Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Page o2048
doi:10.1107/S1600536808030900

N′-(5-Bromo-2-meth­oxy­benzyl­­idene)-2-hy­droxy­benzohydrazide

Jiu-Fu Lua*

aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
*Correspondence e-mail: jiufulu@163.com

(Received 19 September 2008; accepted 25 September 2008; online 30 September 2008)

The title Schiff base compound, C15H13BrN2O3, is derived from the condensation of 5-bromo-2-methoxy­benzaldehyde with 2-hydroxy­benzohydrazide in an ethanol solution. The dihedral angle between the two aromatic rings is 6.9 (9)°. The meth­oxy group is coplanar with the attached ring [C—O—C—C = 3.1 (12)°]. An intra­molecular N—H⋯O hydrogen bond is observed. In the crystal structure, the mol­ecules are linked into chains along the [001] direction by inter­molecular O—H⋯N, O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693.],b[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694.],c[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695.]); Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]); He (2008[He, L. (2008). Acta Cryst. E64, o82.]); Shi et al. (2007[Shi, X.-F., Liu, C.-Y., Liu, B. & Yuan, C.-C. (2007). Acta Cryst. E63, o1295-o1296.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13BrN2O3

  • Mr = 349.18

  • Tetragonal, I 41 /a

  • a = 15.530 (3) Å

  • c = 25.308 (2) Å

  • V = 6103.8 (17) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 2.70 mm−1

  • T = 298 (2) K

  • 0.12 × 0.10 × 0.10 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.737, Tmax = 0.774

  • 25116 measured reflections

  • 3322 independent reflections

  • 1243 reflections with I > 2σ(I)

  • Rint = 0.128
Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.226

  • S = 0.99

  • 3322 reflections

  • 195 parameters

  • 1 restraint

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

  • Δρmax = 0.97 e Å−3

  • Δρmin = −0.86 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O3 0.90 (3) 1.95 (5) 2.606 (6) 129 (5)
O3—H3⋯N1i 0.82 2.56 3.159 (6) 130
O3—H3⋯O2i 0.82 1.81 2.590 (5) 157
C6—H6⋯O3ii 0.93 2.55 3.471 (8) 174
Symmetry codes: (i) [-y+{\script{1\over 4}}, x-{\script{1\over 4}}, z-{\script{1\over 4}}]; (ii) [y+{\script{1\over 4}}, -x+{\script{1\over 4}}, z+{\script{1\over 4}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 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/S1600536808030900/ci2679sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030900/ci2679Isup2.hkl

checkCIF report


Comment top

As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report here the crystal structure of the title new Schiff base compound.

In the title molecule (Fig. 1), the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The methoxy group is coplanar with the attached ring [C15—O1—C2—C3 = 3.1 (12)°]. The dihedral angle between the two aromatic rings is 6.9 (9)°, indicating that the molecule is approximately planar. An intramolecular N—H···O hydrogen bond is observed in the molecule (Table 1).

In the crystal structure, the molecules are linked into chains (Fig. 2) along the [001] by intermolecular O—H···N, O—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For related structures, see: Lu et al. (2008a,b,c); Nie (2008); He (2008); Shi et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 5-bromo-2-methoxybenzaldehyde (0.1 mol) and 2-hydroxybenzohydrazide (0.1 mol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of a 95% ethanol solution at room temperature.

