N′-[(E)-1-(5-Bromo-2-hydroxy­phen­yl)ethyl­idene]benzohydrazide

Zheng, C.-Z.; Ji, C.-Y.; Chang, X.-L.; Zhang, L.

doi:10.1107/S1600536808039755

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2487

doi:10.1107/S1600536808039755

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N′-[(E)-1-(5-Bromo-2-hydroxyphenyl)ethylidene]benzohydrazide

Chang-Zheng Zheng,^a Chang-You Ji,^a ^* Xiu-Li Chang ^b and Li-qin Zhang ^a

^aCollege of Environmental and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China, and ^bDepartment of Materials Science and Chemical Engineering, Sichuan University of Science and Engineering , 643000 Zigong, Sichuan, People's Republic of China
^*Correspondence e-mail: jichangyou789456@126.com

(Received 23 November 2008; accepted 25 November 2008; online 29 November 2008)

The C=N double bond in the title compound, C₁₅H₁₃BrN₂O₂, is trans E configured and the dihedral angle between the aromatic ring planes is 22.3 (1)°. The crystal structure is stabilized by intramolecular O—H⋯O and intermolecular N—H⋯O hydrogen bonds.

Related literature

For aroylhydrazones and their biological activity, see: Singh et al. (1982 ); Salem (1998 ); Carcelli et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₂
M_r = 333.18
Monoclinic, P 2₁ /c
a = 7.3761 (15) Å
b = 28.270 (6) Å
c = 8.6089 (13) Å
β = 116.928 (12)°
V = 1600.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.57 mm⁻¹
T = 298 (2) K
0.12 × 0.08 × 0.06 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.748, T_max = 0.861
8028 measured reflections
2830 independent reflections
1490 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.188
S = 1.01
2830 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.37 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	1.85	2.522 (6)	138
N2—H2⋯O2ⁱ	0.86	2.14	2.889 (6)	146
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 I, global. DOI: 10.1107/S1600536808039755/bt2814sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039755/bt2814Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.

The title molecule displays a trans configured C=N double bond (Fig. 1). The crystal structure is stabilized by intramolecular O—H···O and intermolecular N—H···O hydrogen bonds (Table 1. and Fig. 2).

Related literature top

For aroylhydrazones and their biological activity, see: Singh et al. (1982); Salem (1998); Carcelli et al. (1995); .

Experimental top

Benzoylhydrazine (0.02 mol, 2.72 g) was dissolved in anhydrous ethanol (50 ml), and 1-(5-bromo-2-hydroxyphenyl)ethanone (0.02 mol, 4.30 g) was added. The reaction mixture was refluxed for 6 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 85%). The compound (2.0 mmol, 0.67 g) was dissolved in dimethylformamide (30 ml) and kept at room temperature for 30 d to obtain yellow single crystals suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (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 the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound. Dashed lines show hydrogen bonds.

N'-[(E)-1-(5-Bromo-2-hydroxyphenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₃BrN₂O₂	F(000) = 672
M_r = 333.18	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1189 reflections
a = 7.3761 (15) Å	θ = 2.9–20.7°
b = 28.270 (6) Å	µ = 2.57 mm⁻¹
c = 8.6089 (13) Å	T = 298 K
β = 116.928 (12)°	Block, yellow
V = 1600.5 (5) Å³	0.12 × 0.08 × 0.06 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	1490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.1°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.748, T_max = 0.861	k = −33→33
8028 measured reflections	l = −7→10

