The title mol­ecule, C17H16N4, is a bis-indazole crystallized in the rare 2H-tautomeric form. Indazole heterocycles are connected by a propane C3 chain, and the mol­ecule is placed on a general position, in contrast to the analogous compound with a central C2 ethane bridge, which was previously found to be placed on an inversion center in the same space group. In the title mol­ecule, indazole rings make a dihedral angle of 60.11 (7)°, and the bridging alkyl chain displays a trans conformation, resulting in a W-shaped mol­ecule. In the crystal, mol­ecules inter­act weakly through π–π contacts between inversion-related pyrazole rings, with a centroid–centroid separation of 3.746 (2) Å

Bernès, Sylvain

Elizondo Martínez, Perla

Ovalle, Saúl

Pérez Rodríguez, Nancy

English

PubMed

Ovalle Pérez, Saúl

Repositorio Academico Digital UANL

2,20-(Propane-1,3-diyl)bis(2H-indazole)Sau´l Ovalle,a Sylvain Berne`s,b Nancy Pe´rez Rodrı´guezaand Perla Elizondo Martı´neza*aLaboratorio de Quı´mica Industrial, Centro de Laboratorios Especializados, Facultadde Ciencias Quı´micas, Universidad Auto´noma de Nuevo Leo´n, Pedro de Alba S/N,66451 San Nicola´s de los Garza, NL, Mexico, and bDivisio´n de Estudios dePosgrado, Facultad de Ciencias Quı´micas, Universidad Auto´noma de Nuevo Leo´n,Guerrero y Progreso S/N, Col. Trevin˜o, 64570 Monterrey, NL, MexicoCorrespondence e-mail: sylvain_bernes@hotmail.comReceived 14 June 2011; accepted 18 July 2011Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.004 A˚;R factor = 0.049; wR factor = 0.162; data-to-parameter ratio = 13.7.The title molecule, C17H16N4, is a bis-indazole crystallized inthe rare 2H-tautomeric form. Indazole heterocycles areconnected by a propane C3 chain, and the molecule is placedon a general position, in contrast to the analogous compoundwith a central C2 ethane bridge, which was previously found tobe placed on an inversion center in the same space group. Inthe title molecule, indazole rings make a dihedral angle of60.11 (7), and the bridging alkyl chain displays a transconformation, resulting in a W-shaped molecule. In the crystal,molecules interact weakly through – contacts betweeninversion-related pyrazole rings, with a centroid–centroidseparation of 3.746 (2) A˚.Related literatureFor the synthesis of 2H-indazoles, see: Wu et al. (2010). Forstudies of 1H !2H tautomerism in indazoles, see: Alkorta& Elguero (2005); Yu et al. (2006). For 2H-indazole X-raystructures, see: Saczewski et al. (2001); Rodrı´guez de Barbarı´net al. (2006); Ramos Silva et al. (2008); Hurtado et al. (2009);Zhou et al. (2010); Long et al. (2011).ExperimentalCrystal dataC17H16N4Mr = 276.34Orthorhombic, Pbcaa = 8.182 (2) A˚b = 10.549 (4) A˚c = 34.179 (9) A˚V = 2950.1 (16) A˚3Z = 8Mo K radiation = 0.08 mm1T = 298 K0.60  0.40  0.18 mmData collectionSiemens P4 diffractometer8195 measured reflections2621 independent reflections1607 reflections with I > 2(I)Rint = 0.0423 standard reflections every 97reflectionsintensity decay: 1.5%RefinementR[F 2 > 2(F 2)] = 0.049wR(F 2) = 0.162S = 1.102621 reflections191 parametersH-atom parameters constrainedmax = 0.20 e A˚3min = 0.21 e A˚3Data collection: XSCANS (Siemens, 1996); cell refinement:XSCANS; data reduction: XSCANS; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006);software used to prepare material for publication: SHELXL97.The authors thank the PAICyT program (Programa deApoyo a la Investigacio´n Cientı´fica y Tecnolo´gica) of theUniversidad Auto´noma de Nuevo Leo´n for supporting thiswork (project No. T004–09).Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: AA2015).ReferencesAlkorta, I. & Elguero, J. (2005). J. Phys. Org. Chem. 18, 719–724.Hurtado, J., Mac-Leod Carey, D., Mun˜oz-Castro, A., Arratia-Pe´rez, R.,Quijada, R., Wu, G., Rojas, R. & Valderrama, M. (2009). J. Organomet.Chem. 694, 2636–2641.Long, L., Liu, B.-N., Liu, M. & Liu, D.-K. (2011). Acta Cryst. E67, o1546.Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor,R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.Ramos Silva, M., Moreira, V. M., Cardoso, C., Matos Beja, A. & Salvador, J. A.R. (2008). Acta Cryst. C64, o217–o219.Rodrı´guez de Barbarı´n, C., Na´jera, B., Elizondo, P. & Cerda, P. (2006). ActaCryst. E62, o5423–o5424.Saczewski, F., Saczewski, J. & Gdaniec, M. (2001). Chem. Pharm. Bull. 49,1203–1206.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc.,Madison, Wisconsin, USA.Wu, C., Fang, Y., Larock, R. C. & Shi, F. (2010). Org. Lett. 12, 2234–2237.Yu, H.-Y., Li, B.-Z. & Guo, Y.-M. (2006). Chin. J. Chem. Phys. 19, 233–237.Zhou, X., Qin, X. & Zhang, J. (2010). Acta Cryst. E66, o2732.organic compoundso2144 Ovalle et al. doi:10.1107/S1600536811029011 Acta Cryst. (2011). E67, o2144Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supplementary materialssupplementary materialssup-1Acta Cryst. (2011). E67, o2144    [ doi:10.1107/S1600536811029011 ]2,2'-(Propane-1,3-diyl)bis(2H-indazole)S. Ovalle, S. Bernès, N. Pérez Rodríguez and P. Elizondo MartínezCommentAlthough efficient synthetic routes for 2H-indazoles are available (e.g. Wu et al., 2010) few molecules belonging to thisfamily of heterocyclic compounds have been X-ray characterized up to now. This is due, in part, to the fact that 1H tautomerfor indazoles is frequently more stable than the 2H tautomer, although the opposite situation may occur for some derivatives(Alkorta & Elguero, 2005; Yu et al., 2006). On the other hand, in the case of N2-substituted indazoles, only the 2H tau-tomer is allowed. Tautomerism equilibrium study is important, since bioavailability and other pharmacological propertiesof indazoles may be dependent on such equilibria (e.g. Ramos Silva et al., 2008). Indazole derivatives have been used, forinstance, for their anti-inflammatory activity.The title compound was prepared through a three steps procedure, the key step being the cyclization of a nitroaminederivative (compound P, see Fig. 1 and Experimental). The resulting bis-indazole consists of two 2H-indazole heterocyclesconnected by an alkyl C3 bridge (Fig. 2). The molecule lies in a general position, in space group Pbca. It is worth notingthat the analogue compound with a central C2 bridge, for which we reported the X-ray structure (Rodríguez de Barbarín etal., 2006), was found to crystallize in the same space group, although the molecule was placed on an inversion center. Fromthis pair of structures now determined, we can propose the following general rule for n-alkyl bridged bis(2H-indazoles):even-alkyl compounds should be centrosymmetric, while odd-alkyl derivatives are expected to be non-centrosymmetric,as the title compound.Molecular dimensions observed in the title compound compare well with those reported for other 2H-indazoles(Saczewski et al., 2001; Rodríguez de Barbarín et al., 2006; Hurtado et al., 2009; Zhou et al., 2010; Long et al., 2011). In-dazole rings make a dihedral angle of 60.11 (7)°. Torsion angles N2—C8—C9—C10 and C8—C9—C10—N12, -176.7 (2)and 173.5 (2)° respectively, characterize the trans conformation for the alkyl bridge, resulting in a W-shaped molecule.The crystal structure features π–π interactions of modest strength, between molecules related by inversion (Fig. 3). Theseparation between the centroid of the pyrazole ring N11/N12/C11/C17/C16 and the symmetry-related centroid at position-x, 1 - y, 1 - z, is 3.746 (2) Å.ExperimentalThe title ligand, PI, was obtained by a three steps reaction procedure (Fig. 1). The condensation between 1,3-diaminopropaneand 2-nitrobenzaldehyde produced the corresponding imine. Selective reduction of imine bonds with sodium borohydridein methanol gave amine P, which was isolated. Then, 0.044 g of Pd/C was added to a solution of P (0.005 mol) in ethanol.This mixture was refluxed for 5.5 h, with addition of hydrazine monohydrate (0.110 mol) during the first 3 h. The mixturewas filtered, distilled, and the organic phase was extracted. The product was purified by column chromatography with silicagel and ethyl acetate:hexane (2:1) as eluent. Suitable crystals were obtained by slow evaporation of an ethanol solutionat 298 K. Mp 389.4–390 K; analysis found (calc. for C17H16N4): C 73.6 (73.9), H 5.8 (5.8), N 20.5% (20.3%); IR RTA:3108 (CH Ar. νs), 2950 (–CH2– νs), 1625 (C=N Ar. δs), 1514, 1467 (C=C Ar. νs and νas). 1H NMR (300 MHz, CDCl3):supplementary materialssup-2δ, p.p.m.: 2.73 (2H, m, –CH2–), 4.41 (4H, t, N—CH2), 7.10 (2H, dd, Ar), 7.31 (2H, dd, Ar), 7.66 (2H, dd, Ar), 7.73 (2H,td, Ar), 7.95 (2H, s, NH).RefinementAll H atoms were placed in idealized positions and refined as riding to their parent C atoms, with bond lengths fixed to0.97 (methylene CH2) or 0.93 Å (aromatic CH). Isotropic displacement parameters for H atoms were calculated as Uiso(H)= 1.2 Ueq(carrier atom).FiguresFig. 1. Synthetic route for the title compound. P is the key intermediate and PI is the titlecompound.Fig. 2. ORTEP-like view of the title molecule, with displacement ellipsoids at the 30% prob-ability level for non-H atoms.Fig. 3. A part of the crystal structure representing two molecules related by inversion, whichinteract through a π–π contact involving pyrazole rings (dashed line).2,2'-(Propane-1,3-diyl)bis(2H-indazole)Crystal dataC17H16N4 Dx = 1.244 Mg m−3Mr = 276.34 Melting point: 389 KOrthorhombic, Pbca Mo Kα radiation, λ = 0.71073 ÅHall symbol: -P 2ac 2ab Cell parameters from 77 reflectionsa = 8.182 (2) Å θ = 4.6–12.4°b = 10.549 (4) Å µ = 0.08 mm−1c = 34.179 (9) Å T = 298 KV = 2950.1 (16) Å3 Prism, yellowZ = 8 0.60 × 0.40 × 0.18 mmF(000) = 1168Data collectionSiemens P4diffractometer Rint = 0.042Radiation source: fine-focus sealed tube θmax = 25.1°, θmin = 2.4°graphite h = −9→8ω scans k = −12→128195 measured reflections l = −40→402621 independent reflections 3 standard reflections every 97 reflectionssupplementary materialssup-31607 reflections with I > 2σ(I) intensity decay: 1.5%RefinementRefinement on F2 Secondary atom site location: difference Fourier mapLeast-squares matrix: full Hydrogen site location: inferred from neighbouringsitesR[F2 > 2σ(F2)] = 0.049 H-atom parameters constrainedwR(F2) = 0.162w = 1/[σ2(Fo2) + (0.0659P)2 + 0.9616P]where P = (Fo2 + 2Fc2)/3S = 1.10 (Δ/σ)max < 0.0012621 reflections Δρmax = 0.20 e Å−3191 parameters Δρmin = −0.21 e Å−30 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008),Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/40 constraints Extinction coefficient: 0.0159 (17)Primary atom site location: structure-invariant directmethodsFractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)x y z Uiso*/UeqN1 0.3628 (3) 0.67210 (17) 0.33910 (5) 0.0640 (6)N2 0.2422 (2) 0.75293 (17) 0.34924 (5) 0.0563 (5)C1 0.2608 (3) 0.8690 (2) 0.33476 (6) 0.0622 (7)H1A 0.1914 0.9378 0.3385 0.075*C2 0.4896 (4) 0.9559 (3) 0.29004 (7) 0.0773 (8)H2A 0.4529 1.0390 0.2876 0.093*C3 0.6261 (5) 0.9172 (3) 0.27178 (8) 0.0902 (10)H3A 0.6828 0.9744 0.2561 0.108*C4 0.6856 (4) 0.7935 (4) 0.27562 (9) 0.0986 (11)H4A 0.7815 0.7708 0.2628 0.118*C5 0.6062 (4) 0.7056 (3) 0.29769 (8) 0.0847 (9)H5A 0.6463 0.6235 0.3002 0.102*C6 0.4614 (3) 0.7431 (2) 0.31655 (6) 0.0610 (7)C7 0.4032 (3) 0.8675 (2) 0.31308 (6) 0.0604 (7)C8 0.1158 (3) 0.7097 (2) 0.37586 (6) 0.0639 (7)H8A 0.0822 0.6247 0.3686 0.077*H8B 0.0214 0.7649 0.3737 0.077*C9 0.1757 (3) 0.7094 (2) 0.41760 (7) 0.0646 (7)H9A 0.2737 0.6582 0.4195 0.078*H9B 0.2031 0.7952 0.4254 0.078*C10 0.0474 (3) 0.6575 (3) 0.44453 (6) 0.0671 (7)H10B −0.0458 0.7143 0.4447 0.080*H10C 0.0109 0.5760 0.4348 0.080*N11 0.2399 (2) 0.56892 (18) 0.49101 (5) 0.0611 (6)N12 0.1075 (2) 0.64232 (18) 0.48438 (5) 0.0571 (5)C11 0.0399 (3) 0.6887 (2) 0.51674 (7) 0.0615 (7)supplementary materialssup-4H11B −0.0516 0.7409 0.5181 0.074*C12 0.1239 (4) 0.6545 (2) 0.58912 (7) 0.0696 (7)H12B 0.0444 0.7040 0.6012 0.083*C13 0.2351 (3) 0.5902 (3) 0.61062 (7) 0.0699 (7)H13B 0.2306 0.5947 0.6378 0.084*C14 0.3567 (3) 0.5170 (2) 0.59287 (8) 0.0707 (7)H14C 0.4308 0.4737 0.6086 0.085*C15 0.3702 (3) 0.5070 (2) 0.55328 (7) 0.0683 (7)H15B 0.4538 0.4603 0.5418 0.082*C16 0.2530 (3) 0.5701 (2) 0.53037 (6) 0.0533 (6)C17 0.1312 (3) 0.6448 (2) 0.54797 (7) 0.0555 (6)Atomic displacement parameters (Å2)U11 U22 U33 U12 U13 U23N1 0.0772 (15) 0.0555 (11) 0.0593 (11) 0.0036 (11) 0.0102 (11) 0.0011 (9)N2 0.0647 (13) 0.0543 (10) 0.0499 (10) 0.0009 (10) 0.0040 (10) 0.0007 (8)C1 0.0780 (18) 0.0525 (13) 0.0560 (13) 0.0050 (12) −0.0062 (14) 0.0031 (10)C2 0.107 (2) 0.0695 (16) 0.0558 (14) −0.0202 (17) −0.0037 (16) 0.0056 (12)C3 0.113 (3) 0.095 (2) 0.0633 (17) −0.036 (2) 0.0138 (18) 0.0004 (15)C4 0.100 (3) 0.118 (3) 0.0780 (19) −0.011 (2) 0.0320 (18) −0.0046 (19)C5 0.095 (2) 0.0832 (19) 0.0754 (17) 0.0069 (18) 0.0252 (17) −0.0047 (15)C6 0.0760 (17) 0.0596 (14) 0.0474 (12) −0.0041 (13) 0.0039 (12) −0.0038 (10)C7 0.0796 (18) 0.0570 (13) 0.0447 (12) −0.0064 (13) −0.0031 (12) 0.0003 (10)C8 0.0633 (16) 0.0713 (15) 0.0572 (13) −0.0018 (13) 0.0053 (12) 0.0041 (11)C9 0.0662 (17) 0.0707 (15) 0.0570 (13) −0.0090 (13) 0.0045 (12) 0.0051 (12)C10 0.0665 (17) 0.0764 (16) 0.0583 (14) −0.0086 (14) 0.0020 (13) 0.0044 (12)N11 0.0601 (13) 0.0607 (12) 0.0626 (11) 0.0070 (10) 0.0088 (10) 0.0013 (9)N12 0.0542 (12) 0.0595 (11) 0.0576 (11) 0.0007 (10) 0.0071 (10) 0.0047 (9)C11 0.0608 (16) 0.0610 (14) 0.0628 (15) 0.0081 (12) 0.0103 (12) 0.0004 (11)C12 0.0737 (18) 0.0719 (16) 0.0631 (15) 0.0076 (15) 0.0085 (14) −0.0050 (12)C13 0.0792 (19) 0.0731 (16) 0.0574 (13) 0.0005 (16) −0.0023 (14) 0.0011 (12)C14 0.0732 (19) 