Crystal structure of

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dihydroxylation (AD) of trans-methyl 3-(4-methoxyphenyl) acrylate by using 1,4-bis(9-O-quininyl)phthalazine. [(QN)2PHAL] as chiral ligand [1]. Single crystal of ...
Z. Kristallogr. NCS 227 (2012) 27-28 / DOI 10.1524/ncrs.2012.0012

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Crystal structure of (2R,3S)-methyl 2,3-dihydroxy3-(4-methoxyphenyl)propanoate, C11H14O5 Peng Liu*, Hai-Bo Wang, Ping-An Wang, Xue-Ying Liu and Xiang-Yang Qin Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi'an 710032, P. R. China Received July 11, 2011, accepted and available on-line December 22, 2011; CCDC no. 1267/3623

In the title compound, the benzene ring is almost parallel with the plane defined by O1–C10–O2. The crystal packing is stabilized by intermolecular O–H$$$O hydrogen bonds. These two hydrogen bonds are different in their lengths and angles: the length of O3–H3A$$$O4 is 2.988 Å and the angle is 142.07°, while the length of O4–H4A$$$O2 is 2.766 Å and the angle is 172.98°. The absolute configurations of C8 and C9 for vicinal dihydroxyl groups were deduced from the known structure of the chiral ligand [2-4,7]. Table 1. Data collection and handling.

Abstract C11H14O5, monoclinic, P21 (no. 4), a = 7.770(2) Å, b = 5.706(1) Å, c = 12.719(2) Å, + = 101.316(3)°, V = 552.9 Å3, Z = 2, Rgt(F) = 0.026, wRref(F2) = 0.070, T = 296 K. Source of material The title compound was prepared by Sharpless asymmetric dihydroxylation (AD) of trans-methyl 3-(4-methoxyphenyl) acrylate by using 1,4-bis(9- O-quininyl) phthalazine [(QN)2PHAL] as chiral ligand [1]. Single crystal of the title compound suitable for X-ray diffraction was recrystallized from ethyl acetate/n-hexane (7:4). Experimental details Because there is no atom heavier than Si in the molecule, the absolute structure of the compound could not be determined by the Flack parameter, as we have used Mo K, radiation as the source of the X-ray. We got the absolute structure information based on experimental data ([,] 25 D = +5.5) and also some literature [2-4]. In the structure, all H atoms were discernible in the difference Fourier maps. However, they were constrained by riding model approximation. Discussion The title compound is a typical chiral vicinal diol and has a prominent role in fine chemicals and the synthetic intermediates of chiral drugs because of its versatile utility [4-6].

Crystal: Wavelength: /: Diffractometer, scan mode: 2-max: N(hkl)measured, N(hkl)unique: Criterion for Iobs, N(hkl)gt: N(param)refined: Programs:

colorless block, size 0.18 " 0.25 " 0.32 mm Mo K, radiation (0.71073 Å) 1.08 cm#1 Bruker SMART CCD, #/& 50.1° 2788, 1080 Iobs > 2 *(Iobs), 1065 150 SHELXS-97, SHELXL-97 [8], ORTEP-3 [9]

Table 2. Atomic coordinates and displacement parameters (in Å2). Atom

Site

H(1A) H(1B) H(1C) H(3) H(4) H(6) H(7) H(8) H(9) H(11A) H(11B) H(11C) H(3A) H(4A)

2a 2a 2a 2a 2a 2a 2a 2a 2a 2a 2a 2a 2a 2a

x

y

0.0953 0.2772 0.2526 0.1076 0.0692 0.3195 0.3616 0.1949 0.4214 0.4497 0.2536 0.4057 0.1655 #0.0688

#0.2036 #0.3191 #0.1743 #0.2702 #0.2272 0.3881 0.3453 0.2724 #0.0149 0.2095 0.2889 0.4637 #0.3150 0.1355

z

Uiso

#0.0935 #0.0464 #0.1531 0.0839 0.2582 0.2791 0.1065 0.4257 0.4690 0.7811 0.7462 0.7371 0.4634 0.3919

0.108 0.108 0.108 0.054 0.050 0.051 0.057 0.045 0.042 0.081 0.081 0.081 0.064 0.069

U13

U23

Table 3. Atomic coordinates and displacement parameters (in Å2). Atom

Site

x

C(1) C(2) C(3) C(4)

2a 2a 2a 2a

0.2203(4) 0.2408(3) 0.1517(3) 0.1288(3)

y #0.1858(7) 0.0327(4) #0.1386(4) #0.1119(4)

z #0.0842(2) 0.0774(2) 0.1233(2) 0.2279(2)

U11

U22

U33

0.092(2) 0.0450(9) 0.050(1) 0.048(1)

0.090(2) 0.052(1) 0.045(1) 0.037(1)

0.039(1) 0.0341(9) 0.039(1) 0.041(1)

U12 #0.012(2) 0.004(1) #0.005(1) #0.0044(9)

0.023(1) 0.0075(7) 0.0074(8) 0.0132(8)

#0.009(1) 0.006(1) #0.0044(9) 0.0009(9)

_____________

* Correspondence author (e-mail: [email protected])

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C11H14O5

Table 3. Continued. Atom

Site

x

C(5) C(6) C(7) C(8) C(9) C(10) C(11) O(1) O(2) O(3) O(4) O(5)

2a 2a 2a 2a 2a 2a 2a 2a 2a 2a 2a 2a

0.1923(2) 0.2782(3) 0.3029(3) 0.1740(3) 0.3026(2) 0.2956(2) 0.3694(3) 0.3683(2) 0.2315(2) 0.2686(2) 0.0045(2) 0.2733(2)

y 0.0820(4) 0.2543(4) 0.2293(4) 0.1083(4) #0.0475(3) 0.0155(4) 0.3026(5) 0.2206(3) #0.1044(3) #0.2877(3) 0.0402(3) 0.0213(4)

z 0.2884(2) 0.2405(2) 0.1369(2) 0.4042(1) 0.4804(1) 0.5961(1) 0.7309(2) 0.6229(1) 0.6556(1) 0.4619(1) 0.4207(1) #0.0241(1)

U11

U22

U33

U12

0.0413(9) 0.050(1) 0.052(1) 0.047(1) 0.0358(9) 0.0317(8) 0.059(1) 0.0517(7) 0.079(1) 0.0479(7) 0.0405(7) 0.081(1)

0.033(1) 0.033(1) 0.044(1) 0.0297(9) 0.033(1) 0.040(1) 0.053(1) 0.0429(8) 0.060(1) 0.0328(7) 0.0565(9) 0.071(1)

0.0367(9) 0.042(1) 0.046(1) 0.0369(9) 0.0383(9) 0.0364(9) 0.048(1) 0.0427(7) 0.0382(7) 0.0484(7) 0.0433(7) 0.0366(7)

0.0040(8) #0.0021(9) #0.004(1) 0.0032(8) #0.0007(8) #0.0039(8) #0.009(1) #0.0121(7) #0.0304(9) 0.0040(7) 0.0129(7) #0.011(1)

U13 0.0076(7) 0.0032(8) 0.0102(8) 0.0105(7) 0.0101(7) 0.0042(7) 0.0062(9) 0.0139(6) 0.0147(7) 0.0130(6) 0.0124(5) 0.0179(7)

U23 0.0029(8) 0.0025(9) 0.012(1) #0.0022(8) 0.0005(8) 0.0014(9) #0.014(1) #0.0056(7) #0.0013(7) #0.0001(7) 0.0033(7) 0.0031(8)

Acknowledgment. We thank the Natural Science Foundation of China (grant nos. 81001398 and 2080209292) for financial support.

References 1. Liu, P.; He, W.; Zhao, Y.; Wang, P. A.; Sun, X. L.; Li, X. Y.; Zhang, S. Y.: Synthesis of Chiral Vicinal Diols and Analysis of Them by Capillary Zone Electrophoresis. Chirality 20 (2008) 75-83. 2. Hentges, S. G.; Sharpless, K. B.: Asymmetric induction in the reaction of osmium tetroxide with olefins. J. Am. Chem. Soc. 102 (1980) 4263-4265. 3. Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B.: Asymmetric dihydroxylation via ligand-accelerated catalysis. J. Am. Chem. Soc. 110 (1988) 1968-1970. 4. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B.: Catalytic Asymmetric Dihydroxylation. Chem. Rev. 94 (1994) 2483-2547. 5. Kobayashi, Y.; William, A. D.; Tokoro, Y.: Sharpless, K. B.: Asymmetric Dihydroxylation of trans-Propenylphosphonate by Using a Modified AD-mix-, and the Synthesis of Fosfomycin. J. Org. Chem. 66 (2001) 7903-7906.

6. Lohray, B. B.; Nandanan, E.; Bhushan, V.: Efficient and Practical Polymeric Catalysts for Heterogeneous Asymmetric Dihydroxylation of Olefins. Tetrahedron: Asymmetry 7 (1996) 645-648. 7. Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y.: Osmium tetroxide— (QN)2PHAL in an ionic liquid: a highly efficient and recyclable catalyst system for asymmetric dihydroxylation of olefins. Chem. Commun. (2002) 3038-3039. 8. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112-122. 9. Farrugia, L. J.: ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) J. Appl. Crystallogr. 30 (1997) 565.

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