1-(3,5-Dimethyl­phenyl)-2-(4-fluoro­phenyl)-4,5-dimethyl-1H-imidazole

Rosepriya, S.; Thiruvalluvar, A.; Jayabharathi, J.; Srinivasan, N.; Butcher, R.J.; Jasinski, J.P.; Golen, J.A.

doi:10.1107/S1600536811012098

organic compounds

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Volume 67| Part 5| May 2011| Page o1065

doi:10.1107/S1600536811012098

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1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole

S. Rosepriya,^a A. Thiruvalluvar,^a ^* J. Jayabharathi,^b N. Srinivasan,^b R. J. Butcher,^c J. P. Jasinski ^d and J. A. Golen ^d

^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, ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 26 March 2011; accepted 31 March 2011; online 7 April 2011)

In the title compound, C₁₉H₁₉FN₂, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å] and makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to nitrogen and carbon, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C—H⋯π interaction is found in the crystal structure.

Related literature

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010 ); Rosepriya et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₉FN₂
M_r = 294.36
Triclinic, $[P \overline 1]$
a = 8.4226 (10) Å
b = 9.5572 (10) Å
c = 11.0351 (11) Å
α = 105.423 (9)°
β = 105.677 (9)°
γ = 95.781 (9)°
V = 810.07 (17) Å³
Z = 2
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 170 K
0.25 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.858, T_max = 0.911
5121 measured reflections
3054 independent reflections
2771 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.159
S = 1.07
3054 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg3ⁱ	0.95	2.86	3.7969 (19)	169
Symmetry code: (i) -x, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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/S1600536811012098/hg5018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012098/hg5018Isup2.hkl

checkCIF report

Comment top

Rosepriya et al. (2011) have reported the crystal structure of 1,2-Diphenyl-1H-imidazo[4,5-f][1,10]phenanthroline. As part of our research (Gayathri et al., (2010)), we have synthesized the title compound (I) and report its crystal structure here. Since our group doing the research in organic light emitting devices, we are interested to use the title compound as ligand for synthesizing Ir(III) complexes.

In the title compound (Fig. 1), C₁₉H₁₉FN₂, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å for C4]. The imidazole ring makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to N1 and C2, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C12—H12···π interaction involving (C21—C26) ring is found in the crystal structure (Table 1).

Related literature top

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010); Rosepriya et al. (2011).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), 3,5-xylidine (1.8 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 4-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: 2.1 g (48%). Crystals suitable for X-ray diffraction studies were grown by slow solvent evaporation of a solution of the compound in dichloromethane.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (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.

