In the title compound, C10H10Cl2N4O, the hy­droxy group and benzene ring are disposed to opposite sides of the central 1,2,3-triazolyl ring. The dihedral angle between the five- and six-membered rings is 87.51 (12)°, and the C-O bond of the hy­droxy group lies almost normal to the plane of the 5-membered ring [N-C-C-O = -93.2 (2)°]. An intra­molecular amino-N-H...Cl hydrogen bond is noted. In the extended structure, supra­molecular layers in the ab plane are formed via hy­droxy-O-H...N(ring) and amine-N-H...O(hy­droxy) hydrogen bonds. The layers are connected along the c axis by [pi]-[pi] contacts between benzene rings [inter-centroid distance = 3.7789 (13) Å] and by C-Cl...[pi] inter­actions

Almeida, Maria C. B. de

Cunha, Anna C.

Ferreira, Vitor F.

Jordão, Alessandro K.

Souza, Maria C. B. V. de

Tiekink, Edward R. T. *

Wardell, James L.

In the title compound, C10H10Cl2N4O, the hydroxy group and benzene ring are disposed to opposite sides of the central 1,2,3-triazolyl ring. The dihedral angle between the five- and six-membered rings is 87.51 (12)°, and the C—O bond of the hydroxy group lies almost normal to the plane of the 5-membered ring [N—C—C—O = −93.2 (2)°]. An intramolecular amino-N—H...Cl hydrogen bond is noted. In the extended structure, supramolecular layers in theabplane are formedviahydroxy-O—H...N(ring) and amine-N—H...O(hydroxy) hydrogen bonds. The layers are connected along thecaxis by π–π contacts between benzene rings [inter-centroid distance = 3.7789 (13) Å] and by C—Cl...π interactions.</jats:p

Anna C. Cunha

Alessandro K. Jordão

Maria C. B. V. de Souza

Vitor F. Ferreira

Maria C. B. de Almeida

James L. Wardell

Edward R. T. Tiekink

Crossref

IUCrData

[1-(2,5-Dichloroanilino)-5-methyl-1<i>H</i>-1,2,3-triazol-4-yl]methanol

In the title compound, C10H10Cl2N4O, the hydroxy group and benzene ring are disposed to opposite sides of the central 1,2,3-triazolyl ring. The dihedral angle between the five- and six-membered rings is 87.51 (12)°, and the C—O bond of the hydroxy group lies almost normal to the plane of the 5-membered ring [N—C—C—O = −93.2 (2)°]. An intramolecular amino-N—H...Cl hydrogen bond is noted. In the extended structure, supramolecular layers in the ab plane are formed via hydroxy-O—H...N(ring) and amine-N—H...O(hydroxy) hydrogen bonds. The layers are connected along the c axis by π–π contacts between benzene rings [inter-centroid distance = 3.7789 (13) Å] and by C—Cl...π interactions

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[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol

Sunway Institutional Repository

data reportsIUCrData (2016). 1, x152447 http://dx.doi.org/10.1107/S2414314615024475 1 of 3[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanolAnna C. Cunha,a Alessandro K. Jorda˜o,b Maria C. B. V. de Souza,a Vitor F. Ferreira,aMaria C. B. de Almeida,a James L. Wardellc,d‡ and Edward R. T. Tiekinke*aUniversidade Federal Fluminense, Departamento de Quı´mica Orgaˆnica, Programa de Po´s-Graduac¸o˜ em Quı´mica,24020-141 Nitero´i, RJ, Brazil, bUnidade Universita´ria de Farma´cia, Fundac¸o˜ Centro Universita´rio Estadual da ZonaOeste, 23070-200, Rio de Janeiro, RJ, Brazil, cFioCruz-Fundac¸a˜o Oswaldo Cruz, Instituto de Tecnologia em Fa´rmacos-Far-Manguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil, dDepartment ofChemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK, and eCentre for Crystalline Materials,Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.*Correspondence e-mail: edwardt@sunway.edu.myIn the title compound, C10H10Cl2N4O, the hydroxy group and benzene ring aredisposed to opposite sides of the central 1,2,3-triazolyl ring. The dihedral anglebetween the five- and six-membered rings is 87.51 (12), and the C—O bond ofthe hydroxy group lies almost normal to the plane of the 5-membered ring [N—C—C—O = 93.2 (2)]. An intramolecular amino-N—H  Cl hydrogen bond isnoted. In the extended structure, supramolecular layers in the ab plane areformed via hydroxy-O—H  N(ring) and amine-N—H  O(hydroxy) hydrogenbonds. The layers are connected along the c axis by – contacts betweenbenzene rings [inter-centroid distance = 3.7789 (13) A˚] and by C—Cl  interactions.Structure description1,2,3-Triazole derivatives attract continuing interest as a result of their biological activ-ities (Dehaen & Bakulev, 2014). Diseases that have been evaluated recently includetuberculosis (Jorda˜o et al., 2011), and the susceptibility of Cantagalo virus to 1,2,3-triazoles has also been investigated (Jorda˜o et al., 2009). These studies have provided anumber of crystals enabling systematic studies of the influence of the electronegativity ofaryl-bound substituents upon crystal packing patterns (Cunha et al., 2013; Seth et al.,2015).Received 16 December 2015Accepted 20 December 2015Edited by W. T. A. Harrison, University ofAberdeen, Scotland‡ Additional correspondence author, e-mail:j.wardell@abdn.ac.uk.Keywords: crystal structure; 1,2,3-triazolyl;alcohol; hydrogen bonding.CCDC reference: 672063Structural data: full structural data are availablefrom iucrdata.iucr.orgISSN 2414-31462 of 3 Cunha et al.  C10H10Cl2N4O IUCrData (2016). 1, x152447data reportsThe central 1,2,3-triazolyl ring (r.m.s. deviation = 0.006 A˚)in the title compound, Fig. 1, is flanked by C1-bound hy-droxymethyl and N2-bound amino-2,5-dichlorobenzenesubstituents which lie to opposite sides of the ring. The C—Ogrouping of the hydroxyl group lies almost normal to the ringwith the N4—C1—C10—O1 torsion angle being 93.2 (2).The dihedral angle between the triazolyl and benzene rings is87.51 (12), with the latter being almost perpendicular,forming a N2—N1—C4—C5 torsion angle of 8.9 (3). Thisalignment allows for the formation of an intramolecularamino-N—H  Cl hydrogen bond, Table 1.In the molecular packing, the hydroxy group is pivotal inthe hydrogen-bonding scheme, forming donor hydroxy-O—H  N(ring) and acceptor amine-N—H  O(hydroxy) inter-actions, Table 1. The latter interactions assemble moleculesinto dimers and these are in turn connected into supra-molecular layers in the ab plane by the former interactions.The connections between layers are afforded by inter-digi-tating benzene rings via — contacts [inter-centroid distance= 3.7789 (13) A˚ for symmetry operation 1  x, 12 + y, 32  z]and C—Cl   interactions, Table 1 and Fig. 2.Synthesis and crystallizationA solution of the desired 4-carbethoxy-triazole (Cunha et al.,2013) (1.00 mmol) in anhydrous THF (5 ml) was addeddropwise to a suspension of LiAlH4 (2 mmol) in anhydrousTHF (10 ml) under a nitrogen atmosphere at 0C. The reac-tion mixture was stirred at room temperature for 2 h, water(10 ml) was added, the aqueous layer acidified to pH 1 with1M HCl, and extracted with CH2Cl2 (3 ). The organicFigure 1The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.Table 1Hydrogen-bond geometry (A˚, ).Cg1 is the centroid of the C4–C9 ring.D—H  A D—H H  A D  A D—H  AN1—H1N  Cl2 0.87 (2) 2.67 (2) 2.9530 (19) 100 (2)O1—H1O  N4i 0.84 (2) 2.01 (2) 2.836 (2) 169 (2)N1—H1N  O1ii 0.87 (2) 2.01 (2) 2.848 (3) 165 (2)C6—Cl1  Cg1iii 1.74 (1) 3.73 (1) 5.411 (3) 161 (1)Symmetry codes: (i) xþ 2; y 12;zþ 52; (ii) xþ 2;yþ 1;z þ 2; (iii)x þ 1;yþ 1;zþ 2.Figure 2Aview of the unit cell contents of the title compound shown in projectiondown the b axis. The O—H  O, N—H  O, — and C—Cl  interactions are shown as orange, blue, green and brown dashed lines,respectively.Table 2Experimental details.Crystal dataChemical formula C10H10Cl2N4OMr 273.12Crystal system, space group Monoclinic, P21/cTemperature (K) 120a, b, c (A˚) 12.1802 (5), 7.3646 (4), 13.9001 (8) () 112.276 (3)V (A˚3) 1153.81 (11)Z 4Radiation type Mo K (mm1) 0.55Crystal size (mm) 0.26  0.18  0.16Data collectionDiffractometer Bruker–Nonius 95mm CCDcamera on -goniostatdiffractometerAbsorption correction Multi-scan (SADABS; Sheldrick,2003)Tmin, Tmax 0.768, 1.000No. of measured, independent andobserved [I > 2(I)] reflections12461, 2645, 1963Rint 0.062(sin /	)max (A˚1) 0.649RefinementR[F 2 > 2(F 2)], wR(F 2), S 0.043, 0.117, 1.06No. of reflections 2645No. of parameters 161No. of restraints 2max, min (e A˚3) 0.33, 0.40Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft,1998), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 forWindows (Farrugia, 2012),DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).data reportsIUCrData (2016). 1, x152447 Cunha et al.  C10H10Cl2N4O 3 of 3extracts were combined, dried with Na2SO4, and concentratedunder reduced pressure. The resulting residue was washedwith hexane/dichloromethane (3:1) and dried under vacuum.44% yield. Crystals were obtained from the slow evaporationof its methanol solution. M.p. 197C. IR (KBr) max (cm1):3184 (N—H); 3096 (O—H). 1H NMR (300 MHz, DMSO-d6) :2.18 (s, 3H, CH3), 4.55 (d, 2H, J = 5.6 Hz, CH2OH), 5.19 (t, 1H,J = 5.6 Hz, CH2OH), 5.80 (d, 1H, J = 2.4 Hz, H5), 7.00 (dd, 1H,J = 2.4 & 8.5 Hz, H7), 7.50 (d, 1H, J= 8.5 Hz, H8), 10.21 (s, 1H,NH). 13C NMR (75 MHz, DMSO-d6) : 6.8 (CH3), 54.8 (CH2),112.4 (C5), 116.4 (C6), 121.5 (C7), 131.3 (C8), 132.0 (C9), 132.7(C1or C2), 143.6 (C1 or C2), 143.7 (C4). Anal. calcd. ForC10H10Cl2N4O: C, 43.98; H, 3.69; N, 20.51. Found: C, 44.01; H,3.72; N, 20.09.RefinementCrystal data, data collection and structure refinement detailsare summarized in Table 2.AcknowledgementsThis work was supported by the Brazilian agency FAPERJ.Fellowships granted to Universidade Federal Fluminense byFAPERJ, CAPES and CNPq-PIBIC are gratefully acknowl-edged.ReferencesBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn,Germany.Cunha, A. C., Ferreira, V. F., Jorda˜o, A. K., de Souza, M. C. B. V.,Wardell, S. M. S. V., Wardell, J. L., Tan, P. A., Bettens, R. P. A., Seth,S. K. & Tiekink, E. R. T. (2013). CrystEngComm, 15, 4917–4929.Dehaen, W. & Bakulev, V. A. (2014). Chemistry of 1,2,3-triazoles.Topics in Heterocyclic Chemistry, Vol. 40. Berlin Heidleberg:Springer-Verlag.Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, TheNetherlands.Jorda˜o, A. K., Afonso, P. P., Ferreira, V. F., de Souza, M. C., Almeida,M. C., Beltrame, C. O., Paiva, D. P., Wardell, S. M. S. V., Wardell,J. L., Tiekink, E. R. T., Damaso, R. & Cunha, A. C. (2009). Eur. J.Med. Chem. 44, 3777–3783.Jorda˜o, A. K., Sathler, P. C., Ferreira, V. F., Campos, V. R., de Souza,M. C. B. V., Castro, H. C., Lannes, A., Lourenco, A., Rodrigues,C. R., Bello, M. L., Lourenco, M. C. S., Carvalho, G. S. L., Almeida,M. C. B. & Cunha, A. C. (2011). Bioorg. Med. Chem. 19, 5605–5611.Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol.276, Macromolecular Crystallography, Part A, edited by C. W.Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.Seth, S. K., Lee, V. S., Yana, J., Zain, S. M., Cunha, A. C., Ferreira,V. F., Jorda˜o, A. K., de Souza, M. C. B. V., Wardell, S. M. S. V.,Wardell, J. L. & Tiekink, E. R. T. (2015). CrystEngComm, 17, 2255–2266.Sheldrick, G. M. (2003). SADABS. University of Go¨ttingen,Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.data reportsdata-1IUCrData (2016). 1, x152447    full crystallographic dataIUCrData (2016). 1, x152447    [doi:10.1107/S2414314615024475][1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanolAnna C. Cunha, Alessandro K. Jordão, Maria C. B. V. de Souza, Vitor F. Ferreira, Maria C. B. de Almeida, James L. Wardell and Edward R. T. Tiekink[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol Crystal data C10H10Cl2N4OMr = 273.12Monoclinic, P21/ca = 12.1802 (5) Åb = 7.3646 (4) Åc = 13.9001 (8) Åβ = 112.276 (3)°V = 1153.81 (11) Å3Z = 4F(000) = 560Dx = 1.572 Mg m−3Mo Kα radiation, λ = 0.71069 ÅCell parameters from 