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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 7| July 2009| Pages o1503-o1504

4-Hydr­­oxy-N′-(3,5-di­chloro-2-hy­droxy­benzyl­­idene)benzohydrazide

aDepartment of Chemistry and Chemical Engineering, Zaozhuang University, Zaozhuang Shandong 277160, People's Republic of China
*Correspondence e-mail: renchonggui@163.com

(Received 25 May 2009; accepted 2 June 2009; online 6 June 2009)

In the title compound, C14H10Cl2N2O3, the dihedral angle between the two benzene rings is 5.1 (2)°. The mol­ecule adopts an E configuration with respect to the C=N bond and an intra­molecular O—H⋯N inter­action is present. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999[Jeewoth, T., Bhowon, M. G. & Wah, H. L. K. (1999). Transition Met. Chem. 24, 445-448.]); Ren et al. (2002[Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.]); Eltayeb et al. (2008[Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.]); Sinha et al. (2008[Sinha, D., Tiwari, A. K., Singh, S., Shukla, G., Mishra, P., Chandra, H. & Mishra, A. K. (2008). Eur. J. Med. Chem. 43, 160-165.]). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008[Shivakumar, K., Shashidhar, T., Reddy, P. V. & Halli, M. B. (2008). J. Coord. Chem. 61, 2274-2287.]); Prabhakaran et al. (2006[Prabhakaran, R., Huang, R. & Natarajan, K. (2006). Inorg. Chim. Acta, 359, 3359-3362.]); Dhar et al. (2005[Dhar, S., Nethaji, M. & Chakravarty, A. R. (2005). Inorg. Chim. Acta, 358, 2437-2444.]). For related structures, see: Cui et al. (2007[Cui, J.-C., Pan, Q.-X., Yin, H.-D. & Qiao, Y.-L. (2007). Acta Cryst. E63, o2633.]); Jing et al. (2007[Jing, Z.-L., Yu, M. & Chen, X. (2007). Acta Cryst. E63, o4902.]); Ma et al. (2008[Ma, H.-B., Huang, S.-S. & Diao, Y.-P. (2008). Acta Cryst. E64, o210.]); Salhin et al. (2007[Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880.]); Lin et al. (2007[Lin, X.-C., Yin, H. & Lin, Y. (2007). Acta Cryst. E63, o2864.]); Alhadi et al. (2008[Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584.]); Xue et al. (2008[Xue, L.-W., Han, Y.-J., Hao, C.-J., Zhao, G.-Q. & Liu, Q.-R. (2008). Acta Cryst. E64, o1938.]); Wang et al. (2008[Wang, X.-Y., Cao, G.-B. & Yang, T. (2008). Acta Cryst. E64, o2022.]); Lu (2008[Lu, J.-F. (2008). Acta Cryst. E64, o2032.]); Diao et al. (2008[Diao, Y.-P., Huang, S.-S., Zhang, H.-L. & Kang, T.-G. (2008). Z. Kristallogr. New Cryst. Struct. 223, 165-166.]); Qiu (2009[Qiu, X.-Y. (2009). Z. Kristallogr. New Cryst. Struct. 224, 109-110.]); Mohd Lair et al. (2009a[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, o189.],b[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009b). Acta Cryst. E65, o190.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Cl2N2O3

  • Mr = 325.14

  • Monoclinic, P 21 /c

  • a = 8.030 (1) Å

  • b = 13.546 (2) Å

  • c = 13.433 (2) Å

  • β = 107.247 (2)°

  • V = 1395.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.48 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.911, Tmax = 0.919

  • 8463 measured reflections

  • 3039 independent reflections

  • 2324 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.107

  • S = 1.03

  • 3039 reflections

  • 195 parameters

  • 1 restraint

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

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.82 1.90 2.6164 (19) 145
O3—H3⋯O2i 0.82 1.85 2.658 (2) 168
N2—H2⋯O3ii 0.899 (10) 2.204 (16) 3.000 (2) 147 (2)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. 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: SHELXL97.

Supporting information


Comment top

The Schiff base compounds show excellent biological properties (Jeewoth et al., 1999; Ren et al., 2002; Eltayeb et al., 2008; Sinha et al., 2008). Moreover, the Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006; Dhar et al., 2005). We report here the crystal structure of the title compound. In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 5.1 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and comparable to those in other similar compounds (Cui et al., 2007; Jing et al., 2007; Ma et al., 2008; Salhin et al., 2007; Lin et al., 2007; Alhadi et al., 2008; Xue et al., 2008; Wang et al., 2008; Lu, 2008; Diao et al., 2008; Qiu, 2009; Mohd Lair et al., 2009a,b). —H···N OIn the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), Fig. 2.

Related literature top

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999); Ren et al. (2002); Eltayeb et al. (2008); Sinha et al. (2008). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008); Prabhakaran et al. (2006); Dhar et al. (2005). For related structures, see: Cui et al. (2007); Jing et al. (2007); Ma et al. (2008); Salhin et al. (2007); Lin et al. (2007); Alhadi et al. (2008); Xue et al. (2008); Wang et al. (2008); Lu (2008); Diao et al. (2008); Qiu (2009); Mohd Lair et al. (2009a,b). For reference structural data, see: Allen et al. (1987).

Experimental top

All the starting materials were obtained with AR grade from Lancaster. 3,5-Dichloro-2-hydroxybenzaldehyde (1.0 mmol, 192.2 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152.2 mg) were refluxed in 30 ml methanol solution for 30 min giving a clear yellow solution. Yellow block-shaped single crystals of the compound were obtained by slow evaporation of the solution for a week at room temperature.

Refinement top

H2 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å, and with Uiso restrained to 0.08 Å2. Other H atoms were constrained to ideal geometries, with d(C–H) = 0.93 Å, d(O–H) = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the compound with 30% probability ellipsoids. The intramolecular O–H···N hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. Molecular packing of the compound with hydrogen bonds drawn as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.
(I) top
Crystal data top
C14H10Cl2N2O3F(000) = 664
Mr = 325.14Dx = 1.547 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2634 reflections
a = 8.030 (1) Åθ = 2.2–26.0°
b = 13.546 (2) ŵ = 0.48 mm1
c = 13.433 (2) ÅT = 298 K
β = 107.247 (2)°Block, yellow
V = 1395.5 (3) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3039 independent reflections
Radiation source: fine-focus sealed tube2324 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.911, Tmax = 0.919k = 1717
8463 measured reflectionsl = 1714
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.3954P]
where P = (Fo2 + 2Fc2)/3
3039 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.36 e Å3
Crystal data top
C14H10Cl2N2O3V = 1395.5 (3) Å3
Mr = 325.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.030 (1) ŵ = 0.48 mm1
b = 13.546 (2) ÅT = 298 K
c = 13.433 (2) Å0.20 × 0.20 × 0.18 mm
β = 107.247 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3039 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2324 reflections with I > 2σ(I)
Tmin = 0.911, Tmax = 0.919Rint = 0.023
8463 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.22 e Å3
3039 reflectionsΔρmin = 0.36 e Å3
195 parameters
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
Cl10.05205 (8)0.19042 (4)1.13049 (5)0.0682 (2)
Cl20.17799 (11)0.43904 (5)1.45283 (5)0.0843 (2)
N10.25047 (18)0.49746 (11)1.00303 (11)0.0382 (3)
N20.31078 (19)0.56552 (10)0.94624 (11)0.0387 (3)
O10.08301 (19)0.33479 (10)1.01678 (10)0.0512 (3)
H10.13140.37450.98850.077*
O20.26379 (19)0.45814 (10)0.81320 (10)0.0540 (4)
O30.55673 (19)0.80001 (10)0.59831 (10)0.0512 (3)
H30.62000.84330.63220.077*
C10.1834 (2)0.45241 (12)1.15726 (13)0.0369 (4)
C20.1046 (2)0.36288 (13)1.11609 (14)0.0384 (4)
C30.0458 (2)0.30054 (13)1.18096 (15)0.0422 (4)
C40.0667 (2)0.32330 (14)1.28362 (15)0.0467 (5)
H40.02750.28041.32590.056*
C50.1470 (3)0.41115 (15)1.32275 (14)0.0479 (5)
C60.2037 (2)0.47558 (14)1.26095 (14)0.0436 (4)
H60.25580.53481.28850.052*
C70.2478 (2)0.52136 (13)1.09426 (13)0.0388 (4)
H70.28730.58331.12080.047*
C80.3119 (2)0.54031 (13)0.84892 (13)0.0366 (4)
C90.3736 (2)0.61545 (12)0.78824 (13)0.0354 (4)
C100.3425 (3)0.59603 (15)0.68236 (14)0.0468 (4)
H100.27990.54000.65320.056*
C110.4035 (3)0.65890 (16)0.62059 (14)0.0497 (5)
H110.38150.64540.55000.060*
C120.4974 (2)0.74196 (13)0.66340 (13)0.0402 (4)
C130.5276 (2)0.76339 (13)0.76825 (13)0.0404 (4)
H130.58930.81990.79690.049*
C140.4656 (2)0.70024 (13)0.82994 (13)0.0383 (4)
H140.48560.71470.90020.046*
H20.352 (3)0.6232 (11)0.9766 (18)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0753 (4)0.0500 (3)0.0806 (4)0.0224 (3)0.0252 (3)0.0019 (3)
Cl20.1359 (6)0.0822 (5)0.0491 (3)0.0081 (4)0.0492 (4)0.0052 (3)
N10.0398 (8)0.0373 (7)0.0391 (8)0.0010 (6)0.0143 (6)0.0045 (6)
N20.0462 (8)0.0364 (8)0.0361 (8)0.0036 (6)0.0165 (7)0.0022 (6)
O10.0629 (9)0.0480 (8)0.0433 (7)0.0110 (6)0.0165 (6)0.0057 (6)
O20.0730 (10)0.0428 (7)0.0462 (8)0.0120 (7)0.0174 (7)0.0068 (6)
O30.0679 (10)0.0503 (8)0.0392 (7)0.0019 (6)0.0218 (7)0.0104 (6)
C10.0357 (9)0.0358 (9)0.0422 (9)0.0033 (7)0.0160 (7)0.0027 (7)
C20.0340 (9)0.0394 (9)0.0421 (9)0.0042 (7)0.0117 (7)0.0021 (7)
C30.0347 (9)0.0383 (9)0.0543 (11)0.0006 (7)0.0140 (8)0.0040 (8)
C40.0438 (10)0.0478 (11)0.0553 (11)0.0066 (8)0.0249 (9)0.0130 (9)
C50.0563 (12)0.0525 (11)0.0413 (10)0.0068 (9)0.0241 (9)0.0032 (8)
C60.0500 (11)0.0404 (9)0.0452 (10)0.0000 (8)0.0212 (9)0.0030 (8)
C70.0399 (9)0.0355 (9)0.0427 (10)0.0012 (7)0.0147 (8)0.0003 (7)
C80.0359 (9)0.0382 (9)0.0343 (9)0.0031 (7)0.0080 (7)0.0008 (7)
C90.0345 (9)0.0392 (9)0.0326 (8)0.0059 (7)0.0102 (7)0.0010 (7)
C100.0527 (11)0.0510 (11)0.0347 (9)0.0067 (9)0.0098 (8)0.0043 (8)
C110.0588 (12)0.0615 (12)0.0276 (9)0.0009 (10)0.0107 (8)0.0009 (8)
C120.0453 (10)0.0419 (10)0.0351 (9)0.0116 (8)0.0144 (7)0.0106 (7)
C130.0468 (10)0.0376 (9)0.0373 (9)0.0016 (8)0.0132 (8)0.0003 (7)
C140.0453 (10)0.0412 (9)0.0299 (8)0.0037 (7)0.0135 (7)0.0014 (7)
Geometric parameters (Å, º) top
Cl1—C31.7281 (19)C4—C51.381 (3)
Cl2—C51.7321 (19)C4—H40.9300
N1—C71.274 (2)C5—C61.372 (3)
N1—N21.3732 (19)C6—H60.9300
N2—C81.354 (2)C7—H70.9300
N2—H20.899 (10)C8—C91.478 (2)
O1—C21.348 (2)C9—C141.390 (2)
O1—H10.8200C9—C101.394 (2)
O2—C81.228 (2)C10—C111.376 (3)
O3—C121.363 (2)C10—H100.9300
O3—H30.8200C11—C121.381 (3)
C1—C61.389 (2)C11—H110.9300
C1—C21.403 (2)C12—C131.387 (2)
C1—C71.455 (2)C13—C141.383 (2)
C2—C31.393 (2)C13—H130.9300
C3—C41.374 (3)C14—H140.9300
C7—N1—N2118.23 (15)N1—C7—C1120.45 (16)
C8—N2—N1118.12 (14)N1—C7—H7119.8
C8—N2—H2123.3 (16)C1—C7—H7119.8
N1—N2—H2118.5 (16)O2—C8—N2120.98 (16)
C2—O1—H1109.5O2—C8—C9121.77 (15)
C12—O3—H3109.5N2—C8—C9117.26 (15)
C6—C1—C2119.72 (16)C14—C9—C10118.68 (16)
C6—C1—C7118.80 (16)C14—C9—C8124.85 (15)
C2—C1—C7121.47 (15)C10—C9—C8116.40 (16)
O1—C2—C3118.68 (16)C11—C10—C9120.67 (18)
O1—C2—C1123.01 (16)C11—C10—H10119.7
C3—C2—C1118.30 (16)C9—C10—H10119.7
C4—C3—C2121.93 (17)C10—C11—C12120.06 (16)
C4—C3—Cl1119.57 (14)C10—C11—H11120.0
C2—C3—Cl1118.49 (15)C12—C11—H11120.0
C3—C4—C5118.66 (17)O3—C12—C11117.03 (15)
C3—C4—H4120.7O3—C12—C13122.78 (17)
C5—C4—H4120.7C11—C12—C13120.19 (16)
C6—C5—C4121.27 (17)C14—C13—C12119.56 (17)
C6—C5—Cl2119.84 (16)C14—C13—H13120.2
C4—C5—Cl2118.89 (15)C12—C13—H13120.2
C5—C6—C1120.10 (17)C13—C14—C9120.82 (15)
C5—C6—H6120.0C13—C14—H14119.6
C1—C6—H6120.0C9—C14—H14119.6
C7—N1—N2—C8179.36 (15)C6—C1—C7—N1171.54 (16)
C6—C1—C2—O1178.94 (16)C2—C1—C7—N17.3 (3)
C7—C1—C2—O10.1 (3)N1—N2—C8—O21.5 (2)
C6—C1—C2—C31.3 (2)N1—N2—C8—C9178.67 (14)
C7—C1—C2—C3179.91 (16)O2—C8—C9—C14164.75 (17)
O1—C2—C3—C4178.59 (17)N2—C8—C9—C1415.1 (2)
C1—C2—C3—C41.6 (3)O2—C8—C9—C1012.3 (2)
O1—C2—C3—Cl10.0 (2)N2—C8—C9—C10167.92 (16)
C1—C2—C3—Cl1179.75 (13)C14—C9—C10—C110.8 (3)
C2—C3—C4—C50.6 (3)C8—C9—C10—C11176.42 (17)
Cl1—C3—C4—C5179.25 (14)C9—C10—C11—C120.3 (3)
C3—C4—C5—C60.7 (3)C10—C11—C12—O3178.78 (17)
C3—C4—C5—Cl2178.61 (15)C10—C11—C12—C131.3 (3)
C4—C5—C6—C11.0 (3)O3—C12—C13—C14179.03 (16)
Cl2—C5—C6—C1178.29 (14)C11—C12—C13—C141.0 (3)
C2—C1—C6—C50.0 (3)C12—C13—C14—C90.1 (3)
C7—C1—C6—C5178.85 (16)C10—C9—C14—C131.0 (3)
N2—N1—C7—C1179.32 (14)C8—C9—C14—C13175.92 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.6164 (19)145
O3—H3···O2i0.821.852.658 (2)168
N2—H2···O3ii0.90 (1)2.20 (2)3.000 (2)147 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H10Cl2N2O3
Mr325.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)8.030 (1), 13.546 (2), 13.433 (2)
β (°) 107.247 (2)
V3)1395.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.48
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.911, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections
8463, 3039, 2324
Rint0.023
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.107, 1.03
No. of reflections3039
No. of parameters195
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.36

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.6164 (19)145
O3—H3···O2i0.821.852.658 (2)168
N2—H2···O3ii0.899 (10)2.204 (16)3.000 (2)147 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+3/2, z+1/2.
 

Acknowledgements

The author acknowledges Zaozhuang University for funding this study.

References

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Volume 65| Part 7| July 2009| Pages o1503-o1504
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