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

Akkurt, M.; Mohamed, S.K.; Marzouk, A.A.E.; Abbasov, V.M.; Santoyo-Gonzalez, F.

doi:10.1107/S1600536813014104

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o988-o989

doi:10.1107/S1600536813014104

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

Mehmet Akkurt,^a Shaaban K. Mohamed,^b,^c ^* Adel A. E. Marzouk,^d V. M. Abbasov ^e and Francisco Santoyo-Gonzalez ^f

^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, and ^fDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 15 May 2013; accepted 21 May 2013; online 31 May 2013)

In the title compound, C₂₄H₂₀N₂, one of the ring C atoms and one of the ring N atoms are disordered over two sets of sites in a 0.615 (3):0.385 (3) ratio. The two parts of the disordered imidazole ring adopt an envelope conformation, with the undisordered ring N atom as the flap, displaced by −0.118 (6) and 0.226 (7) Å, respectively, in the two disorder components from the plane through the other ring atoms. The crystal structure features C—H⋯N hydrogen bonds and C—H⋯π interactions, which lead to the formation of infinite chains along [010].

Related literature

For the biological significance of imidazole derivatives, see, for example: Kumar (2010 ); Castaño et al. (2008 ); Banfi et al. (2006 ); Bogle et al. (1994 ). For the synthesis and the structures of similar imidazoles, see: Mohamed et al. (2013a ,b ); Akkurt et al. (2013 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₀N₂
M_r = 336.42
Monoclinic, P 2₁ /n
a = 10.362 (3) Å
b = 8.938 (2) Å
c = 19.387 (5) Å
β = 90.340 (5)°
V = 1795.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.14 × 0.14 × 0.003 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ) T_min = 0.990, T_max = 1.000
17127 measured reflections
3168 independent reflections
2442 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.183
S = 1.04
3168 reflections
299 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17A—H17A⋯N1ⁱ	0.95	2.45	3.246 (8)	141
C21A—H21A⋯Cg3ⁱⁱ	0.95	2.98	3.888 (5)	160
C21B—H21B⋯Cg4ⁱ	0.95	2.99	3.914 (4)	163
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+1.

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: 10.1107/S1600536813014104/zp2005sup1.cif

Structure factors: contains datablock shelxl. DOI: 10.1107/S1600536813014104/zp2005Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813014104/zp2005Isup3.cml

checkCIF report

Comment top

The substituted imidazole derivatives are valuable in treatment of many systemic microbial infections and exhibit different types of pharmacological and biological activities (Kumar 2010). A number of substituted imidazoles, including clotrimazole, are selective inhibitors of nitric oxide synthase, which makes them interesting drug targets in inflammation, neurodegenerative diseases and tumors of the nervous system (Bogle et al., 1994; Castaño et al., 2008). Imidazoles also belong to the class of azole antifungals (Banfi et al., 2006), which includes 1-vinyl imidazole, ketoconazole, miconazole, and clotrimazole. In this aspect we have prepared a series of tetrasubstituted imidazoles including the title compound as potential bio-active precursors. Herein, we report the single-crystal X-ray structure of 2,4,5-Triphenyl-1-(prop-2-en-1-yl)-1H-imidazole (I).

In the title compound (I), (Fig. 1), the two parts of the disordered imidazole ring adopt an envelope conformation [the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.076 (3) Å, ϕ(2) = 357 (4) ° for (N1/N2A/C1/C2A/C3), and Q(2) = 0.146 (4) Å, ϕ(2) = 180 (3) ° for (N1/N2B/C1/C2B/C3)]. The phenyl rings (C4–C9, C10–C15, C16A–C21A and C16B–C21B) makes dihedral angles of 35.91 (7), 18.14 (17), 85.0 (2) and 87.8 (2)°, respectively, with the mean plane of the imadazole ring (N1/N2A/C1/C2A/C3) and the corresponding angles are 18.8 (3), 35.3 (2), 85.7 (3) and 83.6 (3)°, respectively, for (N1/N2B/C1/C2B/C3). The bond lengths in (I) are within normal ranges and are comparable with those reported for the similar structures (Mohamed et al., 2013a,b; Akkurt et al., 2013).

In the crystal structure, molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1, Fig. 2). In addition, C—H···π interactions contribute to the stabilization of the crystal packing.

Related literature top

For the biological significance of imidazole derivatives, see, for example: Kumar (2010); Castaño et al. (2008); Banfi et al. (2006); Bogle et al. (1994). For the synthesis and the structures of similar imidazoles, see: Mohamed et al. (2013a,b); Akkurt et al. (2013). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was synthesized according to our reported method (Mohamed et al. 2013a) in 83% yield. Colourless plates suitable for X-ray analyses were obtained by slow evaporation of a solution of (I) in ethanol, m.p. 377–379 K.

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. View of the major component of the disordered title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing diagram of the title compound viewing along the b axis. The hydrogen atoms not involved in hydrogen bonding and the minor component of the disorder have been omitted for clarity.

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

Crystal data top

C₂₄H₂₀N₂	F(000) = 712
M_r = 336.42	D_x = 1.245 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2698 reflections
a = 10.362 (3) Å	θ = 2.2–21.5°
b = 8.938 (2) Å	µ = 0.07 mm⁻¹
c = 19.387 (5) Å	T = 100 K
β = 90.340 (5)°	Plate, colourless
V = 1795.5 (8) Å³	0.14 × 0.14 × 0.003 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3168 independent reflections
Radiation source: sealed tube	2442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	h = −12→12
T_min = 0.990, T_max = 1.000	k = −10→10
17127 measured reflections	l = −23→23

