2-(1H-Benzimidazol-1-yl)-1-(2-fur­yl)ethanone O-ethyl­oxime

Özel Güven, Ö.; Erdoğan, T.; Tahir, M.N.; Hökelek, T.

doi:10.1107/S1600536809022892

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1621-o1622

doi:10.1107/S1600536809022892

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2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-ethyloxime

Özden Özel Güven,^a Taner Erdoğan,^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 11 June 2009; accepted 15 June 2009; online 20 June 2009)

In the molecule of the title compound, C₁₅H₁₅N₃O₂, the planar benzimidazole ring system [maximum deviation = 0.023 (2) Å] is oriented at a dihedral angle of 74.21 (5)° with respect to the furan ring. In the crystal structure, intermolecular C—H⋯N interactions link the molecules into centrosymmetric R₂²(18) dimers. In addition, the structure is stabilized by π–π contacts between parallel imidazole rings [centroid–centroid distance = 3.726 (1) Å] and a weak C—H⋯π interaction.

Related literature

For general background to oximes and oxime ethers and their biological activity, see: Baji et al. (1995 ); Bhandari et al. (2009 ); Emami et al. (2002 , 2004 ); Milanese et al. (2007 ); Polak (1982 ); Porretta et al. (1993 ); Ramalingan et al. (2006 ); Rossello et al. (2002 ). For related structures, see: Özel Güven et al. (2007a ,b , 2009a ,b ). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₅N₃O₂
M_r = 269.30
Monoclinic, P 2₁ /c
a = 8.4448 (5) Å
b = 17.6345 (11) Å
c = 10.3147 (6) Å
β = 110.755 (2)°
V = 1436.38 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.40 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.967, T_max = 0.979
16676 measured reflections
3742 independent reflections
2291 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.140
S = 1.03
3742 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2ⁱ	0.93	2.54	3.328 (2)	143
C14—H14A⋯Cg2ⁱⁱ	0.97	2.88	3.768 (2)	153
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .Cg2 is the centroid of the C2–C7 ring.

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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022892/xu2539sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022892/xu2539Isup2.hkl

checkCIF report

Comment top

Oximes and oxime ethers show very important antifungal and antibacterial activities. Oxiconazole is a well established drug for treatment of many mycotic infections, having an oxime group (Polak, 1982). Several compounds containing an oxime or an oxime ether function have been reported to exhibit antimicrobial activity (Porretta et al., 1993; Baji et al., 1995; Rossello et al., 2002; Emami et al., 2002; Emami et al., 2004; Ramalingan et al., 2006; Milanese et al., 2007; Bhandari et al., 2009). In our earlier studies, we reported X-ray structures of benzimidazole substituted oxiconazole derivatives (Özel Güven et al., 2007a; Özel Güven et al., 2009a; Özel Güven et al., 2009b). Now, we report herein the crystal structure of the title alkyl oxime ether.

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The planar benzimidazole ring system [with a maximum deviation of 0.023 (2) Å for atom C5] is oriented with respect to the furan ring at a dihedral angle of 74.21 (5)°. Atoms C8, C9 and N3 are -0.066 (2), 0.001 (1) and 0.055 (1) Å away from the furan ring plane, respectively, while atom C8 is at a distance of 0.006 (2) Å to the benzimidazole ring plane. So, they are coplanar with the adjacent rings. The N1—C1—N2 [114.46 (16)°], N2—C2—C7 [110.10 (15)°], C2—C7—C6 [122.57 (15)°], C3—C4—C5 [121.26 (18)°] and C4—C5—C6 [121.86 (18)°] bond angles are enlarged, while C5—C6—C7 [116.19 (17)°] and C2—C3—C4 [118.29 (17)°] bond angles are narrowed.

In the crystal structure, intermolecular C—H···N interactions (Table 1) link the molecules into centrosymmetric dimers through R₂²(18) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the imidazole rings, Cg1—Cg1ⁱ, [symmetry code: (i) 1 - x, -y, 1 - z, where Cg1 is centroid of the ring (N1/N2/C1/C2/C7)] may further stabilize the structure, with centroid-centroid distance of 3.726 (1) Å. A weak C—H···π interaction (Table 1) is also found.

Related literature top

For general background to oximes and oxime ethers and their biological activity, see: Baji et al. (1995); Bhandari et al. (2009); Emami et al. (2002, 2004); Milanese et al. (2007); Polak (1982); Porretta et al. (1993); Ramalingan et al. (2006); Rossello et al. (2002). For related structures, see: Özel Güven et al. (2007a,b, 2009a,b). For ring-motifs, see: Bernstein et al. (1995). Cg2 is the centroid of the C2–C7 ring.

Experimental top

The title compound was synthesized by the reaction of 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone oxime obtained from 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone (Özel Güven et al., 2007b) with ethyl iodide and NaH. To a solution of 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone oxime (400 mg, 1.658 mmol) in DMF (5 ml) was added NaH (66 mg, 1.658 mmol) in small fractions. Then, ethyl iodide (259 mg, 1.658 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h and the excess of hydride was decomposed with a small amount of methyl alcohol. 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 and recrystallized from hexane-ethyl acetate (1:3) mixture to obtain yellow crystals (yield; 270 mg, 61%).

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) and PLATON (Spek, 2009).

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.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-ethyloxime top

Crystal data top

C₁₅H₁₅N₃O₂	F(000) = 568
M_r = 269.30	D_x = 1.245 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1232 reflections
a = 8.4448 (5) Å	θ = 2.3–28.8°
b = 17.6345 (11) Å	µ = 0.09 mm⁻¹
c = 10.3147 (6) Å	T = 296 K
β = 110.755 (2)°	Block, yellow
V = 1436.38 (15) Å³	0.40 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3742 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 28.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→7
T_min = 0.967, T_max = 0.979	k = −23→19
16676 measured reflections	l = −12→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0597P)² + 0.249P] where P = (F_o² + 2F_c²)/3
3742 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₅N₃O₂	V = 1436.38 (15) Å³
M_r = 269.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4448 (5) Å	µ = 0.09 mm⁻¹
b = 17.6345 (11) Å	T = 296 K
c = 10.3147 (6) Å	0.40 × 0.25 × 0.20 mm
β = 110.755 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3742 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2291 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.979	R_int = 0.027
16676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
3742 reflections	Δρ_min = −0.18 e Å⁻³
182 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
O1	−0.07624 (14)	0.47405 (6)	0.69126 (11)	0.0587 (3)
O2	0.12331 (14)	0.34870 (6)	0.45867 (12)	0.0620 (3)
N1	0.30309 (17)	0.45287 (7)	0.87568 (13)	0.0525 (3)
N2	0.2926 (2)	0.43475 (9)	1.08660 (15)	0.0735 (5)
N3	0.23041 (17)	0.39663 (8)	0.55862 (13)	0.0544 (3)
C1	0.2331 (2)	0.47207 (11)	0.97034 (18)	0.0672 (5)
H1	0.1494	0.5089	0.9538	0.081*
C2	0.4123 (2)	0.38660 (10)	1.06784 (16)	0.0561 (4)
C3	0.5178 (2)	0.33399 (11)	1.15764 (18)	0.0691 (5)
H3	0.5126	0.3257	1.2451	0.083*
C4	0.6289 (3)	0.29490 (12)	1.1144 (2)	0.0752 (5)
H4	0.7002	0.2594	1.1732	0.090*
C5	0.6378 (2)	0.30710 (12)	0.9839 (2)	0.0756 (5)
H5	0.7168	0.2802	0.9583	0.091*
C6	0.5329 (2)	0.35802 (10)	0.89142 (19)	0.0629 (4)
H6	0.5373	0.3655	0.8035	0.076*
C7	0.42077 (19)	0.39732 (8)	0.93684 (15)	0.0489 (4)
C8	0.2629 (2)	0.48404 (9)	0.73688 (16)	0.0545 (4)
H8A	0.3672	0.4931	0.7200	0.065*
H8B	0.2060	0.5324	0.7313	0.065*
C9	0.15179 (19)	0.43200 (8)	0.62662 (14)	0.0461 (3)
C10	−0.02592 (19)	0.42668 (8)	0.60758 (15)	0.0460 (3)
C11	−0.1609 (2)	0.38634 (9)	0.52731 (17)	0.0564 (4)
H11	−0.1616	0.3501	0.4616	0.068*
C12	−0.3007 (2)	0.40962 (11)	0.5621 (2)	0.0674 (5)
H12	−0.4112	0.3918	0.5237	0.081*
C13	−0.2438 (2)	0.46193 (11)	0.6602 (2)	0.0679 (5)
H13	−0.3102	0.4869	0.7020	0.081*
C14	0.2185 (2)	0.31439 (13)	0.3830 (2)	0.0813 (6)
H14A	0.3135	0.2863	0.4460	0.098*
H14B	0.2625	0.3534	0.3386	0.098*
C15	0.1095 (3)	0.26391 (19)	0.2798 (3)	0.1340 (12)
H15A	0.1742	0.2382	0.2331	0.201*
H15B	0.0206	0.2926	0.2136	0.201*
H15C	0.0610	0.2273	0.3238	0.201*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0639 (7)	0.0630 (7)	0.0511 (6)	0.0017 (5)	0.0226 (5)	−0.0089 (5)
O2	0.0581 (7)	0.0677 (7)	0.0577 (7)	0.0012 (6)	0.0173 (5)	−0.0193 (6)
N1	0.0589 (8)	0.0543 (7)	0.0408 (7)	−0.0030 (6)	0.0136 (6)	−0.0069 (6)
N2	0.0865 (11)	0.0894 (11)	0.0453 (8)	0.0104 (9)	0.0241 (8)	−0.0082 (8)
N3	0.0554 (7)	0.0591 (8)	0.0453 (7)	−0.0013 (6)	0.0136 (6)	−0.0042 (6)
C1	0.0761 (12)	0.0722 (11)	0.0518 (10)	0.0112 (9)	0.0210 (9)	−0.0116 (9)
C2	0.0597 (9)	0.0634 (10)	0.0400 (8)	−0.0069 (8)	0.0112 (7)	−0.0092 (7)
C3	0.0748 (12)	0.0795 (12)	0.0429 (9)	−0.0053 (10)	0.0083 (8)	0.0017 (8)
C4	0.0676 (11)	0.0768 (12)	0.0647 (12)	0.0044 (10)	0.0029 (10)	0.0055 (10)
C5	0.0636 (11)	0.0796 (13)	0.0809 (14)	0.0112 (10)	0.0222 (10)	−0.0037 (11)
C6	0.0611 (10)	0.0722 (11)	0.0578 (10)	−0.0017 (9)	0.0239 (8)	−0.0043 (9)
C7	0.0477 (8)	0.0516 (8)	0.0420 (8)	−0.0091 (7)	0.0094 (6)	−0.0069 (6)
C8	0.0619 (10)	0.0515 (9)	0.0470 (9)	−0.0101 (7)	0.0153 (7)	−0.0003 (7)
C9	0.0551 (9)	0.0438 (7)	0.0374 (8)	−0.0002 (6)	0.0141 (6)	0.0044 (6)
C10	0.0577 (9)	0.0420 (7)	0.0389 (8)	0.0011 (6)	0.0180 (6)	0.0014 (6)
C11	0.0615 (10)	0.0527 (9)	0.0552 (9)	−0.0061 (7)	0.0210 (8)	−0.0052 (7)
C12	0.0580 (10)	0.0751 (11)	0.0709 (12)	−0.0095 (9)	0.0252 (9)	−0.0033 (10)
C13	0.0632 (11)	0.0810 (12)	0.0684 (12)	0.0060 (9)	0.0342 (9)	0.0004 (10)
C14	0.0680 (12)	0.0984 (15)	0.0776 (13)	0.0098 (11)	0.0257 (10)	−0.0302 (12)
C15	0.0854 (16)	0.165 (3)	0.138 (2)	0.0083 (17)	0.0234 (16)	−0.097 (2)

Geometric parameters (Å, º) top

O1—C10	1.3723 (17)	C7—C6	1.382 (2)
O1—C13	1.352 (2)	C8—H8A	0.9700
O2—N3	1.3909 (16)	C8—H8B	0.9700
O2—C14	1.438 (2)	C9—N3	1.285 (2)
N1—C1	1.351 (2)	C9—C8	1.503 (2)
N1—C7	1.379 (2)	C9—C10	1.446 (2)
N1—C8	1.457 (2)	C10—C11	1.350 (2)
N2—C1	1.303 (2)	C11—C12	1.411 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—N2	1.385 (2)	C12—H12	0.9300
C2—C3	1.388 (2)	C13—C12	1.328 (3)
C3—C4	1.361 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.442 (3)
C4—H4	0.9300	C14—H14A	0.9700
C5—C4	1.391 (3)	C14—H14B	0.9700
C5—H5	0.9300	C15—H15A	0.9600
C6—C5	1.379 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C2	1.391 (2)

C13—O1—C10	106.63 (13)	C9—C8—H8A	109.2
N3—O2—C14	108.44 (12)	C9—C8—H8B	109.2
C1—N1—C7	106.03 (13)	H8A—C8—H8B	107.9
C1—N1—C8	127.31 (15)	N3—C9—C8	113.87 (14)
C7—N1—C8	126.65 (13)	N3—C9—C10	127.33 (14)
C1—N2—C2	104.09 (14)	C10—C9—C8	118.81 (13)
C9—N3—O2	111.93 (13)	O1—C10—C9	114.39 (13)
N1—C1—H1	122.8	C11—C10—O1	108.92 (13)
N2—C1—N1	114.46 (16)	C11—C10—C9	136.69 (14)
N2—C1—H1	122.8	C10—C11—C12	106.94 (15)
N2—C2—C3	130.09 (16)	C10—C11—H11	126.5
N2—C2—C7	110.10 (15)	C12—C11—H11	126.5
C3—C2—C7	119.80 (16)	C11—C12—H12	126.7
C2—C3—H3	120.9	C13—C12—C11	106.65 (16)
C4—C3—C2	118.29 (17)	C13—C12—H12	126.7
C4—C3—H3	120.9	O1—C13—H13	124.6
C3—C4—C5	121.26 (18)	C12—C13—O1	110.85 (16)
C3—C4—H4	119.4	C12—C13—H13	124.6
C5—C4—H4	119.4	O2—C14—C15	109.09 (17)
C4—C5—H5	119.1	O2—C14—H14A	109.9
C6—C5—C4	121.86 (18)	O2—C14—H14B	109.9
C6—C5—H5	119.1	C15—C14—H14A	109.9
C5—C6—C7	116.19 (17)	C15—C14—H14B	109.9
C5—C6—H6	121.9	H14A—C14—H14B	108.3
C7—C6—H6	121.9	C14—C15—H15A	109.5
N1—C7—C6	132.10 (15)	C14—C15—H15B	109.5
N1—C7—C2	105.31 (14)	C14—C15—H15C	109.5
C6—C7—C2	122.57 (15)	H15A—C15—H15B	109.5
N1—C8—C9	112.26 (12)	H15A—C15—H15C	109.5
N1—C8—H8A	109.2	H15B—C15—H15C	109.5
N1—C8—H8B	109.2

C13—O1—C10—C9	179.95 (13)	C7—C6—C5—C4	1.3 (3)
C13—O1—C10—C11	−0.15 (17)	N1—C7—C2—N2	−0.25 (18)
C10—O1—C13—C12	0.1 (2)	N1—C7—C2—C3	−179.41 (14)
C14—O2—N3—C9	177.14 (15)	C6—C7—C2—N2	178.33 (15)
N3—O2—C14—C15	179.4 (2)	C6—C7—C2—C3	−0.8 (2)
C7—N1—C1—N2	−0.1 (2)	N1—C7—C6—C5	177.93 (16)
C8—N1—C1—N2	179.70 (15)	C2—C7—C6—C5	−0.2 (2)
C1—N1—C7—C2	0.23 (17)	C8—C9—N3—O2	179.48 (11)
C1—N1—C7—C6	−178.15 (17)	C10—C9—N3—O2	−0.6 (2)
C8—N1—C7—C2	−179.61 (14)	N3—C9—C8—N1	−104.67 (16)
C8—N1—C7—C6	2.0 (3)	C10—C9—C8—N1	75.41 (17)
C1—N1—C8—C9	−102.12 (19)	N3—C9—C10—O1	−177.03 (14)
C7—N1—C8—C9	77.69 (19)	N3—C9—C10—C11	3.1 (3)
C2—N2—C1—N1	0.0 (2)	C8—C9—C10—O1	2.88 (18)
C3—C2—N2—C1	179.21 (18)	C8—C9—C10—C11	−176.98 (17)
C7—C2—N2—C1	0.16 (19)	O1—C10—C11—C12	0.16 (18)
N2—C2—C3—C4	−178.13 (18)	C9—C10—C11—C12	−179.97 (17)
C7—C2—C3—C4	0.8 (3)	C10—C11—C12—C13	−0.1 (2)
C2—C3—C4—C5	0.2 (3)	O1—C13—C12—C11	0.0 (2)
C6—C5—C4—C3	−1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2ⁱ	0.93	2.54	3.328 (2)	143
C14—H14A···Cg2ⁱⁱ	0.97	2.88	3.768 (2)	153

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃O₂
M_r	269.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.4448 (5), 17.6345 (11), 10.3147 (6)
β (°)	110.755 (2)
V (Å³)	1436.38 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.967, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	16676, 3742, 2291
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.679

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.140, 1.03
No. of reflections	3742
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2ⁱ	0.93	2.54	3.328 (2)	143
C14—H14A···Cg2ⁱⁱ	0.97	2.88	3.768 (2)	153

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, −y−1/2, z−3/2.

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (Project No. 2007/2–13–02–09).

References

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