Supporting Information - Semantic Scholar
An n→π* Interaction in Aspirin: Implications for Structure and Reactivity Amit Choudhary,† Kimberli J. Kamer,§ and Ronald T. Raines*,§,‡ †
Graduate Program in Biophysics, §Department of Biochemistry, and ‡Department of Chemistry, University of Wisconsin–Madison, Madison, Wisconsin 53706, United States *E-mail: [email protected]
Page
Contents
S1
Table of Contents
S2
Table S1. SCF energies of 1–17
S3
Table S2. Atomic coordinates of conformation 1
S4
Table S3. Atomic coordinates of conformation 2
S5
Table S4. Atomic coordinates of conformation 3
S6
Table S5. Atomic coordinates of conformation 4
S7
Table S6. Atomic coordinates of conformation 5
S8
Table S7. Atomic coordinates of conformation 6
S9
Table S8. Atomic coordinates of conformation 7
S10
Table S9. Atomic coordinates of conformation 8
S11
Table S10. Atomic coordinates of optimized conformation of compound 9
S12
Table S11. Atomic coordinates of optimized conformation of compound 10
S13
Table S12. Atomic coordinates of optimized conformation of compound 11
S14
Table S13. Atomic coordinates of optimized conformation of compound 12
S15
Table S14. Atomic coordinates of optimized conformation of compound 13
S16
Table S15. Atomic coordinates of optimized conformation of compound 14
S17
Table S16. Atomic coordinates of optimized conformation of compound 15
S18
Table S17. Atomic coordinates of optimized conformation of compound 16
S19
Table S17. Atomic coordinates of optimized conformation of compound 17
–S1–
Choudhary, Kamer, and Raines
Supporting Information
Table S1. SCF energies (atomic units; au) of conformations 1–8 and compounds 9–17 calculated at B3LYP/6–311+g(2d,p) level of theory. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17
Energy –648.90486736 –648.90352357 –648.89968559 –648.89608416 –648.89632496 –648.89602928 –648.36068901 –648.35897360 –852.94412753 –740.64220400 –762.92065233 –782.36282729 –852.94527260 –740.64241835 –762.91909983 –782.36260440 –836.35529075
Zero-point correction 0.156289 0.156276 0.156511 0.155933 0.156233 0.156205 0.142654 0.142703 0.144945 0.141245 0.174901 0.215057 0.145006 0.141267 0.174853 0.214879 0.144033
–S2–
Energy (corrected) –648.74857836 –648.74724757 –648.74317459 –648.74015116 –648.74008996 –648.73982428 –648.21803501 –648.21627060 –852.79918253 –740.50095900 –762.74575133 –782.14777029 –852.80026660 –740.50115135 –762.74424683 –782.14772540 –836.21125775
Choudhary, Kamer, and Raines
Supporting Information
Table S2. Atomic coordinates of conformation 1. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.230697 –2.962483 –0.855930 –2.718526 –0.099142 –2.327725 –0.234591 –4.023695 1.083083 –0.891156 1.101854 –0.965978 –2.890459 2.044167 –0.305871 –0.450355 1.762207 3.416660 4.160962 3.519900 3.554458
y 0.489144 –0.687391 0.485360 1.434406 1.762837 –1.899451 –0.749617 –0.658819 1.890045 2.843649 –0.843211 –1.927494 –2.825045 –0.690381 3.615338 –2.858535 –0.639924 –0.612520 –0.709935 0.359416 –1.384228
–S3–
z 0.176517 0.201165 –0.093807 0.366055 –0.137471 –0.049511 –0.335898 0.413737 –0.351962 0.087939 –0.683006 –0.317353 –0.033993 0.311725 0.046459 –0.513895 1.474003 –0.285295 0.500991 –0.772337 –1.043246
Choudhary, Kamer, and Raines
Supporting Information
Table S3. Atomic coordinates of conformation 2. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.271795 –2.967594 –0.897837 –2.773624 –0.280396 –2.293169 –0.237138 –4.029977 1.019131 –0.879227 1.109327 –0.930787 –2.824806 2.037807 1.276918 –0.385125 1.745092 3.424904 4.151162 3.571364 3.555546
y 0.463516 –0.733188 0.507663 1.402021 1.863683 –1.923849 –0.703773 –0.738613 1.906301 2.869506 –0.768613 –1.905417 –2.867696 –0.679596 2.839668 –2.819375 –0.593803 –0.715952 –0.708845 0.153713 –1.606519
–S4–
z 0.171187 0.188161 –0.097778 0.364787 –0.095556 –0.064340 –0.342244 0.396609 –0.473995 0.203632 –0.679532 –0.327052 –0.054258 0.329299 –0.410479 –0.523107 1.487453 –0.243617 0.564904 –0.886751 –0.860537
Choudhary, Kamer, and Raines
Supporting Information
Table S4. Atomic coordinates of conformation 3. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.311983 –2.915244 –0.949110 –2.888511 –0.391394 –2.165352 –0.219417 –3.969723 –0.925122 0.710006 1.117224 –0.817654 –2.629201 2.116775 0.982928 –0.221848 1.920709 3.455362 4.239145 3.578705 3.514067
y 0.354510 –0.891385 0.481174 1.257626 1.878423 –2.039522 –0.682389 –0.966058 2.745681 2.131793 –0.649356 –1.932634 –3.016911 –0.544328 1.349460 –2.809392 –0.281421 –0.772534 –0.601480 –0.100127 –1.794579
–S5–
z 0.215422 0.295300 –0.069469 0.369410 –0.138249 0.061189 –0.307102 0.529490 –0.776107 0.590569 –0.744713 –0.253346 0.109855 0.169039 1.107091 –0.472923 1.331179 –0.465519 0.267264 –1.316103 –0.845104
Choudhary, Kamer, and Raines
Supporting Information
Table S5. Atomic coordinates of conformation 4. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.146087 –3.056398 –0.784579 –2.500556 0.165338 –2.607536 –0.354376 –4.109140 1.009279 –0.006563 0.965738 –1.255458 –3.307057 1.939893 –0.586342 –0.883015 1.695836 3.298193 4.041350 3.512834 3.323659
y 0.767709 –0.277969 0.527239 1.790586 1.673484 –1.589056 –0.800118 –0.067981 1.723573 2.715368 –1.130601 –1.848642 –2.413053 –0.748729 2.457515 –2.862231 –0.234913 –1.058791 –0.959409 –0.344318 –2.059281
–S6–
z 0.053715 0.138821 –0.151039 0.109000 –0.326446 0.035854 –0.254160 0.279313 –1.178368 0.525372 –0.513605 –0.153648 0.104538 0.379083 1.254589 –0.228182 1.434601 –0.172513 0.614440 –0.971044 –0.604650
Choudhary, Kamer, and Raines
Supporting Information
Table S6. Atomic coordinates of conformation 5. Atom C C C H C C C H O O O C H C H H C O H H H
x –2.258754 –2.776570 –0.917611 –2.888341 –0.372302 –1.960316 –0.105711 –3.813660 0.779013 –1.330923 1.180934 –0.633626 –2.358889 2.295481 –0.889397 0.007592 2.061075 3.362737 3.027948 1.508722 1.481931
y 0.193126 –1.092525 0.425801 1.038813 1.808001 –2.170345 –0.671873 –1.252637 2.105256 2.746750 –0.505434 –1.958059 –3.177703 –0.474980 3.607330 –2.779543 –0.629975 –0.349816 –0.655789 –1.545333 0.215788
–S7–
z 0.260423 0.286744 –0.066810 0.500676 –0.032595 –0.042537 –0.392010 0.552941 0.173752 –0.231089 –0.858874 –0.391903 –0.040108 –0.035112 –0.156870 –0.685731 1.443133 –0.554103 1.938621 1.662247 1.814743
Choudhary, Kamer, and Raines
Supporting Information
Table S7. Atomic coordinates of conformation 6. Atom C C C H C C C H O O O C H C H H C O H H H
x –2.280052 –2.821321 –0.934670 –2.886600 –0.475234 –2.022518 –0.141835 –3.862339 0.862357 –1.223312 1.156378 –0.691767 –2.437822 2.256737 1.037875 –0.064051 2.000124 3.337265 2.958583 1.469356 1.386707
y 0.259052 –1.015536 0.476002 1.123193 1.894573 –2.104651 –0.632955 –1.159628 2.044147 2.840507 –0.490965 –1.910566 –3.105190 –0.553807 2.998447 –2.740109 –0.792846 –0.428885 –0.824245 –1.733688 0.007187
–S8–
z 0.253272 0.265725 –0.068457 0.490322 –0.053470 –0.071624 –0.400280 0.525547 0.067213 –0.109860 –0.853831 –0.413673 –0.081839 –0.021041 0.052034 –0.714215 1.443884 –0.515014 1.954953 1.599468 1.859650
Choudhary, Kamer, and Raines
Supporting Information
Table S8. Atomic coordinates of conformation 7. Atom C C C H C C C H O O O C H C H O C H H H
x –2.196746 –2.993685 –0.831674 –2.610664 –0.012091 –2.438299 –0.304934 –4.048276 1.219002 –0.686267 1.027514 –1.086998 –3.049337 1.988878 –0.622140 1.791741 3.316684 4.118014 3.287546 3.462132
y 0.632637 –0.506199 0.585713 1.610520 1.905402 –1.740617 –0.668545 –0.431687 1.785958 2.942654 –0.789157 –1.816542 –2.636972 –0.816689 –2.758802 –1.183691 –0.404334 –0.712931 0.683955 –0.825152
–S9–
z 0.251664 0.252234 –0.044928 0.465385 –0.015701 –0.075482 –0.361333 0.497626 0.188221 –0.183665 –0.767196 –0.389942 –0.088113 0.203779 –0.655521 1.331655 –0.364727 0.304490 –0.448066 –1.361306
Choudhary, Kamer, and Raines
Supporting Information
Table S9. Atomic coordinates of conformation 8. Atom C C C H C C C H O O O C H C H C O H H H
x 0.000000 1.389009 –0.746117 –0.549889 –2.287042 2.081690 –0.025788 1.932056 –2.833274 –2.789772 –0.665625 1.366192 3.165815 –1.040858 1.872177 –0.903677 –1.463267 –1.176046 0.113627 –1.582478
y 0.000000 0.000000 1.184206 –0.933628 1.084120 1.208189 2.379219 –0.939333 1.719614 0.343684 3.619801 2.398429 1.225544 4.355567 3.355258 3.713009 5.468065 4.443367 3.354627 2.852485
–S10–
z 0.000000 0.000000 0.000000 –0.016878 0.049157 –0.039212 –0.025950 0.013289 0.981052 –0.816954 –0.141902 –0.068037 –0.061698 0.945599 –0.131833 2.296929 0.756797 3.055692 2.465453 2.310950
Choudhary, Kamer, and Raines
Supporting Information
Table S10. Atomic coordinates of optimized conformation of compound 9. Atom C C C
x –1.215153 –2.076158 0.155723
y 0.799875 –0.288944 0.636489
z 0.017767 –0.040507 –0.169605
H C C C O O C H C H O C H H H N O O
–1.585247 1.068265 –1.614982 0.609006 0.473964 1.943646 –0.259450 –2.309275 2.832935 0.150648 2.514505 4.223517 4.944995 4.283269 4.413853 –3.509997 –4.255622 –3.910485
1.801036 1.897439 –1.574323 –0.660753 2.971073 –0.900531 –1.748477 –2.399952 –0.899494 –2.726385 –1.170714 –0.628638 –0.921484 0.444825 –1.157489 –0.090964 –1.067698 1.033499
0.185809 –0.109775 –0.318228 –0.430788 –0.317241 –0.713946 –0.519142 –0.368019 0.340098 –0.738196 1.464205 –0.151536 0.608854 –0.338375 –1.087176 0.175511 0.058344 0.462862
–S11–
Choudhary, Kamer, and Raines
Supporting Information
Table S11. Atomic coordinates of optimized conformation of compound 10. Atom C C C H C C C O O O C H C H O C C N H H H
x –1.575317 –2.440084 –0.203552 –1.948709 0.684796 –1.933480 0.270845 1.897653 0.067183 1.608898 –0.576446 –2.599765 2.507557 –0.151564 2.207226 3.888814 –3.843632 –4.979161 3.929908 4.624052 4.075511
y 0.765315 –0.332119 0.632372 1.763851 1.909637 –1.604595 –0.650731 1.715896 2.977092 –0.856880 –1.752033 –2.456230 –0.882817 –2.719285 –1.193105 –0.571130 –0.167724 –0.054308 0.510638 –0.886363 –1.053514
–S12–
z 0.062602 0.002516 –0.140532 0.250313 –0.058567 –0.297293 –0.427324 0.182360 –0.233078 –0.735628 –0.517394 –0.354067 0.305983 –0.755542 1.425645 –0.189056 0.228919 0.407882 –0.328228 0.548947 –1.150118
Choudhary, Kamer, and Raines
Supporting Information
Table S12. Atomic coordinates of optimized conformation of compound 11. Atom C C C H C C C O O O C H C H O C H H H C H H H O
x –1.531899 –2.276583 –0.144484 –1.975308 0.595958 –1.645045 0.464725 1.832002 –0.141657 1.830744 –0.272884 –2.233607 2.708952 0.243746 2.434571 4.063954 4.818379 4.004026 4.305279 –4.316401 –5.368769 –3.947481 –4.208513 –3.645099
y 0.528247 –0.643060 0.524561 1.503061 1.893113 –1.862240 –0.706292 1.845348 2.892411 –0.787555 –1.883126 –2.771262 –0.715217 –2.815249 –1.012501 –0.288038 –0.517988 0.790075 –0.768320 0.518594 0.262774 0.996061 1.223189 –0.700403
–S13–
z 0.001271 –0.037139 –0.181019 0.149847 –0.115494 –0.282468 –0.417558 0.079498 –0.252444 –0.709656 –0.475635 –0.318045 0.332674 –0.672364 1.465212 –0.156252 0.594168 –0.317768 –1.106245 0.403224 0.527098 1.316930 –0.427919 0.145475
Choudhary, Kamer, and Raines
Supporting Information
Table S13. Atomic coordinates of optimized conformation of compound 12. Atom C C C H C C C O O O C H C H O C H H H C C H H H H H H N
x –1.112001 –2.016272 0.250482 –1.438831 1.150343 –1.516024 0.712225 2.367830 0.545362 2.051266 –0.154234 –2.167504 2.959870 0.241091 2.685123 4.339413 4.390893 5.084761 4.502024 –4.247332 –4.030548 –3.826322 –5.223025 –4.412712 –3.402729 –4.239871 –4.978152 –3.391689
y 0.792822 –0.272829 0.657308 1.790166 1.919690 –1.528403 –0.617304 1.708973 3.007967 –0.819752 –1.689219 –2.385806 –0.949379 –2.657783 –1.333740 –0.616862 0.472761 –1.001760 –1.016822 –1.226769 1.067446 –1.990206 –0.938660 –1.680476 1.952627 0.860819 1.292210 –0.060524
–S14–
z 0.150127 0.062474 –0.091666 0.413877 0.045662 –0.299561 –0.438470 0.253755 –0.053829 –0.788971 –0.544452 –0.400574 0.221608 –0.828123 1.327540 –0.272078 –0.320697 0.421894 –1.274632 0.399326 –0.294612 1.055024 0.798170 –0.595475 –0.242475 –1.359082 0.202512 0.370211
Choudhary, Kamer, and Raines
Supporting Information
Table S14. Atomic coordinates of optimized conformation of compound 13. Atom C C H C C C O O O C C H O C N O O H H H C H
x –0.569861 0.537251 –0.388419 1.948902 –2.049373 0.293586 2.850473 1.999858 1.358867 –0.979461 2.072375 –1.141214 1.619126 3.447472 –3.396421 –4.329547 –3.548642 3.905815 3.414433 4.016866 –1.855411 –2.706490
y 1.911937 1.123484 2.956083 1.750682 0.066056 –0.213787 1.038362 2.900283 –1.011184 –0.751331 –1.661216 –1.783251 –1.941467 –1.992589 –0.486580 0.241806 –1.657363 –2.738681 –2.341517 –1.060681 1.400099 2.010597
–S15–
z 0.301640 –0.032247 0.522516 –0.032421 –0.030395 –0.364938 0.461184 –0.510333 –0.775102 –0.382573 0.202804 –0.655687 1.277771 –0.295493 –0.039852 0.305905 –0.393571 0.350547 –1.328711 –0.263993 0.323447 0.588521
Choudhary, Kamer, and Raines
Supporting Information
Table S15. Atomic coordinates of optimized conformation of compound 14. Atom C C H C C C O O O C C H O C H H H C N C H
x –0.993933 0.149819 –0.853409 1.529600 –2.411584 –0.034653 2.502907 1.487601 1.051268 –1.285970 1.839450 –1.380726 1.446121 3.204364 3.723464 3.139633 3.732347 –3.709204 –4.761157 –2.256203 –3.126500
y 1.801677 1.066925 2.852056 1.776735 –0.115280 –0.277634 1.061525 2.985900 –1.039515 –0.869713 –1.609636 –1.910697 –1.870471 –1.903494 –2.600949 –2.299854 –0.948124 –0.714291 –1.192046 1.233250 1.821142
–S16–
z 0.300323 –0.026706 0.522446 –0.013326 –0.034769 –0.362126 0.313021 –0.312938 –0.785756 –0.381532 0.183918 –0.661248 1.287480 –0.364196 0.290364 –1.378858 –0.398313 –0.046639 –0.056399 0.315834 0.581254
Choudhary, Kamer, and Raines
Supporting Information
Table S16. Atomic coordinates of optimized conformation of compound 15. Atom C C H C C C O O O C C H O C C H H H O H H H C H
x –0.975221 0.229547 –0.912085 1.542399 –2.253678 0.137623 2.613852 1.379717 1.264778 –1.072146 2.165415 –1.096636 1.876453 3.511326 –4.628210 –5.404250 –4.636159 –4.837465 –3.408613 3.956548 4.128362 3.409659 –2.208555 –3.108471
y 1.643863 0.996597 2.707335 1.827623 –0.365933 –0.372282 1.176115 3.065827 –1.106266 –1.048160 –1.431674 –2.105542 –1.548393 –1.715783 –0.470554 –1.231577 –0.054173 0.334007 –1.120976 –0.745716 –2.258513 –2.280577 0.994424 1.555578
–S17–
z 0.192507 –0.067747 0.388285 –0.049696 –0.104590 –0.348447 –0.022836 –0.057732 –0.718295 –0.377558 0.259719 –0.607776 1.420538 –0.343703 0.135624 0.055003 1.149306 –0.578723 –0.152144 –0.571187 0.370370 –1.272341 0.188565 0.402762
Choudhary, Kamer, and Raines
Supporting Information
Table S17. Atomic coordinates of optimized conformation of compound 16. Atom C C H C C C O O O C C H O C H H H C C H H H H H H N C H
x –0.480649 0.631131 –0.292502 2.029459 –2.015916 0.365648 3.018750 2.011705 1.382062 –0.912265 2.286517 –1.024352 2.043917 3.559516 4.102142 4.144446 3.347704 –3.734038 –4.381318 –2.948621 –4.614848 –3.991399 –4.096321 –4.659946 –5.268725 –3.313375 –1.775493 –2.590965
y 1.864193 1.066262 2.925827 1.732849 –0.006222 –0.297441 0.961976 2.977071 –1.190632 –0.827399 –1.537439 –1.898327 –1.523351 –2.029931 –1.143087 –2.579722 –2.655904 –1.437297 0.289051 –2.140424 –2.011648 –0.858357 0.793456 1.058773 –0.315872 –0.583734 1.360866 2.045962
–S18–
z 0.158862 –0.097571 0.264107 –0.201864 0.072395 –0.261799 –0.162782 –0.308869 –0.607620 –0.183196 0.359031 –0.293240 1.536268 –0.268868 –0.600433 0.466563 –1.137916 –0.915353 0.630900 –1.180864 –0.615418 –1.819819 1.554506 –0.110630 0.832679 0.186969 0.247062 0.438112
Choudhary, Kamer, and Raines
Supporting Information
Table S18. Atomic coordinates of optimized conformation of compound 17. Atom C C C H C C C H O O O C H C O C H H H C O O
x –1.741024 –0.703737 –1.484517 –2.778740 –2.698659 0.613841 –0.142547 –0.923130 –2.601018 –3.682774 0.099015 0.933594 1.446940 0.676776 0.876004 1.048987 1.330203 0.215230 1.895852 2.439223 2.710414 3.243612
y –1.925407 –2.838452 –0.576096 –2.233734 0.383130 –2.420846 –0.191715 –3.882688 1.505650 –0.102676 1.140927 –1.091906 –3.106992 1.964723 1.731868 3.255678 4.000615 3.614389 3.038198 –0.754253 0.359667 –1.667802
–S19–
z 0.223761 0.372452 –0.024612 0.279116 –0.154820 0.225244 –0.148233 0.585785 0.386957 –0.772297 –0.492899 –0.063195 0.315739 0.390798 1.557190 –0.297904 0.445510 –0.903784 –0.952802 –0.309092 –0.815887 0.004941
Graduate Program in Biophysics, §Department of Biochemistry, and ‡Department of Chemistry, University of Wisconsin–Madison, Madison, Wisconsin 53706, United States *E-mail: [email protected]
Page
Contents
S1
Table of Contents
S2
Table S1. SCF energies of 1–17
S3
Table S2. Atomic coordinates of conformation 1
S4
Table S3. Atomic coordinates of conformation 2
S5
Table S4. Atomic coordinates of conformation 3
S6
Table S5. Atomic coordinates of conformation 4
S7
Table S6. Atomic coordinates of conformation 5
S8
Table S7. Atomic coordinates of conformation 6
S9
Table S8. Atomic coordinates of conformation 7
S10
Table S9. Atomic coordinates of conformation 8
S11
Table S10. Atomic coordinates of optimized conformation of compound 9
S12
Table S11. Atomic coordinates of optimized conformation of compound 10
S13
Table S12. Atomic coordinates of optimized conformation of compound 11
S14
Table S13. Atomic coordinates of optimized conformation of compound 12
S15
Table S14. Atomic coordinates of optimized conformation of compound 13
S16
Table S15. Atomic coordinates of optimized conformation of compound 14
S17
Table S16. Atomic coordinates of optimized conformation of compound 15
S18
Table S17. Atomic coordinates of optimized conformation of compound 16
S19
Table S17. Atomic coordinates of optimized conformation of compound 17
–S1–
Choudhary, Kamer, and Raines
Supporting Information
Table S1. SCF energies (atomic units; au) of conformations 1–8 and compounds 9–17 calculated at B3LYP/6–311+g(2d,p) level of theory. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17
Energy –648.90486736 –648.90352357 –648.89968559 –648.89608416 –648.89632496 –648.89602928 –648.36068901 –648.35897360 –852.94412753 –740.64220400 –762.92065233 –782.36282729 –852.94527260 –740.64241835 –762.91909983 –782.36260440 –836.35529075
Zero-point correction 0.156289 0.156276 0.156511 0.155933 0.156233 0.156205 0.142654 0.142703 0.144945 0.141245 0.174901 0.215057 0.145006 0.141267 0.174853 0.214879 0.144033
–S2–
Energy (corrected) –648.74857836 –648.74724757 –648.74317459 –648.74015116 –648.74008996 –648.73982428 –648.21803501 –648.21627060 –852.79918253 –740.50095900 –762.74575133 –782.14777029 –852.80026660 –740.50115135 –762.74424683 –782.14772540 –836.21125775
Choudhary, Kamer, and Raines
Supporting Information
Table S2. Atomic coordinates of conformation 1. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.230697 –2.962483 –0.855930 –2.718526 –0.099142 –2.327725 –0.234591 –4.023695 1.083083 –0.891156 1.101854 –0.965978 –2.890459 2.044167 –0.305871 –0.450355 1.762207 3.416660 4.160962 3.519900 3.554458
y 0.489144 –0.687391 0.485360 1.434406 1.762837 –1.899451 –0.749617 –0.658819 1.890045 2.843649 –0.843211 –1.927494 –2.825045 –0.690381 3.615338 –2.858535 –0.639924 –0.612520 –0.709935 0.359416 –1.384228
–S3–
z 0.176517 0.201165 –0.093807 0.366055 –0.137471 –0.049511 –0.335898 0.413737 –0.351962 0.087939 –0.683006 –0.317353 –0.033993 0.311725 0.046459 –0.513895 1.474003 –0.285295 0.500991 –0.772337 –1.043246
Choudhary, Kamer, and Raines
Supporting Information
Table S3. Atomic coordinates of conformation 2. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.271795 –2.967594 –0.897837 –2.773624 –0.280396 –2.293169 –0.237138 –4.029977 1.019131 –0.879227 1.109327 –0.930787 –2.824806 2.037807 1.276918 –0.385125 1.745092 3.424904 4.151162 3.571364 3.555546
y 0.463516 –0.733188 0.507663 1.402021 1.863683 –1.923849 –0.703773 –0.738613 1.906301 2.869506 –0.768613 –1.905417 –2.867696 –0.679596 2.839668 –2.819375 –0.593803 –0.715952 –0.708845 0.153713 –1.606519
–S4–
z 0.171187 0.188161 –0.097778 0.364787 –0.095556 –0.064340 –0.342244 0.396609 –0.473995 0.203632 –0.679532 –0.327052 –0.054258 0.329299 –0.410479 –0.523107 1.487453 –0.243617 0.564904 –0.886751 –0.860537
Choudhary, Kamer, and Raines
Supporting Information
Table S4. Atomic coordinates of conformation 3. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.311983 –2.915244 –0.949110 –2.888511 –0.391394 –2.165352 –0.219417 –3.969723 –0.925122 0.710006 1.117224 –0.817654 –2.629201 2.116775 0.982928 –0.221848 1.920709 3.455362 4.239145 3.578705 3.514067
y 0.354510 –0.891385 0.481174 1.257626 1.878423 –2.039522 –0.682389 –0.966058 2.745681 2.131793 –0.649356 –1.932634 –3.016911 –0.544328 1.349460 –2.809392 –0.281421 –0.772534 –0.601480 –0.100127 –1.794579
–S5–
z 0.215422 0.295300 –0.069469 0.369410 –0.138249 0.061189 –0.307102 0.529490 –0.776107 0.590569 –0.744713 –0.253346 0.109855 0.169039 1.107091 –0.472923 1.331179 –0.465519 0.267264 –1.316103 –0.845104
Choudhary, Kamer, and Raines
Supporting Information
Table S5. Atomic coordinates of conformation 4. Atom C C C H C C C H O O O C H C H H O C H H H
x –2.146087 –3.056398 –0.784579 –2.500556 0.165338 –2.607536 –0.354376 –4.109140 1.009279 –0.006563 0.965738 –1.255458 –3.307057 1.939893 –0.586342 –0.883015 1.695836 3.298193 4.041350 3.512834 3.323659
y 0.767709 –0.277969 0.527239 1.790586 1.673484 –1.589056 –0.800118 –0.067981 1.723573 2.715368 –1.130601 –1.848642 –2.413053 –0.748729 2.457515 –2.862231 –0.234913 –1.058791 –0.959409 –0.344318 –2.059281
–S6–
z 0.053715 0.138821 –0.151039 0.109000 –0.326446 0.035854 –0.254160 0.279313 –1.178368 0.525372 –0.513605 –0.153648 0.104538 0.379083 1.254589 –0.228182 1.434601 –0.172513 0.614440 –0.971044 –0.604650
Choudhary, Kamer, and Raines
Supporting Information
Table S6. Atomic coordinates of conformation 5. Atom C C C H C C C H O O O C H C H H C O H H H
x –2.258754 –2.776570 –0.917611 –2.888341 –0.372302 –1.960316 –0.105711 –3.813660 0.779013 –1.330923 1.180934 –0.633626 –2.358889 2.295481 –0.889397 0.007592 2.061075 3.362737 3.027948 1.508722 1.481931
y 0.193126 –1.092525 0.425801 1.038813 1.808001 –2.170345 –0.671873 –1.252637 2.105256 2.746750 –0.505434 –1.958059 –3.177703 –0.474980 3.607330 –2.779543 –0.629975 –0.349816 –0.655789 –1.545333 0.215788
–S7–
z 0.260423 0.286744 –0.066810 0.500676 –0.032595 –0.042537 –0.392010 0.552941 0.173752 –0.231089 –0.858874 –0.391903 –0.040108 –0.035112 –0.156870 –0.685731 1.443133 –0.554103 1.938621 1.662247 1.814743
Choudhary, Kamer, and Raines
Supporting Information
Table S7. Atomic coordinates of conformation 6. Atom C C C H C C C H O O O C H C H H C O H H H
x –2.280052 –2.821321 –0.934670 –2.886600 –0.475234 –2.022518 –0.141835 –3.862339 0.862357 –1.223312 1.156378 –0.691767 –2.437822 2.256737 1.037875 –0.064051 2.000124 3.337265 2.958583 1.469356 1.386707
y 0.259052 –1.015536 0.476002 1.123193 1.894573 –2.104651 –0.632955 –1.159628 2.044147 2.840507 –0.490965 –1.910566 –3.105190 –0.553807 2.998447 –2.740109 –0.792846 –0.428885 –0.824245 –1.733688 0.007187
–S8–
z 0.253272 0.265725 –0.068457 0.490322 –0.053470 –0.071624 –0.400280 0.525547 0.067213 –0.109860 –0.853831 –0.413673 –0.081839 –0.021041 0.052034 –0.714215 1.443884 –0.515014 1.954953 1.599468 1.859650
Choudhary, Kamer, and Raines
Supporting Information
Table S8. Atomic coordinates of conformation 7. Atom C C C H C C C H O O O C H C H O C H H H
x –2.196746 –2.993685 –0.831674 –2.610664 –0.012091 –2.438299 –0.304934 –4.048276 1.219002 –0.686267 1.027514 –1.086998 –3.049337 1.988878 –0.622140 1.791741 3.316684 4.118014 3.287546 3.462132
y 0.632637 –0.506199 0.585713 1.610520 1.905402 –1.740617 –0.668545 –0.431687 1.785958 2.942654 –0.789157 –1.816542 –2.636972 –0.816689 –2.758802 –1.183691 –0.404334 –0.712931 0.683955 –0.825152
–S9–
z 0.251664 0.252234 –0.044928 0.465385 –0.015701 –0.075482 –0.361333 0.497626 0.188221 –0.183665 –0.767196 –0.389942 –0.088113 0.203779 –0.655521 1.331655 –0.364727 0.304490 –0.448066 –1.361306
Choudhary, Kamer, and Raines
Supporting Information
Table S9. Atomic coordinates of conformation 8. Atom C C C H C C C H O O O C H C H C O H H H
x 0.000000 1.389009 –0.746117 –0.549889 –2.287042 2.081690 –0.025788 1.932056 –2.833274 –2.789772 –0.665625 1.366192 3.165815 –1.040858 1.872177 –0.903677 –1.463267 –1.176046 0.113627 –1.582478