0.0667 (15) 0.0724 (16) 0.0059 (14) −0.0063 (14) 0.0087 (13)C15 0.0687 (17) 0.0639 (14) 0.0724 (16) 0.0098 (13) 0.0054 (14) 0.0012 (12)C16 0.0535 (14) 0.0470 (11) 0.0593 (13) −0.0014 (11) 0.0061 (11) 0.0023 (10)C17 0.0570 (15) 0.0505 (12) 0.0590 (13) 0.0018 (11) 0.0072 (12) 0.0015 (10)Geometric parameters (Å, °)N1—C6 1.343 (3) C9—H9A 0.9700N1—N2 1.350 (3) C9—H9B 0.9700N2—C1 1.329 (3) C10—N12 1.457 (3)N2—C8 1.451 (3) C10—H10B 0.9700C1—C7 1.381 (4) C10—H10C 0.9700C1—H1A 0.9300 N11—C16 1.350 (3)C2—C3 1.343 (4) N11—N12 1.351 (3)C2—C7 1.410 (3) N12—C11 1.330 (3)C2—H2A 0.9300 C11—C17 1.383 (3)C3—C4 1.400 (5) C11—H11B 0.9300supplementary materialssup-5C3—H3A 0.9300 C12—C13 1.353 (4)C4—C5 1.360 (4) C12—C17 1.411 (3)C4—H4A 0.9300 C12—H12B 0.9300C5—C6 1.406 (4) C13—C14 1.398 (4)C5—H5A 0.9300 C13—H13B 0.9300C6—C7 1.401 (3) C14—C15 1.362 (4)C8—C9 1.509 (3) C14—H14C 0.9300C8—H8A 0.9700 C15—C16 1.405 (3)C8—H8B 0.9700 C15—H15B 0.9300C9—C10 1.499 (3) C16—C17 1.406 (3)C6—N1—N2 103.55 (18) C10—C9—H9B 109.5C1—N2—N1 113.7 (2) C8—C9—H9B 109.5C1—N2—C8 127.2 (2) H9A—C9—H9B 108.1N1—N2—C8 118.95 (18) N12—C10—C9 112.2 (2)N2—C1—C7 106.6 (2) N12—C10—H10B 109.2N2—C1—H1A 126.7 C9—C10—H10B 109.2C7—C1—H1A 126.7 N12—C10—H10C 109.2C3—C2—C7 118.4 (3) C9—C10—H10C 109.2C3—C2—H2A 120.8 H10B—C10—H10C 107.9C7—C2—H2A 120.8 C16—N11—N12 103.05 (18)C2—C3—C4 121.9 (3) C11—N12—N11 113.89 (19)C2—C3—H3A 119.0 C11—N12—C10 126.6 (2)C4—C3—H3A 119.0 N11—N12—C10 119.37 (19)C5—C4—C3 121.5 (3) N12—C11—C17 107.1 (2)C5—C4—H4A 119.3 N12—C11—H11B 126.5C3—C4—H4A 119.3 C17—C11—H11B 126.5C4—C5—C6 117.7 (3) C13—C12—C17 118.5 (2)C4—C5—H5A 121.1 C13—C12—H12B 120.8C6—C5—H5A 121.1 C17—C12—H12B 120.8N1—C6—C7 111.5 (2) C12—C13—C14 121.4 (2)N1—C6—C5 127.7 (2) C12—C13—H13B 119.3C7—C6—C5 120.7 (2) C14—C13—H13B 119.3C1—C7—C6 104.6 (2) C15—C14—C13 122.1 (2)C1—C7—C2 135.6 (3) C15—C14—H14C 118.9C6—C7—C2 119.8 (3) C13—C14—H14C 118.9N2—C8—C9 111.3 (2) C14—C15—C16 117.5 (2)N2—C8—H8A 109.4 C14—C15—H15B 121.2C9—C8—H8A 109.4 C16—C15—H15B 121.2N2—C8—H8B 109.4 N11—C16—C15 127.3 (2)C9—C8—H8B 109.4 N11—C16—C17 112.0 (2)H8A—C8—H8B 108.0 C15—C16—C17 120.7 (2)C10—C9—C8 110.7 (2) C11—C17—C16 103.9 (2)C10—C9—H9A 109.5 C11—C17—C12 136.2 (2)C8—C9—H9A 109.5 C16—C17—C12 119.8 (2)C6—N1—N2—C1 −0.6 (2) C8—C9—C10—N12 173.5 (2)C6—N1—N2—C8 −176.64 (19) C16—N11—N12—C11 0.5 (3)N1—N2—C1—C7 0.3 (3) C16—N11—N12—C10 −176.1 (2)C8—N2—C1—C7 176.0 (2) C9—C10—N12—C11 126.4 (3)supplementary materialssup-6C7—C2—C3—C4 −1.2 (4) C9—C10—N12—N11 −57.4 (3)C2—C3—C4—C5 1.0 (5) N11—N12—C11—C17 0.0 (3)C3—C4—C5—C6 0.2 (5) C10—N12—C11—C17 176.3 (2)N2—N1—C6—C7 0.6 (3) C17—C12—C13—C14 1.0 (4)N2—N1—C6—C5 −179.3 (2) C12—C13—C14—C15 0.3 (4)C4—C5—C6—N1 178.9 (3) C13—C14—C15—C16 −2.1 (4)C4—C5—C6—C7 −1.0 (4) N12—N11—C16—C15 179.2 (2)N2—C1—C7—C6 0.1 (2) N12—N11—C16—C17 −0.8 (2)N2—C1—C7—C2 178.5 (3) C14—C15—C16—N11 −177.3 (2)N1—C6—C7—C1 −0.5 (3) C14—C15—C16—C17 2.7 (4)C5—C6—C7—C1 179.5 (2) N12—C11—C17—C16 −0.5 (3)N1—C6—C7—C2 −179.2 (2) N12—C11—C17—C12 −177.6 (3)C5—C6—C7—C2 0.8 (4) N11—C16—C17—C11 0.8 (3)C3—C2—C7—C1 −177.9 (3) C15—C16—C17—C11 −179.2 (2)C3—C2—C7—C6 0.4 (4) N11—C16—C17—C12 178.5 (2)C1—N2—C8—C9 −97.6 (3) C15—C16—C17—C12 −1.5 (3)N1—N2—C8—C9 77.9 (3) C13—C12—C17—C11 176.4 (3)N2—C8—C9—C10 −176.7 (2) C13—C12—C17—C16 −0.4 (4)supplementary materialssup-7Fig. 1supplementary materialssup-8Fig. 2supplementary materialssup-9Fig. 3

