B. Kalluraya

D. Revannasiddaiah

Isloor

Macrae

N. K. Lokanath

N. Vinutha

Prasath

S. Madan Kumar

S. Shobhitha

Shahani

Sheldrick

Shobhitha

Spek

Acta Crystallographica Section E

In the title compound, C17H13ClN2O2, the phenyl and chlorobenzene rings are inclined to the central pyrazole ring at 40.84 (9) and 65.30 (9)°, respectively. In the crystal, pairs of C—H...π interactions link the molecules into inversion dimers and C—H...O hydrogen bonds link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O...Cl contacts of 3.0913 (16) Å.</jats:p

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5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehydeN. Vinutha,a S. Madan Kumar,a S. Shobhitha,bB. Kalluraya,b N. K. Lokanatha and D. Revannasiddaiaha*aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore570 006, India, and bDepartment of Studies in Chemistry, Mangalore University,Mangalagangotri, Mangalore 574 199, IndiaCorrespondence e-mail: dr@physics.uni-mysore.ac.inReceived 15 March 2014; accepted 9 April 2014Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 A˚;R factor = 0.039; wR factor = 0.105; data-to-parameter ratio = 12.5.In the title compound, C17H13ClN2O2, the phenyl andchlorobenzene rings are inclined to the central pyrazole ringat 40.84 (9) and 65.30 (9), respectively. In the crystal, pairs ofC—H   interactions link the molecules into inversiondimers and C—H  O hydrogen bonds link these dimers intocolumns extended in [010]. The crystal packing exhibits shortintermolecular O  Cl contacts of 3.0913 (16) A˚.Related literatureFor biological properties and pharmocological applications ofaryloxy pyrazole derivatives, see: Rai et al. (2008); Girisha etal. (2010); Isloor et al. (2009, 2010); Shobhitha et al. (2013). Forrelated structures, see: Shahani, Fun, Ragavan et al. (2011);Shahani, Fun, Shetty et al. (2011); Prasath et al. (2011).ExperimentalCrystal dataC17H13ClN2O2Mr = 312.74Monoclinic, P21=ca = 9.1016 (7) A˚b = 7.5298 (6) A˚c = 22.1242 (16) A˚ = 93.908 (3)V = 1512.7 (2) A˚3Z = 4Cu K radiation = 2.31 mm1T = 296 K0.23  0.22  0.21 mmData collectionBruker X8 Proteum diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2013)Tmin = 0.619, Tmax = 0.6439744 measured reflections2501 independent reflections2314 reflections with I > 2(I)Rint = 0.041RefinementR[F 2 > 2(F 2)] = 0.039wR(F 2) = 0.105S = 1.032501 reflections200 parametersH-atom parameters constrainedmax = 0.25 e A˚3min = 0.38 e A˚3Table 1Hydrogen-bond geometry (A˚, ).Cg is the centroid of the C11–C16 ring.D—H  A D—H H  A D  A D—H  AC6—H6  O2i 0.93 2.58 3.503 (2) 171C2—H2  Cgii 0.93 2.63 3.476 (2) 152Symmetry codes: (i) x; y þ 1; z; (ii) xþ 2;yþ 1;zþ 1.Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT(Bruker, 2013); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:Mercury (Macrae et al., 2008); software used to prepare material forpublication: PLATON (Spek, 2009).The authors are thankful to the IOE and UPE, Universityof Mysore, for providing the single-crystal X-ray diffractionfacility and for the financial support. VN is grateful to theUGC for the award of an RFSMS Fellowship. RD acknowl-edges the UGC, New Delhi, for financial support under theMajor Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].Supporting information for this paper is available from the IUCrelectronic archives (Reference: CV5447).ReferencesBruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.Girisha, K. S., Kalluraya, B., Narayana, V. & Padmashree. (2010). Eur. J. Med.Chem. 45, 4640–4644.Isloor, A. M., Kalluraya, B. & Pai, S. K. (2010). Eur. J. Med. Chem. 45, 825–830.Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784–3787.Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P.A. (2008). J. Appl. Cryst. 41, 466–470.Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67,o2650.Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur.J. Med. Chem. 43, 1715–1720.Shahani, T., Fun, H.-K., Ragavan, R. V., Vijayakumar, V. & Venkatesh, M.(2011). Acta Cryst. E67, o475.Shahani, T., Fun, H.-K., Shetty, S. & Kalluraya, B. (2011). Acta Cryst. E67,o2646.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Shobhitha, S., Kalluraya, B., Nithinchandra, B. M., Joshi, C. G., Joshi, H. &Nidavani, R. B. (2013). Indian J. Heterocycl. Chem. 23, 33–38.Spek, A. L. (2009). Acta Cryst. D65, 148–155.organic compoundso560 Vinutha et al. doi:10.1107/S1600536814007879 Acta Cryst. (2014). E70, o560Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2014). E70, o560    supporting informationActa Cryst. (2014). E70, o560    [doi:10.1107/S1600536814007879]5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehydeN. Vinutha, S. Madan Kumar, S. Shobhitha, B. Kalluraya, N. K. Lokanath and D. RevannasiddaiahS1. Comment Aryloxy pyrazoles and their derivatives possess a significant pharmcological activities such as antimicrobial (Rai et al. 2008; Girisha et al., 2010), anti-inflammatory (Isloor et al., 2009) and analgesic activities (Shobhitha et al., 2013). The title compound can serve as an intermediate in the synthesis of various pyrazole derivatives with significant pharmacological activities (Isloor et al., 2010).In the title compound (Fig.1), all bond lengths and angles are normal and correspond well to those observed in the related compounds (Shahani, Fun, Ragavan et al., 2011; Shahani, Fun, Shetty et al., 2011; Prasath et al., 2011). The pyrazole ring makes dihedral angles of 65.30 (9)° with chlorobenzene ring and 40.84 (9)° with benzene ring. The dihedral angle between the chlorobenzene ring and benzene ring is 76.23 (9)°.In the crystal, C–H···π interactions (Table 1) link the molecules into inversion dimers, and intermolecular C–H···O hydrogen bonds (Table 1) link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O···Cl contacts of 3.0913 (16) Å.S2. Experimental The title compound was prepared by refluxing a mixture of 5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-carboxaldehyde (0.1 mol) and 4-chloro phenol (0.1 mol) in 10 ml of dimethyl sulfoxide. To this solution, 0.1 mol of potassium hydroxide was added. The reaction mixture was refluxed for 3 hrs and then it was cooled to room temperature and poured to crushed ice. The solid product that separated was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from slow evaporation of ethanol.S3. Refinement All the H atoms were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.supporting informationsup-2Acta Cryst. (2014). E70, o560    Figure 1The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. 5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde Crystal data C17H13ClN2O2Mr = 312.74Monoclinic, P21/cHall symbol: -P 2ybca = 9.1016 (7) Åb = 7.5298 (6) Åc = 22.1242 (16) Åβ = 93.908 (3)°V = 1512.7 (2) Å3Z = 4F(000) = 648Dx = 1.373 Mg m−3Cu Kα radiation, λ = 1.54178 ÅCell parameters from 2501 reflectionsθ = 4.0–64.4°µ = 2.31 mm−1supporting informationsup-3Acta Cryst. (2014). E70, o560    T = 296 KBlock, brown0.23 × 0.22 × 0.21 mmData collection Bruker X8 Proteum diffractometerRadiation source: Bruker MicroStar microfocus rotating anodeHelios multilayer optics monochromatorDetector resolution: 18.4 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2013)Tmin = 0.619, Tmax = 0.6439744 measured reflections2501 independent reflections2314 reflections with I > 2σ(I)Rint = 0.041θmax = 64.5°, θmin = 4.0°h = −10→10k = −3→8l = −25→25Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.039wR(F2) = 0.105S = 1.032501 reflections200 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0555P)2 + 0.5076P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.25 e Å−3Δρmin = −0.38 e Å−3Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4Extinction coefficient: 0.0171 (10)Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion anglesRefinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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) x y z Uiso*/UeqCl1 0.33674 (5) 0.67384 (7) 0.29951 (2) 0.0525 (2)O1 0.96938 (13) 0.67414 (15) 0.37256 (6) 0.0417 (4)O2 0.96678 (16) 0.16557 (19) 0.27222 (7) 0.0579 (5)N1 1.15356 (14) 0.51714 (19) 0.42604 (6) 0.0354 (4)N2 1.23196 (16) 0.3599 (2) 0.42482 (7) 0.0420 (5)C1 0.81860 (18) 0.6650 (2) 0.35492 (7) 0.0335 (5)C2 0.72891 (19) 0.5340 (3) 0.37544 (8) 0.0419 (5)C3 0.58011 (19) 0.5360 (3) 0.35785 (8) 0.0417 (5)C4 0.52407 (19) 0.6712 (2) 0.32108 (7) 0.0378 (5)C5 0.6139 (2) 0.8024 (2) 0.30129 (8) 0.0438 (6)C6 0.7637 (2) 0.8000 (2) 0.31799 (8) 0.0403 (6)C7 1.04684 (16) 0.5223 (2) 0.38079 (7) 0.0332 (5)supporting informationsup-4Acta Cryst. (2014). E70, o560    C8 1.05021 (18) 0.3640 (2) 0.34914 (7) 0.0354 (5)C9 1.16849 (19) 0.2680 (2) 0.37941 (8) 0.0398 (5)C10 0.9588 (2) 0.3101 (3) 0.29611 (8) 0.0407 (6)C11 1.20153 (18) 0.6520 (2) 0.46814 (7) 0.0336 (5)C12 1.3510 (2) 0.6767 (2) 0.47974 (8) 0.0407 (6)C13 1.4008 (2) 0.8051 (3) 0.52092 (9) 0.0488 (6)C14 1.3028 (2) 0.9086 (3) 0.54945 (9) 0.0533 (7)C15 1.1529 (2) 0.8822 (3) 0.53819 (8) 0.0495 (6)C16 1.10095 (19) 0.7530 (2) 0.49751 (7) 0.0404 (5)C17 1.2243 (2) 0.0881 (3) 0.36473 (11) 0.0592 (7)H02A 1.30480 0.05740 0.39310 0.0890*H2 0.76800 0.44510 0.40090 0.0500*H02B 1.25740 0.08840 0.32440 0.0890*H3 0.51850 0.44700 0.37070 0.0500*H02C 1.14670 0.00270 0.36720 0.0890*H5 0.57430 0.89290 0.27670 0.0530*H6 0.82560 0.88770 0.30450 0.0480*H10 0.89020 0.39080 0.27940 0.0490*H12 1.41770 0.60760 0.46010 0.0490*H13 1.50150 0.82140 0.52930 0.0590*H14 1.33690 0.99660 0.57640 0.0640*H15 1.08660 0.95150 0.55800 0.0590*H16 1.00030 0.73440 0.49010 0.0480*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23Cl1 0.0314 (3) 0.0597 (4) 0.0649 (3) 0.0089 (2) −0.0083 (2) −0.0045 (2)O1 0.0335 (6) 0.0355 (7) 0.0536 (7) 0.0015 (5) −0.0141 (5) 0.0023 (5)O2 0.0543 (9) 0.0558 (9) 0.0619 (9) −0.0033 (6) −0.0090 (7) −0.0195 (7)N1 0.0304 (7) 0.0367 (8) 0.0378 (7) 0.0046 (6) −0.0069 (5) −0.0024 (6)N2 0.0365 (8) 0.0382 (8) 0.0497 (8) 0.0084 (6) −0.0094 (6) −0.0035 (6)C1 0.0294 (8) 0.0379 (9) 0.0321 (8) 0.0039 (6) −0.0057 (6) −0.0005 (6)C2 0.0382 (9) 0.0447 (10) 0.0418 (9) 0.0044 (8) −0.0038 (7) 0.0129 (7)C3 0.0342 (9) 0.0454 (10) 0.0456 (9) 0.0018 (7) 0.0038 (7) 0.0068 (8)C4 0.0316 (9) 0.0442 (10) 0.0368 (8) 0.0072 (7) −0.0034 (7) −0.0030 (7)C5 0.0423 (10) 0.0432 (10) 0.0445 (9) 0.0091 (8) −0.0071 (8) 0.0099 (8)C6 0.0390 (10) 0.0379 (10) 0.0435 (9) 0.0020 (7) −0.0014 (7) 0.0076 (7)C7 0.0258 (7) 0.0365 (9) 0.0364 (8) 0.0000 (6) −0.0044 (6) 0.0037 (7)C8 0.0302 (8) 0.0366 (9) 0.0386 (8) −0.0034 (7) −0.0030 (6) 0.0003 (7)C9 0.0340 (9) 0.0393 (10) 0.0453 (9) 0.0013 (7) −0.0021 (7) −0.0040 (7)C10 0.0360 (9) 0.0442 (11) 0.0409 (9) −0.0062 (7) −0.0037 (7) −0.0020 (8)C11 0.0350 (9) 0.0340 (9) 0.0308 (8) 0.0012 (6) −0.0042 (6) 0.0031 (6)C12 0.0340 (9) 0.0490 (11) 0.0386 (9) 0.0006 (7) −0.0020 (7) −0.0009 (7)C13 0.0440 (10) 0.0539 (12) 0.0468 (10) −0.0090 (9) −0.0097 (8) −0.0019 (8)C14 0.0658 (13) 0.0454 (12) 0.0467 (10) −0.0040 (9) −0.0104 (9) −0.0069 (8)C15 0.0623 (12) 0.0430 (11) 0.0429 (9) 0.0136 (9) 0.0021 (8) −0.0035 (8)C16 0.0360 (9) 0.0432 (10) 0.0412 (9) 0.0062 (7) −0.0023 (7) 0.0021 (8)supporting informationsup-5Acta Cryst. (2014). E70, o560    C17 0.0530 (12) 0.0482 (12) 0.0741 (13) 0.0116 (10) −0.0122 (10) −0.0135 (10)Geometric parameters (Å, º) Cl1—C4 1.7390 (18) C11—C16 1.386 (2)O1—C1 1.403 (2) C12—C13 1.384 (3)O1—C7 1.3490 (19) C13—C14 1.370 (3)O2—C10 1.214 (3) C14—C15 1.384 (3)N1—N2 1.384 (2) C15—C16 1.386 (3)N1—C7 1.347 (2) C2—H2 0.9300N1—C11 1.426 (2) C3—H3 0.9300N2—C9 1.320 (2) C5—H5 0.9300C1—C2 1.377 (3) C6—H6 0.9300C1—C6 1.377 (2) C10—H10 0.9300C2—C3 1.384 (2) C12—H12 0.9300C3—C4 1.379 (3) C13—H13 0.9300C4—C5 1.373 (2) C14—H14 0.9300C5—C6 1.388 (3) C15—H15 0.9300C7—C8 1.384 (2) C16—H16 0.9300C8—C9 1.425 (2) C17—H02A 0.9600C8—C10 1.449 (2) C17—H02B 0.9600C9—C17 1.490 (3) C17—H02C 0.9600C11—C12 1.380 (2)C1—O1—C7 119.23 (12) C13—C14—C15 119.99 (19)N2—N1—C7 110.91 (13) C14—C15—C16 120.39 (18)N2—N1—C11 119.12 (13) C11—C16—C15 118.86 (16)C7—N1—C11 129.64 (14) C1—C2—H2 120.00N1—N2—C9 105.30 (13) C3—C2—H2 120.00O1—C1—C2 122.29 (14) C2—C3—H3 120.00O1—C1—C6 115.95 (14) C4—C3—H3 120.00C2—C1—C6 121.69 (16) C4—C5—H5 120.00C1—C2—C3 119.37 (18) C6—C5—H5 120.00C2—C3—C4 119.31 (18) C1—C6—H6 121.00Cl1—C4—C3 119.12 (13) C5—C6—H6 121.00Cl1—C4—C5 119.89 (13) O2—C10—H10 118.00C3—C4—C5 121.00 (16) C8—C10—H10 118.00C4—C5—C6 120.08 (15) C11—C12—H12 120.00C1—C6—C5 118.54 (15) C13—C12—H12 120.00O1—C7—N1 117.94 (14) C12—C13—H13 120.00O1—C7—C8 133.72 (14) C14—C13—H13 120.00N1—C7—C8 108.15 (13) C13—C14—H14 120.00C7—C8—C9 103.96 (14) C15—C14—H14 120.00C7—C8—C10 128.28 (16) C14—C15—H15 120.00C9—C8—C10 127.72 (15) C16—C15—H15 120.00N2—C9—C8 111.66 (14) C11—C16—H16 121.00N2—C9—C17 120.29 (16) C15—C16—H16 121.00C8—C9—C17 128.05 (16) C9—C17—H02A 109.00supporting informationsup-6Acta Cryst. (2014). E70, o560    O2—C10—C8 123.73 (18) C9—C17—H02B 109.00N1—C11—C12 118.14 (14) C9—C17—H02C 109.00N1—C11—C16 120.96 (14) H02A—C17—H02B 110.00C12—C11—C16 120.89 (15) H02A—C17—H02C 109.00C11—C12—C13 119.43 (16) H02B—C17—H02C 109.00C12—C13—C14 120.43 (17)C7—O1—C1—C2 36.1 (2) C2—C3—C4—C5 0.6 (3)C7—O1—C1—C6 −146.92 (15) Cl1—C4—C5—C6 −179.47 (13)C1—O1—C7—N1 −143.39 (14) C3—C4—C5—C6 0.3 (3)C1—O1—C7—C8 42.4 (2) C4—C5—C6—C1 −0.6 (2)C7—N1—N2—C9 −1.81 (18) O1—C7—C8—C9 174.01 (17)C11—N1—N2—C9 −175.88 (14) O1—C7—C8—C10 −3.9 (3)N2—N1—C7—O1 −174.08 (13) N1—C7—C8—C9 −0.60 (17)N2—N1—C7—C8 1.51 (18) N1—C7—C8—C10 −178.50 (16)C11—N1—C7—O1 −0.8 (2) C7—C8—C9—N2 −0.55 (19)C11—N1—C7—C8 174.78 (15) C7—C8—C9—C17 −179.41 (17)N2—N1—C11—C12 37.2 (2) C10—C8—C9—N2 177.37 (17)N2—N1—C11—C16 −141.54 (15) C10—C8—C9—C17 −1.5 (3)C7—N1—C11—C12 −135.63 (17) C7—C8—C10—O2 −177.79 (18)C7—N1—C11—C16 45.7 (2) C9—C8—C10—O2 4.8 (3)N1—N2—C9—C8 1.42 (19) N1—C11—C12—C13 −179.23 (16)N1—N2—C9—C17 −179.62 (16) C16—C11—C12—C13 −0.5 (2)O1—C1—C2—C3 177.88 (16) N1—C11—C16—C15 179.80 (15)C6—C1—C2—C3 1.0 (3) C12—C11—C16—C15 1.1 (2)O1—C1—C6—C5 −177.13 (15) C11—C12—C13—C14 −0.8 (3)C2—C1—C6—C5 −0.1 (3) C12—C13—C14—C15 1.5 (3)C1—C2—C3—C4 −1.3 (3) C13—C14—C15—C16 −0.9 (3)C2—C3—C4—Cl1 −179.59 (14) C14—C15—C16—C11 −0.4 (3)Hydrogen-bond geometry (Å, º) Cg is the centroid of the C11–C16 ring.D—H···A D—H H···A D···A D—H···AC6—H6···O2i 0.93 2.58 3.503 (2) 171C2—H2···Cgii 0.93 2.63 3.476 (2) 152Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1.

Acta Crystallographica Section E Structure Reports Online

5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1<i>H</i>-pyrazole-4-carbaldehyde

http://journals.iucr.org/e/issues/2014/05/00/cv5447/cv5447.pdf

5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1
                    H

5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1 H

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