1-[2-(2,4-Dichloro­benz­yloxy)-2-phenyl­ethyl]-1H-1,2,4-triazole

Özel Güven, Ö.; Tahtacı, H.; Tahir, M.N.; Hökelek, T.

doi:10.1107/S1600536808039196

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2465

doi:10.1107/S1600536808039196

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1-[2-(2,4-Dichlorobenzyloxy)-2-phenylethyl]-1H-1,2,4-triazole

Özden Özel Güven,^a Hakan Tahtacı,^a M. Nawaz Tahir ^b and Tuncer Hökelek ^c ^*

^aZonguldak Karaelmas University, Department of Chemistry, 67100 Zonguldak, Turkey, ^bSargodha University, Department of Physics, Sargodha, Pakistan, and ^cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 16 November 2008; accepted 21 November 2008; online 29 November 2008)

In the molecule of the title compound, C₁₇H₁₅Cl₂N₃O, the triazole ring is oriented at dihedral angles of 9.24 (6) and 82.49 (6)°, respectively, with respect to the phenyl and dichlorobenzene rings. The dihedral angle between the dichlorobenzene and phenyl rings is 88.57 (5)°. An intramolecular C—H⋯O contact results in the formation of a planar five-membered ring.

Related literature

For general backgroud, see: Paulvannan et al. (2001 ); Godefroi et al. (1969 ); Özel Güven et al. (2007a ,b ); Wahbi et al. (1995 ). For related structures, see: Peeters et al. (1979 ); Freer et al. (1986 ); Özel Güven et al. (2008a ,b ,c ,d ,e ,f ).

Experimental

Crystal data

C₁₇H₁₅Cl₂N₃O
M_r = 348.22
Monoclinic, P 2₁ /n
a = 10.5630 (3) Å
b = 13.7933 (5) Å
c = 11.4437 (4) Å
β = 101.840 (2)°
V = 1631.86 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 296 (2) K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.871, T_max = 0.942
17794 measured reflections
4055 independent reflections
3135 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.04
4055 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.37	2.7191 (18)	102
Symmetry code: (i) -x, -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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039196/su2082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039196/su2082Isup2.hkl

checkCIF report

Comment top

1,2,4-Triazoles are biologically interesting molecules and their chemistry is receiving considerable attention due to their antihypertensive, antifungal and antibacterial properties (Paulvannan et al., 2001). Some ether structures containing the 1H-imidazole ring, like miconazole, econazole and sulconazole, have been synthesized and developed for clinical use as antifungal agents (Godefroi et al., 1969). Also, antifungal activity of aromatic ethers possessing a 1H-1,2,4-triazole ring have been reported (Wahbi et al., 1995). However, similar ether structures possessing a 1H-benzimidazole ring have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). The crystal structures of these ether derivatives, such as miconazole (Peeters et al., 1979) and econazole (Freer et al., 1986), have been reported. The crystal structures of 1H-benzimidazole ring containing ether derivatives (Özel Güven et al., 2008a,b,c,d) and also, 1H-1,2,4-triazole ring containing ether derivative have been reported recently (Özel Güven et al., 2008e). Here we report on the crystal structure of the 2,4-dichloro derivative of a 1H-1,2,4-triazole ring compound containing an ether structure.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. The planar triazole ring is oriented with respect to the phenyl and dichlorobenzene rings at dihedral angles of 9.24 (6)° and 82.49 (6)°, respectively. The dichlorobenzene ring is oriented with respect to the phenyl ring at a dihedral angle of 88.57 (5)°. The intramolecular C—H···O contact results in the formation of a planar five-membered ring (O1/H13/C11—C13), which is oriented with respect to dichlorobenzene ring at a dihedral angle of 0.65 (4)°, hence they are coplanar.

In the crystal structure of the title compound, the molecules stack along the c direction (Fig. 2). There is a weak intermolecular C—H···π contact between the methylene group and the dichlorobenzene ring [Table 1; where Cg3 is the centroid of the ring (C12-C17)].

Related literature top

For general backgroud, see: Paulvannan et al. (2001); Godefroi et al. (1969); Özel Güven et al. (2007a,b); Wahbi et al. (1995). For related structures, see: Peeters et al. (1979); Freer et al. (1986); Özel Güven et al. (2008a,b,c,d,e,f).

Experimental top

The title compound was synthesized by the reaction of 1-phenyl-2-(1H-1,2,4 -triazol-1-yl)ethanol (Özel Güven et al., 2008f) with NaH and the appropriate benzyl halide. To the solution of the alcohol (300 mg, 1.586 mmol) in DMF (4 ml) was added NaH (63 mg, 1.586 mmol) in small fractions. The appropriate benzyl halide (310 mg, 1.586 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, and excess hydride was decomposed with methyl alcohol (5 ml). After evaporation to dryness under reduced pressure, the crude residue was suspended with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude residue was purified by chromatography on a silica-gel column using chloroform as eluent. Crystals of the title compound, suitable for X-ray analysis, were obtained by recrystallization of the ether from 2-propanol (yield; 365 mg, 66%).

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compiund, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular C-H···O contact is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen atoms have been omitted for clarity.

1-[2-(2,4-Dichlorobenzyloxy)-2-phenylethyl]-1H-1,2,4-triazole top

Crystal data top

C₁₇H₁₅Cl₂N₃O	F(000) = 720
M_r = 348.22	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1196 reflections
a = 10.5630 (3) Å	θ = 2.3–28.3°
b = 13.7933 (5) Å	µ = 0.41 mm⁻¹
c = 11.4437 (4) Å	T = 296 K
β = 101.840 (2)°	Rod-shaped, colorless
V = 1631.86 (10) Å³	0.35 × 0.25 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4055 independent reflections
Radiation source: fine-focus sealed tube	3135 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
T_min = 0.871, T_max = 0.942	l = −15→14
17794 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0424P)² + 0.5043P] where P = (F_o² + 2F_c²)/3
4055 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₅Cl₂N₃O	V = 1631.86 (10) Å³
M_r = 348.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5630 (3) Å	µ = 0.41 mm⁻¹
b = 13.7933 (5) Å	T = 296 K
c = 11.4437 (4) Å	0.35 × 0.25 × 0.15 mm
β = 101.840 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4055 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3135 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.942	R_int = 0.026
17794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
4055 reflections	Δρ_min = −0.24 e Å⁻³
208 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.

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 > σ(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
Cl1	0.52852 (6)	0.29276 (4)	−0.26180 (4)	0.07651 (18)
Cl2	0.34215 (4)	0.12684 (4)	0.09114 (5)	0.06649 (16)
O1	0.74240 (10)	0.02400 (8)	0.22002 (9)	0.0471 (3)
N1	0.93446 (12)	−0.11684 (10)	0.21096 (11)	0.0455 (3)
N2	0.90960 (15)	−0.21005 (11)	0.17678 (14)	0.0566 (4)
N3	0.99426 (14)	−0.12858 (12)	0.04041 (13)	0.0576 (4)
C1	0.94814 (17)	−0.21219 (14)	0.07456 (16)	0.0558 (4)
H1	0.9437	−0.2683	0.0288	0.067*
C2	0.98325 (16)	−0.07037 (14)	0.12863 (15)	0.0541 (4)
H2	1.0065	−0.0052	0.1329	0.065*
C3	0.90367 (16)	−0.08020 (14)	0.32066 (13)	0.0508 (4)
H3A	0.9575	−0.0242	0.3472	0.061*
H3B	0.9237	−0.1296	0.3820	0.061*
C4	0.76226 (14)	−0.05147 (12)	0.30597 (12)	0.0420 (3)
H4	0.7075	−0.1069	0.2751	0.050*
C5	0.73484 (14)	−0.02155 (11)	0.42542 (12)	0.0399 (3)
C6	0.77537 (18)	0.06624 (13)	0.47606 (15)	0.0557 (4)
H6	0.8178	0.1096	0.4351	0.067*
C7	0.7537 (2)	0.09083 (14)	0.58750 (16)	0.0615 (5)
H7	0.7809	0.1507	0.6207	0.074*
C8	0.6926 (2)	0.02748 (16)	0.64868 (17)	0.0668 (5)
H8	0.6784	0.0440	0.7237	0.080*
C9	0.6523 (2)	−0.06017 (17)	0.59975 (18)	0.0803 (7)
H9	0.6113	−0.1037	0.6418	0.096*
C10	0.6723 (2)	−0.08442 (14)	0.48764 (16)	0.0612 (5)
H10	0.6431	−0.1438	0.4541	0.073*
C11	0.61158 (14)	0.05336 (12)	0.18708 (13)	0.0423 (3)
H11A	0.5879	0.0904	0.2514	0.051*
H11B	0.5560	−0.0032	0.1725	0.051*
C12	0.59372 (13)	0.11430 (10)	0.07624 (12)	0.0384 (3)
C13	0.69449 (15)	0.13512 (12)	0.01952 (13)	0.0462 (4)
H13	0.7767	0.1113	0.0512	0.055*
C14	0.67532 (17)	0.19065 (13)	−0.08330 (14)	0.0516 (4)
H14	0.7441	0.2042	−0.1201	0.062*
C15	0.55413 (17)	0.22549 (12)	−0.13037 (13)	0.0493 (4)
C16	0.45097 (16)	0.20677 (11)	−0.07723 (14)	0.0472 (4)
H16	0.3689	0.2305	−0.1097	0.057*
C17	0.47304 (14)	0.15158 (11)	0.02584 (13)	0.0414 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0977 (4)	0.0735 (3)	0.0540 (3)	0.0099 (3)	0.0054 (2)	0.0273 (2)
Cl2	0.0427 (2)	0.0853 (4)	0.0740 (3)	0.0131 (2)	0.0178 (2)	0.0169 (2)
O1	0.0397 (5)	0.0633 (7)	0.0391 (5)	0.0109 (5)	0.0102 (4)	0.0171 (5)
N1	0.0429 (7)	0.0529 (8)	0.0419 (7)	0.0123 (6)	0.0114 (5)	0.0047 (6)
N2	0.0617 (9)	0.0497 (8)	0.0615 (9)	0.0087 (7)	0.0194 (7)	0.0056 (7)
N3	0.0511 (8)	0.0718 (10)	0.0559 (8)	0.0001 (7)	0.0246 (7)	−0.0063 (7)
C1	0.0504 (9)	0.0594 (11)	0.0600 (10)	0.0083 (8)	0.0170 (8)	−0.0083 (8)
C2	0.0532 (9)	0.0570 (10)	0.0563 (10)	−0.0027 (8)	0.0214 (8)	−0.0003 (8)
C3	0.0498 (9)	0.0656 (11)	0.0367 (7)	0.0176 (8)	0.0081 (6)	0.0062 (7)
C4	0.0447 (8)	0.0478 (8)	0.0340 (7)	0.0067 (6)	0.0093 (6)	0.0057 (6)
C5	0.0413 (7)	0.0441 (8)	0.0342 (7)	0.0067 (6)	0.0074 (6)	0.0038 (6)
C6	0.0672 (11)	0.0508 (10)	0.0492 (9)	−0.0085 (8)	0.0125 (8)	0.0027 (7)
C7	0.0751 (12)	0.0524 (10)	0.0533 (10)	0.0016 (9)	0.0043 (9)	−0.0124 (8)
C8	0.0790 (13)	0.0802 (14)	0.0453 (9)	0.0048 (11)	0.0223 (9)	−0.0111 (9)
C9	0.1129 (18)	0.0828 (15)	0.0574 (11)	−0.0245 (13)	0.0460 (12)	−0.0075 (11)
C10	0.0840 (13)	0.0552 (10)	0.0509 (9)	−0.0154 (9)	0.0291 (9)	−0.0069 (8)
C11	0.0389 (7)	0.0511 (9)	0.0378 (7)	0.0090 (6)	0.0103 (6)	0.0060 (6)
C12	0.0407 (7)	0.0402 (8)	0.0334 (6)	0.0047 (6)	0.0055 (5)	−0.0018 (6)
C13	0.0413 (8)	0.0567 (9)	0.0402 (8)	0.0082 (7)	0.0073 (6)	0.0060 (7)
C14	0.0535 (9)	0.0578 (10)	0.0448 (8)	0.0019 (7)	0.0128 (7)	0.0085 (7)
C15	0.0646 (10)	0.0430 (9)	0.0373 (7)	0.0048 (7)	0.0033 (7)	0.0056 (6)
C16	0.0493 (9)	0.0432 (8)	0.0442 (8)	0.0108 (7)	−0.0014 (7)	−0.0013 (6)
C17	0.0405 (7)	0.0412 (8)	0.0418 (7)	0.0050 (6)	0.0064 (6)	−0.0037 (6)

Geometric parameters (Å, º) top

Cl1—C15	1.7404 (16)	C6—H6	0.9300
Cl2—C17	1.7351 (16)	C7—H7	0.9300
O1—C4	1.4178 (17)	C8—C7	1.362 (3)
O1—C11	1.4148 (17)	C8—C9	1.363 (3)
N1—N2	1.354 (2)	C8—H8	0.9300
N1—C2	1.328 (2)	C9—C10	1.383 (2)
N1—C3	1.4508 (19)	C9—H9	0.9300
N3—C1	1.341 (2)	C10—H10	0.9300
N3—C2	1.314 (2)	C11—H11A	0.9700
C1—N2	1.315 (2)	C11—H11B	0.9700
C1—H1	0.9300	C12—C11	1.5010 (19)
C2—H2	0.9300	C12—C13	1.386 (2)
C3—H3A	0.9700	C12—C17	1.386 (2)
C3—H3B	0.9700	C13—C14	1.384 (2)
C4—C3	1.521 (2)	C13—H13	0.9300
C4—H4	0.9800	C14—H14	0.9300
C5—C4	1.5117 (19)	C15—C14	1.370 (2)
C5—C6	1.373 (2)	C15—C16	1.377 (2)
C5—C10	1.375 (2)	C16—H16	0.9300
C6—C7	1.383 (2)	C17—C16	1.383 (2)

C11—O1—C4	113.10 (11)	C7—C8—C9	119.91 (17)
N2—N1—C3	121.08 (14)	C7—C8—H8	120.0
C2—N1—N2	109.51 (14)	C9—C8—H8	120.0
C2—N1—C3	129.37 (15)	C8—C9—C10	120.08 (19)
C1—N2—N1	101.60 (14)	C8—C9—H9	120.0
C2—N3—C1	101.94 (14)	C10—C9—H9	120.0
N2—C1—N3	115.92 (16)	C5—C10—C9	120.59 (18)
N2—C1—H1	122.0	C5—C10—H10	119.7
N3—C1—H1	122.0	C9—C10—H10	119.7
N1—C2—H2	124.5	O1—C11—C12	109.39 (11)
N3—C2—N1	111.02 (16)	O1—C11—H11A	109.8
N3—C2—H2	124.5	O1—C11—H11B	109.8
N1—C3—C4	112.62 (13)	C12—C11—H11A	109.8
N1—C3—H3A	109.1	C12—C11—H11B	109.8
N1—C3—H3B	109.1	H11A—C11—H11B	108.2
C4—C3—H3A	109.1	C13—C12—C11	122.44 (13)
C4—C3—H3B	109.1	C17—C12—C11	120.33 (13)
H3A—C3—H3B	107.8	C17—C12—C13	117.22 (13)
O1—C4—C3	105.67 (12)	C12—C13—H13	119.3
O1—C4—C5	113.48 (12)	C14—C13—C12	121.37 (14)
O1—C4—H4	109.3	C14—C13—H13	119.3
C3—C4—H4	109.3	C13—C14—H14	120.3
C5—C4—C3	109.70 (12)	C15—C14—C13	119.37 (15)
C5—C4—H4	109.3	C15—C14—H14	120.3
C6—C5—C4	121.44 (14)	C14—C15—Cl1	119.59 (14)
C6—C5—C10	118.65 (15)	C14—C15—C16	121.40 (14)
C10—C5—C4	119.86 (14)	C15—C16—C17	118.01 (14)
C5—C6—C7	120.62 (17)	C15—C16—H16	121.0
C5—C6—H6	119.7	C16—C15—Cl1	119.00 (13)
C7—C6—H6	119.7	C17—C16—H16	121.0
C6—C7—H7	119.9	C12—C17—Cl2	119.60 (12)
C8—C7—C6	120.13 (17)	C16—C17—Cl2	117.76 (12)
C8—C7—H7	119.9	C16—C17—C12	122.62 (14)

C11—O1—C4—C5	−65.39 (16)	C6—C5—C10—C9	−0.9 (3)
C11—O1—C4—C3	174.37 (13)	C5—C6—C7—C8	0.5 (3)
C4—O1—C11—C12	−166.09 (12)	C9—C8—C7—C6	−0.2 (3)
C2—N1—N2—C1	0.78 (17)	C7—C8—C9—C10	−0.6 (4)
C3—N1—N2—C1	178.59 (14)	C8—C9—C10—C5	1.2 (4)
N2—N1—C2—N3	−0.86 (19)	C13—C12—C11—O1	0.3 (2)
C3—N1—C2—N3	−178.43 (14)	C17—C12—C11—O1	179.72 (13)
N2—N1—C3—C4	−81.93 (18)	C11—C12—C13—C14	179.31 (15)
C2—N1—C3—C4	95.4 (2)	C17—C12—C13—C14	−0.1 (2)
C1—N3—C2—N1	0.51 (19)	C11—C12—C17—Cl2	−0.4 (2)
C2—N3—C1—N2	0.0 (2)	C11—C12—C17—C16	−178.91 (14)
N3—C1—N2—N1	−0.5 (2)	C13—C12—C17—Cl2	179.09 (12)
O1—C4—C3—N1	−61.74 (18)	C13—C12—C17—C16	0.5 (2)
C5—C4—C3—N1	175.58 (14)	C12—C13—C14—C15	−0.3 (3)
C6—C5—C4—O1	−42.85 (19)	Cl1—C15—C14—C13	−178.35 (13)
C6—C5—C4—C3	75.08 (19)	C16—C15—C14—C13	0.3 (3)
C10—C5—C4—O1	139.60 (16)	Cl1—C15—C16—C17	178.75 (12)
C10—C5—C4—C3	−102.47 (18)	C14—C15—C16—C17	0.1 (2)
C4—C5—C6—C7	−177.53 (16)	Cl2—C17—C16—C15	−179.10 (12)
C10—C5—C6—C7	0.0 (3)	C12—C17—C16—C15	−0.5 (2)
C4—C5—C10—C9	176.68 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.37	2.7191 (18)	102

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅Cl₂N₃O
M_r	348.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.5630 (3), 13.7933 (5), 11.4437 (4)
β (°)	101.840 (2)
V (Å³)	1631.86 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.871, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	17794, 4055, 3135
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.04
No. of reflections	4055
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.37	2.7191 (18)	102.00

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (Project No. 2008–13–02–06) for financial support.

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