详细键长表

J.CHEM.SOC.PERKINTRANS.II1987s1TablesofBondLengthsdeterminedbyX-RayandNeutronDiffraction.PartI.BondLengthsinOrganicCompoundsFrankH.Allen,”OlgaKennard,andDavidG.WatsonCambridgeCrystallographicDataCentre,UniversityChemicalLaboratory,LensfieldRoad,CambridgeCB21EWLeeBrammerandA.GuyOrpenSchoolofChemistry,UniversityofBristol,Cantock’sCloseBristolBS81TSRobinTaylorI.C.I.PlantProtectionDivision,Jealott’sHillResearchStation,Bracknell,BerkshireRG126EYTheaveragelengthsofbondsinvolvingtheelementsH,B,C,N,0,F,Si,P,S,CI,As,Se,Br,Te,andIinorganiccompoundsarereported.Thedeterminationofmoleculargeometryisofvitalimportancetoourunderstandingofchemicalstructureandbonding.ThemajorityofexperimentaldatahavecomefromX-rayandneutrondiffraction,microwavespectroscopyandelectrondiffraction.Overtheyearscompilationsofresultsfromthese5000techniqueshaveappearedsporadically.Thefirstmajorcompil-ationwasChemicalSocietySpecialPublicationNo.11:‘Tables4000ofInteratomicDistancesandConfigurationinMoleculesandIons’.Thisvolumesummarizedresultsobtainedbydiffraction3000andspectroscopicmethodspriorto1956;asupplementary2000volume2extendedthiscoverageto1959.Summarytablesofbondlengthsbetweencarbonandotherelementswerealso1000publishedinVolumeI11of‘InternationalTablesforX-RayCry~tallography’.~SomeyearslatertheCambridgeCrystallo-year19651970197519801985graphicDataCentre4producedanatlas-stylecompendiumofallorganic,organometallic,andmetalcomplexcrystalFigure1.GrowthoftheCambridgeStructuralDatabase1965-1985structurespublishedintheperiod1960-1965.Morerecentlyaasno.ofentries(nent)publishedinagivenyearsurveyofgeometriesdeterminedbyspectroscopicmethodshasextendedcoverageinthisareatomid-1977.retrievedfromtheSeptember1985versionofCSD.NeutronTheproductionoffurthercomprehensivecompendiaofX-diffractiondataonlywereusedtoderivemeanbondlengthsrayandneutrondiffractionresultshasbeenprecludedbytheinvolvinghydrogenatoms.ThisversionofCSDcontainedsteepriseinthenumberofpublishedcrystalstructures,asresultsfor49854single-crystalsdiffractionstudiesoforgano-illustratedbyFigure1.Printedcompilationshavebeencarboncompounds10324ofthesesatisfiedtheacceptanceeffectivelysupersededbycomputerizeddatabases.InparticularcriterialistedbelowandwereusedintheaveragingtheCambridgeStructuralDatabase(CSD)nowcontainsbiblio-procedures.graphic,chemicalandnumericalresultsforca.55000organo-(i)Structureis‘organic’,i.e.belongstoCSDclasses1-65orcarboncrystalstructures.Thismachine-readablefilefulfils70.’thefunctionofacomprehensivestructure-by-structurecom-(ii)Atomicco-ordinatesforthestructurehavebeenpublishedpendiumofmoleculargeometries.HowevertheamountofdataandareavailableinCSD.nowheldinCSDissolargethatthereisalsoaneedforconcise,(iii)Structurewasdeterminedfromdiffractometerdata.printedtabulationsofaveragemoleculardimensions.