N′-[(E)-(5-Bromo-2-hydroxy­phen­yl)(phen­yl)methyl­ene]benzohydrazide

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

doi:10.1107/S1600536809002918

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o641

doi:10.1107/S1600536809002918

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N′-[(E)-(5-Bromo-2-hydroxyphenyl)(phenyl)methylene]benzohydrazide

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 24 December 2008; accepted 23 January 2009; online 28 February 2009)

In the title compound, C₂₀H₁₅BrN₂O₂, the C=N double bond displays a trans configuration. The crystal structure features an intramolecular O—H⋯N hydrogen bond.

Related literature

For literature on similar Schiff bases, see: Carcelli et al. (1995 ); Salem (1998 ); Singh et al. (1982 ).

Experimental

Crystal data

C₂₀H₁₅BrN₂O₂
M_r = 395.25
Monoclinic, P 2₁ /c
a = 17.505 (5) Å
b = 13.761 (4) Å
c = 7.219 (2) Å
β = 94.546 (6)°
V = 1733.4 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.39 mm⁻¹
T = 298 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.763, T_max = 0.870
9019 measured reflections
3078 independent reflections
1722 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.101
S = 1.00
3078 reflections
197 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 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	2.562 (4)	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/S1600536809002918/ng2531sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002918/ng2531Isup2.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 C8=N1 double bond (Fig. 1). The crystal structure is stabilized by intramolecular O—H···N and intermolecular N—H···O hydrogen bonds (Table 1. and Fig. 2).

Related literature top

For literature on similar Schiff bases, see: Carcelli et al. (1995); Salem (1998); Singh et al. (1982).

Experimental top

benzoylhydrazine (0.02 mol,2.72 g) was dissolved in anhydrous ethanol (50 ml), and (5-bromo-2-hydroxyphenyl)(phenyl)methanone (0.02 mol, 5.54 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,0.79 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.
	Fig. 2. The crystal packing of (I), viewed along the c axis. Dashed lines show intra-and intermolecular hydrogen bonds.

N'-[(E)-(5-Bromo-2-hydroxyphenyl)(phenyl)methylene]benzohydrazide top

Crystal data top

C₂₀H₁₅BrN₂O₂	F(000) = 800
M_r = 395.25	D_x = 1.515 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1125 reflections
a = 17.505 (5) Å	θ = 2.3–17.9°
b = 13.761 (4) Å	µ = 2.39 mm⁻¹
c = 7.219 (2) Å	T = 298 K
β = 94.546 (6)°	Block, yellow
V = 1733.4 (9) Å³	0.12 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker SMART diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→20
T_min = 0.763, T_max = 0.870	k = −13→16
9019 measured reflections	l = −8→7

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) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.038P)² + 0.0901P] where P = (F_o² + 2F_c²)/3
3078 reflections	(Δ/σ)_max < 0.001
197 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₁₅BrN₂O₂	V = 1733.4 (9) Å³
M_r = 395.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.505 (5) Å	µ = 2.39 mm⁻¹
b = 13.761 (4) Å	T = 298 K
c = 7.219 (2) Å	0.12 × 0.10 × 0.06 mm
β = 94.546 (6)°

Data collection top

Bruker SMART diffractometer	3078 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1722 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.870	R_int = 0.059
9019 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.00	Δρ_max = 0.31 e Å⁻³
3078 reflections	Δρ_min = −0.28 e Å⁻³
197 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	0.42053 (3)	0.11003 (4)	0.37885 (7)	0.0690 (2)
O1	0.69581 (16)	0.35312 (19)	0.2430 (4)	0.0600 (8)
H1	0.7343	0.3203	0.2327	0.090*
O2	0.89683 (17)	0.2957 (2)	0.1320 (5)	0.0729 (9)
N1	0.7724 (2)	0.1958 (2)	0.2165 (4)	0.0524 (9)
N2	0.84133 (19)	0.1530 (2)	0.1895 (5)	0.0573 (9)
H2	0.8456	0.0908	0.1935	0.069*
C1	0.6363 (2)	0.2941 (3)	0.2723 (5)	0.0469 (10)
C2	0.6425 (2)	0.1921 (3)	0.2769 (5)	0.0428 (10)
C3	0.5771 (2)	0.1384 (3)	0.3098 (5)	0.0463 (10)
H3	0.5799	0.0710	0.3158	0.056*
C4	0.5090 (2)	0.1842 (3)	0.3332 (5)	0.0495 (11)
C5	0.5032 (3)	0.2842 (3)	0.3297 (5)	0.0548 (11)
H5	0.4571	0.3148	0.3481	0.066*
C6	0.5670 (3)	0.3371 (3)	0.2983 (5)	0.0566 (12)
H6	0.5635	0.4045	0.2944	0.068*
C7	0.7149 (2)	0.1422 (3)	0.2494 (5)	0.0441 (10)
C8	0.7210 (2)	0.0332 (3)	0.2583 (6)	0.0419 (10)
C9	0.7594 (2)	−0.0103 (3)	0.4116 (6)	0.0553 (12)
H9	0.7792	0.0275	0.5109	0.066*
C10	0.7682 (3)	−0.1098 (3)	0.4170 (6)	0.0641 (12)
H10	0.7951	−0.1388	0.5187	0.077*
C11	0.7376 (3)	−0.1661 (3)	0.2735 (7)	0.0608 (12)
H11	0.7434	−0.2332	0.2783	0.073*
C12	0.6986 (2)	−0.1235 (3)	0.1229 (7)	0.0579 (12)
H12	0.6768	−0.1620	0.0268	0.069*
C13	0.6915 (2)	−0.0232 (3)	0.1130 (6)	0.0513 (11)
H13	0.6667	0.0057	0.0083	0.062*
C14	0.9034 (2)	0.2088 (3)	0.1563 (6)	0.0527 (11)
C15	0.9765 (2)	0.1545 (3)	0.1514 (5)	0.0471 (10)
C16	0.9902 (3)	0.0672 (3)	0.2383 (6)	0.0570 (12)
H16	0.9524	0.0391	0.3043	0.068*
C17	1.0594 (3)	0.0201 (3)	0.2294 (6)	0.0652 (13)
H17	1.0681	−0.0391	0.2895	0.078*
C18	1.1156 (3)	0.0609 (4)	0.1314 (7)	0.0701 (14)
H18	1.1622	0.0293	0.1232	0.084*
C19	1.1021 (3)	0.1485 (4)	0.0465 (7)	0.0726 (14)
H19	1.1401	0.1766	−0.0188	0.087*
C20	1.0337 (3)	0.1958 (3)	0.0553 (6)	0.0584 (12)
H20	1.0256	0.2556	−0.0031	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0514 (3)	0.0762 (4)	0.0801 (4)	0.0014 (3)	0.0099 (2)	0.0023 (3)
O1	0.065 (2)	0.0412 (17)	0.074 (2)	−0.0003 (15)	0.0062 (18)	−0.0016 (16)
O2	0.063 (2)	0.0396 (18)	0.115 (3)	−0.0032 (16)	0.0033 (18)	0.0054 (19)
N1	0.049 (2)	0.047 (2)	0.062 (2)	−0.0002 (19)	0.0078 (18)	−0.0026 (18)
N2	0.047 (2)	0.042 (2)	0.084 (3)	−0.0039 (18)	0.0108 (19)	−0.0040 (19)
C1	0.057 (3)	0.043 (3)	0.041 (2)	0.001 (2)	0.003 (2)	0.000 (2)
C2	0.050 (3)	0.045 (3)	0.034 (2)	0.007 (2)	0.0050 (19)	0.001 (2)
C3	0.049 (3)	0.049 (3)	0.041 (2)	0.007 (2)	−0.0006 (19)	0.003 (2)
C4	0.047 (3)	0.061 (3)	0.041 (2)	0.005 (2)	0.0044 (19)	0.001 (2)
C5	0.054 (3)	0.056 (3)	0.054 (3)	0.013 (2)	0.002 (2)	−0.005 (2)
C6	0.073 (3)	0.041 (3)	0.055 (3)	0.011 (3)	0.000 (2)	−0.001 (2)
C7	0.044 (3)	0.044 (3)	0.044 (2)	−0.002 (2)	0.0040 (19)	−0.001 (2)
C8	0.037 (2)	0.039 (3)	0.050 (3)	−0.0013 (19)	0.0071 (19)	0.002 (2)
C9	0.062 (3)	0.052 (3)	0.051 (3)	0.003 (2)	0.003 (2)	−0.003 (2)
C10	0.075 (3)	0.056 (3)	0.062 (3)	0.012 (3)	0.008 (2)	0.013 (3)
C11	0.063 (3)	0.040 (3)	0.083 (4)	0.005 (2)	0.024 (3)	0.006 (3)
C12	0.054 (3)	0.051 (3)	0.070 (3)	−0.007 (2)	0.012 (2)	−0.012 (3)
C13	0.051 (3)	0.048 (3)	0.054 (3)	0.005 (2)	0.002 (2)	−0.001 (2)
C14	0.054 (3)	0.044 (3)	0.060 (3)	−0.012 (2)	0.000 (2)	−0.003 (2)
C15	0.046 (3)	0.043 (3)	0.052 (3)	−0.008 (2)	−0.001 (2)	−0.003 (2)
C16	0.058 (3)	0.051 (3)	0.062 (3)	−0.004 (2)	0.005 (2)	−0.001 (3)
C17	0.074 (4)	0.049 (3)	0.070 (3)	0.005 (3)	−0.012 (3)	−0.001 (3)
C18	0.050 (3)	0.084 (4)	0.075 (4)	0.009 (3)	−0.003 (3)	−0.022 (3)
C19	0.051 (3)	0.101 (4)	0.067 (3)	−0.012 (3)	0.011 (2)	0.000 (3)
C20	0.057 (3)	0.060 (3)	0.058 (3)	−0.011 (3)	0.003 (2)	0.010 (2)

Geometric parameters (Å, º) top

Br1—C4	1.905 (4)	C9—C10	1.378 (5)
O1—C1	1.350 (4)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.368 (5)
O2—C14	1.213 (4)	C10—H10	0.9300
N1—C7	1.284 (4)	C11—C12	1.369 (5)
N1—N2	1.370 (4)	C11—H11	0.9300
N2—C14	1.367 (5)	C12—C13	1.387 (5)
N2—H2	0.8600	C12—H12	0.9300
C1—C6	1.376 (5)	C13—H13	0.9300
C1—C2	1.409 (5)	C14—C15	1.484 (6)
C2—C3	1.397 (5)	C15—C16	1.369 (5)
C2—C7	1.469 (5)	C15—C20	1.384 (5)
C3—C4	1.370 (5)	C16—C17	1.380 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.380 (5)	C17—C18	1.377 (6)
C5—C6	1.368 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.364 (7)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.506 (5)	C19—C20	1.370 (6)
C8—C13	1.373 (5)	C19—H19	0.9300
C8—C9	1.384 (5)	C20—H20	0.9300

C1—O1—H1	109.5	C11—C10—H10	119.8
C7—N1—N2	119.5 (3)	C9—C10—H10	119.8
C14—N2—N1	120.3 (4)	C10—C11—C12	120.0 (4)
C14—N2—H2	119.9	C10—C11—H11	120.0
N1—N2—H2	119.9	C12—C11—H11	120.0
O1—C1—C6	117.5 (4)	C11—C12—C13	120.2 (4)
O1—C1—C2	123.0 (4)	C11—C12—H12	119.9
C6—C1—C2	119.4 (4)	C13—C12—H12	119.9
C3—C2—C1	117.9 (4)	C8—C13—C12	119.8 (4)
C3—C2—C7	120.2 (4)	C8—C13—H13	120.1
C1—C2—C7	121.8 (4)	C12—C13—H13	120.1
C4—C3—C2	120.7 (4)	O2—C14—N2	120.8 (4)
C4—C3—H3	119.7	O2—C14—C15	124.4 (4)
C2—C3—H3	119.7	N2—C14—C15	114.8 (4)
C3—C4—C5	121.3 (4)	C16—C15—C20	118.8 (4)
C3—C4—Br1	120.2 (3)	C16—C15—C14	123.5 (4)
C5—C4—Br1	118.5 (3)	C20—C15—C14	117.7 (4)
C6—C5—C4	118.3 (4)	C15—C16—C17	121.0 (4)
C6—C5—H5	120.8	C15—C16—H16	119.5
C4—C5—H5	120.8	C17—C16—H16	119.5
C5—C6—C1	122.3 (4)	C18—C17—C16	119.9 (5)
C5—C6—H6	118.8	C18—C17—H17	120.1
C1—C6—H6	118.8	C16—C17—H17	120.1
N1—C7—C2	117.1 (4)	C19—C18—C17	119.1 (5)
N1—C7—C8	121.7 (4)	C19—C18—H18	120.4
C2—C7—C8	121.2 (3)	C17—C18—H18	120.4
C13—C8—C9	119.7 (4)	C18—C19—C20	121.4 (5)
C13—C8—C7	120.6 (4)	C18—C19—H19	119.3
C9—C8—C7	119.6 (4)	C20—C19—H19	119.3
C10—C9—C8	119.9 (4)	C19—C20—C15	119.9 (4)
C10—C9—H9	120.1	C19—C20—H20	120.1
C8—C9—H9	120.1	C15—C20—H20	120.1
C11—C10—C9	120.3 (4)

C7—N1—N2—C14	−179.3 (4)	C2—C7—C8—C9	−106.2 (4)
O1—C1—C2—C3	179.5 (3)	C13—C8—C9—C10	0.5 (6)
C6—C1—C2—C3	−0.6 (5)	C7—C8—C9—C10	−177.1 (4)
O1—C1—C2—C7	−0.1 (6)	C8—C9—C10—C11	−1.6 (6)
C6—C1—C2—C7	179.8 (3)	C9—C10—C11—C12	0.6 (6)
C1—C2—C3—C4	1.2 (5)	C10—C11—C12—C13	1.6 (6)
C7—C2—C3—C4	−179.2 (3)	C9—C8—C13—C12	1.6 (6)
C2—C3—C4—C5	−1.6 (6)	C7—C8—C13—C12	179.1 (4)
C2—C3—C4—Br1	−179.8 (3)	C11—C12—C13—C8	−2.6 (6)
C3—C4—C5—C6	1.3 (6)	N1—N2—C14—O2	−7.3 (6)
Br1—C4—C5—C6	179.5 (3)	N1—N2—C14—C15	173.2 (3)
C4—C5—C6—C1	−0.7 (6)	O2—C14—C15—C16	156.7 (4)
O1—C1—C6—C5	−179.8 (3)	N2—C14—C15—C16	−23.8 (5)
C2—C1—C6—C5	0.3 (6)	O2—C14—C15—C20	−22.5 (6)
N2—N1—C7—C2	−179.9 (3)	N2—C14—C15—C20	157.0 (4)
N2—N1—C7—C8	−0.3 (5)	C20—C15—C16—C17	−0.7 (6)
C3—C2—C7—N1	178.8 (3)	C14—C15—C16—C17	−179.8 (4)
C1—C2—C7—N1	−1.6 (5)	C15—C16—C17—C18	−0.2 (6)
C3—C2—C7—C8	−0.8 (5)	C16—C17—C18—C19	0.9 (7)
C1—C2—C7—C8	178.8 (3)	C17—C18—C19—C20	−0.6 (7)
N1—C7—C8—C13	−103.3 (4)	C18—C19—C20—C15	−0.3 (7)
C2—C7—C8—C13	76.3 (5)	C16—C15—C20—C19	0.9 (6)
N1—C7—C8—C9	74.2 (5)	C14—C15—C20—C19	−179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.562 (4)	145

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅BrN₂O₂
M_r	395.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.505 (5), 13.761 (4), 7.219 (2)
β (°)	94.546 (6)
V (Å³)	1733.4 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.39
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.763, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	9019, 3078, 1722
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.101, 1.00
No. of reflections	3078
No. of parameters	197
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

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	1.846	2.562 (4)	145

Acknowledgements

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

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