Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 SPARTAN SEMIEMPIRICAL PROGRAM: IBM Release 4.0.3c (Job run on vodka) Calculation started: Wed Jun 14 13:44:55 2000 Run type: Geometry optimization Model: RHF/AM1 Number of shells: 67 44 S shells 23 P shells Number of basis functions: 113 Number of electrons: 118 Use of molecular symmetry disabled Molecular charge: 0 Spin multiplicity: 1 Cartesian Coordinates (Angstroms) Atom X Y Z ---- ------------- ------------- ------------- O 1 .2708220 -.7343326 -3.9022085 C 2 .3812734 -.0082796 -2.8956353 C 3 -.6220701 .0754155 -1.8419978 C 4 -1.8113783 -.6376716 -1.8332370 C 5 -2.7803359 -.4527436 -.6982920 H 6 -2.2924545 .0598506 .1686940 H 7 -3.6386774 .1775190 -1.0433790 H 8 -3.1772449 -1.4348881 -.3380057 C 9 -.3389476 1.0307468 -.7460043 C 10 1.5882923 .8652028 -2.7323287 H 11 2.1588647 .5639867 -1.8176386 H 12 2.2566292 .7781595 -3.6225425 H 13 1.2675537 1.9296298 -2.6167181 N 14 -2.1632077 -1.5028687 -2.8295104 H 15 -1.5385270 -1.6300657 -3.6001447 C 16 -3.3863567 -2.2387796 -2.8247611 H 17 -3.3764911 -3.0295600 -2.0248388 H 18 -4.2635113 -1.5606166 -2.6400834 H 19 -3.5160391 -2.7369470 -3.8218271 O 20 -.8906491 2.1318782 -.6599251 C 21 .6738044 .5379358 .2852645 H 22 1.1467896 -.3944617 -.1501839 C 23 1.7675257 1.5325743 .5382205 C 24 3.1023470 1.1191989 .4295734 H 25 3.3359210 .0805993 .1505012 C 26 4.1396733 2.0165349 .6763416 H 27 5.1838595 1.6820234 .5910004 C 28 3.8556822 3.3351516 1.0309695 H 29 4.6749728 4.0422431 1.2258438 C 30 2.5297637 3.7533375 1.1361681 H 31 2.3003517 4.7931019 1.4117236 C 32 1.4895869 2.8575325 .8924565 H 33 .4419565 3.1925700 .9640715 C 34 -.0116910 .1495096 1.5629637 C 35 -.9877936 .9633228 2.1499981 H 36 -1.2733723 1.9103374 1.6623077 C 37 -1.5950648 .5822549 3.3454566 H 38 -2.3583937 1.2305506 3.8006418 C 39 -1.2351466 -.6140178 3.9652366 H 40 -1.7136434 -.9121093 4.9092772 C 41 -.2641169 -1.4296512 3.3848659 H 42 .0249895 -2.3729282 3.8710271 C 43 .3452790 -1.0515041 2.1896796 H 44 1.1133566 -1.6988265 1.7399494 Point Group = C1 Order = 1 Nsymop = 1 This system has 126 degrees of freedom Initial Hessian option Hessian will be estimated using the Sybyl/X forcefield Magnitude of eigenvalue 8 too small, replaced by .000100 Cycle no: 1 Heat of formation = -11.806 rmsG = .0005 rmsD = .0138 Magnitude of eigenvalue 7 too small, replaced by .000100 Cycle no: 2 Heat of formation = -11.699 rmsG = .0007 rmsD = .0138 Magnitude of eigenvalue 6 too small, replaced by .000100 Cycle no: 3 Heat of formation = -11.581 rmsG = .0008 rmsD = .0138 Magnitude of eigenvalue 5 too small, replaced by .000100 Cycle no: 4 Heat of formation = -11.490 rmsG = .0009 rmsD = .0138 Magnitude of eigenvalue 4 too small, replaced by .000100 Cycle no: 5 Heat of formation = -11.431 rmsG = .0011 rmsD = .0138 Magnitude of eigenvalue 3 too small, replaced by .000100 Cycle no: 6 Heat of formation = -11.351 rmsG = .0012 rmsD = .0138 Cycle no: 7 Heat of formation = -11.700 rmsG = .0009 rmsD = .0138 Cycle no: 8 Heat of formation = -11.950 rmsG = .0008 rmsD = .0138 Cycle no: 9 Heat of formation = -11.968 rmsG = .0007 rmsD = .0138 Cycle no: 10 Heat of formation = -12.059 rmsG = .0009 rmsD = .0138 Cycle no: 11 Heat of formation = -12.112 rmsG = .0007 rmsD = .0138 Cycle no: 12 Heat of formation = -12.210 rmsG = .0007 rmsD = .0081 Cycle no: 13 Heat of formation = -12.288 rmsG = .0005 rmsD = .0117 Cycle no: 14 Heat of formation = -12.356 rmsG = .0004 rmsD = .0100 Cycle no: 15 Heat of formation = -12.398 rmsG = .0004 rmsD = .0041 Cycle no: 16 Heat of formation = -12.402 rmsG = .0005 rmsD = .0066 Cycle no: 17 Heat of formation = -12.414 rmsG = .0003 rmsD = .0031 Cycle no: 18 Heat of formation = -12.421 rmsG = .0002 rmsD = .0024 Cycle no: 19 Heat of formation = -12.424 rmsG = .0001 rmsD = .0032 Cycle no: 20 Heat of formation = -12.427 rmsG = .0001 rmsD = .0044 Cycle no: 21 Heat of formation = -12.429 rmsG = .0001 rmsD = .0012 Cycle no: 22 Heat of formation = -12.430 rmsG = .0001 rmsD = .0022 Cycle no: 23 Heat of formation = -12.431 rmsG = .0001 rmsD = .0013 Cycle no: 24 Heat of formation = -12.432 rmsG = .0000 rmsD = .0014 Cycle no: 25 Heat of formation = -12.433 rmsG = .0000 rmsD = .0032 Cycle no: 26 Heat of formation = -12.433 rmsG = .0000 rmsD = .0009 Cycle no: 27 Heat of formation = -12.434 rmsG = .0000 rmsD = .0012 Cycle no: 28 Heat of formation = -12.434 rmsG = .0000 rmsD = .0003 Cycle no: 29 Heat of formation = -12.434 rmsG = .0000 rmsD = .0005 Cycle no: 30 Heat of formation = -12.434 rmsG = .0000 rmsD = .0003 Cycle no: 31 Heat of formation = -12.434 rmsG = .0000 rmsD = .0004 Cycle no: 32 Heat of formation = -12.434 rmsG = .0000 rmsD = .0002 Cycle no: 33 Heat of formation = -12.434 rmsG = .0000 rmsD = .0005 Cycle no: 34 Heat of formation = -12.434 rmsG = .0000 rmsD = .0001 Cycle no: 35 Heat of formation = -12.434 rmsG = .0000 rmsD = .0005 Cycle no: 36 Heat of formation = -12.434 rmsG = .0000 rmsD = .0001 Cycle no: 37 Heat of formation = -12.434 rmsG = .0000 rmsD = .0002 Cycle no: 38 Heat of formation = -12.434 rmsG = .0000 rmsD = .0002 Cycle no: 39 Heat of formation = -12.434 rmsG = .0000 rmsD = .0004 Cycle no: 40 Heat of formation = -12.434 rmsG = .0000 rmsD = .0002 Cycle no: 41 Heat of formation = -12.434 rmsG = .0000 rmsD = .0002 Cycle no: 42 Heat of formation = -12.434 rmsG = .0000 rmsD = .0002 Cycle no: 43 Heat of formation = -12.434 rmsG = .0000 rmsD = .0001 Cycle no: 44 Heat of formation = -12.434 rmsG = .0000 rmsD = .0001 Convergence on Energy - difference below .5000D-03 kcal/mol Cycle no: 45 Heat of formation = -12.434 rmsG = .0000 rmsD = .0001 Cartesian Coordinates (Angstroms) Atom X Y Z ---- ------------- ------------- ------------- O 1 .2928382 -1.3493716 -3.7332084 C 2 .2819447 -.4763896 -2.8441936 C 3 -.7199551 -.4062871 -1.7884478 C 4 -1.9055180 -1.1254353 -1.7822847 C 5 -2.9028248 -.9027591 -.6791611 H 6 -2.4382247 -.3561537 .1799959 H 7 -3.7546212 -.2894606 -1.0682061 H 8 -3.3048271 -1.8725596 -.2927209 C 9 -.4404188 .5434342 -.6864000 C 10 1.3279370 .5968773 -2.8364699 H 11 1.9445300 .5226259 -1.9050494 H 12 1.9972368 .4968582 -3.7245398 H 13 .8363173 1.6006023 -2.8579095 N 14 -2.2285649 -2.0290709 -2.7537647 H 15 -1.5745950 -2.1978649 -3.4913461 C 16 -3.4565516 -2.7567884 -2.7626994 H 17 -3.4763822 -3.5221768 -1.9386135 H 18 -4.3338268 -2.0676063 -2.6260607 H 19 -3.5600607 -3.2850773 -3.7473485 O 20 -.9851902 1.6481193 -.6024012 C 21 .5600555 .0411502 .3522369 H 22 1.0225820 -.8993615 -.0768656 C 23 1.6661194 1.0218352 .6062856 C 24 2.9954186 .5877869 .5120569 H 25 3.2156627 -.4563169 .2429842 C 26 4.0440185 1.4713375 .7606989 H 27 5.0837512 1.1206739 .6863148 C 28 3.7768965 2.7966968 1.1031814 H 29 4.6049929 3.4928366 1.2999121 C 30 2.4565610 3.2354747 1.1938797 H 31 2.2402903 4.2805791 1.4599686 C 32 1.4051831 2.3535476 .9479135 H 33 .3622445 2.7051205 1.0080453 C 34 -.1368503 -.3319695 1.6283213 C 35 -1.0969772 .5029627 2.2121285 H 36 -1.3623964 1.4543150 1.7216982 C 37 -1.7137157 .1371004 3.4074486 H 38 -2.4636036 .8022644 3.8603764 C 39 -1.3796006 -1.0651384 4.0301968 H 40 -1.8647752 -1.3510042 4.9746434 C 41 -.4258045 -1.9024068 3.4522898 H 42 -.1576049 -2.8508083 3.9405080 C 43 .1931604 -1.5393861 2.2573029 H 44 .9476123 -2.2038315 1.8097368 Heat of Formation: -12.434 kcal/mol ** Archive file written to unit 12 ** Total Cpu time: 5 mins. 22.39 secs. Total Wall time: 5 mins. 47.88 secs. Calculation finished: Wed Jun 14 13:50:43 2000