1. R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth,
P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels,
O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski,
and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
******************************************
Gaussian 09: EM64L-G09RevA.02 11-Jun-2009
15-May-2014
******************************************
%chk=ftirone.chk
%mem=3840MB
%nproc=2
Will use up to 2 processors via shared memory.
----------------------
# hf/6-31g Opt pop=nbo
----------------------
1/18=20,19=15,38=1/1,3;
2/9=110,12=2,17=6,18=5,40=1/2;
3/5=1,6=6,11=9,16=1,25=1,30=1,71=1/1,2,3;
4//1;
5/5=2,38=5/2;
6/7=2,8=2,9=2,10=2,28=1/1,7;
7//1,2,3,16;
1/18=20,19=15/3(2);
2/9=110/2;

2. 99//99;
2/9=110/2;
3/5=1,6=6,11=9,16=1,25=1,30=1,71=1/1,2,3;
4/5=5,16=3/1;
5/5=2,38=5/2;
7//1,2,3,16;
1/18=20,19=15/3(-5);
2/9=110/2;
6/7=2,8=2,9=2,10=2,19=2,28=1/1,7;
99/9=1/99;
-----
Title
-----
Symbolic Z-matrix:
Charge = 0 Multiplicity = 1
C -2.36967 0.59208 0.91175
O -3.28943 1.22661 0.06874
C -4.58785 0.93359 0.50561
C -5.3404 2.10754 0.88689
C -4.69144 3.20111 1.52978
C -3.91111 3.93547 2.07663
C -1.63877 1.5141 1.71822
C -1.42183 2.52631 2.32648
C -3.05879 -0.51896 1.52352
O -2.50995 -1.26025 2.53953

3. H -1.57605 -1.03667 2.69367
C -4.53396 -0.3148 1.35654
H -4.9864 -1.16583 0.83834
O -5.14237 -0.14985 2.62793
H -6.10024 -0.13802 2.46975
O -6.70728 2.01883 0.82928
H -7.11922 2.85151 1.1202
C -2.77354 4.55791 2.70198
C -1.56069 3.84855 2.86587
C -0.47297 4.45742 3.4856
C -0.57524 5.77815 3.91745
C -1.75828 6.49287 3.72623
H -1.81613 7.53232 4.03469
C -2.86118 5.88062 3.13004
GradGradGradGradGradGradGradGradGradGradGradGradGradGradGradGradGradGrad
Berny optimization.
Initialization pass.
----------------------------
! Initial Parameters !
! (Angstroms and Degrees) !
-------------------------- -------------------------
-
! Name Definition Value Derivative Info.

4. !
-------------------------------------------------------------------------------
-
! R1 R(1,2) 1.3997 estimate D2E/DX2
!
! R2 R(1,7) 1.4264 estimate D2E/DX2
!
! R3 R(1,9) 1.4435 estimate D2E/DX2
!
! R4 R(2,3) 1.4009 estimate D2E/DX2
!
! R5 R(3,4) 1.4456 estimate D2E/DX2
!
! R6 R(3,12) 1.5118 estimate D2E/DX2
!
! R7 R(4,5) 1.4249 estimate D2E/DX2
!
! R8 R(4,16) 1.371 estimate D2E/DX2
!
! R9 R(5,6) 1.203 estimate D2E/DX2
!
! R10 R(6,18) 1.4396 estimate D2E/DX2
!
! R11 R(7,8) 1.2007 estimate D2E/DX2
!

5. ! R12 R(8,19) 1.4348 estimate D2E/DX2
!
! R13 R(9,10) 1.3722 estimate D2E/DX2
!
! R14 R(9,12) 1.4986 estimate D2E/DX2
!
! R15 R(10,11) 0.9726 estimate D2E/DX2
!
! R16 R(12,13) 1.0943 estimate D2E/DX2
!
! R17 R(12,14) 1.4191 estimate D2E/DX2
!
! R18 R(14,15) 0.9709 estimate D2E/DX2
!
! R19 R(16,17) 0.9735 estimate D2E/DX2
!
! R20 R(18,19) 1.4146 estimate D2E/DX2
!
! R21 R(18,24) 1.393 estimate D2E/DX2
!
! R22 R(19,20) 1.3921 estimate D2E/DX2
!
! R23 R(20,21) 1.3933 estimate D2E/DX2
!
! R24 R(21,22) 1.3953 estimate D2E/DX2

6. !
! R25 R(22,23) 1.0858 estimate D2E/DX2
!
! R26 R(22,24) 1.3952 estimate D2E/DX2
!
! A1 A(2,1,7) 112.5928 estimate D2E/DX2
!
! A2 A(2,1,9) 106.8864 estimate D2E/DX2
!
! A3 A(7,1,9) 120.1674 estimate D2E/DX2
!
! A4 A(1,2,3) 109.0495 estimate D2E/DX2
!
! A5 A(2,3,4) 113.2578 estimate D2E/DX2
!
! A6 A(2,3,12) 108.3734 estimate D2E/DX2
!
! A7 A(4,3,12) 122.7304 estimate D2E/DX2
!
! A8 A(3,4,5) 120.3409 estimate D2E/DX2
!
! A9 A(3,4,16) 117.0898 estimate D2E/DX2
!
! A10 A(5,4,16) 121.5137 estimate D2E/DX2
!

7. ! A11 A(4,5,6) 165.6964 estimate D2E/DX2
!
! A12 A(5,6,18) 166.8872 estimate D2E/DX2
!
! A13 A(1,7,8) 157.5059 estimate D2E/DX2
!
! A14 A(7,8,19) 161.7844 estimate D2E/DX2
!
! A15 A(1,9,10) 122.5925 estimate D2E/DX2
!
! A16 A(1,9,12) 108.5341 estimate D2E/DX2
!
! A17 A(10,9,12) 123.3544 estimate D2E/DX2
!
! A18 A(9,10,11) 112.1612 estimate D2E/DX2
!
! A19 A(3,12,9) 102.1406 estimate D2E/DX2
!
! A20 A(3,12,13) 111.1568 estimate D2E/DX2
!
! A21 A(3,12,14) 113.1424 estimate D2E/DX2
!
! A22 A(9,12,13) 110.7207 estimate D2E/DX2
!
! A23 A(9,12,14) 109.758 estimate D2E/DX2

8. !
! A24 A(13,12,14) 109.7183 estimate D2E/DX2
!
! A25 A(12,14,15) 106.1664 estimate D2E/DX2
!
! A26 A(4,16,17) 110.7317 estimate D2E/DX2
!
! A27 A(6,18,19) 120.7307 estimate D2E/DX2
!
! A28 A(6,18,24) 119.624 estimate D2E/DX2
!
! A29 A(19,18,24) 119.6364 estimate D2E/DX2
!
! A30 A(8,19,18) 120.1031 estimate D2E/DX2
!
! A31 A(8,19,20) 119.6576 estimate D2E/DX2
!
! A32 A(18,19,20) 120.144 estimate D2E/DX2
!
! A33 A(19,20,21) 119.6847 estimate D2E/DX2
!
! A34 A(20,21,22) 120.3512 estimate D2E/DX2
!
! A35 A(21,22,23) 119.7751 estimate D2E/DX2
!

9. ! A36 A(21,22,24) 120.2647 estimate D2E/DX2
!
! A37 A(23,22,24) 119.9577 estimate D2E/DX2
!
! A38 A(18,24,22) 119.8839 estimate D2E/DX2
!
! D1 D(7,1,2,3) -110.6946 estimate D2E/DX2
!
! D2 D(9,1,2,3) 23.3439 estimate D2E/DX2
!
! D3 D(2,1,7,8) 27.5112 estimate D2E/DX2
!
! D4 D(9,1,7,8) -99.7733 estimate D2E/DX2
!
! D5 D(2,1,9,10) -171.4123 estimate D2E/DX2
!
! D6 D(2,1,9,12) -16.9069 estimate D2E/DX2
!
! D7 D(7,1,9,10) -41.5582 estimate D2E/DX2
!
! D8 D(7,1,9,12) 112.9472 estimate D2E/DX2
!
! D9 D(1,2,3,4) 119.109 estimate D2E/DX2
!
! D10 D(1,2,3,12) -20.6094 estimate D2E/DX2

10. !
! D11 D(2,3,4,5) -36.0079 estimate D2E/DX2
!
! D12 D(2,3,4,16) 155.5635 estimate D2E/DX2
!
! D13 D(12,3,4,5) 97.1563 estimate D2E/DX2
!
! D14 D(12,3,4,16) -71.2723 estimate D2E/DX2
!
! D15 D(2,3,12,9) 9.3745 estimate D2E/DX2
!
! D16 D(2,3,12,13) -108.7455 estimate D2E/DX2
!
! D17 D(2,3,12,14) 127.2781 estimate D2E/DX2
!
! D18 D(4,3,12,9) -125.7055 estimate D2E/DX2
!
! D19 D(4,3,12,13) 116.1746 estimate D2E/DX2
!
! D20 D(4,3,12,14) -7.8018 estimate D2E/DX2
!
! D21 D(3,4,5,6) -7.1856 estimate D2E/DX2
!
! D22 D(16,4,5,6) 160.7226 estimate D2E/DX2
!

11. ! D23 D(3,4,16,17) 178.9261 estimate D2E/DX2
!
! D24 D(5,4,16,17) 10.6423 estimate D2E/DX2
!
! D25 D(4,5,6,18) -0.425 estimate D2E/DX2
!
! D26 D(5,6,18,19) -0.9938 estimate D2E/DX2
!
! D27 D(5,6,18,24) 177.919 estimate D2E/DX2
!
! D28 D(1,7,8,19) -5.8324 estimate D2E/DX2
!
! D29 D(7,8,19,18) 8.7543 estimate D2E/DX2
!
! D30 D(7,8,19,20) -167.7025 estimate D2E/DX2
!
! D31 D(1,9,10,11) -8.6605 estimate D2E/DX2
!
! D32 D(12,9,10,11) -159.4134 estimate D2E/DX2
!
! D33 D(1,9,12,3) 4.5569 estimate D2E/DX2
!
! D34 D(1,9,12,13) 122.987 estimate D2E/DX2
!
! D35 D(1,9,12,14) -115.7364 estimate D2E/DX2

12. !
! D36 D(10,9,12,3) 158.8253 estimate D2E/DX2
!
! D37 D(10,9,12,13) -82.7445 estimate D2E/DX2
!
! D38 D(10,9,12,14) 38.5321 estimate D2E/DX2
!
! D39 D(3,12,14,15) 73.8026 estimate D2E/DX2
!
! D40 D(9,12,14,15) -172.835 estimate D2E/DX2
!
! D41 D(13,12,14,15) -50.9577 estimate D2E/DX2
!
! D42 D(6,18,19,8) 4.2725 estimate D2E/DX2
!
! D43 D(6,18,19,20) -179.2881 estimate D2E/DX2
!
! D44 D(24,18,19,8) -174.6401 estimate D2E/DX2
!
! D45 D(24,18,19,20) 1.7993 estimate D2E/DX2
!
! D46 D(6,18,24,22) -179.4429 estimate D2E/DX2
!
! D47 D(19,18,24,22) -0.5181 estimate D2E/DX2
!

13. ! D48 D(8,19,20,21) 175.0657 estimate D2E/DX2
!
! D49 D(18,19,20,21) -1.3897 estimate D2E/DX2
!
! D50 D(19,20,21,22) -0.2935 estimate D2E/DX2
!
! D51 D(20,21,22,23) -177.8434 estimate D2E/DX2
!
! D52 D(20,21,22,24) 1.5806 estimate D2E/DX2
!
! D53 D(21,22,24,18) -1.1598 estimate D2E/DX2
!
! D54 D(23,22,24,18) 178.2632 estimate D2E/DX2
!
-------------------------------------------------------------------------------
-
Trust Radius=3.00D-01 FncErr=1.00D-07 GrdErr=1.00D-07
Number of steps in this run= 128 maximum allowed number of steps= 144.
GradGradGradGradGradGradGradGradGradGradGradGradGradGradGradGradGradGrad
Input orientation:
---------------------------------------------------------------------
Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
---------------------------------------------------------------------

14. 1 6 0 -2.369670 0.592080 0.911750
2 8 0 -3.289430 1.226610 0.068740
3 6 0 -4.587850 0.933590 0.505610
4 6 0 -5.340400 2.107540 0.886890
5 6 0 -4.691440 3.201110 1.529780
6 6 0 -3.911110 3.935470 2.076630
7 6 0 -1.638770 1.514100 1.718220
8 6 0 -1.421830 2.526310 2.326480
9 6 0 -3.058790 -0.518960 1.523520
10 8 0 -2.509950 -1.260250 2.539530
11 1 0 -1.576050 -1.036670 2.693670
12 6 0 -4.533960 -0.314800 1.356540
13 1 0 -4.986400 -1.165830 0.838340
14 8 0 -5.142370 -0.149850 2.627930
15 1 0 -6.100240 -0.138020 2.469750
16 8 0 -6.707280 2.018830 0.829280
17 1 0 -7.119220 2.851510 1.120200
18 6 0 -2.773540 4.557910 2.701980
19 6 0 -1.560690 3.848550 2.865870
20 6 0 -0.472970 4.457420 3.485600
21 6 0 -0.575240 5.778150 3.917450
22 6 0 -1.758280 6.492870 3.726230
23 1 0 -1.816130 7.532320 4.034690
24 6 0 -2.861180 5.880620 3.130040
---------------------------------------------------------------------

15. Distance matrix (angstroms):
1 2 3 4 5
1 C 0.000000
2 O 1.399733 0.000000
3 C 2.280768 1.400932 0.000000
4 C 3.335037 2.377369 1.445636 0.000000
5 C 3.546775 2.828236 2.490241 1.424904 0.000000
6 C 3.861507 3.428707 3.455049 2.607619 1.203015
7 C 1.426439 2.351194 3.241063 3.839967 3.492894
8 C 2.577035 3.205392 3.984471 4.195590 3.432264
9 C 1.443454 2.283986 2.341808 3.536883 4.062574
10 O 2.469913 3.591221 3.642449 4.699434 5.067763
11 H 2.541239 3.866312 4.211944 5.226934 5.386936
12 C 2.388393 2.362886 1.511775 2.595891 3.523696
13 H 3.153238 3.032451 2.162664 3.292814 4.431169
14 O 3.344189 3.446372 2.446544 2.857664 3.555025
15 H 4.108231 3.940522 2.700651 2.850499 3.744069
16 O 4.566977 3.589949 2.403017 1.370967 2.439692
17 H 5.263715 4.291056 3.234806 1.942196 2.486783
18 C 4.369879 4.277576 4.609930 3.985930 2.625509
19 C 3.882992 4.205597 4.819908 4.608002 3.464955
20 C 5.016276 5.481379 6.183038 5.997258 4.816538
21 C 6.256959 6.549497 7.156218 6.735312 5.411581
22 C 6.566157 6.592052 7.020289 6.334395 4.925800
23 H 7.630602 7.593507 7.979980 7.194259 5.770733

16. 24 C 5.755958 5.587018 5.860216 5.041268 3.618074
6 7 8 9 10
6 C 0.000000
7 C 3.339913 0.000000
8 C 2.871354 1.200672 0.000000
9 C 4.568843 2.487508 3.549373 0.000000
10 O 5.401207 3.021675 3.945559 1.372229 0.000000
11 H 5.527696 2.731641 3.585169 1.958518 0.972582
12 C 4.355602 3.443517 4.324123 1.498563 2.527837
13 H 5.358439 4.377538 5.343465 2.145598 3.005955
14 O 4.302298 3.983907 4.592943 2.386895 2.858398
15 H 4.641137 4.816535 5.385787 3.207941 3.762240
16 O 3.612196 5.170567 5.516804 4.498203 5.594184
17 H 3.518764 5.672885 5.832763 5.292431 6.337700
18 C 1.439639 3.394152 2.468910 5.219650 5.826393
19 C 2.480913 2.602471 1.434762 4.808467 5.206480
20 C 3.752124 3.625721 2.443989 5.941429 6.142970
21 C 4.232271 4.914248 3.717844 7.180008 7.428381
22 C 3.727754 5.369780 4.219727 7.463847 7.879349
23 H 4.600029 6.451082 5.304111 8.524863 8.945735
24 C 2.448598 4.749107 3.737490 6.601104 7.173848
11 12 13 14 15
11 H 0.000000
12 C 3.325394 0.000000
13 H 3.884510 1.094297 0.000000

17. 14 O 3.675515 1.419086 2.063777 0.000000
15 H 4.618009 1.929694 2.226776 0.970915 0.000000
16 O 6.256321 3.232205 3.619885 3.222927 2.776984
17 H 6.951294 4.094502 4.557125 3.897351 3.434661
18 C 5.721309 5.352811 6.413353 5.270659 5.759568
19 C 4.888278 5.334032 6.402373 5.373290 6.054516
20 C 5.659414 6.618053 7.681144 6.615575 7.335952
21 C 6.995787 7.704139 8.783969 7.593597 8.223292
22 C 7.602194 7.724261 8.798656 7.535520 8.024965
23 H 8.676610 8.725616 9.794135 8.488733 8.923943
24 C 7.049176 6.657832 7.708496 6.467033 6.866696
16 17 18 19 20
16 O 0.000000
17 H 0.973491 0.000000
18 C 5.042642 4.929378 0.000000
19 C 5.829491 5.910897 1.414587 0.000000
20 C 7.202040 7.235102 2.432443 1.392093 0.000000
21 C 7.827592 7.695031 2.792647 2.408379 1.393299
22 C 7.273373 6.985025 2.413278 2.787775 2.419294
23 H 8.037199 7.650294 3.397038 3.873184 3.400087
24 C 5.916029 5.598738 1.393010 2.427008 2.802761
21 22 23 24
21 C 0.000000
22 C 1.395340 0.000000
23 H 2.151898 1.085795 0.000000

18. 24 C 2.419925 1.395235 2.153749 0.000000
Stoichiometry C15H5O4
Framework group C1[X(C15H5O4)]
Deg. of freedom 66
Full point group C1 NOp 1
Largest Abelian subgroup C1 NOp 1
Largest concise Abelian subgroup C1 NOp 1
Standard orientation:
---------------------------------------------------------------------
Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
---------------------------------------------------------------------
1 6 0 -1.394447 -1.406297 -0.994772
2 8 0 -1.539815 -0.151123 -1.596983
3 6 0 -2.224012 0.700388 -0.719821
4 6 0 -1.454528 1.862483 -0.336030
5 6 0 -0.045925 1.762370 -0.145860
6 6 0 1.089790 1.385430 -0.022113
7 6 0 -0.041125 -1.694255 -0.647885
8 6 0 1.096191 -1.468705 -0.336034
9 6 0 -2.437168 -1.518796 -0.002987
10 8 0 -2.491257 -2.551715 0.898770
11 1 0 -1.839690 -3.246096 0.700751
12 6 0 -2.975342 -0.149101 0.279845
13 1 0 -4.053827 -0.111761 0.098291

19. 14 8 0 -2.704125 0.204086 1.627252
15 1 0 -3.170489 1.040628 1.786558
16 8 0 -2.155079 2.970012 0.066656
17 1 0 -1.548590 3.688582 0.318675
18 6 0 2.315595 0.637387 0.079835
19 6 0 2.313025 -0.772941 -0.029815
20 6 0 3.503509 -1.485255 0.085424
21 6 0 4.701207 -0.800522 0.280206
22 6 0 4.712848 0.592822 0.353890
23 1 0 5.655563 1.118744 0.470705
24 6 0 3.520256 1.311631 0.266026
---------------------------------------------------------------------
Rotational constants (GHZ): 0.7277328 0.2816499 0.2268763
Standard basis: 6-31G (6D, 7F)
The combination of multiplicity 1 and 127 electrons is impossible.
Error termination via Lnk1e in /share/apps/gaussian/g09/l301.exe at Thu May 15
17:05:53 2014.
Job cpu time: 0 days 0 hours 0 minutes 0.8 seconds.
File lengths (MBytes): RWF= 5 Int= 0 D2E= 0 Chk= 1 Scr=