PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2948.
Published online 2009 October 31. doi:  10.1107/S1600536809044808
PMCID: PMC2971343

N-[(R)-(2-Chloro­phen­yl)(cyclo­pent­yl)meth­yl]-N-[(R)-(2-hydr­oxy-5-methyl­phen­yl)(phen­yl)meth­yl]acetamide

Abstract

In the title compound, C28H30ClNO2, the cyclo­pentane ring adopts an envelope conformation. In the crystal structure, mol­ecules are linked by inter­molecular O—H(...)O hydrogen bonds, forming chains running along the a axis.

Related literature

For general background to amides, see: Calligaris et al. (1972 [triangle]); Ali et al. (2002 [triangle]); Cukurovali et al. (2002 [triangle]); Sriram et al. (2006 [triangle]); Kargar et al. (2009 [triangle]); Takenaka et al. (2002 [triangle]); Varlamov et al. (2003 [triangle]); Zhang et al. (2003 [triangle]). For the synthesis, see: Yang et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2948-scheme1.jpg

Experimental

Crystal data

  • C28H30ClNO2
  • M r = 447.98
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2948-efi1.jpg
  • a = 8.8038 (8) Å
  • b = 11.3417 (10) Å
  • c = 25.485 (2) Å
  • V = 2544.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 298 K
  • 0.24 × 0.16 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.960, T max = 0.980
  • 13334 measured reflections
  • 4452 independent reflections
  • 2845 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.186
  • S = 1.05
  • 4452 reflections
  • 290 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.37 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1871 Friedel pairs
  • Flack parameter: 0.04 (16)

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044808/xu2646sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044808/xu2646Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the Natural Science Foundation of Shandong Province, China (grant No. G0231) and the Foundation of the Education Ministry of China for Returned Students (grant No. G0220) for financial support. The X-ray data were collected at Taishan University, China.

supplementary crystallographic information

Comment

The Schiff base compounds have been widely used in organic and bioinorganic chemistry due to their significant biological activities (Ali et al., 2002; Sriram et al., 2006; Cukurovali et al., 2002). These compounds have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Calligaris et al., 1972). Therefore, the design and syntheis of Schiff bases with various functionalities has become an important field of research nowdays (Takenaka et al., 2002; Varlamov et al., 2003; Zhang et al., 2003). As part of our continuing research of Schiff bases, we report the crystal structure of the title compound, which was acetylated from the corresponding aminophenol.

As shown in Fig. 1, the configuration at the new chiral center (C8) is R. The C9—C14 and C18—C23 aromatic rings are approximately vertical, the dihedral angle between their planes being 83.59 (17)°; the dihedral angle between the planes of the C1—C6 and C18—C23 aromatic rings is 17.45 (19)°, while that between the C1—C6 and C9—C14 planes is 78.89 (16)°. The intermolecular O1—H1···O2 hydrogen-bonding interactions are present in the crystal packing (Table 1 and Fig. 2).

Experimental

The chiral aminophenol was prepared by a condensation reaction of (R)-1-(2-chlorophenyl)-1-cyclopentylmethanamine and (2-hydroxy-5-methylphenyl)(phenyl)methanone followed by reduction with NaBH4. The detailed procedure is similar to that reported by Yang et al. (2005). Then the aminophenol was reacted with acetic anhydride (5 equivalents) in a THF solution (10 ml) at room temperature for 12 h to obtain the title compound. After removal of the solvent, water (20 ml) was added to the residue, stirred and filtrated. Further purification of the filter cake was carried out by thin-layer silica-gel chromatography (chloroform) to give a colorless solid (yield 70.1%). Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of the n-hexane/ethyl acetate solution (3:2 v/v).

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C–H = 0.93–0.98 Å and O–H = 0.82 Å, and refined in riding mode with Uiso(H) = 1.5Ueq(C,O) for methyl H atoms and hydroxy-H atoms, and 1.2Ueq(C) for the others.

Figures

Fig. 1.
The structure of the title compound with 30% probability ellipsoids. H atoms are shown as spheres of arbitrary radii.
Fig. 2.
A packing diagram of (I), dashed lines represent hydrogen bonding.

