3-Bromo-N′-[(E)-4-hydroxy­benzyl­idene]benzohydrazide

Yang, T.; Cao, G.-B.; Xiang, J.-M.; Zhang, L.-H.

doi:10.1107/S1600536808015912

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1186

doi:10.1107/S1600536808015912

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3-Bromo-N′-[(E)-4-hydroxybenzylidene]benzohydrazide

Tao Yang,^a Guo-Biao Cao,^a ^* Ji-Ming Xiang ^a and Li-Hui Zhang ^a

^aDepartment of Chemistry, Ankang University, Ankang, Shanxi 725000, People's Republic of China
^*Correspondence e-mail: guobiao_cao@126.com

(Received 23 May 2008; accepted 27 May 2008; online 7 June 2008)

The title compound, C₁₄H₁₁BrN₂O₂, was synthesized by the reaction of 4-hydroxybenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The dihedral angle between the two benzene rings is 40.1 (2)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds to form a three-dimensional network.

Related literature

For related structures, see: Cao (2007a ,b ).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₂
M_r = 319.16
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5576 (11) Å
b = 11.7337 (18) Å
c = 15.021 (2) Å
V = 1332.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 298 (2) K
0.20 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.577, T_max = 0.638
7740 measured reflections
2757 independent reflections
2145 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.059
S = 0.97
2757 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), with 1154 Friedel pairs
Flack parameter: 0.006 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.95	2.750 (2)	166
O1—H1⋯N1ⁱ	0.82	2.56	3.003 (3)	116
N2—H2A⋯O1ⁱⁱ	0.904 (10)	2.136 (14)	3.007 (3)	162 (3)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ .

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/S1600536808015912/sj2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015912/sj2509Isup2.hkl

checkCIF report

Comment top

We have recently reported some transition metal complexes with Schiff base ligands (Cao, 2007a,b). We report herein the crystal structure of the title compound, (I), derived from the reaction of 4-hydroxybenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol.

In compound (I), Fig. 1, the dihedral angle between the two benzene rings is 40.1 (2)°. In the crystal structure, molecules are linked through intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds, Table 1, to form a three-dimensional network, Figure 2.

Related literature top

For related structures, see: Cao (2007a,b).

Experimental top

The compound was prepared by refluxing equimolar quantities of 4-hydroxybenzaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed when the solution was evaporated in air for about a week.

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

3-Bromo-N'-[(E)-4-hydroxybenzylidene]benzohydrazide top

Crystal data top

C₁₄H₁₁BrN₂O₂	F(000) = 640
M_r = 319.16	D_x = 1.591 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1827 reflections
a = 7.5576 (11) Å	θ = 2.3–24.5°
b = 11.7337 (18) Å	µ = 3.09 mm⁻¹
c = 15.021 (2) Å	T = 298 K
V = 1332.0 (3) Å³	Block, colourless
Z = 4	0.20 × 0.17 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2757 independent reflections
Radiation source: fine-focus sealed tube	2145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 26.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.577, T_max = 0.638	k = −10→14
7740 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0151P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
2757 reflections	Δρ_max = 0.17 e Å⁻³
176 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 1154 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (9)

Crystal data top

C₁₄H₁₁BrN₂O₂	V = 1332.0 (3) Å³
M_r = 319.16	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5576 (11) Å	µ = 3.09 mm⁻¹
b = 11.7337 (18) Å	T = 298 K
c = 15.021 (2) Å	0.20 × 0.17 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2757 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2145 reflections with I > 2σ(I)
T_min = 0.577, T_max = 0.638	R_int = 0.038
7740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	Δρ_max = 0.17 e Å⁻³
S = 0.97	Δρ_min = −0.29 e Å⁻³
2757 reflections	Absolute structure: Flack (1983), with 1154 Friedel pairs
176 parameters	Absolute structure parameter: 0.006 (9)
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	0.04594 (5)	0.39161 (3)	0.901456 (17)	0.06805 (13)
O1	0.1347 (3)	−0.14174 (14)	0.15827 (10)	0.0414 (5)
H1	0.0663	−0.1163	0.1208	0.062*
O2	0.0446 (3)	0.45672 (13)	0.48129 (10)	0.0435 (4)
N1	0.1134 (3)	0.23480 (18)	0.46451 (12)	0.0380 (6)
N2	0.1329 (3)	0.29110 (18)	0.54514 (12)	0.0372 (5)
C1	0.1401 (3)	0.0602 (2)	0.38450 (14)	0.0310 (6)
C2	0.0757 (3)	0.1044 (2)	0.30437 (14)	0.0343 (6)
H2	0.0339	0.1789	0.3024	0.041*
C3	0.0735 (3)	0.03889 (19)	0.22853 (14)	0.0331 (6)
H3	0.0315	0.0692	0.1754	0.040*
C4	0.1341 (3)	−0.0726 (2)	0.23148 (14)	0.0309 (6)
C5	0.1975 (3)	−0.1177 (2)	0.31015 (15)	0.0357 (6)
H5	0.2381	−0.1925	0.3120	0.043*
C6	0.2003 (3)	−0.0514 (2)	0.38585 (15)	0.0352 (6)
H6	0.2432	−0.0820	0.4387	0.042*
C7	0.1494 (3)	0.1299 (2)	0.46504 (15)	0.0348 (6)
H7	0.1829	0.0958	0.5183	0.042*
C8	0.0976 (3)	0.4039 (2)	0.54681 (14)	0.0339 (6)
C9	0.1227 (3)	0.4615 (2)	0.63473 (15)	0.0333 (6)
C10	0.0837 (3)	0.4069 (2)	0.71421 (14)	0.0373 (6)
H10	0.0457	0.3315	0.7143	0.045*
C11	0.1020 (4)	0.4657 (2)	0.79290 (15)	0.0405 (7)
C12	0.1571 (4)	0.5781 (2)	0.79396 (18)	0.0482 (8)
H12	0.1689	0.6169	0.8476	0.058*
C13	0.1942 (4)	0.6314 (2)	0.7149 (2)	0.0516 (8)
H13	0.2320	0.7068	0.7151	0.062*
C14	0.1760 (4)	0.5743 (2)	0.63504 (17)	0.0425 (7)
H14	0.1995	0.6116	0.5817	0.051*
H2A	0.195 (4)	0.257 (2)	0.5890 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0960 (3)	0.0793 (2)	0.02888 (14)	0.0102 (2)	0.00631 (17)	−0.00726 (16)
O1	0.0589 (13)	0.0376 (10)	0.0276 (8)	0.0034 (9)	−0.0034 (9)	−0.0093 (8)
O2	0.0655 (12)	0.0350 (10)	0.0301 (8)	0.0023 (10)	−0.0072 (10)	0.0018 (8)
N1	0.0566 (16)	0.0338 (13)	0.0237 (10)	0.0039 (11)	−0.0060 (10)	−0.0063 (9)
N2	0.0581 (16)	0.0306 (13)	0.0230 (11)	0.0104 (11)	−0.0077 (10)	−0.0070 (9)
C1	0.0354 (14)	0.0340 (13)	0.0236 (13)	−0.0019 (11)	−0.0012 (10)	−0.0033 (10)
C2	0.0435 (16)	0.0295 (12)	0.0298 (11)	−0.0011 (13)	0.0013 (11)	−0.0003 (11)
C3	0.0424 (16)	0.0334 (14)	0.0235 (11)	0.0021 (12)	−0.0035 (11)	0.0015 (10)
C4	0.0343 (14)	0.0348 (15)	0.0238 (12)	−0.0046 (11)	0.0011 (11)	−0.0070 (10)
C5	0.0470 (17)	0.0258 (14)	0.0343 (12)	0.0036 (13)	−0.0010 (11)	−0.0011 (12)
C6	0.0452 (16)	0.0362 (14)	0.0243 (13)	0.0032 (11)	−0.0068 (11)	0.0013 (11)
C7	0.0414 (15)	0.0393 (17)	0.0238 (11)	0.0003 (13)	−0.0026 (11)	−0.0027 (11)
C8	0.0370 (16)	0.0361 (15)	0.0287 (12)	−0.0032 (13)	0.0000 (10)	−0.0013 (12)
C9	0.0362 (15)	0.0342 (15)	0.0297 (12)	0.0039 (12)	−0.0045 (11)	−0.0069 (11)
C10	0.0434 (17)	0.0381 (14)	0.0304 (12)	0.0049 (13)	−0.0038 (11)	−0.0097 (12)
C11	0.0450 (18)	0.0456 (17)	0.0308 (13)	0.0094 (13)	−0.0012 (11)	−0.0093 (12)
C12	0.0512 (19)	0.055 (2)	0.0388 (15)	0.0096 (15)	−0.0131 (14)	−0.0196 (14)
C13	0.054 (2)	0.0368 (17)	0.0644 (19)	0.0002 (14)	−0.0103 (15)	−0.0221 (15)
C14	0.0483 (18)	0.0370 (17)	0.0421 (15)	−0.0020 (13)	−0.0031 (13)	−0.0037 (12)

