1-[2-(2,4-Dichloro­benz­yloxy)-2-(furan-2-yl)eth­yl]-1H-benzotriazole

Özel Güven, Ö.; Bayraktar, M.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536811053104

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o139-o140

doi:10.1107/S1600536811053104

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1-[2-(2,4-Dichlorobenzyloxy)-2-(furan-2-yl)ethyl]-1H-benzotriazole

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

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

(Received 9 December 2011; accepted 9 December 2011; online 17 December 2011)

In the title compound, C₁₉H₁₅Cl₂N₃O₂, the benzotriazole ring system is approximately planar [maximum deviation = 0.018 (2) Å] and its mean plane is oriented at dihedral angles of 30.70 (5) and 87.38 (4)°, respectively, to the furan and benzene rings while the dihedral angle between furan and benzene rings is 74.46 (6)°. In the crystal, weak C—H⋯N hydrogen bonds link the molecules into chains along the b axis. π–π stacking interactions between the parallel dichlorobenzene rings of adjacent molecules [centroid–centroid distance = 3.6847 (9) Å] and weak C—H⋯π interactions are also observed.

Related literature

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998 ); Yu et al. (2003 ); Kopanska et al. (2004 ); Özel Güven et al. (2007a ,b ); Peeters et al. (1979 ); Freer et al. (1986 ). For related structures, see: Özel Güven et al. (2008 , 2009 , 2010a ,b , 2011 . For the synthesis of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanol, see: Özel Güven et al. (2012 ).

Experimental

Crystal data

C₁₉H₁₅Cl₂N₃O₂
M_r = 388.24
Monoclinic, P 2₁ /c
a = 11.5452 (2) Å
b = 20.0350 (5) Å
c = 8.3317 (2) Å
β = 105.598 (2)°
V = 1856.21 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 120 K
0.50 × 0.30 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.837, T_max = 0.971
31461 measured reflections
4251 independent reflections
3252 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.103
S = 1.04
4251 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N3ⁱ	0.93	2.59	3.452 (2)	155
C8—H8⋯Cgⁱⁱ	0.93	2.92	3.782 (2)	155
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+1.

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 ); 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/S1600536811053104/xu5406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053104/xu5406Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053104/xu5406Isup3.cml

checkCIF report

Comment top

In recent years, there has been increasing interest in syntheses of heterocyclic compounds that have biological and commercial importance. Miconazole and econazole have been developed for clinical uses as antifungal agents. Similar structures containing benzimidazole ring in place of imidazole ring of miconazole and econazole have been reported showing more antibacterial activity than antifungal activity (Özel Güven et al., 2007a,b). Benzotriazole derivatives also exhibit a good degree of analgesic, anti-inflammatory, diuretic, antiviral and antihypertensive activities (Hirokawa et al., 1998; Yu et al., 2003; Kopanska et al., 2004). The crystal structures of miconazole (Peeters et al., 1979), econazole (Freer et al., 1986) and similar ether compounds (Özel Güven et al., 2008; Özel Güven et al., 2009; Özel Güven et al., 2010a,b; Özel Güven et al., 2011) have been reported, previously. Now, we report herein the crystal structure of a new benzotriazole derivative, (I).

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The benzotriazole [B (N1-N3/C7-C12)] ring system is approximately planar with a maximum deviation of 0.018 (2) Å for atom C9 and its mean plane is oriented with respect to the furan [A (O2/C2-C5)] and benzene [C (C14-C19)] rings at dihedral angles of A/B = 30.70 (5) and B/C = 87.38 (4) °. The dihedral angle between furan and benzene rings is A/C = 74.46 (6)°. Atom C6 is -0.033 (2) Å away from the plane of the benzotriazole ring and atom C1 is 0.050 (2) Å away from the plane of the furan ring, while atoms Cl1, Cl2, O1 and C13 are 0.0309 (5), 0.0223 (5), 0.0817 (11) and 0.0195 (18) Å away from the plane of the benzene ring, respectively.

In the crystal, weak C—H···N hydrogen bonds (Table 1) link the molecules into chains along the b-axis (Fig. 2). There also exists a π–π contact between the benzene rings, Cg4—Cg4ⁱ, may further stabilize the structure [centroid-centroid distance = 3.685 (1) Å; symmetry code: (i) 2 - x, -y, -z; Cg4 is the centroid of the ring C (C14-C19)]. A weak C—H···π interaction (Table 1) may stabilize the structure.

