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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3023.
Published online 2009 November 7. doi:  10.1107/S1600536809045504
PMCID: PMC2971797

2-(Hydrazonomethyl)phenol

Abstract

The conformation of the title compound, C7H8N2O, is stabilized by an intra­molecular O—H(...)N hydrogen bond. The crystal structure shows inter­molecular N—H(...)O hydrogen bonds.

Related literature

For Schiff bases as mixed-donor ligands in coordination chemistry, see: Lee et al. (2005 [triangle]). For the pharmaceutical and medicinal activity of Schiff bases, see: Sriram et al. (2006 [triangle]); Hao (2009 [triangle]); Bedia et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3023-scheme1.jpg

Experimental

Crystal data

  • C7H8N2O
  • M r = 136.15
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3023-efi1.jpg
  • a = 14.1010 (11) Å
  • b = 6.0062 (5) Å
  • c = 8.1979 (6) Å
  • β = 102.5250 (10)°
  • V = 677.78 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.46 × 0.45 × 0.35 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.959, T max = 0.968
  • 3351 measured reflections
  • 1203 independent reflections
  • 1081 reflections with I > 2σ(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.110
  • S = 1.06
  • 1203 reflections
  • 93 parameters
  • .
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Sheldrick, 2008 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045504/bt5112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045504/bt5112Isup2.hkl

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

Acknowledgments

Y-FS acknowledges financial support from the Natural Science Foundation of Nantong University in China (grant No. 07z025).

supplementary crystallographic information

Comment

Schiff bases are one of the most prevalent and important mixed-donor ligand in coordination chemistry (Lee et al., 2005). Recently, the synthesis, structure and properties of Schiff base complexes have stimulated much more interest for their noteworthy contributions in pharmaceutical and medicinal activity (Sriram et al., 2006; Hao 2009; Bedia et al., 2006).

The X-ray structural analysis confirmed the assignment of the structure of the title compound(I). The molecular structure is depicted in Fig. 1, and the crystal packing of the title compound(I) is depicted in Fig. 2. In the crystal structure,intermolecular N—H···O, N—H···N and intramolecular O—H···N hydrogen bonds contribute to form the title compound(I).

Experimental

35% of hydrazine hydrate (0.50 mL, 10 mmol) and salicylidence (0.52 mL, 5 mmol) were mixed in 50.0 mL ethanol and refluxed for 3 h. When the solution was cooled to room temperature, a light yellow solid was obtained, and light yellow block shaped crystals were formed from the filtrate by slow evaporation of the solution in air after a few days. The yield of the isolated yellow solid was 0.62 g.(90%).

Refinement

H atoms attached to C were placed in geometrically idealized positions with Csp2—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms bonded to N and O were located in a difference map. They were refined using a riding model with O—H = 0.82 Å and N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O).

Figures

Fig. 1.
A view of the title compound with displacement ellipsoids drawn at the 30% probability level. Dashed line indicates hydrogen bonding interactions.
Fig. 2.
Crystal packing of the title compound.

Crystal data

C7H8N2OF(000) = 288
Mr = 136.15Dx = 1.334 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2298 reflections
a = 14.1010 (11) Åθ = 3.0–28.4°
b = 6.0062 (5) ŵ = 0.09 mm1
c = 8.1979 (6) ÅT = 296 K
β = 102.525 (1)°Block, yellow
V = 677.78 (9) Å30.46 × 0.45 × 0.35 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1203 independent reflections
Radiation source: fine-focus sealed tube1081 reflections with I > 2σ(I)
graphiteRint = 0.013
[var phi] and ω scansθmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −15→16
Tmin = 0.959, Tmax = 0.968k = −6→7
3351 measured reflectionsl = −9→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.33 e Å3
1203 reflectionsΔρmin = −0.29 e Å3
93 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.129 (12)
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.22022 (10)−0.1162 (2)0.13139 (16)0.0374 (4)
C20.27892 (11)−0.2576 (3)0.24310 (18)0.0462 (4)
H20.2554−0.39580.26700.055*
C30.37226 (12)−0.1944 (3)0.3192 (2)0.0546 (5)
H30.4111−0.28980.39480.065*
C40.40836 (11)0.0097 (3)0.2837 (2)0.0568 (5)
H40.47150.05130.33390.068*
C50.34970 (11)0.1512 (3)0.17277 (19)0.0487 (4)
H50.37430.28810.14870.058*
C60.25465 (9)0.0945 (2)0.09582 (16)0.0372 (4)
C70.19290 (10)0.2536 (2)−0.01248 (16)0.0392 (4)
H70.21900.3883−0.03760.047*
N10.10354 (8)0.21085 (19)−0.07344 (14)0.0407 (3)
N20.04759 (9)0.3659 (2)−0.17427 (15)0.0507 (4)
H2A0.06930.4889−0.20590.061*
H2B−0.00890.3460−0.15300.061*
O10.12928 (7)−0.18636 (16)0.05811 (13)0.0476 (3)
H10.0993−0.08400.00390.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0428 (8)0.0355 (7)0.0358 (7)−0.0005 (6)0.0127 (6)−0.0036 (5)
C20.0587 (9)0.0381 (8)0.0439 (8)0.0040 (6)0.0157 (7)0.0026 (6)
C30.0576 (10)0.0566 (10)0.0467 (9)0.0148 (8)0.0050 (7)0.0038 (7)
C40.0439 (8)0.0645 (11)0.0574 (10)0.0009 (8)0.0007 (7)−0.0041 (8)
C50.0468 (8)0.0447 (8)0.0543 (9)−0.0070 (6)0.0106 (7)−0.0034 (7)
C60.0418 (7)0.0351 (7)0.0363 (7)−0.0016 (6)0.0118 (5)−0.0038 (5)
C70.0471 (8)0.0323 (7)0.0399 (7)−0.0060 (6)0.0130 (6)0.0003 (6)
N10.0468 (7)0.0364 (6)0.0385 (6)−0.0013 (5)0.0083 (5)0.0020 (5)
N20.0523 (8)0.0466 (8)0.0522 (8)0.0037 (6)0.0092 (6)0.0140 (6)
O10.0451 (6)0.0353 (6)0.0607 (7)−0.0054 (4)0.0078 (5)0.0039 (5)

Geometric parameters (Å, °)

C1—O11.3597 (16)C5—C61.3941 (19)
C1—C21.384 (2)C5—H50.9300
C1—C61.409 (2)C6—C71.4574 (19)
C2—C31.382 (2)C7—N11.2768 (18)
C2—H20.9300C7—H70.9300
C3—C41.382 (2)N1—N21.3749 (16)
C3—H30.9300N2—H2A0.8604
C4—C51.381 (2)N2—H2B0.8604
C4—H40.9300O1—H10.8200
O1—C1—C2118.26 (12)C4—C5—H5119.1
O1—C1—C6121.42 (12)C6—C5—H5119.1
C2—C1—C6120.32 (13)C5—C6—C1117.79 (13)
C3—C2—C1120.28 (14)C5—C6—C7120.29 (13)
C3—C2—H2119.9C1—C6—C7121.88 (12)
C1—C2—H2119.9N1—C7—C6121.00 (12)
C2—C3—C4120.46 (15)N1—C7—H7119.5
C2—C3—H3119.8C6—C7—H7119.5
C4—C3—H3119.8C7—N1—N2119.21 (12)
C5—C4—C3119.27 (15)N1—N2—H2A124.6
C5—C4—H4120.4N1—N2—H2B102.7
C3—C4—H4120.4H2A—N2—H2B125.9
C4—C5—C6121.86 (14)C1—O1—H1109.5
O1—C1—C2—C3179.29 (13)O1—C1—C6—C5−178.27 (12)
C6—C1—C2—C3−0.8 (2)C2—C1—C6—C51.82 (19)
C1—C2—C3—C4−0.5 (2)O1—C1—C6—C74.02 (19)
C2—C3—C4—C50.8 (2)C2—C1—C6—C7−175.89 (12)
C3—C4—C5—C60.3 (2)C5—C6—C7—N1−174.54 (13)
C4—C5—C6—C1−1.6 (2)C1—C6—C7—N13.1 (2)
C4—C5—C6—C7176.17 (13)C6—C7—N1—N2179.61 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.563.3076 (17)145
N2—H2B···O1ii0.862.233.0530 (16)160
O1—H1···N10.821.892.6109 (15)147

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5112).

References

  • Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. [PubMed]
  • Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hao, Y.-M. (2009). Acta Cryst. E65, o2600. [PMC free article] [PubMed]
  • Lee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S. I., Yun, H., Lee, H. & Park, Y. W. (2005). J. Am. Chem. Soc. 127, 3031–3037. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography