1-[2-(2,6-Dichloro­benz­yloxy)-2-(2-fur­yl)eth­yl]-1H-1,2,4-triazole

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

doi:10.1107/S1600536809052568

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o107-o108

doi:10.1107/S1600536809052568

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1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole

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

^aDepartment of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak, Turkey, ^bDepartment of Chemistry, Southampton University, Southampton SO17 1BJ, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 4 December 2009; accepted 7 December 2009; online 12 December 2009)

In the molecule of the title compound, C₁₅H₁₃Cl₂N₃O₂, the triazole ring is oriented at dihedral angles of 2.54 (13) and 44.43 (12)°, respectively with respect to the furan and dichlorobenzene rings. The dihedral angle between the dichlorobenzene and furan rings is 46.75 (12)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers and π–π contacts between dichlorobenzene rings [centroid–centroid distance = 3.583 (2) Å] may further stabilize the structure. Intermolecular C—H⋯π contacts between the triazole and furan rings also occur.

Related literature

For general background to antifungal agents, see: Caira et al. (2004 ); Godefroi et al. (1969 ); Özel Güven et al. (2007a ,b ); Paulvannan et al. (2001 ); Peeters et al. (1996 ); Wahbi et al. (1995 ). For related structures, see: Freer et al. (1986 ); Özel Güven et al. (2008a ,b ,c ,d ,e ,f ); Özel Güven et al. (2009 ); Peeters et al. (1979 ).

Experimental

Crystal data

C₁₅H₁₃Cl₂N₃O₂
M_r = 338.18
Monoclinic, P 2₁ /n
a = 10.5853 (3) Å
b = 12.4960 (2) Å
c = 12.5850 (3) Å
β = 114.455 (1)°
V = 1515.32 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.837, T_max = 0.955
33067 measured reflections
3438 independent reflections
2775 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.180
S = 1.04
3438 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.44	3.363 (3)	173
C9—H9B⋯Cl2	0.97	2.62	3.109 (3)	112
C1—H1⋯Cg2ⁱⁱ	0.93	2.79	3.488 (4)	133
C7—H7⋯Cg1ⁱⁱⁱ	0.93	2.93	3.570 (4)	127
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.

Data collection: COLLECT (Nonius, 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052568/xu2704sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052568/xu2704Isup2.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. Some ether structures containing 1H-imidazole ring like micozanole, ecozanole and sulconazole have been synthesized and developed for clinical uses as antifungal agents (Godefroi et al., 1969). The crystal structures of these ether derivatives like miconazole (Peeters et al., 1979), econazole (Freer et al., 1986) have been reported previously. Also, antifungal activity of aromatic ethers possessing 1H-1,2,4-triazole ring have been reported (Wahbi et al., 1995). Itraconazole (Peeters et al., 1996) and fluconazole (Caira et al., 2004) are 1H-1,2,4-triazole ring containing azole derivatives. 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). Ether structures possessing 1H-benzimidazole ring have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). 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 derivatives have been reported recently (Özel Güven et al., 2008e,f; Özel Güven et al., 2009). Now, we report herein the crystal structure of 2,6-dichloro- derivative of 1H-1,2,4-triazole and furyl rings containing 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 furan and dichlorobenzene rings at dihedral angles of 2.54 (13)° and 44.43 (12)°, respectively. Atoms C3, C4 and C9 are -0.064 (3), 0.039 (3) and -0.073 (3) Å away from the planes of the triazole, furan and dichlorobenzene, respectively. So, they are nearly coplanar with the adjacent rings. The dichlorobenzene ring is oriented with respect to the furan ring at a dihedral angle of 46.75 (12)°. An intramolecular C—H···Cl hydrogen bond (Table 1) results in the formation of a five-membered ring (Cl2/H9B/C9/C10/C15) adopting envelope conformation with H9B atom displaced by 0.210 (1) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the dichlorobenzene rings, Cg3—Cg3ⁱ [symmetry code: (i) -x, -y, 1 - z, where Cg3 is centroid of the ring (C10-C15)] may further stabilize the structure, with centroid-centroid distance of 3.583 (2) Å. Intermolecular C—H···π interactions (Table 1) are also observed between the triazole and furan rings.

Related literature top

For general background to antifungal agents, see: Caira et al. (2004); Godefroi et al. (1969); Özel Güven et al. (2007a,b); Paulvannan et al. (2001); Peeters et al. (1996); Wahbi et al. (1995). For related structures, see: Freer et al. (1986); Özel Güven et al. (2008a,b,c,d,e,f); Özel Güven et al. (2009); Peeters et al. (1979).

Experimental top

The title compound was synthesized by the reaction of 1-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol (unpublished results) with NaH and appropriate benzyl halide. To a solution of alcohol (500 mg, 2.791 mmol) in DMF (4 ml) was added NaH (112 mg, 2.791 mmol) in small fractions. The appropriate benzyl halide (669 mg, 2.791 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 isopropanol solution (yield; 500 mg, 53%).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. A partial packing diagram.

1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole top

Crystal data top

C₁₅H₁₃Cl₂N₃O₂	F(000) = 696
M_r = 338.18	D_x = 1.482 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 23020 reflections
a = 10.5853 (3) Å	θ = 2.9–27.5°
b = 12.4960 (2) Å	µ = 0.44 mm⁻¹
c = 12.5850 (3) Å	T = 120 K
β = 114.455 (1)°	Plate, colorless
V = 1515.32 (6) Å³	0.40 × 0.40 × 0.10 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	2775 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −13→13
T_min = 0.837, T_max = 0.955	k = −14→15
33067 measured reflections	l = −16→16

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)] = 0.067	H-atom parameters constrained
wR(F²) = 0.180	w = 1/[σ²(F_o²) + (0.0984P)² + 1.9705P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3438 reflections	Δρ_max = 1.20 e Å⁻³
200 parameters	Δρ_min = −0.76 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: 0.051 (5)

Crystal data top

C₁₅H₁₃Cl₂N₃O₂	V = 1515.32 (6) Å³
M_r = 338.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5853 (3) Å	µ = 0.44 mm⁻¹
b = 12.4960 (2) Å	T = 120 K
c = 12.5850 (3) Å	0.40 × 0.40 × 0.10 mm
β = 114.455 (1)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	3438 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2775 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.955	R_int = 0.058
33067 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.04	Δρ_max = 1.20 e Å⁻³
3438 reflections	Δρ_min = −0.76 e Å⁻³
200 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.32066 (8)	0.66344 (7)	1.08482 (8)	0.0470 (3)
Cl2	0.29005 (8)	0.31220 (7)	0.82358 (9)	0.0497 (3)
O1	0.07950 (17)	0.54757 (14)	0.86960 (15)	0.0231 (4)
O2	−0.1088 (3)	0.5914 (2)	0.5685 (2)	0.0483 (6)
N1	−0.0576 (2)	0.71549 (17)	0.93071 (19)	0.0226 (5)
N2	−0.0121 (2)	0.81516 (18)	0.9183 (2)	0.0284 (5)
N3	0.0458 (2)	0.7770 (2)	1.1089 (2)	0.0298 (5)
C1	0.0483 (3)	0.8475 (2)	1.0282 (3)	0.0300 (6)
H1	0.0898	0.9144	1.0487	0.036*
C2	−0.0207 (3)	0.6947 (2)	1.0435 (2)	0.0255 (5)
H2	−0.0393	0.6309	1.0724	0.031*
C3	−0.1260 (3)	0.6463 (2)	0.8301 (2)	0.0248 (5)
H3A	−0.2023	0.6846	0.7706	0.030*
H3B	−0.1638	0.5842	0.8530	0.030*
C4	−0.0241 (2)	0.6098 (2)	0.7800 (2)	0.0228 (5)
H4	0.0197	0.6727	0.7628	0.027*
C5	−0.0952 (3)	0.5454 (2)	0.6705 (2)	0.0250 (5)
C6	−0.1805 (4)	0.5198 (4)	0.4817 (3)	0.0582 (11)
H6	−0.2048	0.5311	0.4026	0.070*
C7	−0.2101 (3)	0.4328 (3)	0.5259 (3)	0.0457 (9)
H7	−0.2564	0.3726	0.4847	0.055*
C8	−0.1574 (3)	0.4484 (3)	0.6500 (3)	0.0429 (8)
H8	−0.1646	0.4016	0.7047	0.051*
C9	0.2081 (3)	0.5444 (2)	0.8579 (2)	0.0244 (5)
H9A	0.2416	0.6164	0.8565	0.029*
H9B	0.1961	0.5086	0.7859	0.029*
C10	0.3091 (2)	0.4839 (2)	0.9611 (2)	0.0224 (5)
C11	0.3640 (3)	0.5315 (2)	1.0718 (2)	0.0283 (6)
C12	0.4517 (3)	0.4781 (3)	1.1713 (3)	0.0424 (8)
H12	0.4849	0.5122	1.2435	0.051*
C13	0.4890 (3)	0.3753 (3)	1.1629 (3)	0.0459 (9)
H13	0.5469	0.3388	1.2297	0.055*
C14	0.4416 (3)	0.3250 (2)	1.0558 (4)	0.0427 (9)
H14	0.4695	0.2555	1.0500	0.051*
C15	0.3507 (3)	0.3794 (2)	0.9559 (3)	0.0304 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0272 (4)	0.0521 (5)	0.0535 (5)	0.0023 (3)	0.0085 (3)	−0.0273 (4)
Cl2	0.0340 (4)	0.0412 (5)	0.0711 (6)	−0.0067 (3)	0.0191 (4)	−0.0283 (4)
O1	0.0144 (8)	0.0260 (9)	0.0257 (9)	0.0012 (6)	0.0052 (7)	0.0068 (7)
O2	0.0633 (16)	0.0525 (15)	0.0306 (12)	−0.0134 (12)	0.0208 (11)	−0.0054 (10)
N1	0.0183 (10)	0.0227 (11)	0.0247 (11)	−0.0008 (8)	0.0069 (8)	0.0013 (8)
N2	0.0284 (12)	0.0243 (12)	0.0289 (12)	−0.0032 (9)	0.0082 (9)	0.0016 (9)
N3	0.0262 (11)	0.0356 (13)	0.0269 (12)	0.0010 (10)	0.0105 (9)	−0.0031 (9)
C1	0.0244 (13)	0.0283 (14)	0.0341 (15)	−0.0025 (10)	0.0089 (11)	−0.0028 (11)
C2	0.0228 (12)	0.0282 (13)	0.0282 (13)	0.0003 (10)	0.0131 (11)	0.0020 (10)
C3	0.0172 (11)	0.0250 (13)	0.0271 (13)	−0.0020 (9)	0.0041 (10)	−0.0012 (10)
C4	0.0168 (11)	0.0230 (12)	0.0233 (12)	0.0005 (9)	0.0032 (9)	0.0040 (9)
C5	0.0201 (12)	0.0264 (13)	0.0247 (13)	0.0046 (9)	0.0057 (10)	0.0000 (10)
C6	0.065 (3)	0.077 (3)	0.0307 (17)	−0.009 (2)	0.0176 (17)	−0.0201 (17)
C7	0.0299 (15)	0.0392 (18)	0.051 (2)	0.0080 (13)	−0.0004 (14)	−0.0203 (15)
C8	0.0333 (16)	0.0322 (16)	0.0470 (19)	−0.0052 (12)	0.0004 (14)	0.0062 (13)
C9	0.0177 (11)	0.0308 (13)	0.0254 (13)	0.0016 (9)	0.0096 (10)	0.0038 (10)
C10	0.0152 (11)	0.0240 (12)	0.0286 (13)	0.0001 (9)	0.0095 (10)	0.0050 (10)
C11	0.0165 (11)	0.0400 (15)	0.0289 (14)	0.0013 (10)	0.0098 (10)	0.0039 (11)
C12	0.0208 (13)	0.080 (3)	0.0261 (15)	0.0038 (14)	0.0098 (12)	0.0119 (15)
C13	0.0222 (14)	0.068 (2)	0.0461 (19)	0.0056 (14)	0.0131 (13)	0.0354 (17)
C14	0.0233 (14)	0.0281 (15)	0.080 (3)	0.0056 (11)	0.0243 (16)	0.0228 (15)
C15	0.0190 (12)	0.0248 (13)	0.0472 (17)	−0.0040 (10)	0.0134 (12)	−0.0008 (11)

