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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-4-Hy­dr­oxy-N′-(2-meth­­oxy­benzyl­­idene)benzohydrazide

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Biological Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 11 May 2012; accepted 15 May 2012; online 23 May 2012)

In the title compound, C15H14N2O3, the dihedral angle between the benzene rings is 66.56 (5)°. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O inter­actions link the mol­ecules into a three-dimensional network. A ππ inter­action, with a centroid–centroid distance of 3.628 (6) Å, helps to establish the packing.

Related literature

For the properties of hydrazone derivatives, see: Lever (1972[Lever, M. (1972). Anal. Biochem. 47, 273-279.]); Pelizzi & Pelizzi (1980[Pelizzi, C. & Pelizzi, G. (1980). J. Chem. Soc. Dalton Trans. pp. 1970-1973.]). For related structures, see: Shan et al. (2003[Shan, S., Xu, D.-J., Hung, C.-H., Wu, J.-Y. & Chiang, M. Y. (2003). Acta Cryst. C59, o135-o136.]); Fun et al. (1996[Fun, H.-K., Sivakumar, K., Lu, Z.-L., Duan, C.-Y., Tian, Y.-P. & You, X.-Z. (1996). Acta Cryst. C52, 986-988.]); Ferguson et al. (2005[Ferguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o613-o616.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O3

  • Mr = 270.28

  • Orthorhombic, P b c a

  • a = 14.3951 (3) Å

  • b = 8.7449 (2) Å

  • c = 21.1047 (4) Å

  • V = 2656.74 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.49 × 0.28 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.991

  • 32112 measured reflections

  • 4442 independent reflections

  • 3512 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.114

  • S = 1.03

  • 4442 reflections

  • 190 parameters

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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯O2i 0.916 (16) 2.009 (16) 2.9202 (12) 172.8 (15)
O1—H1O1⋯O2ii 0.87 (2) 1.80 (2) 2.6528 (11) 164.2 (17)
C13—H13A⋯O1iii 0.95 2.52 3.4669 (15) 171
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The chemical properties of hydrazone derivatives have been intensively investigated in several research fields mainly due to their facile synthesis, tuneable electronic and steric properties, and good chelating ability (Pelizzi & Pelizzi, 1980). Some derivatives of the title compound, (I), were used for the determination of glucose (Lever, 1972). These compounds crystallize in the E conformation (Shan et al., 2003; Fun et al., 1996) and isomeric compounds have also been prepared (Ferguson et al., 2005).

All parameters in (I), are within normal ranges. The dihedral angle between C1—C6 and C9 C14 benzene ring is 66.56 (5)°. In the crystal structure, the molecules are interconnected by N1—H1N1···O2i, O1—H1O1···O2ii and C13—H13A···O1iii hydrogen bonds. A ππ interaction with centroid-centroid distance of 3.628 (6) Å also occurs (Cg1 = C9—C14, -x, -y, -z).

Related literature top

For the properties of hydrazone derivatives, see: Lever (1972); Pelizzi & Pelizzi (1980). For related structures, see: Shan et al. (2003); Fun et al. (1996); Ferguson et al. (2005).

Experimental top

A solution of 2-methoxybenzaldehyde (136 mg, 1 mmol) in methanol (10 ml) was added dropwise to a methanolic solution (10 ml) of 4-hydroxybenzhydrazide (152 mg, 1 mmol) and the mixture was refluxed for 2 h. The resulting solution was condensed on a steam bath to 5 ml and cooled to room temperature. Yellow plates were separated out, washed with cooled methanol and dried in air.

