organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

(S)-3-[(S)-5-(4-Fluoro­phen­yl)-5-hy­dr­oxy­penta­noyl]-4-phenyl­oxazolidin-2-one 0.67-hydrate

aShandong Jincheng Pharmaceutical Co. Ltd, No. 26 Kunxin Road, Zichuan District, Zibo 255130, People's Republic of China, bCollege of Science, China University of Petroleum, Qingdao 266580, People's Republic of China, and cCollege of Chemical Engineering, China University of Petroleum, Qingdao 266580, People's Republic of China
*Correspondence e-mail: wxg0704@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 20 January 2017; accepted 9 February 2017; online 14 February 2017)

The asymmetric unit of the title compound, 3C20H20FNO4·2H2O, consists of three (S)-3-[(S)-5-(4-fluoro­phen­yl)-5-hy­droxy­penta­noyl]-4-phenyl­oxazolidin-2-one mol­ecules and two solvent water mol­ecules. The carbonyl groups of the oxazolidin-2-one and hy­droxy­penta­noyl units are oriented anti to one another in each mol­ecule. In the crystal, O—H⋯O, C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into a three-dimensional supra­molecular architecture with the organic mol­ecules linked by water mol­ecules and stacked along the b-axis direction.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Phenyl­oxazolidinones have received much attention due to their applications in asymmetric synthesis (Evans et al., 1982[Evans, D. A., Nelson, J. V. & Taber, T. (1982). Top. Stereochem. 13, 1-115.]). We report here the synthesis and crystal structure of the title oxazolidinone compound (Fig. 1[link]). This is an inter­mediate in the synthesis of the cholesterol-lowering agent Ezetimibe, which is a novel and potent drug that selectively inhibits cholesterol absorption across the intestinal wall (van Heek et al., 2000[Heek, M. van, Farley, C., Compton, D. S., Hoos, L., Alton, K. B., Sybertz, E. J. & Davis, H. R. (2000). Br. J. Pharmacol. 129, 1748-1754.]). Clinical studies show that Ezetimibe can significantly decrease plasma LDL cholesterol levels and increase plasma HDL levels with an excellent tolerability profile (Wu et al. 1999[Wu, G., Wong, Y., Chen, X. & Ding, Z. (1999). J. Org. Chem. 64, 3714-3718.]).

[Figure 1]
Figure 1
A view of the title compound showing the three-dimensional supra­molecular architecture linked by pairs of O—H⋯O hydrogen bonds. Displacement ellipsoids are drawn at the 50% probability level.

The asymmetric unit of the title compound consists of three (S)-3-[(S)-5-(4-fluoro­phen­yl)-5-hy­droxy­penta­noyl]-4-phenyl­oxazolidin-2-one mol­ecules (A incorporating F1, B with F2 and C with F3), together with two solvent water mol­ecules. The organic mol­ecules differ mainly in the relative inclination of the two aromatic rings. Each unique mol­ecule has two stereogenic centres, at C7 and C14 for A, C27 and C34 for B and C47 and C54 for C. Each of these adopt an S configuration. Bond lengths and angles are within normal ranges (Yang et al., 2006[Yang, R., Nie, L., Zhang, M.-S., Wang, J. & Lin, J. (2006). Acta Cryst. E62, o3618-o3619.]). In mol­ecule A, the benzene ring is inclined at an angle of 65.36 (12)° to the fluoro­benzene ring. The corresponding angles for mol­ecules B and C are 63.55 (13) and 23.49 (14)°, respectively.

In the crystal, O—H⋯O, C—H⋯O and C—H⋯F hydrogen bonds are found involving both the organic and solvent water mol­ecules (Table 1[link], Fig. 1[link]). These produce a three-dimensional network with the organic mol­ecules linked by water mol­ecules and stacked along the b-axis direction (Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O10—H10⋯O8 0.82 2.02 2.837 (3) 173
O6—H6A⋯O10i 0.82 1.99 2.797 (3) 167
O1—H1⋯O14ii 0.82 1.85 2.669 (4) 174
C22—H22⋯O6iii 0.93 2.65 3.522 (3) 157
C33—H33A⋯O7iv 0.97 2.57 3.337 (4) 137
C30—H30A⋯O6 0.97 2.58 3.149 (3) 118
C30—H30B⋯O8 0.97 2.31 2.860 (4) 115
O14—H14A⋯O1 0.85 1.88 2.728 (3) 173
O14—H14B⋯O13ii 0.85 2.01 2.825 (3) 161
C13—H13B⋯F2iv 0.97 2.51 3.347 (3) 145
C42—H42⋯O3v 0.93 2.37 3.232 (3) 153
O5—H5B⋯O3v 0.85 2.09 2.928 (5) 171
Symmetry codes: (i) [-x-1, y+{\script{1\over 2}}, -z]; (ii) [-x, y+{\script{1\over 2}}, -z+1]; (iii) x, y+1, z; (iv) [-x, y-{\script{1\over 2}}, -z]; (v) x, y-1, z.
[Figure 2]
Figure 2
The crystal packing of the title compound, viewed along the b-axis direction.

Synthesis and crystallization

The title compound was prepared according to a literature procedure (Fu et al. 2003[Fu, X., McAllister, T. L., Thiruvengadam, T. K., Tann, C. & Su, D. (2003). Tetrahedron Lett. 44, 801-804.]; Bertrand et al. 2007[Bertrand, B., Durassier, S., Frein, S. & Burgos, A. (2007). Tetrahedron Lett. 48, 2123-2125.]). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at room temperature over a period of 30 days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula 3C20H20FNO4·2H2O
Mr 1108.14
Crystal system, space group Monoclinic, P21
Temperature (K) 293
a, b, c (Å) 15.4975 (10), 7.8125 (5), 24.1875 (18)
β (°) 107.517 (8)
V3) 2792.7 (3)
Z 2
Radiation type Cu Kα
μ (mm−1) 0.84
Crystal size (mm) 0.42 × 0.26 × 0.22
 
Data collection
Diffractometer Rigaku Xcalibur Eos Gemini
Absorption correction Multi-scan (CrysAlis PRO; Rigaku, 2015[Rigaku (2015). CrysAlis PRO. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.691, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 29311, 9875, 8563
Rint 0.033
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.119, 1.06
No. of reflections 9875
No. of parameters 727
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.20, −0.31
Absolute structure Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])
Absolute structure parameter 0.07 (13)
Computer programs: CrysAlis PRO (Rigaku, 2015[Rigaku (2015). CrysAlis PRO. Rigaku Corporation, Tokyo, Japan.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Rigaku, 2015); cell refinement: CrysAlis PRO (Rigaku, 2015); data reduction: CrysAlis PRO (Rigaku, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(S)-3-[(S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyloxazolidin-2-one 0.67-hydrate top
Crystal data top
3C20H20FNO4·2H2OF(000) = 1168
Mr = 1108.14Dx = 1.318 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 15.4975 (10) ÅCell parameters from 10080 reflections
b = 7.8125 (5) Åθ = 5.5–72.3°
c = 24.1875 (18) ŵ = 0.84 mm1
β = 107.517 (8)°T = 293 K
V = 2792.7 (3) Å3Needle, colourless
Z = 20.42 × 0.26 × 0.22 mm
Data collection top
Rigaku Xcalibur Eos Gemini
diffractometer
9875 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source8563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 16.0355 pixels mm-1θmax = 66.6°, θmin = 5.5°
ω scansh = 1817
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku, 2015)
k = 99
Tmin = 0.691, Tmax = 1.000l = 2728
29311 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0733P)2 + 0.0055P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
9875 reflectionsΔρmax = 0.20 e Å3
727 parametersΔρmin = 0.31 e Å3
1 restraintAbsolute structure: Flack (1983), ??? Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (13)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.22186 (13)0.5917 (2)0.27097 (8)0.0651 (4)
O90.10736 (13)0.0727 (2)0.08775 (9)0.0701 (5)
O130.22269 (11)0.1772 (3)0.41117 (8)0.0670 (5)
O100.34846 (12)0.0634 (3)0.13565 (8)0.0663 (5)
H100.31540.03840.11600.099*
N10.19278 (13)0.3495 (2)0.30979 (8)0.0507 (4)
O20.20106 (12)0.1166 (2)0.36458 (8)0.0634 (4)
N20.13039 (13)0.1743 (2)0.04055 (8)0.0511 (4)
N30.34780 (13)0.2339 (3)0.43586 (8)0.0528 (5)
O60.47429 (13)0.4274 (2)0.06100 (9)0.0674 (5)
H6A0.52290.42370.08670.101*
O10.05047 (15)0.3350 (3)0.44097 (10)0.0830 (6)
H10.05190.43610.44970.124*
O70.13564 (12)0.3822 (2)0.02380 (8)0.0643 (4)
C440.25569 (15)0.2934 (3)0.18945 (9)0.0503 (5)
C510.30383 (15)0.1882 (3)0.39561 (10)0.0506 (5)
F20.44779 (13)1.0810 (2)0.20943 (9)0.0877 (5)
O30.08350 (12)0.5607 (2)0.27908 (9)0.0698 (5)
C240.45010 (14)0.7244 (3)0.08478 (10)0.0494 (5)
C110.15345 (16)0.2291 (3)0.33788 (10)0.0504 (5)
C550.27078 (15)0.0930 (3)0.52883 (9)0.0497 (5)
C40.20339 (16)0.3232 (3)0.37583 (10)0.0527 (5)
C100.05462 (17)0.2476 (3)0.33214 (11)0.0570 (5)
H10A0.01980.23550.29160.068*
H10B0.04380.36150.34450.068*
O80.24876 (14)0.0229 (3)0.05862 (9)0.0759 (5)
C500.35969 (15)0.1553 (3)0.33420 (9)0.0506 (5)
H50A0.39410.05060.33250.061*
H50B0.40220.24850.32090.061*
C140.28594 (16)0.3244 (3)0.30862 (10)0.0532 (5)
H140.32570.30600.34820.064*
C190.37247 (17)0.0785 (3)0.25634 (12)0.0610 (6)
H190.41770.15940.27070.073*
C210.44538 (17)0.9637 (3)0.16697 (13)0.0594 (6)
C260.45009 (19)0.7944 (3)0.18126 (12)0.0611 (6)
H260.45180.75980.21840.073*
C350.02871 (15)0.2855 (3)0.07010 (9)0.0487 (5)
C120.15785 (17)0.5051 (3)0.28622 (10)0.0539 (5)
C150.29514 (15)0.1764 (3)0.27074 (10)0.0493 (5)
F30.14961 (16)0.7748 (3)0.18369 (10)0.0975 (6)
C480.35387 (16)0.1066 (3)0.23169 (10)0.0557 (5)
H48A0.38150.00590.22830.067*
H48B0.40200.19060.21950.067*
C470.29457 (15)0.1167 (3)0.19187 (10)0.0541 (5)
H470.24440.03580.20580.065*
C310.17600 (16)0.3071 (3)0.00470 (11)0.0558 (5)
C270.45808 (16)0.5962 (3)0.03945 (11)0.0554 (5)
H270.50950.63060.02630.067*
C320.16962 (17)0.0417 (3)0.06248 (11)0.0584 (6)
C220.44054 (17)1.0194 (3)0.11293 (13)0.0643 (7)
H220.43581.13540.10390.077*
C250.45224 (16)0.6754 (3)0.13935 (10)0.0530 (5)
H250.45520.55950.14860.064*
O110.50008 (14)0.2329 (4)0.38475 (9)0.0960 (9)
C410.1848 (2)0.6152 (4)0.18596 (12)0.0644 (6)
C160.23945 (17)0.1628 (3)0.21409 (11)0.0575 (6)
H160.19410.24340.19950.069*
C430.16286 (16)0.3218 (4)0.20818 (11)0.0603 (6)
H430.12380.23040.22190.072*
C600.18220 (16)0.0352 (3)0.54343 (10)0.0544 (5)
H600.13870.10030.53370.065*
C230.44282 (17)0.8985 (3)0.07185 (12)0.0603 (6)
H230.43940.93410.03460.072*
C340.03547 (16)0.1386 (3)0.04692 (10)0.0497 (5)
H340.02940.10120.00960.060*
C200.36096 (16)0.0527 (3)0.29121 (10)0.0552 (5)
H200.39810.05860.32940.066*
C170.25083 (18)0.0304 (4)0.17918 (11)0.0636 (6)
H170.21330.02280.14120.076*
C490.30037 (16)0.1390 (4)0.29458 (10)0.0559 (5)
H49A0.25800.04570.30820.067*
H49B0.26560.24340.29690.067*
C590.1581 (2)0.1179 (4)0.57229 (12)0.0675 (7)
H590.09840.15490.58200.081*
C400.10942 (16)0.2918 (3)0.05677 (11)0.0566 (6)
H400.12150.21060.03200.068*
C540.29644 (17)0.2617 (3)0.49713 (10)0.0551 (6)
H540.24200.32940.50000.066*
C180.31706 (18)0.0901 (3)0.20003 (13)0.0630 (6)
H180.32450.17900.17630.076*
C80.07815 (18)0.1388 (3)0.36260 (14)0.0646 (6)
H8A0.11330.12260.32240.078*
H8B0.09550.04940.38500.078*
C450.31084 (16)0.4325 (4)0.16908 (10)0.0576 (6)
H450.37320.41660.15630.069*
C570.3098 (2)0.1605 (4)0.57261 (13)0.0714 (7)
H570.35300.22600.58260.086*
F10.47752 (14)0.3445 (4)0.35090 (15)0.1285 (9)
C460.27641 (19)0.5951 (4)0.16702 (11)0.0640 (6)
H460.31450.68760.15320.077*
C520.4393 (2)0.2631 (4)0.42661 (12)0.0703 (7)
C90.02166 (19)0.1162 (3)0.36768 (13)0.0649 (6)
H9A0.05730.12640.40810.078*
H9B0.03100.00220.35470.078*
O120.45079 (15)0.3331 (4)0.47472 (9)0.0893 (7)
C280.37471 (18)0.5924 (4)0.01321 (12)0.0681 (7)
H28A0.38610.51400.04130.082*
H28B0.36660.70540.03060.082*
C370.0741 (2)0.5354 (4)0.12905 (12)0.0771 (9)
H370.06160.61870.15300.092*
C60.3316 (3)0.2844 (5)0.41097 (18)0.0855 (9)
H60.35550.25360.44050.103*
C390.17225 (19)0.4186 (4)0.08024 (15)0.0758 (8)
H390.22680.42140.07170.091*
C10.3870 (2)0.3373 (4)0.35868 (17)0.0790 (9)
C580.2215 (2)0.2165 (4)0.58683 (12)0.0732 (8)
H580.20500.32000.60610.088*
C50.2391 (2)0.2772 (4)0.41952 (13)0.0725 (7)
H50.20070.24100.45510.087*
C30.26199 (18)0.3771 (4)0.32441 (11)0.0628 (6)
H30.23920.41050.29460.075*
C290.28564 (17)0.5395 (4)0.00236 (13)0.0683 (7)
H29A0.28630.57930.03570.082*
H29B0.23580.59580.03070.082*
C330.01930 (19)0.0126 (4)0.08834 (14)0.0678 (7)
H33A0.01370.10230.07560.081*
H33B0.01540.02260.12710.081*
C70.10324 (17)0.3109 (3)0.38279 (12)0.0612 (6)
H70.08760.40080.35920.073*
C300.26961 (19)0.3539 (4)0.00576 (18)0.0821 (9)
H30A0.31360.29890.02660.098*
H30B0.27860.31070.04120.098*
C360.0118 (2)0.4079 (3)0.10679 (11)0.0643 (6)
H360.04180.40420.11650.077*
O140.05185 (19)0.1703 (4)0.53805 (15)0.1212 (12)
H14A0.01640.21720.50810.182*
H14B0.09570.23740.55340.182*
C530.3653 (2)0.3691 (4)0.51606 (12)0.0766 (9)
H53A0.35110.49000.51590.092*
H53B0.36550.33720.55480.092*
C380.1539 (2)0.5403 (4)0.11621 (14)0.0808 (10)
H380.19590.62590.13180.097*
C130.30596 (19)0.5005 (3)0.28677 (14)0.0649 (6)
H13A0.35110.56100.31700.078*
H13B0.32810.48770.25350.078*
C560.33461 (18)0.0068 (3)0.54337 (12)0.0615 (6)
H560.39450.02950.53350.074*
C20.3539 (2)0.3830 (4)0.31565 (15)0.0778 (8)
H20.39280.41840.28020.093*
C420.12762 (18)0.4843 (4)0.20677 (13)0.0700 (7)
H420.06550.50270.22000.084*
O50.0698 (3)0.0859 (5)0.23695 (19)0.1632 (16)
H5A0.10420.03610.26970.245*
H5B0.06980.19130.24560.245*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0691 (11)0.0534 (9)0.0741 (11)0.0094 (8)0.0237 (9)0.0123 (8)
O90.0742 (12)0.0604 (10)0.0779 (12)0.0054 (9)0.0261 (9)0.0212 (9)
O130.0472 (9)0.0944 (13)0.0528 (9)0.0038 (9)0.0051 (7)0.0029 (9)
O100.0555 (9)0.0905 (13)0.0534 (9)0.0090 (9)0.0172 (7)0.0222 (9)
N10.0535 (10)0.0470 (9)0.0535 (10)0.0015 (8)0.0189 (8)0.0038 (8)
O20.0631 (10)0.0549 (9)0.0730 (11)0.0025 (8)0.0218 (8)0.0146 (8)
N20.0509 (10)0.0508 (10)0.0558 (11)0.0036 (8)0.0225 (8)0.0028 (8)
N30.0497 (10)0.0594 (11)0.0432 (10)0.0019 (8)0.0048 (8)0.0031 (8)
O60.0623 (11)0.0611 (10)0.0728 (12)0.0002 (8)0.0114 (8)0.0094 (9)
O10.0727 (12)0.0783 (13)0.0756 (13)0.0090 (10)0.0114 (10)0.0061 (10)
O70.0593 (10)0.0644 (10)0.0721 (11)0.0057 (8)0.0241 (8)0.0202 (9)
C440.0429 (11)0.0715 (14)0.0369 (10)0.0055 (10)0.0127 (8)0.0036 (10)
C510.0512 (12)0.0498 (11)0.0449 (11)0.0017 (9)0.0054 (9)0.0059 (9)
F20.0934 (12)0.0706 (10)0.1084 (14)0.0012 (9)0.0446 (10)0.0278 (10)
O30.0584 (11)0.0632 (10)0.0812 (12)0.0030 (8)0.0107 (8)0.0207 (9)
C240.0372 (10)0.0566 (12)0.0542 (12)0.0056 (8)0.0136 (8)0.0053 (10)
C110.0556 (12)0.0443 (11)0.0516 (12)0.0027 (9)0.0166 (9)0.0007 (9)
C550.0538 (12)0.0508 (11)0.0390 (10)0.0055 (9)0.0055 (8)0.0079 (9)
C40.0586 (13)0.0465 (11)0.0514 (12)0.0046 (9)0.0140 (10)0.0041 (9)
C100.0570 (13)0.0541 (12)0.0589 (13)0.0052 (10)0.0160 (10)0.0040 (10)
O80.0686 (12)0.0860 (13)0.0778 (13)0.0171 (10)0.0292 (9)0.0154 (11)
C500.0486 (11)0.0548 (12)0.0440 (11)0.0019 (9)0.0070 (8)0.0024 (9)
C140.0500 (11)0.0569 (13)0.0514 (12)0.0048 (10)0.0135 (9)0.0001 (10)
C190.0557 (13)0.0449 (11)0.0757 (16)0.0053 (10)0.0094 (11)0.0066 (11)
C210.0471 (12)0.0567 (13)0.0766 (17)0.0011 (10)0.0219 (11)0.0076 (12)
C260.0650 (15)0.0640 (14)0.0588 (14)0.0010 (12)0.0257 (11)0.0002 (11)
C350.0519 (12)0.0457 (11)0.0454 (11)0.0007 (9)0.0100 (9)0.0048 (8)
C120.0582 (14)0.0515 (12)0.0481 (12)0.0054 (10)0.0104 (9)0.0045 (9)
C150.0464 (11)0.0486 (11)0.0518 (12)0.0036 (9)0.0133 (9)0.0054 (9)
F30.1119 (15)0.0768 (11)0.1071 (15)0.0185 (11)0.0380 (12)0.0004 (11)
C480.0505 (12)0.0663 (14)0.0486 (12)0.0008 (10)0.0126 (9)0.0026 (10)
C470.0478 (11)0.0629 (13)0.0497 (12)0.0062 (10)0.0118 (9)0.0072 (10)
C310.0522 (12)0.0502 (12)0.0654 (14)0.0027 (10)0.0181 (11)0.0039 (11)
C270.0477 (12)0.0649 (14)0.0564 (13)0.0086 (10)0.0198 (10)0.0018 (11)
C320.0619 (14)0.0628 (14)0.0545 (13)0.0113 (11)0.0235 (10)0.0032 (11)
C220.0509 (13)0.0473 (12)0.0906 (19)0.0009 (10)0.0149 (12)0.0083 (12)
C250.0577 (13)0.0476 (11)0.0552 (13)0.0001 (9)0.0192 (10)0.0052 (10)
O110.0525 (10)0.167 (3)0.0593 (12)0.0153 (13)0.0032 (9)0.0261 (13)
C410.0754 (17)0.0653 (15)0.0558 (14)0.0042 (13)0.0249 (12)0.0013 (12)
C160.0532 (13)0.0592 (13)0.0552 (13)0.0103 (10)0.0088 (10)0.0057 (11)
C430.0451 (12)0.0746 (16)0.0599 (14)0.0100 (11)0.0136 (10)0.0069 (12)
C600.0531 (13)0.0603 (13)0.0466 (12)0.0038 (10)0.0103 (9)0.0005 (10)
C230.0551 (13)0.0636 (14)0.0599 (14)0.0077 (11)0.0140 (10)0.0156 (12)
C340.0537 (12)0.0448 (11)0.0521 (12)0.0009 (9)0.0185 (9)0.0002 (9)
C200.0529 (12)0.0538 (12)0.0525 (12)0.0006 (10)0.0062 (9)0.0089 (10)
C170.0613 (14)0.0691 (15)0.0525 (13)0.0013 (12)0.0052 (10)0.0023 (11)
C490.0504 (11)0.0667 (14)0.0478 (12)0.0045 (10)0.0102 (9)0.0038 (10)
C590.0709 (16)0.0680 (15)0.0569 (14)0.0139 (13)0.0092 (12)0.0027 (12)
C400.0487 (12)0.0528 (12)0.0658 (14)0.0010 (10)0.0136 (10)0.0084 (11)
C540.0617 (14)0.0510 (12)0.0441 (11)0.0039 (10)0.0028 (10)0.0047 (9)
C180.0649 (15)0.0471 (12)0.0755 (16)0.0036 (11)0.0188 (12)0.0075 (11)
C80.0595 (15)0.0562 (13)0.0813 (17)0.0127 (11)0.0261 (12)0.0010 (12)
C450.0451 (11)0.0778 (16)0.0460 (11)0.0076 (11)0.0078 (9)0.0041 (11)
C570.090 (2)0.0570 (14)0.0708 (17)0.0228 (14)0.0305 (14)0.0067 (12)
F10.0635 (11)0.1211 (18)0.206 (3)0.0072 (12)0.0488 (14)0.0150 (19)
C460.0725 (16)0.0675 (15)0.0504 (13)0.0133 (12)0.0161 (11)0.0026 (11)
C520.0623 (15)0.0890 (19)0.0518 (14)0.0156 (14)0.0054 (12)0.0103 (13)
C90.0651 (15)0.0510 (12)0.0813 (18)0.0063 (11)0.0257 (13)0.0091 (12)
O120.0756 (13)0.127 (2)0.0581 (11)0.0367 (13)0.0093 (9)0.0189 (12)
C280.0566 (14)0.0882 (19)0.0563 (14)0.0136 (13)0.0120 (11)0.0028 (13)
C370.107 (2)0.0564 (15)0.0549 (15)0.0064 (15)0.0047 (14)0.0062 (12)
C60.095 (2)0.0777 (19)0.103 (3)0.0136 (17)0.059 (2)0.0022 (18)
C390.0538 (14)0.0746 (18)0.087 (2)0.0125 (12)0.0026 (13)0.0205 (16)
C10.0598 (15)0.0631 (16)0.114 (3)0.0066 (13)0.0266 (16)0.0117 (16)
C580.104 (2)0.0490 (13)0.0621 (16)0.0026 (14)0.0178 (14)0.0018 (12)
C50.0826 (19)0.0778 (18)0.0572 (15)0.0028 (14)0.0211 (13)0.0130 (13)
C30.0620 (14)0.0687 (15)0.0539 (13)0.0025 (12)0.0115 (11)0.0076 (11)
C290.0503 (13)0.0754 (17)0.0754 (17)0.0052 (12)0.0131 (11)0.0078 (14)
C330.0664 (16)0.0569 (14)0.0807 (18)0.0027 (11)0.0227 (13)0.0158 (12)
C70.0556 (13)0.0575 (13)0.0635 (15)0.0085 (11)0.0073 (10)0.0073 (11)
C300.0536 (15)0.0722 (17)0.122 (3)0.0019 (13)0.0294 (15)0.0130 (18)
C360.0781 (17)0.0610 (14)0.0534 (13)0.0003 (12)0.0192 (12)0.0026 (11)
O140.0865 (17)0.112 (2)0.126 (2)0.0344 (15)0.0269 (15)0.0572 (18)
C530.097 (2)0.0675 (16)0.0522 (14)0.0190 (15)0.0026 (14)0.0112 (12)
C380.087 (2)0.0602 (16)0.0713 (17)0.0230 (14)0.0125 (15)0.0084 (14)
C130.0673 (16)0.0571 (13)0.0785 (17)0.0080 (12)0.0343 (13)0.0029 (12)
C560.0570 (13)0.0609 (14)0.0657 (15)0.0095 (11)0.0172 (11)0.0097 (11)
C20.0610 (16)0.0759 (18)0.0811 (19)0.0009 (14)0.0017 (14)0.0033 (15)
C420.0502 (13)0.092 (2)0.0668 (16)0.0086 (13)0.0159 (11)0.0009 (14)
O50.190 (4)0.113 (3)0.165 (4)0.010 (3)0.022 (3)0.017 (3)
Geometric parameters (Å, º) top
O4—C121.341 (3)C41—C421.348 (4)
O4—C131.433 (3)C16—H160.9300
O9—C321.322 (3)C16—C171.379 (4)
O9—C331.439 (3)C43—H430.9300
O13—C511.202 (3)C43—C421.387 (4)
O10—H100.8200C60—H600.9300
O10—C471.427 (3)C60—C591.379 (4)
N1—C111.402 (3)C23—H230.9300
N1—C141.466 (3)C34—H340.9800
N1—C121.382 (3)C34—C331.520 (3)
O2—C111.203 (3)C20—H200.9300
N2—C311.400 (3)C17—H170.9300
N2—C321.385 (3)C17—C181.372 (4)
N2—C341.459 (3)C49—H49A0.9700
N3—C511.393 (3)C49—H49B0.9700
N3—C541.472 (3)C59—H590.9300
N3—C521.386 (4)C59—C581.375 (5)
O6—H6A0.8200C40—H400.9300
O6—C271.412 (3)C40—C391.385 (4)
O1—H10.8200C54—H540.9800
O1—C71.411 (3)C54—C531.532 (4)
O7—C311.213 (3)C18—H180.9300
C44—C471.515 (4)C8—H8A0.9700
C44—C431.390 (3)C8—H8B0.9700
C44—C451.379 (3)C8—C91.525 (4)
C51—C501.499 (3)C8—C71.521 (4)
F2—C211.368 (3)C45—H450.9300
O3—C121.194 (3)C45—C461.384 (4)
C24—C271.517 (4)C57—H570.9300
C24—C251.365 (3)C57—C581.378 (5)
C24—C231.392 (4)C57—C561.388 (4)
C11—C101.503 (3)F1—C11.360 (4)
C55—C601.386 (3)C46—H460.9300
C55—C541.516 (3)C52—O121.346 (4)
C55—C561.385 (4)C9—H9A0.9700
C4—C51.380 (4)C9—H9B0.9700
C4—C31.367 (3)O12—C531.427 (4)
C4—C71.513 (4)C28—H28A0.9700
C10—H10A0.9700C28—H28B0.9700
C10—H10B0.9700C28—C291.537 (4)
C10—C91.523 (4)C37—H370.9300
O8—C321.211 (3)C37—C361.378 (4)
C50—H50A0.9700C37—C381.363 (5)
C50—H50B0.9700C6—H60.9300
C50—C491.520 (4)C6—C11.361 (5)
C14—H140.9800C6—C51.387 (5)
C14—C151.508 (3)C39—H390.9300
C14—C131.538 (4)C39—C381.375 (5)
C19—H190.9300C1—C21.339 (5)
C19—C201.373 (4)C58—H580.9300
C19—C181.377 (4)C5—H50.9300
C21—C261.363 (4)C3—H30.9300
C21—C221.358 (4)C3—C21.377 (4)
C26—H260.9300C29—H29A0.9700
C26—C251.384 (4)C29—H29B0.9700
C35—C341.511 (3)C29—C301.469 (4)
C35—C401.383 (4)C33—H33A0.9700
C35—C361.382 (4)C33—H33B0.9700
C15—C161.386 (3)C7—H70.9800
C15—C201.384 (3)C30—H30A0.9700
F3—C411.368 (4)C30—H30B0.9700
C48—H48A0.9700C36—H360.9300
C48—H48B0.9700O14—H14A0.8497
C48—C471.520 (3)O14—H14B0.8504
C48—C491.519 (3)C53—H53A0.9700
C47—H470.9800C53—H53B0.9700
C31—C301.504 (4)C38—H380.9300
C27—H270.9800C13—H13A0.9700
C27—C281.517 (3)C13—H13B0.9700
C22—H220.9300C56—H560.9300
C22—C231.379 (4)C2—H20.9300
C25—H250.9300C42—H420.9300
O11—C521.181 (3)O5—H5A0.9000
C41—C461.363 (4)O5—H5B0.8495
C12—O4—C13111.37 (19)C50—C49—H49B108.9
C32—O9—C33110.00 (19)C48—C49—C50113.21 (19)
C47—O10—H10109.5C48—C49—H49A108.9
C11—N1—C14119.60 (19)C48—C49—H49B108.9
C12—N1—C11128.0 (2)H49A—C49—H49B107.8
C12—N1—C14112.1 (2)C60—C59—H59119.7
C31—N2—C34120.80 (19)C58—C59—C60120.7 (3)
C32—N2—C31126.4 (2)C58—C59—H59119.7
C32—N2—C34111.2 (2)C35—C40—H40119.9
C51—N3—C54120.8 (2)C35—C40—C39120.2 (3)
C52—N3—C51128.41 (19)C39—C40—H40119.9
C52—N3—C54110.8 (2)N3—C54—C55111.16 (18)
C27—O6—H6A109.5N3—C54—H54110.1
C7—O1—H1109.5N3—C54—C5399.64 (19)
C43—C44—C47121.2 (2)C55—C54—H54110.1
C45—C44—C47121.4 (2)C55—C54—C53115.2 (2)
C45—C44—C43117.4 (2)C53—C54—H54110.1
O13—C51—N3119.0 (2)C19—C18—H18120.2
O13—C51—C50122.4 (2)C17—C18—C19119.5 (2)
N3—C51—C50118.59 (19)C17—C18—H18120.2
C25—C24—C27122.0 (2)H8A—C8—H8B107.5
C25—C24—C23117.9 (2)C9—C8—H8A108.4
C23—C24—C27120.1 (2)C9—C8—H8B108.4
N1—C11—C10118.1 (2)C7—C8—H8A108.4
O2—C11—N1117.7 (2)C7—C8—H8B108.4
O2—C11—C10124.3 (2)C7—C8—C9115.3 (2)
C60—C55—C54120.0 (2)C44—C45—H45118.9
C56—C55—C60118.7 (2)C44—C45—C46122.1 (2)
C56—C55—C54121.2 (2)C46—C45—H45118.9
C5—C4—C7122.2 (2)C58—C57—H57119.9
C3—C4—C5117.9 (3)C58—C57—C56120.2 (3)
C3—C4—C7119.9 (2)C56—C57—H57119.9
C11—C10—H10A109.0C41—C46—C45117.9 (2)
C11—C10—H10B109.0C41—C46—H46121.1
C11—C10—C9112.9 (2)C45—C46—H46121.1
H10A—C10—H10B107.8O11—C52—N3128.3 (3)
C9—C10—H10A109.0O11—C52—O12122.9 (3)
C9—C10—H10B109.0O12—C52—N3108.8 (2)
C51—C50—H50A109.4C10—C9—C8112.4 (2)
C51—C50—H50B109.4C10—C9—H9A109.1
C51—C50—C49111.13 (19)C10—C9—H9B109.1
H50A—C50—H50B108.0C8—C9—H9A109.1
C49—C50—H50A109.4C8—C9—H9B109.1
C49—C50—H50B109.4H9A—C9—H9B107.9
N1—C14—H14109.5C52—O12—C53110.4 (2)
N1—C14—C15112.83 (18)C27—C28—H28A108.2
N1—C14—C13100.9 (2)C27—C28—H28B108.2
C15—C14—H14109.5C27—C28—C29116.3 (2)
C15—C14—C13114.3 (2)H28A—C28—H28B107.4
C13—C14—H14109.5C29—C28—H28A108.2
C20—C19—H19120.0C29—C28—H28B108.2
C20—C19—C18120.0 (2)C36—C37—H37119.7
C18—C19—H19120.0C38—C37—H37119.7
C26—C21—F2118.2 (3)C38—C37—C36120.5 (3)
C22—C21—F2119.3 (2)C1—C6—H6120.5
C22—C21—C26122.6 (3)C1—C6—C5119.0 (3)
C21—C26—H26120.7C5—C6—H6120.5
C21—C26—C25118.5 (3)C40—C39—H39120.0
C25—C26—H26120.7C38—C39—C40120.0 (3)
C40—C35—C34118.7 (2)C38—C39—H39120.0
C36—C35—C34122.2 (2)F1—C1—C6118.5 (4)
C36—C35—C40118.9 (2)C2—C1—F1120.1 (3)
O4—C12—N1109.1 (2)C2—C1—C6121.4 (3)
O3—C12—O4122.5 (2)C59—C58—C57119.4 (3)
O3—C12—N1128.4 (2)C59—C58—H58120.3
C16—C15—C14121.0 (2)C57—C58—H58120.3
C20—C15—C14120.8 (2)C4—C5—C6120.7 (3)
C20—C15—C16118.2 (2)C4—C5—H5119.7
H48A—C48—H48B107.9C6—C5—H5119.7
C47—C48—H48A109.2C4—C3—H3119.2
C47—C48—H48B109.2C4—C3—C2121.6 (3)
C49—C48—H48A109.2C2—C3—H3119.2
C49—C48—H48B109.2C28—C29—H29A108.8
C49—C48—C47111.97 (19)C28—C29—H29B108.8
O10—C47—C44110.8 (2)H29A—C29—H29B107.7
O10—C47—C48107.26 (19)C30—C29—C28113.6 (3)
O10—C47—H47108.5C30—C29—H29A108.8
C44—C47—C48113.3 (2)C30—C29—H29B108.8
C44—C47—H47108.5O9—C33—C34106.2 (2)
C48—C47—H47108.5O9—C33—H33A110.5
N2—C31—C30118.7 (2)O9—C33—H33B110.5
O7—C31—N2117.4 (2)C34—C33—H33A110.5
O7—C31—C30123.9 (2)C34—C33—H33B110.5
O6—C27—C24113.2 (2)H33A—C33—H33B108.7
O6—C27—H27107.7O1—C7—C4111.7 (2)
O6—C27—C28107.7 (2)O1—C7—C8108.1 (2)
C24—C27—H27107.7O1—C7—H7108.3
C24—C27—C28112.7 (2)C4—C7—C8111.9 (2)
C28—C27—H27107.7C4—C7—H7108.3
O9—C32—N2109.8 (2)C8—C7—H7108.3
O8—C32—O9122.4 (2)C31—C30—H30A109.0
O8—C32—N2127.8 (3)C31—C30—H30B109.0
C21—C22—H22121.1C29—C30—C31112.8 (2)
C21—C22—C23117.9 (2)C29—C30—H30A109.0
C23—C22—H22121.1C29—C30—H30B109.0
C24—C25—C26121.4 (2)H30A—C30—H30B107.8
C24—C25—H25119.3C35—C36—H36119.8
C26—C25—H25119.3C37—C36—C35120.4 (3)
C46—C41—F3118.6 (3)C37—C36—H36119.8
C42—C41—F3118.7 (3)H14A—O14—H14B109.5
C42—C41—C46122.6 (3)C54—C53—H53A110.7
C15—C16—H16119.8C54—C53—H53B110.7
C17—C16—C15120.4 (2)O12—C53—C54105.4 (2)
C17—C16—H16119.8O12—C53—H53A110.7
C44—C43—H43119.5O12—C53—H53B110.7
C42—C43—C44121.0 (2)H53A—C53—H53B108.8
C42—C43—H43119.5C37—C38—C39120.0 (3)
C55—C60—H60119.7C37—C38—H38120.0
C59—C60—C55120.5 (2)C39—C38—H38120.0
C59—C60—H60119.7O4—C13—C14106.0 (2)
C24—C23—H23119.2O4—C13—H13A110.5
C22—C23—C24121.7 (2)O4—C13—H13B110.5
C22—C23—H23119.2C14—C13—H13A110.5
N2—C34—C35115.10 (19)C14—C13—H13B110.5
N2—C34—H34109.5H13A—C13—H13B108.7
N2—C34—C33100.31 (19)C55—C56—C57120.5 (3)
C35—C34—H34109.5C55—C56—H56119.8
C35—C34—C33112.7 (2)C57—C56—H56119.8
C33—C34—H34109.5C1—C2—C3119.4 (3)
C19—C20—C15121.3 (2)C1—C2—H2120.3
C19—C20—H20119.4C3—C2—H2120.3
C15—C20—H20119.4C41—C42—C43119.0 (2)
C16—C17—H17119.7C41—C42—H42120.5
C18—C17—C16120.6 (2)C43—C42—H42120.5
C18—C17—H17119.7H5A—O5—H5B104.3
C50—C49—H49A108.9
O13—C51—C50—C4910.0 (3)C43—C44—C47—C48117.3 (2)
N1—C11—C10—C9176.3 (2)C43—C44—C45—C460.0 (4)
N1—C14—C15—C1651.3 (3)C60—C55—C54—N3105.9 (2)
N1—C14—C15—C20130.3 (2)C60—C55—C54—C53141.7 (2)
N1—C14—C13—O47.7 (3)C60—C55—C56—C570.7 (4)
O2—C11—C10—C94.5 (4)C60—C59—C58—C570.4 (4)
N2—C31—C30—C29140.7 (3)C23—C24—C27—O6173.8 (2)
N2—C34—C33—O915.2 (3)C23—C24—C27—C2863.7 (3)
N3—C51—C50—C49169.7 (2)C23—C24—C25—C262.0 (4)
N3—C54—C53—O1221.3 (3)C34—N2—C31—O75.2 (3)
N3—C52—O12—C535.9 (4)C34—N2—C31—C30171.9 (2)
O6—C27—C28—C2963.6 (3)C34—N2—C32—O95.6 (3)
O7—C31—C30—C2936.2 (5)C34—N2—C32—O8171.7 (3)
C44—C43—C42—C411.1 (4)C34—C35—C40—C39176.0 (2)
C44—C45—C46—C410.0 (4)C34—C35—C36—C37177.1 (2)
C51—N3—C54—C5578.2 (3)C20—C19—C18—C170.3 (4)
C51—N3—C54—C53159.8 (2)C20—C15—C16—C171.0 (4)
C51—N3—C52—O1111.4 (6)C49—C48—C47—O10172.8 (2)
C51—N3—C52—O12169.3 (3)C49—C48—C47—C4464.7 (3)
C51—C50—C49—C48179.6 (2)C40—C35—C34—N2154.8 (2)
F2—C21—C26—C25176.8 (2)C40—C35—C34—C3391.0 (3)
F2—C21—C22—C23176.8 (2)C40—C35—C36—C370.8 (4)
C24—C27—C28—C2961.9 (3)C40—C39—C38—C370.4 (4)
C11—N1—C14—C1569.8 (3)C54—N3—C51—O132.5 (3)
C11—N1—C14—C13167.9 (2)C54—N3—C51—C50177.8 (2)
C11—N1—C12—O4171.2 (2)C54—N3—C52—O11170.0 (4)
C11—N1—C12—O39.2 (4)C54—N3—C52—O129.4 (3)
C11—C10—C9—C8178.7 (2)C54—C55—C60—C59179.9 (2)
C55—C60—C59—C580.3 (4)C54—C55—C56—C57179.7 (2)
C55—C54—C53—O1297.7 (3)C18—C19—C20—C150.9 (4)
C4—C3—C2—C11.0 (5)C45—C44—C47—O1058.4 (3)
C14—N1—C11—O26.5 (3)C45—C44—C47—C4862.1 (3)
C14—N1—C11—C10172.8 (2)C45—C44—C43—C420.5 (4)
C14—N1—C12—O42.4 (3)F1—C1—C2—C3179.2 (3)
C14—N1—C12—O3177.2 (3)C46—C41—C42—C431.1 (5)
C14—C15—C16—C17177.5 (2)C52—N3—C51—O13176.0 (3)
C14—C15—C20—C19177.2 (2)C52—N3—C51—C503.7 (4)
C21—C26—C25—C240.3 (4)C52—N3—C54—C55103.0 (3)
C21—C22—C23—C240.2 (4)C52—N3—C54—C5318.9 (3)
C26—C21—C22—C231.6 (4)C52—O12—C53—C5417.9 (4)
C35—C34—C33—O9138.1 (2)C9—C8—C7—O157.1 (3)
C35—C40—C39—C381.0 (4)C9—C8—C7—C4179.5 (2)
C12—O4—C13—C147.1 (3)C28—C29—C30—C31170.7 (3)
C12—N1—C11—O2166.7 (2)C6—C1—C2—C30.2 (5)
C12—N1—C11—C1014.0 (3)C1—C6—C5—C40.1 (5)
C12—N1—C14—C15116.0 (2)C58—C57—C56—C550.8 (4)
C12—N1—C14—C136.3 (3)C5—C4—C3—C21.1 (4)
C15—C14—C13—O4113.6 (2)C5—C4—C7—O130.1 (3)
C15—C16—C17—C180.3 (4)C5—C4—C7—C891.3 (3)
F3—C41—C46—C45179.4 (2)C5—C6—C1—F1179.7 (3)
F3—C41—C42—C43178.8 (3)C5—C6—C1—C20.3 (5)
C47—C44—C43—C42178.9 (2)C3—C4—C5—C60.5 (4)
C47—C44—C45—C46179.5 (2)C3—C4—C7—O1151.6 (2)
C47—C48—C49—C50171.7 (2)C3—C4—C7—C887.0 (3)
C31—N2—C32—O9171.3 (2)C33—O9—C32—N25.2 (3)
C31—N2—C32—O86.1 (4)C33—O9—C32—O8177.3 (3)
C31—N2—C34—C3559.3 (3)C7—C4—C5—C6177.7 (3)
C31—N2—C34—C33179.5 (2)C7—C4—C3—C2177.2 (3)
C27—C24—C25—C26176.3 (2)C7—C8—C9—C1060.1 (3)
C27—C24—C23—C22176.3 (2)C36—C35—C34—N229.0 (3)
C27—C28—C29—C3088.3 (4)C36—C35—C34—C3385.2 (3)
C32—O9—C33—C3413.3 (3)C36—C35—C40—C390.4 (3)
C32—N2—C31—O7159.1 (2)C36—C37—C38—C390.8 (4)
C32—N2—C31—C3023.7 (4)C38—C37—C36—C351.4 (4)
C32—N2—C34—C35134.1 (2)C13—O4—C12—N13.2 (3)
C32—N2—C34—C3312.9 (3)C13—O4—C12—O3177.1 (2)
C22—C21—C26—C251.6 (4)C13—C14—C15—C1663.2 (3)
C25—C24—C27—O64.4 (3)C13—C14—C15—C20115.2 (3)
C25—C24—C27—C28118.1 (3)C56—C55—C60—C590.5 (3)
C25—C24—C23—C221.9 (4)C56—C55—C54—N373.6 (3)
O11—C52—O12—C53174.7 (4)C56—C55—C54—C5338.8 (3)
C16—C15—C20—C191.3 (4)C56—C57—C58—C590.6 (4)
C16—C17—C18—C190.0 (4)C42—C41—C46—C450.6 (4)
C43—C44—C47—O10122.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10···O80.822.022.837 (3)173
O6—H6A···O10i0.821.992.797 (3)167
O1—H1···O14ii0.821.852.669 (4)174
C22—H22···O6iii0.932.653.522 (3)157
C33—H33A···O7iv0.972.573.337 (4)137
C30—H30A···O60.972.583.149 (3)118
C30—H30B···O80.972.312.860 (4)115
O14—H14A···O10.851.882.728 (3)173
O14—H14B···O13ii0.852.012.825 (3)161
C13—H13B···F2iv0.972.513.347 (3)145
C42—H42···O3v0.932.373.232 (3)153
O5—H5B···O3v0.852.092.928 (5)171
Symmetry codes: (i) x1, y+1/2, z; (ii) x, y+1/2, z+1; (iii) x, y+1, z; (iv) x, y1/2, z; (v) x, y1, z.
 

Acknowledgements

The authors thank Professor Zhang of Jinan University for providing the single-crystal X-ray diffractometer facility.

Funding information

Funding for this research was provided by: Shandong Jincheng Pharmaceutical Co. Ltd

References

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