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

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ISSN: 2056-9890

(9S,13R,14S)-7,8-Dide­hydro-4-(4-fluoro­benz­yl­oxy)-3,7-dimeth­­oxy-17-methyl­morphinan-6-one sesquihydrate

aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, People's Republic of China
*Correspondence e-mail: xingliangzheng@163.com

(Received 3 June 2011; accepted 1 July 2011; online 9 July 2011)

In the title sinomenine derivative, C26H28FNO4·1.5H2O, the dihedral angle between the two aromatic rings is 55.32 (6)°. The N-containing ring has an approximate chair conformation, while other two rings have approximate envelope and half-chair conformations. One water mol­ecule is located on a twofold symmetry axis. In the crystal, the water mol­ecules form O—H⋯O and O—H⋯N hydrogen bonds, bridging symmetry-related main mol­ecules.

Related literature

For background to the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994[Liu, L., Riese, J., Resch, K. & Kaever, V. (1994). Arzneim. Forsch. 44, 1223-1226.], 1996[Liu, L., Buchner, E., Beitze, D., Schmidt-Weber, C. B., Kaever, V. & Emmricinne, R. W. (1996). Int. J. Immunopharmacol. 18, 529-543.], 1997[Liu, Q., Zhou, L. L. & Li, R. (1997). Chin. Trad. Herb. Drugs, 28, 247-249.]); Mark et al. (2003[Mark, W., Schneeberger, S., Seiler, R., Stroka, D. M., Amberger, A., Offner, F., Candinas, D. & Margreiter, R. (2003). Transplantation, 75, 940-945.]); Ye et al. (2004[Ye, X. R., Yan, K. X., Wu, K. M., Feng, X. Z., Huang, Y. M. & Qiu, P. (2004). Acta Pharmacol. Sin. 39, 180-183.]). For the synthesis of the title compound, see: Mitsunobu (1981[Mitsunobu, O. (1981). Synthesis, pp. 1-28.]). For related structures, see: Li et al. (2009[Li, Y.-F., Qian, Y., Yin, L.-H., Lv, R. & Zhu, H.-J. (2009). Acta Cryst. E65, o689.]); Batterham et al. (1965[Batterham, T. J., Bell, K. H. & Weis, U. (1965). Aust. J. Chem. 18, 1799-1806.]); Zheng & Jiang (2010[Zheng, X.-L. & Jiang, N.-F. (2010). Acta Cryst. E66, o2817.]); Zheng et al. (2011[Zheng, X.-L., Chen, S.-J., Jiang, N.-F. & Zhan, S.-H. (2011). Acta Cryst. E67, o1190.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28FNO4·1.5H2O

  • Mr = 464.52

  • Monoclinic, C 2

  • a = 18.0155 (3) Å

  • b = 7.6776 (1) Å

  • c = 18.1506 (4) Å

  • β = 109.324 (1)°

  • V = 2369.08 (7) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.79 mm−1

  • T = 133 K

  • 0.25 × 0.15 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.826, Tmax = 0.925

  • 7232 measured reflections

  • 3415 independent reflections

  • 3402 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.081

  • S = 1.04

  • 3415 reflections

  • 312 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.18 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1359 Friedel pairs

  • Flack parameter: 0.05 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2S—H22S⋯O4 0.91 2.33 2.9805 (16) 128
O2S—H22S⋯O3 0.91 2.54 3.417 (2) 164
O1S—H11S⋯O2S 0.90 (3) 1.94 (3) 2.8342 (19) 172 (2)
O2S—H21S⋯N1i 0.97 1.81 2.7736 (19) 170
Symmetry code: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

We synthesized a new sinomenine derivative sesquihydrate. Herein, its crystal structure is reported. Biological effects of sinomenine derivatives and related compounds have been described (Liu et al., 1994, 1996, 1997; Mark et al., 2003; Ye et al., 2004).

The molecular structure of the title compound is shown in Fig. 1. The crystal structure is stabilized by O—H···O and O—H···N hydrogen bonds linking the sinomenine derivative and the water molecules, and weak C—H···O hydrogen bonds between molecules (Fig. 2). Significant aromatic stacking interactions were not found. There exist two planes in the molecule of the title compound: atoms C1···C6 form the benzene plane (I), and atoms C21···C26 form the benzene plane substituted by fluorine (II). The angle between the two planes (I) and (II) is 55.32 (6)°. Rings C [C7/C8/C11/C12/C13/C14] and B [C5···C10] in the molecule approximate envelope and half-chair conformations, respectively. In contrast, ring D [C9/N1/C16/C15/C7/C8] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Zheng & Jiang, 2010; Zheng et al., 2011; Li et al., 2009; Batterham et al., 1965).

Related literature top

For background to biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994, 1996, 1997); Mark et al. (2003); Ye et al. (2004). For the synthesis of the title compound, see: Mitsunobu (1981). For related structures, see: Li et al. (2009); Batterham et al. (1965); Zheng & Jiang (2010); Zheng et al. (2011).

Experimental top

The title compound was obtained according to the method of Mitsunobu (1981). Colorless blocks were grown from an acetic ether solution.

Refinement top

The water H atoms (H21S, H22S and H11S) were located in a difference map. H11S was refined with free coordinates and isotropic displacement parameter. H21S and H22S were fixed in their as found positions and allowed to ride on O2S, and their displacement parameters were refined. Other H atoms were positioned geometrically, with C—H = 0.95 (aromatic CH), 0.98 (methyl CH3), 0.99 (methylene CH2) or 1.00 Å (methine CH), and were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(carrier C) or Uiso(H) = 1.5Ueq(carrier C17 C18 C19). 1359 Friedel pairs were used for the Flack parameter refinement.

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A part of the crystal structure of the title compound.
(9S,13R,14S)-7,8-Didehydro-4-(4-fluorobenzyloxy)-3,7- dimethoxy-17-methylmorphinan-6-one sesquihydrate top
Crystal data top
C26H28FNO4·1.5H2OF(000) = 988
Mr = 464.52Dx = 1.302 Mg m3
Monoclinic, C2Cu Kα radiation, λ = 1.54178 Å
Hall symbol: C 2yCell parameters from 6582 reflections
a = 18.0155 (3) Åθ = 2.6–64.7°
b = 7.6776 (1) ŵ = 0.79 mm1
c = 18.1506 (4) ÅT = 133 K
β = 109.324 (1)°Block, colourless
V = 2369.08 (7) Å30.25 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3415 independent reflections
Radiation source: fine-focus sealed tube3402 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 65.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 2021
Tmin = 0.826, Tmax = 0.925k = 99
7232 measured reflectionsl = 1820
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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6114P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3415 reflectionsΔρmax = 0.20 e Å3
312 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Flack (1983), 1359 Friedel pairs
0 constraintsAbsolute structure parameter: 0.05 (12)
Primary atom site location: structure-invariant direct methods
Crystal data top
C26H28FNO4·1.5H2OV = 2369.08 (7) Å3
Mr = 464.52Z = 4
Monoclinic, C2Cu Kα radiation
a = 18.0155 (3) ŵ = 0.79 mm1
b = 7.6776 (1) ÅT = 133 K
c = 18.1506 (4) Å0.25 × 0.15 × 0.10 mm
β = 109.324 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
3415 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
3402 reflections with I > 2σ(I)
Tmin = 0.826, Tmax = 0.925Rint = 0.024
7232 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081Δρmax = 0.20 e Å3
S = 1.04Δρmin = 0.18 e Å3
3415 reflectionsAbsolute structure: Flack (1983), 1359 Friedel pairs
312 parametersAbsolute structure parameter: 0.05 (12)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.49485 (7)0.26627 (16)0.40332 (8)0.0571 (3)
N10.03356 (8)0.4513 (2)0.15607 (8)0.0314 (3)
O10.26142 (6)0.36402 (13)0.34083 (6)0.0237 (2)
O20.29280 (6)0.57951 (14)0.46321 (6)0.0268 (2)
O30.32140 (7)0.48228 (18)0.15878 (7)0.0392 (3)
O40.24651 (6)0.74481 (15)0.07306 (7)0.0307 (3)
C10.21885 (8)0.51681 (19)0.33202 (9)0.0217 (3)
C20.23288 (8)0.6279 (2)0.39717 (9)0.0233 (3)
C30.18682 (9)0.7742 (2)0.39246 (9)0.0265 (3)
H30.19680.85110.43570.032*
C40.12611 (8)0.80691 (19)0.32395 (9)0.0253 (3)
H40.09430.90720.32090.030*
C50.10990 (8)0.6993 (2)0.25971 (9)0.0239 (3)
C60.15775 (8)0.55115 (19)0.26184 (9)0.0220 (3)
C70.13574 (8)0.4223 (2)0.19297 (9)0.0254 (3)
C80.08177 (8)0.5102 (2)0.11800 (9)0.0264 (3)
H80.06200.41710.07770.032*
C90.01057 (9)0.5906 (2)0.13270 (9)0.0285 (3)
H90.02440.63950.08200.034*
C100.03877 (8)0.7424 (2)0.18927 (9)0.0279 (3)
H10A0.05200.84160.16100.033*
H10B0.00480.77990.20750.033*
C110.20578 (9)0.3494 (2)0.17160 (9)0.0275 (3)
H11A0.24210.28880.21760.033*
H11B0.18610.26280.12920.033*
C120.25034 (9)0.4894 (2)0.14564 (9)0.0281 (3)
C130.20238 (9)0.6325 (2)0.09902 (9)0.0266 (3)
C140.12457 (9)0.6423 (2)0.08562 (9)0.0259 (3)
H140.09570.73530.05480.031*
C150.08761 (10)0.2737 (2)0.21185 (10)0.0316 (4)
H15A0.07360.18770.16880.038*
H15B0.11980.21370.26010.038*
C160.01249 (10)0.3444 (2)0.22285 (10)0.0330 (4)
H16A0.02020.24570.22930.040*
H16B0.02670.41560.27100.040*
C170.31222 (10)0.6993 (2)0.52708 (9)0.0332 (4)
H17A0.32280.81420.50920.050*
H17B0.35900.65800.56860.050*
H17C0.26810.70790.54710.050*
C180.20598 (10)0.8932 (2)0.03173 (10)0.0355 (4)
H18A0.16460.85520.01580.053*
H18B0.24310.96850.01770.053*
H18C0.18230.95790.06490.053*
C190.10438 (10)0.5180 (3)0.16953 (12)0.0392 (4)
H19A0.13620.42010.17670.059*
H19B0.13520.58740.12450.059*
H19C0.08900.59110.21640.059*
C200.34415 (9)0.3842 (2)0.35220 (9)0.0273 (3)
H20A0.36870.46210.39710.033*
H20B0.35120.43670.30510.033*
C210.38241 (9)0.2075 (2)0.36728 (9)0.0262 (3)
C220.46433 (10)0.1988 (2)0.39458 (10)0.0323 (4)
H220.49420.30330.40490.039*
C230.50269 (10)0.0401 (3)0.40683 (11)0.0394 (4)
H230.55850.03430.42500.047*
C240.45800 (11)0.1091 (3)0.39200 (12)0.0398 (4)
C250.37742 (11)0.1056 (2)0.36530 (12)0.0397 (4)
H250.34800.21070.35560.048*
C260.33978 (10)0.0545 (2)0.35278 (11)0.0335 (4)
H260.28390.05900.33400.040*
O2S0.39668 (7)0.7129 (2)0.03873 (8)0.0485 (4)
H21S0.42680.78980.08020.043 (6)*
H22S0.36680.65730.06280.131 (15)*
O1S0.50000.4796 (3)0.00000.0471 (5)
H11S0.4712 (14)0.555 (4)0.0168 (15)0.059 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0562 (6)0.0372 (6)0.0885 (9)0.0217 (5)0.0383 (6)0.0200 (6)
N10.0288 (6)0.0374 (8)0.0294 (8)0.0071 (6)0.0115 (5)0.0058 (6)
O10.0254 (5)0.0206 (5)0.0261 (6)0.0017 (4)0.0101 (4)0.0017 (4)
O20.0308 (5)0.0273 (5)0.0195 (6)0.0014 (4)0.0045 (4)0.0017 (4)
O30.0355 (6)0.0483 (8)0.0397 (7)0.0102 (5)0.0205 (5)0.0108 (6)
O40.0313 (5)0.0316 (6)0.0331 (6)0.0011 (5)0.0158 (4)0.0059 (5)
C10.0241 (6)0.0198 (7)0.0241 (8)0.0004 (5)0.0117 (5)0.0022 (6)
C20.0244 (7)0.0244 (7)0.0219 (8)0.0044 (6)0.0088 (6)0.0001 (6)
C30.0298 (7)0.0260 (8)0.0253 (8)0.0044 (6)0.0113 (6)0.0051 (6)
C40.0258 (7)0.0220 (7)0.0299 (9)0.0000 (6)0.0117 (6)0.0004 (6)
C50.0223 (6)0.0252 (8)0.0251 (8)0.0033 (6)0.0091 (6)0.0035 (6)
C60.0248 (7)0.0221 (7)0.0215 (8)0.0046 (6)0.0110 (6)0.0005 (6)
C70.0310 (7)0.0261 (8)0.0194 (8)0.0040 (6)0.0086 (6)0.0019 (6)
C80.0290 (7)0.0287 (8)0.0208 (8)0.0043 (6)0.0072 (6)0.0022 (6)
C90.0263 (7)0.0342 (9)0.0230 (9)0.0044 (7)0.0056 (6)0.0004 (7)
C100.0259 (7)0.0294 (8)0.0271 (9)0.0014 (6)0.0070 (6)0.0018 (6)
C110.0398 (8)0.0236 (8)0.0207 (8)0.0012 (6)0.0120 (6)0.0038 (6)
C120.0346 (8)0.0314 (9)0.0214 (8)0.0022 (7)0.0138 (6)0.0038 (6)
C130.0330 (7)0.0301 (8)0.0188 (8)0.0025 (6)0.0113 (6)0.0019 (6)
C140.0311 (7)0.0286 (8)0.0165 (8)0.0042 (6)0.0060 (6)0.0013 (6)
C150.0391 (8)0.0270 (8)0.0289 (9)0.0083 (7)0.0115 (7)0.0035 (7)
C160.0371 (8)0.0350 (9)0.0296 (9)0.0130 (7)0.0145 (6)0.0028 (7)
C170.0426 (9)0.0300 (8)0.0216 (9)0.0040 (7)0.0034 (6)0.0033 (6)
C180.0374 (8)0.0350 (9)0.0336 (10)0.0049 (8)0.0109 (7)0.0074 (7)
C190.0319 (8)0.0491 (11)0.0393 (10)0.0082 (8)0.0154 (7)0.0081 (8)
C200.0284 (7)0.0261 (8)0.0310 (9)0.0007 (6)0.0146 (6)0.0020 (7)
C210.0332 (7)0.0289 (8)0.0215 (8)0.0050 (6)0.0156 (6)0.0034 (6)
C220.0334 (8)0.0355 (9)0.0283 (9)0.0011 (7)0.0104 (6)0.0009 (7)
C230.0343 (9)0.0478 (11)0.0369 (10)0.0089 (8)0.0128 (7)0.0037 (8)
C240.0459 (9)0.0355 (9)0.0466 (11)0.0143 (8)0.0267 (8)0.0149 (8)
C250.0448 (9)0.0258 (8)0.0596 (12)0.0024 (8)0.0322 (9)0.0078 (8)
C260.0318 (8)0.0301 (9)0.0446 (10)0.0029 (7)0.0208 (7)0.0054 (7)
O2S0.0406 (6)0.0605 (9)0.0520 (8)0.0194 (7)0.0256 (6)0.0300 (7)
O1S0.0402 (10)0.0401 (11)0.0665 (14)0.0000.0251 (10)0.000
Geometric parameters (Å, º) top
F1—C241.360 (2)C12—C131.479 (2)
N1—C191.469 (2)C13—C141.343 (2)
N1—C161.471 (2)C14—H140.9500
N1—C91.476 (2)C15—C161.531 (2)
O1—C11.3815 (18)C15—H15A0.9900
O1—C201.4438 (17)C15—H15B0.9900
O2—C21.3725 (18)C16—H16A0.9900
O2—C171.430 (2)C16—H16B0.9900
O3—C121.2233 (19)C17—H17A0.9800
O4—C131.3585 (19)C17—H17B0.9800
O4—C181.425 (2)C17—H17C0.9800
C1—C61.406 (2)C18—H18A0.9800
C1—C21.411 (2)C18—H18B0.9800
C2—C31.383 (2)C18—H18C0.9800
C3—C41.380 (2)C19—H19A0.9800
C3—H30.9500C19—H19B0.9800
C4—C51.379 (2)C19—H19C0.9800
C4—H40.9500C20—C211.505 (2)
C5—C61.420 (2)C20—H20A0.9900
C5—C101.517 (2)C20—H20B0.9900
C6—C71.540 (2)C21—C261.381 (2)
C7—C151.539 (2)C21—C221.394 (2)
C7—C81.542 (2)C22—C231.381 (3)
C7—C111.543 (2)C22—H220.9500
C8—C141.506 (2)C23—C241.375 (3)
C8—C91.525 (2)C23—H230.9500
C8—H81.0000C24—C251.370 (3)
C9—C101.525 (2)C25—C261.386 (3)
C9—H91.0000C25—H250.9500
C10—H10A0.9900C26—H260.9500
C10—H10B0.9900O2S—H21S0.9694
C11—C121.507 (2)O2S—H22S0.9051
C11—H11A0.9900O1S—H11S0.90 (3)
C11—H11B0.9900
C19—N1—C16109.97 (14)O4—C13—C12111.83 (13)
C19—N1—C9112.02 (14)C13—C14—C8122.02 (15)
C16—N1—C9115.49 (12)C13—C14—H14119.0
C1—O1—C20115.64 (11)C8—C14—H14119.0
C2—O2—C17116.41 (12)C16—C15—C7110.70 (13)
C13—O4—C18115.67 (12)C16—C15—H15A109.5
O1—C1—C6120.15 (13)C7—C15—H15A109.5
O1—C1—C2118.52 (12)C16—C15—H15B109.5
C6—C1—C2121.03 (14)C7—C15—H15B109.5
O2—C2—C3123.80 (14)H15A—C15—H15B108.1
O2—C2—C1116.07 (13)N1—C16—C15111.84 (13)
C3—C2—C1120.13 (13)N1—C16—H16A109.2
C4—C3—C2118.93 (14)C15—C16—H16A109.2
C4—C3—H3120.5N1—C16—H16B109.2
C2—C3—H3120.5C15—C16—H16B109.2
C5—C4—C3122.39 (14)H16A—C16—H16B107.9
C5—C4—H4118.8O2—C17—H17A109.5
C3—C4—H4118.8O2—C17—H17B109.5
C4—C5—C6120.01 (13)H17A—C17—H17B109.5
C4—C5—C10117.71 (14)O2—C17—H17C109.5
C6—C5—C10122.25 (14)H17A—C17—H17C109.5
C1—C6—C5117.47 (13)H17B—C17—H17C109.5
C1—C6—C7121.96 (13)O4—C18—H18A109.5
C5—C6—C7120.11 (13)O4—C18—H18B109.5
C15—C7—C6107.95 (12)H18A—C18—H18B109.5
C15—C7—C8106.49 (12)O4—C18—H18C109.5
C6—C7—C8110.68 (13)H18A—C18—H18C109.5
C15—C7—C11110.81 (13)H18B—C18—H18C109.5
C6—C7—C11115.14 (12)N1—C19—H19A109.5
C8—C7—C11105.44 (12)N1—C19—H19B109.5
C14—C8—C9111.39 (13)H19A—C19—H19B109.5
C14—C8—C7112.60 (12)N1—C19—H19C109.5
C9—C8—C7110.14 (12)H19A—C19—H19C109.5
C14—C8—H8107.5H19B—C19—H19C109.5
C9—C8—H8107.5O1—C20—C21108.57 (12)
C7—C8—H8107.5O1—C20—H20A110.0
N1—C9—C8108.72 (13)C21—C20—H20A110.0
N1—C9—C10116.85 (14)O1—C20—H20B110.0
C8—C9—C10108.37 (12)C21—C20—H20B110.0
N1—C9—H9107.5H20A—C20—H20B108.4
C8—C9—H9107.5C26—C21—C22118.90 (15)
C10—C9—H9107.5C26—C21—C20122.68 (13)
C5—C10—C9113.63 (14)C22—C21—C20118.39 (15)
C5—C10—H10A108.8C23—C22—C21120.94 (16)
C9—C10—H10A108.8C23—C22—H22119.5
C5—C10—H10B108.8C21—C22—H22119.5
C9—C10—H10B108.8C24—C23—C22118.28 (15)
H10A—C10—H10B107.7C24—C23—H23120.9
C12—C11—C7112.63 (13)C22—C23—H23120.9
C12—C11—H11A109.1F1—C24—C25118.55 (17)
C7—C11—H11A109.1F1—C24—C23119.01 (15)
C12—C11—H11B109.1C25—C24—C23122.44 (17)
C7—C11—H11B109.1C24—C25—C26118.62 (17)
H11A—C11—H11B107.8C24—C25—H25120.7
O3—C12—C13121.36 (15)C26—C25—H25120.7
O3—C12—C11122.58 (15)C21—C26—C25120.83 (15)
C13—C12—C11115.97 (13)C21—C26—H26119.6
C14—C13—O4126.68 (15)C25—C26—H26119.6
C14—C13—C12121.49 (14)H21S—O2S—H22S100.4
C20—O1—C1—C6117.00 (14)C7—C8—C9—C1067.54 (17)
C20—O1—C1—C269.19 (16)C4—C5—C10—C9161.88 (13)
C17—O2—C2—C36.5 (2)C6—C5—C10—C916.3 (2)
C17—O2—C2—C1174.39 (13)N1—C9—C10—C576.09 (17)
O1—C1—C2—O24.70 (18)C8—C9—C10—C547.08 (17)
C6—C1—C2—O2178.46 (12)C15—C7—C11—C12174.84 (13)
O1—C1—C2—C3174.47 (12)C6—C7—C11—C1262.30 (18)
C6—C1—C2—C30.7 (2)C8—C7—C11—C1259.99 (16)
O2—C2—C3—C4177.53 (14)C7—C11—C12—O3146.72 (15)
C1—C2—C3—C41.6 (2)C7—C11—C12—C1336.64 (19)
C2—C3—C4—C50.4 (2)C18—O4—C13—C144.3 (2)
C3—C4—C5—C61.7 (2)C18—O4—C13—C12176.15 (14)
C3—C4—C5—C10176.50 (14)O3—C12—C13—C14178.85 (14)
O1—C1—C6—C5172.34 (12)C11—C12—C13—C144.5 (2)
C2—C1—C6—C51.31 (19)O3—C12—C13—O41.6 (2)
O1—C1—C6—C70.16 (19)C11—C12—C13—O4175.12 (12)
C2—C1—C6—C7173.49 (13)O4—C13—C14—C8179.60 (15)
C4—C5—C6—C12.50 (19)C12—C13—C14—C80.9 (2)
C10—C5—C6—C1175.63 (13)C9—C8—C14—C13150.28 (14)
C4—C5—C6—C7174.83 (13)C7—C8—C14—C1326.0 (2)
C10—C5—C6—C73.3 (2)C6—C7—C15—C1660.26 (16)
C1—C6—C7—C1577.55 (16)C8—C7—C15—C1658.62 (17)
C5—C6—C7—C1594.43 (16)C11—C7—C15—C16172.80 (13)
C1—C6—C7—C8166.27 (12)C19—N1—C16—C15179.28 (13)
C5—C6—C7—C821.76 (18)C9—N1—C16—C1551.32 (19)
C1—C6—C7—C1146.83 (19)C7—C15—C16—N152.98 (18)
C5—C6—C7—C11141.20 (14)C1—O1—C20—C21175.38 (12)
C15—C7—C8—C14171.75 (13)O1—C20—C21—C2614.3 (2)
C6—C7—C8—C1471.16 (16)O1—C20—C21—C22167.91 (13)
C11—C7—C8—C1453.97 (17)C26—C21—C22—C230.2 (2)
C15—C7—C8—C963.25 (16)C20—C21—C22—C23177.70 (16)
C6—C7—C8—C953.84 (16)C21—C22—C23—C240.5 (3)
C11—C7—C8—C9178.96 (12)C22—C23—C24—F1179.61 (18)
C19—N1—C9—C8178.64 (13)C22—C23—C24—C250.4 (3)
C16—N1—C9—C854.42 (18)F1—C24—C25—C26179.18 (17)
C19—N1—C9—C1058.37 (18)C23—C24—C25—C260.0 (3)
C16—N1—C9—C1068.57 (18)C22—C21—C26—C250.2 (3)
C14—C8—C9—N1173.90 (13)C20—C21—C26—C25178.05 (17)
C7—C8—C9—N160.41 (17)C24—C25—C26—C210.4 (3)
C14—C8—C9—C1058.15 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2S—H22S···O40.912.332.9805 (16)128
O2S—H22S···O30.912.543.417 (2)164
O1S—H11S···O2S0.90 (3)1.94 (3)2.8342 (19)172 (2)
O2S—H21S···N1i0.971.812.7736 (19)170
Symmetry code: (i) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC26H28FNO4·1.5H2O
Mr464.52
Crystal system, space groupMonoclinic, C2
Temperature (K)133
a, b, c (Å)18.0155 (3), 7.6776 (1), 18.1506 (4)
β (°) 109.324 (1)
V3)2369.08 (7)
Z4
Radiation typeCu Kα
µ (mm1)0.79
Crystal size (mm)0.25 × 0.15 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.826, 0.925
No. of measured, independent and
observed [I > 2σ(I)] reflections
7232, 3415, 3402
Rint0.024
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.081, 1.04
No. of reflections3415
No. of parameters312
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.18
Absolute structureFlack (1983), 1359 Friedel pairs
Absolute structure parameter0.05 (12)

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2S—H22S···O40.912.332.9805 (16)128
O2S—H22S···O30.912.543.417 (2)164
O1S—H11S···O2S0.90 (3)1.94 (3)2.8342 (19)172 (2)
O2S—H21S···N1i0.971.812.7736 (19)170
Symmetry code: (i) x+1/2, y+1/2, z.
 

Acknowledgements

The project was supported by the National Natural Science Foundation of China (No. 20976017) and the Scientific Research Fund of the Hunan Provincial Science and Technology Department, China (No. 2009 C K3070).

References

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