Geometric parameters (Å, º) top

N1—N2	1.367 (3)	C7—C8	1.438 (5)
C1—N2	1.324 (4)	C7—H7	0.9300
C1—N3	1.352 (4)	C8—H8	0.9300
C1—H1	0.9300	C9—O1	1.429 (3)
C2—N3	1.323 (4)	C9—H9A	0.9700
C2—N1	1.333 (3)	C9—H9B	0.9700
C2—H2	0.9300	C10—C9	1.501 (3)
C3—N1	1.455 (3)	C10—C11	1.401 (4)
C3—H3A	0.9700	C10—C15	1.389 (4)
C3—H3B	0.9700	C11—Cl1	1.737 (3)
C4—O1	1.434 (3)	C11—C12	1.383 (4)
C4—C3	1.527 (4)	C12—C13	1.361 (6)
C4—C5	1.501 (4)	C12—H12	0.9300
C4—H4	0.9800	C13—C14	1.380 (6)
C5—O2	1.359 (4)	C13—H13	0.9300
C5—C8	1.352 (4)	C14—C15	1.403 (4)
C6—O2	1.373 (4)	C14—H14	0.9300
C6—C7	1.317 (6)	C15—Cl2	1.733 (3)
C6—H6	0.9300

C9—O1—C4	112.62 (18)	C6—C7—C8	107.1 (3)
C5—O2—C6	106.5 (3)	C6—C7—H7	126.5
N2—N1—C3	120.9 (2)	C8—C7—H7	126.5
C2—N1—N2	109.7 (2)	C5—C8—C7	105.6 (3)
C2—N1—C3	129.2 (2)	C5—C8—H8	127.2
C1—N2—N1	101.5 (2)	C7—C8—H8	127.2
C2—N3—C1	102.1 (2)	O1—C9—C10	107.01 (19)
N2—C1—N3	115.7 (2)	O1—C9—H9A	110.3
N2—C1—H1	122.1	O1—C9—H9B	110.3
N3—C1—H1	122.1	C10—C9—H9A	110.3
N1—C2—H2	124.5	C10—C9—H9B	110.3
N3—C2—N1	110.9 (2)	H9A—C9—H9B	108.6
N3—C2—H2	124.5	C11—C10—C9	120.1 (2)
N1—C3—C4	110.8 (2)	C15—C10—C9	124.0 (2)
N1—C3—H3A	109.5	C15—C10—C11	115.9 (2)
N1—C3—H3B	109.5	C10—C11—Cl1	118.7 (2)
C4—C3—H3A	109.5	C12—C11—C10	122.9 (3)
C4—C3—H3B	109.5	C12—C11—Cl1	118.5 (3)
H3A—C3—H3B	108.1	C11—C12—H12	120.3
O1—C4—C3	106.1 (2)	C13—C12—C11	119.5 (3)
O1—C4—C5	111.1 (2)	C13—C12—H12	120.3
O1—C4—H4	109.3	C12—C13—C14	120.5 (3)
C3—C4—H4	109.3	C12—C13—H13	119.8
C5—C4—C3	111.5 (2)	C14—C13—H13	119.8
C5—C4—H4	109.3	C13—C14—C15	119.5 (3)
O2—C5—C4	117.2 (2)	C13—C14—H14	120.3
C8—C5—O2	110.3 (3)	C15—C14—H14	120.3
C8—C5—C4	132.5 (3)	C10—C15—Cl2	120.2 (2)
O2—C6—H6	124.7	C10—C15—C14	121.8 (3)
C7—C6—O2	110.6 (3)	C14—C15—Cl2	118.1 (2)
C7—C6—H6	124.7

C2—N1—N2—C1	−1.0 (3)	C7—C6—O2—C5	−0.4 (4)
C3—N1—N2—C1	−176.9 (2)	O2—C6—C7—C8	1.3 (4)
N3—C1—N2—N1	0.4 (3)	C6—C7—C8—C5	−1.7 (4)
N2—C1—N3—C2	0.3 (3)	C10—C9—O1—C4	176.0 (2)
N3—C2—N1—N2	1.3 (3)	C11—C10—C9—O1	−73.1 (3)
N3—C2—N1—C3	176.7 (2)	C15—C10—C9—O1	104.8 (3)
N1—C2—N3—C1	−1.0 (3)	C9—C10—C11—Cl1	−3.8 (3)
C4—C3—N1—C2	−107.0 (3)	C9—C10—C11—C12	176.5 (2)
C4—C3—N1—N2	68.0 (3)	C15—C10—C11—Cl1	178.21 (19)
C3—C4—O1—C9	−156.0 (2)	C15—C10—C11—C12	−1.5 (4)
C5—C4—O1—C9	82.6 (3)	C9—C10—C15—Cl2	2.2 (3)
O1—C4—C3—N1	63.3 (3)	C9—C10—C15—C14	−177.5 (2)
C5—C4—C3—N1	−175.5 (2)	C11—C10—C15—Cl2	−179.85 (19)
O1—C4—C5—O2	−132.0 (2)	C11—C10—C15—C14	0.4 (4)
O1—C4—C5—C8	51.7 (4)	C10—C11—C12—C13	0.9 (4)
C3—C4—C5—O2	109.7 (3)	Cl1—C11—C12—C13	−178.8 (2)
C3—C4—C5—C8	−66.6 (4)	C11—C12—C13—C14	0.9 (4)
C4—C5—O2—C6	−177.9 (3)	C12—C13—C14—C15	−2.0 (4)
C8—C5—O2—C6	−0.8 (4)	C13—C14—C15—Cl2	−178.4 (2)
O2—C5—C8—C7	1.5 (4)	C13—C14—C15—C10	1.3 (4)
C4—C5—C8—C7	178.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.44	3.363 (3)	173
C9—H9B···Cl2	0.97	2.62	3.109 (3)	112
C1—H1···Cg2ⁱⁱ	0.93	2.79	3.488 (4)	133
C7—H7···Cg1ⁱⁱⁱ	0.93	2.93	3.570 (4)	127

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃Cl₂N₃O₂
M_r	338.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	10.5853 (3), 12.4960 (2), 12.5850 (3)
β (°)	114.455 (1)
V (Å³)	1515.32 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.40 × 0.40 × 0.10

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.837, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	33067, 3438, 2775
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.180, 1.04
No. of reflections	3438
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.20, −0.76

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.44	3.363 (3)	173
C9—H9B···Cl2	0.97	2.62	3.109 (3)	112
C1—H1···Cg2ⁱⁱ	0.93	2.79	3.488 (4)	133
C7—H7···Cg1ⁱⁱⁱ	0.93	2.93	3.570 (4)	127

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

Acknowledgements

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

References

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