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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1427.
Published online 2008 July 9. doi:  10.1107/S160053680802045X
PMCID: PMC2962060

3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid–triphenyl­phosphine oxide (1/1)

Abstract

In the title 1:1 adduct, C11H10ClN3O2·C18H15OP, the dihedral angle between the pyridine and pyrazole rings is 10.3 (2)°. The two components of the adduct are linked by an O—H(...)O hydrogen bond.

Related literature

For background, see: Mann et al. (1992 [triangle]).

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Object name is e-64-o1427-scheme1.jpg

Experimental

Crystal data

  • C11H10ClN3O2·C18H15OP
  • M r = 529.94
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1427-efi1.jpg
  • a = 16.6694 (14) Å
  • b = 9.8176 (11) Å
  • c = 18.272 (2) Å
  • β = 116.089 (2)°
  • V = 2685.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 (2) K
  • 0.23 × 0.18 × 0.09 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.947, T max = 0.979
  • 13279 measured reflections
  • 4721 independent reflections
  • 2333 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.083
  • S = 1.03
  • 4721 reflections
  • 337 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); 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/S160053680802045X/hb2757sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802045X/hb2757Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant No. 20761002). This research was sponsored by the fund of the Talent Highland research program of Guangxi University (grant No. 205121), the Science Foundation of the State Ethnic Affairs Commission (grant No. 07GX05), the Development Foundation Guangxi Research Institute of Chemical Industry, and the Science Foundation of Guangxi University for Nationalities (grant Nos. 0409032, 0409012, 0509ZD047).

supplementary crystallographic information

Comment

Pyrazoles have been investigated extensively, owing to their chelating ability with metal ions and their potentially beneficial biological activities (e.g. Mann et al., 1992). As part of our studies on these compounds, we report here the synthesis and crystal structure of the title compound, (I), (Fig. 1).

In the 3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid molecule, the dihedral angle between the two ring mean planes is 10.3 (2) °. The two components of the adduct interact by way of an O—H···O hydrogen bond (Table 1).

Experimental

3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 251.04 mg) was dissolved in distilled water (15 ml) and triphenylphosphine oxide (0.5 mmol, 139.04 mg) in distilled water (5 ml) was added with stirring at 323 K. The resulting solution was allowed to react for 5 h and was then filtered. Colourless blocks of (I) were obtained by slow evaporation of a water solution over a period of one month (yield 75%). Elemental analysis: found: C 65.71; H 4.73; N 7.94; O 9.06%. calc. for C29H25ClN3O3P: C 65.72; H 4.75; N 7.93; O 9.06%.

Refinement

The C-bound H atoms were positoned geometrically (C—H = 0.93-0.96Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The O-bound H atom was located in a difference map and refined as riding in its as-found relative position with Uiso(H) =1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms. The hydrogen bond is indicated by a double-dashed line.

Crystal data

C11H10ClN3O2·C18H15OPF000 = 1104
Mr = 529.94Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2022 reflections
a = 16.6694 (14) Åθ = 2.3–25.2º
b = 9.8176 (11) ŵ = 0.24 mm1
c = 18.272 (2) ÅT = 298 (2) K
β = 116.089 (2)ºBlock, colourless
V = 2685.7 (5) Å30.23 × 0.18 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer4721 independent reflections
Radiation source: fine-focus sealed tube2333 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
T = 298(2) Kθmax = 25.0º
ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.947, Tmax = 0.979k = −11→11
13279 measured reflectionsl = −11→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083  w = 1/[σ2(Fo2) + (0.0142P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4721 reflectionsΔρmax = 0.18 e Å3
337 parametersΔρmin = −0.27 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
P10.12197 (5)0.76008 (8)0.14024 (4)0.0528 (2)
O30.16936 (11)0.88630 (18)0.18229 (10)0.0645 (5)
C120.18622 (17)0.6094 (3)0.18123 (18)0.0533 (7)
C130.24643 (19)0.6082 (3)0.2624 (2)0.0723 (9)
H130.25380.68550.29410.087*
C140.2960 (2)0.4923 (4)0.2970 (2)0.0887 (11)
H140.33590.49200.35200.106*
C150.2869 (2)0.3793 (4)0.2513 (3)0.0828 (11)
H150.32160.30270.27450.099*
C160.2266 (2)0.3784 (3)0.1711 (2)0.0783 (10)
H160.21900.30030.14000.094*
C170.17677 (19)0.4932 (3)0.13616 (18)0.0683 (9)
H170.13620.49190.08130.082*
C180.01884 (17)0.7409 (3)0.14774 (15)0.0504 (7)
C19−0.0251 (2)0.6190 (3)0.13663 (17)0.0683 (9)
H19−0.00130.54120.12470.082*
C20−0.1048 (2)0.6108 (3)0.14302 (19)0.0800 (10)
H20−0.13390.52770.13620.096*
C21−0.1400 (2)0.7247 (4)0.15932 (19)0.0793 (10)
H21−0.19390.71930.16270.095*
C22−0.0977 (2)0.8459 (4)0.1707 (2)0.0884 (11)
H22−0.12240.92350.18180.106*
C23−0.0169 (2)0.8536 (3)0.16571 (18)0.0732 (9)
H230.01300.93640.17470.088*
C240.09431 (19)0.7625 (3)0.03445 (16)0.0542 (7)
C250.16220 (19)0.7500 (3)0.01058 (19)0.0682 (9)
H250.22030.73380.04960.082*
C260.1448 (2)0.7614 (3)−0.0703 (2)0.0781 (9)
H260.19090.7529−0.08570.094*
C270.0600 (3)0.7849 (3)−0.1274 (2)0.0841 (11)
H270.04820.7926−0.18190.101*
C28−0.0077 (2)0.7974 (3)−0.1057 (2)0.0905 (12)
H28−0.06550.8133−0.14530.109*
C290.0090 (2)0.7866 (3)−0.02499 (19)0.0721 (9)
H29−0.03780.7956−0.01060.086*
O10.29030 (12)1.0307 (2)0.28946 (12)0.0745 (6)
H10.24710.99010.25950.112*
C10.32200 (18)0.9910 (3)0.36492 (19)0.0551 (8)
O20.29977 (14)0.8882 (2)0.38566 (13)0.0925 (7)
C20.38830 (17)1.0884 (3)0.42273 (18)0.0496 (7)
N10.43821 (15)1.1548 (2)0.39350 (13)0.0558 (6)
C30.39748 (18)1.1108 (3)0.49982 (19)0.0620 (8)
Cl10.33173 (5)1.03306 (10)0.53878 (5)0.0911 (3)
C40.4605 (2)1.2043 (4)0.5487 (2)0.0834 (11)
H4A0.46741.22180.60110.100*
C60.49929 (19)1.2413 (3)0.4415 (2)0.0610 (8)
N20.55065 (16)1.3065 (3)0.4085 (2)0.0720 (8)
C50.5116 (2)1.2697 (3)0.5199 (2)0.0819 (10)
H5A0.55421.33260.55210.098*
N30.60429 (19)1.4127 (3)0.45224 (19)0.0929 (10)
C80.5594 (2)1.2799 (4)0.3382 (3)0.0800 (11)
C70.5137 (2)1.1695 (4)0.27913 (19)0.0996 (12)
H7A0.53101.17280.23550.149*
H7B0.45021.18120.25740.149*
H7C0.53021.08300.30610.149*
C90.6186 (3)1.3730 (5)0.3377 (3)0.1022 (15)
H90.638 (2)1.383 (4)0.298 (2)0.123*
C100.6447 (2)1.4513 (4)0.4071 (3)0.0998 (15)
C110.7108 (2)1.5670 (4)0.4364 (3)0.1496 (18)
H11A0.71451.60110.48710.224*
H11B0.69151.63860.39660.224*
H11C0.76851.53490.44430.224*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0495 (5)0.0512 (5)0.0563 (5)0.0002 (4)0.0221 (4)−0.0042 (4)
O30.0573 (12)0.0545 (13)0.0719 (13)−0.0055 (11)0.0194 (10)−0.0128 (10)
C120.0508 (19)0.051 (2)0.060 (2)0.0008 (15)0.0264 (17)−0.0001 (16)
C130.070 (2)0.061 (2)0.075 (2)−0.0039 (19)0.023 (2)0.0053 (19)
C140.073 (3)0.078 (3)0.091 (3)−0.002 (2)0.013 (2)0.023 (2)
C150.067 (2)0.067 (3)0.115 (3)0.013 (2)0.039 (2)0.026 (2)
C160.085 (3)0.059 (3)0.106 (3)0.012 (2)0.056 (2)0.001 (2)
C170.071 (2)0.061 (2)0.075 (2)0.0125 (19)0.0339 (19)0.002 (2)
C180.0521 (17)0.0464 (19)0.0552 (17)−0.0014 (17)0.0259 (14)−0.0045 (16)
C190.066 (2)0.060 (2)0.088 (2)−0.0017 (18)0.0424 (19)−0.0111 (18)
C200.071 (2)0.066 (3)0.112 (3)−0.010 (2)0.049 (2)−0.009 (2)
C210.063 (2)0.080 (3)0.106 (3)−0.001 (2)0.048 (2)−0.004 (2)
C220.079 (3)0.071 (3)0.134 (3)0.010 (2)0.064 (2)−0.011 (2)
C230.070 (2)0.056 (2)0.106 (3)−0.0042 (19)0.050 (2)−0.007 (2)
C240.0568 (19)0.0489 (19)0.0603 (19)−0.0006 (17)0.0288 (17)−0.0004 (16)
C250.069 (2)0.071 (2)0.072 (2)0.0076 (19)0.0368 (18)0.0017 (19)
C260.099 (3)0.073 (2)0.083 (3)0.010 (2)0.059 (2)0.003 (2)
C270.114 (3)0.082 (3)0.063 (2)−0.008 (2)0.044 (3)0.0024 (19)
C280.081 (3)0.118 (3)0.063 (3)−0.008 (2)0.024 (2)0.019 (2)
C290.063 (2)0.088 (3)0.067 (2)0.0002 (19)0.0297 (19)0.0139 (18)
O10.0828 (15)0.0717 (15)0.0631 (14)−0.0256 (12)0.0267 (12)−0.0080 (12)
C10.053 (2)0.054 (2)0.064 (2)−0.0020 (17)0.0309 (18)0.0027 (19)
O20.1069 (18)0.0782 (18)0.0849 (16)−0.0368 (15)0.0353 (13)0.0044 (14)
C20.0451 (18)0.0485 (19)0.055 (2)−0.0011 (15)0.0213 (16)0.0003 (15)
N10.0491 (15)0.0534 (17)0.0658 (17)−0.0057 (13)0.0262 (14)0.0016 (13)
C30.055 (2)0.072 (2)0.062 (2)−0.0038 (18)0.0289 (17)0.0020 (18)
Cl10.0865 (6)0.1195 (8)0.0837 (6)−0.0107 (6)0.0526 (5)0.0067 (5)
C40.076 (2)0.103 (3)0.069 (2)−0.014 (2)0.030 (2)−0.018 (2)
C60.0494 (19)0.054 (2)0.076 (2)−0.0038 (17)0.0248 (18)0.005 (2)
N20.0549 (17)0.061 (2)0.098 (2)−0.0123 (14)0.0318 (17)0.0078 (17)
C50.069 (2)0.085 (3)0.085 (3)−0.023 (2)0.027 (2)−0.023 (2)
N30.067 (2)0.059 (2)0.149 (3)−0.0130 (16)0.044 (2)−0.0033 (19)
C80.059 (2)0.084 (3)0.098 (3)−0.001 (2)0.035 (2)0.033 (2)
C70.089 (3)0.140 (4)0.075 (2)−0.018 (3)0.041 (2)0.011 (2)
C90.070 (3)0.104 (4)0.136 (5)0.001 (3)0.049 (3)0.050 (3)
C100.062 (3)0.065 (3)0.171 (5)−0.003 (2)0.050 (3)0.030 (3)
C110.094 (3)0.076 (3)0.276 (6)−0.028 (3)0.079 (3)0.018 (3)

Geometric parameters (Å, °)

P1—O31.4887 (17)C27—H270.9300
P1—C241.779 (3)C28—C291.379 (4)
P1—C121.786 (3)C28—H280.9300
P1—C181.794 (3)C29—H290.9300
C12—C171.376 (4)O1—C11.301 (3)
C12—C131.378 (3)O1—H10.7941
C13—C141.384 (4)C1—O21.193 (3)
C13—H130.9300C1—C21.492 (4)
C14—C151.356 (4)C2—N11.339 (3)
C14—H140.9300C2—C31.366 (3)
C15—C161.364 (4)N1—C61.320 (3)
C15—H150.9300C3—C41.385 (4)
C16—C171.378 (4)C3—Cl11.725 (3)
C16—H160.9300C4—C51.344 (4)
C17—H170.9300C4—H4A0.9300
C18—C231.364 (3)C6—C51.385 (4)
C18—C191.371 (3)C6—N21.400 (3)
C19—C201.385 (3)N2—N31.377 (3)
C19—H190.9300N2—C81.379 (4)
C20—C211.355 (4)C5—H5A0.9300
C20—H200.9300N3—C101.330 (4)
C21—C221.351 (4)C8—C91.348 (5)
C21—H210.9300C8—C71.483 (4)
C22—C231.391 (4)C7—H7A0.9600
C22—H220.9300C7—H7B0.9600
C23—H230.9300C7—H7C0.9600
C24—C291.378 (3)C9—C101.379 (5)
C24—C251.386 (3)C9—H90.93 (3)
C25—C261.380 (3)C10—C111.507 (5)
C25—H250.9300C11—H11A0.9600
C26—C271.358 (4)C11—H11B0.9600
C26—H260.9300C11—H11C0.9600
C27—C281.356 (4)
O3—P1—C24112.01 (12)C26—C27—H27119.7
O3—P1—C12112.87 (12)C27—C28—C29120.2 (3)
C24—P1—C12106.73 (14)C27—C28—H28119.9
O3—P1—C18110.91 (12)C29—C28—H28119.9
C24—P1—C18106.58 (13)C24—C29—C28120.6 (3)
C12—P1—C18107.40 (13)C24—C29—H29119.7
C17—C12—C13118.3 (3)C28—C29—H29119.7
C17—C12—P1123.1 (2)C1—O1—H1113.8
C13—C12—P1118.5 (2)O2—C1—O1123.5 (3)
C12—C13—C14120.3 (3)O2—C1—C2123.7 (3)
C12—C13—H13119.8O1—C1—C2112.8 (3)
C14—C13—H13119.8N1—C2—C3121.7 (3)
C15—C14—C13120.6 (3)N1—C2—C1115.2 (3)
C15—C14—H14119.7C3—C2—C1123.0 (3)
C13—C14—H14119.7C6—N1—C2118.8 (3)
C14—C15—C16119.7 (4)C2—C3—C4118.7 (3)
C14—C15—H15120.1C2—C3—Cl1123.4 (3)
C16—C15—H15120.1C4—C3—Cl1117.8 (3)
C15—C16—C17120.1 (3)C5—C4—C3119.7 (3)
C15—C16—H16119.9C5—C4—H4A120.1
C17—C16—H16119.9C3—C4—H4A120.1
C12—C17—C16120.9 (3)N1—C6—C5122.5 (3)
C12—C17—H17119.5N1—C6—N2116.6 (3)
C16—C17—H17119.5C5—C6—N2120.9 (3)
C23—C18—C19118.8 (3)N3—N2—C8112.1 (3)
C23—C18—P1117.9 (2)N3—N2—C6117.4 (3)
C19—C18—P1123.3 (2)C8—N2—C6130.5 (3)
C18—C19—C20120.5 (3)C4—C5—C6118.6 (3)
C18—C19—H19119.7C4—C5—H5A120.7
C20—C19—H19119.7C6—C5—H5A120.7
C21—C20—C19119.6 (3)C10—N3—N2103.4 (3)
C21—C20—H20120.2C9—C8—N2104.8 (4)
C19—C20—H20120.2C9—C8—C7129.3 (5)
C22—C21—C20120.9 (3)N2—C8—C7125.8 (3)
C22—C21—H21119.5C8—C7—H7A109.5
C20—C21—H21119.5C8—C7—H7B109.5
C21—C22—C23119.4 (3)H7A—C7—H7B109.5
C21—C22—H22120.3C8—C7—H7C109.5
C23—C22—H22120.3H7A—C7—H7C109.5
C18—C23—C22120.7 (3)H7B—C7—H7C109.5
C18—C23—H23119.7C8—C9—C10107.9 (4)
C22—C23—H23119.7C8—C9—H9126 (2)
C29—C24—C25118.0 (3)C10—C9—H9126 (2)
C29—C24—P1122.9 (2)N3—C10—C9111.7 (4)
C25—C24—P1118.9 (2)N3—C10—C11119.0 (5)
C26—C25—C24121.0 (3)C9—C10—C11129.3 (5)
C26—C25—H25119.5C10—C11—H11A109.5
C24—C25—H25119.5C10—C11—H11B109.5
C27—C26—C25119.6 (3)H11A—C11—H11B109.5
C27—C26—H26120.2C10—C11—H11C109.5
C25—C26—H26120.2H11A—C11—H11C109.5
C28—C27—C26120.7 (3)H11B—C11—H11C109.5
C28—C27—H27119.7
O3—P1—C12—C17−152.2 (2)C26—C27—C28—C290.2 (5)
C24—P1—C12—C17−28.7 (3)C25—C24—C29—C280.2 (5)
C18—P1—C12—C1785.2 (3)P1—C24—C29—C28175.2 (2)
O3—P1—C12—C1329.6 (3)C27—C28—C29—C24−0.3 (5)
C24—P1—C12—C13153.1 (2)O2—C1—C2—N1147.7 (3)
C18—P1—C12—C13−92.9 (2)O1—C1—C2—N1−32.9 (3)
C17—C12—C13—C140.2 (4)O2—C1—C2—C3−33.1 (4)
P1—C12—C13—C14178.5 (2)O1—C1—C2—C3146.3 (3)
C12—C13—C14—C150.8 (5)C3—C2—N1—C61.8 (4)
C13—C14—C15—C16−1.8 (5)C1—C2—N1—C6−179.0 (2)
C14—C15—C16—C171.7 (5)N1—C2—C3—C4−0.3 (4)
C13—C12—C17—C16−0.3 (4)C1—C2—C3—C4−179.4 (3)
P1—C12—C17—C16−178.5 (2)N1—C2—C3—Cl1177.3 (2)
C15—C16—C17—C12−0.6 (5)C1—C2—C3—Cl1−1.9 (4)
O3—P1—C18—C2319.5 (3)C2—C3—C4—C5−0.7 (5)
C24—P1—C18—C23−102.6 (2)Cl1—C3—C4—C5−178.4 (3)
C12—P1—C18—C23143.3 (2)C2—N1—C6—C5−2.4 (4)
O3—P1—C18—C19−160.2 (2)C2—N1—C6—N2179.0 (2)
C24—P1—C18—C1977.6 (3)N1—C6—N2—N3169.7 (2)
C12—P1—C18—C19−36.5 (3)C5—C6—N2—N3−8.9 (4)
C23—C18—C19—C200.4 (4)N1—C6—N2—C8−12.4 (4)
P1—C18—C19—C20−179.8 (2)C5—C6—N2—C8168.9 (3)
C18—C19—C20—C210.9 (5)C3—C4—C5—C60.2 (5)
C19—C20—C21—C22−1.0 (5)N1—C6—C5—C41.4 (5)
C20—C21—C22—C23−0.1 (5)N2—C6—C5—C4180.0 (3)
C19—C18—C23—C22−1.6 (5)C8—N2—N3—C100.8 (3)
P1—C18—C23—C22178.7 (2)C6—N2—N3—C10179.1 (3)
C21—C22—C23—C181.4 (5)N3—N2—C8—C9−1.0 (4)
O3—P1—C24—C29−104.1 (3)C6—N2—C8—C9−178.9 (3)
C12—P1—C24—C29131.9 (3)N3—N2—C8—C7177.7 (3)
C18—P1—C24—C2917.3 (3)C6—N2—C8—C7−0.2 (5)
O3—P1—C24—C2570.8 (3)N2—C8—C9—C100.8 (4)
C12—P1—C24—C25−53.2 (3)C7—C8—C9—C10−177.9 (3)
C18—P1—C24—C25−167.7 (2)N2—N3—C10—C9−0.3 (4)
C29—C24—C25—C260.0 (4)N2—N3—C10—C11−179.4 (3)
P1—C24—C25—C26−175.2 (2)C8—C9—C10—N3−0.3 (5)
C24—C25—C26—C27−0.1 (5)C8—C9—C10—C11178.7 (3)
C25—C26—C27—C280.0 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O30.791.762.537 (2)165

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2757).

References

  • Mann, F., Chiment, F., Balasco, A., Cenicola, M. L., Amico, M. D., Parrilo, C., Rossi, F. & Marmo, E. (1992). Eur. J. Med. Chem.27, 633–639.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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