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-iodo­benz­yl­oxy)-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 17 August 2010; accepted 8 October 2010; online 20 October 2010)

In the title compound, C26H28INO4·H2O, benzene rings are inclined at a dihedral angle of 69.9 (1)°. The N-containing ring exhibits a chair conformation, while the other rings approximate to envelope conformations. In the crystal, the uncoordinated water mol­ecule forms inter­molecular O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28INO4·H2O

  • Mr = 563.41

  • Monoclinic, P 21

  • a = 8.9005 (8) Å

  • b = 14.9221 (14) Å

  • c = 9.2426 (9) Å

  • β = 91.432 (2)°

  • V = 1227.2 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.34 mm−1

  • T = 293 K

  • 0.31 × 0.30 × 0.23 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.482, Tmax = 1.000

  • 7231 measured reflections

  • 5047 independent reflections

  • 4844 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.087

  • S = 1.07

  • 5047 reflections

  • 309 parameters

  • 4 restraints

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

  • Δρmax = 0.98 e Å−3

  • Δρmin = −0.49 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2311 Friedel pairs

  • Flack parameter: −0.016 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5C⋯O3i 0.84 (3) 2.13 (3) 2.946 (5) 164 (6)
O5—H5D⋯N1ii 0.84 (3) 2.26 (11) 2.924 (6) 135 (13)
Symmetry codes: (i) x, y, z+1; (ii) [-x+2, y+{\script{1\over 2}}, -z+1].

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 synthesized a new sinomenine derivative (9S,13R,14S)-7,8-didehydro-4-(4'-iodiobenzyloxy)-3,7-dimethoxy-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 crystal structure is stabilized by O—H···O and O—H···N hydrogen bonds linking sinomenine derivative and the water molecule, 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/C2/C3/C4/C12/C11 form the benzene plane (I), and atoms C19···C24 form the benzene plane substituted by Iodine (II). The angle between the two planes is 69.9 (1)°. Rings C [C5/C6/C7/C8/C14/C13] and B [C9···C14] in the molecule approximate both an envelope conformation. In contrast, ring D [C9/N1/C16/C15/C13/C14] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Li et al., 2009; Batterham et al., 1965).

Related literature top

For 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). Light yellow blocks of (I) were grown from a dichloromethane 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.

Structure description top

We synthesized a new sinomenine derivative (9S,13R,14S)-7,8-didehydro-4-(4'-iodiobenzyloxy)-3,7-dimethoxy-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 crystal structure is stabilized by O—H···O and O—H···N hydrogen bonds linking sinomenine derivative and the water molecule, 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/C2/C3/C4/C12/C11 form the benzene plane (I), and atoms C19···C24 form the benzene plane substituted by Iodine (II). The angle between the two planes is 69.9 (1)°. Rings C [C5/C6/C7/C8/C14/C13] and B [C9···C14] in the molecule approximate both an envelope conformation. In contrast, ring D [C9/N1/C16/C15/C13/C14] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Li et al., 2009; Batterham et al., 1965).

For 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).

