Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one
Abstract
:1. Introduction
2. Results and Discussion
2.1. Solving Structure Attempts
2.2. Crystal Structure Analysis
2.3. Packing and π–π Stacking Interactions
2.4. Theoretical Investigation of the Rotational Barrier
3. Material and Methods
3.1. Physical Measurements
3.2. Synthesis, Characterization, and Crystallization
3.3. Crystal Structure Determinations and Refinement
3.4. DFT Calculations
4. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Ring | Interplanar Distance, Å | Intercentroid Distance, Å | Ring Offset, Å | Angle θ, ° |
---|---|---|---|---|
1a | ||||
o-Cl-Ar | 3.470(3) | 3.8037(2) | 1.559(7) | 24.19(5) |
Fur-2(3H)-one | 3.478(4) | 3.8037(2) | 1.540(8) | 23.89(3) |
p-Tol | 3.380(3) | 3.8037(2) | 1.745(7) | 27.31(4) |
1b | ||||
o-Cl-Ar | 3.519(3) | 3.8037(2) | 1.444(7) | 22.33(8) |
Fur-2(3H)-one | 3.453(4) | 3.8037(2) | 1.596(8) | 24.81(8) |
p-Tol | 3.464(3) | 3.8037(2) | 1.572(7) | 24.41(9) |
Extremum | Contact | C(5)H–Cl(1) | C(3)H–C(11)H | C(5)H–C(11)H | C(3)H–Cl(1) | |||||
---|---|---|---|---|---|---|---|---|---|---|
Angle | 1a | 1b | 1a | 1b | 1a | 1b | 1a | 1b | ||
Global min | −152.303 | −147.749 | 2.690 | 2.722 | 2.242 | 2.307 | 3.711 | 3.692 | 5.657 | 5.583 |
Local max | −82.303 | −87.749 | 3.647 | 3.535 | 4.095 | 3.899 | 3.014 | 3.121 | 3.776 | 3.995 |
Local min | −52.303 | −47.749 | 4.065 | 4.105 | 4.852 | 4.932 | 2.536 | 2.483 | 2.943 | 2.881 |
Global max * | −2.303 | 2.2511 | 4.409 | 4.409 | 5.551 | 5.551 | 2.070 | 2.070 | 2.502 | 2.502 |
Local min | 47.697 | 52.251 | 4.105 | 4.065 | 4.932 | 4.853 | 2.483 | 2.535 | 2.880 | 2.942 |
Local max | 87.697 | 82.2509 | 3.536 | 3.648 | 3.900 | 4.097 | 3.120 | 3.013 | 3.994 | 3.774 |
Global min | 147.697 | 152.251 | 2.723 | 2.690 | 2.308 | 2.243 | 3.692 | 3.711 | 5.581 | 5.655 |
Local max ** | 177.697 | −177.749 | 2.543 | 2.543 | 1.968 | 1.968 | 3.807 | 3.807 | 6.009 | 6.010 |
Geometrical Parameter | Experimental | Calculated | ||
---|---|---|---|---|
1a | 1b | 1a | 1b | |
C(2)–C(5) | 1.354(4) | 1.351(5) | 1.356 | 1.356 |
C(2)–C(3) | 1.437(5) | 1.447(5) | 1.442 | 1.442 |
C(5)–C(6) | 1.461(5) | 1.452(4) | 1.457 | 1.457 |
O(2)···C(5)H | 2.714(4) | 2.628(4) | 2.629 | 2.629 |
C(5)H···Cl(1) | 2.785(3) | 2.651(3) | 2.690 | 2.690 |
C(3)H···C(11)H | 2.303(5) | 2.151(5) | 2.242 | 2.243 |
C(2)–C(5)–C(6) | 124.4(3) | 128.4(3) | 127.858 | 127.843 |
C(2)–C(5)–C(6)–C(7) | −144.5(3) | 157.6(4) | −152.303 | 152.251 |
Crystal data | |
Chemical formula | C18H13ClO2 |
Mr | 296.73 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 100 |
a, b, c (Å) | 28.2038(14), 25.8791(14), 3.8037(2) |
V (Å3) | 2776.3(3) |
Z | 8 |
Z′ | 2 |
Radiation type | CuKα |
µ (mm−1) | 2.44 |
Crystal size (mm) | 0.30 × 0.05 × 0.05 |
Data collection | |
Diffractometer | Bruker APEX II CCD (charge-coupled device) area detector’ diffractometer |
Absorption correction | Multi-scan SADABS |
No. of measured, independent, and observed [I > 2σ(I)] reflections | 26,357, 4925, 4084 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.119, 1.00 |
No. of reflections | 4925 |
No. of parameters | 382 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.42 |
Absolute structure | Refined as an inversion twin |
Absolute structure parameter | 0.36(2) |
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Grinev, V.S.; Mayorova, O.A.; Anis’kova, T.V.; Tikhomolova, A.S.; Yegorova, A.Y. Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one. Molecules 2021, 26, 2137. https://doi.org/10.3390/molecules26082137
Grinev VS, Mayorova OA, Anis’kova TV, Tikhomolova AS, Yegorova AY. Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one. Molecules. 2021; 26(8):2137. https://doi.org/10.3390/molecules26082137
Chicago/Turabian StyleGrinev, Vyacheslav S., Oksana A. Mayorova, Tatyana V. Anis’kova, Alexandra S. Tikhomolova, and Alevtina Yu. Yegorova. 2021. "Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one" Molecules 26, no. 8: 2137. https://doi.org/10.3390/molecules26082137