2-(4-Fluoro­phen­yl)-4,5-dimethyl-1-(4-methyl­phen­yl)-1H-imidazole

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

doi:10.1107/S1600536810022841

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1703

doi:10.1107/S1600536810022841

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2-(4-Fluorophenyl)-4,5-dimethyl-1-(4-methylphenyl)-1H-imidazole

P. Gayathri,^a J. Jayabharathi,^b N. Srinivasan,^b A. Thiruvalluvar ^a ^* 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: athiru@vsnl.net

(Received 10 June 2010; accepted 14 June 2010; online 18 June 2010)

In the title molecule, C₁₈H₁₇FN₂, the imidazole ring is essentially planar [maximum deviation of 0.005 (1) Å and makes dihedral angles of 72.33 (8) and 18.71 (8)° with the methylphenyl and fluorophenyl rings, respectively. The dihedral angle between the two benzene rings is 75.05 (7)°. The crystal packing is stabilized by intermolecular C—H⋯N hydrogen bonds.

Related literature

For the optical properties of heterocyclic imidazole derivatives, see: Santos et al. (2001 ); Huang et al. (2004 ); Chen & Shi (1998 ). For our general experimental procedure for the preparation of imidazoles, see: Jayabharathi et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₇FN₂
M_r = 280.34
Monoclinic, P 2₁ /n
a = 9.8888 (2) Å
b = 7.6693 (1) Å
c = 20.1017 (3) Å
β = 95.915 (1)°
V = 1516.40 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 295 K
0.49 × 0.35 × 0.17 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 = 0.748, T_max = 1.000
7060 measured reflections
3181 independent reflections
2617 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.153
S = 1.05
3181 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N3ⁱ	0.93	2.55	3.3714 (19)	148
C16—H16⋯N3ⁱⁱ	0.93	2.60	3.5154 (19)	167
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: SHELXS97 (Sheldrick, 2008 ); 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: 10.1107/S1600536810022841/si2269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022841/si2269Isup2.hkl

checkCIF report

Comment top

Imidazole derivatives have been used to construct highly sensitive fluorescent chemisensors for sensing and imaging of metal ions and its chelates in particular those with Ir³⁺ are major components for organic light emitting diodes and are promising candidates for fluorescent chemisensors for metal ions (Santos et al., (2001); Huang et al., (2004) and Chen & Shi (1998)). In this paper we report the crystal and molecular structure of the title compound, a fluorescent chemisensor synthesized in our laboratory.

In the title molecule (Scheme I, Fig. 1), C₁₈H₁₇FN₂, the imidazole ring is essentially planar. The imidazole ring makes dihedral angles of 72.33 (8)° and 18.71 (8)° with the methylphenyl (C11–C16) and fluorophenyl (C21–C26) rings respectively. The dihedral angle between the two benzene rings is 75.05 (7)°. The crystal packing is stabilized by C12—H12···N3 (2 - x, 1 - y, -z) and C16—H16···N3 (2 - x, 2 - y, -z) intermolecular hydrogen bonds (Table 1, Fig. 2).

Related literature top

For the optical properties of heterocyclic imidazole derivatives, see: Santos et al. (2001); Huang et al. (2004); Chen & Shi (1998). For general experimental procedure, see: Jayabharathi et al. (2009).

Experimental top

The experimental procedure was used as the same as described in the recent paper (Jayabharathi et al., 2009). The pure biacetyl (1.48 g, 15 mmol) in ethanol (10 ml), p-toluidine (1.6 g, 15 mmol), ammonium acetate (7.0 g, 15 mmol) and p-fluorobenzaldehyde (1.7 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%).

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: SHELXS97 (Sheldrick, 2008); 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 and displacement ellipsoids 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.

2-(4-Fluorophenyl)-4,5-dimethyl-1-(4-methylphenyl)-1H-imidazole top

Crystal data top

C₁₈H₁₇FN₂	F(000) = 592
M_r = 280.34	D_x = 1.228 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 391 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 9.8888 (2) Å	Cell parameters from 4174 reflections
b = 7.6693 (1) Å	θ = 4.5–77.3°
c = 20.1017 (3) Å	µ = 0.65 mm⁻¹
β = 95.915 (1)°	T = 295 K
V = 1516.40 (4) Å³	Irregular-plate, colourless
Z = 4	0.49 × 0.35 × 0.17 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3181 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2617 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.6°, θ_min = 6.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −8→9
T_min = 0.748, T_max = 1.000	l = −25→15
7060 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0967P)² + 0.1202P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3181 reflections	Δρ_max = 0.18 e Å⁻³
194 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0110 (14)

Crystal data top

C₁₈H₁₇FN₂	V = 1516.40 (4) Å³
M_r = 280.34	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.8888 (2) Å	µ = 0.65 mm⁻¹
b = 7.6693 (1) Å	T = 295 K
c = 20.1017 (3) Å	0.49 × 0.35 × 0.17 mm
β = 95.915 (1)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3181 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2617 reflections with I > 2σ(I)
T_min = 0.748, T_max = 1.000	R_int = 0.018
7060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
3181 reflections	Δρ_min = −0.22 e Å⁻³
194 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 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
F4	0.50712 (11)	0.79381 (18)	−0.20135 (5)	0.0878 (4)
N1	0.96763 (12)	0.71295 (15)	0.05522 (5)	0.0523 (3)
N3	1.08318 (12)	0.78452 (16)	−0.02936 (6)	0.0552 (4)
C2	0.96056 (14)	0.75790 (17)	−0.01134 (6)	0.0506 (4)
C4	1.17256 (15)	0.7577 (2)	0.02668 (7)	0.0579 (4)
C5	1.10396 (15)	0.7121 (2)	0.07926 (7)	0.0570 (4)
C11	0.85905 (13)	0.70419 (18)	0.09791 (6)	0.0508 (4)
C12	0.82752 (15)	0.5472 (2)	0.12584 (7)	0.0578 (4)
C13	0.72685 (15)	0.5424 (2)	0.16936 (7)	0.0615 (5)
C14	0.65756 (14)	0.6921 (2)	0.18449 (7)	0.0620 (5)
C15	0.69119 (16)	0.8470 (2)	0.15546 (8)	0.0662 (5)
C16	0.79222 (15)	0.8549 (2)	0.11215 (7)	0.0590 (4)
C17	0.5499 (2)	0.6850 (3)	0.23290 (10)	0.0871 (7)
C21	0.83724 (14)	0.76750 (18)	−0.05822 (6)	0.0520 (4)
C22	0.71458 (16)	0.6883 (2)	−0.04783 (7)	0.0635 (5)
C23	0.60336 (17)	0.6964 (3)	−0.09575 (8)	0.0695 (5)
C24	0.61596 (17)	0.7847 (2)	−0.15407 (8)	0.0656 (5)
C25	0.73553 (18)	0.8635 (2)	−0.16674 (7)	0.0698 (5)
C26	0.84539 (16)	0.8549 (2)	−0.11881 (7)	0.0617 (5)
C41	1.32237 (17)	0.7824 (3)	0.02535 (10)	0.0767 (6)
C51	1.15183 (18)	0.6712 (3)	0.15018 (8)	0.0736 (6)
H12	0.87286	0.44583	0.11577	0.0693*
H13	0.70568	0.43696	0.18863	0.0738*
H15	0.64539	0.94845	0.16502	0.0794*
H16	0.81419	0.96034	0.09314	0.0708*
H17A	0.49677	0.79000	0.22908	0.1306*
H17B	0.49174	0.58636	0.22254	0.1306*
H17C	0.59289	0.67422	0.27775	0.1306*
H22	0.70704	0.62892	−0.00804	0.0762*
H23	0.52178	0.64294	−0.08845	0.0833*
H25	0.74210	0.92157	−0.20690	0.0837*
H26	0.92660	0.90820	−0.12686	0.0740*
H41A	1.36831	0.75508	0.06850	0.1151*
H41B	1.35437	0.70662	−0.00766	0.1151*
H41C	1.34053	0.90136	0.01434	0.1151*
H51A	1.24837	0.68834	0.15761	0.1104*
H51B	1.10736	0.74684	0.17914	0.1104*
H51C	1.13064	0.55211	0.15952	0.1104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F4	0.0716 (6)	0.1229 (10)	0.0657 (6)	0.0028 (6)	−0.0081 (4)	0.0008 (6)
N1	0.0507 (6)	0.0634 (7)	0.0439 (5)	0.0001 (5)	0.0109 (4)	0.0006 (5)
N3	0.0566 (7)	0.0601 (7)	0.0513 (6)	−0.0017 (5)	0.0173 (5)	−0.0018 (5)
C2	0.0560 (7)	0.0543 (7)	0.0435 (6)	−0.0014 (5)	0.0142 (5)	−0.0027 (5)
C4	0.0520 (7)	0.0641 (8)	0.0591 (8)	0.0004 (6)	0.0134 (6)	−0.0024 (6)
C5	0.0529 (7)	0.0664 (8)	0.0525 (7)	0.0029 (6)	0.0089 (6)	−0.0006 (6)
C11	0.0502 (7)	0.0628 (8)	0.0405 (6)	−0.0017 (5)	0.0104 (5)	−0.0018 (5)
C12	0.0636 (8)	0.0619 (8)	0.0494 (7)	0.0013 (6)	0.0138 (6)	0.0003 (6)
C13	0.0631 (8)	0.0723 (9)	0.0507 (7)	−0.0094 (7)	0.0131 (6)	0.0051 (6)
C14	0.0499 (7)	0.0895 (10)	0.0478 (7)	−0.0054 (7)	0.0115 (5)	−0.0045 (7)
C15	0.0618 (8)	0.0740 (9)	0.0652 (8)	0.0081 (7)	0.0184 (7)	−0.0065 (7)
C16	0.0593 (7)	0.0627 (8)	0.0568 (7)	0.0004 (6)	0.0142 (6)	0.0013 (6)
C17	0.0647 (10)	0.1243 (16)	0.0774 (11)	−0.0073 (10)	0.0317 (9)	−0.0054 (11)
C21	0.0568 (7)	0.0584 (7)	0.0423 (6)	−0.0010 (5)	0.0128 (5)	−0.0047 (5)
C22	0.0629 (8)	0.0802 (10)	0.0485 (7)	−0.0113 (7)	0.0113 (6)	0.0024 (6)
C23	0.0582 (8)	0.0922 (11)	0.0589 (8)	−0.0099 (8)	0.0106 (6)	−0.0043 (8)
C24	0.0615 (8)	0.0833 (10)	0.0510 (7)	0.0061 (7)	0.0016 (6)	−0.0076 (7)
C25	0.0779 (10)	0.0850 (11)	0.0463 (7)	−0.0046 (8)	0.0060 (6)	0.0056 (7)
C26	0.0661 (8)	0.0731 (9)	0.0473 (7)	−0.0079 (7)	0.0127 (6)	0.0012 (6)
C41	0.0538 (9)	0.0939 (12)	0.0847 (11)	−0.0009 (8)	0.0182 (8)	0.0034 (9)
C51	0.0647 (9)	0.0993 (12)	0.0561 (8)	0.0042 (9)	0.0029 (7)	0.0074 (8)

Geometric parameters (Å, º) top

F4—C24	1.362 (2)	C23—C24	1.371 (2)
N1—C2	1.3765 (16)	C24—C25	1.375 (2)
N1—C5	1.3845 (19)	C25—C26	1.377 (2)
N1—C11	1.4435 (17)	C12—H12	0.9300
N3—C2	1.3167 (18)	C13—H13	0.9300
N3—C4	1.3738 (19)	C15—H15	0.9300
C2—C21	1.4642 (19)	C16—H16	0.9300
C4—C5	1.359 (2)	C17—H17A	0.9600
C4—C41	1.497 (2)	C17—H17B	0.9600
C5—C51	1.489 (2)	C17—H17C	0.9600
C11—C12	1.378 (2)	C22—H22	0.9300
C11—C16	1.376 (2)	C23—H23	0.9300
C12—C13	1.392 (2)	C25—H25	0.9300
C13—C14	1.387 (2)	C26—H26	0.9300
C14—C15	1.379 (2)	C41—H41A	0.9600
C14—C17	1.516 (2)	C41—H41B	0.9600
C15—C16	1.393 (2)	C41—H41C	0.9600
C21—C22	1.391 (2)	C51—H51A	0.9600
C21—C26	1.3998 (19)	C51—H51B	0.9600
C22—C23	1.387 (2)	C51—H51C	0.9600

