A DFT Study of the Formation of Xanthydrol Motifs

Supporting information to:

"A DFT Study of the Formation of Xanthydrol Motifs

during Electrophilic Poly Aryl Ether Ketone Synthesis"

by Joubert and co., J. Mol. Model. 2015

For all molecules: Charge: 0, Multiplicity: 1, optimization: 6-311+G(d,p)/ ωB97X-D (vac) Gaussian09 Revision B.01 [Frisch 2009].

Order of appearance: Int4, Pro, Pre, TSP, IntHA, IntHB, TSCA, TSCB, IntCA, IntCB, IntCC, TSDAB, TSDC, IntPAB, IntPC, ProX, ProX'. Energies in Hartree, coordinates in Å.

E_Vac E_Nitro Gibbs correction

Int4 -4590.21111493 -4590.22795193 0.225967

Pro -4590.26181335 -4590.27842724 0.225377

Pre -4590.25764657 -4590.27471150 0.231573

TSP -4590.25413222 -4590.27392964 0.231740

IntHA -4590.25530502 -4590.27892358 0.235484

IntHB -4590.21862110 -4590.25928826 0.234634

TSCA -4590.22762772 -4590.25917675 0.236918

TSCB -4590.20033615 -4590.24529793 0.234647

IntCA -4590.24556213 -4590.28734961 0.234860

IntCB -4590.24223750 -4590.28083032 0.237883

IntCC -4590.24384174 -4590.27268164 0.236898

TSDAB -4590.23469634 -4590.26086354 0.233107

TSDC -4590.22368118 -4590.23946407 0.231533

IntPAB -4590.26226030 -4590.28005664 0.232681

IntPC -4590.22568368 -4590.24205229 0.229289

ProX -4590.27626916 -4590.29003324 0.233738

ProX'+HCl -4590.26135702 -4590.28559075 0.236602

Int4

C 1.907733703 1.5705403071 0.2668484504

O 1.8899148355 1.2311044535 1.4313174252

Cl -1.3857843626 2.1542599763 1.1772068727

Al -1.8586740813 0.3198764871 2.0459074795

Cl -3.7499208005 -0.530233864 1.2946734606

Al -3.9541344496 -0.8173353265 -1.0929672431

Cl -2.6768944719 -2.4641096931 -1.4576355848

Cl -1.7605297387 0.0090590598 4.1039578077

Cl -0.3370368447 -1.2866567237 1.1838808062

Cl -6.0175955231 -1.1717060262 -1.2346081848

Cl -3.2379908884 1.0141962129 -1.867085388

C 1.6029090985 0.5401121295 -0.7933645873

C 0.4849963485 0.6773798162 -1.6276370846

C 2.405081387 -0.6083629445 -0.9071737481

C 0.1257336893 -0.3359592785 -2.5020464499

C 2.045631247 -1.6254803637 -1.7892388464

C 0.9054563582 -1.4856321288 -2.568912188

H 0.4312436524 -0.5219247271 0.3968419663

H -0.1268732289 1.5689749831 -1.5474273309

H -0.7679793029 -0.2386183251 -3.1040713122

H 2.6571063501 -2.5159262402 -1.8632803705

H 0.6225036339 -2.2882420121 -3.2397885837

C 2.6507364663 5.6201813477 -0.8379341764

C 2.7035075446 4.6303226613 -1.8119465442

C 2.4529635651 3.308103074 -1.4692226868

C 2.1599375134 2.9736041038 -0.1463317134

C 2.1157628857 3.9720006559 0.8297935892

C 2.3560431475 5.291188932 0.4830451679

H 2.8389785903 6.65358276 -1.1069045924

H 2.9354545171 4.8875930552 -2.8387718219

H 2.4938744563 2.5361936664 -2.2292655875

H 1.8878704679 3.692806384 1.8515939966

H 2.3134522249 6.06624851 1.2392347271

O 3.532920672 -0.6328007597 -0.1562739937

C 4.1703776217 -1.8429738188 0.0581194767

C 5.3691719243 -2.0881414625 -0.5913951752

C 3.6307395812 -2.754507599 0.9542010403

C 6.0394745481 -3.2805745177 -0.3412933896

H 5.7637126103 -1.3479369561 -1.2771087056

C 4.3061610539 -3.9443050002 1.1925431221

H 2.7018671625 -2.5225373669 1.4620667897

C 5.508831581 -4.2099500925 0.5454929343

H 6.9799057579 -3.4807355637 -0.8415408958

H 3.8959419021 -4.6619503817 1.8935475122

H 6.0331535952 -5.1387184033 0.7369975601

Pro

Cl 1.8623355598 -2.2928967043 2.210171114

Al 0.9435787625 -1.8320098451 0.38304794

Cl 2.4363980084 -1.8457171672 -1.27823251

Al 3.916366407 -0.0237117821 -1.3012786315

Cl 3.0087585295 1.3141374888 -2.6721749234

Cl -0.680015226 -3.0048681948 -0.27539012

Cl 1.4886475251 1.6628961859 3.2820671814

Cl 3.908871963 0.7086507672 0.7032212628

Cl 5.7190054167 -0.9010963705 -1.9235782767

O 0.4747687218 -0.055534958 0.3777730655

C -0.5471842502 0.6038463922 0.7058736551

C -0.5999693506 2.0133703705 0.3923509513

C -1.5991333114 2.8247470311 0.9485664958

C -1.6142811583 4.1789766436 0.6713206248

C -0.6427482847 4.7258968082 -0.1646902689

C 0.3789694078 2.5718111855 -0.4406210354

C 0.3507458369 3.9250082309 -0.7215015205

H 2.3074850762 1.2522960468 2.3667565298

H -2.3411978287 2.3931312506 1.6095481427

H 1.1459918633 1.9419609846 -0.8715998674

H 1.1032014939 4.3534226812 -1.3721536792

C -3.6496990605 -1.5004820443 2.6960182563

C -3.8950943118 -0.9488056517 1.4452155186

C -2.8881355357 -0.2389524236 0.8035180202

C -1.6408381227 -0.0881164551 1.420659181

C -1.4037525944 -0.6628783657 2.6692181633

C -2.4129072166 -1.3603794068 3.3137589339

H -4.8545559474 -1.0812125745 0.9620577403

H -0.4330851396 -0.541634027 3.1360233659

H -2.2303412065 -1.798649064 4.2864597308

H -0.6593800075 5.7886488544 -0.3797834014

H -2.3758071306 4.8140195332 1.1073642495

H -4.4403562338 -2.05373763 3.1896720162

O -3.0146100427 0.3240135803 -0.4260508996

C -6.1850601558 -0.6738524759 -2.9026076645

C -6.14508447 0.5701213077 -2.2844488294

C -5.091309203 0.8970168213 -1.4379193114

C -4.0880263635 -0.0338803257 -1.2275293738

C -4.1041941062 -1.2777145818 -1.8416831435

C -5.1650978405 -1.5941562748 -2.6805314129

H -7.0066231969 -0.9258915094 -3.5627816368

H -6.9339013029 1.2921126641 -2.4611179488

H -5.0342306347 1.8616165781 -0.9479066169

H -3.2956839271 -1.9769159849 -1.6603075946

H -5.1895925116 -2.5615184255 -3.1685037182

Pre

C -3.15985 1.67594 0.2223

C -3.10354 2.94255 -0.34147

C -3.33841 3.08457 -1.70097

C -3.62321 1.97314 -2.48952

C -3.70312 0.71743 -1.90196

C -3.48698 0.56145 -0.53664

H -2.84912 3.78969 0.28348

H -3.28245 4.06945 -2.15048

H -3.78887 2.08807 -3.55393

H -3.93562 -0.15619 -2.49991

O -2.88583 1.59601 1.5748

C -1.51395 -1.85262 3.45362

C -2.57304 -1.10646 3.95918

C -3.01871 0.02843 3.29788

C -2.39647 0.45356 2.13278

C -1.31046 -0.28326 1.61679

C -0.90274 -1.44975 2.28358

H -1.17161 -2.74428 3.96248

H -3.0703 -1.41897 4.87021

H -3.86334 0.59944 3.66216

H -0.0665 -2.01408 1.88703

C -0.5687 0.0779 0.41024

C 0.55978 4.02805 -0.54089

C 0.3925 3.67043 0.79435

C 0.02482 2.37861 1.12063

C -0.16169 1.4369 0.10222

C 0.0188 1.79792 -1.24075

C 0.37188 3.09648 -1.55676

H 0.56216 4.39914 1.57726

H -0.09434 2.08384 2.1561

H -0.17352 1.0709 -2.02225

H 0.49733 3.38511 -2.59289

O -0.21754 -0.83539 -0.39621

H 0.84629 5.04345 -0.79028

H -3.56304 -0.4191 -0.08379

H 1.41401 -0.66343 -1.11576

Cl 2.48378 -0.38553 1.91491

Cl 5.6421 -0.67658 0.19647

Cl 3.73691 2.35407 0.01589

Al 3.78989 0.28311 0.38829

Cl 2.64903 -0.61361 -1.58525

Cl -0.84439 -1.97616 -3.13165

Cl 0.72552 -3.78846 -0.45135

Cl -2.74476 -2.95849 -0.27057

Al -0.83634 -2.50358 -1.0747

TSP

C -3.11272 1.65 0.32331

C -3.07387 2.93653 -0.19249

C -3.3459 3.12801 -1.53953

C -3.65073 2.046 -2.36021

C -3.71405 0.76918 -1.81736

C -3.45999 0.56365 -0.4655

H -2.80356 3.76031 0.45642

H -3.30331 4.12882 -1.9539

H -3.84451 2.19922 -3.41496

H -3.9616 -0.08178 -2.44122

O -2.80509 1.51837 1.66684

C -1.34088 -1.96979 3.40295

C -2.39487 -1.24711 3.95491

C -2.86902 -0.0978 3.34053

C -2.28263 0.37167 2.17393

C -1.1971 -0.3406 1.60999

C -0.76348 -1.52776 2.23354

H -0.97585 -2.86955 3.88032

H -2.86619 -1.59078 4.86859

H -3.71068 0.45113 3.7432

H 0.07569 -2.06395 1.80688

C -0.47592 0.07121 0.42805

C 0.51801 4.03472 -0.53774

C 0.39328 3.66762 0.80112

C 0.06077 2.36991 1.1288

C -0.13147 1.42745 0.10599

C 0.00313 1.80194 -1.24254

C 0.31746 3.10919 -1.55645

H 0.5787 4.39334 1.58282

H -0.00834 2.06085 2.1643

H -0.19275 1.07893 -2.02627

H 0.41146 3.40713 -2.59292

O -0.06949 -0.86301 -0.38213

H 0.78417 5.05554 -0.78745

H -3.52505 -0.43163 -0.04502

H 1.03945 -0.66092 -0.9139

Cl 2.49457 -0.30505 1.9354

Cl 5.53108 -0.69994 0.06747

Cl 3.69831 2.3714 -0.0436

Al 3.67222 0.26944 0.2426

Cl 2.42505 -0.53797 -1.53194

Cl -1.02348 -1.75981 -3.13455

Cl 0.69212 -3.88178 -0.74992

Cl -2.69191 -2.92451 -0.21022

Al -0.84849 -2.51454 -1.16516

IntHA

C -3.04529 1.79778 0.49032

C -2.98494 3.08423 -0.02247

C -3.27493 3.28544 -1.36461

C -3.61931 2.21303 -2.18185

C -3.70346 0.93667 -1.64078

C -3.43009 0.7214 -0.29426

H -2.68922 3.90086 0.62425

H -3.21675 4.28611 -1.77719

H -3.82791 2.37355 -3.23262

H -3.98303 0.09401 -2.26218

O -2.72227 1.655 1.83061

C -1.30486 -1.8713 3.52971

C -2.33913 -1.12982 4.09622

C -2.79644 0.03359 3.49584

C -2.21284 0.5006 2.32733

C -1.14197 -0.22859 1.75008

C -0.72738 -1.43282 2.36063

H -0.95361 -2.7806 3.99911

H -2.80852 -1.47051 5.01205

H -3.62407 0.59477 3.91029

H 0.1029 -1.9769 1.92696

C -0.41946 0.188 0.58245

C 0.6275 4.11731 -0.41754

C 0.49394 3.76324 0.92495

C 0.14058 2.47536 1.26152

C -0.06476 1.52649 0.24292

C 0.08102 1.88936 -1.11049

C 0.41455 3.18897 -1.43133

H 0.69538 4.49034 1.70111

H 0.07431 2.17227 2.29875

H -0.11916 1.16584 -1.89228

H 0.51971 3.4773 -2.46918

O -0.02245 -0.77906 -0.22933

H 0.91505 5.13067 -0.67386

H -3.51044 -0.27332 0.12501

H 0.89817 -0.57574 -0.71672

Cl 2.51413 -0.23121 2.00343

Cl 5.5878 -0.63206 0.23

Cl 3.7791 2.4491 0.09521

Al 3.70832 0.32591 0.28923

Cl 2.5041 -0.41632 -1.45881

Cl -1.07774 -1.55293 -3.00656

Cl 0.65094 -3.81386 -0.74854

Cl -2.69048 -2.78188 -0.07531

Al -0.87509 -2.42538 -1.09561

IntHB

C -0.7149676957 -2.4488363048 -0.3779861411

C -1.6075712684 -3.4745560197 -0.6424093208

C -2.1483440628 -3.5789837936 -1.916139965

C -1.788122927 -2.6700751338 -2.9050031201

C -0.8706521691 -1.6664300045 -2.6183194533

C -0.3173554127 -1.5465781586 -1.3488877758

H -1.8666399182 -4.173318485 0.1430720103

H -2.8484382693 -4.3768194408 -2.1358412933

H -2.2060764721 -2.7560255616 -3.9010286239

H -0.5593339675 -0.9717102211 -3.3888841739

O -0.1912030206 -2.4365097611 0.9145234613

C 1.4569128182 0.8004369253 2.9249094027

C 1.9707721234 -0.5073787841 3.009847463

C 1.3845016409 -1.5615721403 2.3367482356

C 0.2507889676 -1.3614023214 1.5623438902

C -0.3681013391 -0.0530627582 1.5540180509

C 0.3325352652 1.0279709052 2.1971186502

H 1.9685745716 1.6176858224 3.4143509228

H 2.8731495881 -0.6880641489 3.5796797713

H 1.8406985489 -2.5416758464 2.3228637575

H -0.0867621241 2.0226965923 2.1459032033

C -1.6518572002 0.1820060091 1.0992817192

C -4.8895942803 -2.4907056252 0.67334059

C -4.0562041224 -2.5876854153 1.7840227272

C -2.9748407648 -1.7343796418 1.9138032688

C -2.7424300612 -0.7639387759 0.9330134906

C -3.591354145 -0.6564306771 -0.1783965344

C -4.6536315117 -1.5341421171 -0.308901853

H -4.2514842207 -3.3298244267 2.5483808059

H -2.3215437808 -1.7977013264 2.7760309055

H -3.3790483243 0.0651620026 -0.9611826318

H -5.2923857504 -1.4771412026 -1.1813442271

O -2.0088388218 1.473889059 0.8643812607

H -5.7280872988 -3.1699077754 0.5710543138

H 0.4211430805 -0.7807569325 -1.1415779694

H -2.9766295594 1.5726759494 0.9034964691

Cl 2.0835052352 1.0915595084 -0.5918209188

Cl 4.7362552344 0.1115876126 1.4811518812

Cl 5.1785096531 0.1800309879 -2.0426886219

Al 3.8264234644 -0.2245663885 -0.4533878049

Cl 3.0754764876 -2.253410053 -0.5284727274

Cl -3.5591111631 3.6779848492 -0.2891121084

Cl -0.0748903689 4.1738714682 0.3842936195

Cl -1.2220277509 1.8890996668 -2.2597025615

Al -1.5466389079 3.0394928826 -0.5496670449

TSCA

C -3.36444 1.56974 0.36856

C -3.58622 2.85502 -0.10933

C -3.4584 3.08277 -1.46466

C -3.1456 2.0499 -2.37377

C -2.94853 0.78291 -1.90399

C -2.99018 0.5153 -0.50428

H -3.81107 3.6513 0.58785

H -3.59907 4.09023 -1.84079

H -3.07624 2.26652 -3.43204

H -2.72826 -0.03799 -2.57766

O -3.39677 1.385 1.69126

C -1.18578 -1.62449 3.49363

C -2.32812 -1.12359 4.09568

C -3.07971 -0.13457 3.46569

C -2.67122 0.33267 2.23628

C -1.53749 -0.17323 1.59915

C -0.7921 -1.1516 2.2472

H -0.59866 -2.39393 3.97829

H -2.64558 -1.49866 5.06114

H -3.97175 0.27957 3.91826

H 0.10599 -1.53637 1.78008

C -1.11279 0.30539 0.24701

C 0.80399 4.08283 -0.12251

C 0.41502 3.61469 1.12767

C -0.21726 2.38999 1.24622

C -0.46062 1.61803 0.10445

C -0.07892 2.10185 -1.15246

C 0.55778 3.32597 -1.26081

H 0.63398 4.19141 2.01789

H -0.47456 2.0088 2.2261

H -0.26527 1.52067 -2.04611

H 0.88383 3.67598 -2.23191

O -0.61009 -0.69533 -0.53462

H 1.32214 5.03062 -0.20736

H -3.22085 -0.50295 -0.20195

H 0.25993 -0.45962 -1.0328

Cl 2.3631 -0.01197 1.38462

Cl 5.01361 -1.19383 -0.67953

Cl 3.88827 2.1845 -0.92135

Al 3.38732 0.14855 -0.50929

Cl 1.85058 -0.45145 -2.02533

Cl -1.32076 -2.3881 -3.04107

Cl 0.53762 -3.67327 -0.19948

Cl -2.94748 -2.92103 0.04781

Al -1.09659 -2.60544 -0.95004

TSCB

C -0.5650822369 1.5300990409 -0.11406828

C -0.6949219285 2.7941182496 -0.6783521338

C -0.2601972689 2.9854856135 -1.9716326256

C 0.2914653777 1.933257962 -2.7295804019

C 0.3681472308 0.6778601335 -2.1831689853

C -0.02981354 0.4540632286 -0.8478277798

H -1.1230700039 3.5939475706 -0.0889586018

H -0.3530761159 3.9688703847 -2.4184709477

H 0.597339814 2.1094019687 -3.7532856103

H 0.7096455106 -0.1664152359 -2.7709796037

O -0.8749278405 1.413050641 1.1929381675

C 0.7063782464 -1.6953611155 3.4304413079

C -0.5820454455 -1.2309279541 3.65913213

C -1.117620231 -0.197819152 2.8953942556

C -0.34361692 0.3735483731 1.9122592248

C 0.9639397974 -0.0765809529 1.6626682772

C 1.4766393102 -1.1278065861 2.4269315537

H 1.1097315526 -2.5104553809 4.0174436576

H -1.1961114807 -1.6917355524 4.4233485364

H -2.1394433402 0.1417583138 3.0125248335

H 2.4854065173 -1.482839202 2.2528493108

C 1.7586742475 0.5253293316 0.5948278351

C 2.990113974 4.5813261269 0.5682467639

C 2.331813767 4.0588724134 1.6772765684

C 1.9217284652 2.7372784023 1.685411243

C 2.1730448873 1.926247587 0.5717768929

C 2.8322452371 2.459069397 -0.5466473009

C 3.2433530603 3.7812181305 -0.5406289452

H 2.1431645461 4.6825887897 2.5424256454

H 1.4254882882 2.3234418539 2.5541075468

H 2.9785273432 1.8701113975 -1.4484409656

H 3.7432022202 4.192430225 -1.4088975639

O 2.6182115936 -0.321671793 -0.0274920419

H 3.3073545568 5.6176106078 0.5680780723

H -0.2075196349 -0.562732524 -0.5178357788

H 3.3010528728 0.178911659 -0.5042709161

Cl -2.4711498482 -1.8519408413 0.2621552962

Cl -4.2037644324 1.0157082846 1.2749456216

Cl -5.8434330133 -1.4049939012 -0.7392484941

Al -3.9999078789 -0.4181796826 -0.3364282505

Cl -3.246751907 0.6155166518 -2.0855418669

Cl 3.6848369362 -1.4672119566 -2.5310860245

Cl 4.1869830035 -3.0476372158 0.6194793394

Cl 0.8780708479 -3.0227431577 -0.8509176971

Al 2.8164688629 -2.285651134 -0.7747152648

IntCA

C -3.32544 1.62596 0.48544

C -4.11427 2.64372 -0.05247

C -4.09644 2.83485 -1.41191

C -3.32011 2.03992 -2.30434

C -2.53925 1.05677 -1.81116

C -2.52849 0.73335 -0.37193

H -4.70379 3.2638 0.6097

H -4.70535 3.63129 -1.82746

H -3.35447 2.24315 -3.3665

H -1.94477 0.42112 -2.45947

O -3.34163 1.45062 1.7722

C -0.97063 -1.39347 3.62114

C -2.08296 -0.87209 4.26968

C -2.87977 0.07394 3.6373

C -2.53392 0.46012 2.3586

C -1.43217 -0.04363 1.68367

C -0.64185 -0.97802 2.33668

H -0.34752 -2.12987 4.11279

H -2.33538 -1.19835 5.2711

H -3.74921 0.50661 4.11573

H 0.234 -1.37757 1.84167

C -1.1399 0.44883 0.28195

C 1.24122 4.04248 0.14579

C 0.78711 3.55847 1.3629

C 0.03507 2.39174 1.41575

C -0.28045 1.70823 0.24556

C 0.1731 2.2053 -0.97826

C 0.93736 3.35975 -1.0256

H 1.04517 4.06802 2.28337

H -0.2701 2.00395 2.37936

H -0.01258 1.66729 -1.9004

H 1.32472 3.70541 -1.97578

O -0.53042 -0.60929 -0.4808

H 1.85837 4.93195 0.10897

H -3.07405 -0.24425 -0.30771

H 0.40961 -0.41303 -0.7834

Cl 2.58125 0.01767 1.58717

Cl 5.19647 -1.33747 -0.39929

Cl 4.24596 2.07554 -0.76276

Al 3.62259 0.08064 -0.30683

Cl 2.08472 -0.48721 -1.81122

Cl -1.23156 -2.19533 -3.08363

Cl 0.34089 -3.68434 -0.1535

Cl -3.0409 -2.54854 -0.09034

Al -1.08796 -2.39648 -0.97929

IntCB

C 0.3442 -1.93097 -0.46611

C 0.9984 -2.66928 -1.44966

C 0.89069 -2.2589 -2.75211

C 0.1246 -1.12261 -3.15027

C -0.5052 -0.382 -2.22068

C -0.3739 -0.67783 -0.77843

H 1.59326 -3.52226 -1.15413

H 1.41795 -2.82036 -3.51574

H 0.08526 -0.84939 -4.19615

H -1.04266 0.51665 -2.49366

O 0.41637 -2.35812 0.75762

C -1.35001 -0.353 3.90217

C -0.29574 -1.23055 4.12514

C 0.29808 -1.89478 3.06151

C -0.18179 -1.64362 1.79344

C -1.21955 -0.76161 1.5341

C -1.81425 -0.12426 2.61326

H -1.80292 0.17508 4.7319

H 0.07719 -1.39146 5.129

H 1.13583 -2.56816 3.18865

H -2.61905 0.58029 2.44782

C -1.64441 -0.55057 0.09896

C -4.71186 -3.27938 -1.25408

C -4.04539 -3.52137 -0.06089

C -3.06771 -2.6415 0.38866

C -2.74028 -1.51383 -0.36033

C -3.41535 -1.27614 -1.56195

C -4.39868 -2.15058 -2.00175

H -4.29131 -4.39333 0.53346

H -2.5712 -2.83435 1.33175

H -3.18725 -0.40346 -2.16444

H -4.91711 -1.94836 -2.93138

O -2.16317 0.7978 -0.07063

H -5.47724 -3.96461 -1.59905

H 0.35274 0.09823 -0.40068

H -3.12061 0.76618 -0.21094

Cl -3.65694 3.19995 -0.72753

Cl -1.31156 3.25437 1.96052

Cl -0.15639 2.93946 -1.45537

Al -1.68883 2.73291 -0.03353

Cl 3.04263 0.28481 -1.89716

Cl 3.66123 -1.88815 0.77185

Cl 1.79658 1.02294 1.24596

Cl 5.30595 1.26872 0.69159

Al 3.53993 0.20151 0.21089

IntCC

C 0.2714988507 -2.1716005143 0.0026201383

C 0.8406895492 -3.1525625837 -0.8044884706

C 0.8155288378 -2.9688924518 -2.1631770639

C 0.2091730251 -1.8376189071 -2.7902297617

C -0.3243739036 -0.8630384849 -2.0315557586

C -0.2608654942 -0.9132944266 -0.5558871961

H 1.3090494189 -4.012558506 -0.3455119981

H 1.286871515 -3.7196369207 -2.7880609582

H 0.2206329746 -1.7639108808 -3.8695917248

H -0.7469936216 0.0355908929 -2.4626216521

O 0.2495370181 -2.3754422489 1.2857844772

C -1.2372860302 0.4255286214 3.9260804191

C -0.3484809443 -0.5531404898 4.3582111158

C 0.150847757 -1.4841173209 3.4600884448

C -0.2624031181 -1.4035722895 2.1446597672

C -1.1465140328 -0.4431208257 1.6778982553

C -1.6321975358 0.4787544918 2.5953849581

H -1.6150773558 1.1605302281 4.6263392557

H -0.0303140302 -0.5827379311 5.3929471014

H 0.8659190685 -2.2444056881 3.7475073072

H -2.3038573636 1.2615328438 2.2640571653

C -1.5297993681 -0.4397503186 0.2051464286

C -4.841127071 -3.0641157732 -0.7481671933

C -4.1753302496 -3.2077708431 0.4611542421

C -3.1224153987 -2.36030637 0.7875921339

C -2.71763098 -1.3623318087 -0.096754859

C -3.3972330903 -1.2214470133 -1.3095462744

C -4.4517640908 -2.064109923 -1.6317179255

H -4.476743847 -3.9788487673 1.1605249029

H -2.627672342 -2.4784708569 1.7442176865

H -3.1073958188 -0.4423170971 -2.0050562821

H -4.9696649036 -1.9387544673 -2.5755935582

O -1.7648217689 0.8659937039 -0.2719125732

H -5.6627484684 -3.7242621543 -1.0003967894

H 0.5311751635 -0.172982875 -0.2890652807

H -2.6736536246 1.1096897175 -0.0835804237

Cl 3.3147098406 -3.3962419149 1.7725783801

Cl 4.218057358 -3.7601595315 -1.6148350407

Cl 6.6758477264 -4.2535008308 0.9234748082

Al 4.8974736655 -3.2782759436 0.3477763959

Cl 3.0645928396 -0.0630372585 -2.0143531126

Cl 5.5313674473 -1.0644072678 0.3160972692

Cl 2.4813090496 0.4394375495 1.3858836936

Cl 5.0534324431 2.3104176898 -0.2240889972

Al 3.9558029035 0.5120717459 -0.1647574523

TSDAB

C 0.3640959422 -1.9862213919 -0.4370844541

C 1.1960888354 -2.637208659 -1.3410105144

C 1.2670415086 -2.1707264764 -2.6355768038

C 0.5049344637 -1.0706514917 -3.0737994587

C -0.3371092175 -0.4447270491 -2.2020362439

C -0.3736020908 -0.8241526195 -0.8192905573

H 1.8046029373 -3.4601714192 -0.9916529387

H 1.949387381 -2.6507234429 -3.3268198288

H 0.5987212454 -0.7194004631 -4.0927024888

H -0.9123214512 0.4176169784 -2.5136180748

O 0.3516512655 -2.4272434119 0.817628787

C -1.2423539621 -0.1130000448 3.8485780742

C -0.2726171599 -1.0736164745 4.1187831534

C 0.2611556883 -1.8392286526 3.0939163948

C -0.188189781 -1.622235933 1.8032276527

C -1.1440942938 -0.6592365937 1.5053928645

C -1.6784763256 0.0885133742 2.5480921229

H -1.6507256972 0.4902445892 4.6496744856

H 0.080325448 -1.2200661615 5.132423601

H 1.0306786173 -2.5803115198 3.2671372347

H -2.4254886895 0.8446974385 2.3416005465

C -1.5815421802 -0.5240685507 0.0682964923

C -4.8922861906 -3.0986983606 -0.9907661371

C -4.2783088298 -3.2358853981 0.2457995904

C -3.2158839879 -2.4107612055 0.5984647994

C -2.7541871307 -1.4450277743 -0.2912852127

C -3.3718281904 -1.316682667 -1.5393835898

C -4.4384250037 -2.1335334391 -1.8829970136