2,2′-(Propane-1,3-diyl)bis(2H-indazole)

The title molecule, C17H16N4, is a bis-indazole crystallized in the rare 2H-tautomeric form. Indazole heterocycles are connected by a propane C3 chain, and the molecule is placed on a general position, in contrast to the analogous compound with a central C2 ethane bridge, which was previously found to be placed on an inversion center in the same space group. In the title molecule, indazole rings make a dihedral angle of 60.11&amp;#8197;(7)&amp;#176;, and the bridging alkyl chain displays a trans conformation, resulting in a W-shaped molecule. In the crystal, molecules interact weakly through &amp;#960;&amp;#8211;&amp;#960; contacts between inversion-related pyrazole rings, with a centroid&amp;#8211;centroid separation of 3.746&amp;#8197;(2)&amp;#8197;&amp;#197;

Sa&amp

Sylvain Bern&amp

Nancy P&amp

Perla Elizondo Mart&amp

Directory of Open Access Journals (new)

2,2&amp;#8242;-(Propane-1,3-diyl)bis(2H-indazole)

Saúl Ovalle

Sylvain Bernès

Nancy Pérez Rodríguez

Perla Elizondo Martínez

Crossref

Acta Crystallographica Section E Structure Reports Online

2,2′-(Propane-1,3-diyl)bis(2<i>H</i>-indazole)

A part of the crystal structure representing two molecules related by inversion, which interact through a π–π contact involving pyrazole rings (dashed line). 2,2'-(Propane-1,3-diyl)bis(2H-indazole) Crystal data

Acta Cryst.

Acta Cryst. E66, o2732. organic compounds o2144 Ovalle et al. doi:10.1107/S1600536811029011 Acta Cryst.

XSCANS. Siemens Analytical X-ray Instruments Inc.,

http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=3213583

2,2′-(Propane-1,3-di­yl)bis­(2H-indazole)

2,2′-(Propane-1,3-diyl)bis(2H-indazole)

Abstract

Similar works

Full text

Available Versions

Repositorio Academico Digital UANL

Directory of Open Access Journals (new)

Crossref

2,2′-(Propane-1,3-di­yl)bis­(2H-indazole)

Abstract

Similar works

Full text

Available Versions

Repositorio Academico Digital UANL

Directory of Open Access Journals (new)

Crossref

2,2′-(Propane-1,3-diyl)bis(2H-indazole)