supporting information - connecting repositoriesplanar t1 state geometries described by (i) a...

Supporting Information� Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013

Aromaticity Effects on the Profiles of the Lowest Triplet-State Potential-Energy Surfaces for Rotation about the C=C Bonds of Olefins with Five-Membered Ring Substituents: An Example of the Impact of Baird�s Rule

Jun Zhu ,[a, b] Heather A. Fogarty,[a] Helene Mçllerstedt,[c] Maria Brink,[c] andHenrik Ottosson*[a]

chem_201300008_sm_miscellaneous_information.pdf

S1

An analysis of the correlation between excitation localization and T1 PES profile

Figure S1: Energy changes along the T1 PESs (∆E(T1) = E(T1;twisted) - E(T1;planar)) (kcal mol-1) plotted

against the degree of (anti)aromaticity at the planar T1 structure (NICS(T1;planar,1)zz) (ppm) for set A

olefins CH2=CH(C4H3X) (X = CH+, SiH+, BH, AlH, CH2, SiH2, O, S, NH, and CH-). The solid line

displays the least-squares fit against all ten data points whereas the dashed line displays a fit which

excludes the data points of A7 (X = O) and A9 (X = NH). Results from M06-2X/6-311++G(d,p) and

GIAO/M06-2X/6-311++G(d,p)//M06-2X/6-311++G(d,p) calculations.

As can be seen in Figure S1, the correlation between ∆E(T1) and the aromaticity of the planar T1 olefin,

NICS(T1;1)zz, is weakened by the inclusion of two olefins, A7 (X = O) and A9 (X = NH), as these two

species are more aromatic at their planar T1 structures than could be anticipated based on Baird’s rule on

T1 state antiaromaticity of 6π-electron cycles. With A7 and A9 removed from data used in the least-

squares fit, an r2 value of 0.941 is found for a linear fit (see dashed line of Figure S1). A similar yet

stronger deviation is observed for B7 – B9 (vide infra), and this feature is related to where in the molecule

S2

it is most favorable to distribute the two unpaired same-spin electrons of the triplet biradical. It is

noteworthy that none of the five-ring substituents -C4H3X are antiaromatic in the T1 state because the

NICS(1)zz values are negative for each of A1 – A10. The rings should instead be categorized as either

aromatic or nonaromatic.


against the olefinic C=C bond length (Å) for the planar T1 structures of set A olefins CH2=CH(C4H3X) (X

= CH+, SiH+, BH, AlH, CH2, SiH2, O, S, NH, and CH-). Results from M06-2X/6-311++G(d,p) and


In the T1 state, the olefin bond lengths of A1 – A4 are short (1.357 - 1.373 Å, Figure S2) because the

triplet excitation is nearly fully localized to the ring which then becomes aromatic. In contrast, species A7

– A10 have long olefin bonds in the T1 state (1.435 - 1.461 Å, Figure S2) because the antiaromatic 6π-

electron rings force the triplet excitation to be distributed over both the olefinic C=C bond and the ring. In

S3

terms of the olefinic C=C bond length, A5 and A6 with X = CH2 and SiH2 have bond lengths which are in

between those of the olefins with 4n and 4n+2 π-electron substituents, respectively. And once again,

olefin A6 tends toward the olefins with T1 state aromatic 4π-electron substituents whereas olefin A5 tends

toward the olefins with 6π-electron substituents.

In Figure S3 it is seen that olefins B7 – B9 have NICS(T1;planar;1)zz values which are typical of

aromatic species, although these compounds in T1 should be influenced by antiaromaticity according to

Baird’s rule. Indeed, if the data points of B7 – B9 are excluded from the least-squares fit in Figure S3, an

r2 of 0.928 is obtained for a linear fit of the remaining seven data points. This finding strongly resembles

the observation made based on Figure S1.

Even though A9 in Figure S1 is an outlier, a comparison of B9 with A9 gives an explanation to the

exceptionally poor correlation for the complete set B. For planar A9 in the T1 state, the spin density reveal

that the triplet biradical character is distributed both to the C7 atom and the five-membered ring, whereas

in planar B9 it is almost fully localized to the olefinic C=C bond so that the pyrrole-ring can regain 6π-

electron (S0) aromaticity (for spin densities, see Fig. S7). This is also reflected in the NICS(T1;1)zz values

of A9 and B9 which are -6.6 and -15.7 ppm, respectively (in S0 the corresponding NICS(S0;1)zz values are

-27.8 and -28.0 ppm). Thus, the pyrrole-rings in the planar T1 structures of A9 and B9 both have some

influence of S0 aromaticity, however, this influence is greater in B9. As a result, the aromaticity gain upon

twist about the C=C bond in the T1 state of B9 is smaller than in A9 (-9.1 vs. -15.6 ppm, respectively) as

seen in Figures 3 and 6. Clearly, there is a competition between two limiting resonance structures from the

planar T1 state geometries described by (i) a markedly stabilized 6π-electron closed-shell aromatic ring

and a triplet biradical olefin bond with strong Pauli repulsion between the two adjacent same-spin

electrons, and (ii) a destabilized antiaromatic triplet biradical 6π-electron ring and a strong olefin π-bond.

This competition will be determined by the relative magnitudes of the stabilizing and destabilizing factors

in the two situations, and in B7 – B9 the first situation prevails. The extent of coupling between the ring

S4

and the olefin is dictated by the lobe sizes of the HOMO and LUMO in the S0 state (or equivalently, the

two SOMOs of the T1 state) at the C2 and C3 atoms of five-ring substituents, i.e., the connection points to

the olefin.


against the degrees of (anti)aromaticity of the planar T1 structures (NICS(T1;planar,1)zz) (ppm) of set B

olefins CH2=CH(C4H3X) (X = CH+, SiH+, BH, AlH, CH2, SiH2, O, S, NH, and CH-). The solid line

displays the least-squares fit against all ten data points whereas the dashed line displays a fit which

excludes the data points of B7 (X = O), B8 (X = S), and B9 (X = NH). Results from M06-2X/6-

311++G(d,p) and GIAO/M06-2X/6-311++G(d,p)//M06-2X/6-311++G(d,p) calculations.

With regard to the correlation between ∆E(T1) and the olefinic C=C bond lengths, the correlation

displayed in Figure S3 is negligible when compared to that of Figure S1. In this case, one contributing

factor which reduces the correlation is found through a comparison of B6 and A6 (X = SiH2) as there is a

large difference in olefinic C=C bond length in the two species (1.383 Å in A6 vs. 1.353 Å in B6). It is

S5

noteworthy that despite the longer C=C bond in A6 the rotational barrier in the T1 state is even higher for

A6 than for B6. The spin density distributions in the two olefins reveal a significant spin density increase

on the C2 from 0.54 electron in A6 to 0.94 electron in B6 suggesting a triplet excitation almost fully

localized to the ring in the latter olefin. As a consequence, the olefinic C=C bond in the planar T1 structure

of B6 has similar length as in the olefins with 4π-electron substituents, and it is even shorter than in B1

(1.353 vs. 1.367 Å). Interestingly though, the ∆E(T1) of B6 and B1 differ by more than 20 kcal/mol,

although the olefinic C=C bond is longer in the latter compound.


against the olefinic C=C bond length (Å) in the planar T1 structures of set B olefins CH2=CH(C4H3X) (X

= CH+, SiH+, BH, AlH, CH2, SiH2, O, S, NH, and CH-). Results from M06-2X/6-311++G(d,p) and


S6

With regard to the spin density distribution it could be noted that the spin density of the ring is

reflected in the NICS values, and in that way also reflect the degree of triplet state aromaticity. E.g., all set

A olefins with 4π-electron substituents (A1 – A4) prefer planar olefin structures in T1 state because these

structures allow the biradical triplet aromatic character to localize to the ring in accordance with Baird’s

rule. The spin densities in the rings of A1 – A4 (1.610 – 1.864, Table S2) are therefore much higher than

in A7 – A10 with 6π-electron substituents (0.738 – 1.110), and the olefins A5 and A6 have intermediate

values (1.326 and 1.558, respectively). The general tendency for the triplet state is; the larger the spin

density in a ring the higher the aromaticity of that ring which strongly points to the importance of T1 state

aromaticity. Therefore, the spin density in the ring has similar correlation against the energy difference

between planar and twisted olefin structures in T1 (∆E(T1)) as the NICS values, and a moderate correlation

is found between the spin density in the ring and ∆E(T1) (linear fit; r2 = 0.799), which is slightly better

than that between ∆E(T1) and the NICS value of the ring (linear fit; r2 = 0.726).

S7

Table S1. Calculated energies (kcal mol-1), NICS values (ppm), and olefinic C=C bond lengths (Å) at M062X/6-311++G(d,p) level for sets A and B compounds. .

S0 T1(planar) T1(perpendicular) X

E/G NICS(S0;1)zz E NICS(T1;1)zz C6=C7 E/G NICS(T1;1)zz

∆E(T1)/∆G(T1) ∆NICS(T1;1)zz

A1* CH+ 0.0/0.0 80.2 2.8/1.9 -16.1 1.367 28.1/25.4 2.9 25.3/23.5 19.0

A2 SiH+ 0.0/0.0 38.1 11.4/10.3 -14.0 1.373 32.6/30.2 -0.9 21.2/19.9 13.1

A3 BH 0.0/0.0 34.3 17.4/16.6 -15.1 1.357 38.6/35.5 1.5 21.2/18.9 16.6

A4 AlH 0.0/0.0 13 34.2/32.2 -8.6 1.367 48.3/44.8 3.4 14.1/12.6 12.0

A5 CH2 0.0/0.0 -8.3 47.5/44.2 -2.2 1.399 52.4/47.9 -6.1 4.9/3.7 -3.9

A6 SiH2 0.0/0.0 2.5 41.6/39.0 -3.4 1.383 50.1/46.1 0.1 8.5/7.1 3.5

A7 O 0.0/0.0 -24.3 60.9/56.7 -5.0 1.448 57.3/53.0 -19.1 -3.6/-3.7 -14.1

A8 S 0.0/0.0 -23.9 58.6/55.2 -1.3 1.435 55.7/52.2 -18.5 -2.9/-2.9 -17.2

A9 NH 0.0/0.0 -27.8 63.5/59.2 -6.6 1.461 56.5/53.2 -22.2 -7.0/-6.0 -15.6

A10* CH- 0.0/0.0 -27.6 62.2/57.8 -0.2 1.459 58.9/54.8 -21.0 -3.3/-3.0 -20.8

B2 SiH+ 0.0/0.0 23.7 23.4/21.6 -15.2 1.362 42.8/39.6 4.4 19.4/18.0 19.6

B3 BH 0.0/0.0 28.5 24.1/22.4 -17.8 1.343 43.6/40.5 3.6 19.5/18.2 21.4

B4 AlH 0.0/0.0 11.0 40.7/39.1 -12.2 1.345 51.6/48.6 3.1 10.9/9.6 15.3

B5 CH2 0.0/0.0 -10.9 58.6/53.9 -0.5 1.394 57.0/53.1 -8.6 -1.6/-0.9 -8.1

B6 SiH2 0.0/0.0 0.1 50.3/46.5 -3.6 1.353 54.5/50.8 -1.1 4.2/4.2 2.5

B7 O 0.0/0.0 -24.6 70.3/65.5 -11.2 1.483 59.7/55.9 -21.8 -10.6/-9.6 -10.6

B8 S 0.0/0.0 -25.5 68.7/64.2 -7.0 1.474 58.9/55.1 -21.8 -9.8/-9.1 -14.8

B9 NH 0.0/0.0 -28.0 70.9/66.7 -15.7 1.494 59.9/56.6 -24.8 -11.0/-10.1 -9.1

* B1 and B10 are omitted as they are same with A1 and A10.

S8

Table S2. Calculated spin densities at the two olefinic carbons (Colefin) and in the rings of the set A olefins

at M062X/6-311++G(d,p) level.

T1(planar) T1(perpendicular) X

Colefin Ring Colefin Ring

A1 CH+ 0.487 1.610 1.022 1.057

A2 SiH+ 0.399 1.702 0.971 1.105

A3 BH 0.256 1.836 1.057 1.042

A4 AlH 0.229 1.864 1.138 0.930

A5 CH2 0.674 1.326 1.441 0.583

A6 SiH2 0.462 1.558 1.316 0.720

A7 O 1.153 0.974 1.658 0.377

A8 S 1.010 1.110 1.643 0.400

A9 NH 1.269 0.865 1.666 0.367

A10 CH- 1.383 0.738 1.598 0.404

S9

HC

S0 T1-planar T1-twisted

H

H

HC

HH

HC

HH

++ +

1.421

1.4371.391

1.421 1.438

1.409

1.367

1.411

1.448

1.357

1.4541.4501.410

1.396

1.345

1.4521.407

1.3601.4861.334

1.524

HSi

HH

HSi

HH

HSi

HH

+

+ +

1.399

1.4501.400

1.805 1.823

1.404

1.373

1.408

1.449

1.355

1.4591.8351.789

1.397

1.503

1.3481.450

1.3361.8551.796

1.354

HB

HH

HB

HH

HB

HH

1.378

1.4561.430

1.541 1.554

1.420

1.357

1.393

1.462

1.346

1.4661.5791.536

1.407

1.503

1.3461.454

1.3371.6011.570

1.344

HAl

H

H

HAl

HH

HAl

HH

1.373

1.4691.438

1.929 1.949

1.408

1.367

1.417

1.447

1.352

1.4691.9671.932

1.389

1.496

1.3501.456

1.3361.9691.945

1.347

A1

A2

A3

A4

H2C

HH

H2C

HH

H2C

HH

1.364

1.4741.421

1.503 1.517

1.369

1.399

1.420

1.421

1.362

1.4651.5181.503

1.365

1.464

1.3521.454

1.3351.5061.502

1.344

A5

S10

Figure S5: Optimized bond lengths (Å) at M062X/6-311++G(d,p) level for a series of five-membered

ring substituented set A olefins, CH2=CH(C4H4X) (X = CH+, SiH+, BH, AlH, CH2, SiH2, O, S, CH-, and

NH).

S12

Figure S6: Optimized bond lengths (Å) at M062X/6-311++G(d,p) level for a series of five-membered

ring substituented set B olefins, CH2=CH(C4H4X) (X = CH+, SiH+, BH, AlH, CH2, SiH2, O, S, CH-, and

NH).

S13

Figure S7: Spin densities on carbon and nitrogen atoms of planar olefins A9 and B9 in triplet state.

Complete Gaussian 09 reference (reference 44)

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V.

Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov,

J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida,

T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M.

Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K.

Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M.

Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O.

Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G.

Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B.

Foresman, J. V. Ortiz, J. Cioslowski, D. Fox,. Gaussian 09, Revision A.1; Gaussian, Inc., Wallingford, CT,

2009. Table S3. Calculated relative energies of A1, A2 and A10 in gas phase and in THF solvent phase. Calculations performed with the SCRF-PCM model as described in Computational Methods.

S0 T1(planar) T1(perpendicular) Species

X

Gas phase THF Gas phase THF Gas phase THF

A1 CH+ 0.0/0.0 0.0/0.0 2.8/1.9 3.0/2.3 28.1/25.4 27.0/23.9

A2 SiH+ 0.0/0.0 0.0/0.0 11.4/10.3 14.6/13.6 32.6/30.2 34.5/31.5

A10 CH- 0.0/0.0 0.0/0.0 62.2/57.8 62.7/58.4 58.9/54.8 56.4/51.9

S14

Cartesian coordinates for all the compounds calculated in this study

A1-S0 Cs symmetry, NIMAG=0 E = -270.5255447 a.u.

C -0.43451600 -1.87156400 0.00000000

C -1.73529700 -1.07768200 0.00000000

C -1.44713400 0.23559300 0.00000000

C 0.00000000 0.34977900 0.00000000

H -0.38530400 -2.95165500 0.00000000

H -2.71964700 -1.52842800 0.00000000

H -2.13011200 1.07128700 0.00000000

C 0.68918400 1.57642900 0.00000000

H 0.11173200 2.49420800 0.00000000

C 2.04902200 1.61693000 0.00000000

H 2.65162900 0.71530200 0.00000000

H 2.58019700 2.56347300 0.00000000

H 1.63915800 -1.25247900 0.00000000

C 0.58746600 -1.01477000 0.00000000

A1-T1-planar Cs symmetry, NIMAG=0 E = -270.5210658 a.u. C -0.40018400 -1.92669800 0.00000000

C -1.63643300 -1.28964100 0.00000000

C -1.41574000 0.11378300 0.00000000

C 0.00000000 0.35767500 0.00000000

H -0.23223200 -2.99446100 0.00000000

H -2.60393000 -1.77135400 0.00000000

H -2.17953500 0.88061500 0.00000000

C 0.60272800 1.63071600 0.00000000

H -0.05751700 2.49224600 0.00000000

C 1.95501000 1.83359800 0.00000000

H 2.66267500 1.01281900 0.00000000

H 2.36303100 2.83646800 0.00000000

H 1.68404900 -1.14012100 0.00000000

C 0.62186300 -0.93880200 0.00000000

A1-T1-twisted Cs symmetry, NIMAG=1 E = -270.4807636 a.u. C 0.49790700 -1.88905900 0.00000000

C 1.70758100 -1.19263400 0.00000000

C -0.56374900 -0.96047300 0.00000000

C 1.43586900 0.19212300 0.00000000

C 0.00000000 0.37588300 0.00000000

C -0.67118100 1.55536200 0.00000000

C -2.12041000 1.67794300 0.00000000

H 0.38620700 -2.96451000 0.00000000

H 2.69432700 -1.63486300 0.00000000

H -1.62168900 -1.19130100 0.00000000

H 2.17073100 0.98731000 0.00000000

H -0.07485700 2.47237400 0.00000000

H -2.63541400 1.88805900 0.93149100

H -2.63541400 1.88805900 -0.93149100

A2-S0

Cs symmetry, NIMAG=0 E = -521.9157265 a.u. C -1.08996100 -1.89743600 0.00000000

C -1.92737700 -0.83338500 0.00000000

C -1.34414900 0.55183500 0.00000000

C 0.00000000 0.65849700 0.00000000

H -1.40486500 -2.93019100 0.00000000

H -3.00821200 -0.94436800 0.00000000

H -2.00733500 1.41078900 0.00000000

C 0.80218400 1.86697000 0.00000000

H 0.25560600 2.80553900 0.00000000

C 2.13836300 1.86884800 0.00000000

H 2.72254500 0.95282000 0.00000000

H 2.69837200 2.79511100 0.00000000

H 1.87143400 -1.71096100 0.00000000

Si 0.52843500 -1.11933700 0.00000000

A2-T1-planar Cs symmetry, NIMAG=0 E = -521.8975502 a.u. C 0.89232500 -1.93699600 0.00000000

C 1.88263500 -0.94755800 0.00000000

C 1.43454300 0.37737900 0.00000000

C 0.00000000 0.58957000 0.00000000

H 1.12892600 -2.99294100 0.00000000

H 2.93900100 -1.18767600 0.00000000

H 2.11815900 1.21984200 0.00000000

C -0.55368400 1.87970500 0.00000000

H 0.13188600 2.72368400 0.00000000

C -1.90148700 2.13930400 0.00000000

H -2.63680900 1.34138900 0.00000000

H -2.27478900 3.15527100 0.00000000

H -2.08366700 -1.57329000 0.00000000

Si -0.70347900 -1.09247900 0.00000000


C 1.94313200 -0.81983900 0.00000000

C 1.44314700 0.49617200 0.00000000

C 0.00000000 0.62164900 0.00000000

H 1.31351400 -2.90055200 0.00000000

H 3.01097200 -1.00763500 0.00000000

H 2.09208700 1.36493100 0.00000000

C -0.68052600 1.79316500 0.00000000

H -0.10337300 2.72398000 0.00000000

C -2.13553700 1.89831100 0.00000000

H -2.65029000 2.11712300 0.92963100

H -2.65029000 2.11712300 -0.92963100

H -1.96409000 -1.66334500 0.00000000

Si -0.61032900 -1.10854000 0.00000000


C -0.44087600 -2.09639300 0.00000000

C -1.57719100 -1.37955700 0.00000000

C -1.31794100 0.10137000 0.00000000

C 0.00000000 0.37392300 0.00000000

H -0.41878200 -3.17755100 0.00000000

H -2.58610700 -1.78144600 0.00000000

H -2.11962200 0.83410400 0.00000000

C 0.57842800 1.70787500 0.00000000

H -0.11829900 2.54433300 0.00000000

C 1.89181500 1.95597200 0.00000000

H 2.61627400 1.14916500 0.00000000

H 2.27444000 2.96906200 0.00000000

B 0.72979200 -1.05084300 0.00000000

H 1.89772900 -1.26259700 0.00000000


C 1.39219000 -1.54555100 0.00000000

C 1.36580400 -0.16779000 0.00000000

C 0.00000000 0.33588800 0.00000000

H -0.10691600 -3.15149500 0.00000000

H 2.30165200 -2.13427500 0.00000000

H 2.24602800 0.46653700 0.00000000

C -0.28971800 1.72589700 0.00000000

H 0.54792000 2.42164700 0.00000000

C -1.54827700 2.23405700 0.00000000

H -2.41055500 1.57758300 0.00000000

H -1.72604300 3.30187200 0.00000000

B -0.93121500 -0.90792400 0.00000000

H -2.11774600 -0.94451900 0.00000000

A3-T1-twisted Cs symmetry, NIMAG=1 E = -257.5030906 a.u. C -1.85067400 0.94307000 0.00002100

C -2.02908000 -0.45234500 0.00001800

C -0.81853200 -1.14221800 -0.00002200

C 0.30505100 -0.20623000 -0.00004300

H -2.69613800 1.62004800 0.00005200

H -2.99225700 -0.95116100 0.00005100

H -0.71923700 -2.22176400 -0.00002500

C 1.59830500 -0.57824900 -0.00002600

H 1.83682900 -1.64766300 0.00001000

C 2.73380700 0.34975100 0.00002300

H 3.21158100 0.63625700 0.92859500

H 3.21127000 0.63686800 -0.92851600

B -0.34218400 1.23371100 -0.00000600

H 0.22560500 2.27619300 0.00002900

A4-S0 Cs symmetry, NIMAG=0 E = -475.1443517 a.u. C 0.97545500 -2.06354200 0.00000000

C 1.83750800 -1.02796400 0.00000000

C 1.32876000 0.37895000 0.00000000

C 0.00000000 0.61876700 0.00000000

H 1.35805400 -3.07687800 0.00000000

H 2.91849400 -1.16176900 0.00000000

H 2.06356600 1.18502200 0.00000000

C -0.54433000 1.96947700 0.00000000

H 0.17293400 2.79114800 0.00000000

C -1.84986000 2.25461400 0.00000000

H -2.59672200 1.46633300 0.00000000

H -2.20885900 3.27646900 0.00000000

H -2.24777600 -1.72508200 0.00000000

Al -0.76499200 -1.19515800 0.00000000


C 1.83609800 -1.03194300 0.00000000

C 1.43691100 0.28145400 0.00000000

C 0.00000000 0.58481000 0.00000000

H 1.16711600 -3.08802400 0.00000000

H 2.89493800 -1.27572100 0.00000000

H 2.16720600 1.08801900 0.00000000

C -0.41974900 1.92931500 0.00000000

H 0.34432000 2.70878400 0.00000000

C -1.72662100 2.33063100 0.00000000

H -2.53227000 1.60398900 0.00000000

H -1.99835000 3.37839700 0.00000000

H -2.37911200 -1.61150400 0.00000000

Al -0.87638200 -1.15554000 0.00000000


C 1.88122900 -0.95235800 0.00000000

C 1.42684000 0.39001500 0.00000000

C 0.00000000 0.62783400 0.00000000

H 1.36563500 -3.01576300 0.00000000

H 2.95558100 -1.12786500 0.00000000

H 2.13730900 1.21328800 0.00000000

C -0.53072000 1.87130600 0.00000000

H 0.13966300 2.73952500 0.00000000

C -1.97161300 2.15608100 0.00000000

H -2.49152800 2.36967800 0.92679200

H -2.49152800 2.36967800 -0.92679200

H -2.24978400 -1.71961700 0.00000000

Al -0.77282400 -1.18120000 0.00000000

A5-S0 Cs symmetry, NIMAG=0 E = -271.4481473 a.u. C -1.81612800 -0.83086300 -0.00004900

C -2.02891200 0.49610200 -0.00008600

C -0.73895300 1.18858000 0.00011200

C 0.26475600 0.28232100 0.00003500

H -2.56955800 -1.60615000 0.00009200

H -2.99178500 0.98897500 -0.00014600

H -0.61156900 2.26397300 0.00028800

C 1.68957900 0.57062500 -0.00008400

H 1.95737800 1.62453500 -0.00025300

C 2.65713600 -0.34986100 0.00001500

H 2.43177000 -1.41121800 0.00018000

H 3.70248200 -0.06807900 -0.00009200

C -0.33774200 -1.09781200 0.00000500

H -0.02864900 -1.67317700 0.88041800

H -0.02848600 -1.67341400 -0.88017700

A5-T1-planar Cs symmetry, NIMAG=0 E = -271.3724653 a.u. C 1.74218200 0.90682200 -0.00002200

C 2.02093600 -0.48624300 -0.00001200

C 0.86279400 -1.20653200 0.00002200

C -0.28788200 -0.28523900 0.00001500

H 2.47965100 1.69587500 -0.00003900

H 3.01733500 -0.90753500 -0.00002800

H 0.77380600 -2.28399600 0.00004600

C -1.61390400 -0.62564100 -0.00001800

H -1.86636800 -1.68274800 -0.00005000

C -2.65958700 0.30425100 -0.00000400

H -2.46359800 1.36888500 0.00003700

H -3.69239900 -0.01463200 -0.00003200

C 0.25613900 1.13084200 0.00001800

H -0.08622000 1.69728200 0.87849500

H -0.08627100 1.69731100 -0.87842000

A5-T1-twisted Cs symmetry, NIMAG=0 E = -271.3646600 a.u. C -1.75541300 -0.90198300 0.00001600

C -2.03833800 0.43355600 -0.00003100

C -0.83840300 1.19301700 -0.00004800

C 0.27779800 0.31342100 -0.00001000

H -2.47608100 -1.70744700 0.00002100

H -3.03318800 0.85927400 -0.00005900

H -0.77189300 2.27229600 -0.00008100

C 1.59780200 0.64905600 -0.00002700

C 2.68616100 -0.33135000 0.00000600

H 3.14561200 -0.65902600 0.92627800

H 3.14516200 -0.65959800 -0.92628800

H 1.85634600 1.70855800 -0.00004800

C -0.26622200 -1.10387500 0.00007200

H 0.07690200 -1.66264600 -0.87816200

H 0.07682400 -1.66245500 0.87846900


Si -0.47339500 -1.21027200 0.00006800

C -2.13042100 -0.34219500 -0.00001800

C -1.88343700 0.97979700 -0.00003900

C -0.46433800 1.40089000 -0.00003900

C 0.46951300 0.42477700 -0.00000700

C 1.90317500 0.67794300 -0.00003300

C 2.83843100 -0.27524900 -0.00003100

H -3.13678400 -0.73974200 -0.00000500

H -2.66538500 1.73421100 -0.00005900

H -0.20914600 2.45838200 -0.00007100

H 2.21130600 1.72258400 -0.00005600

H 2.57324400 -1.32848500 -0.00000900

H 3.89413600 -0.03437000 -0.00005200

H -0.21873200 -2.03216700 1.20503400

H -0.21863800 -2.03239000 -1.20472500

A6-T1-planar Cs symmetry, NIMAG=0 E = -522.7548033 a.u. Si -0.39300300 -1.25327900 0.00009000

C -2.06237500 -0.43518600 -0.00004300

C -1.88601300 0.99058600 -0.00005300

C -0.60118000 1.45003400 -0.00001300

C 0.45710100 0.42178600 0.00002100

C 1.80825400 0.73540700 -0.00006000

C 2.82724800 -0.19902500 -0.00005200

H -3.05502900 -0.86550100 -0.00006700

H -2.73177200 1.66959700 -0.00009000

H -0.35466400 2.50693000 -0.00001200

H 2.09026800 1.78806500 -0.00013200

H 2.61183400 -1.26186800 0.00001600

H 3.86710000 0.09838000 -0.00011500

H -0.09202800 -2.08557300 1.19346100

H -0.09187800 -2.08574300 -1.19312400

A6-T1-twisted Cs symmetry, NIMAG=1 E = -522.7413041 a.u. Si -0.35568900 -1.22755700 0.00009100

C -2.06506400 -0.47689700 0.00001400

C -1.93277500 0.89269800 -0.00005900

C -0.61938000 1.43554800 -0.00007900

C 0.45133100 0.48192600 -0.00002300

C 1.77184900 0.78666700 -0.00004600

C 2.83513000 -0.22430000 -0.00001200

H -3.03992600 -0.94640800 0.00002400

H -2.79272900 1.55651100 -0.00010300

H -0.43879100 2.50539800 -0.00014200

H 3.29966700 -0.54037900 0.92727300

H 3.29928500 -0.54084100 -0.92733100

H 2.07347900 1.83829400 -0.00009500

H -0.03392900 -2.03042300 -1.20338800

H -0.03396200 -2.03020600 1.20372300

A7-S0

Cs symmetry, NIMAG=0 E = -307.3785473 a.u. C -0.80621400 -1.64193200 0.00000000

C -1.88375800 -0.81948300 0.00000000

C -1.35815600 0.51101100 0.00000000

C 0.00000000 0.38970000 0.00000000

H -0.69379300 -2.71282400 0.00000000

H -2.91839200 -1.12077000 0.00000000

H -1.90922100 1.43759400 0.00000000

C 1.06123400 1.37756700 0.00000000

H 0.72124800 2.40802200 0.00000000

C 2.36287100 1.09058700 0.00000000

H 2.71024000 0.06430800 0.00000000

H 3.10604900 1.87710600 0.00000000

O 0.34100100 -0.92476800 0.00000000


C -1.82754700 -0.92910900 0.00000000

C -1.45862000 0.39742400 0.00000000

C 0.00000000 0.42877900 0.00000000

H -0.48515600 -2.75026000 0.00000000

H -2.82740000 -1.33365400 0.00000000

H -2.08944200 1.27105000 0.00000000

C 0.89338000 1.43644500 0.00000000

H 0.49936200 2.44494000 0.00000000

C 2.32619600 1.22503400 0.00000000

H 2.72709700 0.22257800 0.00000000

H 3.00466500 2.06419900 0.00000000

O 0.44167600 -0.89285500 0.00000000


C 2.03553100 0.28663700 -0.00010500

C 0.92595600 1.15985600 0.00024200

C -0.21985100 0.35463700 -0.00002800

H 1.98764400 -1.95478800 -0.00011900

H 3.08117200 0.54893600 0.00057500

H 0.92900300 2.23753300 -0.00048700

C -1.57153400 0.65245800 -0.00017500

C -2.62169200 -0.36173900 0.00015100

H -3.01789900 -0.75895800 -0.92745600

H -3.01854100 -0.75800700 0.92785400

H -1.83166700 1.70783300 -0.00049000

O 0.17677700 -0.96101400 -0.00009600

A8-S0 Cs symmetry, NIMAG=0 E = -630.3539755 a.u. C -1.13537100 -1.63832400 0.00000000

C -2.01870200 -0.60155500 0.00000000

C -1.36648800 0.66362100 0.00000000

C 0.00000000 0.57009600 0.00000000

S 0.49742600 -1.09229800 0.00000000

H -1.34644200 -2.69653400 0.00000000

H -3.09171400 -0.73356800 0.00000000

H -1.88273500 1.61491400 0.00000000

C 0.94589500 1.67930900 0.00000000

H 0.48038400 2.66146100 0.00000000

C 2.27519400 1.58319900 0.00000000

H 2.78150200 0.62350000 0.00000000

H 2.89701200 2.46891900 0.00000000


C -2.02618300 -0.59114400 0.00000000

C -1.46475200 0.65261800 0.00000000

C 0.00000000 0.62416100 0.00000000

S 0.55415800 -1.08020600 0.00000000

H -1.29549000 -2.70125200 0.00000000

H -3.09205400 -0.77664700 0.00000000

H -2.00679500 1.58781600 0.00000000

C 0.85943500 1.66817800 0.00000000

H 0.42991600 2.66524800 0.00000000

C 2.28889600 1.54231600 0.00000000

H 2.76382200 0.57042500 0.00000000

H 2.91998100 2.41842800 0.00000000


C 1.97415300 0.75031400 0.00005500

C 0.72584800 1.39345300 -0.00013100

C -0.35851500 0.49865200 -0.00002900

S 0.23573400 -1.15663600 -0.00014900

H 2.67843400 -1.34001300 0.00039700

H 2.92237500 1.27058000 0.00009000

H 0.58457000 2.46568800 -0.00023900

C -1.71559200 0.78480700 0.00005300

H -1.99587500 1.83703800 0.00008300

C -2.76187500 -0.23394100 0.00011500

H -3.19959200 -0.58599700 0.92789600

H -3.19970600 -0.58596900 -0.92761800


C -1.85243100 -0.93251400 0.00000000

C -1.38102900 0.40488900 0.00000000

C 0.00000000 0.36861100 0.00000000

H -0.66424400 -2.82457400 0.00000000

H -2.87894100 -1.26141300 0.00000000

H -1.97562900 1.30542200 0.00000000

C 0.94662600 1.46905800 0.00000000

H 0.48397500 2.45138600 0.00000000

C 2.27807900 1.37682800 0.00000000

H 2.79927900 0.42515200 0.00000000

H 2.89742500 2.26398800 0.00000000

H 1.31411500 -1.29133800 0.00000000

N 0.36563900 -0.95558100 0.00000000


C -1.82013900 -0.98878000 0.00000000

C -1.45785500 0.34140700 0.00000000

C 0.00000000 0.41895500 0.00000000

H -0.53010500 -2.83577100 0.00000000

H -2.82215400 -1.38820100 0.00000000

H -2.10408200 1.20448800 0.00000000

C 0.82271600 1.49742700 0.00000000

H 0.36397000 2.47725400 0.00000000

C 2.28020600 1.40316600 0.00000000

H 2.79470300 0.45248700 0.00000000

H 2.88843800 2.29481700 0.00000000

H 1.38835100 -1.21034300 0.00000000

N 0.42706100 -0.91933500 0.00000000

A9-T1-twisted Cs symmetry, NIMAG=0 E = -287.4322835 a.u. C 1.60928000 -0.97014300 -0.00012700

C 2.04658500 0.34247500 -0.00019400

C 0.91103300 1.16917200 -0.00000600

C -0.23198900 0.34095500 0.00024900

H 2.16454500 -1.89375200 0.00017300

H 3.07827200 0.65634700 -0.00013800

H 0.88572000 2.24732600 0.00035600

C -1.58990700 0.65904500 -0.00012700

C -2.64756200 -0.34975000 -0.00000900

H -3.10763600 -0.68474900 -0.92502300

H -3.10792900 -0.68406200 0.92510500

H -1.85192200 1.71350200 -0.00075700

H -0.35350900 -1.77271000 -0.00186700

N 0.24397300 -0.96177500 0.00049000


C -1.64414300 -1.28413700 0.00000000

C -1.40575200 0.09309400 0.00000000

C 0.00000000 0.31025300 0.00000000

H -0.22921200 -3.01404900 0.00000000

H -2.61384100 -1.76714800 0.00000000

H -2.15384900 0.87876800 0.00000000

C 0.62049100 1.61019200 0.00000000

H -0.08615700 2.44338500 0.00000000

C 1.93262900 1.92849300 0.00000000

H 2.70027900 1.16154700 0.00000000

H 2.26077400 2.96186100 0.00000000

H 1.68776200 -1.15357100 0.00000000

C 0.62004600 -0.96845800 0.00000000

A10-T1-planar Cs symmetry, NIMAG=1 E = -270.7884122 a.u. C 0.00000000 0.38751300 0.00000000

C 0.51586200 -0.98013900 0.00000000

C -0.55958500 -1.85671600 0.00000000

C -1.77303300 -1.08693600 0.00000000

C -1.44885500 0.25943800 0.00000000

H 1.56267100 -1.24848600 0.00000000

H -0.50563400 -2.93835700 0.00000000

H -2.77463900 -1.50105000 0.00000000

H -2.13664800 1.09508100 0.00000000

C 0.74442300 1.56440100 0.00000000

C 2.20344800 1.54547600 0.00000000

H 0.23008400 2.51952100 0.00000000

H 2.78047200 2.46221400 0.00000000

H 2.75012700 0.61285700 0.00000000

A10-T1-twisted Cs symmetry, NIMAG=0 E = -270.7936749 a.u. C -0.57767400 -1.86062400 0.00000000

C -1.77950000 -1.09292200 0.00000000

C -1.43472000 0.25714900 0.00000000

C 0.00000000 0.36520200 0.00000000

H -0.52066900 -2.94288300 0.00000000

H -2.78566700 -1.49571500 0.00000000

H -2.11605200 1.10010300 0.00000000

C 0.75096700 1.55727400 0.00000000

C 2.21277200 1.58839500 0.00000000

H 2.79618500 1.53616700 0.92073000

H 2.79618500 1.53616700 -0.92073000

H 0.21397000 2.50617100 0.00000000

H 1.55561700 -1.24504200 0.00000000

C 0.50489300 -0.98030300 0.00000000

B1-S0 (same with A1-S0) B1-T1-planar (same with A1-T1-planar) B1-T1-twisted (same with A1-T1-twisted)

B2-S0 Cs symmetry, NIMAG=0 E = -521.9251661 a.u. C 0.58563000 -1.75644300 0.00000000

C 1.03889800 -0.49710500 0.00000000

C 0.00000000 0.62606900 0.00000000

C -1.30886100 0.22770900 0.00000000

H 1.21387600 -2.63556800 0.00000000

H 2.09525300 -0.25662600 0.00000000

H -2.29237300 -2.56456600 0.00000000

Si -1.23357300 -1.55176900 0.00000000

C 0.40181800 2.01171400 0.00000000

H -0.40223100 2.74000000 0.00000000

C 1.67698800 2.43286500 0.00000000

H 2.52847800 1.76392300 0.00000000

H 1.90159000 3.49292800 0.00000000

H -2.14141500 0.91582600 0.00000000

B2-T1-planar Cs symmetry, NIMAG=0 E = -521.8879518 a.u. C 0.79258300 -1.63729200 0.00000000

C 1.09029500 -0.27992800 0.00000000

C 0.00000000 0.64131100 0.00000000

C -1.29986900 -0.00930500 0.00000000

H 1.56973000 -2.38978900 0.00000000

H 2.11708400 0.06693100 0.00000000

H -1.92574500 -2.92507600 0.00000000

Si -0.98845600 -1.80603000 0.00000000

C 0.09589100 2.05988200 0.00000000

H -0.83881200 2.61140800 0.00000000

C 1.26240400 2.76272200 0.00000000

H 2.23396200 2.28330000 0.00000000

H 1.25029400 3.84511200 0.00000000

H -2.21596300 0.56819500 0.00000000

B2-T1-twisted Cs symmetry, NIMAG=1 E = -521.8569935 a.u. C -1.22573200 1.35225000 -0.00117900

C 0.10853400 1.12146000 -0.00100300

C 0.57221600 -0.29418000 0.00008100

C -0.47847200 -1.25205500 0.00081400

H -1.66002600 2.34172300 -0.00193700

H 0.84809500 1.91749300 -0.00161300

H -3.39087400 -0.73170700 0.00041700

Si -1.99804800 -0.28204600 0.00007200

C 1.89699400 -0.64533300 0.00034900

H 2.12672500 -1.71383900 0.00116700

C 3.00980700 0.28922600 -0.00036700

H 3.50542400 0.53116100 0.93361100

H 3.53654500 0.49364000 -0.92645100

H -0.29329600 -2.31803700 0.00163000

B3-S0 Cs symmetry, NIMAG=0 E = -257.5670171 a.u. C -0.95568900 -1.78870900 0.00000000

C 0.20873500 -1.13143700 0.00000000

C 0.00000000 0.37797300 0.00000000

C -1.31646000 0.67567300 0.00000000

H -1.02529100 -2.86869700 0.00000000

H 1.19578900 -1.58086100 0.00000000

B -2.09287600 -0.68584700 0.00000000

H -3.26750800 -0.85522100 0.00000000

C 1.09550200 1.33501500 0.00000000

H 0.80464400 2.38229400 0.00000000

C 2.39257600 1.01344900 0.00000000

H 2.73238800 -0.01527800 0.00000000

H 3.15782400 1.77994400 0.00000000

H -1.68144800 1.69527500 0.00000000

B3-T1-planar Cs symmetry, NIMAG=0 E = -257.5285871 a.u. C -0.59541500 -1.93537700 0.00000000

C 0.46648100 -1.00479900 0.00000000

C 0.00000000 0.31574800 0.00000000

C -1.45936800 0.30062600 0.00000000

H -0.40115800 -3.00157600 0.00000000

H 1.51765000 -1.27052200 0.00000000

B -1.93133700 -1.16508500 0.00000000

H -3.04019100 -1.58517000 0.00000000

C 0.78859600 1.52694000 0.00000000

H 0.22453300 2.45588200 0.00000000

C 2.12989000 1.58946000 0.00000000

H 2.74556600 0.69720100 0.00000000

H 2.64416600 2.54188400 0.00000000

H -2.01499100 1.23214500 0.00000000

B3-T1-twisted Cs symmetry, NIMAG=1 E = -257.4974644 a.u. C 1.70353900 -1.04340000 -0.00005100

C 0.35164900 -1.05829500 -0.00003600

C -0.22782400 0.30861100 -0.00001400

C 0.87070200 1.25406300 -0.00003500

H 2.28684200 -1.95662500 -0.00020800

H -0.28425300 -1.93866800 -0.00019600

B 2.18240200 0.44434000 0.00032400

H 3.29388700 0.86053900 -0.00029700

C -1.54439300 0.60895900 -0.00016400

H -1.81895100 1.66611100 -0.00020800

C -2.63146700 -0.37391400 0.00012300

H -3.10325500 -0.67499100 0.92795000

H -3.10347300 -0.67533700 -0.92748000

H 0.68395000 2.32111800 -0.00012200


C 0.99364900 -0.53286700 0.00000000

C 0.00000000 0.60882800 0.00000000

C -1.31893100 0.30519100 0.00000000

H 1.29067200 -2.60834000 0.00000000

H 2.05131500 -0.28083500 0.00000000

H -2.55415700 -2.68351400 0.00000000

Al -1.37874600 -1.63791200 0.00000000

H -2.03861100 1.11692300 0.00000000

C 0.48476200 1.99610200 0.00000000

H -0.29999600 2.74846900 0.00000000

C 1.75720900 2.39959500 0.00000000

H 2.59437200 1.71307900 0.00000000

H 1.99911500 3.45556900 0.00000000

B4-T1-planar Cs symmetry, NIMAG=1 E = -475.0786729 a.u. C 0.82607600 -1.66791700 0.00000000

C 1.07483500 -0.27762600 0.00000000

C 0.00000000 0.61518300 0.00000000

C -1.34319100 -0.00612500 0.00000000

H 1.69246000 -2.32141200 0.00000000

H 2.09083100 0.10837300 0.00000000

H -2.06406400 -3.14833100 0.00000000

Al -1.08891200 -1.91952900 0.00000000

H -2.18529700 0.67921400 0.00000000

C 0.13879900 2.05761000 0.00000000

H -0.79589200 2.61261100 0.00000000

C 1.28520300 2.76105000 0.00000000

H 2.25959700 2.28709000 0.00000000

H 1.26789000 3.84327600 0.00000000

B4-T1-twisted Cs symmetry, NIMAG=0 E = -475.0612600 a.u. C -0.59401300 -1.75433700 0.00000000

C -1.00087300 -0.47035500 0.00000000

C 0.00000000 0.64576600 0.00000000

C 1.37325400 0.24878000 0.00000000

H -1.34487200 -2.53694200 0.00000000

H -2.05152800 -0.18104400 0.00000000

H 2.48467200 -2.77173500 0.00000000

Al 1.35032200 -1.68398700 0.00000000

H 2.11669300 1.03839900 0.00000000

C -0.40747900 1.95419200 0.00000000

H 0.37419100 2.71616000 0.00000000

C -1.79526300 2.42018100 0.00000000

H -2.29354900 2.68081500 0.92674400

H -2.29354900 2.68081500 -0.92674400

B5-S0 Cs symmetry, NIMAG=0 E = -271.4459591 a.u. C 1.65027400 0.99155900 0.00013200

C 0.31385700 1.09648200 0.00013200

C -0.28418200 -0.25375700 -0.00007400

C 0.71611900 -1.16024100 0.00005800

H 2.35893900 1.80817100 0.00019600

H -0.24940200 2.02001900 0.00016300

C 2.04053600 -0.45907900 0.00014200

H 2.64323600 -0.71985800 -0.87835200

H 2.64316500 -0.71990500 0.87866900

C -1.71260700 -0.55920700 -0.00020700

H -1.96519700 -1.61662100 -0.00028700

C -2.69173100 0.34561100 -0.00019500

H -2.48732700 1.41025100 -0.00008600

H -3.73211300 0.04528800 -0.00027900

H 0.59510800 -2.23555200 0.00004400

B5-T1-planar Cs symmetry, NIMAG=0 E = -271.3525110 a.u. C 1.60291500 1.01507300 0.00015600

C 0.25012200 1.08214400 0.00008000

C -0.33572300 -0.22764200 -0.00004100

C 0.82191800 -1.18217100 0.00000000

H 2.26387600 1.87250900 0.00024200

H -0.31769000 2.00304300 0.00009100

C 2.10760000 -0.41200500 0.00013800

H 2.73773900 -0.62412800 -0.87629900

H 2.73759700 -0.62420700 0.87665800

C -1.67127700 -0.57866600 -0.00015400

H -1.89260400 -1.64294400 -0.00021500

C -2.75416700 0.29906100 -0.00018600

H -2.61756000 1.37271400 -0.00012700

H -3.76838700 -0.07379800 -0.00027100

H 0.72870400 -2.25796000 -0.00003400

B5-T1-twisted Cs symmetry, NIMAG=0 E = -271.3550591 a.u. C -1.58843300 1.04413600 -0.00014100

C -0.25115500 1.08099800 0.00015600

C 0.29327100 -0.29562800 -0.00003000

C -0.79658900 -1.16527500 0.00001000

H -2.25022700 1.89988500 -0.00023200

H 0.36971500 1.96791400 0.00027100

C -2.07346500 -0.38282400 0.00003100

H -2.69541500 -0.60181300 0.87772000

H -2.69544500 -0.60190600 -0.87760800

C 1.64073700 -0.63329000 -0.00001400

H 1.89496800 -1.69291300 0.00009100

C 2.73103800 0.34113300 -0.00004000

H 3.19056900 0.66907500 0.92623000

H 3.19063500 0.66894100 -0.92631800

H -0.73721800 -2.24469000 0.00001300

B6-S0 Cs symmetry, NIMAG=0 E = -522.8203333 a.u. Si -2.01864100 -0.31605000 0.00008900

C -1.18544000 1.36003100 0.00001300

C 0.13917600 1.15041000 -0.00003300

C 0.60609500 -0.27086300 -0.00002700

C -0.37468400 -1.20058700 0.00002200

H -1.60453500 2.35803600 0.00001200

H 0.86304000 1.95906200 -0.00007600

H -2.84234200 -0.57708700 1.20308700

H -2.84250100 -0.57714800 -1.20278700

C 2.03197400 -0.61673400 -0.00006800

H 2.24364800 -1.68283300 -0.00006000

C 3.05064100 0.24388800 -0.00010800

H 2.90799400 1.31766400 -0.00011500

H 4.07404600 -0.11038700 -0.00013200

H -0.14495100 -2.25947600 0.00003000

B6-T1-planar Cs symmetry, NIMAG=0 E = -522.7400966 a.u. Si -2.07755400 -0.29580000 0.00009800

C -1.17192000 1.33378300 0.00001300

C 0.20973300 1.12513600 -0.00004100

C 0.66558800 -0.19487500 -0.00003200

C -0.45405100 -1.19260400 0.00002700

H -1.56867300 2.34160900 0.00000400

H 0.90818100 1.95591400 -0.00008900

H -2.93393500 -0.54305900 1.18917300

H -2.93407400 -0.54311200 -1.18886500

C 2.03429600 -0.61432300 -0.00007200

H 2.19444700 -1.68948400 -0.00006900

C 3.12665100 0.18373700 -0.00011000

H 3.05383700 1.26467700 -0.00011100

H 4.12165000 -0.24115900 -0.00014000

H -0.21745300 -2.24931100 0.00002000

B6-T1-twisted Cs symmetry, NIMAG=0 E = -522.7334809 a.u. Si -2.04175500 -0.25741700 0.00005400

C -1.11864800 1.37261200 -0.00000800

C 0.19842400 1.11866400 -0.00012800

C 0.62821400 -0.31000500 -0.00004500

C -0.44980700 -1.22100600 0.00000800

H -1.49862400 2.38675400 0.00002800

H 0.96173800 1.89278200 -0.00018100

H -2.88798600 -0.47447200 1.19787000

H -2.88810200 -0.47451600 -1.19767200

C 1.95864100 -0.67570900 -0.00012600

H 2.18051200 -1.74348300 -0.00059300

C 3.08944500 0.25233300 0.00018300

H 3.57247500 0.54129900 0.92686500

H 3.57228400 0.54196700 -0.92638900

H -0.26534400 -2.28782100 0.00002100

B7-S0 Cs symmetry, NIMAG=0

E = -307.3740293 a.u. C 1.70084600 0.85278100 -0.00003300

C 0.36915300 1.08477300 0.00003900

C -0.26354200 -0.21093800 -0.00000200

C 0.76050600 -1.10752100 -0.00008200

H 2.56296500 1.49803500 -0.00003800

H -0.10907700 2.05049400 0.00010900

O 1.95599900 -0.47777800 -0.00010700

C -1.68571200 -0.53803900 0.00004100

H -1.92384600 -1.59849200 -0.00000300

C -2.67617700 0.35227800 0.00013300

H -2.48432100 1.41954400 0.00018000

H -3.71170800 0.03724600 0.00016400

H 0.78754900 -2.18460800 -0.00013200

B7-T1-planar Cs symmetry, NIMAG=1 E = -307.2619207 a.u. C 1.63092800 0.91399000 -0.00003000

C 0.30101500 1.07474400 0.00004100

C -0.29327000 -0.26577100 0.00000200

C 0.85189100 -1.13031200 -0.00009200

H 2.44855300 1.61617600 -0.00003400

H -0.22163800 2.01647700 0.00011400

O 1.99670500 -0.40422900 -0.00011100

C -1.60807300 -0.61883500 0.00004400

H -1.86582900 -1.67167300 0.00000700

C -2.71891900 0.36305200 0.00013700

H -2.52290700 1.42501500 0.00016800

H -3.74476500 0.02823800 0.00016500

H 0.95150600 -2.20161400 -0.00015100

B7-T1-twisted Cs symmetry, NIMAG=0 E = -307.2788627 a.u. C 1.64416700 -0.91611900 0.00006000

C 0.30503300 -1.06877200 -0.00008000

C -0.26129200 0.26765900 -0.00000100

C 0.83537200 1.10879200 -0.00003400

H 2.46591800 -1.61223900 0.00010800

H -0.24284600 -1.99739600 -0.00014400

O 1.98642700 0.39898900 0.00001300

C -1.62823500 0.62653200 0.00000600

H -1.87708500 1.68540000 0.00001700

C -2.70662900 -0.35724400 0.00002200

H -3.15016100 -0.70700900 0.92662100

H -3.15023600 -0.70706900 -0.92650500

H 0.93249800 2.18132100 -0.00004200


C -0.58747600 -0.19520500 0.00005100

C -0.09029800 1.15080900 -0.00005100

C 1.26690600 1.21185500 0.00019400

S 1.98085900 -0.35552600 -0.00012300

H 0.35438200 -2.18092700 0.00017600

H -0.71920800 2.03048200 -0.00009000

H 1.89367100 2.09036800 0.00031000

C -1.99769000 -0.59286200 0.00006000

H -2.17727600 -1.66471200 0.00019600

C -3.04002800 0.23672200 -0.00009200

H -2.91891700 1.31404000 -0.00025000

H -4.05362700 -0.14327600 -0.00007200

B8-T1-planar Cs symmetry, NIMAG=1 E = -630.2433910 a.u. C -0.52139400 -1.14233000 -0.00006200

C 0.62491000 -0.25488700 0.00001400

C 0.15323900 1.13167100 0.00003800

C -1.18271400 1.24653700 -0.00001700

S -2.01451800 -0.29953500 -0.00008800

H -0.49416000 -2.22020900 -0.00009300

H 0.81564100 1.98568000 0.00009000

H -1.76760100 2.15432400 -0.00001500

C 1.92407700 -0.65892600 0.00005700

H 2.13090900 -1.72357900 0.00002200

C 3.08493600 0.24910400 0.00014600

H 2.96247200 1.32170300 0.00021900

H 4.08670100 -0.15237300 0.00013500

B8-T1-twisted Cs symmetry, NIMAG=0 E = -630.2590311 a.u. C 0.50206200 -1.12548000 -0.00009200

C -0.58843300 -0.26229900 0.00000000

C -0.14639000 1.11551900 0.00000500

C 1.20075100 1.24179700 -0.00007400

S 2.00144000 -0.29170700 0.00006000

H 0.47877700 -2.20445500 -0.00014400

H -0.83058000 1.95378700 0.00001100

H 1.78468600 2.14948800 -0.00012000

C -1.94273000 -0.67170200 0.00000800

H -2.14757400 -1.74025700 -0.00004000

C -3.06643400 0.25975300 0.00003700

H -3.53061300 0.58161200 -0.92646800

H -3.53069700 0.58159900 0.92648600

B9-S0 Cs symmetry, NIMAG=0 E = -287.5200212 a.u. C -0.29319500 -1.89807000 0.00000000

C 0.66770800 -0.92266100 0.00000000

C 0.00000000 0.34191900 0.00000000

C -1.35246300 0.07330000 0.00000000

H -0.20821800 -2.97219600 0.00000000

H 1.73249500 -1.09237500 0.00000000

H -2.40591200 -1.75764500 0.00000000

N -1.51936700 -1.28313500 0.00000000

C 0.58431800 1.67960000 0.00000000

H -0.12891200 2.50063300 0.00000000

C 1.88748200 1.95922300 0.00000000

H 2.63799000 1.17639600 0.00000000

H 2.24099200 2.98225000 0.00000000

H -2.19595600 0.74500900 0.00000000

B9-T1-planar Cs symmetry, NIMAG=2 E = -287.4070017 a.u. C -0.40475900 -1.84230000 0.00000000

C 0.59978900 -0.92824500 0.00000000

C 0.00000000 0.40294100 0.00000000

C -1.41019900 0.17077800 0.00000000

H -0.37144900 -2.91979600 0.00000000

H 1.65315000 -1.15399500 0.00000000

H -2.51634200 -1.62433400 0.00000000

N -1.61544800 -1.17782200 0.00000000

C 0.64221600 1.61876000 0.00000000

H 0.05678300 2.52990200 0.00000000

C 2.13144200 1.73947600 0.00000000

H 2.75890000 0.86091800 0.00000000

H 2.60269000 2.71047300 0.00000000

H -2.22652700 0.87313300 0.00000000

B9-T1-twisted Cs symmetry, NIMAG=0 E = -287.4246100 a.u. C 0.45777700 -1.84101200 0.00000000

C -0.57068800 -0.94263600 0.00000000

C 0.00000000 0.38122300 0.00000000

C 1.38541600 0.20267300 0.00000000

H 0.45346400 -2.91857700 0.00000000

H -1.62398800 -1.17559200 0.00000000

H 2.55663800 -1.55323600 0.00000000

N 1.64005900 -1.13969200 0.00000000

C -0.69864500 1.61394900 0.00000000

H -0.11600400 2.53245900 0.00000000

C -2.15572900 1.69660000 0.00000000

H -2.72021800 1.74927400 0.92578400

H -2.72021800 1.74927400 -0.92578400

H 2.18112700 0.92946300 0.00000000

B10-S0 (same with A10-S0) B10-T1-planar (same with A10-T1-planar) B10-T1-twisted (same with A10-T1-twisted)

supporting information - connecting repositoriesplanar t1 state geometries described by (i) a...

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