(iv)StructuredoesnotcontainunresolvednumericdataTheonlytablesofaveragegeometryingeneralusearethoseerrorsfromtheoriginalpublication(sucherrorsareusuallycontainedintheChemicalSocietySpecialPublications‘v2oftypographicalandarenormallyresolvedbyconsultationwith1958and1965,whichlistmeanbondlengthsforavarietyoftheauthors).atompairsandfunctionalgroups.Sincetheseearlytables(v)Structurewasnotreportedtobedisordered.werebasedondataobtainedbefore1960,wehaveusedCSDto(vi)Onlystructuresofhighprecisionwereincludedontheprepareanewtableofaveragebondlengthsinorganicbasisofeither(a)crystallographicRfactorwasd0.07andthecompounds.TheTablegivenherespecificiallylistsaveragereportedmeanestimatedstandarddeviation(e.s.d.)forthelengthsforbondsinvolvingtheelementsH,B,C,N,0,F,Si,P,C-CbondlengthswasdO.010A(correspondstoASflag=1S,C1,As,Se,Br,Te,andI.Meanvaluesarepresentedfor682or2inCSD),or(b)crystallographicRfactordO.05andthedifferentbondtypesinvolvingtheseelements.Averagebondmeane.s.d.forC-Cbondsarenotavailableinthedatabaselengthsinorganometalliccompoundsandmetalcomplexes(AS=OinCSD).willbepresentedinalaterpaper.(vii)Wherethestructureofagivencompoundhadbeendeter-minedmorethanoncewithinthelimitsof(i)-(vi)thenonlythemostprecisedeterminationwasused.MethodologySelectionofCrystallographicData.-AllresultsgivenintheProgramSystem.-AllcalculationswereperformedontheTablearebasedonX-rayandneutrondiffractionresultsUniversityofCambridgeIBM3081Dcomputerusingthes2J.CHEM.SOC.PERKINTRANS.111987programsBIBSER,CONNSER,RETRIEVE,GEOM78,andPLUT078.4Astand-aloneprogramwaswrittentoimplementtheselectioncriteria,whilstanewprogram(STATS)wasusedforstatisticalcalculationsdescribedbelow.ItwasalsonecessarytomodifyCONNSERtoimprovetheprecisionwithwhichitrillocateschemicalsubstructures.Inparticulartheprogramwasalteredtopermitthelocationofatomswithspecifiedco-ordinationnumbers.Thiswasessentialinthecaseofcarbonsothatatomswithco-ordinationnumbers2,3,and4(equivalenttoformalhybridizationstatessp',sp2,sp3)couldbedistin-guishedeasilyandreliably.ConsiderablecarewastakentoensurethatthecorrectmolecularfragmentwaslocatedbyGEOM78inthegenerationofgeometricaltabulations.Thisofteninvolvedtheexplicitspecificationofhydrogenatomsinfragments,andtheextensiveuseofgeometricaltestsonvalenceandtorsionangles.Considerableusewasalsomadeofchemicalstructuraldiagrams,whichareavailableintheCambridgein-Figure2.Effectoftheremovalofoutliers(contributorswhichare>40fromthemean)fortheC-CbondinCar-C-Nfragments.houseversionofCSDforca.65%ofallentries.ChemicalRelevantstatistics(seetext)are:diagramsproveduseful,forexample,inidentifyingthevariousco-ordinationenvironmentscommonlyadoptedbyatomssuchdm0Y14.nasAs,B,P,etc.(a)before:1.4451.4440.0121.4361.44832(b)after:1.4451.4440.0081.4361.44831ClassiJicationofBonds.-TheclassificationofbondsusedintheTableisbasedoncommonfunctionalgroups,ringsandringsystems,co-ordinationspheres,etc.Itisdesignedto:(i)appearlogical,useful,andreasonablyself-explanatorytochemists,crystallographers,andotherswhomayusetheTable;(ii)topermitameaningfulaveragevaluetobecitedforeachbondlength.Withreferenceto(ii),itwasconsideredthatasampleofbondlengthscouldbeaveragedmeaningfullyif(a)thesamplewasunimodallydistributed;(b)thesamplestandarddeviation(0)wasreasonablysmall,ideally40fromthemeanwereautomaticallyeliminatedfromthesamplebySTATS,otheroutlierswereinspectedcarefully);1-2801-420(d)therewerenocompellingchemicalreasonsforfurtherFigure3.SkeweddistributionofB-FbondlengthsinBF,-ions:subdivisionofthesample.d=1.365,m=1.372,(J=0.029,q1=1.352,qu=1.390for84observ-ations.Notethatd#mandthatq1quareasymmetricallydisposedStatistics.-Wheretherearelessthanfourindependentaboutthemeandobservationsofagivenbondlength,theneachindividualobservationisgivenexplicitlyintheTable.InallothercasesthefollowingstatisticsweregeneratedbytheprogramSTATS.(i)Theunweightedsamplemean,d,whereequation(1)holdsnanddiistheithobservationofthebondlengthinatotalsampleofnobservations.Recentwork8-10hasshownthattheunweightedmeanisanacceptable(evenpreferable)alternativetotheweightedmean,wheretheithobservationisassigneda1-311.46weightequaltol/02(di).Thisisespeciallytruewherestructureshavebeenpre-screenedonthebasisofprecision.(a)(ii)Thesamplemedian,rn.Thishasthepropertythathalfoftheobservationsinthesampleexceedrn,andhalffallshortofit.n(iii)Thesamplestandarddeviation,denotedhereas0,whereequation(2)holds.nCT=1[(di-Cq2/(n-1)]+(2)i=1(iv)Thelowerquartileforthesample,ql.Thishasthe1-341-411-411-46propertythat25%oftheobservationsarelessthanq1and75%exceedit.(b)(C1(v)Theupperquartileforthesample,4,,.ThishastheFigure4.ResolutionofthebimodaldistributionofC-Nbondlengthspropertythat25%oftheobservationsexceed4,,,and75%fallinCar-N(Csp3),fragments:(a)completedistribution,(b)distributionshortofit.forplanarN,meanvalenceangleatN>117.5",(c)distributionfor(vi)Thenumbernofobservationsinthesample.pyramidalN,meanvalenceangleatNintherange108-114"J.CHEM.SOC.PERKINTRANS.II1987s3(a)AsBBrCClFHIN0PSSeSiTeASCspLCc'wFOOOlN1'50Figure5.(a)DistributionofmeanbondlengthvaluesreportedintheTablebyelementpair.An*indicatesabondedpairrepresentedbylessthanfourcontributorsintheoriginaldataset.AtindicatesbondedpairslocatedwhenrestrictionsonRfactorandreportede.s.d.limitswerelifted(seetext).(b)DistributionofmeanbondlengthvaluesreportedintheTableforC-C,C-0,andC-NThestatisticsgiveninthefinalTablecorrespondtodistri-containsthenumberofdiscreteaveragebondlengthsgiveninbutionsforwhichtheautomatic40cut-off(seeabove)hadbeentheTableforeachelementpair.Atotalof682averagevaluesareapplied,andanymanualremovalofadditionaloutliers(ancitedfor65elementpairs,ofwhich511(75%)involvecarbon.infrequentoperation)hadbeenperformed.InpracticeaveryBondlengthvaluesfromindividualstructuresaregivenforasmallpercentageofobservationswereexcludedbythesefurther30elementpairs,indicatedby*inFigure5a.Individualmethods.ThemajoreffectofremovingoutliersistoimprovethestructuresareidentifiedbytheirCSDreferencecode(eg.samplestandarddeviation,asshowninFigure2inwhichaBOGSUL)andshort-formliteraturereferences,orderedalpha-singleobservationisdeleted.beticallybyreferencecode,aregiveninAppendix2.AfullThestatisticschosenfortabulationeffectivelydescribethebibliographiclistingisavailableasSupplementaryPublicationdistributionofbondlengthsineachcase.Forasymmetrical,NoSUP56701(12pp.).*For8elementpairstheacceptancenormaldistribution:themean(d)willbeapproximatelyequalcriterion(vi)wasrelaxedtoincludeallavailablestructures,tothemedian(m);thelowerandupperquartiles(ql,4")willbeirrespectiveofprecision.Theseentriesaredenotedbypintheapproximatelysymmetricaboutthemedian:m-q,11qu-m,andTable.Nobondswerefoundfor25elementpairswithinthe95%oftheobservationsmaybeexpectedtoliewithin+20ofsubsetofCSDusedinthisstudy.themeanvalue.ForaskeweddistributiondandmmaydifferEachentryintheTablecontainsninecolumns,ofwhichsixappreciablyandq1andquwillbeasymmetricwithrespecttorecordthestatisticsofthebondlengthdistributiondescribedm.Whenabond-lengthdistributionisnegativelyskewedasinabove.Thecontentoftheremainingthreecolumns:Bond,Figure3,i.e.veryshortvaluesaremorecommonthanverySubstructure,Note,arenowdescribed.longvalues,thenitmaybeduetothermal-motioneffects;thedistancesusedtopreparetheTablewerenotcorrectedforOrderingofEntries:the'Bond'Column.-Foranelementthermallibration.pairX-YtheprimaryorderingisalphabeticbyelementInanumberofcasestheinitialbond-lengthdistributionwassymbolsaccordingtotherowsofFigure5a,i.e.Xchangesclearlybimodal,asinFigure4a.Allcasesofbiomodalitywereslowest,Yfastest.ThecompletesequencerunsfromAs-AstoresolvedonchemicalgroundsbeforeinclusionintheTable,onTe-Tewithbondsinvolvingcarbonintheirnaturalposition:thebasisofhybridization,conformation-dependentconjugativeAs-C...C-C...C-Te.WithinagivenX-Ypairasecondaryinteractions,etc.ForexamplethehistogramofFigure4awasorderingisbasedontheco-ordinationnumbers(j)ofXandresolvedintothetwodiscreteunimodaldistributionsofFiguresY,andonthenatureofthebondbetweenthem.Thebond4b,cwhichcorrespondtoplanarN(sp2)andpyramidalN(sp3),definitionisoftheformXu)-Y(j),withjdecreasingfastestrespectively.ThemeanvalenceangleatNwasusedastheforY,slowestforX,andwithallsinglebondsprecedinganydiscriminator,witharangeof108-114"forN(sp3)andmultiplebonds.Forcarbontheformalhybridizationstate3117.5"forN(sp2).replaces(butisequivalentto)theco-ordinationnumberanditisforthiselementthattheorderingrulesaremostclearlyrequired.TheorderingofthemostpopulousC-C,C-N,C-0sectionsisillustratedinFigure5b.The13possibleC-CcombinationsContentandArrangementoftheTableTheuppertriangularmatrixofFigure5ashowsthe120possibleelementpaircombinationswhichcanbeformedfromthe15*FordetailsofSupplementaryPublicationsseeInstructionsforelements:As,B,Br,C,Cl,F,H,I,N,0,P.S,Se,Si,Te.Figure5aAuthors,J.Chem.SOC.,PerkinTrans.2,1987,Issue1.s4J.CHEM.SOC.PERKINTRANS.111987CH20HI15891CHOH1143[?"r3K5c0):5104HOHanthraceneazetidineaziridineturanfuranose117110N''N25(iN;li4'8O'y:I4Ir34N34furazanfuroxanimidaroleindoleisoxazole16pgN\p2III33"1"18,5NQp/N34oxetaneoxiranenaphthalenephenothiazinephosphazene11I143544a.,0p5rN"q260:3Oa1piperidinepyranosepyrazabolepyrazinepyrazole111":54"m::NC"r07:44TCNQpyridazinepyrirnidine1H-pyrroletetracyanoquinodimethanetetrahydrofuran11116cJ:5L45rNT:4":TII:5tetrahydropyrantetrahydropyrroletetrahydrothiophenetetrahydrothiopyrantetraselenafuIvalene1"c;:"c;:3451;si]23tetrathiafulvalenethietanethiopheneFigure6.AlphabeticizedindexofringsystemsreferredtointheTable;thenumberingschemeusedinassemblingthebondlengthdataisgivenwherenecessaryfollowthesequenceCsp3-Csp3,Csp3-Csp2,Csp3-Car,Csp3-DeJnitionof'Substructures'.-ThechemicalenvironmentofCsp',Csp2-Csp2,Csp2-Car,Csp2-Csp',Car-Car,Car-Csp',eachbondisnormallydefinedbyalinearformulationofthesub-Csp'-Csp',Csp2=Csp2,CarNCar,Csp'=Csp'.ThesymbolCarstructure.Thetargetbondissetinboldtype,e.g.Car-CsN(arylrepresentsarylcarboninsix-memberedrings,whichistreatedcyanides);C-CH2-0-Car(primary-alkylarylethers);(C-O),-separatelyfromCsp2throughouttheTable.Thesymbol2:isP(NO),(phosphatediesters).Occasionallythechemicalnameusedtoindicateadelocalizeddoubleoraromaticbondofafunctionalgrouporringsystemisusedtodefinebondaccordingtocontext.environment,e.g.innaphthalene,C2-C3;inimidazole,Nl-C2.J.CHEM.SOC.PERKINTRANS.II1987s5Toavoidanypossibleambiguityinthesecases,weincludeconjugatedsystems;(c)anypeculiaritiesofaparticularbondnumberedchemicaldiagramsinFigure6.Acombinationoflengthdistribution,e.g.sampledominatedbyC*=methyl;(d)chemicalnameandlinearformulationisoftenemployedtoreferencestopreviouslypublishedsurveysofcrystallographicincreasetheprecisionofthedefinition,e.g.NH,-C=Oinacylicresultsrelevanttothesubstructureinquestion.Wedonotclaimamides;C=C-C(=O)-C=Oinbenzoquinone.Finally,forverythatthesereferencesareinanywaycomprehensiveandwesimpleions,theacceptedconventionalrepresentationisdeemedwouldbegratefultoauthorsfornotification(toF.H.A.)ofanytobesufficient,e.g.inNO,-inSO4-,etc.omissions.ThiswillservetoimprovethecontentofanyfutureThechemicaldefinitionofsubstructuremaybefollowedbyversionoftheTable.briefqualifyinginformation,concerningsubstitution,conform-ationalrestrictions,etc.Forexample:Csp3-Csp3:incyclobutane(anysubstituent);X-C-F,(X=C,H,N,0);Car-NH-Csp3(Nsp3:pyramidal).WherethegenericsymbolXisunqualifieditDiscussiondenotesanyelementtype,includinghydrogen.IfthequalifyingItshouldberememberedthatthisTablehasbeenderivedfrominformationistooextensivethenitwillbegivenasaTabletheorganicsectionofCSD.Weareawarethatanumberoffootnote(seebelow).organicbondtypeswhichoccurveryfrequentlyinorgano-The‘Substructure’columnisdesignedtoconveyasmuchmetalliccompoundsandmetalcomplexes(e.g.CNCincyclo-unambiguousinformationaspossiblewithinasmallspace.Forpentadienyl,C-Pintriphenylphosphine,etc.)areeitherabsentCsp3wehaveemployedtheshortformsC*andC#.C*indicatesorpoorlyrepresentedinthiswork.TheseomissionswillbeCsp3whosebonds,additionaltothosespecifiedinthelinearrectifiedinPart2whichisinpreparation.Wealsonotethatformulation,aretoCorHatomsonly.C*-OHwouldthencertainbondtypeslistedhere(e.g.As-0,Si-0,Si-N,etc.)willrepresentthegroupofalcoholsCH,-OH,-C-CH,-OH,occurwithgreaterfrequencyininorganiccompounds.The-C,-CH-OH,and-C,-C-OH.C*isfrequentlyusedtorestrictinterestedreaderisreferredtotheInorganicCrystalStructurethesecondaryenvironmentofagivenbondtoavoidtheDatabasel1foramachine-readablecompendiumofmoreperturbinginfluencesofe.g.electronegativesubstituents.Therelevantstructuraldata.symbolC#ismerelyaspace-savingdevicetoindicateanyCsp3ThetabulationgivenhererepresentsthefirststageinamajoratomandincludesC*asasubset.projectdesignedtoobtaintheaveragegeometriesoffunctionalgroups,rigidringsandthelow-energyconformationsofflexibleUseofthe‘Note’Column.-The‘Note’columnreferstotherings.Detailsofmeanbondlengths,valenceangles,andcon-footnotescollectedinAppendix1.Theserecordadditionalformationalpreferencesinawiderangeofsubstructureswillinformationasfollows:(a)additionaldetailsconcerningtheformthebasisofamachine-readable‘fragmentlibrary’forusechemicaldefinitionofsubstructures,e.g.theomissionofinmolecularmodelingandotherareasofresearch.Thesyste-three-andfour-memberedrings;(b)statementsofgeometricalmaticsurveywillbeextendedtoderiveinformationaboutconstraintsusedinobtainingthecitedaverage,e.g.definitiondistances,angles,directionality,andenvironmentaldependenceofplanarityorpyramidalityatN,torsionalconstraintsinofhydrogenbondsandnon-bondedinteractions.Table.BondSubstructuredrntT414”nNoteAs(3)-As(3)X~-AS-AS-X~2.4592.4570.0112.4562.4668AS-BseeCUDLOC(2.065),CUDLUI(2.041)As-BrseeCODDEE,CODDII(2.346-3.203)AS(4)-CX~-AS-CH~1.9031.9070.0161.8931.91612(X),(C,0,S)As-Csp31.9271.9290.0171.9211.93716As-CarinPh,As+1.9051.9090.0121.8971.912108(X),(C,O,S=)As-Car1.9221.9270.0161.9081.93436As(3)-Cx2-As-c~~~1.9631.9650.0171.9481.9786X2-As-Car1.9561.9560.0151.9441.96441AS(3)-C1XZ-As-CI2.2682.2560.0392.2472.28110As(6)-FinAsF,-1.6781.6760.0201.6591.69536As(3)-IseeOPIMAS(2.579,2.590)As(3)-N(3)X,-As-N-X~1.8581.8580.0291.8391.87319As(4)=N(2)seeTPASSN(1.837)As(4)-0(X),(=)As-OH1.7101.7120.0171.6951.7266As(3t-OseeASAZOC,PHASOCO1(1.787-1.845)As(4)=0X3-Ad1.6611.6610.0161.6521.6679As(3tP(3)seeBELNIP(2.350,2.362)tAs(3t-P(3)seeBUTHAZIO(2.124)tAs(3)-SX2-As-S2.2752.2660.0322.2472.29814As(4)=SX3-AM2.0832.0820.0042.0802.0869As(3)-Se(2)seeCOSDIX,ESEARS(2.355-2.401)tAs(3)-Si(4)seeBICGEZ,MESIAD(2.351-2.365)tAs(3)-Te(2)seeETEARS(2.571,2.576)tB(n)-B(n)n=5-7inboroncages1.7751.7730.0311.7631.786688B(4)-B(4)seeCETTAW(2.041)B(4)-B(3)seeCOFVOI(1.698)B(3)-B(3)x2-B-B-x,1.7011.7000.0141.6911.7128B(6)-Br1.9671.9710.0141.9541.9797tB(4)-Br2.0172.0080.0311.9902.04415tB(ntCn=5-7:B-Cincages1.7161.7170.0201.7071.72896n=3-4:B-Csp3notcages1.5971.5990.0221.5851.611291n=4:&Car1.6061.6070.0121.5961.61541S6J.CHEM.SOC.PERKINTRANS.I11987Table(continued)BondSubstructuredm(T414"nNoten=4:B-CarinPh,B-1.6431.6430.0061.6411.64516WnkCn=3:B-Car1.5561.5520.0151.5461.56624B(n)-CIB(5)-C1andB(3)-CI1.7511.7510.0111.7431.76114B(4)-CI1.8331.8330.0131.8211.84322B(4)-FB-F(Bneutral)1.3661.3680.0171.3561.37525B--FinBF,-1.3651.3720.0291.3521.39084B(4)-IseeTMPBTI(2.220,2.253)B(4)-N(3)X,-B-N(=C)(X)1.6111.6170.0131.6011.6258inpyrazaboles1.5491.5520.0151.5361.56010B(3)-N(3)X,-B-N-C,:allcoplanar1.4041.4040.0141.3891.408402forz(BN)>30"seeBOGSUL,BUSHAY,CILRUK(1.434-1.530)S2-B-N-X21.4471.4430.0131.4351.47014B(4)-0B--0inB04-1.4681.4680.0221.4531.47924forneutralB-0seeNote33B(3)-0(2)X2-B-0-X1.3671.3670.0241.3491.38235B(n)-Pn=4B-P1.9221.9270.0271.9001.95410n=3:seeBUPSIBlO(1.892,1.893)B(4)-SB(4)-S(3)1.9301.9270.0091.9251.93410B(4)-S(2)1.8961.8960.0041.8931.8996W3kSN-BS21.8061.8060.0101.7991.81628(=X-)(N-)BS1.8511.8540.0131.8421.85910Br-BrseeBEPZEB,TPASTB2.5422.5480.0152.5262.5514Br-CBr-C*1.9661.9670.0291.9511.9831004Br-Csp3(cyclopropane)1.9101.9100.0101.9001.9148Br-Csp21.8831.8810.0151.8741.894314Br-Car(mono-Br+m,p-Br,)1.8991.8990.0121.8921.9061194Br-Car(o-Br,)1.8751.8720.0111.8641.88484-Br(2)-ClseeTEACBR(2.362-2.402)tBr-IseeDTHIBRlO(2.646),TPHOSI(2.695)Br-NseeNBBZAM(1.843)Br-0seeCIYFOF1.5811.5810.0071.5741.5874Br-PseeCISTED(2.366)Br-S(2)seeBEMLIO(2.206)tBr-S(3)seeCIWYIQ(2.435,2.453)tBr-S(3)+seeTHINBR(2.321)tBr-SeseeCIFZUM(2.508,2.619)Br-SiseeBIZJAV(2.284)Br-TeInBr,Te2-seeCUGBAH(2.692-2.716)Br-Te(4)seeBETUTElO(3.079,3.015)Br-Te(3)seeBTUPTE(2.835)csp3-csp3C#-CH2-CH31.5131.5140.0141.5071.523192(C#),-CH-CH31.5241.5260.0151.5181.534226(C#)3-C-CH21.5341.5340.0111.5271.541825C#-CH,-CH,-C#1.5241.5240.0141.5161.5322459(C#),-CH-CH,-C#1.5311.5310.0121.5241.5381217(C#)3-C-CH2-C#1.5381.5390.0101.5331.544330(C#),-CH-CH-(C#),1.5421.5420.0111.5361.549321(c#)3-c-cH-(C#)21.5561.5560.0111.5491.562215(C#),-C-C-(C#),1.5881.5800.0251.5661.61021C*-C*(overall)1.5301.5300.0151.5211.539577756incyclopropane(anysubst.)1.5101.5090.0261.4971.5238887incyclobutane(anysubst.)1.5541.5530.0211.5401.5676798incyclopentane(C,H-subst.)1.5431.5430.0181.5321.5541641incyclohexane(C,H-subst.)1.5351.5350.0161.5251.5452814cyclopropyl-C*(exocyclic)1.5181.5180.0191.5051.5313667cyclobutyl-C*(exocyclic)1.5291.5290.0161.5191.5393768cyclopentyl-C*(exocyclic)1.5401.5410.0171.5271.549956cyclohexyl-C*(exocyclic)1.5391.5380.0161.5291.5492682incyclobutene(anysubst.)1.5731.5740.0171.5661.586258incyclopentene(C,H-subst.)1.5411.5390.0151.5321.549208incyclohexene(C,H-subst.)1.5411.5410.0201.5281.554586inoxirane(epoxide