Quantum chemical Calculations and Molecular Docking Studies of 5-(4-chlorobenzylidene)thiazolidine-2,4-dione(CTD) and its mannich product 5-(4-chlorobenzylidene)-3-(morpholinomethyl)thiazolidine-2,4-dione (CMTD)

Shaheen Fatmaa, Abha Bishnoia*, Anil Kumar Vermaa, Vineeta Singhb , Krishna Srivastavac

aDepartment of Chemistry, University of Lucknow, Lucknow 226007, India

bDepartment of Biotechnology, Institute of Engineering and Technology, Lucknow-226021.

cDepartment of Chemistry, Shri Ramswaroop Memorial University, Lucknow 226001,India.

Corresponding author: Dr. Abha Bishnoi, Professor, Department of Chemistry, University of Lucknow, Lucknow-226007, India.

Email-abhabishnoi5@gmail.com, dr.abhabishnoi@gmail.com, shaheenfatma3@gmail.com

Phone - +91-9415028822, +91-0522-2662777.

Fig S1a. 1HNMR spectra of CTD

Fig S1b. 1HNMR spectra of CMTD

Fig S2a. 13CNMR spectra of CTD

Fig S2b. 13CNMR spectra of CMTD

Fig S3a. Mass spectra of CTD

Fig S3b. Mass spectra of CMTD

Fig.S4a. A Pictorial representation of Zone of Inhibition (mm) of CTD and CMTD against various bacterial and fungal strains.

Fig.S4b. A Pictorial representation of MIC Values of CTD and CMTD against various bacterial and fungal strains.

Supplementary Table 1.(ST1a) Comparison of experimental and calculated optimized geometrical parameters for CTD using B3LYP /6-31G (d, p) method.

Bond Length

Bond Angle

Dihedral Angle

B3LYP

Exp

B3LYP

Exp

B3LYP

C1-C2

1.4883

1.483

C2-C1-C4

131.0587

120.2

C4-C1-C2-N17

179.9772

C1-C4

1.359

1.348

C2-C1-S18

109.7703

110.5

C4-C1-C2-O19

-0.0174

C1-S18

1.7952

1.752

C4-C1-S18

119.171

119.16

S18-C1-C2-N17

0.0056

C2-N17

1.3937

1.38

C1-C2-N17

109.557

109.6

S18-C1-C2-O19

180.0111

C2-O19

1.2201

1.213

C1-C2-O19

128.6813

126.3

C2-C1-C4-C5

0.0404

C3-N17

1.3851

1.363

N17-C2-O19

121.7616

124.1

C2-C1-C4-H15

-179.956

C3-S18

1.8029

1.779

N17-C3-S18

107.9253

109.9

S18-C1-C4-C5

-179.99

C3-O20

1.2051

1.198

N17-C3-O20

126.3768

124

S18-C1-C4-H15

0.0131

C4-C5

1.4589

1.446

S18-C3-O20

125.6979

C2-C1-S18-C3

0.0033

C4-H15

1.0899

C1-C4-C5

135.6301

130

C4-C1-S18-C3

-179.972

C5-C6

1.411

1.397

C1-C4-H15

113.0348

C1-C2-N17-C3

-0.0161

C5-C7

1.4134

1.4

C5-C4-H15

111.3351

C1-C2-N17-H16

-179.981

C6-C9

1.3904

1.387

C4-C5-C6

126.3906

117.8

O19-C2-N17-C3

-180.021

C6-H14

1.0813

C4-C5-C7

115.8283

O19-C2-N17-H16

0.0139

C7-C8

1.3885

1.387

C6-C5-C7

117.781

S18-C3-N17-C2)

0.0183

C7-H11

1.0865

C5-C6-C9

120.7522

S18-C3-N17-H16

-180.017

C8-C10

1.3951

C5-C6-H14

119.4033

O20-C3-N17-C2)

180.0162

C8-H12

1.0839

C9-C6-H14

119.8445

O20-C3-N17-H16

-0.0188

C9-C10

1.3955

1.396

C5-C7-C8

121.8583

N17-C3-S18-C1

-0.0113

C9-H13

1.0842

C5-C7-H11

119.3621

O20-C3-S18-C1

179.9908

C10-Cl21

1.7533

C8-C7-H11

118.7795

C1-C4-C5-C6

0.0045

H16-N17

1.0126

C7-C8-C10

118.82

C1-C4-C5-C7

180.0064

C7-C8-H12

120.8716

H15-C4-C5-C6

-179.999

C10-C8-H12

120.3085

H15-C4-C5-C7

0.003

C6-C9-C10

119.8785

C4-C5-C6-C9

179.9905

C6-C9-H13

120.2175

C4-C5-C6-H14

-0.0069

C10-C9-H13

119.9041

C7-C5-C6-C9

-0.0114

C8-C9-C9

120.91

C7-C5-C6-H14

-180.009

C8-C9-Cl21

119.4659

C4-C5-C7-C8

-179.998

C9-C9-Cl21

119.6241

C4-C5-C7-H11

-0.0014

C2-N17-C3

120.279

118.4

C6-C5-C7-C8

0.0041

C2-N17-H16

119.9047

C6-C5-C7-H11

-180

C3-N17-H16

119.8163

C5-C6-C9-C10

0.0141

C1-S18-C3

92.4684

91.7

C5-C6-C9-H13

-179.996

H14-C6-C9-C10

180.0115

H14-C6-C9-H13

0.0014

C5-C7-C8-C10

0.0004

C5-C7-C8-H12

-180.004

H11-C7-C8-C10

180.0042

H11-C7-C8-H12

-0.0003

C7-C8-C10-C9

0.0022

C7-C8-C10-Cl21

179.9972

H12-C8-C10-C9

180.0066

H12-C8-C10-Cl21

0.0016

C6-C9-C10-C8

-0.0094

C6-C9-C10-Cl21

-180.005

H13-C9-C10-C8

180.0007

H13-C9-C10-Cl21

0.0057

Supplementary Table 1.(ST1b) Comparison of experimental and calculated optimized geometrical parameters for CMTD using B3LYP /6-31G (d, p) method.

Bond length

Bond Angle

B3LYP

Exp

B3LYP

Exp

S1-C2

1.8167

1.779

C2-S1-C5

91.4785

C5-S1-C2-N3

1.5261

S1-C5

1.7713

1.752

S1-C2-N3

109.7249

C5-S1-C2-O6

-179.082

C2-N3

1.3825

1.363

S1-C2-O6

123.8281

C2-S1-C5-C4

0.0666

C2-O6

1.2079

1.198

N3-C2-O6

126.4438

C2-S1-C5-C8

-179.565

N3-C4

1.3949

1.38

C2-N3-C4

117.5814

S1-C2-N3-C4

-2.9483

N3-C15

1.4809

C2-N3-C15

120.6666

S1-C2-N3-C15

-177.384

C4-C5

1.4922

1.483

C4-N3-C15

121.5103

O6-C2-N3-C4

177.6797

C4-O7

1.2199

1.213

N3-C4-C5

110.7298

O6-C2-N3-C15

3.2437

C5-C8

1.3515

1.348

N3-C4-O7

123.4411

C2-N3-C4-C5

3.0315

C8-C9

1.4547

1.446

C5-C4-O7

125.8274

C2-N3-C4-O7

-177.418

C8-H23

1.0888

S1-C5-C4

110.408

C15-N3-C4-C5

177.4177

C9-C10

1.4106

1.4

S1-C5-C8

130.3165

C15-N3-C4-O7

-3.0317

C9-C14

1.4099

1.397

C4-C5-C8

119.2745

C2-N3-C15-N16

85.9694

C10-C11

1.3893

1.387

C5-C8-C9

131.8216

C2-N3-C15-H28

-152.064

C10-H24

1.0862

C5-C8-H23

112.7496

C2-N3-C15-H29

-36.3725

C11-C12

1.3952

C9-C8-H23

115.4284

C4-N3-C15-N16

-88.2452

C11-H25

1.084

C8-C9-C10

117.54

C4-N3-C15-H28

33.7219

C12-C13

1.3957

1.396

C8-C9-C14

124.7577

C4-N3-C15-H29

149.4129

C12-Cl22

1.7532

C10-C9-C14

117.7023

N3-C4-C5-S1

-1.6405

C13-C14

1.3903

1.387

C9-C10-C11

121.7257

N3-C4-C5-C8

178.0372

C13-H26

1.084

C9-C10-H24

119.1128

O7-C4-C5-S1

178.822

C14-H27

1.0834

C11-C10-H24

119.1614

O7-C4-C5-C8

-1.5003

C15-N16

1.4395

C10-C11-C12

118.9828

S1-C5-C8-C9

-0.026

C15-H28

1.0927

C10-C11-H25

120.8311

S1-C5-C8-H23

179.7293

C15-H29

1.0926

C12-C11-H25

120.1861

C4-C5-C8-C9

-179.63

N16-C17

1.4653

1.485

C11-C12-C13

120.9274

C4-C5-C8-H23

0.1255

N16-C21

1.4651

1.486

C11-C12-Cl22

119.5693

C5-C8-C9-C10

178.2568

C17-C18

1.5267

1.511

C13-C12-Cl22

119.5033

C5-C8-C9-C14

-1.7408

C17-H30

1.0944

1.01

C12-C13-C14

119.4947

H23-C8-C9-C10

-1.4934

C17-H31

1.1061

0.98

C12-C13-H26

120.0027

H23-C8-C9-C14

178.509

C18-O19

1.4222

1.416

C14-C13-H26

120.5026

C8-C9-C10-C11

-179.796

C18-H32

1.0937

0.95

C9-C14-C13

121.1667

C8-C9-C10-H24

0.1019

C18-H33

1.102

0.97

C9-C14-H27

120.6843

C14-C9-C10-C11

0.2014

O19-C20

1.4223

1.428

C13-C14-H27

118.1486

C14-C9-C10-H24

-179.9

C20-C21

1.5269

1.505

N3-C15-N16

112.7868

C8-C9-C14-C13

179.8628

C20-H34

1.0937

0.95

N3-C15-H28

105.1545

C8-C9-C14-H27

-0.3627

C20-H35

1.102

0.97

N3-C15-H29

105.798

C10-C9-C14-C13

-0.1349

C21-H36

1.0944

1.01

N16-C15-H28

111.7087

C10-C9-C14-H27

179.6397

C21-H37

1.1061

0.95

N16-C15-H29

111.6629

C9-C10-C11-C12

-0.1098

A(28,15-H29

109.3577

C9-C10-C11-H25

179.908

C15-N16-C17

115.3423

H24-C10-C11-C12

179.9919

C15-N16-C21

115.4412

H24-C10-C11-H25

0.0098

C17-N16-C21

112.1784

C10-C11-C12-C13

-0.0535

N16-C17-C18

109.1287

C10-C11-C12-Cl22

179.9852

N16-C17-H30

108.8336

H25-C11-C12-C13

179.9288

N16-C17-H31

111.7767

H25-C11-C12-Cl22

-0.0325

C18-C17-H30

110.0527

C11-C12-C13-C14

0.1176

C18-C17-H31

108.8287

C11-C12-C13-H26

-179.855

H30-C17-H31

108.2089

Cl22-C12-C13-C14

-179.921

C17-C18-O19

111.2751

Cl22-C12-C13-H26

0.1068

C17-C18-H32

110.631

C12-C13-C14-C9

-0.0201

C17-C18-H33

109.3231

C12-C13-C14-H27

-179.8

O19-C18-H32

106.5998

H26-C13-C14-C9

179.9518

O19-C18-H33

110.1893

H26-C13-C14-H27

0.1717

H32-C18-H33

108.7662

N3-C15-N16-C17

112.3656

C18-O19-C20

110.9449

N3-C15-N16-C21

-114.175

O19-C20-C21

111.2875

H28-C15-N16-C17

-5.8276

O19-C20-H34

106.5995

H28-C15-N16-C21

127.6319

O19-C20-H35

110.1822

H29-C15-N16-C17

-128.649

C21-C20-H34

110.6188

H29-C15-N16-C21

4.811

C21-C20-H35

109.3276

C15-N16-C17-C18

-169.866

H34-C20-H35

108.7688

C15-N16-C17-H30

-49.7494

N16-C21-C20

109.1309

C15-N16-C17-H31

69.7091

N16-C21-H36

108.8899

C21-N16-C17-C18

55.1941

N16-C21-H37

111.8131

C21-N16-C17-H30

175.3102

C20-C21-H36

109.8992

C21-N16-C17-H31

-65.2312

C20-C21-H37

108.8367

C15-N16-C21-C20

169.9378

H36-C21-H37

108.2551

C15-N16-C21-H36

49.9731

C15-N16-C21-H37

-69.6021

C17-N16-C21-C20

-55.1689

C17-N16-C21-H36

-175.134

C17-N16-C21-H37

65.2911

N16-C17-C18-O19

-56.4574

N16-C17-C18-H32

-174.764

N16-C17-C18-H33

65.4812

H30-C17-C18-O19

-175.82

H30-C17-C18-H32

65.8733

H30-C17-C18-H33

-53.8816

H31-C17-C18-O19

65.7605

H31-C17-C18-H32

-52.546

H31-C17-C18-H33

-172.301

C17-C18-O19-C20

59.2624

H32-C18-O19-C20

179.9689

H33-C18-O19-C20

-62.1722

C18-O19-C20-C21

-59.2417

C18-O19-C20-H34

-179.94

C18-O19-C20-H35

62.2019

O19-C20-C21-N16

56.4163

O19-C20-C21-H36

175.757

O19-C20-C21-H37

-65.8527

H34-C20-C21-N16

174.7224

H34-C20-C21-H36

-65.937

H34-C20-C21-H37

52.4534

H35-C20-C21-N16

-65.5243

H35-C20-C21-H36

53.8163

H35-C20-C21-H37

172.2067

Table.S2a. The recorded (FT-IR ) and computed vibrational wavenumbers by B3LYP/6-31G(d,p), IR activities along with the assignments of vibrational modes of CTD based on PED results.

unscaled

Scaled

Exp

IIR(km/mol)

Vibrational Assignment (PED in (%;>3%)

1

29.55

28.60145

0.01

τ(C1-C4)( 28.), τ(C3-S18)( 25.), -δ(O19-C1-C2-S18)( 18.), -δ(O19-C9-C8-H12)( 16.), -δ(S18-C4-C1-C5)( 6.),

2

38.69

37.44805

0.06

δ(S18-C4-C1-C5)( 80.), -τ(C1-C4)( 8.), τ(C3-S18)( 7.),

3

82.44

79.79368

0.79

δ(S18-C4-C1-C5)( 53.), -τ(C3-S18)( 28.), -δ(C1-C5-C4-C7)( 15.),

4

102.51

99.21943

1.15

δ(S18-C4-C1-C5)( 63.), -δ(O19-C1-C2-S18)( 16.), δ(O19-C9-C8-H12)( 13.), -δ(C1-C5-C4-C7)( 4.),

5

155.55

150.5568

7.49

τ(C1-C2)( 50.), π(H16-C2-C3-N17)( 24.), -τ(C3-S18)( 23.),

6

187.41

181.3941

0.07

δ(S18-C4-C1-C5)( 63.), -τ(C3-S18)( 17.), -τ(C1-C4)( 12.), τ(C5-C7)( 3.),

7

193.11

186.9112

3.11

δ(C1-C5-C4-C7)( 44.), -δ(O19-C1-C2-S18)( 18.), -δ(O19-C9-C8-H12)( 11.), -δ(S18-C4-C1-C5)( 8.), β(C6-C7-C5)( 4.), -ν(C4-C5)( 3.),

8

231.39

223.9624

1.07

δ(C1-C5-C4-C7)( 24.), -β(S18-C2-C1)( 16.), -δ(O19-C1-C2-S18)( 13.), β(C8-Cl21-C10)( 10.), -δ(S18-C4-C1-C5)( 8.), -β(C6-C7-C5)( 6.), ν(C4-C5)( 4.), ν(C1-C4)( 4.),

9

322.75

312.3897

0.36

β(C8-Cl21-C10)( 31.), δ(S18-C4-C1-C5)( 21.), δ(O19-C1-C2-S18)( 12.), -β(C1-O19-C2)( 9.), -δ(C1-C5-C4-C7)( 8.), δ(O19-C9-C8-H12)( 7.), β(C5-C8-C7)( 5.),

10

344.03

332.9866

0.11

τ(C3-S18)( 31.), -δ(C1-C5-C4-C7)( 31.), -π(Cl21-C8-C9-C10)( 12.), -δ(S18-C4-C1-C5)( 6.), -τ(C5-C7)( 5.), τ(C1-C2)( 3.), τ(C1-C4)( 3.),

11

372.65

360.6879

27.37

δ(O19-C1-C2-S18)( 23.), β(N17-O20-C3)( 21.), -β(C1-O19-C2)( 15.), -δ(S18-C4-C1-C5)( 11.), -ν(C3-S18)( 8.), -β(S18-C2-C1)( 7.), -ν(C1-S18)( 4.),

12

388.96

376.4744

0.98

τ(C1-C4)( 35.), -δ(S18-C4-C1-C5)( 21.), -τ(C5-C7)( 14.), π(O19-C1-N17-C2)( 6.), δ(C1-C5-C4-C7)( 5.), -π(Cl21-C8-C9-C10)( 4.),

13

427.92

414.1838

0.22

τ(C5-C7)( 62.), τ(C1-C4)( 9.), -δ(S18-C4-C1-C5)( 8.), -π(H12-C7-C10-C8)( 4.), π(H11-C5-C8-C7)( 3.),

14

432.97

419.0717

72.65

β(S18-C2-C1)( 42.), ν(C10-Cl21)( 24.), -β(C6-C7-C5)( 15.),

15

486.76

471.135

30.32

β(C1-O19-C2)( 24.), ν(C1-S18)( 20.), -ν(C3-S18)( 16.), β(S18-C2-C1)( 9.), β(N17-O20-C3)( 8.), -δ(S18-C4-C1-C5)( 6.), ν(C1-C2)( 5.), -δ(O19-C1-C2-S18)( 4.),

16

520.31

503.608

21.5

τ(C5-C7)( 39.), π(Cl21-C8-C9-C10)( 30.), τ(C1-C4)( 14.), -δ(C1-C5-C4-C7)( 6.),

17

528.22

511.2641

21.5

β(S18-C2-C1)( 23.), δ(S18-C4-C1-C5)( 22.), -β(C1-O19-C2)( 19.), δ(O19-C1-C2-S18)( 13.), δ(C1-C5-C4-C7)( 5.), -β(C1--N17-C2)( 5.), ν(C1-S18)( 4.),

18

600.07

580.8078

101.79

π(H16-C2-C3-N17)( 82.), π(O20-N17-S18-C3)( 13.),

19

616.11

596.3329

29.55

β(C1--N17-C2)( 51.), ν(C1-S18)( 10.), ν(C3-N17)( 8.), ν(C2-N17)( 7.), -δ(S18-C4-C1-C5)( 6.), β(S18-C2-C1)( 6.),

20

642.72

622.0887

13.43

β(C5-C8-C7)( 60.), -δ(O19-C9-C8-H12)( 18.), ν(C3-S18)( 5.),

21

644.82

624.1213

61.62

π(O20-N17-S18-C3)( 59.), -τ(C1-C2)( 22.), -π(H16-C2-C3-N17)( 17.),

22

671.69

650.1288

27.1

β(C6-C7-C5)( 18.), -ν(C3-S18)( 18.), ν(C10-Cl21)( 14.), -ν(C1-C2)( 7.), δ(S18-C4-C1-C5)( 6.), ν(C1-S18)( 5.), -δ(O19-C9-C8-H12)( 4.), -β(C1-O19-C2)( 4.), β(C5-C8-C7)( 4.), -β(N17-O20-C3)( 3.),

23

680.53

658.685

680

59.48

ν(C3-S18)( 27.), β(C6-C7-C5)( 14.), β(N17-O20-C3)( 14.), ν(C10-Cl21)( 11.), β(C1-O19-C2)( 7.), -β(C1--N17-C2)( 4.), δ(S18-C4-C1-C5)( 4.),

24

717.73

694.6909

0.33

τ(C5-C7)( 65.), -π(Cl21-C8-C9-C10)( 13.), τ(C3-S18)( 5.), π(O19-C1-N17-C2)( 3.), -δ(C1-C5-C4-C7)( 3.),

25

760.39

735.9815

35.19

τ(C3-S18)( 44.), π(O19-C1-N17-C2)( 35.), -τ(C1-C4)( 7.), -τ(C1-C2)( 5.), -τ(C5-C7)( 3.),

26

792.82

767.3705

55.54

β(C1-O19-C2)( 21.), δ(S18-C4-C1-C5)( 20.), -ν(C1-C2)( 15.), β(N17-O20-C3)( 7.), -β(C6-C7-C5)( 6.), ν(C3-S18)( 5.), -ν(C5-C6)( 4.), -β(C2-H16-N17)( 3.),

27

833.42

806.6672

17.86

π(H12-C7-C10-C8)( 45.), π(H11-C5-C8-C7)( 40.), -τ(C5-C7)( 6.), -τ(C1-C4)( 5.),

28

847.36

820.1597

820

53.43

ν(C1-S18)( 16.), -β(S18-C2-C1)( 16.), -ν(C4-C5)( 9.), -β(C1-O19-C2)( 8.), -ν(C6-C7)( 8.), β(C7-C5)( 7.), -β(C6-C7-C5)( 7.), -ν(C5-C6)( 7.), -β(C1--N17-C2)( 4.), -δ(S18-C4-C1-C5)( 3.),

29

853.31

825.9187

24.97

π(H14-C5-C9-C6)( 29.), τ(C5-C7)( 6.), π(Cl21-C8-C9-C10)( 3.),

30

943.3

913.0201

18.65

τ(C1-C4)( 37.), π(H12-C7-C10-C8)( 29.), δ(S18-C4-C1-C5)( 16.), -π(H11-C5-C8-C7)( 9.),

31

979.85

948.3968

4.02

π(H11-C5-C8-C7)( 49.), -π(H12-C7-C10-C8)( 31.), -τ(C5-C7)( 9.), τ(C5-C7)( 4.), τ(C1-C4)( 3.),

32

999.86

967.7645

900

50.52

ν(C1-S18)( 24.), -δ(S18-C4-C1-C5)( 21.), -ν(C1-C2)( 16.), δ(C1-C5-C4-C7)( 13.), -δ(O19-C1-C2-S18)( 4.), -β(S18-C2-C1)( 4.),

33

1000.61

968.4904

0.88

π(H14-C5-C9-C6)( 59.), -3ν(C3-S18)( 29.), τ(C5-C7)( 8.), τ(C5-C7)( 4.),

34

1025.15

992.2427

89.05

β(C7-C5)( 64.), ν(C5-C6)( 11.), ν(C6-C7)( 9.), -ν(C10-Cl21)( 6.),

35

1104.79

1069.326

1010

154.91

ν(C9-C10)( 25.), ν(C8-C10)( 24.), -ν(C10-Cl21)( 22.), -β(C7-H12-C8)( 7.), -β(C6--H13-C9)( 5.), ν(C6-C9)( 4.),

36

1141.33

1104.693

1085

213.44

ν(C3-N17)( 14.), -β(C5--H14-C6)( 12.), -β(C7-H12-C8)( 10.), -ν(C7-C8)( 10.), -ν(C2-N17)( 10.), β(C6--H13-C9)( 9.), ν(C6-C9)( 6.), -ν(C6-C7)( 4.), β(C5-H11-C7)( 4.),

37

1157.48

1120.325

1168

196.82

ν(C3-N17)( 30.), -ν(C2-N17)( 17.), -β(C2-H16-N17)( 7.), -β(C6--H13-C9)( 5.), -β(S18-C2-C1)( 5.), -β(C1-O19-C2)( 4.), β(C7-H12-C8)( 4.), ν(C1-C2)( 4.), -β(C5-H11-C7)( 4.), -β(N17-O20-C3)( 4.), -ν(C6-C9)( 4.), ν(C7-C8)( 3.), -ν(C3-S18)( 3.),

38

1218.96

1179.831

17.91

β(C5-H11-C7)( 25.), -β(C7-H12-C8)( 18.), β(C5--H14-C6)( 18.), -β(C6--H13-C9)( 14.), -ν(C7-C8)( 8.), ν(C6-C7)( 6.), -ν(C6-C9)( 5.),

39

1240.65

1200.825

1230

53.45

ν(C4-C5)( 30.), -ν(C6-C7)( 14.), -ν(C6-C9)( 11.), β(C7-C5)( 8.), β(S18-C2-C1)( 5.), -ν(C3-N17)( 5.), -β(C6--H13-C9)( 4.), -β(C5-H11-C7)( 4.),

40

1299.11

1257.409

535.73

β(C1-O19-C2)( 26.), ν(C2-N17)( 19.), ν(C3-N17)( 15.), -β(C1--N17-C2)( 9.), -ν(C1-C2)( 6.), -β(N17-O20-C3)( 6.), -ν(C3-S18)( 3.),

41

1338.6

1295.631

1282

4.01

ν(C9-C10)( 18.), -ν(C8-C10)( 17.), β(C5-H11-C7)( 15.), -β(C5--H14-C6)( 12.), β(C7-H12-C8)( 10.), -β(C6--H13-C9)( 9.), ν(C5-C6)( 5.), -ν(C6-C7)( 5.), β(C8-Cl21-C10)( 3.),

42

1343.88

1300.741

1300

26.43

ν(C5-C6)( 18.), -ν(C6-C7)( 11.), ν(C7-C8)( 10.), β(C6--H13-C9)( 8.), ν(C9-C10)( 8.), -ν(C4-C5)( 7.), β(C5--H14-C6)( 7.), -ν(C8-C10)( 5.), ν(C1-C2)( 5.), -ν(C6-C9)( 4.), -β(C7-H12-C8)( 4.), -β(C1-O19-C2)( 3.),

43

1392.34

1347.646

116.81

β(C2-H16-N17)( 65.), -ν(C2-N17)( 13.), ν(C3-N17)( 11.), -ν(C2-O19)( 5.), ν(C3-O20)( 4.),

44

1426.88

1381.077

1325

84.02

ν(C6-C9)( 27.), -ν(C7-C8)( 20.), -β(C6--H13-C9)( 12.), β(C7-H12-C8)( 11.), β(C5--H14-C6)( 6.), ν(C1-C2)( 6.),

45

1464.91

1417.886

125.93

β(C5--H14-C6)( 15.), -ν(C7-C8)( 14.), ν(C1-C4)( 13.), ν(C6-C9)( 12.), -β(C5-H11-C7)( 10.), -ν(C1-C2)( 8.), β(C7-H12-C8)( 6.), β(S18-C2-C1)( 5.),

46

1528.86

1479.784

107.19

β(C5-H11-C7)( 18.), β(C6--H13-C9)( 16.), β(C7-H12-C8)( 15.), ν(C8-C10)( 13.), β(C5--H14-C6)( 10.), ν(C9-C10)( 7.), -ν(C5-C6)( 7.), -ν(C6-C7)( 6.), ν(C4-C5)( 4.),

47

1599.66

1548.311

1490

61.42

ν(C5-C6)( 17.), ν(C8-C10)( 17.), -ν(C9-C10)( 14.), ν(C1-C4)( 12.), -ν(C6-C7)( 7.), β(C5-C8-C7)( 7.), -β(C5--H14-C6)( 5.), -ν(C4-C5)( 5.),

48

1626.94

1574.715

1550

279.86

ν(C1-C4)( 16.), ν(C6-C7)( 13.), -ν(C6-C9)( 13.), -ν(C7-C8)( 12.), ν(C9-C10)( 8.), -ν(C4-C5)( 8.), -β(C5-H11-C7)( 6.), -β(C6-C7-C5)( 6.), β(C6--H13-C9)( 4.),

49

1651.72

1598.7

1593

84.02

ν(C1-C4)( 33.), ν(C7-C8)( 13.), ν(C6-C9)( 11.), -ν(C5-C6)( 7.), -ν(C8-C10)( 5.), β(C6-C7-C5)( 4.), β(C5--H14-C6)( 4.), -ν(C1-C2)( 4.),

50

1760.16

1703.659

1699

770.8

ν(C2-O19)( 54.), -β(S18-C2-C1)( 14.), -ν(C3-O20)( 12.), -ν(C2-N17)( 4.), β(C2-H16-N17)( 3.), -ν(C1-C2)( 3.),

51

1808.12

1750.079

1745

966.58

ν(C3-O20)( 66.), ν(C2-O19)( 14.), -β(C1--N17-C2)( 8.), -ν(C3-N17)( 8.),

52

3151.83

3050.656

2767

9.17

ν(C4-H15)( 99.),

53

3197.86

3095.209

9.17

ν(C7-H11)( 94.), -ν(C8-H12)( 5.),

54

3221.49

3118.08

3.98

ν(C9-H13)( 97.),

55

3228.17

3124.546

3138

5.71

ν(C8-H12)( 94.), ν(C7-H11)( 5.),

56

3256.9

3152.354

3051

58.46

ν(C6-H14)( 98.),

57

3607.11

3491.322

3400

169.65

ν(H16-N17)( 99.),

Table.S2b. The recorded (FT-IR ) and computed vibrational wavenumbers by B3LYP/6-31G(d,p), IR activities along with the assignments of vibrational modes of CMTD based on PED results.

