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

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809012136

organic compounds

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Volume 65| Part 5| May 2009| Page o969

doi:10.1107/S1600536809012136

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

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^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 ). For the 2-hydroxy substituted compound, 1,2-disalicyloylhydrazine, see: Chen et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₂N₂O₄
M_r = 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)
R_int = 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
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012136/xu2507sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012136/xu2507Isup2.hkl

checkCIF report

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.

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

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

C₁₄H₁₂N₂O₄	F(000) = 568
M_r = 272.26	D_x = 1.492 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3150 reflections
a = 8.7058 (7) Å	θ = 2.7–28.1°
b = 9.7646 (8) Å	µ = 0.11 mm⁻¹
c = 14.258 (1) Å	T = 123 K
V = 1212.05 (16) Å³	Prism, light yellow
Z = 4	0.40 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	1475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −7→11
6928 measured reflections	k = −12→12
1599 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0567P)² + 0.1781P] where P = (F_o² + 2F_c²)/3
1599 reflections	(Δ/σ)_max = 0.001
197 parameters	Δρ_max = 0.27 e Å⁻³
4 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O₄	V = 1212.05 (16) Å³
M_r = 272.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7058 (7) Å	µ = 0.11 mm⁻¹
b = 9.7646 (8) Å	T = 123 K
c = 14.258 (1) Å	0.40 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	1475 reflections with I > 2σ(I)
6928 measured reflections	R_int = 0.021
1599 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	4 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
1599 reflections	Δρ_min = −0.17 e Å⁻³
197 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.60946 (17)	0.59285 (14)	0.90517 (8)	0.0287 (3)
O2	0.72656 (15)	0.62247 (13)	0.46567 (8)	0.0247 (3)
O3	0.65093 (19)	0.92446 (15)	0.39648 (9)	0.0364 (4)
O4	0.63007 (17)	0.90074 (14)	−0.04878 (8)	0.0310 (3)
N1	0.49389 (17)	0.72003 (15)	0.47376 (9)	0.0217 (3)
N2	0.49553 (19)	0.74438 (15)	0.37802 (9)	0.0223 (3)
C1	0.6163 (2)	0.60858 (17)	0.81114 (11)	0.0206 (3)
C2	0.7010 (2)	0.52136 (18)	0.75329 (12)	0.0224 (4)