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.089P)² + 0.7896P] where P = (F_o² + 2F_c²)/3
2830 reflections	(Δ/σ)_max = 0.002
183 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₂	V = 1600.5 (5) Å³
M_r = 333.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3761 (15) Å	µ = 2.57 mm⁻¹
b = 28.270 (6) Å	T = 298 K
c = 8.6089 (13) Å	0.12 × 0.08 × 0.06 mm
β = 116.928 (12)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2830 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1490 reflections with I > 2σ(I)
T_min = 0.748, T_max = 0.861	R_int = 0.062
8028 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.01	Δρ_max = 0.87 e Å⁻³
2830 reflections	Δρ_min = −0.37 e Å⁻³
183 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	0.81952 (14)	1.00196 (2)	0.69361 (11)	0.0935 (4)
O1	0.6647 (7)	0.79484 (14)	0.7321 (5)	0.0613 (11)
H1	0.6183	0.7820	0.6365	0.092*
O2	0.3297 (6)	0.70963 (13)	0.4419 (5)	0.0602 (11)
N1	0.4384 (6)	0.79657 (14)	0.4079 (5)	0.0391 (10)
N2	0.3180 (6)	0.76994 (15)	0.2660 (5)	0.0416 (10)
H2	0.2720	0.7810	0.1620	0.050*
C1	0.6935 (8)	0.84139 (19)	0.7143 (6)	0.0442 (13)
C2	0.6016 (8)	0.86503 (17)	0.5556 (6)	0.0390 (12)
C3	0.6426 (8)	0.91292 (19)	0.5540 (7)	0.0497 (14)
H3	0.5829	0.9294	0.4491	0.060*
C4	0.7677 (8)	0.9363 (2)	0.7018 (8)	0.0555 (15)
C5	0.8592 (10)	0.9132 (2)	0.8592 (8)	0.0655 (17)
H5	0.9461	0.9293	0.9598	0.079*
C6	0.8202 (9)	0.8661 (2)	0.8654 (8)	0.0658 (18)
H6	0.8789	0.8503	0.9716	0.079*
C7	0.4633 (7)	0.84066 (17)	0.3902 (6)	0.0370 (12)
C8	0.2737 (8)	0.72504 (18)	0.2962 (7)	0.0430 (13)
C9	0.1524 (8)	0.69622 (19)	0.1385 (7)	0.0460 (13)
C10	0.0099 (8)	0.7153 (2)	−0.0181 (7)	0.0509 (14)
H10	−0.0132	0.7477	−0.0273	0.061*
C11	−0.0978 (9)	0.6865 (2)	−0.1603 (8)	0.0581 (16)
H11	−0.1931	0.6994	−0.2649	0.070*
C12	−0.0621 (10)	0.6383 (2)	−0.1449 (9)	0.0641 (17)
H12	−0.1335	0.6186	−0.2400	0.077*
C13	0.0790 (11)	0.6191 (2)	0.0110 (9)	0.0618 (16)
H13	0.1027	0.5866	0.0200	0.074*
C14	0.1832 (9)	0.64743 (19)	0.1507 (7)	0.0496 (14)
H14	0.2760	0.6342	0.2557	0.060*
C15	0.3682 (9)	0.86765 (19)	0.2249 (6)	0.0535 (15)
H15A	0.4673	0.8733	0.1836	0.080*
H15B	0.3186	0.8973	0.2445	0.080*
H15C	0.2571	0.8498	0.1395	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1011 (7)	0.0462 (5)	0.0962 (7)	−0.0133 (4)	0.0123 (5)	−0.0172 (4)
O1	0.073 (3)	0.058 (3)	0.040 (2)	−0.003 (2)	0.014 (2)	0.0092 (19)
O2	0.103 (3)	0.040 (2)	0.041 (2)	0.000 (2)	0.037 (2)	0.0038 (17)
N1	0.051 (3)	0.036 (3)	0.029 (2)	0.002 (2)	0.0173 (19)	−0.0012 (19)
N2	0.054 (3)	0.037 (3)	0.032 (2)	−0.006 (2)	0.019 (2)	−0.0022 (19)
C1	0.043 (3)	0.045 (3)	0.037 (3)	−0.003 (2)	0.011 (2)	0.004 (2)
C2	0.034 (3)	0.039 (3)	0.044 (3)	0.002 (2)	0.017 (2)	−0.005 (2)
C3	0.047 (3)	0.049 (3)	0.040 (3)	0.008 (3)	0.009 (3)	−0.005 (3)
C4	0.047 (3)	0.048 (4)	0.062 (4)	0.001 (3)	0.015 (3)	−0.014 (3)
C5	0.064 (4)	0.067 (4)	0.051 (4)	−0.005 (3)	0.013 (3)	−0.020 (3)
C6	0.062 (4)	0.079 (5)	0.040 (3)	0.002 (3)	0.008 (3)	−0.003 (3)
C7	0.044 (3)	0.037 (3)	0.028 (3)	0.004 (2)	0.014 (2)	−0.001 (2)
C8	0.064 (4)	0.032 (3)	0.041 (3)	0.006 (3)	0.031 (3)	0.000 (2)
C9	0.057 (3)	0.043 (3)	0.049 (3)	−0.009 (3)	0.033 (3)	−0.004 (3)
C10	0.057 (3)	0.040 (3)	0.053 (4)	−0.006 (3)	0.022 (3)	0.004 (3)
C11	0.058 (4)	0.052 (4)	0.055 (4)	−0.013 (3)	0.017 (3)	−0.006 (3)
C12	0.070 (4)	0.062 (4)	0.064 (4)	−0.024 (3)	0.034 (4)	−0.027 (3)
C13	0.082 (4)	0.041 (3)	0.079 (5)	−0.009 (3)	0.050 (4)	−0.011 (3)
C14	0.066 (4)	0.036 (3)	0.053 (3)	−0.004 (3)	0.033 (3)	−0.003 (3)
C15	0.071 (4)	0.036 (3)	0.034 (3)	0.001 (3)	0.006 (3)	0.002 (2)

Geometric parameters (Å, º) top

Br1—C4	1.902 (6)	C6—H6	0.9300
O1—C1	1.353 (6)	C7—C15	1.482 (7)
O1—H1	0.8200	C8—C9	1.485 (7)
O2—C8	1.210 (6)	C9—C10	1.389 (7)
N1—C7	1.279 (6)	C9—C14	1.394 (7)
N1—N2	1.366 (5)	C10—C11	1.382 (7)
N2—C8	1.365 (6)	C10—H10	0.9300
N2—H2	0.8600	C11—C12	1.384 (8)
C1—C2	1.391 (7)	C11—H11	0.9300
C1—C6	1.397 (8)	C12—C13	1.383 (9)
C2—C3	1.389 (7)	C12—H12	0.9300
C2—C7	1.492 (7)	C13—C14	1.358 (8)
C3—C4	1.358 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.376 (8)	C15—H15A	0.9600
C5—C6	1.367 (9)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600

C1—O1—H1	109.5	O2—C8—C9	122.1 (5)
C7—N1—N2	120.1 (4)	N2—C8—C9	115.7 (4)
C8—N2—N1	117.2 (4)	C10—C9—C14	118.9 (5)
C8—N2—H2	121.4	C10—C9—C8	123.5 (5)
N1—N2—H2	121.4	C14—C9—C8	117.6 (5)
O1—C1—C2	123.2 (4)	C11—C10—C9	120.7 (6)
O1—C1—C6	117.0 (5)	C11—C10—H10	119.6
C2—C1—C6	119.8 (5)	C9—C10—H10	119.6
C3—C2—C1	117.8 (5)	C10—C11—C12	119.1 (6)
C3—C2—C7	119.9 (4)	C10—C11—H11	120.4
C1—C2—C7	122.3 (5)	C12—C11—H11	120.4
C4—C3—C2	121.6 (5)	C13—C12—C11	120.4 (5)
C4—C3—H3	119.2	C13—C12—H12	119.8
C2—C3—H3	119.2	C11—C12—H12	119.8
C3—C4—C5	120.9 (6)	C14—C13—C12	120.2 (6)
C3—C4—Br1	120.2 (5)	C14—C13—H13	119.9
C5—C4—Br1	118.9 (4)	C12—C13—H13	119.9
C6—C5—C4	118.9 (6)	C13—C14—C9	120.7 (6)
C6—C5—H5	120.6	C13—C14—H14	119.7
C4—C5—H5	120.6	C9—C14—H14	119.7
C5—C6—C1	121.0 (6)	C7—C15—H15A	109.5
C5—C6—H6	119.5	C7—C15—H15B	109.5
C1—C6—H6	119.5	H15A—C15—H15B	109.5
N1—C7—C15	125.8 (4)	C7—C15—H15C	109.5
N1—C7—C2	114.2 (4)	H15A—C15—H15C	109.5
C15—C7—C2	120.0 (5)	H15B—C15—H15C	109.5
O2—C8—N2	122.2 (5)

C7—N1—N2—C8	−170.7 (5)	C1—C2—C7—N1	−0.3 (7)
O1—C1—C2—C3	179.8 (5)	C3—C2—C7—C15	−0.6 (7)
C6—C1—C2—C3	0.8 (8)	C1—C2—C7—C15	179.6 (5)
O1—C1—C2—C7	−0.4 (8)	N1—N2—C8—O2	3.3 (7)
C6—C1—C2—C7	−179.4 (5)	N1—N2—C8—C9	−176.6 (4)
C1—C2—C3—C4	−0.2 (8)	O2—C8—C9—C10	149.0 (5)
C7—C2—C3—C4	−180.0 (5)	N2—C8—C9—C10	−31.1 (7)
C2—C3—C4—C5	0.2 (9)	O2—C8—C9—C14	−30.3 (8)
C2—C3—C4—Br1	−180.0 (4)	N2—C8—C9—C14	149.6 (5)
C3—C4—C5—C6	−0.8 (9)	C14—C9—C10—C11	−0.8 (8)
Br1—C4—C5—C6	179.3 (5)	C8—C9—C10—C11	179.9 (5)
C4—C5—C6—C1	1.5 (10)	C9—C10—C11—C12	0.0 (8)
O1—C1—C6—C5	179.4 (6)	C10—C11—C12—C13	0.3 (9)
C2—C1—C6—C5	−1.5 (9)	C11—C12—C13—C14	0.3 (9)
N2—N1—C7—C15	1.2 (8)	C12—C13—C14—C9	−1.2 (9)
N2—N1—C7—C2	−178.9 (4)	C10—C9—C14—C13	1.4 (8)
C3—C2—C7—N1	179.5 (5)	C8—C9—C14—C13	−179.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.522 (6)	138
N2—H2···O2ⁱ	0.86	2.14	2.889 (6)	146

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₂
M_r	333.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.3761 (15), 28.270 (6), 8.6089 (13)
β (°)	116.928 (12)
V (Å³)	1600.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.57
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.748, 0.861
No. of measured, independent and observed [I > 2σ(I)] reflections	8028, 2830, 1490
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.188, 1.01
No. of reflections	2830
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.37

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···N1	0.820	1.854	2.522 (6)	137.71
N2—H2···O2ⁱ	0.860	2.138	2.889 (6)	145.55

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

This project was supported by the Postgraduate Foundation of Xi'an Polytechnic University (grant No. Y05–2–09)

References

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