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Acta Cryst. (2009). E65, o969    [ doi:10.1107/S1600536809012136 ]

4-Hydroxy-N'-(4-hydroxybenzoyl)benzohydrazide

K. M. Lo and S. W. Ng

Abstract top

In the molecule of the title compound, C14H12N2O4, the two benzene rings make a dihedral angle of 84.53 (8)°. O-H...O and N-H...O hydrogen bonds link adjacent molecules into a layer structure.

Related literature top

For the unsubstituted parent compound, 1,2-dibenzoylhydrazine, see: Shanmuga Sundara Raj et al. (2000). For the 2-hydroxysubstituted compound, 1,2-disalicyloylhydrazine, see: Chen et al. (2008).

Experimental top

4-Hydroxybenzoylhydrazine (0.31 g, 2 mmol) and pyruvic acid (0.16 g, 2 mmol) were heated in ethanol (100 ml) for 3 h in an attemp to synthesize a Schiff base. Slow cooling of the filtered solution gave crystals of the hydrazide.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 Å and N–H 0.88±0.01 Å. Their temperature factors were refined.

Some 1159 Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H12N2O4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
4-Hydroxy-N'-(4-hydroxybenzoyl)benzohydrazide top
Crystal data top
C14H12N2O4F(000) = 568
Mr = 272.26Dx = 1.492 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3150 reflections
a = 8.7058 (7) Åθ = 2.7–28.1°
b = 9.7646 (8) ŵ = 0.11 mm−1
c = 14.258 (1) ÅT = 123 K
V = 1212.05 (16) Å3Prism, light yellow
Z = 40.40 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		1475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
graphiteθmax = 27.5°, θmin = 2.5°
ω scansh = −7→11
6928 measured reflectionsk = −12→12
1599 independent reflectionsl = −18→18
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.1781P]
where P = (Fo2 + 2Fc2)/3
1599 reflections(Δ/σ)max = 0.001
197 parametersΔρmax = 0.27 e Å−3
4 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C14H12N2O4V = 1212.05 (16) Å3
Mr = 272.26Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.7058 (7) ŵ = 0.11 mm−1
b = 9.7646 (8) ÅT = 123 K
c = 14.258 (1) Å0.40 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		1475 reflections with I > 2σ(I)
6928 measured reflectionsRint = 0.021
1599 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088Δρmax = 0.27 e Å−3
S = 1.04Δρmin = −0.17 e Å−3
1599 reflectionsAbsolute structure: ?
197 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.60946 (17)0.59285 (14)0.90517 (8)0.0287 (3)
O20.72656 (15)0.62247 (13)0.46567 (8)0.0247 (3)
O30.65093 (19)0.92446 (15)0.39648 (9)0.0364 (4)
O40.63007 (17)0.90074 (14)−0.04878 (8)0.0310 (3)
N10.49389 (17)0.72003 (15)0.47376 (9)0.0217 (3)
N20.49553 (19)0.74438 (15)0.37802 (9)0.0223 (3)
C10.6163 (2)0.60858 (17)0.81114 (11)0.0206 (3)
C20.7010 (2)0.52136 (18)0.75329 (12)0.0224 (4)
H20.75910.44870.77990.027*
C30.7002 (2)0.54091 (17)0.65708 (12)0.0222 (4)
H30.75850.48180.61790.027*
C40.61465 (19)0.64672 (17)0.61727 (11)0.0191 (3)
C50.5318 (2)0.73400 (18)0.67564 (11)0.0214 (3)
H50.47350.80650.64910.026*
C60.5334 (2)0.71626 (18)0.77205 (11)0.0235 (4)
H60.47810.77740.81140.028*
C70.6172 (2)0.66161 (17)0.51417 (11)0.0197 (3)
C80.5846 (2)0.84605 (18)0.34327 (12)0.0226 (4)
C90.5944 (2)0.85689 (17)0.23956 (12)0.0210 (4)
C100.7023 (2)0.94658 (17)0.20197 (12)0.0224 (4)
H100.76640.99790.24290.027*
C110.7180 (2)0.96226 (18)0.10568 (12)0.0233 (4)
H110.79281.02320.08090.028*
C120.6230 (2)0.88771 (17)0.04537 (11)0.0222 (4)
C130.5156 (2)0.79694 (19)0.08191 (11)0.0265 (4)
H130.45170.74550.04090.032*
C140.5017 (2)0.78146 (18)0.17811 (12)0.0247 (4)
H140.42850.71890.20270.030*
H1O0.668 (3)0.529 (2)0.9222 (17)0.045 (7)*
H4O0.698 (2)0.958 (2)−0.0659 (18)0.050 (8)*
H1N0.4167 (19)0.757 (2)0.5039 (15)0.031 (6)*
H2N0.467 (3)0.6748 (17)0.3437 (14)0.046 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0391 (8)0.0299 (7)0.0172 (6)0.0076 (6)−0.0011 (5)0.0049 (5)
O20.0253 (6)0.0290 (6)0.0199 (5)0.0028 (6)0.0036 (5)−0.0039 (5)
O30.0500 (9)0.0399 (8)0.0194 (6)−0.0174 (7)−0.0003 (6)−0.0066 (6)
O40.0440 (9)0.0313 (7)0.0179 (6)−0.0098 (7)0.0005 (6)0.0030 (5)
N10.0219 (7)0.0300 (7)0.0132 (6)0.0027 (7)0.0014 (6)−0.0001 (6)
N20.0265 (8)0.0276 (7)0.0128 (6)−0.0014 (7)−0.0012 (6)−0.0004 (5)
C10.0244 (9)0.0209 (7)0.0167 (7)−0.0032 (7)−0.0023 (6)0.0014 (6)
C20.0238 (9)0.0207 (7)0.0227 (8)0.0008 (7)−0.0022 (7)0.0036 (6)
C30.0216 (9)0.0221 (8)0.0230 (8)0.0012 (7)0.0014 (7)−0.0016 (6)
C40.0192 (8)0.0208 (7)0.0173 (7)−0.0039 (7)−0.0004 (6)0.0002 (6)
C50.0236 (9)0.0206 (7)0.0199 (7)0.0021 (7)−0.0005 (7)0.0008 (6)
C60.0283 (9)0.0236 (8)0.0186 (8)0.0026 (8)0.0019 (7)−0.0018 (7)
C70.0208 (8)0.0188 (7)0.0194 (8)−0.0029 (7)0.0009 (6)−0.0025 (6)
C80.0231 (9)0.0247 (8)0.0201 (8)0.0015 (7)0.0006 (7)−0.0026 (7)
C90.0231 (8)0.0217 (8)0.0181 (8)0.0019 (7)−0.0001 (6)−0.0009 (6)
C100.0230 (9)0.0217 (8)0.0224 (8)−0.0009 (7)−0.0038 (7)−0.0022 (6)
C110.0262 (9)0.0210 (8)0.0227 (8)−0.0018 (7)−0.0007 (7)0.0027 (7)
C120.0282 (9)0.0219 (8)0.0166 (8)0.0012 (8)−0.0005 (6)0.0014 (6)
C130.0296 (10)0.0295 (9)0.0206 (8)−0.0065 (8)−0.0028 (7)−0.0026 (7)
C140.0267 (9)0.0268 (8)0.0206 (8)−0.0064 (8)0.0011 (7)−0.0005 (7)
Geometric parameters (Å, °) top
O1—C11.3506 (19)C7—N11.345 (2)
O1—H1O0.839 (10)C8—N21.354 (2)
O2—C71.237 (2)C8—C91.485 (2)
O3—C81.223 (2)C9—C101.392 (2)
O4—C121.3497 (19)C9—C141.400 (2)
O4—H4O0.846 (10)C10—C111.388 (2)
C1—C61.392 (2)C10—H100.9500
C1—C21.396 (2)C11—C121.398 (2)
C2—C31.385 (2)C11—H110.9500
C2—H20.9500C12—C131.390 (2)
C3—C41.395 (2)C13—C141.385 (2)
C3—H30.9500C13—H130.9500
