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

Abstract

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,

• a = 8.7058 (7) Å

• b = 9.7646 (8) Å

• c = 14.258 (1) Å

• V = 1212.05 (16) ų

• 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[F ² > 2σ(F ²)] = 0.030

• wR(F ²) = 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

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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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) ; (ii) ; (iii) .

supplementary crystallographic information

Experimental

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

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.

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C14H12N2O4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C14H12N2O4	F(000) = 568
Mr = 272.26	Dx = 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

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

Refinement

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(Fo2) + (0.0567P)2 + 0.1781P] where P = (Fo2 + 2Fc2)/3
1599 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 0.27 e Å−3
4 restraints	Δρmin = −0.17 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.