F4···H13ⁱ	2.7800	C41···H51A	2.9200
F4···H15ⁱⁱ	2.6300	C51···H41A	2.9000
F4···H51Bⁱⁱⁱ	2.7100	C51···H25^vi	3.0000
N3···C12^iv	3.3714 (19)	H12···N3^iv	2.5500
N1···H22	2.8300	H13···H17B	2.5600
N3···H26	2.5500	H13···F4ⁱ	2.7800
N3···H12^iv	2.5500	H15···H17A	2.3800
N3···H16^v	2.6000	H15···F4ⁱⁱ	2.6300
C4···C26^v	3.515 (2)	H16···C2	3.0900
C5···C26^v	3.439 (2)	H16···N3^v	2.6000
C11···C22	3.1266 (19)	H17A···H15	2.3800
C12···C51	3.333 (2)	H17B···H13	2.5600
C12···N3^iv	3.3714 (19)	H22···N1	2.8300
C16···C22	3.472 (2)	H22···C11	2.5400
C16···C21	3.5624 (19)	H22···C12	2.9000
C21···C16	3.5624 (19)	H22···C16	3.0200
C22···C16	3.472 (2)	H23···H41B^vii	2.4800
C22···C11	3.1266 (19)	H25···C51ⁱⁱⁱ	3.0000
C26···C4^v	3.515 (2)	H26···N3	2.5500
C26···C5^v	3.439 (2)	H26···C5^v	3.0900
C51···C12	3.333 (2)	H41A···C51	2.9000
C2···H16	3.0900	H41A···H51A	2.3100
C5···H26^v	3.0900	H41B···H23^viii	2.4800
C11···H51C	3.0700	H51A···C41	2.9200
C11···H51B	2.8200	H51A···H41A	2.3100
C11···H22	2.5400	H51B···C11	2.8200
C12···H51C	3.0000	H51B···F4^vi	2.7100
C12···H22	2.9000	H51C···C11	3.0700
C16···H22	3.0200	H51C···C12	3.0000

C2—N1—C5	106.89 (11)	C13—C12—H12	120.00
C2—N1—C11	128.55 (11)	C12—C13—H13	119.00
C5—N1—C11	123.33 (10)	C14—C13—H13	119.00
C2—N3—C4	106.51 (12)	C14—C15—H15	119.00
N1—C2—N3	110.50 (12)	C16—C15—H15	119.00
N1—C2—C21	126.42 (12)	C11—C16—H16	120.00
N3—C2—C21	123.00 (11)	C15—C16—H16	121.00
N3—C4—C5	110.22 (13)	C14—C17—H17A	109.00
N3—C4—C41	121.39 (14)	C14—C17—H17B	109.00
C5—C4—C41	128.38 (14)	C14—C17—H17C	109.00
N1—C5—C4	105.87 (12)	H17A—C17—H17B	109.00
N1—C5—C51	122.51 (13)	H17A—C17—H17C	109.00
C4—C5—C51	131.61 (14)	H17B—C17—H17C	109.00
N1—C11—C12	119.76 (12)	C21—C22—H22	119.00
N1—C11—C16	119.15 (12)	C23—C22—H22	119.00
C12—C11—C16	121.04 (13)	C22—C23—H23	121.00
C11—C12—C13	119.07 (14)	C24—C23—H23	121.00
C12—C13—C14	121.17 (14)	C24—C25—H25	121.00
C13—C14—C15	118.31 (13)	C26—C25—H25	121.00
C13—C14—C17	120.45 (15)	C21—C26—H26	119.00
C15—C14—C17	121.24 (15)	C25—C26—H26	119.00
C14—C15—C16	121.45 (14)	C4—C41—H41A	109.00
C11—C16—C15	118.97 (14)	C4—C41—H41B	109.00
C2—C21—C22	124.23 (12)	C4—C41—H41C	109.00
C2—C21—C26	117.73 (13)	H41A—C41—H41B	109.00
C22—C21—C26	117.96 (13)	H41A—C41—H41C	109.00
C21—C22—C23	121.16 (14)	H41B—C41—H41C	109.00
C22—C23—C24	118.74 (16)	C5—C51—H51A	109.00
F4—C24—C23	119.15 (15)	C5—C51—H51B	109.00
F4—C24—C25	118.75 (14)	C5—C51—H51C	109.00
C23—C24—C25	122.10 (15)	H51A—C51—H51B	109.00
C24—C25—C26	118.74 (14)	H51A—C51—H51C	109.00
C21—C26—C25	121.30 (14)	H51B—C51—H51C	109.00
C11—C12—H12	120.00

C5—N1—C2—N3	−0.05 (15)	C41—C4—C5—N1	177.88 (17)
C5—N1—C2—C21	176.96 (13)	C41—C4—C5—C51	−0.7 (3)
C11—N1—C2—N3	167.43 (13)	N1—C11—C12—C13	177.03 (12)
C11—N1—C2—C21	−15.6 (2)	C16—C11—C12—C13	−0.3 (2)
C2—N1—C5—C4	0.51 (16)	N1—C11—C16—C15	−177.49 (13)
C2—N1—C5—C51	179.20 (15)	C12—C11—C16—C15	−0.1 (2)
C11—N1—C5—C4	−167.78 (13)	C11—C12—C13—C14	0.5 (2)
C11—N1—C5—C51	10.9 (2)	C12—C13—C14—C15	−0.2 (2)
C2—N1—C11—C12	117.62 (15)	C12—C13—C14—C17	−178.96 (15)
C2—N1—C11—C16	−64.96 (18)	C13—C14—C15—C16	−0.2 (2)
C5—N1—C11—C12	−76.77 (17)	C17—C14—C15—C16	178.50 (15)
C5—N1—C11—C16	100.65 (16)	C14—C15—C16—C11	0.4 (2)
C4—N3—C2—N1	−0.43 (15)	C2—C21—C22—C23	−177.15 (15)
C4—N3—C2—C21	−177.56 (13)	C26—C21—C22—C23	−0.4 (2)
C2—N3—C4—C5	0.77 (17)	C2—C21—C26—C25	177.29 (13)
C2—N3—C4—C41	−178.00 (15)	C22—C21—C26—C25	0.3 (2)
N1—C2—C21—C22	−18.3 (2)	C21—C22—C23—C24	−0.1 (3)
N1—C2—C21—C26	164.92 (13)	C22—C23—C24—F4	−179.80 (16)
N3—C2—C21—C22	158.32 (14)	C22—C23—C24—C25	0.7 (3)
N3—C2—C21—C26	−18.4 (2)	F4—C24—C25—C26	179.73 (14)
N3—C4—C5—N1	−0.79 (17)	C23—C24—C25—C26	−0.8 (2)
N3—C4—C5—C51	−179.32 (17)	C24—C25—C26—C21	0.3 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+2, −y+1, −z; (v) −x+2, −y+2, −z; (vi) x+1/2, −y+3/2, z+1/2; (vii) x−1, y, 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···N3^iv	0.93	2.55	3.3714 (19)	148
C16—H16···N3^v	0.93	2.60	3.5154 (19)	167

Symmetry codes: (iv) −x+2, −y+1, −z; (v) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FN₂
M_r	280.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.8888 (2), 7.6693 (1), 20.1017 (3)
β (°)	95.915 (1)
V (Å³)	1516.40 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.49 × 0.35 × 0.17

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.748, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7060, 3181, 2617
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.153, 1.05
No. of reflections	3181
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), 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	0.93	2.55	3.3714 (19)	148
C16—H16···N3ⁱⁱ	0.93	2.60	3.5154 (19)	167

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

Acknowledgements

JJ is grateful to the Department of Science and Technology (No. SR/S1/IC-07/2007) and the University Grants Commission [F. No. 36–21/2008 (SR)] for financial support of this work. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Chen, C. H. & Shi, J. (1998). Coord. Chem. Rev. 171, 161–174. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Huang, W. S., Lin, J. T., Chien, C. H., Tao, Y. T., Sun, S. S. & Wen, Y. S. (2004). Chem. Mater. 16, 2480–2488. Web of Science CSD CrossRef CAS Google Scholar
Jayabharathi, J., Thanikachalam, V. & Saravanan, K. (2009). J. Photochem. Photobiol. A, 208, 13–20. Web of Science CrossRef CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Santos, J., Mintz, E. A., Zehnder, O., Bosshard, C., Bu, X. R. & Günter, P. (2001). Tetrahedron Lett. 42, 805–808. Web of Science CrossRef CAS 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