Startseite Naturwissenschaften Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
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Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3

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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 230 Heft 4

Abstract

C31H33N2O3, orthorhombic, P212121 (no. 19), a = 7.8122(11) Å, b = 12.2682(18) Å, c = 28.837(4) Å, V = 2763.8(7) Å3, Z = 4, Rgt(F) = 0.0574, wRref(F2) = 0.1189, T = 273 K.

CCDC no.:: 1267/4361

Table 1

Data collection and handling.

Crystal:Red, block,
size 0.22 × 0.28 × 0.43 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.74 cm−1
Diffractometer, scan mode:CCD area detector, φ and ω scans
2θmax:50°
N(hkl)measured, N(hkl)unique:14700, 4882
N(param)refined:332
Programs:SHELXS-97 [8], ORTEP-3 [9], PLATON [10]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomSitexyzUiso
H(1A)4a0.89910.49820.29190.162
H(1B)4a1.09160.50660.30680.162
H(1C)4a1.01910.39630.28770.162
H(2A)4a0.92620.65220.23950.157
H(2B)4a1.06150.65270.19930.157
H(2C)4a1.12080.66810.25090.157
H(5A)4a1.30220.37730.27630.164
H(5B)4a1.39340.49060.27120.164
H(5C)4a1.4520.39180.24060.164
H(6A)4a1.41490.48750.16970.165
H(6B)4a1.36190.59350.19650.165
H(6C)4a1.24310.54680.15750.165
H(9)4a1.11640.23370.11970.06
H(10)4a0.98690.09430.08150.059
H(13)4a0.68310.30640.18550.065
H(14)4a0.42280.19360.17150.069
H(15)4a0.29120.0510.13470.066
H(18A)4a0.2087−0.1580.05760.086
H(18B)4a0.1805−0.05570.08930.086
H(19A)4a0.3357−0.24680.12050.151
H(19B)4a0.1434−0.21760.12990.151
H(19C)4a0.2894−0.14640.15170.151
H(20A)4a0.72370.2843−0.02440.285
H(20B)4a0.90210.3116−0.04640.285
H(20C)4a0.88830.28550.00660.285
H(21A)4a0.8290.1282−0.06420.18
H(21B)4a0.99250.1286−0.03180.18
H(25)4a0.6898−0.16230.1290.078
H(26)4a0.737−0.34380.14620.108
H(27)4a0.8815−0.45230.09280.126
H(28)4a0.9752−0.38320.02490.12
H(30)4a0.995−0.2242−0.03070.106
H(31)4a0.9403−0.0465−0.04840.104
Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
C(1)4a1.0133(6)0.4742(4)0.2852(2)0.140(5)0.097(5)0.088(4)−0.017(4)0.032(4)−0.022(3)
C(2)4a1.0405(6)0.6318(4)0.2309(2)0.127(5)0.043(3)0.145(5)−0.008(3)−0.009(4)−0.021(3)
C(3)4a1.0615(6)0.5085(4)0.2358(2)0.083(3)0.045(3)0.080(4)−0.011(3)−0.003(3)−0.021(3)
C(4)4a1.2273(6)0.4595(4)0.2177(2)0.059(3)0.060(3)0.084(3)−0.012(3)−0.004(3)−0.020(3)
C(5)4a1.3555(6)0.4268(4)0.2549(2)0.078(3)0.129(6)0.121(5)0.011(4)−0.033(3)−0.042(4)
C(6)4a1.3203(6)0.5281(4)0.1821(2)0.099(4)0.082(4)0.148(5)−0.038(4)0.038(4)−0.018(4)
C(7)4a1.0099(6)0.3665(3)0.1846(1)0.059(3)0.039(3)0.058(3)−0.002(2)0.002(2)−0.005(2)
C(8)4a0.9117(5)0.2834(3)0.1577(1)0.047(3)0.033(2)0.057(3)0.000(2)−0.003(2)0.001(2)
C(9)4a1.0016(5)0.2190(3)0.1254(1)0.040(2)0.047(3)0.063(3)0.002(2)0.002(2)0.000(2)
C(10)4a0.9239(5)0.1355(3)0.1025(1)0.046(2)0.046(3)0.055(3)−0.006(2)0.005(2)−0.007(2)
C(11)4a0.7511(5)0.1104(3)0.1100(1)0.044(2)0.039(3)0.047(2)0.003(2)−0.002(2)0.002(2)
C(12)4a0.6570(5)0.1754(3)0.1420(1)0.044(2)0.037(3)0.055(3)0.002(2)0.002(2)−0.002(2)
C(13)4a0.7438(6)0.2627(3)0.1650(1)0.057(3)0.042(3)0.063(3)0.006(2)0.005(2)−0.004(2)
C(14)4a0.4844(5)0.1512(4)0.1506(1)0.051(3)0.052(3)0.069(3)0.007(2)0.012(2)−0.014(2)
C(15)4a0.4057(5)0.0662(3)0.1287(1)0.042(2)0.048(3)0.074(3)−0.004(2)0.002(2)−0.003(2)
C(16)4a0.4974(5)0.0022(3)0.0972(1)0.045(2)0.044(3)0.053(3)−0.004(2)0.000(2)−0.008(2)
C(17)4a0.6654(5)0.0218(3)0.0875(1)0.044(2)0.041(3)0.049(2)0.002(2)0.005(2)−0.001(2)
C(18)4a0.2547(5)−0.1177(4)0.0837(2)0.049(3)0.065(3)0.101(4)−0.008(3)−0.005(3)−0.026(3)
C(19)4a0.2559(6)−0.1883(4)0.1251(2)0.105(4)0.077(4)0.119(4)−0.016(4)0.030(4)0.010(3)
C(20)4a0.844(1)0.2685(7)−0.0236(2)0.194(8)0.22(1)0.154(7)−0.044(8)0.008(6)0.091(7)
C(21)4a0.872(1)0.1478(5)−0.0338(2)0.218(8)0.096(6)0.135(6)−0.011(6)0.008(6)0.047(5)
C(22)4a0.8146(6)−0.0110(4)0.0120(2)0.059(3)0.077(4)0.062(3)−0.002(3)0.004(3)−0.015(3)
C(23)4a0.7608(5)−0.0494(3)0.0540(1)0.042(2)0.052(3)0.054(3)−0.006(2)0.001(2)−0.011(2)
C(24)4a0.7963(5)−0.1605(4)0.0653(2)0.044(3)0.055(3)0.070(3)0.001(2)−0.005(2)−0.019(3)
C(25)4a0.7452(5)−0.2062(4)0.1074(2)0.058(3)0.056(3)0.082(4)0.004(3)−0.003(3)−0.013(3)
C(26)4a0.7743(6)−0.3147(5)0.1182(2)0.085(4)0.058(4)0.127(5)0.010(3)−0.016(4)−0.006(3)
C(27)4a0.8610(8)−0.3794(5)0.0860(3)0.102(5)0.057(4)0.156(6)0.012(4)−0.021(5)−0.014(5)
C(28)4a0.9156(7)−0.3384(5)0.0453(2)0.080(4)0.087(5)0.133(6)0.013(4)−0.013(4)−0.044(4)
C(29)4a0.8837(5)−0.2259(4)0.0326(2)0.047(3)0.065(4)0.098(4)0.007(3)−0.011(3)−0.035(4)
C(30)4a0.9364(7)−0.1808(5)−0.0096(2)0.066(4)0.110(5)0.088(5)−0.006(4)0.012(3)−0.044(4)
C(31)4a0.9041(6)−0.0756(5)−0.0203(2)0.075(4)0.120(5)0.065(3)−0.021(4)0.013(3)−0.031(4)
N(1)4a0.9327(5)0.4563(3)0.2044(1)0.064(2)0.038(2)0.092(3)0.002(2)−0.003(2)−0.024(2)
N(2)4a1.1742(4)0.3594(3)0.1920(1)0.056(2)0.057(3)0.084(3)−0.009(2)0.000(2)−0.016(2)
O(1)4a0.7768(4)0.4838(3)0.2019(1)0.068(2)0.056(2)0.168(3)0.006(2)0.001(2)−0.035(2)
O(2)4a0.7739(4)0.0964(3)0.0028(1)0.105(3)0.087(3)0.072(2)−0.010(3)0.014(2)0.009(2)
O(3)4a0.4225(3)−0.0794(2)0.07236(9)0.045(2)0.060(2)0.072(2)−0.012(2)0.003(2)−0.015(2)

Source of material

The title compound was synthesized according to our previous reported method [1]. Single crystals of compound were obtained from the mixed solution of n-heptane and ethyl acetate (the ratio of volume is 3 to 1) at room temperature.

Experimental details

All hydrogen atoms were placed in calculated positions and refined isotropically using a riding model with Uiso(H) = 1.2(Ueq(C)).

Discussion

Nitroxide radicals are a class of important functionalized molecules, which have wildly used as biophysical tools for electron paramagnetic resonance (EPR) spectroscopic studies such as spin label/oxymetry and spin trapping [2]. Recent studies showed that nitroxide radicals also exhibited interesting biological activities such as anticancer, antiradiation, anti-oxidation properties [3–5]. We here report the crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetramethyl-2-imidazoline-1-oxyle, a strong intramolecular quencher of the fluorescence from fluorophores [1]. In the title structure, the dihedral angle between the two naphthalene ring systems is 68.25(9)°. The molecule is twisted around the central C17—C23 bond with a torsion angle (C16—C17—C23—C24) of −67.4(5)°. The chirality of the molecule, which has a known S configuration, was deduced from the known chiral centres in the substrates used in chemical synthesis, but this could not be confirmed from this X-ray crystal structure analysis. The nitroxide ring and the naphthalene rings are twisted with respect to each other making a dihedral angle of 24.59(13)°. The puckering parameters of the nitroxide ring were Q(2) = 0.204(5) Å and φ = 227.0(13)° [6]. The pseudorotation parameters for the nitroxide ring were P = 28.6(8)° and τ(M) = 21.1(3)° for the C3—N1 reference bond with the closest puckering descriptor being twisted on C3—C4 [7]. No conventional hydrogen bonds was found.

Corresponding author: Hai-Bo Wang, Department of Chemistry School of Pharmacy, Fourth Military Medical University, Xi-An Shaanxi 710032, P. R. China, e-mail:

Acknowledgements:

We acknowledge the financial support from the National Natural Science Foundation of China (NO. 81202458), China Postdoctoral Science Foundation (NO. 2012M521926) and Scientific Research Foundation of Gansu Province (NO. 1308RJYA061).

References

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2. Soule, B. P.; Hyodo, F.; Matsumoto, K.-i.; Simone, N. L.; Cook, J. A.; Krishna, M. C.; Mitchell, J. B. The chemistry and biology of nitroxide compounds. Free Radic. Biol. Med. 42 (2007) 1632–1650.10.1016/j.freeradbiomed.2007.02.030Suche in Google Scholar PubMed PubMed Central

3. Ramachandran, L.; Nair, C. K. K. Prevention of γ-radiation induced cellular genotoxicity by tempol: Protection of hematopoietic system. Environ. Toxicol. Pharmacol. 34 (2012) 253–262.10.1016/j.etap.2012.04.008Suche in Google Scholar PubMed

4. Fleenor, B. S.; Seals, D. R.; Zigler, M. L.; Sindler, A. L. Superoxide-lowering therapy with TEMPOL reverses arterial dysfunction with aging in mice. Aging Cell. 11 (2012) 269–276.Suche in Google Scholar

5. Queiroz, R. F.; Jordão, A. K.; Cunha, A. C.; Ferreira, V. F.; Brigagão, M. R. P. L.; Malvezzi, A.; Amaral, A. T. d.; Augusto, O. Nitroxides attenuate carrageenan-induced inflammation in rat paws by reducing neutrophil infiltration and the resulting myeloperoxidase-mediated damage. Free Radical Biology and Medicine 53 (2012) 1942–1953.Suche in Google Scholar

6. Cremer, D. Pople, J.A. General definition of ring puckering coordinates. J. Amer. Chem. Soc. 97 (1975) 1354–1358.Suche in Google Scholar

7. Rao, S. T.; Westhof, E.; Sundaralingam, M. Exact method for the calculation of pseudorotation parameters P, τm and their errors. A comparison of the Altona-Sundaralingam and Cremer-Pople treatment of puckering of five-membered rings. Acta Cryst. A37 (1981) 421–425.Suche in Google Scholar

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Received: 2015-2-15
Accepted: 2015-11-3
Published Online: 2015-12-7
Published in Print: 2015-12-1

©2015 Lin-Lin Jing et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
https://doi.org/10.1515/ncrs-2015-0027
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Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
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Heruntergeladen am 27.3.2026 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2015-0027/html
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