H2	0.7591	0.4487	0.7799	0.027*
C3	0.7002 (2)	0.54091 (17)	0.65708 (12)	0.0222 (4)
H3	0.7585	0.4818	0.6179	0.027*
C4	0.61465 (19)	0.64672 (17)	0.61727 (11)	0.0191 (3)
C5	0.5318 (2)	0.73400 (18)	0.67564 (11)	0.0214 (3)
H5	0.4735	0.8065	0.6491	0.026*
C6	0.5334 (2)	0.71626 (18)	0.77205 (11)	0.0235 (4)
H6	0.4781	0.7774	0.8114	0.028*
C7	0.6172 (2)	0.66161 (17)	0.51417 (11)	0.0197 (3)
C8	0.5846 (2)	0.84605 (18)	0.34327 (12)	0.0226 (4)
C9	0.5944 (2)	0.85689 (17)	0.23956 (12)	0.0210 (4)
C10	0.7023 (2)	0.94658 (17)	0.20197 (12)	0.0224 (4)
H10	0.7664	0.9979	0.2429	0.027*
C11	0.7180 (2)	0.96226 (18)	0.10568 (12)	0.0233 (4)
H11	0.7928	1.0232	0.0809	0.028*
C12	0.6230 (2)	0.88771 (17)	0.04537 (11)	0.0222 (4)
C13	0.5156 (2)	0.79694 (19)	0.08191 (11)	0.0265 (4)
H13	0.4517	0.7455	0.0409	0.032*
C14	0.5017 (2)	0.78146 (18)	0.17811 (12)	0.0247 (4)
H14	0.4285	0.7189	0.2027	0.030*
H1O	0.668 (3)	0.529 (2)	0.9222 (17)	0.045 (7)*
H4O	0.698 (2)	0.958 (2)	−0.0659 (18)	0.050 (8)*
H1N	0.4167 (19)	0.757 (2)	0.5039 (15)	0.031 (6)*
H2N	0.467 (3)	0.6748 (17)	0.3437 (14)	0.046 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0391 (8)	0.0299 (7)	0.0172 (6)	0.0076 (6)	−0.0011 (5)	0.0049 (5)
O2	0.0253 (6)	0.0290 (6)	0.0199 (5)	0.0028 (6)	0.0036 (5)	−0.0039 (5)
O3	0.0500 (9)	0.0399 (8)	0.0194 (6)	−0.0174 (7)	−0.0003 (6)	−0.0066 (6)
O4	0.0440 (9)	0.0313 (7)	0.0179 (6)	−0.0098 (7)	0.0005 (6)	0.0030 (5)
N1	0.0219 (7)	0.0300 (7)	0.0132 (6)	0.0027 (7)	0.0014 (6)	−0.0001 (6)
N2	0.0265 (8)	0.0276 (7)	0.0128 (6)	−0.0014 (7)	−0.0012 (6)	−0.0004 (5)
C1	0.0244 (9)	0.0209 (7)	0.0167 (7)	−0.0032 (7)	−0.0023 (6)	0.0014 (6)
C2	0.0238 (9)	0.0207 (7)	0.0227 (8)	0.0008 (7)	−0.0022 (7)	0.0036 (6)
C3	0.0216 (9)	0.0221 (8)	0.0230 (8)	0.0012 (7)	0.0014 (7)	−0.0016 (6)
C4	0.0192 (8)	0.0208 (7)	0.0173 (7)	−0.0039 (7)	−0.0004 (6)	0.0002 (6)
C5	0.0236 (9)	0.0206 (7)	0.0199 (7)	0.0021 (7)	−0.0005 (7)	0.0008 (6)
C6	0.0283 (9)	0.0236 (8)	0.0186 (8)	0.0026 (8)	0.0019 (7)	−0.0018 (7)
C7	0.0208 (8)	0.0188 (7)	0.0194 (8)	−0.0029 (7)	0.0009 (6)	−0.0025 (6)
C8	0.0231 (9)	0.0247 (8)	0.0201 (8)	0.0015 (7)	0.0006 (7)	−0.0026 (7)
C9	0.0231 (8)	0.0217 (8)	0.0181 (8)	0.0019 (7)	−0.0001 (6)	−0.0009 (6)
C10	0.0230 (9)	0.0217 (8)	0.0224 (8)	−0.0009 (7)	−0.0038 (7)	−0.0022 (6)
C11	0.0262 (9)	0.0210 (8)	0.0227 (8)	−0.0018 (7)	−0.0007 (7)	0.0027 (7)
C12	0.0282 (9)	0.0219 (8)	0.0166 (8)	0.0012 (8)	−0.0005 (6)	0.0014 (6)
C13	0.0296 (10)	0.0295 (9)	0.0206 (8)	−0.0065 (8)	−0.0028 (7)	−0.0026 (7)
C14	0.0267 (9)	0.0268 (8)	0.0206 (8)	−0.0064 (8)	0.0011 (7)	−0.0005 (7)

Geometric parameters (Å, º) top

O1—C1	1.3506 (19)	C7—N1	1.345 (2)
O1—H1O	0.839 (10)	C8—N2	1.354 (2)
O2—C7	1.237 (2)	C8—C9	1.485 (2)
O3—C8	1.223 (2)	C9—C10	1.392 (2)
O4—C12	1.3497 (19)	C9—C14	1.400 (2)
O4—H4O	0.846 (10)	C10—C11	1.388 (2)
C1—C6	1.392 (2)	C10—H10	0.9500
C1—C2	1.396 (2)	C11—C12	1.398 (2)
C2—C3	1.385 (2)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.390 (2)
C3—C4	1.395 (2)	C13—C14	1.385 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.393 (2)	C14—H14	0.9500
C4—C7	1.477 (2)	N1—N2	1.3856 (18)
C5—C6	1.386 (2)	N1—H1N	0.877 (10)
C5—H5	0.9500	N2—H2N	0.874 (10)
C6—H6	0.9500

C1—O1—H1O	110.1 (18)	N2—C8—C9	116.72 (15)
C12—O4—H4O	112.4 (19)	C10—C9—C14	118.62 (15)
O1—C1—C6	117.41 (15)	C10—C9—C8	117.85 (15)
O1—C1—C2	122.70 (15)	C14—C9—C8	123.53 (16)
C6—C1—C2	119.88 (15)	C11—C10—C9	121.10 (16)
C3—C2—C1	119.90 (16)	C11—C10—H10	119.5
C3—C2—H2	120.1	C9—C10—H10	119.5
C1—C2—H2	120.1	C10—C11—C12	119.54 (17)
C2—C3—C4	120.52 (16)	C10—C11—H11	120.2
C2—C3—H3	119.7	C12—C11—H11	120.2
C4—C3—H3	119.7	O4—C12—C13	117.63 (15)
C5—C4—C3	119.15 (15)	O4—C12—C11	122.39 (16)
C5—C4—C7	122.84 (15)	C13—C12—C11	119.98 (15)
C3—C4—C7	118.02 (15)	C14—C13—C12	119.96 (16)
C6—C5—C4	120.74 (16)	C14—C13—H13	120.0
C6—C5—H5	119.6	C12—C13—H13	120.0
C4—C5—H5	119.6	C13—C14—C9	120.80 (17)
C5—C6—C1	119.80 (16)	C13—C14—H14	119.6
C5—C6—H6	120.1	C9—C14—H14	119.6
C1—C6—H6	120.1	C7—N1—N2	119.10 (14)
O2—C7—N1	120.37 (14)	C7—N1—H1N	125.3 (15)
O2—C7—C4	122.52 (15)	N2—N1—H1N	114.8 (16)
N1—C7—C4	117.11 (14)	C8—N2—N1	119.49 (14)
O3—C8—N2	120.18 (16)	C8—N2—H2N	121.9 (16)
O3—C8—C9	123.09 (17)	N1—N2—H2N	114.5 (16)

O1—C1—C2—C3	178.36 (16)	N2—C8—C9—C14	9.1 (3)
C6—C1—C2—C3	−1.0 (3)	C14—C9—C10—C11	0.4 (3)
C1—C2—C3—C4	−0.4 (3)	C8—C9—C10—C11	−179.92 (17)
C2—C3—C4—C5	1.0 (3)	C9—C10—C11—C12	0.6 (3)
C2—C3—C4—C7	−179.43 (16)	C10—C11—C12—O4	178.43 (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—C14	0.6 (3)
O1—C1—C6—C5	−177.59 (17)	C12—C13—C14—C9	0.3 (3)
C2—C1—C6—C5	1.8 (3)	C10—C9—C14—C13	−0.9 (3)
C5—C4—C7—O2	152.83 (17)	C8—C9—C14—C13	179.49 (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—N2	175.75 (14)
C3—C4—C7—N1	153.10 (16)	O3—C8—N2—N1	−7.3 (3)
O3—C8—C9—C10	10.2 (3)	C9—C8—N2—N1	173.48 (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, º) top

D—H···A	D—H	H···A	D···A	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+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.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₄
M_r	272.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	123
a, b, c (Å)	8.7058 (7), 9.7646 (8), 14.258 (1)
V (Å³)	1212.05 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6928, 1599, 1475
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.088, 1.04
No. of reflections	1599
No. of parameters	197
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+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

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

References

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