FREQ

Unscaled

Scaled

Experimental

Intensity

CONTRIBUTIONS .. COORD(%;>3%)

1

12.44

12.040676

0.02

τ(N3-C15)( 52.) δ(C15-C21-N16-C20)( 39.) -δ(O6-N3-C2-C4)( 7.)

2

19.86

19.222494

0.05

τ(N3-C15)( 68.) -δ(O6-N3-C2-C4)( 29.)τ

3

25.17

24.362043

0.04

δ(O6-N3-C2-C4)( 45.) -τ(N3-C15)( 42.) -δ(C15-C21-N16-C20)( 4.) δ(C15-C21-N16-C20)( 4.)

4

35.75

34.602425

0.08

τ(N3-C15)( 79.) -δ(O6-N3-C2-C4)( 14.) δ(C15-C21-N16-C20)( 3.)

5

50.5

48.87895

0.02

δ(O6-N3-C2-C4)( 43.) τ(S1-C2)( 14.) -τ(N3-C15)( 12.) δ(C15-C21-N16-C20)( 10.) π(C15-C17-C21)( 9.) π(C15-C2-C4)( 8.)

6

72.89

70.550231

0.05

τ(N3-C15)( 66.) δ(C15-C21-N16-C20)( 13.) -δ(O6-N3-C2-C4) 11.)

7

82.43

79.783997

1.45

τ(N3-C15)( 54.) τ(S1-C2)( 23.) -δ(O6-N3-C2-C4)( 14.) τ(C4-C5)( 3.)

8

109.58

106.062482

4.4

δ(O6-N3-C2-C4)( 61.) τ(S1-C2)( 23.) -τ(C4-C5)( 7.) π(C15-C17-C21)( 4.)

9

139.27

134.799433

1.7

τ(S1-C2)( 46.) δ(O6-N3-C2-C4)( 38.) π(C15-C2-C4)( 8.)

10

174.71

169.101809

1.36

τ(S1-C2)( 31.) τ(N3-C15)( 19.) δ(O6-N3-C2-C4)( 18.) -β(C2-C15-N3)( 9.) δ(C15-C21-N16-C20)( 6.) π(C15-C2-C4)( 6.) -β(C17-C15-N16)( 4.)

11

184.03

178.122637

0.16

τ(S1-C2)( 50.) τ(C4-C5)( 20.) τ(C9-C10)( 9.) -π(C8-S1-C4-C5)( 4.) -π(H22-C11-C13-C12)( 3.)

12

213.97

207.101563

0.43

δ(O6-N3-C2-C4)( 14.) -β(C14-C8-C9)( 12.) τ(S1-C2)( 10.) δ(O6-N3-C2-C4)( 10.) β(C11-Cl22-C12)( 9.) -β(C2-C15-N3)( 9.) δ(Cl22-C13-C12-C14)( 6.) -β(C17-C15-N16)( 6.) β(S1-C8-C5)( 6.) π(C15-C2-C4)( 4.)

13

229.4

222.03626

3.94

β(C2-C15-N3)( 26.) δ(O6-N3-C2-C4)( 18.) τ(S1-C2)( 17.) β(C17-C15-N16)( 16.) -δ(O6-N3-C2-C4) 6.) π(C15-C2-C4)( 6.)

14

260.25

251.895975

0.14

τ(N3-C15)( 36.) τ(N16-C17)( 27.) -β(C2-C15-N3)( 13.) β(N3-H28-C15)( 9.) -β(C17-C15-N16)( 6.) δ(C15-C21-N16-C20)( 4.)

15

263.57

255.109403

10.44

τ(S1-C2)( 30.) δ(O6-N3-C2-C4)( 27.) -π(C15-C17-C21)( 18.) π(C15-C2-C4)( 11.) τ(N16-C17)( 5.)

16

303.89

294.135131

11.02

π(C15-C17-C21)( 23.) τ(S1-C2)( 18.) δ(O6-N3-C2-C4)( 18.) δ(C15-C21-N16-C20)( 12.) -τ(N16-C17)( 5.) β(H28-H29-C15)( 4.)

17

331.39

320.752381

0.03

τ(N3-C15)( 23.) β(C11-Cl22-C12)( 22.) π(C8-S1-C4-C5)( 10.) β(C14-C8-C9)( 8.) δ(O6-N3-C2-C4)( 5.) -τ(C4-C5)( 5.) -δ(O6-N3-C2-C4) 3.)

18

336.74

325.930646

3.94

π(C8-S1-C4-C5)( 22.) δ(O6-N3-C2-C4)( 21.) -τ(C4-C5)( 12.) π(C15-C2-C4)( 9.) -β(C11-Cl22-C12)( 5.) -π(H22-C11-C13-C12)( 5.) τ(S1-C2)( 4.)

19

390.42

377.887518

2.54

τ(N3-C15)( 78.) β(C17-C15-N16)( 7.) δ(C15-C21-N16-C20)( 7.) β(N3-H28-C15)( 5.)

20

394.94

382.262426

14.48

τ(N3-C15)( 25.) -δ(O6-N3-C2-C4) 22.) -β(S1-O6-C2)( 20.) -ν(S1-C2)( 6.) β(C21-C17-N16)( 4.) -β(C5-O7-C4)( 4.)

21

412.95

399.694305

0.38

τ(C9-C10)( 69.) π(C8-S1-C4-C5)( 9.) π(H26-C12-C14-C13)( 5.) π(H24-C9-C11-C10)( 3.) -π(H25-C10-C12-C11)( 3.)

22

414.95

401.630105

0.63

τ(N16-C17)( 49.) -π(C15-C17-C21)( 30.) -δ(C15-C21-N16-C20)( 3.)

23

430.71

416.884209

524

39.49

ν(C12-Cl22)( 22.) -β(C14-C10-C9)( 18.) -τ(N3-C15)( 14.) -β(C5-C2-S1)( 11.) β(S1-O6-C2)( 5.) -β(N3-H28-C15)( 4.) ν(S1-C2)( 3.)

24

453.19

438.642601

2.63

π(C8-S1-C4-C5)( 38.) τ(C9-C10)( 15.) π(H22-C11-C13-C12)( 8.) τ(N3-C15)( 7.) -τ(C4-C5)( 7.) -β(C21-C17-N16)( 6.) δ(C15-C21-N16-C20)( 4.) -τ(C9-C10)( 3.)

25

469.04

453.983816

33.21

β(C21-C17-N16)( 19.) π(C8-S1-C4-C5)( 13.) τ(N3-C15)( 10.) π(C15-C2-C4)( 7.) δ(O6-N3-C2-C4)( 7.) -π(C15-C17-C21)( 6.) -δ(C15-C21-N16-C20)( 6.) ν(S1-C2)( 5.) π(O6-S1-N3-C2)( 4.) τ(C9-C10)( 3.)

26

483.62

468.095798

3.06

δ(C15-C21-N16-C20)( 23.) β(C5-C2-S1)( 17.) -ν(S1-C5)( 7.) -β(C21-C17-N16)( 6.) -β(C5-O7-C4)( 5.) -ν(C4-C5)( 5.) -π(O6-S1-N3-C2)( 4.) β(S1-O6-C2)( 4.) δ(O6-N3-C2-C4)( 4.) ν(S1-C2)( 3.) -β(N16-C18-C17)( 3.)

27

498.22

482.227138

0.71

τ(N3-C15)( 29.) β(N16-C18-C17)( 19.) β(C17-C15-N16)( 17.) β(N3-H28-C15)( 14.) -δ(C15-C21-N16-C20)( 9.)

28

538.27

520.991533

6.81

τ(C9-C10)( 27.) π(C8-C14-C10-C9)( 24.) -π(C8-S1-C4-C5)( 19.) π(H22-C11-C13-C12)( 15.) -τ(C9-C10)( 5.)

29

579.39

560.791581

38.22

π(O6-S1-N3-C2)( 40.) β(H28-H29-C15)( 12.) τ(N3-C15)( 11.) -τ(S1-C2)( 6.) δ(O6-N3-C2-C4)( 5.) π(C15-C17-C21)( 5.)

30

606.44

586.973276

29.05

π(O6-S1-N3-C2)( 28.) β(S1-N3-C2)( 22.) ν(S1-C5)( 10.) ν(C2-N3)( 5.) δ(O6-N3-C2-C4)( 5.) ν(N3-C4)( 5.) β(H28-H29-C15)( 4.) -τ(S1-C2)( 3.)

31

619.94

600.039926

7.75

π(O6-S1-N3-C2)( 41.) β(C21-C17-N16)( 14.) -τ(S1-C2)( 11.) -δ(C15-C21-N16-C20)( 10.) τ(N3-C15)( 4.)

32

635.97

615.555363

10.55

π(O6-S1-N3-C2)( 37.) -β(C9-C11-C10)( 31.) -τ(S1-C2)( 8.) β(S1-N3-C2)( 4.)

33

656.7

635.61993

6.64

π(O6-S1-N3-C2)( 69.) -τ(S1-C2)( 13.) τ(N3-C15)( 10.)

34

675.54

653.855166

49.73

π(O6-S1-N3-C2)( 37.) τ(N3-C15)( 26.) β(C14-C10-C9)( 5.) ν(C12-Cl22)( 4.) β(N3-H28-C15)( 4.) -β(H28-H29-C15)( 3.) -τ(S1-C2)( 3.)

35

695.3

672.98087

6.14

β(C14-C8-C9)( 17.) τ(N3-C15)( 15.) ν(S1-C5)( 15.) -β(S1-N3-C2)( 10.) π(O6-S1-N3-C2)( 6.) β(N3-H28-C15)( 5.) β(S1-C8-C5)( 4.) -β(C9-C11-C10)( 4.) -β(S1-O6-C2)( 4.)

36

716.43

693.432597

3.9

τ(S1-C2)( 39.) τ(C9-C10)( 32.) π(C8-C14-C10-C9)( 8.) -π(H22-C11-C13-C12)( 6.)

37

741.09

717.301011

4.47

τ(S1-C2)( 73.) τ(N3-C15)( 9.) π(O7-C5-N3-C4)( 6.) π(C15-C2-C4)( 3.)

38

775.89

750.983931

2.33

β(N3-H28-C15)( 38.) τ(N3-C15)( 27.) -β(C2-C15-N3)( 7.) -β(S1-O6-C2)( 7.) β(C5-O7-C4)( 4.) -β(C14-C10-C9)( 3.)

39

809.18

783.205322

18.07

τ(S1-C2)( 26.) β(H28-H29-C15)( 14.) π(C15-C17-C21)( 10.) -ν(N16-C21)( 7.) -ν(N16-C17)( 7.) -π(O6-S1-N3-C2)( 7.) π(C15-C2-C4)( 7.) -ν(C15-N16)( 5.)

40

825.81

799.301499

10.95

π(H27-C9-C13-C14)( 46.) -π(H26-C12-C14-C13)( 32.) π(C8-C14-C10-C9)( 6.) τ(C9-C10)( 5.)

41

837.53

810.645287

36.17

π(H25-C10-C12-C11)( 32.) π(H24-C9-C11-C10)( 30.) τ(S1-C2)( 11.) -τ(C9-C10)( 10.) -π(C8-C14-C10-C9)( 7.)

42

856.92

829.412868

17.25

β(N3-H28-C15)( 45.) τ(N3-C15)( 32.)

43

873.09

845.063811

2.6

β(O19-H34-C20)( 13.) -β(C17-H32-C18)( 12.) -β(N16-H36-C21)( 12.) β(N16-H30-C17)( 11.) τ(N3-C15)( 5.) δ(C15-C21-N16-C20)( 5.) ν(N16-C21)( 5.) β(C2-C15-N3)( 4.) -ν(N16-C17)( 4.)

44

882.17

853.852343

858

22.51

ν(O19-C20)( 27.) ν(C18-O19)( 27.) -δ(C15-C21-N16-C20)( 5.) β(H28-H29-C15)( 5.) -ν(C15-N16)( 4.) β(N16-H36-C21)( 4.) ν(C17-C18)( 4.) β(N16-H30-C17)( 4.) ν(C20-C21)( 3.)

45

914.54

885.183266

14.48

β(N3-H28-C15)( 40.) τ(N3-C15)( 34.) β(C17-C15-N16)( 5.) -δ(C15-C21-N16-C20)( 3.) -ν(C17-C18)( 3.) ν(C20-C21)( 3.)

46

943.61

913.320119

0.57

τ(S1-C2)( 31.) -π(H25-C10-C12-C11)( 23.) -π(C8-S1-C4-C5)( 14.) π(H24-C9-C11-C10)( 8.) τ(N3-C15)( 5.) -π(H26-C12-C14-C13)( 5.) π(C8-C14-C10-C9)( 3.) -τ(C9-C10)( 3.)

47

957.33

926.599707

0.3

π(H26-C12-C14-C13)( 47.) π(H27-C9-C13-C14)( 36.) τ(C9-C10)( 8.) τ(C9-C10)( 5.)

48

964.49

933.529871

904

4.15

ν(N3-C15)( 26.) β(S1-C8-C5)( 11.) β(S1-O6-C2)( 9.) -β(H28-H29-C15)( 8.) δ(O6-N3-C2-C4)( 5.) -π(C15-C17-C21)( 5.) -ν(S1-C2)( 4.) -ν(S1-C5)( 4.) β(S1-N3-C2)( 4.) -β(N3-H28-C15)( 3.)

49

975.01

943.712179

0.07

π(H24-C9-C11-C10)( 45.) -π(H25-C10-C12-C11)( 29.) -τ(C9-C10)( 10.) -π(C8-C14-C10-C9)( 5.) -τ(S1-C2)( 3.) τ(C9-C10)( 3.)

50

989.37

957.611223

17.61

β(N3-H28-C15)( 68.) τ(N3-C15)( 21.) -β(C17-C15-N16)( 4.)

51

1022.99

990.152021

1009

69.95

ν(C17-C18)( 19.) ν(C20-C21)( 17.) -ν(O19-C20)( 12.) -ν(C18-O19)( 11.) -ν(C15-N16)( 10.) β(C21-C17-N16)( 4.) β(N3-H28-C15)( 3.) -δ(C15-C21-N16-C20)( 3.)

52

1026.07

993.133153

24.99

β(C14-C10-C9)( 61.) ν(C9-C14)( 10.) ν(C9-C10)( 9.) -ν(C12-Cl22)( 4.)

53

1050.3

1016.58537

53.17

β(C21-C17-N16)( 25.) β(N16-H30-C17)( 10.) β(N16-H36-C21)( 10.) ν(N16-C17)( 10.) ν(N16-C21)( 10.) -ν(C15-N16)( 5.) -β(O19-H34-C20)( 4.) -ν(C17-C18)( 4.) -β(C17-H32-C18)( 4.) -ν(C20-C21)( 4.) -β(C21-C17-N16)( 4.)

54

1090.63

1055.620777

74.74

β(N3-H28-C15)( 34.) τ(N3-C15)( 20.) ν(C4-C5)( 14.) β(C2-C15-N3)( 7.) β(S1-C8-C5)( 5.)

55

1104.24

1068.793896

1.27

β(N16-H30-C17)( 21.) -β(N16-H36-C21)( 21.) β(C17-H32-C18)( 16.) -β(O19-H34-C20)( 14.) -β(N3-H28-C15)( 4.) τ(N16-C17)( 4.)

56

1113.23

1077.495317

1110

102.04

ν(C12-Cl22)( 21.) -ν(C12-H23)( 20.) -ν(C11-C12)( 18.) β(C10-H25-C11)( 6.) -β(C14-C10-C9)( 5.) -β(N3-H28-C15)( 4.) -β(C12-H26-C13)( 4.) -τ(N3-C15)( 4.) -ν(C13-C14)( 3.)

57

1133.02

1096.650058

67.9

δ(C15-C21-N16-C20)( 15.) π(C15-C17-C21)( 12.) β(C17-H32-C18)( 12.) β(O19-H34-C20)( 12.) -ν(C15-N16)( 9.) -τ(N16-C17)( 8.) -β(C21-C17-N16)( 7.) β(N16-H36-C21)( 5.) β(N16-H30-C17)( 4.)

58

1146.64

1109.832856

1174

60.8

ν(O19-C20)( 18.) -ν(C18-O19)( 18.) τ(N3-C15)( 11.) ν(C17-C18)( 8.) -ν(C20-C21)( 7.) δ(C15-C21-N16-C20)( 6.) ν(N16-C21)( 5.) -ν(N16-C17)( 5.) -β(N3-H28-C15)( 3.)

59

1149.25

1112.359075

3.21

β(C10-H25-C11)( 13.) ν(C10-C11)( 11.) β(C12-H26-C13)( 11.) -β(C9-H24-C10)( 9.) β(C9-H27-C14)( 8.) -ν(C13-C14)( 8.) -ν(O19-C20)( 7.) ν(C18-O19)( 7.) β(C14-C8-C9)( 4.) β(N3-H28-C15)( 3.)

60

1166.08

1128.648832

1134

76

τ(N3-C15)( 30.) -β(N3-H28-C15)( 17.) -ν(C2-N3)( 8.) β(C17-C15-N16)( 8.) ν(N3-C4)( 6.) ν(N16-C21)( 5.) β(C2-C15-N3)( 4.) -ν(N16-C17)( 3.)

61

1181.11

1143.196369

1228

214.17

ν(C15-N16)( 27.) -β(N16-H36-C21)( 8.) -β(N16-H30-C17)( 8.) -δ(C15-C21-N16-C20)( 7.) β(C21-C17-N16)( 6.) β(N16-H36-C21)( 6.) -ν(N16-C17)( 6.) β(N16-H30-C17)( 5.) -τ(N16-C17)( 4.) β(C17-H32-C18)( 3.)

62

1216.4

1177.35356

3.53

β(C9-H24-C10)( 23.) β(C9-H27-C14)( 21.) β(C12-H26-C13)( 16.) -β(C10-H25-C11)( 14.) -ν(C13-C14)( 6.) -ν(C10-C11)( 6.) ν(C9-C10)( 4.)

63

1240.61

1200.786419

2.44

β(N16-H30-C17)( 28.) -β(N16-H36-C21)( 28.) β(C17-H32-C18)( 18.) β(O19-H34-C20)( 18.)

64

1249.71

1209.594309

11.47

β(N3-H28-C15)( 47.) -ν(C8-C9)( 8.) τ(N3-C15)( 5.) -β(C17-C15-N16)( 4.) β(C2-C15-N3)( 4.) ν(C9-C10)( 4.) -δ(C15-C21-N16-C20)( 3.)

65

1260.59

1220.125061

14.6

β(N3-H28-C15)( 41.) τ(N3-C15)( 13.) -β(N3-H28-C15)( 5.) β(C2-C15-N3)( 4.) -ν(C2-N3)( 4.) -δ(C15-C21-N16-C20)( 3.) ν(C8-C9)( 3.)

66

1320.43

1278.044197

150.6

β(N3-H28-C15)( 60.) -β(C17-C15-N16)( 10.) β(C2-C15-N3)( 5.) -ν(C2-N3)( 3.)

67

1327.73

1285.109867

214.04

β(N3-H28-C15)( 32.) ν(C9-C14)( 7.) -β(C17-C15-N16)( 5.) -ν(C9-C10)( 5.) ν(N3-C4)( 5.) -β(C14-C8-C9)( 4.) β(C9-H27-C14)( 4.) -ν(C8-C9)( 3.)

68

1330.88

1288.158752

11.28

β(O19-H34-C20)( 28.) -β(C17-H32-C18)( 27.) -β(N16-H36-C21)( 7.) -β(N16-H30-C17)( 7.) β(O19-H34-C20)( 4.) β(C17-H32-C18)( 4.) -β(C21-C17-N16)( 4.)

69

1334.44

1291.604476

1300

7

ν(C12-H23)( 18.) -ν(C11-C12)( 17.) β(C9-H24-C10)( 13.) -β(C9-H27-C14)( 12.) β(C10-H25-C11)( 10.) β(C12-H26-C13)( 8.) ν(C9-C14)( 5.) -ν(C9-C10)( 5.) β(C11-Cl22-C12)( 5.) ν(C10-C11)( 3.)

70

1340.62

1297.586098

1280

530.32

ν(N3-C4)( 14.) β(N3-H28-C15)( 11.) β(N3-H28-C15)( 10.) -ν(N3-C15)( 7.) β(C5-O7-C4)( 6.) β(S1-O6-C2)( 5.) -ν(C4-C5)( 4.) ν(C2-N3)( 4.) ν(C8-C9)( 3.)

71

1352.02

1308.620158

2.4

β(N16-H36-C21)( 20.) β(N16-H30-C17)( 19.) β(O19-H34-C20)( 11.) -β(C17-H32-C18)( 11.) -δ(C15-C21-N16-C20)( 7.) ν(C15-N16)( 7.) β(C21-C17-N16)( 5.)

72

1369.01

1325.064779

6.82

β(N3-H28-C15)( 18.) β(N16-H30-C17)( 17.) -β(N16-H36-C21)( 15.) β(N3-H28-C15)( 14.) β(O19-H34-C20)( 10.) β(C17-H32-C18)( 10.) -τ(N3-C15)( 4.) -β(C17-C15-N16)( 4.)

73

1377.31

1333.098349

15.54

ν(C13-C14)( 12.) -ν(C10-C11)( 9.) ν(C9-C10)( 9.) -ν(C5-C8)( 9.) -ν(C12-H23)( 8.) β(C12-H26-C13)( 8.) -ν(C9-C14)( 8.) ν(C11-C12)( 7.) β(C10-H25-C11)( 7.) ν(S1-C5)( 5.) -β(S1-C8-C5)( 4.)

74

1391.74

1347.065146

1.98

β(N3-H28-C15)( 45.) -τ(N3-C15)( 18.) -β(O19-H34-C20)( 8.) -β(C17-H32-C18)( 8.) β(N3-H28-C15)( 6.) β(C2-C15-N3)( 4.)

75

1418.57

1373.033903

8.74

β(N3-H28-C15)( 38.) -τ(N3-C15)( 20.) β(N16-H36-C21)( 13.) β(C17-C15-N16)( 9.) β(C17-H32-C18)( 6.)

76

1421.51

1375.879529

30.1

β(N16-H30-C17)( 23.) -β(N3-H28-C15)( 15.) -β(O19-H34-C20)( 8.) τ(N3-C15)( 7.) β(N16-H36-C21)( 6.) -δ(C15-C21-N16-C20)( 5.) β(N3-H28-C15)( 5.) -ν(N3-C4)( 3.) -ν(N16-C21)( 3.)

77

1431.07

1385.132653

1395

35.75

β(C17-H32-C18)( 26.) -β(O19-H34-C20)( 25.) -β(N3-H28-C15)( 18.)

78

1441.38

1395.111702

1405

27.52

β(N3-H28-C15)( 27.) -β(H28-H29-C15)( 13.) -β(N16-H36-C21)( 9.) -β(N16-H30-C17)( 8.) -β(O19-H34-C20)( 6.) β(C17-H32-C18)( 6.) -ν(C20-C21)( 3.)

79

1448.45

1401.954755

1423

23.89

ν(C13-C14)( 23.) -ν(C10-C11)( 23.) β(C9-H27-C14)( 13.) β(C10-H25-C11)( 10.) -β(C9-H24-C10)( 9.) -β(C14-C8-C9)( 7.) β(C12-H26-C13)( 7.)

80

1487.77

1440.012583

45.75

β(H28-H29-C15)( 68.) β(N3-H28-C15)( 11.) β(H28-H29-C15)( 7.) -β(H30-H31-C17)( 3.)

81

1496.91

1448.859189

0.06

β(H32-H33-C18)( 47.) -β(C34-H35-C20)( 42.) β(H36-H37-C21)( 4.) -β(H30-H31-C17)( 4.)

82

1503.14

1454.889206

0.33

β(H36-H37-C21)( 45.) -β(H30-H31-C17)( 43.) -β(H32-H33-C18)( 4.) β(C34-H35-C20)( 3.)

83

1509.29

1460.841791

16.21

β(C34-H35-C20)( 42.) β(H32-H33-C18)( 37.) -β(H30-H31-C17)( 4.) -β(H36-H37-C21)( 4.)

84

1519.67

1470.888593

5.58

β(H30-H31-C17)( 39.) β(H36-H37-C21)( 37.) β(C34-H35-C20)( 5.) β(H32-H33-C18)( 5.)

85

1533.47

1484.245613

89.35

β(C12-H26-C13)( 16.) -β(C10-H25-C11)( 16.) -β(C9-H24-C10)( 15.) -ν(C11-C12)( 13.) -β(C9-H27-C14)( 11.) -ν(C12-H23)( 7.) ν(C9-C10)( 7.) ν(C9-C14)( 6.) -ν(C8-C9)( 4.)

86

1607.82

1556.208978

1493

5.98

ν(C12-H23)( 19.) -ν(C9-C14)( 18.) -ν(C11-C12)( 18.) ν(C9-C10)( 13.) -β(C9-C11-C10)( 9.) β(C9-H27-C14)( 5.) -ν(C5-C8)( 3.)

87

1643.11

1590.366169

1587

134.52

ν(C10-C11)( 18.) ν(C13-C14)( 18.) β(C14-C10-C9)( 10.) -ν(C9-C10)( 9.) ν(C8-C9)( 7.) β(C9-H24-C10)( 7.) -ν(C5-C8)( 6.) β(C9-H27-C14)( 6.) -ν(C12-H23)( 4.) -ν(C9-C14)( 4.) β(C12-H26-C13)( 3.)

88

1666.71

1613.208609

1613

89.35

ν(C5-C8)( 58.) -ν(C8-C9)( 7.) ν(C10-C11)( 5.) -ν(C4-C5)( 5.) β(C14-C8-C9)( 3.) ν(C4-O7)( 3.) ν(C13-C14)( 3.)

89

1774.3

1717.34497

1692

343.63

ν(C4-O7)( 55.) -ν(C2-O6)( 14.) -β(C2-C15-N3)( 8.) -β(S1-N3-C2)( 5.) -ν(N3-C4)( 4.)

90

1833.51

1774.654329

1748

473.1

ν(C2-O6)( 63.) ν(C4-O7)( 14.) -β(S1-N3-C2)( 8.) -ν(C2-N3)( 6.)

91

2941.12

2846.710048

29.86

ν(C17-H31)( 49.) -ν(C21-H37)( 47.)

92

2946.59

2852.004461

2854

128.64

ν(C21-H37)( 49.) ν(C17-H31)( 47.)

93

2991.25

2895.230875

17.08

ν(C18-H33)( 51.) -ν(C20-H35)( 42.)

94

2997.62

2901.396398

96.06

ν(C20-H35)( 51.) ν(C18-H33)( 42.)

95

3077.89

2979.089731

23.82

ν(C15-H28)( 49.) ν(C15-H29)( 47.)

96

3097.95

2998.505805

10.39

ν(C21-H36)( 83.) -ν(C17-H30)( 12.)

97

3099.92

3000.412568

6.98

ν(C17-H30)( 83.) ν(C21-H36)( 11.)

98

3106.09

3006.384511

41.42

ν(C18-H32)( 66.) -ν(C20-H34)( 28.) -ν(C18-H33)( 4.)

99

3108.2

3008.42678

2658

43.17

ν(C20-H34)( 66.) ν(C18-H32)( 28.) -ν(C20-H35)( 3.)

100

3137.48

3036.766892

2959

2.06

ν(C15-H29)( 44.) -ν(C15-H28)( 43.) β(N3-H28-C15)( 10.)

101

3166.71

3065.058609

3010

0.59

ν(C8-H23)( 99.)

102

3193.2

3090.69828

4.51

ν(C10-H24)( 93.) -ν(C11-H25)( 5.)

103

3215.47

3112.253413

4.06

ν(C13-H26)( 53.) -ν(C14-H27)( 46.)

104

3224.72

3121.206488

3.83

ν(C11-H25)( 92.) ν(C10-H24)( 5.)

105

3229.3

3125.63947

3014

1.27

ν(C14-H27)( 52.) ν(C13-H26)( 44.)