3-Bromo-N'-(2-hydr-oxy-3,5-diiodo-benzyl-idene)benzohydrazide monohydrate.

Crystals of the title compound, C(14)H(9)BrI(2)N(2)O(2)·H(2)O, were obtained from a condensation reaction of 3-bromo-benzohydrazide with 3,5-diiodo-salicylaldehyde. The Schiff base mol-ecule 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 intra-molecular O-H⋯N hydrogen bond is observed in the Schiff base mol-ecule and may contribute to its overall near planarity. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming layers parallel to the bc plane. Short inter-molecular I⋯O contacts [2.930 (5) Å] are also found, linking the mol-ecules into zigzag chains along b.

Related literature

For the biological activity of Schiff bases, see: Bedia et al. (2006 ▶); Richardson & Bernhardt (1999 ▶); n class="Chemical">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·n class="Chemical">H2O

M = 588.96

Monoclinic,

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[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 ▶); 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.

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

C14H9BrI2N2O2·H2O	F(000) = 1096
Mr = 588.96	Dx = 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

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

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(Fo2) + (0.0296P)2] where P = (Fo2 + 2Fc2)/3
3656 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.63 e Å−3
4 restraints	Δρmin = −0.69 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .