(E)-N′-(4-Bromo­benzyl­idene)-3,4-dihydroxy­benzohydrazide monohydrate

Zhao, D.-Y.; Li, C.-X.; Huang, S.; Zhong, M.-T.; Zhang, H.-L.

doi:10.1107/S1600536809036964

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2489

doi:10.1107/S1600536809036964

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(E)-N′-(4-Bromobenzylidene)-3,4-dihydroxybenzohydrazide monohydrate

Dan-Yu Zhao,^a Chuan-Xun Li,^b Shan-shan Huang,^b Min-Tao Zhong ^b ^* and Hou-Li Zhang ^b ^*

^aLiaoning University of Traditional Chinese Medicine, Shenyang, 110032, People's Republic of China, and ^bDalian Medical University, Liaoning 116044, People's Republic of China
^*Correspondence e-mail: dalianzhongmintao@163.com, syzhaody@163.com

(Received 6 September 2009; accepted 12 September 2009; online 19 September 2009)

In the title compound, C₁₄H₁₁BrN₂O₃·H₂O, the dihedral angle between the two benzene rings of the Schiff base is 22.7 (2)° and an intramolecular O—H⋯O hydrogen bond is observed. In the crystal, molecules are linked into layers parallel to the ab plane by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff base compounds from the reaction of aldehydes with primary amines, see: Herrick et al. (2008 ); Suresh et al. (2007 ). For a related structure, see: Ma et al. (2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₃·H₂O
M_r = 353.17
Monoclinic, P 2₁ /c
a = 7.8119 (5) Å
b = 13.8504 (9) Å
c = 13.0764 (9) Å
β = 91.708 (1)°
V = 1414.21 (16) Å³
Z = 4
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 295 K
0.18 × 0.16 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan SADABS (Sheldrick, 1996 ) T_min = 0.621, T_max = 0.668
7384 measured reflections
2511 independent reflections
1810 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.02
2511 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.76 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
O1—H1⋯O2	0.82	2.30	2.734 (3)	114
O4—H16⋯O2ⁱ	0.85	2.03	2.760 (3)	143
O4—H15⋯O3ⁱⁱ	0.85	1.94	2.761 (3)	163
O2—H2⋯O3ⁱⁱⁱ	0.82	1.91	2.675 (3)	154
O1—H1⋯O4^iv	0.82	2.16	2.929 (4)	155
N1—H1A⋯O4^v	0.86	2.07	2.898 (4)	162
Symmetry codes: (i) x, y-1, z+1; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x, y+1, z-1; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036964/hb5092sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036964/hb5092Isup2.hkl

checkCIF report

Comment top

Schiff base compounds can be easily synthesized from the reaction of aldehydes with primary amines (Herrick et al., 2008; Suresh et al., 2007). In this paper, the crystal structure of a new Schiff base compound derived from the condensation reaction of 3,4-dihydroxybenzohydrazide with 4-bromobenzaldehyde is reported.

The Schiff base molecule of the title compound, (I), displays a trans configuration with respect to the C=N and C—N bonds (Fig. 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to those in the related compound 3,4-Dihydroxy-N'-(2-hydroxybenzylidene)benzohydrazide- methanol-water (2/1/3) (Ma et al., 2008). The dihedral angle between the two benzene rings in (I) is 22.7 (2)°. An intramolecular O—H···O hydrogen bond is observed. In the crystal structure the water molecule links three symmetry related molecules through O—H···O and O—H···N hydrogen bonds (Table 1). Together with two further intermolecular O—H···O hydrogen bonds, layers parallel to the ab plane are formed (Fig. 2).

Related literature top

For the synthesis of Schiff base compounds from the reaction of aldehydes with primary amines, see: Herrick et al. (2008); Suresh et al. (2007). For a related structures, see: Ma et al. (2008). For reference structural data, see: Allen et al. (1987).

Experimental top

4-Bromosalicylaldehyde (0.1 mmol, 15.6 mg) and 3,4-dihydroxybenzoic acid hydrazide (0.1 mmol, 16.8 mg) were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Light yellow blokcs of (I) were formed by gradual evaporation of the solvent over a period of nine days at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
	Fig. 2. The molecular packing of (I). Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.

(E)-N'-(4-Bromobenzylidene)-3,4-dihydroxybenzohydrazide monohydrate top

Crystal data top

C₁₄H₁₁BrN₂O₃·H₂O	F(000) = 712
M_r = 353.17	D_x = 1.659 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2538 reflections
a = 7.8119 (5) Å	θ = 2.7–24.2°
b = 13.8504 (9) Å	µ = 2.92 mm⁻¹
c = 13.0764 (9) Å	T = 295 K
β = 91.708 (1)°	Block, light yellow
V = 1414.21 (16) Å³	0.18 × 0.16 × 0.15 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	2511 independent reflections
Radiation source: fine-focus sealed tube	1810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −9→9
T_min = 0.621, T_max = 0.668	k = −12→16
7384 measured reflections	l = −12→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.053P)² + 0.0453P] where P = (F_o² + 2F_c²)/3
2511 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₄H₁₁BrN₂O₃·H₂O	V = 1414.21 (16) Å³
M_r = 353.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8119 (5) Å	µ = 2.92 mm⁻¹
b = 13.8504 (9) Å	T = 295 K
c = 13.0764 (9) Å	0.18 × 0.16 × 0.15 mm
β = 91.708 (1)°

Data collection top

Siemens SMART CCD diffractometer	2511 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	1810 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.668	R_int = 0.096
7384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.76 e Å⁻³
2511 reflections	Δρ_min = −0.69 e Å⁻³
192 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Br1	1.08523 (6)	0.16874 (3)	0.20512 (4)	0.0710 (2)
O1	0.2102 (4)	1.04968 (18)	−0.1288 (2)	0.0561 (7)
H1	0.2496	1.0583	−0.1855	0.084*
O2	0.4375 (4)	0.94026 (17)	−0.23369 (19)	0.0590 (8)
H2	0.4882	0.8962	−0.2617	0.089*
O3	0.4997 (3)	0.72271 (16)	0.16417 (17)	0.0439 (6)
O4	0.4061 (3)	0.12989 (17)	0.70360 (19)	0.0500 (7)
H15	0.4361	0.1660	0.7536	0.075*
H16	0.4622	0.0787	0.7172	0.075*
N1	0.5896 (3)	0.66104 (17)	0.0155 (2)	0.0349 (6)
H1A	0.5932	0.6652	−0.0500	0.042*
N2	0.6628 (3)	0.58384 (19)	0.0659 (2)	0.0364 (7)
C1	0.4411 (4)	0.8144 (2)	0.0139 (2)	0.0310 (7)
C2	0.4779 (4)	0.8365 (2)	−0.0866 (3)	0.0343 (8)
H2A	0.5545	0.7982	−0.1215	0.041*
C3	0.4030 (5)	0.9141 (2)	−0.1350 (3)	0.0379 (8)
C4	0.2885 (4)	0.9734 (2)	−0.0836 (3)	0.0375 (8)
C5	0.2535 (4)	0.9517 (2)	0.0159 (3)	0.0435 (9)
H5	0.1770	0.9901	0.0508	0.052*
C6	0.3290 (4)	0.8743 (2)	0.0652 (3)	0.0378 (8)
H6	0.3050	0.8619	0.1331	0.045*
C7	0.5118 (4)	0.7306 (2)	0.0699 (3)	0.0335 (7)
C8	0.7358 (4)	0.5211 (2)	0.0103 (3)	0.0357 (8)
H8	0.7339	0.5285	−0.0604	0.043*
C9	0.8220 (4)	0.4381 (2)	0.0570 (3)	0.0344 (8)
C10	0.8858 (4)	0.3655 (2)	−0.0043 (3)	0.0419 (9)
H10	0.8742	0.3708	−0.0750	0.050*
C11	0.9666 (4)	0.2852 (2)	0.0382 (3)	0.0456 (9)
H11	1.0085	0.2367	−0.0034	0.055*
C12	0.9835 (4)	0.2786 (2)	0.1423 (3)	0.0423 (9)
C13	0.9267 (5)	0.3516 (3)	0.2044 (3)	0.0454 (9)
H13	0.9435	0.3474	0.2750	0.054*
C14	0.8455 (4)	0.4301 (2)	0.1623 (3)	0.0412 (8)
H14	0.8056	0.4786	0.2045	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0630 (3)	0.0516 (3)	0.0988 (5)	0.02020 (19)	0.0116 (3)	0.0259 (2)
O1	0.0711 (18)	0.0459 (15)	0.0516 (17)	0.0227 (13)	0.0093 (14)	0.0098 (13)
O2	0.114 (2)	0.0323 (13)	0.0316 (14)	0.0185 (14)	0.0206 (14)	0.0067 (11)
O3	0.0707 (16)	0.0354 (13)	0.0260 (14)	0.0040 (11)	0.0064 (12)	−0.0001 (10)
O4	0.0816 (18)	0.0311 (12)	0.0372 (14)	0.0045 (12)	−0.0024 (13)	0.0006 (11)
N1	0.0483 (16)	0.0296 (14)	0.0268 (15)	0.0035 (12)	0.0031 (12)	0.0025 (12)
N2	0.0420 (16)	0.0286 (14)	0.0386 (17)	0.0000 (12)	0.0029 (13)	0.0034 (13)
C1	0.0393 (17)	0.0260 (15)	0.0277 (18)	−0.0034 (13)	0.0021 (14)	−0.0021 (14)
C2	0.0491 (19)	0.0243 (16)	0.0302 (19)	0.0000 (14)	0.0104 (15)	−0.0018 (14)
C3	0.058 (2)	0.0268 (17)	0.0290 (19)	−0.0029 (15)	0.0086 (16)	0.0006 (15)
C4	0.0461 (19)	0.0287 (17)	0.038 (2)	0.0047 (15)	0.0014 (16)	−0.0007 (15)
C5	0.050 (2)	0.040 (2)	0.042 (2)	0.0093 (16)	0.0136 (17)	−0.0038 (17)
C6	0.048 (2)	0.0382 (18)	0.0273 (18)	0.0036 (16)	0.0103 (15)	0.0009 (15)
C7	0.0406 (18)	0.0287 (17)	0.031 (2)	−0.0053 (14)	0.0025 (15)	−0.0014 (15)
C8	0.0424 (18)	0.0322 (18)	0.0326 (19)	−0.0023 (15)	0.0033 (15)	0.0000 (15)
C9	0.0321 (16)	0.0298 (17)	0.042 (2)	−0.0036 (13)	0.0041 (15)	0.0006 (15)
C10	0.046 (2)	0.0390 (19)	0.041 (2)	−0.0008 (16)	0.0039 (17)	−0.0066 (17)
C11	0.0411 (19)	0.0340 (19)	0.062 (3)	0.0026 (15)	0.0049 (18)	−0.0069 (18)
C12	0.0335 (18)	0.0343 (19)	0.059 (3)	0.0005 (14)	0.0078 (17)	0.0066 (18)
C13	0.047 (2)	0.052 (2)	0.037 (2)	0.0060 (17)	0.0031 (17)	0.0067 (18)
C14	0.046 (2)	0.0391 (19)	0.039 (2)	0.0044 (16)	0.0041 (16)	−0.0044 (16)

Geometric parameters (Å, º) top

Br1—C12	1.893 (3)	C3—C4	1.402 (5)
O1—C4	1.348 (4)	C4—C5	1.372 (5)
O1—H1	0.8200	C5—C6	1.374 (5)
O2—C3	1.374 (4)	C5—H5	0.9300
O2—H2	0.8200	C6—H6	0.9300
O3—C7	1.244 (4)	C8—C9	1.458 (5)
O4—H15	0.8499	C8—H8	0.9300
O4—H16	0.8500	C9—C10	1.387 (5)
N1—C7	1.353 (4)	C9—C14	1.387 (5)
N1—N2	1.372 (4)	C10—C11	1.387 (5)
N1—H1A	0.8600	C10—H10	0.9300
N2—C8	1.277 (4)	C11—C12	1.367 (5)
C1—C2	1.387 (5)	C11—H11	0.9300
C1—C6	1.393 (4)	C12—C13	1.378 (5)
C1—C7	1.471 (4)	C13—C14	1.367 (5)
C2—C3	1.369 (5)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14	0.9300

C4—O1—H1	109.5	O3—C7—N1	120.5 (3)
C3—O2—H2	109.5	O3—C7—C1	121.6 (3)
H15—O4—H16	101.6	N1—C7—C1	117.9 (3)
C7—N1—N2	119.3 (3)	N2—C8—C9	120.4 (3)
C7—N1—H1A	120.3	N2—C8—H8	119.8
N2—N1—H1A	120.3	C9—C8—H8	119.8
C8—N2—N1	116.3 (3)	C10—C9—C14	118.4 (3)
C2—C1—C6	118.4 (3)	C10—C9—C8	119.9 (3)
C2—C1—C7	124.1 (3)	C14—C9—C8	121.6 (3)
C6—C1—C7	117.5 (3)	C11—C10—C9	121.1 (3)
C3—C2—C1	120.9 (3)	C11—C10—H10	119.4
C3—C2—H2A	119.5	C9—C10—H10	119.4
C1—C2—H2A	119.5	C12—C11—C10	118.8 (3)
C2—C3—O2	123.3 (3)	C12—C11—H11	120.6
C2—C3—C4	120.6 (3)	C10—C11—H11	120.6
O2—C3—C4	116.1 (3)	C11—C12—C13	121.0 (3)
O1—C4—C5	119.2 (3)	C11—C12—Br1	120.8 (3)
O1—C4—C3	122.5 (3)	C13—C12—Br1	118.2 (3)
C5—C4—C3	118.3 (3)	C14—C13—C12	119.9 (3)
C4—C5—C6	121.4 (3)	C14—C13—H13	120.0
C4—C5—H5	119.3	C12—C13—H13	120.0
C6—C5—H5	119.3	C13—C14—C9	120.7 (3)
C5—C6—C1	120.4 (3)	C13—C14—H14	119.7
C5—C6—H6	119.8	C9—C14—H14	119.7
C1—C6—H6	119.8

C7—N1—N2—C8	−179.3 (3)	C6—C1—C7—O3	−13.4 (5)
C6—C1—C2—C3	−1.4 (5)	C2—C1—C7—N1	−13.4 (5)
C7—C1—C2—C3	177.9 (3)	C6—C1—C7—N1	165.9 (3)
C1—C2—C3—O2	178.7 (3)	N1—N2—C8—C9	178.0 (3)
C1—C2—C3—C4	0.6 (5)	N2—C8—C9—C10	173.5 (3)
C2—C3—C4—O1	−179.1 (3)	N2—C8—C9—C14	−7.8 (5)
O2—C3—C4—O1	2.7 (5)	C14—C9—C10—C11	2.0 (5)
C2—C3—C4—C5	−0.2 (5)	C8—C9—C10—C11	−179.3 (3)
O2—C3—C4—C5	−178.4 (3)	C9—C10—C11—C12	−0.3 (5)
O1—C4—C5—C6	179.5 (3)	C10—C11—C12—C13	−2.1 (5)
C3—C4—C5—C6	0.5 (5)	C10—C11—C12—Br1	177.7 (2)
C4—C5—C6—C1	−1.4 (5)	C11—C12—C13—C14	2.8 (5)
C2—C1—C6—C5	1.8 (5)	Br1—C12—C13—C14	−177.0 (3)
C7—C1—C6—C5	−177.5 (3)	C12—C13—C14—C9	−1.1 (5)
N2—N1—C7—O3	−3.3 (5)	C10—C9—C14—C13	−1.3 (5)
N2—N1—C7—C1	177.5 (2)	C8—C9—C14—C13	−180.0 (3)
C2—C1—C7—O3	167.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.30	2.734 (3)	114
O4—H16···O2ⁱ	0.85	2.03	2.760 (3)	143
O4—H15···O3ⁱⁱ	0.85	1.94	2.761 (3)	163
O2—H2···O3ⁱⁱⁱ	0.82	1.91	2.675 (3)	154
O1—H1···O4^iv	0.82	2.16	2.929 (4)	155
N1—H1A···O4^v	0.86	2.07	2.898 (4)	162

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrN₂O₃·H₂O
M_r	353.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8119 (5), 13.8504 (9), 13.0764 (9)
β (°)	91.708 (1)
V (Å³)	1414.21 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.18 × 0.16 × 0.15

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1996)
T_min, T_max	0.621, 0.668
No. of measured, independent and observed [I > 2σ(I)] reflections	7384, 2511, 1810
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 1.02
No. of reflections	2511
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.69

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.30	2.734 (3)	114
O4—H16···O2ⁱ	0.85	2.03	2.760 (3)	143
O4—H15···O3ⁱⁱ	0.85	1.94	2.761 (3)	163
O2—H2···O3ⁱⁱⁱ	0.82	1.91	2.675 (3)	154
O1—H1···O4^iv	0.82	2.16	2.929 (4)	155
N1—H1A···O4^v	0.86	2.07	2.898 (4)	162

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

References

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