32 Ζ. Kristallogr. NCS 217 (2002) 32-34 © by Oldenbourg Wissenschaftsverlag,zyxwvutsrponmlkjih München Crystal structure of 2-(0,0-isopropyledene-2,3-dihydroxypropoxy)-3cyano-4,6-diphenylpyridine, C24H22N2O3 U . H. Pate l 1, C. G. D a ve ", M. M. Jo t a n i *j m and H. C. Sh a h " ' Saldar Patel University, Department of Physics, Vallabh Vidya Nagar, Gujarat 388 120, India " M. G. Science Institute, Organic Syntheses Laboratory, Navrangpura, Ahmedabad, Gujarat 380 009, India 111 College of Science, Β. V. B's R. A. Ahmedabd, Gujarat 380 001, India Received October 3,2001, accepted February 11,2002; CCDC-No. 1267/740 Source of material The title compound has been synthesized according to [ 1 ]. Detai 1 s of the synthesis will be published elsewhere. Rectangular crystals of the compound are grown from chloroform­ethanol solution by slow evaporation. Discussion C9* The title compound is studied as a part of our systematic investiga­ tions on a series of 3­cyano­2­pyridine derivatives. These compounds belongs to a class having wide range of biological activities such as antibacterial, antiviral, analgesic, antiinflammatory, etc. There are two molecules in the asymmetric unit. Propyloxy group which links the central pyridine ring to isopropyledene dihydroxy moiety adopts a zigzag conformation. Phenyl rings of both the molecules are planar within themselves (r.m.s. deviations of the fitted atoms are 0.014 Â and 0.013 Â formolecule Aand 0.013 ΐ and 0.011 ΐ for molecule B. Steric hindrances force the phenyl rings out of the respective pyridine ring plane by 40.06(6)° and 25.17(2)° (molecule A) and 39.31(2)° and 23.44(2)° (molecule B), respectively. However, these dihedral angles are comparatively smaller in range than those observed in other related structures [2­5], The tripple bond character of the C—Ν bond (1.16(1) Â (molecule A) and 1.11 ( 1 ) Â (molecule B) and the linearity of the angle C2­C18­N2 of cyano moiety (174.8(8)° for molecule A and 178.6(9)° formolecule B) are the typical characteristics ex­ hibited by 2­pyridine­3­cyano derivatives recently reported by us [3­6], Opening up of the angle N 1 ­ C 1 ­ C 2 (123.7(6)° for mole­ cule A and 125.8(6)° for molecule B) and considerable shorten­ ing of the C—Ν distances may directly be attributed to the bulky substituents at the ortho position. The conformation about C19—C20 bond of propyl carbon C21 (molecule A) and C21' (molecule B) is cis. Isopropyledene dihydroxy moiety of molecule A and molecule Β have pyramide like conformation with one of the oxygen at apical position. The terminal isopropyledene carbon C23, C24 and 0 3 of molecule A and C24' of molecule