Geometric parameters (Å, º) top

Br1—C11	1.896 (3)	C5—C6	1.378 (3)
O1—C4	1.367 (3)	C5—H5	0.9300
O1—H1	0.8200	C6—H6	0.9300
O2—C8	1.230 (3)	C7—H7	0.9300
N1—C7	1.260 (3)	C8—C9	1.495 (3)
N1—N2	1.387 (2)	C9—C14	1.384 (4)
N2—C8	1.351 (3)	C9—C10	1.387 (3)
N2—H2A	0.904 (10)	C10—C11	1.376 (3)
C1—C6	1.386 (3)	C10—H10	0.9300
C1—C2	1.398 (3)	C11—C12	1.382 (4)
C1—C7	1.462 (3)	C12—C13	1.371 (4)
C2—C3	1.374 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.381 (4)
C3—C4	1.386 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.381 (3)

C4—O1—H1	109.5	N1—C7—H7	119.0
C7—N1—N2	115.88 (19)	C1—C7—H7	119.0
C8—N2—N1	117.51 (19)	O2—C8—N2	122.9 (2)
C8—N2—H2A	121.7 (19)	O2—C8—C9	121.4 (2)
N1—N2—H2A	119 (2)	N2—C8—C9	115.7 (2)
C6—C1—C2	118.5 (2)	C14—C9—C10	120.1 (2)
C6—C1—C7	120.0 (2)	C14—C9—C8	118.2 (2)
C2—C1—C7	121.4 (2)	C10—C9—C8	121.7 (2)
C3—C2—C1	120.7 (2)	C11—C10—C9	119.1 (2)
C3—C2—H2	119.7	C11—C10—H10	120.5
C1—C2—H2	119.7	C9—C10—H10	120.5
C2—C3—C4	119.8 (2)	C10—C11—C12	121.3 (2)
C2—C3—H3	120.1	C10—C11—Br1	119.1 (2)
C4—C3—H3	120.1	C12—C11—Br1	119.65 (19)
O1—C4—C5	117.4 (2)	C13—C12—C11	119.1 (2)
O1—C4—C3	122.4 (2)	C13—C12—H12	120.4
C5—C4—C3	120.2 (2)	C11—C12—H12	120.4
C6—C5—C4	119.7 (2)	C12—C13—C14	120.7 (3)
C6—C5—H5	120.2	C12—C13—H13	119.6
C4—C5—H5	120.2	C14—C13—H13	119.6
C5—C6—C1	121.1 (2)	C13—C14—C9	119.7 (3)
C5—C6—H6	119.5	C13—C14—H14	120.1
C1—C6—H6	119.5	C9—C14—H14	120.1
N1—C7—C1	122.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.95	2.750 (2)	166
O1—H1···N1ⁱ	0.82	2.56	3.003 (3)	116
N2—H2A···O1ⁱⁱ	0.90 (1)	2.14 (1)	3.007 (3)	162 (3)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1/2, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrN₂O₂
M_r	319.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.5576 (11), 11.7337 (18), 15.021 (2)
V (Å³)	1332.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.09
Crystal size (mm)	0.20 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.577, 0.638
No. of measured, independent and observed [I > 2σ(I)] reflections	7740, 2757, 2145
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.059, 0.97
No. of reflections	2757
No. of parameters	176
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)	0.17, −0.29
Absolute structure	Flack (1983), with 1154 Friedel pairs
Absolute structure parameter	0.006 (9)

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···O2ⁱ	0.82	1.95	2.750 (2)	166
O1—H1···N1ⁱ	0.82	2.56	3.003 (3)	116
N2—H2A···O1ⁱⁱ	0.904 (10)	2.136 (14)	3.007 (3)	162 (3)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1/2, −y, z+1/2.

Acknowledgements

The Natural Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 07JK177) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 04JK302) are gratefully acknowledged.

References

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Cao, G.-B. (2007b). Acta Cryst. E63, m1149–m1150. Web of Science CSD CrossRef IUCr Journals Google Scholar
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