Electronic Supplementary information
Unusual Reverse Face-to-Face Stacking in Propylene Linked Pyrazole System: Perspective of Organic Materials
Sunil Kumar Rai,[1]Priyanka Srivastava,[1] Hariom Gupta,[2] Maria del C. Puerta,[3] Pedro Valerga,[3] and Ashish Kumar Tewari*[1]
1Department of Chemistry (Center of Advanced Studies), Faculty of Science, Banaras HinduUniversity, Varanasi 221005, India.
Table of content
- NMR spectra (1H, 13C and 2D NOESY)...... 1-5
- Single crystal X-rays diffraction analysis of compound 1 and 2...... 6-10
- Computational studies...... 11-20
- References...... 21
1. NMR spectra (1H, 13C and 2D NOESY).
Figure S1.1H NMR spectra of compound 1 in CDCl3.
Figure S2.13C NMR spectra of compound 1 in CDCl3.
Figure S3.1H NMR spectra of compound 2 in CDCl3.
Figure S4.13C NMR spectra of compound 2 in CDCl3.
Figure S5.1H NMR spectra of compound 3 in CDCl3.
Figure S6.13C NMR spectra of compound 3 in CDCl3.
Figure S7. Full 2DNOESY spectra of compound 1 in CDCl3at 400 MHz.
Figure S8.Full2DNOESY spectra of compound 2 in CDCl3at 400 MHz.
Figure S9.Full 2DNOESY spectra of compound 3 in CDCl3at 400 MHz.
2. Single crystal X-rays diffraction analysis
The X-ray diffraction data of compound 1was collected on Bruker SMART APEX CCD area detector diffractometer. The structure was solved and refined by using SHELXS program.1 Molecular graphics were designed by using Mercury version-3.2
Single crystal X-rays structure of compound 1.
Table S1:Geometric parameters for compound 1.
Bond distances (Å)O2—C7 / 1.3492 (19) / C5—C4 / 1.385 (3)
O2—C21 / 1.448 (2) / C5—H5 / 0.962 (19)
N3—C7 / 1.357 (2) / C8—C9 / 1.396 (3)
N3—N4 / 1.3830 (18) / C8—H8 / 0.901 (18)
N3—C6 / 1.424 (2) / C18—H18 / 0.95 (2)
N1—C17 / 1.362 (2) / C15—C14 / 1.381 (3)
N1—N2 / 1.385 (2) / C15—H15 / 0.969 (18)
N1—C16 / 1.420 (2) / C1—C2 / 1.379 (3)
O1—C17 / 1.341 (2) / C1—H1 / 0.974 (19)
O1—C23 / 1.442 (2) / C13—C14 / 1.371 (3)
C7—C8 / 1.357 (2) / C13—C12 / 1.369 (3)
N4—C9 / 1.319 (2) / C13—H13 / 0.98 (2)
N2—C19 / 1.318 (2) / C3—C2 / 1.370 (3)
C16—C11 / 1.386 (2) / C3—C4 / 1.379 (3)
C16—C15 / 1.384 (3) / C3—H3 / 0.95 (2)
C17—C18 / 1.360 (3) / C11—C12 / 1.374 (3)
C6—C5 / 1.378 (2) / C11—H11 / 0.93 (2)
C6—C1 / 1.388 (2) / C4—H4 / 0.963 (17)
C22—C23 / 1.501 (3) / C9—C10 / 1.501 (3)
C22—C21 / 1.504 (3) / C2—H2 / 1.02 (2)
C22—H22A / 0.99 (2) / C12—H12 / 0.98 (2)
C22—H22B / 0.94 (2) / C14—H14 / 0.96 (2)
C19—C18 / 1.403 (2) / C20—H20A / 0.9600
C19—C20 / 1.490 (3) / C20—H20B / 0.9600
C23—H23A / 1.00 (2) / C20—H20C / 0.9600
C23—H23B / 0.996 (19) / C10—H10A / 0.9600
C21—H21B / 0.987 (19) / C10—H10B / 0.9600
C21—H21A / 1.04 (2) / C10—H10C / 0.9600
C17—C18 / 1.360 (3) / C11—C12 / 1.374 (3)
Bond angels (°)
C7—O2—C21 / 112.87 (13) / C7—C8—H8 / 127.1 (12)
C7—N3—N4 / 110.14 (13) / C9—C8—H8 / 127.7 (12)
C7—N3—C6 / 131.30 (14) / C17—C18—C19 / 104.95 (18)
N4—N3—C6 / 118.56 (13) / C17—C18—H18 / 125.3 (12)
C17—N1—N2 / 109.56 (15) / C19—C18—H18 / 129.6 (12)
C17—N1—C16 / 131.77 (14) / C14—C15—C16 / 119.50 (19)
N2—N1—C16 / 118.60 (13) / C14—C15—H15 / 120.3 (11)
C17—O1—C23 / 114.60 (14) / C16—C15—H15 / 120.2 (12)
O2—C7—N3 / 119.31 (14) / C2—C1—C6 / 119.42 (19)
O2—C7—C8 / 132.79 (15) / C2—C1—H1 / 120.7 (12)
N3—C7—C8 / 107.90 (15) / C6—C1—H1 / 119.9 (12)
C9—N4—N3 / 104.79 (14) / C14—C13—C12 / 118.9 (2)
C19—N2—N1 / 105.42 (14) / C14—C13—H13 / 120.7 (12)
C11—C16—C15 / 118.80 (19) / C12—C13—H13 / 120.3 (12)
C11—C16—N1 / 118.05 (17) / C2—C3—C4 / 119.57 (19)
C15—C16—N1 / 123.15 (15) / C2—C3—H3 / 119.9 (13)
O1—C17—C18 / 132.79 (16) / C4—C3—H3 / 120.5 (13)
O1—C17—N1 / 118.91 (16) / C12—C11—C16 / 120.7 (2)
C18—C17—N1 / 108.30 (15) / C12—C11—H11 / 122.0 (12)
C5—C6—C1 / 120.38 (16) / C16—C11—H11 / 117.3 (12)
C5—C6—N3 / 121.68 (15) / C3—C4—C5 / 120.7 (2)
C1—C6—N3 / 117.91 (15) / C3—C4—H4 / 119.0 (11)
C23—C22—C21 / 112.54 (18) / C5—C4—H4 / 120.3 (11)
C23—C22—H22A / 106.8 (10) / N4—C9—C8 / 111.97 (16)
C21—C22—H22A / 112.2 (11) / N4—C9—C10 / 120.58 (18)
C23—C22—H22B / 107.9 (12) / C8—C9—C10 / 127.38 (18)
C21—C22—H22B / 109.1 (11) / C3—C2—C1 / 120.7 (2)
H22A—C22—H22B / 108.1 (17) / C3—C2—H2 / 119.3 (12)
N2—C19—C18 / 111.76 (17) / C1—C2—H2 / 119.9 (12)
N2—C19—C20 / 120.14 (17) / C13—C12—C11 / 120.6 (2)
C18—C19—C20 / 128.09 (19) / C13—C12—H12 / 120.0 (13)
O1—C23—C22 / 106.55 (16) / C11—C12—H12 / 119.3 (13)
O1—C23—H23A / 108.9 (11) / C13—C14—C15 / 121.5 (2)
C22—C23—H23A / 111.4 (10) / C13—C14—H14 / 121.2 (13)
O1—C23—H23B / 107.9 (10) / C15—C14—H14 / 117.3 (13)
C22—C23—H23B / 112.8 (10) / C19—C20—H20A / 109.5
H23A—C23—H23B / 109.2 (16) / C19—C20—H20B / 109.5
O2—C21—C22 / 108.43 (15) / H20A—C20—H20B / 109.5
O2—C21—H21B / 108.1 (11) / C19—C20—H20C / 109.5
C22—C21—H21B / 112.5 (11) / H20A—C20—H20C / 109.5
O2—C21—H21A / 106.2 (11) / H20B—C20—H20C / 109.5
C22—C21—H21A / 112.4 (11) / C9—C10—H10A / 109.5
H21B—C21—H21A / 108.9 (15) / C9—C10—H10B / 109.5
C6—C5—C4 / 119.18 (18) / H10A—C10—H10B / 109.5
C6—C5—H5 / 120.7 (10) / C9—C10—H10C / 109.5
C4—C5—H5 / 120.1 (10) / H10A—C10—H10C / 109.5
C7—C8—C9 / 105.19 (16) / H10B—C10—H10C / 109.5
Torsion angles (°)
C21—O2—C7—N3 / 174.64 (16) / C7—O2—C21—C22 / 173.77 (15)
C21—O2—C7—C8 / −5.2 (3) / C23—C22—C21—O2 / −74.9 (2)
N4—N3—C7—O2 / 179.22 (14) / C1—C6—C5—C4 / −1.0 (3)
C6—N3—C7—O2 / −1.5 (3) / N3—C6—C5—C4 / 177.15 (16)
N4—N3—C7—C8 / −0.9 (2) / O2—C7—C8—C9 / −179.16 (18)
C6—N3—C7—C8 / 178.36 (16) / N3—C7—C8—C9 / 1.0 (2)
C7—N3—N4—C9 / 0.42 (19) / O1—C17—C18—C19 / −178.91 (17)
C6—N3—N4—C9 / −178.96 (15) / N1—C17—C18—C19 / 0.68 (19)
C17—N1—N2—C19 / 0.14 (17) / N2—C19—C18—C17 / −0.6 (2)
C16—N1—N2—C19 / 177.48 (13) / C20—C19—C18—C17 / 178.26 (18)
C17—N1—C16—C11 / 176.89 (16) / C11—C16—C15—C14 / 0.0 (3)
N2—N1—C16—C11 / 0.2 (2) / N1—C16—C15—C14 / −179.32 (16)
C17—N1—C16—C15 / −3.8 (3) / C5—C6—C1—C2 / 0.9 (3)
N2—N1—C16—C15 / 179.58 (14) / N3—C6—C1—C2 / −177.30 (17)
C23—O1—C17—C18 / 3.6 (3) / C15—C16—C11—C12 / −0.5 (3)
C23—O1—C17—N1 / −175.96 (15) / N1—C16—C11—C12 / 178.92 (17)
N2—N1—C17—O1 / 179.12 (14) / C2—C3—C4—C5 / 1.2 (3)
C16—N1—C17—O1 / 2.2 (3) / C6—C5—C4—C3 / 0.0 (3)
N2—N1—C17—C18 / −0.53 (19) / N3—N4—C9—C8 / 0.2 (2)
C16—N1—C17—C18 / −177.41 (16) / N3—N4—C9—C10 / −177.11 (18)
C7—N3—C6—C5 / 25.8 (3) / C7—C8—C9—N4 / −0.8 (2)
N4—N3—C6—C5 / −154.95 (16) / C7—C8—C9—C10 / 176.3 (2)
C7—N3—C6—C1 / −155.97 (18) / C4—C3—C2—C1 / −1.2 (3)
N4—N3—C6—C1 / 23.3 (2) / C6—C1—C2—C3 / 0.2 (3)
N1—N2—C19—C18 / 0.30 (19) / C14—C13—C12—C11 / −0.1 (3)
N1—N2—C19—C20 / −178.68 (15) / C16—C11—C12—C13 / 0.5 (3)
C17—O1—C23—C22 / 176.12 (16) / C12—C13—C14—C15 / −0.4 (3)
C21—C22—C23—O1 / −179.07 (16) / C16—C15—C14—C13 / 0.4 (3)
3. Computational studies.
All the calculations have been carried out with the Gaussian-093 programs at the M06-2X/6-31G (d, p) and ωB97X-D/6-31G (d, p) level of theory. The single point energy and optimised structure energy of the molecules in open as well as in folded conformation have been calculated in order to compare the structural stability in gaseous state.
Cartesian Coordinates of the Structures Involved in this Study
Compound 1: single point energy calculation
Standard orientation:
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Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
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1 1 0 -0.088600 -0.240435 -1.790572
2 1 0 -0.788321 -1.962823 0.381814
3 1 0 2.317232 3.690064 0.828367
4 1 0 -0.264954 -0.431276 0.564124
5 1 0 -4.806123 0.624180 -3.693730
6 1 0 -6.588093 0.441173 0.575973
7 1 0 2.314822 1.372681 0.418322
8 1 0 3.659281 -3.065721 -0.827770
9 1 0 1.707243 -1.961781 -2.186259
10 1 0 1.424133 -2.479662 -0.647679
11 1 0 -7.088302 1.198394 -3.378364
12 1 0 4.316528 4.888775 0.754877
13 1 0 -0.565318 -1.725123 -1.934641
14 1 0 6.340154 1.519160 -0.266006
15 1 0 -3.447721 0.058022 -1.907826
16 1 0 -1.774600 -1.063665 2.480586
17 1 0 6.346956 3.862635 0.180703
18 1 0 -7.979267 1.105983 -1.199932
19 8 0 2.200362 -0.641623 -0.777895
20 7 0 4.396847 -0.168234 -0.140058
21 7 0 -4.130188 -0.115155 0.666859
22 8 0 -2.055523 -0.562702 -0.290699
23 6 0 3.457863 -1.065456 -0.534337
24 7 0 5.605506 -0.806162 0.072373
25 7 0 -4.750058 -0.131854 1.905215
26 6 0 -4.905443 0.212651 -0.477264
27 6 0 -2.829236 -0.495770 0.803054
28 6 0 4.326072 1.240498 0.058897
29 6 0 -0.056084 -1.152261 -1.395483
30 6 0 -3.820399 -0.515394 2.757346
31 6 0 -0.724002 -1.062360 -0.054380
32 6 0 1.347309 -1.685186 -1.306481
33 6 0 3.139899 1.868679 0.369194
34 6 0 4.048900 -2.285347 -0.600929
35 6 0 -2.593702 -0.748253 2.118756
36 6 0 -4.380936 0.265334 -1.757438
37 6 0 5.503980 1.969850 -0.031131
38 6 0 -6.526209 0.903391 -2.626355
39 6 0 4.311740 3.958724 0.542699
40 6 0 -6.247492 0.505132 -0.292633
41 6 0 3.140967 3.232825 0.610399
42 6 0 5.370916 -2.073608 -0.207735
43 6 0 5.481217 3.326262 0.211107
44 6 0 -7.042579 0.850835 -1.359107
45 6 0 -5.201027 0.606564 -2.814794
46 6 0 -4.149757 -0.674155 4.201383
47 1 0 -5.068087 -0.437855 4.348611
48 1 0 -3.584057 -0.099896 4.723697
49 1 0 -4.008249 -1.587151 4.463333
50 6 0 6.445690 -3.106394 -0.030293
51 1 0 7.259193 -2.678087 0.245519
52 1 0 6.591364 -3.564085 -0.861445
53 1 0 6.175187 -3.738447 0.639470
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Compound 1: optimizedin open conformation
Standard orientation:
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Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
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1 1 0 -0.088600 -0.240435 -1.790572
2 1 0 -0.788321 -1.962823 0.381814
3 1 0 2.317232 3.690064 0.828367
4 1 0 -0.264954 -0.431276 0.564124
5 1 0 -4.806123 0.624180 -3.693730
6 1 0 -6.588093 0.441173 0.575973
7 1 0 2.314822 1.372681 0.418322
8 1 0 3.659281 -3.065721 -0.827770
9 1 0 1.707243 -1.961781 -2.186259
10 1 0 1.424133 -2.479662 -0.647679
11 1 0 -7.088302 1.198394 -3.378364
12 1 0 4.316528 4.888775 0.754877
13 1 0 -0.565318 -1.725123 -1.934641
14 1 0 6.340154 1.519160 -0.266006
15 1 0 -3.447721 0.058022 -1.907826
16 1 0 -1.774600 -1.063665 2.480586
17 1 0 6.346956 3.862635 0.180703
18 1 0 -7.979267 1.105983 -1.199932
19 8 0 2.200362 -0.641623 -0.777895
20 7 0 4.396847 -0.168234 -0.140058
21 7 0 -4.130188 -0.115155 0.666859
22 8 0 -2.055523 -0.562702 -0.290699
23 6 0 3.457863 -1.065456 -0.534337
24 7 0 5.605506 -0.806162 0.072373
25 7 0 -4.750058 -0.131854 1.905215
26 6 0 -4.905443 0.212651 -0.477264
27 6 0 -2.829236 -0.495770 0.803054
28 6 0 4.326072 1.240498 0.058897
29 6 0 -0.056084 -1.152261 -1.395483
30 6 0 -3.820399 -0.515394 2.757346
31 6 0 -0.724002 -1.062360 -0.054380
32 6 0 1.347309 -1.685186 -1.306481
33 6 0 3.139899 1.868679 0.369194
34 6 0 4.048900 -2.285347 -0.600929
35 6 0 -2.593702 -0.748253 2.118756
36 6 0 -4.380936 0.265334 -1.757438
37 6 0 5.503980 1.969850 -0.031131
38 6 0 -6.526209 0.903391 -2.626355
39 6 0 4.311740 3.958724 0.542699
40 6 0 -6.247492 0.505132 -0.292633
41 6 0 3.140967 3.232825 0.610399
42 6 0 5.370916 -2.073608 -0.207735
43 6 0 5.481217 3.326262 0.211107
44 6 0 -7.042579 0.850835 -1.359107
45 6 0 -5.201027 0.606564 -2.814794
46 6 0 -4.149757 -0.674155 4.201383
47 1 0 -5.068087 -0.437855 4.348611
48 1 0 -3.584057 -0.099896 4.723697
49 1 0 -4.008249 -1.587151 4.463333
50 6 0 6.445690 -3.106394 -0.030293
51 1 0 7.259193 -2.678087 0.245519
52 1 0 6.591364 -3.564085 -0.861445
53 1 0 6.175187 -3.738447 0.639470
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Compound 1: optimizedin folded conformation
Standard orientation:
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Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
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1 8 0 -1.771716 -0.596373 2.015687
2 7 0 -2.488890 -0.942729 -0.175593
3 7 0 -3.472455 -0.568069 -1.059961
4 6 0 -1.468520 -1.834035 -0.609582
5 6 0 -0.944134 -2.803658 0.252085
6 1 0 -1.314837 -2.883981 1.266026
7 6 0 0.048425 -3.666999 -0.212953
8 1 0 0.454592 -4.419088 0.456808
9 6 0 0.502603 -3.582519 -1.529462
10 1 0 1.271148 -4.261163 -1.886301
11 6 0 -0.042337 -2.624521 -2.386937
12 1 0 0.301257 -2.555008 -3.414632
13 6 0 -1.023538 -1.746255 -1.932930
14 1 0 -1.458607 -0.998607 -2.584544
15 6 0 -4.255519 0.265996 -0.397628
16 6 0 -3.803016 0.450230 0.950392
17 6 0 -2.650195 -0.342672 1.037783
18 6 0 -5.444156 0.853852 -1.091573
19 1 0 -5.398959 1.946711 -1.096934
20 1 0 -6.374742 0.578559 -0.587332
21 1 0 -5.471264 0.488661 -2.120301
22 6 0 -1.167184 0.537434 2.708455
23 1 0 -1.924470 0.993008 3.346578
24 1 0 -0.832157 1.260650 1.958339
25 6 0 -0.000295 0.000185 3.520571
26 1 0 -0.360570 -0.802472 4.174717
27 8 0 1.771447 0.596344 2.015882
28 7 0 2.488797 0.942547 -0.175387
29 7 0 3.472233 0.567517 -1.059741
30 6 0 1.468781 1.834242 -0.609408
31 6 0 0.944872 2.804216 0.252157
32 1 0 1.315659 2.884504 1.266069
33 6 0 -0.047305 3.667959 -0.212950
34 1 0 -0.453096 4.420322 0.456732
35 6 0 -0.501565 3.583533 -1.529434
36 1 0 -1.269807 4.262491 -1.886331
37 6 0 0.042905 2.625181 -2.386812
38 1 0 -0.300754 2.555707 -3.414488
39 6 0 1.023718 1.746521 -1.932734
40 1 0 1.458425 0.998597 -2.584275
41 6 0 4.255007 -0.266809 -0.397396
42 6 0 3.802365 -0.450958 0.950585
43 6 0 2.649846 0.342387 1.037977
44 6 0 5.443471 -0.855057 -1.091307
45 1 0 5.397822 -1.947898 -1.096825
46 1 0 6.374121 -0.580222 -0.586938
47 1 0 5.470826 -0.489741 -2.119984
48 6 0 1.166657 -0.537298 2.708698
49 1 0 1.923791 -0.992885 3.346991
50 1 0 0.831662 -1.260575 1.958624
51 1 0 0.359932 0.803030 4.174514
52 1 0 -4.244390 1.054785 1.714985
53 1 0 4.243466 -1.055738 1.715157
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Compound 2: single point energy calculation
Standard orientation:
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Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
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1 8 0 4.149286 0.753750 1.784562
2 8 0 5.062507 0.499183 -0.259737
3 8 0 1.134806 1.450043 1.671460
4 7 0 0.794476 1.871768 -0.574141
5 7 0 1.440254 1.907151 -1.789641
6 6 0 -0.577124 2.274457 -0.483242
7 6 0 -0.932366 3.289616 0.391354
8 1 0 -0.279093 3.698753 0.945953
9 6 0 -2.253792 3.695921 0.443353
10 1 0 -2.506669 4.402283 1.025050
11 6 0 -3.211629 3.079652 -0.346345
12 1 0 -4.118726 3.355163 -0.295546
13 6 0 -2.843239 2.061443 -1.210141
14 1 0 -3.500886 1.639365 -1.750640
15 6 0 -1.516091 1.654969 -1.289440
16 1 0 -1.257207 0.963013 -1.887638
17 6 0 2.688273 1.541779 -1.525840
18 6 0 2.870174 1.276511 -0.142039
19 6 0 1.623689 1.504770 0.425760
20 6 0 3.676446 1.493543 -2.646440
21 1 0 3.989657 0.572987 -2.766337
22 1 0 4.438546 2.072892 -2.435442
23 1 0 3.249786 1.804190 -3.472341
24 6 0 4.058990 0.833480 0.580262
25 6 0 6.246485 -0.009313 0.393264
26 1 0 6.583469 0.659289 1.025862
27 1 0 6.933542 -0.199133 -0.278435
28 1 0 6.025565 -0.833502 0.875867
29 6 0 1.259622 0.182231 2.386765
30 1 0 2.052281 0.199072 2.979064
31 1 0 1.362861 -0.564402 1.744867
32 6 0 0.000041 0.000005 3.204065
33 1 0 -0.114679 0.790209 3.789363
34 8 0 -4.149330 -0.753685 1.784569
35 8 0 -5.062521 -0.499227 -0.259732
36 8 0 -1.134724 -1.450044 1.671471
37 7 0 -0.794395 -1.871784 -0.574128
38 7 0 -1.440173 -1.907175 -1.789628
39 6 0 0.577110 -2.274502 -0.483227
40 6 0 0.932322 -3.289561 0.391377
41 1 0 0.279049 -3.698693 0.945978
42 6 0 2.253748 -3.695865 0.443378
43 1 0 2.506751 -4.402288 1.025080
44 6 0 3.211615 -3.079696 -0.346324
45 1 0 4.118712 -3.355208 -0.295524
46 6 0 2.843194 -2.061398 -1.210128
47 1 0 3.500937 -1.639294 -1.750629
48 6 0 1.516046 -1.654925 -1.289429
49 1 0 1.257192 -0.963068 -1.887631
50 6 0 -2.688288 -1.541832 -1.525829
51 6 0 -2.870188 -1.276554 -0.142030
52 6 0 -1.623638 -1.504684 0.425771
53 6 0 -3.676461 -1.493604 -2.646429
54 1 0 -3.989672 -0.573049 -2.766332
55 1 0 -4.438466 -2.072921 -2.435427
56 1 0 -3.249801 -1.804256 -3.472328
57 6 0 -4.059035 -0.833423 0.580269
58 6 0 -6.246499 0.009273 0.393266
59 1 0 -6.583483 -0.659324 1.025869
60 1 0 -6.933587 0.199184 -0.278434
61 1 0 -6.025483 0.833496 0.875863
62 6 0 -1.259635 -0.182257 2.386766
63 1 0 -2.052294 -0.199094 2.979066
64 1 0 -1.362904 0.564467 1.744864
65 1 0 0.114666 -0.790225 3.789368
------
Compound 2: optimizedin open conformation
Standard orientation:
------
Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
------
1 8 0 1.902555 -3.490138 -0.285692
2 8 0 3.293951 -3.541603 -2.047505
3 8 0 2.068728 -0.777522 1.259283
4 7 0 3.793351 0.334331 0.173117
5 7 0 4.661929 0.195895 -0.870737
6 6 0 3.813750 1.532212 0.933929
7 6 0 3.460139 1.538056 2.282739
8 1 0 3.176398 0.617061 2.773925
9 6 0 3.469044 2.739953 2.983737
10 1 0 3.182839 2.745748 4.030215
11 6 0 3.858218 3.919815 2.359298
12 1 0 3.875594 4.850941 2.916270
13 6 0 4.239637 3.895429 1.020243
14 1 0 4.547341 4.811580 0.527274
15 6 0 4.213713 2.708276 0.300914
16 1 0 4.492996 2.671896 -0.744804
17 6 0 4.388317 -0.970049 -1.415843
18 6 0 3.326729 -1.629845 -0.727682
19 6 0 2.973362 -0.742709 0.284692
20 6 0 5.182944 -1.434609 -2.590755
21 1 0 4.533924 -1.621844 -3.449523
22 1 0 5.697567 -2.372516 -2.369093
23 1 0 5.917919 -0.670572 -2.849253
24 6 0 2.753504 -2.949705 -0.963399
25 6 0 2.749745 -4.816825 -2.369084
26 1 0 2.868163 -5.513806 -1.536697
27 1 0 1.686050 -4.727843 -2.604299
28 6 0 1.034109 -1.783005 1.217754
29 1 0 1.293930 -2.569014 1.925599
30 1 0 0.999011 -2.221765 0.218750
31 6 0 -0.280623 -1.111521 1.567980
32 1 0 -0.241834 -0.692266 2.579704
33 8 0 -1.330778 3.326468 -0.226681
34 8 0 -2.794498 3.832802 -1.852646
35 8 0 -1.933562 0.545059 1.067339
36 7 0 -3.911339 -0.092130 0.031624
37 7 0 -4.800290 0.321788 -0.917930
38 6 0 -4.120946 -1.338752 0.676740
39 6 0 -3.689532 -1.557555 1.984553
40 1 0 -3.197008 -0.766397 2.533636
41 6 0 -3.892563 -2.803866 2.568950
42 1 0 -3.546518 -2.977118 3.582508
43 6 0 -4.548320 -3.813004 1.872469
44 1 0 -4.714944 -4.778037 2.339872
45 6 0 -5.002560 -3.571848 0.578387
46 1 0 -5.517617 -4.353517 0.029980
47 6 0 -4.787030 -2.341199 -0.026993
48 1 0 -5.120168 -2.139524 -1.037532
49 6 0 -4.335706 1.465595 -1.373218
50 6 0 -3.122030 1.831811 -0.718441
51 6 0 -2.887857 0.789478 0.173470
52 6 0 -5.095933 2.197694 -2.428563
53 1 0 -4.479253 2.348872 -3.317724
54 1 0 -5.398370 3.187227 -2.077853
55 1 0 -5.983271 1.620854 -2.694362
56 6 0 -2.314064 3.035147 -0.877642
57 6 0 -2.029348 5.007439 -2.098735
58 1 0 -1.953273 5.620452 -1.198127
59 1 0 -1.021872 4.742506 -2.429614
60 6 0 -0.674667 0.002254 0.615971
61 1 0 0.065116 0.801157 0.587157
62 1 0 -0.805378 -0.378157 -0.398899
63 1 0 -1.052193 -1.889677 1.572271
64 1 0 -2.558880 5.546421 -2.883685
65 1 0 3.304822 -5.164363 -3.239805
------
Compound 2: optimizedin folded conformation
Standard orientation:
------
Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
------
1 8 0 3.799242 1.210913 1.646042
2 8 0 4.545026 1.005535 -0.463238
3 8 0 0.684165 1.573842 1.732641
4 7 0 0.139967 1.876583 -0.504394
5 7 0 0.706416 1.891644 -1.746823
6 6 0 -1.261397 2.068283 -0.387469
7 6 0 -1.829765 2.604695 0.767403
8 1 0 -1.201295 2.899106 1.596917
9 6 0 -3.212168 2.750621 0.842590
10 1 0 -3.652869 3.157184 1.746821
11 6 0 -4.020558 2.402373 -0.233394
12 1 0 -5.096711 2.530114 -0.172153
13 6 0 -3.437679 1.898572 -1.393204
14 1 0 -4.059143 1.628510 -2.240901
15 6 0 -2.063871 1.720739 -1.474219
16 1 0 -1.595895 1.315605 -2.362496
17 6 0 1.983900 1.635785 -1.565604
18 6 0 2.287495 1.455842 -0.182969
19 6 0 1.063131 1.616003 0.458215
20 6 0 2.898406 1.602142 -2.744905
21 1 0 3.392177 0.631428 -2.827124
22 1 0 3.686084 2.353607 -2.650519
23 1 0 2.320331 1.796340 -3.649875
24 6 0 3.580393 1.217671 0.450727
25 6 0 5.839615 0.690244 0.056668
26 1 0 6.243754 1.548325 0.551914
27 1 0 5.757121 -0.117718 0.753298
28 6 0 1.166657 0.503879 2.571515
29 1 0 1.974073 0.891956 3.190991
30 1 0 1.570831 -0.290951 1.941833
31 6 0 -0.000350 0.001398 3.400660
32 1 0 -0.370142 0.801365 4.051939
33 8 0 -3.799409 -1.210390 1.646579
34 8 0 -4.545137 -1.006660 -0.462875
35 8 0 -0.684367 -1.572520 1.733679
36 7 0 -0.139795 -1.876321 -0.503211
37 7 0 -0.706152 -1.892206 -1.745664
38 6 0 1.261546 -2.068090 -0.386159
39 6 0 1.829922 -2.603499 0.769178
40 1 0 1.201496 -2.896935 1.599072
41 6 0 3.212300 -2.749727 0.844329
42 1 0 3.652986 -3.155537 1.748906
43 6 0 4.020649 -2.402819 -0.232116
44 1 0 5.096768 -2.530846 -0.170914
45 6 0 3.437750 -1.899946 -1.392323
46 1 0 4.059169 -1.630921 -2.240381
47 6 0 2.063997 -1.721750 -1.473313
48 1 0 1.596053 -1.317216 -2.361882
49 6 0 -1.983725 -1.636591 -1.564683
50 6 0 -2.287466 -1.456058 -0.182175
51 6 0 -1.063112 -1.615530 0.459206
52 6 0 -2.898061 -1.603657 -2.744125
53 1 0 -3.392067 -0.633096 -2.826785
54 1 0 -3.685542 -2.355318 -2.649615
55 1 0 -2.319775 -1.798041 -3.648926
56 6 0 -3.580485 -1.217883 0.451280
57 6 0 -5.839838 -0.691291 0.056767
58 1 0 -6.244234 -1.549424 0.551714
59 1 0 -5.757411 0.116503 0.753599
60 6 0 -1.167042 -0.501764 2.571523
61 1 0 -1.974767 -0.889243 3.190967
62 1 0 -1.570912 0.292488 1.940907
63 1 0 0.369209 -0.798015 4.052765
64 1 0 -6.486434 -0.405024 -0.746268
65 1 0 6.486465 0.404251 -0.746259
------
Compound 3: optimizedin open conformation
Standard orientation:
------
Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
------
1 8 0 4.031348 -2.918035 0.421538
2 8 0 5.486461 -2.093368 -1.076469
3 8 0 2.039761 -0.722806 1.440831
4 7 0 2.976638 1.232689 0.618767
5 7 0 3.982996 1.675753 -0.191320
6 6 0 2.106372 2.183916 1.220258
7 6 0 1.499309 1.931972 2.449343
8 1 0 1.675100 0.996055 2.962576
9 6 0 0.669036 2.898124 3.007028
10 1 0 0.187845 2.696459 3.958169
11 6 0 0.465773 4.113586 2.365379
12 1 0 -0.177585 4.864815 2.811113
13 6 0 1.095486 4.361915 1.149804
14 1 0 0.950539 5.312096 0.645154
15 6 0 1.908705 3.399447 0.567061
16 1 0 2.412843 3.579089 -0.374376
17 6 0 4.604212 0.599446 -0.623402
18 6 0 4.019022 -0.587431 -0.086681
19 6 0 2.966493 -0.120564 0.699927
20 6 0 5.777472 0.744409 -1.535839
21 1 0 5.613121 0.208515 -2.473542
22 1 0 6.679940 0.327939 -1.081872
23 1 0 5.935323 1.803926 -1.743990
24 6 0 4.473441 -1.969207 -0.196422
25 6 0 6.011673 -3.410815 -1.215373
26 1 0 6.406295 -3.774289 -0.263750
27 1 0 5.238702 -4.101163 -1.560862
28 6 0 1.377068 -1.889947 0.914743
29 1 0 1.861627 -2.774952 1.324582
30 1 0 1.503942 -1.909318 -0.173128
31 6 0 -0.088130 -1.809501 1.294795
32 1 0 -0.188365 -1.770321 2.384312
33 8 0 -1.450659 2.231887 0.453805
34 8 0 -2.568168 3.105611 -1.286571
35 8 0 -2.178878 -0.715157 0.980292
36 7 0 -4.081255 -1.030215 -0.314651
37 7 0 -4.852955 -0.397677 -1.246828
38 6 0 -4.370070 -2.375798 0.035976
39 6 0 -4.085719 -2.865512 1.310089
40 1 0 -3.644913 -2.217839 2.056018
41 6 0 -4.377290 -4.192512 1.608627
42 1 0 -4.154271 -4.574478 2.599553
43 6 0 -4.964950 -5.020634 0.658065
44 1 0 -5.196783 -6.052392 0.900751
45 6 0 -5.262196 -4.514131 -0.604428
46 1 0 -5.726987 -5.150339 -1.350553
47 6 0 -4.963218 -3.195874 -0.923072
48 1 0 -5.191080 -2.783241 -1.898048
49 6 0 -4.300582 0.783435 -1.433057
50 6 0 -3.149318 0.952413 -0.607640
51 6 0 -3.047733 -0.248957 0.087313
52 6 0 -4.912997 1.744339 -2.397877
53 1 0 -4.194886 2.028413 -3.170842
54 1 0 -5.219757 2.663673 -1.892782
55 1 0 -5.784249 1.279547 -2.862090
56 6 0 -2.301327 2.121710 -0.405233
57 6 0 -1.769400 4.276478 -1.128827
58 1 0 -1.914620 4.713815 -0.138135
59 1 0 -0.709833 4.037372 -1.246763
60 6 0 -0.775568 -0.607842 0.673680
61 1 0 -0.400145 0.337981 1.063735
62 1 0 -0.650162 -0.608857 -0.416093
63 1 0 -0.580616 -2.726978 0.954341
64 6 0 -2.236970 5.250592 -2.226133
65 1 0 -3.267444 5.493829 -2.071670
66 1 0 -1.649458 6.143877 -2.184036
67 1 0 -2.118877 4.790890 -3.185105
68 6 0 7.139209 -3.299834 -2.258419
69 1 0 7.902144 -2.645911 -1.890704
70 1 0 7.555966 -4.268907 -2.437613
71 1 0 6.742936 -2.907573 -3.171654
------
Compound 3: optimizedin folded conformation
Standard orientation:
------
Center Atomic Atomic Coordinates (Angstroms)
Number Number Type X Y Z
------
1 8 0 4.234720 -2.593706 0.034224
2 8 0 5.859112 -1.037083 -0.152650
3 8 0 1.530156 -1.369825 1.079957
4 7 0 2.136747 0.818124 1.611627
5 7 0 3.196489 1.690438 1.539642
6 6 0 0.904088 1.268532 2.160779
7 6 0 0.106116 0.418838 2.934651
8 1 0 0.423970 -0.598594 3.123594
9 6 0 -1.091528 0.900091 3.464671
10 1 0 -1.710192 0.239439 4.064661
11 6 0 -1.484352 2.220849 3.245997
12 1 0 -2.414875 2.590234 3.665818
13 6 0 -0.670021 3.066303 2.489647
14 1 0 -0.964975 4.097310 2.319020
15 6 0 0.521204 2.596115 1.941899
16 1 0 1.165575 3.238248 1.354319
17 6 0 4.183275 1.014663 0.976144
18 6 0 3.790536 -0.330267 0.672049
19 6 0 2.454557 -0.401191 1.090914
20 6 0 5.499711 1.694124 0.763322
21 1 0 5.780884 1.691217 -0.293658
22 1 0 6.301585 1.184495 1.304858
23 1 0 5.427787 2.725410 1.115023
24 6 0 4.599583 -1.434556 0.162703
25 6 0 6.740682 -2.076076 -0.631537
26 1 0 6.811799 -2.860681 0.128269
27 1 0 6.303252 -2.528744 -1.527010
28 6 0 1.271887 -2.058481 -0.180979
29 1 0 2.126785 -2.696920 -0.404063
30 1 0 1.156510 -1.305602 -0.967049
31 6 0 -0.000104 -2.870187 0.000417
32 1 0 0.116025 -3.524134 0.872661
33 8 0 -4.234799 -2.593633 -0.033953
34 8 0 -5.859248 -1.037011 0.152401
35 8 0 -1.530088 -1.369841 -1.079534
36 7 0 -2.136705 0.817974 -1.611716
37 7 0 -3.196503 1.690248 -1.540076
38 6 0 -0.903969 1.268341 -2.160733
39 6 0 -0.105827 0.418532 -2.934303
40 1 0 -0.423607 -0.598949 -3.123105
41 6 0 1.091886 0.899734 -3.464212
42 1 0 1.710684 0.238992 -4.063966
43 6 0 1.484611 2.220555 -3.245733
44 1 0 2.415190 2.589899 -3.665464
45 6 0 0.670110 3.066120 -2.489689
46 1 0 0.964986 4.097175 -2.319221
47 6 0 -0.521187 2.595986 -1.942051
48 1 0 -1.165694 3.238207 -1.354717
49 6 0 -4.183337 1.014546 -0.976575
50 6 0 -3.790579 -0.330303 -0.672148
51 6 0 -2.454533 -0.401250 -1.090804
52 6 0 -5.499839 1.693990 -0.764098
53 1 0 -5.781179 1.691300 0.292837
54 1 0 -6.301603 1.184205 -1.305650
55 1 0 -5.427909 2.725202 -1.116014
56 6 0 -4.599668 -1.434514 -0.162697
57 6 0 -6.740860 -2.075935 0.631358
58 1 0 -6.811903 -2.860652 -0.128339
59 1 0 -6.303511 -2.528470 1.526938
60 6 0 -1.271946 -2.058200 0.181589
61 1 0 -2.126956 -2.696433 0.404836
62 1 0 -1.156425 -1.305129 0.967453
63 1 0 -0.116347 -3.524370 -0.871631
64 6 0 -8.086590 -1.437164 0.916595
65 1 0 -8.508760 -0.991165 0.011535
66 1 0 -8.785787 -2.194549 1.284321
67 1 0 -7.996850 -0.655223 1.676140
68 6 0 8.086385 -1.437347 -0.916996
69 1 0 8.508636 -0.991213 -0.012040
70 1 0 8.785549 -2.194787 -1.284670
71 1 0 7.996579 -0.655519 -1.676650
------
4. Reference:
- Sheldrick GM (2008) Acta Cryst A A64: 112-122.
- Bruno IJ, Cole JC, Edgington PR, Kessler MK, Macrae CF, McCabe P, Pearson J, Taylor R(2002) Acta Crystallogr B58: 389-397.
- Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Hratchian X, Li HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota V, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta Jr JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) Gaussian Inc., Wallingford CT.
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