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0987P)² + 0.7593P] where P = (F_o² + 2F_c²)/3
3168 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.49 e Å⁻³
12 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₄H₂₀N₂	V = 1795.5 (8) Å³
M_r = 336.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.362 (3) Å	µ = 0.07 mm⁻¹
b = 8.938 (2) Å	T = 100 K
c = 19.387 (5) Å	0.14 × 0.14 × 0.003 mm
β = 90.340 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3168 independent reflections
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	2442 reflections with I > 2σ(I)
T_min = 0.990, T_max = 1.000	R_int = 0.046
17127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	12 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	Δρ_max = 0.49 e Å⁻³
3168 reflections	Δρ_min = −0.29 e Å⁻³
299 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	Occ. (<1)
N1	−0.08400 (18)	0.74686 (19)	0.49897 (9)	0.0410 (6)
N2A	0.1170 (5)	0.7384 (5)	0.5420 (2)	0.0353 (16)	0.615 (3)
C1	−0.0060 (2)	0.8077 (2)	0.45077 (12)	0.0403 (7)
C2A	0.1231 (6)	0.8099 (6)	0.4794 (3)	0.0360 (17)	0.615 (3)
C3	−0.0081 (2)	0.6952 (2)	0.54940 (11)	0.0402 (7)
C4	−0.0590 (2)	0.6243 (2)	0.61210 (11)	0.0394 (7)
C5	0.0089 (2)	0.5150 (2)	0.64866 (11)	0.0437 (7)
C6	−0.0425 (2)	0.4520 (3)	0.70782 (12)	0.0486 (8)
C7	−0.1627 (3)	0.4953 (3)	0.73117 (12)	0.0515 (8)
C8	−0.2316 (2)	0.6021 (3)	0.69493 (13)	0.0489 (8)
C9	−0.1804 (2)	0.6654 (3)	0.63597 (13)	0.0454 (8)
C10	−0.0566 (2)	0.8751 (2)	0.38715 (11)	0.0390 (7)
C11	−0.1781 (2)	0.8326 (3)	0.36242 (12)	0.0441 (8)
C12	−0.2281 (2)	0.8935 (3)	0.30231 (12)	0.0482 (8)
C13	−0.1588 (2)	0.9992 (3)	0.26605 (12)	0.0496 (8)
C14	−0.0392 (2)	1.0439 (3)	0.29035 (12)	0.0494 (8)
C15	0.0118 (2)	0.9824 (2)	0.35016 (11)	0.0429 (7)
C16A	0.2459 (4)	0.8604 (4)	0.44996 (18)	0.0334 (11)	0.615 (3)
C17A	0.2941 (6)	0.9947 (9)	0.4667 (4)	0.0396 (16)	0.615 (3)
C18A	0.4150 (3)	1.0459 (4)	0.43689 (18)	0.0403 (11)	0.615 (3)
C19A	0.4771 (4)	0.9553 (5)	0.39306 (19)	0.0470 (14)	0.615 (3)
C20A	0.4300 (4)	0.8172 (5)	0.3761 (2)	0.0543 (14)	0.615 (3)
C21A	0.3143 (5)	0.7684 (5)	0.4041 (2)	0.0500 (16)	0.615 (3)
C22A	0.2230 (4)	0.7339 (5)	0.5920 (2)	0.0505 (10)	0.615 (3)
C23A	0.3217 (4)	0.6142 (5)	0.5810 (2)	0.0505 (10)	0.615 (3)
C24A	0.3129 (6)	0.5098 (6)	0.5380 (2)	0.0505 (10)	0.615 (3)
C24B	0.3213 (17)	0.999 (2)	0.4606 (8)	0.060 (2)	0.385 (3)
C17B	0.2961 (4)	0.5016 (5)	0.5314 (2)	0.085 (4)	0.385 (3)
C18B	0.4132 (4)	0.4561 (4)	0.5598 (2)	0.0480 (19)	0.385 (3)
C19B	0.4774 (3)	0.5477 (5)	0.6067 (2)	0.058 (2)	0.385 (3)
C20B	0.4245 (4)	0.6848 (5)	0.6252 (2)	0.063 (3)	0.385 (3)
N2B	0.1125 (8)	0.7634 (8)	0.4574 (4)	0.039 (2)	0.385 (3)
C2B	0.1184 (10)	0.6892 (9)	0.5210 (5)	0.038 (3)	0.385 (3)
C16B	0.2432 (3)	0.6387 (5)	0.5499 (2)	0.0393 (19)	0.385 (3)
C23B	0.3136 (8)	0.8876 (10)	0.4214 (4)	0.060 (2)	0.385 (3)
C21B	0.3074 (4)	0.7303 (4)	0.5968 (2)	0.059 (3)	0.385 (3)
C22B	0.2197 (8)	0.7681 (9)	0.4076 (4)	0.060 (2)	0.385 (3)
H6	0.00520	0.37850	0.73250	0.0580*
H7	−0.19750	0.45210	0.77180	0.0620*
H8	−0.31430	0.63210	0.71050	0.0590*
H9	−0.22900	0.73820	0.61130	0.0540*
H5	0.09120	0.48350	0.63290	0.0530*
H22B	0.26730	0.83200	0.59130	0.0610*	0.615 (3)
H23A	0.39730	0.61750	0.60890	0.0610*	0.615 (3)
H24A	0.23890	0.50240	0.50900	0.0610*	0.615 (3)
H24B	0.38020	0.43820	0.53430	0.0610*	0.615 (3)
H11	−0.22710	0.76080	0.38720	0.0530*
H12	−0.31050	0.86250	0.28590	0.0580*
H13	−0.19300	1.04080	0.22470	0.0600*
H14	0.00840	1.11730	0.26590	0.0590*
H15	0.09440	1.01370	0.36610	0.0510*
H17A	0.24920	1.05690	0.49830	0.0480*	0.615 (3)
H18A	0.44920	1.14150	0.44820	0.0490*	0.615 (3)
H19A	0.55590	0.98800	0.37330	0.0560*	0.615 (3)
H20A	0.47620	0.75470	0.34530	0.0650*	0.615 (3)
H21A	0.28130	0.67260	0.39230	0.0600*	0.615 (3)
H22A	0.18590	0.72080	0.63850	0.0610*	0.615 (3)
H17B	0.25230	0.43900	0.49930	0.1020*	0.385 (3)
H18B	0.44940	0.36250	0.54720	0.0570*	0.385 (3)
H19B	0.55740	0.51670	0.62610	0.0700*	0.385 (3)
H20B	0.46830	0.74740	0.65720	0.0760*	0.385 (3)
H21B	0.27130	0.82390	0.60940	0.0710*	0.385 (3)
H22C	0.26510	0.67060	0.40850	0.0730*	0.385 (3)
H22D	0.18350	0.78200	0.36070	0.0730*	0.385 (3)
H23B	0.38800	0.87800	0.39330	0.0730*	0.385 (3)
H24C	0.25300	1.02150	0.49140	0.0730*	0.385 (3)
H24D	0.39560	1.06170	0.45950	0.0730*	0.385 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0465 (10)	0.0351 (10)	0.0414 (11)	−0.0013 (8)	0.0027 (9)	0.0000 (8)
N2A	0.046 (2)	0.028 (3)	0.032 (3)	0.004 (2)	−0.0003 (18)	0.0005 (16)
C1	0.0441 (13)	0.0320 (12)	0.0449 (13)	0.0033 (9)	0.0037 (10)	0.0038 (9)
C2A	0.049 (3)	0.029 (3)	0.030 (3)	0.005 (2)	−0.003 (2)	−0.0054 (18)
C3	0.0446 (13)	0.0327 (12)	0.0432 (13)	0.0008 (9)	0.0022 (10)	0.0040 (9)
C4	0.0460 (13)	0.0309 (11)	0.0413 (12)	−0.0001 (9)	0.0022 (10)	−0.0008 (9)
C5	0.0513 (14)	0.0391 (12)	0.0409 (12)	0.0048 (10)	0.0069 (10)	0.0014 (10)
C6	0.0609 (16)	0.0417 (13)	0.0433 (13)	0.0056 (11)	0.0074 (11)	0.0063 (10)
C7	0.0666 (16)	0.0457 (14)	0.0422 (13)	−0.0032 (12)	0.0094 (12)	0.0021 (11)
C8	0.0518 (14)	0.0391 (13)	0.0559 (15)	−0.0005 (11)	0.0143 (12)	−0.0039 (11)
C9	0.0502 (14)	0.0319 (12)	0.0540 (14)	0.0001 (10)	0.0025 (11)	0.0034 (10)
C10	0.0455 (13)	0.0305 (11)	0.0411 (12)	0.0009 (9)	0.0034 (10)	−0.0004 (9)
C11	0.0456 (13)	0.0334 (12)	0.0533 (14)	0.0013 (10)	0.0012 (11)	−0.0001 (10)
C12	0.0486 (14)	0.0419 (13)	0.0539 (14)	−0.0003 (11)	−0.0080 (11)	−0.0054 (11)
C13	0.0610 (15)	0.0465 (14)	0.0413 (13)	0.0024 (12)	−0.0080 (11)	0.0011 (11)
C14	0.0612 (16)	0.0450 (14)	0.0418 (13)	−0.0069 (12)	−0.0030 (11)	0.0060 (11)
C15	0.0500 (13)	0.0384 (12)	0.0401 (12)	−0.0043 (10)	−0.0033 (10)	0.0009 (10)
C16A	0.0321 (19)	0.041 (2)	0.0270 (18)	0.0065 (16)	0.0013 (15)	−0.0007 (15)
C17A	0.030 (3)	0.038 (2)	0.051 (3)	0.005 (2)	0.010 (2)	0.000 (2)
C18A	0.0308 (19)	0.050 (2)	0.040 (2)	−0.0044 (17)	0.0001 (15)	−0.0003 (17)
C19A	0.041 (2)	0.059 (3)	0.041 (2)	0.0007 (18)	−0.0045 (16)	−0.0068 (18)
C20A	0.050 (2)	0.063 (3)	0.050 (2)	0.000 (2)	0.0207 (19)	−0.020 (2)
C21A	0.064 (3)	0.048 (3)	0.038 (2)	−0.006 (2)	0.003 (2)	−0.0151 (18)
C22A	0.0504 (16)	0.061 (2)	0.0401 (14)	0.0030 (14)	0.0057 (13)	0.0122 (12)
C23A	0.0504 (16)	0.061 (2)	0.0401 (14)	0.0030 (14)	0.0057 (13)	0.0122 (12)
C24A	0.0504 (16)	0.061 (2)	0.0401 (14)	0.0030 (14)	0.0057 (13)	0.0122 (12)
C24B	0.060 (4)	0.073 (4)	0.048 (3)	−0.007 (3)	−0.011 (3)	0.010 (2)
C17B	0.080 (7)	0.040 (5)	0.136 (10)	−0.013 (5)	0.001 (7)	−0.001 (5)
C18B	0.033 (3)	0.066 (4)	0.045 (3)	−0.002 (3)	−0.002 (3)	0.004 (3)
C19B	0.060 (4)	0.055 (4)	0.060 (4)	−0.009 (3)	0.029 (3)	−0.015 (3)
C20B	0.058 (4)	0.069 (5)	0.062 (4)	−0.004 (4)	−0.031 (4)	−0.018 (4)
N2B	0.053 (4)	0.036 (4)	0.029 (4)	−0.008 (3)	0.001 (3)	0.003 (3)
C2B	0.052 (4)	0.024 (5)	0.039 (5)	−0.005 (4)	−0.004 (4)	0.000 (3)
C16B	0.037 (3)	0.050 (4)	0.031 (3)	−0.014 (3)	0.003 (3)	−0.008 (3)
C23B	0.060 (4)	0.073 (4)	0.048 (3)	−0.007 (3)	−0.011 (3)	0.010 (2)
C21B	0.085 (6)	0.052 (4)	0.040 (4)	0.007 (4)	0.004 (4)	−0.018 (3)
C22B	0.060 (4)	0.073 (4)	0.048 (3)	−0.007 (3)	−0.011 (3)	0.010 (2)

Geometric parameters (Å, º) top

N1—C1	1.353 (3)	C20A—C21A	1.389 (6)
N1—C3	1.334 (3)	C20B—C21B	1.390 (6)
N2A—C2A	1.373 (7)	C22A—C23A	1.496 (6)
N2A—C3	1.361 (6)	C22B—C23B	1.468 (12)
N2A—C22A	1.461 (6)	C23A—C24A	1.254 (6)
N2B—C2B	1.401 (12)	C23B—C24B	1.255 (19)
N2B—C22B	1.477 (11)	C5—H5	0.9500
N2B—C1	1.296 (8)	C6—H6	0.9500
C1—C2A	1.445 (7)	C7—H7	0.9500
C1—C10	1.467 (3)	C8—H8	0.9500
C2A—C16A	1.469 (7)	C9—H9	0.9500
C2B—C3	1.426 (10)	C11—H11	0.9500
C2B—C16B	1.477 (11)	C12—H12	0.9500
C3—C4	1.471 (3)	C13—H13	0.9500
C4—C5	1.395 (3)	C14—H14	0.9500
C4—C9	1.392 (3)	C15—H15	0.9500
C5—C6	1.387 (3)	C17A—H17A	0.9500
C6—C7	1.383 (4)	C17B—H17B	0.9500
C7—C8	1.382 (4)	C18A—H18A	0.9500
C8—C9	1.384 (4)	C18B—H18B	0.9500
C10—C11	1.397 (3)	C19A—H19A	0.9500
C10—C15	1.394 (3)	C19B—H19B	0.9500
C11—C12	1.384 (3)	C20A—H20A	0.9500
C12—C13	1.381 (3)	C20B—H20B	0.9500
C13—C14	1.382 (3)	C21A—H21A	0.9500
C14—C15	1.385 (3)	C21B—H21B	0.9500
C16A—C17A	1.339 (9)	C22A—H22A	0.9900
C16A—C21A	1.406 (6)	C22A—H22B	0.9900
C16B—C17B	1.390 (6)	C22B—H22C	0.9900
C16B—C21B	1.390 (6)	C22B—H22D	0.9900
C17A—C18A	1.457 (7)	C23A—H23A	0.9500
C17B—C18B	1.390 (6)	C23B—H23B	0.9500
C18A—C19A	1.341 (5)	C24A—H24A	0.9500
C18B—C19B	1.390 (6)	C24A—H24B	0.9500
C19A—C20A	1.367 (6)	C24B—H24C	0.9500
C19B—C20B	1.390 (6)	C24B—H24D	0.9500

C1—N1—C3	107.06 (18)	C6—C5—H5	120.00
C2A—N2A—C3	105.9 (4)	C5—C6—H6	120.00
C2A—N2A—C22A	124.1 (5)	C7—C6—H6	120.00
C3—N2A—C22A	129.4 (3)	C6—C7—H7	120.00
C2B—N2B—C22B	124.0 (8)	C8—C7—H7	120.00
C1—N2B—C2B	105.6 (7)	C7—C8—H8	120.00
C1—N2B—C22B	130.0 (7)	C9—C8—H8	120.00
N1—C1—C2A	107.2 (3)	C4—C9—H9	119.00
N2B—C1—C10	122.9 (4)	C8—C9—H9	119.00
N1—C1—C10	122.26 (19)	C10—C11—H11	120.00
N1—C1—N2B	112.2 (4)	C12—C11—H11	120.00
C2A—C1—C10	130.0 (3)	C11—C12—H12	120.00
N2A—C2A—C1	106.6 (5)	C13—C12—H12	120.00
N2A—C2A—C16A	122.1 (5)	C12—C13—H13	120.00
C1—C2A—C16A	131.1 (4)	C14—C13—H13	120.00
N2B—C2B—C3	106.7 (7)	C13—C14—H14	120.00
C3—C2B—C16B	132.1 (7)	C15—C14—H14	120.00
N2B—C2B—C16B	120.8 (8)	C10—C15—H15	120.00
C2B—C3—C4	129.6 (4)	C14—C15—H15	120.00
N1—C3—C4	122.82 (19)	C16A—C17A—H17A	120.00
N1—C3—C2B	105.6 (4)	C18A—C17A—H17A	120.00
N1—C3—N2A	112.5 (2)	C16B—C17B—H17B	120.00
N2A—C3—C4	123.8 (2)	C18B—C17B—H17B	120.00
C5—C4—C9	118.0 (2)	C17A—C18A—H18A	121.00
C3—C4—C5	122.63 (19)	C19A—C18A—H18A	121.00
C3—C4—C9	119.34 (19)	C17B—C18B—H18B	120.00
C4—C5—C6	120.6 (2)	C19B—C18B—H18B	120.00
C5—C6—C7	120.5 (2)	C18A—C19A—H19A	119.00
C6—C7—C8	119.4 (2)	C20A—C19A—H19A	119.00
C7—C8—C9	120.2 (2)	C18B—C19B—H19B	120.00
C4—C9—C8	121.2 (2)	C20B—C19B—H19B	120.00
C11—C10—C15	118.1 (2)	C19A—C20A—H20A	120.00
C1—C10—C11	119.59 (19)	C21A—C20A—H20A	120.00
C1—C10—C15	122.34 (19)	C19B—C20B—H20B	120.00
C10—C11—C12	120.9 (2)	C21B—C20B—H20B	120.00
C11—C12—C13	120.3 (2)	C16A—C21A—H21A	120.00
C12—C13—C14	119.5 (2)	C20A—C21A—H21A	120.00
C13—C14—C15	120.5 (2)	C20B—C21B—H21B	120.00
C10—C15—C14	120.7 (2)	C16B—C21B—H21B	120.00
C17A—C16A—C21A	119.3 (5)	N2A—C22A—H22B	108.00
C2A—C16A—C21A	120.5 (4)	N2A—C22A—H22A	108.00
C2A—C16A—C17A	120.3 (4)	H22A—C22A—H22B	107.00
C2B—C16B—C17B	121.1 (5)	C23A—C22A—H22A	108.00
C17B—C16B—C21B	120.0 (3)	C23A—C22A—H22B	108.00
C2B—C16B—C21B	118.9 (5)	N2B—C22B—H22D	109.00
C16A—C17A—C18A	120.4 (6)	H22C—C22B—H22D	108.00
C16B—C17B—C18B	120.0 (4)	C23B—C22B—H22C	109.00
C17A—C18A—C19A	118.6 (4)	C23B—C22B—H22D	109.00
C17B—C18B—C19B	120.0 (4)	N2B—C22B—H22C	109.00
C18A—C19A—C20A	121.7 (4)	C22A—C23A—H23A	117.00
C18B—C19B—C20B	120.0 (3)	C24A—C23A—H23A	117.00
C19A—C20A—C21A	119.8 (4)	C22B—C23B—H23B	112.00
C19B—C20B—C21B	120.0 (4)	C24B—C23B—H23B	112.00
C16A—C21A—C20A	120.2 (4)	H24A—C24A—H24B	120.00
C16B—C21B—C20B	120.0 (4)	C23A—C24A—H24A	120.00
N2A—C22A—C23A	115.9 (4)	C23A—C24A—H24B	120.00
N2B—C22B—C23B	113.7 (7)	C23B—C24B—H24C	120.00
C22A—C23A—C24A	125.4 (4)	C23B—C24B—H24D	120.00
C22B—C23B—C24B	136.7 (11)	H24C—C24B—H24D	120.00
C4—C5—H5	120.00

