N,N'-disalicyloylhydrazine.

The approximately planar mol-ecule of the title compound, C(14)H(12)N(2)O(4), is centrosymmetric and has an E configuration with respect to the N-N bond. This compound adopts the ketoamine form with C=O and C-N distances of 1.233 (3) and 1.331 (4) Å, respectively. Adjacent mol-ecules are assembled into a two-dimensional supra-molecular structure parallel to the (101) plane via inter-molecular O-H⋯O hydrogen bonds.

Related literature

For metallacrowns with unsymmetrical aroylhydrazone ligands, see: John et al. (2006 ▶); Dou et al. (2006 ▶). For the crystal structure of an n class="Chemical">iron compound with N,N′-bis-picolinoyl hydrazine, see: Bernhardt et al. (2005 ▶). For the preparation of 2-acetyl-2-hydroxy­naphthohydrazide, see: Liu et al. (2006 ▶).

Experimental

Crystal data

C14H12N2O4

M = 272.26

Monoclinic,

a = 8.3816 (18) Å

b = 6.2909 (15) Å

c = 12.376 (2) Å

β = 105.463 (2)°

V = 628.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.18 × 0.15 × 0.14 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

3082 measured reflections

1102 independent reflections

618 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.163

S = 1.03

1102 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SMART; data reduction: SAINT (Siemens, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706312X/si2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706312X/si2060Isup2.hkl

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

C14H12N2O4	F000 = 284
Mr = 272.26	Dx = 1.438 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 678 reflections
a = 8.3816 (18) Å	θ = 2.6–25.5º
b = 6.2909 (15) Å	µ = 0.11 mm−1
c = 12.376 (2) Å	T = 298 (2) K
β = 105.463 (2)º	Block, colorless
V = 628.9 (2) Å3	0.18 × 0.15 × 0.14 mm
Z = 2

Bruker SMART 1000 CCD area-detector diffractometer	1102 independent reflections
Radiation source: fine-focus sealed tube	618 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.981, Tmax = 0.985	k = −7→7
3082 measured reflections	l = −6→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0827P)2 + 0.0895P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1102 reflections	Δρmax = 0.30 e Å−3
92 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.9962 (3)	0.5894 (4)	0.53095 (19)	0.0462 (7)
H1	1.0781	0.6229	0.5867	0.055*
O1	0.7444 (2)	0.6612 (3)	0.42420 (17)	0.0576 (7)
O2	1.1131 (3)	0.8180 (4)	0.70745 (18)	0.0696 (8)
H2	1.1607	0.8443	0.7730	0.104*
C1	0.8612 (4)	0.7109 (5)	0.5042 (2)	0.0419 (8)
C2	0.8605 (3)	0.9011 (4)	0.5739 (2)	0.0372 (7)
C3	0.9807 (3)	0.9503 (5)	0.6721 (2)	0.0419 (7)
C4	0.9670 (4)	1.1325 (5)	0.7318 (3)	0.0502 (9)
H4	1.0485	1.1646	0.7971	0.060*
C5	0.8344 (4)	1.2655 (6)	0.6953 (3)	0.0550 (9)
H5	0.8257	1.3872	0.7360	0.066*
C6	0.7137 (4)	1.2198 (5)	0.5984 (3)	0.0550 (9)
H6	0.6238	1.3105	0.5737	0.066*
C7	0.7265 (3)	1.0410 (5)	0.5388 (3)	0.0475 (8)
H7	0.6446	1.0114	0.4734	0.057*

	U11	U22	U33	U12	U13	U23
N1	0.0449 (14)	0.0496 (16)	0.0396 (15)	−0.0013 (12)	0.0033 (12)	−0.0122 (11)
O1	0.0524 (13)	0.0698 (16)	0.0397 (12)	−0.0048 (11)	−0.0066 (10)	−0.0061 (11)
O2	0.0648 (16)	0.0800 (17)	0.0481 (14)	0.0250 (13)	−0.0125 (11)	−0.0230 (13)
C1	0.0430 (18)	0.0471 (18)	0.0336 (15)	−0.0016 (14)	0.0067 (14)	0.0045 (14)
C2	0.0375 (16)	0.0409 (17)	0.0357 (16)	−0.0006 (13)	0.0141 (13)	0.0018 (13)
C3	0.0370 (15)	0.0487 (17)	0.0384 (16)	0.0066 (14)	0.0073 (13)	−0.0016 (15)
C4	0.0476 (19)	0.056 (2)	0.0465 (18)	−0.0038 (16)	0.0127 (15)	−0.0124 (16)
C5	0.063 (2)	0.0485 (19)	0.061 (2)	−0.0016 (17)	0.0303 (19)	−0.0077 (17)
C6	0.054 (2)	0.050 (2)	0.065 (2)	0.0137 (16)	0.0226 (18)	0.0076 (18)
C7	0.0389 (16)	0.055 (2)	0.0465 (18)	0.0052 (15)	0.0079 (14)	0.0074 (16)

N1—C1	1.331 (3)	C3—C4	1.384 (4)
N1—N1i	1.372 (4)	C4—C5	1.368 (4)
N1—H1	0.8600	C4—H4	0.9300
O1—C1	1.233 (3)	C5—C6	1.377 (5)
O2—C3	1.363 (3)	C5—H5	0.9300
O2—H2	0.8200	C6—C7	1.365 (4)
C1—C2	1.476 (4)	C6—H6	0.9300
C2—C3	1.391 (4)	C7—H7	0.9300
C2—C7	1.402 (4)
C1—N1—N1i	119.7 (3)	C5—C4—C3	120.4 (3)
C1—N1—H1	120.2	C5—C4—H4	119.8
N1i—N1—H1	120.2	C3—C4—H4	119.8
C3—O2—H2	109.5	C4—C5—C6	120.2 (3)
O1—C1—N1	119.6 (3)	C4—C5—H5	119.9
O1—C1—C2	123.3 (3)	C6—C5—H5	119.9
N1—C1—C2	117.1 (2)	C7—C6—C5	119.8 (3)
C3—C2—C7	117.7 (3)	C7—C6—H6	120.1
C3—C2—C1	125.2 (2)	C5—C6—H6	120.1
C7—C2—C1	117.1 (2)	C6—C7—C2	121.4 (3)
O2—C3—C4	120.7 (3)	C6—C7—H7	119.3
O2—C3—C2	118.8 (3)	C2—C7—H7	119.3
C4—C3—C2	120.5 (3)
N1i—N1—C1—O1	0.1 (5)	C1—C2—C3—C4	−179.4 (3)
N1i—N1—C1—C2	−180.0 (3)	O2—C3—C4—C5	179.4 (3)
O1—C1—C2—C3	172.2 (3)	C2—C3—C4—C5	0.5 (4)
N1—C1—C2—C3	−7.7 (4)	C3—C4—C5—C6	−0.4 (5)
O1—C1—C2—C7	−6.7 (4)	C4—C5—C6—C7	0.1 (5)
N1—C1—C2—C7	173.3 (3)	C5—C6—C7—C2	0.1 (5)
C7—C2—C3—O2	−179.3 (3)	C3—C2—C7—C6	0.1 (4)
C1—C2—C3—O2	1.7 (4)	C1—C2—C7—C6	179.1 (3)
C7—C2—C3—C4	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ii	0.82	1.81	2.617 (3)	166
N1—H1···O2	0.86	1.89	2.580 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ii	0.82	1.81	2.617 (3)	166
N1—H1⋯O2	0.86	1.89	2.580 (3)	136

Symmetry code: (ii) .