(E)-N′-(5-Bromo-2-hy­droxy­benzyl­idene)-3,5-dihy­droxy­benzohydrazide monohydrate

Saharin, S.M.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810027856

organic compounds

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Volume 66| Part 8| August 2010| Page o2045

https://doi.org/10.1107/S1600536810027856

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(E)-N′-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate

Siti Munirah Saharin,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 6 July 2010; accepted 13 July 2010; online 17 July 2010)

The Schiff base molecule in the title compound, C₁₄H₁₁BrN₂O₄·H₂O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.16 Å. In the crystal structure, the Schiff base molecules and the water molecules are linked together by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, leading to layers parallel to the bc plane. An intramolecular O—H⋯N hydrogen bond involving the imine N atom and a hydroxy substituent is also observed.

Related literature

For the isotypic Cl analogue C₁₄H₁₁ClN₂O₄·H₂O, see: Deng et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₄·H₂O
M_r = 369.17
Monoclinic, P 2₁ /c
a = 13.5685 (3) Å
b = 8.0532 (2) Å
c = 13.2447 (2) Å
β = 100.186 (1)°
V = 1424.44 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 296 K
0.58 × 0.33 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.283, T_max = 0.845
9148 measured reflections
2579 independent reflections
2183 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.077
S = 1.04
2579 reflections
217 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.81 (2)	1.95 (2)	2.657 (2)	145 (3)
N2—H2N⋯O2	0.85 (2)	2.07 (2)	2.913 (3)	170 (2)
O11—H11⋯O8ⁱ	0.83 (2)	1.94 (2)	2.750 (2)	168 (3)
O13—H13⋯O1ⁱⁱ	0.79 (2)	2.19 (2)	2.959 (2)	165 (3)
O2—H2A⋯O8ⁱ	0.81 (2)	1.98 (2)	2.776 (3)	171 (4)
O2—H2B⋯O11ⁱⁱⁱ	0.83 (2)	2.06 (2)	2.861 (3)	165 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810027856/bh2299sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027856/bh2299Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1, and the crystal structure in Fig. 2. The present study shows that Br and Cl analogues (Deng et al., 2009) are isotypic crystals.

Related literature top

For the isotypic Cl analogue C₁₄H₁₁ClN₂O₄.H₂O, see: Deng et al. (2009).

Experimental top

An ethanolic solution (15 ml) of 3,5-dihydroxybenzohydrazide (0.67 g, 4 mmol) and 5-bromosalicylaldehyde (0.8 g, 4 mmol) was refluxed for 2 h. The solution was then cooled and the solid product formed was filtered off, washed with cold ethanol, and dried over silica gel. Crystals of the title compound were obtained by slow evaporation of a DMSO solution at room temperature.

Structure description top

The molecular structure of the title compound is shown in Fig. 1, and the crystal structure in Fig. 2. The present study shows that Br and Cl analogues (Deng et al., 2009) are isotypic crystals.

For the isotypic Cl analogue C₁₄H₁₁ClN₂O₄.H₂O, see: Deng et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Packing view looking down the crystallographic b unit cell edge.

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate top

Crystal data top

C₁₄H₁₁BrN₂O₄·H₂O	F(000) = 744
M_r = 369.17	D_x = 1.721 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3109 reflections
a = 13.5685 (3) Å	θ = 3.0–26.1°
b = 8.0532 (2) Å	µ = 2.91 mm⁻¹
c = 13.2447 (2) Å	T = 296 K
β = 100.186 (1)°	Plate, yellow
V = 1424.44 (5) Å³	0.58 × 0.33 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2579 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.3°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.283, T_max = 0.845	k = −9→9
9148 measured reflections	l = −15→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0328P)² + 0.7124P] where P = (F_o² + 2F_c²)/3
2579 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.45 e Å⁻³
6 restraints	Δρ_min = −0.56 e Å⁻³
0 constraints

Crystal data top

C₁₄H₁₁BrN₂O₄·H₂O	V = 1424.44 (5) Å³
M_r = 369.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5685 (3) Å	µ = 2.91 mm⁻¹
b = 8.0532 (2) Å	T = 296 K
c = 13.2447 (2) Å	0.58 × 0.33 × 0.06 mm
β = 100.186 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2579 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2183 reflections with I > 2σ(I)
T_min = 0.283, T_max = 0.845	R_int = 0.034
9148 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	6 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
2579 reflections	Δρ_min = −0.56 e Å⁻³
217 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.54976 (2)	0.19522 (4)	0.67677 (2)	0.05405 (13)
O1	0.25489 (15)	0.4914 (3)	0.33122 (13)	0.0448 (5)
H1	0.210 (2)	0.542 (4)	0.351 (2)	0.067*
O8	−0.01522 (14)	0.6853 (2)	0.34596 (12)	0.0375 (4)
O11	−0.18429 (14)	0.9113 (2)	0.71231 (12)	0.0378 (4)
H11	−0.1355 (18)	0.868 (4)	0.749 (2)	0.057*
O13	−0.29944 (14)	1.0800 (2)	0.37286 (13)	0.0440 (5)
H13	−0.285 (3)	1.075 (4)	0.3181 (17)	0.066*
N1	0.15274 (14)	0.5993 (2)	0.47190 (14)	0.0279 (4)
N2	0.07629 (15)	0.6835 (2)	0.50575 (14)	0.0277 (4)
H2N	0.088 (2)	0.712 (3)	0.5686 (14)	0.033*
C1	0.31939 (19)	0.4270 (3)	0.41219 (17)	0.0312 (5)
C2	0.3994 (2)	0.3354 (3)	0.39071 (19)	0.0402 (6)
H2	0.4072	0.3208	0.3229	0.048*
C3	0.4676 (2)	0.2657 (3)	0.4683 (2)	0.0391 (6)
H3	0.5211	0.2037	0.4534	0.047*
C4	0.45524 (18)	0.2895 (3)	0.56914 (18)	0.0330 (6)
C5	0.37678 (18)	0.3807 (3)	0.59223 (17)	0.0319 (5)
H5	0.3701	0.3951	0.6603	0.038*
C6	0.30662 (17)	0.4524 (3)	0.51387 (16)	0.0278 (5)
C7	0.22369 (18)	0.5450 (3)	0.54062 (17)	0.0300 (5)
H7	0.2219	0.5656	0.6094	0.036*
C8	−0.00598 (18)	0.7237 (3)	0.43815 (16)	0.0266 (5)
C9	−0.08615 (17)	0.8158 (3)	0.47789 (16)	0.0248 (5)
C10	−0.09485 (18)	0.8153 (3)	0.58150 (16)	0.0274 (5)
H10	−0.0499	0.7559	0.6293	0.033*
C11	−0.17126 (17)	0.9044 (3)	0.61131 (16)	0.0276 (5)
C12	−0.23974 (18)	0.9932 (3)	0.54147 (17)	0.0303 (5)
H12	−0.2908	1.0530	0.5632	0.036*
C13	−0.23079 (18)	0.9912 (3)	0.43882 (16)	0.0291 (5)
C14	−0.15405 (17)	0.9038 (3)	0.40695 (16)	0.0283 (5)
H14	−0.1479	0.9040	0.3381	0.034*
O2	0.12746 (16)	0.7432 (3)	0.72574 (13)	0.0428 (5)
H2A	0.091 (2)	0.772 (4)	0.764 (2)	0.064*
H2B	0.153 (3)	0.656 (3)	0.750 (2)	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03931 (19)	0.0753 (2)	0.04679 (19)	0.02026 (15)	0.00548 (13)	0.01280 (14)
O1	0.0449 (12)	0.0626 (13)	0.0261 (9)	0.0149 (10)	0.0044 (8)	−0.0005 (8)
O8	0.0353 (10)	0.0545 (11)	0.0224 (8)	0.0033 (9)	0.0047 (7)	−0.0065 (7)
O11	0.0417 (11)	0.0525 (11)	0.0209 (8)	0.0101 (9)	0.0098 (7)	0.0018 (7)
O13	0.0447 (11)	0.0571 (12)	0.0291 (9)	0.0212 (10)	0.0033 (8)	0.0079 (8)
N1	0.0269 (11)	0.0292 (10)	0.0281 (10)	0.0012 (9)	0.0061 (8)	−0.0039 (8)
N2	0.0273 (11)	0.0341 (11)	0.0221 (9)	0.0035 (9)	0.0048 (8)	−0.0063 (8)
C1	0.0308 (13)	0.0351 (13)	0.0275 (12)	0.0001 (11)	0.0047 (10)	0.0000 (10)
C2	0.0397 (16)	0.0533 (17)	0.0302 (13)	0.0037 (13)	0.0133 (11)	−0.0057 (11)
C3	0.0316 (15)	0.0451 (15)	0.0431 (15)	0.0054 (12)	0.0135 (11)	−0.0041 (11)
C4	0.0266 (14)	0.0382 (14)	0.0338 (13)	0.0010 (11)	0.0039 (10)	0.0021 (10)
C5	0.0316 (14)	0.0382 (13)	0.0271 (12)	0.0016 (11)	0.0082 (10)	−0.0020 (10)
C6	0.0268 (13)	0.0294 (12)	0.0276 (11)	−0.0035 (10)	0.0058 (9)	−0.0041 (9)
C7	0.0306 (13)	0.0348 (13)	0.0251 (11)	0.0009 (11)	0.0066 (10)	−0.0049 (9)
C8	0.0278 (13)	0.0289 (12)	0.0233 (12)	−0.0034 (10)	0.0053 (9)	−0.0001 (9)
C9	0.0243 (12)	0.0269 (11)	0.0233 (11)	−0.0032 (9)	0.0041 (9)	−0.0015 (9)
C10	0.0290 (13)	0.0307 (12)	0.0216 (11)	0.0007 (10)	0.0015 (9)	0.0012 (9)
C11	0.0301 (13)	0.0315 (12)	0.0222 (11)	−0.0034 (10)	0.0072 (9)	−0.0009 (9)
C12	0.0290 (13)	0.0327 (13)	0.0304 (12)	0.0029 (10)	0.0080 (10)	−0.0006 (9)
C13	0.0289 (13)	0.0299 (12)	0.0271 (11)	0.0012 (10)	0.0008 (10)	0.0032 (9)
C14	0.0322 (14)	0.0340 (13)	0.0182 (10)	−0.0018 (11)	0.0034 (9)	−0.0002 (9)
O2	0.0497 (13)	0.0487 (11)	0.0308 (10)	0.0051 (10)	0.0093 (8)	0.0000 (8)

Geometric parameters (Å, º) top

Br1—C4	1.899 (2)	C4—C5	1.372 (3)
O1—C1	1.361 (3)	C5—C6	1.402 (3)
O1—H1	0.812 (18)	C5—H5	0.9300
O8—C8	1.244 (3)	C6—C7	1.445 (3)
O11—C11	1.381 (3)	C7—H7	0.9300
O11—H11	0.827 (18)	C8—C9	1.487 (3)
O13—C13	1.361 (3)	C9—C14	1.389 (3)
O13—H13	0.785 (18)	C9—C10	1.398 (3)
N1—C7	1.279 (3)	C10—C11	1.375 (3)
N1—N2	1.379 (3)	C10—H10	0.9300
N2—C8	1.341 (3)	C11—C12	1.388 (3)
N2—H2N	0.851 (17)	C12—C13	1.386 (3)
C1—C2	1.383 (4)	C12—H12	0.9300
C1—C6	1.403 (3)	C13—C14	1.383 (3)
C2—C3	1.375 (4)	C14—H14	0.9300
C2—H2	0.9300	O2—H2A	0.807 (18)
C3—C4	1.389 (3)	O2—H2B	0.825 (18)
C3—H3	0.9300

C1—O1—H1	110 (2)	N1—C7—C6	121.5 (2)
C11—O11—H11	109 (2)	N1—C7—H7	119.2
C13—O13—H13	108 (3)	C6—C7—H7	119.2
C7—N1—N2	116.85 (18)	O8—C8—N2	121.5 (2)
C8—N2—N1	119.13 (18)	O8—C8—C9	121.2 (2)
C8—N2—H2N	125.0 (18)	N2—C8—C9	117.29 (18)
N1—N2—H2N	115.7 (18)	C14—C9—C10	120.3 (2)
O1—C1—C2	117.4 (2)	C14—C9—C8	117.02 (19)
O1—C1—C6	122.0 (2)	C10—C9—C8	122.7 (2)
C2—C1—C6	120.6 (2)	C11—C10—C9	118.6 (2)
C3—C2—C1	120.9 (2)	C11—C10—H10	120.7
C3—C2—H2	119.6	C9—C10—H10	120.7
C1—C2—H2	119.6	C10—C11—O11	122.1 (2)
C2—C3—C4	118.8 (2)	C10—C11—C12	121.8 (2)
C2—C3—H3	120.6	O11—C11—C12	116.1 (2)
C4—C3—H3	120.6	C13—C12—C11	118.9 (2)
C5—C4—C3	121.3 (2)	C13—C12—H12	120.5
C5—C4—Br1	119.64 (18)	C11—C12—H12	120.5
C3—C4—Br1	119.10 (19)	O13—C13—C14	122.5 (2)
C4—C5—C6	120.5 (2)	O13—C13—C12	117.0 (2)
C4—C5—H5	119.8	C14—C13—C12	120.4 (2)
C6—C5—H5	119.8	C13—C14—C9	119.91 (19)
C5—C6—C1	117.9 (2)	C13—C14—H14	120.0
C5—C6—C7	119.1 (2)	C9—C14—H14	120.0
C1—C6—C7	123.0 (2)	H2A—O2—H2B	105 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.81 (2)	1.95 (2)	2.657 (2)	145 (3)
N2—H2N···O2	0.85 (2)	2.07 (2)	2.913 (3)	170 (2)
O1—H1···O2ⁱ	0.81 (2)	2.52 (3)	2.942 (3)	114 (3)
O11—H11···O8ⁱⁱ	0.83 (2)	1.94 (2)	2.750 (2)	168 (3)
O13—H13···O1ⁱⁱⁱ	0.79 (2)	2.19 (2)	2.959 (2)	165 (3)
O2—H2A···O8ⁱⁱ	0.81 (2)	1.98 (2)	2.776 (3)	171 (4)
O2—H2B···O11^iv	0.83 (2)	2.06 (2)	2.861 (3)	165 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrN₂O₄·H₂O
M_r	369.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.5685 (3), 8.0532 (2), 13.2447 (2)
β (°)	100.186 (1)
V (Å³)	1424.44 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.58 × 0.33 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.283, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	9148, 2579, 2183
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.077, 1.04
No. of reflections	2579
No. of parameters	217
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.56

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.812 (18)	1.95 (2)	2.657 (2)	145 (3)
N2—H2N···O2	0.851 (17)	2.071 (17)	2.913 (3)	170 (2)
O11—H11···O8ⁱ	0.827 (18)	1.937 (19)	2.750 (2)	168 (3)
O13—H13···O1ⁱⁱ	0.785 (18)	2.19 (2)	2.959 (2)	165 (3)
O2—H2A···O8ⁱ	0.807 (18)	1.976 (19)	2.776 (3)	171 (4)
O2—H2B···O11ⁱⁱⁱ	0.825 (18)	2.06 (2)	2.861 (3)	165 (3)

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

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C)

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deng, S., Han, L., Huang, S., Zhang, H., Diao, Y. & Liu, K. (2009). Acta Cryst. E65, o721. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS 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′-(5-Bromo-2-hy­dr­oxy­benzyl­­idene)-3,5-dihy­dr­oxy­benzohydrazide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate