Abstract
This article reports the single-crystal X-ray diffraction dataset of some isobutyl-1,2,6-triaryl-4-(arylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (1-3) derivatives with Hirshfeld surface analysis. Pictorial representations of intramolecular hydrogen bonding in 1-3 with the characteristics of Resonance Assisted Hydrogen Bonding (RAHB) are presented. The data corresponding to the Hirshfeld surface analysis is given.
Keywords: Tetrahydropyridine, XRD, Hirshfeld surface, RAHB
Specifications Table
| Subject | Organic Chemistry |
| Specific subject area | Structural Chemistry |
| Type of data | Figure, Table |
| How data were acquired |
Single Crystal X-ray diffraction: Bruker, 2004 APEX 2 diffractometer (for 1 and 3) and Bruker D8 QUEST diffractometer (for 2). Hirshfled: Crystal Explorer 3.1 version software. |
| Data format | Raw data and Analyzed. |
| Parameters for data collection |
SXRD: Diffraction data were collected on a Bruker, 2004 APEX 2 diffractometer using graphite monochromated Mo Kα radiation (λ = 0.71073 Å) at 296 K for 1 and 3, and for 2 Bruker D8 QUEST diffractometer was used with graphite monochromated Mo Kα radiation (λ = 0.71073 Å) at 100 K. Hirshfled: The fingerprint plots and Hirshfeld surface data were generated by using Crystal Explorer 3.1 software program. |
| Description of data collection | Crystals of compounds were immersed in cryo-oil, mounted in a nylon loop. |
| Data source location | Department of Chemistry, Annamalai University, Annamalainagar, Chidambaram, 608 002, Tamil Nadu, India. |
| Data accessibility | Single crystal X-ray structural and Hirshfeld surface analysis data can be accessed at https://data.mendeley.com/datasets/4p5t89zs4v/draft?a=b8bfd08f-a27c-4919-ae70-0648f7ed9116. The Cambridge Crystallographic Data Centre. CCDC 1978944 (for 1), 1978942 (for 2) and 1978943 (for 3), Copies of the data can be obtained free of charge via (http://www.ccdc.cam.ac.uk/conts/retrieving.html, Email: deposit@ccdc.cam.ac.uk.). |
| Related research article | Poyyamozhi Surendar Anand, Annamalai Sethukumar, Chandran Udhaya Kumar, Kuppusamy Krishnasamy, Sivakolunthu Senthan, Govindhasamy Manikandan, Balasubramaniam Arul Prakasam, Synthesis, stereochemical, single crystal X-ray structural and antimicrobial studies of some isobutyl-1,2,6-triaryl-4-(arylamino)-1,2,5,6-tetrahydropyridine-3-carboxylates: Exploring RAHB with S(6) graph set, J. Mol. Struct. 2020, 129563, https://doi.org/10.1016/j.molstruc.2020.129563. |
Value of the Data
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The presented single crystal X-ray diffraction data will be of interest to researchers in the field of structural chemistry for the comparison with other XRD reports.
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The data will be useful to the researchers who are interested in studying Resonance Assisted Hydrogen Bonding (RAHB).
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The quantified intermolecular interactions in the crystal structures by Hirshfeld surface analysis is the modern approach towards the packing analysis in the crystals.
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The data in this article will be useful for the investigators who are interested in studying non bonded interactions.
1. Data Description
The single crystal X-ray structural data of compounds 1-3 are presented with their Hirshfeld surface analysis in this report. Selected bond distances, bond angles, torsion angles, anisotropic atomic displacement and atomic coordinates for 1-3 are depicted in Table 1-15. The molecular structure of the compounds 1-3 are given in Fig. 1. The pseudo six-membered rings formed due to Resonance Assisted Hydrogen Bonding (RAHB) are shown in Fig. 2. Hirshfeld surface analysis and fingerprint plots were carried out and the intermolecular interactions are quantified [1], [2], [3], [4], [5], [6], [7], [8]. Hirshfeld surface mapped with dnorm, di, de, shape index and curvedness of compounds 1, 2, and 3 are shown in Fig. 3, 5, and 7 where, dnorm = Normalized contact distance, di = Distance from the surface to the nearest nucleus internal to the surface, de = Distance from the surface to the nearest nucleus external to the surface, Shape index = Qualitative measure of shape and Curvedness = Function of the root-mean-square curvature of the surface. The bright red spots in the sub sects’ b and c of Fig. 3, 5, and 7 are the hydrogen bonding centers and the weak and long range intermolecular interactions are indicated with the pale colours. In the shape index, the bright-red spot exemplifies the hydrogen bonding interactions while the blue spots indicate the complementary hydrogen bonding interactions.
Table 2.
Anisotropic atomic displacement parameters (Å) for compound 1.
| U11 | U22 | U33 | U23 | U13 | U12 | |
|---|---|---|---|---|---|---|
| C1 | 0.0664(10) | 0.0511(9) | 0.0572(9) | -0.0093(7) | -0.0172(8) | -0.0187(8) |
| C2 | 0.1018(15) | 0.0672(12) | 0.0630(11) | -0.0178(10) | -0.0368(11) | -0.0136(11) |
| C3 | 0.1127(17) | 0.0666(12) | 0.0404(9) | -0.0131(8) | -0.0197(10) | 0.0086(11) |
| C4 | 0.0914(14) | 0.0666(11) | 0.0486(10) | 0.0016(8) | 0.0117(9) | -0.0135(10) |
| C5 | 0.0637(10) | 0.0585(10) | 0.0515(9) | -0.0073(7) | 0.0014(7) | -0.0235(8) |
| C6 | 0.0429(7) | 0.0364(7) | 0.0357(7) | -0.0100(5) | -0.0026(5) | -0.0060(5) |
| C7 | 0.0356(6) | 0.0355(7) | 0.0348(6) | -0.0058(5) | -0.0012(5) | -0.0124(5) |
| C8 | 0.0407(7) | 0.0378(7) | 0.0302(6) | -0.0034(5) | -0.0035(5) | -0.0091(5) |
| C9 | 0.0376(7) | 0.0385(7) | 0.0294(6) | -0.0048(5) | -0.0056(5) | -0.0057(5) |
| C10 | 0.0382(7) | 0.0351(6) | 0.0310(6) | -0.0036(5) | -0.0075(5) | -0.0066(5) |
| C11 | 0.0398(7) | 0.0337(6) | 0.0370(7) | -0.0048(5) | -0.0060(5) | -0.0110(5) |
| C12 | 0.0371(6) | 0.0342(6) | 0.0294(6) | -0.0077(5) | -0.0063(5) | -0.0051(5) |
| C13 | 0.0411(7) | 0.0328(7) | 0.0558(8) | -0.0126(6) | -0.0133(6) | -0.0020(6) |
| C14 | 0.0370(7) | 0.0443(8) | 0.0564(9) | -0.0163(6) | -0.0112(6) | -0.0048(6) |
| C15 | 0.0469(7) | 0.0423(7) | 0.0353(7) | -0.0118(5) | -0.0043(5) | -0.0160(6) |
| C16 | 0.0501(8) | 0.0313(6) | 0.0416(7) | -0.0049(5) | -0.0059(6) | -0.0072(6) |
| C17 | 0.0357(7) | 0.0363(7) | 0.0390(7) | -0.0039(5) | -0.0068(5) | -0.0034(5) |
| C18 | 0.0905(13) | 0.0529(10) | 0.0721(12) | -0.0199(8) | -0.0018(10) | -0.0361(9) |
| C19 | 0.0402(7) | 0.0426(7) | 0.0312(6) | -0.0054(5) | -0.0007(5) | -0.0153(6) |
| C20 | 0.0441(8) | 0.0598(9) | 0.0327(7) | -0.0076(6) | -0.0049(6) | -0.0128(7) |
| C21 | 0.0606(9) | 0.0726(11) | 0.0313(7) | -0.0119(7) | -0.0026(6) | -0.0195(8) |
| C22 | 0.0581(9) | 0.0745(11) | 0.0378(8) | -0.0183(7) | 0.0091(7) | -0.0153(8) |
| C23 | 0.0418(8) | 0.0675(10) | 0.0483(8) | -0.0151(7) | 0.0046(6) | -0.0117(7) |
| C24 | 0.0399(7) | 0.0559(8) | 0.0374(7) | -0.0100(6) | -0.0025(6) | -0.0144(6) |
| C25 | 0.0374(7) | 0.0515(8) | 0.0314(6) | -0.0119(6) | -0.0026(5) | -0.0100(6) |
| C26 | 0.0475(8) | 0.0519(9) | 0.0571(9) | -0.0063(7) | -0.0119(7) | -0.0145(7) |
| C27 | 0.0568(10) | 0.0576(10) | 0.0769(12) | -0.0155(8) | -0.0031(8) | -0.0217(8) |
| C28 | 0.0499(9) | 0.0849(13) | 0.0596(10) | -0.0312(9) | 0.0028(7) | -0.0299(9) |
| C29 | 0.0494(9) | 0.1078(15) | 0.0464(9) | -0.0151(9) | -0.0129(7) | -0.0269(9) |
| C30 | 0.0463(8) | 0.0746(11) | 0.0391(8) | -0.0017(7) | -0.0096(6) | -0.0178(7) |
| C31 | 0.0801(15) | 0.179(3) | 0.0954(17) | -0.0430(17) | -0.0093(13) | -0.0758(17) |
| C32 | 0.0532(8) | 0.0350(7) | 0.0434(7) | -0.0041(6) | -0.0120(6) | -0.0134(6) |
| N1 | 0.0352(6) | 0.0461(6) | 0.0299(5) | -0.0082(4) | -0.0058(4) | -0.0081(5) |
| N2 | 0.0551(7) | 0.0361(6) | 0.0374(6) | -0.0075(5) | -0.0077(5) | -0.0100(5) |
| O1 | 0.0790(8) | 0.0337(5) | 0.0574(7) | -0.0105(5) | -0.0192(6) | -0.0066(5) |
| O2 | 0.0942(9) | 0.0348(5) | 0.0507(6) | -0.0021(4) | -0.0326(6) | -0.0002(5) |
| O3 | 0.0583(7) | 0.0518(6) | 0.0704(7) | -0.0157(5) | -0.0097(5) | -0.0250(5) |
| O4 | 0.0743(9) | 0.1212(13) | 0.0967(11) | -0.0385(9) | -0.0052(8) | -0.0553(9) |
| C33 | 0.117(6) | 0.052(4) | 0.078(4) | 0.000(3) | -0.050(3) | 0.015(4) |
| C34 | 0.182(6) | 0.050(3) | 0.070(3) | 0.005(2) | -0.053(3) | 0.014(4) |
| C35 | 0.208(6) | 0.181(8) | 0.088(5) | 0.033(4) | -0.017(4) | -0.012(5) |
| C36 | 0.212(9) | 0.075(3) | 0.083(5) | 0.017(3) | -0.053(5) | 0.024(5) |
Table 3.
