N′-(5-Bromo-2-hydroxy­benzyl­idene)-4-chloro­benzohydrazide

Zhou, C.-S.; Yang, T.

doi:10.1107/S160053681000752X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o751

doi:10.1107/S160053681000752X

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N′-(5-Bromo-2-hydroxybenzylidene)-4-chlorobenzohydrazide

Cong-Shan Zhou ^a and Tao Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006, People's Republic of China
^*Correspondence e-mail: zhoucongsh@gmail.com

(Received 25 February 2010; accepted 27 February 2010; online 6 March 2010)

The title Schiff base, C₁₄H₁₀BrClN₂O₂, exists in a trans configuration with respect to the C=N bond and the dihedral angle between the two benzene rings is 0.8 (2)°. There is an intramolecular O—H⋯N hydrogen bond in the molecule, which generates an S(6) loop. In the crystal, intermolecular N—H⋯O hydrogen bonds link adjacent molecules into extended chains propagating along the c-axis direction.

Related literature

For background to the biological properties of Schiff bases, see: Ritter et al. (2009 ); Bagihalli et al. (2008 ). For related structures, see: Fun et al. (2008 ); Shafiq et al. (2009 ); Goh et al. (2010 ). Zhou et al. (2009 ); Zhou & Yang (2009 , 2010a ,b ).

Experimental

Crystal data

C₁₄H₁₀BrClN₂O₂
M_r = 353.60
Monoclinic, P 2₁ /n
a = 5.893 (2) Å
b = 31.708 (11) Å
c = 7.437 (3) Å
β = 92.017 (8)°
V = 1388.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 3.15 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.616, T_max = 0.649
7670 measured reflections
2661 independent reflections
1555 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.02
2661 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.51 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	1.93	2.642 (4)	145
N2—H2⋯O2ⁱ	0.90 (1)	1.96 (2)	2.829 (3)	163 (4)
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/S160053681000752X/hb5343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000752X/hb5343Isup2.hkl

checkCIF report

Comment top

Some Schiff bases possess biological properties, such as antibacterial, antimicrobial, and antitumor activities (Ritter et al., 2009; Bagihalli et al., 2008). Recently, a large number of Schiff bases derived from the reaction of aldehydes with benzohydrazides have been reported (Fun et al., 2008; Shafiq et al., 2009; Goh et al., 2010). As a continuation of these studies, in this paper, the crystal structure of the title Schiff base, (I), derived from the condensing of 5-bromo-2-hydroxybenzaldehyde with 4-chlorobenzohydrazide in methanol is reported.

In the title compound, Fig. 1, all the bond lengths are comparable with those observed in other similar compounds (Zhou et al., 2009; Zhou & Yang, 2009; Zhou & Yang, 2010a,b). The molecule exists in a trans configuration with respect to the acyclic C═N bond. There is an intramolecular O—H···N hydrogen bond in the molecule (Table 1). The dihedral angle between the two benzene rings is 0.8 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link adjacent molecules into extended chains along the c axis (Table 1 and Fig. 2).

Related literature top

For background to the biological properties of Schiff bases, see: Ritter et al. (2009); Bagihalli et al. (2008). For related structures, see: Fun et al. (2008); Shafiq et al. (2009); Goh et al. (2010). Zhou et al. (2009); Zhou & Yang (2009, 2010a,b).

Experimental top

5-Bromo-2-hydroxybenzaldehyde (1.0 mmol, 201 mg) and 4-chlorobenzohydrazide (1.0 mmol, 170 mg) were dissolved in a methanol solution (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding colourless blocks of (I).

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.
	Fig. 2. The packing of (I), viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

N'-(5-Bromo-2-hydroxybenzylidene)-4-chlorobenzohydrazide top

Crystal data top

C₁₄H₁₀BrClN₂O₂	F(000) = 704
M_r = 353.60	D_x = 1.691 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1461 reflections
a = 5.893 (2) Å	θ = 2.5–24.5°
b = 31.708 (11) Å	µ = 3.15 mm⁻¹
c = 7.437 (3) Å	T = 298 K
β = 92.017 (8)°	Block, colourless
V = 1388.8 (9) Å³	0.17 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	2661 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 25.9°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.616, T_max = 0.649	k = −38→36
7670 measured reflections	l = −9→5

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0584P)²] where P = (F_o² + 2F_c²)/3
2661 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 0.58 e Å⁻³
1 restraint	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₄H₁₀BrClN₂O₂	V = 1388.8 (9) Å³
M_r = 353.60	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.893 (2) Å	µ = 3.15 mm⁻¹
b = 31.708 (11) Å	T = 298 K
c = 7.437 (3) Å	0.17 × 0.15 × 0.15 mm
β = 92.017 (8)°

Data collection top

Bruker SMART 1000 CCD diffractometer	2661 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1555 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.649	R_int = 0.043
7670 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.58 e Å⁻³
2661 reflections	Δρ_min = −0.51 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	0.22343 (9)	0.007519 (14)	0.69748 (8)	0.0934 (3)
Cl1	−0.31634 (18)	0.42871 (3)	0.73651 (14)	0.0726 (4)
N1	0.3457 (5)	0.20659 (9)	0.8247 (3)	0.0456 (7)
N2	0.2126 (5)	0.24185 (9)	0.7948 (4)	0.0508 (8)
O1	0.7208 (4)	0.16526 (8)	0.9180 (4)	0.0621 (7)
H1	0.6422	0.1863	0.8999	0.093*
O2	0.4098 (4)	0.27888 (7)	1.0046 (3)	0.0604 (7)
C1	0.3853 (6)	0.13282 (10)	0.7884 (4)	0.0418 (8)
C2	0.6036 (6)	0.13063 (12)	0.8651 (4)	0.0479 (9)
C3	0.7070 (6)	0.09163 (14)	0.8872 (5)	0.0617 (11)
H3	0.8539	0.0902	0.9369	0.074*
C4	0.5988 (7)	0.05541 (13)	0.8381 (5)	0.0665 (11)
H4	0.6702	0.0295	0.8553	0.080*
C5	0.3815 (7)	0.05740 (11)	0.7622 (5)	0.0561 (10)
C6	0.2773 (6)	0.09556 (11)	0.7367 (4)	0.0485 (9)
H6	0.1320	0.0966	0.6840	0.058*
C7	0.2645 (6)	0.17218 (11)	0.7635 (4)	0.0446 (9)
H7	0.1247	0.1723	0.7015	0.054*
C8	0.2553 (6)	0.27691 (10)	0.8913 (5)	0.0430 (8)
C9	0.1038 (5)	0.31345 (10)	0.8524 (4)	0.0385 (8)
C10	−0.1114 (6)	0.30975 (11)	0.7758 (4)	0.0470 (9)
H10	−0.1700	0.2832	0.7491	0.056*
C11	−0.2404 (6)	0.34505 (12)	0.7387 (5)	0.0506 (9)
H11	−0.3850	0.3425	0.6856	0.061*
C12	−0.1537 (6)	0.38413 (11)	0.7806 (4)	0.0471 (9)
C13	0.0603 (6)	0.38863 (11)	0.8575 (4)	0.0511 (9)
H13	0.1184	0.4153	0.8838	0.061*
C14	0.1861 (6)	0.35333 (11)	0.8947 (4)	0.0465 (9)
H14	0.3297	0.3561	0.9495	0.056*
H2	0.107 (5)	0.2405 (12)	0.705 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1054 (5)	0.0446 (3)	0.1297 (5)	−0.0038 (2)	−0.0018 (3)	0.0039 (3)
Cl1	0.0765 (8)	0.0562 (7)	0.0844 (8)	0.0210 (5)	−0.0079 (6)	−0.0056 (5)
N1	0.0462 (18)	0.0458 (18)	0.0441 (17)	0.0073 (14)	−0.0094 (13)	−0.0009 (13)
N2	0.055 (2)	0.0462 (19)	0.050 (2)	0.0044 (15)	−0.0177 (14)	−0.0068 (15)
O1	0.0459 (15)	0.0723 (18)	0.0670 (18)	0.0040 (13)	−0.0124 (13)	−0.0054 (15)
O2	0.0676 (17)	0.0470 (15)	0.0639 (17)	−0.0021 (13)	−0.0335 (14)	0.0001 (12)
C1	0.043 (2)	0.046 (2)	0.037 (2)	0.0041 (16)	0.0006 (15)	0.0014 (15)
C2	0.046 (2)	0.057 (2)	0.040 (2)	0.0024 (18)	0.0003 (17)	−0.0009 (17)
C3	0.044 (2)	0.079 (3)	0.062 (3)	0.019 (2)	−0.0053 (18)	0.008 (2)
C4	0.068 (3)	0.060 (3)	0.071 (3)	0.024 (2)	0.003 (2)	0.008 (2)
C5	0.065 (3)	0.047 (2)	0.057 (2)	0.0047 (19)	0.006 (2)	0.0083 (17)
C6	0.048 (2)	0.045 (2)	0.052 (2)	0.0037 (16)	−0.0027 (17)	0.0042 (16)
C7	0.043 (2)	0.048 (2)	0.042 (2)	0.0044 (17)	−0.0053 (16)	0.0019 (16)
C8	0.041 (2)	0.043 (2)	0.045 (2)	−0.0061 (15)	−0.0073 (17)	0.0019 (16)
C9	0.042 (2)	0.0411 (19)	0.0325 (18)	−0.0023 (15)	−0.0044 (15)	−0.0008 (15)
C10	0.051 (2)	0.042 (2)	0.048 (2)	−0.0024 (16)	−0.0004 (17)	−0.0065 (16)
C11	0.048 (2)	0.053 (3)	0.051 (2)	0.0031 (18)	−0.0027 (17)	−0.0043 (17)
C12	0.056 (2)	0.045 (2)	0.041 (2)	0.0075 (17)	0.0085 (17)	−0.0042 (16)
C13	0.060 (3)	0.041 (2)	0.052 (2)	−0.0033 (18)	0.0023 (18)	−0.0062 (17)
C14	0.045 (2)	0.050 (2)	0.045 (2)	−0.0046 (17)	−0.0068 (16)	−0.0041 (16)

Geometric parameters (Å, º) top

Br1—C5	1.889 (4)	C4—H4	0.9300
Cl1—C12	1.733 (4)	C5—C6	1.367 (5)
N1—C7	1.269 (4)	C6—H6	0.9300
N1—N2	1.379 (4)	C7—H7	0.9300
N2—C8	1.342 (4)	C8—C9	1.485 (4)
N2—H2	0.898 (10)	C9—C10	1.377 (4)
O1—C2	1.349 (4)	C9—C14	1.387 (4)
O1—H1	0.8200	C10—C11	1.376 (5)
O2—C8	1.220 (4)	C10—H10	0.9300
C1—C6	1.390 (5)	C11—C12	1.372 (5)
C1—C2	1.391 (5)	C11—H11	0.9300
C1—C7	1.445 (5)	C12—C13	1.373 (5)
C2—C3	1.386 (5)	C13—C14	1.366 (5)
C3—C4	1.358 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.383 (5)

C7—N1—N2	115.7 (3)	N1—C7—H7	119.4
C8—N2—N1	119.4 (3)	C1—C7—H7	119.4
C8—N2—H2	123 (3)	O2—C8—N2	122.2 (3)
N1—N2—H2	117 (3)	O2—C8—C9	121.6 (3)
C2—O1—H1	109.5	N2—C8—C9	116.2 (3)
C6—C1—C2	118.6 (3)	C10—C9—C14	118.8 (3)
C6—C1—C7	118.7 (3)	C10—C9—C8	123.6 (3)
C2—C1—C7	122.7 (3)	C14—C9—C8	117.7 (3)
O1—C2—C3	118.3 (3)	C11—C10—C9	120.6 (3)
O1—C2—C1	122.4 (3)	C11—C10—H10	119.7
C3—C2—C1	119.3 (3)	C9—C10—H10	119.7
C4—C3—C2	121.5 (4)	C12—C11—C10	119.3 (3)
C4—C3—H3	119.2	C12—C11—H11	120.3
C2—C3—H3	119.2	C10—C11—H11	120.3
C3—C4—C5	119.4 (4)	C11—C12—C13	121.2 (3)
C3—C4—H4	120.3	C11—C12—Cl1	119.6 (3)
C5—C4—H4	120.3	C13—C12—Cl1	119.2 (3)
C6—C5—C4	120.1 (4)	C14—C13—C12	118.9 (3)
C6—C5—Br1	119.4 (3)	C14—C13—H13	120.5
C4—C5—Br1	120.5 (3)	C12—C13—H13	120.5
C5—C6—C1	121.0 (3)	C13—C14—C9	121.2 (3)
C5—C6—H6	119.5	C13—C14—H14	119.4
C1—C6—H6	119.5	C9—C14—H14	119.4
N1—C7—C1	121.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.93	2.642 (4)	145
N2—H2···O2ⁱ	0.90 (1)	1.96 (2)	2.829 (3)	163 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrClN₂O₂
M_r	353.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.893 (2), 31.708 (11), 7.437 (3)
β (°)	92.017 (8)
V (Å³)	1388.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.15
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.616, 0.649
No. of measured, independent and observed [I > 2σ(I)] reflections	7670, 2661, 1555
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.02
No. of reflections	2661
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)	0.58, −0.51

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	1.93	2.642 (4)	145
N2—H2···O2ⁱ	0.898 (10)	1.957 (15)	2.829 (3)	163 (4)

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

Acknowledgements

The authors acknowledge support of this project by Hunan Provincial Natural Science Foundation of China Scientific Research (09JJ6022) and the Fund of Hunan Provincial Education Department (08B031), People's Republic of China.

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