google Scholar
Rambo, B. M., Silver, E. S., Bielawski, C. W. & Sessler, J. L. (2010). Heterocycl. Chem. 1, 1–37. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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