1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole top

Crystal data top

C₁₉H₁₉FN₂	Z = 2
M_r = 294.36	F(000) = 312
Triclinic, P1	D_x = 1.207 Mg m⁻³
Hall symbol: -P 1	Melting point: 377 K
a = 8.4226 (10) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.5572 (10) Å	Cell parameters from 3721 reflections
c = 11.0351 (11) Å	θ = 5.6–71.2°
α = 105.423 (9)°	µ = 0.63 mm⁻¹
β = 105.677 (9)°	T = 170 K
γ = 95.781 (9)°	Block, colourless
V = 810.07 (17) Å³	0.25 × 0.20 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3054 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2771 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Detector resolution: 16.1500 pixels mm^-1	θ_max = 71.3°, θ_min = 5.6°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −11→11
T_min = 0.858, T_max = 0.911	l = −13→10
5121 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0944P)² + 0.144P] where P = (F_o² + 2F_c²)/3
3054 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₉FN₂	γ = 95.781 (9)°
M_r = 294.36	V = 810.07 (17) Å³
Triclinic, P1	Z = 2
a = 8.4226 (10) Å	Cu Kα radiation
b = 9.5572 (10) Å	µ = 0.63 mm⁻¹
c = 11.0351 (11) Å	T = 170 K
α = 105.423 (9)°	0.25 × 0.20 × 0.15 mm
β = 105.677 (9)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3054 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2771 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.911	R_int = 0.011
5121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
3054 reflections	Δρ_min = −0.23 e Å⁻³
203 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	0.29950 (19)	0.53513 (14)	0.86850 (14)	0.0964 (5)
N1	0.19985 (15)	−0.06005 (14)	0.37504 (12)	0.0449 (4)
N3	0.32289 (16)	−0.11576 (15)	0.55605 (13)	0.0520 (4)
C2	0.27033 (18)	−0.00885 (17)	0.50979 (14)	0.0453 (4)
C4	0.2859 (2)	−0.23874 (19)	0.44868 (16)	0.0532 (5)
C5	0.20944 (19)	−0.20827 (17)	0.33550 (15)	0.0488 (5)
C11	0.14226 (18)	0.02522 (16)	0.28741 (14)	0.0435 (4)
C12	−0.02859 (18)	0.01651 (18)	0.23336 (15)	0.0480 (5)
C13	−0.08585 (19)	0.10368 (18)	0.15377 (15)	0.0494 (5)
C14	0.0323 (2)	0.19566 (17)	0.12941 (14)	0.0515 (5)
C15	0.2035 (2)	0.20141 (16)	0.17950 (15)	0.0487 (5)
C16	0.25852 (18)	0.11506 (16)	0.26059 (14)	0.0464 (4)
C17	−0.2713 (2)	0.0990 (2)	0.0987 (2)	0.0692 (7)
C18	0.3276 (3)	0.2979 (2)	0.1464 (2)	0.0698 (7)
C21	0.28022 (18)	0.14031 (17)	0.59540 (15)	0.0472 (5)
C22	0.1660 (2)	0.2313 (2)	0.56533 (17)	0.0566 (5)
C23	0.1740 (3)	0.3655 (2)	0.6562 (2)	0.0654 (6)
C24	0.2952 (3)	0.4060 (2)	0.77740 (19)	0.0660 (6)
C25	0.4109 (2)	0.3201 (2)	0.81121 (19)	0.0655 (6)
C26	0.4030 (2)	0.1881 (2)	0.71957 (16)	0.0558 (5)
C41	0.3314 (3)	−0.3824 (2)	0.4636 (2)	0.0787 (8)
C51	0.1442 (2)	−0.3012 (2)	0.19482 (17)	0.0623 (6)
H12	−0.10645	−0.04873	0.25055	0.0575*
H14	−0.00553	0.25686	0.07653	0.0618*
H16	0.37514	0.11800	0.29712	0.0556*
H17A	−0.29302	0.13147	0.01961	0.1037*
H17B	−0.30948	0.16460	0.16526	0.1037*
H17C	−0.33197	−0.00229	0.07526	0.1037*
H18A	0.34608	0.24283	0.06431	0.1046*
H18B	0.43413	0.32742	0.21839	0.1046*
H18C	0.28339	0.38610	0.13490	0.1046*
H22	0.08176	0.20091	0.48163	0.0679*
H23	0.09729	0.42825	0.63510	0.0784*
H25	0.49398	0.35114	0.89552	0.0785*
H26	0.48261	0.12777	0.74092	0.0670*
H41A	0.45009	−0.38100	0.47068	0.1181*
H41B	0.26202	−0.46386	0.38633	0.1181*
H41C	0.31177	−0.39629	0.54360	0.1181*
H51A	0.14887	−0.40467	0.18925	0.0934*
H51B	0.21302	−0.26845	0.14515	0.0934*
H51C	0.02775	−0.29169	0.15728	0.0934*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F4	0.1034 (10)	0.0696 (8)	0.0947 (9)	0.0084 (7)	0.0297 (8)	−0.0060 (7)
N1	0.0417 (6)	0.0541 (7)	0.0451 (7)	0.0131 (5)	0.0125 (5)	0.0248 (5)
N3	0.0508 (7)	0.0622 (8)	0.0497 (7)	0.0169 (6)	0.0121 (6)	0.0291 (6)
C2	0.0399 (7)	0.0568 (9)	0.0451 (7)	0.0108 (6)	0.0128 (6)	0.0250 (6)
C4	0.0533 (9)	0.0573 (9)	0.0561 (9)	0.0180 (7)	0.0150 (7)	0.0279 (7)
C5	0.0466 (8)	0.0547 (9)	0.0516 (8)	0.0152 (6)	0.0156 (6)	0.0243 (7)
C11	0.0430 (7)	0.0527 (8)	0.0410 (7)	0.0148 (6)	0.0131 (6)	0.0222 (6)
C12	0.0418 (8)	0.0586 (9)	0.0494 (8)	0.0121 (6)	0.0143 (6)	0.0250 (7)
C13	0.0469 (8)	0.0581 (9)	0.0445 (8)	0.0182 (7)	0.0102 (6)	0.0187 (7)
C14	0.0634 (10)	0.0533 (9)	0.0448 (8)	0.0218 (7)	0.0150 (7)	0.0243 (7)
C15	0.0567 (9)	0.0479 (8)	0.0496 (8)	0.0139 (6)	0.0223 (7)	0.0206 (6)
C16	0.0418 (7)	0.0533 (8)	0.0490 (8)	0.0134 (6)	0.0155 (6)	0.0207 (6)
C17	0.0519 (10)	0.0793 (12)	0.0756 (12)	0.0238 (9)	0.0056 (8)	0.0327 (10)
C18	0.0764 (12)	0.0665 (11)	0.0864 (13)	0.0152 (9)	0.0385 (11)	0.0419 (10)
C21	0.0437 (7)	0.0569 (9)	0.0481 (8)	0.0075 (6)	0.0178 (6)	0.0248 (7)
C22	0.0565 (9)	0.0630 (10)	0.0535 (9)	0.0151 (7)	0.0163 (7)	0.0224 (8)
C23	0.0670 (11)	0.0609 (10)	0.0762 (12)	0.0192 (8)	0.0287 (9)	0.0248 (9)
C24	0.0680 (11)	0.0561 (10)	0.0684 (11)	−0.0007 (8)	0.0275 (9)	0.0082 (8)
C25	0.0548 (10)	0.0716 (11)	0.0589 (10)	−0.0022 (8)	0.0124 (8)	0.0123 (8)
C26	0.0460 (8)	0.0654 (10)	0.0559 (9)	0.0054 (7)	0.0132 (7)	0.0227 (8)
C41	0.1018 (16)	0.0660 (12)	0.0736 (12)	0.0332 (11)	0.0157 (11)	0.0351 (10)
C51	0.0685 (11)	0.0640 (10)	0.0532 (9)	0.0186 (8)	0.0135 (8)	0.0192 (8)

Geometric parameters (Å, º) top

F4—C24	1.359 (2)	C24—C25	1.375 (3)
N1—C2	1.3713 (19)	C25—C26	1.374 (3)
N1—C5	1.385 (2)	C12—H12	0.9500
N1—C11	1.442 (2)	C14—H14	0.9500
N3—C2	1.322 (2)	C16—H16	0.9500
N3—C4	1.367 (2)	C17—H17A	0.9800
C2—C21	1.466 (2)	C17—H17B	0.9800
C4—C5	1.362 (2)	C17—H17C	0.9800
C4—C41	1.500 (3)	C18—H18A	0.9800
C5—C51	1.486 (2)	C18—H18B	0.9800
C11—C12	1.385 (2)	C18—H18C	0.9800
C11—C16	1.381 (2)	C22—H22	0.9500
C12—C13	1.393 (2)	C23—H23	0.9500
C13—C14	1.389 (2)	C25—H25	0.9500
C13—C17	1.507 (2)	C26—H26	0.9500
C14—C15	1.387 (2)	C41—H41A	0.9800
C15—C16	1.394 (2)	C41—H41B	0.9800
C15—C18	1.506 (3)	C41—H41C	0.9800
C21—C22	1.393 (2)	C51—H51A	0.9800
C21—C26	1.401 (2)	C51—H51B	0.9800
C22—C23	1.385 (3)	C51—H51C	0.9800
C23—C24	1.374 (3)

C2—N1—C5	107.12 (13)	C13—C14—H14	119.00
C2—N1—C11	127.30 (14)	C15—C14—H14	119.00
C5—N1—C11	125.28 (12)	C11—C16—H16	120.00
C2—N3—C4	106.09 (13)	C15—C16—H16	120.00
N1—C2—N3	110.65 (14)	C13—C17—H17A	109.00
N1—C2—C21	126.33 (14)	C13—C17—H17B	109.00
N3—C2—C21	122.95 (13)	C13—C17—H17C	109.00
N3—C4—C5	110.80 (16)	H17A—C17—H17B	110.00
N3—C4—C41	121.02 (15)	H17A—C17—H17C	109.00
C5—C4—C41	128.18 (16)	H17B—C17—H17C	110.00
N1—C5—C4	105.35 (14)	C15—C18—H18A	109.00
N1—C5—C51	122.36 (14)	C15—C18—H18B	109.00
C4—C5—C51	132.29 (16)	C15—C18—H18C	109.00
N1—C11—C12	119.20 (14)	H18A—C18—H18B	109.00
N1—C11—C16	119.31 (14)	H18A—C18—H18C	109.00
C12—C11—C16	121.49 (15)	H18B—C18—H18C	110.00
C11—C12—C13	119.80 (15)	C21—C22—H22	120.00
C12—C13—C14	118.19 (15)	C23—C22—H22	120.00
C12—C13—C17	120.13 (16)	C22—C23—H23	121.00
C14—C13—C17	121.67 (16)	C24—C23—H23	121.00
C13—C14—C15	122.39 (15)	C24—C25—H25	121.00
C14—C15—C16	118.59 (15)	C26—C25—H25	121.00
C14—C15—C18	120.88 (16)	C21—C26—H26	119.00
C16—C15—C18	120.54 (16)	C25—C26—H26	119.00
C11—C16—C15	119.50 (15)	C4—C41—H41A	109.00
C2—C21—C22	123.84 (14)	C4—C41—H41B	109.00
C2—C21—C26	117.57 (15)	C4—C41—H41C	109.00
C22—C21—C26	118.34 (16)	H41A—C41—H41B	109.00
C21—C22—C23	120.67 (17)	H41A—C41—H41C	109.00
C22—C23—C24	118.6 (2)	H41B—C41—H41C	109.00
F4—C24—C23	118.8 (2)	C5—C51—H51A	109.00
F4—C24—C25	118.53 (18)	C5—C51—H51B	109.00
C23—C24—C25	122.71 (19)	C5—C51—H51C	109.00
C24—C25—C26	118.09 (17)	H51A—C51—H51B	109.00
C21—C26—C25	121.54 (17)	H51A—C51—H51C	109.00
C11—C12—H12	120.00	H51B—C51—H51C	109.00
C13—C12—H12	120.00

C5—N1—C2—N3	0.02 (19)	C41—C4—C5—C51	1.4 (3)
C5—N1—C2—C21	−176.74 (15)	N1—C11—C12—C13	176.87 (14)
C11—N1—C2—N3	−173.88 (14)	C16—C11—C12—C13	−2.3 (2)
C11—N1—C2—C21	9.4 (3)	N1—C11—C16—C15	−177.86 (14)
C2—N1—C5—C4	−0.20 (18)	C12—C11—C16—C15	1.3 (2)
C2—N1—C5—C51	179.77 (15)	C11—C12—C13—C14	1.1 (2)
C11—N1—C5—C4	173.87 (15)	C11—C12—C13—C17	−177.75 (15)
C11—N1—C5—C51	−6.2 (2)	C12—C13—C14—C15	1.1 (2)
C2—N1—C11—C12	−105.84 (19)	C17—C13—C14—C15	179.93 (15)
C2—N1—C11—C16	73.4 (2)	C13—C14—C15—C16	−2.1 (2)
C5—N1—C11—C12	81.3 (2)	C13—C14—C15—C18	177.47 (16)
C5—N1—C11—C16	−99.51 (18)	C14—C15—C16—C11	0.9 (2)
C4—N3—C2—N1	0.16 (18)	C18—C15—C16—C11	−178.71 (15)
C4—N3—C2—C21	177.05 (15)	C2—C21—C22—C23	174.03 (18)
C2—N3—C4—C5	−0.3 (2)	C26—C21—C22—C23	0.0 (3)
C2—N3—C4—C41	178.74 (17)	C2—C21—C26—C25	−173.55 (16)
N1—C2—C21—C22	27.5 (3)	C22—C21—C26—C25	0.9 (3)
N1—C2—C21—C26	−158.45 (16)	C21—C22—C23—C24	−1.0 (3)
N3—C2—C21—C22	−148.95 (17)	C22—C23—C24—F4	−177.64 (19)
N3—C2—C21—C26	25.2 (2)	C22—C23—C24—C25	1.3 (3)
N3—C4—C5—N1	0.30 (19)	F4—C24—C25—C26	178.47 (18)
N3—C4—C5—C51	−179.66 (17)	C23—C24—C25—C26	−0.5 (3)
C41—C4—C5—N1	−178.63 (19)	C24—C25—C26—C21	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C21–C26 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg3ⁱ	0.95	2.86	3.7969 (19)	169

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉FN₂
M_r	294.36
Crystal system, space group	Triclinic, P1
Temperature (K)	170
a, b, c (Å)	8.4226 (10), 9.5572 (10), 11.0351 (11)
α, β, γ (°)	105.423 (9), 105.677 (9), 95.781 (9)
V (Å³)	810.07 (17)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.858, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	5121, 3054, 2771
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.159, 1.07
No. of reflections	3054
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C21–C26 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg3ⁱ	0.95	2.86	3.7969 (19)	169

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2776. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Venkatesh Perumal, M., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o989. Web of Science CSD CrossRef IUCr Journals 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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Volume 67| Part 5| May 2011| Page o1065

doi:10.1107/S1600536811012098

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