Crystal data

C28H30ClNO2F(000) = 952
Mr = 447.98Dx = 1.169 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2267 reflections
a = 8.8038 (8) Åθ = 2.5–19.1°
b = 11.3417 (10) ŵ = 0.17 mm1
c = 25.485 (2) ÅT = 298 K
V = 2544.7 (4) Å3Block, colourless
Z = 40.24 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer4452 independent reflections
Radiation source: fine-focus sealed tube2845 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→10
Tmin = 0.960, Tmax = 0.980k = −12→13
13334 measured reflectionsl = −26→30

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.186w = 1/[σ2(Fo2) + (0.1097P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4452 reflectionsΔρmax = 0.33 e Å3
290 parametersΔρmin = −0.36 e Å3
0 restraintsAbsolute structure: Flack (1983), 1871 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (16)

Special details

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)

xyzUiso*/Ueq
Cl10.8441 (4)1.17857 (19)0.06402 (7)0.1811 (11)
O10.2924 (3)0.8872 (3)0.12767 (13)0.0864 (9)
H10.20200.90410.12560.130*
O21.0028 (3)0.9464 (3)0.13070 (14)0.0927 (10)
N10.7501 (3)0.9350 (2)0.13768 (11)0.0520 (7)
C10.3627 (4)0.9125 (3)0.08087 (15)0.0626 (9)
C20.5208 (3)0.9060 (3)0.08034 (14)0.0536 (9)
C30.5941 (4)0.9335 (3)0.03418 (15)0.0628 (10)
H30.69960.92970.03330.075*
C40.5179 (5)0.9666 (4)−0.01089 (15)0.0746 (12)
C50.3620 (6)0.9721 (4)−0.00895 (17)0.0834 (13)
H50.30810.9942−0.03870.100*
C60.2852 (4)0.9457 (4)0.03610 (19)0.0769 (12)
H60.17970.95010.03660.092*
C70.6058 (8)0.9962 (6)−0.06040 (18)0.125 (2)
H7A0.69820.9512−0.06130.188*
H7B0.62971.0788−0.06070.188*
H7C0.54530.9773−0.09060.188*
C80.6007 (3)0.8750 (3)0.13155 (14)0.0512 (8)
H80.53650.90940.15900.061*
C90.6029 (4)0.7431 (4)0.14369 (18)0.0672 (11)
C100.5359 (5)0.6629 (4)0.1108 (3)0.0967 (16)
H100.49090.68910.07990.116*
C110.5336 (7)0.5430 (5)0.1227 (4)0.127 (2)
H110.48500.49060.10030.152*
C120.6012 (8)0.5029 (6)0.1664 (4)0.135 (3)
H120.60320.42240.17330.162*
C130.6684 (7)0.5812 (6)0.2016 (3)0.121 (2)
H130.71330.55340.23220.146*
C140.6677 (5)0.7034 (5)0.1903 (2)0.0923 (14)
H140.71020.75680.21390.111*
C150.8845 (4)0.8931 (4)0.12091 (16)0.0655 (10)
C160.8935 (4)0.7808 (4)0.0899 (2)0.0860 (14)
H16A0.97200.78750.06390.129*
H16B0.79790.76660.07290.129*
H16C0.91620.71630.11300.129*
C170.7476 (4)1.0531 (3)0.16311 (13)0.0566 (8)
H170.84681.08920.15640.068*
C180.6322 (6)1.1299 (4)0.13737 (15)0.0781 (12)
C190.6669 (10)1.1861 (4)0.0904 (2)0.127 (2)
C200.5516 (12)1.2498 (6)0.0618 (3)0.149 (2)
H200.57301.28800.03040.179*
C210.4125 (12)1.2510 (7)0.0828 (4)0.156 (3)
H210.33631.28900.06400.187*
C220.3740 (9)1.2019 (6)0.1287 (4)0.152 (3)
H220.27551.20790.14160.182*
C230.4846 (6)1.1424 (5)0.1564 (3)0.1053 (17)
H230.45991.10950.18870.126*
C240.7295 (5)1.0460 (4)0.22294 (17)0.0842 (12)
H240.63171.00950.23160.101*
C250.8582 (7)0.9781 (6)0.24986 (19)0.1152 (16)
H25A0.82330.89970.25910.138*
H25B0.94320.97010.22590.138*
C260.9037 (9)1.0362 (7)0.2938 (3)0.150 (2)
H26A1.01371.03560.29580.180*
H26B0.86460.99590.32460.180*
C270.8506 (8)1.1554 (7)0.2936 (2)0.1364 (19)
H27A0.93551.20910.28930.164*
H27B0.80081.17330.32660.164*
C280.7391 (7)1.1699 (5)0.24837 (19)0.1022 (14)
H28A0.77591.22760.22330.123*
H28B0.64041.19480.26110.123*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.303 (3)0.1376 (15)0.1031 (11)−0.0737 (18)0.0624 (16)0.0110 (10)
O10.0368 (13)0.119 (3)0.103 (2)0.0043 (13)0.0143 (14)0.021 (2)
O20.0339 (12)0.114 (2)0.130 (3)−0.0049 (14)0.0073 (15)−0.034 (2)
N10.0335 (12)0.0595 (17)0.0629 (16)0.0023 (12)−0.0005 (13)−0.0064 (13)
C10.0391 (18)0.074 (2)0.075 (2)−0.0015 (17)0.0032 (18)0.0019 (19)
C20.0383 (17)0.056 (2)0.067 (2)−0.0048 (14)0.0028 (15)−0.0060 (16)
C30.053 (2)0.071 (2)0.065 (2)−0.0095 (17)0.0037 (18)−0.0108 (18)
C40.080 (3)0.084 (3)0.060 (2)−0.031 (2)0.003 (2)−0.009 (2)
C50.091 (3)0.087 (3)0.071 (3)−0.012 (3)−0.024 (3)−0.003 (2)
C60.049 (2)0.088 (3)0.093 (3)−0.0030 (19)−0.020 (2)−0.005 (2)
C70.149 (5)0.164 (6)0.063 (3)−0.065 (4)0.003 (3)0.010 (3)
C80.0328 (15)0.057 (2)0.064 (2)0.0000 (13)0.0049 (15)0.0002 (16)
C90.0408 (17)0.060 (2)0.101 (3)−0.0027 (16)0.0080 (19)0.008 (2)
C100.073 (3)0.066 (3)0.151 (5)−0.008 (2)0.007 (3)−0.002 (3)
C110.109 (4)0.060 (3)0.212 (7)−0.004 (3)0.001 (5)−0.004 (4)
C120.109 (5)0.074 (4)0.221 (8)0.019 (4)0.044 (5)0.028 (5)
C130.103 (4)0.103 (5)0.157 (6)0.023 (4)0.021 (4)0.058 (5)
C140.075 (3)0.093 (4)0.109 (3)0.009 (2)0.010 (3)0.030 (3)
C150.0380 (19)0.079 (3)0.080 (2)0.0035 (18)0.0028 (17)−0.008 (2)
C160.049 (2)0.093 (3)0.116 (3)0.013 (2)0.022 (2)−0.024 (3)
C170.0516 (18)0.060 (2)0.058 (2)0.0015 (18)−0.0008 (17)−0.0073 (16)
C180.113 (3)0.055 (2)0.066 (2)0.020 (2)−0.028 (2)−0.0157 (19)
C190.227 (6)0.063 (3)0.091 (3)0.020 (4)−0.053 (4)−0.011 (3)
C200.237 (7)0.098 (4)0.111 (4)0.032 (5)−0.063 (5)−0.011 (3)
C210.215 (7)0.099 (4)0.153 (6)0.060 (5)−0.088 (6)−0.031 (4)
C220.152 (5)0.115 (5)0.187 (6)0.066 (4)−0.051 (5)−0.060 (4)
C230.085 (3)0.088 (3)0.143 (4)0.044 (3)−0.048 (3)−0.046 (3)
C240.082 (3)0.106 (3)0.065 (2)0.003 (2)−0.019 (2)−0.016 (2)
C250.129 (4)0.132 (4)0.084 (3)0.010 (3)−0.048 (3)−0.006 (3)
C260.147 (4)0.177 (5)0.126 (4)0.022 (4)−0.053 (3)−0.028 (4)
C270.133 (4)0.156 (4)0.120 (3)0.000 (4)−0.044 (3)−0.042 (3)
C280.102 (3)0.126 (3)0.078 (3)0.010 (3)−0.015 (3)−0.037 (3)

Geometric parameters (Å, °)

Cl1—C191.701 (9)C14—H140.9300
O1—C11.374 (5)C15—C161.501 (6)
O1—H10.8200C16—H16A0.9600
O2—C151.230 (4)C16—H16B0.9600
N1—C151.345 (4)C16—H16C0.9600
N1—C171.488 (4)C17—C181.490 (5)
N1—C81.489 (4)C17—C241.535 (6)
C1—C61.382 (6)C17—H170.9800
C1—C21.394 (5)C18—C191.391 (8)
C2—C31.377 (5)C18—C231.394 (7)
C2—C81.524 (5)C19—C201.443 (9)
C3—C41.382 (6)C20—C211.337 (12)
C3—H30.9300C20—H200.9300
C4—C51.374 (7)C21—C221.340 (11)
C4—C71.518 (6)C21—H210.9300
C5—C61.366 (6)C22—C231.379 (9)
C5—H50.9300C22—H220.9300
C6—H60.9300C23—H230.9300
C7—H7A0.9600C24—C251.532 (7)
C7—H7B0.9600C24—C281.550 (7)
C7—H7C0.9600C24—H240.9800
C8—C91.528 (5)C25—C261.361 (8)
C8—H80.9800C25—H25A0.9700
C9—C101.370 (7)C25—H25B0.9700
C9—C141.394 (6)C26—C271.430 (10)
C10—C111.393 (8)C26—H26A0.9700
C10—H100.9300C26—H26B0.9700
C11—C121.343 (11)C27—C281.523 (8)
C11—H110.9300C27—H27A0.9700
C12—C131.394 (10)C27—H27B0.9700
C12—H120.9300C28—H28A0.9700
C13—C141.415 (8)C28—H28B0.9700
C13—H130.9300
C1—O1—H1109.5C15—C16—H16C109.5
C15—N1—C17118.0 (3)H16A—C16—H16C109.5
C15—N1—C8125.6 (3)H16B—C16—H16C109.5
C17—N1—C8116.3 (2)N1—C17—C18110.2 (3)
O1—C1—C6123.5 (3)N1—C17—C24112.8 (3)
O1—C1—C2116.6 (3)C18—C17—C24113.4 (3)
C6—C1—C2119.9 (4)N1—C17—H17106.7
C3—C2—C1117.7 (3)C18—C17—H17106.7
C3—C2—C8124.6 (3)C24—C17—H17106.7
C1—C2—C8117.7 (3)C19—C18—C23117.2 (5)
C2—C3—C4122.9 (3)C19—C18—C17119.8 (5)
C2—C3—H3118.5C23—C18—C17122.8 (4)
C4—C3—H3118.5C18—C19—C20120.6 (8)
C5—C4—C3117.9 (4)C18—C19—Cl1121.2 (5)
C5—C4—C7122.0 (4)C20—C19—Cl1118.1 (6)
C3—C4—C7120.2 (4)C21—C20—C19116.6 (8)
C6—C5—C4121.0 (4)C21—C20—H20121.7
C6—C5—H5119.5C19—C20—H20121.7
C4—C5—H5119.5C20—C21—C22125.2 (8)
C5—C6—C1120.6 (4)C20—C21—H21117.4
C5—C6—H6119.7C22—C21—H21117.4
C1—C6—H6119.7C21—C22—C23118.2 (8)
C4—C7—H7A109.5C21—C22—H22120.9
C4—C7—H7B109.5C23—C22—H22120.9
H7A—C7—H7B109.5C22—C23—C18122.0 (7)
C4—C7—H7C109.5C22—C23—H23119.0
H7A—C7—H7C109.5C18—C23—H23119.0
H7B—C7—H7C109.5C25—C24—C17113.2 (4)
N1—C8—C2113.1 (3)C25—C24—C28103.2 (4)
N1—C8—C9114.5 (3)C17—C24—C28111.2 (4)
C2—C8—C9113.9 (3)C25—C24—H24109.7
N1—C8—H8104.6C17—C24—H24109.7
C2—C8—H8104.6C28—C24—H24109.7
C9—C8—H8104.6C26—C25—C24110.1 (5)
C10—C9—C14118.9 (4)C26—C25—H25A109.6
C10—C9—C8121.4 (4)C24—C25—H25A109.6
C14—C9—C8119.6 (4)C26—C25—H25B109.6
C9—C10—C11121.4 (6)C24—C25—H25B109.6
C9—C10—H10119.3H25A—C25—H25B108.2
C11—C10—H10119.3C25—C26—C27111.0 (6)
C12—C11—C10120.3 (7)C25—C26—H26A109.4
C12—C11—H11119.8C27—C26—H26A109.4
C10—C11—H11119.8C25—C26—H26B109.4
C11—C12—C13120.4 (6)C27—C26—H26B109.4
C11—C12—H12119.8H26A—C26—H26B108.0
C13—C12—H12119.8C26—C27—C28108.4 (5)
C12—C13—C14119.5 (6)C26—C27—H27A110.0
C12—C13—H13120.3C28—C27—H27A110.0
C14—C13—H13120.3C26—C27—H27B110.0
C9—C14—C13119.4 (6)C28—C27—H27B110.0
C9—C14—H14120.3H27A—C27—H27B108.4
C13—C14—H14120.3C27—C28—C24104.7 (4)
O2—C15—N1120.4 (3)C27—C28—H28A110.8
O2—C15—C16118.6 (3)C24—C28—H28A110.8
N1—C15—C16120.9 (3)C27—C28—H28B110.8
C15—C16—H16A109.5C24—C28—H28B110.8
C15—C16—H16B109.5H28A—C28—H28B108.9
H16A—C16—H16B109.5
O1—C1—C2—C3−178.6 (3)C8—N1—C15—O2−175.7 (4)
C6—C1—C2—C3−0.1 (5)C17—N1—C15—C16−173.5 (4)
O1—C1—C2—C8−1.6 (5)C8—N1—C15—C164.4 (6)
C6—C1—C2—C8176.9 (3)C15—N1—C17—C18127.5 (4)
C1—C2—C3—C4−0.1 (6)C8—N1—C17—C18−50.6 (4)
C8—C2—C3—C4−176.9 (3)C15—N1—C17—C24−104.7 (4)
C2—C3—C4—C50.1 (6)C8—N1—C17—C2477.2 (4)
C2—C3—C4—C7179.8 (4)N1—C17—C18—C19−80.3 (5)
C3—C4—C5—C60.0 (7)C24—C17—C18—C19152.2 (4)
C7—C4—C5—C6−179.7 (5)N1—C17—C18—C2395.1 (4)
C4—C5—C6—C1−0.1 (7)C24—C17—C18—C23−32.4 (5)
O1—C1—C6—C5178.6 (4)C23—C18—C19—C20−2.8 (7)
C2—C1—C6—C50.2 (6)C17—C18—C19—C20172.9 (5)
C15—N1—C8—C2−89.0 (4)C23—C18—C19—Cl1179.0 (4)
C17—N1—C8—C288.9 (3)C17—C18—C19—Cl1−5.3 (6)
C15—N1—C8—C943.7 (5)C18—C19—C20—C21−0.2 (9)
C17—N1—C8—C9−138.3 (3)Cl1—C19—C20—C21178.1 (6)
C3—C2—C8—N130.9 (5)C19—C20—C21—C222.6 (12)
C1—C2—C8—N1−145.9 (3)C20—C21—C22—C23−1.8 (12)
C3—C2—C8—C9−102.2 (4)C21—C22—C23—C18−1.5 (9)
C1—C2—C8—C981.0 (4)C19—C18—C23—C223.7 (7)
N1—C8—C9—C10−133.2 (4)C17—C18—C23—C22−171.8 (5)
C2—C8—C9—C10−0.9 (5)N1—C17—C24—C2560.2 (5)
N1—C8—C9—C1449.9 (5)C18—C17—C24—C25−173.7 (4)
C2—C8—C9—C14−177.7 (3)N1—C17—C24—C28175.9 (3)
C14—C9—C10—C11−1.1 (7)C18—C17—C24—C28−58.1 (5)
C8—C9—C10—C11−177.9 (4)C17—C24—C25—C26136.6 (6)
C9—C10—C11—C12−1.7 (9)C28—C24—C25—C2616.2 (7)
C10—C11—C12—C132.9 (10)C24—C25—C26—C27−16.4 (10)
C11—C12—C13—C14−1.4 (10)C25—C26—C27—C289.3 (10)
C10—C9—C14—C132.6 (7)C26—C27—C28—C241.3 (8)
C8—C9—C14—C13179.5 (4)C25—C24—C28—C27−9.9 (6)
C12—C13—C14—C9−1.4 (8)C17—C24—C28—C27−131.6 (5)
C17—N1—C15—O26.4 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.822.637 (3)172

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2646).

References

  • Ali, M. A., Mirza, A. H., Butcher, R. J. & Tarafder, M. T. H. (2002). Inorg. Biochem.92, 141–148. [PubMed]
  • Bruker (1999). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Calligaris, M., Nardin, G. & Randaccio, L. (1972). Coord. Chem. Rev.7, 385–403.
  • Cukurovali, A., Yilmaz, I., Ozmen, H. & Ahmedzade, M. (2002). Transition Met. Chem.27, 171–176.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403–m404. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Gottingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett.16, 2127–2129. [PubMed]
  • Takenaka, N., Huang, Y. & Rawal, V. H. (2002). Tetrahedron, 58, 8299–8305.
  • Varlamov, A. V., Zubkov, F. I., Boltukhina, E. V., Sidorenko, N. V. & Borisov, R. S. (2003). Tetrahedron Lett.44, 3641–3643.
  • Yang, X.-F., Zhang, G.-Y., Zhang, Y., Zhao, J.-Y. & Wang, X.-B. (2005). Acta Cryst. C61, o262–o264. [PubMed]
  • Zhang, G.-Y., Liao, Y.-Q., Wang, Z.-H., Nohira, H. & Hirose, T. (2003). Tetrahedron Asymmetry, 14, 3297–3300.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography