(E)-3-Bromo-N′-(5-bromo-2-hydroxy­benzyl­idene)benzohydrazide

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

doi:10.1107/S1600536808030675

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2061

doi:10.1107/S1600536808030675

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(E)-3-Bromo-N′-(5-bromo-2-hydroxybenzylidene)benzohydrazide

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

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

(Received 21 September 2008; accepted 23 September 2008; online 4 October 2008)

The title compound, C₁₄H₁₀Br₂N₂O₂, was synthesized by the reaction of 5-bromosalicylaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The dihedral angle between the two benzene rings is 10.5 (4)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds to form chains parallel to the c axis, and an intramolecular O—H⋯N interaction also occurs.

Related literature

For related structures, see: Cao (2007a ,b ); Yang et al. (2008 ); Zhen & Han (2005 ); Peng & Hou (2008 ); Tang (2008 ); Salhin et al. (2007 ); Yathirajan et al. (2007 ).

Experimental

Crystal data

C₁₄H₁₀Br₂N₂O₂
M_r = 398.06
Monoclinic, P 2₁ /n
a = 5.657 (5) Å
b = 32.08 (3) Å
c = 7.856 (7) Å
β = 93.217 (13)°
V = 1423 (2) Å³
Z = 4
Mo Kα radiation
μ = 5.70 mm⁻¹
T = 298 (2) K
0.13 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.525, T_max = 0.691
8526 measured reflections
3227 independent reflections
1830 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.108
S = 1.06
3227 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.63 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	1.92	2.638 (5)	145
N2—H2⋯O2ⁱ	0.90 (4)	1.98 (2)	2.838 (5)	160 (5)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536808030675/bx2182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030675/bx2182Isup2.hkl

checkCIF report

Comment top

We have recently reported some transition metal complexes with Schiff base ligands (Cao, 2007a,b) and a hydrazone compound (Yang et al., 2008). We report herein the crystal structure of the title compound, (I), derived from the reaction of 5-bromosalicylaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol.

In compound (I), Fig. 1, the dihedral angle between the two benzene rings is 10.5 (4)°. All the bond values are comparable to those in other similar hydrazones (Zhen & Han, 2005; Peng & Hou, 2008; Tang, 2008; Salhin et al., 2007; Yathirajan et al., 2007). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds, Table 1, to form chains parallel to the c axis, Fig. 2.

Related literature top

For related structures, see: Cao (2007a,b); Yang et al. (2008); Zhen & Han (2005); Peng & Hou (2008); Tang (2008); Salhin et al. (2007); Yathirajan et al. (2007).

Experimental top

The compound was prepared by refluxing equimolar quantities of 5-bromosalicylaldehyde with 3-bromobenzohydrazide in methanol. Colorless block-like crystals were formed when the solution was evaporated in air for about a week.

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. Dashed lines indicate intramolecular hydrogen bond.
	Fig. 2. The molecular packing of (I), viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

(E)-3-Bromo-N'-(5-bromo-2-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₀Br₂N₂O₂	F(000) = 776
M_r = 398.06	D_x = 1.858 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.657 (5) Å	Cell parameters from 1979 reflections
b = 32.08 (3) Å	θ = 2.5–25.3°
c = 7.856 (7) Å	µ = 5.70 mm⁻¹
β = 93.217 (13)°	T = 298 K
V = 1423 (2) Å³	Block, colorless
Z = 4	0.13 × 0.08 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3227 independent reflections
Radiation source: fine-focus sealed tube	1830 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→5
T_min = 0.525, T_max = 0.691	k = −40→40
8526 measured reflections	l = −10→8

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0261P)² + 2.1967P] where P = (F_o² + 2F_c²)/3
3227 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₄H₁₀Br₂N₂O₂	V = 1423 (2) Å³
M_r = 398.06	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.657 (5) Å	µ = 5.70 mm⁻¹
b = 32.08 (3) Å	T = 298 K
c = 7.856 (7) Å	0.13 × 0.08 × 0.07 mm
β = 93.217 (13)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3227 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1830 reflections with I > 2σ(I)
T_min = 0.525, T_max = 0.691	R_int = 0.044
8526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.36 e Å⁻³
3227 reflections	Δρ_min = −0.63 e Å⁻³
185 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
Br1	0.52024 (14)	0.488709 (18)	0.25097 (9)	0.0871 (3)
Br2	0.48529 (11)	0.059801 (15)	0.43970 (8)	0.0683 (2)
O1	0.9846 (6)	0.33095 (11)	0.5203 (5)	0.0569 (9)
H1	0.8927	0.3112	0.5117	0.085*
O2	0.6434 (6)	0.22201 (10)	0.6015 (4)	0.0607 (10)
N1	0.5896 (7)	0.29247 (11)	0.4185 (5)	0.0451 (9)
N2	0.4480 (7)	0.25766 (12)	0.3888 (5)	0.0482 (10)
C1	0.6522 (8)	0.36456 (14)	0.3700 (5)	0.0398 (10)
C2	0.8762 (8)	0.36571 (15)	0.4560 (6)	0.0455 (11)
C3	0.9919 (10)	0.40362 (17)	0.4777 (7)	0.0596 (14)
H3	1.1409	0.4045	0.5339	0.072*
C4	0.8888 (11)	0.43984 (17)	0.4170 (7)	0.0655 (15)
H4	0.9687	0.4650	0.4317	0.079*
C5	0.6659 (10)	0.43900 (15)	0.3338 (6)	0.0572 (13)
C6	0.5510 (9)	0.40199 (14)	0.3089 (6)	0.0485 (12)
H6	0.4034	0.4015	0.2505	0.058*
C7	0.5168 (8)	0.32626 (14)	0.3474 (6)	0.0437 (11)
H7	0.3758	0.3264	0.2806	0.052*
C8	0.4901 (8)	0.22345 (14)	0.4857 (6)	0.0431 (11)
C9	0.3421 (8)	0.18595 (14)	0.4356 (5)	0.0398 (10)
C10	0.4437 (8)	0.14749 (13)	0.4676 (5)	0.0419 (11)
H10	0.5908	0.1456	0.5261	0.050*
C11	0.3267 (9)	0.11187 (14)	0.4127 (6)	0.0472 (12)
C12	0.1049 (9)	0.11408 (17)	0.3310 (6)	0.0568 (14)
H12	0.0270	0.0899	0.2939	0.068*
C13	0.0001 (9)	0.15246 (17)	0.3051 (6)	0.0547 (13)
H13	−0.1513	0.1542	0.2530	0.066*
C14	0.1181 (8)	0.18839 (15)	0.3557 (6)	0.0471 (12)
H14	0.0472	0.2142	0.3362	0.057*
H2	0.339 (7)	0.2580 (16)	0.301 (5)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1139 (6)	0.0458 (3)	0.1014 (5)	0.0013 (3)	0.0025 (4)	0.0130 (3)
Br2	0.0836 (4)	0.0420 (3)	0.0786 (4)	−0.0039 (3)	−0.0013 (3)	0.0049 (3)
O1	0.038 (2)	0.064 (2)	0.067 (2)	−0.0044 (17)	−0.0141 (17)	0.0082 (19)
O2	0.068 (2)	0.0479 (19)	0.062 (2)	0.0009 (17)	−0.0422 (19)	0.0007 (16)
N1	0.049 (2)	0.039 (2)	0.045 (2)	−0.0038 (18)	−0.0151 (18)	−0.0009 (17)
N2	0.051 (3)	0.040 (2)	0.051 (2)	−0.0048 (19)	−0.027 (2)	0.0026 (18)
C1	0.034 (3)	0.050 (3)	0.035 (2)	−0.002 (2)	0.002 (2)	−0.006 (2)
C2	0.040 (3)	0.052 (3)	0.044 (3)	−0.007 (2)	0.001 (2)	−0.001 (2)
C3	0.050 (3)	0.069 (4)	0.058 (3)	−0.013 (3)	−0.007 (3)	−0.010 (3)
C4	0.073 (4)	0.057 (3)	0.065 (4)	−0.027 (3)	0.001 (3)	−0.006 (3)
C5	0.070 (4)	0.047 (3)	0.055 (3)	−0.007 (3)	0.006 (3)	0.002 (2)
C6	0.060 (3)	0.046 (3)	0.039 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C7	0.039 (3)	0.052 (3)	0.039 (3)	−0.003 (2)	−0.009 (2)	−0.002 (2)
C8	0.043 (3)	0.043 (3)	0.042 (3)	0.004 (2)	−0.011 (2)	−0.001 (2)
C9	0.042 (3)	0.049 (3)	0.027 (2)	−0.002 (2)	−0.009 (2)	0.0001 (19)
C10	0.039 (3)	0.049 (3)	0.037 (3)	0.000 (2)	−0.007 (2)	0.001 (2)
C11	0.057 (3)	0.046 (3)	0.039 (3)	−0.005 (2)	0.003 (2)	−0.001 (2)
C12	0.053 (3)	0.061 (3)	0.056 (3)	−0.022 (3)	−0.002 (3)	−0.002 (3)
C13	0.039 (3)	0.072 (4)	0.052 (3)	−0.011 (3)	−0.008 (2)	−0.004 (3)
C14	0.038 (3)	0.059 (3)	0.043 (3)	0.000 (2)	−0.001 (2)	0.001 (2)

Geometric parameters (Å, º) top

Br1—C5	1.893 (5)	C4—H4	0.9300
Br2—C11	1.902 (5)	C5—C6	1.362 (6)
O1—C2	1.356 (5)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C8	1.222 (5)	C8—C9	1.505 (6)
N1—C7	1.277 (5)	C9—C10	1.378 (6)
N1—N2	1.386 (5)	C9—C14	1.385 (6)
N2—C8	1.349 (6)	C10—C11	1.377 (6)
N2—H2	0.90 (4)	C10—H10	0.9300
C1—C2	1.402 (6)	C11—C12	1.379 (7)
C1—C6	1.403 (6)	C12—C13	1.376 (7)
C1—C7	1.453 (6)	C12—H12	0.9300
C2—C3	1.387 (6)	C13—C14	1.379 (6)
C3—C4	1.373 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.387 (7)

C2—O1—H1	109.5	N1—C7—H7	119.7
C7—N1—N2	116.2 (4)	C1—C7—H7	119.7
C8—N2—N1	118.6 (3)	O2—C8—N2	123.1 (4)
C8—N2—H2	122 (4)	O2—C8—C9	121.7 (4)
N1—N2—H2	119 (4)	N2—C8—C9	115.1 (4)
C2—C1—C6	118.9 (4)	C10—C9—C14	119.7 (4)
C2—C1—C7	122.5 (4)	C10—C9—C8	116.6 (4)
C6—C1—C7	118.6 (4)	C14—C9—C8	123.7 (4)
O1—C2—C3	118.3 (4)	C11—C10—C9	119.8 (4)
O1—C2—C1	122.3 (4)	C11—C10—H10	120.1
C3—C2—C1	119.3 (5)	C9—C10—H10	120.1
C4—C3—C2	120.7 (5)	C10—C11—C12	120.8 (5)
C4—C3—H3	119.6	C10—C11—Br2	118.6 (4)
C2—C3—H3	119.6	C12—C11—Br2	120.6 (4)
C3—C4—C5	120.3 (5)	C13—C12—C11	119.2 (5)
C3—C4—H4	119.9	C13—C12—H12	120.4
C5—C4—H4	119.9	C11—C12—H12	120.4
C6—C5—C4	119.9 (5)	C12—C13—C14	120.5 (5)
C6—C5—Br1	119.3 (4)	C12—C13—H13	119.8
C4—C5—Br1	120.8 (4)	C14—C13—H13	119.8
C5—C6—C1	120.9 (5)	C13—C14—C9	119.9 (5)
C5—C6—H6	119.5	C13—C14—H14	120.0
C1—C6—H6	119.5	C9—C14—H14	120.0
N1—C7—C1	120.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.638 (5)	145
N2—H2···O2ⁱ	0.90 (4)	1.98 (2)	2.838 (5)	160 (5)

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀Br₂N₂O₂
M_r	398.06
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.657 (5), 32.08 (3), 7.856 (7)
β (°)	93.217 (13)
V (Å³)	1423 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.70
Crystal size (mm)	0.13 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.525, 0.691
No. of measured, independent and observed [I > 2σ(I)] reflections	8526, 3227, 1830
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.108, 1.06
No. of reflections	3227
No. of parameters	185
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.63

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	1.92	2.638 (5)	145
N2—H2···O2ⁱ	0.90 (4)	1.98 (2)	2.838 (5)	160 (5)

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Acknowledgements

The Natural Scientific Research Foundation of the Education Office of Shanxi Province (project No. 07 J K177) 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
Peng, S.-J. & Hou, H.-Y. (2008). Acta Cryst. E64, o1864. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880. 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
Tang, C.-B. (2008). Acta Cryst. E64, o1382. Web of Science CSD CrossRef 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
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Sunil, K. & Bolte, M. (2007). Acta Cryst. E63, o2719. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhen, X.-L. & Han, J.-R. (2005). Acta Cryst. E61, o4360–o4361. Web of Science CSD CrossRef IUCr Journals Google Scholar