Refinement top

N and O bound H atoms were located in a difference Fourier map and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. A rotating group model was applied to the methyl group.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
(E)-4-Hydroxy-N'-(2-methoxybenzylidene)benzohydrazide top
Crystal data top
C15H14N2O3F(000) = 1136
Mr = 270.28Dx = 1.351 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8771 reflections
a = 14.3951 (3) Åθ = 2.4–31.5°
b = 8.7449 (2) ŵ = 0.10 mm1
c = 21.1047 (4) ÅT = 100 K
V = 2656.74 (10) Å3Plate, yellow
Z = 80.49 × 0.28 × 0.09 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4442 independent reflections
Radiation source: fine-focus sealed tube3512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 31.6°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2121
Tmin = 0.954, Tmax = 0.991k = 1212
32112 measured reflectionsl = 3031
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.959P]
where P = (Fo2 + 2Fc2)/3
4442 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C15H14N2O3V = 2656.74 (10) Å3
Mr = 270.28Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.3951 (3) ŵ = 0.10 mm1
b = 8.7449 (2) ÅT = 100 K
c = 21.1047 (4) Å0.49 × 0.28 × 0.09 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4442 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3512 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.991Rint = 0.036
32112 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.37 e Å3
4442 reflectionsΔρmin = 0.20 e Å3
190 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
xyzUiso*/Ueq
O10.48726 (6)0.48027 (10)0.36875 (4)0.02079 (17)
O20.16105 (5)0.45718 (9)0.17195 (4)0.01884 (16)
O30.13520 (6)0.20688 (9)0.02729 (4)0.02154 (18)
N10.22355 (7)0.22544 (11)0.14758 (4)0.01752 (18)
N20.17102 (6)0.21485 (11)0.09246 (4)0.01848 (19)
C10.38142 (7)0.31733 (13)0.22565 (5)0.0181 (2)
H1A0.39700.25440.19050.022*
C20.44845 (7)0.35161 (13)0.27091 (5)0.0184 (2)
H2A0.50980.31300.26650.022*
C30.42528 (7)0.44303 (13)0.32286 (5)0.0170 (2)
C40.33481 (8)0.49850 (14)0.32950 (5)0.0204 (2)
H4A0.31850.55830.36540.024*
C50.26913 (7)0.46623 (13)0.28374 (5)0.0187 (2)
H5A0.20820.50660.28780.022*
C60.29126 (7)0.37485 (12)0.23154 (5)0.01578 (19)
C70.21981 (7)0.35457 (12)0.18194 (5)0.01583 (19)
C80.17442 (7)0.08270 (13)0.06597 (5)0.0185 (2)
H8A0.20480.00080.08710.022*
C90.13238 (7)0.05622 (13)0.00393 (5)0.0176 (2)
C100.11156 (8)0.17623 (13)0.03728 (5)0.0210 (2)
H10A0.12400.27850.02460.025*
C110.07298 (8)0.14849 (14)0.09648 (5)0.0229 (2)
H11A0.05820.23100.12400.027*
C120.05632 (8)0.00132 (15)0.11500 (5)0.0227 (2)
H12A0.03010.02080.15550.027*
C130.07724 (8)0.12288 (14)0.07539 (5)0.0209 (2)
H13A0.06590.22480.08890.025*
C140.11498 (7)0.09490 (13)0.01561 (5)0.0176 (2)
C150.11450 (9)0.36068 (13)0.00934 (6)0.0237 (2)
H15A0.12940.42970.04450.036*
H15B0.15160.38860.02780.036*
H15C0.04830.36920.00090.036*
H1N10.2628 (11)0.1465 (19)0.1575 (7)0.027 (4)*
H1O10.5437 (14)0.455 (2)0.3577 (9)0.050 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0171 (4)0.0257 (4)0.0195 (3)0.0008 (3)0.0020 (3)0.0037 (3)
O20.0166 (3)0.0165 (4)0.0233 (4)0.0005 (3)0.0012 (3)0.0014 (3)
O30.0272 (4)0.0151 (4)0.0223 (4)0.0010 (3)0.0063 (3)0.0006 (3)
N10.0184 (4)0.0148 (4)0.0194 (4)0.0003 (4)0.0037 (3)0.0015 (3)
N20.0178 (4)0.0190 (4)0.0187 (4)0.0013 (4)0.0023 (3)0.0012 (3)
C10.0176 (5)0.0176 (5)0.0192 (4)0.0007 (4)0.0017 (3)0.0031 (4)
C20.0152 (4)0.0187 (5)0.0213 (4)0.0012 (4)0.0011 (3)0.0024 (4)
C30.0169 (4)0.0167 (5)0.0174 (4)0.0022 (4)0.0004 (3)0.0007 (4)
C40.0199 (5)0.0234 (5)0.0178 (4)0.0015 (5)0.0011 (4)0.0039 (4)
C50.0169 (4)0.0201 (5)0.0191 (4)0.0021 (4)0.0010 (4)0.0018 (4)
C60.0158 (4)0.0140 (4)0.0175 (4)0.0009 (4)0.0002 (3)0.0005 (4)
C70.0153 (4)0.0146 (5)0.0175 (4)0.0023 (4)0.0021 (3)0.0003 (4)
C80.0185 (5)0.0175 (5)0.0196 (4)0.0014 (4)0.0022 (3)0.0001 (4)
C90.0168 (4)0.0180 (5)0.0180 (4)0.0020 (4)0.0007 (3)0.0014 (4)
C100.0233 (5)0.0169 (5)0.0229 (5)0.0019 (4)0.0017 (4)0.0007 (4)
C110.0258 (5)0.0215 (5)0.0213 (5)0.0004 (5)0.0023 (4)0.0043 (4)
C120.0233 (5)0.0261 (6)0.0186 (4)0.0013 (5)0.0031 (4)0.0002 (4)
C130.0230 (5)0.0195 (5)0.0201 (4)0.0016 (5)0.0027 (4)0.0026 (4)
C140.0173 (4)0.0172 (5)0.0183 (4)0.0000 (4)0.0008 (3)0.0001 (4)
C150.0288 (6)0.0146 (5)0.0278 (5)0.0019 (5)0.0038 (4)0.0006 (4)
Geometric parameters (Å, º) top
O1—C31.3565 (12)C5—H5A0.9500
O1—H1O10.87 (2)C6—C71.4782 (14)
O2—C71.2510 (13)C8—C91.4609 (14)
O3—C141.3650 (13)C8—H8A0.9500
O3—C151.4287 (14)C9—C101.3956 (15)
N1—C71.3432 (14)C9—C141.4068 (16)
N1—N21.3905 (12)C10—C111.3885 (15)
N1—H1N10.917 (16)C10—H10A0.9500
N2—C81.2848 (14)C11—C121.3880 (17)
C1—C21.3904 (14)C11—H11A0.9500
C1—C61.3974 (15)C12—C131.3856 (16)
C1—H1A0.9500C12—H12A0.9500
C2—C31.3973 (15)C13—C141.3953 (14)
C2—H2A0.9500C13—H13A0.9500
C3—C41.3969 (15)C15—H15A0.9800
C4—C51.3806 (15)C15—H15B0.9800
C4—H4A0.9500C15—H15C0.9800
C5—C61.3978 (14)
C3—O1—H1O1111.1 (12)N2—C8—C9121.12 (10)
C14—O3—C15117.06 (8)N2—C8—H8A119.4
C7—N1—N2119.07 (9)C9—C8—H8A119.4
C7—N1—H1N1122.3 (9)C10—C9—C14119.05 (10)
N2—N1—H1N1118.5 (9)C10—C9—C8121.89 (10)
C8—N2—N1113.78 (9)C14—C9—C8119.03 (10)
C2—C1—C6120.38 (10)C11—C10—C9121.01 (11)
C2—C1—H1A119.8C11—C10—H10A119.5
C6—C1—H1A119.8C9—C10—H10A119.5
C1—C2—C3119.79 (10)C12—C11—C10119.17 (10)
C1—C2—H2A120.1C12—C11—H11A120.4
C3—C2—H2A120.1C10—C11—H11A120.4
O1—C3—C4117.28 (9)C13—C12—C11121.11 (10)
O1—C3—C2122.73 (10)C13—C12—H12A119.4
C4—C3—C2119.99 (10)C11—C12—H12A119.4
C5—C4—C3119.82 (10)C12—C13—C14119.72 (11)
C5—C4—H4A120.1C12—C13—H13A120.1
C3—C4—H4A120.1C14—C13—H13A120.1
C4—C5—C6120.81 (10)O3—C14—C13123.85 (10)
C4—C5—H5A119.6O3—C14—C9116.20 (9)
C6—C5—H5A119.6C13—C14—C9119.93 (10)
C1—C6—C5119.18 (9)O3—C15—H15A109.5
C1—C6—C7122.68 (9)O3—C15—H15B109.5
C5—C6—C7117.92 (9)H15A—C15—H15B109.5
O2—C7—N1122.63 (9)O3—C15—H15C109.5
O2—C7—C6120.24 (9)H15A—C15—H15C109.5
N1—C7—C6117.09 (9)H15B—C15—H15C109.5
C7—N1—N2—C8175.07 (10)N1—N2—C8—C9172.79 (9)
C6—C1—C2—C30.55 (17)N2—C8—C9—C1019.20 (16)
C1—C2—C3—O1179.77 (10)N2—C8—C9—C14162.77 (10)
C1—C2—C3—C40.59 (17)C14—C9—C10—C110.93 (17)
O1—C3—C4—C5179.00 (10)C8—C9—C10—C11178.95 (10)
C2—C3—C4—C51.77 (17)C9—C10—C11—C120.96 (18)
C3—C4—C5—C61.84 (17)C10—C11—C12—C130.22 (18)
C2—C1—C6—C50.50 (16)C11—C12—C13—C140.54 (18)
C2—C1—C6—C7173.99 (10)C15—O3—C14—C131.07 (16)
C4—C5—C6—C10.70 (16)C15—O3—C14—C9177.53 (10)
C4—C5—C6—C7175.45 (10)C12—C13—C14—O3177.98 (10)
N2—N1—C7—O210.90 (15)C12—C13—C14—C90.57 (16)
N2—N1—C7—C6166.78 (9)C10—C9—C14—O3178.81 (10)
C1—C6—C7—O2145.49 (11)C8—C9—C14—O33.10 (14)
C5—C6—C7—O229.07 (15)C10—C9—C14—C130.15 (16)
C1—C6—C7—N132.25 (15)C8—C9—C14—C13178.24 (10)
C5—C6—C7—N1153.19 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.916 (16)2.009 (16)2.9202 (12)172.8 (15)
O1—H1O1···O2ii0.87 (2)1.80 (2)2.6528 (11)164.2 (17)
C13—H13A···O1iii0.952.523.4669 (15)171
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y, z+1/2; (iii) x+1/2, y, z1/2.

Experimental details

Crystal data
Chemical formulaC15H14N2O3
Mr270.28
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)100
a, b, c (Å)14.3951 (3), 8.7449 (2), 21.1047 (4)
V3)2656.74 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.49 × 0.28 × 0.09
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.954, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
32112, 4442, 3512
Rint0.036
(sin θ/λ)max1)0.737
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.114, 1.03
No. of reflections4442
No. of parameters190
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.916 (16)2.009 (16)2.9202 (12)172.8 (15)
O1—H1O1···O2ii0.87 (2)1.80 (2)2.6528 (11)164.2 (17)
C13—H13A···O1iii0.952.523.4669 (15)171
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y, z+1/2; (iii) x+1/2, y, z1/2.
 

Footnotes

Additional correspondence author, e-mail: abdussalam@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

We thank Universiti Sains Malaysia for awarding an RU (1001/PKIMIA/811196) grant. HKF thank USM for the Research University Grant No. 1001/PFIZIK/811160.

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFerguson, G., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o613–o616.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationFun, H.-K., Sivakumar, K., Lu, Z.-L., Duan, C.-Y., Tian, Y.-P. & You, X.-Z. (1996). Acta Cryst. C52, 986–988.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationLever, M. (1972). Anal. Biochem. 47, 273–279.  CrossRef CAS PubMed Web of Science Google Scholar
First citationPelizzi, C. & Pelizzi, G. (1980). J. Chem. Soc. Dalton Trans. pp. 1970–1973.  CSD CrossRef Web of Science Google Scholar
First citationShan, S., Xu, D.-J., Hung, C.-H., Wu, J.-Y. & Chiang, M. Y. (2003). Acta Cryst. C59, o135–o136.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS 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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds