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In the title compound, C14H12N2O3, the dihedral angle between the two benzene rings is 21.70 (4)°. An intra­molecular O—H...N hydrogen bond generates an S(6) ring motif. In the crystal structure, the mol­ecules are linked by inter­molecular O—H...O, N—H...O and C—H...O hydrogen bonds into a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021745/ci2382sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021745/ci2382Isup2.hkl
Contains datablock I

CCDC reference: 651419

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C)= 0.001 Å
  • R factor = 0.044
  • wR factor = 0.138
  • Data-to-parameter ratio = 28.2

checkCIF/PLATON results

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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 et al., 1972). These compounds crystallize in the E conformation (Shan et al., 2003; Fun et al., 1996; Naidu et al., 1996), and isomeric compounds have also been prepared (Ferguson et al., 2005). We report here the crystal structure of the title compound, (I).

The bond lengths and angles in (I) have normal values (Allen et al., 1987) and are comparable to those in a related structure (Lyubchova et al., 1995). The molecule is slightly twisted about C6—C7 bond, with diheral angle between the two benzene rings (C1—C6 and C9—C14) being 21.70 (4)°. The hydroxyl groups at C3 and C14 lie almost coplanar to the benzene rings to which they are attached, with out-of-plane distances for O1 and O3 atoms of 0.018 (1) and 0.024 (1) Å, respectively.

An intramolecular O3—H3A···N2 interaction (Table 1 and Fig. 1) generates an S(6) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are linked by intermolecular O—H···O, N—H···O and C—H···O type hydrogen bonds into a three-dimensional framework (Fig. 2).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see: Lyubchova et al. (1995); Ferguson et al. (2005); Fun et al. (1996); Lever (1972); Mani Naidu et al. (1996); Pelizzi & Pelizzi (1980); Shan et al. (2003).

Experimental top

A solution of salicylaldehyde (122 mg, 1 mmol) in methanol (10 m) was added dropwise to a methanol solution (10 ml) of 4-hydroxybenzhydrazide (136 mg, 1 mmol) and the mixture was refluxed for 2 h. The resulting solution was evaporated on a steam bath to 5 ml and cooled to room temperature. Yellow crystals of (I) suitable for X-ray diffraction separated out and were filtered off, then washed with 5 ml of cooled methanol and dried in air.

Refinement top

H atoms on N and O atoms were located in a difference map and refined isotropically [N—H = 0.88 (2) Å and O—H = 0.88 (2)–0.89 (2) Å]. The remaining H atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Structure description 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 et al., 1972). These compounds crystallize in the E conformation (Shan et al., 2003; Fun et al., 1996; Naidu et al., 1996), and isomeric compounds have also been prepared (Ferguson et al., 2005). We report here the crystal structure of the title compound, (I).

The bond lengths and angles in (I) have normal values (Allen et al., 1987) and are comparable to those in a related structure (Lyubchova et al., 1995). The molecule is slightly twisted about C6—C7 bond, with diheral angle between the two benzene rings (C1—C6 and C9—C14) being 21.70 (4)°. The hydroxyl groups at C3 and C14 lie almost coplanar to the benzene rings to which they are attached, with out-of-plane distances for O1 and O3 atoms of 0.018 (1) and 0.024 (1) Å, respectively.

An intramolecular O3—H3A···N2 interaction (Table 1 and Fig. 1) generates an S(6) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are linked by intermolecular O—H···O, N—H···O and C—H···O type hydrogen bonds into a three-dimensional framework (Fig. 2).

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see: Lyubchova et al. (1995); Ferguson et al. (2005); Fun et al. (1996); Lever (1972); Mani Naidu et al. (1996); Pelizzi & Pelizzi (1980); Shan et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed line indicates a hydrogen bond.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
4-Hydroxy-N'-[(E)-(2-hydroxyphenyl)methylidene]benzohydrazide top
Crystal data top
C14H12N2O3F(000) = 536
Mr = 256.26Dx = 1.440 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5136 reflections
a = 13.5978 (5) Åθ = 1.6–35.0°
b = 8.0656 (3) ŵ = 0.10 mm1
c = 11.4128 (4) ÅT = 100 K
β = 109.238 (2)°Block, colourless
V = 1181.80 (8) Å30.41 × 0.21 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5185 independent reflections
Radiation source: fine-focus sealed tube4394 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 8.33 pixels mm-1θmax = 35.0°, θmin = 1.6°
ω scansh = 2121
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1212
Tmin = 0.878, Tmax = 0.991l = 1818
34050 measured reflections
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) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0831P)2 + 0.2009P]
where P = (Fo2 + 2Fc2)/3
5185 reflections(Δ/σ)max = 0.001
184 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H12N2O3V = 1181.80 (8) Å3
Mr = 256.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.5978 (5) ŵ = 0.10 mm1
b = 8.0656 (3) ÅT = 100 K
c = 11.4128 (4) Å0.41 × 0.21 × 0.09 mm
β = 109.238 (2)°
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5185 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4394 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.991Rint = 0.034
34050 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.54 e Å3
5185 reflectionsΔρmin = 0.29 e Å3
184 parameters
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O10.03503 (5)1.28061 (9)0.00201 (6)0.01848 (13)
O20.21825 (4)0.84194 (9)0.46567 (5)0.01660 (13)
O30.44856 (5)0.60515 (9)0.67431 (6)0.01678 (13)
N10.34439 (5)0.87903 (9)0.38035 (6)0.01407 (13)
N20.41034 (5)0.78729 (9)0.47462 (6)0.01335 (13)
C10.08643 (6)1.07094 (10)0.29951 (7)0.01423 (14)
H1A0.07551.05310.37480.017*
C20.01575 (6)1.16534 (11)0.20889 (7)0.01492 (14)
H2A0.04191.21110.22350.018*
C30.03152 (6)1.19150 (11)0.09501 (7)0.01459 (14)
C40.11898 (6)1.12422 (12)0.07450 (7)0.01746 (15)
H4A0.12991.14250.00070.021*
C50.18981 (6)1.03015 (12)0.16573 (7)0.01678 (15)
H5A0.24790.98570.15130.020*
C60.17425 (5)1.00178 (10)0.27965 (7)0.01306 (13)
C70.24494 (5)0.90150 (10)0.38087 (7)0.01272 (13)
C80.50372 (6)0.76244 (10)0.47417 (7)0.01381 (14)
H8A0.52450.80460.41020.017*
C90.57653 (5)0.66847 (10)0.57382 (6)0.01236 (13)
C100.67930 (6)0.64939 (11)0.57431 (7)0.01548 (14)
H10A0.69880.69680.51100.019*
C110.75215 (6)0.56124 (12)0.66729 (8)0.01823 (16)
H11A0.81990.54920.66630.022*
C120.72291 (6)0.49078 (12)0.76224 (7)0.01814 (15)
H12A0.77170.43260.82540.022*
C130.62144 (6)0.50647 (11)0.76368 (7)0.01626 (15)
H13A0.60270.45820.82730.020*
C140.54761 (6)0.59453 (10)0.66996 (7)0.01319 (13)
H1B0.0923 (12)1.303 (2)0.0209 (14)0.029 (4)*
H1C0.3652 (12)0.914 (2)0.3191 (15)0.034 (4)*
H3A0.4105 (13)0.661 (2)0.6095 (17)0.043 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0146 (2)0.0239 (3)0.0172 (3)0.0055 (2)0.00550 (19)0.0054 (2)
O20.0139 (2)0.0230 (3)0.0136 (2)0.0001 (2)0.00554 (18)0.0013 (2)
O30.0159 (2)0.0211 (3)0.0160 (2)0.0003 (2)0.0088 (2)0.0024 (2)
N10.0115 (2)0.0174 (3)0.0135 (3)0.0025 (2)0.0044 (2)0.0030 (2)
N20.0123 (2)0.0151 (3)0.0123 (2)0.0016 (2)0.0036 (2)0.0009 (2)
C10.0130 (3)0.0159 (3)0.0149 (3)0.0005 (2)0.0061 (2)0.0003 (2)
C20.0127 (3)0.0164 (3)0.0166 (3)0.0021 (2)0.0061 (2)0.0014 (3)
C30.0124 (3)0.0161 (3)0.0151 (3)0.0006 (2)0.0043 (2)0.0007 (2)
C40.0150 (3)0.0244 (4)0.0143 (3)0.0047 (3)0.0067 (2)0.0022 (3)
C50.0140 (3)0.0226 (4)0.0148 (3)0.0044 (3)0.0061 (2)0.0012 (3)
C60.0113 (3)0.0149 (3)0.0129 (3)0.0008 (2)0.0039 (2)0.0002 (2)
C70.0112 (3)0.0144 (3)0.0123 (3)0.0002 (2)0.0035 (2)0.0018 (2)
C80.0132 (3)0.0161 (3)0.0127 (3)0.0010 (2)0.0049 (2)0.0020 (2)
C90.0121 (3)0.0134 (3)0.0115 (3)0.0003 (2)0.0038 (2)0.0009 (2)
C100.0127 (3)0.0190 (4)0.0153 (3)0.0013 (3)0.0053 (2)0.0029 (3)
C110.0142 (3)0.0215 (4)0.0180 (3)0.0028 (3)0.0039 (2)0.0033 (3)
C120.0192 (3)0.0190 (4)0.0140 (3)0.0036 (3)0.0025 (2)0.0024 (3)
C130.0206 (3)0.0160 (3)0.0127 (3)0.0020 (3)0.0063 (2)0.0020 (2)
C140.0149 (3)0.0133 (3)0.0124 (3)0.0000 (2)0.0059 (2)0.0007 (2)
Geometric parameters (Å, º) top
O1—C31.3524 (10)C4—H4A0.93
O1—H1B0.892 (15)C5—C61.4031 (11)
O2—C71.2372 (9)C5—H5A0.93
O3—C141.3666 (9)C6—C71.4768 (10)
O3—H3A0.877 (19)C8—C91.4513 (10)
N1—C71.3663 (9)C8—H8A0.93
N1—N21.3687 (9)C9—C101.4040 (10)
N1—H1C0.884 (16)C9—C141.4137 (10)
N2—C81.2872 (9)C10—C111.3857 (11)
C1—C21.3849 (11)C10—H10A0.93
C1—C61.4025 (10)C11—C121.3925 (12)
C1—H1A0.93C11—H11A0.93
C2—C31.4012 (11)C12—C131.3911 (11)
C2—H2A0.93C12—H12A0.93
C3—C41.3953 (11)C13—C141.3959 (11)
C4—C51.3880 (11)C13—H13A0.93
C3—O1—H1B109.3 (10)O2—C7—N1119.86 (7)
C14—O3—H3A108.5 (11)O2—C7—C6122.78 (6)
C7—N1—N2117.47 (6)N1—C7—C6117.34 (6)
C7—N1—H1C122.4 (10)N2—C8—C9119.83 (7)
N2—N1—H1C119.9 (10)N2—C8—H8A120.1
C8—N2—N1118.21 (6)C9—C8—H8A120.1
C2—C1—C6121.08 (7)C10—C9—C14118.80 (7)
C2—C1—H1A119.5C10—C9—C8118.78 (7)
C6—C1—H1A119.5C14—C9—C8122.42 (6)
C1—C2—C3119.66 (7)C11—C10—C9121.25 (7)
C1—C2—H2A120.2C11—C10—H10A119.4
C3—C2—H2A120.2C9—C10—H10A119.4
O1—C3—C4117.51 (7)C10—C11—C12119.34 (7)
O1—C3—C2122.73 (7)C10—C11—H11A120.3
C4—C3—C2119.76 (7)C12—C11—H11A120.3
C5—C4—C3120.39 (7)C13—C12—C11120.71 (7)
C5—C4—H4A119.8C13—C12—H12A119.6
C3—C4—H4A119.8C11—C12—H12A119.6
C4—C5—C6120.33 (7)C12—C13—C14120.20 (7)
C4—C5—H5A119.8C12—C13—H13A119.9
C6—C5—H5A119.8C14—C13—H13A119.9
C1—C6—C5118.77 (7)O3—C14—C13118.20 (7)
C1—C6—C7117.44 (6)O3—C14—C9122.09 (7)
C5—C6—C7123.79 (7)C13—C14—C9119.71 (7)
C7—N1—N2—C8178.74 (7)C5—C6—C7—N120.95 (12)
C6—C1—C2—C30.48 (12)N1—N2—C8—C9178.82 (7)
C1—C2—C3—O1179.17 (8)N2—C8—C9—C10177.14 (8)
C1—C2—C3—C40.89 (12)N2—C8—C9—C143.29 (12)
O1—C3—C4—C5179.38 (8)C14—C9—C10—C110.55 (12)
C2—C3—C4—C50.67 (13)C8—C9—C10—C11179.87 (8)
C3—C4—C5—C60.04 (13)C9—C10—C11—C120.23 (14)
C2—C1—C6—C50.15 (12)C10—C11—C12—C130.75 (14)
C2—C1—C6—C7179.41 (7)C11—C12—C13—C140.48 (13)
C4—C5—C6—C10.37 (13)C12—C13—C14—O3179.26 (8)
C4—C5—C6—C7179.17 (8)C12—C13—C14—C90.31 (12)
N2—N1—C7—O21.13 (11)C10—C9—C14—O3178.74 (7)
N2—N1—C7—C6179.47 (7)C8—C9—C14—O30.83 (12)
C1—C6—C7—O218.77 (12)C10—C9—C14—C130.81 (12)
C5—C6—C7—O2160.76 (8)C8—C9—C14—C13179.62 (7)
C1—C6—C7—N1159.51 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N20.88 (2)1.85 (2)2.616 (1)146 (2)
O1—H1B···O2i0.89 (2)1.80 (2)2.682 (1)171 (2)
N1—H1C···O3ii0.88 (2)2.30 (2)3.122 (1)156 (1)
C12—H12A···O2iii0.932.453.176 (1)134
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC14H12N2O3
Mr256.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)13.5978 (5), 8.0656 (3), 11.4128 (4)
β (°) 109.238 (2)
V3)1181.80 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.41 × 0.21 × 0.09
Data collection
DiffractometerBruker SMART APEX2 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.878, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
34050, 5185, 4394
Rint0.034
(sin θ/λ)max1)0.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.138, 1.07
No. of reflections5185
No. of parameters184
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.54, 0.29

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N20.88 (2)1.85 (2)2.616 (1)146 (2)
O1—H1B···O2i0.89 (2)1.80 (2)2.682 (1)171 (2)
N1—H1C···O3ii0.88 (2)2.30 (2)3.122 (1)156 (1)
C12—H12A···O2iii0.932.453.176 (1)134
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x+1, y1/2, z+3/2.
 

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