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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1190

(8S,9S,10R)-4-(4-Chloro­benz­yl­oxy)-7,8-dide­hydro-3,7-dimeth­­oxy-17-methyl­morphinan-6-one monohydrate

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 4 April 2011; accepted 13 April 2011; online 22 April 2011)

In the title compound, C26H28ClNO4·H2O, the dihedral angle betwene the two aromatic rings is 69.73 (6)°. The N-containing ring exhibits a chair conformation, while the other non-aromatic rings are in approximate envelope conformations. In the crystal, the water mol­ecule forms O—H⋯O and O—H⋯N hydrogen bonds and a C—H⋯O link also occurs.

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. Herbal 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28ClNO4·H2O

  • Mr = 471.96

  • Monoclinic, P 21

  • a = 8.8866 (4) Å

  • b = 14.6386 (7) Å

  • c = 9.1860 (4) Å

  • β = 91.618 (1)°

  • V = 1194.51 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 296 K

  • 0.45 × 0.36 × 0.32 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.917, Tmax = 0.940

  • 13795 measured reflections

  • 4185 independent reflections

  • 3974 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.082

  • S = 1.05

  • 4185 reflections

  • 303 parameters

  • 3 restraints

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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1991 Friedel pairs

  • Flack parameter: −0.02 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8A⋯O1i 0.98 2.56 3.469 (2) 155
O1W—H1WB⋯O4ii 0.85 2.04 2.879 (2) 169
O1W—H1WA⋯N1 0.85 2.16 2.899 (2) 146
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, 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.

Supporting information


Comment top

We synthesised a new sinomenine derivative (8S,9S,10R)-7,8-didehydro-4-(4'-chlorobenzyloxy)-3,7-δimethoxy-17-methyl-morphinan-6-one monohydrate. 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 (I) is shown in Fig. 1. The angle between the two benzene planes is 69.736°. Rings C [C9/C10/C11/C12/C13/C14] and B [C5···.C10], both, are in an envelope conformation. In contrast, ring D [C8/N1/C15/C16/C10/C9] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Li et al., 2009; Batterham et al., 1965). The crystal structure is stabilised by O—H···O and O—H···N hydrogen bonds linking sinomenine derivative and the water molecule; weak C—H···O hydrogen bonds (Table 1 and Fig. 2) also occurred.

Related literature top

For background to the 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).

Experimental top

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

Refinement top

The water H atoms (H5C and H5D) were located in a difference map, and refined freely, although the geometry was restrained to O—H = 0.83 (3) Å and H5C···H5D separation to 1.45 (2) Å. Other H atoms were positioned geometrically, with C—H = 0.93 (aromatic CH), 0.96 (methyl CH3), 0.97 (methylene CH2) or 0.98 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 C). 2311 Friedel pairs were used for the Flack parameter refinement.

Computing details top

Data collection: SMART (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 (I) showing 50% probability displacement ellipsoids [Symmetry codes: (i) 1 - x, 2 - y, 2 - z].
[Figure 2] Fig. 2. Crystal packing of (I) with hydrogen bond interactions (dashed lines).
(8S,9S,10R)-4-(4-Chlorobenzyloxy)-7,8-didehydro-3,7- dimethoxy-17-methylmorphinan-6-one monohydrate top
Crystal data top
C26H28ClNO4·H2OF(000) = 500
Mr = 471.96Dx = 1.312 Mg m3
Monoclinic, P21Melting point: 383 K
a = 8.8866 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.6386 (7) ŵ = 0.20 mm1
c = 9.1860 (4) ÅT = 296 K
β = 91.618 (1)°Block, colourless
V = 1194.51 (9) Å30.45 × 0.36 × 0.32 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
4185 independent reflections
Radiation source: fine-focus sealed tube3974 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.917, Tmax = 0.940k = 1717
13795 measured reflectionsl = 1010
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)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0458P)2 + 0.1696P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4185 reflectionsΔρmax = 0.20 e Å3
303 parametersΔρmin = 0.21 e Å3
3 restraintsAbsolute structure: Flack (1983), 1991 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
Crystal data top
C26H28ClNO4·H2OV = 1194.51 (9) Å3
Mr = 471.96Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.8866 (4) ŵ = 0.20 mm1
b = 14.6386 (7) ÅT = 296 K
c = 9.1860 (4) Å0.45 × 0.36 × 0.32 mm
β = 91.618 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4185 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
3974 reflections with I > 2σ(I)
Tmin = 0.917, Tmax = 0.940Rint = 0.022
13795 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082Δρmax = 0.20 e Å3
S = 1.05Δρmin = 0.21 e Å3
4185 reflectionsAbsolute structure: Flack (1983), 1991 Friedel pairs
303 parametersAbsolute structure parameter: 0.02 (6)
3 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl10.52194 (7)0.27734 (5)0.40802 (7)0.07659 (19)
O10.15952 (17)0.04761 (10)0.27652 (16)0.0553 (4)
O20.12278 (13)0.08829 (9)0.21247 (13)0.0412 (3)
O30.07164 (16)0.20241 (10)0.34261 (14)0.0524 (3)
O40.23766 (16)0.08573 (9)0.18937 (17)0.0563 (4)
N10.22663 (19)0.45473 (11)0.17465 (19)0.0501 (4)
C10.2087 (2)0.28319 (15)0.1494 (2)0.0487 (4)
H1A0.28390.32690.13710.058*
C20.2467 (2)0.19781 (15)0.1984 (2)0.0510 (5)
H2A0.34670.18350.21530.061*
C30.1356 (2)0.13375 (13)0.22213 (19)0.0427 (4)
C40.01413 (18)0.15522 (11)0.18989 (17)0.0355 (3)
C50.05174 (17)0.23996 (11)0.13104 (16)0.0337 (3)
C60.06217 (19)0.30630 (12)0.11783 (19)0.0393 (4)
C70.0312 (2)0.40384 (13)0.0731 (2)0.0473 (4)
H7A0.08930.41670.01550.057*
H7B0.06740.44410.14830.057*
C80.1333 (2)0.42725 (12)0.0471 (2)0.0441 (4)
H8A0.13480.47750.02340.053*
C90.2069 (2)0.34492 (11)0.02251 (19)0.0383 (4)
H9A0.31100.36170.04300.046*
C100.21264 (18)0.26412 (11)0.08633 (18)0.0355 (3)
C110.29450 (18)0.18780 (12)0.00569 (19)0.0392 (4)
H11A0.29970.13420.06780.047*
