(E)-N′-(3,5-Dibromo-2-hydroxy­benzyl­idene)-4-hydroxy­benzohydrazide monohydrate

Wang, X.-Y.; Cao, G.-B.; Yang, T.

doi:10.1107/S1600536808030304

organic compounds

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Volume 64| Part 10| October 2008| Page o2022

doi:10.1107/S1600536808030304

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(E)-N′-(3,5-Dibromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide monohydrate

Xiao-Ya Wang,^a Guo-Biao Cao ^b ^* and Tao Yang ^b

^aDepartment of Biology, Ankang University, Ankang Shanxi 725000, People's Republic of China, and ^bDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
^*Correspondence e-mail: guobiao_cao@126.com

(Received 3 September 2008; accepted 21 September 2008; online 27 September 2008)

The title compound, C₁₄H₁₀Br₂N₂O₃·H₂O, was synthesized by the reaction of 3,5-dibromo-2-hydroxybenzaldehyde with an equimolar amount of 4-hydroxybenzohydrazide in methanol. The structure comprises a Schiff base unit and a water molecule of crystallization. The dihedral angle between the benzene rings in the Schiff base is 1.3 (3)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds, with the water molecule serving as both donor and acceptor. As a result, layers are formed, which are approximately parallel to the bc plane.

Related literature

For related structures, see: Cao (2007a ,b ); Yang et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀Br₂N₂O₃·H₂O
M_r = 432.08
Monoclinic, P 2₁ /c
a = 6.9840 (16) Å
b = 12.678 (3) Å
c = 17.722 (4) Å
β = 96.999 (4)°
V = 1557.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 5.22 mm⁻¹
T = 298 (2) K
0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.307, T_max = 0.318
12695 measured reflections
3366 independent reflections
2045 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.106
S = 0.99
3366 reflections
210 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.578 (4)	146
O3—H3⋯O2ⁱ	0.82	1.83	2.642 (4)	173
O4—H4A⋯O3ⁱⁱ	0.847 (10)	2.038 (14)	2.878 (4)	171 (5)
O4—H4B⋯O1ⁱ	0.851 (10)	2.24 (3)	2.969 (5)	144 (4)
N2—H2⋯O4ⁱⁱⁱ	0.898 (10)	2.01 (2)	2.874 (5)	162 (5)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536808030304/bh2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030304/bh2193Isup2.hkl

checkCIF report

Comment top

We have recently reported some transition metal complexes with Schiff base ligands (Cao, 2007a; Cao, 2007b). We report herein the crystal structure of the title compound, (I), derived from the reaction of 3,5-dibromo-2-hydroxybenzaldehyde with an equimolar quantity of 4-hydroxybenzohydrazide in methanol.

The compound (I), Fig. 1, comprises a Schiff base unit and a water molecule of crystallization. The dihedral angle between the two benzene rings in the Schiff base unit is 1.3 (3)°. All bond lengths are comparable to the similar compound, 3-bromo-N'-[(E)-4-hydroxybenzylidene]benzohydrazide, which we reported previously (Yang et al., 2008). In the crystal structure, molecules are linked through intermolecular hydrogen bonds of types O—H···O and N—H···O (Table 1), forming 2D layers approximately parallel to the bc plane, as shown in Fig. 2.

Related literature top

For related structures, see: Cao (2007a,b); Yang et al. (2008).

Experimental top

The compound was prepared by refluxing equimolar quantities of 3,5-dibromo-2-hydroxybenzaldehyde with 4-hydroxybenzohydrazide in methanol. Colorless block crystals were formed when the solution was evaporated in air over five days.

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 ellipsoids drawn at the 30% probability level. Water and main molecule are placed in two different asymmetric units.
	Fig. 2. The molecular packing of (I), viewed along the c axis. Hydrogen bonds are drawn as dashed lines.

(E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide monohydrate top

Crystal data top

C₁₄H₁₀Br₂N₂O₃·H₂O	F(000) = 848
M_r = 432.08	D_x = 1.843 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1545 reflections
a = 6.9840 (16) Å	θ = 2.3–24.9°
b = 12.678 (3) Å	µ = 5.22 mm⁻¹
c = 17.722 (4) Å	T = 298 K
β = 96.999 (4)°	Block, colourless
V = 1557.4 (6) Å³	0.23 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3366 independent reflections
Radiation source: fine-focus sealed tube	2045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.308, T_max = 0.318	k = −16→15
12695 measured reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0361P)²] where P = (F_o² + 2F_c²)/3
3366 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.42 e Å⁻³
4 restraints	Δρ_min = −0.42 e Å⁻³
0 constraints

Crystal data top

C₁₄H₁₀Br₂N₂O₃·H₂O	V = 1557.4 (6) Å³
M_r = 432.08	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9840 (16) Å	µ = 5.22 mm⁻¹
b = 12.678 (3) Å	T = 298 K
c = 17.722 (4) Å	0.23 × 0.23 × 0.22 mm
β = 96.999 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3366 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2045 reflections with I > 2σ(I)
T_min = 0.308, T_max = 0.318	R_int = 0.075
12695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.42 e Å⁻³
3366 reflections	Δρ_min = −0.42 e Å⁻³
210 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.07183 (8)	0.86697 (4)	−0.00493 (3)	0.0601 (2)
Br2	0.05286 (8)	0.71867 (5)	−0.30593 (3)	0.0664 (2)
O1	0.1871 (5)	0.6446 (2)	0.03203 (16)	0.0405 (7)
H1	0.2190	0.5834	0.0420	0.061*
O2	0.3386 (4)	0.4075 (2)	0.14777 (16)	0.0426 (8)
O3	0.5946 (6)	−0.0702 (2)	0.20309 (16)	0.0594 (10)
H3	0.6086	−0.0733	0.2497	0.089*
O4	0.4571 (5)	0.2539 (3)	0.39995 (18)	0.0494 (8)
N1	0.2698 (5)	0.4520 (3)	0.00247 (19)	0.0323 (8)
N2	0.3257 (5)	0.3529 (3)	0.02714 (19)	0.0336 (8)
C1	0.1784 (6)	0.5746 (3)	−0.0955 (2)	0.0301 (10)
C2	0.1564 (6)	0.6572 (3)	−0.0440 (2)	0.0336 (10)
C3	0.1013 (6)	0.7560 (3)	−0.0737 (3)	0.0388 (11)
C4	0.0691 (6)	0.7749 (4)	−0.1503 (3)	0.0422 (11)
H4	0.0323	0.8414	−0.1687	0.051*
C5	0.0927 (6)	0.6928 (4)	−0.1997 (2)	0.0385 (11)
C6	0.1470 (6)	0.5942 (4)	−0.1731 (2)	0.0398 (11)
H6	0.1628	0.5401	−0.2073	0.048*
C7	0.2368 (6)	0.4704 (3)	−0.0687 (2)	0.0358 (10)
H7	0.2504	0.4166	−0.1033	0.043*
C8	0.3580 (6)	0.3355 (3)	0.1033 (2)	0.0311 (10)
C9	0.4152 (6)	0.2264 (3)	0.1270 (2)	0.0292 (9)
C10	0.4475 (7)	0.2041 (3)	0.2037 (2)	0.0430 (12)
H10	0.4294	0.2573	0.2383	0.052*
C11	0.5056 (7)	0.1059 (3)	0.2311 (2)	0.0438 (12)
H11	0.5262	0.0933	0.2832	0.053*
C12	0.5325 (7)	0.0275 (3)	0.1807 (2)	0.0385 (11)
C13	0.4980 (7)	0.0477 (3)	0.1040 (2)	0.0528 (14)
H13	0.5146	−0.0059	0.0696	0.063*
C14	0.4397 (7)	0.1452 (3)	0.0773 (2)	0.0462 (12)
H14	0.4163	0.1569	0.0252	0.055*
H2	0.356 (7)	0.307 (3)	−0.008 (2)	0.080*
H4A	0.436 (6)	0.309 (3)	0.373 (3)	0.080*
H4B	0.5787 (19)	0.245 (4)	0.408 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0799 (4)	0.0359 (3)	0.0643 (4)	0.0158 (3)	0.0076 (3)	−0.0051 (3)
Br2	0.0707 (4)	0.0883 (5)	0.0380 (3)	0.0029 (3)	−0.0022 (2)	0.0233 (3)
O1	0.061 (2)	0.0292 (17)	0.0304 (16)	0.0048 (16)	0.0005 (15)	0.0034 (13)
O2	0.066 (2)	0.0267 (16)	0.0348 (17)	0.0075 (15)	0.0035 (15)	−0.0053 (14)
O3	0.122 (3)	0.0215 (17)	0.0333 (18)	0.0134 (19)	0.003 (2)	0.0046 (14)
O4	0.070 (2)	0.041 (2)	0.0359 (18)	−0.0058 (18)	0.0031 (17)	0.0069 (15)
N1	0.035 (2)	0.026 (2)	0.034 (2)	0.0008 (16)	0.0007 (16)	0.0021 (16)
N2	0.046 (2)	0.023 (2)	0.031 (2)	0.0049 (17)	0.0024 (17)	0.0037 (15)
C1	0.032 (2)	0.032 (2)	0.026 (2)	0.0011 (19)	0.0028 (18)	0.0022 (19)
C2	0.032 (2)	0.035 (3)	0.033 (2)	0.001 (2)	0.0032 (19)	0.004 (2)
C3	0.039 (3)	0.030 (2)	0.047 (3)	0.004 (2)	0.004 (2)	0.001 (2)
C4	0.041 (3)	0.035 (3)	0.050 (3)	0.006 (2)	0.001 (2)	0.016 (2)
C5	0.035 (2)	0.049 (3)	0.030 (2)	0.000 (2)	0.0011 (19)	0.015 (2)
C6	0.042 (3)	0.045 (3)	0.032 (2)	0.004 (2)	0.001 (2)	0.000 (2)
C7	0.043 (3)	0.032 (3)	0.032 (2)	0.003 (2)	0.002 (2)	−0.0007 (19)
C8	0.029 (2)	0.029 (2)	0.034 (2)	−0.0019 (19)	0.0004 (19)	0.000 (2)
C9	0.034 (2)	0.023 (2)	0.030 (2)	−0.0003 (19)	0.0010 (18)	0.0003 (18)
C10	0.067 (3)	0.033 (3)	0.030 (2)	0.007 (2)	0.006 (2)	−0.010 (2)
C11	0.073 (3)	0.032 (3)	0.026 (2)	0.009 (2)	0.006 (2)	0.001 (2)
C12	0.064 (3)	0.019 (2)	0.033 (3)	0.003 (2)	0.009 (2)	0.0036 (19)
C13	0.104 (4)	0.025 (3)	0.029 (3)	0.014 (3)	0.006 (3)	−0.008 (2)
C14	0.081 (4)	0.030 (3)	0.026 (2)	0.009 (3)	0.001 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Br1—C3	1.888 (4)	C3—C4	1.371 (6)
Br2—C5	1.897 (4)	C4—C5	1.382 (6)
O1—C2	1.348 (5)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.374 (6)
O2—C8	1.225 (5)	C6—H6	0.9300
O3—C12	1.355 (5)	C7—H7	0.9300
O3—H3	0.8200	C8—C9	1.486 (5)
O4—H4A	0.847 (10)	C9—C14	1.379 (5)
O4—H4B	0.851 (10)	C9—C10	1.379 (6)
N1—C7	1.275 (5)	C10—C11	1.380 (6)
N1—N2	1.371 (4)	C10—H10	0.9300
N2—C8	1.359 (5)	C11—C12	1.365 (6)
N2—H2	0.898 (10)	C11—H11	0.9300
C1—C6	1.387 (5)	C12—C13	1.375 (6)
C1—C2	1.411 (6)	C13—C14	1.368 (6)
C1—C7	1.446 (6)	C13—H13	0.9300
C2—C3	1.395 (6)	C14—H14	0.9300

C2—O1—H1	109.5	N1—C7—C1	120.2 (4)
C12—O3—H3	109.5	N1—C7—H7	119.9
H4A—O4—H4B	108 (2)	C1—C7—H7	119.9
C7—N1—N2	119.5 (4)	O2—C8—N2	120.0 (4)
C8—N2—N1	118.2 (3)	O2—C8—C9	123.9 (4)
C8—N2—H2	124 (4)	N2—C8—C9	116.1 (4)
N1—N2—H2	117 (4)	C14—C9—C10	117.3 (4)
C6—C1—C2	119.4 (4)	C14—C9—C8	124.3 (4)
C6—C1—C7	119.6 (4)	C10—C9—C8	118.4 (4)
C2—C1—C7	120.9 (4)	C9—C10—C11	122.5 (4)
O1—C2—C3	119.1 (4)	C9—C10—H10	118.7
O1—C2—C1	122.8 (4)	C11—C10—H10	118.7
C3—C2—C1	118.1 (4)	C12—C11—C10	119.0 (4)
C4—C3—C2	122.3 (4)	C12—C11—H11	120.5
C4—C3—Br1	119.5 (3)	C10—C11—H11	120.5
C2—C3—Br1	118.2 (3)	O3—C12—C11	122.6 (4)
C3—C4—C5	118.6 (4)	O3—C12—C13	118.1 (4)
C3—C4—H4	120.7	C11—C12—C13	119.3 (4)
C5—C4—H4	120.7	C14—C13—C12	121.3 (4)
C6—C5—C4	121.1 (4)	C14—C13—H13	119.4
C6—C5—Br2	120.0 (4)	C12—C13—H13	119.4
C4—C5—Br2	118.9 (3)	C13—C14—C9	120.6 (4)
C5—C6—C1	120.5 (4)	C13—C14—H14	119.7
C5—C6—H6	119.7	C9—C14—H14	119.7
C1—C6—H6	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.578 (4)	146
O3—H3···O2ⁱ	0.82	1.83	2.642 (4)	173
O4—H4A···O3ⁱⁱ	0.85 (1)	2.04 (1)	2.878 (4)	171 (5)
O4—H4B···O1ⁱ	0.85 (1)	2.24 (3)	2.969 (5)	144 (4)
N2—H2···O4ⁱⁱⁱ	0.90 (1)	2.01 (2)	2.874 (5)	162 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀Br₂N₂O₃·H₂O
M_r	432.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.9840 (16), 12.678 (3), 17.722 (4)
β (°)	96.999 (4)
V (Å³)	1557.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.22
Crystal size (mm)	0.23 × 0.23 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.308, 0.318
No. of measured, independent and observed [I > 2σ(I)] reflections	12695, 3366, 2045
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.106, 1.00
No. of reflections	3366
No. of parameters	210
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)	0.42, −0.42

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
O1—H1···N1	0.82	1.86	2.578 (4)	145.7
O3—H3···O2ⁱ	0.82	1.83	2.642 (4)	173.1
O4—H4A···O3ⁱⁱ	0.847 (10)	2.038 (14)	2.878 (4)	171 (5)
O4—H4B···O1ⁱ	0.851 (10)	2.24 (3)	2.969 (5)	144 (4)
N2—H2···O4ⁱⁱⁱ	0.898 (10)	2.01 (2)	2.874 (5)	162 (5)

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

Acknowledgements

The Natural Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 07JK177) is acknowledged.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, G.-B. (2007a). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 37, 639–642. CAS Google Scholar
Cao, G.-B. (2007b). Acta Cryst. E63, m1149–m1150. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

(E)-N′-(3,5-Di­bromo-2-hy­droxy­benzyl­­idene)-4-hy­droxy­benzohydrazide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-(3,5-Dibromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide monohydrate