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- Acta Crystallogr Sect E Struct Rep Online
- v.66(Pt 1); 2010 Jan 1
- PMC2980028
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![1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (1)](https://i0.wp.com/www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/logo-actae.gif "1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (1)"){kind=logo}
Acta Crystallogr Sect E Struct Rep Online. 2010 Jan 1; 66(Pt 1): o107–o108.
Published online 2009 Dec 12. doi:10.1107/S1600536809052568
PMCID: PMC2980028
PMID: 21579997
Özden Özel Güven,a Hakan Tahtacı,a Simon J. Coles,b and Tuncer Hökelekc,*
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Associated Data
- Supplementary Materials
Abstract
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,
![1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (3)](data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw== "1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (3)")
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
See AlsoGenetic polymorphisms associated with cardiovascular disorders and drug response, methods of detection and uses thereofAgromax New Holland está contratando SUPERVISOR DE SERVIÇOS PÓS VENDAS- SANTARÉM em: Santarem, Pará, Brazil | LinkedIn— [MICRO UPDATE #5] HOW WE HAVE EFFECTED A SUFFOCATION OF THE ANZAC TRADITION ASSOCIATED TO ANY IDOLATROUS AND DELUSIONAL ROMAN CATHOLICISMMo Kα radiation
μ = 0.44 mm−1
T = 120 K
0.40 × 0.40 × 0.10 mm
![1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (3)](https://i0.wp.com/www.ncbi.nlm.nih.gov/pmc/articles/PMC2980028/bin/e-66-0o107-efi1.jpg "1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (3)")
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[F 2 > 2σ(F 2)] = 0.067
wR(F 2) = 0.180
S = 1.04
3438 reflections
200 parameters
H-atom parameters constrained
Δρmax = 1.20 e Å−3
Δρmin = −0.76 e Å−3
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.
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 |
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Symmetry codes: (i) ![1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (4)](https://i0.wp.com/www.ncbi.nlm.nih.gov/pmc/articles/PMC2980028/bin/e-66-0o107-efi2.jpg "1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (4)")
; (ii) ![1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (5)](https://i0.wp.com/www.ncbi.nlm.nih.gov/pmc/articles/PMC2980028/bin/e-66-0o107-efi3.jpg "1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (5)")
; (iii) ![1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (6)](https://i0.wp.com/www.ncbi.nlm.nih.gov/pmc/articles/PMC2980028/bin/e-66-0o107-efi4.jpg "1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole (6)")
. Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052568/xu2704sup1.cif
Click here to view.(19K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052568/xu2704Isup2.hkl
Click here to view.(165K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge Zonguldak Karaelmas University Research Fund (project No. 2008–13–02–06) for financial support.
supplementary crystallographic information
Comment
In recent years, among antifungal agents, azole derivatives still have animportant place in the class of systemic antifungal drugs. Some etherstructures containing 1H-imidazole ring like micozanole, ecozanole andsulconazole have been synthesized and developed for clinical uses asantifungal agents (Godefroi et al., 1969). The crystalstructures ofthese 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-triazolering have been reported (Wahbi et al., 1995). Itraconazole(Peeterset al., 1996) and fluconazole (Caira et al.,2004) are1H-1,2,4-triazole ring containing azole derivatives. 1,2,4-Triazolesare biologically interesting molecules and their chemistry is receivingconsiderable attention due to antihypertensive, antifungal and antibacterialproperties (Paulvannan et al., 2001). Ether structurespossessing1H-benzimidazole ring have been reported to show antibacterial activitymore than antifungal activity (Özel Güven et al.,2007a,b).The crystal structures of 1H-benzimidazole ring containing etherderivatives (Özel Güven et al.,2008a,b,c,d) andalso,1H-1,2,4-triazole ring containing ether derivatives have beenreported recently (Özel Güven et al., 2008e,f;Özel Güvenet al., 2009). Now, we report herein the crystal structure of2,6-dichloro- derivative of 1H-1,2,4-triazole and furyl ringscontaining ether structure.
In the molecule of the title compound (Fig. 1) the bond lengths and angles aregenerally within normal ranges. The planar triazole ring is oriented withrespect 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. Thedichlorobenzene ring is oriented with respect to the furan ring at a dihedralangle 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) adoptingenvelope conformation with H9B atom displaced by 0.210(1) Å from the planeof the other ring atoms.
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) linkthe molecules into centrosymmetric dimers (Fig. 2), in which they may beeffective in the stabilization of the structure. The π–π contact betweenthe dichlorobenzene rings, Cg3—Cg3i [symmetry code: (i) -x, -y, 1 - z,where Cg3 is centroid of the ring (C10-C15)] may further stabilize thestructure, with centroid-centroid distance of 3.583(2) Å. IntermolecularC—H···π interactions (Table 1) are also observed between the triazole andfuran rings.
Experimental
The title compound was synthesized by the reaction of1-(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 smallfractions. The appropriate benzyl halide (669 mg, 2.791 mmol) was addeddropwise. The mixture was stirred at room temperature for 3 h, and excesshydride was decomposed with methyl alcohol (5 ml). After evaporation todryness under reduced pressure, the crude residue was suspended with water andextracted with methylene chloride. The organic layer was dried over anhydroussodium sulfate and then evaporated to dryness. The crude residue was purifiedby chromatography on a silica-gel column using chloroform as eluent. Crystalssuitable for X-ray analysis were obtained by the recrystallization of theether from isopropanol solution (yield; 500 mg, 53%).
Refinement
H atoms were positioned geometrically, with C–H = 0.93, 0.98 and 0.97 Å foraromatic, methine and methylene H, respectively, and constrained to ride ontheir parent atoms with Uiso(H) = 1.2Ueq(C).
Figures
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.
Crystal data
| C15H13Cl2N3O2 | F(000) = 696 |
| Mr = 338.18 | Dx = 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 |
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Data collection
| Bruker–Nonius KappaCCD diffractometer | 3438 independent reflections |
| Radiation source: fine-focus sealed tube | 2775 reflections with I > 2σ(I) |
| graphite | Rint = 0.058 |
| φ and ω scans | θmax = 27.5°, θmin = 3.3° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −13→13 |
| Tmin = 0.837, Tmax = 0.955 | k = −14→15 |
| 33067 measured reflections | l = −16→16 |
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Refinement
| 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(Fo2) + (0.0984P)2 + 1.9705P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3438 reflections | Δρmax = 1.20 e Å−3 |
| 200 parameters | Δρmin = −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) |
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Special details
| 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. |
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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) |
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Atomic displacement parameters (Å2)
| 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) |
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Geometric parameters (Å, °)
| 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) |
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Hydrogen-bond geometry (Å, °)
Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings,respectively.
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| 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 |
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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.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2704).
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