y 0.000000 0.000000 1.184206 –0.933628 1.084120 1.208189 2.379219 –0.939333 1.719614 0.343684 3.619801 2.398429 1.225544 4.355567 3.355258 3.713009 5.468065 4.443367 3.354627 2.852485
–S10–
z 0.000000 0.000000 0.000000 –0.016878 0.049157 –0.039212 –0.025950 0.013289 0.981052 –0.816954 –0.141902 –0.068037 –0.061698 0.945599 –0.131833 2.296929 0.756797 3.055692 2.465453 2.310950
Choudhary, Kamer, and Raines
Supporting Information
Table S10. Atomic coordinates of optimized conformation of compound 9. Atom C C C
x –1.215153 –2.076158 0.155723
y 0.799875 –0.288944 0.636489
z 0.017767 –0.040507 –0.169605
H C C C O O C H C H O C H H H N O O
–1.585247 1.068265 –1.614982 0.609006 0.473964 1.943646 –0.259450 –2.309275 2.832935 0.150648 2.514505 4.223517 4.944995 4.283269 4.413853 –3.509997 –4.255622 –3.910485
1.801036 1.897439 –1.574323 –0.660753 2.971073 –0.900531 –1.748477 –2.399952 –0.899494 –2.726385 –1.170714 –0.628638 –0.921484 0.444825 –1.157489 –0.090964 –1.067698 1.033499
0.185809 –0.109775 –0.318228 –0.430788 –0.317241 –0.713946 –0.519142 –0.368019 0.340098 –0.738196 1.464205 –0.151536 0.608854 –0.338375 –1.087176 0.175511 0.058344 0.462862
–S11–
Choudhary, Kamer, and Raines
Supporting Information
Table S11. Atomic coordinates of optimized conformation of compound 10. Atom C C C H C C C O O O C H C H O C C N H H H
x –1.575317 –2.440084 –0.203552 –1.948709 0.684796 –1.933480 0.270845 1.897653 0.067183 1.608898 –0.576446 –2.599765 2.507557 –0.151564 2.207226 3.888814 –3.843632 –4.979161 3.929908 4.624052 4.075511
y 0.765315 –0.332119 0.632372 1.763851 1.909637 –1.604595 –0.650731 1.715896 2.977092 –0.856880 –1.752033 –2.456230 –0.882817 –2.719285 –1.193105 –0.571130 –0.167724 –0.054308 0.510638 –0.886363 –1.053514
–S12–
z 0.062602 0.002516 –0.140532 0.250313 –0.058567 –0.297293 –0.427324 0.182360 –0.233078 –0.735628 –0.517394 –0.354067 0.305983 –0.755542 1.425645 –0.189056 0.228919 0.407882 –0.328228 0.548947 –1.150118
Choudhary, Kamer, and Raines
Supporting Information
Table S12. Atomic coordinates of optimized conformation of compound 11. Atom C C C H C C C O O O C H C H O C H H H C H H H O
x –1.531899 –2.276583 –0.144484 –1.975308 0.595958 –1.645045 0.464725 1.832002 –0.141657 1.830744 –0.272884 –2.233607 2.708952 0.243746 2.434571 4.063954 4.818379 4.004026 4.305279 –4.316401 –5.368769 –3.947481 –4.208513 –3.645099
y 0.528247 –0.643060 0.524561 1.503061 1.893113 –1.862240 –0.706292 1.845348 2.892411 –0.787555 –1.883126 –2.771262 –0.715217 –2.815249 –1.012501 –0.288038 –0.517988 0.790075 –0.768320 0.518594 0.262774 0.996061 1.223189 –0.700403
–S13–
z 0.001271 –0.037139 –0.181019 0.149847 –0.115494 –0.282468 –0.417558 0.079498 –0.252444 –0.709656 –0.475635 –0.318045 0.332674 –0.672364 1.465212 –0.156252 0.594168 –0.317768 –1.106245 0.403224 0.527098 1.316930 –0.427919 0.145475
Choudhary, Kamer, and Raines
Supporting Information
Table S13. Atomic coordinates of optimized conformation of compound 12. Atom C C C H C C C O O O C H C H O C H H H C C H H H H H H N
x –1.112001 –2.016272 0.250482 –1.438831 1.150343 –1.516024 0.712225 2.367830 0.545362 2.051266 –0.154234 –2.167504 2.959870 0.241091 2.685123 4.339413 4.390893 5.084761 4.502024 –4.247332 –4.030548 –3.826322 –5.223025 –4.412712 –3.402729 –4.239871 –4.978152 –3.391689
y 0.792822 –0.272829 0.657308 1.790166 1.919690 –1.528403 –0.617304 1.708973 3.007967 –0.819752 –1.689219 –2.385806 –0.949379 –2.657783 –1.333740 –0.616862 0.472761 –1.001760 –1.016822 –1.226769 1.067446 –1.990206 –0.938660 –1.680476 1.952627 0.860819 1.292210 –0.060524
–S14–
z 0.150127 0.062474 –0.091666 0.413877 0.045662 –0.299561 –0.438470 0.253755 –0.053829 –0.788971 –0.544452 –0.400574 0.221608 –0.828123 1.327540 –0.272078 –0.320697 0.421894 –1.274632 0.399326 –0.294612 1.055024 0.798170 –0.595475 –0.242475 –1.359082 0.202512 0.370211
Choudhary, Kamer, and Raines
Supporting Information
Table S14. Atomic coordinates of optimized conformation of compound 13. Atom C C H C C C O O O C C H O C N O O H H H C H
x –0.569861 0.537251 –0.388419 1.948902 –2.049373 0.293586 2.850473 1.999858 1.358867 –0.979461 2.072375 –1.141214 1.619126 3.447472 –3.396421 –4.329547 –3.548642 3.905815 3.414433 4.016866 –1.855411 –2.706490
y 1.911937 1.123484 2.956083 1.750682 0.066056 –0.213787 1.038362 2.900283 –1.011184 –0.751331 –1.661216 –1.783251 –1.941467 –1.992589 –0.486580 0.241806 –1.657363 –2.738681 –2.341517 –1.060681 1.400099 2.010597
–S15–
z 0.301640 –0.032247 0.522516 –0.032421 –0.030395 –0.364938 0.461184 –0.510333 –0.775102 –0.382573 0.202804 –0.655687 1.277771 –0.295493 –0.039852 0.305905 –0.393571 0.350547 –1.328711 –0.263993 0.323447 0.588521
Choudhary, Kamer, and Raines
Supporting Information
Table S15. Atomic coordinates of optimized conformation of compound 14. Atom C C H C C C O O O C C H O C H H H C N C H
x –0.993933 0.149819 –0.853409 1.529600 –2.411584 –0.034653 2.502907 1.487601 1.051268 –1.285970 1.839450 –1.380726 1.446121 3.204364 3.723464 3.139633 3.732347 –3.709204 –4.761157 –2.256203 –3.126500
y 1.801677 1.066925 2.852056 1.776735 –0.115280 –0.277634 1.061525 2.985900 –1.039515 –0.869713 –1.609636 –1.910697 –1.870471 –1.903494 –2.600949 –2.299854 –0.948124 –0.714291 –1.192046 1.233250 1.821142
–S16–
z 0.300323 –0.026706 0.522446 –0.013326 –0.034769 –0.362126 0.313021 –0.312938 –0.785756 –0.381532 0.183918 –0.661248 1.287480 –0.364196 0.290364 –1.378858 –0.398313 –0.046639 –0.056399 0.315834 0.581254
Choudhary, Kamer, and Raines
Supporting Information
Table S16. Atomic coordinates of optimized conformation of compound 15. Atom C C H C C C O O O C C H O C C H H H O H H H C H
x –0.975221 0.229547 –0.912085 1.542399 –2.253678 0.137623 2.613852 1.379717 1.264778 –1.072146 2.165415 –1.096636 1.876453 3.511326 –4.628210 –5.404250 –4.636159 –4.837465 –3.408613 3.956548 4.128362 3.409659 –2.208555 –3.108471
y 1.643863 0.996597 2.707335 1.827623 –0.365933 –0.372282 1.176115 3.065827 –1.106266 –1.048160 –1.431674 –2.105542 –1.548393 –1.715783 –0.470554 –1.231577 –0.054173 0.334007 –1.120976 –0.745716 –2.258513 –2.280577 0.994424 1.555578
–S17–
z 0.192507 –0.067747 0.388285 –0.049696 –0.104590 –0.348447 –0.022836 –0.057732 –0.718295 –0.377558 0.259719 –0.607776 1.420538 –0.343703 0.135624 0.055003 1.149306 –0.578723 –0.152144 –0.571187 0.370370 –1.272341 0.188565 0.402762
Choudhary, Kamer, and Raines
Supporting Information
Table S17. Atomic coordinates of optimized conformation of compound 16. Atom C C H C C C O O O C C H O C H H H C C H H H H H H N C H
x –0.480649 0.631131 –0.292502 2.029459 –2.015916 0.365648 3.018750 2.011705 1.382062 –0.912265 2.286517 –1.024352 2.043917 3.559516 4.102142 4.144446 3.347704 –3.734038 –4.381318 –2.948621 –4.614848 –3.991399 –4.096321 –4.659946 –5.268725 –3.313375 –1.775493 –2.590965
y 1.864193 1.066262 2.925827 1.732849 –0.006222 –0.297441 0.961976 2.977071 –1.190632 –0.827399 –1.537439 –1.898327 –1.523351 –2.029931 –1.143087 –2.579722 –2.655904 –1.437297 0.289051 –2.140424 –2.011648 –0.858357 0.793456 1.058773 –0.315872 –0.583734 1.360866 2.045962
–S18–
z 0.158862 –0.097571 0.264107 –0.201864 0.072395 –0.261799 –0.162782 –0.308869 –0.607620 –0.183196 0.359031 –0.293240 1.536268 –0.268868 –0.600433 0.466563 –1.137916 –0.915353 0.630900 –1.180864 –0.615418 –1.819819 1.554506 –0.110630 0.832679 0.186969 0.247062 0.438112
Choudhary, Kamer, and Raines
Supporting Information
Table S18. Atomic coordinates of optimized conformation of compound 17. Atom C C C H C C C H O O O C H C O C H H H C O O
x –1.741024 –0.703737 –1.484517 –2.778740 –2.698659 0.613841 –0.142547 –0.923130 –2.601018 –3.682774 0.099015 0.933594 1.446940 0.676776 0.876004 1.048987 1.330203 0.215230 1.895852 2.439223 2.710414 3.243612
y –1.925407 –2.838452 –0.576096 –2.233734 0.383130 –2.420846 –0.191715 –3.882688 1.505650 –0.102676 1.140927 –1.091906 –3.106992 1.964723 1.731868 3.255678 4.000615 3.614389 3.038198 –0.754253 0.359667 –1.667802
–S19–
z 0.223761 0.372452 –0.024612 0.279116 –0.154820 0.225244 –0.148233 0.585785 0.386957 –0.772297 –0.492899 –0.063195 0.315739 0.390798 1.557190 –0.297904 0.445510 –0.903784 –0.952802 –0.309092 –0.815887 0.004941
