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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o905–o906.
Published online 2009 March 28. doi:  10.1107/S1600536809010964
PMCID: PMC2968873

3-Bromo-N′-(2-hydr­oxy-3,5-diiodo­benzyl­idene)benzohydrazide monohydrate

Abstract

Crystals of the title compound, C14H9BrI2N2O2·H2O, were obtained from a condensation reaction of 3-bromo­benzohydrazide with 3,5-diiodo­salicylaldehyde. The Schiff base mol­ecule assumes an E configuration with respect to the C=N bond, and the dihedral angle between the two benzene rings is 6.9 (2)°. An intra­molecular O—H(...)N hydrogen bond is observed in the Schiff base mol­ecule and may contribute to its overall near planarity. In the crystal structure, mol­ecules are linked through inter­molecular O—H(...)O and N—H(...)O hydrogen bonds, forming layers parallel to the bc plane. Short inter­molecular I(...)O contacts [2.930 (5) Å] are also found, linking the mol­ecules into zigzag chains along b.

Related literature

For the biological activity of Schiff bases, see: Bedia et al. (2006 [triangle]); Richardson & Bernhardt (1999 [triangle]); Koh et al. (1998 [triangle]); Prasad et al. (2007 [triangle]). For metal complexes of Schiff bases, see: Adams et al. (2000 [triangle]); Ainscough et al. (1998 [triangle]); Roth et al. (2007 [triangle]). For related structures, see: Fun et al. (2008 [triangle]); Butcher et al. (2007 [triangle]); Zhi & Yang (2007 [triangle]); Ejsmont et al. (2008 [triangle]); Yathirajan et al. (2007 [triangle]); Narayana et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For short inter­molecular I(...)O contacts, see, for example: Britton (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o905-scheme1.jpg

Experimental

Crystal data

  • C14H9BrI2N2O2·H2O
  • M r = 588.96
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o905-efi1.jpg
  • a = 15.181 (3) Å
  • b = 7.611 (2) Å
  • c = 15.516 (3) Å
  • β = 110.628 (3)°
  • V = 1677.8 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 6.14 mm−1
  • T = 298 K
  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.261, T max = 0.293
  • 13552 measured reflections
  • 3656 independent reflections
  • 2651 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.090
  • S = 1.00
  • 3656 reflections
  • 209 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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 global, I. DOI: 10.1107/S1600536809010964/sj2600sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010964/sj2600Isup2.hkl

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

Acknowledgments

We are grateful for financial support of this work from the Natural Science Foundation of Hunan Province, People’s Republic of China (Project No. 07 J J6023).

supplementary crystallographic information

Comment

Schiff bases have been demonstrated to possess interesting biological activities (Bedia et al., 2006; Richardson & Bernhardt, 1999; Koh et al., 1998; Prasad et al., 2007). These compounds have been widely used as versatile ligands in coordination chemistry (Adams et al., 2000; Ainscough et al., 1998; Roth et al., 2007). Recently, the crystal structures of such compounds have been extensively reported (Fun et al., 2008; Butcher et al., 2007; Zhi & Yang, 2007). In this paper, the new title Schiff base, (I), Fig. 1, is reported.

The asymmetric unit of (I) contains a Schiff base molecule and a water molecule of crystallization. The Schiff base molecule assumes an E configuration with respect to the C═N bond. The dihedral angle between the two benzene rings is 6.9 (2)°, indicating that the molecule is essentially planar. An intramolecular O—H···N hydrogen bond is observed in the Schiff base molecule and may contribute to its overall planarity. All bond lengths in (I) are within normal ranges (Allen et al., 1987) and comparable to the corresponding values in other similar compounds (Ejsmont et al., 2008; Yathirajan et al., 2007; Narayana et al., 2007).

In the crystal structure, molecules are linked through intermolecular O–H···O and N–H···O (Table 1) hydrogen bonds, forming layers parallel to the bc plane (Fig. 2). Additional short intermolecular I1···O12i contacts, 2.930 (5)Å, i = 1-x, -1/2+y, 1/2+z, are also observed linking molecules into zig-zag chains along b. Similar short I···O contacts have been reported previously (Britton, 2003).

Experimental

3-Bromobenzohydrazide (1.0 mmol, 215.2 mg) and 3,5-diiodosalicylaldehyde (1.0 mmol, 374.9 mg) were stirred at room temperature for two hours. The filtrate was kept in air for a week to obtain yellow block-shaped crystals of (I).

Refinement

Atoms H2, H3A and H3B were located in a difference Fourier map and refined isotropically, with the N–H, O–H, and H···H distances restrained to 0.90 (1), 0.85 (1), and 1.37 (2) Å, respectively. Other H atoms were positioned geometrically and refined using a riding model with d(C–H) = 0.93 Å, d(O–H) = 0.82 Å and Uiso = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I), with 30% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.
Fig. 2.
Molecular packing of (I), viewed along the b axis. H atoms not involved in the interactions have been omitted for clarity. Intermolecular hydrogen bonds and short I···O contacts are shown as dashed lines.

Crystal data

C14H9BrI2N2O2·H2OF(000) = 1096
Mr = 588.96Dx = 2.331 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2004 reflections
a = 15.181 (3) Åθ = 2.6–24.5°
b = 7.611 (2) ŵ = 6.14 mm1
c = 15.516 (3) ÅT = 298 K
β = 110.628 (3)°Block, yellow
V = 1677.8 (6) Å30.23 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer3656 independent reflections
Radiation source: fine-focus sealed tube2651 reflections with I > 2σ(I)
graphiteRint = 0.059
ω scansθmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −19→19
Tmin = 0.261, Tmax = 0.293k = −9→9
13552 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0296P)2] where P = (Fo2 + 2Fc2)/3
3656 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.63 e Å3
4 restraintsΔρmin = −0.69 e Å3

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
I10.32291 (3)−0.01495 (5)0.20582 (3)0.04369 (14)
I20.14532 (3)−0.04420 (6)0.49489 (3)0.04849 (15)
Br11.04870 (5)0.64844 (11)0.62538 (6)0.0699 (3)
O10.4774 (3)0.1800 (5)0.3704 (2)0.0362 (9)
H10.52120.21900.41400.054*
O20.6948 (3)0.4091 (6)0.4847 (3)0.0465 (11)
O30.4178 (4)0.0028 (7)0.7467 (3)0.0636 (14)
N10.5549 (3)0.3106 (5)0.5331 (3)0.0303 (10)
N20.6303 (3)0.3938 (6)0.5939 (3)0.0318 (10)
C10.4070 (4)0.1717 (7)0.4882 (4)0.0301 (12)
C20.4058 (4)0.1324 (6)0.3995 (3)0.0260 (11)
C30.3290 (4)0.0455 (7)0.3393 (4)0.0314 (12)
C40.2549 (4)−0.0061 (7)0.3655 (4)0.0312 (13)
H40.2040−0.06600.32440.037*
C50.2572 (4)0.0324 (7)0.4540 (4)0.0333 (13)
C60.3317 (4)0.1209 (7)0.5138 (4)0.0325 (13)
H60.33230.14760.57240.039*
C70.4852 (4)0.2632 (7)0.5544 (4)0.0323 (13)
H70.48440.28720.61290.039*
C80.7013 (4)0.4386 (7)0.5641 (4)0.0304 (12)
C90.7872 (4)0.5200 (6)0.6326 (4)0.0301 (12)
C100.8620 (4)0.5467 (7)0.6036 (4)0.0389 (14)
H100.85760.51400.54440.047*
C110.9424 (4)0.6211 (8)0.6616 (4)0.0429 (15)
C120.9500 (4)0.6747 (9)0.7478 (5)0.0530 (17)
H121.00520.72690.78630.064*
C130.8755 (4)0.6511 (8)0.7772 (4)0.0489 (16)
H130.88020.68840.83570.059*
C140.7934 (5)0.5721 (7)0.7204 (4)0.0422 (15)
H140.74330.55430.74070.051*
H20.626 (5)0.411 (9)0.649 (2)0.080*
H3A0.414 (6)−0.082 (4)0.709 (3)0.080*
H3B0.414 (5)0.097 (3)0.717 (3)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.0401 (3)0.0640 (3)0.0293 (2)−0.00844 (19)0.01519 (18)−0.01025 (18)
I20.0423 (3)0.0602 (3)0.0522 (3)−0.0090 (2)0.0281 (2)−0.0014 (2)
Br10.0381 (4)0.0888 (6)0.0902 (6)−0.0056 (4)0.0317 (4)0.0133 (5)
O10.029 (2)0.054 (3)0.027 (2)−0.0065 (19)0.0114 (18)−0.0023 (18)
O20.047 (3)0.067 (3)0.025 (2)−0.009 (2)0.013 (2)−0.004 (2)
O30.062 (3)0.079 (3)0.058 (3)0.014 (3)0.031 (3)0.017 (3)
N10.024 (2)0.032 (2)0.030 (3)0.0035 (19)0.003 (2)0.000 (2)
N20.026 (3)0.042 (3)0.026 (3)−0.005 (2)0.007 (2)−0.005 (2)
C10.027 (3)0.032 (3)0.029 (3)−0.001 (2)0.008 (2)0.004 (2)
C20.028 (3)0.030 (3)0.021 (3)0.004 (2)0.009 (2)0.003 (2)
C30.037 (3)0.033 (3)0.026 (3)0.001 (3)0.012 (3)−0.003 (2)
C40.025 (3)0.041 (3)0.027 (3)−0.006 (2)0.009 (2)−0.002 (2)
C50.030 (3)0.035 (3)0.037 (3)0.003 (2)0.014 (3)0.006 (2)
C60.035 (3)0.035 (3)0.031 (3)0.000 (2)0.015 (3)−0.001 (2)
C70.033 (3)0.039 (3)0.024 (3)−0.001 (3)0.010 (3)0.000 (2)
C80.030 (3)0.029 (3)0.029 (3)0.002 (2)0.006 (3)0.004 (2)
C90.028 (3)0.029 (3)0.031 (3)−0.003 (2)0.008 (3)0.004 (2)
C100.039 (4)0.038 (3)0.039 (3)−0.005 (3)0.013 (3)0.001 (3)
C110.032 (3)0.048 (4)0.045 (4)−0.001 (3)0.009 (3)0.009 (3)
C120.031 (4)0.062 (4)0.053 (4)−0.009 (3)0.000 (3)0.011 (3)
C130.048 (4)0.065 (4)0.031 (3)−0.010 (3)0.011 (3)−0.002 (3)
C140.046 (4)0.044 (4)0.042 (4)−0.002 (3)0.022 (3)0.003 (3)

Geometric parameters (Å, °)

I1—C32.092 (5)C4—C51.394 (7)
I2—C52.094 (6)C4—H40.9300
Br1—C111.898 (6)C5—C61.362 (7)
O1—C21.364 (6)C6—H60.9300
O1—H10.8200C7—H70.9300
O2—C81.222 (6)C8—C91.496 (7)
O3—H3A0.86 (4)C9—C101.377 (8)
O3—H3B0.84 (3)C9—C141.390 (8)
N1—C71.267 (6)C10—C111.359 (8)
N1—N21.356 (6)C10—H100.9300
N2—C81.357 (7)C11—C121.363 (9)
N2—H20.89 (4)C12—C131.373 (8)
C1—C61.390 (7)C12—H120.9300
C1—C21.403 (7)C13—C141.384 (8)
C1—C71.445 (7)C13—H130.9300
C2—C31.380 (7)C14—H140.9300
C3—C41.379 (7)
C2—O1—H1109.5N1—C7—C1120.3 (5)
H3A—O3—H3B107 (3)N1—C7—H7119.9
C7—N1—N2121.9 (5)C1—C7—H7119.9
N1—N2—C8117.2 (4)O2—C8—N2120.4 (5)
N1—N2—H2114 (5)O2—C8—C9122.2 (5)
C8—N2—H2129 (5)N2—C8—C9117.4 (5)
C6—C1—C2119.5 (5)C10—C9—C14120.0 (5)
C6—C1—C7118.9 (5)C10—C9—C8116.2 (5)
C2—C1—C7121.5 (5)C14—C9—C8123.7 (5)
O1—C2—C3119.0 (4)C11—C10—C9119.8 (6)
O1—C2—C1122.1 (5)C11—C10—H10120.1
C3—C2—C1118.8 (5)C9—C10—H10120.1
C4—C3—C2121.3 (5)C10—C11—C12121.4 (6)
C4—C3—I1118.2 (4)C10—C11—Br1120.5 (5)
C2—C3—I1120.5 (4)C12—C11—Br1118.1 (5)
C3—C4—C5119.4 (5)C11—C12—C13119.4 (6)
C3—C4—H4120.3C11—C12—H12120.3
C5—C4—H4120.3C13—C12—H12120.3
C6—C5—C4120.0 (5)C12—C13—C14120.5 (6)
C6—C5—I2120.0 (4)C12—C13—H13119.7
C4—C5—I2120.0 (4)C14—C13—H13119.7
C5—C6—C1120.9 (5)C13—C14—C9118.8 (6)
C5—C6—H6119.5C13—C14—H14120.6
C1—C6—H6119.5C9—C14—H14120.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.86 (4)2.50 (6)3.131 (6)132 (6)
N2—H2···O3ii0.89 (4)2.08 (6)2.934 (6)162 (7)
O1—H1···N10.821.872.579 (6)144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2600).

References

  • Adams, H., Fenton, D. E., Minardi, G., Mura, E., Pistuddi, A. M. & Solinas, C. (2000). Inorg. Chem. Commun.3, 24–28.
  • Ainscough, E. W., Brodie, A. M., Dobbs, A. J., Ranford, J. D. & Waters, J. M. (1998). Inorg. Chim. Acta, 267, 27–38.
  • 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.
  • Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem.41, 1253–1261. [PubMed]
  • Britton, D. (2003). Acta Cryst. E59, o1332–o1333.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652.
  • Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. [PMC free article] [PubMed]
  • Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S. & Kalluraya, B. (2008). Acta Cryst. E64, o1907–o1908. [PMC free article] [PubMed]
  • Koh, L. L., Kon, O. L., Loh, K. W., Long, Y. C., Ranford, J. D., Tan, A. L. C. & Tjan, Y. Y. (1998). J. Inorg. Biochem.72, 155–162. [PubMed]
  • Narayana, B., Siddaraju, B. P., Raju, C. R., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3522.
  • Prasad, C. V. C., Zheng, M., Vig, S., Bergstrom, C., Smith, D. W., Gao, Q., Yeola, S., Polson, C. T., Corsa, J. A., Guss, V. L., Loo, A., Wang, J., Sleczka, B. G., Dangler, C., Robertson, B. J., Hendrick, J. P., Roberts, S. B. & Barten, D. M. (2007). Bioorg. Med. Chem. Lett.17, 4006–4011. [PubMed]
  • Richardson, D. R. & Bernhardt, P. V. (1999). J. Biol. Inorg. Chem.4, 266–273. [PubMed]
  • Roth, A., Buchholz, A., Gärtner, M., Malassa, A., Görls, H., Vaughan, G. & Plass, W. (2007). Z. Anorg. Allg. Chem.633, 2009–2018.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yathirajan, H. S., Sarojini, B. K., Narayana, B., Sunil, K. & Bolte, M. (2007). Acta Cryst. E63, o2719.
  • Zhi, F. & Yang, Y.-L. (2007). Acta Cryst. E63, o4471.

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