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

Özel Güven, Ö.; Tahtacı, H.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536808027748

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1914-o1915

doi:10.1107/S1600536808027748

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

Özden Özel Güven,^a Hakan Tahtacı,^a Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aZonguldak Karaelmas University, Department of Chemistry, 67100, Zonguldak, Turkey, ^bSouthampton University, Department of Chemistry, Southampton, SO17 1BJ, England, and ^cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 22 August 2008; accepted 29 August 2008; online 13 September 2008)

In the molecule of the title compound, C₁₇H₁₆BrN₃O, the triazole ring is oriented at dihedral angles of 6.14 (9)° and 82.08 (9)°, respectively, with respect to the phenyl and bromobenzene rings. The dihedral angle between the bromobenzene and phenyl rings is 87.28 (7)°. The intramolecular C—H⋯O hydrogen bond results in the formation of a planar five-membered ring, which is oriented at a dihedral angle of 0.13 (6)° with respect to the bromobenzene ring. There is an intermolecular C—H⋯π contact between a methylene group and the bromobenzene 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 literature, see: Peeters et al. (1979 ); Freer et al. (1986 ); Özel Güven et al. (2008a ,b ,c ,d ); Özel Güven, Tahtacı et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₆BrN₃O
M_r = 358.24
Monoclinic, P 2₁ /n
a = 10.2070 (2) Å
b = 13.7948 (3) Å
c = 11.4007 (2) Å
β = 100.317 (1)°
V = 1579.31 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.61 mm⁻¹
T = 120 (2) K
0.38 × 0.30 × 0.20 mm

Data collection

Bruker–Nonius Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.400, T_max = 0.590
18914 measured reflections
3617 independent reflections
2901 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.082
S = 1.05
3617 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O	0.93	2.37	2.723 (3)	102
C11—H11A⋯Cg3ⁱ	0.97	2.84	3.687 (2)	147
Symmetry code: (i) -x+1, -y, -z. Cg3 is the centroid of the C12–C17 ring.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; 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 publication routines (Farrugia, 1999 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027748/xu2450sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027748/xu2450Isup2.hkl

checkCIF report

Comment top

In recent years, among antifungal agents, azole derivatives still have an important place in the class of systemic antifungal drugs. 1,2,4-Triazoles are biologically interesting molecules and their chemistry is receiving considerable attention due to antihypertensive, antifungal and antibacterial properties (Paulvannan et al., 2001). Similar structures possessing imidazole ring such as miconazole, econazole and sulconazole have been developed for clinical uses as antifungal agents (Godefroi et al., 1969) and also similar structures possessing benzimidazole ring have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). Antifungal activity of aromatic ethers possessing 1,2,4-triazole ring have been reported (Wahbi et al., 1995). The crystal structures of miconazole (Peeters et al., 1979), econazole (Freer et al., 1986) and similar structures possessing benzimidazole ring (Özel Güven et al., 2008a,b,c,d) have been reported, previously, and now we report herein the crystal structure of the title 1,2,4-triazole ring substituted 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 bromobenzene rings at dihedral angles of 6.14 (9)° and 82.08 (9)°, respectively. Atoms C3, C4 and C11 are 0.114 (2), -0.076 (2) and 0.015 (2) Å away from the ring planes of the corresponding triazole, phenyl and bromobenzene, respectively. So, they are nearly coplanar with the adjacent rings. The bromobenzene ring is oriented with respect to the phenyl ring at a dihedral angle of 87.28 (7)°. The intramolecular C—H···O hydrogen bond results in the formation of a planar five-membered ring (O/H13/C11—C13), which is oriented with respect to bromobenzene ring at a dihedral angle of 0.13 (6)°. So, they are coplanar.

In the crystal structure, the molecules are elongated along [010], and stacked along the c axis. There is a C—H···π contact (Table 1) between the methylene group and the bromobenzene ring.

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 literature, see: Peeters et al. (1979); Freer et al. (1986); Özel Güven et al. (2008a,b,c,d); Özel Güven, Tahtacı et al. (2008). Cg3 is the centroid of the C12–C17 ring.

Experimental top

The title compound was synthesized by the reaction of 1-phenyl-2-(1H-1,2,4 -triazol-1-yl)ethanol (Özel Güven, Tahtacı et al., 2008) with NaH and appropriate benzyl halide. To the solution of 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 (396 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 suitable for X-ray analysis were obtained by the recrystallization of the ether from ethyl acetate (yield; 368 mg, 65%).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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 publication routines (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data top

C₁₇H₁₆BrN₃O	F(000) = 728
M_r = 358.24	D_x = 1.507 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3224 reflections
a = 10.2070 (2) Å	θ = 2.9–27.5°
b = 13.7948 (3) Å	µ = 2.61 mm⁻¹
c = 11.4007 (2) Å	T = 120 K
β = 100.317 (1)°	Block, colorless
V = 1579.31 (5) Å³	0.38 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker–Nonius Kappa CCD diffractometer	3617 independent reflections
Radiation source: fine-focus sealed tube	2901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ϕ & ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→17
T_min = 0.400, T_max = 0.590	l = −14→14
18914 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) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0282P)² + 1.0904P] where P = (F_o² + 2F_c²)/3
3617 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₇H₁₆BrN₃O	V = 1579.31 (5) Å³
M_r = 358.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2070 (2) Å	µ = 2.61 mm⁻¹
b = 13.7948 (3) Å	T = 120 K
c = 11.4007 (2) Å	0.38 × 0.30 × 0.20 mm
β = 100.317 (1)°

Data collection top

Bruker–Nonius Kappa CCD diffractometer	3617 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2901 reflections with I > 2σ(I)
T_min = 0.400, T_max = 0.590	R_int = 0.051
18914 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
3617 reflections	Δρ_min = −0.53 e Å⁻³
199 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
Br	0.01308 (3)	0.204749 (18)	0.24099 (2)	0.03377 (10)
O	0.23831 (15)	0.48903 (11)	0.72395 (13)	0.0219 (3)
N1	0.43625 (18)	0.62535 (13)	0.70844 (15)	0.0209 (4)
N2	0.4116 (2)	0.71851 (14)	0.67091 (18)	0.0262 (4)
N3	0.4832 (2)	0.62873 (15)	0.52812 (17)	0.0264 (4)
C1	0.4421 (2)	0.71587 (17)	0.5630 (2)	0.0260 (5)
H1	0.4357	0.7703	0.5141	0.031*
C2	0.4777 (2)	0.57391 (17)	0.62277 (19)	0.0250 (5)
H2	0.4998	0.5085	0.6287	0.030*
C3	0.4052 (2)	0.59254 (17)	0.82170 (18)	0.0230 (5)
H3A	0.4249	0.6441	0.8800	0.028*
H3B	0.4615	0.5377	0.8500	0.028*
C4	0.2599 (2)	0.56308 (16)	0.81142 (18)	0.0209 (5)
H4	0.2028	0.6187	0.7839	0.025*
C5	0.2348 (2)	0.53134 (16)	0.93291 (18)	0.0203 (5)
C6	0.2718 (2)	0.43995 (17)	0.9773 (2)	0.0264 (5)
H6	0.3090	0.3959	0.9308	0.032*
C7	0.2536 (2)	0.41385 (19)	1.0911 (2)	0.0292 (5)
H7	0.2780	0.3523	1.1202	0.035*
C8	0.1994 (3)	0.47886 (19)	1.1609 (2)	0.0306 (6)
H8	0.1876	0.4614	1.2371	0.037*
C9	0.1627 (3)	0.57037 (19)	1.1170 (2)	0.0323 (6)
H9	0.1269	0.6147	1.1640	0.039*
C10	0.1791 (2)	0.59612 (18)	1.0031 (2)	0.0263 (5)
H10	0.1527	0.6572	0.9734	0.032*
C11	0.1027 (2)	0.45894 (17)	0.69514 (19)	0.0220 (5)
H11A	0.0452	0.5153	0.6806	0.026*
H11B	0.0788	0.4230	0.7613	0.026*
C12	0.0843 (2)	0.39583 (16)	0.58547 (18)	0.0199 (5)
C13	0.1877 (2)	0.37627 (17)	0.52494 (19)	0.0224 (5)
H13	0.2718	0.4021	0.5525	0.027*
C14	0.1669 (2)	0.31831 (17)	0.42329 (19)	0.0240 (5)
H14	0.2367	0.3050	0.3833	0.029*
C15	0.0416 (2)	0.28084 (16)	0.38240 (19)	0.0242 (5)
C16	−0.0634 (2)	0.30004 (17)	0.4409 (2)	0.0247 (5)
H16	−0.1475	0.2748	0.4125	0.030*
C17	−0.0413 (2)	0.35727 (17)	0.54222 (19)	0.0225 (5)
H17	−0.1114	0.3702	0.5820	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04619 (18)	0.02724 (15)	0.02419 (14)	−0.00004 (12)	−0.00363 (11)	−0.00854 (10)
O	0.0210 (8)	0.0264 (8)	0.0189 (7)	−0.0031 (7)	0.0056 (6)	−0.0072 (6)
N1	0.0236 (10)	0.0210 (10)	0.0190 (9)	−0.0032 (8)	0.0061 (8)	0.0008 (8)
N2	0.0307 (11)	0.0202 (10)	0.0295 (10)	−0.0027 (8)	0.0105 (9)	0.0003 (8)
N3	0.0287 (11)	0.0280 (11)	0.0247 (10)	0.0014 (9)	0.0107 (8)	0.0027 (8)
C1	0.0263 (12)	0.0263 (13)	0.0274 (12)	0.0006 (10)	0.0102 (10)	0.0078 (10)
C2	0.0322 (13)	0.0219 (12)	0.0222 (11)	0.0022 (10)	0.0082 (10)	0.0008 (9)
C3	0.0273 (12)	0.0274 (12)	0.0143 (10)	−0.0054 (10)	0.0040 (9)	−0.0010 (9)
C4	0.0250 (12)	0.0220 (11)	0.0165 (10)	−0.0026 (9)	0.0059 (9)	−0.0032 (9)
C5	0.0196 (11)	0.0245 (12)	0.0166 (10)	−0.0050 (9)	0.0026 (9)	−0.0037 (9)
C6	0.0304 (13)	0.0241 (12)	0.0247 (11)	0.0010 (10)	0.0047 (10)	−0.0028 (10)
C7	0.0306 (13)	0.0290 (13)	0.0261 (12)	−0.0018 (11)	0.0002 (10)	0.0080 (10)
C8	0.0322 (14)	0.0404 (15)	0.0207 (11)	−0.0049 (12)	0.0084 (10)	0.0043 (11)
C9	0.0379 (15)	0.0354 (14)	0.0270 (12)	0.0019 (12)	0.0150 (11)	−0.0017 (11)
C10	0.0315 (13)	0.0244 (12)	0.0247 (11)	−0.0008 (10)	0.0097 (10)	0.0010 (10)
C11	0.0217 (11)	0.0250 (12)	0.0197 (11)	−0.0049 (9)	0.0047 (9)	−0.0017 (9)
C12	0.0251 (12)	0.0189 (11)	0.0156 (10)	0.0004 (9)	0.0033 (9)	0.0027 (8)
C13	0.0232 (12)	0.0238 (12)	0.0196 (10)	−0.0020 (9)	0.0018 (9)	−0.0013 (9)
C14	0.0276 (12)	0.0247 (12)	0.0201 (11)	0.0017 (10)	0.0053 (10)	0.0003 (9)
C15	0.0345 (13)	0.0185 (11)	0.0176 (10)	−0.0005 (10)	−0.0009 (10)	0.0012 (9)
C16	0.0244 (12)	0.0233 (12)	0.0236 (11)	−0.0056 (10)	−0.0034 (9)	0.0044 (10)
C17	0.0217 (12)	0.0233 (12)	0.0229 (11)	0.0000 (9)	0.0048 (9)	0.0042 (9)

Geometric parameters (Å, º) top

Br—C15	1.902 (2)	C1—H1	0.9300
O—C4	1.417 (3)	C2—H2	0.9300
O—C11	1.426 (3)	C3—C4	1.523 (3)
N1—C2	1.336 (3)	C3—H3A	0.9700
N1—N2	1.363 (3)	C3—H3B	0.9700
N1—C3	1.456 (3)	C4—C5	1.517 (3)
N2—C1	1.323 (3)	C4—H4	0.9800
N3—C2	1.327 (3)	C5—C10	1.387 (3)
C12—C13	1.387 (3)	C6—C5	1.386 (3)
C12—C11	1.507 (3)	C6—C7	1.390 (3)
C13—C14	1.393 (3)	C6—H6	0.9300
C13—H13	0.9300	C7—H7	0.9300
C14—H14	0.9300	C8—C7	1.379 (4)
C15—C14	1.381 (3)	C8—C9	1.385 (4)
C15—C16	1.385 (3)	C8—H8	0.9300
C16—C17	1.384 (3)	C9—H9	0.9300
C16—H16	0.9300	C10—C9	1.385 (3)
C17—C12	1.394 (3)	C10—H10	0.9300
C17—H17	0.9300	C11—H11A	0.9700
C1—N3	1.356 (3)	C11—H11B	0.9700

C4—O—C11	113.20 (16)	C7—C8—C9	119.6 (2)
C2—N1—N2	109.63 (18)	C7—C8—H8	120.2
C2—N1—C3	129.13 (19)	C9—C8—H8	120.2
N2—N1—C3	120.95 (18)	C8—C9—C10	120.2 (2)
C1—N2—N1	101.85 (19)	C8—C9—H9	119.9
C2—N3—C1	101.93 (19)	C10—C9—H9	119.9
N2—C1—N3	115.7 (2)	C9—C10—C5	120.4 (2)
N2—C1—H1	122.2	C9—C10—H10	119.8
N3—C1—H1	122.2	C5—C10—H10	119.8
N3—C2—N1	110.9 (2)	O—C11—C12	109.32 (18)
N3—C2—H2	124.5	O—C11—H11A	109.8
N1—C2—H2	124.5	C12—C11—H11A	109.8
N1—C3—C4	112.24 (18)	O—C11—H11B	109.8
N1—C3—H3A	109.2	C12—C11—H11B	109.8
C4—C3—H3A	109.2	H11A—C11—H11B	108.3
N1—C3—H3B	109.2	C13—C12—C17	118.9 (2)
C4—C3—H3B	109.2	C13—C12—C11	122.1 (2)
H3A—C3—H3B	107.9	C17—C12—C11	118.9 (2)
O—C4—C5	113.84 (18)	C12—C13—C14	120.6 (2)
O—C4—C3	105.84 (17)	C12—C13—H13	119.7
C5—C4—C3	109.14 (18)	C14—C13—H13	119.7
O—C4—H4	109.3	C15—C14—C13	119.3 (2)
C5—C4—H4	109.3	C15—C14—H14	120.3
C3—C4—H4	109.3	C13—C14—H14	120.3
C6—C5—C10	119.3 (2)	C14—C15—C16	121.0 (2)
C6—C5—C4	121.1 (2)	C14—C15—Br	118.98 (18)
C10—C5—C4	119.6 (2)	C16—C15—Br	119.97 (18)
C5—C6—C7	120.2 (2)	C17—C16—C15	119.1 (2)
C5—C6—H6	119.9	C17—C16—H16	120.4
C7—C6—H6	119.9	C15—C16—H16	120.4
C8—C7—C6	120.3 (2)	C16—C17—C12	121.0 (2)
C8—C7—H7	119.8	C16—C17—H17	119.5
C6—C7—H7	119.8	C12—C17—H17	119.5

C11—O—C4—C5	65.5 (2)	C4—C5—C10—C9	−176.2 (2)
C11—O—C4—C3	−174.60 (17)	C7—C6—C5—C10	−0.2 (3)
C4—O—C11—C12	168.62 (17)	C7—C6—C5—C4	177.1 (2)
C2—N1—N2—C1	−0.5 (2)	C5—C6—C7—C8	−0.5 (4)
C3—N1—N2—C1	−174.8 (2)	C9—C8—C7—C6	0.3 (4)
N2—N1—C2—N3	0.4 (3)	C7—C8—C9—C10	0.6 (4)
C3—N1—C2—N3	174.1 (2)	C5—C10—C9—C8	−1.3 (4)
N2—N1—C3—C4	83.5 (2)	C13—C12—C11—O	−1.9 (3)
C2—N1—C3—C4	−89.6 (3)	C17—C12—C11—O	179.24 (19)
N1—N2—C1—N3	0.4 (3)	C11—C12—C13—C14	−179.4 (2)
C1—N3—C2—N1	−0.1 (3)	C17—C12—C13—C14	−0.6 (3)
N2—C1—N3—C2	−0.2 (3)	C12—C13—C14—C15	0.5 (3)
N1—C3—C4—O	58.0 (2)	Br—C15—C14—C13	178.28 (17)
N1—C3—C4—C5	−179.15 (18)	C16—C15—C14—C13	0.0 (3)
O—C4—C5—C6	38.9 (3)	Br—C15—C16—C17	−178.62 (17)
O—C4—C5—C10	−143.9 (2)	C14—C15—C16—C17	−0.4 (3)
C3—C4—C5—C6	−79.1 (3)	C15—C16—C17—C12	0.2 (3)
C3—C4—C5—C10	98.1 (2)	C16—C17—C12—C11	179.1 (2)
C6—C5—C10—C9	1.1 (4)	C16—C17—C12—C13	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O	0.93	2.37	2.723 (3)	102
C11—H11A···Cg3ⁱ	0.97	2.84	3.687 (2)	147

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆BrN₃O
M_r	358.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	10.2070 (2), 13.7948 (3), 11.4007 (2)
β (°)	100.317 (1)
V (Å³)	1579.31 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.61
Crystal size (mm)	0.38 × 0.30 × 0.20

Data collection
Diffractometer	Bruker–Nonius Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.400, 0.590
No. of measured, independent and observed [I > 2σ(I)] reflections	18914, 3617, 2901
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.082, 1.05
No. of reflections	3617
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.53

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O	0.93	2.37	2.723 (3)	102.00
C11—H11A···Cg3ⁱ	0.97	2.84	3.687 (2)	146.63

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (grant No. 2004–13-02–16).

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