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

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 31 March 2009; accepted 1 April 2009; online 8 April 2009)

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

For the unsubstituted parent compound, 1,2-dibenzoyl­hydrazine, see: Shanmuga Sundara Raj et al. (2000[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.]). For the 2-hydroxy ­substituted compound, 1,2-disalicyloylhydrazine, see: Chen et al. (2008[Chen, Y.-T., Li, D.-C., Wang, D.-Q. & Zhu, Y.-H. (2008). Acta Cryst. E64, o120.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2O4

  • Mr = 272.26

  • Orthorhombic, P 21 21 21

  • a = 8.7058 (7) Å

  • b = 9.7646 (8) Å

  • c = 14.258 (1) Å

  • V = 1212.05 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 123 K

  • 0.40 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 6928 measured reflections

  • 1599 independent reflections

  • 1475 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.088

  • S = 1.04

  • 1599 reflections

  • 197 parameters

  • 4 restraints

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O2i 0.84 (1) 1.85 (1) 2.684 (2) 172 (3)
O4—H4o⋯O3ii 0.85 (1) 1.83 (1) 2.675 (2) 178 (3)
N1—H1n⋯O2iii 0.88 (1) 2.08 (1) 2.920 (2) 162 (2)
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 m3
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 mm1
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
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
ω scansh = 711
6928 measured reflectionsk = 1212
1599 independent reflectionsl = 1818
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 Å3
4 restraintsΔρmin = 0.17 e Å3
Crystal data top
C14H12N2O4V = 1212.05 (16) Å3
Mr = 272.26Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.7058 (7) ŵ = 0.11 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0304 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.27 e Å3
1599 reflectionsΔρmin = 0.17 e Å3
197 parameters
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, º) 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—C31.0 (3)C14—C9—C10—C110.4 (3)
C1—C2—C3—C40.4 (3)C8—C9—C10—C11179.92 (17)
C2—C3—C4—C51.0 (3)C9—C10—C11—C120.6 (3)
C2—C3—C4—C7179.43 (16)C10—C11—C12—O4178.43 (16)
C3—C4—C5—C60.2 (3)C10—C11—C12—C131.1 (3)
C7—C4—C5—C6179.74 (16)O4—C12—C13—C14178.89 (17)
C4—C5—C6—C11.2 (3)C11—C12—C13—C140.6 (3)
O1—C1—C6—C5177.59 (17)C12—C13—C14—C90.3 (3)
C2—C1—C6—C51.8 (3)C10—C9—C14—C130.9 (3)
C5—C4—C7—O2152.83 (17)C8—C9—C14—C13179.49 (17)
C3—C4—C7—O226.7 (2)O2—C7—N1—N24.4 (2)
C5—C4—C7—N127.4 (2)C4—C7—N1—N2175.75 (14)
C3—C4—C7—N1153.10 (16)O3—C8—N2—N17.3 (3)
O3—C8—C9—C1010.2 (3)C9—C8—N2—N1173.48 (15)
N2—C8—C9—C10170.57 (16)C7—N1—N2—C872.5 (2)
O3—C8—C9—C14170.11 (19)
Hydrogen-bond geometry (Å, º) 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, z1/2; (iii) x1/2, y+3/2, z+1.

Experimental details

Crystal data
Chemical formulaC14H12N2O4
Mr272.26
Crystal system, space groupOrthorhombic, P212121
Temperature (K)123
a, b, c (Å)8.7058 (7), 9.7646 (8), 14.258 (1)
V3)1212.05 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.40 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6928, 1599, 1475
Rint0.021
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.088, 1.04
No. of reflections1599
No. of parameters197
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.17

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) 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, z1/2; (iii) x1/2, y+3/2, z+1.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, Y.-T., Li, D.-C., Wang, D.-Q. & Zhu, Y.-H. (2008). Acta Cryst. E64, o120.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShanmuga 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.  CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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