Β have large thermal parameters. Weak van der Waal forces are responsible for the stability of the structure as observed in other closed heterocycles. Abstract C24H22N2O3, monoclinic, C12/cl (No. 15), a = 15.462(4) À, 6=11.446(2)Â, c = 23.005(4)Â, tsroihcV β = 94.20(2)°, V = 4060.5 Â 3 , Z = 8 , p m = 1.232 g em" 3 ,wRF R&(F) = 0.065, wR^F2) = 0.209, T = 293 K. * Correspondence author (e-mail: mmjotani@rediffmail.com) Unauthenticated Download Date | 2/25/20 7:32 AM 33 C24H22N203 Table 2. Continued. Table 1. Data collection and handling. Atom Site colourless, rectangular. size 0.1utsrponmliedcbaXVUTSRPONLKIHFEDCBA χ 0.2 χ 0.2 mm H(I9B) 4 / Wavelength: ytrpnkhfedaXUNID Cu Ku radiation (1.54180 λ ) H(20) 4/ 6.76 cm"1 fH(21A) 4 / CAD4. ω/20 Diffractometer. scan mode: H(21B) 4 / 136.04° 2φmav H(23A) 4 / 3794. 3791 hkl Wasured. 'Vfllkl)unique: H(23B) 4f lob- > 2 σ ί / o b s A 2936 Criterion for /0bs­ NthkDp. H(23C) 4 / 524 Nf parant IreUned'· H(24A) 4f SHELXS­97 [7], SHHLXL­97 [8], Programs: H(24B) 4 / ORTEP [9], PLUTON [10] H(24C) 4 / H(4') 4/ H(7') 4/ H(8') 4/ H(9) 4/ H(10') 4/ H(1 Γ) 4/ Table 2. Atomic coordinates and displacement parameters (in ΐ 2 ). H(13') 4f H(14') 4/ Site X Atom ζ t/iso H(15') 4/ H(16') 4/ 0.6940 ­0.1591 0.8530 0.053 H(4) H(17') 4/ 4/ 0.7794 ­0.3366 0.8736 0.068 H(7) 4/ H(19C) 4 / ­0.5352 0.084 0.7745 0.8692 H(8) 4/ H(19D) 4 / 0.7035 ­0.6403 0.082 0.9391 H(9) 4/ H(20') 4/ 0.077 0.6208 ­0.5412 0.9994 H(10) H(21C) 4 / 4/ 0.6230 ­0.3446 1.0046 0.069 HCl I) H(21D) 4 / 4/ 0.6553 0.070 0.2143 0.8712 H(13) 4/ H(23D) 4 / 0.6398 0.3232 0.083 0.7868 H( 14) H(23E) 4 / 4/ 0.6874 0.2459 0.7027 0.079 H(15) H(23F) 4 / 4/ 0.7293 0.074 0.0581 0.6989 H(16) H(24D) 4 / 4/ 0.7481 0.065 ­0.0533 0.7865 H(17) H(24E) 4 / 4/ 0.2104 0.6775 1.0174 0.076 H(19A) 4 / H(24F) 4 / V X Crystal: 0.7792 0.7584 0.6412 0.5924 0.6387 0.6413 0.7271 0.7364 0.6809 0.7745 0.9500 0.8704 0.8626 0.9390 1.0176 1.0202 0.9924 0.9972 0.9635 0.9089 0.9035 0.9728 0.8707 0.8757 1.0514 1.0097 0.9286 1.0218 1.0042 0.8578 0.8953 0.9472 0.2027 0.1637 0.1405 0.1549 0.5274 0.5114 0.5370 0.2657 0.3670 0.3925 ­0.1635 ­0.3310 ­0.5352 ­0.6398 ­0.5484 ­0.3442 0.2140 0.3254 0.2443 0.0535 ­0.0555 0.2155 0.2082 0.1611 0.1648 0.1373 0.5442 0.5231 0.5054 0.3935 0.2662 0.3688 ζ i/iso 1.0299 1.1310 1.1660 1.1035 1.1797 I.I 121 1.1507 1.2216 1.2457 1.2268 1.0797 1.0650 1.0656 1.0043 0.9336 0.9298 1.0625 1.1462 1.2351 1.2349 1.1539 0.9107 0.9073 0.8049 0.8365 0.7735 0.7861 0.7654 0.8311 0.7137 0.7144 0.6881 0.076 0.080 0.090 0.090 0.179 0.179 0.179 0.143 0.143 0.143 0.051 0.061 0.078 0.086 0.076 0.059 0.063 0.077 0.075 0.072 0.063 0.071 0.071 0.066 0.092 0.092 0.116 0.116 0.116 0.160 0.160 0.160 Table 3. Atomic coordinates and displacement parameters (in ΐ2). Atom Site X 0(1) 0(2) 0(3) N(l) N(2) C(5) C(4) C(3) C(2) C(l) C(6) C(7) C(8) C(9) C(10) C(U) C(12) C(13) C(14) C(15) C(16) C(17) C(18) C(19) C(20) C(21) C(22) C(23) C(24) O(l') 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 0.7187(4) 0.7375(4) 0.6103(4) 0.7102(4) 0.7275(6) 0.7041(4) 0.6998(4) 0.7042(4) 0.7097(4) 0.7123(5) 0.6992(4) 0.7467(5) 0.7456(7) 0.7009(7) 0.6544(6) 0.6543(5) 0.6984(4) 0.6699(5) 0.6623(6) 0.6886(6) 0.7159(6) 0.7247(5) 0.7181(5) 0.7239(7) 0.7145(6) 0.6346(7) 0.6858(5) 0.6721(9) 0.7228(8) 0.9274(3) y 0.0537(5) 0.3289(5) 0.3084(5) 0.0600(5) ­0.2133(7) ­0.0055(6) ­0.1217(6) ­0.1879(6) ­0.1212(6) ­0.0013(6) ­0.3137(7) ­0.3773(7) ­0.4959(7) ­0.5591(6) ­0.4999(8) ­0.3814(7) 0.0677(6) 0.1814(7) 0.2479(8) 0.2004(8) 0.0906(8) 0.0216(7) ­0.1768(7) 0.1764(7) 0.2084(7) 0.1897(8) 0.3738(7) 0.498(1) 0.347(1) 0.0531(4) ζ Un t/22 t/33 1.0426(2) 1.1131(2) 1.1463(3) 0.9420(2) 1.0962(3) 0.8920(3) 0.8889(3) 0.9415(2) 0.9939(3) 0.9918(3) 0.9395(3) 0.8992(4) 0.8974(4) 0.9379(4) 0.9746(4) 0.9769(4) 0.8361(3) 0.8363(3) 0.7864(4) 0.7362(3) 0.7342(3) 0.7868(3) 1.0499(3) 1.0425(3) 1.1075(3) 1.1316(4) 1.1575(3) 1.1493(6) 1.2184(4) 0.8929(2) 0.093(4) 0.063(3) 0.061(3) 0.039(3) 0.108(6) 0.040(4) 0.037(3) 0.029(3) 0.034(3) 0.041(4) 0.034(3) 0.056(4) 0.073(6) 0.094(6) 0.061(5) 0.046(4) 0.034(4) 0.063(5) 0.080(6) 0.071(5) 0.069(5) 0.053(4) 0.052(4) 0.091(6) 0.109(7) 0.096(7) 0.049(4) 0.14(1) 0.103(7) 0.066(3) 0.047(3) 0.059(3) 0.059(3) 0.043(3) 0.070(5) 0.055(4) 0.056(4) 0.051(4) 0.055(4) 0.054(4) 0.058(4) 0.058(4) 0.057(5) 0.043(4) 0.066(5) 0.057(5) 0.053(4) 0.061(5) 0.053(4) 0.075(6) 0.079(5) 0.060(5) 0.054(4) 0.049(4) 0.055(4) 0.064(5) 0.058(5) 0.096(8) 0.120(8) 0.043(3) 0.041(2) 0.062(3) 0.157(6) 0.053(3) 0.057(4) 0.035(3) 0.038(3) 0.041(3) 0.040(3) 0.044(3) 0.047(3) 0.058(4) 0.080(5) 0.067(5) 0.066(5) 0.070(4) 0.051(4) 0.050(4) 0.074(5) 0.052(4) 0.038(3) 0.049(4) 0.041(3) 0.050(4) 0.036(3) 0.069(5) 0.057(4) 0.118(8) 0.061(5) 0.043(2) t/12 0.005(3) 0.002(3) 0.013(3) 0.002(2) 0.006(5) 0.000(3) ­0.002(3) 0.002(3) 0.011(3) ­0.005(3) 0.002(3) ­0.005(4) 0.006(4) ­0.031(4) ­0.035(4) ­0.013(4) ­0.013(3) ­0.002(4) ­0.008(4) ­0.009(5) ­0.012(4) 0.007(4) 0.002(3) 0.009(4) ­0.008(4) ­0.014(5) 0.010(4) 0.065(7) ­0.027(6) 0.004(2) 1/13 ­0.003(3) 0.001(2) ­0.029(3) ­0.004(2) 0.021(4) ­0.003(2) ­0.001(3) 0.000(2) ­0.003(2) 0.000(3) ­0.002(3) 0.020(3) 0.017(5) 0.004(4) 0.006(4) 0.010(3) 0.002(3) 0.007(3) ­0.008(4) 0.000(4) 0.007(3) 0.005(3) ­0.002(3) 0.007(4) ­0.002(3) 0.022(4) ­0.008(3) ­0.052(7) ­0.005(5) 0.002(2) t/23 ­0.003(2) ­0.013(2) ­0.034(3) ­0.003(2) 0.002(3) 0.004(3) 0.002(3) 0.005(3) 0.005(3) ­0.005(3) ­0.004(3) ­0.009(3) ­0.014(4) 0.001(3) ­0.003(4) ­0.009(4) 0.016(3) 0.002(3) 0.019(4) 0.021(4) 0.017(3) 0.011(3) ­0.001(3) ­0.004(3) ­0.007(3) ­0.005(4) ­0.012(3) ­0.044(6) ­0.016(5) 0.004(2) Unauthenticated Download Date | 2/25/20 7:32 AM 34 C24H22N2O3 Table 3. Continued. Atom Site X 0(2') 0(3') 4/ 4/ N(l') 4/ 4/ 4/ 4/ 0.9037(4) 1.0363(3) 0.9338(4) 0.9164(6) 0.9404(4) 0.9450(5) 0.9422(4) 0.9336(4) 0.9323(4) 0.9413(4) 0.8980(5) 0.8953(7) 0.9396(7) 0.9875(6) 0.9886(5) 0.9434(5) 0.9746(5) 0.9792(6) 0.9575(6) 0.9264(5) 0.9216(5) 0.9250(6) 0.9223(6) 0.9189(4) 1.0111(6) 0.9577(5) 0.9801(7) 0.9098(9) N(2') C(5') C(4') C(3') C(2') C(l') C(6') C(7') C(8') C(9') C(10') C(ll') C(12') C(13') C(14') C(15') C(16') C(17') C(18') C(19') C(20') C(21') C(22') C(23') C(24') 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4f 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4/ 4f 4/ 4/ y 0.3288(5) 0.3026(6) 0.0588(5) ­0.2138(7) 0.0015(5) ­Ό. 1238(6) ­0.1864(6) ­0.1253(6) ­0.0015(5) ­0.3191(5) ­0.3743(6) ­0.4971(7) ­0.5587(7) ­0.5040(7) ­0.3826(6) 0.0686(6) 0.1821(7) 0.2480(7) 0.2009(8) 0.0858(8) 0.0218(6) ­0.1743(6) 0.1803(7) 0.2085(6) 0.1929(8) 0.3711(7) 0.4974(7) 0.348(1) ζ Un Un Í/33 0.8192(3) 0.7866(2) 0.9935(2) 0.8391(3) 1.0447(3) 1.0443(3) 0.9940(3) 0.9418(3) 0.9457(3) 0.9959(3) 1.0376(3) 1.0389(4) 1.0020(4) 0.9594(4) 0.9569(3) 1.0975(3) 1.0969(3) 1.1476(3) 1.2009(3) 1.2006(3) 1.1521(3) 0.8844(3) 0.8902(3) 0.8274(4) 0.8053(5) 0.7795(3) 0.7916(5) 0.7179(5) 0.072(4) 0.050(3) 0.051(3) 0.123(7) 0.028(3) 0.044(4) 0.032(3) 0.040(3) 0.041(4) 0.036(3) 0053(4) 0.079(6) 0.084(6) 0.076(6) 0.051(4) 0.044(4) 0.058(5) 0.087(6) 0.074(5) 0.064(5) 0.061(5) 0.062(5) 0.077(5) 0.035(3) 0.052(5) 0.038(4) 0.083(6) 0.109(8) 0.053(3) 0.096(4) 0.050(3) 0.065(4) 0.038(3) 0.039(3) 0.042(4) 0.043(3) 0.039(3) 0.032(3) 0.047(4) 0.052(4) 0.047(4) 0.045(4) 0.052(4) 0.048(4) 0.054(4) 0.056(4) 0.061(5) 0.063(5) 0.050(4) 0.043(4) 0.043(4) 0.044(4) 0.055(5) 0.061(5) 0.053(4) 0.118(9) 0.116(5) 0.067(3) 0.040(3) 0.043(3) 0.053(3) 0.045(3) 0.051(3) 0.045(3) 0.042(3) 0.049(3) 0.053(4) 0.064(4) 0.082(5) 0.070(5) 0.046(3) 0.042(3) 0.046(3) 0.051(4) 0.051(4) 0.052(4) 0.047(3) 0.057(4) 0.056(4) 0.087(5) 0.121(7) 0.064(4) 0.095(6) 0.087(6) Un 0.015(3) 0.001(3) 0.010(3) ­0.018(5) 0.007(2) 0.004(3) 0.008(3) 0.008(3) ­0.008(3) 0.009(3) ­0.001(3) 0.004(4) ­0.014(4) 0.004(4) 0.009(3) 0.006(3) 0.001(3) ­0.017(4) 0.001(4) 0.002(4) 0.010(4) ­0.005(3) 0.013(4) ­0.008(3) ­0.002(4) 0.000(3) ­0.010(4) ­0.031(7) Un 0.043(4) 0.026(2) 0.001(2) 0.002(4) 0.002(3) ­0.001(3) 0.007(2) 0.011(3) ­0.001(3) ­0.001(2) 0.004(3) 0.012(4) ­0.006(5) 0.010(4) 0.008(3) ­0.008(3) 0.000(3) 0.010(4) 0.000(4) 0.003(3) 0.007(3) 0.017(3) ­0.004(4) 0.003(3) ­0.012(4) 0.009(3) ­0.005(5) ­0.033(6) Í/23 0.018(3) 0.006(3) ­O.OOK2) ­0.006(3) 0.005(3) 0.003(3) 0.007(3) 0.003(3) ­0.002(2) 0.001(3) 0.002(3) 0.014(4) 0.014(4) ­0.007(3) ­0.003(3) 0.012(3) 0.002(3) ­0.004(3) ­0.006(3) 0.013(3) 0.009(3) 0.004(3) 0.006(3) 0.004(3) 0.009(5) 0.018(3) 0.011(4) 0.003(6) Acknowledgments. Authors are thankful to X­ray laboratory RSIC, ΙΓΓ Ma­ dras, India for providing us CAD­4 facility for collecting intensity data. Fi­ nancial support from Department of Physics, SPU to carry out the work is gratefully acknowledged. One of the author Mr. M. M. Jotani is also thankful to UGC, Pune (WRO) for the teacher fellowship award. References 1. Dave, C. G.; Shah, H. C.: Study of phase transfer catalysis in Heterocyclic compounds carried out at Organic Syntheses Laboratory, M. G. Science Institute, Ahmedabad and reported in Ph.D. Thesis of Shah, H. C.submit­ ted to Gujarat University, Ahmedabad, Gujarat, India (2000). 2. Hursthouse, M. B.; Karaulov, A. I.; Ciechanowicz­Rutkowska, M.; Kolasa, Α.; Zankowska Jasinska, W.: Structure of 3­Benzoyl­4­me«hyl­1­phenyl­1,2,3,4­ tetrahydro­5//­indeno­[ 1,2­6] pyridine­2^­dione. Acta Crystallogr. C48(1992) 1257­1260. 3. Patel, U. H.; Dave, C. G.; Jotani, M. M.; Shah H. C.: Crystal Structure of a Novel Tetrahydro pyridine derivative: l,3­dimethyl­2­oxo­4,6­diphenyl­ 1,2,3,4­tetrahydropyridine­3­carbonitrile. Submitted to Acta Crystallogr. C (2001). 4. Patel, U. H.; Dave, C. G.; Jotani, M. M.; Shah H. C.: Crystal Structure of a Novel Tetrahydro pyridine derivative: l,3­diethyl­2­oxo­4,6­diphenyl­ l,2,3,4­tetrahydropyridine­3­carbonitrile. Submitted to Crystal Research and Technology (2001). 5. Patel, U. H.; Dave, C. G.; Jotani, M. M.; Shah H. C.: Crystal structure of 1,3­dibenzy l­2­oxo­4,6­dipheny 1­1,2,3,4­tetrahydropyridine­3­ caibonitrile, C 3 2 H 2 6 N 2 O . Z. Kristallogr. NCS 217 (2002) 29­31. 6. Patel, U. H.; Dave, C. G.; Jotani, M. M.; Shah H. C.: 5,7­Diphenyl tetrazolo[l,5­a]pyridine­8­carbonitrile. Submitted to Acta Crystallogr. E (2002). 7. Sheldrick, G. M.: SHELXS­97. Program for Crystal Structure Solution, University of Gφttingen, Germany 1997. 8. Sheldrick, G. M.: SHELXL­97. Program for Crystal Structure Refine­ ment, University of Gφttingen, Germany 1997. 9. Johnson, C. K.: ORTEP, Report on ORNL­3794, Oak Ridge National Laboratory, Oak Ridge, TN, USA 1976. 10. Speak, A. L.; PLUTON­92, University OF Utrecht, Utrecht, The Nether­ lands 1992. Unauthenticated Download Date | 2/25/20 7:32 AM