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.
[Figure 2] Fig. 2. Packing structure of the title compound.
(9S,13R,14S)-7,8-Didehydro-4-(4-iodobenzyloxy)-3,7- dimethoxy-17-methylmorphinan-6-one monohydrate top
Crystal data top
C26H28INO4·H2OF(000) = 572
Mr = 563.41Dx = 1.525 Mg m3
Monoclinic, P21Melting point: 412 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 8.9005 (8) ÅCell parameters from 4522 reflections
b = 14.9221 (14) Åθ = 4.6–56.4°
c = 9.2426 (9) ŵ = 1.34 mm1
β = 91.432 (2)°T = 293 K
V = 1227.2 (2) Å3Prismatic, colourless
Z = 20.31 × 0.30 × 0.23 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5047 independent reflections
Radiation source: fine-focus sealed tube4844 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000
h = 611
Tmin = 0.482, Tmax = 1.000k = 1819
7231 measured reflectionsl = 1111
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)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0909P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.004
5047 reflectionsΔρmax = 0.98 e Å3
309 parametersΔρmin = 0.49 e Å3
4 restraintsAbsolute structure: Flack (1983), 2311 Friedel pairs
0 constraintsAbsolute structure parameter: 0.016 (17)
Primary atom site location: structure-invariant direct methods
Crystal data top
C26H28INO4·H2OV = 1227.2 (2) Å3
Mr = 563.41Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.9005 (8) ŵ = 1.34 mm1
b = 14.9221 (14) ÅT = 293 K
c = 9.2426 (9) Å0.31 × 0.30 × 0.23 mm
β = 91.432 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5047 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000
4844 reflections with I > 2σ(I)
Tmin = 0.482, Tmax = 1.000Rint = 0.038
7231 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087Δρmax = 0.98 e Å3
S = 1.07Δρmin = 0.49 e Å3
5047 reflectionsAbsolute structure: Flack (1983), 2311 Friedel pairs
309 parametersAbsolute structure parameter: 0.016 (17)
4 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I11.01684 (3)1.24508 (2)0.40697 (3)0.05793 (10)
N10.7186 (4)0.5021 (2)0.1708 (4)0.0481 (8)
O10.3354 (3)0.90402 (19)0.2691 (3)0.0528 (7)
O20.6158 (3)0.86212 (17)0.2123 (2)0.0381 (5)
O30.7304 (3)0.86778 (19)0.1786 (3)0.0532 (7)
O40.5676 (3)0.7548 (3)0.3349 (3)0.0504 (7)
O50.9701 (6)0.9909 (3)0.9213 (6)0.0898 (14)
C10.2856 (4)0.6717 (3)0.1460 (5)0.0474 (9)
H10.21040.62900.13300.057*
C20.2469 (4)0.7561 (4)0.1937 (4)0.0497 (10)
H20.14690.77050.20920.060*
C30.3580 (4)0.8183 (3)0.2179 (4)0.0412 (8)
C40.5086 (4)0.7971 (2)0.1890 (4)0.0342 (7)
C50.7896 (4)0.7650 (2)0.0106 (4)0.0386 (8)
H5A0.79680.81640.07450.046*
H5B0.89100.74510.00820.046*
C60.7159 (4)0.7938 (2)0.1298 (4)0.0392 (8)
C70.6302 (4)0.7238 (2)0.2098 (4)0.0381 (8)
C80.6280 (4)0.6389 (2)0.1618 (4)0.0407 (8)
H80.57900.59550.21780.049*
C90.6273 (4)0.5306 (2)0.0456 (4)0.0422 (8)
H100.62900.48200.02560.051*
C100.4626 (4)0.5535 (3)0.0708 (4)0.0471 (9)
H11A0.40550.54170.01790.056*
H11B0.42540.51330.14430.056*
C110.4318 (4)0.6484 (3)0.1170 (4)0.0382 (7)
C120.5457 (4)0.7138 (2)0.1318 (4)0.0314 (7)
C130.7065 (4)0.6896 (2)0.0881 (4)0.0348 (7)
C140.7012 (4)0.6117 (2)0.0221 (4)0.0364 (7)
H90.80530.59520.04220.044*
C150.7966 (4)0.6576 (3)0.2203 (4)0.0442 (8)
H15A0.89990.64730.19370.053*
H15B0.79670.70410.29380.053*
C160.7328 (5)0.5722 (3)0.2826 (4)0.0494 (9)
H16A0.79820.55110.36100.059*
H16B0.63490.58440.32180.059*
C170.6656 (6)0.4173 (4)0.2330 (6)0.0710 (14)
H17A0.56840.42620.27340.107*
H17B0.73520.39790.30770.107*
H17C0.65880.37250.15860.107*
C180.6493 (5)0.8804 (3)0.3618 (4)0.0435 (8)
H18A0.70190.82990.40570.052*
H18B0.55710.89000.41320.052*
C190.7461 (4)0.9628 (2)0.3707 (4)0.0369 (7)
C200.7795 (5)0.9999 (3)0.5060 (4)0.0464 (9)
H200.74780.97130.58920.056*
C210.8598 (5)1.0793 (3)0.5171 (4)0.0479 (9)
H210.88081.10450.60740.057*
C220.9082 (4)1.1204 (3)0.3940 (4)0.0410 (8)
C230.8819 (4)1.0833 (3)0.2597 (4)0.0443 (9)
H230.91721.11100.17710.053*
C240.8021 (4)1.0042 (3)0.2494 (4)0.0398 (8)
H240.78550.97810.15900.048*
C250.4769 (6)0.6931 (5)0.4172 (5)0.0738 (16)
H25A0.53930.64630.45390.111*
H25B0.42850.72410.49660.111*
H25C0.40220.66770.35640.111*
C260.1839 (6)0.9304 (4)0.2891 (7)0.0756 (16)
H26A0.12390.91350.20580.113*
H26B0.17940.99420.30160.113*
H26C0.14610.90140.37350.113*
H5C0.913 (6)0.954 (4)0.879 (7)0.10 (2)*
H5D1.060 (5)0.976 (7)0.937 (14)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05580 (15)0.06209 (16)0.05586 (15)0.02060 (14)0.00072 (10)0.00469 (15)
N10.0504 (19)0.0413 (17)0.0528 (19)0.0021 (14)0.0037 (15)0.0087 (14)
O10.0508 (16)0.0474 (16)0.0610 (17)0.0130 (12)0.0148 (13)0.0009 (13)
O20.0438 (14)0.0384 (13)0.0321 (11)0.0044 (10)0.0006 (10)0.0043 (10)
O30.0535 (17)0.0367 (15)0.0698 (18)0.0028 (12)0.0062 (14)0.0022 (13)
O40.0530 (14)0.0547 (19)0.0433 (12)0.0036 (16)0.0010 (10)0.0055 (15)
O50.072 (3)0.088 (3)0.111 (3)0.028 (2)0.029 (2)0.041 (3)
C10.0345 (18)0.057 (3)0.051 (2)0.0086 (17)0.0049 (17)0.0091 (18)
C20.0323 (15)0.061 (3)0.056 (2)0.0032 (19)0.0095 (14)0.003 (2)
C30.0401 (19)0.047 (2)0.0368 (18)0.0065 (16)0.0071 (15)0.0082 (15)
C40.0339 (18)0.0390 (19)0.0299 (17)0.0021 (14)0.0027 (14)0.0023 (14)
C50.0313 (15)0.039 (2)0.0459 (17)0.0061 (13)0.0084 (13)0.0071 (13)
C60.0322 (17)0.0351 (19)0.051 (2)0.0019 (14)0.0151 (15)0.0063 (15)
C70.0383 (16)0.042 (2)0.0345 (16)0.0025 (13)0.0064 (13)0.0022 (13)
C80.046 (2)0.0396 (19)0.0372 (18)0.0082 (16)0.0044 (15)0.0095 (15)
C90.049 (2)0.039 (2)0.0388 (18)0.0050 (16)0.0037 (16)0.0026 (14)
C100.049 (2)0.042 (2)0.050 (2)0.0103 (16)0.0032 (17)0.0006 (16)
C110.0362 (17)0.0435 (19)0.0349 (17)0.0070 (15)0.0007 (13)0.0034 (14)
C120.0296 (16)0.0366 (18)0.0279 (16)0.0020 (12)0.0014 (13)0.0027 (12)
C130.0327 (16)0.0387 (18)0.0330 (16)0.0015 (13)0.0019 (13)0.0044 (14)
C140.0392 (19)0.0327 (18)0.0376 (17)0.0018 (14)0.0065 (14)0.0045 (13)
C150.0372 (18)0.052 (2)0.044 (2)0.0054 (16)0.0039 (15)0.0057 (16)
C160.047 (2)0.059 (3)0.042 (2)0.0088 (18)0.0034 (17)0.0075 (18)
C170.080 (4)0.054 (3)0.079 (3)0.002 (2)0.002 (3)0.024 (2)
C180.054 (2)0.040 (2)0.0365 (18)0.0025 (17)0.0015 (16)0.0011 (14)
C190.0350 (17)0.0387 (18)0.0369 (18)0.0058 (14)0.0029 (14)0.0005 (14)
C200.055 (2)0.051 (2)0.0335 (18)0.0047 (18)0.0038 (16)0.0015 (16)
C210.050 (2)0.064 (3)0.0301 (17)0.0084 (18)0.0003 (15)0.0069 (16)
C220.0321 (17)0.048 (2)0.0431 (19)0.0019 (15)0.0014 (14)0.0044 (15)
C230.0392 (19)0.060 (2)0.0335 (18)0.0021 (17)0.0041 (14)0.0028 (16)
C240.0414 (19)0.049 (2)0.0295 (16)0.0028 (16)0.0013 (14)0.0054 (14)
C250.084 (4)0.092 (4)0.044 (3)0.024 (3)0.017 (3)0.009 (2)
C260.063 (3)0.065 (3)0.100 (4)0.023 (2)0.036 (3)0.007 (3)
Geometric parameters (Å, º) top
I1—C222.099 (4)C10—H11B0.9700
N1—C91.461 (5)C11—C121.411 (5)
N1—C171.472 (6)C12—C131.541 (5)
N1—C161.474 (6)C13—C151.521 (5)
O1—C31.380 (5)C13—C141.546 (4)
O1—C261.421 (5)C14—H90.9800
O2—C41.374 (4)C15—C161.516 (6)
O2—C181.432 (4)C15—H15A0.9700
O3—C61.201 (5)C15—H15B0.9700
O4—C71.353 (4)C16—H16A0.9700
O4—C251.430 (6)C16—H16B0.9700
O5—H5C0.84 (3)C17—H17A0.9600
O5—H5D0.84 (3)C17—H17B0.9600
C1—C111.380 (5)C17—H17C0.9600
C1—C21.381 (7)C18—C191.502 (5)
C1—H10.9300C18—H18A0.9700
C2—C31.370 (6)C18—H18B0.9700
C2—H20.9300C19—C241.384 (5)
C3—C41.410 (5)C19—C201.393 (5)
C4—C121.392 (5)C20—C211.387 (6)
C5—C61.501 (5)C20—H200.9300
C5—C131.534 (5)C21—C221.371 (5)
C5—H5A0.9700C21—H210.9300
C5—H5B0.9700C22—C231.375 (5)
C6—C71.480 (5)C23—C241.379 (6)
C7—C81.343 (5)C23—H230.9300
C8—C141.488 (5)C24—H240.9300
C8—H80.9300C25—H25A0.9600
C9—C141.520 (5)C25—H25B0.9600
C9—C101.528 (5)C25—H25C0.9600
C9—H100.9800C26—H26A0.9600
C10—C111.507 (6)C26—H26B0.9600
C10—H11A0.9700C26—H26C0.9600
C9—N1—C17112.5 (4)C8—C14—C13111.8 (3)
C9—N1—C16112.6 (3)C9—C14—C13109.5 (3)
C17—N1—C16111.0 (4)C8—C14—H9107.4
C3—O1—C26116.6 (4)C9—C14—H9107.4
C4—O2—C18114.4 (3)C13—C14—H9107.4
C7—O4—C25116.7 (4)C16—C15—C13111.9 (3)
H5C—O5—H5D118 (5)C16—C15—H15A109.2
C11—C1—C2122.4 (4)C13—C15—H15A109.2
C11—C1—H1118.8C16—C15—H15B109.2
C2—C1—H1118.8C13—C15—H15B109.2
C3—C2—C1119.0 (3)H15A—C15—H15B107.9
C3—C2—H2120.5N1—C16—C15110.9 (3)
C1—C2—H2120.5N1—C16—H16A109.4
C2—C3—O1124.9 (4)C15—C16—H16A109.4
C2—C3—C4120.2 (4)N1—C16—H16B109.4
O1—C3—C4114.9 (4)C15—C16—H16B109.4
O2—C4—C12121.3 (3)H16A—C16—H16B108.0
O2—C4—C3118.1 (3)N1—C17—H17A109.5
C12—C4—C3120.5 (4)N1—C17—H17B109.5
C6—C5—C13114.1 (3)H17A—C17—H17B109.5
C6—C5—H5A108.7N1—C17—H17C109.5
C13—C5—H5A108.7H17A—C17—H17C109.5
C6—C5—H5B108.7H17B—C17—H17C109.5
C13—C5—H5B108.7O2—C18—C19108.3 (3)
H5A—C5—H5B107.6O2—C18—H18A110.0
O3—C6—C7121.3 (4)C19—C18—H18A110.0
O3—C6—C5122.6 (3)O2—C18—H18B110.0
C7—C6—C5116.0 (3)C19—C18—H18B110.0
C8—C7—O4126.6 (3)H18A—C18—H18B108.4
C8—C7—C6120.8 (3)C24—C19—C20118.5 (4)
O4—C7—C6112.5 (3)C24—C19—C18122.6 (3)
C7—C8—C14122.3 (3)C20—C19—C18119.0 (3)
C7—C8—H8118.8C21—C20—C19120.3 (4)
C14—C8—H8118.8C21—C20—H20119.8
N1—C9—C14108.7 (3)C19—C20—H20119.8
N1—C9—C10117.5 (3)C22—C21—C20119.5 (4)
C14—C9—C10108.2 (3)C22—C21—H21120.2
N1—C9—H10107.4C20—C21—H21120.2
C14—C9—H10107.4C21—C22—C23121.3 (4)
C10—C9—H10107.4C21—C22—I1120.2 (3)
C11—C10—C9115.8 (3)C23—C22—I1118.5 (3)
C11—C10—H11A108.3C22—C23—C24118.9 (3)
C9—C10—H11A108.3C22—C23—H23120.6
C11—C10—H11B108.3C24—C23—H23120.6
C9—C10—H11B108.3C23—C24—C19121.5 (3)
H11A—C10—H11B107.4C23—C24—H24119.3
C1—C11—C12119.0 (4)C19—C24—H24119.3
C1—C11—C10118.1 (3)O4—C25—H25A109.5
C12—C11—C10122.9 (3)O4—C25—H25B109.5
C4—C12—C11118.5 (3)H25A—C25—H25B109.5
C4—C12—C13122.6 (3)O4—C25—H25C109.5
C11—C12—C13118.8 (3)H25A—C25—H25C109.5
C15—C13—C5110.8 (3)H25B—C25—H25C109.5
C15—C13—C12109.7 (3)O1—C26—H26A109.5
C5—C13—C12114.3 (3)O1—C26—H26B109.5
C15—C13—C14107.5 (3)H26A—C26—H26B109.5
C5—C13—C14104.5 (3)O1—C26—H26C109.5
C12—C13—C14109.6 (3)H26A—C26—H26C109.5
C8—C14—C9112.9 (3)H26B—C26—H26C109.5
C11—C1—C2—C32.2 (6)C6—C5—C13—C1261.4 (4)
C1—C2—C3—O1178.2 (3)C6—C5—C13—C1458.5 (4)
C1—C2—C3—C42.4 (6)C4—C12—C13—C1584.0 (4)
C26—O1—C3—C24.1 (6)C11—C12—C13—C1594.3 (4)
C26—O1—C3—C4175.4 (4)C4—C12—C13—C541.1 (4)
C18—O2—C4—C12110.7 (3)C11—C12—C13—C5140.6 (3)
C18—O2—C4—C372.3 (4)C4—C12—C13—C14158.1 (3)
C2—C3—C4—O2178.8 (3)C11—C12—C13—C1423.6 (4)
O1—C3—C4—O20.7 (5)C7—C8—C14—C9152.3 (3)
C2—C3—C4—C121.9 (5)C7—C8—C14—C1328.2 (5)
O1—C3—C4—C12177.6 (3)N1—C9—C14—C8172.5 (3)
C13—C5—C6—O3153.4 (3)C10—C9—C14—C859.0 (4)
C13—C5—C6—C729.9 (4)N1—C9—C14—C1362.2 (4)
C25—O4—C7—C86.9 (6)C10—C9—C14—C1366.4 (4)
C25—O4—C7—C6177.4 (4)C15—C13—C14—C8174.5 (3)
O3—C6—C7—C8172.9 (4)C5—C13—C14—C856.7 (4)
C5—C6—C7—C83.9 (5)C12—C13—C14—C866.3 (4)
O3—C6—C7—O43.1 (5)C15—C13—C14—C959.6 (4)
C5—C6—C7—O4179.9 (3)C5—C13—C14—C9177.3 (3)
O4—C7—C8—C14179.8 (3)C12—C13—C14—C959.7 (4)
C6—C7—C8—C144.4 (5)C5—C13—C15—C16169.2 (3)
C17—N1—C9—C14173.1 (4)C12—C13—C15—C1663.7 (4)
C16—N1—C9—C1460.6 (4)C14—C13—C15—C1655.5 (4)
C17—N1—C9—C1063.8 (5)C9—N1—C16—C1556.4 (4)
C16—N1—C9—C1062.6 (4)C17—N1—C16—C15176.4 (4)
N1—C9—C10—C1186.5 (4)C13—C15—C16—N154.0 (4)
C14—C9—C10—C1136.9 (4)C4—O2—C18—C19170.1 (3)
C2—C1—C11—C122.1 (6)O2—C18—C19—C246.3 (5)
C2—C1—C11—C10177.7 (4)O2—C18—C19—C20172.8 (3)
C9—C10—C11—C1177.8 (3)C24—C19—C20—C213.6 (6)
C9—C10—C11—C122.0 (5)C18—C19—C20—C21175.6 (4)
O2—C4—C12—C11177.0 (3)C19—C20—C21—C221.0 (6)
C3—C4—C12—C116.2 (5)C20—C21—C22—C231.6 (6)
O2—C4—C12—C131.3 (5)C20—C21—C22—I1175.7 (3)
C3—C4—C12—C13175.5 (3)C21—C22—C23—C241.5 (6)
C1—C11—C12—C46.3 (5)I1—C22—C23—C24175.9 (3)
C10—C11—C12—C4173.6 (3)C22—C23—C24—C191.2 (6)
C1—C11—C12—C13175.4 (3)C20—C19—C24—C233.7 (6)
C10—C11—C12—C134.8 (5)C18—C19—C24—C23175.4 (4)
C6—C5—C13—C15174.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5C···O3i0.84 (3)2.13 (3)2.946 (5)164 (6)
O5—H5D···N1ii0.84 (3)2.26 (11)2.924 (6)135 (13)
Symmetry codes: (i) x, y, z+1; (ii) x+2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC26H28INO4·H2O
Mr563.41
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)8.9005 (8), 14.9221 (14), 9.2426 (9)
β (°) 91.432 (2)
V3)1227.2 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.34
Crystal size (mm)0.31 × 0.30 × 0.23
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000
Tmin, Tmax0.482, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7231, 5047, 4844
Rint0.038
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.087, 1.07
No. of reflections5047
No. of parameters309
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.98, 0.49
Absolute structureFlack (1983), 2311 Friedel pairs
Absolute structure parameter0.016 (17)

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
O5—H5C···O3i0.84 (3)2.13 (3)2.946 (5)164 (6)
O5—H5D···N1ii0.84 (3)2.26 (11)2.924 (6)135 (13)
Symmetry codes: (i) x, y, z+1; (ii) x+2, y+1/2, z+1.
 

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

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