N′-[(E)-(5-Bromo-2-hydroxy­phen­yl)(phen­yl)methyl­idene]-4-chloro­benzo­hydrazide

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

doi:10.1107/S1600536809027949

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1944

doi:10.1107/S1600536809027949

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N′-[(E)-(5-Bromo-2-hydroxyphenyl)(phenyl)methylidene]-4-chlorobenzohydrazide

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

^aCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China, and ^bDepartment of Material 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 13 July 2009; accepted 16 July 2009; online 22 July 2009)

The Schiff base, C₂₀H₁₄BrClN₂O₂, displays a trans conformation with respect to the C=N double bond. The aromatic rings at either end of the –C(=O)–NH–N=C– fragment are nearly parallel [dihedral angle = 3.4 (5)°]. The hydroxy group forms an intramolecular hydrogen bond to the imino N atom.

Related literature

The chemistry of aroylhydrazones continues to attract much attention due to their ability to coordinate to metal ions (Singh et al., 1982 ; Salem, 1998 ) and their biological activity (Singh et al., 1982; Carcelli et al., 1995 ).

Experimental

Crystal data

C₂₀H₁₄BrClN₂O₂
M_r = 429.69
Triclinic, $[P \overline 1]$
a = 7.3664 (8) Å
b = 10.6894 (11) Å
c = 12.3029 (14) Å
α = 71.976 (2)°
β = 82.228 (2)°
γ = 85.466 (2)°
V = 912.05 (17) Å³
Z = 2
Mo Kα radiation
μ = 2.42 mm⁻¹
T = 273 K
0.20 × 0.16 × 0.13 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.644, T_max = 0.744
4841 measured reflections
3189 independent reflections
2467 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.085
S = 1.04
3189 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.44 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	1.84	2.554 (3)	145

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 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/S1600536809027949/ng2613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027949/ng2613Isup2.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, (I),was synthesized and its crystal structure is reported here.

The title molecule displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The crystal structure is stabilized by intramolecular O—H···N hydrogen bonds (Table).

Related literature top

Experimental top

4-chlorobenzohydrazide(0.02 mol,3.42 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,0.68 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 (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 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 compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

N'-[(E)-(5-Bromo-2-hydroxyphenyl)(phenyl)methylidene]-4- chlorobenzohydrazide top

Crystal data top

C₂₀H₁₄BrClN₂O₂	Z = 2
M_r = 429.69	F(000) = 432
Triclinic, P1	D_x = 1.565 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3664 (8) Å	Cell parameters from 1806 reflections
b = 10.6894 (11) Å	θ = 2.8–25.3°
c = 12.3029 (14) Å	µ = 2.42 mm⁻¹
α = 71.976 (2)°	T = 273 K
β = 82.228 (2)°	Block, yellow
γ = 85.466 (2)°	0.20 × 0.16 × 0.13 mm
V = 912.05 (17) Å³

Data collection top

Bruker SMART area-detector diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	2467 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.644, T_max = 0.744	k = −8→12
4841 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0366P)² + 0.3768P] where P = (F_o² + 2F_c²)/3
3189 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₀H₁₄BrClN₂O₂	γ = 85.466 (2)°
M_r = 429.69	V = 912.05 (17) Å³
Triclinic, P1	Z = 2
a = 7.3664 (8) Å	Mo Kα radiation
b = 10.6894 (11) Å	µ = 2.42 mm⁻¹
c = 12.3029 (14) Å	T = 273 K
α = 71.976 (2)°	0.20 × 0.16 × 0.13 mm
β = 82.228 (2)°

Data collection top

Bruker SMART area-detector diffractometer	3189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2467 reflections with I > 2σ(I)
T_min = 0.644, T_max = 0.744	R_int = 0.015
4841 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
3189 reflections	Δρ_min = −0.44 e Å⁻³
237 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	0.36717 (5)	1.17236 (4)	1.00467 (3)	0.06975 (17)
Cl1	0.08513 (13)	0.47987 (9)	0.23226 (8)	0.0729 (3)
O1	0.3069 (3)	1.25145 (19)	0.50596 (17)	0.0627 (6)
H1	0.2882	1.1830	0.4931	0.094*
O2	0.2209 (3)	1.0374 (2)	0.33927 (17)	0.0587 (6)
N1	0.2632 (3)	1.0045 (2)	0.55663 (18)	0.0454 (6)
N2	0.2388 (3)	0.9007 (2)	0.51767 (19)	0.0480 (6)
H2	0.2367	0.8215	0.5636	0.058*
C1	0.3457 (4)	1.1936 (3)	0.8483 (2)	0.0465 (7)
C2	0.3209 (4)	1.0858 (3)	0.8134 (2)	0.0432 (6)
H2A	0.3141	1.0027	0.8673	0.052*
C3	0.3060 (3)	1.0998 (2)	0.6988 (2)	0.0389 (6)
C4	0.3189 (4)	1.2264 (3)	0.6188 (2)	0.0455 (7)
C5	0.3465 (4)	1.3328 (3)	0.6566 (3)	0.0540 (8)
H5	0.3564	1.4163	0.6036	0.065*
C6	0.3595 (4)	1.3169 (3)	0.7695 (3)	0.0534 (8)
H6	0.3775	1.3891	0.7932	0.064*
C7	0.2801 (4)	0.9829 (3)	0.6636 (2)	0.0397 (6)
C8	0.2759 (4)	0.8493 (2)	0.7500 (2)	0.0380 (6)
C9	0.4302 (4)	0.7655 (3)	0.7577 (2)	0.0474 (7)
H9	0.5367	0.7920	0.7083	0.057*
C10	0.4261 (5)	0.6424 (3)	0.8389 (3)	0.0544 (8)
H10	0.5296	0.5861	0.8433	0.065*
C11	0.2707 (5)	0.6030 (3)	0.9127 (3)	0.0524 (8)
H11	0.2690	0.5206	0.9677	0.063*
C12	0.1173 (4)	0.6854 (3)	0.9054 (3)	0.0534 (8)
H12	0.0117	0.6586	0.9557	0.064*
C13	0.1186 (4)	0.8074 (3)	0.8242 (2)	0.0485 (7)
H13	0.0134	0.8620	0.8190	0.058*
C14	0.2180 (4)	0.9262 (3)	0.4043 (2)	0.0415 (6)
C15	0.1925 (4)	0.8100 (3)	0.3660 (2)	0.0394 (6)
C16	0.1873 (4)	0.6816 (3)	0.4374 (2)	0.0548 (8)
H16	0.2020	0.6634	0.5147	0.066*
C17	0.1604 (5)	0.5797 (3)	0.3946 (3)	0.0593 (8)
H17	0.1600	0.4931	0.4423	0.071*
C18	0.1345 (4)	0.6076 (3)	0.2821 (2)	0.0480 (7)
C19	0.1422 (4)	0.7332 (3)	0.2085 (3)	0.0555 (8)
H19	0.1275	0.7504	0.1312	0.067*
C20	0.1724 (4)	0.8337 (3)	0.2515 (2)	0.0491 (7)
H20	0.1792	0.9193	0.2021	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0901 (3)	0.0740 (3)	0.0629 (2)	0.00901 (19)	−0.02581 (18)	−0.04231 (19)
Cl1	0.0828 (6)	0.0743 (6)	0.0825 (6)	−0.0160 (5)	−0.0070 (5)	−0.0520 (5)
O1	0.1015 (18)	0.0392 (12)	0.0457 (12)	−0.0063 (12)	−0.0087 (11)	−0.0094 (9)
O2	0.0902 (16)	0.0397 (12)	0.0469 (12)	−0.0099 (11)	−0.0193 (11)	−0.0075 (10)
N1	0.0639 (15)	0.0360 (13)	0.0407 (13)	−0.0063 (11)	−0.0108 (11)	−0.0149 (10)
N2	0.0763 (17)	0.0328 (13)	0.0384 (12)	−0.0087 (11)	−0.0132 (11)	−0.0115 (10)
C1	0.0478 (16)	0.0488 (18)	0.0520 (16)	0.0021 (13)	−0.0122 (13)	−0.0270 (14)
C2	0.0476 (16)	0.0391 (15)	0.0463 (16)	−0.0007 (12)	−0.0086 (13)	−0.0167 (13)
C3	0.0420 (15)	0.0330 (14)	0.0442 (15)	−0.0023 (11)	−0.0072 (12)	−0.0144 (12)
C4	0.0516 (17)	0.0392 (16)	0.0470 (17)	−0.0034 (13)	−0.0054 (13)	−0.0149 (13)
C5	0.068 (2)	0.0306 (15)	0.0629 (19)	−0.0036 (14)	−0.0084 (16)	−0.0122 (14)
C6	0.0555 (18)	0.0443 (18)	0.072 (2)	−0.0012 (14)	−0.0137 (15)	−0.0313 (16)
C7	0.0448 (15)	0.0379 (15)	0.0390 (15)	−0.0021 (12)	−0.0059 (12)	−0.0150 (12)
C8	0.0512 (16)	0.0305 (14)	0.0368 (14)	−0.0066 (12)	−0.0078 (12)	−0.0143 (11)
C9	0.0522 (18)	0.0433 (17)	0.0482 (16)	−0.0037 (14)	−0.0039 (13)	−0.0161 (13)
C10	0.064 (2)	0.0395 (17)	0.0618 (19)	0.0082 (15)	−0.0187 (17)	−0.0169 (15)
C11	0.077 (2)	0.0326 (16)	0.0472 (17)	−0.0099 (15)	−0.0152 (16)	−0.0066 (13)
C12	0.063 (2)	0.0460 (18)	0.0503 (17)	−0.0166 (16)	−0.0007 (15)	−0.0128 (14)
C13	0.0518 (18)	0.0431 (17)	0.0523 (17)	−0.0014 (13)	−0.0086 (14)	−0.0158 (14)
C14	0.0458 (16)	0.0412 (17)	0.0382 (15)	−0.0038 (12)	−0.0082 (12)	−0.0109 (13)
C15	0.0433 (15)	0.0388 (15)	0.0380 (14)	−0.0041 (12)	−0.0084 (12)	−0.0122 (12)
C16	0.083 (2)	0.0445 (17)	0.0403 (16)	−0.0140 (15)	−0.0156 (15)	−0.0112 (13)
C17	0.084 (2)	0.0423 (17)	0.0538 (19)	−0.0151 (16)	−0.0114 (17)	−0.0132 (14)
C18	0.0465 (16)	0.0549 (19)	0.0530 (17)	−0.0078 (14)	−0.0055 (13)	−0.0300 (15)
C19	0.069 (2)	0.064 (2)	0.0417 (16)	−0.0029 (16)	−0.0131 (14)	−0.0250 (15)
C20	0.0633 (19)	0.0458 (17)	0.0373 (15)	−0.0027 (14)	−0.0085 (13)	−0.0102 (13)

Geometric parameters (Å, º) top

Br1—C1	1.893 (3)	C8—C13	1.386 (4)
Cl1—C18	1.740 (3)	C9—C10	1.384 (4)
O1—C4	1.344 (3)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.368 (4)
O2—C14	1.210 (3)	C10—H10	0.9300
N1—C7	1.285 (3)	C11—C12	1.372 (4)
N1—N2	1.370 (3)	C11—H11	0.9300
N2—C14	1.364 (3)	C12—C13	1.376 (4)
N2—H2	0.8600	C12—H12	0.9300
C1—C6	1.375 (4)	C13—H13	0.9300
C1—C2	1.380 (4)	C14—C15	1.491 (4)
C2—C3	1.390 (4)	C15—C20	1.378 (4)
C2—H2A	0.9300	C15—C16	1.382 (4)
C3—C4	1.407 (4)	C16—C17	1.385 (4)
C3—C7	1.476 (3)	C16—H16	0.9300
C4—C5	1.392 (4)	C17—C18	1.359 (4)
C5—C6	1.363 (4)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.368 (4)
C6—H6	0.9300	C19—C20	1.381 (4)
C7—C8	1.493 (4)	C19—H19	0.9300
C8—C9	1.385 (4)	C20—H20	0.9300

C4—O1—H1	109.5	C11—C10—H10	119.8
C7—N1—N2	119.3 (2)	C9—C10—H10	119.8
C14—N2—N1	118.3 (2)	C10—C11—C12	119.8 (3)
C14—N2—H2	120.8	C10—C11—H11	120.1
N1—N2—H2	120.8	C12—C11—H11	120.1
C6—C1—C2	120.4 (3)	C11—C12—C13	120.4 (3)
C6—C1—Br1	119.3 (2)	C11—C12—H12	119.8
C2—C1—Br1	120.2 (2)	C13—C12—H12	119.8
C1—C2—C3	120.9 (3)	C12—C13—C8	120.4 (3)
C1—C2—H2A	119.6	C12—C13—H13	119.8
C3—C2—H2A	119.6	C8—C13—H13	119.8
C2—C3—C4	118.4 (2)	O2—C14—N2	121.2 (2)
C2—C3—C7	119.9 (2)	O2—C14—C15	122.5 (2)
C4—C3—C7	121.8 (2)	N2—C14—C15	116.3 (2)
O1—C4—C5	117.2 (2)	C20—C15—C16	118.5 (3)
O1—C4—C3	123.5 (2)	C20—C15—C14	117.1 (2)
C5—C4—C3	119.3 (3)	C16—C15—C14	124.4 (2)
C6—C5—C4	121.3 (3)	C15—C16—C17	120.5 (3)
C6—C5—H5	119.3	C15—C16—H16	119.8
C4—C5—H5	119.3	C17—C16—H16	119.8
C5—C6—C1	119.7 (3)	C18—C17—C16	119.3 (3)
C5—C6—H6	120.2	C18—C17—H17	120.4
C1—C6—H6	120.2	C16—C17—H17	120.4
N1—C7—C3	116.0 (2)	C17—C18—C19	121.8 (3)
N1—C7—C8	123.7 (2)	C17—C18—Cl1	118.7 (2)
C3—C7—C8	120.2 (2)	C19—C18—Cl1	119.5 (2)
C9—C8—C13	118.9 (2)	C18—C19—C20	118.4 (3)
C9—C8—C7	120.4 (2)	C18—C19—H19	120.8
C13—C8—C7	120.7 (2)	C20—C19—H19	120.8
C10—C9—C8	120.1 (3)	C15—C20—C19	121.5 (3)
C10—C9—H9	120.0	C15—C20—H20	119.2
C8—C9—H9	120.0	C19—C20—H20	119.2
C11—C10—C9	120.4 (3)

C7—N1—N2—C14	178.9 (2)	C13—C8—C9—C10	−0.3 (4)
C6—C1—C2—C3	−1.2 (4)	C7—C8—C9—C10	179.2 (3)
Br1—C1—C2—C3	−179.6 (2)	C8—C9—C10—C11	−0.6 (4)
C1—C2—C3—C4	0.7 (4)	C9—C10—C11—C12	0.7 (4)
C1—C2—C3—C7	179.8 (2)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—O1	179.8 (3)	C11—C12—C13—C8	−1.0 (4)
C7—C3—C4—O1	0.8 (4)	C9—C8—C13—C12	1.1 (4)
C2—C3—C4—C5	0.2 (4)	C7—C8—C13—C12	−178.4 (3)
C7—C3—C4—C5	−178.9 (3)	N1—N2—C14—O2	0.0 (4)
O1—C4—C5—C6	179.7 (3)	N1—N2—C14—C15	179.8 (2)
C3—C4—C5—C6	−0.7 (4)	O2—C14—C15—C20	0.2 (4)
C4—C5—C6—C1	0.2 (5)	N2—C14—C15—C20	−179.6 (2)
C2—C1—C6—C5	0.7 (4)	O2—C14—C15—C16	−179.6 (3)
Br1—C1—C6—C5	179.2 (2)	N2—C14—C15—C16	0.5 (4)
N2—N1—C7—C3	180.0 (2)	C20—C15—C16—C17	−0.7 (5)
N2—N1—C7—C8	0.4 (4)	C14—C15—C16—C17	179.1 (3)
C2—C3—C7—N1	178.4 (2)	C15—C16—C17—C18	−1.6 (5)
C4—C3—C7—N1	−2.5 (4)	C16—C17—C18—C19	2.9 (5)
C2—C3—C7—C8	−2.0 (4)	C16—C17—C18—Cl1	−175.6 (2)
C4—C3—C7—C8	177.1 (2)	C17—C18—C19—C20	−1.7 (5)
N1—C7—C8—C9	79.9 (3)	Cl1—C18—C19—C20	176.7 (2)
C3—C7—C8—C9	−99.7 (3)	C16—C15—C20—C19	1.9 (4)
N1—C7—C8—C13	−100.6 (3)	C14—C15—C20—C19	−177.9 (3)
C3—C7—C8—C13	79.9 (3)	C18—C19—C20—C15	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.554 (3)	145

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄BrClN₂O₂
M_r	429.69
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.3664 (8), 10.6894 (11), 12.3029 (14)
α, β, γ (°)	71.976 (2), 82.228 (2), 85.466 (2)
V (Å³)	912.05 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.42
Crystal size (mm)	0.20 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.644, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	4841, 3189, 2467
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.085, 1.04
No. of reflections	3189
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.44

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 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	1.839	2.554 (3)	145

Acknowledgements

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

References

Bruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62. CrossRef CAS PubMed Web of Science Google Scholar
Salem, A. A. (1998). Microchem. J. 60, 51–66. Web of Science CrossRef CAS 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
Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77–84. CrossRef PubMed CAS Web of Science Google Scholar

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Volume 65| Part 8| August 2009| Page o1944

doi:10.1107/S1600536809027949

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(E)-(5-Bromo-2-hy­droxy­phen­yl)(phen­yl)methyl­­idene]-4-chloro­benzo­hydrazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(E)-(5-Bromo-2-hydroxyphenyl)(phenyl)methylidene]-4-chlorobenzohydrazide