Bond distance (Å) for compound 1.
| Bond distances (Å) | |||
|---|---|---|---|
| C1-C6 | 1.374(2) | C19-C24 | 1.4017(19) |
| C1-C2 | 1.377(3) | C19-C20 | 1.4058(19) |
| C1-H1 | 0.93 | C20-C21 | 1.383(2) |
| C2-C3 | 1.357(3) | C20-H20 | 0.93 |
| C2-H2 | 0.93 | C21-C22 | 1.379(2) |
| C3-C4 | 1.371(3) | C21-H21 | 0.93 |
| C3-H3 | 0.93 | C22-C23 | 1.376(2) |
| C4-C5 | 1.386(3) | C22-H22 | 0.93 |
| C4-H4 | 0.93 | C23-C24 | 1.379(2) |
| C5-C6 | 1.380(2) | C23-H23 | 0.93 |
| C5-H5 | 0.93 | C24-H24 | 0.93 |
| C6-N2 | 1.4214(17) | C25-C30 | 1.383(2) |
| C7-N2 | 1.3529(17) | C25-C26 | 1.386(2) |
| C7-C11 | 1.3669(18) | C26-C27 | 1.381(2) |
| C7-C8 | 1.4978(18) | C26-H26 | 0.93 |
| C8-C9 | 1.5456(17) | C27-C28 | 1.376(3) |
| C8-H8A | 0.97 | C27-H27 | 0.93 |
| C8-H8B | 0.97 | C28-C29 | 1.373(3) |
| C9-N1 | 1.4602(15) | C28-O4 | 1.376(2) |
| C9-C25 | 1.5188(18) | C29-C30 | 1.395(2) |
| C9-H9 | 0.98 | C29-H29 | 0.93 |
| C10-N1 | 1.4678(16) | C30-H30 | 0.93 |
| C10-C11 | 1.5159(17) | C31-O4 | 1.405(3) |
| C10-C12 | 1.5328(18) | C31-H31A | 0.96 |
| C10-H10 | 0.98 | C31-H31B | 0.96 |
| C11-C32 | 1.4412(19) | C31-H31C | 0.96 |
| C12-C17 | 1.3804(18) | C32-O1 | 1.2232(17) |
| C12-C13 | 1.3964(18) | C32-O2 | 1.3465(17) |
| C13-C14 | 1.376(2) | N2-H2A | 0.877(19) |
| C13-H13 | 0.93 | O2-C33 | 1.513(18) |
| C14-C15 | 1.383(2) | C33-C34 | 1.490(13) |
| C14-H14 | 0.93 | C33-H33A | 0.97 |
| C15-O3 | 1.3738(17) | C33-H33B | 0.97 |
| C15-C16 | 1.378(2) | C34-C35 | 1.481(11) |
| C16-C17 | 1.3884(19) | C34-C36 | 1.523(8) |
| C16-H16 | 0.93 | C34-H34 | 0.98 |
| C17-H17 | 0.93 | C35-H35A | 0.96 |
| C18-O3 | 1.415(2) | C35-H35B | 0.96 |
| C18-H18A | 0.96 | C35-H35C | 0.96 |
| C18-H18B | 0.96 | C36-H36A | 0.96 |
| C18-H18C | 0.96 | C36-H36B | 0.96 |
| C19-N1 | 1.3925(16) | C36-H36C | 0.96 |
| H(2A) ••••O(1) | 2.000(19) | N(2)-H(2A) ••••O(1) | 2.6933(16) |
Table 4.
Bond angles (°) for compound 1.
| Bond angles (°) | |||||
|---|---|---|---|---|---|
| C6-C1-C2 | 120.09(17) | C13-C14-C15 | 120.13(13) | C28-C29-C30 | 119.78(15) |
| C6-C1-H1 | 120 | C13-C14-H14 | 119.9 | C28-C29-H29 | 120.1 |
| C2-C1-H1 | 120 | C15-C14-H14 | 119.9 | C30-C29 H29 | 120.1 |
| C3-C2-C1 | 120.49(18) | O3-C15-C16 | 124.07(13) | C25-C30-C29 | 121.34(16) |
| C3-C2-H2 | 119.8 | O3-C15-C14 | 116.20(12) | C25-C30-H30 | 119.3 |
| C1-C2-H2 | 119.8 | C16-C15-C14 | 119.74(13) | C29-C30-H30 | 119.3 |
| C2-C3-C4 | 120.26(17) | C15-C16-C17 | 119.44(12) | O4-C31-H31A | 109.5 |
| C2-C3-H3 | 119.9 | C15-C16-H16 | 120.3 | O4-C31-H31B | 109.5 |
| C4-C3-H3 | 119.9 | C17-C16-H16 | 120.3 | H31A-C31-H31B | 109.5 |
| C3-C4-C5 | 119.78(18) | C12-C17-C16 | 122.01(12) | O4-C31-H31C | 109.5 |
| C3-C4-H4 | 120.1 | C12-C17-H17 | 119 | H31A-C31-H31C | 109.5 |
| C5-C4-H4 | 120.1 | C16-C17-H17 | 119 | H31B-C31-H31C | 109.5 |
| C6-C5-C4 | 119.89(17) | O3-C18-H18A | 109.5 | O1-C32-O2 | 121.47(12) |
| C6-C5-H5 | 120.1 | O3-C18-H18B | 109.5 | O1-C32-C11 | 125.80(13) |
| C4-C5-H5 | 120.1 | H18A-C18-H18B | 109.5 | O2-C32-C11 | 112.73(12) |
| C1-C6-C5 | 119.47(14) | O3-C18-H18C | 109.5 | C19-N1-C9 | 119.62(10) |
| C1-C6-N2 | 119.21(13) | H18A-C18-H18C | 109.5 | C19-N1-C10 | 120.10(10) |
| C5-C6-N2 | 121.27(13) | H18B-C18-H18C | 109.5 | C9-N1-C10 | 119.18(10) |
| N2-C7-C11 | 124.31(12) | N1-C19-C24 | 121.31(12) | C7-N2-C6 | 126.84(12) |
| N2-C7-C8 | 119.92(11) | N1-C19-C20 | 121.62(12) | C7-N2-H2A | 114.7(12) |
| C11-C7-C8 | 115.65(11) | C24-C19-C20 | 117.06(12) | C6-N2-H2A | 118.0(12) |
| C7-C8-C9 | 109.52(10) | C21-C20-C19 | 120.94(14) | C32-O2-C33 | 118.4(5) |
| C7-C8-H8A | 109.8 | C21-C20-H20 | 119.5 | C15-O3-C18 | 116.80(13) |
| C9-C8-H8A | 109.8 | C19-C20-H20 | 119.5 | C28-O4-C31 | 117.84(19) |
| C7-C8-H8B | 109.8 | C22-C21-C20 | 121.21(14) | C34-C33-O2 | 104.1(12) |
| C9-C8-H8B | 109.8 | C22-C21-H21 | 119.4 | C34-C33-H33A | 110.9 |
| H8A-C8-H8B | 108.2 | C20-C21-H21 | 119.4 | O2-C33-H33A | 110.9 |
| N1-C9-C25 | 113.99(10) | C23-C22-C21 | 118.27(14) | C34-C33-H33B | 110.9 |
| N1-C9-C8 | 109.98(10) | C23-C22-H22 | 120.9 | O2-C33-H33B | 110.9 |
| C25-C9-C8 | 109.69(10) | C21-C22-H22 | 120.9 | H33A-C33-H33B | 109 |
| N1-C9-H9 | 107.6 | C22-C23-C24 | 121.75(14) | C35-C34-C33 | 115.1(10) |
| C25-C9-H9 | 107.6 | C22-C23-H23 | 119.1 | C35-C34-C36 | 106.0(8) |
| C8-C9-H9 | 107.6 | C24-C23-H23 | 119.1 | C33-C34-C36 | 107.2(10) |
| N1-C10-C11 | 110.35(10) | C23-C24-C19 | 120.77(13) | C35-C34-H34 | 109.4 |
| N1-C10-C12 | 112.97(10) | C23-C24-H24 | 119.6 | C33-C34-H34 | 109.4 |
| C11-C10-C12 | 113.22(10) | C19-C24-H24 | 119.6 | C36-C34-H34 | 109.4 |
| N1-C10-H10 | 106.6 | C30-C25-C26 | 117.56(14) | C34-C35-H35A | 109.5 |
| C11-C10-H10 | 106.6 | C30-C25-C9 | 119.69(13) | C34-C35-H35B | 109.5 |
| C12-C10-H10 | 106.6 | C26-C25-C9 | 122.69(12) | H35A-C35-H35B | 109.5 |
| C7-C11-C32 | 120.97(12) | C27-C26-C25 | 121.44(15) | C34-C35-H35C | 109.5 |
| C7-C11-C10 | 117.77(11) | C27-C26-H26 | 119.3 | H35A-C35-H35C | 109.5 |
| C32-C11-C10 | 121.25(11) | C25-C26-H26 | 119.3 | H35B-C35-H35C | 109.5 |
| C17-C12-C13 | 117.28(12) | C28-C27-C26 | 120.21(17) | C34-C36-H36A | 109.5 |
| C17-C12-C10 | 122.32(11) | C28-C27-H27 | 119.9 | C34-C36-H36B | 109.5 |
| C13-C12-C10 | 120.33(11) | C26-C27-H27 | 119.9 | H36A-C36-H36B | 109.5 |
| C14-C13-C12 | 121.41(12) | C29-C28-O4 | 124.72(17) | C34-C36-H36C | 109.5 |
| C14-C13-H13 | 119.3 | C29-C28-C27 | 119.65(15) | H36A-C36-H36C | 109.5 |
| C12-C13-H13 | 119.3 | O4-C28-C27 | 115.61(18) | H36B-C36-H36C | 109.5 |
| N(2)-H(2A)••••O(1) | 135.0(16) | ||||
Table 5.
