(E)-N′-(5-Bromo-2-hy­droxy­benzyl­idene)-3-meth­oxy­benzohydrazide

Liu, S.-Y.; Wang, X.

doi:10.1107/S1600536810024001

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1805

doi:10.1107/S1600536810024001

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(E)-N′-(5-Bromo-2-hydroxybenzylidene)-3-methoxybenzohydrazide

Shi-Yong Liu ^a ^* and Xiaoling Wang ^b

^aCollege of Chemistry & Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, and ^bDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 18 June 2010; accepted 21 June 2010; online 26 June 2010)

In the title compound, C₁₅H₁₃BrN₂O₃, the two benzene rings form a dihedral angle of 16.9 (2)°. An intramolecular O—H⋯N hydrogen bond affects the molecular conformation. In the crystal structure, molecules are linked through N—H⋯O hydrogen bonds into chains running along the a axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ); Zhu et al. (2009 ); Jimenez-Pulido et al. (2008 ); Raj et al. (2007 ); Zhong et al. (2007 ). For hydrazones we have reported previously, see: Liu & You (2010a ,b ,c ). For the structures of similar hydrazone compounds, see: Khaledi et al. (2009 ); Warad et al. (2009 ); Back et al. (2009 ); Vijayakumar et al. (2009 ). For related structures, see: Cao (2009 ); Xu et al. (2009 ); Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₃
M_r = 349.18
Monoclinic, P 2₁ /n
a = 6.865 (2) Å
b = 30.726 (3) Å
c = 7.257 (2) Å
β = 104.437 (15)°
V = 1482.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.78 mm⁻¹
T = 298 K
0.27 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.520, T_max = 0.567
8593 measured reflections
3079 independent reflections
1832 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.093
S = 1.01
3079 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.45 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	1.90	2.625 (3)	146
N2—H2⋯O2ⁱ	0.90 (1)	1.98 (1)	2.852 (3)	163 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536810024001/sj5025sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024001/sj5025Isup2.hkl

checkCIF report

Comment top

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Zhu et al., 2009; Jimenez-Pulido et al., 2008; Raj et al., 2007; Zhong et al., 2007). The study on the crystal structures of such compounds is of particular interest (Khaledi et al., 2009; Warad et al., 2009; Back et al., 2009; Vijayakumar et al., 2009). As a continuation of our work on such compounds (Liu & You, 2010a,b,c), we report herein the crystal structure of the title compound a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 16.9 (2)°. All the bond lengths are comparable to those observed in related structures (Cao, 2009; Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N—H···O hydrogen bonds, to form one-dimensional chains running along the a axis (Fig. 2 and Table 1).

Related literature top

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010); Zhu et al. (2009); Jimenez-Pulido et al. (2008); Raj et al. (2007); Zhong et al. (2007). For hydrazones we have reported previously, see: Liu & You (2010a,b,c). For the structures of similar hydrazone compounds, see: Khaledi et al. (2009); Warad et al. (2009); Back et al. (2009); Vijayakumar et al. (2009). For related structures, see: Cao (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 5-bromosalicylaldehyde (0.05 mol, 10 g) and 3-methoxybenzohydrazide (0.05 mol, 8.3 g) in anhydrous methanol (200 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for a period of 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 the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius and the intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₃BrN₂O₃	F(000) = 704
M_r = 349.18	D_x = 1.565 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2100 reflections
a = 6.865 (2) Å	θ = 2.6–25.0°
b = 30.726 (3) Å	µ = 2.78 mm⁻¹
c = 7.257 (2) Å	T = 298 K
β = 104.437 (15)°	Block, colourless
V = 1482.2 (7) Å³	0.27 × 0.25 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3079 independent reflections
Radiation source: fine-focus sealed tube	1832 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 26.8°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→8
T_min = 0.520, T_max = 0.567	k = −37→38
8593 measured reflections	l = −9→9

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0443P)²] where P = (F_o² + 2F_c²)/3
3079 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₃	V = 1482.2 (7) Å³
M_r = 349.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.865 (2) Å	µ = 2.78 mm⁻¹
b = 30.726 (3) Å	T = 298 K
c = 7.257 (2) Å	0.27 × 0.25 × 0.23 mm
β = 104.437 (15)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3079 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1832 reflections with I > 2σ(I)
T_min = 0.520, T_max = 0.567	R_int = 0.033
8593 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.25 e Å⁻³
3079 reflections	Δρ_min = −0.45 e Å⁻³
195 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	−0.14621 (6)	0.006913 (10)	0.72146 (5)	0.08082 (18)
N1	−0.0463 (3)	0.21192 (6)	0.5786 (3)	0.0474 (5)
N2	0.1078 (3)	0.24188 (7)	0.6071 (3)	0.0486 (6)
O1	−0.4272 (3)	0.18973 (6)	0.5066 (3)	0.0620 (5)
H1	−0.3314	0.2060	0.5117	0.093*
O2	−0.0895 (3)	0.29146 (5)	0.4185 (3)	0.0522 (5)
O3	0.3228 (3)	0.43040 (6)	0.6485 (3)	0.0755 (6)
C1	−0.1528 (4)	0.14004 (8)	0.6243 (3)	0.0415 (6)
C2	−0.3592 (4)	0.14938 (8)	0.5621 (4)	0.0458 (6)
C3	−0.4970 (4)	0.11647 (10)	0.5578 (4)	0.0568 (7)
H3	−0.6336	0.1229	0.5227	0.068*
C4	−0.4370 (5)	0.07446 (9)	0.6041 (4)	0.0599 (8)
H4	−0.5324	0.0526	0.5971	0.072*
C5	−0.2338 (5)	0.06462 (8)	0.6614 (4)	0.0524 (7)
C6	−0.0948 (4)	0.09725 (8)	0.6719 (4)	0.0481 (7)
H6	0.0414	0.0906	0.7119	0.058*
C7	0.0005 (4)	0.17332 (8)	0.6411 (4)	0.0457 (7)
H7	0.1341	0.1666	0.6979	0.055*
C8	0.0728 (4)	0.28138 (8)	0.5248 (4)	0.0419 (6)
C9	0.2439 (4)	0.31261 (8)	0.5746 (3)	0.0400 (6)
C10	0.1979 (4)	0.35642 (8)	0.5838 (3)	0.0423 (6)
H10	0.0642	0.3652	0.5579	0.051*
C11	0.3486 (4)	0.38683 (8)	0.6308 (4)	0.0502 (7)
C12	0.5471 (5)	0.37320 (10)	0.6659 (4)	0.0631 (8)
H12	0.6500	0.3936	0.6975	0.076*
C13	0.5937 (4)	0.33037 (10)	0.6550 (4)	0.0621 (8)
H13	0.7276	0.3219	0.6773	0.074*
C14	0.4423 (4)	0.29916 (9)	0.6106 (4)	0.0507 (7)
H14	0.4738	0.2698	0.6053	0.061*
C15	0.1241 (6)	0.44666 (9)	0.6235 (5)	0.0788 (10)
H15A	0.0484	0.4413	0.4953	0.118*
H15B	0.1290	0.4774	0.6477	0.118*
H15C	0.0605	0.4323	0.7106	0.118*
H2	0.218 (3)	0.2361 (10)	0.700 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1138 (3)	0.03462 (19)	0.0917 (3)	−0.00088 (16)	0.0212 (2)	0.00419 (16)
N1	0.0508 (13)	0.0366 (12)	0.0480 (13)	−0.0043 (10)	−0.0004 (11)	−0.0010 (10)
N2	0.0427 (14)	0.0343 (12)	0.0584 (16)	−0.0037 (10)	−0.0071 (11)	0.0051 (10)
O1	0.0508 (11)	0.0485 (12)	0.0798 (15)	0.0094 (9)	0.0034 (11)	0.0064 (10)
O2	0.0459 (11)	0.0399 (10)	0.0576 (12)	0.0025 (8)	−0.0118 (9)	0.0016 (9)
O3	0.0952 (17)	0.0360 (12)	0.0915 (17)	−0.0141 (11)	0.0163 (13)	−0.0061 (10)
C1	0.0455 (17)	0.0356 (14)	0.0398 (15)	0.0018 (11)	0.0036 (12)	−0.0031 (11)
C2	0.0503 (18)	0.0417 (15)	0.0416 (15)	0.0045 (13)	0.0044 (13)	−0.0005 (12)
C3	0.0486 (18)	0.059 (2)	0.0592 (19)	−0.0049 (14)	0.0069 (15)	0.0009 (15)
C4	0.068 (2)	0.0556 (19)	0.0536 (19)	−0.0215 (15)	0.0104 (16)	−0.0057 (14)
C5	0.074 (2)	0.0326 (14)	0.0478 (17)	−0.0020 (13)	0.0092 (15)	−0.0011 (12)
C6	0.0494 (17)	0.0400 (15)	0.0506 (17)	0.0037 (12)	0.0045 (13)	0.0006 (12)
C7	0.0455 (17)	0.0367 (15)	0.0493 (17)	0.0011 (12)	0.0014 (13)	−0.0012 (12)
C8	0.0438 (16)	0.0340 (14)	0.0431 (16)	0.0030 (12)	0.0016 (13)	−0.0029 (11)
C9	0.0407 (16)	0.0384 (14)	0.0380 (14)	−0.0012 (11)	0.0042 (12)	−0.0005 (11)
C10	0.0421 (15)	0.0398 (15)	0.0420 (15)	0.0006 (11)	0.0049 (12)	0.0016 (11)
C11	0.059 (2)	0.0419 (16)	0.0476 (17)	−0.0059 (13)	0.0095 (14)	0.0020 (13)
C12	0.059 (2)	0.063 (2)	0.063 (2)	−0.0242 (16)	0.0088 (16)	−0.0016 (16)
C13	0.0425 (18)	0.069 (2)	0.072 (2)	−0.0037 (15)	0.0091 (15)	0.0009 (17)
C14	0.0472 (17)	0.0466 (16)	0.0550 (18)	0.0078 (13)	0.0069 (14)	0.0016 (13)
C15	0.108 (3)	0.0404 (18)	0.092 (3)	0.0104 (18)	0.032 (2)	−0.0006 (16)

Geometric parameters (Å, º) top

Br1—C5	1.888 (3)	C5—C6	1.373 (4)
N1—C7	1.282 (3)	C6—H6	0.9300
N1—N2	1.379 (3)	C7—H7	0.9300
N2—C8	1.347 (3)	C8—C9	1.490 (3)
N2—H2	0.898 (10)	C9—C14	1.384 (3)
O1—C2	1.350 (3)	C9—C10	1.388 (3)
O1—H1	0.8200	C10—C11	1.373 (3)
O2—C8	1.226 (3)	C10—H10	0.9300
O3—C11	1.361 (3)	C11—C12	1.387 (4)
O3—C15	1.421 (4)	C12—C13	1.361 (4)
C1—C6	1.392 (3)	C12—H12	0.9300
C1—C2	1.405 (3)	C13—C14	1.392 (4)
C1—C7	1.451 (3)	C13—H13	0.9300
C2—C3	1.380 (4)	C14—H14	0.9300
C3—C4	1.371 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.386 (4)	C15—H15C	0.9600
C4—H4	0.9300

C7—N1—N2	116.7 (2)	O2—C8—N2	122.7 (2)
C8—N2—N1	119.3 (2)	O2—C8—C9	121.9 (2)
C8—N2—H2	122.3 (19)	N2—C8—C9	115.5 (2)
N1—N2—H2	117.0 (19)	C14—C9—C10	120.3 (2)
C2—O1—H1	109.5	C14—C9—C8	122.2 (2)
C11—O3—C15	118.5 (2)	C10—C9—C8	117.5 (2)
C6—C1—C2	118.4 (2)	C11—C10—C9	120.4 (2)
C6—C1—C7	119.2 (2)	C11—C10—H10	119.8
C2—C1—C7	122.4 (2)	C9—C10—H10	119.8
O1—C2—C3	118.8 (2)	O3—C11—C10	125.8 (3)
O1—C2—C1	122.0 (2)	O3—C11—C12	115.1 (2)
C3—C2—C1	119.2 (2)	C10—C11—C12	119.0 (3)
C4—C3—C2	121.5 (3)	C13—C12—C11	121.0 (3)
C4—C3—H3	119.3	C13—C12—H12	119.5
C2—C3—H3	119.3	C11—C12—H12	119.5
C3—C4—C5	119.8 (3)	C12—C13—C14	120.5 (3)
C3—C4—H4	120.1	C12—C13—H13	119.8
C5—C4—H4	120.1	C14—C13—H13	119.8
C6—C5—C4	119.4 (3)	C9—C14—C13	118.7 (3)
C6—C5—Br1	119.7 (2)	C9—C14—H14	120.6
C4—C5—Br1	120.9 (2)	C13—C14—H14	120.6
C5—C6—C1	121.6 (3)	O3—C15—H15A	109.5
C5—C6—H6	119.2	O3—C15—H15B	109.5
C1—C6—H6	119.2	H15A—C15—H15B	109.5
N1—C7—C1	120.6 (2)	O3—C15—H15C	109.5
N1—C7—H7	119.7	H15A—C15—H15C	109.5
C1—C7—H7	119.7	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.625 (3)	146
N2—H2···O2ⁱ	0.90 (1)	1.98 (1)	2.852 (3)	163 (3)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₃
M_r	349.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.865 (2), 30.726 (3), 7.257 (2)
β (°)	104.437 (15)
V (Å³)	1482.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.78
Crystal size (mm)	0.27 × 0.25 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.520, 0.567
No. of measured, independent and observed [I > 2σ(I)] reflections	8593, 3079, 1832
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.635

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 1.01
No. of reflections	3079
No. of parameters	195
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)	0.25, −0.45

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···N1	0.82	1.90	2.625 (3)	146
N2—H2···O2ⁱ	0.898 (10)	1.983 (13)	2.852 (3)	163 (3)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge Taizhou University for financial support.

References

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