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organic compounds
1,2-Bis(3-hydroxybenzylidene)diazane
aSchool of Chemistry and Life Science, Maoming University, Maoming 525000, People's Republic of China, and bSchool of Public Health, Guangdong Pharmaceutical University, Guangzhou 510006, People's Republic of China
*Correspondence e-mail: zhaoxh_gpu@163.com
The 14H12N2O2, which was synthesized unexpectedly by refluxing an ethanolic solution of isonicotinic hydrazide and 3-hydroxybenzaldehyde, contains one half-molecule with the center of the N—N bond lying on a crystallographic center of inversion. In the molecules are linked by intermolecular O—H⋯N hydrogen bonds into an infinite layer structure parallel to (110).
of the title compound, CRelated literature
For general background to salicyclic aldehyde complexes, see: Zelewsky & von Knof (1999); Alam et al. (2003
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell 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.
Supporting information
10.1107/S1600536809027652/im2128sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809027652/im2128Isup2.hkl
An ethanolic solution of isonicotinic hydrazide (10 mmol) and 3-hydroxybenzaldehyde (10 mmol) refluxed for five hours. After filtration a yellow powder was obtained. Suitable crystals for X-ray diffraction were obtained by recrystallization from dichloromethane. Anal. Calc. for C14H12N2O2: C 69.92, H 4.99, N 9.99%; Found: C 69.89, H 4.79, N 9.78.
All H atoms were placed in calculated positions with C—H = 0.93Å and refined as riding with Uiso(H) = 1.2Ueq(carrier). The H atom of the hydroxy group was located from difference density maps and was refined with a distance restraint of d(O–H) = 0.82 (1) Å.
Data collection: APEX2 (Bruker, 2004); cell
SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008). ![]() | Fig. 1. The molecular structure of (I), drawn with 50% probability displacement ellipsoids. |
![]() | Fig. 2. Three-dimensional network formed by hydrogen bonds (dashed lines). |
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 monochromator | 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 |
C14H12N2O2 | V = 582.0 (4) Å3 |
Mr = 240.26 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.883 (2) Å | µ = 0.09 mm−1 |
b = 8.212 (3) Å | T = 295 K |
c = 14.575 (6) Å | 0.12 × 0.10 × 0.08 mm |
β = 95.267 (6)° |
Bruker APEXII CCD area-detector diffractometer | 1079 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 814 reflections with I > 2σ(I) |
Tmin = 0.989, Tmax = 0.993 | Rint = 0.039 |
4234 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.185 | H-atom parameters not refined |
S = 1.00 | Δρmax = 0.62 e Å−3 |
1079 reflections | Δρmin = −0.23 e Å−3 |
83 parameters |
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 |
Symmetry code: (i) −x, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H2···N1ii | 0.82 | 2.03 | 2.811 (3) | 159 |
Symmetry code: (ii) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C14H12N2O2 |
Mr | 240.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 4.883 (2), 8.212 (3), 14.575 (6) |
β (°) | 95.267 (6) |
V (Å3) | 582.0 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.12 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.989, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4234, 1079, 814 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.185, 1.00 |
No. of reflections | 1079 |
No. of parameters | 83 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.62, −0.23 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H2···N1i | 0.82 | 2.03 | 2.811 (3) | 158.9 |
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2. |
Acknowledgements
The authors acknowledge financial support from the scientific research start-up funds of talent introduction in Guangdong Pharmaceutical University.
References
Alam, M. A., Nethaji, M. & Ray, M. (2003). Angew. Chem. Int. Ed. 42, 1940–1942. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zelewsky, A. & von Knof, U. (1999). Angew. Chem. Int. Ed. 38, 302–322. Google Scholar
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The synthesis of complexes consisting of ligands derived from salicylic aldehyde has attracted continuous research interest not only with regard to their appealing structural and topological novelty, but also due to their unusual optical, electronic, magnetic and catalytic properties as well as their potential medical application (Zelewsky et al. 1999; Alam et al. 2003). In the present paper, we describe the synthesis and structural characterization of N,N'-di(3-hydroxybenzylidene)-hydrazine.
As shown in Fig. 1, the asymmetrical unit contains one half of the molecule. The center of the N-N bond represents a crystallographic center of inversion. One intermolecular hydrogen bond O(1)—H(2)···N(1) (2.811 (3) Å) is observed in the crystal structure leading to infinite layers of molecules (Fig. 2).