1,2-Bis(3-hydroxy-benzyl-idene)diazane.

The asymmetric unit of the title compound, C(14)H(12)N(2)O(2), which was synthesized unexpectedly by refluxing an ethano-lic solution of isonicotinic hydrazide and 3-hydroxy-benzaldehyde, contains one half-mol-ecule with the center of the N-N bond lying on a crystallographic center of inversion. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯N hydrogen bonds into an infinite layer structure parallel to (110).

Related literature

For general background to salicyclic aldehyde complexes, see: Zelewsky & von Knof (1999 ▶); Alam et al. (2003 ▶).

Experimental

Crystal data

C14H12N2O2

M = 240.26

Monoclinic,

a = 4.883 (2) Å

b = 8.212 (3) Å

c = 14.575 (6) Å

β = 95.267 (6)°

V = 582.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.989, T max = 0.993

4234 measured reflections

1079 independent reflections

814 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.185

S = 1.00

1079 reflections

83 parameters

H-atom parameters not refined

Δρmax = 0.62 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027652/im2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027652/im2128Isup2.hkl

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

C14H12N2O2	F(000) = 252
Mr = 240.26	Dx = 1.371 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1079 reflections
a = 4.883 (2) Å	θ = 2.8–25.5°
b = 8.212 (3) Å	µ = 0.09 mm−1
c = 14.575 (6) Å	T = 295 K
β = 95.267 (6)°	Block, yellow
V = 582.0 (4) Å3	0.12 × 0.10 × 0.08 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1079 independent reflections
Radiation source: fine-focus sealed tube	814 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→5
Tmin = 0.989, Tmax = 0.993	k = −9→9
4234 measured reflections	l = −17→17

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters not refined
S = 1.00	w = 1/[σ2(Fo2) + (0.103P)2 + 0.3322P] where P = (Fo2 + 2Fc2)/3
1079 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
C1	0.3137 (6)	0.2100 (3)	0.82062 (17)	0.0364 (7)
H3	0.1725	0.1396	0.7996	0.044*
C2	0.4468 (6)	0.2997 (3)	0.75848 (18)	0.0380 (7)
C3	0.6607 (6)	0.4021 (4)	0.7888 (2)	0.0434 (8)
H6	0.7546	0.4600	0.7467	0.052*
C4	0.7340 (6)	0.4175 (4)	0.8822 (2)	0.0469 (8)
H9	0.8749	0.4882	0.9031	0.056*
C5	0.6000 (6)	0.3292 (4)	0.94433 (19)	0.0414 (8)
H7	0.6516	0.3401	1.0070	0.050*
C6	0.3891 (6)	0.2240 (3)	0.91470 (17)	0.0342 (7)
C7	0.2426 (6)	0.1379 (3)	0.98224 (18)	0.0367 (7)
H4	0.2836	0.1634	1.0441	0.044*
N1	0.0615 (5)	0.0295 (3)	0.96142 (14)	0.0358 (6)
O1	0.3545 (6)	0.2849 (3)	0.66792 (14)	0.0637 (8)
H2	0.4174	0.3590	0.6386	0.096*

	U11	U22	U33	U12	U13	U23
C1	0.0469 (16)	0.0311 (14)	0.0322 (15)	0.0014 (12)	0.0096 (12)	0.0011 (11)
C2	0.0528 (17)	0.0348 (15)	0.0280 (14)	0.0046 (13)	0.0126 (12)	0.0034 (11)
C3	0.0420 (16)	0.0442 (17)	0.0463 (18)	0.0016 (13)	0.0157 (13)	0.0103 (14)
C4	0.0448 (17)	0.0431 (17)	0.0520 (18)	−0.0014 (14)	−0.0003 (14)	0.0064 (14)
C5	0.0475 (17)	0.0418 (17)	0.0343 (15)	0.0059 (14)	0.0004 (13)	0.0027 (12)
C6	0.0413 (15)	0.0338 (15)	0.0286 (13)	0.0092 (12)	0.0095 (11)	0.0029 (11)
C7	0.0501 (17)	0.0369 (16)	0.0241 (13)	0.0076 (13)	0.0085 (12)	0.0016 (11)
N1	0.0514 (14)	0.0354 (12)	0.0228 (11)	0.0081 (11)	0.0150 (9)	0.0040 (9)
O1	0.105 (2)	0.0549 (15)	0.0329 (12)	−0.0206 (14)	0.0170 (12)	0.0046 (10)

C1—C2	1.376 (4)	C4—H9	0.9300
C1—C6	1.392 (4)	C5—C6	1.382 (4)
C1—H3	0.9300	C5—H7	0.9300
C2—O1	1.360 (3)	C6—C7	1.453 (4)
C2—C3	1.382 (4)	C7—N1	1.272 (4)
C3—C4	1.382 (4)	C7—H4	0.9300
C3—H6	0.9300	N1—N1i	1.409 (4)
C4—C5	1.372 (4)	O1—H2	0.8200
C2—C1—C6	120.4 (3)	C4—C5—C6	120.7 (3)
C2—C1—H3	119.8	C4—C5—H7	119.6
C6—C1—H3	119.8	C6—C5—H7	119.6
O1—C2—C1	117.2 (3)	C5—C6—C1	118.8 (3)
O1—C2—C3	122.5 (3)	C5—C6—C7	119.4 (2)
C1—C2—C3	120.3 (3)	C1—C6—C7	121.7 (3)
C2—C3—C4	119.4 (3)	N1—C7—C6	123.6 (2)
C2—C3—H6	120.3	N1—C7—H4	118.2
C4—C3—H6	120.3	C6—C7—H4	118.2
C5—C4—C3	120.4 (3)	C7—N1—N1i	112.8 (3)
C5—C4—H9	119.8	C2—O1—H2	109.5
C3—C4—H9	119.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···N1ii	0.82	2.03	2.811 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2⋯N1i	0.82	2.03	2.811 (3)	159

Symmetry code: (i) .