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

Ning, J.-H.; Xu, X.-W.

doi:10.1107/S1600536809010964

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o905-o906

doi:10.1107/S1600536809010964

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

Jing-Heng Ning ^a ^* and Xiao-Wu Xu ^b

^aCollege of Chemical and Biological Engineering, Changsha University of Science and Technology, Changsha 410004, People's Republic of China, and ^bChangsha Chemical Industry Research Institute, Changsha 410007, People's Republic of China
^*Correspondence e-mail: ningjingheng@126.com

(Received 23 March 2009; accepted 25 March 2009; online 28 March 2009)

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

Experimental

Crystal data

C₁₄H₉BrI₂N₂O₂·H₂O
M_r = 588.96
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.090
S = 1.00
3656 reflections
209 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.86 (4)	2.50 (6)	3.131 (6)	132 (6)
N2—H2⋯O3ⁱⁱ	0.89 (4)	2.08 (6)	2.934 (6)	162 (7)
O1—H1⋯N1	0.82	1.87	2.579 (6)	144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010964/sj2600sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	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.

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

Crystal data top

C₁₄H₉BrI₂N₂O₂·H₂O	F(000) = 1096
M_r = 588.96	D_x = 2.331 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2004 reflections
a = 15.181 (3) Å	θ = 2.6–24.5°
b = 7.611 (2) Å	µ = 6.14 mm⁻¹
c = 15.516 (3) Å	T = 298 K
β = 110.628 (3)°	Block, yellow
V = 1677.8 (6) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	2651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→19
T_min = 0.261, T_max = 0.293	k = −9→9
13552 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0296P)²] where P = (F_o² + 2F_c²)/3
3656 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.63 e Å⁻³
4 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₄H₉BrI₂N₂O₂·H₂O	V = 1677.8 (6) Å³
M_r = 588.96	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.181 (3) Å	µ = 6.14 mm⁻¹
b = 7.611 (2) Å	T = 298 K
c = 15.516 (3) Å	0.23 × 0.20 × 0.20 mm
β = 110.628 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3656 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2651 reflections with I > 2σ(I)
T_min = 0.261, T_max = 0.293	R_int = 0.059
13552 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	4 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.63 e Å⁻³
3656 reflections	Δρ_min = −0.69 e Å⁻³
209 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
I1	0.32291 (3)	−0.01495 (5)	0.20582 (3)	0.04369 (14)
I2	0.14532 (3)	−0.04420 (6)	0.49489 (3)	0.04849 (15)
Br1	1.04870 (5)	0.64844 (11)	0.62538 (6)	0.0699 (3)
O1	0.4774 (3)	0.1800 (5)	0.3704 (2)	0.0362 (9)
H1	0.5212	0.2190	0.4140	0.054*
O2	0.6948 (3)	0.4091 (6)	0.4847 (3)	0.0465 (11)
O3	0.4178 (4)	0.0028 (7)	0.7467 (3)	0.0636 (14)
N1	0.5549 (3)	0.3106 (5)	0.5331 (3)	0.0303 (10)
N2	0.6303 (3)	0.3938 (6)	0.5939 (3)	0.0318 (10)
C1	0.4070 (4)	0.1717 (7)	0.4882 (4)	0.0301 (12)
C2	0.4058 (4)	0.1324 (6)	0.3995 (3)	0.0260 (11)
C3	0.3290 (4)	0.0455 (7)	0.3393 (4)	0.0314 (12)
C4	0.2549 (4)	−0.0061 (7)	0.3655 (4)	0.0312 (13)
H4	0.2040	−0.0660	0.3244	0.037*
C5	0.2572 (4)	0.0324 (7)	0.4540 (4)	0.0333 (13)
C6	0.3317 (4)	0.1209 (7)	0.5138 (4)	0.0325 (13)
H6	0.3323	0.1476	0.5724	0.039*
C7	0.4852 (4)	0.2632 (7)	0.5544 (4)	0.0323 (13)
H7	0.4844	0.2872	0.6129	0.039*
C8	0.7013 (4)	0.4386 (7)	0.5641 (4)	0.0304 (12)
C9	0.7872 (4)	0.5200 (6)	0.6326 (4)	0.0301 (12)
C10	0.8620 (4)	0.5467 (7)	0.6036 (4)	0.0389 (14)
H10	0.8576	0.5140	0.5444	0.047*
C11	0.9424 (4)	0.6211 (8)	0.6616 (4)	0.0429 (15)
C12	0.9500 (4)	0.6747 (9)	0.7478 (5)	0.0530 (17)
H12	1.0052	0.7269	0.7863	0.064*
C13	0.8755 (4)	0.6511 (8)	0.7772 (4)	0.0489 (16)
H13	0.8802	0.6884	0.8357	0.059*
C14	0.7934 (5)	0.5721 (7)	0.7204 (4)	0.0422 (15)
H14	0.7433	0.5543	0.7407	0.051*
H2	0.626 (5)	0.411 (9)	0.649 (2)	0.080*
H3A	0.414 (6)	−0.082 (4)	0.709 (3)	0.080*
H3B	0.414 (5)	0.097 (3)	0.717 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0401 (3)	0.0640 (3)	0.0293 (2)	−0.00844 (19)	0.01519 (18)	−0.01025 (18)
I2	0.0423 (3)	0.0602 (3)	0.0522 (3)	−0.0090 (2)	0.0281 (2)	−0.0014 (2)
Br1	0.0381 (4)	0.0888 (6)	0.0902 (6)	−0.0056 (4)	0.0317 (4)	0.0133 (5)
O1	0.029 (2)	0.054 (3)	0.027 (2)	−0.0065 (19)	0.0114 (18)	−0.0023 (18)
O2	0.047 (3)	0.067 (3)	0.025 (2)	−0.009 (2)	0.013 (2)	−0.004 (2)
O3	0.062 (3)	0.079 (3)	0.058 (3)	0.014 (3)	0.031 (3)	0.017 (3)
N1	0.024 (2)	0.032 (2)	0.030 (3)	0.0035 (19)	0.003 (2)	0.000 (2)
N2	0.026 (3)	0.042 (3)	0.026 (3)	−0.005 (2)	0.007 (2)	−0.005 (2)
C1	0.027 (3)	0.032 (3)	0.029 (3)	−0.001 (2)	0.008 (2)	0.004 (2)
C2	0.028 (3)	0.030 (3)	0.021 (3)	0.004 (2)	0.009 (2)	0.003 (2)
C3	0.037 (3)	0.033 (3)	0.026 (3)	0.001 (3)	0.012 (3)	−0.003 (2)
C4	0.025 (3)	0.041 (3)	0.027 (3)	−0.006 (2)	0.009 (2)	−0.002 (2)
C5	0.030 (3)	0.035 (3)	0.037 (3)	0.003 (2)	0.014 (3)	0.006 (2)
C6	0.035 (3)	0.035 (3)	0.031 (3)	0.000 (2)	0.015 (3)	−0.001 (2)
C7	0.033 (3)	0.039 (3)	0.024 (3)	−0.001 (3)	0.010 (3)	0.000 (2)
C8	0.030 (3)	0.029 (3)	0.029 (3)	0.002 (2)	0.006 (3)	0.004 (2)
C9	0.028 (3)	0.029 (3)	0.031 (3)	−0.003 (2)	0.008 (3)	0.004 (2)
C10	0.039 (4)	0.038 (3)	0.039 (3)	−0.005 (3)	0.013 (3)	0.001 (3)
C11	0.032 (3)	0.048 (4)	0.045 (4)	−0.001 (3)	0.009 (3)	0.009 (3)
C12	0.031 (4)	0.062 (4)	0.053 (4)	−0.009 (3)	0.000 (3)	0.011 (3)
C13	0.048 (4)	0.065 (4)	0.031 (3)	−0.010 (3)	0.011 (3)	−0.002 (3)
C14	0.046 (4)	0.044 (4)	0.042 (4)	−0.002 (3)	0.022 (3)	0.003 (3)

Geometric parameters (Å, º) top

I1—C3	2.092 (5)	C4—C5	1.394 (7)
I2—C5	2.094 (6)	C4—H4	0.9300
Br1—C11	1.898 (6)	C5—C6	1.362 (7)
O1—C2	1.364 (6)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C8	1.222 (6)	C8—C9	1.496 (7)
O3—H3A	0.86 (4)	C9—C10	1.377 (8)
O3—H3B	0.84 (3)	C9—C14	1.390 (8)
N1—C7	1.267 (6)	C10—C11	1.359 (8)
N1—N2	1.356 (6)	C10—H10	0.9300
N2—C8	1.357 (7)	C11—C12	1.363 (9)
N2—H2	0.89 (4)	C12—C13	1.373 (8)
C1—C6	1.390 (7)	C12—H12	0.9300
C1—C2	1.403 (7)	C13—C14	1.384 (8)
C1—C7	1.445 (7)	C13—H13	0.9300
C2—C3	1.380 (7)	C14—H14	0.9300
C3—C4	1.379 (7)

C2—O1—H1	109.5	N1—C7—C1	120.3 (5)
H3A—O3—H3B	107 (3)	N1—C7—H7	119.9
C7—N1—N2	121.9 (5)	C1—C7—H7	119.9
N1—N2—C8	117.2 (4)	O2—C8—N2	120.4 (5)
N1—N2—H2	114 (5)	O2—C8—C9	122.2 (5)
C8—N2—H2	129 (5)	N2—C8—C9	117.4 (5)
C6—C1—C2	119.5 (5)	C10—C9—C14	120.0 (5)
C6—C1—C7	118.9 (5)	C10—C9—C8	116.2 (5)
C2—C1—C7	121.5 (5)	C14—C9—C8	123.7 (5)
O1—C2—C3	119.0 (4)	C11—C10—C9	119.8 (6)
O1—C2—C1	122.1 (5)	C11—C10—H10	120.1
C3—C2—C1	118.8 (5)	C9—C10—H10	120.1
C4—C3—C2	121.3 (5)	C10—C11—C12	121.4 (6)
C4—C3—I1	118.2 (4)	C10—C11—Br1	120.5 (5)
C2—C3—I1	120.5 (4)	C12—C11—Br1	118.1 (5)
C3—C4—C5	119.4 (5)	C11—C12—C13	119.4 (6)
C3—C4—H4	120.3	C11—C12—H12	120.3
C5—C4—H4	120.3	C13—C12—H12	120.3
C6—C5—C4	120.0 (5)	C12—C13—C14	120.5 (6)
C6—C5—I2	120.0 (4)	C12—C13—H13	119.7
C4—C5—I2	120.0 (4)	C14—C13—H13	119.7
C5—C6—C1	120.9 (5)	C13—C14—C9	118.8 (6)
C5—C6—H6	119.5	C13—C14—H14	120.6
C1—C6—H6	119.5	C9—C14—H14	120.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.86 (4)	2.50 (6)	3.131 (6)	132 (6)
N2—H2···O3ⁱⁱ	0.89 (4)	2.08 (6)	2.934 (6)	162 (7)
O1—H1···N1	0.82	1.87	2.579 (6)	144

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

Experimental details

Crystal data
Chemical formula	C₁₄H₉BrI₂N₂O₂·H₂O
M_r	588.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.181 (3), 7.611 (2), 15.516 (3)
β (°)	110.628 (3)
V (Å³)	1677.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.14
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.261, 0.293
No. of measured, independent and observed [I > 2σ(I)] reflections	13552, 3656, 2651
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.090, 1.00
No. of reflections	3656
No. of parameters	209
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.69

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.86 (4)	2.50 (6)	3.131 (6)	132 (6)
N2—H2···O3ⁱⁱ	0.89 (4)	2.08 (6)	2.934 (6)	162 (7)
O1—H1···N1	0.82	1.87	2.579 (6)	144.1

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

Acknowledgements

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).

References

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