Weak Intermolecular Interactions in a Series of Bioactive Oxazoles
Abstract
1. Introduction
2. Results
3. Materials and Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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1 | 2 | 3 | 4 | 5 | 6A | 6B | 7 | 8 | 9 | CSDB | |
---|---|---|---|---|---|---|---|---|---|---|---|
C1-C2 | 1.355(4) | 1.350(6) | 1.367(2) | 1.363(5) | 1.3595(19) | 1.362(4) | 1.363(4) | 1.354(11) | 1.361(3) | 1.354(5) | 1.357(14) 1.348(15) |
C1-N5 | 1.403(3) | 1.387(6) | 1.408(2) | 1.409(4) | 1.4099(17) | 1.401(4) | 1.401(4) | 1.423(10) | 1.397(3) | 1.404(5) | 1.398(10) 1.393(12) |
C2-O3 | 1.385(3) | 1.381(5) | 1.3906(18) | 1.395(4) | 1.3899(16) | 1.391(3) | 1.391(3) | 1.376(9) | 1.378(3) | 1.387(5) | 1.296(15) 1.294(15) |
O3-C4 | 1.352(3) | 1.346(5) | 1.3504(19) | 1.346(4) | 1.3550(16) | 1.347(4) | 1.353(4) | 1.350(10) | 1.356(4) | 1.345(4) | 1.350(16) 1.359(18) |
C4-N5 | 1.287(4) | 1.256(6) | 1.292(2) | 1.287(5) | 1.2874(18) | 1.276(4) | 1.275(4) | 1.286(11) | 1.276(4) | 1.288(5) | 1.387(11) 1.379(13) |
C2-C1-N5 | 108.8(3) | 109.0(4) | 108.62(13) | 108.5(3) | 108.51(12) | 108.9(3) | 109.0(2) | 109.5(8) | 109.1(2) | 108.8(4) | 108.6(6) 109.5(11) |
C1-C2-O3 | 107.8(2) | 107.1(5) | 107.25(13) | 107.0(3) | 107.57(12) | 106.8(3) | 106.8(3) | 107.2(8) | 107.2(2) | 107.1(3) | 107.4(6) 107.4(11) |
C2-O3-C4 | 103.9(2) | 103.3(4) | 104.54(12) | 104.9(3) | 104.36(10) | 104.4(2) | 104.2(2) | 104.5(7) | 104.0(2) | 104.9(3) | 104.9(8) 104.7(9) |
O3-C4-N5 | 115.3(3) | 116.2(5) | 115.06(14) | 114.8(3) | 114.85(12) | 115.3(3) | 115.4(3) | 116.1(9) | 115.5(3) | 114.5(4) | 114.0(11) 113.9(10) |
C1-N5-C4 | 104.3(2) | 104.3(4) | 104.50(13) | 104.9(3) | 104.68(11) | 104.6(3) | 104.5(3) | 102.6(8) | 104.1(2) | 104.7(3) | 105.1(8) 104.6(9) |
C12-C13-C14 | 120.5(3) | 119.3(5) | 120.42(14) | 121.3(3) | 120.62(13) | 121.5(3) | 121.3(3) | 121.8(8) | 121.7(4) | 122.9(4) | |
C13-C14-C15 | 119.7(3) | 119.2(5) | 119.60(14) | 118.4(3) | 118.46(12) | 117.9(2) | 118.4(2) | 119.9(9) | 118.8(2) | 116.8(4) | |
C14-C15-C16 | 120.1(3) | 120.6(5) | 120.28(14) | 120.8(3) | 121.24(12) | 120.8(3) | 120.3(3) | 116.7(10) | 119.4(3) | 121.0(4) | |
C22-C23-C24 | 121.1(3) | 122.6(5) | 119.76(14) | 120.2(3) | 123.31(13) | 119.7(3) | 120.0(3) | 117.3(9) | 120.7(2) | 119.6(4) | |
C23-C24-C25 | 118.2(3) | 116.2(4) | 119.60(14) | 119.3(3) | 117.34(13) | 119.7(3) | 119.9(3) | 121.5(9) | 118.4(2) | 120.6(4) | |
C2-C1-C11-C12 | −26.2(5) | −16.8(9) | −13.0(3) | −40.5(6) | −18.1(3) | −7.1(6) | −20.8(6) | −30.5(15) | −28.6(10) 144.9(13) | −39.6(7) | |
C2-C1-C11-C16 | 154.4(3) | 162.5(5) | 168.67(16) | 142.1(4) | 163.19(14) | 173.6(4) | 161.2(4) | 152.9(10) | 146.6(6) −54(2) | 144.2(5) | |
N5-C1-C11-C12 | 149.3(3) | 163.3(5) | 163.65(14) | 140.2(4) | 158.95(13) | 171.5(3) | 157.7(3) | 148.1(8) | 143.7(7) −22(2) | 141.0(4) | |
N5-C1-C11-C16 | −30.1(4) | −17.4(7) | −14.6(2) | −37.3(5) | −19.78(19) | −7.8(5) | −20.4(5) | −28.5(13) | −41.1(9) 139.7(13) | −35.2(6) | |
C1-C2-C21-C22 | −36.1(6) | −28.4(9) | 147.51(19) | 154.5(4) | 143.26(17) | 139.7(5) | 145.3(4) | −22.2(18) | −30.5(5) | 153.8(5) | |
C1-C2-C21-C26 | 142.4(4) | 155.0(6) | −38.3(3) | −26.5(7) | −38.2(3) | −40.5(7) | −34.9(6) | 162.0(12) | 151.6(4) | −28.3(8) | |
O3-C2-C21-C22 | 139.8(3) | 149.4(5) | −35.70(19) | −28.2(5) | −39.97(18) | −37.5(5) | −31.5(4) | 157.1(8) | 145.1(3) | −28.9(6) | |
O3-C2-C21-C26 | −41.7(4) | −27.2(7) | 138.51(14) | 150.8(3) | 138.57(13) | 142.3(3) | 148.3(3) | −18.7(13) | −32.9(4) | 149.0(4) | |
A/B | 28.36(14) | 17.04(18) | 14.51(6) | 39.20(10) | 19.42(7) | 7.3(3) | 20.56(19) | 30.8(3) | 35.4(2) | 37.53(11) | |
B/C | 39.72(14) | 27.75(11) | 38.28(5) | 28.08(16) | 39.63(4) | 38.46(14) | 32.64(18) | 20.2(4) | 32.79(17) | 29.31(18) | |
A/C | 51.51(11) | 32.47(12) | 47.42(4) | 51.84(11) | 47.83(4) | 38.69(1) | 39.00(14) | 42.5(3) | 49.6(2) | 51.54(13) | |
A/OMe3 | 6.5(2) | 4.7(3) | 3.15(14) | 8.3(2) | 13.09(15) | 2.0(7) | 5.6(5) | ||||
A/O(S)Me4 | 73.27(13) | 81.2(3) | 80.09(13) | 50.39(13) | 60.10(5) | 86.7(2) | 69.44(15) | 79.4(5) | 79.6(3) | 50.25(16) | |
A/OMe5 | 0.9(2) | 6.6(3) | 4.09(15) | 9.0(3) | 4.84(17) | 8.7(5) | 3.5(5) | 2.5(7) | 5.6(7) | 7.3(3) | |
B/OMe3 | 12.3(3) | 3.24(18) | 1.3(5) | 6.19(18) | |||||||
B/SMe4 | 1.2(2) | 85.6(2) | 1.2(2) | ||||||||
B/OMe4 | 0.80(16) | 1.3(5) | 4.42(17) | 3.10(17) | 1.4(5) | 2.3(11) | 2.3(5) |
Atom1 | Atom2 | Gcp | Vcp | DEN | LAP | X···Y | H···Y | X-H···Y | Pix | HF B3LYP |
---|---|---|---|---|---|---|---|---|---|---|
C16 | C12 i | 4.35 | −2.77 | 0.01834 | 0.218 | 3.742 | −78.9 | −69.1 −67.4 | ||
C14 | H13C i | 8.55 | −6.18 | 0.03675 | 0.401 | 3.717 | 2.90 | 131 | ||
O15 | H14B i | 10.27 | −6.41 | 0.02888 | 0.519 | 3.447 | 2.78 | 119 | ||
O14 | H14B i | 3.86 | −2.43 | 0.01651 | 0.194 | 4.173 | 3.14 | 158 | ||
H15C | C11 i | 8.86 | −7.02 | 0.0442 | 0.393 | 3.980 | 2.90 | 170 | ||
H22 | H12 i | 0.98 | −0.58 | 0.00581 | 0.051 | 3.39 | ||||
O23 | H24A i | 14.83 | −10.65 | 0.05047 | 0.698 | 3.452 | 2.53 | 142 | ||
H23C | C24 i | 12.94 | −10.26 | 0.05547 | 0.574 | 3.550 | 2.69 | 136 | ||
S24 | H24A i | 9.07 | −6.53 | 0.03773 | 0.427 | 3.894 | 2.96 | 144 | ||
H13A | O13 ii | 12.71 | −8.13 | 0.03529 | 0.634 | 3.259 | 2.74 | 109 | −40.9 | −53.7 −46.1 |
O13 | H23B ii | 2.3 | −1.28 | 0.00743 | 0.122 | 4.084 | 3.37 | 124 | ||
H13A | O14 ii | 7.86 | −4.98 | 0.02567 | 0.394 | 3.613 | 2.84 | 128 | ||
H14A | O23 ii | 12.93 | −8.69 | 0.04038 | 0.63 | 3.429 | 2.63 | 130 | ||
H14A | S24 ii | 6.97 | −5.34 | 0.03615 | 0.316 | 4.137 | 3.07 | 167 | ||
H23A | O14 iii | 22.51 | −17.79 | 0.077 | 0.999 | 3.308 | 2.34 | 147 | −11.2 | −30.6 −24.2 |
H14B | O14 iii | 3.86 | −2.43 | 0.01651 | 0.194 | |||||
H4 | N5 iv | 19.54 | −13.48 | 0.05478 | 0.94 | 3.413 | 2.48 | 143 | −5.9 | −27.1 −22.7 |
R | E_ele | E_pol | E_dis | E_rep | E_tot |
---|---|---|---|---|---|
5.13 | −18.7 −19.2 | −10.0 −5.9 | −90.3 −90.3 | 46.7 58.2 | −69.1 −67.4 |
7.84 | −25.4 −21.0 | −9.4 −5.7 | −46.4 −46.4 | 24.7 33.5 | −53.7 −46.1 |
8.78 | −20.3 −16.6 | −7.3 −4.2 | −18.0 −18.0 | 13.6 19.5 | −30.6 −24.2 |
11.39 | −21.9 −18.8 | −4.0 −3.1 | −12.2 −12.2 | 10.9 16.3 | −27.1 −22.7 |
Atom1 | Atom2 | Gcp | Vcp | DEN | LAP | X···Y | H···Y | X-H···Y | pixel | HF |
---|---|---|---|---|---|---|---|---|---|---|
C2 | C15 i | 4.51 | −2.93 | 0.01966 | 0.224 | 4.382 | −89.8 | −66.4 | ||
C11 | H26 i | 9.44 | −6.67 | 0.03728 | 0.448 | 3.733 | 2.85 | 139 | ||
O3 | S14 i | 7.59 | −5 | 0.02788 | 0.374 | 3.538 | ||||
H12 | C16 i | 6.21 | −3.89 | 0.02169 | 0.313 | 3.766 | 3.05 | 124 | ||
H12 | H15C i | 2.9 | −1.98 | 0.01708 | 0.14 | 2.73 | ||||
H13C | H16 i | 11.03 | −7.61 | 0.03883 | 0.531 | 2.28 | ||||
H13C | N5 i | 12.59 | −10.2 | 0.05647 | 0.55 | 3.651 | 2.66 | 151 | ||
H14B | C23 i | 7.24 | −5.36 | 0.03481 | 0.335 | 3.953 | 2.98 | 150 | ||
H15B | H24C i | 7.2 | −4.85 | 0.02851 | 0.351 | 2.46 | ||||
C22 | O15 i | 14.28 | −10.14 | 0.04821 | 0.677 | 3.096 | ||||
H22 | S14 i | 6.18 | −4.27 | 0.02755 | 0.297 | 4.095 | 3.17 | 143 | ||
H23 | N5 ii | 56.52 | −82.77 | 0.27482 | 1.112 | 2.763 | 1.83 | 156 | −39.6 | −60.0 |
O23 | H15B ii | 12.04 | −8.8 | 0.0461 | 0.561 | 3.620 | 2.60 | 155 | ||
O23 | H16 ii | 21.77 | −15.63 | 0.06353 | 1.025 | 3.216 | 2.38 | 132 | ||
O24 | H4 ii | 15.58 | −10.72 | 0.04758 | 0.75 | 3.211 | 2.63 | 113 |
Atom1 | Atom2 | Gcp | Vcp | DEN | LAP | X···Y | H···Y | X-H···Y | pixel | HF |
---|---|---|---|---|---|---|---|---|---|---|
C13 | C15 i | 7.73 | −5.48 | 0.03329 | 0.366 | 3.490 | −105.0 | −67.8 | ||
C4 | N5 i | 2.08 | −1.22 | 0.0089 | 0.108 | 4.083 | ||||
C16 | H15B i | 11.62 | −9.11 | 0.05108 | 0.519 | 3.673 | 2.69 | 150 | ||
H12 | H23B i | 7.18 | −5.23 | 0.0336 | 0.335 | 2.29 | ||||
Br13 | C231 i | 8.05 | −5.3 | 0.02884 | 0.397 | 3.636 | ||||
Br13 | O14 i | 9.33 | −6.44 | 0.03524 | 0.449 | 3.505 | ||||
H14C | O14 i | 14.14 | −11.04 | 0.05703 | 0.633 | 3.593 | 2.52 | 171 | ||
H14C | O15 i | 9.03 | −5.54 | 0.02533 | 0.459 | 3.463 | 2.87 | 115 | ||
C22 | H23B i | 8.91 | −6.4 | 0.03717 | 0.419 | 3.900 | 2.89 | 155 | ||
C24 | S23 i | 7.59 | −5.42 | 0.03341 | 0.358 | 3.674 | ||||
C25 | C23 i | 6.72 | −4.71 | 0.02986 | 0.321 | 3.600 | ||||
H24B | O24 i | 7.52 | −5.33 | 0.03276 | 0.356 | 3.815 | 2.80 | 155 | ||
Br13 | Br13 ii | 12.28 | −9.6 | 0.0526 | 0.549 | 3.564 | −14.2 | −14.4 | ||
Br13 | H23A ii | 8.14 | −5.2 | 0.02691 | 0.407 | 3.838 | 3.19 | 118 | ||
O14 | H23A ii | 4.73 | −3.05 | 0.01997 | 0.235 | 4.057 | 3.00 | 165 | ||
H14A | S23 ii | 3.24 | −1.99 | 0.01374 | 0.165 | 4.232 | 3.51 | 125 |
Atom1 | Atom2 | Gcp | Vcp | DEN | LAP | X···Y | H···Y | X-H···Y | pixel | HF |
---|---|---|---|---|---|---|---|---|---|---|
H14C | O3 i | 2.97 | −1.78 | 0.01199 | 0.153 | 4.188 | 3.22 | 148 | −76.0 | −72.9 |
C15 | H22 i | 6.48 | −4.37 | 0.02686 | 0.315 | 3.803 | 2.99 | 131 | ||
N5 | C12 i | 6.97 | −4.66 | 0.02749 | 0.341 | 3.568 | ||||
H14C | H22 i | 10.3 | −7.12 | 0.03753 | 0.495 | 2.25 | ||||
C4 | H13A i | 13.33 | −9.18 | 0.04339 | 0.642 | 3.467 | 2.76 | 122 | ||
C13 | S14 ii | 4.69 | −3.13 | 0.02168 | 0.229 | 3.886 | −54.5 | −54.0 | ||
H13C | S14 ii | 11.01 | −8.54 | 0.04862 | 0.495 | 3.886 | 2.89 | 142 | ||
H26 | S14 ii | 11.53 | −8.35 | 0.04412 | 0.54 | 3.693 | 2.86 | 133 |
Compound | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
Formula | C20H21NO5S | C20H20BrNO5S | C19H19NO5S | C19H19NO5S | C19H18FNO4S |
Formula weight | 387.44 | 466.34 | 373.41 | 373.41 | 375.40 |
Crystal system | triclinic | monoclinic | triclinic | orthorhombic | triclinic |
Space group | P-1 | P21/c | P-1 | P212121 | P-1 |
a(Å) | 5.1299(4) | 12.3841(4) | 7.7068(3) | 8.3865(4) | 7.8698(8) |
b(Å) | 11.4060(10) | 7.7755(4) | 10.2384(3) | 11.1560(6) | 10.4011(8) |
c(Å) | 16.0097(13) | 21.2517(7) | 11.9461(4) | 19.1503(9) | 12.0236(7) |
α(°) | 97.245(7) | 90 | 108.544(3) | 90 | 72.165(6) |
β(°) | 94.098(7) | 101.623(3) | 94.602(3) | 90 | 88.285(6) |
γ(°) | 99.063(7) | 90 | 100.912(3) | 90 | 68.924(8) |
V(Å3) | 913.68(13) | 2004.42(14) | 867.47(5) | 1791.70(15) | 870.64(13) |
Z | 2 | 4 | 2 | 4 | 2 |
Dx(g cm−3) | 1.408 | 1.545 | 1.430 | 1.384 | 1.432 |
F(000) | 408 | 952 | 392 | 784 | 392 |
μ(mm−1) | 0.210 | 2.186 | 0.218 | 0.211 | 0.221 |
Reflections: | |||||
collected | 17518 | 19235 | 16633 | 6970 | 11038 |
unique (Rint) | 4187 (0.0778) | 3463 (0.0708) | 3837 (0.0227) | 3324 (0.0439) | 3493 (0.0246) |
with I > 2σ(I) | 2504 | 1493 | 3234 | 2876 | 3168 |
R(F) [I > 2σ(I)] | 0.0620 | 0.0535 | 0.0369 | 0.0436 | 0.0325 |
wR(F2) [I > 2σ(I)] | 0.1073 | 0.1045 | 0.0917 | 0.0986 | 0.0806 |
R(F) [all data] | 0.1234 | 0.1402 | 0.0467 | 0.0594 | 0.0362 |
wR(F2) [all data] | 0.1303 | 0.1117 | 0.0956 | 0.1052 | 0.0831 |
Goodness of fit | 1.022 | 0.991 | 1.037 | 1.050 | 1.032 |
Flack parameter | −0.07(6) | ||||
max/min Δ (e·Å−3) | 0.45/−0.38 | 0.41/−0.53 | 0.48/−0.31 | 0.23/−0.26 | 0.27/−0.27 |
CCDC number | 2040699 | 2040698 | 2040700 | 2040701 | 2040702 |
Compound | 6 | 7 | 8 | 9 | |
Formula | C20H21NO4S | C19H18BrNO4S | C19H18BrNO4S | C18H16BrNO4S | |
Formula weight | 371.44 | 436.31 | 436.31 | 422.29 | |
Crystal system | triclinic | monoclinic | monoclinic | orthorhombic | |
Space group | P-1 | P21/c | P21/c | P212121 | |
a(Å) | 8.97622(14) | 12.4359(9) | 19.8673(3) | 8.2803(3) | |
b(Å) | 9.83530(14) | 4.1836(3) | 4.79320(10) | 11.3223(2) | |
c(Å) | 21.8875(3) | 17.9998(12) | 20.3846(4) | 19.3117(4) | |
α(°) | 101.0102(13) | 90 | 90 | 90 | |
β(°) | 94.2346(13) | 103.988(7) | 105.164(2) | 90 | |
γ(°) | 90.0267(12) | 90 | 90 | 90 | |
V(Å3) | 1891.36(5) | 908.70(11) | 1873.59(6) | 1810.51(8) | |
Z | 4 | 2 | 4 | 4 | |
Dx(g cm−3) | 1.304 | 1.595 | 1.547 | 1.549 | |
F(000) | 784 | 444 | 888 | 856 | |
μ(mm−1) | 1.728 | 2.402 | 4.244 | 2.408 | |
Reflections: | |||||
collected | 36875 | 9380 | 16185 | 10218 | |
unique (Rint) | 36875 (0.0160) | 3151 (0.0907) | 3535 (0.0291) | 3269 (0.0307) | |
with I > 2σ(I) | 32098 | 1829 | 3067 | 2882 | |
R(F) [I > 2σ(I)] | 0.0656 | 0.0593 | 0.0392 | 0.0336 | |
wR(F2) [I > 2σ(I)] | 0.1879 | 0.0605 | 0.1147 | 0.0755 | |
R(F) [all data] | 0.0722 | 0.1341 | 0.0479 | 0.0415 | |
wR(F2) [all data] | 0.1879 | 0.0703 | 0.1206 | 0.0782 | |
Goodness of fit | 1.024 | 0.965 | 1.045 | 1.045 | |
Flack parameter | −0.002(4) | ||||
max/min Δ (e·Å−3) | 0.57/−0.32 | 0.40/−0.32 | 0.89/−0.82 | 0.66/−0.37 | |
CCDC number | 2040703 | 2040704 | 2040705 | 2040706 |
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Grześkiewicz, A.M.; Stefański, T.; Kubicki, M. Weak Intermolecular Interactions in a Series of Bioactive Oxazoles. Molecules 2021, 26, 3024. https://doi.org/10.3390/molecules26103024
Grześkiewicz AM, Stefański T, Kubicki M. Weak Intermolecular Interactions in a Series of Bioactive Oxazoles. Molecules. 2021; 26(10):3024. https://doi.org/10.3390/molecules26103024
Chicago/Turabian StyleGrześkiewicz, Anita M., Tomasz Stefański, and Maciej Kubicki. 2021. "Weak Intermolecular Interactions in a Series of Bioactive Oxazoles" Molecules 26, no. 10: 3024. https://doi.org/10.3390/molecules26103024
APA StyleGrześkiewicz, A. M., Stefański, T., & Kubicki, M. (2021). Weak Intermolecular Interactions in a Series of Bioactive Oxazoles. Molecules, 26(10), 3024. https://doi.org/10.3390/molecules26103024