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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 7| July 2010| Page o1658
doi:10.1107/S1600536810022002

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

Shi-Yong Liua* and Zhonglu Youb

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 7 June 2010; accepted 8 June 2010; online 16 June 2010)

In the title compound, C15H13BrN2O3, the mol­ecule adopts an E configuration about the C=N bond and the two benzene rings form a dihedral angle of 20.3 (3)°. In the mol­ecule, there are two intra­molecular hydrogen bonds, viz. O—H⋯N and N—H⋯O, involving the hy­droxy substituent, the meth­oxy O atom and the hydrazide NH group and N atom. In the crystal structure, mol­ecules are linked through N—H⋯O hydrogen bonds, forming chains propagating along [010].

Related literature

For background to hydrazones and their medicinal applications, see: Hillmer et al. (2010[Hillmer, A. S., Putcha, P., Levin, J., Hogen, T., Hyman, B. T., Kretzschmar, H., McLean, P. J. & Giese, A. (2010). Biochem. Biophys. Res. Commun. 391, 461-466.]); Zhu et al. (2009[Zhu, Q.-Y., Wei, Y.-J. & Wang, F.-W. (2009). Pol. J. Chem. 83, 1233-1240.]); Jimenez-Pulido et al. (2008[Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem. 102, 1677-1683.]); Raj et al. (2007[Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425-429.]); Zhong et al. (2007[Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774-3777.]). For the crystal structures of hydrazones, see: Khaledi et al. (2009[Khaledi, H., Saharin, S. M., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2009). Acta Cryst. E65, o1920.]); Warad et al. (2009[Warad, I., Al-Nuri, M., Al-Resayes, S., Al-Farhan, K. & Ghazzali, M. (2009). Acta Cryst. E65, o1597.]); Back et al. (2009[Back, D. F., Ballin, M. A. & de Oliveira, G. M. (2009). J. Mol. Struct. 935, 151-155.]); Vijayakumar et al. (2009[Vijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564-1569.]). For similar compounds, see: Cao (2009[Cao, G.-B. (2009). Acta Cryst. E65, o2086.]); Xu et al. (2009[Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412.]); Shafiq et al. (2009[Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13BrN2O3

  • Mr = 349.18

  • Orthorhombic, P b c a

  • a = 15.587 (3) Å

  • b = 9.1281 (19) Å

  • c = 20.399 (4) Å

  • V = 2902.3 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.84 mm−1

  • T = 298 K

  • 0.23 × 0.20 × 0.20 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.561, Tmax = 0.600

  • 16311 measured reflections

  • 3154 independent reflections

  • 1496 reflections with I > 2σ(I)

  • Rint = 0.074
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.127

  • S = 1.00

  • 3154 reflections

  • 195 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.78 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O2i 0.89 (1) 2.14 (2) 2.978 (4) 157 (4)
N2—H2⋯O3 0.89 (1) 2.28 (4) 2.726 (4) 111 (3)
O1—H1⋯N1 0.82 1.93 2.646 (4) 146
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022002/su2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022002/su2186Isup2.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 of 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), and herein we report on the crystal structure of the new title hydrazone.

In the title molecule, illustrated in Fig. 1, the dihedral angle between the two benzene rings is 20.3 (3)°, indicating that the molecule is somewhat twisted. Atom C15 deviates from the plane of the benzene ring (C9-C14) by 0.075 (2) Å. All the bond lengths are comparable to those in similar compounds (Cao, 2009; Xu et al., 2009; Shafiq et al., 2009). In the molecule there are two intramolecular hydrogen bonds; O-H···N involving the hydroxyl group and the adjacent N hydrazide atom, and N-H···O involving the NH group and the adjacent O-atom of the methyl group (Table 1). The molecule has the E configuration about the C═N bond.

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

Related literature top

For background to hydrazones and their medicinal applications, see: Hillmer et al. (2010); Zhu et al. (2009); Jimenez-Pulido et al. (2008); Raj et al. (2007); Zhong et al. (2007). For the crystal structures of hydrazones, see: Khaledi et al. (2009); Warad et al. (2009); Back et al. (2009); Vijayakumar et al. (2009). For similar compounds, 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 2-methoxybenzohydrazide (0.05 mol, 8.3 g) in anhydrous methanol (200 mL) at RT. Colourless block-shaped single crystals, suitable for X-ray structure analysis, were obtained by slow evaporation of the solution over a period of a week.

Refinement top

H-atom H2, attached to N2, was located from a difference Fourier map and refined with a distance restraint of N-H = 0.90 (1) Å. The other H-atoms were placed in idealized positions and constrained to ride on their parent atoms: C-H = 0.93 - 0.96 Å, O-H = 0.82 Å, with Uiso(H) = k × Ueq(parent C-, O-atom), where k = 1.5 for H-hydroxyl and H-methyl, and = 1.2 for all other H-atoms.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. Hydrogen bonds are shown as dashed lines (see Table 1 for details).
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details). Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
(E)-N'-(5-Bromo-2-hydroxybenzylidene)-2-methoxybenzohydrazide top
Crystal data top
C15H13BrN2O3Dx = 1.598 Mg m−3
Mr = 349.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1832 reflections
a = 15.587 (3) Åθ = 2.5–24.0°
b = 9.1281 (19) ŵ = 2.84 mm−1
c = 20.399 (4) ÅT = 298 K
V = 2902.3 (10) Å3Block, colourless
Z = 80.23 × 0.20 × 0.20 mm
F(000) = 1408
Data collection top
Bruker SMART CCD area-detector
diffractometer		3154 independent reflections
Radiation source: fine-focus sealed tube1496 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −19→18
Tmin = 0.561, Tmax = 0.600k = −11→11
16311 measured reflectionsl = −26→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.6195P]
where P = (Fo2 + 2Fc2)/3
3154 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.64 e Å−3
1 restraintΔρmin = −0.78 e Å−3
Crystal data top
C15H13BrN2O3V = 2902.3 (10) Å3
Mr = 349.18Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 15.587 (3) ŵ = 2.84 mm−1
b = 9.1281 (19) ÅT = 298 K
c = 20.399 (4) Å0.23 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3154 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1496 reflections with I > 2σ(I)
Tmin = 0.561, Tmax = 0.600Rint = 0.074
16311 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.64 e Å−3
3154 reflectionsΔρmin = −0.78 e Å−3
195 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
Br11.23601 (3)0.49891 (6)0.43968 (3)0.0855 (2)
N10.8301 (2)0.4179 (3)0.38746 (13)0.0464 (7)
N20.76415 (19)0.4977 (3)0.35837 (15)0.0484 (7)
O10.89179 (19)0.2082 (3)0.46358 (15)0.0674 (8)
H10.85430.25420.44430.101*
O20.67329 (16)0.3058 (3)0.36404 (13)0.0598 (7)
O30.71532 (17)0.6580 (3)0.25197 (13)0.0629 (8)
C10.9761 (2)0.4067 (4)0.42007 (16)0.0425 (9)
C20.9676 (3)0.2766 (4)0.45609 (18)0.0524 (10)
C31.0386 (3)0.2181 (4)0.4871 (2)0.0659 (12)
H31.03290.13280.51170.079*
C41.1175 (3)0.2842 (5)0.4823 (2)0.0662 (12)
H41.16440.24440.50410.079*
C51.1271 (2)0.4091 (5)0.44529 (18)0.0547 (10)
C61.0566 (2)0.4699 (4)0.41518 (18)0.0504 (10)
H61.06320.55540.39100.061*
C70.9037 (2)0.4779 (4)0.38856 (17)0.0443 (9)
H70.91130.56890.36890.053*
C80.6876 (2)0.4335 (4)0.34843 (16)0.0436 (9)
C90.6191 (2)0.5270 (4)0.31930 (18)0.0446 (9)
C100.6332 (3)0.6357 (4)0.27206 (18)0.0498 (9)
C110.5635 (3)0.7133 (4)0.2475 (2)0.0636 (11)
H110.57230.78440.21550.076*
C120.4824 (3)0.6865 (5)0.2696 (2)0.0698 (12)
H120.43680.74060.25300.084*
C130.4671 (3)0.5804 (5)0.3162 (2)0.0674 (12)
H130.41170.56240.33110.081*
C140.5358 (3)0.5011 (4)0.34027 (18)0.0557 (10)
H140.52590.42850.37140.067*
C150.7306 (3)0.7746 (5)0.2062 (2)0.0778 (14)
H15A0.70060.75480.16610.117*
H15B0.79100.78160.19750.117*
H15C0.71060.86530.22440.117*
H20.777 (3)0.5907 (17)0.3488 (19)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0504 (3)0.1095 (5)0.0967 (4)0.0050 (3)−0.0067 (2)−0.0282 (3)
N10.051 (2)0.0402 (18)0.0483 (18)0.0045 (16)−0.0080 (15)0.0006 (14)
N20.0499 (18)0.0346 (17)0.0607 (19)−0.0031 (17)−0.0110 (15)0.0081 (17)
O10.077 (2)0.0522 (18)0.073 (2)0.0002 (16)0.0031 (16)0.0167 (15)
O20.0614 (17)0.0400 (16)0.0781 (19)−0.0060 (13)−0.0051 (14)0.0116 (14)