Refinement top

The imino H atom was located in a difference map and refined with a N-H distance restraint of 0.90 (1) Å and a fixed Uiso of 0.08 Å2. The other H atoms were positioned geometrically (C-H = 0.93-0.96 Å, O-H = 0.82 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl and O). A rotating group model was used for methyl and hydroxyl groups.The ratio of observed to unique reflections is low (37%), which is due to the poor diffraction quality of the crystal.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown by a dashed line.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.
N'-(5-Bromo-2-methoxybenzylidene)-2-hydroxybenzohydrazide top
Crystal data top
C15H13BrN2O3Dx = 1.520 Mg m−3
Mr = 349.18Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 1836 reflections
Hall symbol: -I 4adθ = 2.4–24.3°
a = 15.530 (3) ŵ = 2.70 mm−1
c = 25.308 (2) ÅT = 298 K
V = 6103.8 (17) Å3Block, colourless
Z = 160.12 × 0.10 × 0.10 mm
F(000) = 2816
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3322 independent reflections
Radiation source: fine-focus sealed tube1243 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.128
ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −19→19
Tmin = 0.737, Tmax = 0.774k = −19→19
25116 measured reflectionsl = −32→32
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0861P)2 + 12.6195P]
where P = (Fo2 + 2Fc2)/3
3322 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.97 e Å−3
1 restraintΔρmin = −0.86 e Å−3
Crystal data top
C15H13BrN2O3Z = 16
Mr = 349.18Mo Kα radiation
Tetragonal, I41/aµ = 2.70 mm−1
a = 15.530 (3) ÅT = 298 K
c = 25.308 (2) Å0.12 × 0.10 × 0.10 mm
V = 6103.8 (17) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3322 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1243 reflections with I > 2σ(I)
Tmin = 0.737, Tmax = 0.774Rint = 0.128
25116 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0681 restraint
wR(F2) = 0.226H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0861P)2 + 12.6195P]
where P = (Fo2 + 2Fc2)/3
3322 reflectionsΔρmax = 0.97 e Å−3
195 parametersΔρmin = −0.86 e Å−3
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
Br10.13353 (7)0.23636 (7)0.44885 (4)0.1335 (6)
O10.0993 (4)0.3108 (3)0.2169 (3)0.1107 (18)
O20.2734 (3)−0.0626 (3)0.28327 (15)0.0760 (13)
O30.2429 (3)−0.0129 (3)0.12353 (14)0.0729 (13)
H30.2527−0.00720.09190.109*
N10.2045 (3)0.0897 (4)0.26121 (18)0.0624 (14)
N20.2295 (4)0.0325 (3)0.22229 (18)0.0642 (14)
C10.1451 (4)0.2232 (4)0.2860 (3)0.0715 (19)
C20.1073 (5)0.3000 (6)0.2705 (4)0.090 (2)
C30.0784 (6)0.3586 (5)0.3092 (5)0.110 (3)
H3A0.05240.41010.29930.132*
C40.0888 (6)0.3391 (7)0.3611 (5)0.114 (3)
H40.07050.37800.38670.137*
C50.1251 (5)0.2647 (6)0.3760 (4)0.096 (3)
C60.1538 (5)0.2065 (4)0.3385 (3)0.080 (2)
H60.17940.15540.34930.095*
C70.1749 (4)0.1611 (5)0.2463 (3)0.0705 (19)
H70.17200.17440.21050.085*
C80.2622 (4)−0.0430 (4)0.2367 (2)0.0581 (16)
C90.2842 (4)−0.1056 (4)0.19439 (19)0.0512 (15)
C100.2728 (4)−0.0908 (4)0.1401 (2)0.0572 (16)
C110.2912 (4)−0.1555 (5)0.1043 (2)0.0662 (18)
H110.2822−0.14670.06840.079*
C120.3224 (5)−0.2320 (5)0.1218 (3)0.079 (2)
H120.3352−0.27520.09760.095*
C130.3354 (5)−0.2465 (5)0.1747 (3)0.084 (2)
H130.3582−0.29870.18620.100*
C140.3148 (4)−0.1842 (4)0.2101 (2)0.0687 (18)
H140.3217−0.19520.24600.082*
C150.0626 (6)0.3886 (6)0.1961 (5)0.143 (4)
H15A0.00620.39680.21070.215*
H15B0.05850.38420.15830.215*
H15C0.09850.43660.20520.215*
H20.221 (4)0.050 (4)0.1888 (9)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1547 (11)0.1402 (10)0.1057 (8)−0.0250 (7)0.0402 (6)−0.0549 (6)
O10.108 (5)0.077 (4)0.147 (6)0.014 (3)−0.005 (4)0.014 (4)
O20.113 (4)0.083 (3)0.032 (2)0.018 (3)0.002 (2)0.002 (2)
O30.107 (4)0.078 (3)0.034 (2)0.019 (3)0.007 (2)0.004 (2)
N10.081 (4)0.059 (4)0.048 (3)−0.004 (3)0.012 (3)−0.006 (3)
N20.092 (4)0.063 (4)0.038 (3)0.006 (3)0.002 (3)−0.004 (3)
C10.063 (5)0.061 (5)0.090 (6)−0.003 (4)0.013 (4)−0.004 (4)
C20.078 (5)0.073 (6)0.120 (7)−0.016 (5)0.006 (5)0.001 (6)
C30.092 (7)0.057 (5)0.181 (10)0.005 (4)0.019 (7)−0.010 (7)
C40.107 (7)0.085 (8)0.150 (10)−0.009 (6)0.036 (7)−0.034 (7)
C50.085 (6)0.075 (6)0.129 (7)−0.016 (5)0.026 (5)−0.026 (5)
C60.082 (5)0.066 (5)0.091 (6)−0.012 (4)0.020 (4)−0.025 (4)
C70.085 (5)0.065 (5)0.061 (4)−0.004 (4)0.007 (3)0.005 (4)
C80.066 (4)0.065 (5)0.043 (4)−0.007 (3)0.007 (3)−0.001 (3)
C90.061 (4)0.058 (4)0.034 (3)−0.009 (3)0.005 (3)−0.001 (3)
C100.055 (4)0.072 (5)0.045 (3)−0.005 (3)0.008 (3)−0.001 (3)
C110.074 (5)0.075 (5)0.049 (4)−0.007 (4)0.008 (3)−0.008 (4)
C120.103 (6)0.062 (5)0.073 (5)−0.007 (4)0.017 (4)−0.020 (4)
C130.116 (6)0.067 (5)0.067 (5)0.018 (4)0.015 (4)0.011 (4)
C140.089 (5)0.066 (5)0.052 (4)0.006 (4)0.013 (3)0.002 (3)
C150.109 (7)0.100 (7)0.221 (12)0.011 (6)−0.014 (7)0.048 (7)
Geometric parameters (Å, º) top
Br1—C51.900 (10)C5—C61.385 (10)
O1—C21.373 (10)C6—H60.93
O1—C151.436 (9)C7—H70.93
O2—C81.230 (7)C8—C91.485 (8)
O3—C101.362 (7)C9—C141.370 (8)
O3—H30.82C9—C101.405 (7)
N1—C71.259 (7)C10—C111.383 (8)
N1—N21.381 (7)C11—C121.356 (9)
N2—C81.330 (7)C11—H110.93
N2—H20.90 (3)C12—C131.373 (10)
C1—C61.360 (10)C12—H120.93
C1—C21.386 (10)C13—C141.357 (9)
C1—C71.467 (9)C13—H130.93
C2—C31.411 (12)C14—H140.93
C3—C41.356 (13)C15—H15A0.96
C3—H3A0.93C15—H15B0.96
C4—C51.340 (12)C15—H15C0.96
C4—H40.93
C2—O1—C15120.1 (8)O2—C8—N2122.4 (5)
C10—O3—H3109.5O2—C8—C9119.7 (6)
C7—N1—N2117.0 (5)N2—C8—C9117.9 (5)
C8—N2—N1118.6 (5)C14—C9—C10118.3 (5)
C8—N2—H2125 (4)C14—C9—C8117.0 (5)
N1—N2—H2116 (4)C10—C9—C8124.7 (6)
C6—C1—C2118.7 (7)O3—C10—C11121.0 (5)
C6—C1—C7120.9 (7)O3—C10—C9119.3 (5)
C2—C1—C7120.4 (8)C11—C10—C9119.7 (6)
O1—C2—C1115.0 (8)C12—C11—C10119.7 (6)
O1—C2—C3125.4 (9)C12—C11—H11120.1
C1—C2—C3119.6 (9)C10—C11—H11120.1
C4—C3—C2119.3 (9)C11—C12—C13121.1 (6)
C4—C3—H3A120.3C11—C12—H12119.5
C2—C3—H3A120.3C13—C12—H12119.5
C5—C4—C3121.1 (9)C14—C13—C12119.4 (7)
C5—C4—H4119.5C14—C13—H13120.3
C3—C4—H4119.5C12—C13—H13120.3
C4—C5—C6120.3 (9)C13—C14—C9121.8 (6)
C4—C5—Br1120.2 (8)C13—C14—H14119.1
C6—C5—Br1119.5 (8)C9—C14—H14119.1
C1—C6—C5121.0 (8)O1—C15—H15A109.5
C1—C6—H6119.5O1—C15—H15B109.5
C5—C6—H6119.5H15A—C15—H15B109.5
N1—C7—C1119.2 (6)O1—C15—H15C109.5
N1—C7—H7120.4H15A—C15—H15C109.5
C1—C7—H7120.4H15B—C15—H15C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.90 (3)1.95 (5)2.606 (6)129 (5)
O3—H3···N1i0.822.563.159 (6)130
O3—H3···O2i0.821.812.590 (5)157
C6—H6···O3ii0.932.553.471 (8)174
Symmetry codes: (i) −y+1/4, x−1/4, z−1/4; (ii) y+1/4, −x+1/4, z+1/4.

Experimental details

Crystal data
Chemical formulaC15H13BrN2O3
Mr349.18
Crystal system, space groupTetragonal, I41/a
Temperature (K)298
a, c (Å)15.530 (3), 25.308 (2)
V (Å3)6103.8 (17)
Z16
Radiation typeMo Kα
µ (mm−1)2.70
Crystal size (mm)0.12 × 0.10 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.737, 0.774
No. of measured, independent and
observed [I > 2σ(I)] reflections		25116, 3322, 1243
Rint0.128
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.226, 0.99
No. of reflections3322
No. of parameters195
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0861P)2 + 12.6195P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.97, −0.86

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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···O30.90 (3)1.95 (5)2.606 (6)129 (5)
O3—H3···N1i0.822.563.159 (6)130
O3—H3···O2i0.821.812.590 (5)157
C6—H6···O3ii0.932.553.471 (8)174
Symmetry codes: (i) −y+1/4, x−1/4, z−1/4; (ii) y+1/4, −x+1/4, z+1/4.
 

Acknowledgements

The author thanks the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.  CrossRef Web of Science Google Scholar
 First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHe, L. (2008). Acta Cryst. E64, o82.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNie, Y. (2008). Acta Cryst. E64, o471.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShi, X.-F., Liu, C.-Y., Liu, B. & Yuan, C.-C. (2007). Acta Cryst. E63, o1295–o1296.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Page o2048
doi:10.1107/S1600536808030900
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS