1-(2,3,4,5,6-Penta­methyl­benz­yl)-2-(pyridin-2-yl)-1H-benzimidazole

Anĝay, F.; Çelik, Ö.; Barlık, O.; Ulusoy, M.

doi:10.1107/S1600536814007934

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o563-o564

doi:10.1107/S1600536814007934

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1-(2,3,4,5,6-Pentamethylbenzyl)-2-(pyridin-2-yl)-1H-benzimidazole

Fırat Anĝay,^a Ömer Çelik,^b,^c ^* Orhan Barlık ^d and Mahmut Ulusoy ^d

^aDepartment of Physics, Institute of Sciences, Dicle University, 21280, Diyarbakır, Turkey, ^bDepartment of Physics, Faculty of Education, Dicle University, 21280, Diyarbakır, Turkey, ^cScience and Technology Application and Research Center, Dicle University, 21280, Diyarbakır, Turkey, and ^dDepartment of Chemistry, Faculty of Science & Art, Harran University, 63300, Şanlıurfa, Turkey
^*Correspondence e-mail: omer.celik@dicle.edu.tr

(Received 28 March 2014; accepted 9 April 2014; online 16 April 2014)

In the title compound, C₂₄H₂₅N₃, the benzimidazole ring system is essentially planar, with an r.m.s. deviation of 0.017 Å, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the pyridine and benzene rings, respectively. An intramolecular C—H⋯N hydrogen bond is observed. In the crystal, molecules are stacked along the a axis by weak C—H⋯π interactions.

CCDC reference: 996309

Related literature

For the use of 2-(2-pyridyl)benzimidazole in coordination chemistry, see: Sahin et al. (2010 ); Harkins et al. (1956 ); Chiswell et al. (1964 ); De Castro et al. (1991 ); Maekawa et al. (1994 ); Khalil et al. (2001 ); Boca et al. (1997 ). For the use of N—N-type ligand systems involving 2,2′-bipyridine, see: Lippert (1999 ); Wong & Giandomenico (1999 ), Kelland & Farrell (2000 ). For related structures, see: Çelik et al. (2007 , 2009 , 2014 ).

Experimental

Crystal data

C₂₄H₂₅N₃
M_r = 355.47
Monoclinic, P 2₁ /n
a = 5.3470 (3) Å
b = 21.0622 (12) Å
c = 17.0379 (9) Å
β = 97.699 (3)°
V = 1901.50 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.982, T_max = 0.989
25354 measured reflections
3741 independent reflections
3056 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.150
S = 1.04
3741 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgⁱ	0.97	2.91	3.6941 (18)	139
C13—H13B⋯N1	0.97	2.30	3.029 (2)	131
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 996309

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814007934/rz5115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007934/rz5115Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007934/rz5115Isup3.cml

checkCIF report

Comment top

The N—N type ligand system 2-(2-pyridyl)benzimidazole has a venerable history in coordination chemistry (Sahin et al., 2010; Harkins et al., 1956; Chiswell et al., 1964; De Castro et al., 1991; Maekawa et al., 1994; Khalil et al., 2001; Boca et al., 1997). Lots of platinum chemistry bearing N—N type ligand systems involving 2,2'-bipyridine has been reported aimed at the design of drugs having less serious side-effects than those of cisplatin, or which could extend the scope of Pt based chemotherapy to tumours (Lippert, 1999; Wong & Giandomenico, 1999; Kelland & Farrell, 2000).

The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles are in good agreement with those reported for related structures (Çelik et al., 2007; Çelik et al., 2009; Çelik et al., 2014). The benzimidazole ring system is substantially planar, the maximum deviation being 0.027 (2) Å for atom C8, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the mean planes through the pyridine (N1/C1–C5) and phenyl (C14–C19) rings, respectively. An intramolecular C—H···N hydrogen bond is present (Table 1). In the crystal structure (Fig. 2), molecules are stacked along the a axis by weak C—H···π hydrogen interactions (Table 1) involving the C7—C12 benzene ring of the benzimidazole moiety.

Related literature top

For the use of 2-(2-pyridyl)benzimidazole in coordination chemistry, see: Sahin et al. (2010); Harkins et al. (1956); Chiswell et al. (1964); De Castro et al. (1991); Maekawa et al. (1994); Khalil et al. (2001); Boca et al. (1997). For the use of N—N-type ligand systems involving 2,2'-bipyridine, see: Lippert (1999); Wong & Giandomenico (1999), Kelland & Farrell (2000). For related structures, see: Çelik et al. (2007, 2009, 2014).

Experimental top

NaH (60%) (398 mg, 11.0 mmol) was washed two times with dry hexane, filtered off via cannula and a solution of the 2-pyridiylbenzimidazole (1.95 g, 10.0 mmol) in dry toluene (10 ml) was added, then the solution was heated at 90°C for 24 h. Evolution of hydrogen was observed at this temperature. 2,3,4,5,6-Pentamethylbenzyl bromide (2.45 g, 10.0 mmol) was added to this mixture at room temperature and then heated again at 90°C for 1 day. Then volatiles were evaporated in vacuum to dryness. The residue was dissolved in CH₂C_l2 and filtered via cannula on celite. The desired product was obtained after concentration of CH₂C_l2 (15 ml) and then precipitated with hexane (30 ml). The off-white solid obtained in 86% yield. M. p. 416–418 K. ¹H NMR (400 MHz, CDCl₃, δ p.p.m.): 1.26 (s, 6H, o-(CH₃)₂); 1.36(s, 6H, m-(CH₃)₂); 2.13–2.20 (s, 3H, p-CH₃); 5.50 (s, 2H, N—CH₂); 6.86 (s, 1H, Ar—CH); 7.11 (s, 1H, Ar—CH); 7.26 (s, 1H, Ar—CH); 7.35 (s, 1H, Ar—CH); 7.49 (s, 1H, Ar—CH); 8.46 (s, 1H, Ar—CH); 10.19 (s, 2H, Ar—CH). ¹³C NMR (100.56 MHz, CDCl₃, δ p.p.m.): 17.0; 17.4; 29.6; 31.7; 34.4; 35.2; 48.7; 49.3; 56.2; 117.9; 121.2; 122.4; 125.5; 126.5; 133.8; 134.0; 137.5; 140.7; 158.0; 167.9.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. ORTEP-3 of the title compound, showing displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The stacking of the title compound along the a axis with C—H···π type hydrogen-bond interactions (dashed lines). Displacement ellipsoids are drawn at the 50% probability level.

1-(2,3,4,5,6-Pentamethylbenzyl)-2-(pyridin-2-yl)-1H-benzimidazole top

Crystal data top

C₂₄H₂₅N₃	F(000) = 760
M_r = 355.47	D_x = 1.242 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.3470 (3) Å	Cell parameters from 1276 reflections
b = 21.0622 (12) Å	θ = 2.3–31.5°
c = 17.0379 (9) Å	µ = 0.07 mm⁻¹
β = 97.699 (3)°	T = 296 K
V = 1901.50 (18) Å³	Prism, yellow
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −6→6
T_min = 0.982, T_max = 0.989	k = −25→25
25354 measured reflections	l = −21→20
3741 independent reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0775P)² + 0.5927P] where P = (F_o² + 2F_c²)/3
3741 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₄H₂₅N₃	V = 1901.50 (18) Å³
M_r = 355.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.3470 (3) Å	µ = 0.07 mm⁻¹
b = 21.0622 (12) Å	T = 296 K
c = 17.0379 (9) Å	0.25 × 0.20 × 0.15 mm
β = 97.699 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3741 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3056 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.989	R_int = 0.026
25354 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
3741 reflections	Δρ_min = −0.17 e Å⁻³
254 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.0873 (5)	0.86580 (11)	0.44231 (14)	0.0724 (6)
H1	1.2174	0.8428	0.4246	0.087*
C2	1.0060 (5)	0.91952 (12)	0.40152 (14)	0.0737 (6)
H2	1.0790	0.9327	0.3577	0.088*
C3	0.8151 (5)	0.95308 (12)	0.42706 (16)	0.0842 (7)
H3	0.7548	0.9900	0.4011	0.101*
C4	0.7133 (5)	0.93151 (10)	0.49165 (15)	0.0771 (7)
H4	0.5809	0.9535	0.5094	0.092*
C5	0.8068 (3)	0.87716 (7)	0.53054 (11)	0.0465 (4)
C6	0.6926 (3)	0.85653 (7)	0.60059 (10)	0.0452 (4)
C7	0.4595 (4)	0.86110 (8)	0.69313 (11)	0.0507 (4)
C8	0.2891 (4)	0.87790 (10)	0.74483 (13)	0.0658 (6)
H8	0.2014	0.9161	0.7387	0.079*
C9	0.2541 (4)	0.83708 (10)	0.80460 (13)	0.0667 (6)
H9	0.1414	0.8477	0.8396	0.080*
C10	0.3850 (4)	0.77962 (10)	0.81392 (12)	0.0598 (5)
H10	0.3597	0.7531	0.8558	0.072*
C11	0.5507 (4)	0.76104 (9)	0.76284 (10)	0.0505 (4)
H11	0.6360	0.7225	0.7690	0.061*
C12	0.5841 (3)	0.80251 (8)	0.70185 (10)	0.0432 (4)
C13	0.8894 (3)	0.74472 (7)	0.62583 (10)	0.0422 (4)
H13A	1.0264	0.7410	0.6691	0.051*
H13B	0.9632	0.7525	0.5777	0.051*
C14	0.7459 (3)	0.68215 (7)	0.61734 (9)	0.0370 (4)
C15	0.5434 (3)	0.67529 (7)	0.55618 (9)	0.0391 (4)
C16	0.4047 (3)	0.61901 (8)	0.54888 (10)	0.0452 (4)
C17	0.4753 (3)	0.56796 (8)	0.59946 (11)	0.0471 (4)
C18	0.6838 (3)	0.57318 (7)	0.65801 (10)	0.0448 (4)
C19	0.8190 (3)	0.63066 (7)	0.66771 (10)	0.0412 (4)
C20	0.4783 (4)	0.72858 (9)	0.49769 (10)	0.0511 (4)
H20A	0.406 (3)	0.7111 (2)	0.4472 (7)	0.077*
H20B	0.630 (2)	0.7521 (5)	0.4912 (6)	0.077*
H20C	0.357 (2)	0.7567 (5)	0.5172 (5)	0.077*
C21	0.1762 (4)	0.61342 (11)	0.48609 (14)	0.0703 (6)
H21A	0.2254 (10)	0.5965 (8)	0.4399 (8)	0.105*
H21B	0.106 (2)	0.6535 (6)	0.4754 (8)	0.105*
H21C	0.057 (2)	0.5868 (8)	0.5043 (5)	0.105*
C22	0.3235 (5)	0.50692 (10)	0.59025 (15)	0.0710 (6)
H22A	0.314 (3)	0.4923 (5)	0.5373 (9)	0.107*
H22B	0.158 (3)	0.5146 (2)	0.6025 (10)	0.107*
H22C	0.403 (2)	0.4757 (5)	0.6251 (9)	0.107*
C23	0.7616 (5)	0.51661 (9)	0.71064 (13)	0.0655 (6)
H23A	0.626 (2)	0.5047 (5)	0.7383 (8)	0.098*
H23B	0.904 (3)	0.5276 (3)	0.7476 (8)	0.098*
H23C	0.803 (3)	0.4820 (6)	0.6790 (5)	0.098*
C24	1.0435 (4)	0.63574 (10)	0.73176 (13)	0.0630 (5)
H24A	1.168 (2)	0.6592 (7)	0.7134 (4)	0.094*
H24B	1.104 (2)	0.5960 (6)	0.7452 (7)	0.094*
H24C	0.9950 (10)	0.6551 (7)	0.7754 (7)	0.094*
N1	0.9926 (3)	0.84413 (8)	0.50574 (10)	0.0616 (4)
N2	0.5315 (3)	0.89400 (7)	0.63031 (10)	0.0561 (4)
N3	0.7309 (3)	0.79969 (6)	0.64092 (8)	0.0406 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0797 (15)	0.0651 (13)	0.0780 (14)	0.0052 (11)	0.0312 (12)	0.0205 (11)
C2	0.0844 (16)	0.0737 (14)	0.0641 (13)	−0.0104 (12)	0.0138 (12)	0.0232 (11)
C3	0.1041 (19)	0.0620 (14)	0.0871 (17)	0.0111 (13)	0.0152 (15)	0.0351 (13)
C4	0.0940 (17)	0.0516 (12)	0.0889 (16)	0.0184 (11)	0.0244 (14)	0.0216 (11)
C5	0.0539 (10)	0.0329 (8)	0.0517 (10)	−0.0066 (7)	0.0031 (8)	0.0006 (7)
C6	0.0522 (10)	0.0305 (8)	0.0519 (10)	−0.0019 (7)	0.0034 (8)	−0.0032 (7)
C7	0.0580 (11)	0.0396 (9)	0.0551 (10)	−0.0025 (8)	0.0099 (9)	−0.0119 (8)
C8	0.0756 (14)	0.0522 (11)	0.0726 (13)	0.0050 (10)	0.0212 (11)	−0.0188 (10)
C9	0.0737 (14)	0.0657 (13)	0.0651 (13)	−0.0053 (11)	0.0261 (11)	−0.0210 (11)
C10	0.0732 (13)	0.0590 (11)	0.0490 (10)	−0.0122 (10)	0.0152 (9)	−0.0084 (9)
C11	0.0582 (11)	0.0457 (9)	0.0476 (10)	−0.0050 (8)	0.0070 (8)	−0.0042 (7)
C12	0.0451 (9)	0.0397 (8)	0.0442 (9)	−0.0072 (7)	0.0038 (7)	−0.0087 (7)
C13	0.0405 (9)	0.0345 (8)	0.0514 (9)	0.0012 (6)	0.0059 (7)	0.0014 (7)
C14	0.0395 (8)	0.0319 (7)	0.0407 (8)	0.0008 (6)	0.0096 (6)	−0.0031 (6)
C15	0.0416 (8)	0.0382 (8)	0.0389 (8)	0.0030 (6)	0.0108 (7)	−0.0045 (6)
C16	0.0441 (9)	0.0449 (9)	0.0479 (9)	−0.0036 (7)	0.0108 (7)	−0.0122 (7)
C17	0.0536 (10)	0.0381 (9)	0.0538 (10)	−0.0077 (7)	0.0227 (8)	−0.0116 (7)
C18	0.0574 (10)	0.0339 (8)	0.0473 (9)	0.0041 (7)	0.0230 (8)	−0.0003 (7)
C19	0.0453 (9)	0.0367 (8)	0.0426 (8)	0.0044 (7)	0.0094 (7)	0.0000 (6)
C20	0.0573 (11)	0.0504 (10)	0.0441 (9)	0.0048 (8)	0.0010 (8)	0.0003 (8)
C21	0.0589 (12)	0.0747 (14)	0.0738 (14)	−0.0118 (11)	−0.0033 (11)	−0.0163 (11)
C22	0.0808 (15)	0.0505 (11)	0.0862 (15)	−0.0231 (10)	0.0274 (12)	−0.0111 (10)
C23	0.0940 (16)	0.0398 (10)	0.0665 (13)	0.0052 (10)	0.0247 (11)	0.0093 (9)
C24	0.0675 (13)	0.0540 (11)	0.0624 (12)	0.0037 (9)	−0.0094 (10)	0.0093 (9)
N1	0.0691 (10)	0.0521 (9)	0.0671 (10)	0.0057 (8)	0.0216 (8)	0.0180 (8)
N2	0.0697 (10)	0.0346 (7)	0.0650 (10)	0.0040 (7)	0.0129 (8)	−0.0039 (7)
N3	0.0456 (7)	0.0305 (6)	0.0455 (7)	−0.0029 (5)	0.0056 (6)	−0.0021 (5)

Geometric parameters (Å, º) top

C1—N1	1.334 (3)	C13—H13B	0.9700
C1—C2	1.368 (3)	C14—C19	1.405 (2)
C1—H1	0.9300	C14—C15	1.406 (2)
C2—C3	1.360 (4)	C15—C16	1.395 (2)
C2—H2	0.9300	C15—C20	1.510 (2)
C3—C4	1.369 (3)	C16—C17	1.398 (3)
C3—H3	0.9300	C16—C21	1.517 (3)
C4—C5	1.382 (3)	C17—C18	1.397 (3)
C4—H4	0.9300	C17—C22	1.517 (2)
C5—N1	1.328 (2)	C18—C19	1.408 (2)
C5—C6	1.477 (3)	C18—C23	1.515 (2)
C6—N2	1.319 (2)	C19—C24	1.514 (3)
C6—N3	1.382 (2)	C20—H20A	0.968 (12)
C7—N2	1.373 (2)	C20—H20B	0.968 (13)
C7—C8	1.395 (3)	C20—H20C	0.968 (12)
C7—C12	1.401 (2)	C21—H21A	0.933 (14)
C8—C9	1.365 (3)	C21—H21B	0.933 (14)
C8—H8	0.9300	C21—H21C	0.933 (14)
C9—C10	1.396 (3)	C22—H22A	0.948 (14)
C9—H9	0.9300	C22—H22B	0.948 (14)
C10—C11	1.379 (3)	C22—H22C	0.948 (14)
C10—H10	0.9300	C23—H23A	0.951 (14)
C11—C12	1.387 (2)	C23—H23B	0.951 (14)
C11—H11	0.9300	C23—H23C	0.951 (13)
C12—N3	1.384 (2)	C24—H24A	0.915 (14)
C13—N3	1.478 (2)	C24—H24B	0.915 (13)
C13—C14	1.522 (2)	C24—H24C	0.915 (13)
C13—H13A	0.9700

N1—C1—C2	124.4 (2)	C15—C16—C17	120.14 (16)
N1—C1—H1	117.8	C15—C16—C21	119.82 (17)
C2—C1—H1	117.8	C17—C16—C21	120.05 (16)
C3—C2—C1	117.9 (2)	C18—C17—C16	120.23 (15)
C3—C2—H2	121.0	C18—C17—C22	120.34 (17)
C1—C2—H2	121.0	C16—C17—C22	119.42 (18)
C2—C3—C4	118.7 (2)	C17—C18—C19	119.95 (15)
C2—C3—H3	120.6	C17—C18—C23	119.35 (16)
C4—C3—H3	120.6	C19—C18—C23	120.69 (17)
C3—C4—C5	120.2 (2)	C14—C19—C18	119.69 (15)
C3—C4—H4	119.9	C14—C19—C24	120.95 (15)
C5—C4—H4	119.9	C18—C19—C24	119.35 (15)
N1—C5—C4	121.30 (19)	C15—C20—H20A	109.5
N1—C5—C6	120.74 (15)	C15—C20—H20B	109.5
C4—C5—C6	117.96 (18)	H20A—C20—H20B	109.5
N2—C6—N3	112.86 (16)	C15—C20—H20C	109.5
N2—C6—C5	119.77 (15)	H20A—C20—H20C	109.5
N3—C6—C5	127.37 (15)	H20B—C20—H20C	109.5
N2—C7—C8	129.74 (18)	C16—C21—H21A	109.5
N2—C7—C12	110.39 (16)	C16—C21—H21B	109.5
C8—C7—C12	119.87 (18)	H21A—C21—H21B	109.5
C9—C8—C7	118.6 (2)	C16—C21—H21C	109.5
C9—C8—H8	120.7	H21A—C21—H21C	109.5
C7—C8—H8	120.7	H21B—C21—H21C	109.5
C8—C9—C10	120.93 (19)	C17—C22—H22A	109.5
C8—C9—H9	119.5	C17—C22—H22B	109.5
C10—C9—H9	119.5	H22A—C22—H22B	109.5
C11—C10—C9	121.92 (19)	C17—C22—H22C	109.5
C11—C10—H10	119.0	H22A—C22—H22C	109.5
C9—C10—H10	119.0	H22B—C22—H22C	109.5
C10—C11—C12	116.88 (18)	C18—C23—H23A	109.5
C10—C11—H11	121.6	C18—C23—H23B	109.5
C12—C11—H11	121.6	H23A—C23—H23B	109.5
N3—C12—C11	132.66 (16)	C18—C23—H23C	109.5
N3—C12—C7	105.53 (15)	H23A—C23—H23C	109.5
C11—C12—C7	121.80 (17)	H23B—C23—H23C	109.5
N3—C13—C14	113.67 (13)	C19—C24—H24A	109.5
N3—C13—H13A	108.8	C19—C24—H24B	109.5
C14—C13—H13A	108.8	H24A—C24—H24B	109.5
N3—C13—H13B	108.8	C19—C24—H24C	109.5
C14—C13—H13B	108.8	H24A—C24—H24C	109.5
H13A—C13—H13B	107.7	H24B—C24—H24C	109.5
C19—C14—C15	119.78 (14)	C5—N1—C1	117.39 (17)
C19—C14—C13	120.99 (14)	C6—N2—C7	105.26 (15)
C15—C14—C13	119.19 (14)	C6—N3—C12	105.94 (13)
C16—C15—C14	120.06 (15)	C6—N3—C13	129.98 (14)
C16—C15—C20	119.99 (15)	C12—N3—C13	124.08 (13)
C14—C15—C20	119.95 (14)

N1—C1—C2—C3	−0.2 (4)	C15—C16—C17—C22	−179.52 (16)
C1—C2—C3—C4	−0.3 (4)	C21—C16—C17—C22	0.7 (3)
C2—C3—C4—C5	1.0 (4)	C16—C17—C18—C19	1.9 (2)
C3—C4—C5—N1	−1.2 (4)	C22—C17—C18—C19	−178.06 (16)
C3—C4—C5—C6	179.1 (2)	C16—C17—C18—C23	−178.23 (16)
N1—C5—C6—N2	171.36 (17)	C22—C17—C18—C23	1.8 (2)
C4—C5—C6—N2	−9.0 (3)	C15—C14—C19—C18	−1.9 (2)
N1—C5—C6—N3	−9.7 (3)	C13—C14—C19—C18	−179.49 (14)
C4—C5—C6—N3	169.96 (19)	C15—C14—C19—C24	177.28 (16)
N2—C7—C8—C9	−178.4 (2)	C13—C14—C19—C24	−0.3 (2)
C12—C7—C8—C9	1.9 (3)	C17—C18—C19—C14	−1.2 (2)
C7—C8—C9—C10	−0.1 (3)	C23—C18—C19—C14	178.93 (15)
C8—C9—C10—C11	−1.2 (3)	C17—C18—C19—C24	179.62 (16)
C9—C10—C11—C12	0.7 (3)	C23—C18—C19—C24	−0.3 (2)
C10—C11—C12—N3	−179.82 (17)	C4—C5—N1—C1	0.7 (3)
C10—C11—C12—C7	1.1 (3)	C6—C5—N1—C1	−179.67 (18)
N2—C7—C12—N3	−1.48 (19)	C2—C1—N1—C5	0.1 (4)
C8—C7—C12—N3	178.23 (17)	N3—C6—N2—C7	0.2 (2)
N2—C7—C12—C11	177.79 (16)	C5—C6—N2—C7	179.26 (15)
C8—C7—C12—C11	−2.5 (3)	C8—C7—N2—C6	−178.8 (2)
N3—C13—C14—C19	−121.53 (16)	C12—C7—N2—C6	0.8 (2)
N3—C13—C14—C15	60.88 (19)	N2—C6—N3—C12	−1.10 (19)
C19—C14—C15—C16	4.3 (2)	C5—C6—N3—C12	179.91 (16)
C13—C14—C15—C16	−178.05 (14)	N2—C6—N3—C13	178.34 (15)
C19—C14—C15—C20	−174.84 (15)	C5—C6—N3—C13	−0.7 (3)
C13—C14—C15—C20	2.8 (2)	C11—C12—N3—C6	−177.65 (18)
C14—C15—C16—C17	−3.6 (2)	C7—C12—N3—C6	1.50 (17)
C20—C15—C16—C17	175.52 (15)	C11—C12—N3—C13	2.9 (3)
C14—C15—C16—C21	176.10 (16)	C7—C12—N3—C13	−177.98 (14)
C20—C15—C16—C21	−4.7 (2)	C14—C13—N3—C6	−125.33 (17)
C15—C16—C17—C18	0.5 (2)	C14—C13—N3—C12	54.0 (2)
C21—C16—C17—C18	−179.21 (16)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.97	2.91	3.6941 (18)	139
C13—H13B···N1	0.97	2.30	3.029 (2)	131

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.97	2.91	3.6941 (18)	139
C13—H13B···N1	0.97	2.30	3.029 (2)	131

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are indebted to the X-ray laboratory of Dicle University Science and the Technology Application and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer.

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Volume 70| Part 5| May 2014| Pages o563-o564

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