O30.0557 (18)0.0630 (18)0.0700 (18)0.0012 (14)−0.0027 (14)0.0282 (15)
C10.048 (2)0.039 (2)0.040 (2)0.0074 (18)−0.0037 (17)−0.0015 (17)
C20.066 (3)0.047 (3)0.045 (2)0.006 (2)0.000 (2)−0.0005 (19)
C30.090 (3)0.050 (3)0.057 (3)0.019 (3)−0.010 (2)0.007 (2)
C40.070 (3)0.073 (3)0.056 (3)0.030 (3)−0.017 (2)−0.015 (2)
C50.048 (2)0.064 (3)0.052 (2)0.011 (2)−0.0031 (19)−0.013 (2)
C60.053 (3)0.047 (2)0.051 (2)0.0085 (19)−0.0009 (18)−0.0040 (19)
C70.053 (2)0.035 (2)0.045 (2)0.0053 (18)−0.0015 (17)0.0026 (17)
C80.052 (3)0.036 (2)0.043 (2)−0.0034 (18)−0.0039 (17)−0.0031 (18)
C90.045 (2)0.038 (2)0.051 (2)−0.0002 (17)−0.0100 (17)−0.0037 (18)
C100.056 (3)0.041 (2)0.053 (2)0.0036 (19)−0.010 (2)−0.001 (2)
C110.064 (3)0.057 (3)0.070 (3)0.006 (2)−0.012 (2)0.010 (2)
C120.060 (3)0.063 (3)0.086 (3)0.015 (2)−0.016 (2)−0.003 (3)
C130.046 (3)0.073 (3)0.083 (3)0.005 (2)−0.010 (2)−0.016 (3)
C140.056 (3)0.055 (3)0.057 (2)−0.006 (2)−0.0048 (18)−0.002 (2)
C150.079 (3)0.077 (3)0.077 (3)−0.009 (2)−0.006 (2)0.029 (2)
Geometric parameters (Å, º) top
Br1—C51.888 (4)C5—C61.376 (5)
N1—C71.271 (4)C6—H60.9300
N1—N21.393 (4)C7—H70.9300
N2—C81.344 (4)C8—C91.491 (5)
N2—H20.892 (10)C9—C141.388 (5)
O1—C21.345 (5)C9—C101.401 (5)
O1—H10.8200C10—C111.390 (5)
O2—C81.229 (4)C11—C121.364 (6)
O3—C101.359 (4)C11—H110.9300
O3—C151.436 (4)C12—C131.377 (6)
C1—C61.386 (5)C12—H120.9300
C1—C21.403 (5)C13—C141.382 (5)
C1—C71.451 (5)C13—H130.9300
C2—C31.383 (5)C14—H140.9300
C3—C41.372 (6)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.375 (5)C15—H15C0.9600
C4—H40.9300
C7—N1—N2116.7 (3)O2—C8—N2122.4 (3)
C8—N2—N1119.4 (3)O2—C8—C9121.1 (3)
C8—N2—H2125 (3)N2—C8—C9116.5 (3)
N1—N2—H2115 (3)C14—C9—C10118.7 (3)
C2—O1—H1109.5C14—C9—C8116.7 (3)
C10—O3—C15117.6 (3)C10—C9—C8124.6 (3)
C6—C1—C2118.4 (3)O3—C10—C11123.4 (4)
C6—C1—C7119.1 (3)O3—C10—C9117.5 (3)
C2—C1—C7122.6 (4)C11—C10—C9119.1 (4)
O1—C2—C3118.2 (4)C12—C11—C10120.9 (4)
O1—C2—C1122.3 (4)C12—C11—H11119.5
C3—C2—C1119.5 (4)C10—C11—H11119.5
C4—C3—C2120.9 (4)C11—C12—C13120.9 (4)
C4—C3—H3119.5C11—C12—H12119.5
C2—C3—H3119.5C13—C12—H12119.5
C3—C4—C5120.1 (4)C12—C13—C14118.7 (4)
C3—C4—H4119.9C12—C13—H13120.7
C5—C4—H4119.9C14—C13—H13120.7
C4—C5—C6119.5 (4)C13—C14—C9121.7 (4)
C4—C5—Br1119.5 (3)C13—C14—H14119.2
C6—C5—Br1121.0 (3)C9—C14—H14119.2
C5—C6—C1121.6 (4)O3—C15—H15A109.5
C5—C6—H6119.2O3—C15—H15B109.5
C1—C6—H6119.2H15A—C15—H15B109.5
N1—C7—C1121.1 (3)O3—C15—H15C109.5
N1—C7—H7119.5H15A—C15—H15C109.5
C1—C7—H7119.5H15B—C15—H15C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.89 (1)2.14 (2)2.978 (4)157 (4)
N2—H2···O30.89 (1)2.28 (4)2.726 (4)111 (3)
O1—H1···N10.821.932.646 (4)146
Symmetry code: (i) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H13BrN2O3
Mr349.18
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)15.587 (3), 9.1281 (19), 20.399 (4)
V (Å3)2902.3 (10)
Z8
Radiation typeMo Kα
µ (mm−1)2.84
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.561, 0.600
No. of measured, independent and
observed [I > 2σ(I)] reflections		16311, 3154, 1496
Rint0.074
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.127, 1.00
No. of reflections3154
No. of parameters195
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.64, −0.78

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.892 (10)2.136 (18)2.978 (4)157 (4)
N2—H2···O30.892 (10)2.28 (4)2.726 (4)111 (3)
O1—H1···N10.821.932.646 (4)145.5
Symmetry code: (i) −x+3/2, y+1/2, z.
 

Acknowledgements

We acknowledge Taizhou University for financial support.

References

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ISSN: 2056-9890
Volume 66| Part 7| July 2010| Page o1658
doi:10.1107/S1600536810022002
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