C4—C51.393 (2)C14—H140.9500
C4—C71.477 (2)N1—N21.3856 (18)
C5—C61.386 (2)N1—H1N0.877 (10)
C5—H50.9500N2—H2N0.874 (10)
C6—H60.9500
C1—O1—H1O110.1 (18)N2—C8—C9116.72 (15)
C12—O4—H4O112.4 (19)C10—C9—C14118.62 (15)
O1—C1—C6117.41 (15)C10—C9—C8117.85 (15)
O1—C1—C2122.70 (15)C14—C9—C8123.53 (16)
C6—C1—C2119.88 (15)C11—C10—C9121.10 (16)
C3—C2—C1119.90 (16)C11—C10—H10119.5
C3—C2—H2120.1C9—C10—H10119.5
C1—C2—H2120.1C10—C11—C12119.54 (17)
C2—C3—C4120.52 (16)C10—C11—H11120.2
C2—C3—H3119.7C12—C11—H11120.2
C4—C3—H3119.7O4—C12—C13117.63 (15)
C5—C4—C3119.15 (15)O4—C12—C11122.39 (16)
C5—C4—C7122.84 (15)C13—C12—C11119.98 (15)
C3—C4—C7118.02 (15)C14—C13—C12119.96 (16)
C6—C5—C4120.74 (16)C14—C13—H13120.0
C6—C5—H5119.6C12—C13—H13120.0
C4—C5—H5119.6C13—C14—C9120.80 (17)
C5—C6—C1119.80 (16)C13—C14—H14119.6
C5—C6—H6120.1C9—C14—H14119.6
C1—C6—H6120.1C7—N1—N2119.10 (14)
O2—C7—N1120.37 (14)C7—N1—H1N125.3 (15)
O2—C7—C4122.52 (15)N2—N1—H1N114.8 (16)
N1—C7—C4117.11 (14)C8—N2—N1119.49 (14)
O3—C8—N2120.18 (16)C8—N2—H2N121.9 (16)
O3—C8—C9123.09 (17)N1—N2—H2N114.5 (16)
O1—C1—C2—C3178.36 (16)N2—C8—C9—C149.1 (3)
C6—C1—C2—C3−1.0 (3)C14—C9—C10—C110.4 (3)
C1—C2—C3—C4−0.4 (3)C8—C9—C10—C11−179.92 (17)
C2—C3—C4—C51.0 (3)C9—C10—C11—C120.6 (3)
C2—C3—C4—C7−179.43 (16)C10—C11—C12—O4178.43 (16)
C3—C4—C5—C6−0.2 (3)C10—C11—C12—C13−1.1 (3)
C7—C4—C5—C6−179.74 (16)O4—C12—C13—C14−178.89 (17)
C4—C5—C6—C1−1.2 (3)C11—C12—C13—C140.6 (3)
O1—C1—C6—C5−177.59 (17)C12—C13—C14—C90.3 (3)
C2—C1—C6—C51.8 (3)C10—C9—C14—C13−0.9 (3)
C5—C4—C7—O2152.83 (17)C8—C9—C14—C13179.49 (17)
C3—C4—C7—O2−26.7 (2)O2—C7—N1—N2−4.4 (2)
C5—C4—C7—N1−27.4 (2)C4—C7—N1—N2175.75 (14)
C3—C4—C7—N1153.10 (16)O3—C8—N2—N1−7.3 (3)
O3—C8—C9—C1010.2 (3)C9—C8—N2—N1173.48 (15)
N2—C8—C9—C10−170.57 (16)C7—N1—N2—C8−72.5 (2)
O3—C8—C9—C14−170.11 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.84 (1)1.85 (1)2.684 (2)172 (3)
O4—H4o···O3ii0.85 (1)1.83 (1)2.675 (2)178 (3)
N1—H1n···O2iii0.88 (1)2.08 (1)2.920 (2)162 (2)
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+3/2, −y+2, z−1/2; (iii) x−1/2, −y+3/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.84 (1)1.85 (1)2.684 (2)172 (3)
O4—H4o···O3ii0.85 (1)1.83 (1)2.675 (2)178 (3)
N1—H1n···O2iii0.88 (1)2.08 (1)2.920 (2)162 (2)
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+3/2, −y+2, z−1/2; (iii) x−1/2, −y+3/2, −z+1.
Acknowledgements top

We thank the University of Malaya (FS339/2008 A) for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Chen, Y.-T., Li, D.-C., Wang, D.-Q. & Zhu, Y.-H. (2008). Acta Cryst. E64, o120.

Shanmuga Sundara Raj, S., Yamin, B. M., Boshaala, A. M. A., Tarafder, M. T. H., Crouse, K. A. & Fun, H.-K. (2000). Acta Cryst. C56, 1011–1012.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.