Related literature top

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998); Yu et al. (2003); Kopanska et al. (2004); Özel Güven et al. (2007a,b); Peeters et al. (1979); Freer et al. (1986). For related structures, see: Özel Güven et al. (2008, 2009, 2010a,b, 2011. For the synthesis of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanol, see: Özel Güven et al. (2012).

Experimental top

The title compound, (I), was synthesized by the reaction of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanol (Özel Güven et al., 2012) with aryl halide using NaH. 2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol (219 mg, 0.95 mmol) was dissolved in DMF (4 ml). NaH (38 mg, 0.96 mmol) was added to the solution portionwise. After stirring the mixture a few minutes, 2,4-dichlorobenzyl bromide (229 mg, 0.95 mmol) was added dropwise. Then, the reaction mixture was stirred additional 3 h at room temperature. Adding methanol (5 ml), the reaction was stopped. After evaporation of the solvent, dichloromethane was added to the reaction mixture and extracted with water. Then, the organic phase was separated, dried, filtered and evaporated. The precipitate formed was purified by column chromatography using chloroform and crystallized from 2-propanol to obtain colorless crystals suitable for X-ray analysis (yield; 295 mg, 80%).

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); 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.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

1-[2-(2,4-Dichlorobenzyloxy)-2-(furan-2-yl)ethyl]-1H-benzotriazole top

Crystal data top

C₁₉H₁₅Cl₂N₃O₂	F(000) = 800
M_r = 388.24	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11553 reflections
a = 11.5452 (2) Å	θ = 2.9–27.5°
b = 20.0350 (5) Å	µ = 0.37 mm⁻¹
c = 8.3317 (2) Å	T = 120 K
β = 105.598 (2)°	Slab, colorless
V = 1856.21 (7) Å³	0.50 × 0.30 × 0.08 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	4251 independent reflections
Radiation source: fine-focus sealed tube	3252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 27.6°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
T_min = 0.837, T_max = 0.971	k = −26→26
31461 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0497P)² + 0.507P] where P = (F_o² + 2F_c²)/3
4251 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₉H₁₅Cl₂N₃O₂	V = 1856.21 (7) Å³
M_r = 388.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5452 (2) Å	µ = 0.37 mm⁻¹
b = 20.0350 (5) Å	T = 120 K
c = 8.3317 (2) Å	0.50 × 0.30 × 0.08 mm
β = 105.598 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4251 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3252 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.971	R_int = 0.061
31461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
4251 reflections	Δρ_min = −0.34 e Å⁻³
235 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	0.89226 (4)	0.18886 (2)	0.01379 (7)	0.04089 (16)
Cl2	1.28141 (4)	0.02933 (3)	0.12097 (6)	0.03513 (14)
O1	0.75307 (10)	0.03838 (5)	0.30260 (14)	0.0220 (3)
O2	0.66612 (11)	0.09918 (6)	0.57356 (14)	0.0268 (3)
N1	0.60882 (12)	−0.07713 (7)	0.26337 (16)	0.0203 (3)
N2	0.51947 (12)	−0.09229 (7)	0.12492 (17)	0.0243 (3)
N3	0.55075 (13)	−0.14513 (7)	0.05429 (18)	0.0256 (3)
C1	0.62928 (14)	0.04521 (8)	0.3022 (2)	0.0207 (3)
H1	0.5806	0.0518	0.1873	0.025*
C2	0.60997 (14)	0.10283 (8)	0.4057 (2)	0.0210 (3)
C3	0.63944 (16)	0.15769 (9)	0.6416 (2)	0.0291 (4)
H3	0.6660	0.1687	0.7540	0.035*
C4	0.57008 (18)	0.19676 (9)	0.5242 (2)	0.0335 (4)
H4	0.5407	0.2388	0.5395	0.040*
C5	0.55017 (17)	0.16100 (9)	0.3709 (2)	0.0320 (4)
H5	0.5046	0.1752	0.2668	0.038*
C6	0.59430 (14)	−0.02090 (8)	0.3666 (2)	0.0209 (3)
H6A	0.6437	−0.0281	0.4794	0.025*
H6B	0.5111	−0.0186	0.3701	0.025*
C7	0.70139 (14)	−0.12118 (8)	0.28229 (19)	0.0190 (3)
C8	0.81400 (14)	−0.12713 (8)	0.3997 (2)	0.0227 (3)
H8	0.8386	−0.0980	0.4894	0.027*
C9	0.88576 (16)	−0.17884 (8)	0.3736 (2)	0.0258 (4)
H9	0.9616	−0.1843	0.4470	0.031*
C10	0.84755 (16)	−0.22394 (8)	0.2385 (2)	0.0275 (4)
H10	0.8986	−0.2584	0.2265	0.033*
C11	0.73701 (16)	−0.21804 (8)	0.1249 (2)	0.0266 (4)
H11	0.7121	−0.2478	0.0367	0.032*
C12	0.66331 (15)	−0.16504 (8)	0.1477 (2)	0.0214 (3)
C13	0.79095 (15)	0.09078 (8)	0.2133 (2)	0.0251 (4)
H13A	0.7933	0.1326	0.2729	0.030*
H13B	0.7345	0.0956	0.1043	0.030*
C14	0.91411 (14)	0.07481 (8)	0.1944 (2)	0.0207 (3)
C15	0.96919 (15)	0.11711 (8)	0.1043 (2)	0.0250 (4)
C16	1.08124 (15)	0.10456 (9)	0.0812 (2)	0.0269 (4)
H16	1.1158	0.1338	0.0207	0.032*
C17	1.14060 (14)	0.04695 (9)	0.1510 (2)	0.0242 (4)
C18	1.09010 (15)	0.00307 (8)	0.2414 (2)	0.0238 (4)
H18	1.1309	−0.0354	0.2874	0.029*
C19	0.97711 (15)	0.01756 (8)	0.2619 (2)	0.0228 (4)
H19	0.9427	−0.0118	0.3223	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0253 (3)	0.0312 (3)	0.0594 (3)	−0.00467 (18)	−0.0003 (2)	0.0213 (2)
Cl2	0.0204 (2)	0.0536 (3)	0.0334 (3)	−0.00010 (18)	0.01082 (18)	0.0020 (2)
O1	0.0185 (6)	0.0211 (6)	0.0288 (6)	0.0031 (4)	0.0106 (5)	0.0030 (5)
O2	0.0287 (7)	0.0240 (6)	0.0246 (6)	0.0066 (5)	0.0017 (5)	−0.0029 (5)
N1	0.0196 (7)	0.0203 (7)	0.0211 (7)	−0.0007 (5)	0.0057 (5)	−0.0026 (5)
N2	0.0227 (7)	0.0253 (7)	0.0242 (7)	−0.0021 (6)	0.0053 (6)	−0.0028 (6)
N3	0.0268 (8)	0.0248 (7)	0.0251 (8)	−0.0028 (6)	0.0070 (6)	−0.0032 (6)
C1	0.0183 (8)	0.0209 (8)	0.0231 (8)	0.0027 (6)	0.0061 (6)	−0.0021 (7)
C2	0.0182 (8)	0.0234 (8)	0.0207 (8)	0.0019 (6)	0.0043 (6)	−0.0007 (7)
C3	0.0329 (10)	0.0261 (9)	0.0274 (9)	0.0007 (7)	0.0066 (8)	−0.0091 (7)
C4	0.0404 (11)	0.0246 (9)	0.0357 (11)	0.0114 (8)	0.0107 (9)	−0.0035 (8)
C5	0.0408 (11)	0.0299 (10)	0.0229 (9)	0.0132 (8)	0.0041 (8)	0.0007 (8)
C6	0.0209 (8)	0.0208 (8)	0.0228 (8)	0.0010 (6)	0.0092 (6)	−0.0038 (7)
C7	0.0219 (8)	0.0166 (8)	0.0205 (8)	−0.0010 (6)	0.0093 (6)	0.0019 (6)
C8	0.0240 (9)	0.0208 (8)	0.0228 (8)	−0.0010 (6)	0.0057 (7)	0.0001 (7)
C9	0.0243 (9)	0.0244 (9)	0.0290 (9)	0.0029 (7)	0.0073 (7)	0.0045 (7)
C10	0.0328 (10)	0.0222 (9)	0.0310 (10)	0.0056 (7)	0.0147 (8)	0.0033 (7)
C11	0.0363 (10)	0.0190 (8)	0.0274 (9)	−0.0010 (7)	0.0136 (8)	−0.0027 (7)
C12	0.0246 (9)	0.0196 (8)	0.0211 (8)	−0.0030 (6)	0.0079 (7)	−0.0011 (7)
C13	0.0263 (9)	0.0172 (8)	0.0336 (10)	0.0007 (6)	0.0112 (7)	0.0038 (7)
C14	0.0199 (8)	0.0186 (8)	0.0231 (8)	−0.0032 (6)	0.0047 (6)	−0.0034 (6)
C15	0.0224 (9)	0.0235 (9)	0.0260 (9)	−0.0042 (7)	0.0010 (7)	0.0037 (7)
C16	0.0229 (9)	0.0326 (9)	0.0251 (9)	−0.0103 (7)	0.0060 (7)	0.0035 (7)
C17	0.0179 (8)	0.0336 (9)	0.0211 (8)	−0.0049 (7)	0.0054 (6)	−0.0052 (7)
C18	0.0226 (8)	0.0238 (8)	0.0249 (9)	0.0004 (7)	0.0063 (7)	−0.0022 (7)
C19	0.0234 (9)	0.0203 (8)	0.0254 (9)	−0.0016 (6)	0.0077 (7)	0.0017 (7)

Geometric parameters (Å, º) top

Cl1—C15	1.7504 (17)	C7—C8	1.406 (2)
Cl2—C17	1.7461 (17)	C7—C12	1.399 (2)
O1—C1	1.4348 (18)	C8—C9	1.380 (2)
O1—C13	1.4220 (19)	C8—H8	0.9300
O2—C2	1.376 (2)	C9—H9	0.9300
O2—C3	1.373 (2)	C10—C9	1.418 (3)
N1—C6	1.454 (2)	C10—H10	0.9300
N1—C7	1.362 (2)	C11—C10	1.375 (2)
N2—N1	1.3591 (18)	C11—H11	0.9300
N2—N3	1.3084 (19)	C12—C11	1.405 (2)
N3—C12	1.382 (2)	C13—H13A	0.9700
C1—C2	1.493 (2)	C13—H13B	0.9700
C1—C6	1.524 (2)	C14—C13	1.506 (2)
C1—H1	0.9800	C14—C15	1.394 (2)
C2—C5	1.346 (2)	C14—C19	1.393 (2)
C3—C4	1.338 (3)	C15—C16	1.381 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—H4	0.9300	C17—C16	1.388 (2)
C5—C4	1.429 (3)	C17—C18	1.384 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—H6A	0.9700	C19—C18	1.391 (2)
C6—H6B	0.9700	C19—H19	0.9300

C13—O1—C1	112.00 (12)	C8—C9—C10	122.12 (17)
C3—O2—C2	106.11 (13)	C8—C9—H9	118.9
N2—N1—C6	119.55 (13)	C10—C9—H9	118.9
N2—N1—C7	110.26 (13)	C9—C10—H10	119.2
C7—N1—C6	130.18 (13)	C11—C10—C9	121.67 (16)
N3—N2—N1	108.92 (13)	C11—C10—H10	119.2
N2—N3—C12	108.15 (13)	C10—C11—C12	117.10 (16)
O1—C1—C2	112.06 (13)	C10—C11—H11	121.4
O1—C1—C6	105.93 (12)	C12—C11—H11	121.4
O1—C1—H1	108.9	N3—C12—C7	108.39 (14)
C2—C1—C6	111.94 (13)	N3—C12—C11	130.82 (15)
C2—C1—H1	108.9	C7—C12—C11	120.78 (15)
C6—C1—H1	108.9	O1—C13—C14	109.25 (13)
O2—C2—C1	116.31 (13)	O1—C13—H13A	109.8
C5—C2—O2	109.84 (14)	O1—C13—H13B	109.8
C5—C2—C1	133.82 (16)	C14—C13—H13A	109.8
O2—C3—H3	124.6	C14—C13—H13B	109.8
C4—C3—O2	110.77 (16)	H13A—C13—H13B	108.3
C4—C3—H3	124.6	C15—C14—C13	120.49 (15)
C3—C4—C5	106.32 (15)	C19—C14—C13	122.53 (15)
C3—C4—H4	126.8	C19—C14—C15	116.98 (15)
C5—C4—H4	126.8	C14—C15—Cl1	118.63 (13)
C2—C5—C4	106.96 (16)	C16—C15—Cl1	118.37 (13)
C2—C5—H5	126.5	C16—C15—C14	122.99 (16)
C4—C5—H5	126.5	C15—C16—C17	117.93 (15)
N1—C6—C1	112.43 (13)	C15—C16—H16	121.0
N1—C6—H6A	109.1	C17—C16—H16	121.0
N1—C6—H6B	109.1	C16—C17—Cl2	118.82 (13)
C1—C6—H6A	109.1	C18—C17—Cl2	119.61 (14)
C1—C6—H6B	109.1	C18—C17—C16	121.57 (16)
H6A—C6—H6B	107.9	C17—C18—C19	118.72 (16)
N1—C7—C12	104.27 (14)	C17—C18—H18	120.6
N1—C7—C8	133.26 (15)	C19—C18—H18	120.6
C12—C7—C8	122.47 (15)	C14—C19—H19	119.1
C7—C8—H8	122.1	C18—C19—C14	121.81 (16)
C9—C8—C7	115.84 (15)	C18—C19—H19	119.1
C9—C8—H8	122.1

C13—O1—C1—C2	−69.97 (17)	N1—C7—C12—N3	0.40 (17)
C13—O1—C1—C6	167.70 (13)	N1—C7—C8—C9	−178.39 (17)
C1—O1—C13—C14	−170.80 (13)	C12—C7—C8—C9	0.5 (2)
C3—O2—C2—C1	177.97 (14)	N1—C7—C12—C11	179.67 (15)
C3—O2—C2—C5	−0.38 (19)	C8—C7—C12—N3	−178.76 (14)
C2—O2—C3—C4	0.0 (2)	C8—C7—C12—C11	0.5 (2)
N2—N1—C6—C1	−84.26 (17)	C7—C8—C9—C10	−1.1 (2)
C7—N1—C6—C1	96.81 (19)	C11—C10—C9—C8	0.7 (3)
N2—N1—C7—C8	178.45 (16)	C12—C11—C10—C9	0.3 (2)
N2—N1—C7—C12	−0.58 (17)	N3—C12—C11—C10	178.19 (16)
C6—N1—C7—C8	−2.5 (3)	C7—C12—C11—C10	−0.9 (2)
C6—N1—C7—C12	178.42 (15)	C15—C14—C13—O1	177.03 (15)
N3—N2—N1—C6	−178.57 (13)	C19—C14—C13—O1	−1.8 (2)
N3—N2—N1—C7	0.56 (17)	C13—C14—C15—Cl1	−0.1 (2)
N1—N2—N3—C12	−0.28 (17)	C13—C14—C15—C16	−179.17 (16)
N2—N3—C12—C7	−0.08 (18)	C19—C14—C15—Cl1	178.80 (13)
N2—N3—C12—C11	−179.25 (17)	C19—C14—C15—C16	−0.3 (3)
O1—C1—C2—O2	−63.48 (18)	C13—C14—C19—C18	179.09 (15)
O1—C1—C2—C5	114.4 (2)	C15—C14—C19—C18	0.2 (2)
C6—C1—C2—O2	55.36 (18)	Cl1—C15—C16—C17	−178.90 (13)
C6—C1—C2—C5	−126.8 (2)	C14—C15—C16—C17	0.2 (3)
O1—C1—C6—N1	−59.57 (16)	Cl2—C17—C16—C15	179.06 (13)
C2—C1—C6—N1	178.02 (13)	C18—C17—C16—C15	0.0 (3)
O2—C2—C5—C4	0.6 (2)	Cl2—C17—C18—C19	−179.11 (12)
C1—C2—C5—C4	−177.35 (18)	C16—C17—C18—C19	0.0 (3)
O2—C3—C4—C5	0.4 (2)	C14—C19—C18—C17	−0.1 (3)
C2—C5—C4—C3	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N3ⁱ	0.93	2.59	3.452 (2)	155
C8—H8···Cgⁱⁱ	0.93	2.92	3.782 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅Cl₂N₃O₂
M_r	388.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	11.5452 (2), 20.0350 (5), 8.3317 (2)
β (°)	105.598 (2)
V (Å³)	1856.21 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.50 × 0.30 × 0.08

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.837, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	31461, 4251, 3252
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 1.04
No. of reflections	4251
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.34

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), 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

Cg is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N3ⁱ	0.93	2.59	3.452 (2)	155
C8—H8···Cgⁱⁱ	0.93	2.92	3.782 (2)	155

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

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2010-13-02-05).

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Volume 68| Part 1| January 2012| Pages o139-o140

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