2686 reflectionsθ = 2.9–27.5°µ = 0.55 mm−1T = 120 KBlock, colourless0.26 × 0.18 × 0.16 mmData collection Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometerRadiation source: Bruker-Nonius FR591 rotating anodeGraphite monochromatorDetector resolution: 9.091 pixels mm-1φ & ω scansAbsorption correction: multi-scan (SADABS; Sheldrick, 2003)Tmin = 0.768, Tmax = 1.00012461 measured reflections2645 independent reflections1963 reflections with I > 2σ(I)Rint = 0.062θmax = 27.5°, θmin = 3.0°h = −15→14k = −9→9l = −18→17Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.043wR(F2) = 0.117S = 1.062645 reflections161 parameters2 restraintsHydrogen site location: mixedw = 1/[σ2(Fo2) + (0.0528P)2 + 0.5445P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.33 e Å−3Δρmin = −0.39 e Å−3Special 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.data reportsdata-2IUCrData (2016). 1, x152447    Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqCl1 0.37932 (5) 0.38765 (8) 0.87969 (5) 0.02943 (19)Cl2 0.68215 (5) 0.39438 (8) 0.60698 (4) 0.02549 (18)O1 1.07381 (14) 0.3879 (2) 1.25648 (13) 0.0289 (4)H1O 1.098 (2) 0.319 (3) 1.3086 (16) 0.043*N1 0.78023 (15) 0.4396 (3) 0.83509 (14) 0.0188 (4)H1N 0.8125 (19) 0.503 (3) 0.8004 (17) 0.023*N2 0.82967 (15) 0.4789 (2) 0.94015 (13) 0.0163 (4)N3 0.83152 (15) 0.6498 (2) 0.97786 (14) 0.0190 (4)N4 0.87624 (15) 0.6334 (2) 1.07929 (14) 0.0190 (4)C1 0.90092 (17) 0.4551 (3) 1.10644 (16) 0.0177 (5)C2 0.87186 (17) 0.3534 (3) 1.01696 (17) 0.0175 (5)C3 0.8799 (2) 0.1582 (3) 0.99578 (19) 0.0249 (5)H3A 0.8016 0.1136 0.9502 0.037*H3B 0.9070 0.0906 1.0614 0.037*H3C 0.9364 0.1410 0.9617 0.037*C4 0.65537 (18) 0.4209 (3) 0.79153 (16) 0.0164 (4)C5 0.58710 (19) 0.4161 (3) 0.85238 (17) 0.0190 (5)H5 0.6234 0.4282 0.9258 0.023*C6 0.46531 (19) 0.3934 (3) 0.80412 (18) 0.0195 (5)C7 0.40899 (19) 0.3747 (3) 0.69811 (18) 0.0227 (5)H7 0.3252 0.3615 0.6670 0.027*C8 0.4772 (2) 0.3757 (3) 0.63790 (18) 0.0231 (5)H8 0.4404 0.3614 0.5647 0.028*C9 0.59873 (19) 0.3976 (3) 0.68423 (17) 0.0185 (5)C10 0.94792 (19) 0.3937 (3) 1.21697 (17) 0.0211 (5)H10A 0.9215 0.4782 1.2592 0.025*H10B 0.9164 0.2715 1.2216 0.025*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23Cl1 0.0241 (3) 0.0385 (4) 0.0300 (4) −0.0026 (2) 0.0151 (3) −0.0009 (3)Cl2 0.0269 (3) 0.0356 (4) 0.0139 (3) 0.0017 (2) 0.0077 (2) −0.0017 (2)O1 0.0178 (8) 0.0412 (11) 0.0218 (9) −0.0036 (7) 0.0011 (7) 0.0160 (7)N1 0.0197 (9) 0.0277 (10) 0.0083 (9) −0.0043 (7) 0.0045 (7) −0.0016 (7)N2 0.0177 (8) 0.0190 (10) 0.0111 (9) −0.0001 (7) 0.0041 (7) −0.0008 (7)N3 0.0193 (9) 0.0213 (10) 0.0143 (10) −0.0011 (7) 0.0038 (7) −0.0008 (7)N4 0.0195 (9) 0.0230 (10) 0.0128 (10) −0.0006 (7) 0.0043 (7) −0.0009 (7)C1 0.0149 (10) 0.0225 (11) 0.0155 (11) −0.0018 (8) 0.0055 (8) 0.0003 (9)C2 0.0147 (10) 0.0228 (12) 0.0151 (11) −0.0004 (8) 0.0060 (8) 0.0020 (9)C3 0.0324 (13) 0.0213 (12) 0.0226 (13) 0.0030 (9) 0.0122 (10) 0.0026 (10)C4 0.0161 (10) 0.0163 (10) 0.0142 (11) 0.0004 (8) 0.0030 (8) 0.0005 (8)C5 0.0211 (11) 0.0224 (12) 0.0114 (11) −0.0003 (8) 0.0037 (9) −0.0013 (8)C6 0.0193 (11) 0.0182 (11) 0.0224 (12) −0.0003 (8) 0.0095 (9) −0.0004 (9)C7 0.0170 (11) 0.0217 (12) 0.0242 (13) −0.0011 (8) 0.0020 (9) −0.0015 (9)data reportsdata-3IUCrData (2016). 1, x152447    C8 0.0248 (12) 0.0238 (12) 0.0143 (11) 0.0000 (9) 0.0002 (9) −0.0013 (9)C9 0.0232 (11) 0.0176 (11) 0.0146 (11) 0.0014 (8) 0.0070 (9) −0.0002 (8)C10 0.0201 (11) 0.0281 (13) 0.0140 (11) −0.0008 (9) 0.0055 (9) 0.0014 (9)Geometric parameters (Å, º) Cl1—C6 1.742 (2) C3—H3A 0.9800Cl2—C9 1.736 (2) C3—H3B 0.9800O1—C10 1.420 (3) C3—H3C 0.9800O1—H1O 0.839 (10) C4—C5 1.393 (3)N1—N2 1.383 (2) C4—C9 1.396 (3)N1—C4 1.414 (3) C5—C6 1.387 (3)N1—H1N 0.866 (10) C5—H5 0.9500N2—C2 1.357 (3) C6—C7 1.376 (3)N2—N3 1.361 (3) C7—C8 1.385 (3)N3—N4 1.310 (3) C7—H7 0.9500N4—C1 1.368 (3) C8—C9 1.382 (3)C1—C2 1.378 (3) C8—H8 0.9500C1—C10 1.492 (3) C10—H10A 0.9900C2—C3 1.478 (3) C10—H10B 0.9900C10—O1—H1O 109 (2) C9—C4—N1 119.01 (18)N2—N1—C4 116.08 (16) C6—C5—C4 119.0 (2)N2—N1—H1N 111.5 (16) C6—C5—H5 120.5C4—N1—H1N 117.1 (16) C4—C5—H5 120.5C2—N2—N3 112.40 (17) C7—C6—C5 122.5 (2)C2—N2—N1 124.87 (18) C7—C6—Cl1 118.26 (16)N3—N2—N1 122.50 (17) C5—C6—Cl1 119.24 (17)N4—N3—N2 105.56 (16) C6—C7—C8 118.48 (19)N3—N4—C1 110.12 (17) C6—C7—H7 120.8N4—C1—C2 108.56 (19) C8—C7—H7 120.8N4—C1—C10 122.24 (19) C9—C8—C7 120.1 (2)C2—C1—C10 129.2 (2) C9—C8—H8 120.0N2—C2—C1 103.36 (18) C7—C8—H8 120.0N2—C2—C3 122.65 (19) C8—C9—C4 121.3 (2)C1—C2—C3 134.0 (2) C8—C9—Cl2 119.02 (17)C2—C3—H3A 109.5 C4—C9—Cl2 119.63 (16)C2—C3—H3B 109.5 O1—C10—C1 110.11 (17)H3A—C3—H3B 109.5 O1—C10—H10A 109.6C2—C3—H3C 109.5 C1—C10—H10A 109.6H3A—C3—H3C 109.5 O1—C10—H10B 109.6H3B—C3—H3C 109.5 C1—C10—H10B 109.6C5—C4—C9 118.58 (19) H10A—C10—H10B 108.2C5—C4—N1 122.34 (19)C4—N1—N2—C2 93.4 (2) N2—N1—C4—C9 174.27 (18)C4—N1—N2—N3 −80.6 (2) C9—C4—C5—C6 −1.7 (3)C2—N2—N3—N4 0.6 (2) N1—C4—C5—C6 −178.6 (2)data reportsdata-4IUCrData (2016). 1, x152447    N1—N2—N3—N4 175.36 (16) C4—C5—C6—C7 0.2 (3)N2—N3—N4—C1 −1.0 (2) C4—C5—C6—Cl1 −179.89 (16)N3—N4—C1—C2 1.0 (2) C5—C6—C7—C8 1.1 (3)N3—N4—C1—C10 −177.30 (18) Cl1—C6—C7—C8 −178.78 (17)N3—N2—C2—C1 0.0 (2) C6—C7—C8—C9 −0.9 (3)N1—N2—C2—C1 −174.61 (17) C7—C8—C9—C4 −0.7 (3)N3—N2—C2—C3 −179.43 (18) C7—C8—C9—Cl2 178.92 (17)N1—N2—C2—C3 6.0 (3) C5—C4—C9—C8 2.0 (3)N4—C1—C2—N2 −0.6 (2) N1—C4—C9—C8 178.94 (19)C10—C1—C2—N2 177.57 (19) C5—C4—C9—Cl2 −177.60 (16)N4—C1—C2—C3 178.7 (2) N1—C4—C9—Cl2 −0.6 (3)C10—C1—C2—C3 −3.1 (4) N4—C1—C10—O1 −93.2 (2)N2—N1—C4—C5 −8.9 (3) C2—C1—C10—O1 88.9 (3)Hydrogen-bond geometry (Å, º) Cg1 is the centroid of the C4–C9 ring.D—H···A D—H H···A D···A D—H···AN1—H1N···Cl2 0.87 (2) 2.67 (2) 2.9530 (19) 100 (2)O1—H1O···N4i 0.84 (2) 2.01 (2) 2.836 (2) 169 (2)N1—H1N···O1ii 0.87 (2) 2.01 (2) 2.848 (3) 165 (2)C6—Cl1···Cg1iii 1.74 (1) 3.73 (1) 5.411 (3) 161 (1)Symmetry codes: (i) −x+2, y−1/2, −z+5/2; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+2.

[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol

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