4,5-Dimethyl-2-phenyl-1-(p-tol­yl)-1H-imidazole

Gayathri, P.; Thiruvalluvar, A.; Srinivasan, N.; Jayabharathi, J.; Butcher, R.J.

doi:10.1107/S1600536810040535

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2826

https://doi.org/10.1107/S1600536810040535

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4,5-Dimethyl-2-phenyl-1-(p-tolyl)-1H-imidazole

P. Gayathri,^a A. Thiruvalluvar,^a ^* N. Srinivasan,^b J. Jayabharathi ^b and R. J. Butcher ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 10 September 2010; accepted 9 October 2010; online 20 October 2010)

In the title compound, C₁₈H₁₈N₂, the imidazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 68.91 (8) and 20.43 (9)° with the tolyl and phenyl rings, respectively. The dihedral angle between the latter rings is 73.62 (8)°. The crystal packing is stabilized by intermolecular C—H⋯N hydrogen bonds.

Related literature

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a ,b ,c ,d ).

Experimental

Crystal data

C₁₈H₁₈N₂
M_r = 262.34
Monoclinic, P 2₁ /n
a = 9.6971 (3) Å
b = 7.5458 (2) Å
c = 19.8407 (7) Å
β = 96.604 (3)°
V = 1442.16 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.55 mm⁻¹
T = 123 K
0.49 × 0.43 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.606, T_max = 1.000
5113 measured reflections
2849 independent reflections
2529 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.138
S = 1.11
2849 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N3ⁱ	0.95	2.51	3.324 (2)	144
C16—H16⋯N3ⁱⁱ	0.95	2.54	3.465 (2)	164
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810040535/rk2234sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040535/rk2234Isup2.hkl

checkCIF report

Comment top

As part of our research (Gayathri et al., (2010a, b, c & d)), we have synthesized the title compound, I and report its crystal structure here.

In I (Fig. 1), C₁₈H₁₈N₂, the imidazole ring is essentially planar with maximum deviation = 0.004 (1)Å for N3. The imidazole ring makes dihedral angles of 68.91 (8)° and 20.43 (9)° with the benzene (C11-C16) and phenyl (C21-C26) rings respectively. The dihedral angle between the benzene and phenyl rings is 73.62 (8)°. The crystal packing is stabilized by C12–H12···N3ⁱ and C16–H16···N3ⁱⁱ intermolecular non-classical hydrogen bonds (Table 1, Fig. 2). Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -z.

Related literature top

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a,b,c,d).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), p-toluidine (1.6 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and benzaldehyde (1.5 g, 15 mmol) was added about 1 h by maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane: ethyl acetate as the eluent. Yield: 1.93 g (46%).

Structure description top

As part of our research (Gayathri et al., (2010a, b, c & d)), we have synthesized the title compound, I and report its crystal structure here.

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a,b,c,d).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

4,5-Dimethyl-2-phenyl-1-(p-tolyl)-1H-imidazole top

Crystal data top

C₁₈H₁₈N₂	F(000) = 560
M_r = 262.34	D_x = 1.208 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 388 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 9.6971 (3) Å	Cell parameters from 3666 reflections
b = 7.5458 (2) Å	θ = 4.6–74.1°
c = 19.8407 (7) Å	µ = 0.55 mm⁻¹
β = 96.604 (3)°	T = 123 K
V = 1442.16 (8) Å³	Block, colourless
Z = 4	0.49 × 0.43 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2849 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2529 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.2°, θ_min = 6.3°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −8→9
T_min = 0.606, T_max = 1.000	l = −24→23
5113 measured 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0624P)² + 0.7809P] where P = (F_o² + 2F_c²)/3
2849 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₈N₂	V = 1442.16 (8) Å³
M_r = 262.34	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.6971 (3) Å	µ = 0.55 mm⁻¹
b = 7.5458 (2) Å	T = 123 K
c = 19.8407 (7) Å	0.49 × 0.43 × 0.22 mm
β = 96.604 (3)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2849 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2529 reflections with I > 2σ(I)
T_min = 0.606, T_max = 1.000	R_int = 0.024
5113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.11	Δρ_max = 0.28 e Å⁻³
2849 reflections	Δρ_min = −0.19 e Å⁻³
184 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) 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
N1	0.96551 (13)	0.70974 (17)	0.05414 (6)	0.0239 (4)
N3	1.08249 (13)	0.78862 (17)	−0.03075 (7)	0.0248 (4)
C2	0.95773 (16)	0.7589 (2)	−0.01276 (7)	0.0229 (4)
C4	1.17482 (16)	0.7599 (2)	0.02618 (8)	0.0260 (5)
C5	1.10567 (16)	0.7104 (2)	0.07911 (8)	0.0266 (5)
C11	0.85639 (16)	0.6994 (2)	0.09746 (7)	0.0235 (4)
C12	0.83053 (17)	0.5406 (2)	0.12883 (8)	0.0272 (5)
C13	0.73060 (17)	0.5358 (2)	0.17385 (8)	0.0281 (5)
C14	0.65519 (16)	0.6861 (2)	0.18734 (8)	0.0276 (5)
C15	0.68211 (17)	0.8429 (2)	0.15400 (8)	0.0302 (5)
C16	0.78331 (16)	0.8514 (2)	0.10983 (8)	0.0272 (5)
C17	0.54875 (18)	0.6791 (3)	0.23712 (9)	0.0367 (6)
C21	0.83051 (16)	0.7676 (2)	−0.06104 (8)	0.0241 (4)
C22	0.70724 (17)	0.6803 (2)	−0.05163 (8)	0.0289 (5)
C23	0.59439 (18)	0.6860 (3)	−0.10129 (9)	0.0337 (5)
C24	0.60157 (19)	0.7807 (3)	−0.16077 (9)	0.0348 (5)
C25	0.72376 (19)	0.8686 (2)	−0.17049 (8)	0.0334 (5)
C26	0.83700 (17)	0.8621 (2)	−0.12112 (8)	0.0281 (5)
C41	1.32767 (17)	0.7884 (3)	0.02550 (9)	0.0341 (5)
C51	1.15590 (18)	0.6676 (3)	0.15102 (8)	0.0338 (5)
H12	0.88031	0.43652	0.11971	0.0327*
H13	0.71349	0.42749	0.19587	0.0338*
H15	0.63014	0.94623	0.16166	0.0362*
H16	0.80206	0.95996	0.08843	0.0326*
H17A	0.48146	0.58494	0.22381	0.0550*
H17B	0.50045	0.79313	0.23719	0.0550*
H17C	0.59525	0.65460	0.28267	0.0550*
H22	0.70063	0.61651	−0.01086	0.0346*
H23	0.51153	0.62463	−0.09456	0.0404*
H24	0.52377	0.78531	−0.19451	0.0417*
H25	0.72962	0.93342	−0.21111	0.0401*
H26	0.92003	0.92255	−0.12823	0.0338*
H41A	1.34705	0.91576	0.02429	0.0512*
H41B	1.35792	0.73153	−0.01470	0.0512*
H41C	1.37795	0.73656	0.06647	0.0512*
H51A	1.25562	0.69209	0.15961	0.0507*
H51B	1.13901	0.54201	0.15960	0.0507*
H51C	1.10612	0.74057	0.18117	0.0507*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0248 (7)	0.0269 (7)	0.0204 (6)	0.0011 (5)	0.0039 (5)	0.0000 (5)
N3	0.0272 (7)	0.0242 (7)	0.0238 (7)	0.0009 (5)	0.0064 (5)	−0.0016 (5)
C2	0.0278 (8)	0.0214 (7)	0.0200 (7)	0.0008 (6)	0.0056 (6)	−0.0013 (6)
C4	0.0262 (8)	0.0248 (8)	0.0273 (8)	0.0020 (6)	0.0047 (6)	−0.0010 (6)
C5	0.0256 (8)	0.0281 (8)	0.0260 (8)	0.0038 (6)	0.0026 (6)	−0.0012 (6)
C11	0.0230 (7)	0.0294 (8)	0.0185 (7)	−0.0001 (6)	0.0036 (6)	−0.0012 (6)
C12	0.0309 (8)	0.0264 (8)	0.0246 (8)	0.0023 (7)	0.0044 (6)	−0.0004 (6)
C13	0.0312 (8)	0.0297 (9)	0.0238 (8)	−0.0032 (7)	0.0045 (6)	0.0025 (6)
C14	0.0231 (8)	0.0374 (9)	0.0224 (8)	−0.0030 (6)	0.0031 (6)	−0.0030 (7)
C15	0.0294 (8)	0.0312 (9)	0.0307 (8)	0.0054 (7)	0.0063 (7)	−0.0025 (7)
C16	0.0295 (8)	0.0261 (8)	0.0263 (8)	0.0014 (6)	0.0043 (6)	0.0014 (6)
C17	0.0295 (9)	0.0477 (11)	0.0347 (9)	−0.0034 (8)	0.0114 (7)	−0.0030 (8)
C21	0.0280 (8)	0.0248 (8)	0.0199 (7)	0.0018 (6)	0.0041 (6)	−0.0043 (6)
C22	0.0314 (8)	0.0328 (9)	0.0233 (8)	−0.0006 (7)	0.0068 (6)	−0.0024 (7)
C23	0.0278 (8)	0.0420 (10)	0.0315 (9)	−0.0018 (7)	0.0045 (7)	−0.0085 (8)
C24	0.0324 (9)	0.0422 (10)	0.0280 (8)	0.0063 (8)	−0.0038 (7)	−0.0077 (7)
C25	0.0417 (10)	0.0367 (10)	0.0216 (8)	0.0039 (8)	0.0026 (7)	0.0000 (7)
C26	0.0321 (8)	0.0296 (8)	0.0234 (8)	−0.0004 (7)	0.0063 (6)	−0.0025 (6)
C41	0.0263 (8)	0.0398 (10)	0.0369 (9)	0.0004 (7)	0.0061 (7)	0.0006 (8)
C51	0.0320 (9)	0.0442 (10)	0.0245 (8)	0.0041 (8)	0.0007 (7)	0.0020 (7)

Geometric parameters (Å, º) top

N1—C2	1.3719 (18)	C24—C25	1.391 (3)
N1—C5	1.392 (2)	C25—C26	1.386 (2)
N1—C11	1.4400 (19)	C12—H12	0.9500
N3—C2	1.319 (2)	C13—H13	0.9500
N3—C4	1.375 (2)	C15—H15	0.9500
C2—C21	1.474 (2)	C16—H16	0.9500
C4—C5	1.362 (2)	C17—H17A	0.9800
C4—C41	1.499 (2)	C17—H17B	0.9800
C5—C51	1.489 (2)	C17—H17C	0.9800
C11—C12	1.386 (2)	C22—H22	0.9500
C11—C16	1.385 (2)	C23—H23	0.9500
C12—C13	1.392 (2)	C24—H24	0.9500
C13—C14	1.392 (2)	C25—H25	0.9500
C14—C15	1.395 (2)	C26—H26	0.9500
C14—C17	1.509 (2)	C41—H41A	0.9800
C15—C16	1.390 (2)	C41—H41B	0.9800
C21—C22	1.396 (2)	C41—H41C	0.9800
C21—C26	1.397 (2)	C51—H51A	0.9800
C22—C23	1.386 (2)	C51—H51B	0.9800
C23—C24	1.388 (3)	C51—H51C	0.9800

N3···C12ⁱ	3.324 (2)	C21···H41Aⁱⁱ	3.0800
N1···H22	2.8300	C23···H41B^vi	3.0400
N3···H26	2.5600	C24···H17A^v	3.1000
N3···H12ⁱ	2.5100	C24···H15^vii	3.0500
N3···H16ⁱⁱ	2.5400	C41···H22ⁱ	3.0800
C4···C22ⁱ	3.530 (2)	C41···H51A	2.9200
C4···C26ⁱⁱ	3.427 (2)	C51···H41C	2.9200
C5···C22ⁱ	3.537 (2)	C51···H25^iv	2.8500
C5···C26ⁱⁱ	3.362 (2)	H12···N3ⁱ	2.5100
C11···C22	3.143 (2)	H15···H17B	2.3700
C12···N3ⁱ	3.324 (2)	H15···C24^vii	3.0500
C12···C51	3.278 (2)	H16···C2	3.0500
C16···C21	3.530 (2)	H16···N3ⁱⁱ	2.5400
C16···C22	3.454 (2)	H17A···H51A^vi	2.5400
C21···C16	3.530 (2)	H17A···C24^v	3.1000
C22···C41ⁱ	3.596 (3)	H17B···H15	2.3700
C22···C4ⁱ	3.530 (2)	H22···N1	2.8300
C22···C11	3.143 (2)	H22···C11	2.5600
C22···C16	3.454 (2)	H22···C12	2.9700
C22···C5ⁱ	3.537 (2)	H22···C16	3.0100
C25···C51ⁱⁱⁱ	3.537 (2)	H22···C41ⁱ	3.0800
C26···C4ⁱⁱ	3.427 (2)	H23···H41B^vi	2.4300
C26···C5ⁱⁱ	3.362 (2)	H23···C13^v	2.9300
C26···C51ⁱⁱ	3.600 (3)	H25···C51ⁱⁱⁱ	2.8500
C41···C22ⁱ	3.596 (3)	H26···N3	2.5600
C51···C12	3.278 (2)	H26···C5ⁱⁱ	2.9600
C51···C25^iv	3.537 (2)	H41A···C21ⁱⁱ	3.0800
C51···C26ⁱⁱ	3.600 (3)	H41B···C23^viii	3.0400
C2···H16	3.0500	H41B···H23^viii	2.4300
C5···H26ⁱⁱ	2.9600	H41C···C51	2.9200
C11···H22	2.5600	H41C···H51A	2.3300
C11···H51C	2.7900	H51A···C17^viii	3.0700
C12···H51B	2.9800	H51A···C41	2.9200
C12···H22	2.9700	H51A···H17A^viii	2.5400
C13···H23^v	2.9300	H51A···H41C	2.3300
C16···H22	3.0100	H51B···C12	2.9800
C17···H51A^vi	3.0700	H51B···C21ⁱ	3.0800
C21···H51Bⁱ	3.0800	H51C···C11	2.7900

C2—N1—C5	106.63 (12)	C14—C13—H13	119.00
C2—N1—C11	129.03 (13)	C14—C15—H15	119.00
C5—N1—C11	122.83 (12)	C16—C15—H15	119.00
C2—N3—C4	106.36 (13)	C11—C16—H16	120.00
N1—C2—N3	110.95 (13)	C15—C16—H16	120.00
N1—C2—C21	126.14 (14)	C14—C17—H17A	109.00
N3—C2—C21	122.80 (13)	C14—C17—H17B	109.00
N3—C4—C5	110.17 (14)	C14—C17—H17C	109.00
N3—C4—C41	121.39 (14)	H17A—C17—H17B	109.00
C5—C4—C41	128.41 (15)	H17A—C17—H17C	109.00
N1—C5—C4	105.89 (13)	H17B—C17—H17C	109.00
N1—C5—C51	122.59 (14)	C21—C22—H22	120.00
C4—C5—C51	131.50 (15)	C23—C22—H22	120.00
N1—C11—C12	119.87 (14)	C22—C23—H23	120.00
N1—C11—C16	119.14 (13)	C24—C23—H23	120.00
C12—C11—C16	120.90 (14)	C23—C24—H24	120.00
C11—C12—C13	119.07 (14)	C25—C24—H24	120.00
C12—C13—C14	121.47 (14)	C24—C25—H25	120.00
C13—C14—C15	117.96 (14)	C26—C25—H25	120.00
C13—C14—C17	120.75 (15)	C21—C26—H26	120.00
C15—C14—C17	121.29 (15)	C25—C26—H26	120.00
C14—C15—C16	121.48 (14)	C4—C41—H41A	109.00
C11—C16—C15	119.09 (14)	C4—C41—H41B	109.00
C2—C21—C22	123.89 (14)	C4—C41—H41C	109.00
C2—C21—C26	117.45 (14)	H41A—C41—H41B	109.00
C22—C21—C26	118.58 (14)	H41A—C41—H41C	109.00
C21—C22—C23	120.55 (15)	H41B—C41—H41C	109.00
C22—C23—C24	120.50 (17)	C5—C51—H51A	109.00
C23—C24—C25	119.36 (16)	C5—C51—H51B	109.00
C24—C25—C26	120.24 (15)	C5—C51—H51C	109.00
C21—C26—C25	120.77 (15)	H51A—C51—H51B	109.00
C11—C12—H12	120.00	H51A—C51—H51C	109.00
C13—C12—H12	120.00	H51B—C51—H51C	109.00
C12—C13—H13	119.00

C5—N1—C2—N3	0.36 (17)	N3—C4—C5—C51	−178.79 (17)
C5—N1—C2—C21	176.54 (14)	C41—C4—C5—N1	177.62 (16)
C11—N1—C2—N3	166.40 (14)	C41—C4—C5—C51	−0.7 (3)
C11—N1—C2—C21	−17.4 (2)	N1—C11—C12—C13	176.00 (14)
C2—N1—C5—C4	0.06 (16)	C16—C11—C12—C13	−0.7 (2)
C2—N1—C5—C51	178.60 (16)	N1—C11—C16—C15	−177.22 (14)
C11—N1—C5—C4	−167.05 (13)	C12—C11—C16—C15	−0.5 (2)
C11—N1—C5—C51	11.5 (2)	C11—C12—C13—C14	0.8 (2)
C2—N1—C11—C12	122.48 (17)	C12—C13—C14—C15	0.3 (2)
C2—N1—C11—C16	−60.8 (2)	C12—C13—C14—C17	−179.07 (15)
C5—N1—C11—C12	−73.49 (19)	C13—C14—C15—C16	−1.6 (2)
C5—N1—C11—C16	103.27 (17)	C17—C14—C15—C16	177.82 (15)
C4—N3—C2—N1	−0.62 (17)	C14—C15—C16—C11	1.7 (2)
C4—N3—C2—C21	−176.95 (14)	C2—C21—C22—C23	−176.04 (16)
C2—N3—C4—C5	0.66 (17)	C26—C21—C22—C23	0.7 (2)
C2—N3—C4—C41	−177.56 (15)	C2—C21—C26—C25	176.69 (14)
N1—C2—C21—C22	−19.2 (2)	C22—C21—C26—C25	−0.3 (2)
N1—C2—C21—C26	164.06 (15)	C21—C22—C23—C24	−0.9 (3)
N3—C2—C21—C22	156.57 (15)	C22—C23—C24—C25	0.7 (3)
N3—C2—C21—C26	−20.2 (2)	C23—C24—C25—C26	−0.2 (3)
N3—C4—C5—N1	−0.43 (17)	C24—C25—C26—C21	0.0 (2)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) x−1/2, −y+3/2, z−1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+1, −y+1, −z; (vi) x−1, y, z; (vii) −x+1, −y+2, −z; (viii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N3ⁱ	0.95	2.51	3.324 (2)	144
C16—H16···N3ⁱⁱ	0.95	2.54	3.465 (2)	164

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂
M_r	262.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	9.6971 (3), 7.5458 (2), 19.8407 (7)
β (°)	96.604 (3)
V (Å³)	1442.16 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.49 × 0.43 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.606, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5113, 2849, 2529
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.138, 1.11
No. of reflections	2849
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N3ⁱ	0.95	2.51	3.324 (2)	144
C16—H16···N3ⁱⁱ	0.95	2.54	3.465 (2)	164

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

Acknowledgements

JJ is thankful tothe Department of Science and Technology [No. SR/S1/IC-07/2007], University Grants commission (F. No. 36-21/2008 (SR)) for providing funding for this research work. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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