ONIOM Study on the Alkylation of the Lithium Enolate in Microsolvation Cluster: CH2=Choli

Supporting Information

ONIOM Study on the Alkylation of the Lithium Enolate in Microsolvation Cluster: CH2=CHOLi + CH3Cl + (THF)0-6

Kaori Ando*† and Keiji Morokuma*‡

Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan and Fukui Institute for Fundamental Chemistry, Kyoto University, Takano-Nishihiraki-cho 34-4, Sakyou-ku, Kyoto 606-8103, Japan and Cherry l. Emerson Center for Scientific Computation and Department of Chemistry, Emory University, Atlanta, GA 30322

Contents

1) Table 5. The relative Gibbs free energies for the reaction of CH2=CHOLi with MeCl in the presence of two to six THF molecules at the B3LYP/6-31(+)G*, ONIOM, B3LYP/6-31(+)G*//HF/

3-21G*, HF/3-21G*, B3LYP/6-31(+)G*,PCM(SP), B3LYP/6-31(+)G*,PCM(SP)//ONIOM, B3LYP/6-31(+)G*,PCM(SP)//HF/3-21G*, HF/3-21G*,PCM(SP) levels. page 1

2) The xyz coordinates for the calculated structures 1, 1-ts, 1-pr, 2, 2-ts, 2-pr, 3, 3-ts, 3-pr, 3-tsA, 3-tsB, 4-ts, 5-ts, 6-ts, 7-ts, 8-ts at the B3LYP/6-31(+)G* level. page 2-6

1) Table 5

2) The xyz coordinates:

1

6 2.64630 0.97000 -0.10395

6 2.45241 -0.35921 0.23133

1 3.11933 -0.72236 1.05729

8 1.62592 -1.20893 -0.24990

1 2.09327 1.44210 -0.91687

1 3.40112 1.56035 0.41417

6 -0.92245 0.55969 0.03000

1 -0.87582 1.32306 -0.74615

17 -2.63778 -0.10015 0.02348

1 -0.21004 -0.25226 -0.16406

1 -0.75056 1.00015 1.01129

1-ts

6 1.72001 1.08312 -0.17744

6 2.35465 -0.04911 0.36135

1 2.47276 -0.01848 1.47696

8 2.73811 -1.09002 -0.23170

1 1.70062 1.22430 -1.25796

1 1.61610 1.97160 0.44499

6 -0.64961 0.33972 -0.01121

1 -0.77679 1.27547 -0.52961

17 -2.74720 -0.22557 0.01079

1 -0.26445 -0.50708 -0.55611

1 -0.50105 0.36658 1.05572

1-pr

6 1.10340 0.62515 0.62207

6 1.23236 -0.70411 -0.07668

1 0.28965 -1.08402 -0.51478

8 2.27899 -1.33276 -0.17047

1 2.05400 0.86520 1.11533

1 0.30642 0.51522 1.37050

6 0.66610 1.72649 -0.36411

1 0.56942 2.68552 0.16003

17 -2.38513 -0.32520 0.00606

1 1.39742 1.85346 -1.17400

1 -0.31276 1.46984 -0.78405

2

6 2.34194 -0.30799 0.30011

6 2.82136 0.75213 -0.39284

1 2.28357 1.17075 -1.24167

1 3.77980 1.18972 -0.13015

8 1.19883 -0.93151 0.09737

1 2.94710 -0.70172 1.13066

3 -0.26959 -1.60231 -0.24209

17 -2.23683 -0.23877 -0.13387

6 -1.24933 1.24767 0.31040

1 -1.59949 1.57390 1.28844

1 -0.20215 0.94044 0.32662

1 -1.44843 1.99418 -0.45678

2-ts

6 2.00262 -0.38260 0.31263

6 2.20544 0.88684 -0.22504

1 2.03578 1.08192 -1.28025

1 2.86593 1.57295 0.29775

8 1.24774 -1.30205 -0.16947

1 2.44819 -0.58064 1.30292

3 -0.54143 -1.46804 -0.20373

17 -2.29768 -0.02123 0.01674

6 -0.22297 1.10812 0.09240

1 -0.03937 0.68101 1.05938

1 0.01481 0.60593 -0.82107

1 -0.53287 2.14601 0.04365

2-pr

6 -1.95246 -0.94526 0.01608

6 -2.36362 0.49451 0.04099

1 -2.96805 0.62227 0.95475

1 -3.08903 0.62127 -0.77965

8 -0.79832 -1.35182 -0.03498

1 -2.76829 -1.69108 0.04830

3 1.00993 -0.86435 -0.04993

17 2.83952 0.12418 0.01561

6 -1.22875 1.51504 -0.03765

1 -0.65439 1.41186 -0.96427

1 -0.53002 1.41636 0.79971

1 -1.63644 2.53022 -0.01117

3

6 2.277449 2.185846 -0.384184

6 2.982503 2.590958 0.702914

1 2.870951 2.103456 1.670016

1 3.659533 3.437354 0.631882

8 1.431644 1.184788 -0.452988

1 2.428275 2.740621 -1.325431

3 0.348247 -0.103817 -0.400730

8 -1.550064 -0.127060 -0.342803

6 -2.506150 -1.125011 0.100886

6 -3.850881 -0.395976 0.212682

1 -2.512738 -1.942656 -0.626807

1 -2.165429 -1.512368 1.068527

6 3.190536 -1.450336 0.158439

17 1.553166 -2.256715 0.000361

1 3.024995 -0.378950 0.037865

1 3.573334 -1.699601 1.147160

1 3.823809 -1.860136 -0.627359

6 -2.180924 1.183953 -0.407884

6 -3.424487 1.060343 0.468287

1 -1.445401 1.916528 -0.067444

1 -2.438066 1.392314 -1.454445

1 -3.165871 1.210465 1.523319

1 -4.197520 1.786721 0.198846

1 -4.478048 -0.808954 1.008693

1 -4.407303 -0.469673 -0.729273

3-ts

6 -3.191113 -1.082010 -0.360158

6 -3.590720 -0.151848 0.591099

1 -3.283433 -0.275845 1.626564

1 -4.505497 0.407632 0.414931

8 -2.197699 -1.885255 -0.258029

1 -3.710916 -1.067596 -1.332987

3 -0.485385 -2.065922 -0.207081

8 1.257222 -1.440359 -0.108228

6 1.977328 -1.206006 1.140889

6 2.794567 0.061798 0.904818

1 1.238874 -1.110250 1.943435

1 2.608979 -2.082285 1.333437

6 -1.926825 1.255557 0.142107

17 0.010291 2.549373 -0.126603

1 -1.287316 0.479650 0.519230

1 -2.352190 1.985411 0.811911

1 -2.128456 1.330930 -0.912533

6 1.817917 -0.590765 -1.171498

6 3.116236 -0.030957 -0.596240

1 1.955264 -1.223735 -2.053137

1 1.101145 0.210757 -1.374477

1 3.954671 -0.714632 -0.779112

1 3.356203 0.943011 -1.031718

1 3.689090 0.095405 1.534829

1 2.184264 0.950261 1.097064

3-pr

6 2.566759 -1.462853 -0.223008

6 3.525562 -0.327002 -0.402650

8 1.344434 -1.370985 -0.199262

1 3.013972 -2.470505 -0.100157

1 2.974100 0.619889 -0.427996

1 4.003925 -0.479107 -1.384616

3 0.185187 0.197098 -0.213377

8 -1.671658 -0.226801 -0.299205

6 -2.363791 -1.448028 0.064507

6 -3.846909 -1.071188 0.192549

6 -2.608076 0.885811 -0.356631

6 -3.789345 0.436326 0.497948

1 -2.170643 -2.199502 -0.707867

1 -1.944491 -1.802079 1.013760

1 -4.353352 -1.651580 0.970193

1 -4.371624 -1.246769 -0.754295

1 -2.077513 1.770358 0.002288

1 -2.899925 1.039928 -1.404062

1 -3.579774 0.610878 1.560169

1 -4.714937 0.961017 0.240700

6 4.612114 -0.326205 0.690542

1 4.176673 -0.121302 1.674300

1 5.344580 0.459255 0.481295

1 5.147291 -1.282939 0.739637

17 0.878593 2.227193 -0.003237

3-tsA

6 -3.165200 -1.144616 -0.367982

6 -3.686569 -0.118940 0.410599

1 -3.507279 -0.113022 1.482835

1 -4.577480 0.394892 0.059718

8 -2.181470 -1.903594 -0.053620

1 -3.564411 -1.258183 -1.390078

3 -0.476587 -2.024256 0.173532

8 1.268434 -1.395577 0.189416

6 1.789674 -0.509018 1.237979

6 3.141284 -0.030451 0.717142

1 1.095595 0.330163 1.350205

1 1.844472 -1.096185 2.159267

6 -1.979015 1.249769 0.006225

17 -0.009440 2.511418 -0.164211

1 -1.398326 0.524549 0.544050

1 -2.477496 2.047944 0.532304

1 -2.048081 1.203716 -1.066955

6 2.021881 -1.192040 -1.048073

6 2.895400 0.036780 -0.799586

1 2.611798 -2.099019 -1.228061

1 1.304662 -1.056518 -1.863879

1 3.819314 0.005501 -1.385725

1 2.342973 0.949030 -1.045998

1 3.411559 0.941355 1.139974

1 3.932507 -0.751089 0.959143

3-tsB

6 -2.579314 -1.778342 -0.391449

6 -3.684306 -1.521950 0.421928

1 -3.570379 -1.396296 1.495291

1 -4.668731 -1.815814 0.067360

8 -1.359621 -1.491386 -0.132956

1 -2.794082 -2.163324 -1.405609

3 -0.382753 0.081788 -0.167018

17 -1.250158 2.321499 -0.051145

6 -3.008266 0.783164 0.155956

1 -2.920525 0.571162 -0.892123

1 -2.400800 0.302856 0.892208

1 -3.820154 1.422188 0.483438

8 1.499027 -0.082022 -0.157264

6 2.454997 1.000694 0.016828

6 2.178895 -1.364749 -0.164559

6 3.836589 0.342898 -0.057881

1 2.266846 1.461714 0.993034

1 2.272928 1.743842 -0.764012

6 3.554206 -1.085302 0.439180

1 2.252929 -1.712601 -1.203096

1 1.563790 -2.068388 0.401303

1 4.197997 0.321442 -1.093124

1 4.578227 0.872399 0.548190

1 4.306626 -1.811114 0.114880

1 3.504221 -1.110133 1.534532

4ts

6 -0.308809 2.956387 0.626271

6 -1.098003 3.503062 -0.379634

1 -0.874791 3.273244 -1.419018

1 -1.617871 4.436854 -0.182192

8 0.470606 1.949539 0.517222

1 -0.427853 3.378800 1.640444

3 0.808621 0.246483 0.192369

8 -0.367120 -1.259396 0.207283

6 -0.649314 -2.086503 -0.956502

6 -2.013491 -2.726283 -0.692542

1 -0.634290 -1.444969 -1.843701

1 0.151406 -2.833375 -1.041117

6 -2.735598 1.981334 -0.227261

17 -4.333551 0.289834 -0.246514

1 -1.985000 1.249015 -0.462800

1 -3.253165 2.506252 -1.013049

1 -2.967921 2.210120 0.798574

6 -1.360771 -1.515021 1.251108

6 -2.047315 -2.815587 0.842460

1 -0.824487 -1.570583 2.203377

1 -2.072313 -0.684118 1.263464

1 -1.484592 -3.687017 1.201556

1 -3.067370 -2.869992 1.233060

1 -2.110823 -3.700303 -1.183086

1 -2.817956 -2.069331 -1.038216

8 2.645809 -0.108867 -0.240717

6 3.433069 -1.308055 -0.022622

6 3.520351 1.035336 -0.438368

1 3.627443 1.211257 -1.517273

6 4.844045 0.624193 0.199561

1 3.029914 1.896543 0.019593

1 3.143241 -2.054417 -0.769378

1 3.188687 -1.692427 0.974606

6 4.903069 -0.877063 -0.134011

1 5.694063 1.185421 -0.200965

1 4.809670 0.780855 1.284415

1 5.270040 -1.024445 -1.156646

1 5.550730 -1.445019 0.540905

5ts

6 0.218613 -0.563037 2.983276

6 1.082503 -1.612055 3.285918

1 0.958969 -2.571231 2.788291

1 1.579223 -1.618969 4.252805

8 -0.519361 -0.460653 1.948527

1 0.244801 0.307702 3.667913

3 -0.722249 0.139456 0.221672

8 0.004001 -1.113261 -1.162150

6 0.055447 -2.541372 -0.923408

6 1.381311 -3.009410 -1.524073

1 -0.037355 -2.699274 0.154530

1 -0.801662 -3.012271 -1.427673

6 2.671349 -0.906404 1.809090

17 4.108507 -0.310224 0.112087

1 1.872211 -0.982639 1.095655

1 3.259469 -1.770151 2.073393

1 2.842769 0.018011 2.333307

6 0.994958 -0.740822 -2.165668

6 1.542454 -2.057706 -2.721328

1 0.493431 -0.121869 -2.917157

1 1.780940 -0.161553 -1.672321

1 0.944295 -2.404054 -3.574041

1 2.582725 -1.957426 -3.044088

1 1.357301 -4.065786 -1.811569

1 2.203290 -2.858419 -0.815978

8 -2.698960 0.298499 -0.117851

6 -3.539900 0.413335 1.065078

6 -3.393303 -0.447183 -1.136517

1 -3.922912 0.250812 -1.802757

6 -4.372321 -1.336541 -0.372352

1 -2.639838 -0.987966 -1.714402

1 -3.750459 1.475002 1.237267

1 -2.957751 0.021999 1.903357

6 -4.810702 -0.404788 0.772600

1 -5.207765 -1.677522 -0.992644

1 -3.852751 -2.217501 0.022617

1 -5.625597 0.248383 0.437854

1 -5.159630 -0.949023 1.655578

8 0.081941 1.889911 -0.240763

6 -0.506287 2.878136 -1.113521

6 1.284066 2.419905 0.388449

6 0.149721 4.206002 -0.730520

1 -1.590093 2.852675 -0.967714

1 -0.282812 2.606842 -2.155394

6 1.558568 3.754266 -0.310216

1 2.089564 1.690422 0.267803

1 1.069681 2.553823 1.456192

1 0.152770 4.923734 -1.557381

1 -0.377169 4.662679 0.116586

1 2.193190 3.600659 -1.191122

1 2.063472 4.468425 0.347661

6ts

6 -1.984004 0.407430 3.116738

6 -1.134574 -0.284883 3.974016

1 -0.893381 -1.325771 3.770771

1 -1.037803 0.053409 5.002466

8 -2.296982 0.079526 1.924786

1 -2.358132 1.384681 3.480941

3 -1.994574 0.131949 0.116648

8 -0.729648 -1.275271 -0.519455

6 -0.661981 -2.546158 0.176269

6 0.815518 -2.941943 0.169667

1 -1.089934 -2.401616 1.172197

1 -1.275102 -3.274996 -0.373640

6 0.767413 0.495330 2.939357

17 2.619140 1.090645 1.736234

1 0.335802 0.033632 2.070272

1 1.337406 -0.087846 3.644185

1 0.537976 1.519524 3.178029

6 0.536615 -1.011789 -1.194250

6 1.310101 -2.329364 -1.151749

1 0.306264 -0.665118 -2.206830

1 1.060843 -0.219534 -0.648581

1 1.027404 -2.970630 -1.997248

8 4.739741 -1.556781 -1.214102

1 0.955403 -4.026616 0.222938

1 1.340718 -2.486065 1.017019

8 -3.745367 -0.226353 -0.806972

6 -4.941474 -0.067862 0.007363

6 -3.944971 -1.296048 -1.750481

1 -4.356959 -0.887055 -2.685880

6 -4.939805 -2.233394 -1.068995

1 -2.965566 -1.736006 -1.953363

1 -5.383054 0.911191 -0.212030

1 -4.613704 -0.087735 1.049633

6 -5.877244 -1.234949 -0.363817

1 -5.461895 -2.885421 -1.777029

1 -4.421705 -2.863549 -0.336616

1 -6.660790 -0.899892 -1.053830

1 -6.368012 -1.661880 0.516163

8 -1.299777 1.827024 -0.650502

6 -1.669560 2.360274 -1.940856

6 -0.504812 2.796926 0.089750

6 -1.381469 3.861214 -1.865118

1 -2.720298 2.113285 -2.118318

1 -1.055889 1.872951 -2.712057

6 -0.175223 3.905572 -0.911990

1 0.380012 2.292008 0.485969

1 -1.117316 3.166947 0.921703

1 -1.174152 4.295846 -2.848453

1 -2.236223 4.393944 -1.429944

1 0.750346 3.670174 -1.450857

1 -0.043613 4.876771 -0.424906

6 5.250051 -1.378829 0.125732

6 4.998746 -0.378895 -1.996572

6 5.486841 0.695219 -1.016305

1 4.075506 -0.099452 -2.519153

1 5.763396 -0.617227 -2.751737

6 6.166606 -0.152571 0.071823

1 5.767646 -2.301224 0.412568

1 4.408722 -1.204973 0.808374

1 4.638525 1.237780 -0.584526

1 6.161374 1.418100 -1.488586

1 6.225644 0.361537 1.036045

1 7.181233 -0.438186 -0.235580

1 2.393249 -2.174629 -1.179561

7ts

6 2.373440 3.264043 0.015196

6 1.463864 3.869774 -0.845507

1 1.386921 3.530414 -1.875980

1 1.134962 4.883751 -0.632844

8 2.940998 2.134100 -0.147787

1 2.557175 3.782246 0.977405

3 3.021716 0.317237 0.081505

8 2.024491 -0.728876 -1.290565

6 1.691303 -0.168582 -2.587319

6 0.291276 -0.691661 -2.910170

1 1.767244 0.918910 -2.506247

1 2.432197 -0.522272 -3.319167

6 -0.289897 2.540553 -0.141248

17 -1.938357 1.055663 0.385055

1 0.363898 1.737235 -0.428305

1 -0.893240 3.046466 -0.876992

1 -0.250099 2.935971 0.859342

6 1.093232 -1.801339 -0.963905

6 0.306242 -2.078276 -2.244673

1 1.678488 -2.656489 -0.609860

1 0.439070 -1.450474 -0.158628

1 0.840406 -2.799892 -2.876940

8 -2.790221 -3.243576 -1.080544

1 0.101271 -0.731336 -3.987865

1 -0.473743 -0.059738 -2.444542

8 4.948443 -0.232226 -0.021075

6 5.910469 0.806573 0.318729

6 5.464814 -1.039299 -1.099624

1 5.970111 -1.922638 -0.680937

6 6.449397 -0.131218 -1.834090

1 4.611328 -1.367386 -1.697932

1 6.213561 0.667443 1.362674

1 5.391091 1.763575 0.218706

6 7.080340 0.650176 -0.667597

1 7.182893 -0.691719 -2.422971

1 5.909735 0.545601 -2.506943

1 7.893291 0.067144 -0.218161

1 7.490699 1.617580 -0.973139

8 2.354607 -0.382988 1.819081

6 2.936718 -1.477281 2.560764

6 1.291692 0.243706 2.591774

6 2.457014 -1.298045 4.002420

1 4.022417 -1.426937 2.437904

1 2.577057 -2.424446 2.133713

6 1.067653 -0.670992 3.798472

1 0.410083 0.348163 1.953236

1 1.639809 1.239763 2.892698

1 2.429817 -2.243927 4.553149

1 3.116215 -0.607245 4.542728

1 0.708300 -0.120203 4.673266

6 -3.876185 -2.356719 -1.420850

6 -2.818780 -3.527155 0.330213

6 -3.921576 -2.644415 0.932964

1 -1.826729 -3.318095 0.750040

1 -3.032893 -4.597857 0.463852

6 -4.870558 -2.446764 -0.261425

1 -4.285282 -2.686642 -2.382173

1 -3.486554 -1.334479 -1.527098

1 -3.508571 -1.678607 1.245752

1 -4.405287 -3.110949 1.798219

8 -6.623171 0.703984 0.208511

1 -5.521703 -3.322429 -0.384682

1 -0.692212 -2.471972 -2.031690

1 0.327982 -1.444628 3.560084

6 -6.591992 1.447548 -1.019714

6 -5.891209 1.411731 1.231204

6 -5.511047 2.520015 -0.843230

1 -7.582227 1.897677 -1.192399

1 -6.383817 0.749283 -1.838872

6 -5.595975 2.805963 0.665167

1 -4.960021 0.869872 1.440417

1 -6.506106 1.430286 2.138621

1 -4.522276 2.114559 -1.085680

1 -5.690724 3.404425 -1.464920

1 -4.670793 3.226577 1.070872

1 -6.420775 3.497403 0.882591

1 -5.498642 -1.555329 -0.167025

8ts

6 -2.170319 -1.422625 -2.724479

6 -1.179973 -0.720896 -3.403927

1 -1.164582 0.366086 -3.366240

1 -0.694989 -1.193950 -4.253822

8 -2.936070 -0.976401 -1.809043

1 -2.246548 -2.504105 -2.953653

3 -3.646534 -0.412253 -0.230599

8 -3.704277 1.576496 -0.057334

6 -3.639034 2.353001 -1.280508

6 -2.591075 3.433877 -1.018375

1 -3.390049 1.664071 -2.091598

1 -4.629763 2.792571 -1.468245

6 0.408495 -0.965128 -1.760579

17 1.941157 -1.023586 -0.066899

1 -0.279805 -0.406237 -1.152508

1 1.082698 -0.455180 -2.428555

1 0.347236 -2.038982 -1.797822

6 -3.084123 2.316022 1.032864

6 -2.781005 3.711469 0.482470

1 -3.781344 2.318967 1.877707

1 -2.167868 1.792559 1.324247

1 -3.631264 4.387046 0.641913

8 0.437615 3.290884 1.587919

1 -2.740499 4.319785 -1.644414

1 -1.583908 3.044698 -1.207436

8 -5.592514 -0.969740 -0.168681

6 -5.965138 -2.088237 -1.020989

6 -6.692550 -0.042064 -0.074485

1 -7.287793 -0.274343 0.821707

6 -7.503307 -0.262187 -1.350331

1 -6.265561 0.958135 0.029273

1 -5.917344 -3.007754 -0.426702

1 -5.219208 -2.138954 -1.818933

6 -7.382605 -1.785433 -1.537100

1 -8.539696 0.078473 -1.256761

1 -7.039803 0.269657 -2.189709

1 -8.135978 -2.301687 -0.929969

1 -7.516993 -2.101195 -2.576298

8 -2.824146 -1.132808 1.423883

6 -3.552559 -1.311782 2.659066

6 -1.594353 -1.915136 1.444406

6 -2.925772 -2.533543 3.334027

1 -4.610781 -1.432164 2.409252

1 -3.431122 -0.408199 3.273146

6 -1.460533 -2.430428 2.879126

1 -0.764133 -1.277791 1.132650

1 -1.704317 -2.733079 0.722417

1 -3.044952 -2.515466 4.422264

1 -3.382600 -3.456724 2.956086

1 -0.923077 -3.382347 2.925679

6 1.473260 3.759543 0.702272

6 1.016608 2.458262 2.614118

6 2.500644 2.292407 2.258698

1 0.478058 1.503421 2.634905

1 0.878270 2.961175 3.582485

6 2.791718 3.571484 1.454702

1 1.252077 4.802652 0.449776

1 1.456697 3.161399 -0.221048

1 2.640685 1.405768 1.630409

1 3.132202 2.188959 3.147884

8 5.433584 2.834012 -0.896383

1 2.967926 4.420882 2.128154

1 -1.892231 4.137505 0.954617

1 -0.916303 -1.706079 3.496866

6 4.820117 2.334524 -2.097995

6 6.284176 1.822004 -0.323034

6 5.107344 0.828363 -2.136473

1 5.261268 2.854966 -2.961910

1 3.749936 2.570446 -2.062086

6 6.453176 0.741181 -1.395898

1 5.798186 1.416341 0.576251

1 7.225501 2.297804 -0.025703

1 4.333839 0.275257 -1.590749

1 5.151827 0.437933 -3.159549

8 6.528182 -2.510746 0.238604

1 7.279886 1.001154 -2.070409

1 3.651150 3.474706 0.783723

1 6.649543 -0.246989 -0.968031

6 6.288449 -3.619125 -0.642222

6 5.456857 -2.405880 1.200706

6 4.827385 -4.029383 -0.426102

1 6.977801 -4.438795 -0.385065

1 6.505301 -3.296192 -1.667200

6 4.617470 -3.680703 1.056778

1 4.857347 -1.516572 0.968865

1 5.902925 -2.287339 2.195089

1 3.566488 -3.507969 1.306479

1 5.008830 -4.479842 1.700196

1 4.158505 -3.421652 -1.046105

1 4.649144 -5.086205 -0.654594