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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1805.
Published online 2010 June 26. doi:  10.1107/S1600536810024001
PMCID: PMC3006758

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

Abstract

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

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Object name is e-66-o1805-scheme1.jpg

Experimental

Crystal data

  • C15H13BrN2O3
  • M r = 349.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1805-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.093
  • S = 1.01
  • 3079 reflections
  • 195 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024001/sj5025sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge Taizhou University for financial support.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H2 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. The remaining H atoms were positioned geometrically and constrained to ride on their parent atoms, with C–H distances of 0.93–0.96 Å, O–H distance of 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and Cmethyl).

Figures

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.

Crystal data

C15H13BrN2O3F(000) = 704
Mr = 349.18Dx = 1.565 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2100 reflections
a = 6.865 (2) Åθ = 2.6–25.0°
b = 30.726 (3) ŵ = 2.78 mm1
c = 7.257 (2) ÅT = 298 K
β = 104.437 (15)°Block, colourless
V = 1482.2 (7) Å30.27 × 0.25 × 0.23 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3079 independent reflections
Radiation source: fine-focus sealed tube1832 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 26.8°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −5→8
Tmin = 0.520, Tmax = 0.567k = −37→38
8593 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0443P)2] where P = (Fo2 + 2Fc2)/3
3079 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = −0.45 e Å3

Special details

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)

xyzUiso*/Ueq
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)
N20.1078 (3)0.24188 (7)0.6071 (3)0.0486 (6)
O1−0.4272 (3)0.18973 (6)0.5066 (3)0.0620 (5)
H1−0.33140.20600.51170.093*
O2−0.0895 (3)0.29146 (5)0.4185 (3)0.0522 (5)
O30.3228 (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)
H3−0.63360.12290.52270.068*
C4−0.4370 (5)0.07446 (9)0.6041 (4)0.0599 (8)
H4−0.53240.05260.59710.072*
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)
H60.04140.09060.71190.058*
C70.0005 (4)0.17332 (8)0.6411 (4)0.0457 (7)
H70.13410.16660.69790.055*
C80.0728 (4)0.28138 (8)0.5248 (4)0.0419 (6)
C90.2439 (4)0.31261 (8)0.5746 (3)0.0400 (6)
C100.1979 (4)0.35642 (8)0.5838 (3)0.0423 (6)
H100.06420.36520.55790.051*
C110.3486 (4)0.38683 (8)0.6308 (4)0.0502 (7)
C120.5471 (5)0.37320 (10)0.6659 (4)0.0631 (8)
H120.65000.39360.69750.076*
C130.5937 (4)0.33037 (10)0.6550 (4)0.0621 (8)
H130.72760.32190.67730.074*
C140.4423 (4)0.29916 (9)0.6106 (4)0.0507 (7)
H140.47380.26980.60530.061*
C150.1241 (6)0.44666 (9)0.6235 (5)0.0788 (10)
H15A0.04840.44130.49530.118*
H15B0.12900.47740.64770.118*
H15C0.06050.43230.71060.118*
H20.218 (3)0.2361 (10)0.700 (3)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1138 (3)0.03462 (19)0.0917 (3)−0.00088 (16)0.0212 (2)0.00419 (16)
N10.0508 (13)0.0366 (12)0.0480 (13)−0.0043 (10)−0.0004 (11)−0.0010 (10)
N20.0427 (14)0.0343 (12)0.0584 (16)−0.0037 (10)−0.0071 (11)0.0051 (10)
O10.0508 (11)0.0485 (12)0.0798 (15)0.0094 (9)0.0034 (11)0.0064 (10)
O20.0459 (11)0.0399 (10)0.0576 (12)0.0025 (8)−0.0118 (9)0.0016 (9)
O30.0952 (17)0.0360 (12)0.0915 (17)−0.0141 (11)0.0163 (13)−0.0061 (10)
C10.0455 (17)0.0356 (14)0.0398 (15)0.0018 (11)0.0036 (12)−0.0031 (11)
C20.0503 (18)0.0417 (15)0.0416 (15)0.0045 (13)0.0044 (13)−0.0005 (12)
C30.0486 (18)0.059 (2)0.0592 (19)−0.0049 (14)0.0069 (15)0.0009 (15)
C40.068 (2)0.0556 (19)0.0536 (19)−0.0215 (15)0.0104 (16)−0.0057 (14)
C50.074 (2)0.0326 (14)0.0478 (17)−0.0020 (13)0.0092 (15)−0.0011 (12)
C60.0494 (17)0.0400 (15)0.0506 (17)0.0037 (12)0.0045 (13)0.0006 (12)
C70.0455 (17)0.0367 (15)0.0493 (17)0.0011 (12)0.0014 (13)−0.0012 (12)
C80.0438 (16)0.0340 (14)0.0431 (16)0.0030 (12)0.0016 (13)−0.0029 (11)
C90.0407 (16)0.0384 (14)0.0380 (14)−0.0012 (11)0.0042 (12)−0.0005 (11)
C100.0421 (15)0.0398 (15)0.0420 (15)0.0006 (11)0.0049 (12)0.0016 (11)
C110.059 (2)0.0419 (16)0.0476 (17)−0.0059 (13)0.0095 (14)0.0020 (13)
C120.059 (2)0.063 (2)0.063 (2)−0.0242 (16)0.0088 (16)−0.0016 (16)
C130.0425 (18)0.069 (2)0.072 (2)−0.0037 (15)0.0091 (15)0.0009 (17)
C140.0472 (17)0.0466 (16)0.0550 (18)0.0078 (13)0.0069 (14)0.0016 (13)
C150.108 (3)0.0404 (18)0.092 (3)0.0104 (18)0.032 (2)−0.0006 (16)

Geometric parameters (Å, °)

Br1—C51.888 (3)C5—C61.373 (4)
N1—C71.282 (3)C6—H60.9300
N1—N21.379 (3)C7—H70.9300
N2—C81.347 (3)C8—C91.490 (3)
N2—H20.898 (10)C9—C141.384 (3)
O1—C21.350 (3)C9—C101.388 (3)
O1—H10.8200C10—C111.373 (3)
O2—C81.226 (3)C10—H100.9300
O3—C111.361 (3)C11—C121.387 (4)
O3—C151.421 (4)C12—C131.361 (4)
C1—C61.392 (3)C12—H120.9300
C1—C21.405 (3)C13—C141.392 (4)
C1—C71.451 (3)C13—H130.9300
C2—C31.380 (4)C14—H140.9300
C3—C41.371 (4)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.386 (4)C15—H15C0.9600
C4—H40.9300
C7—N1—N2116.7 (2)O2—C8—N2122.7 (2)
C8—N2—N1119.3 (2)O2—C8—C9121.9 (2)
C8—N2—H2122.3 (19)N2—C8—C9115.5 (2)
N1—N2—H2117.0 (19)C14—C9—C10120.3 (2)
C2—O1—H1109.5C14—C9—C8122.2 (2)
C11—O3—C15118.5 (2)C10—C9—C8117.5 (2)
C6—C1—C2118.4 (2)C11—C10—C9120.4 (2)
C6—C1—C7119.2 (2)C11—C10—H10119.8
C2—C1—C7122.4 (2)C9—C10—H10119.8
O1—C2—C3118.8 (2)O3—C11—C10125.8 (3)
O1—C2—C1122.0 (2)O3—C11—C12115.1 (2)
C3—C2—C1119.2 (2)C10—C11—C12119.0 (3)
C4—C3—C2121.5 (3)C13—C12—C11121.0 (3)
C4—C3—H3119.3C13—C12—H12119.5
C2—C3—H3119.3C11—C12—H12119.5
C3—C4—C5119.8 (3)C12—C13—C14120.5 (3)
C3—C4—H4120.1C12—C13—H13119.8
C5—C4—H4120.1C14—C13—H13119.8
C6—C5—C4119.4 (3)C9—C14—C13118.7 (3)
C6—C5—Br1119.7 (2)C9—C14—H14120.6
C4—C5—Br1120.9 (2)C13—C14—H14120.6
C5—C6—C1121.6 (3)O3—C15—H15A109.5
C5—C6—H6119.2O3—C15—H15B109.5
C1—C6—H6119.2H15A—C15—H15B109.5
N1—C7—C1120.6 (2)O3—C15—H15C109.5
N1—C7—H7119.7H15A—C15—H15C109.5
C1—C7—H7119.7H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.625 (3)146
N2—H2···O2i0.90 (1)1.98 (1)2.852 (3)163 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5025).

References

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