On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis and Spectral Characteristics of Compounds 3 and 4 (General Method)
2.2. XRD Experimental Part
2.3. Computational Details
3. Results and Discussion
3.1. Structural Description of Compounds 3 and 4
3.2. DFT Calculations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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Compound | 3 | 4 |
---|---|---|
CCDC number | 2118649 | 2118650 |
Empirical formula | C14H11NO2FClBrI | C15H11NO2F3ClBrI |
Formula weight | 486.50 | 536.51 |
Temperature/K | 100(2) | 100(2) |
Crystal system | orthorhombic | monoclinic |
Space group | Pca21 | P21/c |
a/Å | 19.310(2) | 12.2575(9) |
b/Å | 7.2206(8) | 7.0718(5) |
c/Å | 22.530(3) | 19.2040(13) |
α/° | 90 | 90 |
β/° | 90 | 90.781(4) |
γ/° | 90 | 90 |
Volume/Å3 | 3141.4(6) | 1664.5(2) |
Z | 8 | 4 |
ρcalcg/cm3 | 2.057 | 2.141 |
μ/mm−1 | 4.765 | 4.524 |
F(000) | 1856.0 | 1024.0 |
Crystal size/mm3 | 0.16 × 0.12 × 0.08 | 0.4 × 0.18 × 0.14 |
Radiation | MoKα (λ = 0.71073) | MoKα (λ = 0.71073) |
2Θ range for data collection/° | 8.378 to 54.998 | 6.968 to 70 |
Index ranges | −25 ≤ h ≤ 25, −9 ≤ k ≤ 8, −29 ≤ l ≤ 29 | −19 ≤ h ≤ 19, −11 ≤ k ≤ 10, −30 ≤ l ≤ 30 |
Reflections collected | 44,518 | 42,785 |
Independent reflections | 7191 [Rint = 0.0816, Rsigma = 0.0605] | 7322 [Rint = 0.0282, Rsigma = 0.0217] |
Data/restraints/parameters | 7191/1/380 | 7322/0/245 |
Goodness-of-fit on F2 | 1.016 | 1.030 |
Final R indexes [I ≥ 2σ (I)] | R1 = 0.0344, wR2 = 0.0575 | R1 = 0.0216, wR2 = 0.0443 |
Final R indexes [all data] | R1 = 0.0503, wR2 = 0.0617 | R1 = 0.0310, wR2 = 0.0468 |
Largest diff. peak/hole/e Å−3 | 0.93/−0.67 | 0.57/−1.00 |
Bond | Length/Å | Length/Å | Length/Å |
---|---|---|---|
3, molecule A | 3, molecule B | 4 | |
I1-C5 | 2.146(8) | 2.138(7) | 2.1361(12) |
Br1-C6 | 1.922(7) | 1.913(7) | 1.9150(12) |
Cl1-C4 | 1.815(7) | 1.814(8) | 1.8202(12) |
O1-C1 | 1.236(9) | 1.224(9) | 1.2262(16) |
O8-C4 | 1.420(9) | 1.416(9) | 1.4177(15) |
O8-C6 | 1.453(8) | 1.446(8) | 1.4457(16) |
N2-C1 | 1.354(9) | 1.364(10) | 1.3576(17) |
N2-C3 | 1.465(9) | 1.461(9) | 1.4621(16) |
N2-C11 | 1.437(9) | 1.446(9) | 1.4369(17) |
C1-C7A | 1.501(10) | 1.526(10) | 1.5111(18) |
C3-C4 | 1.523(10) | 1.492(10) | 1.5159(18) |
C4-C4A | 1.506(10) | 1.518(10) | 1.5189(18) |
C4A-C5 | 1.534(10) | 1.535(10) | 1.5394(18) |
C4A-C7A | 1.573(10) | 1.560(10) | 1.5612(18) |
C5-C6 | 1.523(10) | 1.526(10) | 1.5261(18) |
C6-C7 | 1.506(10) | 1.531(10) | 1.5219(18) |
C7-C7A | 1.585(11) | 1.567(11) | 1.5755(18) |
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Mertsalov, D.F.; Gomila, R.M.; Zaytsev, V.P.; Grigoriev, M.S.; Nikitina, E.V.; Zubkov, F.I.; Frontera, A. On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms. Crystals 2021, 11, 1406. https://doi.org/10.3390/cryst11111406
Mertsalov DF, Gomila RM, Zaytsev VP, Grigoriev MS, Nikitina EV, Zubkov FI, Frontera A. On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms. Crystals. 2021; 11(11):1406. https://doi.org/10.3390/cryst11111406
Chicago/Turabian StyleMertsalov, Dmitriy F., Rosa M. Gomila, Vladimir P. Zaytsev, Mikhail S. Grigoriev, Eugeniya V. Nikitina, Fedor I. Zubkov, and Antonio Frontera. 2021. "On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms" Crystals 11, no. 11: 1406. https://doi.org/10.3390/cryst11111406