N′-[(E)-1-(5-Bromo-2-hy­droxy­phen­yl)ethyl­idene]-4-nitro­benzohydrazide

Zheng, C.-Z.; Wang, L.; Liu, J.; Wang, Y.-J.

doi:10.1107/S1600536811023609

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1809

doi:10.1107/S1600536811023609

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N′-[(E)-1-(5-Bromo-2-hydroxyphenyl)ethylidene]-4-nitrobenzohydrazide

Chang-Zheng Zheng,^a Liang Wang,^a ^* Juan Liu ^a and Yu-Jie Wang ^a

^aCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an,Shaanxi, People's Republic of China
^*Correspondence e-mail: wllily315668256@yahoo.com.cn

(Received 25 May 2011; accepted 16 June 2011; online 25 June 2011)

The title compound, C₁₅H₁₂BrN₃O₄, displays a trans conformation with respect to the C=N double bond. The central atoms around the C=N double bond are not coplanar, in contrast to the aromatic rings, which exhibit a dihedral angle of 1.80 (4)° between their mean planes. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, molecules are connected via intermolecular N—H⋯O hydrogen bonding into chains along the a axis.

Related literature

For the coordination properties of aroylhydrazones, see: Ali et al. (2004 ); Carcelli et al. (1995 ); Zhang et al. (2011 ); Zheng et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₂BrN₃O₄
M_r = 378.19
Orthorhombic, P n a 2₁
a = 40.381 (13) Å
b = 5.0598 (16) Å
c = 7.168 (2) Å
V = 1464.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.83 mm⁻¹
T = 298 K
0.35 × 0.23 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.441, T_max = 0.689
6753 measured reflections
2520 independent reflections
2074 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.157
S = 0.95
2520 reflections
210 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.75 e Å⁻³
Absolute structure: Flack (1983), 1075 Friedel pairs
Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.23	2.981 (6)	146
O1—H1⋯N1	0.82	1.81	2.531 (7)	145
Symmetry code: (i) x, y+1, z.

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/S1600536811023609/zq2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023609/zq2106Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023609/zq2106Isup3.cml

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Zhang et al., 2011; Zheng et al., 2008; Ali et al., 2004) and their biological activity (Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound, C₁₅H₁₂N₃O₄Br, was synthesized and its crystal structure is reported here.

The title compound, C₁₅H₁₂N₃O₄Br, displays a trans conformation with respect to the C=N double bond (Fig. 1). The central atoms around the C=N double bond are not coplanar since the dihedral angle C7—N1—N2—C9 is 154.7 (5)° in contrast to the aromatic rings which exhibit a dihedral angle of 1.80 (4)° between their mean planes. In the crystal structure, one intramolecular O—H···N hydrogen bond occurs (Table 1). The molecules are connected via intermolecular N—H···O into one-dimensional linear chains along the a axis (Table 1; Fig. 2).

Related literature top

For the coordination properties of aroylhydrazones, see: Ali et al. (2004); Carcelli et al. (1995); Zhang et al. (2011); Zheng et al. (2008) .

Experimental top

Ethyl 4-nitrobenzoate (9.76 g, 0.05 mol) was dissolved in ethanol (40 ml) at room temperature and heated at 363 K, followed by the addition of hydrazine hydrate (2.50 g, 0.05 mol). Subsequently, the mixture was refluxed for 10 h, and then cooled to room temperature. The crystals were precipitated and collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to give compound of 4-nitrobenzhydrazide. 4-Nitrobenzhydrazide (4.53 g, 0.025 mol) was dissolved in ethanol (20 ml) at room temperature and heated at 363 K, followed by the addition of 5-bromo-2-hydroxyphenyl ethyl ketone (5.38 g, 0.025 mol). Subsequently, the mixture was refluxed for 9 h, and then cooled to room temperature. The crystals were precipitated and collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to the title compound.

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 the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Dashed lines show intra- and intermolecular hydrogen bonds.

N'-[(E)-1-(5-Bromo-2-hydroxyphenyl)ethylidene]-4- nitrobenzohydrazide top

Crystal data top

C₁₅H₁₂BrN₃O₄	F(000) = 760
M_r = 378.19	D_x = 1.715 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2077 reflections
a = 40.381 (13) Å	θ = 3.0–23.4°
b = 5.0598 (16) Å	µ = 2.83 mm⁻¹
c = 7.168 (2) Å	T = 298 K
V = 1464.5 (8) Å³	Block, red
Z = 4	0.35 × 0.23 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2520 independent reflections
Radiation source: fine-focus sealed tube	2074 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −39→48
T_min = 0.441, T_max = 0.689	k = −6→6
6753 measured reflections	l = −7→8

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.120P)² + 0.2524P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.157	(Δ/σ)_max = 0.002
S = 0.95	Δρ_max = 0.95 e Å⁻³
2520 reflections	Δρ_min = −0.75 e Å⁻³
210 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.0113 (15)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1075 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (2)

Crystal data top

C₁₅H₁₂BrN₃O₄	V = 1464.5 (8) Å³
M_r = 378.19	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 40.381 (13) Å	µ = 2.83 mm⁻¹
b = 5.0598 (16) Å	T = 298 K
c = 7.168 (2) Å	0.35 × 0.23 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2520 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2074 reflections with I > 2σ(I)
T_min = 0.441, T_max = 0.689	R_int = 0.040
6753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.157	Δρ_max = 0.95 e Å⁻³
S = 0.95	Δρ_min = −0.75 e Å⁻³
2520 reflections	Absolute structure: Flack (1983), 1075 Friedel pairs
210 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

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	0.748669 (14)	0.63795 (13)	0.8107 (3)	0.0527 (3)
N1	0.63083 (12)	0.3604 (9)	0.2325 (8)	0.0407 (12)
N2	0.61516 (12)	0.4290 (9)	0.0655 (7)	0.0398 (12)
H2A	0.6165	0.5855	0.0194	0.048*
N3	0.53035 (13)	0.4393 (12)	−0.7014 (9)	0.0537 (14)
O1	0.63214 (10)	0.0383 (8)	0.5025 (7)	0.0454 (10)
H1	0.6246	0.1078	0.4084	0.068*
O2	0.59928 (11)	0.0029 (8)	0.0369 (7)	0.0534 (12)
O3	0.50841 (18)	0.2902 (13)	−0.7491 (10)	0.094 (2)
O4	0.53936 (16)	0.6248 (14)	−0.7978 (10)	0.087 (2)
C1	0.71150 (13)	0.4542 (11)	0.7103 (8)	0.0383 (13)
C2	0.69852 (14)	0.2403 (12)	0.8090 (10)	0.0460 (13)
H2	0.7078	0.1873	0.9219	0.055*
C3	0.67161 (18)	0.1098 (12)	0.7345 (10)	0.0477 (16)
H3	0.6625	−0.0310	0.8000	0.057*
C4	0.65783 (15)	0.1816 (11)	0.5655 (9)	0.0363 (13)
C5	0.67081 (14)	0.4039 (10)	0.4651 (8)	0.0330 (12)
C6	0.69784 (13)	0.5350 (10)	0.5410 (8)	0.0352 (12)
H6	0.7070	0.6784	0.4781	0.042*
C7	0.65665 (13)	0.4916 (10)	0.2846 (7)	0.0329 (12)
C8	0.67260 (16)	0.7035 (12)	0.1733 (9)	0.0434 (15)
H8A	0.6657	0.6895	0.0455	0.065*
H8B	0.6962	0.6853	0.1804	0.065*
H8C	0.6662	0.8728	0.2218	0.065*
C9	0.59767 (14)	0.2338 (11)	−0.0194 (9)	0.0405 (14)
C10	0.57928 (12)	0.3074 (10)	−0.1896 (10)	0.0353 (11)
C11	0.55293 (16)	0.1454 (12)	−0.2431 (10)	0.0451 (17)
H11	0.5465	0.0060	−0.1667	0.054*
C12	0.53649 (15)	0.1907 (12)	−0.4076 (10)	0.0462 (15)
H12	0.5186	0.0856	−0.4425	0.055*
C13	0.54701 (15)	0.3955 (11)	−0.5200 (9)	0.0411 (14)
C14	0.57239 (14)	0.5633 (11)	−0.4717 (9)	0.0410 (13)
H14	0.5786	0.7022	−0.5492	0.049*
C15	0.58848 (15)	0.5181 (11)	−0.3029 (9)	0.0432 (14)
H15	0.6055	0.6298	−0.2655	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0513 (4)	0.0578 (4)	0.0490 (4)	0.0046 (3)	−0.0137 (3)	−0.0030 (5)
N1	0.050 (3)	0.036 (3)	0.035 (3)	0.004 (2)	−0.007 (2)	0.000 (2)
N2	0.053 (3)	0.032 (2)	0.034 (3)	−0.004 (2)	−0.011 (2)	0.002 (2)
N3	0.055 (3)	0.057 (3)	0.050 (4)	0.001 (2)	−0.015 (3)	−0.001 (3)
O1	0.060 (3)	0.030 (2)	0.046 (3)	−0.0088 (19)	0.002 (2)	0.013 (2)
O2	0.077 (3)	0.030 (2)	0.054 (3)	−0.003 (2)	−0.018 (2)	0.001 (2)
O3	0.112 (4)	0.084 (4)	0.086 (6)	−0.029 (4)	−0.056 (4)	0.015 (3)
O4	0.079 (4)	0.115 (5)	0.067 (4)	−0.022 (3)	−0.021 (3)	0.032 (4)
C1	0.046 (3)	0.039 (3)	0.031 (3)	0.007 (2)	−0.004 (2)	−0.010 (3)
C2	0.066 (3)	0.047 (3)	0.025 (3)	0.011 (3)	−0.004 (3)	0.013 (3)
C3	0.072 (4)	0.038 (3)	0.033 (3)	0.005 (3)	0.006 (3)	0.012 (3)
C4	0.044 (3)	0.029 (3)	0.035 (3)	0.005 (2)	0.005 (2)	0.001 (2)
C5	0.037 (3)	0.028 (3)	0.034 (3)	0.005 (2)	0.006 (2)	0.004 (2)
C6	0.044 (3)	0.028 (3)	0.034 (3)	0.000 (2)	0.002 (2)	0.006 (2)
C7	0.044 (3)	0.023 (2)	0.031 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
C8	0.056 (4)	0.041 (3)	0.033 (4)	−0.004 (3)	−0.005 (3)	0.005 (3)
C9	0.039 (3)	0.034 (3)	0.048 (4)	0.000 (3)	0.000 (3)	−0.009 (3)
C10	0.037 (2)	0.030 (2)	0.039 (3)	0.0031 (19)	−0.005 (3)	−0.009 (3)
C11	0.045 (3)	0.035 (3)	0.055 (5)	−0.004 (2)	0.001 (3)	0.004 (3)
C12	0.044 (3)	0.041 (3)	0.053 (4)	−0.007 (3)	−0.009 (3)	0.002 (3)
C13	0.040 (3)	0.044 (3)	0.040 (4)	0.003 (2)	−0.007 (2)	−0.012 (3)
C14	0.048 (3)	0.036 (3)	0.039 (4)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C15	0.047 (3)	0.036 (3)	0.047 (4)	−0.004 (3)	−0.003 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Br1—C1	1.906 (6)	C5—C6	1.388 (8)
N1—C7	1.291 (7)	C5—C7	1.483 (8)
N1—N2	1.397 (7)	C6—H6	0.9300
N2—C9	1.358 (7)	C7—C8	1.484 (8)
N2—H2A	0.8600	C8—H8A	0.9600
N3—O3	1.213 (8)	C8—H8B	0.9600
N3—O4	1.221 (8)	C8—H8C	0.9600
N3—C13	1.480 (8)	C9—C10	1.476 (9)
O1—C4	1.344 (8)	C10—C15	1.391 (9)
O1—H1	0.8200	C10—C11	1.396 (8)
O2—C9	1.238 (7)	C11—C12	1.373 (10)
C1—C6	1.394 (8)	C11—H11	0.9300
C1—C2	1.395 (9)	C12—C13	1.380 (9)
C2—C3	1.380 (10)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.375 (8)
C3—C4	1.381 (10)	C14—C15	1.393 (9)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.435 (8)	C15—H15	0.9300

C7—N1—N2	119.1 (5)	C5—C7—C8	121.2 (5)
C9—N2—N1	116.0 (5)	C7—C8—H8A	109.5
C9—N2—H2A	122.0	C7—C8—H8B	109.5
N1—N2—H2A	122.0	H8A—C8—H8B	109.5
O3—N3—O4	122.4 (7)	C7—C8—H8C	109.5
O3—N3—C13	119.1 (6)	H8A—C8—H8C	109.5
O4—N3—C13	118.5 (5)	H8B—C8—H8C	109.5
C4—O1—H1	109.5	O2—C9—N2	120.8 (6)
C6—C1—C2	121.3 (5)	O2—C9—C10	122.3 (5)
C6—C1—Br1	119.8 (4)	N2—C9—C10	116.7 (5)
C2—C1—Br1	118.9 (5)	C15—C10—C11	119.6 (6)
C3—C2—C1	118.1 (6)	C15—C10—C9	122.8 (5)
C3—C2—H2	121.0	C11—C10—C9	117.5 (5)
C1—C2—H2	121.0	C12—C11—C10	120.4 (6)
C2—C3—C4	122.1 (6)	C12—C11—H11	119.8
C2—C3—H3	119.0	C10—C11—H11	119.8
C4—C3—H3	119.0	C11—C12—C13	118.6 (6)
O1—C4—C3	117.6 (6)	C11—C12—H12	120.7
O1—C4—C5	122.4 (5)	C13—C12—H12	120.7
C3—C4—C5	119.9 (6)	C14—C13—C12	123.1 (6)
C6—C5—C4	117.7 (5)	C14—C13—N3	117.8 (6)
C6—C5—C7	120.1 (5)	C12—C13—N3	119.0 (5)
C4—C5—C7	122.1 (5)	C13—C14—C15	117.7 (6)
C5—C6—C1	120.8 (5)	C13—C14—H14	121.1
C5—C6—H6	119.6	C15—C14—H14	121.1
C1—C6—H6	119.6	C10—C15—C14	120.6 (5)
N1—C7—C5	114.2 (5)	C10—C15—H15	119.7
N1—C7—C8	124.5 (5)	C14—C15—H15	119.7

C7—N1—N2—C9	154.7 (5)	N1—N2—C9—O2	−8.8 (8)
C6—C1—C2—C3	−0.1 (9)	N1—N2—C9—C10	176.3 (5)
Br1—C1—C2—C3	179.9 (5)	O2—C9—C10—C15	−149.2 (6)
C1—C2—C3—C4	1.2 (10)	N2—C9—C10—C15	25.6 (8)
C2—C3—C4—O1	178.5 (6)	O2—C9—C10—C11	26.5 (8)
C2—C3—C4—C5	−2.2 (9)	N2—C9—C10—C11	−158.7 (5)
O1—C4—C5—C6	−178.7 (5)	C15—C10—C11—C12	1.0 (9)
C3—C4—C5—C6	1.9 (8)	C9—C10—C11—C12	−174.9 (5)
O1—C4—C5—C7	0.2 (8)	C10—C11—C12—C13	1.3 (10)
C3—C4—C5—C7	−179.2 (5)	C11—C12—C13—C14	−2.6 (10)
C4—C5—C6—C1	−0.8 (8)	C11—C12—C13—N3	177.5 (6)
C7—C5—C6—C1	−179.8 (5)	O3—N3—C13—C14	178.3 (7)
C2—C1—C6—C5	−0.1 (8)	O4—N3—C13—C14	−1.5 (9)
Br1—C1—C6—C5	179.9 (4)	O3—N3—C13—C12	−1.8 (10)
N2—N1—C7—C5	179.1 (4)	O4—N3—C13—C12	178.4 (7)
N2—N1—C7—C8	−4.0 (8)	C12—C13—C14—C15	1.5 (9)
C6—C5—C7—N1	−177.5 (5)	N3—C13—C14—C15	−178.6 (5)
C4—C5—C7—N1	3.6 (7)	C11—C10—C15—C14	−2.2 (9)
C6—C5—C7—C8	5.5 (8)	C9—C10—C15—C14	173.5 (5)
C4—C5—C7—C8	−173.4 (6)	C13—C14—C15—C10	0.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.23	2.981 (6)	146
O1—H1···N1	0.82	1.81	2.531 (7)	145

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrN₃O₄
M_r	378.19
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	40.381 (13), 5.0598 (16), 7.168 (2)
V (Å³)	1464.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.83
Crystal size (mm)	0.35 × 0.23 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.441, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	6753, 2520, 2074
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.157, 0.95
No. of reflections	2520
No. of parameters	210
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −0.75
Absolute structure	Flack (1983), 1075 Friedel pairs
Absolute structure parameter	0.01 (2)

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
N2—H2A···O2ⁱ	0.860	2.227	2.981 (6)	146.26
O1—H1···N1	0.820	1.813	2.531 (7)	145.31

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

Acknowledgements

The authors thank the National Natural Science Foundation of Shaanxi Province, China (2009JM2012) for financial support.

References

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