Directory UMM :wiley:Public:journals:jcc:suppmat:18:
1
INPUT STRUCTURE OF CYCLOUNDECANE
11
10
8
7
6
9
1
4
2
3
Cycloundecane 68.38 kcal
0
1
1.5000000
22
1
2
3
4
5
6
1
12
1
13
2
14
5
20
5
21
6
22
9
28
9
29
10
30
1.07542
2.15456
0.10734
-0.24101
1.40716
0.29906
-1.70115
1.85339
0.24938
-2.60588
0.71004 -0.33508
-2.60587 -0.71004
0.33508
-1.70115 -1.85340 -0.24938
-0.24101 -1.40716 -0.29906
1.07543 -2.15456 -0.10735
2.07918 -1.23215
0.65815
2.76461
0.00000
0.00000
2.07918
1.23216 -0.65815
1.50051
2.48133
1.08296
0.88766
3.07339 -0.49521
-0.21659
0.75485 -0.58589
-0.12220
0.83946
1.25024
-1.79115
2.75667 -0.39728
-2.05096
2.14555
1.26566
-3.65492
1.09085 -0.30865
-2.37585
0.58262 -1.41830
-3.65492 -1.09085
0.30865
-2.37585 -0.58262
1.41830
-1.79114 -2.75667
0.39728
-2.05096 -2.14555 -1.26566
-0.21659 -0.75484
0.58589
-0.12220 -0.83946 -1.25024
0.88767 -3.07339
0.49521
1.50052 -2.48133 -1.08296
2.90604 -1.90013
1.00294
1.60000 -0.89006
1.60480
3.44981
0.41836
0.77718
3.44981 -0.41835 -0.77718
1.60000
0.89006 -1.60480
2.90604
1.90014 -1.00294
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
6
10
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
15
23
31
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
25)
26)
27)
28)
29)
30)
31)
32)
33)
5
0
9
3
7
11
0
10
16
24
32
0
11
3
7
11
0
0
1
17
25
33
33 0
1
4
8
0 0
18
26
0
1
1.0
0
4
8
19
27
2
LISTING OF THE STRUCTURE ANALYSIS OF CYCLOUNDECANE BY HUNTER
HUNTER for MM3
VERSION 3.1 DOS
CALCULATION STARTED AT 16:11:47
CHEMICAL FORMULA :
FORMULA WEIGHT
:
10/1995
DATE : 15.02.1996
C( 11) H( 22)
154.176
NAME OF MOLECULE: Cycloundecane 68.38 kcal
------------ CONNECTION TABLE -----------ATOM TYPE
#1
#2
#3
#4
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
2
1
2
3
4
5
6
7
8
9
10
1
1
2
2
3
3
4
4
5
5
6
6
7
7
8
8
9
9
10
10
11
11
11
3
4
5
6
7
8
9
10
11
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
12
14
16
18
20
22
24
26
28
30
32
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
13
15
17
19
21
23
25
27
29
31
33
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
1
1
1
1
1
1
1
1
1
1
1
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
------------------------------------------------------------------------------1 RING(S) FOUND IN CONNECTION TABLE
RING
1:
1
2
3
4
5
6
7
8
9
10
11
BRIDGE-HEAD-ATOMS:NONE
SPIRO-ATOMS:NONE
------------------------------------------------------------------------------THE STRUCTURE IS DEFINED BY
ATOMS:
ATOMS:
ATOMS:
ATOMS:
1
3
5
7
2
4
6
8
3
5
7
9
5 TORSION ANGLES
4
6
8
10
3
ATOMS:
9
10
11
1
THE MOLECULE IS A CYCLOALCANE
------------------------------------------------------------------------------THE MOLECULE HAS
0 ROTATABLE BOND(S). ROTATION ANGLE: 105.0°
------------------------------------------------------------------------------THE MOLECULE HAS
STEREO-ATOM
0 STEREOGENIC ATOM(S)
PRIORITY
CONFIGURATION
------------------------------------------------------------------------------THE MOLECULE HAS
0 STEREOGENIC DOUBLE BOND(S)
------------------------------------------------------------------------------CONJUGATED SYSTEM: NO
------------------------------------------------------------------------------FLAPPING WILL BE PERFORMED ON
ATOM
ANGLE
1
2
3
4
5
6
7
8
9
10
11
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
11 ATOMS:
------------------------------------------------------------------------------STRUCTURE FOR PERTURBATON HAS ALWAYS STEREOCHEMISTRY OF INPUT STRUCTURE
------------------------------------------------------------------------------FULL-MATRIX-NR-ALGORITHM IS USED FOR OPTIMIZATION
------------------------------------------------------------------------------MAX. CALCULATION TIME [HH:MM:SS]
3:00:00
------------------------------------------------------------------------------INITIAL ENERGY CALCULATION
HEAT OF FORMATION:
STERIC ENERGY:
-3.279 KCAL/MOL
68.384 KCAL/MOL
TIME FOR SETUP: 0.9 SECONDS
---------------- START OF ANNEALING SEQUENCE ---------------
4
-------------------------- ANNEALING ------------------------Annealing Runs
Runs at 3000.0 K
Accepted Steps
Energy Window Faults
Boltzmann Critereon Faults
Aver. Uphill Energy Diff.
:
:
:
:
:
:
10 (
0. s)
10 (
0.1 s)
10
(100.0 %)
0
( 0.0 %)
0
( 0.0 %)
-0.8 kCal
------------------ STRUCTURE PERTURBATION -----------------ATM
FLAPS
1
2
3
4
5
6
7
8
9
10
11
0
0
2
2
0
2
1
0
1
2
0
|
BOND
|
|
|
|
|
|
|
|
|
|
|
00000000000-
0
0
0
0
0
0
0
0
0
0
0
ROTATIONS
0
0
0
0
0
0
0
0
0
0
0
------------------------------ NR-OPTIMIZATION -------------------------------COUNT
ISOMER
FOUND
SE(pert.)
SE(optimized) I_FREQ
TIME
5
GLOBAL MINIMUM OF CYCLOUNDECANE
10
9
8
2
1
11
5
7
6
3
4
Cycloundecane 28.38 kcal
0
1
1.5000000
22
1
2
3
4
5
6
1
12
1
13
2
14
5
20
5
21
6
22
9
28
9
29
10
30
1.17608
0.15063 -2.22841
2.16561
0.43735 -1.07876
2.52127 -0.73871 -0.14485
1.40681 -1.29807
0.75736
0.78491 -0.26347
1.71509
-0.55092 -0.71640
2.33511
-1.75318 -0.66968
1.37022
-2.18518
0.76588
0.96254
-2.30196
1.03808 -0.55366
-0.95680
1.28037 -1.27821
-0.31030
0.00756 -1.85517
1.26152
0.97205 -2.97847
1.50611 -0.77495 -2.75534
1.81779
1.30684 -0.48162
3.12000
0.78055 -1.54625
2.92657 -1.57165 -0.76592
3.36333 -0.41642
0.51247
1.82774 -2.13107
1.36828
0.62622 -1.77400
0.13122
1.51515 -0.05337
2.53116
0.62963
0.70287
1.19324
-0.77952 -0.07606
3.21889
-0.43280 -1.75261
2.72881
-1.54815 -1.28700
0.47206
-2.61950 -1.16649
1.86743
-1.50096
1.51626
1.41750
-3.18008
0.96549
1.42680
-2.86626
0.21676 -1.05041
-2.92561
1.95472 -0.68326
-0.26146
1.79679 -0.58321
-1.12173
1.99414 -2.11925
-0.43425 -0.83514 -1.15258
-0.88013 -0.29085 -2.76651
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
6
10
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
15
23
31
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
25)
26)
27)
28)
29)
30)
31)
32)
33)
0
9
3
7
11
0
10
16
24
32
0
11
3
7
11
0
0
1
17
25
33
33 0
1
4
8
0 0
18
26
0
1
1.0
0
4
8
19
27
6
INPUT STRUCTURE OF (Z)-OCT-3-ENE
1
5
2
3
6
7
4
8
(Z)-oct-3-ene 13.56
1
1
0.0000300
1
2
3
4
1
9
1
10
4
17
5
18
-1.92830
1.70445
-2.19519
0.22854
-0.97810 -0.69887
-0.65293 -1.08765
-0.16932
0.05412
1.05014
0.61135
2.33204
0.30286
2.55810 -1.11925
-2.80409
2.33880
-1.72847
1.86900
-1.05526
2.09781
-3.04551 -0.14395
-2.53127
0.16539
-0.08610 -0.23379
-1.17355 -1.63892
-1.55970 -1.53305
0.10197 -1.90278
-0.95341
0.49466
1.14359
1.47279
3.17558
0.53902
2.42552
1.02075
3.59253 -1.23864
2.42841 -1.87894
1.87402 -1.37499
kcal
16
5
6
1
11
6
19
0.93644
1.26197
1.08139
-0.37152
-1.23807
-1.30619
-0.56753
-0.04490
1.20075
-0.14344
1.50339
0.64585
2.32405
1.55919
1.65034
-0.84171
-0.38026
-1.88144
-1.99459
-1.25876
0.27998
0.34930
-0.84781
0.79223
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
7
1(
1(
1(
1(
2(
2(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
12
20
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
0
0
0
0
24 0
1
2
7
13
21
3
8
14
22
3
8
0 0
15
23
1
1
0.2
0
4
8
16
24
7
LISTING OF THE STRUCTURE ANALYSIS OF (Z)-OCT-3-ENE BY HUNTER
HUNTER for MM3
VERSION 3.2 DOS
CALCULATION STARTED AT 16:42:48
CHEMICAL FORMULA :
FORMULA WEIGHT
:
12/1996
DATE : 07.01.1997
C( 8) H( 16)
112.128
NAME OF MOLECULE: (Z)-oct-3-ene
------------ CONNECTION TABLE -----------ATOM TYPE
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
1
1
1
1
2
2
1
1
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
#1
#2
#3
#4
2
1
2
3
4
5
6
7
1
1
1
2
2
3
3
4
4
5
6
7
7
8
8
8
9
3
4
5
6
7
8
22
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
12
14
16
18
19
20
23
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
11
13
15
17
0
0
21
24
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
------------------------------------------------------------------------------0 RING(S) FOUND IN CONNECTION TABLE
BRIDGE-HEAD-ATOMS:NONE
SPIRO-ATOMS:NONE
------------------------------------------------------------------------------THE STRUCTURE IS DEFINED BY
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
1
2
3
4
5
2
3
4
5
6
5 TORSION ANGLES
3
4
5
6
7
4
5
6
7
8
------------------------------------------------------------------------------THE MOLECULE HAS
4 ROTATABLE BOND(S). ROTATION ANGLE: 105.0°
NR.
1: 16 ATOMS AT BOND
2-
3:
NR.
2: 13 ATOMS AT BOND
3-
4:
4
21
5
24
14
22
16
15
23
17
5
24
6
16
17
6
18
7
19
8
20
18
7
19
8
20
21
22
23
8
NR.
NR.
3: 10 ATOMS AT BOND
4: 6 ATOMS AT BOND
46-
5:
7:
6
8
18
20
7
21
19
22
8
23
20
24
21
22
23
24
------------------------------------------------------------------------------THE MOLECULE HAS
STEREO-ATOM
0 STEREOGENIC ATOM(S)
PRIORITY
CONFIGURATION
------------------------------------------------------------------------------THE MOLECULE HAS
ATOMS:
4-
1 STEREOGENIC DOUBLE BOND(S)
5=
6-
7
CIS
------------------------------------------------------------------------------CONJUGATED SYSTEM: NO
------------------------------------------------------------------------------FLAPPING WILL BE PERFORMED ON
ATOM
0 ATOMS:
ANGLE
------------------------------------------------------------------------------STRUCTURE FOR PERTURBATON HAS ALWAYS STEREOCHEMISTRY OF INPUT STRUCTURE
------------------------------------------------------------------------------FULL-MATRIX-NR-ALGORITHM IS USED FOR OPTIMIZATION
------------------------------------------------------------------------------MAX. CALCULATION TIME [HH:MM:SS] 0001:30:00
------------------------------------------------------------------------------INITIAL ENERGY CALCULATION
HEAT OF FORMATION:
STERIC ENERGY:
-17.764 KCAL/MOL
13.560 KCAL/MOL
TIME FOR SETUP: 0.5 SECONDS
---------------- START OF ANNEALING SEQUENCE ---------------------------------------- ANNEALING ------------------------Annealing Runs
Runs at 3000.0 K
Accepted Steps
Energy Window Faults
Boltzmann Critereon Faults
Aver. Uphill Energy Diff.
:
:
:
:
:
:
10 (
0. s)
10 (
0.0 s)
10
(100.0 %)
0
( 0.0 %)
0
( 0.0 %)
0.8 kCal
------------------ STRUCTURE PERTURBATION -----------------ATM
0
0
FLAPS
0
0
|
BOND
|
|
23-
3
4
ROTATIONS
3
1
9
0
0
0
0
|
|
46-
5
7
2
4
------------------------------ NR-OPTIMIZATION -------------------------------COUNT
ISOMER
FOUND
SE(pert.)
SE(optimized) I_FREQ
TIME
10
GLOBAL MINIMUM OF (Z)-OCT-3-ENE
5
3
1
6
7
4
8
2
(Z)-oct-3-ene 7.65 kcal
1
1
0.0000300
16
1
2
3
4
5
6
1
9
1
10
1
11
4
17
5
18
6
19
-3.88053 -0.55405
0.45338
-2.64930 -0.45347 -0.45619
-1.51712
0.36798
0.17997
-0.28309
0.46918 -0.72958
0.81880
1.27886 -0.09235
1.94228
0.80632
0.46955
2.34949 -0.64002
0.59978
3.44830 -1.01460 -0.40194
-4.68949 -1.15207 -0.02317
-4.30235
0.44991
0.68301
-3.63418 -1.04305
1.42229
-2.94577
0.00916 -1.42595
-2.28010 -1.47910 -0.68895
-1.89085
1.39168
0.41415
-1.22406 -0.09734
1.14963
-0.56484
0.94572 -1.69634
0.07808 -0.55108 -0.98452
0.65932
2.37223 -0.08986
2.66316
1.53720
0.87825
2.71119 -0.82124
1.63797
1.47433 -1.31166
0.45891
3.74733 -2.08163 -0.29613
4.36376 -0.39840 -0.25619
3.11026 -0.86807 -1.45237
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
7
1(
1(
1(
1(
2(
2(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
12
20
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
0
0
0
0
24 0
1
2
7
13
21
3
8
14
22
3
8
0 0
15
23
1
1
0.2
0
4
8
16
24
11
INPUT STRUCTURE OF SIPHOLENOL-A-MONOACETATE
34 39
31
30
22
32
33
23
24
28 21
25
26
29
6 3
7
19
20
36
4
2
9
27
5 35
1
37
8 11
18
15
14
17
10
12
16
13
38
1
Sipholenol-A-monoacetate 143.17
13
0.0000300
55
0
1
2
3
2
4
5
35
36
2
11
10
4
6
7
8
9
8
10
12
13
14
15
18
8
15
14
16
14
17
20
26
21
28
21
29
22
30
31
32
33
23
32
34
35
37
17
38
34
39
1
3
45
4
46
6
47
6
9
53
10
54
12
55
12
16
61
16
62
18
63
18
23
69
24
70
24
71
25
28
77
28
78
29
79
29
31
85
33
86
33
87
33
5.69326
1.40702 -1.22044 C 1(
4.17182
1.60123 -1.33147 C 1(
3.91844
2.76535 -2.30507 C 1(
3.54657
1.94638
0.04923 C 1(
4.25699
1.19849
1.07074 O 75(
2.02832
1.69518
0.23853 C 1(
1.26812
0.89341 -0.82923 C 1(
1.67973 -0.58750 -1.06360 C 1(
1.07614 -0.99702 -2.43068 C 1(
3.21422 -0.61761 -1.12574 C 1(
3.64328
0.43834 -1.97542 O 6(
3.75066 -1.94855 -1.64421 C 1(
2.98540 -3.13922 -1.03624 C 1(
2.19213 -2.81119
0.24264 C 1(
1.22860 -1.55938
0.08716 C 1(
3.13197 -2.63564
1.45190 C 1(
1.39602 -3.97782
0.53518 O 6(
-0.25354 -2.02265
0.02379 C 1(
-1.34235 -0.93605
0.10520 C 1(
-2.77319 -1.53092
0.32695 C 1(
-3.94788 -1.09076 -0.64054 C 1(
-5.00558 -0.10581 -0.02127 C 1(
-4.61841
1.17328
0.76960 C 1(
-3.36045
1.05422
1.62329 C 1(
0
91 0
1
0 0
0
1
5.0
0
0
0
0
0
19
20
21
22
23
24
25
26
27
40
48
56
64
72
80
88
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
1
7
13
19
27
29
36
41
49
57
65
73
81
89
1
7
13
19
27
30
36
42
50
58
66
74
82
90
3
9
15
20
27
30
36
43
51
59
67
75
83
91
3
9
16
22
28
31
44
52
60
68
76
84
12
-3.38052
-3.14383
-3.19349
-3.38971
-4.73928
-6.01171
-5.42793
-4.67463
-3.33111
-5.48734
4.40038
3.86747
4.94753
1.96658
-5.07004
5.96313
6.16189
6.18604
2.83598
4.40451
4.31686
3.73606
1.84922
1.53248
1.34938
0.18922
1.18688
-0.01049
1.54894
3.62161
3.68948
4.83268
3.70713
2.28724
1.32074
2.56013
3.81065
3.78453
-0.41602
-0.43374
-1.32287
-1.06956
-2.64320
-5.60246
-5.45737
-3.29567
-2.46207
-3.65598
-3.47459
-3.93955
-2.20499
-4.18012
-2.90148
-2.63936
-5.60703
-4.10431
-5.13965
-6.20365
-6.99457
-6.22619
-4.72965
-2.80790
-2.63721
-3.46633
3.97878
2.78961
4.42811
-0.25251
-1.44067
-2.73513
-0.62259
-2.39958
0.48652
1.84769
2.38060
3.00413
3.41534
1.64260
3.01299
0.95466
-4.72263
3.72022
0.51430
1.26645
2.28596
2.98551
3.70446
2.54828
3.02721
1.21770
2.69153
1.44628
0.94514
-2.07563
-0.77642
-0.44499
-0.47648
-1.99248
-2.02756
-3.96271
-3.55261
-0.98313
-2.49843
-1.76499
-3.52370
-2.63753
-2.70037
-0.32603
-0.26100
-2.62266
-0.73227
1.32670
1.90553
1.12552
-0.20651
-2.57825
-3.43465
-3.24471
-0.54638
0.37079
-1.33906
-2.22515
-3.16077
-2.87488
-0.16692
0.64994
2.54472
1.72444
3.44988
2.26737
3.82068
3.24926
3.10798
3.79221
2.38983
1.80546
2.57711
-2.00269
-0.94986
-1.04412
-1.45613
-0.21394
-0.60392
0.36997
2.35424
2.64022
3.19242
0.66792
1.16452
-0.61577
-2.21910
-0.75016
-2.42218
-1.96143
-3.32049
0.20346
1.22694
0.30900
-1.79187
-0.58020
-2.65816
-2.49119
-3.27279
-0.11027
-2.75479
-1.39118
-0.83258
-1.79689
1.03787
2.39600
1.36042
1.60044
-0.89041
0.89007
-0.81574
0.94507
0.13098
0.68863
1.49546
2.33835
0.98213
3.45683
3.64154
2.14027
2.56987
-2.77954
-1.94496
-2.40495
-1.62146
-1.45592
-0.02705
-1.92030
-0.54327
-1.79339
-2.31078
0.26974
-1.05823
-1.34680
3.71522
2.40307
2.08299
C 2( 25)
C 2( 26)
C 1( 27)
C 1( 28)
C 1( 29)
C 1( 30)
C 1( 31)
C 1( 32)
C 1( 33)
O 6( 34)
C 3( 35)
C 1( 36)
O 78( 37)
H 21( 38)
H 21( 39)
H 5( 40)
H 5( 41)
H 5( 42)
H 5( 43)
H 5( 44)
H 5( 45)
H 5( 46)
H 5( 47)
H 5( 48)
H 5( 49)
H 5( 50)
H 5( 51)
H 5( 52)
H 5( 53)
H 5( 54)
H 5( 55)
H 5( 56)
H 5( 57)
H 5( 58)
H 5( 59)
H 5( 60)
H 5( 61)
H 5( 62)
H 5( 63)
H 5( 64)
H 5( 65)
H 5( 66)
H 5( 67)
H 5( 68)
H 5( 69)
H 5( 70)
H 5( 71)
H 5( 72)
H 5( 73)
H 5( 74)
H 5( 75)
H 5( 76)
H 5( 77)
H 5( 78)
H 5( 79)
H 5( 80)
H 5( 81)
H 5( 82)
H 5( 83)
H 5( 84)
H 5( 85)
H 5( 86)
H 5( 87)
H 5( 88)
H 5( 89)
H 5( 90)
H 5( 91)
13
LISTING OF THE STRUCTURE ANALYSIS OF SIPHOLENOL-A-MONOACETATE BY HUNTER
HUNTER for MM3
VERSION 3.1 DOS
CALCULATION STARTED AT 15:49:43
CHEMICAL FORMULA :
FORMULA WEIGHT
:
10/1995
DATE : 15.02.1996
C( 32) H( 54)
518.407
O(
5)
NAME OF MOLECULE: Sipholenol-A-monoacetate
------------ CONNECTION TABLE -----------ATOM TYPE
#1
#2
#3
#4
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
2
1
2
2
4
4
6
7
8
11
2
10
12
13
14
14
14
15
18
19
20
21
22
23
24
25
26
21
21
22
30
31
32
32
5
35
35
17
34
1
1
1
3
3
3
4
6
6
7
7
9
9
9
40
3
43
5
35
7
8
9
51
8
10
13
14
15
18
60
38
19
20
21
22
23
24
25
26
27
73
76
79
31
32
33
86
39
36
89
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
41
4
44
6
0
47
49
10
52
12
0
55
57
16
8
61
0
63
65
26
28
30
32
70
72
20
74
77
80
82
84
23
87
0
37
90
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
42
11
45
46
0
48
50
15
53
54
0
56
58
17
59
62
0
64
66
67
29
68
69
71
0
0
75
78
81
83
85
34
88
0
0
91
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
1
1
1
1
75
1
1
1
1
1
6
1
1
1
1
1
6
1
1
1
1
1
1
1
2
2
1
1
1
1
1
1
1
6
3
1
78
21
21
5
5
5
5
5
5
5
5
5
5
5
5
5
5
14
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
10
12
12
13
13
15
16
16
16
18
18
19
19
20
22
23
24
24
25
27
27
27
28
28
28
29
29
29
30
30
31
31
33
33
33
36
36
36
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
------------------------------------------------------------------------------4 RING(S) FOUND IN CONNECTION TABLE
RING
RING
RING
RING
1:
2:
3:
4:
4
12
21
30
2
10
20
22
11
8
26
23
10
15
25
32
8
14
24
31
7
13
23
6
22
BRIDGE-HEAD-ATOMS: 8- 10- 22- 23SPIRO-ATOMS:NONE
------------------------------------------------------------------------------THE STRUCTURE IS DEFINED BY
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
4
11
8
2
4
7
12
8
14
15
21
26
24
2
10
7
4
5
8
10
15
15
18
20
25
23
11
8
6
5
35
10
8
14
18
19
26
24
22
17 TORSION ANGLES
10
7
4
35
36
12
15
13
19
20
25
23
21
15
ATOMS:
ATOMS:
ATOMS:
ATOMS:
26
21
30
23
20
22
22
32
19
23
23
31
18
32
32
30
------------------------------------------------------------------------------THE MOLECULE HAS
5 ROTATABLE BOND(S). ROTATION ANGLE: 105.0°
NR.
NR.
NR.
1: 6 ATOMS AT BOND 4- 5:
2: 5 ATOMS AT BOND 5- 35:
3: 43 ATOMS AT BOND 15- 18:
NR.
4: 40 ATOMS AT BOND 18- 19:
NR.
5: 37 ATOMS AT BOND 19- 20:
35
36
19
25
72
34
20
30
75
86
21
77
31
39
36
37
63
27
73
84
65
68
32
87
26
78
82
37
89
64
23
74
85
66
76
69
88
67
79
83
89
90
20
30
75
86
21
77
31
39
22
80
70
90
91
65
68
32
87
26
78
82
91
66
76
69
88
67
79
83
21
77
31
39
22
80
70
26
78
82
67
79
83
22
80
70
28
81
71
29
24
33
28
81
71
29
24
33
25
72
34
27
73
84
23
74
85
28
81
71
29
24
33
25
72
34
27
73
84
23
74
85
30
75
86
68
32
87
76
69
88
------------------------------------------------------------------------------THE MOLECULE HAS
STEREO-ATOM
9 STEREOGENIC ATOM(S)
PRIORITY
4
10
8
15
14
20
23
22
32
2810141521322123-
6121581319222331-
CONFIGURATION
5
11
7
18
16
26
24
30
33
R
R
R
R
R
R
R
R
S
------------------------------------------------------------------------------THE MOLECULE HAS
ATOMS:
1 STEREOGENIC DOUBLE BOND(S)
24- 25= 26- 20
CIS
------------------------------------------------------------------------------CONJUGATED SYSTEM: NO
------------------------------------------------------------------------------FLAPPING WILL BE PERFORMED ON
ATOM
ANGLE
21
20
12
13
24
14
15
30
32
31
2
11
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
15 ATOMS:
16
4
6
7
60.0
60.0
60.0
------------------------------------------------------------------------------STRUCTURE FOR PERTURBATON HAS ALWAYS STEREOCHEMISTRY OF INPUT STRUCTURE
------------------------------------------------------------------------------FULL-MATRIX-NR-ALGORITHM IS USED FOR OPTIMIZATION
------------------------------------------------------------------------------MAX. CALCULATION TIME [HH:MM:SS]
16:00:00
------------------------------------------------------------------------------INITIAL ENERGY CALCULATION
HEAT OF FORMATION:
STERIC ENERGY:
-248.110 KCAL/MOL
143.166 KCAL/MOL
TIME FOR SETUP: 3.7 SECONDS
---------------- START OF ANNEALING SEQUENCE ---------------------------------------- ANNEALING ------------------------Annealing Runs
Runs at 3000.0 K
Accepted Steps
Energy Window Faults
Boltzmann Critereon Faults
Aver. Uphill Energy Diff.
:
:
:
:
:
:
10 (
2. s)
10 (
2.0 s)
10
(100.0 %)
0
( 0.0 %)
0
( 0.0 %)
289.8 kCal
------------------ STRUCTURE PERTURBATION -----------------ATM
21
20
12
13
24
14
15
30
32
31
2
11
4
6
7
FLAPS
|
0
0
1
1
0
2
2
2
0
0
0
2
0
0
0
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
BOND
451518190000000000-
5
35
18
19
20
0
0
0
0
0
0
0
0
0
0
ROTATIONS
2
2
3
2
1
0
0
0
0
0
0
0
0
0
0
------------------------------ NR-OPTIMIZATION -------------------------------COUNT
ISOMER
FOUND
SE(pert.)
SE(optimized) I_FREQ
TIME
17
GLOBAL MINIMUM OF SIPHOLENOL-A-MONOACETATE
39
34
32 31
30
33
22
28
23
29
21
24
20
19
25
7
26
18 15
16
8 10
13
27
14
12
17
9
38
Sipholenol-A-monoacetate
100.78 kcal
0 13
1.5000000
55
0
1
2
3
2
4
5
35
36
2
11
10
4
6
7
8
9
8
10
12
13
14
15
18
19
8
15
14
16
14
17
20
26
21
28
21
29
22
30
31
32
33
23
32
34
35
37
17
38
34
39
1
40
3
45
4
46
6
47
6
48
9
53
10
54
12
55
12
56
16
61
16
62
18
63
18
64
23
69
24
70
24
71
25
72
28
77
28
78
29
79
29
80
31
85
33
86
33
87
33
88
5.13464 -1.38180 -3.09485 C 1( 1)
5.12377 -0.60633 -1.76881 C 1( 2)
6.56416 -0.14601 -1.48256 C 1( 3)
4.61960 -1.45394 -0.58122 C 1( 4)
3.59618 -2.36257 -1.05251 O 75( 5)
4.06282 -0.61341
0.57694 C 1( 6)
2.61564 -0.11035
0.40514 C 1( 7)
2.33519
0.96833 -0.68046 C 1( 8)
2.95893
2.30774 -0.22020 C 1( 9)
2.96042
0.50910 -2.01815 C 1( 10)
4.37849
0.59628 -1.91878 O 6( 11)
2.56763
1.41160 -3.18857 C 1( 12)
1.05224
1.45425 -3.35839 C 1( 13)
0.33403
1.92748 -2.08715 C 1( 14)
0.78025
1.07263 -0.87104 C 1( 15)
-1.18442
1.83301 -2.32113 C 1( 16)
0.65981
3.30606 -1.84400 O 6( 17)
0.03620
1.51181
0.43269 C 1( 18)
-1.03132
0.49425
0.87994 C 1( 19)
-1.77123
0.89295
2.17672 C 1( 20)
-2.64224 -0.21281
2.85163 C 1( 21)
-3.82738 -0.82601
2.05212 C 1( 22)
-4.92530
0.08848
1.45188 C 1( 23)
-4.39765
1.20567
0.54060 C 1( 24)
36
37
35
5
6
4
1
2
3
11
0
0
91 0
1
0
0
0
20
21
22
23
24
1
7
13
19
27
29
36
41
49
57
65
73
81
89
1
7
13
19
27
30
36
42
50
58
66
74
82
90
3
9
15
20
27
30
36
0 0
0
1
5.0
0
25
26
27
43
51
59
67
75
83
91
3
9
16
22
28
31
44
52
60
68
76
84
18
-3.67243
-2.53596
-1.94074
-1.71310
-3.22273
-3.48517
-4.73438
-5.78089
-6.79505
-6.50282
3.33230
2.22990
3.93096
0.35454
-7.12211
4.12251
5.55149
5.75940
6.63624
7.26206
6.95896
5.48490
4.09516
4.74013
2.29044
1.96061
2.84052
2.51782
4.05094
2.62662
2.96375
3.03130
0.69109
0.79228
0.43697
-1.77308
-1.51816
-1.49227
0.75106
-0.43229
-0.52632
-1.75528
-0.96611
-4.36355
-5.53656
-5.25636
-3.75068
-4.14654
-1.92723
-0.89434
-2.51277
-2.26223
-1.25723
-0.87482
-3.76182
-2.42516
-3.94645
-2.59971
-3.26559
-5.11327
-4.47130
-7.48431
-6.30720
-7.42255
2.01861
2.49504
1.29583
2.31162
2.19715
3.40409
-1.37494
0.38440
-1.80454
-1.83595
-0.93783
-0.36610
-1.76002
-3.45665
-4.27293
-3.71983
3.83057
-1.21709
-1.70475
-0.76799
-2.29887
0.44276
-1.00604
0.49956
-2.04371
-1.23263
0.24173
0.28378
-0.99094
3.12056
2.68060
2.21863
-0.53193
2.44063
1.02809
0.43579
2.11341
0.03501
2.27692
0.77879
2.36862
1.65403
2.50758
-0.48567
0.35650
1.12594
-1.46105
0.54953
1.68266
0.79387
3.30677
3.26770
3.58768
4.33519
-2.13810
-1.91174
-1.01597
-0.37969
0.80035
1.20561
-1.48193
-2.82223
-2.87112
-1.43374
0.35848
0.15692
-1.17021
-5.16436
-4.61917
-3.67759
1.27588
1.97843
2.66697
3.29291
4.16313
0.89751
-0.02026
0.66408
-0.32898
1.60081
-0.29030
-0.87637
0.73302
-2.57159
2.06979
-3.41802
-3.92315
-3.02316
-0.54257
-1.38468
-2.29769
-0.21204
1.50254
0.78499
1.39434
0.21879
-0.96477
0.72823
-0.03594
-2.25587
-3.04660
-4.12642
-3.62793
-4.21743
-1.10024
-1.49071
-2.43614
-3.24574
1.26922
0.28006
1.02898
0.05234
2.91633
2.80277
2.26180
0.01702
-0.26142
1.21166
3.77082
2.33994
2.46136
3.88797
2.43446
3.93037
4.76589
4.81796
3.97068
0.31499
1.29293
-0.16717
-1.02381
0.15733
-1.17880
-0.77242
-0.25686
-1.89707
-0.95011
C 2( 25)
C 2( 26)
C 1( 27)
C 1( 28)
C 1( 29)
C 1( 30)
C 1( 31)
C 1( 32)
C 1( 33)
O 6( 34)
C 3( 35)
C 1( 36)
O 78( 37)
H 21( 38)
H 21( 39)
H 5( 40)
H 5( 41)
H 5( 42)
H 5( 43)
H 5( 44)
H 5( 45)
H 5( 46)
H 5( 47)
H 5( 48)
H 5( 49)
H 5( 50)
H 5( 51)
H 5( 52)
H 5( 53)
H 5( 54)
H 5( 55)
H 5( 56)
H 5( 57)
H 5( 58)
H 5( 59)
H 5( 60)
H 5( 61)
H 5( 62)
H 5( 63)
H 5( 64)
H 5( 65)
H 5( 66)
H 5( 67)
H 5( 68)
H 5( 69)
H 5( 70)
H 5( 71)
H 5( 72)
H 5( 73)
H 5( 74)
H 5( 75)
H 5( 76)
H 5( 77)
H 5( 78)
H 5( 79)
H 5( 80)
H 5( 81)
H 5( 82)
H 5( 83)
H 5( 84)
H 5( 85)
H 5( 86)
H 5( 87)
H 5( 88)
H 5( 89)
H 5( 90)
H 5( 91)
INPUT STRUCTURE OF CYCLOUNDECANE
11
10
8
7
6
9
1
4
2
3
Cycloundecane 68.38 kcal
0
1
1.5000000
22
1
2
3
4
5
6
1
12
1
13
2
14
5
20
5
21
6
22
9
28
9
29
10
30
1.07542
2.15456
0.10734
-0.24101
1.40716
0.29906
-1.70115
1.85339
0.24938
-2.60588
0.71004 -0.33508
-2.60587 -0.71004
0.33508
-1.70115 -1.85340 -0.24938
-0.24101 -1.40716 -0.29906
1.07543 -2.15456 -0.10735
2.07918 -1.23215
0.65815
2.76461
0.00000
0.00000
2.07918
1.23216 -0.65815
1.50051
2.48133
1.08296
0.88766
3.07339 -0.49521
-0.21659
0.75485 -0.58589
-0.12220
0.83946
1.25024
-1.79115
2.75667 -0.39728
-2.05096
2.14555
1.26566
-3.65492
1.09085 -0.30865
-2.37585
0.58262 -1.41830
-3.65492 -1.09085
0.30865
-2.37585 -0.58262
1.41830
-1.79114 -2.75667
0.39728
-2.05096 -2.14555 -1.26566
-0.21659 -0.75484
0.58589
-0.12220 -0.83946 -1.25024
0.88767 -3.07339
0.49521
1.50052 -2.48133 -1.08296
2.90604 -1.90013
1.00294
1.60000 -0.89006
1.60480
3.44981
0.41836
0.77718
3.44981 -0.41835 -0.77718
1.60000
0.89006 -1.60480
2.90604
1.90014 -1.00294
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
6
10
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
15
23
31
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
25)
26)
27)
28)
29)
30)
31)
32)
33)
5
0
9
3
7
11
0
10
16
24
32
0
11
3
7
11
0
0
1
17
25
33
33 0
1
4
8
0 0
18
26
0
1
1.0
0
4
8
19
27
2
LISTING OF THE STRUCTURE ANALYSIS OF CYCLOUNDECANE BY HUNTER
HUNTER for MM3
VERSION 3.1 DOS
CALCULATION STARTED AT 16:11:47
CHEMICAL FORMULA :
FORMULA WEIGHT
:
10/1995
DATE : 15.02.1996
C( 11) H( 22)
154.176
NAME OF MOLECULE: Cycloundecane 68.38 kcal
------------ CONNECTION TABLE -----------ATOM TYPE
#1
#2
#3
#4
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
2
1
2
3
4
5
6
7
8
9
10
1
1
2
2
3
3
4
4
5
5
6
6
7
7
8
8
9
9
10
10
11
11
11
3
4
5
6
7
8
9
10
11
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
12
14
16
18
20
22
24
26
28
30
32
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
13
15
17
19
21
23
25
27
29
31
33
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
1
1
1
1
1
1
1
1
1
1
1
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
------------------------------------------------------------------------------1 RING(S) FOUND IN CONNECTION TABLE
RING
1:
1
2
3
4
5
6
7
8
9
10
11
BRIDGE-HEAD-ATOMS:NONE
SPIRO-ATOMS:NONE
------------------------------------------------------------------------------THE STRUCTURE IS DEFINED BY
ATOMS:
ATOMS:
ATOMS:
ATOMS:
1
3
5
7
2
4
6
8
3
5
7
9
5 TORSION ANGLES
4
6
8
10
3
ATOMS:
9
10
11
1
THE MOLECULE IS A CYCLOALCANE
------------------------------------------------------------------------------THE MOLECULE HAS
0 ROTATABLE BOND(S). ROTATION ANGLE: 105.0°
------------------------------------------------------------------------------THE MOLECULE HAS
STEREO-ATOM
0 STEREOGENIC ATOM(S)
PRIORITY
CONFIGURATION
------------------------------------------------------------------------------THE MOLECULE HAS
0 STEREOGENIC DOUBLE BOND(S)
------------------------------------------------------------------------------CONJUGATED SYSTEM: NO
------------------------------------------------------------------------------FLAPPING WILL BE PERFORMED ON
ATOM
ANGLE
1
2
3
4
5
6
7
8
9
10
11
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
90.0
11 ATOMS:
------------------------------------------------------------------------------STRUCTURE FOR PERTURBATON HAS ALWAYS STEREOCHEMISTRY OF INPUT STRUCTURE
------------------------------------------------------------------------------FULL-MATRIX-NR-ALGORITHM IS USED FOR OPTIMIZATION
------------------------------------------------------------------------------MAX. CALCULATION TIME [HH:MM:SS]
3:00:00
------------------------------------------------------------------------------INITIAL ENERGY CALCULATION
HEAT OF FORMATION:
STERIC ENERGY:
-3.279 KCAL/MOL
68.384 KCAL/MOL
TIME FOR SETUP: 0.9 SECONDS
---------------- START OF ANNEALING SEQUENCE ---------------
4
-------------------------- ANNEALING ------------------------Annealing Runs
Runs at 3000.0 K
Accepted Steps
Energy Window Faults
Boltzmann Critereon Faults
Aver. Uphill Energy Diff.
:
:
:
:
:
:
10 (
0. s)
10 (
0.1 s)
10
(100.0 %)
0
( 0.0 %)
0
( 0.0 %)
-0.8 kCal
------------------ STRUCTURE PERTURBATION -----------------ATM
FLAPS
1
2
3
4
5
6
7
8
9
10
11
0
0
2
2
0
2
1
0
1
2
0
|
BOND
|
|
|
|
|
|
|
|
|
|
|
00000000000-
0
0
0
0
0
0
0
0
0
0
0
ROTATIONS
0
0
0
0
0
0
0
0
0
0
0
------------------------------ NR-OPTIMIZATION -------------------------------COUNT
ISOMER
FOUND
SE(pert.)
SE(optimized) I_FREQ
TIME
5
GLOBAL MINIMUM OF CYCLOUNDECANE
10
9
8
2
1
11
5
7
6
3
4
Cycloundecane 28.38 kcal
0
1
1.5000000
22
1
2
3
4
5
6
1
12
1
13
2
14
5
20
5
21
6
22
9
28
9
29
10
30
1.17608
0.15063 -2.22841
2.16561
0.43735 -1.07876
2.52127 -0.73871 -0.14485
1.40681 -1.29807
0.75736
0.78491 -0.26347
1.71509
-0.55092 -0.71640
2.33511
-1.75318 -0.66968
1.37022
-2.18518
0.76588
0.96254
-2.30196
1.03808 -0.55366
-0.95680
1.28037 -1.27821
-0.31030
0.00756 -1.85517
1.26152
0.97205 -2.97847
1.50611 -0.77495 -2.75534
1.81779
1.30684 -0.48162
3.12000
0.78055 -1.54625
2.92657 -1.57165 -0.76592
3.36333 -0.41642
0.51247
1.82774 -2.13107
1.36828
0.62622 -1.77400
0.13122
1.51515 -0.05337
2.53116
0.62963
0.70287
1.19324
-0.77952 -0.07606
3.21889
-0.43280 -1.75261
2.72881
-1.54815 -1.28700
0.47206
-2.61950 -1.16649
1.86743
-1.50096
1.51626
1.41750
-3.18008
0.96549
1.42680
-2.86626
0.21676 -1.05041
-2.92561
1.95472 -0.68326
-0.26146
1.79679 -0.58321
-1.12173
1.99414 -2.11925
-0.43425 -0.83514 -1.15258
-0.88013 -0.29085 -2.76651
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
6
10
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
15
23
31
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
25)
26)
27)
28)
29)
30)
31)
32)
33)
0
9
3
7
11
0
10
16
24
32
0
11
3
7
11
0
0
1
17
25
33
33 0
1
4
8
0 0
18
26
0
1
1.0
0
4
8
19
27
6
INPUT STRUCTURE OF (Z)-OCT-3-ENE
1
5
2
3
6
7
4
8
(Z)-oct-3-ene 13.56
1
1
0.0000300
1
2
3
4
1
9
1
10
4
17
5
18
-1.92830
1.70445
-2.19519
0.22854
-0.97810 -0.69887
-0.65293 -1.08765
-0.16932
0.05412
1.05014
0.61135
2.33204
0.30286
2.55810 -1.11925
-2.80409
2.33880
-1.72847
1.86900
-1.05526
2.09781
-3.04551 -0.14395
-2.53127
0.16539
-0.08610 -0.23379
-1.17355 -1.63892
-1.55970 -1.53305
0.10197 -1.90278
-0.95341
0.49466
1.14359
1.47279
3.17558
0.53902
2.42552
1.02075
3.59253 -1.23864
2.42841 -1.87894
1.87402 -1.37499
kcal
16
5
6
1
11
6
19
0.93644
1.26197
1.08139
-0.37152
-1.23807
-1.30619
-0.56753
-0.04490
1.20075
-0.14344
1.50339
0.64585
2.32405
1.55919
1.65034
-0.84171
-0.38026
-1.88144
-1.99459
-1.25876
0.27998
0.34930
-0.84781
0.79223
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
7
1(
1(
1(
1(
2(
2(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
12
20
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
0
0
0
0
24 0
1
2
7
13
21
3
8
14
22
3
8
0 0
15
23
1
1
0.2
0
4
8
16
24
7
LISTING OF THE STRUCTURE ANALYSIS OF (Z)-OCT-3-ENE BY HUNTER
HUNTER for MM3
VERSION 3.2 DOS
CALCULATION STARTED AT 16:42:48
CHEMICAL FORMULA :
FORMULA WEIGHT
:
12/1996
DATE : 07.01.1997
C( 8) H( 16)
112.128
NAME OF MOLECULE: (Z)-oct-3-ene
------------ CONNECTION TABLE -----------ATOM TYPE
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
1
1
1
1
2
2
1
1
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
#1
#2
#3
#4
2
1
2
3
4
5
6
7
1
1
1
2
2
3
3
4
4
5
6
7
7
8
8
8
9
3
4
5
6
7
8
22
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
12
14
16
18
19
20
23
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
11
13
15
17
0
0
21
24
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
------------------------------------------------------------------------------0 RING(S) FOUND IN CONNECTION TABLE
BRIDGE-HEAD-ATOMS:NONE
SPIRO-ATOMS:NONE
------------------------------------------------------------------------------THE STRUCTURE IS DEFINED BY
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
1
2
3
4
5
2
3
4
5
6
5 TORSION ANGLES
3
4
5
6
7
4
5
6
7
8
------------------------------------------------------------------------------THE MOLECULE HAS
4 ROTATABLE BOND(S). ROTATION ANGLE: 105.0°
NR.
1: 16 ATOMS AT BOND
2-
3:
NR.
2: 13 ATOMS AT BOND
3-
4:
4
21
5
24
14
22
16
15
23
17
5
24
6
16
17
6
18
7
19
8
20
18
7
19
8
20
21
22
23
8
NR.
NR.
3: 10 ATOMS AT BOND
4: 6 ATOMS AT BOND
46-
5:
7:
6
8
18
20
7
21
19
22
8
23
20
24
21
22
23
24
------------------------------------------------------------------------------THE MOLECULE HAS
STEREO-ATOM
0 STEREOGENIC ATOM(S)
PRIORITY
CONFIGURATION
------------------------------------------------------------------------------THE MOLECULE HAS
ATOMS:
4-
1 STEREOGENIC DOUBLE BOND(S)
5=
6-
7
CIS
------------------------------------------------------------------------------CONJUGATED SYSTEM: NO
------------------------------------------------------------------------------FLAPPING WILL BE PERFORMED ON
ATOM
0 ATOMS:
ANGLE
------------------------------------------------------------------------------STRUCTURE FOR PERTURBATON HAS ALWAYS STEREOCHEMISTRY OF INPUT STRUCTURE
------------------------------------------------------------------------------FULL-MATRIX-NR-ALGORITHM IS USED FOR OPTIMIZATION
------------------------------------------------------------------------------MAX. CALCULATION TIME [HH:MM:SS] 0001:30:00
------------------------------------------------------------------------------INITIAL ENERGY CALCULATION
HEAT OF FORMATION:
STERIC ENERGY:
-17.764 KCAL/MOL
13.560 KCAL/MOL
TIME FOR SETUP: 0.5 SECONDS
---------------- START OF ANNEALING SEQUENCE ---------------------------------------- ANNEALING ------------------------Annealing Runs
Runs at 3000.0 K
Accepted Steps
Energy Window Faults
Boltzmann Critereon Faults
Aver. Uphill Energy Diff.
:
:
:
:
:
:
10 (
0. s)
10 (
0.0 s)
10
(100.0 %)
0
( 0.0 %)
0
( 0.0 %)
0.8 kCal
------------------ STRUCTURE PERTURBATION -----------------ATM
0
0
FLAPS
0
0
|
BOND
|
|
23-
3
4
ROTATIONS
3
1
9
0
0
0
0
|
|
46-
5
7
2
4
------------------------------ NR-OPTIMIZATION -------------------------------COUNT
ISOMER
FOUND
SE(pert.)
SE(optimized) I_FREQ
TIME
10
GLOBAL MINIMUM OF (Z)-OCT-3-ENE
5
3
1
6
7
4
8
2
(Z)-oct-3-ene 7.65 kcal
1
1
0.0000300
16
1
2
3
4
5
6
1
9
1
10
1
11
4
17
5
18
6
19
-3.88053 -0.55405
0.45338
-2.64930 -0.45347 -0.45619
-1.51712
0.36798
0.17997
-0.28309
0.46918 -0.72958
0.81880
1.27886 -0.09235
1.94228
0.80632
0.46955
2.34949 -0.64002
0.59978
3.44830 -1.01460 -0.40194
-4.68949 -1.15207 -0.02317
-4.30235
0.44991
0.68301
-3.63418 -1.04305
1.42229
-2.94577
0.00916 -1.42595
-2.28010 -1.47910 -0.68895
-1.89085
1.39168
0.41415
-1.22406 -0.09734
1.14963
-0.56484
0.94572 -1.69634
0.07808 -0.55108 -0.98452
0.65932
2.37223 -0.08986
2.66316
1.53720
0.87825
2.71119 -0.82124
1.63797
1.47433 -1.31166
0.45891
3.74733 -2.08163 -0.29613
4.36376 -0.39840 -0.25619
3.11026 -0.86807 -1.45237
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0
7
2
7
1(
1(
1(
1(
2(
2(
1(
1(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
5(
8
12
20
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
0
0
0
0
24 0
1
2
7
13
21
3
8
14
22
3
8
0 0
15
23
1
1
0.2
0
4
8
16
24
11
INPUT STRUCTURE OF SIPHOLENOL-A-MONOACETATE
34 39
31
30
22
32
33
23
24
28 21
25
26
29
6 3
7
19
20
36
4
2
9
27
5 35
1
37
8 11
18
15
14
17
10
12
16
13
38
1
Sipholenol-A-monoacetate 143.17
13
0.0000300
55
0
1
2
3
2
4
5
35
36
2
11
10
4
6
7
8
9
8
10
12
13
14
15
18
8
15
14
16
14
17
20
26
21
28
21
29
22
30
31
32
33
23
32
34
35
37
17
38
34
39
1
3
45
4
46
6
47
6
9
53
10
54
12
55
12
16
61
16
62
18
63
18
23
69
24
70
24
71
25
28
77
28
78
29
79
29
31
85
33
86
33
87
33
5.69326
1.40702 -1.22044 C 1(
4.17182
1.60123 -1.33147 C 1(
3.91844
2.76535 -2.30507 C 1(
3.54657
1.94638
0.04923 C 1(
4.25699
1.19849
1.07074 O 75(
2.02832
1.69518
0.23853 C 1(
1.26812
0.89341 -0.82923 C 1(
1.67973 -0.58750 -1.06360 C 1(
1.07614 -0.99702 -2.43068 C 1(
3.21422 -0.61761 -1.12574 C 1(
3.64328
0.43834 -1.97542 O 6(
3.75066 -1.94855 -1.64421 C 1(
2.98540 -3.13922 -1.03624 C 1(
2.19213 -2.81119
0.24264 C 1(
1.22860 -1.55938
0.08716 C 1(
3.13197 -2.63564
1.45190 C 1(
1.39602 -3.97782
0.53518 O 6(
-0.25354 -2.02265
0.02379 C 1(
-1.34235 -0.93605
0.10520 C 1(
-2.77319 -1.53092
0.32695 C 1(
-3.94788 -1.09076 -0.64054 C 1(
-5.00558 -0.10581 -0.02127 C 1(
-4.61841
1.17328
0.76960 C 1(
-3.36045
1.05422
1.62329 C 1(
0
91 0
1
0 0
0
1
5.0
0
0
0
0
0
19
20
21
22
23
24
25
26
27
40
48
56
64
72
80
88
1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)
20)
21)
22)
23)
24)
1
7
13
19
27
29
36
41
49
57
65
73
81
89
1
7
13
19
27
30
36
42
50
58
66
74
82
90
3
9
15
20
27
30
36
43
51
59
67
75
83
91
3
9
16
22
28
31
44
52
60
68
76
84
12
-3.38052
-3.14383
-3.19349
-3.38971
-4.73928
-6.01171
-5.42793
-4.67463
-3.33111
-5.48734
4.40038
3.86747
4.94753
1.96658
-5.07004
5.96313
6.16189
6.18604
2.83598
4.40451
4.31686
3.73606
1.84922
1.53248
1.34938
0.18922
1.18688
-0.01049
1.54894
3.62161
3.68948
4.83268
3.70713
2.28724
1.32074
2.56013
3.81065
3.78453
-0.41602
-0.43374
-1.32287
-1.06956
-2.64320
-5.60246
-5.45737
-3.29567
-2.46207
-3.65598
-3.47459
-3.93955
-2.20499
-4.18012
-2.90148
-2.63936
-5.60703
-4.10431
-5.13965
-6.20365
-6.99457
-6.22619
-4.72965
-2.80790
-2.63721
-3.46633
3.97878
2.78961
4.42811
-0.25251
-1.44067
-2.73513
-0.62259
-2.39958
0.48652
1.84769
2.38060
3.00413
3.41534
1.64260
3.01299
0.95466
-4.72263
3.72022
0.51430
1.26645
2.28596
2.98551
3.70446
2.54828
3.02721
1.21770
2.69153
1.44628
0.94514
-2.07563
-0.77642
-0.44499
-0.47648
-1.99248
-2.02756
-3.96271
-3.55261
-0.98313
-2.49843
-1.76499
-3.52370
-2.63753
-2.70037
-0.32603
-0.26100
-2.62266
-0.73227
1.32670
1.90553
1.12552
-0.20651
-2.57825
-3.43465
-3.24471
-0.54638
0.37079
-1.33906
-2.22515
-3.16077
-2.87488
-0.16692
0.64994
2.54472
1.72444
3.44988
2.26737
3.82068
3.24926
3.10798
3.79221
2.38983
1.80546
2.57711
-2.00269
-0.94986
-1.04412
-1.45613
-0.21394
-0.60392
0.36997
2.35424
2.64022
3.19242
0.66792
1.16452
-0.61577
-2.21910
-0.75016
-2.42218
-1.96143
-3.32049
0.20346
1.22694
0.30900
-1.79187
-0.58020
-2.65816
-2.49119
-3.27279
-0.11027
-2.75479
-1.39118
-0.83258
-1.79689
1.03787
2.39600
1.36042
1.60044
-0.89041
0.89007
-0.81574
0.94507
0.13098
0.68863
1.49546
2.33835
0.98213
3.45683
3.64154
2.14027
2.56987
-2.77954
-1.94496
-2.40495
-1.62146
-1.45592
-0.02705
-1.92030
-0.54327
-1.79339
-2.31078
0.26974
-1.05823
-1.34680
3.71522
2.40307
2.08299
C 2( 25)
C 2( 26)
C 1( 27)
C 1( 28)
C 1( 29)
C 1( 30)
C 1( 31)
C 1( 32)
C 1( 33)
O 6( 34)
C 3( 35)
C 1( 36)
O 78( 37)
H 21( 38)
H 21( 39)
H 5( 40)
H 5( 41)
H 5( 42)
H 5( 43)
H 5( 44)
H 5( 45)
H 5( 46)
H 5( 47)
H 5( 48)
H 5( 49)
H 5( 50)
H 5( 51)
H 5( 52)
H 5( 53)
H 5( 54)
H 5( 55)
H 5( 56)
H 5( 57)
H 5( 58)
H 5( 59)
H 5( 60)
H 5( 61)
H 5( 62)
H 5( 63)
H 5( 64)
H 5( 65)
H 5( 66)
H 5( 67)
H 5( 68)
H 5( 69)
H 5( 70)
H 5( 71)
H 5( 72)
H 5( 73)
H 5( 74)
H 5( 75)
H 5( 76)
H 5( 77)
H 5( 78)
H 5( 79)
H 5( 80)
H 5( 81)
H 5( 82)
H 5( 83)
H 5( 84)
H 5( 85)
H 5( 86)
H 5( 87)
H 5( 88)
H 5( 89)
H 5( 90)
H 5( 91)
13
LISTING OF THE STRUCTURE ANALYSIS OF SIPHOLENOL-A-MONOACETATE BY HUNTER
HUNTER for MM3
VERSION 3.1 DOS
CALCULATION STARTED AT 15:49:43
CHEMICAL FORMULA :
FORMULA WEIGHT
:
10/1995
DATE : 15.02.1996
C( 32) H( 54)
518.407
O(
5)
NAME OF MOLECULE: Sipholenol-A-monoacetate
------------ CONNECTION TABLE -----------ATOM TYPE
#1
#2
#3
#4
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
2
1
2
2
4
4
6
7
8
11
2
10
12
13
14
14
14
15
18
19
20
21
22
23
24
25
26
21
21
22
30
31
32
32
5
35
35
17
34
1
1
1
3
3
3
4
6
6
7
7
9
9
9
40
3
43
5
35
7
8
9
51
8
10
13
14
15
18
60
38
19
20
21
22
23
24
25
26
27
73
76
79
31
32
33
86
39
36
89
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
41
4
44
6
0
47
49
10
52
12
0
55
57
16
8
61
0
63
65
26
28
30
32
70
72
20
74
77
80
82
84
23
87
0
37
90
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
42
11
45
46
0
48
50
15
53
54
0
56
58
17
59
62
0
64
66
67
29
68
69
71
0
0
75
78
81
83
85
34
88
0
0
91
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
1
1
1
1
75
1
1
1
1
1
6
1
1
1
1
1
6
1
1
1
1
1
1
1
2
2
1
1
1
1
1
1
1
6
3
1
78
21
21
5
5
5
5
5
5
5
5
5
5
5
5
5
5
14
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
10
12
12
13
13
15
16
16
16
18
18
19
19
20
22
23
24
24
25
27
27
27
28
28
28
29
29
29
30
30
31
31
33
33
33
36
36
36
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
------------------------------------------------------------------------------4 RING(S) FOUND IN CONNECTION TABLE
RING
RING
RING
RING
1:
2:
3:
4:
4
12
21
30
2
10
20
22
11
8
26
23
10
15
25
32
8
14
24
31
7
13
23
6
22
BRIDGE-HEAD-ATOMS: 8- 10- 22- 23SPIRO-ATOMS:NONE
------------------------------------------------------------------------------THE STRUCTURE IS DEFINED BY
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
ATOMS:
4
11
8
2
4
7
12
8
14
15
21
26
24
2
10
7
4
5
8
10
15
15
18
20
25
23
11
8
6
5
35
10
8
14
18
19
26
24
22
17 TORSION ANGLES
10
7
4
35
36
12
15
13
19
20
25
23
21
15
ATOMS:
ATOMS:
ATOMS:
ATOMS:
26
21
30
23
20
22
22
32
19
23
23
31
18
32
32
30
------------------------------------------------------------------------------THE MOLECULE HAS
5 ROTATABLE BOND(S). ROTATION ANGLE: 105.0°
NR.
NR.
NR.
1: 6 ATOMS AT BOND 4- 5:
2: 5 ATOMS AT BOND 5- 35:
3: 43 ATOMS AT BOND 15- 18:
NR.
4: 40 ATOMS AT BOND 18- 19:
NR.
5: 37 ATOMS AT BOND 19- 20:
35
36
19
25
72
34
20
30
75
86
21
77
31
39
36
37
63
27
73
84
65
68
32
87
26
78
82
37
89
64
23
74
85
66
76
69
88
67
79
83
89
90
20
30
75
86
21
77
31
39
22
80
70
90
91
65
68
32
87
26
78
82
91
66
76
69
88
67
79
83
21
77
31
39
22
80
70
26
78
82
67
79
83
22
80
70
28
81
71
29
24
33
28
81
71
29
24
33
25
72
34
27
73
84
23
74
85
28
81
71
29
24
33
25
72
34
27
73
84
23
74
85
30
75
86
68
32
87
76
69
88
------------------------------------------------------------------------------THE MOLECULE HAS
STEREO-ATOM
9 STEREOGENIC ATOM(S)
PRIORITY
4
10
8
15
14
20
23
22
32
2810141521322123-
6121581319222331-
CONFIGURATION
5
11
7
18
16
26
24
30
33
R
R
R
R
R
R
R
R
S
------------------------------------------------------------------------------THE MOLECULE HAS
ATOMS:
1 STEREOGENIC DOUBLE BOND(S)
24- 25= 26- 20
CIS
------------------------------------------------------------------------------CONJUGATED SYSTEM: NO
------------------------------------------------------------------------------FLAPPING WILL BE PERFORMED ON
ATOM
ANGLE
21
20
12
13
24
14
15
30
32
31
2
11
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
60.0
15 ATOMS:
16
4
6
7
60.0
60.0
60.0
------------------------------------------------------------------------------STRUCTURE FOR PERTURBATON HAS ALWAYS STEREOCHEMISTRY OF INPUT STRUCTURE
------------------------------------------------------------------------------FULL-MATRIX-NR-ALGORITHM IS USED FOR OPTIMIZATION
------------------------------------------------------------------------------MAX. CALCULATION TIME [HH:MM:SS]
16:00:00
------------------------------------------------------------------------------INITIAL ENERGY CALCULATION
HEAT OF FORMATION:
STERIC ENERGY:
-248.110 KCAL/MOL
143.166 KCAL/MOL
TIME FOR SETUP: 3.7 SECONDS
---------------- START OF ANNEALING SEQUENCE ---------------------------------------- ANNEALING ------------------------Annealing Runs
Runs at 3000.0 K
Accepted Steps
Energy Window Faults
Boltzmann Critereon Faults
Aver. Uphill Energy Diff.
:
:
:
:
:
:
10 (
2. s)
10 (
2.0 s)
10
(100.0 %)
0
( 0.0 %)
0
( 0.0 %)
289.8 kCal
------------------ STRUCTURE PERTURBATION -----------------ATM
21
20
12
13
24
14
15
30
32
31
2
11
4
6
7
FLAPS
|
0
0
1
1
0
2
2
2
0
0
0
2
0
0
0
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
BOND
451518190000000000-
5
35
18
19
20
0
0
0
0
0
0
0
0
0
0
ROTATIONS
2
2
3
2
1
0
0
0
0
0
0
0
0
0
0
------------------------------ NR-OPTIMIZATION -------------------------------COUNT
ISOMER
FOUND
SE(pert.)
SE(optimized) I_FREQ
TIME
17
GLOBAL MINIMUM OF SIPHOLENOL-A-MONOACETATE
39
34
32 31
30
33
22
28
23
29
21
24
20
19
25
7
26
18 15
16
8 10
13
27
14
12
17
9
38
Sipholenol-A-monoacetate
100.78 kcal
0 13
1.5000000
55
0
1
2
3
2
4
5
35
36
2
11
10
4
6
7
8
9
8
10
12
13
14
15
18
19
8
15
14
16
14
17
20
26
21
28
21
29
22
30
31
32
33
23
32
34
35
37
17
38
34
39
1
40
3
45
4
46
6
47
6
48
9
53
10
54
12
55
12
56
16
61
16
62
18
63
18
64
23
69
24
70
24
71
25
72
28
77
28
78
29
79
29
80
31
85
33
86
33
87
33
88
5.13464 -1.38180 -3.09485 C 1( 1)
5.12377 -0.60633 -1.76881 C 1( 2)
6.56416 -0.14601 -1.48256 C 1( 3)
4.61960 -1.45394 -0.58122 C 1( 4)
3.59618 -2.36257 -1.05251 O 75( 5)
4.06282 -0.61341
0.57694 C 1( 6)
2.61564 -0.11035
0.40514 C 1( 7)
2.33519
0.96833 -0.68046 C 1( 8)
2.95893
2.30774 -0.22020 C 1( 9)
2.96042
0.50910 -2.01815 C 1( 10)
4.37849
0.59628 -1.91878 O 6( 11)
2.56763
1.41160 -3.18857 C 1( 12)
1.05224
1.45425 -3.35839 C 1( 13)
0.33403
1.92748 -2.08715 C 1( 14)
0.78025
1.07263 -0.87104 C 1( 15)
-1.18442
1.83301 -2.32113 C 1( 16)
0.65981
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C 2( 26)
C 1( 27)
C 1( 28)
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C 1( 31)
C 1( 32)
C 1( 33)
O 6( 34)
C 3( 35)
C 1( 36)
O 78( 37)
H 21( 38)
H 21( 39)
H 5( 40)
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