H11B0.39680.20740.01100.047*
C120.22199 (18)0.16152 (12)0.1371 (2)0.0400 (4)
C130.13513 (19)0.23343 (13)0.21620 (18)0.0411 (4)
C140.1311 (2)0.31859 (13)0.16395 (19)0.0419 (4)
H14A0.07940.36310.21740.050*
C150.2405 (2)0.38269 (15)0.2849 (2)0.0516 (5)
H15A0.30560.40350.36470.062*
H15B0.14220.36980.32340.062*
C160.3050 (2)0.29596 (13)0.2203 (2)0.0441 (4)
H16A0.40800.30710.19290.053*
H16B0.30620.24810.29330.053*
C170.1749 (4)0.54114 (17)0.2379 (3)0.0758 (7)
H17A0.23810.55660.32080.114*
H17B0.17990.58880.16640.114*
H17C0.07290.53440.26790.114*
C180.2921 (2)0.05280 (14)0.5062 (2)0.0491 (5)
H18A0.25970.02390.58990.059*
C190.3747 (2)0.13208 (15)0.5183 (2)0.0515 (5)
H19A0.39790.15690.60940.062*
C200.4226 (2)0.17419 (14)0.3939 (2)0.0472 (4)
C210.3920 (2)0.13761 (14)0.2589 (2)0.0468 (4)
H21A0.42610.16620.17560.056*
C220.3096 (2)0.05773 (13)0.2481 (2)0.0433 (4)
H22A0.28970.03220.15690.052*
C230.25623 (19)0.01518 (13)0.37027 (19)0.0394 (4)
C240.3108 (3)0.02259 (19)0.3035 (3)0.0779 (8)
H24A0.31310.03860.34100.117*
H24B0.35170.06370.37350.117*
H24C0.36960.02570.21440.117*
C250.0249 (3)0.2642 (2)0.4189 (2)0.0710 (7)
H25A0.06390.23550.50610.106*
H25B0.10670.28090.35830.106*
H25C0.03060.31790.44400.106*
C260.15968 (16)0.06997 (10)0.36153 (16)0.0480 (4)
H26A0.21400.12130.40420.058*
H26B0.06840.06090.41520.058*
O1W0.53363 (16)0.46331 (10)0.07692 (16)0.0895 (6)
H1WB0.592 (4)0.502 (2)0.118 (4)0.121 (13)*
H1WA0.4437 (18)0.481 (3)0.084 (4)0.116 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0763 (4)0.0731 (4)0.0804 (4)0.0350 (3)0.0019 (3)0.0121 (3)
O10.0574 (8)0.0452 (8)0.0640 (9)0.0130 (6)0.0149 (6)0.0006 (6)
O20.0484 (7)0.0366 (6)0.0386 (6)0.0066 (5)0.0034 (5)0.0041 (5)
O30.0583 (8)0.0525 (8)0.0461 (7)0.0059 (6)0.0052 (6)0.0095 (6)
O40.0588 (8)0.0376 (8)0.0724 (9)0.0072 (6)0.0007 (7)0.0089 (7)
N10.0532 (9)0.0424 (9)0.0548 (9)0.0022 (7)0.0011 (7)0.0092 (7)
C10.0357 (9)0.0530 (12)0.0576 (11)0.0082 (8)0.0053 (8)0.0031 (9)
C20.0348 (9)0.0597 (13)0.0589 (12)0.0038 (8)0.0082 (8)0.0071 (9)
C30.0454 (9)0.0412 (10)0.0419 (9)0.0072 (8)0.0072 (8)0.0052 (8)
C40.0370 (8)0.0349 (9)0.0345 (8)0.0023 (7)0.0009 (6)0.0031 (7)
C50.0327 (8)0.0360 (9)0.0322 (7)0.0021 (6)0.0009 (6)0.0026 (7)
C60.0377 (8)0.0406 (10)0.0396 (8)0.0063 (7)0.0013 (7)0.0028 (7)
C70.0485 (10)0.0398 (10)0.0536 (10)0.0117 (8)0.0007 (8)0.0022 (8)
C80.0542 (10)0.0316 (9)0.0464 (10)0.0030 (8)0.0027 (8)0.0013 (8)
C90.0405 (9)0.0320 (9)0.0426 (9)0.0009 (7)0.0059 (7)0.0025 (7)
C100.0338 (8)0.0332 (8)0.0396 (8)0.0025 (6)0.0017 (7)0.0033 (7)
C110.0329 (8)0.0380 (9)0.0470 (9)0.0060 (7)0.0069 (7)0.0063 (7)
C120.0339 (8)0.0326 (9)0.0540 (10)0.0007 (7)0.0124 (7)0.0030 (8)
C130.0403 (9)0.0417 (10)0.0415 (9)0.0016 (8)0.0055 (7)0.0003 (8)
C140.0483 (9)0.0371 (9)0.0403 (9)0.0048 (7)0.0034 (7)0.0059 (7)
C150.0498 (10)0.0588 (13)0.0461 (10)0.0044 (9)0.0010 (8)0.0094 (9)
C160.0380 (8)0.0461 (10)0.0480 (10)0.0018 (8)0.0044 (7)0.0040 (8)
C170.0948 (18)0.0526 (14)0.0798 (16)0.0033 (13)0.0015 (14)0.0272 (12)
C180.0534 (11)0.0556 (12)0.0380 (9)0.0021 (9)0.0005 (8)0.0007 (8)
C190.0499 (10)0.0632 (13)0.0410 (10)0.0067 (9)0.0045 (8)0.0142 (9)
C200.0345 (8)0.0515 (11)0.0556 (11)0.0050 (8)0.0009 (7)0.0091 (9)
C210.0415 (9)0.0541 (11)0.0450 (10)0.0039 (8)0.0055 (8)0.0027 (9)
C220.0412 (9)0.0494 (10)0.0391 (9)0.0006 (8)0.0016 (7)0.0052 (8)
C230.0389 (9)0.0396 (9)0.0395 (9)0.0036 (7)0.0008 (7)0.0029 (7)
C240.0695 (15)0.0659 (16)0.1001 (19)0.0209 (13)0.0321 (14)0.0023 (14)
C250.0798 (16)0.0815 (17)0.0508 (12)0.0221 (13)0.0132 (11)0.0118 (12)
C260.0613 (12)0.0406 (11)0.0418 (9)0.0037 (8)0.0030 (8)0.0013 (8)
O1W0.0715 (13)0.0886 (15)0.1095 (15)0.0265 (11)0.0246 (11)0.0396 (12)
Geometric parameters (Å, º) top
Cl1—C201.752 (2)C11—H11B0.9700
O1—C31.375 (2)C12—C131.483 (3)
O1—C241.422 (3)C13—C141.337 (3)
O2—C41.387 (2)C14—H14A0.9300
O2—C261.4244 (19)C15—C161.521 (3)
O3—C131.355 (2)C15—H15A0.9700
O3—C251.418 (3)C15—H15B0.9700
O4—C121.218 (2)C16—H16A0.9700
N1—C151.465 (3)C16—H16B0.9700
N1—C171.471 (3)C17—H17A0.9600
N1—C81.473 (2)C17—H17B0.9600
C1—C21.374 (3)C17—H17C0.9600
C1—C61.384 (3)C18—C191.376 (3)
C1—H1A0.9300C18—C231.393 (3)
C2—C31.375 (3)C18—H18A0.9300
C2—H2A0.9300C19—C201.377 (3)
C3—C41.407 (2)C19—H19A0.9300
C4—C51.397 (2)C20—C211.371 (3)
C5—C61.406 (2)C21—C221.382 (3)
C5—C101.540 (2)C21—H21A0.9300
C6—C71.513 (3)C22—C231.379 (3)
C7—C81.526 (3)C22—H22A0.9300
C7—H7A0.9700C23—C261.514 (2)
C7—H7B0.9700C24—H24A0.9600
C8—C91.521 (2)C24—H24B0.9600
C8—H8A0.9800C24—H24C0.9600
C9—C141.497 (2)C25—H25A0.9600
C9—C101.549 (2)C25—H25B0.9600
C9—H9A0.9800C25—H25C0.9600
C10—C161.532 (2)C26—H26A0.9700
C10—C111.535 (2)C26—H26B0.9700
C11—C121.495 (3)O1W—H1WB0.851 (10)
C11—H11A0.9700O1W—H1WA0.846 (10)
C3—O1—C24117.17 (18)O3—C13—C12112.34 (16)
C4—O2—C26114.65 (12)C13—C14—C9122.41 (16)
C13—O3—C25116.20 (16)C13—C14—H14A118.8
C15—N1—C17111.53 (18)C9—C14—H14A118.8
C15—N1—C8112.83 (15)N1—C15—C16110.88 (15)
C17—N1—C8111.96 (18)N1—C15—H15A109.5
C2—C1—C6122.20 (18)C16—C15—H15A109.5
C2—C1—H1A118.9N1—C15—H15B109.5
C6—C1—H1A118.9C16—C15—H15B109.5
C1—C2—C3119.34 (17)H15A—C15—H15B108.1
C1—C2—H2A120.3C15—C16—C10111.60 (14)
C3—C2—H2A120.3C15—C16—H16A109.3
C2—C3—O1124.42 (16)C10—C16—H16A109.3
C2—C3—C4119.58 (17)C15—C16—H16B109.3
O1—C3—C4116.00 (16)C10—C16—H16B109.3
O2—C4—C5120.78 (14)H16A—C16—H16B108.0
O2—C4—C3117.98 (15)N1—C17—H17A109.5
C5—C4—C3121.18 (15)N1—C17—H17B109.5
C4—C5—C6117.85 (15)H17A—C17—H17B109.5
C4—C5—C10122.76 (14)N1—C17—H17C109.5
C6—C5—C10119.35 (15)H17A—C17—H17C109.5
C1—C6—C5119.51 (17)H17B—C17—H17C109.5
C1—C6—C7117.85 (16)C19—C18—C23120.93 (18)
C5—C6—C7122.62 (15)C19—C18—H18A119.5
C6—C7—C8115.91 (15)C23—C18—H18A119.5
C6—C7—H7A108.3C18—C19—C20119.15 (17)
C8—C7—H7A108.3C18—C19—H19A120.4
C6—C7—H7B108.3C20—C19—H19A120.4
C8—C7—H7B108.3C21—C20—C19121.19 (18)
H7A—C7—H7B107.4C21—C20—Cl1119.39 (16)
N1—C8—C9108.14 (15)C19—C20—Cl1119.42 (15)
N1—C8—C7117.17 (16)C20—C21—C22119.11 (18)
C9—C8—C7108.27 (15)C20—C21—H21A120.4
N1—C8—H8A107.6C22—C21—H21A120.4
C9—C8—H8A107.6C23—C22—C21121.18 (17)
C7—C8—H8A107.6C23—C22—H22A119.4
C14—C9—C8112.35 (15)C21—C22—H22A119.4
C14—C9—C10111.68 (14)C22—C23—C18118.39 (18)
C8—C9—C10109.92 (14)C22—C23—C26122.41 (15)
C14—C9—H9A107.6C18—C23—C26119.20 (16)
C8—C9—H9A107.6O1—C24—H24A109.5
C10—C9—H9A107.6O1—C24—H24B109.5
C16—C10—C11111.01 (14)H24A—C24—H24B109.5
C16—C10—C5109.63 (13)O1—C24—H24C109.5
C11—C10—C5114.69 (14)H24A—C24—H24C109.5
C16—C10—C9107.05 (14)H24B—C24—H24C109.5
C11—C10—C9104.58 (13)O3—C25—H25A109.5
C5—C10—C9109.50 (13)O3—C25—H25B109.5
C12—C11—C10114.34 (13)H25A—C25—H25B109.5
C12—C11—H11A108.7O3—C25—H25C109.5
C10—C11—H11A108.7H25A—C25—H25C109.5
C12—C11—H11B108.7H25B—C25—H25C109.5
C10—C11—H11B108.7O2—C26—C23108.70 (12)
H11A—C11—H11B107.6O2—C26—H26A109.9
O4—C12—C13121.13 (17)C23—C26—H26A109.9
O4—C12—C11121.91 (17)O2—C26—H26B109.9
C13—C12—C11116.90 (15)C23—C26—H26B109.9
C14—C13—O3127.28 (17)H26A—C26—H26B108.3
C14—C13—C12120.32 (16)H1WB—O1W—H1WA109 (4)
C6—C1—C2—C32.4 (3)C8—C9—C10—C1659.88 (18)
C1—C2—C3—O1177.22 (17)C14—C9—C10—C1156.88 (17)
C1—C2—C3—C42.8 (3)C8—C9—C10—C11177.73 (14)
C24—O1—C3—C22.9 (3)C14—C9—C10—C566.49 (17)
C24—O1—C3—C4177.09 (19)C8—C9—C10—C558.90 (18)
C26—O2—C4—C5110.58 (16)C16—C10—C11—C12172.20 (15)
C26—O2—C4—C372.10 (18)C5—C10—C11—C1262.86 (19)
C2—C3—C4—O2178.72 (15)C9—C10—C11—C1257.09 (18)
O1—C3—C4—O21.3 (2)C10—C11—C12—O4154.14 (17)
C2—C3—C4—C51.4 (2)C10—C11—C12—C1328.5 (2)
O1—C3—C4—C5178.57 (14)C25—O3—C13—C148.4 (3)
O2—C4—C5—C6176.86 (14)C25—O3—C13—C12174.43 (18)
C3—C4—C5—C65.9 (2)O4—C12—C13—C14173.55 (17)
O2—C4—C5—C100.7 (2)C11—C12—C13—C143.8 (2)
C3—C4—C5—C10176.50 (15)O4—C12—C13—O33.8 (2)
C2—C1—C6—C52.2 (3)C11—C12—C13—O3178.80 (14)
C2—C1—C6—C7176.47 (18)O3—C13—C14—C9179.57 (15)
C4—C5—C6—C16.2 (2)C12—C13—C14—C92.6 (3)
C10—C5—C6—C1176.07 (16)C8—C9—C14—C13154.08 (17)
C4—C5—C6—C7172.38 (15)C10—C9—C14—C1330.0 (2)
C10—C5—C6—C75.3 (2)C17—N1—C15—C16175.80 (18)
C1—C6—C7—C8176.95 (16)C8—N1—C15—C1657.2 (2)
C5—C6—C7—C81.7 (3)N1—C15—C16—C1054.9 (2)
C15—N1—C8—C960.6 (2)C11—C10—C16—C15169.38 (15)
C17—N1—C8—C9172.57 (18)C5—C10—C16—C1562.88 (19)
C15—N1—C8—C762.0 (2)C9—C10—C16—C1555.82 (18)
C17—N1—C8—C764.8 (2)C23—C18—C19—C200.2 (3)
C6—C7—C8—N186.1 (2)C18—C19—C20—C211.3 (3)
C6—C7—C8—C936.5 (2)C18—C19—C20—Cl1177.68 (16)
N1—C8—C9—C14172.93 (14)C19—C20—C21—C220.9 (3)
C7—C8—C9—C1459.18 (19)Cl1—C20—C21—C22178.01 (15)
N1—C8—C9—C1062.06 (18)C20—C21—C22—C230.9 (3)
C7—C8—C9—C1065.83 (18)C21—C22—C23—C182.4 (3)
C4—C5—C10—C1683.19 (19)C21—C22—C23—C26177.14 (16)
C6—C5—C10—C1694.37 (18)C19—C18—C23—C222.0 (3)
C4—C5—C10—C1142.5 (2)C19—C18—C23—C26177.50 (16)
C6—C5—C10—C11139.97 (15)C4—O2—C26—C23169.61 (13)
C4—C5—C10—C9159.65 (14)C22—C23—C26—O26.9 (2)
C6—C5—C10—C922.8 (2)C18—C23—C26—O2172.64 (16)
C14—C9—C10—C16174.73 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.982.563.469 (2)155
O1W—H1WB···O4ii0.852.042.879 (2)169
O1W—H1WA···N10.852.162.899 (2)146
Symmetry codes: (i) x, y1/2, z; (ii) x+1, y1/2, z.

Experimental details

Crystal data
Chemical formulaC26H28ClNO4·H2O
Mr471.96
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)8.8866 (4), 14.6386 (7), 9.1860 (4)
β (°) 91.618 (1)
V3)1194.51 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.45 × 0.36 × 0.32
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.917, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
13795, 4185, 3974
Rint0.022
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.082, 1.05
No. of reflections4185
No. of parameters303
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.21
Absolute structureFlack (1983), 1991 Friedel pairs
Absolute structure parameter0.02 (6)

Computer programs: SMART (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
C8—H8A···O1i0.982.5573.469 (2)155
O1W—H1WB···O4ii0.852.0402.879 (2)169
O1W—H1WA···N10.852.1572.899 (2)146
Symmetry codes: (i) x, y1/2, z; (ii) x+1, y1/2, z.
 

Acknowledgements

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

References

First citationBatterham, T. J., Bell, K. H. & Weis, U. (1965). Aust. J. Chem. 18, 1799–1806.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationLi, Y.-F., Qian, Y., Yin, L.-H., Lv, R. & Zhu, H.-J. (2009). Acta Cryst. E65, o689.  CSD CrossRef IUCr Journals Google Scholar
First citationLiu, L., Buchner, E., Beitze, D., Schmidt-Weber, C. B., Kaever, V. & Emmricinne, R. W. (1996). Int. J. Immunopharmacol. 18, 529–543.  CrossRef CAS PubMed Web of Science Google Scholar
First citationLiu, L., Riese, J., Resch, K. & Kaever, V. (1994). Arzneim. Forsch. 44, 1223–1226.  CAS Google Scholar
First citationLiu, Q., Zhou, L. L. & Li, R. (1997). Chin. Trad. Herbal Drugs, 28, 247–249.  Google Scholar
First citationMark, W., Schneeberger, S., Seiler, R., Stroka, D. M., Amberger, A., Offner, F., Candinas, D. & Margreiter, R. (2003). Transplantation, 75, 940–945.  Web of Science CrossRef PubMed CAS Google Scholar
First citationMitsunobu, O. (1981). Synthesis, pp. 1–28.  CrossRef Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYe, X. R., Yan, K. X., Wu, K. M., Feng, X. Z., Huang, Y. M. & Qiu, P. (2004). Acta Pharmacol. Sin. 39, 180–183.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1190
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds