4-Hydr-oxy-N'-(4-hydroxy-benzo-yl)benzo-hydrazide.

In the mol-ecule of the title compound, C(14)H(12)N(2)O(4), the two benzene rings make a dihedral angle of 84.53 (8)°. O-H⋯O and N-H⋯O hydrogen bonds link adjacent mol-ecules 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 = 272.26

Orthorhombic,

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[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

Δρmax = 0.27 e Å−3

Δρmin = −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 ▶).

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

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

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

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

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 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

	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)*

	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)

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)

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)

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) .