Torsional angles [°] for compound 1.
| Torsional angles [°] | |||
|---|---|---|---|
| C6-C1-C2-C3 | 0.9(3) | C8-C9-C25-C30 | 82.97(15) |
| C1-C2-C3-C4 | 0.8(3) | N1-C9-C25-C26 | 29.73(18) |
| C2-C3-C4-C5 | -1.5(3) | C8-C9-C25-C26 | -94.09(15) |
| C3-C4-C5-C6 | 0.6(3) | C30-C25-C26-C27 | -1.4(2) |
| C2-C1-C6-C5 | -1.7(2) | C9-C25-C26-C27 | 175.71(14) |
| C2-C1-C6-N2 | 175.59(15) | C25-C26-C27-C28 | -0.1(3) |
| C4-C5-C6-C1 | 1.0(2) | C26-C27-C28-C29 | 1.4(3) |
| C4-C5-C6-N2 | -176.28(15) | C26-C27-C28-O4 | -179.98(15) |
| N2-C7-C8-C9 | -127.50(12) | O4-C28-C29-C30 | -179.69(15) |
| C11-C7-C8-C9 | 48.80(15) | C27-C28-C29-C30 | -1.2(3) |
| C7-C8-C9-N1 | -53.98(14) | C26-C25-C30-C29 | 1.6(2) |
| C7-C8-C9-C25 | 72.15(13) | C9-C25-C30-C29 | -175.61(14) |
| N2-C7-C11-C32 | -2.0(2) | C28-C29-C30-C25 | -0.3(3) |
| C8-C7-C11-C32 | -178.08(12) | C7-C11-C32-O1 | 2.1(2) |
| N2-C7-C11-C10 | 177.19(12) | C10-C11-C32-O1 | -177.05(14) |
| C8-C7-C11-C10 | 1.08(17) | C7-C11-C32-O2 | -177.53(12) |
| N1-C10-C11-C7 | -44.49(15) | C10-C11-C32-O2 | 3.33(19) |
| C12-C10-C11-C7 | 83.25(14) | C24-C19-N1-C9 | -15.20(19) |
| N1-C10-C11-C32 | 134.67(13) | C20-C19-N1-C9 | 163.97(12) |
| C12-C10-C11-C32 | -97.59(14) | C24-C19-N1-C10 | 176.91(12) |
| N1-C10-C12-C17 | -0.03(17) | C20-C19-N1-C10 | -3.92(19) |
| C11-C10-C12-C17 | -126.39(13) | C25-C9-N1-C19 | 79.21(14) |
| N1-C10-C12-C13 | -176.83(11) | C8-C9-N1-C19 | -157.13(11) |
| C11-C10-C12-C13 | 56.80(16) | C25-C9-N1-C10 | -112.79(12) |
| C17-C12-C13-C14 | -0.3(2) | C8-C9-N1-C10 | 10.87(15) |
| C10-C12-C13-C14 | 176.66(12) | C11-C10-N1-C19 | -155.38(11) |
| C12-C13-C14-C15 | -0.1(2) | C12-C10-N1-C19 | 76.75(14) |
| C13-C14-C15-O3 | -179.79(13) | C11-C10-N1-C9 | 36.68(15) |
| C13-C14-C15-C16 | 0.6(2) | C12-C10-N1-C9 | -91.19(13) |
| O3-C15-C16-C17 | 179.76(12) | C11-C7-N2-C6 | 170.34(13) |
| C14-C15-C16-C17 | -0.7(2) | C8-C7-N2-C6 | -13.7(2) |
| C13-C12-C17-C16 | 0.24(19) | C1-C6-N2-C7 | 122.95(16) |
| C10-C12-C17-C16 | -176.66(12) | C5-C6-N2-C7 | -59.8(2) |
| C15-C16-C17-C12 | 0.2(2) | O1-C32-O2-C33 | -7.1(8) |
| N1-C19-C20-C21 | -179.44(14) | C11-C32-O2-C33 | 172.6(8) |
| C24-C19-C20-C21 | -0.2(2) | C16-C15-O3-C18 | -21.3(2) |
| C19-C20-C21-C22 | 0.0(2) | C14-C15-O3-C18 | 159.08(14) |
| C20-C21-C22-C23 | -0.2(3) | C29-C28-O4-C31 | -5.5(3) |
| C21-C22-C23-C24 | 0.6(3) | C27-C28-O4-C31 | 175.94(19) |
| C22-C23-C24-C19 | -0.8(2) | C32-O2-C33-C34 | 160.3(7) |
| N1-C19-C24-C23 | 179.82(13) | O2-C33-C34-C35 | -58.3(13) |
| C20-C19-C24-C23 | 0.6(2) | O2-C33-C34-C36 | -175.9(10) |
| N1-C9-C25-C30 | -153.21(13) | ||
Table 6.
Atomic coordinates and equivalent isotropic atomic displacement parameters (Å) for compound 2.
| x/a | y/b | z/c | U (eq) | |
|---|---|---|---|---|
| F1 | 0.65860(14) | 0.21604(13) | 1.08335(10) | 0.0389(4) |
| F2 | 0.54046(17) | 0.94085(17) | 0.09024(11) | 0.0545(5) |
| O1 | 0.91637(16) | 0.85354(15) | 0.58988(13) | 0.0330(4) |
| O2 | -0.03237(16) | 0.32345(14) | 0.71665(12) | 0.0290(4) |
| O3 | 0.11899(15) | 0.79776(13) | 0.80742(11) | 0.0255(3) |
| O4 | 0.18907(16) | 0.93830(14) | 0.66745(12) | 0.0288(4) |
| N1 | 0.45448(17) | 0.54527(16) | 0.74331(13) | 0.0241(4) |
| N2 | 0.36618(19) | 0.85201(17) | 0.51325(14) | 0.0251(4) |
| C1 | 0.5411(2) | 0.56523(19) | 0.64186(16) | 0.0232(4) |
| C2 | 0.4529(2) | 0.62907(19) | 0.55678(16) | 0.0241(4) |
| C3 | 0.3638(2) | 0.74323(19) | 0.58258(16) | 0.0225(4) |
| C4 | 0.2911(2) | 0.72934(19) | 0.68088(16) | 0.0226(4) |
| C5 | 0.1986(2) | 0.8314(2) | 0.71535(16) | 0.0241(4) |
| C6 | 0.0185(2) | 0.8935(2) | 0.84360(18) | 0.0307(5) |
| C7 | -0.0533(2) | 0.8423(2) | 0.95052(18) | 0.0323(5) |
| C8 | -0.1582(3) | 0.9456(3) | 0.9884(2) | 0.0460(7) |
| C9 | -0.1177(3) | 0.7413(3) | 0.9534(2) | 0.0573(9) |
| C10 | 0.3100(2) | 0.60340(19) | 0.75265(16) | 0.0223(4) |
| C11 | 0.2238(2) | 0.52575(19) | 0.73899(16) | 0.0227(4) |
| C12 | 0.0858(2) | 0.57350(19) | 0.73648(17) | 0.0258(4) |
| C13 | 0.0032(2) | 0.50388(19) | 0.73017(17) | 0.0268(5) |
| C14 | 0.0575(2) | 0.38449(19) | 0.72480(16) | 0.0245(4) |
| C15 | 0.1934(2) | 0.3351(2) | 0.72629(17) | 0.0266(5) |
| C16 | 0.2750(2) | 0.40632(19) | 0.73358(17) | 0.0262(5) |
| C17 | 0.0050(3) | 0.1952(2) | 0.74688(19) | 0.0335(5) |
| C18 | 0.5057(2) | 0.46183(19) | 0.82859(16) | 0.0240(4) |
| C19 | 0.4200(2) | 0.4211(2) | 0.92133(16) | 0.0264(5) |
| C20 | 0.4714(2) | 0.3394(2) | 1.00634(17) | 0.0293(5) |
| C21 | 0.6086(2) | 0.2966(2) | 0.99904(17) | 0.0291(5) |
| C22 | 0.6958(2) | 0.3324(2) | 0.91019(18) | 0.0289(5) |
| C23 | 0.6449(2) | 0.4145(2) | 0.82468(17) | 0.0260(5) |
| C24 | 0.6431(2) | 0.63967(19) | 0.63083(16) | 0.0231(4) |
| C25 | 0.7550(2) | 0.6342(2) | 0.55142(17) | 0.0272(5) |
| C26 | 0.8475(2) | 0.7048(2) | 0.53391(18) | 0.0303(5) |
| C27 | 0.8295(2) | 0.7820(2) | 0.59755(17) | 0.0257(5) |
| C28 | 0.7190(2) | 0.7878(2) | 0.67746(18) | 0.0277(5) |
| C29 | 0.6264(2) | 0.71774(19) | 0.69350(17) | 0.0252(4) |
| C30 | 1.0326(2) | 0.8465(2) | 0.51033(19) | 0.0359(6) |
| C31 | 0.4154(2) | 0.86947(19) | 0.40466(16) | 0.0240(4) |
| C32 | 0.5076(2) | 0.9417(2) | 0.35809(18) | 0.0287(5) |
| C33 | 0.5505(2) | 0.9667(2) | 0.25166(19) | 0.0340(5) |
| C34 | 0.4998(2) | 0.9168(2) | 0.19434(17) | 0.0354(6) |
| C35 | 0.4105(2) | 0.8435(2) | 0.23796(18) | 0.0338(5) |
| C36 | 0.3663(2) | 0.8204(2) | 0.34432(17) | 0.0293(5) |
Table 7.
Anisotropic atomic displacement parameters (Å) for compound 2.
| U11 | U22 | U33 | U23 | U13 | U12 | |
|---|---|---|---|---|---|---|
| F1 | 0.0428(8) | 0.0428(8) | 0.0283(7) | 0.0050(6) | -0.0170(6) | -0.0108(7) |
| F2 | 0.0513(10) | 0.0811(13) | 0.0190(7) | -0.0019(7) | 0.0002(6) | -0.0125(9) |
| O1 | 0.0303(9) | 0.0381(9) | 0.0342(9) | -0.0083(7) | -0.0036(7) | -0.0156(7) |
| O2 | 0.0310(8) | 0.0240(8) | 0.0360(9) | -0.0101(6) | -0.0061(7) | -0.0092(7) |
| O3 | 0.0269(8) | 0.0272(8) | 0.0226(8) | -0.0095(6) | -0.0005(6) | -0.0062(6) |
| O4 | 0.0361(9) | 0.0236(8) | 0.0277(8) | -0.0071(6) | -0.0031(7) | -0.0095(7) |
| N1 | 0.0209(9) | 0.0283(10) | 0.0202(9) | -0.0031(7) | -0.0036(7) | -0.0042(7) |
| N2 | 0.0301(10) | 0.0246(10) | 0.0210(9) | -0.0064(7) | -0.0026(7) | -0.0077(8) |
| C1 | 0.0244(10) | 0.0255(11) | 0.0192(10) | -0.0035(8) | -0.0052(8) | -0.0057(8) |
| C2 | 0.0265(11) | 0.0260(11) | 0.0204(10) | -0.0066(8) | -0.0052(8) | -0.0047(9) |
| C3 | 0.0225(10) | 0.0276(11) | 0.0206(10) | -0.0073(8) | -0.0067(8) | -0.0064(8) |
| C4 | 0.0252(10) | 0.0237(10) | 0.0205(10) | -0.0070(8) | -0.0044(8) | -0.0059(8) |
| C5 | 0.0278(11) | 0.0285(11) | 0.0199(10) | -0.0074(8) | -0.0036(8) | -0.0113(9) |
| C6 | 0.0324(12) | 0.0309(12) | 0.0270(12) | -0.0113(9) | -0.0024(9) | -0.0024(10) |
| C7 | 0.0321(12) | 0.0414(14) | 0.0250(12) | -0.0115(10) | -0.0036(9) | -0.0080(10) |
| C8 | 0.0356(14) | 0.0613(18) | 0.0338(14) | -0.0173(13) | -0.0013(11) | 0.0025(13) |
| C9 | 0.069(2) | 0.073(2) | 0.0418(17) | -0.0225(15) | 0.0145(15) | -0.0463(18) |
| C10 | 0.0219(10) | 0.0244(10) | 0.0209(10) | -0.0063(8) | -0.0028(8) | -0.0058(8) |
| C11 | 0.0252(10) | 0.0236(10) | 0.0196(10) | -0.0046(8) | -0.0043(8) | -0.0062(8) |
| C12 | 0.0243(11) | 0.0215(10) | 0.0310(12) | -0.0072(8) | -0.0044(9) | -0.0035(8) |
| C13 | 0.0246(11) | 0.0239(11) | 0.0323(12) | -0.0059(9) | -0.0062(9) | -0.0059(9) |
| C14 | 0.0296(11) | 0.0229(10) | 0.0223(11) | -0.0052(8) | -0.0048(8) | -0.0085(9) |
| C15 | 0.0305(11) | 0.0233(11) | 0.0263(11) | -0.0092(8) | -0.0056(9) | -0.0029(9) |
| C16 | 0.0264(11) | 0.0261(11) | 0.0257(11) | -0.0076(9) | -0.0084(9) | -0.0006(9) |
| C17 | 0.0469(14) | 0.0255(12) | 0.0327(13) | -0.0066(9) | -0.0105(11) | -0.0128(11) |
| C18 | 0.0270(11) | 0.0253(11) | 0.0201(10) | -0.0035(8) | -0.0063(8) | -0.0071(9) |
| C19 | 0.0252(11) | 0.0316(12) | 0.0230(11) | -0.0045(9) | -0.0057(8) | -0.0088(9) |
| C20 | 0.0341(12) | 0.0341(12) | 0.0204(11) | -0.0015(9) | -0.0059(9) | -0.0133(10) |
| C21 | 0.0368(13) | 0.0286(11) | 0.0233(11) | 0.0002(9) | -0.0137(9) | -0.0097(10) |
| C22 | 0.0269(11) | 0.0314(12) | 0.0286(12) | -0.0052(9) | -0.0105(9) | -0.0044(9) |
| C23 | 0.0265(11) | 0.0278(11) | 0.0237(11) | -0.0040(8) | -0.0070(8) | -0.0066(9) |
| C24 | 0.0231(10) | 0.0274(11) | 0.0188(10) | -0.0046(8) | -0.0047(8) | -0.0059(9) |
| C25 | 0.0273(11) | 0.0337(12) | 0.0225(11) | -0.0088(9) | -0.0028(8) | -0.0089(9) |
| C26 | 0.0287(12) | 0.0375(13) | 0.0247(11) | -0.0075(9) | -0.0011(9) | -0.0108(10) |
| C27 | 0.0250(11) | 0.0270(11) | 0.0259(11) | -0.0029(8) | -0.0081(8) | -0.0076(9) |
| C28 | 0.0285(11) | 0.0272(11) | 0.0289(12) | -0.0088(9) | -0.0069(9) | -0.0050(9) |
| C29 | 0.0240(11) | 0.0274(11) | 0.0228(11) | -0.0062(8) | -0.0048(8) | -0.0031(9) |
| C30 | 0.0316(13) | 0.0475(15) | 0.0324(13) | -0.0068(11) | -0.0055(10) | -0.0183(11) |
| C31 | 0.0249(11) | 0.0238(10) | 0.0201(10) | -0.0047(8) | -0.0023(8) | -0.0027(8) |
| C32 | 0.0301(12) | 0.0255(11) | 0.0305(12) | -0.0067(9) | -0.0037(9) | -0.0077(9) |
| C33 | 0.0343(13) | 0.0296(12) | 0.0294(13) | 0.0004(9) | 0.0013(10) | -0.0076(10) |
| C34 | 0.0355(13) | 0.0427(14) | 0.0180(11) | -0.0003(10) | -0.0030(9) | -0.0020(11) |
| C35 | 0.0342(13) | 0.0434(14) | 0.0231(12) | -0.0084(10) | -0.0075(9) | -0.0054(11) |
| C36 | 0.0301(12) | 0.0337(12) | 0.0254(11) | -0.0061(9) | -0.0061(9) | -0.0096(10) |
Table 8.
Bond distances (Å) for compound 2.
| Bond distances (Å) | |||||
|---|---|---|---|---|---|
| F1-C21 | 1.365(2) | C7-C8 | 1.525(4) | C20-H20 | 0.95 |
| F2-C34 | 1.349(3) | C7-H7 | 1.00 | C21-C22 | 1.365(3) |
| O1-C27 | 1.373(3) | C8-H8A | 0.98 | C22-C23 | 1.387(3) |
| O1-C30 | 1.424(3) | C8-H8B | 0.98 | C22-H22 | 0.95 |
| O2-C14 | 1.377(2) | C8-H8C | 0.98 | C23-H23 | 0.95 |
| O2-C17 | 1.417(3) | C9-H9A | 0.98 | C24-C29 | 1.390(3) |
| O3-C5 | 1.348(3) | C9-H9B | 0.98 | C24-C25 | 1.393(3) |
| O3-C6 | 1.434(3) | C9-H9C | 0.98 | C25-C26 | 1.384(3) |
| O4-C5 | 1.229(3) | C10-C11 | 1.531(3) | C25-H25 | 0.95 |
| N1-C18 | 1.392(3) | C10-H10 | 1.00 | C26-C27 | 1.390(3) |
| N1-C1 | 1.456(3) | C11-C16 | 1.384(3) | C26-H26 | 0.95 |
| N1-C10 | 1.466(3) | C11-C12 | 1.399(3) | C27-C28 | 1.388(3) |
| N2-C3 | 1.356(3) | C12-C13 | 1.383(3) | C28-C29 | 1.384(3) |
| N2-C31 | 1.420(3) | C12-H12 | 0.95 | C28-H28 | 0.95 |
| N2-H2 | 0.89(3) | C13-C14 | 1.387(3) | C29-H29 | 0.95 |
| C1-C24 | 1.519(3) | C13-H13 | 0.95 | C30-H30A | 0.98 |
| C1-C2 | 1.540(3) | C14-C15 | 1.379(3) | C30-H30B | 0.98 |
| C1-H1 | 1.00 | C15-C16 | 1.394(3) | C30-H30C | 0.98 |
| C2-C3 | 1.499(3) | C15-H15 | 0.95 | C31-C32 | 1.382(3) |
| C2-H2A | 0.99 | C16-H16 | 0.95 | C31-C36 | 1.392(3) |
| C2-H2AB | 0.99 | C17-H17A | 0.98 | C32-C33 | 1.381(3) |
| C3-C4 | 1.362(3) | C17-H17B | 0.98 | C32-H32 | 0.95 |
| C4-C5 | 1.445(3) | C17-H17C | 0.98 | C33-C34 | 1.377(4) |
| C4-C10 | 1.511(3) | C18-C23 | 1.399(3) | C33-H33 | 0.95 |
| C6-C7 | 1.505(3) | C18-C19 | 1.404(3) | C34-C35 | 1.363(4) |
| C6-H6A | 0.99 | C19-C20 | 1.383(3) | C35-C36 | 1.382(3) |
| C6-H6AB | 0.99 | C19-H19 | 0.95 | C35-H35 | 0.95 |
| C7-C9 | 1.515(4) | C20-C21 | 1.370(3) | C36-H36 | 0.95 |
| H(2) ••••O(4) | 1.986(3) | N(2)-H(2) ••••O(4) | 2.696(3) | ||
Table 9.
Bond angles (°) for compound 2.
| Bond angles (°) | |||||
|---|---|---|---|---|---|
| C27-O1-C30 | 116.52(18) | C7-C9-H9A | 109.5 | C21-C22-C23 | 119.4(2) |
| C14-O2-C17 | 116.38(17) | C7-C9-H9B | 109.5 | C21-C22-C22 | 120.3 |
| C5-O3-C6 | 116.02(17) | H9A-C9-H9B | 109.5 | C23-C22-H22 | 120.3 |
| C18-N1-C1 | 119.95(17) | C7-C9-H9C | 109.5 | C22-C23-C18 | 121.0(2) |
| C18-N1-C10 | 120.12(17) | H9A-C9-H9C | 109.5 | C22-C23-H23 | 119.5 |
| C1-N1-C10 | 119.60(16) | H9B-C9-H9C | 109.5 | C18-C23-H23 | 119.5 |
| C3-N2-C31 | 125.41(19) | N1-C10-C4 | 109.45(17) | C29-C24-C25 | 118.3(2) |
| C3-N2-H2 | 114.0(18) | N1-C10-C11 | 113.21(17) | C29-C24-C1 | 122.81(19) |
| C31-N2-H2 | 119.3(18) | C4-C10-C11 | 113.77(17) | C25-C24-C1 | 118.80(19) |
| N1-C1-C24 | 114.43(17) | N1-C10-H10 | 106.6 | C26-C25-C24 | 121.5(2) |
| N1-C1-C2 | 109.36(17) | C4-C10-H10 | 106.6 | C26-C25-H25 | 119.3 |
| C24-C1-C2 | 108.60(17) | C11-C10-H10 | 106.6 | C24-C25-H25 | 119.3 |
| N1-C1-H1 | 108.1 | C16-C11-C12 | 117.4(2) | C25-C26-C27 | 119.4(2) |
| C24-C1-H1 | 108.1 | C16-C11-C10 | 122.74(19) | C25-C26-H26 | 120.3 |
| C2-C1-H1 | 108.1 | C12-C11-C10 | 119.78(18) | C27-C26-H26 | 120.3 |
| C3-C2-C1 | 108.16(17) | C13-C12-C11 | 121.4(2) | O1-C27-C28 | 115.5(2) |
| C3-C2-H2A | 110.1 | C13-C12-H12 | 119.3 | O1-C27-C26 | 124.8(2) |
| C1-C2-H2A | 110.1 | C11-C12-H12 | 119.3 | C28-C27-C26 | 119.7(2) |
| C3-C2-H2AB | 110.1 | C12-C13-C14 | 119.8(2) | C29-C28-C27 | 120.3(2) |
| C1-C2-H2AB | 110.1 | C12-C13-H13 | 120.1 | C29-C28-H28 | 119.8 |
| H2A-C2-H2AB | 108.4 | C14-C13-H13 | 120.1 | C27-C28-H28 | 119.8 |
| N2-C3-C4 | 124.0(2) | O2-C14-C15 | 124.41(19) | C28-C29-C24 | 120.7(2) |
| N2-C3-C2 | 120.41(19) | O2-C14-C13 | 115.45(19) | C28-C29-H29 | 119.6 |
| C4-C3-C2 | 115.37(18) | C15-C14-C13 | 120.1(2) | C24-C29-H29 | 119.6 |
| C3-C4-C5 | 121.21(19) | C14-C15-C16 | 119.3(2) | O1-C30-H30A | 109.5 |
| C3-C4-C10 | 117.74(19) | C14-C15-H15 | 120.4 | O1-C30-H30B | 109.5 |
| C5-C4-C10 | 121.05(18) | C16-C15-H15 | 120.4 | H30A-C30-H30B | 109.5 |
| O4-C5-O3 | 121.9(2) | C11-C16-C15 | 121.9(2) | O1-C30-H30C | 109.5 |
| O4-C5-C4 | 125.4(2) | C11-C16-H16 | 119 | H30A-C30-H30C | 109.5 |
| O3-C5-C4 | 112.76(18) | C15-C16-H16 | 119 | H30B-C30-H30C | 109.5 |
| O3-C6-C7 | 109.18(19) | O2-C17-H17A | 109.5 | C32-C31-C36 | 120.0(2) |
| O3-C6-H6A | 109.8 | O2-C17-H17B | 109.5 | C32-C31-N2 | 119.13(19) |
| C7-C6-H6A | 109.8 | H17A-C17-H17B | 109.5 | C36-C31-N2 | 120.8(2) |
| O3-C6-H6AB | 109.8 | O2-C17-H17C | 109.5 | C33-C32-C31 | 120.5(2) |
| C7-C6-H6AB | 109.8 | H17A-C17-H17C | 109.5 | C33-C32-H32 | 119.8 |
| H6A-C6-H6AB | 108.3 | H17B-C17-H17C | 109.5 | C31-C32-H32 | 119.8 |
| C6-C7-C9 | 112.8(2) | N1-C18-C23 | 121.07(19) | C34-C33-C32 | 118.0(2) |
| C6-C7-C8 | 108.5(2) | N1-C18-C19 | 121.43(19) | C34-C33-H33 | 121 |
| C9-C7-C8 | 111.2(2) | C23-C18-C19 | 117.50(19) | C32-C33-H33 | 121 |
| C6-C7-H7 | 108.1 | C20-C19-C18 | 121.3(2) | F2-C34-C35 | 118.3(2) |
| C9-C7-H7 | 108.1 | C20-C19-H19 | 119.4 | F2-C34-C33 | 118.7(2) |
| C8-C7-H7 | 108.1 | C18-C19-H19 | 119.4 | C35-C34-C33 | 123.0(2) |
| C7-C8-H8A | 109.5 | C21-C20-C19 | 119.1(2) | C34-C35-C36 | 118.6(2) |
| C7-C8-H8B | 109.5 | C21-C20-H20 | 120.5 | C34-C35-H35 | 120.7 |
| H8A-C8-H8B | 109.5 | C19-C20-H20 | 120.5 | C36-C35-H35 | 120.7 |
| C7-C8-H8C | 109.5 | F1-C21-C22 | 119.4(2) | C35-C36-C31 | 119.9(2) |
| H8A-C8-H8C | 109.5 | F1-C21-C20 | 118.7(2) | C35-C36-H36 | 120 |
| H8B-C8-H8C | 109.5 | C22-C21-C20 | 121.8(2) | C31-C36-H36 | 120 |
| N(2)-H(2)••••O(1) | 135.99(2) | ||||
Table 10.
Torsional angles [°] for compound 2.
| Torsional angles [°] | |||||
|---|---|---|---|---|---|
| C30-O1-C27-C26 | -0.0(3) | C3-C4-C10-N1 | 44.0(3) | N1-C18-C23-H23 | -0.7 |
| C30-O1-C27-C28 | 178.3(2) | C3-C4-C10-H10 | 159 | C19-C18-C23-C22 | -1.3(3) |
| C27-O1-C30-H30A | 62.6 | C3-C4-C10-C11 | -83.7(2) | C19-C18-C23-H23 | 178.7 |
| C27-O1-C30-H30B | -57.4 | C5-C4-C10-N1 | -136.2(2) | C18-C19-C20-H20 | 179.3 |
| C27-O1-C30-H30C | -177.4 | C5-C4-C10-H10 | -21.3 | C18-C19-C20-C21 | -0.8(3) |
| C17-O2-C14-C13 | -158.8(2) | C5-C4-C10-C11 | 96.0(2) | H19-C19-C20-H20 | -0.6 |
| C17-O2-C14-C15 | 22.2(3) | O3-C6-C7-H7 | 62.2 | H19-C19-C20-C21 | 179.3 |
| C14-O2-C17-H17A | 171.2 | O3-C6-C7-C8 | 179.1(2) | C19-C20-C21-F1 | 179.9(2) |
| C14-O2-C17-H17B | 51.3 | O3-C6-C7-C9 | -57.2(3) | C19-C20-C21-C22 | -0.0(3) |
| C14-O2-C17-H17C | -68.8 | H6A-C6-C7-H7 | -177.3 | H20-C20-C21-F1 | -0.1 |
| C6-O3-C5-O4 | 2.8(3) | H6A-C6-C7-C8 | -60.3 | H20-C20-C21-C22 | 179.9 |
| C6-O3-C5-C4 | -176.2(2) | H6A-C6-C7-C9 | 63.3 | F1-C21-C22-H22 | 0.1 |
| C5-O3-C6-H6A | 64.1 | H6AB-C6-C7-H7 | -58.3 | F1-C21-C22-C23 | -179.8(2) |
| C5-O3-C6-H6AB | -54.9 | H6AB-C6-C7-C8 | 58.6 | C20-C21-C22-H22 | -180 |
| C5-O3-C6-C7 | -175.4(2) | H6AB-C6-C7-C9 | -177.7 | C20-C21-C22-C23 | 0.1(4) |
| C10-N1-C1-H1 | -128.2 | C6-C7-C8-H8A | -56 | C21-C22-C23-C18 | 0.6(3) |
| C10-N1-C1-C2 | -10.7(3) | C6-C7-C8-H8B | -176 | C21-C22-C23-H23 | -179.4 |
| C10-N1-C1-C24 | 111.4(2) | C6-C7-C8-H8C | 64 | H22-C22-C23-C18 | -179.3 |
| C18-N1-C1-H1 | 45.2 | H7-C7-C8-H8A | 61 | H22-C22-C23-H23 | 0.7 |
| C18-N1-C1-C2 | 162.7(2) | H7-C7-C8-H8B | -59.1 | C1-C24-C25-H25 | -3.5 |
| C18-N1-C1-C24 | -75.2(2) | H7-C7-C8-H8C | -179 | C1-C24-C25-C26 | 176.5(2) |
| C1-N1-C10-C4 | -37.8(3) | C9-C7-C8-H8A | 179.4 | C29-C24-C25-H25 | 179.5 |
| C1-N1-C10-H10 | -152.8 | C9-C7-C8-H8B | 59.4 | C29-C24-C25-C26 | -0.5(3) |
| C1-N1-C10-C11 | 90.3(2) | C9-C7-C8-H8C | -60.5 | C1-C24-C29-C28 | -177.1(2) |
| C18-N1-C10-C4 | 148.8(2) | C6-C7-C9-H9A | -58.3 | C1-C24-C29-H29 | 2.9 |
| C18-N1-C10-H10 | 33.8 | C6-C7-C9-H9B | -178.3 | C25-C24-C29-C28 | -0.2(3) |
| C18-N1-C10-C11 | -83.1(2) | C6-C7-C9-H9C | 61.8 | C25-C24-C29-H29 | 179.8 |
| C1-N1-C18-C19 | -166.2(2) | H7-C7-C9-H9A | -177.7 | C24-C25-C26-H26 | -179.3 |
| C1-N1-C18-C23 | 13.2(3) | H7-C7-C9-H9B | 62.3 | C24-C25-C26-C27 | 0.7(3) |
| C10-N1-C18-C19 | 7.1(3) | H7-C7-C9-H9C | -57.6 | H25-C25-C26-H26 | 0.7 |
| C10-N1-C18-C23 | -173.5(2) | C8-C7-C9-H9A | 63.8 | H25-C25-C26-C27 | -179.3 |
| H2-N2-C3-C2 | -174(2) | C8-C7-C9-H9B | -56.2 | C25-C26-C27-O1 | 177.9(2) |
| H2-N2-C3-C4 | 1(2) | C8-C7-C9-H9C | -176.1 | C25-C26-C27-C28 | -0.3(3) |
| C31-N2-C3-C2 | 19.7(3) | N1-C10-C11-C12 | -174.3(2) | H26-C26-C27-O1 | -2.1 |
| C31-N2-C3-C4 | -165.4(2) | N1-C10-C11-C16 | 8.8(3) | H26-C26-C27-C28 | 179.7 |
| H2-N2-C31-C32 | 65(2) | C4-C10-C11-C12 | -48.5(3) | O1-C27-C28-H28 | 1.2 |
| H2-N2-C31-C36 | -112(2) | C4-C10-C11-C16 | 134.6(2) | O1-C27-C28-C29 | -178.8(2) |
| C3-N2-C31-C32 | -129.4(2) | H10-C10-C11-C12 | 68.8 | C26-C27-C28-H28 | 179.5 |
| C3-N2-C31-C36 | 54.2(3) | H10-C10-C11-C16 | -108.1 | C26-C27-C28-C29 | -0.4(3) |
| N1-C1-C2-H2A | 175.9 | C10-C11-C12-H12 | 3.7 | C27-C28-C29-C24 | 0.7(3) |
| N1-C1-C2-H2AB | -64.7 | C10-C11-C12-C13 | -176.3(2) | C27-C28-C29-H29 | -179.3 |
| N1-C1-C2-C3 | 55.6(2) | C16-C11-C12-H12 | -179.2 | H28-C28-C29-C24 | -179.3 |
| H1-C1-C2-H2A | -66.6 | C16-C11-C12-C13 | 0.8(3) | H28-C28-C29-H29 | 0.7 |
| H1-C1-C2-H2AB | 52.8 | C10-C11-C16-C15 | 176.8(2) | N2-C31-C32-H32 | 4.2 |
| H1-C1-C2-C3 | 173.1 | C10-C11-C16-H16 | -3.2 | N2-C31-C32-C33 | -175.8(2) |
| C24-C1-C2-H2A | 50.4 | C12-C11-C16-C15 | -0.2(3) | C36-C31-C32-H32 | -179.3 |
| C24-C1-C2-H2AB | 169.8 | C12-C11-C16-H16 | 179.8 | C36-C31-C32-C33 | 0.7(3) |
| C24-C1-C2-C3 | -69.9(2) | C11-C12-C13-H13 | 179.1 | N2-C31-C36-C35 | 176.8(2) |
| N1-C1-C24-C25 | 161.1(2) | C11-C12-C13-C14 | -0.9(3) | N2-C31-C36-H36 | -3.2 |
| N1-C1-C24-C29 | -22.1(3) | H12-C12-C13-H13 | -0.9 | C32-C31-C36-C35 | 0.4(3) |
| H1-C1-C24-C25 | 40.6 | H12-C12-C13-C14 | 179.1 | C32-C31-C36-H36 | -179.6 |
| H1-C1-C24-C29 | -142.6 | C12-C13-C14-O2 | -178.8(2) | C31-C32-C33-H33 | 179.4 |
| C2-C1-C24-C25 | -76.4(2) | C12-C13-C14-C15 | 0.3(3) | C31-C32-C33-C34 | -0.6(3) |
| C2-C1-C24-C29 | 100.4(2) | H13-C13-C14-O2 | 1.2 | H32-C32-C33-H33 | -0.6 |
| C1-C2-C3-N2 | 123.2(2) | H13-C13-C14-C15 | -179.7 | H32-C32-C33-C34 | 179.4 |
| C1-C2-C3-C4 | -52.1(2) | O2-C14-C15-H15 | -0.8 | C32-C33-C34-F2 | 179.8(2) |
| H2A-C2-C3-N2 | 3 | O2-C14-C15-C16 | 179.2(2) | C32-C33-C34-C35 | -0.5(4) |
| H2A-C2-C3-C4 | -172.4 | C13-C14-C15-H15 | -179.8 | H33-C33-C34-F2 | -0.3 |
| H2AB-C2-C3-N2 | -116.5 | C13-C14-C15-C16 | 0.2(3) | H33-C33-C34-C35 | 179.4 |
| H2AB-C2-C3-C4 | 68.2 | C14-C15-C16-C11 | -0.3(3) | F2-C34-C35-H35 | 1.3 |
| N2-C3-C4-C5 | 6.4(3) | C14-C15-C16-H16 | 179.7 | F2-C34-C35-C36 | -178.7(2) |
| N2-C3-C4-C10 | -173.8(2) | H15-C15-C16-C11 | 179.7 | C33-C34-C35-H35 | -178.5 |
| C2-C3-C4-C5 | -178.5(2) | H15-C15-C16-H16 | -0.3 | C33-C34-C35-C36 | 1.6(4) |
| C2-C3-C4-C10 | 1.3(3) | N1-C18-C19-H19 | 0.7 | C34-C35-C36-C31 | -1.4(3) |
| C3-C4-C5-O3 | 169.2(2) | N1-C18-C19-C20 | -179.1(2) | C34-C35-C36-H36 | 178.6 |
| C3-C4-C5-O4 | -9.8(4) | C23-C18-C19-H19 | -178.7 | H35-C35-C36-C31 | 178.6 |
| C10-C4-C5-O3 | -10.6(3) | C23-C18-C19-C20 | 1.4(3) | H35-C35-C36-H36 | -1.4 |
| C10-C4-C5-O4 | 170.5(2) | N1-C18-C23-C22 | 179.3(2) | ||
Table 11.
Atomic coordinates and equivalent isotropic atomic displacement parameters (Å) for compound 3.
| x/a | y/b | z/c | U (eq) | |
|---|---|---|---|---|
| C1 | 0.2868(4) | 0.6370(4) | 0.6679(3) | 0.0875(10) |
| C2 | 0.2375(4) | 0.5099(3) | 0.6300(3) | 0.0871(9) |
| C3 | 0.2932(3) | 0.4491(3) | 0.6825(2) | 0.0731(8) |
| C4 | 0.4019(3) | 0.5143(2) | 0.77396(19) | 0.0580(6) |
| C5 | 0.4507(4) | 0.6410(3) | 0.8127(2) | 0.0763(8) |
| C6 | 0.3926(4) | 0.7008(3) | 0.7609(3) | 0.0922(10) |
| C7 | 0.2263(6) | 0.7029(5) | 0.6090(4) | 0.1317(17) |
| C8 | 0.4730(3) | 0.4509(2) | 0.83023(18) | 0.0549(6) |
| C9 | 0.6107(3) | 0.4439(2) | 0.80342(19) | 0.0602(7) |
| C10 | 0.5728(3) | 0.3593(2) | 0.69196(19) | 0.0555(6) |
| C11 | 0.4706(3) | 0.2480(2) | 0.66044(18) | 0.0537(6) |
| C12 | 0.4104(3) | 0.2199(2) | 0.74122(17) | 0.0523(6) |
| C13 | 0.4989(3) | 0.1663(2) | 0.79844(18) | 0.0541(6) |
| C14 | 0.5192(3) | 0.0574(2) | 0.7432(2) | 0.0714(8) |
| C15 | 0.5970(4) | 0.0056(3) | 0.7924(3) | 0.0813(9) |
| C16 | 0.6566(3) | 0.0585(3) | 0.8980(3) | 0.0755(8) |
| C17 | 0.6354(3) | 0.1666(3) | 0.9529(2) | 0.0780(8) |
| C18 | 0.5585(3) | 0.2200(2) | 0.9042(2) | 0.0667(7) |
| C19 | 0.7388(4) | -0.0009(4) | 0.9520(3) | 0.1093(12) |
| C20 | 0.2806(2) | 0.3154(2) | 0.85956(17) | 0.0542(6) |
| C21 | 0.2140(3) | 0.2025(3) | 0.8611(2) | 0.0663(7) |
| C22 | 0.1125(3) | 0.1929(3) | 0.9125(2) | 0.0814(9) |
| C23 | 0.0770(3) | 0.2940(4) | 0.9608(2) | 0.0846(10) |
| C24 | 0.1382(3) | 0.4050(3) | 0.9605(2) | 0.0764(9) |
| C25 | 0.2397(3) | 0.4159(2) | 0.90977(18) | 0.0617(7) |
| C26 | 0.7257(3) | 0.5207(2) | 0.6576(2) | 0.0631(7) |
| C27 | 0.8640(3) | 0.5607(3) | 0.7166(3) | 0.0961(11) |
| C28 | 0.9526(4) | 0.6796(4) | 0.7447(3) | 0.1082(12) |
| C29 | 0.9009(5) | 0.7533(3) | 0.7116(3) | 0.0973(11) |
| C30 | 0.7655(5) | 0.7182(3) | 0.6539(3) | 0.1064(12) |
| C31 | 0.6762(4) | 0.6002(3) | 0.6268(3) | 0.0878(9) |
| C32 | 0.4138(3) | 0.1644(2) | 0.5523(2) | 0.0598(6) |
| C33 | 0.2409(4) | -0.0255(3) | 0.4257(2) | 0.0880(10) |
| C34 | 0.1640(4) | -0.1468(3) | 0.4201(3) | 0.0925(11) |
| C35 | 0.0531(5) | -0.1448(4) | 0.4758(4) | 0.1184(14) |
| C36 | 0.1070(5) | -0.2385(3) | 0.3066(3) | 0.1292(17) |
| N1 | 0.3846(2) | 0.32806(17) | 0.81028(15) | 0.0544(5) |
| N2 | 0.6333(3) | 0.3987(2) | 0.6288(2) | 0.0681(6) |
| O1 | 0.3068(2) | 0.06252(17) | 0.53247(13) | 0.0757(6) |
| O2 | 0.4561(2) | 0.18069(18) | 0.48289(14) | 0.0796(6) |
| F2 | 0.9889(3) | 0.8703(2) | 0.7395(2) | 0.1537(11) |
| F1 | -0.0228(2) | 0.2842(2) | 1.01174(18) | 0.1325(9) |
Table 12.
Anisotropic atomic displacement parameters (Å) for compound 3.
| U11 | U22 | U33 | U23 | U13 | U12 | |
|---|---|---|---|---|---|---|
| C1 | 0.109(3) | 0.101(3) | 0.102(3) | 0.067(2) | 0.059(2) | 0.059(2) |
| C2 | 0.087(2) | 0.101(3) | 0.077(2) | 0.0401(19) | 0.0169(17) | 0.0400(19) |
| C3 | 0.0764(19) | 0.0638(17) | 0.0681(18) | 0.0214(14) | 0.0105(15) | 0.0226(15) |
| C4 | 0.0629(16) | 0.0518(14) | 0.0558(15) | 0.0186(12) | 0.0235(13) | 0.0150(12) |
| C5 | 0.091(2) | 0.0578(16) | 0.0743(19) | 0.0250(15) | 0.0295(16) | 0.0161(15) |
| C6 | 0.120(3) | 0.0682(19) | 0.108(3) | 0.047(2) | 0.054(2) | 0.033(2) |
| C7 | 0.171(4) | 0.170(4) | 0.151(4) | 0.121(4) | 0.089(3) | 0.109(4) |
| C8 | 0.0545(14) | 0.0493(13) | 0.0450(13) | 0.0086(10) | 0.0132(11) | 0.0085(11) |
| C9 | 0.0526(14) | 0.0564(14) | 0.0571(15) | 0.0163(12) | 0.0137(12) | 0.0072(11) |
| C10 | 0.0502(14) | 0.0593(15) | 0.0544(14) | 0.0211(12) | 0.0175(11) | 0.0166(12) |
| C11 | 0.0549(14) | 0.0534(14) | 0.0482(13) | 0.0178(11) | 0.0161(11) | 0.0147(11) |
| C12 | 0.0504(13) | 0.0470(13) | 0.0479(13) | 0.0140(10) | 0.0126(11) | 0.0071(10) |
| C13 | 0.0556(14) | 0.0460(13) | 0.0528(14) | 0.0162(11) | 0.0178(11) | 0.0094(11) |
| C14 | 0.100(2) | 0.0561(15) | 0.0601(16) | 0.0235(13) | 0.0300(15) | 0.0264(15) |
| C15 | 0.111(3) | 0.0610(17) | 0.089(2) | 0.0367(17) | 0.046(2) | 0.0373(17) |
| C16 | 0.0724(19) | 0.0712(18) | 0.095(2) | 0.0469(18) | 0.0266(17) | 0.0256(15) |
| C17 | 0.0723(19) | 0.082(2) | 0.0664(18) | 0.0258(16) | 0.0054(15) | 0.0227(16) |
| C18 | 0.0667(17) | 0.0616(16) | 0.0585(16) | 0.0129(13) | 0.0122(13) | 0.0225(13) |
| C19 | 0.113(3) | 0.100(3) | 0.133(3) | 0.067(2) | 0.026(2) | 0.047(2) |
| C20 | 0.0472(13) | 0.0605(15) | 0.0452(13) | 0.0171(11) | 0.0091(11) | 0.0128(11) |
| C21 | 0.0597(16) | 0.0725(17) | 0.0686(17) | 0.0320(14) | 0.0232(13) | 0.0185(14) |
| C22 | 0.0672(18) | 0.096(2) | 0.081(2) | 0.0443(18) | 0.0277(16) | 0.0131(17) |
| C23 | 0.0577(17) | 0.115(3) | 0.0670(19) | 0.0260(18) | 0.0292(15) | 0.0167(18) |
| C24 | 0.0525(16) | 0.091(2) | 0.0591(17) | 0.0070(15) | 0.0144(13) | 0.0186(15) |
| C25 | 0.0495(14) | 0.0665(16) | 0.0507(14) | 0.0114(12) | 0.0090(12) | 0.0131(12) |
| C26 | 0.0670(17) | 0.0620(16) | 0.0633(16) | 0.0277(13) | 0.0286(14) | 0.0174(13) |
| C27 | 0.068(2) | 0.090(2) | 0.139(3) | 0.067(2) | 0.023(2) | 0.0163(17) |
| C28 | 0.071(2) | 0.100(3) | 0.137(3) | 0.057(3) | 0.023(2) | -0.002(2) |
| C29 | 0.118(3) | 0.067(2) | 0.100(3) | 0.0367(19) | 0.044(2) | 0.009(2) |
| C30 | 0.147(4) | 0.071(2) | 0.106(3) | 0.045(2) | 0.031(3) | 0.037(2) |
| C31 | 0.096(2) | 0.077(2) | 0.080(2) | 0.0298(17) | 0.0124(18) | 0.0275(18) |
| C32 | 0.0622(16) | 0.0578(15) | 0.0542(15) | 0.0203(12) | 0.0169(13) | 0.0160(13) |
| C33 | 0.105(2) | 0.0731(19) | 0.0500(16) | 0.0070(14) | 0.0095(16) | 0.0073(17) |
| C34 | 0.085(2) | 0.0656(19) | 0.085(2) | 0.0077(16) | -0.0147(18) | 0.0216(17) |
| C35 | 0.104(3) | 0.091(3) | 0.136(4) | 0.045(3) | 0.017(3) | 0.010(2) |
| C36 | 0.127(3) | 0.081(2) | 0.105(3) | -0.012(2) | -0.027(2) | 0.031(2) |
| N1 | 0.0555(12) | 0.0481(11) | 0.0553(12) | 0.0167(9) | 0.0218(10) | 0.0135(9) |
| N2 | 0.0716(15) | 0.0654(14) | 0.0585(14) | 0.0227(12) | 0.0254(12) | 0.0079(12) |
| O1 | 0.0836(13) | 0.0643(11) | 0.0472(10) | 0.0078(8) | 0.0136(9) | -0.0013(10) |
| O2 | 0.1001(15) | 0.0756(13) | 0.0514(11) | 0.0207(9) | 0.0267(11) | 0.0152(11) |
| F2 | 0.187(3) | 0.0768(14) | 0.165(2) | 0.0451(15) | 0.061(2) | -0.0090(15) |
| F1 | 0.0960(15) | 0.168(2) | 0.1248(17) | 0.0462(16) | 0.0723(14) | 0.0232(14) |
Table 13.
Bond distances (Å) for compound 3.
| Bond distances (Å) | |||||
|---|---|---|---|---|---|
| C1-C6 | 1.379(5) | C13-C18 | 1.378(3) | C26-C27 | 1.372(4) |
| C1-C2 | 1.381(5) | C13-C14 | 1.381(4) | C26-N2 | 1.429(3) |
| C1-C7 | 1.518(5) | C14-C15 | 1.379(4) | C27-C28 | 1.388(5) |
| C2-C3 | 1.383(4) | C14-H14 | 0.93 | C27-H27 | 0.93 |
| C2-H2 | 0.93 | C15-C16 | 1.377(4) | C28-C29 | 1.333(5) |
| C3-C4 | 1.379(4) | C15-H15 | 0.93 | C28-H28 | 0.93 |
| C3-H3 | 0.93 | C16-C17 | 1.377(4) | C29-C30 | 1.349(6) |
| C4-C5 | 1.377(4) | C16-C19 | 1.519(4) | C29-F2 | 1.368(4) |
| C4-C8 | 1.518(4) | C17-C18 | 1.384(4) | C30-C31 | 1.385(5) |
| C5-C6 | 1.376(4) | C17-H17 | 0.93 | C30-H30 | 0.93 |
| C5-H5 | 0.93 | C18-H18 | 0.93 | C31-H31 | 0.93 |
| C6-H6 | 0.93 | C19-H19A | 0.96 | C32-O2 | 1.226(3) |
| C7-H7A | 0.96 | C19-H19B | 0.96 | C32-O1 | 1.347(3) |
| C7-H7B | 0.96 | C19-H19C | 0.96 | C33-O1 | 1.447(3) |
| C7-H7C | 0.96 | C20-N1 | 1.392(3) | C33-C34 | 1.475(5) |
| C8-N1 | 1.456(3) | C20-C25 | 1.396(4) | C33-H33A | 0.97 |
| C8-C9 | 1.536(3) | C20-C21 | 1.401(4) | C33-H33B | 0.97 |
| C8-H8 | 0.98 | C21-C22 | 1.387(4) | C34-C35 | 1.505(5) |
| C9-C10 | 1.491(3) | C21-H21 | 0.93 | C34-C36 | 1.527(5) |
| C9-H9A | 0.97 | C22-C23 | 1.362(5) | C34-H34 | 0.98 |
| C9-H9B | 0.97 | C22-H22 | 0.93 | C35-H35A | 0.96 |
| C10-N2 | 1.356(3) | C23-C24 | 1.361(5) | C35-H35B | 0.96 |
| C10-C11 | 1.365(3) | C23-F1 | 1.370(3) | C35-H35C | 0.96 |
| C11-C32 | 1.443(3) | C24-C25 | 1.382(4) | C36-H36A | 0.96 |
| C11-C12 | 1.524(3) | C24-H24 | 0.93 | C36-H36B | 0.96 |
| C12-N1 | 1.468(3) | C25-H25 | 0.93 | C36-H36C | 0.96 |
| C12-C13 | 1.528(3) | C26-C31 | 1.369(4) | N2-H2A | 0.87(3) |
| C12-H12 | 0.98 | H(2A)••••O(2) | 1.98(3) | N(2)-H(2A)••••O(2) | 2.675(3) |
Table 14.
Bond angles (°) for compound 3.
| Bond angles (°) | |||||
|---|---|---|---|---|---|
| C6-C1-C2 | 117.2(3) | C18-C13-C14 | 117.3(2) | C29-C28-C27 | 118.5(4) |
| C6-C1-C7 | 121.7(4) | C18-C13-C12 | 123.3(2) | C29-C28-H28 | 120.8 |
| C2-C1-C7 | 121.0(4) | C14-C13-C12 | 119.4(2) | C27-C28-H28 | 120.8 |
| C3-C2-C1 | 121.3(3) | C15-C14-C13 | 121.0(3) | C28-C29-C30 | 122.8(3) |
| C3-C2-H2 | 119.3 | C15-C14-H14 | 119.5 | C28-C29-F2 | 118.2(4) |
| C1-C2-H2 | 119.3 | C13-C14-H14 | 119.5 | C30-C29-F2 | 119.0(4) |
| C4-C3-C2 | 120.6(3) | C16-C15-C14 | 122.1(3) | C29-C30-C31 | 118.9(3) |
| C4-C3-H3 | 119.7 | C16-C15-H15 | 119 | C29-C30-H30 | 120.6 |
| C2-C3-H3 | 119.7 | C14-C15-H15 | 119 | C31-C30-H30 | 120.6 |
| C5-C4-C3 | 118.4(3) | C17-C16-C15 | 116.8(3) | C26-C31-C30 | 120.2(3) |
| C5-C4-C8 | 119.2(2) | C17-C16-C19 | 121.4(3) | C26-C31-H31 | 119.9 |
| C3-C4-C8 | 122.3(2) | C15-C16-C19 | 121.8(3) | C30-C31-H31 | 119.9 |
| C6-C5-C4 | 120.6(3) | C16-C17-C18 | 121.6(3) | O2-C32-O1 | 121.3(2) |
| C6-C5-H5 | 119.7 | C16-C17-H17 | 119.2 | O2-C32-C11 | 125.2(2) |
| C4-C5-H5 | 119.7 | C18-C17-H17 | 119.2 | O1-C32-C11 | 113.5(2) |
| C1-C6-C5 | 121.8(3) | C13-C18-C17 | 121.2(3) | O1-C33-C34 | 110.2(3) |
| C1-C6-H6 | 119.1 | C13-C18-H18 | 119.4 | O1-C33-H33A | 109.6 |
| C5-C6-H6 | 119.1 | C17-C18-H18 | 119.4 | C34-C33-H33A | 109.6 |
| C1-C7-H7A | 109.5 | C16-C19-H19A | 109.5 | O1-C33-H33B | 109.6 |
| C1-C7-H7B | 109.5 | C16-C19-H19B | 109.5 | C34-C33-H33B | 109.6 |
| H7A-C7-H7B | 109.5 | H19A-C19-H19B | 109.5 | H33A-C33-H33B | 108.1 |
| C1-C7-H7C | 109.5 | C16-C19-H19C | 109.5 | C33-C34-C35 | 114.4(3) |
| H7A-C7-H7C | 109.5 | H19A-C19-H19C | 109.5 | C33-C34-C36 | 108.1(3) |
| H7B-C7-H7C | 109.5 | H19B-C19-H19C | 109.5 | C35-C34-C36 | 113.6(3) |
| N1-C8-C4 | 114.5(2) | N1-C20-C25 | 120.6(2) | C33-C34-H34 | 106.8 |
| N1-C8-C9 | 109.31(19) | N1-C20-C21 | 121.6(2) | C35-C34-H34 | 106.8 |
| C4-C8-C9 | 110.1(2) | C25-C20-C21 | 117.8(2) | C36-C34-H34 | 106.8 |
| N1-C8-H8 | 107.6 | C22-C21-C20 | 120.5(3) | C34-C35-H35A | 109.5 |
| C4-C8-H8 | 107.6 | C22-C21-H21 | 119.8 | C34-C35-H35B | 109.5 |
| C9-C8-H8 | 107.6 | C20-C21-H21 | 119.8 | H35A-C35-H35B | 109.5 |
| C10-C9-C8 | 108.2(2) | C23-C22-C21 | 119.4(3) | C34-C35-H35C | 109.5 |
| C10-C9-H9A | 110.1 | C23-C22-H22 | 120.3 | H35A-C35-H35C | 109.5 |
| C8-C9-H9A | 110.1 | C21-C22-H22 | 120.3 | H35B-C35-H35C | 109.5 |
| C10-C9-H9B | 110.1 | C24-C23-C22 | 122.0(3) | C34-C36-H36A | 109.5 |
| C8-C9-H9B | 110.1 | C24-C23-F1 | 118.8(3) | C34-C36-H36B | 109.5 |
| H9A-C9-H9B | 108.4 | C22-C23-F1 | 119.2(3) | H36A-C36-H36B | 109.5 |
| N2-C10-C11 | 124.8(2) | C23-C24-C25 | 119.1(3) | C34-C36-H36C | 109.5 |
| N2-C10-C9 | 119.5(2) | C23-C24-H24 | 120.4 | H36A-C36-H36C | 109.5 |
| C11-C10-C9 | 115.6(2) | C25-C24-H24 | 120.4 | H36B-C36-H36C | 109.5 |
| C10-C11-C32 | 120.4(2) | C24-C25-C20 | 121.2(3) | C20-N1-C8 | 119.50(19) |
| C10-C11-C12 | 118.1(2) | C24-C25-H25 | 119.4 | C20-N1-C12 | 121.27(19) |
| C32-C11-C12 | 121.3(2) | C20-C25-H25 | 119.4 | C8-N1-C12 | 119.20(18) |
| N1-C12-C11 | 110.56(18) | C31-C26-C27 | 118.8(3) | C10-N2-C26 | 125.4(2) |
| N1-C12-C13 | 113.52(19) | C31-C26-N2 | 119.9(3) | C10-N2-H2A | 113(2) |
| C11-C12-C13 | 112.8(2) | C27-C26-N2 | 121.2(3) | C26-N2-H2A | 119(2) |
| N1-C12-H12 | 106.5 | C26-C27-C28 | 120.8(3) | C32-O1-C33 | 117.5(2) |
| C11-C12-H12 | 106.5 | C26-C27-H27 | 119.6 | N(2)-H(2A)••••O(2) | 136(3) |
| C13-C12-H12 | 106.5 | C28-C27-H27 | 119.6 | ||
Table 1.
Atomic coordinates and equivalent isotropic atomic displacement parameters (Å) for compound 1.
| x/a | y/b | z/c | U (eq) | |
|---|---|---|---|---|
| C1 | 0.46891(17) | 0.87888(14) | 0.64988(13) | 0.0565(4) |
| C2 | 0.4792(2) | 0.85604(18) | 0.75671(16) | 0.0758(6) |
| C3 | 0.4165(2) | 0.78351(18) | 0.82011(14) | 0.0795(7) |
| C4 | 0.3432(2) | 0.73104(17) | 0.77819(14) | 0.0745(6) |
| C5 | 0.33077(17) | 0.75441(15) | 0.67094(13) | 0.0575(4) |
| C6 | 0.39321(13) | 0.82940(11) | 0.60676(10) | 0.0392(3) |
| C7 | 0.40657(12) | 0.78689(11) | 0.42506(10) | 0.0350(3) |
| C8 | 0.49144(13) | 0.66295(11) | 0.45111(10) | 0.0370(3) |
| C9 | 0.60848(13) | 0.63552(11) | 0.36493(9) | 0.0363(3) |
| C10 | 0.41857(13) | 0.72723(11) | 0.25121(10) | 0.0355(3) |
| C11 | 0.37124(13) | 0.81913(11) | 0.32429(10) | 0.0366(3) |
| C12 | 0.32985(12) | 0.64689(11) | 0.26362(9) | 0.0341(3) |
| C13 | 0.19476(13) | 0.69441(12) | 0.25093(12) | 0.0436(3) |
| C14 | 0.11446(14) | 0.62387(12) | 0.25639(12) | 0.0457(3) |
| C15 | 0.16693(14) | 0.50315(12) | 0.27460(10) | 0.0400(3) |
| C16 | 0.29973(14) | 0.45379(12) | 0.28822(11) | 0.0421(3) |
| C17 | 0.37949(13) | 0.52617(11) | 0.28238(10) | 0.0386(3) |
| C18 | 0.1349(2) | 0.32154(15) | 0.26096(16) | 0.0675(5) |
| C19 | 0.63647(13) | 0.60777(12) | 0.17860(10) | 0.0376(3) |
| C20 | 0.58244(15) | 0.60704(14) | 0.08635(11) | 0.0459(3) |
| C21 | 0.66073(17) | 0.55173(15) | 0.00515(11) | 0.0545(4) |
| C22 | 0.79407(17) | 0.49552(16) | 0.01192(12) | 0.0579(4) |
| C23 | 0.84792(15) | 0.49602(15) | 0.10179(12) | 0.0536(4) |
| C24 | 0.77203(14) | 0.54988(13) | 0.18424(11) | 0.0441(3) |
| C25 | 0.70710(13) | 0.69922(13) | 0.37462(10) | 0.0402(3) |
| C26 | 0.70408(15) | 0.80837(14) | 0.31754(13) | 0.0517(4) |
| C27 | 0.78949(17) | 0.86769(16) | 0.33293(15) | 0.0622(4) |
| C28 | 0.88021(16) | 0.81895(18) | 0.40624(14) | 0.0605(4) |
| C29 | 0.88731(17) | 0.70988(19) | 0.46244(13) | 0.0656(5) |
| C30 | 0.80094(15) | 0.65038(16) | 0.44619(12) | 0.0537(4) |
| C31 | 1.0489(2) | 0.8429(3) | 0.4939(2) | 0.1061(9) |
| C32 | 0.29313(15) | 0.93706(12) | 0.28857(11) | 0.0432(3) |
| N1 | 0.55871(10) | 0.66221(10) | 0.26143(8) | 0.0374(3) |
| N2 | 0.37621(13) | 0.86057(11) | 0.49752(9) | 0.0430(3) |
| O1 | 0.25499(12) | 1.01787(9) | 0.34048(9) | 0.0572(3) |
| O2 | 0.26345(13) | 0.95158(9) | 0.18869(9) | 0.0622(3) |
| O3 | 0.07968(11) | 0.43958(10) | 0.27847(9) | 0.0568(3) |
| O4 | 0.96053(15) | 0.88513(15) | 0.41546(13) | 0.0885(5) |
| C33 | 0.1679(18) | 1.0666(17) | 0.1453(9) | 0.089(3) |
| C34 | 0.1944(10) | 1.0710(8) | 0.0289(5) | 0.110(3) |
| C35 | 0.3327(10) | 1.0644(9) | -0.0139(7) | 0.176(4) |
| C36 | 0.1085(13) | 1.1892(9) | -0.0206(8) | 0.139(4) |
Table 15.
Torsional angles [°] for compound 3.
| Torsional angles [°] | |||||
|---|---|---|---|---|---|
| C6-C1-C2-C3 | -0.9(5) | C11-C12-C13-C14 | -59.5(3) | C27-C26-C31-C30 | 0.9(5) |
| C7-C1-C2-C3 | 179.2(3) | C18-C13-C14-C15 | -0.4(4) | N2-C26-C31-C30 | -179.6(3) |
| C1-C2-C3-C4 | -1.1(5) | C12-C13-C14-C15 | -179.2(3) | C29-C30-C31-C26 | -0.6(6) |
| C2-C3-C4-C5 | 1.7(4) | C13-C14-C15-C16 | 0.6(5) | C10-C11-C32-O2 | 4.9(4) |
| C2-C3-C4-C8 | -175.6(3) | C14-C15-C16-C17 | -0.2(5) | C12-C11-C32-O2 | 179.8(3) |
| C3-C4-C5-C6 | -0.4(4) | C14-C15-C16-C19 | 178.3(3) | C10-C11-C32-O1 | -175.4(2) |
| C8-C4-C5-C6 | 177.0(3) | C15-C16-C17-C18 | -0.3(5) | C12-C11-C32-O1 | -0.6(3) |
| C2-C1-C6-C5 | 2.2(5) | C19-C16-C17-C18 | -178.8(3) | O1-C33-C34-C35 | 57.0(4) |
| C7-C1-C6-C5 | -177.9(3) | C14-C13-C18-C17 | -0.1(4) | O1-C33-C34-C36 | -175.4(3) |
| C4-C5-C6-C1 | -1.6(5) | C12-C13-C18-C17 | 178.6(2) | C25-C20-N1-C8 | 13.7(3) |
| C5-C4-C8-N1 | 156.7(2) | C16-C17-C18-C13 | 0.5(5) | C21-C20-N1-C8 | -166.0(2) |
| C3-C4-C8-N1 | -26.1(3) | N1-C20-C21-C22 | 178.8(2) | C25-C20-N1-C12 | -168.5(2) |
| C5-C4-C8-C9 | -79.7(3) | C25-C20-C21-C22 | -0.9(4) | C21-C20-N1-C12 | 11.9(3) |
| C3-C4-C8-C9 | 97.5(3) | C20-C21-C22-C23 | 0.5(4) | C4-C8-N1-C20 | -77.7(3) |
| N1-C8-C9-C10 | 59.7(3) | C21-C22-C23-C24 | 0.0(5) | C9-C8-N1-C20 | 158.3(2) |
| C4-C8-C9-C10 | -66.8(2) | C21-C22-C23-F1 | -179.7(3) | C4-C8-N1-C12 | 104.4(2) |
| C8-C9-C10-N2 | 126.7(2) | C22-C23-C24-C25 | -0.1(5) | C9-C8-N1-C12 | -19.6(3) |
| C8-C9-C10-C11 | -49.4(3) | F1-C23-C24-C25 | 179.6(2) | C11-C12-N1-C20 | 152.6(2) |
| N2-C10-C11-C32 | -3.0(4) | C23-C24-C25-C20 | -0.3(4) | C13-C12-N1-C20 | -79.4(3) |
| C9-C10-C11-C32 | 172.9(2) | N1-C20-C25-C24 | -178.9(2) | C11-C12-N1-C8 | -29.5(3) |
| N2-C10-C11-C12 | -178.0(2) | C21-C20-C25-C24 | 0.8(4) | C13-C12-N1-C8 | 98.4(2) |
| C9-C10-C11-C12 | -2.1(3) | C31-C26-C27-C28 | -0.1(5) | C11-C10-N2-C26 | 170.9(3) |
| C10-C11-C12-N1 | 42.8(3) | N2-C26-C27-C28 | -179.6(3) | C9-C10-N2-C26 | -4.8(4) |
| C32-C11-C12-N1 | -132.2(2) | C26-C27-C28-C29 | -1.1(6) | C31-C26-N2-C10 | -103.8(3) |
| C10-C11-C12-C13 | -85.6(3) | C27-C28-C29-C30 | 1.4(7) | C27-C26-N2-C10 | 75.7(4) |
| C32-C11-C12-C13 | 99.4(3) | C27-C28-C29-F2 | -179.9(3) | O2-C32-O1-C33 | -1.7(4) |
| N1-C12-C13-C18 | -5.0(3) | C28-C29-C30-C31 | -0.6(6) | C11-C32-O1-C33 | 178.6(2) |
| C11-C12-C13-C18 | 121.8(3) | F2-C29-C30-C31 | -179.3(3) | C34-C33-O1-C32 | 160.5(3) |
| N1-C12-C13-C14 | 173.7(2) | ||||
Fig. 1.
Molecular structure of compounds 1-3.
Fig. 2.
Plane of pseudo six membered ring (RAHB) in 1, 2 and 3.
Fig. 3.
Hirshfeld surfaces of 1; (a) dnorm (b) di (c) de (d) Shape index (e) Curvedness.
Fig. 5.
Hirshfeld surfaces of 2; (a) dnorm (b) di (c) de (d) Shape index (e) Curvedness.
Fig. 7.
Hirshfeld surfaces of 3; (a) dnorm (b) di (c) de (d) Shape index (e) Curvedness.
Fingerprint plots are depicted in Fig. 4, 6 and 8. Percentile contributions of the finger print plots are given as supplementary data (as MS Excel spreadsheet) and it can be accessed at https://data.mendeley.com/datasets/4p5t89zs4v/draft?a=b8bfd08f-a27c-4919-ae70-0648f7ed9116. In the finger prints, the colour of each point corresponds to the relative area of the surface with that (de, di) pair. Grey area is indicative of no contribution on the surface and blue colour is indicative of the relative area of the surface corresponding to each kind of interaction.
Fig. 4.
Finger print plots for 1 (di and de in Å).
Fig. 6.
Finger print plots for 2 (di and de in Å).
Fig. 8.
Finger print plots for 3 (di and de in Å).
2. Experimental Design, Materials and Methods
2.1. Synthesis of isobutyl-1,2,6-triaryl-4-(arylamino)-1,2,5,6-tetrahydropyridine-3-carboxylates (1-3)
The procedure for the synthesis of 1-3 is given in the source article.“The reactions were performed at room temperature under atmospheric pressure without any inert atmospheric conditions. In a 100 mL round bottomed flask, aromatic amine (1.0 mmol), isobutyl acetoacetate (0.5 mmol), sulfamic acid (catalyst; 0.1 mmol) and ethanol (75 mL) were added successively, and finally the aromatic aldehyde (1.0 mmol) was added. Initially, the reaction mixture was stirred at a slower rate and after the uniform mixing was ensured, the reaction mixture was vigorously agitated up to the completion of the reaction (7-12 hrs). The reaction was monitored by thin layer chromatography (TLC) at regular intervals. When the reaction is completed, the separated solid was filtered and washed thoroughly with aqueous ethanol. The crude products were further purified by column chromatography on silica gel (Ethyl Acetate (EtOAc)/Pet.ether, 1:9 ratio). Single crystals suitable for X-ray diffraction were obtained by the slow evaporation technique using ethanol:dichloromethane (7:3) solvent mixture”.
Declaration of Competing Interest
The authors state that they have no known competing financial interests or personal relationships that could have appeared to influence of the work reported in this paper.
Acknowledgments
One of the authors Dr. P. Surendar Anand is thankful to UGC, India for providing Rajiv Gandhi National Fellowship.
References
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