C3—N1—C1—C2A	−8.2 (3)	N1—C3—C4—C5	150.5 (2)
C3—N1—C1—C10	179.56 (17)	N2A—C3—C4—C9	139.5 (3)
C1—N1—C3—N2A	9.1 (3)	C9—C4—C5—C6	−1.4 (3)
C1—N1—C3—C4	178.39 (17)	C3—C4—C5—C6	179.5 (2)
C3—N2A—C22A—C23A	105.6 (5)	C5—C4—C9—C8	1.2 (3)
C2A—N2A—C3—N1	−6.0 (4)	C3—C4—C9—C8	−179.6 (2)
C22A—N2A—C3—N1	165.4 (4)	C4—C5—C6—C7	0.7 (3)
C2A—N2A—C3—C4	−175.2 (3)	C5—C6—C7—C8	0.1 (4)
C22A—N2A—C3—C4	−3.8 (6)	C6—C7—C8—C9	−0.2 (4)
C3—N2A—C2A—C16A	−174.0 (4)	C7—C8—C9—C4	−0.4 (4)
C3—N2A—C2A—C1	0.6 (5)	C1—C10—C11—C12	−179.6 (2)
C22A—N2A—C2A—C1	−171.4 (4)	C11—C10—C15—C14	−0.5 (3)
C2A—N2A—C22A—C23A	−84.4 (6)	C1—C10—C15—C14	−179.8 (2)
C22A—N2A—C2A—C16A	14.0 (8)	C15—C10—C11—C12	1.1 (3)
N1—C1—C10—C11	−23.1 (3)	C10—C11—C12—C13	−0.8 (4)
N1—C1—C2A—N2A	4.7 (4)	C11—C12—C13—C14	−0.1 (4)
C2A—C1—C10—C15	−14.0 (4)	C12—C13—C14—C15	0.7 (4)
C2A—C1—C10—C11	166.6 (3)	C13—C14—C15—C10	−0.4 (3)
N1—C1—C2A—C16A	178.7 (5)	C2A—C16A—C17A—C18A	−179.2 (5)
C10—C1—C2A—N2A	176.1 (3)	C17A—C16A—C21A—C20A	−0.6 (7)
C10—C1—C2A—C16A	−9.9 (7)	C21A—C16A—C17A—C18A	1.0 (8)
N1—C1—C10—C15	156.25 (19)	C2A—C16A—C21A—C20A	179.6 (4)
N2A—C2A—C16A—C17A	−86.4 (7)	C16A—C17A—C18A—C19A	−0.6 (8)
N2A—C2A—C16A—C21A	93.4 (6)	C17A—C18A—C19A—C20A	−0.2 (6)
C1—C2A—C16A—C21A	−79.8 (6)	C18A—C19A—C20A—C21A	0.6 (6)
C1—C2A—C16A—C17A	100.4 (7)	C19A—C20A—C21A—C16A	−0.2 (6)
N1—C3—C4—C9	−28.6 (3)	N2A—C22A—C23A—C24A	−8.4 (7)
N2A—C3—C4—C5	−41.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17A—H17A···N1ⁱ	0.95	2.45	3.246 (8)	141
C24A—H24A···N2A	0.95	2.54	2.882 (8)	101
C21A—H21A···Cg3ⁱⁱ	0.95	2.98	3.888 (5)	160
C21B—H21B···Cg4ⁱ	0.95	2.99	3.914 (4)	163

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂
M_r	336.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.362 (3), 8.938 (2), 19.387 (5)
β (°)	90.340 (5)
V (Å³)	1795.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.14 × 0.14 × 0.003

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)
T_min, T_max	0.990, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17127, 3168, 2442
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.183, 1.04
No. of reflections	3168
No. of parameters	299
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.29

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

Cg3 and Cg4 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17A—H17A···N1ⁱ	0.95	2.45	3.246 (8)	141
C21A—H21A···Cg3ⁱⁱ	0.95	2.98	3.888 (5)	160
C21B—H21B···Cg4ⁱ	0.95	2.99	3.914 (4)	163

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1.

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

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Volume 69| Part 6| June 2013| Pages o988-o989

doi:10.1107/S1600536813014104

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